metal-organic compounds
The title complex, [Fe(C12H8N2)3]Cl2·6CH3OH, contains a slightly distorted octahedral [Fe(phen)3]2+ cation (phen is 1,10-phenanthroline). Chloride anions and solvent methanol molecules form two distinct hydrogen-bonded anionic clusters, formulated as [Cl(MeOH)2]− and [Cl(MeOH)4]−, which complete the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019873/bh2092sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019873/bh2092Isup2.hkl |
CCDC reference: 646725
Computing details top
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
[Fe(C12H8N2)3]Cl2·6CH4O | F(000) = 3600 |
Mr = 859.61 | Dx = 1.409 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 19317 reflections |
a = 18.5808 (9) Å | θ = 2.0–32.5° |
b = 23.6715 (14) Å | µ = 0.56 mm−1 |
c = 18.4205 (11) Å | T = 120 K |
V = 8102.0 (8) Å3 | Prism, red |
Z = 8 | 0.31 × 0.19 × 0.19 mm |
Data collection top
Oxford Diffraction KM-4-CCD area-detector diffractometer | 7162 independent reflections |
Graphite monochromator | 5069 reflections with I > 2σ(I) |
Detector resolution: 8.1883 pixels mm-1 | Rint = 0.073 |
ω scans | θmax = 25.1°, θmin = 2.1° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) | h = −22→22 |
Tmin = 0.898, Tmax = 0.956 | k = −28→27 |
46880 measured reflections | l = −18→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.093P)2 + 11.3547P] where P = (Fo2 + 2Fc2)/3 |
7162 reflections | (Δ/σ)max = 0.023 |
526 parameters | Δρmax = 1.33 e Å−3 |
0 restraints | Δρmin = −0.71 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.2249 (2) | 0.40459 (17) | 0.2190 (2) | 0.0224 (9) | |
H1 | 0.2473 | 0.4092 | 0.2649 | 0.027* | |
C2 | 0.2656 (2) | 0.41413 (19) | 0.1563 (2) | 0.0271 (10) | |
H2 | 0.3144 | 0.4259 | 0.1604 | 0.033* | |
C3 | 0.2353 (2) | 0.40658 (18) | 0.0889 (2) | 0.0249 (9) | |
H3 | 0.2628 | 0.4128 | 0.0462 | 0.030* | |
C4 | 0.1627 (2) | 0.38947 (16) | 0.0844 (2) | 0.0212 (9) | |
C5 | 0.1253 (2) | 0.37972 (17) | 0.0173 (2) | 0.0242 (9) | |
H5 | 0.1501 | 0.3844 | −0.0274 | 0.029* | |
C6 | 0.0555 (2) | 0.36401 (18) | 0.0169 (2) | 0.0261 (9) | |
H6 | 0.0322 | 0.3573 | −0.0282 | 0.031* | |
C7 | 0.0159 (2) | 0.35722 (17) | 0.0832 (2) | 0.0206 (8) | |
C8 | −0.0579 (2) | 0.34255 (17) | 0.0866 (2) | 0.0249 (9) | |
H8 | −0.0845 | 0.3354 | 0.0435 | 0.030* | |
C9 | −0.0902 (2) | 0.33881 (18) | 0.1533 (2) | 0.0252 (9) | |
H9 | −0.1398 | 0.3295 | 0.1565 | 0.030* | |
