Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106043484/fa3038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106043484/fa3038Isup2.hkl |
CCDC reference: 632916
A mixture of NaOH (0.012 g, 0.3 mmol) and 6-methylpyridine-2-carboxylic acid (0.041 g, 0.3 mmol) in water (10 ml) was stirred for 10 min, and then CrCl3·6H2O (0.027 g, 0.1 mmol) was added. A purple solid was collected by filtration after stirring for 30 min. The solid was redissolved in methanol (15 ml), and Ph3SnCl (0.039 g, 0.1 mmol) was added to the purple solution. After refluxing for 2 h, the mixture was filtered. Purple block crystals of (I) were obtained by evaporating the filtrate at room temperature for several days.
The H atoms on the disordered methyl group of methanol were not located. Other H atoms bound to carbon were refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H. The hydroxy H atom was located in a difference Fourier map. Its coordinates were refined and its Uiso(H) was set to 1.5 Ueq(O).
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.
[CrSn(C6H5)3(C7H6NO2)3Cl][Sn(C6H5)3Cl(CH4O)] | Z = 2 |
Mr = 1263.31 | F(000) = 1270 |
Triclinic, P1 | Dx = 1.475 Mg m−3 |
Hall symbol: -P 1 | Melting point: not measured K |
a = 12.767 (5) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 14.095 (5) Å | Cell parameters from 22 reflections |
c = 15.967 (5) Å | θ = 1.6–25.0° |
α = 96.122 (5)° | µ = 1.21 mm−1 |
β = 91.784 (5)° | T = 293 K |
γ = 94.944 (5)° | Block, purple |
V = 2843.9 (17) Å3 | 0.52 × 0.40 × 0.32 mm |
Siemens P4 diffractometer | 7137 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
ω scans | h = −1→15 |
Absorption correction: ψ scan (North et al., 1968) | k = −16→16 |
Tmin = 0.228, Tmax = 0.303 | l = −18→18 |
11436 measured reflections | 3 standard reflections every 97 reflections |
9854 independent reflections | intensity decay: none |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0263P)2] where P = (Fo2 + 2Fc2)/3 |
9854 reflections | (Δ/σ)max = 0.006 |
673 parameters | Δρmax = 0.60 e Å−3 |
5 restraints | Δρmin = −0.36 e Å−3 |
[CrSn(C6H5)3(C7H6NO2)3Cl][Sn(C6H5)3Cl(CH4O)] | γ = 94.944 (5)° |
Mr = 1263.31 | V = 2843.9 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.767 (5) Å | Mo Kα radiation |
b = 14.095 (5) Å | µ = 1.21 mm−1 |
c = 15.967 (5) Å | T = 293 K |
α = 96.122 (5)° | 0.52 × 0.40 × 0.32 mm |
β = 91.784 (5)° |
Siemens P4 diffractometer | 7137 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.020 |
Tmin = 0.228, Tmax = 0.303 | 3 standard reflections every 97 reflections |
11436 measured reflections | intensity decay: none |
9854 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 5 restraints |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | Δρmax = 0.60 e Å−3 |
9854 reflections | Δρmin = −0.36 e Å−3 |
673 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cr1 | 0.78149 (4) | 0.27289 (3) | 0.76728 (3) | 0.03346 (13) | |
Sn1 | 1.121480 (19) | 0.042045 (16) | 0.751782 (15) | 0.04067 (7) | |
Sn2 | 0.50490 (2) | 0.667362 (17) | 0.732214 (15) | 0.04664 (8) | |
C1 | 0.3456 (3) | 0.6044 (3) | 0.7268 (2) | 0.0495 (9) | |
C2 | 0.3222 (4) | 0.5056 (3) | 0.7233 (3) | 0.0688 (12) | |
H2 | 0.3768 | 0.4662 | 0.7261 | 0.083* | |
C3 | 0.2194 (5) | 0.4650 (4) | 0.7158 (3) | 0.0823 (14) | |
H3 | 0.2057 | 0.3988 | 0.7135 | 0.099* | |
C4 | 0.1398 (5) | 0.5197 (5) | 0.7119 (3) | 0.0859 (16) | |
H4 | 0.0708 | 0.4919 | 0.7068 | 0.103* | |
C5 | 0.1597 (4) | 0.6161 (4) | 0.7155 (3) | 0.0773 (14) | |
H5 | 0.1038 | 0.6539 | 0.7126 | 0.093* | |
C6 | 0.2625 (4) | 0.6597 (3) | 0.7234 (2) | 0.0621 (11) | |
H6 | 0.2746 | 0.7260 | 0.7263 | 0.074* | |
C7 | 0.6184 (3) | 0.6006 (2) | 0.6556 (2) | 0.0490 (9) | |
C8 | 0.6034 (4) | 0.5921 (3) | 0.5683 (2) | 0.0684 (12) | |
H8 | 0.5419 | 0.6106 | 0.5446 | 0.082* | |
C9 | 0.6784 (5) | 0.5568 (3) | 0.5166 (3) | 0.0826 (15) | |
H9 | 0.6673 | 0.5509 | 0.4584 | 0.099* | |
C10 | 0.7686 (5) | 0.5306 (3) | 0.5507 (4) | 0.0878 (16) | |
H10 | 0.8199 | 0.5084 | 0.5155 | 0.105* | |
C11 | 0.7851 (4) | 0.5364 (3) | 0.6364 (3) | 0.0742 (13) | |
H11 | 0.8468 | 0.5174 | 0.6592 | 0.089* | |
C12 | 0.7093 (3) | 0.5709 (3) | 0.6885 (3) | 0.0601 (11) | |
H12 | 0.7199 | 0.5741 | 0.7467 | 0.072* | |
C13 | 0.5587 (3) | 0.7730 (2) | 0.8323 (2) | 0.0479 (9) | |
C14 | 0.6637 (4) | 0.8053 (3) | 0.8427 (3) | 0.0745 (13) | |
H14 | 0.7108 | 0.7829 | 0.8036 | 0.089* | |
C15 | 0.7004 (4) | 0.8710 (3) | 0.9108 (4) | 0.0909 (17) | |
