Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062307/dn2284sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062307/dn2284Isup2.hkl |
CCDC reference: 672773
The reaction was carried out under nitrogen atmosphere. o-vanillin 4-chlorobenzhydrazone(1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of benzene(30 ml) in a Schlenk flask and stirred for 0.5 h. Diphenyltin dichloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 4 h at 313 K·The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1)·Analysis calculated for C27H21ClN2O3Sn (Mr = 575.63): C, 56.34; H, 3.68; N, 4.87, found: C, 56.28; H, 3.61; N, 4.95.
All H atoms attached to C atoms were fixed geometrically and treated as riding with aromatic C—H distances of 0.93 Å, methyl C—H distances of 0.96 Å. The Uiso(H) values were set at 1.5Uiso(C) for the methyl H atoms, and at 1.2Uiso(C) for the other H atoms.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity. |
[Sn(C6H5)2(C15H11ClN2O3)] | F(000) = 2304 |
Mr = 575.60 | Dx = 1.554 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4610 reflections |
a = 19.178 (2) Å | θ = 2.3–27.3° |
b = 27.968 (3) Å | µ = 1.18 mm−1 |
c = 9.4230 (13) Å | T = 298 K |
β = 103.238 (2)° | Block, orange |
V = 4920.1 (10) Å3 | 0.37 × 0.17 × 0.12 mm |
Z = 8 |
CCD area-detector diffractometer | 8658 independent reflections |
Radiation source: fine-focus sealed tube | 5197 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→22 |
Tmin = 0.670, Tmax = 0.872 | k = −25→33 |
20342 measured reflections | l = −10→11 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0253P)2 + 2.1263P] where P = (Fo2 + 2Fc2)/3 |
8658 reflections | (Δ/σ)max = 0.002 |
615 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
[Sn(C6H5)2(C15H11ClN2O3)] | V = 4920.1 (10) Å3 |
Mr = 575.60 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.178 (2) Å | µ = 1.18 mm−1 |
b = 27.968 (3) Å | T = 298 K |
c = 9.4230 (13) Å | 0.37 × 0.17 × 0.12 mm |
β = 103.238 (2)° |
CCD area-detector diffractometer | 8658 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5197 reflections with I > 2σ(I) |
Tmin = 0.670, Tmax = 0.872 | Rint = 0.045 |
20342 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.54 e Å−3 |
8658 reflections | Δρmin = −0.76 e Å−3 |
615 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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.144802 (18) | 0.519068 (13) | 0.41711 (4) | 0.04606 (12) | |
Sn2 | 0.501802 (19) | 0.854204 (13) | 0.48215 (4) | 0.05022 (13) | |
Cl1 | 0.12874 (10) | 0.25504 (6) | 0.9118 (2) | 0.1020 (6) | |
Cl2 | 0.14114 (9) | 0.77336 (6) | 0.8586 (2) | 0.0956 (6) | |
N1 | 0.0499 (2) | 0.47593 (15) | 0.3566 (5) | 0.0479 (11) | |
N2 | 0.0496 (2) | 0.43350 (15) | 0.4343 (5) | 0.0559 (12) | |
N3 | 0.4951 (2) | 0.78151 (15) | 0.5491 (5) | 0.0497 (12) | |
N4 | 0.4407 (2) | 0.77048 (15) | 0.6197 (5) | 0.0547 (12) | |
