Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048647/hg2308sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048647/hg2308Isup2.hkl |
CCDC reference: 667133
The title compound was synthesized by the reaction of diphenyltin dichloride (0.69 g, 2 mmol) with potassium N-(5-chlorosalicylidene)-(L)-valinate (0.59 g, 2 mmol) in the presence of Et3N (0.20 g, 2 mmol) in 60 ml benzene. The reaction mixture was refluxed for 3 h and filtered. The yellow solid obtained, (I), by removal of solvent under reduce pressure was recrystallized from dichloromethane-petroleum ether (60–90) (1:2, V/V) and crystals of (I) were obtained from chloroform-hexane (1:1, V/V) by slow evaporation at temperature (yield 61%, m.p. 523–524 K).
One phenyl group (C19–C24) is disordered over two positions; ipso atom C19 was refined with full occupancy, while the other atoms were refined in two parts, with site occupancy factors of 0.58 (3) (atoms C20–C24) and 0.42 (3) (atoms C20'–C24'). The phenyl rings were restrained to be planar regular hexagons, with target C?C distances of 1.39 (1) Å. The absolute configuration of the compound (I) was assigned on the basis of the known configuration of the starting reagent, (L)-valine. H atoms were placed at calculated positions and were included in the refinement in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, and C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine H atoms.
The structural chemistry of diorganotin complexes with Schiff bases derived from α-amino acids receives attention since their antitumour activities and the quadratic nonlinear optical properties (Beltran et al., 2003; Dakternieks et al., 1998; Tian et al., 2005, 2006, 2007; Rivera et al., 2006). The structures of several diorganotin complexes with the Schiff base ligand, [N-(2-oxidohydroxyphenylmethylene)valine, such as [N-(2-oxidophenylmethylene)valinato]dibutyltin(IV), [N-(2-oxidophenylmethylene)valinato]diphenyltin(IV) (Beltran et al., 2003), [N-(4-diethylamino-2-oxidophenylmethylene)valinato]diphenyltin(IV) (Rivera et al., 2006), [N-(2-oxidophenylmethylene)valinato]di-t-butyltin(IV) (Ding et al., 2006), [N-(5-bromo-2-oxidophenylmethylene)valinato]diphenyltin(IV), [N-(3,5-dibromo-2-oxidophenylmethylene)valinato]diphenyltin(IV) and [N-(3,5-dibromo-2-oxidophenylmethylene)valinato]dibutyltin(IV) (Tian et al., 2005, 2006, 2007) have been reported.
The coordination geometry about the tin atom in the title compound, (I), is that of a distorted trigonal bipyramid with two phenyl groups and the imino N1 atom occupying the equatorial positions and the axial positions being occupied by a unidentate carboxylate O1 atom and phenoxide O2 atom (Fig. 1). The bond length of Sn—O2 was longer than that of Sn—O1 and the bond angle O1—Sn—O2 was 157.87 (11)°. The monodentate mode of coordination of carboxylate is reflected in the disparate C9—O2 and C9—O3 bond lengths of 1.290 (6) and 1.200 (6) Å, respectively. The distances of bonds around the tin atom were comparable to those observed in the diphenyltin complexes mentioned above.