H15 | 0.7717 | 0.8911 | 0.9175 | 0.109* | |
C16 | 0.6320 (6) | 0.9060 (4) | 0.9680 (3) | 0.0965 (19) | |
H16 | 0.6562 | 0.9489 | 1.0142 | 0.116* | |
C17 | 0.5285 (6) | 0.8769 (4) | 0.9558 (4) | 0.128 (3) | |
H17 | 0.4816 | 0.9007 | 0.9944 | 0.154* | |
C18 | 0.4902 (4) | 0.8127 (4) | 0.8879 (3) | 0.0940 (18) | |
H18 | 0.4181 | 0.7965 | 0.8799 | 0.113* | |
C19 | 0.9995 (3) | −0.0619 (3) | 0.6968 (2) | 0.0484 (9) | |
C20 | 0.9533 (3) | −0.0512 (3) | 0.6197 (3) | 0.0615 (11) | |
H20 | 0.9731 | 0.0025 | 0.5928 | 0.074* | |
C21 | 0.8770 (4) | −0.1202 (4) | 0.5819 (3) | 0.0784 (15) | |
H21 | 0.8453 | −0.1128 | 0.5301 | 0.094* | |
C22 | 0.8487 (4) | −0.2003 (4) | 0.6223 (4) | 0.0885 (18) | |
H22 | 0.7974 | −0.2464 | 0.5974 | 0.106* | |
C23 | 0.8955 (4) | −0.2122 (3) | 0.6984 (4) | 0.0883 (16) | |
H23 | 0.8772 | −0.2668 | 0.7245 | 0.106* | |
C24 | 0.9700 (3) | −0.1428 (3) | 0.7360 (3) | 0.0649 (11) | |
H24 | 1.0007 | −0.1502 | 0.7882 | 0.078* | |
C25 | 1.2399 (3) | 0.0726 (3) | 0.6646 (2) | 0.0452 (9) | |
C26 | 1.2889 (3) | −0.0027 (3) | 0.6250 (3) | 0.0636 (11) | |
H26 | 1.2719 | −0.0646 | 0.6387 | 0.076* | |
C27 | 1.3625 (4) | 0.0129 (4) | 0.5657 (3) | 0.0934 (17) | |
H27 | 1.3946 | −0.0383 | 0.5392 | 0.112* | |
C28 | 1.3889 (4) | 0.1043 (4) | 0.5452 (3) | 0.0889 (16) | |
H28 | 1.4389 | 0.1148 | 0.5053 | 0.107* | |
C29 | 1.3416 (4) | 0.1780 (4) | 0.5834 (3) | 0.0812 (15) | |
H29 | 1.3589 | 0.2398 | 0.5696 | 0.097* | |
C30 | 1.2680 (3) | 0.1628 (3) | 0.6427 (3) | 0.0608 (11) | |
H30 | 1.2365 | 0.2147 | 0.6687 | 0.073* | |
C31 | 1.1062 (3) | 0.1349 (3) | 0.8637 (2) | 0.0536 (10) | |
C32 | 1.0476 (4) | 0.1062 (3) | 0.9285 (3) | 0.0733 (13) | |
H32 | 1.0156 | 0.0440 | 0.9242 | 0.088* | |
C33 | 1.0347 (5) | 0.1689 (5) | 1.0014 (3) | 0.101 (2) | |
H33 | 0.9953 | 0.1488 | 1.0454 | 0.121* | |
C34 | 1.0816 (6) | 0.2597 (6) | 1.0056 (4) | 0.125 (3) | |
H34 | 1.0723 | 0.3026 | 1.0527 | 0.150* | |
C35 | 1.1410 (6) | 0.2892 (4) | 0.9435 (5) | 0.129 (3) | |
H35 | 1.1734 | 0.3513 | 0.9483 | 0.155* | |
C36 | 1.1537 (5) | 0.2264 (3) | 0.8722 (3) | 0.0938 (17) | |
H36 | 1.1952 | 0.2469 | 0.8296 | 0.113* | |
C37 | 0.5650 (3) | 0.2137 (2) | 0.7928 (2) | 0.0435 (8) | |
C38 | 0.4730 (3) | 0.1649 (3) | 0.8102 (3) | 0.0596 (11) | |
H38 | 0.4166 | 0.1973 | 0.8298 | 0.072* | |
C39 | 0.4654 (3) | 0.0658 (3) | 0.7978 (3) | 0.0673 (12) | |
H39 | 0.4055 | 0.0302 | 0.8128 | 0.081* | |
C40 | 0.5460 (3) | 0.0217 (3) | 0.7637 (3) | 0.0598 (11) | |
H40 | 0.5391 | −0.0445 | 0.7507 | 0.072* | |
C41 | 0.6392 (3) | 0.0739 (2) | 0.7476 (2) | 0.0459 (9) | |
C42 | 0.5775 (3) | 0.3209 (3) | 0.7992 (2) | 0.0463 (9) | |
C43 | 0.7277 (4) | 0.0245 (3) | 0.7095 (3) | 0.0747 (13) | |
H43A | 0.7561 | 0.0594 | 0.6657 | 0.112* | |
H43B | 0.7023 | −0.0392 | 0.6861 | 0.112* | |
H43C | 0.7816 | 0.0214 | 0.7521 | 0.112* | |
C44 | 0.8921 (3) | 0.2271 (2) | 0.6201 (2) | 0.0424 (8) | |
C45 | 0.9336 (4) | 0.2255 (3) | 0.5423 (2) | 0.0626 (11) | |
H45 | 1.0010 | 0.2072 | 0.5334 | 0.075* | |
C46 | 0.8725 (4) | 0.2520 (3) | 0.4771 (2) | 0.0752 (14) | |
H46 | 0.8984 | 0.2516 | 0.4233 | 0.090* | |
C47 | 0.7750 (4) | 0.2784 (3) | 0.4922 (2) | 0.0642 (11) | |
H47 | 0.7338 | 0.2959 | 0.4484 | 0.077* | |
C48 | 0.7354 (3) | 0.2797 (2) | 0.5728 (2) | 0.0446 (9) | |
C49 | 0.9473 (3) | 0.1903 (2) | 0.6929 (2) | 0.0429 (8) | |
C50 | 0.6272 (3) | 0.3067 (3) | 0.5885 (2) | 0.0552 (10) | |
H50A | 0.5920 | 0.2618 | 0.6217 | 0.083* | |
H50B | 0.5889 | 0.3059 | 0.5357 | 0.083* | |
H50C | 0.6308 | 0.3699 | 0.6183 | 0.083* | |
C51 | 0.8532 (3) | 0.3930 (2) | 0.9133 (2) | 0.0447 (9) | |
C52 | 0.8676 (3) | 0.4383 (3) | 0.9945 (2) | 0.0612 (11) | |
H52 | 0.8963 | 0.5015 | 1.0044 | 0.073* | |
C53 | 0.8387 (4) | 0.3877 (3) | 1.0600 (3) | 0.0760 (14) | |
H53 | 0.8442 | 0.4175 | 1.1150 | 0.091* | |
C54 | 0.8020 (4) | 0.2938 (3) | 1.0445 (2) | 0.0648 (12) | |
H54 | 0.7860 | 0.2584 | 1.0891 | 0.078* | |
C55 | 0.7883 (3) | 0.2509 (3) | 0.9622 (2) | 0.0493 (9) | |
C56 | 0.8881 (3) | 0.4415 (3) | 0.8382 (2) | 0.0469 (9) | |
C57 | 0.7519 (4) | 0.1464 (3) | 0.9439 (2) | 0.0661 (12) | |
H57A | 0.6767 | 0.1388 | 0.9358 | 0.099* | |
H57B | 0.7723 | 0.1132 | 0.9904 | 0.099* | |
H57C | 0.7834 | 0.1203 | 0.8937 | 0.099* | |
C58 | 0.6188 (12) | 0.5746 (8) | 0.9132 (10) | 0.144 (5) | 0.56 |
C59 | 0.5241 (15) | 0.5827 (9) | 0.9262 (8) | 0.120 (6) | 0.44 |
N1 | 0.6500 (2) | 0.17042 (17) | 0.76501 (16) | 0.0350 (6) | |