C10 | −0.0504 (2) | 0.34870 (16) | 0.2170 (2) | 0.0199 (8) | |
H10 | −0.0740 | 0.3459 | 0.2626 | 0.024* | |
C11 | 0.0514 (2) | 0.36634 (15) | 0.14882 (19) | 0.0167 (8) | |
C12 | 0.1256 (2) | 0.38191 (15) | 0.1499 (2) | 0.0163 (8) | |
C13 | 0.0778 (2) | 0.50063 (16) | 0.2617 (2) | 0.0217 (9) | |
H13 | 0.1111 | 0.4948 | 0.2233 | 0.026* | |
C14 | 0.0519 (2) | 0.55504 (17) | 0.2740 (2) | 0.0241 (9) | |
H14 | 0.0677 | 0.5853 | 0.2441 | 0.029* | |
C15 | 0.0039 (2) | 0.56514 (17) | 0.3287 (2) | 0.0239 (9) | |
H15 | −0.0131 | 0.6023 | 0.3375 | 0.029* | |
C16 | −0.0202 (2) | 0.51939 (16) | 0.3721 (2) | 0.0193 (8) | |
C17 | −0.0714 (2) | 0.52391 (17) | 0.4302 (2) | 0.0216 (9) | |
H17 | −0.0909 | 0.5598 | 0.4421 | 0.026* | |
C18 | −0.0923 (2) | 0.47794 (17) | 0.4681 (2) | 0.0206 (8) | |
H18 | −0.1256 | 0.4823 | 0.5068 | 0.025* | |
C19 | −0.06540 (19) | 0.42273 (16) | 0.4512 (2) | 0.0185 (8) | |
C20 | −0.0873 (2) | 0.37285 (17) | 0.4869 (2) | 0.0202 (8) | |
H20 | −0.1198 | 0.3744 | 0.5268 | 0.024* | |
C21 | −0.0607 (2) | 0.32192 (17) | 0.4629 (2) | 0.0226 (9) | |
H21 | −0.0764 | 0.2878 | 0.4851 | 0.027* | |
C22 | −0.0107 (2) | 0.32004 (16) | 0.4061 (2) | 0.0184 (8) | |
H22 | 0.0067 | 0.2843 | 0.3906 | 0.022* | |
C23 | −0.01495 (19) | 0.41738 (15) | 0.39515 (19) | 0.0162 (8) | |
C24 | 0.00821 (19) | 0.46599 (16) | 0.35581 (19) | 0.0160 (8) | |
C25 | 0.1861 (2) | 0.43137 (16) | 0.4053 (2) | 0.0197 (8) | |
H25 | 0.1684 | 0.4670 | 0.3899 | 0.024* | |
C26 | 0.2371 (2) | 0.43014 (17) | 0.4608 (2) | 0.0197 (8) | |
H26 | 0.2535 | 0.4644 | 0.4820 | 0.024* | |
C27 | 0.2637 (2) | 0.37941 (17) | 0.4847 (2) | 0.0203 (8) | |
H27 | 0.2974 | 0.3782 | 0.5233 | 0.024* | |
C28 | 0.2403 (2) | 0.32917 (16) | 0.4512 (2) | 0.0181 (8) | |
C29 | 0.2657 (2) | 0.27353 (17) | 0.4694 (2) | 0.0210 (8) | |
H29 | 0.2996 | 0.2692 | 0.5076 | 0.025* | |
C30 | 0.2423 (2) | 0.22694 (17) | 0.4333 (2) | 0.0200 (8) | |
H30 | 0.2602 | 0.1908 | 0.4465 | 0.024* | |
C31 | 0.1908 (2) | 0.23180 (16) | 0.3755 (2) | 0.0174 (8) | |
C32 | 0.1646 (2) | 0.18544 (17) | 0.3344 (2) | 0.0213 (8) | |
H32 | 0.1815 | 0.1482 | 0.3435 | 0.026* | |
C33 | 0.1145 (2) | 0.19540 (17) | 0.2814 (2) | 0.0223 (9) | |
H33 | 0.0955 | 0.1647 | 0.2543 | 0.027* | |
C34 | 0.0907 (2) | 0.25059 (16) | 0.2669 (2) | 0.0184 (8) | |
H34 | 0.0562 | 0.2563 | 0.2296 | 0.022* | |