O1 | 0.15977 (18) | 0.45977 (12) | 0.5633 (4) | 0.0584 (10) | |
O2 | 0.09344 (17) | 0.56387 (12) | 0.2515 (4) | 0.0527 (10) | |
O3 | 0.05732 (19) | 0.63653 (14) | 0.0770 (4) | 0.0699 (12) | |
O4 | 0.40729 (17) | 0.84888 (13) | 0.5635 (4) | 0.0620 (11) | |
O5 | 0.59883 (17) | 0.83215 (13) | 0.4450 (4) | 0.0575 (10) | |
O6 | 0.7019 (2) | 0.82949 (16) | 0.3078 (5) | 0.0771 (12) | |
C1 | 0.1073 (3) | 0.4291 (2) | 0.5375 (6) | 0.0484 (14) | |
C2 | 0.1135 (3) | 0.3856 (2) | 0.6272 (6) | 0.0508 (14) | |
C3 | 0.0614 (3) | 0.3497 (2) | 0.5990 (7) | 0.0724 (18) | |
H3 | 0.0224 | 0.3526 | 0.5201 | 0.087* | |
C4 | 0.0673 (4) | 0.3101 (2) | 0.6865 (8) | 0.0750 (19) | |
H4 | 0.0325 | 0.2864 | 0.6663 | 0.090* | |
C5 | 0.1236 (4) | 0.3053 (2) | 0.8025 (8) | 0.0665 (18) | |
C6 | 0.1762 (3) | 0.3391 (2) | 0.8317 (7) | 0.0737 (19) | |
H6 | 0.2155 | 0.3351 | 0.9095 | 0.088* | |
C7 | 0.1706 (3) | 0.3793 (2) | 0.7444 (7) | 0.0630 (16) | |
H7 | 0.2061 | 0.4026 | 0.7654 | 0.076* | |
C8 | −0.0062 (3) | 0.48431 (19) | 0.2528 (6) | 0.0520 (14) | |
H8 | −0.0416 | 0.4609 | 0.2375 | 0.062* | |
C9 | −0.0202 (3) | 0.52482 (19) | 0.1600 (5) | 0.0439 (13) | |
C10 | 0.0286 (3) | 0.56267 (19) | 0.1631 (6) | 0.0472 (14) | |
C11 | 0.0074 (3) | 0.6005 (2) | 0.0660 (6) | 0.0484 (14) | |
C12 | −0.0584 (3) | 0.6004 (2) | −0.0299 (6) | 0.0636 (17) | |
H12 | −0.0715 | 0.6258 | −0.0941 | 0.076* | |
C13 | −0.1056 (3) | 0.5626 (2) | −0.0319 (7) | 0.0667 (17) | |
H13 | −0.1501 | 0.5628 | −0.0969 | 0.080* | |
C14 | −0.0870 (3) | 0.5258 (2) | 0.0593 (6) | 0.0562 (15) | |
H14 | −0.1187 | 0.5004 | 0.0563 | 0.067* | |
C15 | 0.0361 (3) | 0.6782 (2) | −0.0083 (7) | 0.089 (2) | |
H15A | 0.0290 | 0.6703 | −0.1098 | 0.133* | |
H15B | 0.0728 | 0.7021 | 0.0168 | 0.133* | |
H15C | −0.0078 | 0.6903 | 0.0105 | 0.133* | |
C16 | 0.1542 (2) | 0.57022 (19) | 0.5832 (6) | 0.0425 (13) | |
C17 | 0.1312 (3) | 0.6159 (2) | 0.5540 (6) | 0.0654 (17) | |
H17 | 0.1108 | 0.6247 | 0.4584 | 0.078* | |
C18 | 0.1376 (4) | 0.6494 (2) | 0.6643 (8) | 0.084 (2) | |
H18 | 0.1214 | 0.6805 | 0.6423 | 0.101* | |
C19 | 0.1677 (4) | 0.6372 (2) | 0.8048 (7) | 0.0751 (19) | |
H19 | 0.1721 | 0.6597 | 0.8789 | 0.090* | |
C20 | 0.1911 (3) | 0.5918 (3) | 0.8352 (7) | 0.080 (2) | |
H20 | 0.2110 | 0.5830 | 0.9312 | 0.096* | |
C21 | 0.1858 (3) | 0.5588 (2) | 0.7265 (7) | 0.0636 (17) | |
H21 | 0.2037 | 0.5282 | 0.7491 | 0.076* | |
C22 | 0.2308 (3) | 0.5003 (2) | 0.3235 (6) | 0.0464 (13) | |
C23 | 0.2741 (3) | 0.4618 (2) | 0.3749 (7) | 0.0796 (19) | |
H23 | 0.2664 | 0.4440 | 0.4534 | 0.096* | |
C24 | 0.3291 (4) | 0.4496 (3) | 0.3086 (10) | 0.112 (3) | |
H24 | 0.3578 | 0.4233 | 0.3425 | 0.134* | |
C25 | 0.3419 (4) | 0.4752 (3) | 0.1961 (9) | 0.100 (3) | |
H25 | 0.3793 | 0.4666 | 0.1533 | 0.120* | |
C26 | 0.3006 (4) | 0.5131 (3) | 0.1460 (8) | 0.090 (2) | |
