Dalton I - Supplemental Information 1-16-20121 Supplemental Material Synthesis, Characterization and...

Supplemental Material

Synthesis, Characterization and Reactivity of Iron (II) and Iron (III) Compounds with fac-N2O1, cis-N2O2 and N2O3 Donor

Ligands: Models for the 2-His 1-Carboxylate Motif of Mononuclear Nonheme Iron Oxygenases

Patrick J. Cappillino,† John R. Miecznikowski,‡ Laurie A. Tyler,II Paul Tarves,†

Joshua S. McNally,† Wayne Lo,§ Bala Sundari T. Kasibhatla,† Matthew D. Krzyaniak,# John McCracken,# Feng Wang,† William H. Armstrong,§ and John P.

Caradonna†*

† Department of Chemistry, Boston University, Boston, MA 02215 ‡ Department of Chemistry, Fairfield University, Fairfield, CT 06824 II Department of Chemistry, Union College, Schenectady NY 12308

§ Department of Chemistry, Boston College, Chestnut Hill, MA 02467 # Department of Chemistry, Michigan State University, East Lansing, MI 48824

* Corresponding author: Tel – (617) 353-1692 E-mail: caradonn@bu.edu

Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is © The Royal Society of Chemistry 2012

Figure S1 - Infrared Spectrum of N2O3 ligand Page 4 Figure S2 - Infrared Spectrum of N2O2 ligand Page 5 Figure S3 - Infrared Spectrum of N2O1 ligand Page 6 Figure S4 - Infrared Spectrum of (1a) Page 7 Figure S5 - Infrared Spectrum of (2a) Page 8 Figure S6 - Infrared Spectrum of (3a) Page 9 Figure S7 - Infrared Spectrum of (1b) Page 10 Figure S8 - Infrared Spectrum of (2b) Page 11 Figure S9 - Infrared Spectrum of (3b) Page 12 Figure S10 - Infrared Spectrum of (1c) Page 13 Figure S11 - Infrared Spectrum of (2c) Page 14 Figure S12 - Infrared Spectrum of (3c) Page 15 Figure S13 - N2O3 Ligand 1H NMR spectrum Page 16 Figure S14 - N2O3 Ligand 13C NMR spectrum Page 17 Figure S15 - N2O3 Ligand gHMQC NMR spectrum Page 18 Figure S16 - N2O2 Ligand 1H NMR spectrum Page 19 Figure S17 - N2O2 Ligand 13C NMR spectrum Page 20 Figure S18 - N2O2 Ligand gHMQC NMR spectrum Page 21 Figure S19 - N2O1 Ligand 1H NMR Spectrum Page 22 Figure S20 - N2O1 Ligand 13C NMR Spectrum Page 23 Figure S21 - N2O1 Ligand gHMQC NMR Spectrum Page 24 Figure S22 - (1-3a) UV/vis spectra Page 25 Figure S23 - (1-3c) UV/vis spectra Page 26 Figure S24 - Mass Spectrum of (1a) Page 27 Figure S25 - Mass Spectrum of (2a) Page 28 Figure S26 - Mass Spectrum of (3a) Page 29 Figure S27 - Mass Spectrum of (1b) Page 30 Figure S28 - Mass Spectrum of (3b) Page 31 Figure S29 – Electrochemistry of (1b-3b) Page 32-42 Tables S1-S5 - Crystal data and refinement information, atomic coordinates,

bond lengths and angles, anisotropic displacement parameters, and hydrogen coordinates for (1a)

52 Tables S6-S10 - Crystal data and refinement information, atomic coordinates, bond lengths and angles, anisotropic displacement parameters, and hydrogen coordinates for (2a)

63 Tables S11-S15 - Crystal data and refinement information, atomic coordinates, bond lengths and angles, anisotropic displacement parameters, and hydrogen coordinates for (3a)

69 Tables S16-S20 - Crystal data and refinement information, atomic coordinates, bond lengths and angles, anisotropic displacement parameters, and hydrogen coordinates for (1c)

75 Tables S21-S25 - Crystal data and refinement information, atomic coordinates, bond lengths and angles, anisotropic displacement parameters, and hydrogen coordinates for (2c)

Table S26 - Iron ligand bond distances for geometry optimized [FeII(N2O1)(H2O)3]

+ and [FeII(N2O1)2]. Figure S29 - Geometry optimized [FeII(N2O1)(H2O)3]

+ and [FeII(N2O1)2] Figure S30 - Space filling models of [FeII(N2O1)(H2O)3]

+ and [FeII(N2O1)2] Page 76 Figure S31 - Computational models of the configurations for [FeII(N2O1)2] Page 77 Table S27 - Optimized atomic coordinates for [FeII(N2O1)2] Page 78 Table S28 - Optimized atomic coordinates for mer-[FeII(N2O1)Cl3]

Figure S1: Infrared spectrum of N2O3 ligand.

Figure S4: Infrared spectrum of [NEt4][FeIII(N2O3)Cl] (1a) complex.

Figure S5: Infrared spectrum of [NEt4][FeIII(N2O2)Cl2] (2a) complex.

Figure S6: Infrared spectrum of [PSH][FeIII (N2O1)Cl3] (3a) complex.

Figure S7: Infrared spectrum of [Na]2[FeII(N2O3)(OCH3)] (1b) complex.

Figure S8: Infrared spectrum of [FeII(N2O2)(CH3OH)] (2b) complex.

Figure S9: Infrared spectrum of [PSH][FeII(N2O1)Cl2](3b) complex.

Figure S10: Infrared spectrum of [Na]2[(μ−O)(FeIII(N2O3))2] (1c) complex.

Figure S11: Infrared spectrum of [(µ-O)(FeIII(N2O2))2]2 (2c) complex.

Figure S12: Infrared spectrum of [(µ-O)(FeIII(N2O1)Cl)2]n (3c) complex.

Figure S13: 1H NMR spectrum of N2O3 ligand.

Figure S14: 13C NMR spectrum of N2O3 ligand.

Figure S15: gHMQC NMR spectrum of N2O3 ligand.

Figure S22: UV/vis spectra of FeIII complexes (1a–3a) in CH3OH.

Figure S23: UV/vis spectra of FeIII µ-O complexes (1c-3c) in CH3OH.

Figure S24: Mass spectrum of [NEt4][FeIII(N2O3)Cl] (1a) complex.

Figure S25: Mass spectrum of [NEt4][FeIII(N2O2)Cl2] (2a) complex.

Figure S26: Mass spectrum of [PSH][FeIII(N2O1)Cl3] (3a) complex.

Figure S27: Mass spectrum of [Na]2[FeII(N2O3)(OCH3)] (1b) complex.

Figure S28: Mass spectrum of [PSH][FeII(N2O1)Cl2] (3b) complex.

Eº (mV vs. NHE)

Figure S29 – Electrochemistry of (1b-3b)

[PSH][FeII(N2O3)] (1a) (green), [FeII(N2O2)(CH3OH)] (2a) (red), and [PSH][FeII(N2O1)Cl2] (3a) (blue) in DMSO

Table S1. Crystal data and structure refinement for 1a.

Identification code 1a

Empirical formula C17 H33 Cl Fe N3 O6

Formula weight 466.76

Temperature 193(2) K

Wavelength 0.71073 Å

Crystal system Monoclinic

Space group P2(1)

Unit cell dimensions a = 9.5847(19) Å α= 90°.

b = 11.024(2) Å β= 105.97(3)°.

c = 10.765(2) Å γ = 90°.

Volume 1093.5(4) Å3

Density (calculated) 1.418 Mg/m3

Absorption coefficient 0.848 mm-1

F(000) 494

Crystal size .3 x .08 x .08 mm3

Theta range for data collection 1.97 to 23.31°.

Index ranges -10<=h<=10, -9<=k<=12, -11<=l<=10

Reflections collected 4534

Independent reflections 2430 [R(int) = 0.0515]

Completeness to theta = 23.31° 99.6 %

Absorption correction Semi-empirical from equivalents

Max. and min. transmission .92 and .84

Refinement method Full-matrix least-squares on F2

Data / restraints / parameters 2430 / 1 / 259

Goodness-of-fit on F2 0.996

Final R indices [I>2sigma(I)] R1 = 0.0362, wR2 = 0.0693

R indices (all data) R1 = 0.0457, wR2 = 0.0727

Absolute structure parameter 0.52(3)

Largest diff. peak and hole 0.234 and -0.263 e.Å-3

Table S2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103)

for 1a. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

Fe(1) 2507(1) 5127(1) 8949(1) 23(1)

Cl(1) 1078(2) 6736(1) 8122(1) 37(1)

O(2) 3698(3) 5932(3) 10547(3) 28(1)

O(5) 3988(4) 6421(3) 12610(3) 37(1)

O(6) 1151(4) 1956(3) 7175(4) 53(1)

O(3) 1370(4) 3884(3) 7792(3) 32(1)

O(1) 4154(3) 5299(4) 8193(3) 34(1)

O(4) 6537(3) 5041(5) 8596(3) 50(1)

C(7) 3301(6) 5972(5) 11595(5) 26(1)

N(2) 1369(4) 4538(4) 10397(4) 30(1)

C(6) 1828(5) 5407(5) 11478(5) 38(2)

C(4) 5331(5) 3866(5) 9826(5) 37(1)

C(5) 5366(5) 4800(5) 8788(5) 34(2)

C(9) 1825(5) 2768(5) 7823(5) 32(1)

C(1) 3532(5) 3170(5) 10941(5) 36(1)

N(1) 3809(4) 3492(4) 9708(4) 29(1)

C(3) -241(5) 4506(5) 9921(5) 41(2)

C(2) 1916(5) 3289(5) 10822(5) 38(1)

C(8) 3310(5) 2524(4) 8721(5) 35(1)

N(3) 7383(4) 4105(4) 5051(4) 27(1)

C(16) 7864(5) 5096(6) 6056(4) 36(1)

C(12) 7838(5) 2920(5) 5757(5) 31(1)

C(10) 8079(6) 4261(5) 3965(5) 40(1)

C(13) 7484(6) 1792(5) 4923(5) 47(2)

C(15) 4857(5) 4042(5) 5423(6) 49(2)

C(14) 5772(5) 4138(5) 4467(5) 41(2)

C(17) 7467(7) 6372(5) 5572(6) 59(2)

C(11) 9722(6) 4209(6) 4360(6) 57(2)

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Table S3. Bond lengths [Å] and angles [°] for 1a.