N2 | 0.7955 (2) | 0.25554 (17) | 0.63662 (16) | 0.0362 (6) | |
N3 | 0.8106 (2) | 0.30178 (19) | 0.89732 (16) | 0.0397 (7) | |
O1 | 0.66929 (18) | 0.35730 (15) | 0.78253 (14) | 0.0411 (5) | |
O2 | 0.5032 (2) | 0.36720 (18) | 0.8173 (2) | 0.0701 (8) | |
O3 | 0.89799 (18) | 0.19122 (16) | 0.76041 (14) | 0.0449 (6) | |
O4 | 1.0335 (2) | 0.15843 (18) | 0.68137 (16) | 0.0536 (6) | |
O5 | 0.87799 (19) | 0.38630 (16) | 0.76783 (14) | 0.0455 (6) | |
O6 | 0.9253 (3) | 0.5240 (2) | 0.84637 (17) | 0.0768 (9) | |
O7 | 0.5433 (3) | 0.56069 (18) | 0.83625 (17) | 0.0631 (8) | |
Cl1 | 1.21367 (8) | −0.07609 (7) | 0.82594 (6) | 0.0587 (3) | |
Cl2 | 0.46983 (10) | 0.78780 (7) | 0.63496 (6) | 0.0640 (3) | |
H7O | 0.533 (3) | 0.4995 (15) | 0.8194 (16) | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cr1 | 0.0348 (3) | 0.0345 (3) | 0.0309 (3) | 0.0026 (2) | 0.0005 (2) | 0.0036 (2) |
Sn1 | 0.03828 (14) | 0.04065 (14) | 0.04290 (14) | 0.00423 (11) | 0.00309 (11) | 0.00277 (10) |
Sn2 | 0.06054 (18) | 0.03848 (14) | 0.03995 (14) | 0.00568 (12) | −0.00060 (12) | −0.00023 (10) |
C1 | 0.064 (3) | 0.051 (2) | 0.0328 (19) | 0.004 (2) | 0.0022 (18) | −0.0006 (16) |
C2 | 0.073 (3) | 0.056 (3) | 0.075 (3) | 0.004 (2) | 0.004 (3) | −0.003 (2) |
C3 | 0.082 (4) | 0.072 (3) | 0.085 (3) | −0.022 (3) | 0.005 (3) | −0.004 (3) |
C4 | 0.074 (4) | 0.126 (5) | 0.054 (3) | −0.015 (4) | 0.004 (3) | 0.014 (3) |
C5 | 0.061 (3) | 0.122 (5) | 0.055 (3) | 0.020 (3) | 0.008 (2) | 0.026 (3) |
C6 | 0.074 (3) | 0.070 (3) | 0.046 (2) | 0.019 (3) | 0.009 (2) | 0.016 (2) |
C7 | 0.068 (3) | 0.0364 (19) | 0.044 (2) | 0.0099 (19) | 0.007 (2) | 0.0050 (16) |
C8 | 0.095 (4) | 0.066 (3) | 0.046 (2) | 0.023 (3) | 0.001 (2) | 0.000 (2) |
C9 | 0.116 (5) | 0.077 (3) | 0.056 (3) | 0.021 (3) | 0.020 (3) | 0.000 (2) |
C10 | 0.104 (4) | 0.064 (3) | 0.102 (4) | 0.028 (3) | 0.049 (4) | 0.014 (3) |
C11 | 0.062 (3) | 0.062 (3) | 0.104 (4) | 0.013 (2) | 0.015 (3) | 0.026 (3) |
C12 | 0.069 (3) | 0.048 (2) | 0.066 (3) | 0.009 (2) | 0.008 (2) | 0.013 (2) |
C13 | 0.059 (3) | 0.0378 (19) | 0.046 (2) | 0.0069 (18) | −0.0020 (19) | 0.0003 (16) |
C14 | 0.065 (3) | 0.067 (3) | 0.088 (3) | 0.014 (2) | −0.004 (3) | −0.014 (2) |
C15 | 0.072 (3) | 0.071 (3) | 0.121 (5) | 0.002 (3) | −0.043 (3) | −0.011 (3) |
C16 | 0.150 (6) | 0.072 (3) | 0.058 (3) | −0.017 (4) | −0.013 (4) | −0.012 (3) |
C17 | 0.136 (6) | 0.132 (5) | 0.095 (4) | −0.039 (5) | 0.056 (4) | −0.064 (4) |
C18 | 0.079 (4) | 0.098 (4) | 0.089 (4) | −0.028 (3) | 0.032 (3) | −0.041 (3) |
C19 | 0.041 (2) | 0.050 (2) | 0.050 (2) | −0.0005 (18) | 0.0095 (18) | −0.0152 (17) |
C20 | 0.055 (3) | 0.065 (3) | 0.059 (3) | 0.013 (2) | 0.002 (2) | −0.020 (2) |
C21 | 0.053 (3) | 0.103 (4) | 0.071 (3) | 0.020 (3) | −0.008 (2) | −0.039 (3) |
C22 | 0.053 (3) | 0.084 (4) | 0.114 (5) | −0.011 (3) | 0.019 (3) | −0.047 (3) |
C23 | 0.072 (4) | 0.066 (3) | 0.117 (5) | −0.020 (3) | 0.012 (3) | −0.016 (3) |
C24 | 0.061 (3) | 0.059 (3) | 0.071 (3) | −0.011 (2) | 0.014 (2) | 0.000 (2) |
C25 | 0.034 (2) | 0.051 (2) | 0.053 (2) | 0.0042 (17) | 0.0031 (17) | 0.0134 (17) |
C26 | 0.065 (3) | 0.062 (3) | 0.069 (3) | 0.019 (2) | 0.027 (2) | 0.013 (2) |
C27 | 0.092 (4) | 0.105 (4) | 0.095 (4) | 0.042 (3) | 0.052 (3) | 0.026 (3) |
C28 | 0.064 (3) | 0.123 (5) | 0.089 (4) | 0.014 (3) | 0.034 (3) | 0.039 (3) |
C29 | 0.063 (3) | 0.085 (3) | 0.103 (4) | −0.003 (3) | 0.011 (3) | 0.051 (3) |
C30 | 0.055 (3) | 0.053 (2) | 0.077 (3) | 0.003 (2) | 0.003 (2) | 0.018 (2) |
C31 | 0.051 (2) | 0.053 (2) | 0.055 (2) | 0.018 (2) | −0.008 (2) | −0.0071 (19) |
C32 | 0.084 (3) | 0.087 (3) | 0.051 (3) | 0.023 (3) | 0.003 (2) | 0.001 (2) |
C33 | 0.118 (5) | 0.142 (5) | 0.045 (3) | 0.057 (4) | −0.001 (3) | −0.012 (3) |
C34 | 0.154 (7) | 0.128 (6) | 0.088 (5) | 0.082 (6) | −0.050 (5) | −0.059 (4) |
C35 | 0.167 (7) | 0.079 (4) | 0.128 (6) | 0.019 (4) | −0.010 (5) | −0.046 (4) |
C36 | 0.112 (4) | 0.060 (3) | 0.103 (4) | 0.006 (3) | 0.006 (3) | −0.023 (3) |
C37 | 0.040 (2) | 0.044 (2) | 0.047 (2) | 0.0068 (17) | −0.0026 (17) | 0.0070 (16) |
C38 | 0.039 (2) | 0.061 (3) | 0.082 (3) | 0.005 (2) | 0.005 (2) | 0.021 (2) |
C39 | 0.044 (2) | 0.061 (3) | 0.098 (3) | −0.012 (2) | −0.006 (2) | 0.026 (2) |
C40 | 0.066 (3) | 0.038 (2) | 0.072 (3) | −0.008 (2) | −0.012 (2) | 0.0061 (19) |
C41 | 0.059 (2) | 0.0364 (19) | 0.040 (2) | 0.0007 (18) | −0.0045 (18) | 0.0016 (15) |