C35 | 0.16423 (18) | 0.28553 (15) | 0.35744 (19) | 0.0147 (8) | |
C36 | 0.18969 (19) | 0.33445 (15) | 0.39552 (19) | 0.0162 (8) | |
Fe1 | 0.08701 (3) | 0.37572 (2) | 0.29657 (3) | 0.01420 (16) | |
N1 | 0.15577 (16) | 0.38927 (13) | 0.21698 (16) | 0.0171 (7) | |
N2 | 0.01923 (16) | 0.36184 (12) | 0.21574 (16) | 0.0167 (7) | |
N3 | 0.05766 (16) | 0.45599 (13) | 0.30205 (16) | 0.0174 (7) | |
N4 | 0.01350 (16) | 0.36642 (12) | 0.37274 (16) | 0.0154 (7) | |
N5 | 0.16072 (16) | 0.38478 (12) | 0.37262 (16) | 0.0157 (7) | |
N6 | 0.11508 (16) | 0.29543 (13) | 0.30380 (16) | 0.0160 (7) | |
Cl1 | 0.91187 (6) | 0.17551 (5) | 0.38597 (6) | 0.0332 (3) | |
Cl2 | 0.77439 (5) | 0.07279 (4) | 0.10148 (5) | 0.0227 (2) | |
C37 | 0.8830 (2) | 0.1941 (2) | 0.1814 (2) | 0.0345 (11) | |
H37A | 0.8442 | 0.2165 | 0.2032 | 0.052* | |
H37B | 0.8696 | 0.1541 | 0.1817 | 0.052* | |
H37C | 0.8908 | 0.2065 | 0.1313 | 0.052* | |
C38 | 0.5935 (3) | 0.2150 (2) | 0.4261 (3) | 0.0391 (12) | |
H38A | 0.6022 | 0.2173 | 0.4785 | 0.059* | |
H38B | 0.5416 | 0.2153 | 0.4169 | 0.059* | |
H38C | 0.6159 | 0.2474 | 0.4020 | 0.059* | |
C39 | 0.7673 (3) | 0.2661 (2) | 0.3312 (3) | 0.0485 (13) | |
H39A | 0.7401 | 0.2878 | 0.3673 | 0.073* | |
H39B | 0.7495 | 0.2751 | 0.2825 | 0.073* | |
H39C | 0.8184 | 0.2758 | 0.3345 | 0.073* | |
C40 | 0.7366 (4) | 0.0723 (3) | 0.3035 (3) | 0.0648 (17) | |
H40A | 0.7548 | 0.0598 | 0.3508 | 0.097* | |
H40B | 0.6858 | 0.0826 | 0.3080 | 0.097* | |
H40C | 0.7643 | 0.1051 | 0.2871 | 0.097* | |
C41 | 0.9285 (4) | 0.0270 (3) | 0.4510 (4) | 0.079 (2) | |
H41A | 0.9768 | 0.0362 | 0.4333 | 0.118* | |
H41C | 0.9243 | −0.0139 | 0.4579 | 0.118* | |
H41B | 0.9202 | 0.0462 | 0.4975 | 0.118* | |
C42 | 0.5941 (3) | −0.0086 (3) | 0.1622 (3) | 0.0589 (16) | |
H42A | 0.5838 | 0.0313 | 0.1721 | 0.088* | |
H42B | 0.5494 | −0.0279 | 0.1485 | 0.088* | |
H42C | 0.6289 | −0.0114 | 0.1224 | 0.088* | |
O1 | 0.94677 (17) | 0.20163 (15) | 0.22163 (16) | 0.0379 (8) | |
H1A | 0.9373 | 0.2005 | 0.2662 | 0.045* | |
O2 | 0.6234 (2) | 0.16474 (14) | 0.3988 (2) | 0.0497 (9) | |
H2A | 0.6659 | 0.1708 | 0.3853 | 0.060* | |
O3 | 0.7582 (2) | 0.20684 (16) | 0.3448 (2) | 0.0531 (10) | |
H3A | 0.7982 | 0.1924 | 0.3549 | 0.064* | |
O4 | 0.7441 (3) | 0.02625 (17) | 0.2505 (2) | 0.0657 (12) | |
H4A | 0.7524 | 0.0399 | 0.2092 | 0.079* | |
O5 | 0.8770 (3) | 0.0452 (2) | 0.4002 (3) | 0.0768 (13) | |
H5A | 0.8865 | 0.0783 | 0.3871 | 0.092* | |