_____________________________________________________

Fe(1)-O(3) 1.967(3)

Fe(1)-O(1) 1.975(3)

Fe(1)-O(2) 1.992(3)

Fe(1)-N(1) 2.216(4)

Fe(1)-N(2) 2.231(4)

Fe(1)-Cl(1) 2.2685(15)

O(2)-C(7) 1.287(6)

O(5)-C(7) 1.215(6)

O(6)-C(9) 1.207(6)

O(3)-C(9) 1.303(6)

O(1)-C(5) 1.286(5)

O(4)-C(5) 1.225(5)

C(7)-C(6) 1.515(7)

N(2)-C(6) 1.478(6)

N(2)-C(3) 1.486(5)

N(2)-C(2) 1.499(6)

C(6)-H(6A) 0.9700

C(6)-H(6B) 0.9700

C(4)-N(1) 1.487(6)

C(4)-C(5) 1.526(7)

C(4)-H(4A) 0.9700

C(4)-H(4B) 0.9700

C(9)-C(8) 1.508(6)

C(1)-N(1) 1.467(6)

C(1)-C(2) 1.524(7)

C(1)-H(1A) 0.9700

C(1)-H(1B) 0.9700

N(1)-C(8) 1.489(6)

C(3)-H(3A) 0.9600

C(3)-H(3B) 0.9600

C(3)-H(3C) 0.9600

C(2)-H(2A) 0.9700

C(2)-H(2B) 0.9700

C(8)-H(8A) 0.9700

C(8)-H(8B) 0.9700

N(3)-C(14) 1.499(6)

N(3)-C(10) 1.507(7)

N(3)-C(12) 1.514(6)

N(3)-C(16) 1.517(7)

C(16)-C(17) 1.512(8)

C(16)-H(16A) 0.9700

C(16)-H(16B) 0.9700

C(12)-C(13) 1.516(7)

C(12)-H(12A) 0.9700

C(12)-H(12B) 0.9700

C(10)-C(11) 1.516(7)

C(10)-H(10A) 0.9700

C(10)-H(10B) 0.9700

C(13)-H(13A) 0.9600

C(13)-H(13B) 0.9600

C(13)-H(13C) 0.9600

C(15)-C(14) 1.528(7)

C(15)-H(15A) 0.9600

C(15)-H(15B) 0.9600

C(15)-H(15C) 0.9600

C(14)-H(14A) 0.9700

C(14)-H(14B) 0.9700

C(17)-H(17A) 0.9600

C(17)-H(17B) 0.9600

C(17)-H(17C) 0.9600

C(11)-H(11A) 0.9600

C(11)-H(11B) 0.9600

C(11)-H(11C) 0.9600

O(3)-Fe(1)-O(1) 99.92(15)

O(3)-Fe(1)-O(2) 160.60(14)

O(1)-Fe(1)-O(2) 88.83(13)

O(3)-Fe(1)-N(1) 79.91(14)

O(1)-Fe(1)-N(1) 78.28(16)

O(2)-Fe(1)-N(1) 85.03(14)

O(3)-Fe(1)-N(2) 87.00(14)

O(1)-Fe(1)-N(2) 156.39(14)

O(2)-Fe(1)-N(2) 78.53(14)

N(1)-Fe(1)-N(2) 80.80(15)

O(3)-Fe(1)-Cl(1) 97.27(11)

O(1)-Fe(1)-Cl(1) 103.15(12)

O(2)-Fe(1)-Cl(1) 97.53(10)

N(1)-Fe(1)-Cl(1) 177.06(12)

N(2)-Fe(1)-Cl(1) 98.26(11)

C(7)-O(2)-Fe(1) 122.3(3)

C(9)-O(3)-Fe(1) 121.2(3)

C(5)-O(1)-Fe(1) 117.9(3)

O(5)-C(7)-O(2) 125.7(5)

O(5)-C(7)-C(6) 120.3(5)

O(2)-C(7)-C(6) 114.0(4)

C(6)-N(2)-C(3) 110.1(4)

C(6)-N(2)-C(2) 110.6(4)

C(3)-N(2)-C(2) 109.0(4)

C(6)-N(2)-Fe(1) 105.3(3)

C(3)-N(2)-Fe(1) 115.3(3)

C(2)-N(2)-Fe(1) 106.4(3)

N(2)-C(6)-C(7) 113.7(4)

N(2)-C(6)-H(6A) 108.8

C(7)-C(6)-H(6A) 108.8

N(2)-C(6)-H(6B) 108.8

C(7)-C(6)-H(6B) 108.8

H(6A)-C(6)-H(6B) 107.7

N(1)-C(4)-C(5) 110.1(4)

N(1)-C(4)-H(4A) 109.6

C(5)-C(4)-H(4A) 109.6

N(1)-C(4)-H(4B) 109.6

C(5)-C(4)-H(4B) 109.6

H(4A)-C(4)-H(4B) 108.2

O(4)-C(5)-O(1) 124.6(5)

O(4)-C(5)-C(4) 118.4(5)

O(1)-C(5)-C(4) 117.0(4)

O(6)-C(9)-O(3) 124.3(5)

O(6)-C(9)-C(8) 119.9(5)

O(3)-C(9)-C(8) 115.8(5)

N(1)-C(1)-C(2) 109.7(4)

N(1)-C(1)-H(1A) 109.7

C(2)-C(1)-H(1A) 109.7

N(1)-C(1)-H(1B) 109.7

C(2)-C(1)-H(1B) 109.7

H(1A)-C(1)-H(1B) 108.2

C(1)-N(1)-C(4) 114.1(4)

C(1)-N(1)-C(8) 111.7(4)

C(4)-N(1)-C(8) 112.0(4)

C(1)-N(1)-Fe(1) 107.8(3)

C(4)-N(1)-Fe(1) 104.3(3)

C(8)-N(1)-Fe(1) 106.4(3)

N(2)-C(3)-H(3A) 109.5

N(2)-C(3)-H(3B) 109.5

H(3A)-C(3)-H(3B) 109.5

N(2)-C(3)-H(3C) 109.5

H(3A)-C(3)-H(3C) 109.5

H(3B)-C(3)-H(3C) 109.5

N(2)-C(2)-C(1) 111.5(4)

N(2)-C(2)-H(2A) 109.3

C(1)-C(2)-H(2A) 109.3

N(2)-C(2)-H(2B) 109.3

C(1)-C(2)-H(2B) 109.3

H(2A)-C(2)-H(2B) 108.0

N(1)-C(8)-C(9) 113.0(4)

N(1)-C(8)-H(8A) 109.0

C(9)-C(8)-H(8A) 109.0

N(1)-C(8)-H(8B) 109.0

C(9)-C(8)-H(8B) 109.0

H(8A)-C(8)-H(8B) 107.8

C(14)-N(3)-C(10) 107.3(4)

C(14)-N(3)-C(12) 110.7(4)

C(10)-N(3)-C(12) 111.1(4)

C(14)-N(3)-C(16) 110.9(4)

C(10)-N(3)-C(16) 111.0(4)

C(12)-N(3)-C(16) 105.9(4)

C(17)-C(16)-N(3) 115.2(4)

C(17)-C(16)-H(16A) 108.5

N(3)-C(16)-H(16A) 108.5

C(17)-C(16)-H(16B) 108.5

N(3)-C(16)-H(16B) 108.5

H(16A)-C(16)-H(16B) 107.5

N(3)-C(12)-C(13) 115.1(4)

N(3)-C(12)-H(12A) 108.5

C(13)-C(12)-H(12A) 108.5

N(3)-C(12)-H(12B) 108.5

C(13)-C(12)-H(12B) 108.5

H(12A)-C(12)-H(12B) 107.5

N(3)-C(10)-C(11) 115.2(4)

N(3)-C(10)-H(10A) 108.5

C(11)-C(10)-H(10A) 108.5

N(3)-C(10)-H(10B) 108.5

C(11)-C(10)-H(10B) 108.5

H(10A)-C(10)-H(10B) 107.5

C(12)-C(13)-H(13A) 109.5

C(12)-C(13)-H(13B) 109.5

H(13A)-C(13)-H(13B) 109.5

C(12)-C(13)-H(13C) 109.5

H(13A)-C(13)-H(13C) 109.5

H(13B)-C(13)-H(13C) 109.5

C(14)-C(15)-H(15A) 109.5

C(14)-C(15)-H(15B) 109.5

H(15A)-C(15)-H(15B) 109.5

C(14)-C(15)-H(15C) 109.5

H(15A)-C(15)-H(15C) 109.5

H(15B)-C(15)-H(15C) 109.5

N(3)-C(14)-C(15) 115.6(4)