H26 | 0.3095 | 0.5309 | 0.0688 | 0.108* | |
C27 | 0.2453 (3) | 0.5254 (2) | 0.2085 (7) | 0.0681 (17) | |
H27 | 0.2167 | 0.5516 | 0.1720 | 0.082* | |
C28 | 0.3999 (3) | 0.8073 (2) | 0.6217 (6) | 0.0497 (14) | |
C29 | 0.3380 (3) | 0.80035 (18) | 0.6884 (6) | 0.0450 (13) | |
C30 | 0.2846 (3) | 0.83445 (19) | 0.6718 (6) | 0.0517 (15) | |
H30 | 0.2893 | 0.8629 | 0.6237 | 0.062* | |
C31 | 0.2243 (3) | 0.82690 (19) | 0.7259 (6) | 0.0546 (15) | |
H31 | 0.1885 | 0.8500 | 0.7147 | 0.065* | |
C32 | 0.2182 (3) | 0.7847 (2) | 0.7965 (6) | 0.0587 (16) | |
C33 | 0.2704 (3) | 0.7508 (2) | 0.8147 (7) | 0.0763 (19) | |
H33 | 0.2657 | 0.7225 | 0.8632 | 0.092* | |
C34 | 0.3297 (3) | 0.7589 (2) | 0.7611 (7) | 0.0689 (18) | |
H34 | 0.3653 | 0.7357 | 0.7740 | 0.083* | |
C35 | 0.5305 (3) | 0.7454 (2) | 0.5154 (6) | 0.0590 (16) | |
H35 | 0.5175 | 0.7154 | 0.5433 | 0.071* | |
C36 | 0.5869 (3) | 0.7465 (2) | 0.4408 (6) | 0.0554 (15) | |
C37 | 0.6176 (3) | 0.7894 (2) | 0.4070 (6) | 0.0512 (15) | |
C38 | 0.6743 (3) | 0.7866 (2) | 0.3343 (6) | 0.0590 (16) | |
C39 | 0.6974 (3) | 0.7431 (3) | 0.2950 (7) | 0.0726 (19) | |
H39 | 0.7342 | 0.7419 | 0.2459 | 0.087* | |
C40 | 0.6663 (4) | 0.7012 (3) | 0.3279 (7) | 0.082 (2) | |
H40 | 0.6826 | 0.6720 | 0.3012 | 0.099* | |
C41 | 0.6117 (3) | 0.7024 (2) | 0.3992 (7) | 0.0727 (19) | |
H41 | 0.5909 | 0.6740 | 0.4203 | 0.087* | |
C42 | 0.7613 (3) | 0.8289 (2) | 0.2383 (8) | 0.099 (2) | |
H42A | 0.7992 | 0.8097 | 0.2945 | 0.149* | |
H42B | 0.7783 | 0.8610 | 0.2319 | 0.149* | |
H42C | 0.7461 | 0.8157 | 0.1421 | 0.149* | |
C43 | 0.4510 (3) | 0.86868 (17) | 0.2621 (6) | 0.0517 (15) | |
C44 | 0.4930 (3) | 0.87867 (19) | 0.1658 (7) | 0.0666 (17) | |
H44 | 0.5425 | 0.8767 | 0.1969 | 0.080* | |
C45 | 0.4628 (4) | 0.8915 (2) | 0.0243 (8) | 0.084 (2) | |
H45 | 0.4920 | 0.8991 | −0.0389 | 0.101* | |
C46 | 0.3906 (5) | 0.8930 (3) | −0.0232 (8) | 0.101 (3) | |
H46 | 0.3704 | 0.9014 | −0.1193 | 0.121* | |
C47 | 0.3473 (4) | 0.8823 (2) | 0.0689 (10) | 0.091 (2) | |
H47 | 0.2977 | 0.8828 | 0.0354 | 0.109* | |
C48 | 0.3776 (3) | 0.8707 (2) | 0.2124 (8) | 0.0718 (18) | |
H48 | 0.3482 | 0.8641 | 0.2760 | 0.086* | |
C49 | 0.5474 (3) | 0.91054 (18) | 0.6191 (6) | 0.0481 (14) | |
C50 | 0.5057 (3) | 0.9406 (2) | 0.6795 (7) | 0.080 (2) | |
H50 | 0.4570 | 0.9343 | 0.6659 | 0.096* | |
C51 | 0.5347 (5) | 0.9802 (3) | 0.7605 (8) | 0.105 (3) | |
H51 | 0.5057 | 0.9999 | 0.8016 | 0.126* | |
C52 | 0.6051 (5) | 0.9899 (3) | 0.7797 (9) | 0.108 (3) | |
H52 | 0.6243 | 1.0167 | 0.8327 | 0.130* | |
C53 | 0.6480 (4) | 0.9606 (3) | 0.7221 (8) | 0.097 (2) | |
H53 | 0.6966 | 0.9674 | 0.7363 | 0.117* | |
C54 | 0.6196 (3) | 0.9211 (2) | 0.6425 (7) | 0.0704 (18) | |
H54 | 0.6493 | 0.9011 | 0.6039 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0419 (2) | 0.0469 (2) | 0.0478 (2) | −0.00302 (17) | 0.00702 (17) | 0.0001 (2) |