O6 | 0.6228 (3) | −0.0340 (2) | 0.2247 (3) | 0.0871 (15) | |
H6A | 0.6633 | −0.0200 | 0.2338 | 0.105* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.017 (2) | 0.031 (2) | 0.0193 (19) | 0.0005 (17) | −0.0028 (16) | 0.0009 (17) |
C2 | 0.014 (2) | 0.040 (3) | 0.027 (2) | −0.0046 (18) | 0.0008 (17) | 0.0040 (19) |
C3 | 0.021 (2) | 0.029 (2) | 0.024 (2) | −0.0010 (18) | 0.0075 (17) | 0.0055 (18) |
C4 | 0.021 (2) | 0.020 (2) | 0.022 (2) | 0.0046 (16) | 0.0011 (16) | −0.0010 (16) |
C5 | 0.026 (2) | 0.030 (2) | 0.0170 (19) | 0.0028 (18) | 0.0007 (16) | 0.0000 (17) |
C6 | 0.026 (2) | 0.032 (2) | 0.020 (2) | 0.0009 (19) | −0.0029 (17) | −0.0032 (17) |
C7 | 0.018 (2) | 0.022 (2) | 0.022 (2) | 0.0023 (16) | −0.0027 (16) | −0.0012 (17) |
C8 | 0.022 (2) | 0.027 (2) | 0.026 (2) | −0.0024 (18) | −0.0066 (17) | 0.0001 (18) |
C9 | 0.016 (2) | 0.029 (2) | 0.030 (2) | −0.0023 (17) | −0.0033 (17) | 0.0031 (18) |
C10 | 0.0137 (19) | 0.021 (2) | 0.025 (2) | 0.0011 (16) | 0.0004 (16) | 0.0028 (16) |
C11 | 0.018 (2) | 0.0140 (19) | 0.0180 (18) | 0.0024 (15) | 0.0003 (15) | 0.0002 (15) |
C12 | 0.0151 (19) | 0.0141 (19) | 0.0198 (19) | 0.0034 (15) | 0.0010 (15) | 0.0016 (15) |
C13 | 0.017 (2) | 0.021 (2) | 0.027 (2) | −0.0011 (16) | 0.0020 (16) | 0.0030 (17) |
C14 | 0.023 (2) | 0.017 (2) | 0.032 (2) | 0.0001 (17) | −0.0021 (18) | 0.0082 (17) |
C15 | 0.027 (2) | 0.014 (2) | 0.031 (2) | 0.0004 (16) | −0.0006 (18) | 0.0022 (17) |
C16 | 0.018 (2) | 0.018 (2) | 0.0220 (19) | 0.0008 (15) | −0.0029 (16) | −0.0011 (16) |
C17 | 0.017 (2) | 0.020 (2) | 0.028 (2) | 0.0040 (16) | 0.0000 (16) | −0.0064 (17) |
C18 | 0.0153 (19) | 0.025 (2) | 0.0215 (19) | 0.0008 (16) | 0.0031 (16) | −0.0042 (17) |
C19 | 0.0128 (18) | 0.021 (2) | 0.0212 (19) | 0.0006 (15) | −0.0028 (15) | 0.0015 (16) |
C20 | 0.0131 (18) | 0.026 (2) | 0.0218 (19) | −0.0007 (16) | 0.0029 (16) | −0.0001 (17) |
C21 | 0.019 (2) | 0.022 (2) | 0.027 (2) | −0.0035 (17) | 0.0019 (17) | 0.0068 (17) |
C22 | 0.020 (2) | 0.0121 (19) | 0.0236 (19) | 0.0018 (15) | 0.0009 (16) | 0.0015 (16) |
C23 | 0.0133 (18) | 0.0164 (19) | 0.0189 (18) | 0.0011 (15) | −0.0031 (15) | 0.0002 (15) |
C24 | 0.0109 (18) | 0.020 (2) | 0.0174 (18) | 0.0000 (15) | −0.0019 (14) | −0.0006 (15) |
C25 | 0.020 (2) | 0.015 (2) | 0.025 (2) | −0.0008 (16) | 0.0038 (16) | −0.0019 (16) |
C26 | 0.0168 (19) | 0.020 (2) | 0.0227 (19) | −0.0019 (16) | 0.0016 (16) | −0.0054 (17) |