N(3)-C(14)-H(14A) 108.4

C(15)-C(14)-H(14A) 108.4

N(3)-C(14)-H(14B) 108.4

C(15)-C(14)-H(14B) 108.4

H(14A)-C(14)-H(14B) 107.4

C(16)-C(17)-H(17A) 109.5

C(16)-C(17)-H(17B) 109.5

H(17A)-C(17)-H(17B) 109.5

C(16)-C(17)-H(17C) 109.5

H(17A)-C(17)-H(17C) 109.5

H(17B)-C(17)-H(17C) 109.5

C(10)-C(11)-H(11A) 109.5

C(10)-C(11)-H(11B) 109.5

H(11A)-C(11)-H(11B) 109.5

C(10)-C(11)-H(11C) 109.5

H(11A)-C(11)-H(11C) 109.5

H(11B)-C(11)-H(11C) 109.5

_____________________________________________________________

Symmetry transformations used to generate equivalent atoms:

Table S4. Anisotropic displacement parameters (Å2x 103) for 1a. The anisotropic

displacement factor exponent takes the form: -2π2[ h2 a*2U11 + ... + 2 h k a* b* U12 ]

______________________________________________________________________________

U11 U22 U33 U23 U13 U12

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Fe(1) 25(1) 20(1) 25(1) 1(1) 7(1) 2(1)

Cl(1) 41(1) 28(1) 43(1) 8(1) 12(1) 11(1)

O(2) 27(2) 28(2) 29(2) -2(2) 11(2) -5(2)

O(5) 45(2) 36(2) 27(2) -10(2) 4(2) -1(2)

O(6) 41(2) 34(3) 68(3) -28(2) -12(2) 4(2)

O(3) 32(2) 26(2) 33(2) -4(2) 2(2) 4(2)

O(1) 31(2) 40(2) 33(2) -3(2) 11(2) 5(2)

O(4) 28(2) 63(3) 62(2) -6(3) 19(2) -4(3)

C(7) 36(3) 14(3) 28(3) -1(2) 7(3) 4(2)

N(2) 25(2) 26(3) 39(3) 0(2) 8(2) -4(2)

C(6) 39(3) 39(4) 41(3) -9(3) 21(2) 0(3)

C(4) 33(3) 28(3) 46(3) -4(3) 2(3) 6(3)

C(5) 32(3) 40(4) 31(3) -17(3) 11(2) -1(3)

C(9) 28(3) 28(4) 36(3) -3(3) 4(3) 7(3)

C(1) 40(3) 21(3) 41(3) 6(3) -2(3) 5(3)

N(1) 24(2) 27(3) 29(2) 1(2) -1(2) 1(2)

C(3) 25(3) 45(4) 55(4) 4(3) 13(3) -10(3)

C(2) 39(3) 36(4) 35(3) 5(3) 7(3) -7(3)

C(8) 33(3) 18(3) 47(4) -14(3) -1(3) 2(3)

N(3) 35(3) 20(3) 22(2) 1(2) 2(2) 0(2)

C(16) 40(3) 37(3) 26(2) -8(3) 4(2) -6(4)

C(12) 33(3) 31(3) 30(3) 15(3) 7(2) 5(3)

C(10) 71(4) 25(3) 27(3) 3(3) 21(3) -5(3)

C(13) 61(4) 34(4) 53(4) 11(3) 28(3) 3(3)

C(15) 31(3) 41(4) 65(4) 7(3) -3(3) 6(3)

C(14) 42(3) 31(4) 37(3) -5(3) -10(3) 5(3)

C(17) 83(5) 33(4) 53(4) -13(3) 8(4) -10(4)

C(11) 65(4) 61(5) 58(4) -4(3) 38(4) -22(4)

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Table S5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2x 10 3)

for 1a.

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x y z U(eq)

________________________________________________________________________________

H(6A) 1856 4992 12279 46

H(6B) 1110 6048 11361 46

H(4A) 5900 3162 9730 45

H(4B) 5756 4211 10674 45

H(1A) 4079 3703 11618 43

H(1B) 3844 2343 11170 43

H(3A) -529 3937 9222 62

H(3B) -597 5298 9623 62

H(3C) -636 4262 10610 62

H(2A) 1382 2700 10202 45

H(2B) 1744 3113 11651 45

H(8A) 3291 1757 9157 42

H(8B) 4001 2451 8215 42

H(16A) 7439 4937 6760 43

H(16B) 8910 5050 6404 43

H(12A) 7369 2855 6446 38

H(12B) 8877 2943 6154 38

H(10A) 7778 5037 3552 47

H(10B) 7713 3633 3327 47

H(13A) 6451 1729 4568 70

H(13B) 7838 1089 5439 70

H(13C) 7938 1844 4233 70

H(15A) 5115 3317 5928 73

H(15B) 3848 4014 4957 73

H(15C) 5035 4736 5984 73

H(14A) 5506 3478 3852 49

H(14B) 5526 4891 3990 49

H(17A) 7838 6528 4845 88

H(17B) 7880 6940 6248 88

H(17C) 6430 6457 5314 88

H(11A) 10102 4833 4983 86

H(11B) 10070 4329 3614 86

H(11C) 10036 3430 4733 86

Empirical formula C16 H34 Cl2 Fe N3 O4

Space group P2(1)/c

b = 10.2705(8) Å β= 94.228(2)°.

c = 25.975(2) Å γ = 90°.

Volume 2153.3(3) Å3

F(000) 972

Index ranges -9<=h<=9, -12<=k<=12, -24<=l<=30

Max. and min. transmission 1 and .829234

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

C(1) 4411(3) 8302(3) 7716(1) 36(1)

C(2) 5716(3) 7410(3) 7528(1) 35(1)

C(3) 8154(3) 8803(3) 7685(1) 41(1)

C(4) 7752(3) 9954(3) 8013(1) 40(1)

C(5) 8385(4) 6451(3) 7726(1) 50(1)

C(6) 3350(3) 6851(2) 8360(1) 36(1)

C(7) 3212(4) 9200(3) 8456(1) 45(1)

C(8) 4540(3) 5735(3) 8472(1) 36(1)

C(9A) 6817(6) 1870(4) 9469(2) 39(1)

C(10A) 7699(6) 4188(4) 9595(2) 40(1)

C(11A) 8225(6) 3033(5) 8794(2) 41(1)

C(12A) 9759(6) 2418(5) 9634(2) 43(1)

C(13A) 5090(30) 2190(20) 9276(8) 52(4)

C(14A) 7362(12) 4189(8) 10160(3) 45(2)

C(15A) 9679(12) 3848(9) 8637(5) 56(2)

C(16A) 10453(16) 1201(13) 9403(4) 61(2)

C(9B) 6709(9) 2819(7) 8979(3) 36(2)

C(10B) 7898(10) 3147(8) 9891(3) 45(2)

C(11B) 9512(10) 3688(8) 9148(4) 49(2)

C(12B) 8887(10) 1358(7) 9355(3) 44(2)

C(13B) 5190(30) 2140(30) 9155(13) 37(5)

C(14B) 7160(20) 4468(16) 9940(5) 59(4)

C(15B) 10180(20) 3344(16) 8632(7) 63(4)

C(16B) 10610(30) 1140(20) 9629(6) 60(4)

Cl(1) 9466(1) 7495(1) 8938(1) 52(1)

Cl(2) 5831(1) 8360(1) 9452(1) 47(1)

Fe(1) 6750(1) 7882(1) 8663(1) 30(1)

N(1) 4196(3) 8099(2) 8272(1) 32(1)

N(2) 7331(3) 7588(2) 7829(1) 33(1)

N(3) 8178(3) 2835(2) 9365(1) 34(1)

O(1) 7061(2) 9697(2) 8434(1) 38(1)

O(2) 8082(3) 11055(2) 7873(1) 55(1)

O(3) 6041(2) 6050(2) 8617(1) 38(1)

O(4) 4037(3) 4619(2) 8434(1) 55(1)

________________________________________________________________________________

_____________________________________________________

C(1)-N(1) 1.483(4)

C(1)-C(2) 1.506(4)

C(2)-N(2) 1.484(3)

C(3)-N(2) 1.476(4)

C(3)-C(4) 1.508(4)

C(4)-O(2) 1.223(4)

C(4)-O(1) 1.290(3)

C(5)-N(2) 1.482(4)

C(6)-N(1) 1.479(3)

C(6)-C(8) 1.511(4)

C(7)-N(1) 1.483(3)

C(8)-O(4) 1.218(3)

C(8)-O(3) 1.286(3)

C(9A)-C(13A) 1.48(2)

C(9A)-N(3) 1.520(4)

C(10A)-C(14A) 1.513(8)

C(10A)-N(3) 1.573(5)

C(11A)-N(3) 1.499(5)

C(11A)-C(15A) 1.523(11)

C(12A)-N(3) 1.476(5)

C(12A)-C(16A) 1.513(13)

C(9B)-N(3) 1.497(8)

C(9B)-C(13B) 1.51(3)