Sn2 | 0.0486 (2) | 0.0417 (2) | 0.0617 (3) | −0.00054 (18) | 0.01537 (19) | 0.0007 (2) |
Cl1 | 0.1256 (16) | 0.0735 (13) | 0.1236 (16) | 0.0273 (10) | 0.0628 (13) | 0.0444 (12) |
Cl2 | 0.0946 (13) | 0.0798 (13) | 0.1330 (17) | −0.0108 (10) | 0.0691 (12) | 0.0045 (11) |
N1 | 0.044 (3) | 0.047 (3) | 0.051 (3) | −0.004 (2) | 0.009 (2) | 0.002 (2) |
N2 | 0.056 (3) | 0.048 (3) | 0.063 (3) | −0.008 (2) | 0.012 (3) | 0.010 (3) |
N3 | 0.048 (3) | 0.037 (3) | 0.064 (3) | 0.003 (2) | 0.013 (2) | 0.007 (2) |
N4 | 0.049 (3) | 0.038 (3) | 0.079 (4) | 0.002 (2) | 0.019 (3) | 0.009 (2) |
O1 | 0.051 (2) | 0.053 (2) | 0.064 (3) | −0.0073 (19) | −0.0029 (19) | 0.013 (2) |
O2 | 0.043 (2) | 0.057 (2) | 0.053 (2) | −0.0029 (17) | 0.0003 (19) | 0.0101 (19) |
O3 | 0.063 (3) | 0.064 (3) | 0.079 (3) | −0.001 (2) | 0.008 (2) | 0.021 (2) |
O4 | 0.060 (2) | 0.040 (2) | 0.095 (3) | 0.0040 (18) | 0.037 (2) | 0.014 (2) |
O5 | 0.051 (2) | 0.046 (2) | 0.080 (3) | 0.0015 (17) | 0.022 (2) | −0.008 (2) |
O6 | 0.063 (3) | 0.083 (3) | 0.093 (3) | −0.001 (2) | 0.032 (2) | −0.012 (3) |
C1 | 0.044 (3) | 0.058 (4) | 0.046 (4) | −0.001 (3) | 0.016 (3) | 0.004 (3) |
C2 | 0.055 (4) | 0.048 (4) | 0.054 (4) | 0.001 (3) | 0.022 (3) | −0.001 (3) |
C3 | 0.068 (4) | 0.063 (5) | 0.083 (5) | 0.001 (4) | 0.011 (4) | 0.011 (4) |
C4 | 0.091 (5) | 0.045 (4) | 0.098 (6) | −0.005 (4) | 0.040 (5) | 0.014 (4) |
C5 | 0.074 (5) | 0.055 (4) | 0.079 (5) | 0.019 (4) | 0.033 (4) | 0.014 (4) |
C6 | 0.072 (5) | 0.075 (5) | 0.076 (5) | 0.020 (4) | 0.020 (4) | 0.015 (4) |
C7 | 0.067 (4) | 0.055 (4) | 0.066 (4) | 0.001 (3) | 0.013 (4) | 0.008 (4) |
C8 | 0.043 (3) | 0.051 (4) | 0.062 (4) | 0.001 (3) | 0.012 (3) | −0.008 (3) |
C9 | 0.044 (3) | 0.047 (4) | 0.039 (3) | 0.009 (3) | 0.006 (3) | −0.007 (3) |
C10 | 0.047 (3) | 0.055 (4) | 0.041 (3) | 0.008 (3) | 0.012 (3) | −0.002 (3) |
C11 | 0.051 (4) | 0.048 (4) | 0.046 (4) | 0.002 (3) | 0.010 (3) | 0.000 (3) |
C12 | 0.070 (4) | 0.066 (5) | 0.052 (4) | 0.020 (4) | 0.007 (3) | 0.004 (3) |
C13 | 0.053 (4) | 0.070 (5) | 0.069 (5) | 0.000 (4) | −0.003 (3) | −0.011 (4) |
C14 | 0.047 (4) | 0.062 (4) | 0.053 (4) | 0.003 (3) | −0.001 (3) | −0.006 (3) |
C15 | 0.076 (5) | 0.078 (5) | 0.113 (6) | 0.008 (4) | 0.024 (4) | 0.037 (5) |
C16 | 0.039 (3) | 0.044 (4) | 0.047 (4) | −0.004 (2) | 0.015 (3) | 0.000 (3) |
C17 | 0.085 (5) | 0.061 (5) | 0.043 (4) | 0.009 (3) | 0.000 (3) | −0.005 (3) |
C18 | 0.123 (6) | 0.058 (5) | 0.066 (5) | 0.024 (4) | 0.012 (4) | −0.002 (4) |
C19 | 0.102 (5) | 0.064 (5) | 0.060 (5) | −0.013 (4) | 0.018 (4) | −0.018 (4) |
C20 | 0.113 (6) | 0.080 (6) | 0.044 (4) | −0.005 (4) | 0.010 (4) | 0.005 (4) |
C21 | 0.077 (4) | 0.053 (4) | 0.056 (4) | 0.013 (3) | 0.004 (3) | −0.002 (3) |
C22 | 0.041 (3) | 0.055 (4) | 0.042 (3) | 0.004 (3) | 0.006 (3) | −0.007 (3) |
C23 | 0.075 (5) | 0.085 (5) | 0.082 (5) | 0.020 (4) | 0.024 (4) | 0.007 (4) |
