In the title compound, [Fe(C10H7NO3)2(H2O)2]2·C10H7NO3·2H2O, two cis-diaquabis(quinoline-2-carboxylato)iron(II) molecules, one free quinoline-2-carboxylic acid molecule and two water molecules are present in the asymmetric unit. In the complex, the central FeII ion has a distorted octahedral coordination geometry, involving two N and two O atoms of the two bidentate organic ligands, together with two aqua O atoms in a cis configuration.
Supporting information
CCDC reference: 214553
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.008 Å
- R factor = 0.045
- wR factor = 0.174
- Data-to-parameter ratio = 16.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_725 Alert C D-H Calc 0.81909, Rep 0.83000, Dev. 0.01 Ang.
O14 -H14 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Purple plate-shaped crystals were obtained by slow evapolation from a mixture of quinoline-2-carboxylic acid and Fe(NH4)2(SO4)2·6H2O (4:1) dissolved in water.
All H atoms were located in a difference Fourier map. Those of the quinoline rings were then positioned geometrically and refined as riding, while those of the water molecules were fixed at the positions found in the map.
Data collection: MSC/AFC (Molecular Structure Corporation & Rigaku Corporation, 1999); cell refinement: MSC/AFC; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
[Fe(C8H8NO2)2(H2O)2]2·C10H7NO2·2H2O | Z = 2 |
Mr = 1081.59 | F(000) = 1116 |
Triclinic, P1 | Dx = 1.544 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 12.662 (3) Å | Cell parameters from 25 reflections |
b = 13.438 (3) Å | θ = 12.7–14.3° |
c = 16.340 (3) Å | µ = 0.71 mm−1 |
α = 97.20 (2)° | T = 296 K |
β = 101.94 (2)° | Plate, purple |
γ = 117.79 (1)° | 0.30 × 0.20 × 0.10 mm |
V = 2326.0 (10) Å3 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.054 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = −16→14 |
Tmin = 0.844, Tmax = 0.932 | k = 0→17 |
11146 measured reflections | l = −21→21 |
10701 independent reflections | 3 standard reflections every 150 reflections |
4869 reflections with I > 2σ(I) | intensity decay: 0.3% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.174 | (Δ/σ)max < 0.001 |
S = 0.84 | Δρmax = 0.37 e Å−3 |
10701 reflections | Δρmin = −0.48 e Å−3 |
658 parameters | |
Crystal data top
[Fe(C8H8NO2)2(H2O)2]2·C10H7NO2·2H2O | γ = 117.79 (1)° |
Mr = 1081.59 | V = 2326.0 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.662 (3) Å | Mo Kα radiation |
b = 13.438 (3) Å | µ = 0.71 mm−1 |
c = 16.340 (3) Å | T = 296 K |
α = 97.20 (2)° | 0.30 × 0.20 × 0.10 mm |
β = 101.94 (2)° | |
Data collection top
Rigaku AFC-5R diffractometer | 4869 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.054 |
Tmin = 0.844, Tmax = 0.932 | 3 standard reflections every 150 reflections |
11146 measured reflections | intensity decay: 0.3% |
10701 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 658 parameters |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 0.84 | Δρmax = 0.37 e Å−3 |
10701 reflections | Δρmin = −0.48 e Å−3 |
Special details top
Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 0.10728 (5) | 0.42207 (5) | 0.90227 (4) | 0.0294 (2) | |
Fe2 | 0.10239 (5) | 0.39937 (5) | 0.36371 (4) | 0.0302 (2) | |
O1 | 0.1752 (3) | 0.4706 (3) | 0.8033 (2) | 0.0372 (7) | |
O2 | 0.3132 (3) | 0.4862 (3) | 0.7335 (2) | 0.0530 (9) | |
O3 | 0.0265 (3) | 0.3717 (3) | 0.9983 (2) | 0.0400 (7) | |
O4 | −0.1469 (4) | 0.2446 (3) | 1.0225 (3) | 0.061 (1) | |
O5 | −0.0217 (3) | 0.4812 (3) | 0.8575 (2) | 0.0408 (7) | |
O6 | 0.2286 (3) | 0.5980 (3) | 0.9848 (2) | 0.0399 (7) | |
O7 | 0.1857 (3) | 0.4532 (3) | 0.2707 (2) | 0.0375 (7) | |
O8 | 0.3663 (3) | 0.5305 (3) | 0.2411 (2) | 0.0467 (8) | |
O9 | 0.0231 (3) | 0.3686 (3) | 0.4640 (2) | 0.0371 (7) | |
O10 | −0.1416 (3) | 0.2477 (3) | 0.4994 (2) | 0.0542 (10) | |
O11 | 0.2069 (3) | 0.5821 (3) | 0.4372 (2) | 0.0538 (9) | |
O12 | −0.0410 (3) | 0.4195 (4) | 0.2885 (3) | 0.061 (1) | |
O13 | 0.2722 (4) | −0.2478 (3) | 0.3397 (3) | 0.076 (1) | |
O14 | 0.3135 (3) | −0.0957 (3) | 0.4398 (2) | 0.0570 (10) | |
O15 | 0.7226 (3) | 0.3480 (3) | 0.8397 (2) | 0.0460 (8) | |
O16 | 0.1872 (3) | 0.5523 (3) | 0.6177 (2) | 0.0562 (10) | |
N1 | 0.2694 (3) | 0.3910 (3) | 0.9211 (2) | 0.0290 (8) | |
N2 | −0.0390 (3) | 0.2291 (3) | 0.8430 (2) | 0.0350 (8) | |
N3 | 0.2764 (3) | 0.3850 (3) | 0.4003 (2) | 0.0282 (8) | |
N4 | −0.0319 (3) | 0.2101 (3) | 0.3240 (2) | 0.0287 (8) | |
N5 | 0.4168 (3) | −0.1022 (3) | 0.2567 (3) | 0.0375 (9) | |
C1 | 0.3217 (4) | 0.4151 (4) | 0.8585 (3) | 0.0284 (9) | |
C2 | 0.4228 (4) | 0.4009 (4) | 0.8508 (3) | 0.036 (1) | |