C42 | 0.047 (2) | 0.044 (2) | 0.050 (2) | 0.0108 (19) | 0.0037 (18) | 0.0086 (16) |
C43 | 0.090 (4) | 0.038 (2) | 0.095 (3) | 0.010 (2) | 0.022 (3) | −0.006 (2) |
C44 | 0.047 (2) | 0.0428 (19) | 0.0389 (19) | 0.0127 (17) | 0.0041 (17) | 0.0037 (15) |
C45 | 0.069 (3) | 0.076 (3) | 0.049 (2) | 0.029 (2) | 0.015 (2) | 0.013 (2) |
C46 | 0.092 (4) | 0.108 (4) | 0.033 (2) | 0.038 (3) | 0.014 (2) | 0.014 (2) |
C47 | 0.075 (3) | 0.085 (3) | 0.036 (2) | 0.019 (3) | −0.004 (2) | 0.010 (2) |
C48 | 0.053 (2) | 0.044 (2) | 0.0354 (19) | 0.0068 (18) | −0.0080 (17) | 0.0003 (15) |
C49 | 0.043 (2) | 0.0382 (19) | 0.048 (2) | 0.0085 (17) | 0.0016 (18) | 0.0022 (16) |
C50 | 0.049 (2) | 0.073 (3) | 0.044 (2) | 0.011 (2) | −0.0128 (18) | 0.0109 (19) |
C51 | 0.045 (2) | 0.048 (2) | 0.0397 (19) | 0.0018 (18) | 0.0002 (17) | −0.0004 (16) |
C52 | 0.078 (3) | 0.059 (2) | 0.044 (2) | 0.005 (2) | 0.000 (2) | −0.0066 (19) |
C53 | 0.105 (4) | 0.082 (3) | 0.037 (2) | 0.003 (3) | −0.003 (2) | −0.009 (2) |
C54 | 0.081 (3) | 0.080 (3) | 0.033 (2) | 0.003 (3) | 0.005 (2) | 0.012 (2) |
C55 | 0.051 (2) | 0.061 (2) | 0.037 (2) | 0.0031 (19) | 0.0001 (17) | 0.0104 (17) |
C56 | 0.049 (2) | 0.045 (2) | 0.042 (2) | −0.0124 (18) | 0.0019 (18) | 0.0026 (17) |
C57 | 0.089 (3) | 0.062 (3) | 0.047 (2) | −0.011 (2) | −0.007 (2) | 0.0219 (19) |
C58 | 0.152 (13) | 0.074 (7) | 0.206 (15) | 0.016 (8) | −0.020 (12) | 0.016 (8) |
C59 | 0.192 (16) | 0.085 (9) | 0.112 (11) | 0.073 (10) | 0.091 (11) | 0.064 (8) |
N1 | 0.0408 (16) | 0.0301 (14) | 0.0341 (14) | 0.0027 (12) | −0.0005 (12) | 0.0050 (11) |
N2 | 0.0418 (17) | 0.0348 (14) | 0.0325 (14) | 0.0066 (13) | −0.0009 (13) | 0.0035 (11) |
N3 | 0.0389 (17) | 0.0460 (16) | 0.0337 (15) | 0.0006 (14) | −0.0001 (13) | 0.0046 (12) |
O1 | 0.0441 (15) | 0.0335 (12) | 0.0458 (14) | 0.0046 (11) | 0.0042 (11) | 0.0035 (10) |
O2 | 0.0524 (17) | 0.0529 (16) | 0.110 (2) | 0.0219 (14) | 0.0256 (17) | 0.0133 (16) |
O3 | 0.0437 (14) | 0.0564 (15) | 0.0388 (13) | 0.0148 (12) | 0.0043 (12) | 0.0149 (11) |
O4 | 0.0451 (16) | 0.0617 (16) | 0.0590 (16) | 0.0222 (13) | 0.0078 (13) | 0.0143 (13) |
O5 | 0.0494 (15) | 0.0490 (14) | 0.0353 (13) | −0.0094 (12) | 0.0009 (11) | 0.0036 (11) |
O6 | 0.100 (2) | 0.0570 (17) | 0.0649 (19) | −0.0304 (17) | 0.0063 (17) | −0.0019 (14) |
O7 | 0.087 (2) | 0.0505 (15) | 0.0537 (17) | 0.0108 (16) | −0.0015 (16) | 0.0134 (13) |
Cl1 | 0.0593 (6) | 0.0533 (5) | 0.0678 (6) | 0.0097 (5) | −0.0002 (5) | 0.0234 (5) |
Cl2 | 0.0925 (8) | 0.0451 (5) | 0.0555 (6) | 0.0069 (5) | −0.0070 (6) | 0.0122 (4) |
Cr1—O1 | 1.944 (2) | C28—H28 | 0.9300 |
Cr1—O3 | 1.957 (2) | C29—C30 | 1.375 (6) |
Cr1—O5 | 1.931 (2) | C29—H29 | 0.9300 |
Cr1—N1 | 2.115 (3) | C30—H30 | 0.9300 |
Cr1—N2 | 2.090 (3) | C31—C36 | 1.370 (6) |
Cr1—N3 | 2.088 (3) | C31—C32 | 1.370 (6) |
Sn1—C31 | 2.124 (4) | C32—C33 | 1.407 (6) |
Sn1—C25 | 2.135 (3) | C32—H32 | 0.9300 |
Sn1—C19 | 2.143 (4) | C33—C34 | 1.360 (9) |
Sn1—O4 | 2.419 (2) | C33—H33 | 0.9300 |
Sn1—Cl1 | 2.4963 (11) | C34—C35 | 1.347 (9) |
Sn2—C13 | 2.119 (4) | C34—H34 | 0.9300 |
Sn2—C7 | 2.140 (4) | C35—C36 | 1.388 (7) |
Sn2—C1 | 2.143 (4) | C35—H35 | 0.9300 |
Sn2—O7 | 2.423 (3) | C36—H36 | 0.9300 |
Sn2—Cl2 | 2.4786 (11) | C37—N1 | 1.354 (4) |
C1—C6 | 1.373 (5) | C37—C38 | 1.360 (5) |
C1—C2 | 1.394 (5) | C37—C42 | 1.498 (5) |
C2—C3 | 1.382 (6) | C38—C39 | 1.384 (5) |
C2—H2 | 0.9300 | C38—H38 | 0.9300 |
C3—C4 | 1.332 (7) | C39—C40 | 1.347 (6) |
C3—H3 | 0.9300 | C39—H39 | 0.9300 |
C4—C5 | 1.355 (7) | C40—C41 | 1.391 (5) |
C4—H4 | 0.9300 | C40—H40 | 0.9300 |
C5—C6 | 1.396 (6) | C41—N1 | 1.353 (4) |
C5—H5 | 0.9300 | C41—C43 | 1.489 (5) |
C6—H6 | 0.9300 | C42—O2 | 1.221 (4) |
C7—C12 | 1.376 (5) | C42—O1 | 1.285 (4) |
C7—C8 | 1.392 (5) | C43—H43A | 0.9600 |
C8—C9 | 1.374 (6) | C43—H43B | 0.9600 |
C8—H8 | 0.9300 | C43—H43C | 0.9600 |
C9—C10 | 1.354 (7) | C44—N2 | 1.354 (4) |
C9—H9 | 0.9300 | C44—C45 | 1.363 (5) |
C10—C11 | 1.370 (7) | C44—C49 | 1.503 (5) |
C10—H10 | 0.9300 | C45—C46 | 1.384 (6) |
C11—C12 | 1.383 (6) | C45—H45 | 0.9300 |
C11—H11 | 0.9300 | C46—C47 | 1.351 (6) |
C12—H12 | 0.9300 | C46—H46 | 0.9300 |
C13—C14 | 1.377 (6) | C47—C48 | 1.395 (5) |
C13—C18 | 1.377 (6) | C47—H47 | 0.9300 |
C14—C15 | 1.392 (6) | C48—N2 | 1.347 (4) |
C14—H14 | 0.9300 | C48—C50 | 1.486 (5) |
C15—C16 | 1.366 (7) | C49—O4 | 1.235 (4) |
C15—H15 | 0.9300 | C49—O3 | 1.265 (4) |
C16—C17 | 1.351 (8) | C50—H50A | 0.9600 |
C16—H16 | 0.9300 | C50—H50B | 0.9600 |