C24 | 0.103 (6) | 0.111 (7) | 0.135 (8) | 0.053 (5) | 0.056 (6) | 0.013 (6) |
C25 | 0.067 (5) | 0.134 (8) | 0.105 (7) | 0.022 (5) | 0.034 (5) | −0.025 (6) |
C26 | 0.075 (5) | 0.124 (7) | 0.082 (5) | 0.004 (5) | 0.041 (4) | 0.010 (5) |
C27 | 0.056 (4) | 0.077 (5) | 0.073 (5) | 0.009 (3) | 0.021 (3) | 0.005 (4) |
C28 | 0.050 (3) | 0.042 (4) | 0.055 (4) | −0.007 (3) | 0.010 (3) | 0.000 (3) |
C29 | 0.044 (3) | 0.039 (4) | 0.050 (4) | −0.006 (3) | 0.006 (3) | 0.005 (3) |
C30 | 0.057 (4) | 0.044 (4) | 0.054 (4) | 0.002 (3) | 0.013 (3) | 0.014 (3) |
C31 | 0.057 (4) | 0.040 (4) | 0.068 (4) | 0.009 (3) | 0.019 (3) | −0.003 (3) |
C32 | 0.056 (4) | 0.055 (4) | 0.066 (4) | −0.006 (3) | 0.015 (3) | 0.000 (3) |
C33 | 0.084 (5) | 0.060 (4) | 0.094 (5) | −0.001 (4) | 0.039 (4) | 0.034 (4) |
C34 | 0.055 (4) | 0.060 (4) | 0.090 (5) | 0.008 (3) | 0.014 (3) | 0.033 (4) |
C35 | 0.058 (4) | 0.044 (4) | 0.071 (4) | 0.006 (3) | 0.006 (3) | 0.003 (3) |
C36 | 0.049 (4) | 0.056 (4) | 0.056 (4) | 0.009 (3) | 0.002 (3) | −0.008 (3) |
C37 | 0.040 (3) | 0.056 (4) | 0.050 (4) | 0.010 (3) | −0.004 (3) | −0.007 (3) |
C38 | 0.051 (4) | 0.055 (5) | 0.069 (4) | −0.001 (3) | 0.009 (3) | −0.014 (3) |
C39 | 0.063 (4) | 0.078 (5) | 0.075 (5) | 0.010 (4) | 0.013 (3) | −0.018 (4) |
C40 | 0.087 (5) | 0.065 (5) | 0.096 (6) | 0.019 (4) | 0.022 (4) | −0.024 (4) |
C41 | 0.073 (4) | 0.052 (4) | 0.089 (5) | 0.013 (3) | 0.008 (4) | −0.004 (4) |
C42 | 0.084 (5) | 0.108 (6) | 0.121 (7) | −0.001 (4) | 0.057 (5) | −0.006 (5) |
C43 | 0.055 (4) | 0.033 (3) | 0.065 (4) | −0.004 (3) | 0.010 (3) | −0.008 (3) |
C44 | 0.070 (4) | 0.059 (4) | 0.070 (5) | −0.006 (3) | 0.014 (4) | 0.002 (4) |
C45 | 0.112 (6) | 0.088 (6) | 0.053 (5) | 0.008 (5) | 0.019 (4) | 0.009 (4) |
C46 | 0.129 (8) | 0.094 (6) | 0.065 (6) | 0.010 (6) | −0.009 (6) | −0.008 (5) |
C47 | 0.070 (5) | 0.092 (6) | 0.092 (6) | −0.001 (4) | −0.023 (5) | −0.013 (5) |
C48 | 0.058 (4) | 0.066 (5) | 0.086 (5) | −0.006 (3) | 0.005 (4) | −0.008 (4) |
C49 | 0.052 (4) | 0.037 (3) | 0.055 (4) | 0.005 (3) | 0.012 (3) | 0.005 (3) |
C50 | 0.071 (4) | 0.075 (5) | 0.090 (5) | 0.004 (4) | 0.010 (4) | −0.027 (4) |
C51 | 0.117 (7) | 0.083 (6) | 0.109 (7) | 0.029 (5) | 0.012 (5) | −0.036 (5) |
C52 | 0.122 (7) | 0.063 (6) | 0.119 (7) | −0.002 (5) | −0.014 (6) | −0.032 (5) |
C53 | 0.078 (5) | 0.072 (6) | 0.130 (7) | −0.014 (4) | −0.003 (5) | −0.022 (5) |
C54 | 0.061 (4) | 0.057 (4) | 0.090 (5) | −0.003 (3) | 0.013 (4) | −0.010 (4) |
Sn1—O2 | 2.067 (3) | C20—H20 | 0.9300 |
Sn1—C16 | 2.097 (5) | C21—H21 | 0.9300 |
Sn1—C22 | 2.107 (5) | C22—C27 | 1.372 (7) |
Sn1—O1 | 2.133 (3) | C22—C23 | 1.379 (7) |
Sn1—N1 | 2.149 (4) | C23—C24 | 1.387 (8) |
Sn2—O5 | 2.065 (3) | C23—H23 | 0.9300 |
Sn2—C49 | 2.097 (5) | C24—C25 | 1.347 (9) |
Sn2—C43 | 2.119 (6) | C24—H24 | 0.9300 |