C3 | 0.4724 (4) | 0.3613 (4) | 0.9119 (3) | 0.040 (1) | |
C4 | 0.4217 (4) | 0.3358 (4) | 0.9810 (3) | 0.0319 (10) | |
C5 | 0.4702 (4) | 0.2965 (4) | 1.0474 (3) | 0.042 (1) | |
C6 | 0.4182 (5) | 0.2737 (4) | 1.1124 (3) | 0.048 (1) | |
C7 | 0.3171 (4) | 0.2906 (4) | 1.1156 (3) | 0.040 (1) | |
C8 | 0.2689 (4) | 0.3290 (4) | 1.0528 (3) | 0.036 (1) | |
C9 | 0.3186 (4) | 0.3520 (3) | 0.9838 (3) | 0.0289 (9) | |
C10 | 0.2670 (4) | 0.4619 (4) | 0.7926 (3) | 0.034 (1) | |
C11 | −0.1009 (4) | 0.1862 (4) | 0.8986 (3) | 0.040 (1) | |
C12 | −0.1893 (5) | 0.0675 (5) | 0.8838 (4) | 0.055 (1) | |
C13 | −0.2104 (5) | −0.0073 (5) | 0.8112 (4) | 0.058 (2) | |
C14 | −0.1473 (4) | 0.0322 (4) | 0.7505 (4) | 0.047 (1) | |
C15 | −0.1647 (5) | −0.0425 (5) | 0.6731 (4) | 0.063 (2) | |
C16 | −0.1066 (6) | −0.0006 (5) | 0.6151 (4) | 0.066 (2) | |
C17 | −0.0284 (5) | 0.1192 (5) | 0.6305 (4) | 0.058 (1) | |
C18 | −0.0064 (5) | 0.1964 (5) | 0.7045 (3) | 0.047 (1) | |
C19 | −0.0642 (4) | 0.1526 (4) | 0.7674 (3) | 0.038 (1) | |
C20 | −0.0732 (5) | 0.2724 (5) | 0.9802 (3) | 0.043 (1) | |
C21 | 0.3450 (4) | 0.4241 (4) | 0.3478 (3) | 0.0303 (9) | |
C22 | 0.4561 (4) | 0.4227 (4) | 0.3516 (3) | 0.038 (1) | |
C23 | 0.4974 (4) | 0.3790 (4) | 0.4131 (3) | 0.041 (1) | |
C24 | 0.4303 (4) | 0.3370 (4) | 0.4716 (3) | 0.036 (1) | |
C25 | 0.4701 (5) | 0.2927 (4) | 0.5379 (3) | 0.043 (1) | |
C26 | 0.4051 (5) | 0.2585 (4) | 0.5953 (3) | 0.049 (1) | |
C27 | 0.2963 (5) | 0.2672 (4) | 0.5886 (3) | 0.047 (1) | |
C28 | 0.2541 (4) | 0.3077 (4) | 0.5249 (3) | 0.039 (1) | |
C29 | 0.3193 (4) | 0.3427 (4) | 0.4641 (3) | 0.0317 (9) | |
C30 | 0.2964 (4) | 0.4738 (4) | 0.2812 (3) | 0.0330 (10) | |
C31 | −0.0977 (4) | 0.1749 (4) | 0.3784 (3) | 0.0337 (10) | |
C32 | −0.1883 (4) | 0.0574 (4) | 0.3678 (3) | 0.045 (1) | |
C33 | −0.2092 (5) | −0.0230 (4) | 0.2985 (4) | 0.048 (1) | |
C34 | −0.1446 (4) | 0.0102 (4) | 0.2370 (3) | 0.039 (1) | |
C35 | −0.1648 (5) | −0.0693 (5) | 0.1626 (3) | 0.051 (1) | |
C36 | −0.1049 (5) | −0.0314 (5) | 0.1031 (4) | 0.057 (1) | |
C37 | −0.0203 (5) | 0.0871 (5) | 0.1160 (3) | 0.052 (1) | |
C38 | 0.0036 (4) | 0.1671 (4) | 0.1885 (3) | 0.041 (1) | |
C39 | −0.0571 (4) | 0.1293 (4) | 0.2513 (3) | 0.0325 (10) | |
C40 | −0.0707 (4) | 0.2700 (4) | 0.4537 (3) | 0.036 (1) | |
C41 | 0.4117 (4) | −0.0573 (4) | 0.3309 (3) | 0.038 (1) | |
C42 | 0.4803 (5) | 0.0618 (4) | 0.3726 (3) | 0.048 (1) | |
C43 | 0.5604 (5) | 0.1363 (4) | 0.3345 (4) | 0.051 (1) | |
C44 | 0.5695 (4) | 0.0928 (4) | 0.2560 (3) | 0.044 (1) | |
C45 | 0.6517 (5) | 0.1634 (5) | 0.2128 (4) | 0.061 (2) | |
C46 | 0.6582 (5) | 0.1160 (6) | 0.1376 (4) | 0.068 (2) | |
C47 | 0.5823 (6) | −0.0040 (6) | 0.0995 (4) | 0.065 (2) | |
C48 | 0.5020 (5) | −0.0746 (5) | 0.1381 (3) | 0.052 (1) | |
C49 | 0.4945 (4) | −0.0288 (4) | 0.2177 (3) | 0.038 (1) | |
C50 | 0.3253 (5) | −0.1441 (5) | 0.3705 (3) | 0.043 (1) | |
H2 | 0.4552 | 0.4182 | 0.8050 | 0.0432* | |
H3 | 0.5392 | 0.3512 | 0.9081 | 0.0476* | |
H5 | 0.5378 | 0.2864 | 1.0465 | 0.0510* | |
H5A | −0.0971 | 0.4317 | 0.8400 | 0.0488* | |
H5B | −0.0094 | 0.5347 | 0.8960 | 0.0488* | |
H6 | 0.4495 | 0.2465 | 1.1552 | 0.0574* | |
H6A | 0.2160 | 0.6495 | 0.9708 | 0.0476* | |
H6B | 0.2517 | 0.6108 | 1.0378 | 0.0476* | |
H7 | 0.2831 | 0.2754 | 1.1610 | 0.0484* | |
H8 | 0.2025 | 0.3401 | 1.0559 | 0.0432* | |
H11A | 0.2171 | 0.6274 | 0.3984 | 0.0645* | |
H11B | 0.1909 | 0.6385 | 0.4584 | 0.0645* | |
H12 | −0.2322 | 0.0413 | 0.9235 | 0.0663* | |
H12A | −0.0316 | 0.4531 | 0.2497 | 0.0728* | |
H12B | −0.0900 | 0.4274 | 0.3109 | 0.0728* | |
H13 | −0.2675 | −0.0861 | 0.8011 | 0.0698* | |
H14 | 0.2664 | −0.1463 | 0.4591 | 0.0855* | |
H15 | −0.2177 | −0.1223 | 0.6624 | 0.0750* | |
H15A | 0.6890 | 0.3840 | 0.8181 | 0.0573* | |
H15B | 0.6782 | 0.2710 | 0.8080 | 0.0573* | |
H16 | −0.1182 | −0.0508 | 0.5651 | 0.0787* | |
H16A | 0.1920 | 0.5623 | 0.5638 | 0.0700* | |
H16B | 0.2282 | 0.5295 | 0.6550 | 0.0700* | |
H17 | 0.0101 | 0.1479 | 0.5893 | 0.0694* | |
H18 | 0.0457 | 0.2760 | 0.7131 | 0.0564* | |
H22 | 0.5003 | 0.4510 | 0.3129 | 0.0451* | |
H23 | 0.5705 | 0.3768 | 0.4165 | 0.0488* | |
H25 | 0.5413 | 0.2869 | 0.5422 | 0.0510* | |
H26 | 0.4317 | 0.2295 | 0.6389 | 0.0594* | |
H27 | 0.2529 | 0.2447 | 0.6286 | 0.0567* | |
H28 | 0.1823 | 0.3122 | 0.5215 | 0.0467* | |
H32 | −0.2324 | 0.0360 | 0.4076 | 0.0539* | |
H33 | −0.2668 | −0.1010 | 0.2912 | 0.0580* | |
H35 | −0.2196 | −0.1483 | 0.1540 | 0.0607* | |
H36 | −0.1202 | −0.0846 | 0.0536 | 0.0685* | |
H37 | 0.0202 | 0.1119 | 0.0749 | 0.0629* | |
H38 | 0.0593 | 0.2458 | 0.1963 | 0.0497* | |
H42 | 0.4720 | 0.0896 | 0.4245 | 0.0571* | |