C17—C18 | 1.384 (7) | C50—H50C | 0.9600 |
C17—H17 | 0.9300 | C51—N3 | 1.347 (4) |
C18—H18 | 0.9300 | C51—C52 | 1.382 (5) |
C19—C20 | 1.377 (5) | C51—C56 | 1.503 (5) |
C19—C24 | 1.388 (5) | C52—C53 | 1.370 (6) |
C20—C21 | 1.391 (6) | C52—H52 | 0.9300 |
C20—H20 | 0.9300 | C53—C54 | 1.359 (6) |
C21—C22 | 1.384 (7) | C53—H53 | 0.9300 |
C21—H21 | 0.9300 | C54—C55 | 1.387 (5) |
C22—C23 | 1.371 (7) | C54—H54 | 0.9300 |
C22—H22 | 0.9300 | C55—N3 | 1.346 (4) |
C23—C24 | 1.379 (6) | C55—C57 | 1.500 (5) |
C23—H23 | 0.9300 | C56—O6 | 1.210 (4) |
C24—H24 | 0.9300 | C56—O5 | 1.293 (4) |
C25—C30 | 1.375 (5) | C57—H57A | 0.9600 |
C25—C26 | 1.383 (5) | C57—H57B | 0.9600 |
C26—C27 | 1.377 (6) | C57—H57C | 0.9600 |
C26—H26 | 0.9300 | C58—O7 | 1.522 (12) |
C27—C28 | 1.378 (7) | C59—O7 | 1.469 (11) |
C27—H27 | 0.9300 | O7—H7O | 0.873 (18) |
C28—C29 | 1.347 (7) | ||
O5—Cr1—O1 | 87.58 (10) | C29—C28—H28 | 120.3 |
O5—Cr1—O3 | 91.03 (11) | C27—C28—H28 | 120.3 |
O1—Cr1—O3 | 175.81 (10) | C28—C29—C30 | 120.5 (4) |
O5—Cr1—N3 | 81.46 (10) | C28—C29—H29 | 119.8 |
O1—Cr1—N3 | 85.98 (10) | C30—C29—H29 | 119.8 |
O3—Cr1—N3 | 89.91 (10) | C29—C30—C25 | 121.5 (4) |
O5—Cr1—N2 | 86.46 (10) | C29—C30—H30 | 119.2 |
O1—Cr1—N2 | 103.20 (10) | C25—C30—H30 | 119.2 |
O3—Cr1—N2 | 80.64 (10) | C36—C31—C32 | 118.1 (4) |
N3—Cr1—N2 | 164.53 (11) | C36—C31—Sn1 | 120.3 (3) |
O5—Cr1—N1 | 167.22 (11) | C32—C31—Sn1 | 121.6 (3) |
O1—Cr1—N1 | 79.85 (10) | C31—C32—C33 | 121.5 (5) |
O3—Cr1—N1 | 101.67 (11) | C31—C32—H32 | 119.3 |
N3—Cr1—N1 | 99.81 (10) | C33—C32—H32 | 119.3 |
N2—Cr1—N1 | 94.11 (10) | C34—C33—C32 | 117.9 (6) |
C31—Sn1—C25 | 121.44 (16) | C34—C33—H33 | 121.0 |
C31—Sn1—C19 | 124.04 (15) | C32—C33—H33 | 121.0 |
C25—Sn1—C19 | 112.05 (14) | C35—C34—C33 | 121.8 (6) |
C31—Sn1—O4 | 85.42 (12) | C35—C34—H34 | 119.1 |
C25—Sn1—O4 | 82.19 (11) | C33—C34—H34 | 119.1 |
C19—Sn1—O4 | 86.64 (13) | C34—C35—C36 | 119.7 (7) |
C31—Sn1—Cl1 | 93.88 (11) | C34—C35—H35 | 120.2 |
C25—Sn1—Cl1 | 97.77 (10) | C36—C35—H35 | 120.2 |
C19—Sn1—Cl1 | 94.17 (11) | C31—C36—C35 | 121.0 (6) |
O4—Sn1—Cl1 | 179.14 (7) | C31—C36—H36 | 119.5 |
C13—Sn2—C7 | 118.75 (15) | C35—C36—H36 | 119.5 |
C13—Sn2—C1 | 120.07 (14) | N1—C37—C38 | 123.4 (3) |
C7—Sn2—C1 | 119.49 (14) | N1—C37—C42 | 114.8 (3) |
C13—Sn2—O7 | 82.03 (12) | C38—C37—C42 | 121.7 (3) |
C7—Sn2—O7 | 87.40 (12) | C37—C38—C39 | 118.3 (4) |
C1—Sn2—O7 | 87.59 (13) | C37—C38—H38 | 120.8 |
C13—Sn2—Cl2 | 93.19 (10) | C39—C38—H38 | 120.8 |
C7—Sn2—Cl2 | 95.15 (10) | C40—C39—C38 | 119.1 (4) |
C1—Sn2—Cl2 | 94.65 (10) | C40—C39—H39 | 120.5 |
O7—Sn2—Cl2 | 175.21 (7) | C38—C39—H39 | 120.5 |
C6—C1—C2 | 117.3 (4) | C39—C40—C41 | 120.8 (4) |
C6—C1—Sn2 | 121.2 (3) | C39—C40—H40 | 119.6 |
C2—C1—Sn2 | 121.5 (3) | C41—C40—H40 | 119.6 |
C3—C2—C1 | 121.2 (4) | N1—C41—C40 | 120.4 (3) |
C3—C2—H2 | 119.4 | N1—C41—C43 | 119.2 (3) |
C1—C2—H2 | 119.4 | C40—C41—C43 | 120.4 (3) |
C4—C3—C2 | 120.6 (5) | O2—C42—O1 | 124.7 (3) |
C4—C3—H3 | 119.7 | O2—C42—C37 | 120.4 (3) |
C2—C3—H3 | 119.7 | O1—C42—C37 | 114.9 (3) |
C3—C4—C5 | 119.7 (5) | C41—C43—H43A | 109.5 |
C3—C4—H4 | 120.2 | C41—C43—H43B | 109.5 |
C5—C4—H4 | 120.2 | H43A—C43—H43B | 109.5 |
C4—C5—C6 | 121.3 (5) | C41—C43—H43C | 109.5 |
C4—C5—H5 | 119.3 | H43A—C43—H43C | 109.5 |
C6—C5—H5 | 119.3 | H43B—C43—H43C | 109.5 |
C1—C6—C5 | 119.8 (4) | N2—C44—C45 | 123.2 (3) |
C1—C6—H6 | 120.1 | N2—C44—C49 | 114.5 (3) |
C5—C6—H6 | 120.1 | C45—C44—C49 | 122.2 (3) |
C12—C7—C8 | 118.1 (4) | C44—C45—C46 | 118.0 (4) |
C12—C7—Sn2 | 122.9 (3) | C44—C45—H45 | 121.0 |
C8—C7—Sn2 | 118.9 (3) | C46—C45—H45 | 121.0 |
C9—C8—C7 | 120.8 (4) | C47—C46—C45 | 119.5 (4) |
C9—C8—H8 | 119.6 | C47—C46—H46 | 120.2 |
C7—C8—H8 | 119.6 | C45—C46—H46 | 120.2 |
C10—C9—C8 | 119.9 (5) | C46—C47—C48 | 120.8 (4) |
C10—C9—H9 | 120.1 | C46—C47—H47 | 119.6 |
C8—C9—H9 | 120.1 | C48—C47—H47 | 119.6 |
C9—C10—C11 | 120.9 (5) | N2—C48—C47 | 119.7 (3) |
C9—C10—H10 | 119.6 | N2—C48—C50 | 119.8 (3) |
C11—C10—H10 | 119.6 | C47—C48—C50 | 120.6 (3) |
C10—C11—C12 | 119.4 (5) | O4—C49—O3 | 125.6 (3) |
C10—C11—H11 | 120.3 | O4—C49—C44 | 118.3 (3) |
C12—C11—H11 | 120.3 | O3—C49—C44 | 115.9 (3) |
C7—C12—C11 | 120.9 (4) | C48—C50—H50A | 109.5 |
C7—C12—H12 | 119.5 | C48—C50—H50B | 109.5 |
C11—C12—H12 | 119.5 | H50A—C50—H50B | 109.5 |
C14—C13—C18 | 117.8 (4) | C48—C50—H50C | 109.5 |
C14—C13—Sn2 | 120.8 (3) | H50A—C50—H50C | 109.5 |
C18—C13—Sn2 | 121.4 (3) | H50B—C50—H50C | 109.5 |