For related literature, see: Beltran et al. (2003); Dakternieks et al. (1998); Ding et al. (2006); Rivera et al. (2006); Tian et al. (2005, 2006, 2007).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Sn(C6H5)2(C12H12ClNO3)] | F(000) = 528 |
Mr = 526.57 | Dx = 1.543 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3681 reflections |
a = 9.5105 (11) Å | θ = 2.6–23.6° |
b = 11.3594 (13) Å | µ = 1.27 mm−1 |
c = 10.4939 (12) Å | T = 295 K |
β = 91.305 (2)° | Block, yellow |
V = 1133.4 (2) Å3 | 0.13 × 0.10 × 0.07 mm |
Z = 2 |
Bruker SMART APEX area-detector diffractometer | 4590 independent reflections |
Radiation source: fine-focus sealed tube | 4284 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 26.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.852, Tmax = 0.916 | k = −14→14 |
9180 measured reflections | l = −12→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0252P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4590 reflections | Δρmax = 0.40 e Å−3 |
289 parameters | Δρmin = −0.45 e Å−3 |
19 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (2) |
[Sn(C6H5)2(C12H12ClNO3)] | V = 1133.4 (2) Å3 |
Mr = 526.57 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.5105 (11) Å | µ = 1.27 mm−1 |
b = 11.3594 (13) Å | T = 295 K |
c = 10.4939 (12) Å | 0.13 × 0.10 × 0.07 mm |
β = 91.305 (2)° |
Bruker SMART APEX area-detector diffractometer | 4590 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4284 reflections with I > 2σ(I) |
Tmin = 0.852, Tmax = 0.916 | Rint = 0.028 |
9180 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.067 | Δρmax = 0.40 e Å−3 |
S = 1.02 | Δρmin = −0.45 e Å−3 |
4590 reflections | Absolute structure: Flack (1983) |
289 parameters | Absolute structure parameter: 0.03 (2) |
19 restraints |
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) | |
Sn1 | 0.70895 (2) | 0.99509 (4) | 0.831297 (19) | 0.03600 (8) | |
Cl1 | 1.13466 (16) | 0.52770 (11) | 0.54971 (14) | 0.0832 (5) | |
O1 | 0.8224 (3) | 0.8460 (3) | 0.8791 (3) | 0.0450 (7) | |
O2 | 0.5607 (3) | 1.1018 (3) | 0.7298 (3) | 0.0493 (7) | |
O3 | 0.4190 (4) | 1.1202 (3) | 0.5617 (4) | 0.0694 (11) | |
N1 | 0.6499 (3) | 0.8924 (3) | 0.6661 (3) | 0.0338 (7) | |
C1 | 0.8890 (4) | 0.7729 (4) | 0.8023 (5) | 0.0398 (11) | |
C2 | 1.0045 (4) | 0.7085 (4) | 0.8506 (4) | 0.0466 (10) | |
H2 | 1.0327 | 0.7175 | 0.9355 | 0.056* | |
C3 | 1.0755 (5) | 0.6330 (4) | 0.7744 (5) | 0.0545 (12) | |
H3 | 1.1514 | 0.5905 | 0.8077 | 0.065* | |
C4 | 1.0353 (5) | 0.6191 (4) | 0.6476 (4) | 0.0494 (11) | |
C5 | 0.9224 (5) | 0.6768 (4) | 0.5986 (4) | 0.0471 (10) | |
H5 | 0.8946 | 0.6643 | 0.5141 | 0.056* | |
C6 | 0.8465 (4) | 0.7554 (3) | 0.6741 (4) | 0.0362 (8) | |
C7 | 0.7225 (4) | 0.8101 (3) | 0.6175 (4) | 0.0389 (9) | |
H7 | 0.6929 | 0.7825 | 0.5379 | 0.047* | |
C8 | 0.5227 (5) | 0.9352 (5) | 0.5940 (5) | 0.0399 (12) | |
H8 | 0.5401 | 0.9296 | 0.5025 | 0.048* | |