H43 | 0.6084 | 0.2157 | 0.3611 | 0.0616* | |
H45 | 0.7016 | 0.2433 | 0.2368 | 0.0726* | |
H46 | 0.7134 | 0.1631 | 0.1108 | 0.0819* | |
H47 | 0.5870 | −0.0355 | 0.0473 | 0.0780* | |
H48 | 0.4516 | −0.1538 | 0.1116 | 0.0625* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0298 (3) | 0.0359 (4) | 0.0295 (3) | 0.0191 (3) | 0.0146 (3) | 0.0110 (3) |
Fe2 | 0.0292 (3) | 0.0304 (4) | 0.0328 (4) | 0.0136 (3) | 0.0152 (3) | 0.0111 (3) |
O1 | 0.041 (2) | 0.050 (2) | 0.037 (2) | 0.030 (2) | 0.021 (1) | 0.020 (2) |
O2 | 0.049 (2) | 0.089 (3) | 0.044 (2) | 0.043 (2) | 0.028 (2) | 0.033 (2) |
O3 | 0.048 (2) | 0.046 (2) | 0.037 (2) | 0.027 (2) | 0.022 (2) | 0.014 (2) |
O4 | 0.074 (3) | 0.067 (3) | 0.082 (3) | 0.046 (2) | 0.060 (2) | 0.045 (2) |
O5 | 0.033 (2) | 0.045 (2) | 0.044 (2) | 0.021 (2) | 0.009 (1) | 0.010 (2) |
O6 | 0.042 (2) | 0.042 (2) | 0.038 (2) | 0.023 (2) | 0.012 (1) | 0.007 (1) |
O7 | 0.035 (2) | 0.048 (2) | 0.039 (2) | 0.022 (2) | 0.019 (1) | 0.021 (2) |
O8 | 0.048 (2) | 0.063 (2) | 0.051 (2) | 0.033 (2) | 0.033 (2) | 0.034 (2) |
O9 | 0.037 (2) | 0.038 (2) | 0.035 (2) | 0.016 (2) | 0.017 (1) | 0.009 (1) |
O10 | 0.061 (2) | 0.057 (2) | 0.061 (2) | 0.029 (2) | 0.045 (2) | 0.026 (2) |
O11 | 0.061 (2) | 0.036 (2) | 0.066 (2) | 0.022 (2) | 0.031 (2) | 0.008 (2) |
O12 | 0.056 (2) | 0.081 (3) | 0.074 (3) | 0.046 (2) | 0.031 (2) | 0.048 (2) |
O13 | 0.111 (4) | 0.044 (2) | 0.090 (3) | 0.033 (2) | 0.071 (3) | 0.029 (2) |
O14 | 0.064 (2) | 0.059 (2) | 0.050 (2) | 0.026 (2) | 0.035 (2) | 0.016 (2) |
O15 | 0.051 (2) | 0.039 (2) | 0.043 (2) | 0.020 (2) | 0.009 (2) | 0.012 (2) |
O16 | 0.067 (2) | 0.072 (3) | 0.044 (2) | 0.044 (2) | 0.020 (2) | 0.024 (2) |
N1 | 0.029 (2) | 0.027 (2) | 0.031 (2) | 0.014 (2) | 0.011 (2) | 0.007 (2) |
N2 | 0.030 (2) | 0.036 (2) | 0.044 (2) | 0.019 (2) | 0.013 (2) | 0.015 (2) |
N3 | 0.027 (2) | 0.029 (2) | 0.029 (2) | 0.013 (2) | 0.012 (1) | 0.008 (2) |
N4 | 0.030 (2) | 0.032 (2) | 0.028 (2) | 0.016 (2) | 0.011 (1) | 0.011 (2) |
N5 | 0.038 (2) | 0.034 (2) | 0.043 (2) | 0.017 (2) | 0.017 (2) | 0.012 (2) |
C1 | 0.027 (2) | 0.029 (2) | 0.031 (2) | 0.013 (2) | 0.013 (2) | 0.008 (2) |
C2 | 0.027 (2) | 0.040 (3) | 0.040 (3) | 0.016 (2) | 0.012 (2) | 0.008 (2) |
C3 | 0.028 (2) | 0.042 (3) | 0.055 (3) | 0.020 (2) | 0.018 (2) | 0.013 (2) |
C4 | 0.025 (2) | 0.029 (2) | 0.037 (2) | 0.012 (2) | 0.006 (2) | 0.006 (2) |
C5 | 0.031 (2) | 0.039 (3) | 0.056 (3) | 0.022 (2) | 0.004 (2) | 0.010 (2) |
C6 | 0.049 (3) | 0.053 (3) | 0.047 (3) | 0.028 (3) | 0.010 (2) | 0.027 (3) |
C7 | 0.041 (3) | 0.043 (3) | 0.040 (3) | 0.021 (2) | 0.013 (2) | 0.017 (2) |
C8 | 0.035 (2) | 0.039 (3) | 0.034 (2) | 0.018 (2) | 0.012 (2) | 0.010 (2) |
C9 | 0.026 (2) | 0.023 (2) | 0.031 (2) | 0.010 (2) | 0.006 (2) | 0.001 (2) |
C10 | 0.033 (2) | 0.039 (3) | 0.032 (2) | 0.017 (2) | 0.015 (2) | 0.010 (2) |
C11 | 0.034 (2) | 0.044 (3) | 0.051 (3) | 0.024 (2) | 0.015 (2) | 0.020 (2) |
C12 | 0.039 (3) | 0.053 (3) | 0.083 (4) | 0.022 (3) | 0.027 (3) | 0.039 (3) |
C13 | 0.041 (3) | 0.036 (3) | 0.080 (4) | 0.012 (3) | 0.005 (3) | 0.013 (3) |
C14 | 0.035 (3) | 0.041 (3) | 0.062 (3) | 0.022 (2) | 0.005 (2) | 0.011 (3) |
C15 | 0.057 (4) | 0.041 (3) | 0.067 (4) | 0.024 (3) | −0.010 (3) | −0.007 (3) |
C16 | 0.068 (4) | 0.058 (4) | 0.055 (4) | 0.034 (3) | −0.004 (3) | −0.007 (3) |
C17 | 0.055 (3) | 0.071 (4) | 0.044 (3) | 0.034 (3) | 0.010 (3) | 0.002 (3) |
C18 | 0.046 (3) | 0.047 (3) | 0.040 (3) | 0.020 (3) | 0.011 (2) | 0.004 (2) |
C19 | 0.027 (2) | 0.034 (3) | 0.044 (3) | 0.015 (2) | −0.001 (2) | 0.001 (2) |
C20 | 0.049 (3) | 0.053 (3) | 0.056 (3) | 0.036 (3) | 0.031 (3) | 0.036 (3) |
C21 | 0.031 (2) | 0.024 (2) | 0.031 (2) | 0.012 (2) | 0.009 (2) | 0.001 (2) |
C22 | 0.031 (2) | 0.042 (3) | 0.043 (3) | 0.020 (2) | 0.016 (2) | 0.009 (2) |
C23 | 0.032 (2) | 0.040 (3) | 0.054 (3) | 0.021 (2) | 0.014 (2) | 0.010 (2) |
C24 | 0.031 (2) | 0.031 (2) | 0.038 (3) | 0.014 (2) | 0.004 (2) | 0.001 (2) |
C25 | 0.040 (3) | 0.039 (3) | 0.048 (3) | 0.023 (2) | 0.006 (2) | 0.014 (2) |
C26 | 0.050 (3) | 0.049 (3) | 0.046 (3) | 0.024 (3) | 0.007 (2) | 0.020 (3) |
C27 | 0.046 (3) | 0.048 (3) | 0.049 (3) | 0.022 (3) | 0.015 (2) | 0.024 (3) |
C28 | 0.041 (3) | 0.042 (3) | 0.039 (3) | 0.022 (2) | 0.018 (2) | 0.016 (2) |
C29 | 0.032 (2) | 0.030 (2) | 0.032 (2) | 0.016 (2) | 0.007 (2) | 0.005 (2) |
C30 | 0.033 (2) | 0.036 (3) | 0.032 (2) | 0.017 (2) | 0.016 (2) | 0.004 (2) |
C31 | 0.029 (2) | 0.036 (2) | 0.040 (3) | 0.016 (2) | 0.015 (2) | 0.015 (2) |
C32 | 0.043 (3) | 0.043 (3) | 0.053 (3) | 0.019 (2) | 0.025 (2) | 0.022 (3) |
C33 | 0.043 (3) | 0.031 (3) | 0.065 (4) | 0.010 (2) | 0.020 (3) | 0.023 (3) |