C(10B)-N(3) 1.438(8)

C(10B)-C(14B) 1.493(19)

C(11B)-C(15B) 1.523(19)

C(11B)-N(3) 1.530(7)

C(12B)-C(16B) 1.535(19)

C(12B)-N(3) 1.622(8)

Cl(1)-Fe(1) 2.2953(8)

Cl(2)-Fe(1) 2.2835(8)

Fe(1)-O(3) 1.9677(18)

Fe(1)-O(1) 1.9795(18)

Fe(1)-N(1) 2.246(2)

Fe(1)-N(2) 2.271(2)

N(1)-C(1)-C(2) 111.4(2)

N(2)-C(2)-C(1) 111.5(2)

N(2)-C(3)-C(4) 113.5(2)

O(2)-C(4)-O(1) 124.0(3)

O(2)-C(4)-C(3) 119.7(2)

O(1)-C(4)-C(3) 116.3(2)

N(1)-C(6)-C(8) 113.0(2)

O(4)-C(8)-O(3) 124.3(3)

O(4)-C(8)-C(6) 119.6(3)

O(3)-C(8)-C(6) 116.1(2)

C(13A)-C(9A)-N(3) 118.1(10)

C(14A)-C(10A)-N(3) 115.9(5)

N(3)-C(11A)-C(15A) 114.5(6)

N(3)-C(12A)-C(16A) 112.7(5)

N(3)-C(9B)-C(13B) 115.3(12)

N(3)-C(10B)-C(14B) 112.1(8)

C(15B)-C(11B)-N(3) 119.8(9)

C(16B)-C(12B)-N(3) 116.0(11)

O(3)-Fe(1)-O(1) 157.69(8)

O(3)-Fe(1)-N(1) 79.21(8)

O(1)-Fe(1)-N(1) 84.46(8)

O(3)-Fe(1)-N(2) 83.95(8)

O(1)-Fe(1)-N(2) 78.34(8)

N(1)-Fe(1)-N(2) 80.19(8)

O(3)-Fe(1)-Cl(2) 98.50(6)

O(1)-Fe(1)-Cl(2) 97.16(6)

N(1)-Fe(1)-Cl(2) 91.99(6)

N(2)-Fe(1)-Cl(2) 171.27(6)

O(3)-Fe(1)-Cl(1) 96.99(6)

O(1)-Fe(1)-Cl(1) 96.69(6)

N(1)-Fe(1)-Cl(1) 170.43(6)

N(2)-Fe(1)-Cl(1) 90.71(6)

Cl(2)-Fe(1)-Cl(1) 97.28(3)

C(6)-N(1)-C(1) 111.2(2)

C(6)-N(1)-C(7) 110.2(2)

C(1)-N(1)-C(7) 108.1(2)

C(6)-N(1)-Fe(1) 105.36(16)

C(1)-N(1)-Fe(1) 106.55(15)

C(7)-N(1)-Fe(1) 115.32(18)

C(3)-N(2)-C(5) 110.1(2)

C(3)-N(2)-C(2) 111.5(2)

C(5)-N(2)-C(2) 107.7(2)

C(3)-N(2)-Fe(1) 105.01(16)

C(5)-N(2)-Fe(1) 116.08(19)

C(2)-N(2)-Fe(1) 106.42(15)

C(10B)-N(3)-C(12A) 78.8(4)

C(10B)-N(3)-C(9B) 117.7(5)

C(12A)-N(3)-C(9B) 158.8(4)

C(10B)-N(3)-C(11A) 157.9(4)

C(12A)-N(3)-C(11A) 115.1(3)

C(9B)-N(3)-C(11A) 54.3(3)

C(10B)-N(3)-C(9A) 79.0(4)

C(12A)-N(3)-C(9A) 109.9(3)

C(9B)-N(3)-C(9A) 64.0(3)

C(11A)-N(3)-C(9A) 109.6(3)

C(10B)-N(3)-C(11B) 112.8(5)

C(12A)-N(3)-C(11B) 74.4(4)

C(9B)-N(3)-C(11B) 107.9(5)

C(11A)-N(3)-C(11B) 59.2(4)

C(9A)-N(3)-C(11B) 168.2(4)

C(10B)-N(3)-C(10A) 51.7(4)

C(12A)-N(3)-C(10A) 107.8(3)

C(9B)-N(3)-C(10A) 93.3(4)

C(11A)-N(3)-C(10A) 106.3(3)

C(9A)-N(3)-C(10A) 107.8(3)

C(11B)-N(3)-C(10A) 80.5(4)

C(10B)-N(3)-C(12B) 107.7(5)

C(12A)-N(3)-C(12B) 56.0(3)

C(9B)-N(3)-C(12B) 104.1(4)

C(11A)-N(3)-C(12B) 94.4(4)

C(9A)-N(3)-C(12B) 69.9(3)

C(11B)-N(3)-C(12B) 105.6(4)

C(10A)-N(3)-C(12B) 158.3(4)

C(4)-O(1)-Fe(1) 121.36(18)

C(8)-O(3)-Fe(1) 121.53(17)

_____________________________________________________________

______________________________________________________________________________

U11 U22 U33 U23 U13 U12

______________________________________________________________________________

C(1) 36(1) 39(1) 31(2) 5(1) -5(1) 0(1)

C(2) 34(1) 47(2) 22(1) -2(1) -1(1) -5(1)

C(3) 36(1) 60(2) 28(2) -4(1) 8(1) -14(1)

C(4) 39(2) 54(2) 27(2) 2(1) 0(1) -16(1)

C(5) 41(2) 65(2) 45(2) -20(2) 3(1) 11(2)

C(6) 30(1) 42(1) 38(2) 1(1) 6(1) -4(1)

C(7) 42(2) 45(2) 49(2) 0(2) 6(1) 10(1)

C(8) 43(2) 39(2) 27(1) 6(1) 1(1) -5(1)

C(9A) 51(3) 34(2) 33(3) 0(2) 7(2) -12(2)

C(10A) 50(3) 34(2) 35(3) -5(2) 3(2) -6(2)

C(11A) 51(3) 46(3) 26(3) 0(2) 8(2) -3(2)

C(12A) 45(3) 45(3) 39(3) -1(2) -6(2) -1(2)

C(13A) 55(7) 62(6) 38(8) 6(5) 3(5) -16(4)

C(14A) 57(4) 47(4) 32(4) -7(3) 7(3) -5(3)

C(15A) 60(6) 62(5) 48(4) 6(4) 25(4) -9(4)

C(16A) 54(5) 55(4) 72(7) 3(6) -5(6) 23(3)

C(9B) 37(4) 37(4) 32(4) 6(3) -6(3) 0(3)

C(10B) 41(4) 63(5) 29(4) -2(4) -3(3) -6(4)

C(11B) 46(5) 48(4) 55(6) 2(4) 12(4) -17(4)

C(12B) 46(5) 42(4) 42(5) 0(4) -4(4) 2(3)

C(13B) 23(6) 45(7) 41(14) 6(7) 1(6) -7(5)

C(14B) 74(8) 67(9) 37(9) -11(7) 10(8) -2(6)

C(15B) 67(11) 84(12) 40(7) 0(9) 16(7) -22(8)

C(16B) 50(7) 65(7) 61(10) 8(9) -18(9) 4(5)

Cl(1) 31(1) 85(1) 38(1) -7(1) -6(1) 2(1)

Cl(2) 54(1) 62(1) 27(1) 0(1) 12(1) -7(1)

Fe(1) 29(1) 37(1) 23(1) 0(1) 1(1) -2(1)

N(1) 31(1) 35(1) 31(1) 3(1) 4(1) 1(1)

N(2) 29(1) 45(1) 26(1) -6(1) 3(1) -1(1)

N(3) 39(1) 36(1) 28(1) 3(1) 0(1) -7(1)

O(1) 49(1) 39(1) 28(1) -2(1) 9(1) -10(1)

O(2) 75(2) 53(1) 36(1) 4(1) 6(1) -26(1)

O(3) 36(1) 34(1) 44(1) 5(1) -5(1) 1(1)

O(4) 64(1) 37(1) 63(2) 9(1) -10(1) -11(1)

______________________________________________________________________________

for 2a.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

H(1A) 4726 9199 7659 43

H(1B) 3367 8143 7518 43

H(2A) 5358 6513 7559 42

H(2B) 5849 7584 7167 42

H(3A) 7825 9000 7327 49

H(3B) 9343 8668 7714 49

H(5A) 8516 6393 7363 76

H(5B) 7871 5671 7840 76

H(5C) 9452 6553 7909 76

H(6A) 2628 6641 8057 44

H(6B) 2664 6952 8648 44

H(7A) 2155 9229 8263 68

H(7B) 3793 10002 8409 68

H(7C) 3052 9084 8816 68

H(9A1) 7102 1040 9320 47

H(9A2) 6831 1748 9839 47

H(10A) 8590 4797 9547 48

H(10B) 6719 4509 9398 48

H(11A) 7203 3451 8665 49

H(11B) 8270 2187 8629 49

H(12A) 9588 2258 9995 52

H(12B) 10561 3116 9620 52

H(13A) 4740 2962 9445 77

H(13B) 4376 1479 9348 77

H(13C) 5052 2336 8910 77

H(14A) 6475 3596 10215 68

H(14B) 7055 5051 10261 68

H(14C) 8342 3922 10364 68

H(15A) 9561 4726 8756 84

H(15B) 9697 3844 8268 84

H(15C) 10695 3487 8789 84

H(16A) 9695 491 9436 91

H(16B) 11500 991 9582 91

H(16C) 10604 1347 9045 91

H(9B1) 7026 2394 8668 43

H(9B2) 6419 3712 8890 43

H(10C) 8943 3108 10099 53

H(10D) 7162 2503 10023 53

H(11C) 9075 4567 9119 59

H(11D) 10447 3712 9403 59

H(12C) 8109 790 9511 52

H(12D) 8924 1092 8997 52

H(13D) 5428 1240 9216 55

H(13E) 4295 2224 8892 55

H(13F) 4874 2540 9468 55

H(14D) 7891 5110 9815 88

H(14E) 6994 4639 10296 88

H(14F) 6112 4505 9740 88

H(15D) 10641 2483 8650 95

H(15E) 11024 3957 8556 95

H(15F) 9295 3377 8365 95

H(16D) 11436 1522 9429 90

H(16E) 10815 225 9668 90

H(16F) 10658 1544 9964 90 ________________________________________________________________________________

Empirical formula C21 H34 Cl3 Fe N4 O2

Space group P 21/c

b = 10.9015(11) Å β= 104.284(2)°.

c = 15.4710(14) Å γ = 90°.