Sn2—O4 | 2.129 (3) | C25—C26 | 1.343 (9) |
Sn2—N3 | 2.141 (4) | C25—H25 | 0.9300 |
Cl1—C5 | 1.733 (6) | C26—C27 | 1.370 (8) |
Cl2—C32 | 1.739 (6) | C26—H26 | 0.9300 |
N1—C8 | 1.299 (6) | C27—H27 | 0.9300 |
N1—N2 | 1.395 (5) | C28—C29 | 1.477 (7) |
N2—C1 | 1.301 (6) | C29—C34 | 1.375 (7) |
N3—C35 | 1.296 (6) | C29—C30 | 1.382 (6) |
N3—N4 | 1.395 (5) | C30—C31 | 1.383 (7) |
N4—C28 | 1.297 (6) | C30—H30 | 0.9300 |
O1—C1 | 1.303 (6) | C31—C32 | 1.372 (7) |
O2—C10 | 1.330 (5) | C31—H31 | 0.9300 |
O3—C11 | 1.377 (6) | C32—C33 | 1.361 (7) |
O3—C15 | 1.421 (6) | C33—C34 | 1.364 (7) |
O4—C28 | 1.307 (6) | C33—H33 | 0.9300 |
O5—C37 | 1.321 (6) | C34—H34 | 0.9300 |
O6—C38 | 1.358 (6) | C35—C36 | 1.418 (7) |
O6—C42 | 1.439 (6) | C35—H35 | 0.9300 |
C1—C2 | 1.469 (7) | C36—C37 | 1.406 (7) |
C2—C7 | 1.377 (7) | C36—C41 | 1.410 (7) |
C2—C3 | 1.400 (7) | C37—C38 | 1.413 (7) |
C3—C4 | 1.368 (7) | C38—C39 | 1.373 (7) |
C3—H3 | 0.9300 | C39—C40 | 1.382 (8) |
C4—C5 | 1.355 (8) | C39—H39 | 0.9300 |
C4—H4 | 0.9300 | C40—C41 | 1.367 (8) |
C5—C6 | 1.363 (8) | C40—H40 | 0.9300 |
C6—C7 | 1.383 (7) | C41—H41 | 0.9300 |
C6—H6 | 0.9300 | C42—H42A | 0.9600 |
C7—H7 | 0.9300 | C42—H42B | 0.9600 |
C8—C9 | 1.419 (7) | C42—H42C | 0.9600 |
C8—H8 | 0.9300 | C43—C44 | 1.373 (7) |
C9—C10 | 1.408 (7) | C43—C48 | 1.379 (7) |
C9—C14 | 1.409 (6) | C44—C45 | 1.374 (8) |
C10—C11 | 1.398 (7) | C44—H44 | 0.9300 |
C11—C12 | 1.374 (7) | C45—C46 | 1.355 (9) |
C12—C13 | 1.389 (7) | C45—H45 | 0.9300 |
C12—H12 | 0.9300 | C46—C47 | 1.365 (9) |
C13—C14 | 1.335 (7) | C46—H46 | 0.9300 |
C13—H13 | 0.9300 | C47—C48 | 1.383 (9) |
C14—H14 | 0.9300 | C47—H47 | 0.9300 |
C15—H15A | 0.9600 | C48—H48 | 0.9300 |
C15—H15B | 0.9600 | C49—C50 | 1.371 (7) |
C15—H15C | 0.9600 | C49—C54 | 1.382 (7) |
C16—C17 | 1.358 (7) | C50—C51 | 1.386 (8) |
C16—C21 | 1.385 (7) | C50—H50 | 0.9300 |
C17—C18 | 1.385 (7) | C51—C52 | 1.347 (9) |
C17—H17 | 0.9300 | C51—H51 | 0.9300 |
C18—C19 | 1.361 (8) | C52—C53 | 1.360 (9) |
C18—H18 | 0.9300 | C52—H52 | 0.9300 |
C19—C20 | 1.355 (8) | C53—C54 | 1.377 (8) |
C19—H19 | 0.9300 | C53—H53 | 0.9300 |
C20—C21 | 1.364 (8) | C54—H54 | 0.9300 |
O2—Sn1—C16 | 95.42 (18) | C27—C22—Sn1 | 121.5 (4) |
O2—Sn1—C22 | 96.78 (18) | C23—C22—Sn1 | 120.9 (4) |
C16—Sn1—C22 | 122.71 (18) | C22—C23—C24 | 119.5 (7) |
O2—Sn1—O1 | 158.35 (13) | C22—C23—H23 | 120.2 |
C16—Sn1—O1 | 94.18 (18) | C24—C23—H23 | 120.2 |
C22—Sn1—O1 | 94.26 (18) | C25—C24—C23 | 121.2 (7) |
O2—Sn1—N1 | 84.94 (15) | C25—C24—H24 | 119.4 |
C16—Sn1—N1 | 120.24 (16) | C23—C24—H24 | 119.4 |
C22—Sn1—N1 | 116.48 (17) | C26—C25—C24 | 119.8 (7) |
O1—Sn1—N1 | 73.46 (15) | C26—C25—H25 | 120.1 |
O5—Sn2—C49 | 93.66 (17) | C24—C25—H25 | 120.1 |
O5—Sn2—C43 | 96.99 (19) | C25—C26—C27 | 120.1 (7) |
C49—Sn2—C43 | 119.50 (19) | C25—C26—H26 | 120.0 |
O5—Sn2—O4 | 156.18 (14) | C27—C26—H26 | 120.0 |