C13—C14—C15 | 121.0 (5) | N3—C51—C52 | 121.8 (3) |
C13—C14—H14 | 119.5 | N3—C51—C56 | 116.3 (3) |
C15—C14—H14 | 119.5 | C52—C51—C56 | 121.9 (3) |
C14—C15—C16 | 120.3 (5) | C53—C52—C51 | 118.4 (4) |
C14—C15—H15 | 119.9 | C53—C52—H52 | 120.8 |
C16—C15—H15 | 119.9 | C51—C52—H52 | 120.8 |
C17—C16—C15 | 118.5 (5) | C54—C53—C52 | 119.9 (4) |
C17—C16—H16 | 120.7 | C54—C53—H53 | 120.1 |
C15—C16—H16 | 120.7 | C52—C53—H53 | 120.1 |
C16—C17—C18 | 122.2 (5) | C53—C54—C55 | 120.0 (4) |
C16—C17—H17 | 118.9 | C53—C54—H54 | 120.0 |
C18—C17—H17 | 118.9 | C55—C54—H54 | 120.0 |
C17—C18—C13 | 119.9 (5) | N3—C55—C54 | 120.3 (3) |
C17—C18—H18 | 120.0 | N3—C55—C57 | 118.9 (3) |
C13—C18—H18 | 120.0 | C54—C55—C57 | 120.8 (3) |
C20—C19—C24 | 119.4 (4) | O6—C56—O5 | 125.1 (3) |
C20—C19—Sn1 | 119.9 (3) | O6—C56—C51 | 120.8 (3) |
C24—C19—Sn1 | 120.7 (3) | O5—C56—C51 | 114.0 (3) |
C19—C20—C21 | 120.3 (4) | C55—C57—H57A | 109.5 |
C19—C20—H20 | 119.9 | C55—C57—H57B | 109.5 |
C21—C20—H20 | 119.9 | H57A—C57—H57B | 109.5 |
C22—C21—C20 | 119.3 (5) | C55—C57—H57C | 109.5 |
C22—C21—H21 | 120.3 | H57A—C57—H57C | 109.5 |
C20—C21—H21 | 120.3 | H57B—C57—H57C | 109.5 |
C23—C22—C21 | 120.7 (5) | C41—N1—C37 | 117.6 (3) |
C23—C22—H22 | 119.6 | C41—N1—Cr1 | 132.4 (2) |
C21—C22—H22 | 119.6 | C37—N1—Cr1 | 109.8 (2) |
C22—C23—C24 | 119.6 (5) | C48—N2—C44 | 118.7 (3) |
C22—C23—H23 | 120.2 | C48—N2—Cr1 | 132.2 (2) |
C24—C23—H23 | 120.2 | C44—N2—Cr1 | 108.3 (2) |
C23—C24—C19 | 120.7 (5) | C55—N3—C51 | 119.3 (3) |
C23—C24—H24 | 119.7 | C55—N3—Cr1 | 132.7 (2) |
C19—C24—H24 | 119.7 | C51—N3—Cr1 | 107.8 (2) |
C30—C25—C26 | 117.6 (4) | C42—O1—Cr1 | 118.5 (2) |
C30—C25—Sn1 | 123.8 (3) | C49—O3—Cr1 | 115.2 (2) |
C26—C25—Sn1 | 118.5 (3) | C49—O4—Sn1 | 130.9 (2) |
C27—C26—C25 | 120.6 (4) | C56—O5—Cr1 | 115.5 (2) |
C27—C26—H26 | 119.7 | C59—O7—Sn2 | 122.6 (5) |
C25—C26—H26 | 119.7 | C58—O7—Sn2 | 131.2 (5) |
C28—C27—C26 | 120.3 (5) | C59—O7—H7O | 113 (2) |
C28—C27—H27 | 119.8 | C58—O7—H7O | 109 (2) |
C26—C27—H27 | 119.8 | Sn2—O7—H7O | 115.9 (19) |
C29—C28—C27 | 119.4 (4) | ||
C13—Sn2—C1—C6 | 58.8 (3) | C38—C37—C42—O1 | 178.7 (3) |
C7—Sn2—C1—C6 | −136.2 (3) | N2—C44—C45—C46 | −1.7 (6) |
O7—Sn2—C1—C6 | 138.1 (3) | C49—C44—C45—C46 | 173.7 (4) |
Cl2—Sn2—C1—C6 | −37.6 (3) | C44—C45—C46—C47 | 0.1 (7) |
C13—Sn2—C1—C2 | −123.8 (3) | C45—C46—C47—C48 | 0.3 (7) |
C7—Sn2—C1—C2 | 41.2 (3) | C46—C47—C48—N2 | 0.8 (6) |
O7—Sn2—C1—C2 | −44.4 (3) | C46—C47—C48—C50 | −178.6 (4) |
Cl2—Sn2—C1—C2 | 139.8 (3) | N2—C44—C49—O4 | 176.3 (3) |
C6—C1—C2—C3 | 0.6 (6) | C45—C44—C49—O4 | 0.6 (5) |
Sn2—C1—C2—C3 | −176.9 (3) | N2—C44—C49—O3 | −0.7 (4) |
C1—C2—C3—C4 | −0.1 (7) | C45—C44—C49—O3 | −176.4 (3) |
C2—C3—C4—C5 | −0.1 (8) | N3—C51—C52—C53 | 0.8 (6) |
C3—C4—C5—C6 | −0.2 (7) | C56—C51—C52—C53 | −176.6 (4) |
C2—C1—C6—C5 | −0.9 (5) | C51—C52—C53—C54 | 3.4 (7) |
Sn2—C1—C6—C5 | 176.7 (3) | C52—C53—C54—C55 | −3.6 (7) |
C4—C5—C6—C1 | 0.7 (6) | C53—C54—C55—N3 | −0.4 (7) |
C13—Sn2—C7—C12 | 43.0 (3) | C53—C54—C55—C57 | 177.6 (4) |
C1—Sn2—C7—C12 | −122.2 (3) | N3—C51—C56—O6 | 178.6 (4) |
O7—Sn2—C7—C12 | −36.5 (3) | C52—C51—C56—O6 | −3.9 (6) |
Cl2—Sn2—C7—C12 | 139.5 (3) | N3—C51—C56—O5 | −3.8 (5) |
C13—Sn2—C7—C8 | −132.8 (3) | C52—C51—C56—O5 | 173.7 (4) |
C1—Sn2—C7—C8 | 62.0 (3) | C40—C41—N1—C37 | −4.4 (5) |
O7—Sn2—C7—C8 | 147.7 (3) | C43—C41—N1—C37 | 174.5 (3) |
Cl2—Sn2—C7—C8 | −36.3 (3) | C40—C41—N1—Cr1 | 169.7 (3) |
C12—C7—C8—C9 | −1.3 (6) | C43—C41—N1—Cr1 | −11.4 (5) |
Sn2—C7—C8—C9 | 174.7 (3) | C38—C37—N1—C41 | 5.3 (5) |
C7—C8—C9—C10 | −0.6 (7) | C42—C37—N1—C41 | −171.7 (3) |
C8—C9—C10—C11 | 1.8 (8) | C38—C37—N1—Cr1 | −170.1 (3) |
C9—C10—C11—C12 | −1.0 (7) | C42—C37—N1—Cr1 | 12.9 (3) |
C8—C7—C12—C11 | 2.0 (6) | O5—Cr1—N1—C41 | 161.7 (4) |
Sn2—C7—C12—C11 | −173.8 (3) | O1—Cr1—N1—C41 | 172.3 (3) |
C10—C11—C12—C7 | −0.9 (6) | O3—Cr1—N1—C41 | −11.7 (3) |
C7—Sn2—C13—C14 | 6.6 (4) | N3—Cr1—N1—C41 | −103.6 (3) |
C1—Sn2—C13—C14 | 171.7 (3) | N2—Cr1—N1—C41 | 69.6 (3) |
O7—Sn2—C13—C14 | 89.2 (3) | O5—Cr1—N1—C37 | −23.8 (6) |
Cl2—Sn2—C13—C14 | −91.1 (3) | O1—Cr1—N1—C37 | −13.2 (2) |
C7—Sn2—C13—C18 | −174.6 (4) | O3—Cr1—N1—C37 | 162.8 (2) |
C1—Sn2—C13—C18 | −9.5 (4) | N3—Cr1—N1—C37 | 70.9 (2) |
O7—Sn2—C13—C18 | −92.0 (4) | N2—Cr1—N1—C37 | −115.9 (2) |
Cl2—Sn2—C13—C18 | 87.7 (4) | C47—C48—N2—C44 | −2.4 (5) |
C18—C13—C14—C15 | 4.6 (7) | C50—C48—N2—C44 | 177.1 (3) |
Sn2—C13—C14—C15 | −176.6 (4) | C47—C48—N2—Cr1 | 166.1 (3) |