Volume 2563.6(4) Å3

F(000) 1124

Index ranges -12<=h<=18, -12<=k<=12, -18<=l<=17

Max. and min. transmission 1 and 0.648159

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

C(1) 8975(10) 4841(12) 2520(10) 125(5)

C(2) 8798(7) 4465(12) 1654(7) 96(3)

C(5) 7873(6) 3356(10) 459(6) 82(3)

C(6) 7802(8) 6015(9) 2889(8) 98(3)

C(50) 5852(5) 10152(8) 3791(6) 67(2)

C(51) 5867(6) 8597(9) 2644(5) 74(2)

C(52) 5636(6) 6009(8) 4134(7) 74(3)

C(53) 5334(5) 7384(8) 5248(5) 59(2)

C(60) 6837(5) 7147(6) 5056(5) 47(2)

C(61) 7187(6) 6401(7) 5760(6) 61(2)

C(62) 8089(6) 6382(8) 6138(6) 69(2)

C(63) 8640(6) 7074(7) 5817(5) 60(2)

C(64) 8894(5) 8579(7) 4713(6) 59(2)

C(65) 8586(5) 9347(7) 4025(6) 58(2)

C(66) 7680(5) 9452(7) 3648(5) 53(2)

C(67) 7106(4) 8758(6) 3976(4) 41(2)

C(68) 7393(4) 7926(6) 4694(4) 39(1)

C(69) 8320(5) 7858(6) 5076(5) 47(2)

C(3A) 8893(9) 2297(14) 1687(10) 86(4)

C(4A) 8947(8) 1918(11) 2670(8) 71(3)

C(7A) 8612(11) 4689(16) 3949(10) 107(5)

C(3B) 8870(30) 4280(30) 3690(30) 85(15)

C(4B) 8820(30) 2850(30) 3680(30) 93(16)

C(7B) 8680(20) 1980(20) 1410(20) 45(8)

Cl(1) 6728(2) 1474(2) 1636(2) 66(1)

Cl(2) 6629(2) 3321(2) 3443(2) 75(1)

Cl(3) 6426(2) 4585(2) 1360(2) 81(1)

Fe(1) 7361(1) 3249(1) 2333(1) 48(1)

N(1) 8255(5) 4842(6) 2943(5) 67(2)

N(2) 8286(4) 3302(6) 1413(4) 55(2)

N(30) 6153(4) 8918(6) 3607(4) 46(1)

N(31) 5901(4) 7157(5) 4639(4) 47(1)

O(1A) 8429(11) 2370(20) 3118(14) 161(15)

O(2A) 9571(7) 1257(10) 3023(7) 108(3)

O(1B) 8327(6) 2244(9) 3020(7) 16(3)

O(2B) 9360(20) 2330(30) 4270(20) 116(13)

________________________________________________________________________________

_____________________________________________________

C(1)-C(2) 1.362(16)

C(1)-N(1) 1.439(13)

C(2)-N(2) 1.498(12)

C(5)-N(2) 1.459(10)

C(6)-N(1) 1.455(11)

C(50)-N(30) 1.477(10)

C(51)-N(30) 1.487(10)

C(52)-N(31) 1.481(9)

C(53)-N(31) 1.467(9)

C(60)-C(61) 1.362(11)

C(60)-C(68) 1.427(9)

C(60)-N(31) 1.451(9)

C(61)-C(62) 1.392(12)

C(62)-C(63) 1.332(12)

C(63)-C(69) 1.419(10)

C(64)-C(65) 1.347(11)

C(64)-C(69) 1.411(11)

C(65)-C(66) 1.402(11)

C(66)-C(67) 1.365(10)

C(67)-C(68) 1.418(9)

C(67)-N(30) 1.473(9)

C(68)-C(69) 1.430(10)

C(3A)-N(2) 1.445(14)

C(3A)-C(4A) 1.558(18)

C(4A)-O(2A) 1.230(14)

C(4A)-O(1A) 1.29(2)

C(7A)-N(1) 1.527(15)

C(3B)-N(1) 1.45(2)

C(3B)-C(4B) 1.56(3)

C(4B)-O(2B) 1.22(2)

C(4B)-O(1B) 1.30(3)

C(7B)-N(2) 1.57(2)

Cl(1)-Fe(1) 2.316(2)

Cl(2)-Fe(1) 2.290(2)

Cl(3)-Fe(1) 2.335(2)

Fe(1)-O(1B) 1.957(8)

Fe(1)-O(1A) 2.051(13)

Fe(1)-N(2) 2.271(6)

Fe(1)-N(1) 2.285(7)

C(2)-C(1)-N(1) 117.1(12)

C(1)-C(2)-N(2) 117.8(9)

C(61)-C(60)-C(68) 120.3(7)

C(61)-C(60)-N(31) 121.6(6)

C(68)-C(60)-N(31) 118.1(6)

C(60)-C(61)-C(62) 120.8(7)

C(63)-C(62)-C(61) 121.4(8)

C(62)-C(63)-C(69) 120.7(8)

C(65)-C(64)-C(69) 121.4(7)

C(64)-C(65)-C(66) 120.5(7)

C(67)-C(66)-C(65) 119.6(7)

C(66)-C(67)-C(68) 122.3(6)

C(66)-C(67)-N(30) 119.3(6)

C(68)-C(67)-N(30) 118.3(6)

C(67)-C(68)-C(60) 125.5(6)

C(67)-C(68)-C(69) 116.8(6)

C(60)-C(68)-C(69) 117.7(6)

C(64)-C(69)-C(63) 121.6(7)

C(64)-C(69)-C(68) 119.3(7)

C(63)-C(69)-C(68) 119.1(7)

N(2)-C(3A)-C(4A) 111.2(11)

O(2A)-C(4A)-O(1A) 121.5(13)

O(2A)-C(4A)-C(3A) 115.7(11)

O(1A)-C(4A)-C(3A) 122.4(12)

N(1)-C(3B)-C(4B) 113(3)

O(2B)-C(4B)-O(1B) 121(2)

O(2B)-C(4B)-C(3B) 115(2)

O(1B)-C(4B)-C(3B) 122(3)

O(1B)-Fe(1)-O(1A) 6.1(8)

O(1B)-Fe(1)-N(2) 80.0(3)

O(1A)-Fe(1)-N(2) 80.1(6)

O(1B)-Fe(1)-N(1) 83.5(4)

O(1A)-Fe(1)-N(1) 77.5(7)

N(2)-Fe(1)-N(1) 79.5(3)

O(1B)-Fe(1)-Cl(2) 94.4(3)

O(1A)-Fe(1)-Cl(2) 93.4(6)

N(2)-Fe(1)-Cl(2) 170.20(18)

N(1)-Fe(1)-Cl(2) 91.96(19)

O(1B)-Fe(1)-Cl(1) 88.3(3)

O(1A)-Fe(1)-Cl(1) 94.4(7)

N(2)-Fe(1)-Cl(1) 89.78(18)

N(1)-Fe(1)-Cl(1) 167.5(2)

Cl(2)-Fe(1)-Cl(1) 98.11(9)

O(1B)-Fe(1)-Cl(3) 168.1(3)

O(1A)-Fe(1)-Cl(3) 165.1(6)

N(2)-Fe(1)-Cl(3) 88.67(16)

N(1)-Fe(1)-Cl(3) 90.93(19)

Cl(2)-Fe(1)-Cl(3) 96.34(9)

Cl(1)-Fe(1)-Cl(3) 95.28(10)

C(1)-N(1)-C(3B) 85(2)

C(1)-N(1)-C(6) 113.7(9)

C(3B)-N(1)-C(6) 129.6(19)

C(1)-N(1)-C(7A) 109.3(10)

C(3B)-N(1)-C(7A) 30(2)

C(6)-N(1)-C(7A) 101.9(9)

C(1)-N(1)-Fe(1) 106.4(6)

C(3B)-N(1)-Fe(1) 103.2(16)

C(6)-N(1)-Fe(1) 113.8(6)

C(7A)-N(1)-Fe(1) 111.8(7)

C(3A)-N(2)-C(5) 115.1(8)