C49—Sn2—O4 | 95.77 (18) | C26—C27—C22 | 121.8 (6) |
C43—Sn2—O4 | 97.29 (19) | C26—C27—H27 | 119.1 |
O5—Sn2—N3 | 83.29 (15) | C22—C27—H27 | 119.1 |
C49—Sn2—N3 | 125.24 (18) | N4—C28—O4 | 125.2 (5) |
C43—Sn2—N3 | 115.12 (17) | N4—C28—C29 | 116.6 (5) |
O4—Sn2—N3 | 73.40 (15) | O4—C28—C29 | 118.1 (5) |
C8—N1—N2 | 116.5 (4) | C34—C29—C30 | 118.1 (5) |
C8—N1—Sn1 | 127.1 (4) | C34—C29—C28 | 121.3 (5) |
N2—N1—Sn1 | 116.3 (3) | C30—C29—C28 | 120.5 (5) |
C1—N2—N1 | 111.6 (4) | C29—C30—C31 | 120.9 (5) |
C35—N3—N4 | 115.8 (4) | C29—C30—H30 | 119.5 |
C35—N3—Sn2 | 126.7 (4) | C31—C30—H30 | 119.5 |
N4—N3—Sn2 | 116.9 (3) | C32—C31—C30 | 118.7 (5) |
C28—N4—N3 | 110.6 (4) | C32—C31—H31 | 120.6 |
C1—O1—Sn1 | 114.1 (3) | C30—C31—H31 | 120.6 |
C10—O2—Sn1 | 132.3 (3) | C33—C32—C31 | 121.3 (5) |
C11—O3—C15 | 116.9 (4) | C33—C32—Cl2 | 119.1 (5) |
C28—O4—Sn2 | 113.4 (3) | C31—C32—Cl2 | 119.6 (5) |
C37—O5—Sn2 | 129.0 (3) | C32—C33—C34 | 119.2 (6) |
C38—O6—C42 | 117.2 (5) | C32—C33—H33 | 120.4 |
N2—C1—O1 | 124.4 (5) | C34—C33—H33 | 120.4 |
N2—C1—C2 | 116.9 (5) | C33—C34—C29 | 121.7 (5) |
O1—C1—C2 | 118.7 (5) | C33—C34—H34 | 119.1 |
C7—C2—C3 | 117.5 (6) | C29—C34—H34 | 119.1 |
C7—C2—C1 | 120.8 (5) | N3—C35—C36 | 127.3 (5) |
C3—C2—C1 | 121.7 (6) | N3—C35—H35 | 116.4 |
C4—C3—C2 | 120.6 (6) | C36—C35—H35 | 116.4 |
C4—C3—H3 | 119.7 | C37—C36—C41 | 119.9 (6) |
C2—C3—H3 | 119.7 | C37—C36—C35 | 122.5 (5) |
C5—C4—C3 | 120.5 (6) | C41—C36—C35 | 117.6 (6) |
C5—C4—H4 | 119.8 | O5—C37—C36 | 123.8 (5) |
C3—C4—H4 | 119.8 | O5—C37—C38 | 118.1 (5) |
C4—C5—C6 | 120.7 (6) | C36—C37—C38 | 118.0 (5) |
C4—C5—Cl1 | 119.1 (6) | O6—C38—C39 | 124.7 (6) |
C6—C5—Cl1 | 120.2 (6) | O6—C38—C37 | 114.5 (5) |
C5—C6—C7 | 119.4 (6) | C39—C38—C37 | 120.8 (6) |
C5—C6—H6 | 120.3 | C38—C39—C40 | 120.5 (6) |
C7—C6—H6 | 120.3 | C38—C39—H39 | 119.7 |
C2—C7—C6 | 121.3 (6) | C40—C39—H39 | 119.7 |
C2—C7—H7 | 119.3 | C41—C40—C39 | 120.6 (6) |
C6—C7—H7 | 119.3 | C41—C40—H40 | 119.7 |
N1—C8—C9 | 128.0 (5) | C39—C40—H40 | 119.7 |
N1—C8—H8 | 116.0 | C40—C41—C36 | 120.1 (6) |
C9—C8—H8 | 116.0 | C40—C41—H41 | 119.9 |
C10—C9—C14 | 119.8 (5) | C36—C41—H41 | 119.9 |
C10—C9—C8 | 123.8 (5) | O6—C42—H42A | 109.5 |
C14—C9—C8 | 116.4 (5) | O6—C42—H42B | 109.5 |
O2—C10—C11 | 118.8 (5) | H42A—C42—H42B | 109.5 |
O2—C10—C9 | 123.6 (5) | O6—C42—H42C | 109.5 |
C11—C10—C9 | 117.6 (5) | H42A—C42—H42C | 109.5 |
C12—C11—O3 | 124.7 (5) | H42B—C42—H42C | 109.5 |
C12—C11—C10 | 121.0 (5) | C44—C43—C48 | 118.4 (6) |
O3—C11—C10 | 114.3 (5) | C44—C43—Sn2 | 118.5 (4) |
C11—C12—C13 | 120.5 (6) | C48—C43—Sn2 | 123.0 (5) |
C11—C12—H12 | 119.7 | C43—C44—C45 | 120.9 (6) |
C13—C12—H12 | 119.7 | C43—C44—H44 | 119.5 |
C14—C13—C12 | 120.1 (6) | C45—C44—H44 | 119.5 |
C14—C13—H13 | 120.0 | C46—C45—C44 | 120.0 (7) |
C12—C13—H13 | 120.0 | C46—C45—H45 | 120.0 |
C13—C14—C9 | 121.0 (6) | C44—C45—H45 | 120.0 |