C27 | 0.0143 (19) | 0.026 (2) | 0.0209 (19) | −0.0005 (16) | 0.0001 (15) | −0.0022 (17) |
C28 | 0.0132 (19) | 0.021 (2) | 0.0201 (19) | 0.0007 (15) | 0.0051 (15) | −0.0029 (16) |
C29 | 0.0147 (19) | 0.029 (2) | 0.0194 (19) | 0.0047 (17) | −0.0030 (16) | 0.0011 (17) |
C30 | 0.0172 (19) | 0.021 (2) | 0.0222 (19) | 0.0040 (16) | −0.0017 (16) | 0.0044 (17) |
C31 | 0.0154 (19) | 0.0174 (19) | 0.0195 (18) | 0.0020 (15) | 0.0028 (15) | −0.0009 (15) |
C32 | 0.020 (2) | 0.017 (2) | 0.027 (2) | 0.0027 (16) | 0.0006 (17) | −0.0004 (16) |
C33 | 0.023 (2) | 0.019 (2) | 0.025 (2) | 0.0007 (17) | 0.0013 (17) | −0.0062 (16) |
C34 | 0.018 (2) | 0.020 (2) | 0.0168 (18) | −0.0001 (16) | −0.0022 (15) | −0.0027 (16) |
C35 | 0.0097 (17) | 0.0171 (19) | 0.0173 (18) | 0.0025 (14) | 0.0030 (14) | 0.0000 (15) |
C36 | 0.0145 (19) | 0.0166 (19) | 0.0176 (18) | 0.0014 (15) | 0.0060 (15) | 0.0008 (15) |
Fe1 | 0.0126 (3) | 0.0136 (3) | 0.0164 (3) | 0.0009 (2) | 0.0009 (2) | 0.0007 (2) |
N1 | 0.0153 (16) | 0.0158 (17) | 0.0202 (16) | 0.0019 (13) | −0.0001 (13) | −0.0011 (13) |
N2 | 0.0155 (16) | 0.0129 (16) | 0.0217 (16) | 0.0033 (13) | 0.0014 (13) | 0.0048 (13) |
N3 | 0.0128 (15) | 0.0192 (17) | 0.0201 (16) | 0.0009 (13) | −0.0004 (13) | 0.0027 (14) |
N4 | 0.0132 (15) | 0.0149 (16) | 0.0181 (15) | 0.0008 (12) | −0.0024 (12) | −0.0015 (13) |
N5 | 0.0154 (16) | 0.0132 (16) | 0.0186 (15) | 0.0009 (12) | 0.0051 (13) | 0.0007 (13) |
N6 | 0.0125 (15) | 0.0188 (17) | 0.0168 (15) | 0.0012 (13) | 0.0020 (13) | 0.0003 (13) |
Cl1 | 0.0325 (6) | 0.0397 (6) | 0.0276 (5) | 0.0035 (5) | −0.0024 (5) | 0.0040 (5) |
Cl2 | 0.0236 (5) | 0.0199 (5) | 0.0245 (5) | 0.0039 (4) | 0.0038 (4) | −0.0012 (4) |
C37 | 0.033 (3) | 0.035 (3) | 0.035 (2) | −0.004 (2) | −0.007 (2) | 0.002 (2) |
C38 | 0.033 (3) | 0.049 (3) | 0.035 (2) | 0.003 (2) | 0.004 (2) | 0.005 (2) |
C39 | 0.051 (3) | 0.035 (3) | 0.059 (3) | 0.007 (2) | −0.004 (3) | 0.005 (3) |
C40 | 0.073 (4) | 0.068 (4) | 0.053 (3) | 0.011 (3) | 0.010 (3) | −0.003 (3) |
C41 | 0.078 (5) | 0.063 (5) | 0.096 (5) | 0.002 (4) | −0.024 (4) | 0.002 (4) |
C42 | 0.045 (4) | 0.068 (4) | 0.063 (4) | 0.011 (3) | 0.003 (3) | 0.007 (3) |
O1 | 0.0330 (18) | 0.049 (2) | 0.0313 (17) | −0.0154 (16) | −0.0066 (14) | 0.0060 (16) |
O2 | 0.049 (2) | 0.035 (2) | 0.066 (2) | −0.0008 (17) | −0.012 (2) | −0.0030 (18) |