C(3A)-N(2)-C(2) 107.1(9)

C(5)-N(2)-C(2) 107.2(7)

C(3A)-N(2)-C(7B) 22.1(13)

C(5)-N(2)-C(7B) 96.4(12)

C(2)-N(2)-C(7B) 126.5(16)

C(3A)-N(2)-Fe(1) 105.8(7)

C(5)-N(2)-Fe(1) 116.2(5)

C(2)-N(2)-Fe(1) 104.6(6)

C(7B)-N(2)-Fe(1) 106.6(14)

C(67)-N(30)-C(50) 112.0(6)

C(67)-N(30)-C(51) 112.8(6)

C(50)-N(30)-C(51) 112.0(7)

C(60)-N(31)-C(53) 115.0(6)

C(60)-N(31)-C(52) 110.5(6)

C(53)-N(31)-C(52) 110.2(6)

C(4A)-O(1A)-Fe(1) 113.0(13)

C(4B)-O(1B)-Fe(1) 111.9(17)

_____________________________________________________________

______________________________________________________________________________

U11 U22 U33 U23 U13 U12

______________________________________________________________________________

C(1) 162(12) 89(8) 148(9) -44(8) 82(10) -63(8)

C(2) 84(7) 114(9) 89(6) 6(6) 21(6) -44(6)

C(5) 83(6) 109(8) 56(5) -5(5) 20(5) -4(6)

C(6) 136(10) 53(5) 103(8) -16(5) 23(7) 20(6)

C(50) 51(4) 60(5) 85(6) 0(4) 8(4) 5(4)

C(51) 86(6) 84(6) 44(4) 5(4) 1(4) -16(5)

C(52) 71(5) 59(5) 99(7) -35(5) 37(5) -19(4)

C(53) 59(5) 58(5) 67(5) -11(4) 31(4) -6(4)

C(60) 63(4) 32(3) 51(4) -4(3) 25(3) -2(3)

C(61) 79(6) 42(4) 68(5) 12(4) 31(4) 6(4)

C(62) 84(6) 53(5) 71(5) 22(4) 20(5) 21(4)

C(63) 62(5) 51(4) 64(5) 1(4) 7(4) 16(4)

C(64) 48(4) 57(5) 74(5) -9(4) 22(4) 3(4)

C(65) 57(5) 56(4) 70(5) 1(4) 31(4) -7(4)

C(66) 67(5) 48(4) 49(4) 10(3) 24(4) 1(3)

C(67) 48(4) 40(3) 39(3) -6(3) 15(3) -1(3)

C(68) 52(4) 30(3) 35(3) -7(3) 13(3) -1(3)

C(69) 52(4) 39(4) 50(4) -7(3) 12(3) 6(3)

Cl(1) 81(1) 49(1) 68(1) -5(1) 19(1) -8(1)

Cl(2) 105(2) 57(1) 79(1) 1(1) 53(1) 9(1)

Cl(3) 69(1) 80(2) 90(2) 29(1) 16(1) 33(1)

Fe(1) 58(1) 36(1) 52(1) 5(1) 18(1) 9(1)

N(1) 82(5) 47(4) 76(5) 3(3) 25(4) 3(3)

N(2) 55(4) 57(4) 52(4) 9(3) 11(3) 11(3)

N(30) 50(3) 45(3) 42(3) 4(3) 11(3) -9(3)

N(31) 57(3) 37(3) 53(3) -7(3) 24(3) -8(3)

______________________________________________________________________________

for 3a.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

H(1A) 9211 5667 2551 150

H(1B) 9434 4317 2866 150

H(2A) 9354 4370 1493 115

H(2B) 8478 5118 1286 115

H(5A) 8319 3387 133 123

H(5B) 7512 4077 331 123

H(5C) 7515 2640 285 123

H(6A) 7385 5989 3251 147

H(6B) 7499 6175 2281 147

H(6C) 8223 6654 3100 147

H(50A) 5999 10292 4423 101

H(50B) 5226 10209 3561 101

H(50C) 6135 10758 3508 101

H(51A) 6100 9186 2302 111

H(51B) 5236 8604 2458 111

H(51C) 6080 7794 2552 111

H(52A) 6012 5868 3740 111

H(52B) 5037 6078 3792 111

H(52C) 5685 5334 4542 111

H(53A) 5360 6694 5638 88

H(53B) 4738 7502 4908 88

H(53C) 5532 8106 5595 88

H(61) 6818 5897 5991 73

H(62) 8312 5875 6625 83

H(63) 9240 7043 6081 72

H(64) 9497 8523 4955 71

H(65) 8979 9812 3798 70

H(66) 7471 9990 3177 64

H(3A1) 9472 2538 1632 103

H(3A2) 8703 1600 1298 103

H(7A1) 8813 3862 4078 161

H(7A2) 8155 4865 4244 161

H(7A3) 9094 5245 4157 161

H(3B1) 8755 4579 4243 102

H(3B2) 9464 4525 3686 102

H(7B1) 9180 2002 1165 67

H(7B2) 8238 1444 1058 67

H(7B3) 8847 1673 2012 67

H(99) 5910(50) 8460(70) 3900(50) 40(19) ________________________________________________________________________________

Table S16. Crystal data and structure refinement for 1c.

Identification code 1c

Empirical formula

Space group C2/c

b = 11.2284(17) Å β= 102.109(2)°.

c = 14.423(2) Å γ = 90°.

Volume 3123.6(8) Å3

F(000) 1676

Index ranges -23<=h<=23, -13<=k<=13, -17<=l<=17

for 1c. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

C(1) 2661(3) 139(5) 1563(4) 20(1)

C(2) 3082(3) -114(5) 821(4) 19(1)

C(3) 4010(3) -1357(5) 1715(4) 21(1)

C(4) 3959(3) -1315(5) 2754(4) 20(1)

C(5) 2682(3) 2314(5) 1511(4) 24(1)

C(6) 3258(3) 2939(5) 1152(4) 22(1)

C(7) 2759(3) 1350(5) 3021(4) 21(1)

C(8) 3294(3) 2156(5) 3650(4) 17(1)

C(9) 4245(3) -47(6) 485(4) 25(1)

C(10) 5815(4) 5038(6) 2236(5) 33(2)

Fe(1) 4085(1) 1160(1) 2351(1) 10(1)

Fe(2) 5000 5000 0 34(1)

N(1) 2912(2) 1232(4) 2087(3) 19(1)

N(2) 3836(2) -186(4) 1232(3) 19(1)

O(1) 3112(2) 3861(4) 696(3) 32(1)

O(2) 3860(2) 2473(3) 1361(3) 19(1)

O(3) 3143(2) 2692(4) 4318(3) 23(1)

O(4) 3892(2) 2185(3) 3424(3) 17(1)

O(5) 3995(2) -297(3) 3129(3) 20(1)

O(6) 3885(2) -2256(4) 3177(3) 31(1)

O(7) 5000 1306(5) 2500 16(1)

O(8) 5489(3) 5672(4) 1399(3) 37(1)

O(9) 3988(2) 5524(4) 232(3) 31(1)

O(10) 4928(2) 3246(4) 556(3) 26(1)

________________________________________________________________________________

Table S18. Bond lengths [Å] and angles [°] for 1c.

_____________________________________________________

C(1)-N(1) 1.470(7)

C(1)-C(2) 1.513(8)

C(2)-N(2) 1.484(7)

C(3)-N(2) 1.494(7)

C(3)-C(4) 1.523(8)

C(4)-O(6) 1.243(7)

C(4)-O(5) 1.260(7)

C(5)-N(1) 1.489(7)

C(5)-C(6) 1.517(8)

C(6)-O(1) 1.228(7)

C(6)-O(2) 1.274(7)

C(7)-N(1) 1.447(7)

C(7)-C(8) 1.533(8)

C(8)-O(3) 1.224(7)

C(8)-O(4) 1.290(7)

C(9)-N(2) 1.484(7)

C(10)-O(8) 1.433(8)

Fe(1)-O(7) 1.7795(9)

Fe(1)-O(5) 2.013(4)

Fe(1)-O(4) 2.028(4)

Fe(1)-O(2) 2.035(4)

Fe(1)-N(2) 2.190(5)

Fe(1)-N(1) 2.267(5)

Fe(2)-O(10) 2.143(4)

Fe(2)-O(10)#1 2.143(4)

Fe(2)-O(9) 2.174(5)

Fe(2)-O(9)#1 2.174(5)

Fe(2)-O(8)#1 2.180(5)

Fe(2)-O(8) 2.180(5)

O(7)-Fe(1)#2 1.7795(9)

N(1)-C(1)-C(2) 110.2(4)

N(2)-C(2)-C(1) 112.4(4)

N(2)-C(3)-C(4) 112.1(4)

O(6)-C(4)-O(5) 124.2(6)

O(6)-C(4)-C(3) 119.6(5)

O(5)-C(4)-C(3) 116.1(5)

N(1)-C(5)-C(6) 113.9(5)

O(1)-C(6)-O(2) 125.2(6)

O(1)-C(6)-C(5) 117.6(5)

O(2)-C(6)-C(5) 117.2(5)

N(1)-C(7)-C(8) 110.7(5)

O(3)-C(8)-O(4) 124.9(5)

O(3)-C(8)-C(7) 120.4(5)

O(4)-C(8)-C(7) 114.7(5)