C13—C14—C15—C16 | −1.2 (8) | C50—C48—N2—Cr1 | −14.4 (5) |
C14—C15—C16—C17 | −1.3 (9) | C45—C44—N2—C48 | 2.9 (5) |
C15—C16—C17—C18 | 0.3 (10) | C49—C44—N2—C48 | −172.8 (3) |
C16—C17—C18—C13 | 3.1 (10) | C45—C44—N2—Cr1 | −168.1 (3) |
C14—C13—C18—C17 | −5.4 (8) | C49—C44—N2—Cr1 | 16.2 (3) |
Sn2—C13—C18—C17 | 175.8 (5) | O5—Cr1—N2—C48 | −97.0 (3) |
C31—Sn1—C19—C20 | 113.4 (3) | O1—Cr1—N2—C48 | −10.4 (3) |
C25—Sn1—C19—C20 | −49.0 (3) | O3—Cr1—N2—C48 | 171.3 (3) |
O4—Sn1—C19—C20 | 31.2 (3) | N3—Cr1—N2—C48 | −135.6 (4) |
Cl1—Sn1—C19—C20 | −149.1 (3) | N1—Cr1—N2—C48 | 70.2 (3) |
C31—Sn1—C19—C24 | −69.9 (3) | O5—Cr1—N2—C44 | 72.3 (2) |
C25—Sn1—C19—C24 | 127.8 (3) | O1—Cr1—N2—C44 | 159.0 (2) |
O4—Sn1—C19—C24 | −152.0 (3) | O3—Cr1—N2—C44 | −19.3 (2) |
Cl1—Sn1—C19—C24 | 27.7 (3) | N3—Cr1—N2—C44 | 33.7 (5) |
C24—C19—C20—C21 | 0.6 (6) | N1—Cr1—N2—C44 | −120.5 (2) |
Sn1—C19—C20—C21 | 177.4 (3) | C54—C55—N3—C51 | 4.5 (5) |
C19—C20—C21—C22 | −0.5 (6) | C57—C55—N3—C51 | −173.5 (3) |
C20—C21—C22—C23 | −0.4 (7) | C54—C55—N3—Cr1 | −169.5 (3) |
C21—C22—C23—C24 | 1.4 (7) | C57—C55—N3—Cr1 | 12.6 (5) |
C22—C23—C24—C19 | −1.3 (7) | C52—C51—N3—C55 | −4.7 (5) |
C20—C19—C24—C23 | 0.3 (6) | C56—C51—N3—C55 | 172.8 (3) |
Sn1—C19—C24—C23 | −176.4 (3) | C52—C51—N3—Cr1 | 170.6 (3) |
C31—Sn1—C25—C30 | −40.1 (4) | C56—C51—N3—Cr1 | −11.9 (4) |
C19—Sn1—C25—C30 | 122.7 (3) | O5—Cr1—N3—C55 | −168.6 (3) |
O4—Sn1—C25—C30 | 39.6 (3) | O1—Cr1—N3—C55 | 103.3 (3) |
Cl1—Sn1—C25—C30 | −139.5 (3) | O3—Cr1—N3—C55 | −77.5 (3) |
C31—Sn1—C25—C26 | 142.4 (3) | N2—Cr1—N3—C55 | −129.5 (4) |
C19—Sn1—C25—C26 | −54.8 (3) | N1—Cr1—N3—C55 | 24.3 (3) |
O4—Sn1—C25—C26 | −137.9 (3) | O5—Cr1—N3—C51 | 17.0 (2) |
Cl1—Sn1—C25—C26 | 43.0 (3) | O1—Cr1—N3—C51 | −71.2 (2) |
C30—C25—C26—C27 | −0.4 (6) | O3—Cr1—N3—C51 | 108.0 (2) |
Sn1—C25—C26—C27 | 177.2 (4) | N2—Cr1—N3—C51 | 56.0 (5) |
C25—C26—C27—C28 | 0.4 (8) | N1—Cr1—N3—C51 | −150.1 (2) |
C26—C27—C28—C29 | −0.4 (9) | O2—C42—O1—Cr1 | 173.3 (3) |
C27—C28—C29—C30 | 0.3 (8) | C37—C42—O1—Cr1 | −8.2 (4) |
C28—C29—C30—C25 | −0.3 (7) | O5—Cr1—O1—C42 | −170.4 (2) |
C26—C25—C30—C29 | 0.4 (6) | N3—Cr1—O1—C42 | −88.8 (2) |
Sn1—C25—C30—C29 | −177.1 (3) | N2—Cr1—O1—C42 | 103.8 (2) |
C25—Sn1—C31—C36 | 16.1 (4) | N1—Cr1—O1—C42 | 12.0 (2) |
C19—Sn1—C31—C36 | −144.7 (4) | O4—C49—O3—Cr1 | 166.1 (3) |
O4—Sn1—C31—C36 | −61.8 (4) | C44—C49—O3—Cr1 | −17.1 (4) |
Cl1—Sn1—C31—C36 | 117.7 (4) | O5—Cr1—O3—C49 | −65.8 (2) |
C25—Sn1—C31—C32 | −165.1 (3) | N3—Cr1—O3—C49 | −147.3 (2) |
C19—Sn1—C31—C32 | 34.2 (4) | N2—Cr1—O3—C49 | 20.4 (2) |
O4—Sn1—C31—C32 | 117.0 (3) | N1—Cr1—O3—C49 | 112.7 (2) |
Cl1—Sn1—C31—C32 | −63.5 (3) | O3—C49—O4—Sn1 | 22.9 (5) |
C36—C31—C32—C33 | 1.0 (7) | C44—C49—O4—Sn1 | −153.8 (2) |
Sn1—C31—C32—C33 | −177.9 (3) | C31—Sn1—O4—C49 | −57.0 (3) |
C31—C32—C33—C34 | 0.6 (8) | C25—Sn1—O4—C49 | −179.6 (3) |
C32—C33—C34—C35 | −1.7 (10) | C19—Sn1—O4—C49 | 67.5 (3) |
C33—C34—C35—C36 | 1.3 (11) | O6—C56—O5—Cr1 | −162.9 (3) |
C32—C31—C36—C35 | −1.5 (8) | C51—C56—O5—Cr1 | 19.6 (4) |
Sn1—C31—C36—C35 | 177.4 (5) | O1—Cr1—O5—C56 | 65.6 (3) |
C34—C35—C36—C31 | 0.4 (10) | O3—Cr1—O5—C56 | −110.5 (3) |
N1—C37—C38—C39 | −0.8 (6) | N3—Cr1—O5—C56 | −20.7 (3) |
C42—C37—C38—C39 | 176.0 (4) | N2—Cr1—O5—C56 | 169.0 (3) |
C37—C38—C39—C40 | −4.6 (6) | N1—Cr1—O5—C56 | 76.0 (5) |
C38—C39—C40—C41 | 5.4 (6) | C13—Sn2—O7—C59 | 37.2 (10) |
C39—C40—C41—N1 | −0.8 (6) | C7—Sn2—O7—C59 | 156.7 (10) |
C39—C40—C41—C43 | −179.7 (4) | C1—Sn2—O7—C59 | −83.6 (10) |
N1—C37—C42—O2 | 174.3 (3) | C13—Sn2—O7—C58 | −24.7 (9) |
C38—C37—C42—O2 | −2.7 (6) | C7—Sn2—O7—C58 | 94.8 (9) |
N1—C37—C42—O1 | −4.2 (4) | C1—Sn2—O7—C58 | −145.5 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7O···O2 | 0.87 (2) | 1.87 (2) | 2.714 (4) | 163 (3) |
C39—H39···Cl1i | 0.93 | 2.78 | 3.702 (4) | 169 |
C40—H40···Cl2ii | 0.93 | 2.90 | 3.730 (4) | 150 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [CrSn(C6H5)3(C7H6NO2)3Cl][Sn(C6H5)3Cl(CH4O)] |
Mr | 1263.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 12.767 (5), 14.095 (5), 15.967 (5) |
α, β, γ (°) | 96.122 (5), 91.784 (5), 94.944 (5) |
V (Å3) | 2843.9 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.21 |
Crystal size (mm) | 0.52 × 0.40 × 0.32 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.228, 0.303 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11436, 9854, 7137 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.070, 0.88 |
No. of reflections | 9854 |