O3 | 0.042 (2) | 0.051 (2) | 0.066 (2) | 0.0056 (17) | −0.003 (2) | 0.004 (2) |
O4 | 0.091 (3) | 0.052 (3) | 0.054 (2) | −0.001 (2) | 0.009 (2) | 0.004 (2) |
O5 | 0.088 (4) | 0.070 (3) | 0.072 (3) | 0.003 (3) | −0.004 (3) | −0.014 (3) |
O6 | 0.099 (4) | 0.074 (3) | 0.088 (4) | −0.017 (3) | −0.022 (3) | 0.008 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.334 (5) | C27—H27 | 0.9500 |
C1—C2 | 1.398 (5) | C28—C36 | 1.398 (5) |
C1—H1 | 0.9500 | C28—C29 | 1.438 (5) |
C2—C3 | 1.375 (6) | C29—C30 | 1.359 (6) |
C2—H2 | 0.9500 | C29—H29 | 0.9500 |
C3—C4 | 1.412 (6) | C30—C31 | 1.437 (5) |
C3—H3 | 0.9500 | C30—H30 | 0.9500 |
C4—C12 | 1.401 (5) | C31—C35 | 1.404 (5) |
C4—C5 | 1.436 (5) | C31—C32 | 1.419 (5) |
C5—C6 | 1.349 (6) | C32—C33 | 1.370 (5) |
C5—H5 | 0.9500 | C32—H32 | 0.9500 |
C6—C7 | 1.436 (5) | C33—C34 | 1.405 (5) |
C6—H6 | 0.9500 | C33—H33 | 0.9500 |
C7—C11 | 1.394 (5) | C34—N6 | 1.340 (5) |
C7—C8 | 1.415 (5) | C34—H34 | 0.9500 |
C8—C9 | 1.370 (6) | C35—N6 | 1.366 (5) |
C8—H8 | 0.9500 | C35—C36 | 1.434 (5) |
C9—C10 | 1.408 (5) | C36—N5 | 1.374 (5) |
C9—H9 | 0.9500 | Fe1—N1 | 1.971 (3) |
C10—N2 | 1.330 (5) | Fe1—N2 | 1.978 (3) |
C10—H10 | 0.9500 | Fe1—N3 | 1.979 (3) |
C11—N2 | 1.374 (5) | Fe1—N4 | 1.970 (3) |
C11—C12 | 1.427 (5) | Fe1—N5 | 1.971 (3) |
C12—N1 | 1.369 (5) | Fe1—N6 | 1.975 (3) |
C13—N3 | 1.345 (5) | C37—O1 | 1.409 (5) |
C13—C14 | 1.393 (5) | C37—H37A | 0.9800 |
C13—H13 | 0.9500 | C37—H37B | 0.9800 |
C14—C15 | 1.367 (6) | C37—H37C | 0.9800 |
C14—H14 | 0.9500 | C38—O2 | 1.406 (6) |
C15—C16 | 1.419 (5) | C38—H38A | 0.9800 |
C15—H15 | 0.9500 | C38—H38B | 0.9800 |
C16—C24 | 1.402 (5) | C38—H38C | 0.9800 |
C16—C17 | 1.436 (5) | C39—O3 | 1.434 (6) |
C17—C18 | 1.350 (6) | C39—H39A | 0.9800 |
C17—H17 | 0.9500 | C39—H39B | 0.9800 |
C18—C19 | 1.434 (5) | C39—H39C | 0.9800 |
C18—H18 | 0.9500 | C40—O4 | 1.470 (7) |
C19—C23 | 1.400 (5) | C40—H40A | 0.9800 |
C19—C20 | 1.412 (5) | C40—H40B | 0.9800 |
C20—C21 | 1.376 (6) | C40—H40C | 0.9800 |
C20—H20 | 0.9500 | C41—O5 | 1.406 (7) |
C21—C22 | 1.401 (5) | C41—H41A | 0.9800 |
C21—H21 | 0.9500 | C41—H41C | 0.9800 |
C22—N4 | 1.336 (5) | C41—H41B | 0.9800 |
C22—H22 | 0.9500 | C42—O6 | 1.405 (7) |
C23—N4 | 1.380 (5) | C42—H42A | 0.9800 |
C23—C24 | 1.426 (5) | C42—H42B | 0.9800 |
C24—N3 | 1.372 (5) | C42—H42C | 0.9800 |
C25—N5 | 1.343 (5) | O1—H1A | 0.8400 |
C25—C26 | 1.394 (5) | O2—H2A | 0.8400 |