O(7)-Fe(1)-O(5) 102.29(18)

O(7)-Fe(1)-O(4) 101.73(15)

O(5)-Fe(1)-O(4) 89.02(16)

O(7)-Fe(1)-O(2) 94.88(16)

O(5)-Fe(1)-O(2) 161.45(15)

O(4)-Fe(1)-O(2) 94.37(16)

O(7)-Fe(1)-N(2) 102.56(17)

O(5)-Fe(1)-N(2) 79.48(17)

O(4)-Fe(1)-N(2) 154.83(16)

O(2)-Fe(1)-N(2) 90.06(17)

O(7)-Fe(1)-N(1) 172.3(2)

O(5)-Fe(1)-N(1) 85.18(16)

O(4)-Fe(1)-N(1) 76.08(16)

O(2)-Fe(1)-N(1) 77.99(16)

N(2)-Fe(1)-N(1) 80.66(17)

O(10)-Fe(2)-O(10)#1 180.0(2)

O(10)-Fe(2)-O(9) 93.19(16)

O(10)#1-Fe(2)-O(9) 86.81(16)

O(10)-Fe(2)-O(9)#1 86.81(16)

O(10)#1-Fe(2)-O(9)#1 93.19(16)

O(9)-Fe(2)-O(9)#1 180.0(2)

O(10)-Fe(2)-O(8)#1 88.67(17)

O(10)#1-Fe(2)-O(8)#1 91.33(17)

O(9)-Fe(2)-O(8)#1 89.65(18)

O(9)#1-Fe(2)-O(8)#1 90.35(18)

O(10)-Fe(2)-O(8) 91.33(17)

O(10)#1-Fe(2)-O(8) 88.67(17)

O(9)-Fe(2)-O(8) 90.34(18)

O(9)#1-Fe(2)-O(8) 89.66(18)

O(8)#1-Fe(2)-O(8) 179.998(1)

C(7)-N(1)-C(1) 116.3(4)

C(7)-N(1)-C(5) 110.2(5)

C(1)-N(1)-C(5) 111.3(4)

C(7)-N(1)-Fe(1) 104.6(3)

C(1)-N(1)-Fe(1) 106.1(3)

C(5)-N(1)-Fe(1) 107.6(3)

C(2)-N(2)-C(9) 110.9(4)

C(2)-N(2)-C(3) 110.3(4)

C(9)-N(2)-C(3) 109.0(5)

C(2)-N(2)-Fe(1) 107.9(3)

C(9)-N(2)-Fe(1) 113.0(3)

C(3)-N(2)-Fe(1) 105.7(3)

C(6)-O(2)-Fe(1) 121.3(4)

C(8)-O(4)-Fe(1) 120.4(3)

C(4)-O(5)-Fe(1) 120.1(4)

Fe(1)#2-O(7)-Fe(1) 169.5(3)

C(10)-O(8)-Fe(2) 129.9(4)

_____________________________________________________________

#1 -x+1,-y+1,-z #2 -x+1,y,-z+1/2

Table S19. Anisotropic displacement parameters (Å2x 103) for 1c. The anisotropic

______________________________________________________________________________

U11 U22 U33 U23 U13 U12

______________________________________________________________________________

C(1) 9(2) 24(3) 23(3) -2(2) -1(2) -5(2)

C(2) 11(3) 27(3) 16(3) -3(2) -3(2) -4(2)

C(3) 22(3) 16(3) 27(3) -3(2) 7(2) 0(2)

C(4) 13(3) 18(3) 27(3) 4(2) -4(2) 0(2)

C(5) 17(3) 23(3) 31(3) 11(3) 0(2) 3(2)

C(6) 20(3) 22(3) 18(3) 3(2) -6(2) -5(2)

C(7) 16(3) 24(3) 23(3) -2(2) 5(2) -1(2)

C(8) 19(3) 8(2) 20(3) 5(2) -2(2) 3(2)

C(9) 20(3) 39(4) 15(3) -9(3) 3(2) -6(3)

C(10) 35(4) 32(4) 35(4) 0(3) 11(3) 0(3)

Fe(1) 8(1) 10(1) 10(1) 1(1) -2(1) -1(1)

Fe(2) 33(1) 30(1) 35(1) 6(1) -1(1) -5(1)

N(1) 12(2) 20(2) 22(2) 1(2) 1(2) -3(2)

N(2) 15(2) 26(3) 14(2) -3(2) 2(2) -3(2)

O(1) 22(2) 25(2) 41(3) 21(2) -5(2) -4(2)

O(2) 13(2) 18(2) 22(2) 8(2) -5(2) -2(2)

O(3) 27(2) 21(2) 22(2) -6(2) 10(2) 4(2)

O(4) 16(2) 17(2) 19(2) -5(2) 4(2) -2(2)

O(5) 20(2) 20(2) 17(2) 4(2) -3(2) -2(2)

O(6) 36(3) 18(2) 37(3) 11(2) 2(2) 1(2)

O(7) 7(2) 22(3) 18(3) 0 -3(2) 0

O(8) 53(3) 25(2) 29(2) 3(2) 1(2) -8(2)

O(9) 29(2) 25(2) 36(3) 12(2) -2(2) -11(2)

O(10) 20(2) 28(2) 29(2) 7(2) 3(2) -2(2)

______________________________________________________________________________

for 1c.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

H(1A) 2177 232 1260 23

H(1B) 2700 -526 2001 23

H(2A) 2929 -861 509 23

H(2B) 2999 510 346 23

H(3A) 4477 -1583 1673 26

H(3B) 3695 -1960 1391 26

H(5A) 2481 2870 1892 29

H(5B) 2322 2090 972 29

H(7A) 2764 571 3312 25

H(7B) 2299 1686 2967 25

H(9A) 4132 -679 31 37

H(9B) 4731 -76 768 37

H(9C) 4137 705 172 37

H(10A) 5591 4282 2254 50

H(10B) 5777 5494 2786 50

H(10C) 6295 4915 2230 50

H(9) 3761 4927 291 47

H(10) 4730 3277 1001 39

________________________________________________________________________________

Table S21. Crystal data and structure refinement for 2c.

Identification code 2c

Empirical formula C17 H32 Fe2 N4 O10

Temperature 193 K

Crystal system Tetragonal

Space group P-42(1)c

b = 12.8820(5) Å β= 90°.

c = 13.7401(7) Å γ = 90°.

Volume 2280.11(17) Å3

F(000) 1176

Index ranges -12<=h<=15, -15<=k<=13, -16<=l<=11

Absolute structure parameter 0.00(3)

for 2c. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

C(1) 2657(3) 2205(3) 1499(3) 30(1)

C(2) 2423(3) 2159(3) 2558(3) 32(1)

C(3) 1326(3) 1175(4) 3661(3) 36(1)

C(4) 2010(4) 194(4) 3677(3) 37(1)

C(5) 536(4) 2409(4) 2588(5) 48(1)

C(6) 2460(3) 1217(3) 14(3) 22(1)

C(7) 3689(3) 628(4) 1210(3) 35(1)

C(8) 1283(3) 1355(3) -126(3) 22(1)

C(100) 5000 10000 3855(7) 109(5)

Fe(1) 1281(1) 311(1) 1728(1) 19(1)

N(1) 2677(2) 1148(2) 1062(2) 23(1)

N(2) 1380(3) 1642(3) 2701(2) 29(1)

O(1) 2141(2) -241(2) 2836(2) 29(1)

O(2) 2377(3) -113(4) 4440(2) 58(1)

O(3) 712(2) 1178(2) 575(2) 21(1)

O(4) 984(2) 1649(2) -960(2) 25(1)

O(5) 0 0 2148(3) 27(1)

O(100) 4228(6) 9049(6) 4355(6) 116(2)

________________________________________________________________________________

Table S23. Bond lengths [Å] and angles [°] for 2c.

_____________________________________________________

C(1)-N(1) 1.489(5)

C(1)-C(2) 1.487(6)

C(2)-N(2) 1.512(5)

C(3)-N(2) 1.452(6)

C(3)-C(4) 1.541(8)

C(4)-O(2) 1.216(6)

C(4)-O(1) 1.295(6)

C(5)-N(2) 1.478(6)

C(6)-N(1) 1.470(5)

C(6)-C(8) 1.538(5)

C(7)-N(1) 1.479(5)

C(8)-O(3) 1.233(5)

C(8)-O(4) 1.267(5)

C(100)-O(100) 1.720(7)

C(100)-O(100)#1 1.720(7)

Fe(1)-O(5) 1.7940(13)

Fe(1)-O(1) 2.014(3)

Fe(1)-O(4)#2 2.030(3)

Fe(1)-O(3) 2.071(3)

Fe(1)-N(2) 2.178(3)

Fe(1)-N(1) 2.287(3)

O(4)-Fe(1)#3 2.030(3)

O(5)-Fe(1)#4 1.7940(13)

N(1)-C(1)-C(2) 111.2(3)

C(1)-C(2)-N(2) 109.0(3)

N(2)-C(3)-C(4) 109.0(3)

O(2)-C(4)-O(1) 125.3(5)

O(2)-C(4)-C(3) 120.1(4)

O(1)-C(4)-C(3) 114.6(4)

N(1)-C(6)-C(8) 108.5(3)

O(3)-C(8)-O(4) 125.5(4)

O(3)-C(8)-C(6) 117.9(3)