C34 | 0.039 (3) | 0.028 (2) | 0.048 (3) | 0.017 (2) | 0.008 (2) | 0.006 (2) |
C35 | 0.052 (3) | 0.036 (3) | 0.056 (3) | 0.020 (3) | 0.010 (3) | 0.003 (2) |
C36 | 0.059 (3) | 0.048 (3) | 0.049 (3) | 0.027 (3) | 0.001 (3) | −0.013 (3) |
C37 | 0.064 (3) | 0.055 (3) | 0.037 (3) | 0.031 (3) | 0.017 (3) | 0.000 (2) |
C38 | 0.047 (3) | 0.038 (3) | 0.039 (3) | 0.020 (2) | 0.017 (2) | 0.012 (2) |
C39 | 0.031 (2) | 0.034 (2) | 0.037 (2) | 0.020 (2) | 0.008 (2) | 0.010 (2) |
C40 | 0.044 (3) | 0.047 (3) | 0.033 (2) | 0.030 (2) | 0.021 (2) | 0.019 (2) |
C41 | 0.036 (2) | 0.040 (3) | 0.042 (3) | 0.022 (2) | 0.013 (2) | 0.016 (2) |
C42 | 0.050 (3) | 0.043 (3) | 0.047 (3) | 0.022 (3) | 0.017 (2) | 0.005 (2) |
C43 | 0.046 (3) | 0.027 (3) | 0.065 (4) | 0.010 (2) | 0.014 (3) | 0.004 (2) |
C44 | 0.034 (3) | 0.045 (3) | 0.056 (3) | 0.020 (2) | 0.015 (2) | 0.021 (3) |
C45 | 0.043 (3) | 0.045 (3) | 0.089 (5) | 0.012 (3) | 0.025 (3) | 0.034 (3) |
C46 | 0.058 (4) | 0.079 (5) | 0.086 (5) | 0.034 (4) | 0.045 (4) | 0.048 (4) |
C47 | 0.069 (4) | 0.086 (5) | 0.055 (4) | 0.041 (4) | 0.035 (3) | 0.033 (3) |
C48 | 0.057 (3) | 0.053 (3) | 0.052 (3) | 0.026 (3) | 0.027 (3) | 0.020 (3) |
C49 | 0.031 (2) | 0.038 (3) | 0.046 (3) | 0.018 (2) | 0.012 (2) | 0.016 (2) |
C50 | 0.048 (3) | 0.049 (3) | 0.042 (3) | 0.028 (3) | 0.021 (2) | 0.019 (2) |
Geometric parameters (Å, º) top
Fe1—O1 | 2.025 (3) | C12—C13 | 1.345 (9) |
Fe1—O3 | 2.061 (4) | C12—H12 | 0.930 |
Fe1—O5 | 2.166 (4) | C13—C14 | 1.402 (9) |
Fe1—O6 | 2.173 (3) | C13—H13 | 0.930 |
Fe1—N1 | 2.248 (5) | C14—C15 | 1.420 (9) |
Fe1—N2 | 2.290 (3) | C14—C19 | 1.408 (6) |
Fe2—O7 | 2.043 (3) | C15—C16 | 1.338 (10) |
Fe2—O9 | 2.080 (4) | C15—H15 | 0.930 |
Fe2—O11 | 2.190 (3) | C16—C17 | 1.395 (8) |
Fe2—O12 | 2.122 (5) | C16—H16 | 0.930 |
Fe2—N3 | 2.265 (4) | C17—C18 | 1.376 (8) |
Fe2—N4 | 2.209 (3) | C17—H17 | 0.930 |
O1—C10 | 1.264 (7) | C18—C19 | 1.414 (8) |
O2—C10 | 1.231 (6) | C18—H18 | 0.930 |
O3—C20 | 1.280 (5) | C21—C22 | 1.404 (8) |
O4—C20 | 1.223 (8) | C21—C30 | 1.516 (7) |
O5—H5A | 0.826 | C22—C23 | 1.359 (8) |
O5—H5B | 0.824 | C22—H22 | 0.930 |
O6—H6A | 0.827 | C23—C24 | 1.406 (7) |
O6—H6B | 0.822 | C23—H23 | 0.930 |
O7—C30 | 1.264 (6) | C24—C25 | 1.414 (8) |
O8—C30 | 1.236 (6) | C24—C29 | 1.423 (8) |
O9—C40 | 1.260 (5) | C25—C26 | 1.358 (8) |
O10—C40 | 1.240 (7) | C25—H25 | 0.930 |
O11—H11A | 0.921 | C26—C27 | 1.418 (10) |
O11—H11B | 0.917 | C26—H26 | 0.930 |
O12—H12A | 0.820 | C27—C28 | 1.359 (8) |
O12—H12B | 0.822 | C27—H27 | 0.930 |
O13—C50 | 1.208 (7) | C28—C29 | 1.410 (7) |
O14—C50 | 1.306 (7) | C28—H28 | 0.930 |
O14—H14 | 0.819 | C31—C32 | 1.414 (6) |
O15—H15A | 0.845 | C31—C40 | 1.512 (7) |
O15—H15B | 0.927 | C32—C33 | 1.350 (8) |
O16—H16A | 0.918 | C32—H32 | 0.930 |
O16—H16B | 0.894 | C33—C34 | 1.411 (8) |
N1—C1 | 1.324 (6) | C33—H33 | 0.930 |
N1—C9 | 1.375 (6) | C34—C35 | 1.404 (8) |
N2—C11 | 1.332 (7) | C34—C39 | 1.411 (6) |
N2—C19 | 1.377 (6) | C35—C36 | 1.360 (9) |
N3—C21 | 1.327 (6) | C35—H35 | 0.930 |
N3—C29 | 1.381 (7) | C36—C37 | 1.400 (7) |
N4—C31 | 1.323 (6) | C36—H36 | 0.930 |
N4—C39 | 1.374 (6) | C37—C38 | 1.372 (8) |
N5—C41 | 1.314 (7) | C37—H37 | 0.930 |
N5—C49 | 1.362 (6) | C38—C39 | 1.412 (7) |
C1—C2 | 1.407 (8) | C38—H38 | 0.930 |
C1—C10 | 1.517 (7) | C41—C42 | 1.402 (6) |
C2—C3 | 1.364 (8) | C41—C50 | 1.505 (7) |
C2—H2 | 0.930 | C42—C43 | 1.375 (8) |
C3—C4 | 1.412 (7) | C42—H42 | 0.930 |
C3—H3 | 0.930 | C43—C44 | 1.391 (9) |
C4—C5 | 1.416 (8) | C43—H43 | 0.930 |
C4—C9 | 1.429 (8) | C44—C45 | 1.426 (8) |
C5—C6 | 1.355 (8) | C44—C49 | 1.420 (6) |
C5—H5 | 0.930 | C45—C46 | 1.35 (1) |
C6—C7 | 1.411 (9) | C45—H45 | 0.930 |
C6—H6 | 0.930 | C46—C47 | 1.402 (9) |
C7—C8 | 1.364 (8) | C46—H46 | 0.930 |
C7—H7 | 0.930 | C47—C48 | 1.358 (9) |
C8—C9 | 1.401 (7) | C47—H47 | 0.930 |
C8—H8 | 0.930 | C48—C49 | 1.409 (8) |
C11—C12 | 1.408 (7) | C48—H48 | 0.930 |
C11—C20 | 1.511 (8) | | |
| | | |
O1···O12i | 3.026 (7) | O12···O16i | 2.757 (7) |
O2···C22ii | 3.277 (6) | O13···O15xi | 3.096 (6) |
O2···C6iii | 3.537 (5) | O14···C17x | 3.402 (8) |
O3···O5iv | 2.910 (5) | O14···C42xi | 3.413 (7) |
O3···O6iv | 3.500 (6) | O14···C16x | 3.438 (10) |
O4···O6iv | 2.760 (7) | O15···N5xi | 2.936 (5) |
O4···O5iv | 3.332 (4) | O15···C30ii | 3.350 (7) |
O4···C46v | 3.372 (8) | O15···C48xi | 3.570 (6) |
O4···C37vi | 3.513 (9) | O16···C40i | 3.537 (8) |
O4···C38vi | 3.534 (7) | N5···C12x | 3.546 (8) |
O5···O15vii | 2.801 (4) | C1···C5iii | 3.411 (5) |
O5···O12i | 2.949 (6) | C1···C4iii | 3.574 (4) |
O5···O7i | 3.139 (5) | C2···C4iii | 3.575 (6) |