C25—H25 | 0.9500 | O3—H3A | 0.8400 |
C26—C27 | 1.370 (5) | O4—H4A | 0.8400 |
C26—H26 | 0.9500 | O5—H5A | 0.8400 |
C27—C28 | 1.408 (5) | O6—H6A | 0.8400 |
N1—C1—C2 | 122.9 (4) | C32—C31—C30 | 124.2 (3) |
N1—C1—H1 | 118.6 | C33—C32—C31 | 118.7 (4) |
C2—C1—H1 | 118.6 | C33—C32—H32 | 120.6 |
C3—C2—C1 | 120.1 (4) | C31—C32—H32 | 120.6 |
C3—C2—H2 | 119.9 | C32—C33—C34 | 120.6 (4) |
C1—C2—H2 | 119.9 | C32—C33—H33 | 119.7 |
C2—C3—C4 | 118.8 (4) | C34—C33—H33 | 119.7 |
C2—C3—H3 | 120.6 | N6—C34—C33 | 122.3 (3) |
C4—C3—H3 | 120.6 | N6—C34—H34 | 118.9 |
C12—C4—C3 | 117.2 (3) | C33—C34—H34 | 118.9 |
C12—C4—C5 | 118.8 (4) | N6—C35—C31 | 124.2 (3) |
C3—C4—C5 | 124.0 (4) | N6—C35—C36 | 115.8 (3) |
C6—C5—C4 | 121.0 (4) | C31—C35—C36 | 120.0 (3) |
C6—C5—H5 | 119.5 | N5—C36—C28 | 124.5 (3) |
C4—C5—H5 | 119.5 | N5—C36—C35 | 114.9 (3) |
C5—C6—C7 | 121.3 (4) | C28—C36—C35 | 120.6 (3) |
C5—C6—H6 | 119.4 | N1—Fe1—N2 | 83.10 (12) |
C7—C6—H6 | 119.4 | N1—Fe1—N3 | 93.45 (13) |
C11—C7—C8 | 117.3 (4) | N1—Fe1—N4 | 175.70 (13) |
C11—C7—C6 | 118.5 (3) | N1—Fe1—N5 | 93.47 (12) |
C8—C7—C6 | 124.2 (4) | N1—Fe1—N6 | 92.04 (12) |
C9—C8—C7 | 118.6 (4) | N2—Fe1—N3 | 91.28 (12) |
C9—C8—H8 | 120.7 | N2—Fe1—N4 | 94.37 (12) |
C7—C8—H8 | 120.7 | N2—Fe1—N5 | 174.73 (12) |
C8—C9—C10 | 120.5 (4) | N2—Fe1—N6 | 93.39 (12) |
C8—C9—H9 | 119.8 | N3—Fe1—N4 | 83.11 (12) |
C10—C9—H9 | 119.8 | N3—Fe1—N5 | 92.91 (12) |
N2—C10—C9 | 122.3 (4) | N3—Fe1—N6 | 173.18 (12) |
N2—C10—H10 | 118.8 | N4—Fe1—N5 | 89.30 (12) |
C9—C10—H10 | 118.8 | N4—Fe1—N6 | 91.58 (12) |
N2—C11—C7 | 124.1 (3) | N5—Fe1—N6 | 82.72 (12) |
N2—C11—C12 | 115.3 (3) | C1—N1—C12 | 117.0 (3) |
C7—C11—C12 | 120.6 (3) | C1—N1—Fe1 | 130.4 (3) |
N1—C12—C4 | 124.0 (3) | C12—N1—Fe1 | 112.7 (2) |
N1—C12—C11 | 116.2 (3) | C10—N2—C11 | 117.2 (3) |
C4—C12—C11 | 119.8 (3) | C10—N2—Fe1 | 130.1 (3) |
N3—C13—C14 | 122.7 (4) | C11—N2—Fe1 | 112.7 (2) |
N3—C13—H13 | 118.6 | C13—N3—C24 | 116.7 (3) |
C14—C13—H13 | 118.6 | C13—N3—Fe1 | 130.5 (3) |
C15—C14—C13 | 120.4 (4) | C24—N3—Fe1 | 112.8 (2) |
C15—C14—H14 | 119.8 | C22—N4—C23 | 116.9 (3) |
C13—C14—H14 | 119.8 | C22—N4—Fe1 | 130.7 (3) |
C14—C15—C16 | 119.2 (4) | C23—N4—Fe1 | 112.4 (2) |
C14—C15—H15 | 120.4 | C25—N5—C36 | 115.9 (3) |
C16—C15—H15 | 120.4 | C25—N5—Fe1 | 130.7 (3) |
C24—C16—C15 | 116.6 (3) | C36—N5—Fe1 | 113.3 (2) |
C24—C16—C17 | 118.4 (3) | C34—N6—C35 | 117.2 (3) |