O(4)-C(8)-C(6) 116.5(3)

O(100)-C(100)-O(100)#1 133.0(8)

O(5)-Fe(1)-O(1) 100.57(13)

O(5)-Fe(1)-O(4)#2 101.42(10)

O(1)-Fe(1)-O(4)#2 88.50(12)

O(5)-Fe(1)-O(3) 92.38(12)

O(1)-Fe(1)-O(3) 164.46(11)

O(4)#2-Fe(1)-O(3) 97.40(11)

O(5)-Fe(1)-N(2) 91.83(11)

O(1)-Fe(1)-N(2) 77.37(12)

O(4)#2-Fe(1)-N(2) 162.23(12)

O(3)-Fe(1)-N(2) 93.78(12)

O(5)-Fe(1)-N(1) 163.23(9)

O(1)-Fe(1)-N(1) 92.07(11)

O(4)#2-Fe(1)-N(1) 89.79(12)

O(3)-Fe(1)-N(1) 73.67(11)

N(2)-Fe(1)-N(1) 80.13(12)

C(6)-N(1)-C(7) 109.2(3)

C(6)-N(1)-C(1) 109.7(3)

C(7)-N(1)-C(1) 112.0(3)

C(6)-N(1)-Fe(1) 105.7(2)

C(7)-N(1)-Fe(1) 115.1(2)

C(1)-N(1)-Fe(1) 104.8(2)

C(3)-N(2)-C(5) 109.7(4)

C(3)-N(2)-C(2) 110.0(3)

C(5)-N(2)-C(2) 110.3(4)

C(3)-N(2)-Fe(1) 103.2(2)

C(5)-N(2)-Fe(1) 114.8(3)

C(2)-N(2)-Fe(1) 108.6(2)

C(4)-O(1)-Fe(1) 116.8(3)

C(8)-O(3)-Fe(1) 119.1(2)

C(8)-O(4)-Fe(1)#3 130.5(2)

Fe(1)#4-O(5)-Fe(1) 142.4(2)

_____________________________________________________________

#1 -x+1,-y+2,z #2 y,-x,-z #3 -y,x,-z #4 -x,-y,z

Table S24. Anisotropic displacement parameters (Å2x 103) for 2c. The anisotropic

______________________________________________________________________________

U11 U22 U33 U23 U13 U12

______________________________________________________________________________

C(1) 29(2) 25(2) 36(2) -4(2) -4(2) -11(1)

C(2) 34(2) 32(2) 31(2) -7(2) -1(2) -13(2)

C(3) 31(2) 52(3) 24(2) -15(2) 4(2) -12(2)

C(4) 36(2) 56(3) 19(2) 3(2) -5(2) -20(2)

C(5) 42(3) 50(3) 53(3) -24(2) 0(2) 22(2)

C(6) 19(2) 25(2) 21(2) 1(2) 0(1) -3(1)

C(7) 22(2) 52(2) 29(2) 7(2) -7(2) -2(2)

C(8) 23(2) 17(2) 24(2) 0(2) 1(2) 0(1)

C(100) 141(11) 149(12) 37(4) 0 0 85(10)

Fe(1) 19(1) 22(1) 17(1) -1(1) -1(1) -3(1)

N(1) 21(2) 25(2) 23(2) -1(1) -2(1) -4(1)

N(2) 24(2) 32(2) 30(2) -12(1) -1(1) -3(1)

O(1) 29(1) 35(2) 24(1) 5(1) -4(1) -4(1)

O(2) 68(2) 84(3) 23(2) 12(2) -11(2) -18(2)

O(3) 22(1) 22(1) 21(1) 0(1) 1(1) -2(1)

O(4) 24(1) 29(1) 22(1) 8(1) -3(1) -3(1)

O(5) 24(2) 37(2) 19(2) 0 0 -8(2)

O(100) 123(6) 116(6) 108(5) 8(4) -8(5) 6(4)

______________________________________________________________________________

for 2c.

________________________________________________________________________________

x y z U(eq)

________________________________________________________________________________

H(1A) 2134 2622 1174 36

H(1B) 3325 2537 1402 36

H(2A) 2409 2854 2828 39

H(2B) 2957 1766 2892 39

H(3A) 613 993 3813 43

H(3B) 1568 1665 4147 43

H(6A) 2691 589 -311 26

H(6B) 2828 1802 -266 26

H(100) 3616 9195 4265 173 ________________________________________________________________________________

Figure S29. Geometry optimized [FeII(N2O1)(H2O)3]+ and [FeII(N2O1)2].

Table S26. Iron ligand bond distances for geometry optimized [FeII(N2O1)(H2O)3]

+ and [FeII(N2O1)2].

Figure S30. Space filling models of [FeII(N2O1)(H2O)3]+ and [FeII(N2O1)2].

[FeII(N2O1)(H2O)3]+ [FeII(N2O1)2]

N(1) 2.28 N(1) 2.52 N(2) 2.29 N(2) 2.32

H2(O1) 2.25 N(3) 2.51 H2(O2) 2.19 N(4) 2.32 H2(O3) 2.18 O(1) 2.04

O(1) 2.03 O(2) 2.04

Figure S31: Computational models of the configurations for [FeII(N2O1)2].

# Z X (Å) Y (Å) Z (Å) 1 26 0.0000 0.0000 0.0000 2 8 1.2130 0.8704 1.3930 3 8 -1.2197 -0.8669 -1.38994 7 0.9317 -2.2936 0.4382 5 7 -2.0486 -0.0955 1.0748 6 7 -0.9320 2.2989 -0.43587 7 2.0519 0.0984 -1.06738 6 2.3230 1.4146 1.0392 9 6 2.7173 1.2580 -0.441810 6 2.8128 -1.1378 -0.734511 6 1.9297 -2.3701 -0.653612 6 1.9355 0.2584 -2.531113 8 3.0610 2.0749 1.7791 14 6 -2.3303 -1.4084 -1.033615 6 -2.7202 -1.2517 0.4488 16 6 -2.8067 1.1443 0.7482 17 6 -1.9202 2.3741 0.6645 18 6 -1.9288 -0.2585 2.5381 19 8 -3.0730 -2.0644 -1.772720 1 -2.4124 -2.1664 0.9597 21 1 -3.8115 -1.1904 0.5381 22 1 -1.3461 -1.1525 2.7625 23 1 -2.9143 -0.3478 3.0147 24 1 -1.4079 0.6003 2.9629 25 1 2.5707 -3.2572 -0.525026 1 1.3813 -2.5019 -1.590227 1 3.6041 -1.3033 -1.478128 1 3.3170 -0.9828 0.2205 29 1 1.4200 -0.6035 -2.956330 1 1.3492 1.1492 -2.758731 1 2.9219 0.3514 -3.005232 1 3.8092 1.2011 -0.527533 1 2.4064 2.1696 -0.955734 1 -3.3186 0.9923 -0.203335 1 -3.5920 1.3116 1.4977 36 1 -1.3642 2.5006 1.5974 37 1 -2.5602 3.2634 0.5445 38 6 0.0249 -3.4483 0.3022 39 6 1.5768 -2.3657 1.7647 40 6 -0.0261 3.4558 -0.309241 6 -1.5897 2.3692 -1.755942 1 2.2027 -3.2663 1.8548 43 1 2.1856 -1.4844 1.9524 44 1 0.8063 -2.4035 2.5363 45 1 0.5832 -4.3956 0.3430 46 1 -0.6985 -3.4540 1.1180 47 1 -0.5043 -3.3994 -0.649148 1 -0.8264 2.4067 -2.534849 1 -2.2170 3.2693 -1.841250 1 -2.1996 1.4873 -1.937 51 1 0.5103 3.4104 0.6382 52 1 -0.5868 4.4019 -0.346853 1 0.6907 3.4619 -1.1309

Table S27: Geometry optimized atomic coordinates for [FeII(N2O1)2] (Figure S31A).

# Z X (Å) Y (Å) Z (Å) 1 26 0.0000 0.0000 0.00002 17 -1.7862 -1.4577 -1.17443 17 -0.4248 -0.7149 2.42064 17 6.5757 -0.4282 -0.17825 7 1.8323 1.2580 0.54706 7 1.6777 -1.3086 -0.71827 6 3.0031 -0.6313 -0.53828 1 3.8051 -1.3461 -0.40999 1 3.2249 -0.0830 -1.4407

10 6 2.9811 0.3190 0.652511 1 3.9356 0.8303 0.701312 1 2.8428 -0.2390 1.568713 6 1.6047 -2.5556 0.096314 1 0.6238 -2.9921 -0.023015 1 2.3702 -3.2590 -0.225016 1 1.7428 -2.3182 1.139117 6 1.4670 -1.6443 -2.152418 1 0.5075 -2.1202 -2.263319 1 1.4627 -0.7305 -2.732320 1 2.2621 -2.2928 -2.515421 6 1.9269 2.2417 -0.552322 1 2.5206 3.1053 -0.277223 1 2.3873 1.7837 -1.417224 8 -0.3974 1.8105 -0.737725 6 0.5089 2.6971 -0.968126 8 0.3744 3.7903 -1.499127 6 1.5984 1.9737 1.825028 1 1.4381 1.2564 2.612129 1 2.4426 2.6193 2.062130 1 0.7036 2.5734 1.7294

Table S28: Geometry optimized atomic coordinates for mer-[FeII(N2O1)Cl3]2-.

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