No. of parameters | 673 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.60, −0.36 |
Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1994), SHELXL97.
Cr1—O1 | 1.944 (2) | Cr1—N3 | 2.088 (3) |
Cr1—O3 | 1.957 (2) | Sn1—O4 | 2.419 (2) |
Cr1—O5 | 1.931 (2) | Sn1—Cl1 | 2.4963 (11) |
Cr1—N1 | 2.115 (3) | Sn2—O7 | 2.423 (3) |
Cr1—N2 | 2.090 (3) | Sn2—Cl2 | 2.4786 (11) |
O4—Sn1—Cl1 | 179.14 (7) | O7—Sn2—Cl2 | 175.21 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7O···O2 | 0.873 (18) | 1.87 (2) | 2.714 (4) | 163 (3) |
C39—H39···Cl1i | 0.93 | 2.78 | 3.702 (4) | 169.1 |
C40—H40···Cl2ii | 0.93 | 2.90 | 3.730 (4) | 149.8 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z. |
Organotin compounds have attracted much interest, not only because of their applications as catalysts in organic reactions (Orita et al., 1998), but also for use in medicinal chemistry (Arakawa, 1998). For example, the triorganotin compounds, R3SnX, have been known for several years as having a specific action on mitochondrial oxidative phosphorylation (Barnes & Magos, 1968). To the best of our knowledge, little attention (Döring et al., 1997; Yang et al., 2006) has been given to heterobimetallic organotin compounds. It is known that R3Sn+ cations usually prefer a trigonal–bipyramidal (tbp) configuration. Thus, triorganotin compounds are good Lewis acids, despite the fact that they carry three R groups. Given the Lewis acidity of triorganotin compounds, a complex with surplus coordinating atoms can react with triphenyltin to form an adduct. We report here the crystal structure of such a compound, [Ph3SnClCr(C7H6NO2)3][Ph3SnClMeOH], (I).
As shown in Fig. 1, compound (I) possesses two kinds of molecules, [Ph3SnClMeOH] (A) and [Ph3SnClCr(C7H6NO2)3] (B). In molecule A, the Sn atom of Ph3SnCl is coordinated by one methanol molecule, the C atom of which is disordered over two positions with unequal populations for each orientation (the ratio of the occupancies of C58–C59 is 1.27:1). Molecule B contains Ph3SnCl which is coordinated by one carboxylate O atom of a [Cr(C7H6NO2)3] fragment. In the latter, the Cr centre is six-coordinated by N and O atoms of three 6-methylpyridine-2-carboxylate anions, displaying a distorted octahedral configuration. The three N atoms are meridional, as are the three O atoms.
Each Sn atom of (I) shows a trans-ClSn(R3)O trigonal–bipyramidal coordination environment, with three phenyl groups in equatorial positions (C19, C25 and C31 for Sn1, and C1, C7 and C13 for Sn2) and Cl and O atoms in axial positions (Cl1 and O4 for Sn1, and Cl2 and O7 for Sn2). The axial-O—Sn—axial-Cl angles are 179.14 (7) (O4—Sn1—Cl1) and 175.21 (7)° (O7—Sn2—Cl2), so the structures can be described as slightly distorted trigonal bipyramids. Molecules A and B are connected through an O—H···O hydrogen bond between the carboxylate O atom and the hydroxyl H atom of methanol.
In the complex [Cr(C7H6NO2)3], the Cr—O distances of 1.944 (2), 1.957 (2) and 1.931 (2) Å are near the values found in other chromium complexes with pyridine-2-carboxylate (Steams & Armsbong, 1992). However, the Cr—N distances of 2.115 (3), 2.090 (3) and 2.088 (3) Å are somewhat longer. The Sn—O bond distances of (I) are longer than the value found in (Ph3Sn)2O (1.955 Å; Glidewell & Liles, 1978), but shorter than the value in [Sn2(C6H5)6(C8H4O4)] (2.724 Å; Zhang et al., 2006). The Sn—Cl bond distances are significantly longer than those found for Ph3SnCl (2.321 and 2.315 Å; Bokii et al., 1970).
As shown in Fig. 2 and Table 2, molecules B form a one-dimensional zigzag chain via weak C—H···Cl interactions between the C atoms of the pyridine rings and Cl anions bound to Sn atoms. Adjacent one-dimensional chains are parallel to each other. The zigzag chains are connected together through O—H···O hydrogen bonds and weak C—H···Cl interactions between molecules A and B to form a two-dimensional network. There are no π–π interactions between the aromatic rings in the structure of (I).
The molecular structure of (I) can be viewed as a donor–acceptor adduct, in which the electron-rich Cr complex interacts with the electrophilic Sn centre, without causing the loss of Cl− anions. It can be predicted that the Lewis acidity of organotin can facilitate the formation of adducts. Thus, it is conceivable that compounds with new properties can be prepared by introducing a second metal into organotin compounds.