C15—C16—C17 | 124.9 (4) | C34—N6—Fe1 | 129.7 (3) |
C18—C17—C16 | 121.1 (4) | C35—N6—Fe1 | 113.0 (2) |
C18—C17—H17 | 119.5 | O1—C37—H37A | 109.5 |
C16—C17—H17 | 119.5 | O1—C37—H37B | 109.5 |
C17—C18—C19 | 121.4 (4) | H37A—C37—H37B | 109.5 |
C17—C18—H18 | 119.3 | O1—C37—H37C | 109.5 |
C19—C18—H18 | 119.3 | H37A—C37—H37C | 109.5 |
C23—C19—C20 | 117.5 (3) | H37B—C37—H37C | 109.5 |
C23—C19—C18 | 118.5 (3) | O2—C38—H38A | 109.5 |
C20—C19—C18 | 124.0 (3) | O2—C38—H38B | 109.5 |
C21—C20—C19 | 118.6 (3) | H38A—C38—H38B | 109.5 |
C21—C20—H20 | 120.7 | O2—C38—H38C | 109.5 |
C19—C20—H20 | 120.7 | H38A—C38—H38C | 109.5 |
C20—C21—C22 | 120.4 (4) | H38B—C38—H38C | 109.5 |
C20—C21—H21 | 119.8 | O3—C39—H39A | 109.5 |
C22—C21—H21 | 119.8 | O3—C39—H39B | 109.5 |
N4—C22—C21 | 122.7 (3) | H39A—C39—H39B | 109.5 |
N4—C22—H22 | 118.6 | O3—C39—H39C | 109.5 |
C21—C22—H22 | 118.6 | H39A—C39—H39C | 109.5 |
N4—C23—C19 | 123.8 (3) | H39B—C39—H39C | 109.5 |
N4—C23—C24 | 115.9 (3) | O4—C40—H40A | 109.5 |
C19—C23—C24 | 120.2 (3) | O4—C40—H40B | 109.5 |
N3—C24—C16 | 124.2 (3) | H40A—C40—H40B | 109.5 |
N3—C24—C23 | 115.4 (3) | O4—C40—H40C | 109.5 |
C16—C24—C23 | 120.3 (3) | H40A—C40—H40C | 109.5 |
N5—C25—C26 | 123.4 (4) | H40B—C40—H40C | 109.5 |
N5—C25—H25 | 118.3 | O5—C41—H41A | 109.5 |
C26—C25—H25 | 118.3 | O5—C41—H41C | 109.5 |
C27—C26—C25 | 119.9 (4) | H41A—C41—H41C | 109.5 |
C27—C26—H26 | 120.1 | O5—C41—H41B | 109.5 |
C25—C26—H26 | 120.1 | H41A—C41—H41B | 109.5 |
C26—C27—C28 | 119.3 (4) | H41C—C41—H41B | 109.5 |
C26—C27—H27 | 120.4 | O6—C42—H42A | 109.5 |
C28—C27—H27 | 120.4 | O6—C42—H42B | 109.5 |
C36—C28—C27 | 116.9 (3) | H42A—C42—H42B | 109.5 |
C36—C28—C29 | 118.3 (3) | O6—C42—H42C | 109.5 |
C27—C28—C29 | 124.8 (3) | H42A—C42—H42C | 109.5 |
C30—C29—C28 | 121.6 (3) | H42B—C42—H42C | 109.5 |
C30—C29—H29 | 119.2 | C37—O1—H1A | 109.5 |
C28—C29—H29 | 119.2 | C38—O2—H2A | 109.5 |
C29—C30—C31 | 120.7 (4) | C39—O3—H3A | 109.5 |
C29—C30—H30 | 119.6 | C40—O4—H4A | 109.5 |
C31—C30—H30 | 119.6 | C41—O5—H5A | 109.5 |
C35—C31—C32 | 116.9 (3) | C42—O6—H6A | 109.5 |
C35—C31—C30 | 118.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1 | 0.84 | 2.33 | 3.157 (3) | 167 |
O2—H2A···O3 | 0.84 | 2.06 | 2.873 (5) | 164 |
O3—H3A···Cl1 | 0.84 | 2.22 | 3.046 (4) | 166 |
O4—H4A···Cl2 | 0.84 | 2.17 | 3.011 (4) | 178 |
O5—H5A···Cl1 | 0.84 | 2.35 | 3.164 (5) | 164 |
O6—H6A···O4 | 0.84 | 1.88 | 2.711 (7) | 168 |