O5···C20iv | 3.494 (6) | C3···C9iii | 3.425 (5) |
O6···O15iii | 2.731 (4) | C4···C35x | 3.576 (5) |
O6···C20iv | 3.263 (8) | C5···C10iii | 3.555 (5) |
O6···C3iii | 3.560 (6) | C7···C30vi | 3.559 (8) |
O6···C5iii | 3.578 (6) | C9···C35x | 3.584 (6) |
O7···O15ii | 3.305 (5) | C13···C41x | 3.572 (9) |
O7···O13viii | 3.587 (6) | C13···C37x | 3.59 (1) |
O8···O15ii | 2.704 (6) | C14···C41x | 3.523 (9) |
O8···C2ii | 3.154 (6) | C14···C36x | 3.577 (9) |
O8···C26ii | 3.287 (5) | C15···C39x | 3.572 (10) |
O8···C7ix | 3.306 (7) | C19···C50x | 3.538 (8) |
O8···C8ix | 3.397 (6) | C19···C35x | 3.599 (9) |
O8···C3ii | 3.576 (7) | C21···C25ii | 3.399 (6) |
O9···O16i | 3.395 (6) | C21···C24ii | 3.570 (5) |
O10···O14x | 2.675 (5) | C22···C24ii | 3.529 (6) |
O10···O11i | 2.917 (7) | C22···C29ii | 3.579 (5) |
O10···O13x | 3.382 (7) | C23···C29ii | 3.391 (6) |
O10···C50x | 3.411 (7) | C25···C30ii | 3.568 (5) |
O11···O13viii | 2.854 (6) | C32···C44vii | 3.497 (9) |
O11···C25ii | 3.529 (7) | C47···C47xii | 3.52 (1) |
| | | |
O1—Fe1—O3 | 176.0 (2) | C16—C15—H15 | 119.3 |
O1—Fe1—O5 | 86.4 (2) | C15—C16—C17 | 119.3 (6) |
O1—Fe1—O6 | 91.2 (1) | C15—C16—H16 | 120.3 |
O1—Fe1—N1 | 76.5 (2) | C17—C16—H16 | 120.3 |
O1—Fe1—N2 | 102.6 (1) | C16—C17—C18 | 122.2 (6) |
O3—Fe1—O5 | 89.9 (2) | C16—C17—H17 | 118.9 |
O3—Fe1—O6 | 90.1 (1) | C18—C17—H17 | 118.9 |
O3—Fe1—N1 | 107.3 (2) | C17—C18—C19 | 118.8 (5) |
O3—Fe1—N2 | 76.1 (1) | C17—C18—H18 | 120.6 |
O5—Fe1—O6 | 85.3 (1) | C19—C18—H18 | 120.6 |
O5—Fe1—N1 | 162.4 (1) | N2—C19—C14 | 121.8 (5) |
O5—Fe1—N2 | 94.2 (1) | N2—C19—C18 | 119.1 (4) |
O6—Fe1—N1 | 90.9 (1) | C14—C19—C18 | 119.1 (5) |
O6—Fe1—N2 | 166.2 (1) | O3—C20—O4 | 125.0 (5) |
N1—Fe1—N2 | 93.5 (1) | O3—C20—C11 | 116.0 (5) |
O7—Fe2—O9 | 171.9 (1) | O4—C20—C11 | 119.0 (4) |
O7—Fe2—O11 | 87.4 (1) | N3—C21—C22 | 124.5 (5) |
O7—Fe2—O12 | 83.5 (2) | N3—C21—C30 | 115.3 (5) |
O7—Fe2—N3 | 76.2 (1) | C22—C21—C30 | 120.2 (4) |
O7—Fe2—N4 | 111.3 (1) | C21—C22—C23 | 118.3 (5) |
O9—Fe2—O11 | 85.1 (1) | C21—C22—H22 | 120.8 |
O9—Fe2—O12 | 93.7 (2) | C23—C22—H22 | 120.8 |
O9—Fe2—N3 | 106.9 (1) | C22—C23—C24 | 120.4 (5) |
O9—Fe2—N4 | 76.0 (1) | C22—C23—H23 | 119.8 |
O11—Fe2—O12 | 92.2 (2) | C24—C23—H23 | 119.8 |
O11—Fe2—N3 | 91.3 (1) | C23—C24—C25 | 122.9 (5) |
O11—Fe2—N4 | 161.1 (2) | C23—C24—C29 | 117.8 (5) |
O12—Fe2—N3 | 159.3 (2) | C25—C24—C29 | 119.3 (5) |
O12—Fe2—N4 | 87.4 (2) | C24—C25—C26 | 120.5 (6) |
N3—Fe2—N4 | 95.7 (1) | C24—C25—H25 | 119.7 |
Fe1—O1—C10 | 120.8 (3) | C26—C25—H25 | 119.7 |
Fe1—O3—C20 | 119.0 (3) | C25—C26—C27 | 119.7 (6) |
Fe1—O5—H5A | 117.0 | C25—C26—H26 | 120.2 |
Fe1—O5—H5B | 109.2 | C27—C26—H26 | 120.2 |
H5A—O5—H5B | 109.5 | C26—C27—C28 | 121.5 (5) |
Fe1—O6—H6A | 117.5 | C26—C27—H27 | 119.2 |
Fe1—O6—H6B | 121.6 | C28—C27—H27 | 119.2 |
H6A—O6—H6B | 110.1 | C27—C28—C29 | 119.9 (6) |
Fe2—O7—C30 | 119.0 (3) | C27—C28—H28 | 120.1 |
Fe2—O9—C40 | 118.4 (3) | C29—C28—H28 | 120.1 |
Fe2—O11—H11A | 108.1 | N3—C29—C24 | 121.5 (4) |
Fe2—O11—H11B | 138.7 | N3—C29—C28 | 119.4 (5) |
H11A—O11—H11B | 74.5 | C24—C29—C28 | 119.1 (5) |
Fe2—O12—H12A | 122.5 | O7—C30—O8 | 124.7 (5) |
Fe2—O12—H12B | 119.4 | O7—C30—C21 | 116.7 (4) |
H12A—O12—H12B | 110.6 | O8—C30—C21 | 118.6 (5) |
C50—O14—H14 | 109.5 | N4—C31—C32 | 123.3 (5) |
H15A—O15—H15B | 109.2 | N4—C31—C40 | 115.3 (4) |
H16A—O16—H16B | 129.9 | C32—C31—C40 | 121.3 (5) |
Fe1—N1—C1 | 110.8 (3) | C31—C32—C33 | 118.4 (5) |
Fe1—N1—C9 | 131.2 (3) | C31—C32—H32 | 120.8 |
C1—N1—C9 | 118.0 (5) | C33—C32—H32 | 120.8 |
Fe1—N2—C11 | 109.9 (3) | C32—C33—C34 | 120.6 (4) |
Fe1—N2—C19 | 132.1 (3) | C32—C33—H33 | 119.7 |
C11—N2—C19 | 117.7 (4) | C34—C33—H33 | 119.7 |
Fe2—N3—C21 | 110.7 (3) | C33—C34—C35 | 123.1 (4) |
Fe2—N3—C29 | 131.9 (3) | C33—C34—C39 | 117.6 (5) |
C21—N3—C29 | 117.4 (4) | C35—C34—C39 | 119.3 (5) |
Fe2—N4—C31 | 112.6 (3) | C34—C35—C36 | 120.5 (5) |
Fe2—N4—C39 | 128.9 (3) | C34—C35—H35 | 119.8 |
C31—N4—C39 | 118.4 (3) | C36—C35—H35 | 119.8 |
C41—N5—C49 | 118.2 (4) | C35—C36—C37 | 120.4 (5) |
N1—C1—C2 | 124.3 (5) | C35—C36—H36 | 119.8 |
N1—C1—C10 | 116.0 (5) | C37—C36—H36 | 119.8 |
C2—C1—C10 | 119.7 (4) | C36—C37—C38 | 120.8 (5) |
C1—C2—C3 | 118.7 (5) | C36—C37—H37 | 119.6 |
C1—C2—H2 | 120.7 | C38—C37—H37 | 119.6 |
C3—C2—H2 | 120.7 | C37—C38—C39 | 119.6 (4) |
C2—C3—C4 | 119.6 (5) | C37—C38—H38 | 120.2 |
C2—C3—H3 | 120.2 | C39—C38—H38 | 120.2 |
C4—C3—H3 | 120.2 | N4—C39—C34 | 121.5 (4) |
C3—C4—C5 | 122.5 (5) | N4—C39—C38 | 119.1 (4) |
C3—C4—C9 | 118.2 (5) | C34—C39—C38 | 119.4 (4) |
C5—C4—C9 | 119.3 (5) | O9—C40—O10 | 124.6 (5) |
C4—C5—C6 | 120.1 (6) | O9—C40—C31 | 116.2 (5) |
C4—C5—H5 | 120.0 | O10—C40—C31 | 119.2 (4) |