C13—C14—H14 | 119.5 | C45—C46—C47 | 120.5 (7) |
C9—C14—H14 | 119.5 | C45—C46—H46 | 119.7 |
O3—C15—H15A | 109.5 | C47—C46—H46 | 119.7 |
O3—C15—H15B | 109.5 | C46—C47—C48 | 119.5 (7) |
H15A—C15—H15B | 109.5 | C46—C47—H47 | 120.2 |
O3—C15—H15C | 109.5 | C48—C47—H47 | 120.2 |
H15A—C15—H15C | 109.5 | C43—C48—C47 | 120.6 (7) |
H15B—C15—H15C | 109.5 | C43—C48—H48 | 119.7 |
C17—C16—C21 | 117.5 (5) | C47—C48—H48 | 119.7 |
C17—C16—Sn1 | 121.5 (4) | C50—C49—C54 | 117.4 (5) |
C21—C16—Sn1 | 121.0 (4) | C50—C49—Sn2 | 121.0 (4) |
C16—C17—C18 | 121.1 (6) | C54—C49—Sn2 | 121.3 (4) |
C16—C17—H17 | 119.5 | C49—C50—C51 | 121.3 (6) |
C18—C17—H17 | 119.5 | C49—C50—H50 | 119.3 |
C19—C18—C17 | 120.3 (6) | C51—C50—H50 | 119.3 |
C19—C18—H18 | 119.8 | C52—C51—C50 | 119.9 (7) |
C17—C18—H18 | 119.8 | C52—C51—H51 | 120.1 |
C20—C19—C18 | 119.2 (6) | C50—C51—H51 | 120.1 |
C20—C19—H19 | 120.4 | C51—C52—C53 | 120.3 (7) |
C18—C19—H19 | 120.4 | C51—C52—H52 | 119.8 |
C19—C20—C21 | 120.6 (6) | C53—C52—H52 | 119.8 |
C19—C20—H20 | 119.7 | C52—C53—C54 | 120.0 (7) |
C21—C20—H20 | 119.7 | C52—C53—H53 | 120.0 |
C20—C21—C16 | 121.2 (6) | C54—C53—H53 | 120.0 |
C20—C21—H21 | 119.4 | C53—C54—C49 | 121.0 (6) |
C16—C21—H21 | 119.4 | C53—C54—H54 | 119.5 |
C27—C22—C23 | 117.6 (5) | C49—C54—H54 | 119.5 |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)2(C15H11ClN2O3)] |
Mr | 575.60 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 19.178 (2), 27.968 (3), 9.4230 (13) |
β (°) | 103.238 (2) |
V (Å3) | 4920.1 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.18 |
Crystal size (mm) | 0.37 × 0.17 × 0.12 |
Data collection | |
Diffractometer | CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.670, 0.872 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20342, 8658, 5197 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.087, 1.01 |
No. of reflections | 8658 |
No. of parameters | 615 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.76 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Recently, we have reported some organotin(IV) complexes with Schiff base of o-vanillin-2-thiophenoylhydrazone (Yin, Chen, 2006). As an extension of our work on the organotin(IV) Schiff bases chemistry, the title compound, (I), is reported here (Fig. 1).
In the title compound, (I), the Sn atom has a distorted trigonal-bipyramidal geometry, with atoms O1 (O4) and O2 (O5) in axial positions [O1—Sn1—O2 = 158.33 (13)°, O4—Sn2—O5 = 156.14 (15)°] and the atoms C16 (C43), C22 (C49)] and N1 (N3) in equatorial positions. The sum of the equatorial angles is 359.43 ° (359.86 °), indicating approximate coplanarity for these atoms. The Sn1—N1 (Sn2—N3) bond length is 2.150 (4) Å (2.141 (4) Å) close to the sum of the non-polar covalent radii 2.15 Å, indicate a strong Sn—N interaction. The O atoms coordinate to the Sn atom with one shorter and one longer Sn—O bond.