C6—C5—H5 | 120.0 | N5—C41—C42 | 124.2 (5) |
C5—C6—C7 | 120.7 (6) | N5—C41—C50 | 115.0 (4) |
C5—C6—H6 | 119.6 | C42—C41—C50 | 120.8 (5) |
C7—C6—H6 | 119.6 | C41—C42—C43 | 118.1 (5) |
C6—C7—C8 | 120.6 (5) | C41—C42—H42 | 121.0 |
C6—C7—H7 | 119.7 | C43—C42—H42 | 121.0 |
C8—C7—H7 | 119.7 | C42—C43—C44 | 119.8 (4) |
C7—C8—C9 | 120.6 (5) | C42—C43—H43 | 120.1 |
C7—C8—H8 | 119.7 | C44—C43—H43 | 120.1 |
C9—C8—H8 | 119.7 | C43—C44—C45 | 123.6 (5) |
N1—C9—C4 | 121.2 (4) | C43—C44—C49 | 118.2 (5) |
N1—C9—C8 | 120.0 (5) | C45—C44—C49 | 118.2 (5) |
C4—C9—C8 | 118.8 (5) | C44—C45—C46 | 120.9 (5) |
O1—C10—O2 | 125.8 (5) | C44—C45—H45 | 119.5 |
O1—C10—C1 | 115.9 (4) | C46—C45—H45 | 119.5 |
O2—C10—C1 | 118.3 (5) | C45—C46—C47 | 120.4 (6) |
N2—C11—C12 | 123.3 (5) | C45—C46—H46 | 119.8 |
N2—C11—C20 | 116.6 (4) | C47—C46—H46 | 119.8 |
C12—C11—C20 | 120.2 (5) | C46—C47—C48 | 120.7 (6) |
C11—C12—C13 | 118.7 (6) | C46—C47—H47 | 119.6 |
C11—C12—H12 | 120.7 | C48—C47—H47 | 119.6 |
C13—C12—H12 | 120.7 | C47—C48—C49 | 120.6 (5) |
C12—C13—C14 | 120.8 (5) | C47—C48—H48 | 119.7 |
C12—C13—H13 | 119.6 | C49—C48—H48 | 119.7 |
C14—C13—H13 | 119.6 | N5—C49—C44 | 121.5 (5) |
C13—C14—C15 | 123.4 (5) | N5—C49—C48 | 119.5 (4) |
C13—C14—C19 | 117.6 (5) | C44—C49—C48 | 119.0 (5) |
C15—C14—C19 | 119.0 (5) | O13—C50—O14 | 124.2 (5) |
C14—C15—C16 | 121.5 (5) | O13—C50—C41 | 122.5 (5) |
C14—C15—H15 | 119.3 | O14—C50—C41 | 113.3 (4) |
| | | |
Fe1—O1—C10—O2 | 178.1 (3) | N3—Fe2—O9—C40 | −101.9 (4) |
Fe1—O1—C10—C1 | −0.7 (4) | N3—Fe2—N4—C31 | 109.8 (4) |
Fe1—O3—C20—O4 | −160.2 (5) | N3—Fe2—N4—C39 | −72.8 (4) |
Fe1—O3—C20—C11 | 18.0 (7) | N3—C21—C22—C23 | −0.3 (6) |
Fe1—N1—C1—C2 | −178.0 (3) | N3—C29—C24—C23 | 1.7 (6) |
Fe1—N1—C1—C10 | 2.6 (4) | N3—C29—C24—C25 | −179.8 (4) |
Fe1—N1—C9—C4 | 178.2 (2) | N3—C29—C28—C27 | −179.2 (4) |
Fe1—N1—C9—C8 | −2.7 (5) | N4—Fe2—O7—C30 | −102.6 (3) |
Fe1—N2—C11—C12 | −174.3 (5) | N4—Fe2—O9—C40 | −10.0 (4) |
Fe1—N2—C11—C20 | 6.4 (6) | N4—Fe2—N3—C21 | 114.3 (3) |
Fe1—N2—C19—C14 | 170.0 (4) | N4—Fe2—N3—C29 | −64.6 (3) |
Fe1—N2—C19—C18 | −10.9 (8) | N4—C31—C32—C33 | −0.3 (9) |
Fe2—O7—C30—O8 | −162.9 (4) | N4—C39—C34—C33 | 2.4 (8) |
Fe2—O7—C30—C21 | 17.4 (5) | N4—C39—C34—C35 | −178.4 (5) |
Fe2—O9—C40—O10 | −164.5 (5) | N4—C39—C38—C37 | 179.5 (6) |
Fe2—O9—C40—C31 | 14.0 (7) | N5—C41—C42—C43 | −1.6 (9) |
Fe2—N3—C21—C22 | −177.5 (3) | N5—C49—C44—C43 | −1.0 (9) |
Fe2—N3—C21—C30 | 3.2 (4) | N5—C49—C44—C45 | 177.8 (6) |
Fe2—N3—C29—C24 | 176.5 (3) | N5—C49—C48—C47 | −177.4 (6) |
Fe2—N3—C29—C28 | −5.4 (5) | C1—N1—C9—C4 | −1.1 (5) |
Fe2—N4—C31—C32 | −179.0 (4) | C1—N1—C9—C8 | 177.9 (3) |
Fe2—N4—C31—C40 | 1.6 (6) | C1—C2—C3—C4 | −0.1 (6) |
Fe2—N4—C39—C34 | 178.4 (4) | C2—C1—N1—C9 | 1.5 (5) |
Fe2—N4—C39—C38 | −3.2 (7) | C2—C3—C4—C5 | −178.8 (4) |
O1—Fe1—N1—C1 | −2.3 (2) | C2—C3—C4—C9 | 0.4 (5) |
O1—Fe1—N1—C9 | 178.3 (3) | C3—C2—C1—C10 | 178.4 (3) |
O1—Fe1—N2—C11 | −174.6 (4) | C3—C4—C5—C6 | 179.8 (4) |
O1—Fe1—N2—C19 | 11.8 (5) | C3—C4—C9—C8 | −178.8 (3) |
O1—C10—C1—N1 | −1.5 (5) | C4—C5—C6—C7 | −1.2 (6) |
O1—C10—C1—C2 | 179.0 (3) | C4—C9—C8—C7 | −0.8 (5) |
O2—C10—C1—N1 | 179.6 (3) | C5—C4—C9—C8 | 0.4 (5) |
O2—C10—C1—C2 | 0.2 (5) | C5—C6—C7—C8 | 0.8 (6) |
O3—Fe1—N1—C1 | 176.4 (2) | C6—C5—C4—C9 | 0.6 (6) |
O3—Fe1—N1—C9 | −3.0 (3) | C6—C7—C8—C9 | 0.2 (6) |
O3—Fe1—N2—C11 | 1.5 (4) | C9—N1—C1—C10 | −177.9 (3) |
O3—Fe1—N2—C19 | −172.1 (5) | C11—N2—C19—C14 | −3.2 (8) |
O3—C20—C11—N2 | −16.1 (8) | C11—N2—C19—C18 | 175.8 (5) |
O3—C20—C11—C12 | 164.6 (6) | C11—C12—C13—C14 | −1 (1) |
O4—C20—C11—N2 | 162.3 (6) | C12—C11—N2—C19 | 0.4 (9) |
O4—C20—C11—C12 | −17.0 (9) | C12—C13—C14—C15 | 179.4 (7) |
O5—Fe1—O1—C10 | 177.4 (3) | C12—C13—C14—C19 | −1.6 (10) |
O5—Fe1—O3—C20 | 83.3 (5) | C13—C12—C11—C20 | −179.0 (6) |
O5—Fe1—N1—C1 | −16.1 (5) | C13—C14—C15—C16 | 177.1 (7) |
O5—Fe1—N1—C9 | 164.5 (3) | C13—C14—C19—C18 | −175.2 (6) |
O5—Fe1—N2—C11 | −87.3 (4) | C14—C15—C16—C17 | 0 (1) |
O5—Fe1—N2—C19 | 99.0 (5) | C14—C19—C18—C17 | −3.2 (9) |
O6—Fe1—O1—C10 | 92.2 (3) | C15—C14—C19—C18 | 3.8 (9) |
O6—Fe1—O3—C20 | 168.6 (5) | C15—C16—C17—C18 | 1 (1) |
O6—Fe1—N1—C1 | −93.3 (2) | C16—C15—C14—C19 | −1 (1) |
O6—Fe1—N1—C9 | 87.4 (3) | C16—C17—C18—C19 | 0 (1) |
O6—Fe1—N2—C11 | 0.2 (9) | C19—N2—C11—C20 | −178.9 (5) |
O6—Fe1—N2—C19 | −173.4 (6) | C21—N3—C29—C24 | −2.3 (5) |
O7—Fe2—N3—C21 | 3.7 (2) | C21—N3—C29—C28 | 175.7 (4) |
O7—Fe2—N3—C29 | −175.2 (4) | C21—C22—C23—C24 | −0.4 (6) |
O7—Fe2—N4—C31 | −172.7 (3) | C22—C21—N3—C29 | 1.6 (6) |
O7—Fe2—N4—C39 | 4.6 (5) | C22—C23—C24—C25 | −178.7 (4) |
O7—C30—C21—N3 | −13.3 (5) | C22—C23—C24—C29 | −0.3 (6) |
O7—C30—C21—C22 | 167.4 (4) | C23—C22—C21—C30 | 179.0 (4) |
O8—C30—C21—N3 | 166.9 (4) | C23—C24—C25—C26 | 176.8 (4) |
O8—C30—C21—C22 | −12.4 (6) | C23—C24—C29—C28 | −176.3 (4) |
O9—Fe2—N3—C21 | −168.6 (2) | C24—C25—C26—C27 | 0.1 (7) |
O9—Fe2—N3—C29 | 12.5 (4) | C24—C29—C28—C27 | −1.2 (6) |
O9—Fe2—N4—C31 | 3.8 (4) | C25—C24—C29—C28 | 2.1 (6) |
O9—Fe2—N4—C39 | −178.9 (5) | C25—C26—C27—C28 | 1.0 (7) |
O9—C40—C31—N4 | −10.1 (7) | C26—C25—C24—C29 | −1.6 (6) |
O9—C40—C31—C32 | 170.5 (5) | C26—C27—C28—C29 | −0.4 (7) |
O10—C40—C31—N4 | 168.5 (5) | C29—N3—C21—C30 | −177.7 (3) |
O10—C40—C31—C32 | −10.9 (8) | C31—N4—C39—C34 | −4.4 (8) |
O11—Fe2—O7—C30 | 80.2 (3) | C31—N4—C39—C38 | 174.0 (5) |
O11—Fe2—O9—C40 | 168.3 (4) | C31—C32—C33—C34 | −1.8 (9) |
O11—Fe2—N3—C21 | −83.3 (3) | C32—C31—N4—C39 | 3.3 (8) |
O11—Fe2—N3—C29 | 97.8 (3) | C32—C33—C34—C35 | −178.4 (6) |
O11—Fe2—N4—C31 | −1.5 (7) | C32—C33—C34—C39 | 0.8 (9) |
O11—Fe2—N4—C39 | 175.9 (5) | C33—C32—C31—C40 | 179.0 (5) |
O12—Fe2—O7—C30 | 172.7 (3) | C33—C34—C35—C36 | 176.3 (6) |
O12—Fe2—O9—C40 | 76.4 (4) | C33—C34—C39—C38 | −176.0 (5) |
O12—Fe2—N3—C21 | 16.3 (5) | C34—C35—C36—C37 | 1 (1) |
O12—Fe2—N3—C29 | −162.6 (4) | C34—C39—C38—C37 | −2.1 (9) |
O12—Fe2—N4—C31 | −90.7 (4) | C35—C34—C39—C38 | 3.2 (8) |
O12—Fe2—N4—C39 | 86.6 (5) | C35—C36—C37—C38 | 0 (1) |
O13—C50—C41—N5 | 5.5 (9) | C36—C35—C34—C39 | −2.8 (9) |
O13—C50—C41—C42 | −174.3 (6) | C36—C37—C38—C39 | 0.6 (10) |
O14—C50—C41—N5 | −173.9 (5) | C39—N4—C31—C40 | −176.0 (5) |
O14—C50—C41—C42 | 6.3 (8) | C41—N5—C49—C44 | 0.7 (8) |
N1—Fe1—O1—C10 | 1.6 (3) | C41—N5—C49—C48 | 179.9 (6) |
N1—Fe1—O3—C20 | −100.4 (5) | C41—C42—C43—C44 | 1.2 (9) |
N1—Fe1—N2—C11 | 108.5 (4) | C42—C41—N5—C49 | 0.6 (9) |
N1—Fe1—N2—C19 | −65.1 (5) | C42—C43—C44—C45 | −178.7 (6) |
N1—C1—C2—C3 | −0.9 (6) | C42—C43—C44—C49 | 0.0 (9) |
N1—C9—C4—C3 | 0.2 (5) | C43—C42—C41—C50 | 178.1 (6) |
N1—C9—C4—C5 | 179.4 (3) | C43—C44—C45—C46 | 178.7 (7) |
N1—C9—C8—C7 | −179.8 (3) | C43—C44—C49—C48 | 179.8 (6) |
N2—Fe1—O1—C10 | −89.1 (3) | C44—C45—C46—C47 | 1 (1) |
N2—Fe1—O3—C20 | −11.1 (5) | C44—C49—C48—C47 | 1.8 (10) |
N2—Fe1—N1—C1 | 99.8 (3) | C45—C44—C49—C48 | −1.4 (9) |
N2—Fe1—N1—C9 | −79.6 (3) | C45—C46—C47—C48 | 0 (1) |
N2—C11—C12—C13 | 1.8 (10) | C46—C45—C44—C49 | 0.0 (10) |
N2—C19—C14—C13 | 3.9 (9) | C46—C47—C48—C49 | 0 (1) |
N2—C19—C14—C15 | −177.1 (6) | C49—N5—C41—C50 | −179.1 (5) |
N2—C19—C18—C17 | 177.7 (6) | C49—N5—C41—C50 | −179.1 (5) |
N3—Fe2—O7—C30 | −11.8 (3) | | |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+1, −z+2; (v) x−1, y, z+1; (vi) x, y, z+1; (vii) x−1, y, z; (viii) x, y+1, z; (ix) x, y, z−1; (x) −x, −y, −z+1; (xi) −x+1, −y, −z+1; (xii) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O15vii | 0.83 | 2.02 | 2.801 (4) | 158 |
O6—H6B···O15iii | 0.82 | 1.92 | 2.731 (4) | 167 |
O5—H5B···O3iv | 0.82 | 2.12 | 2.910 (4) | 162 |
O6—H6A···O4iv | 0.83 | 1.99 | 2.760 (5) | 154 |
O11—H11A···O13viii | 0.92 | 1.95 | 2.854 (5) | 166 |
O11—H11B···O10i | 0.92 | 2.00 | 2.917 (5) | 175 |
O14—H14···O10x | 0.83 | 1.87 | 2.675 (5) | 169 |
O15—H15A···O8ii | 0.84 | 1.87 | 2.704 (5) | 170 |
O12—H12A···O5i | 0.82 | 2.15 | 2.949 (5) | 165 |
O15—H15B···N5xi | 0.93 | 2.01 | 2.936 (5) | 178 |
O12—H12B···O16i | 0.82 | 1.94 | 2.757 (5) | 170 |
O16—H16A···O11 | 0.92 | 2.15 | 3.071 (5) | 178 |
O16—H16B···O2 | 0.89 | 1.83 | 2.722 (5) | 178 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+1, −z+2; (vii) x−1, y, z; (viii) x, y+1, z; (x) −x, −y, −z+1; (xi) −x+1, −y, −z+1. |
Experimental details
Crystal data |
Chemical formula | [Fe(C8H8NO2)2(H2O)2]2·C10H7NO2·2H2O |
Mr | 1081.59 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 12.662 (3), 13.438 (3), 16.340 (3) |
α, β, γ (°) | 97.20 (2), 101.94 (2), 117.79 (1) |
V (Å3) | 2326.0 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.71 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.844, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11146, 10701, 4869 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.174, 0.84 |
No. of reflections | 10701 |
No. of parameters | 658 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.48 |
Selected geometric parameters (Å, º) topFe1—O1 | 2.025 (3) | Fe2—O7 | 2.043 (3) |
Fe1—O3 | 2.061 (4) | Fe2—O9 | 2.080 (4) |
Fe1—O5 | 2.166 (4) | Fe2—O11 | 2.190 (3) |
Fe1—O6 | 2.173 (3) | Fe2—O12 | 2.122 (5) |
Fe1—N1 | 2.248 (5) | Fe2—N3 | 2.265 (4) |
Fe1—N2 | 2.290 (3) | Fe2—N4 | 2.209 (3) |
| | | |
O1—Fe1—O3 | 176.0 (2) | O9—Fe2—O12 | 93.7 (2) |
O1—Fe1—O5 | 86.4 (2) | O9—Fe2—N3 | 106.9 (1) |
O1—Fe1—O6 | 91.2 (1) | O9—Fe2—N4 | 76.0 (1) |
O1—Fe1—N1 | 76.5 (2) | O11—Fe2—O12 | 92.2 (2) |
O1—Fe1—N2 | 102.6 (1) | O11—Fe2—N3 | 91.3 (1) |
O3—Fe1—O5 | 89.9 (2) | O11—Fe2—N4 | 161.1 (2) |
O3—Fe1—O6 | 90.1 (1) | O12—Fe2—N3 | 159.3 (2) |
O3—Fe1—N1 | 107.3 (2) | O12—Fe2—N4 | 87.4 (2) |
O3—Fe1—N2 | 76.1 (1) | N3—Fe2—N4 | 95.7 (1) |
O5—Fe1—O6 | 85.3 (1) | Fe1—O1—C10 | 120.8 (3) |
O5—Fe1—N1 | 162.4 (1) | Fe1—O3—C20 | 119.0 (3) |
O5—Fe1—N2 | 94.2 (1) | Fe2—O7—C30 | 119.0 (3) |
O6—Fe1—N1 | 90.9 (1) | Fe2—O9—C40 | 118.4 (3) |
O6—Fe1—N2 | 166.2 (1) | Fe1—N1—C1 | 110.8 (3) |
N1—Fe1—N2 | 93.5 (1) | Fe1—N1—C9 | 131.2 (3) |
O7—Fe2—O9 | 171.9 (1) | Fe1—N2—C11 | 109.9 (3) |
O7—Fe2—O11 | 87.4 (1) | Fe1—N2—C19 | 132.1 (3) |
O7—Fe2—O12 | 83.5 (2) | Fe2—N3—C21 | 110.7 (3) |
O7—Fe2—N3 | 76.2 (1) | Fe2—N3—C29 | 131.9 (3) |
O7—Fe2—N4 | 111.3 (1) | Fe2—N4—C31 | 112.6 (3) |
O9—Fe2—O11 | 85.1 (1) | Fe2—N4—C39 | 128.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O15i | 0.83 | 2.02 | 2.801 (4) | 158 |
O6—H6B···O15ii | 0.82 | 1.92 | 2.731 (4) | 167 |
O5—H5B···O3iii | 0.82 | 2.12 | 2.910 (4) | 162 |
O6—H6A···O4iii | 0.83 | 1.99 | 2.760 (5) | 154 |
O11—H11A···O13iv | 0.92 | 1.95 | 2.854 (5) | 166 |
O11—H11B···O10v | 0.92 | 2.00 | 2.917 (5) | 175 |
O14—H14···O10vi | 0.83 | 1.87 | 2.675 (5) | 169 |
O15—H15A···O8vii | 0.84 | 1.87 | 2.704 (5) | 170 |
O12—H12A···O5v | 0.82 | 2.15 | 2.949 (5) | 165 |
O15—H15B···N5viii | 0.93 | 2.01 | 2.936 (5) | 178 |
O12—H12B···O16v | 0.82 | 1.94 | 2.757 (5) | 170 |
O16—H16A···O11 | 0.92 | 2.15 | 3.071 (5) | 178 |
O16—H16B···O2 | 0.89 | 1.83 | 2.722 (5) | 178 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+2; (iv) x, y+1, z; (v) −x, −y+1, −z+1; (vi) −x, −y, −z+1; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y, −z+1. |
Quinoline-2-carboxylic acid is a tryptophan metabolite (Martell & Smith, 1974). Crystal structures of its metal complexes have been determined with CuII (Haendler, 1986), MnII (Haendler, 1996; Okabe & Koizumi, 1997), FeII, CoII (Okabe & Makino, 1998, 1999), NiII (Odoko et al., 2001) and VIV (Okabe & Muranishi, 2002). The iron complex improves the Fenton oxidation reaction by Fenton's reagent (FeSO4·7H2O and H2O2) (Shul'pin, 2002), acting as a co-catalyst. Although the FeII complex has already been structurally characterized as trans-diaquabis(2-quinolinecarboxylato-N,O)iron(II)–ethanol–water (1/2/2) (Okabe & Makino, 1998), the structure of the FeII complex in a cis configuration has now also been determined as the title mixed solvate, (I).
The structure of the complex is shown in Fig. 1, and selected geometric parameters are listed in Table 1. Two cis-diaquabis(quinoline-2-carboxylato)iron(II) molecules, one free quinoline-2-carboxylic acid molecule and two water molecules are present in the asymmetric unit. The structures of the two independent complex molecules are almost the same. The bidentate organic ligands in each complex are nearly perpendicular to each other [N1—Fe1—N2 = 93.5 (1)° and N3—Fe2—N4 = 95.7 (1)°]. In each complex, the central FeII ion is coordinated by two N and two O atoms of the two organic ligands and by two aqua O atoms, in a distorted octahedral geometry. The ligand atoms are coordinated in a cis configuration. This cis configuration is quite different from trans-diaquabis(2-quinolinecarboxylato)iron(II) (Okabe & Makino, 1998), in which the quinoline rings of the two ligands lie in the same plane. The carboxyl groups of the ligands are ionized. The organic ligands and the central FeII ion form five-membered rings in a slightly distorted manner, as reflected by the torsion angles [O1—C10—C1—N1 = −1.5 (5), O3—C20—C11—N2 = −16.1 (8), O7—C30—C21—N3 = −13.3 (5) and O9—C40—C31—N4 − 10.1 (7)°]. Five-membered ring formation is usually observed in the metal complexes of quinoline-2-carboxylic acid (Okabe & Makino, 1999). The ligand–Fe distances are a little different from each other: Fe—O(carboxylate) = 2.025 (3)–2.080 (4) Å, Fe—N = 2.209 (3)–2.290 (3) Å and Fe—O(water) = 2.122 (5)–2.190 (3) Å. These values are somewhat different from those in the trans complex: Fe—O(carboxylate, trans) = 2.087 (1) Å, Fe—N(trans) = 2.270 (1) Å and Fe—O(water, trans) = 2.131 (1) Å. These cis and trans configurations of FeII complexes of quinoline-2-carboxylic acid should influence differently the metal–H2O2 binding interaction in the Fenton reaction (Shul'pin, 2002).
In the crystal packing, shown in Fig. 2, quinoline rings of the complex and the free quinoline-2-carboxylic acid stack alternately. The FeII complex, the free quinoline-2-carboxylic acid and the water molecule are linked to each other by a hydrogen-bonding network, as shown in Table 2.