C9 | 0.4979 (5) | 1.0633 (4) | 0.6278 (5) | 0.0426 (13) | |
C10 | 0.3968 (5) | 0.8528 (5) | 0.6264 (5) | 0.0549 (13) | |
H10 | 0.4284 | 0.7716 | 0.6135 | 0.066* | |
C11 | 0.3545 (5) | 0.8629 (5) | 0.7628 (5) | 0.0758 (16) | |
H11A | 0.3239 | 0.9419 | 0.7793 | 0.114* | |
H11B | 0.4334 | 0.8443 | 0.8178 | 0.114* | |
H11C | 0.2791 | 0.8091 | 0.7786 | 0.114* | |
C12 | 0.2732 (6) | 0.8735 (6) | 0.5346 (6) | 0.101 (2) | |
H12A | 0.2016 | 0.8159 | 0.5492 | 0.151* | |
H12B | 0.3044 | 0.8670 | 0.4485 | 0.151* | |
H12C | 0.2357 | 0.9509 | 0.5480 | 0.151* | |
C13 | 0.5895 (3) | 0.9951 (6) | 0.9989 (3) | 0.0409 (7) | |
C14 | 0.5991 (5) | 0.9052 (4) | 1.0871 (4) | 0.0499 (11) | |
H14 | 0.6574 | 0.8413 | 1.0718 | 0.060* | |
C15 | 0.5231 (6) | 0.9088 (5) | 1.1980 (5) | 0.0666 (14) | |
H15 | 0.5311 | 0.8483 | 1.2575 | 0.080* | |
C16 | 0.4367 (5) | 1.0019 (8) | 1.2188 (4) | 0.0779 (14) | |
H16 | 0.3838 | 1.0041 | 1.2921 | 0.094* | |
C17 | 0.4268 (7) | 1.0916 (6) | 1.1336 (6) | 0.090 (2) | |
H17 | 0.3683 | 1.1553 | 1.1494 | 0.108* | |
C18 | 0.5042 (6) | 1.0885 (5) | 1.0227 (5) | 0.0669 (14) | |
H18 | 0.4976 | 1.1502 | 0.9647 | 0.080* | |
C19 | 0.8775 (4) | 1.1131 (4) | 0.8039 (4) | 0.0468 (10) | |
C20 | 0.849 (3) | 1.2326 (8) | 0.7949 (19) | 0.065 (4) | 0.58 (3) |
H20 | 0.7547 | 1.2552 | 0.7978 | 0.077* | 0.58 (3) |
C21 | 0.948 (3) | 1.321 (2) | 0.782 (2) | 0.089 (6) | 0.58 (3) |
H21 | 0.9219 | 1.4001 | 0.7803 | 0.107* | 0.58 (3) |
C22 | 1.086 (3) | 1.288 (2) | 0.771 (3) | 0.079 (6) | 0.58 (3) |
H22 | 1.1558 | 1.3438 | 0.7581 | 0.094* | 0.58 (3) |
C23 | 1.121 (2) | 1.1703 (19) | 0.7802 (19) | 0.062 (4) | 0.58 (3) |
H23 | 1.2145 | 1.1477 | 0.7730 | 0.074* | 0.58 (3) |
C24 | 1.0194 (9) | 1.085 (2) | 0.800 (2) | 0.056 (4) | 0.58 (3) |
H24 | 1.0471 | 1.0071 | 0.8105 | 0.067* | 0.58 (3) |
C20' | 0.846 (4) | 1.2225 (12) | 0.751 (2) | 0.065 (4) | 0.42 (3) |
H20' | 0.7541 | 1.2456 | 0.7301 | 0.077* | 0.42 (3) |
C21' | 0.961 (4) | 1.294 (3) | 0.733 (3) | 0.089 (6) | 0.42 (3) |
H21' | 0.9491 | 1.3706 | 0.7025 | 0.107* | 0.42 (3) |
C22' | 1.095 (5) | 1.252 (4) | 0.760 (4) | 0.079 (6) | 0.42 (3) |
H22' | 1.1710 | 1.2991 | 0.7373 | 0.094* | 0.42 (3) |
C23' | 1.124 (3) | 1.146 (3) | 0.818 (3) | 0.062 (4) | 0.42 (3) |
H23' | 1.2152 | 1.1251 | 0.8441 | 0.074* | 0.42 (3) |
C24' | 1.0109 (14) | 1.071 (3) | 0.836 (3) | 0.056 (4) | 0.42 (3) |
H24' | 1.0238 | 0.9957 | 0.8681 | 0.067* | 0.42 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03674 (12) | 0.03590 (12) | 0.03530 (12) | 0.00080 (17) | −0.00019 (8) | −0.00332 (18) |
Cl1 | 0.1032 (10) | 0.0702 (12) | 0.0778 (8) | 0.0400 (8) | 0.0352 (7) | −0.0003 (6) |
O1 | 0.0523 (17) | 0.0489 (17) | 0.0337 (15) | 0.0148 (14) | −0.0012 (13) | −0.0038 (13) |
O2 | 0.0505 (17) | 0.0423 (16) | 0.0547 (19) | 0.0069 (13) | −0.0089 (15) | 0.0054 (14) |
O3 | 0.068 (2) | 0.062 (2) | 0.076 (3) | 0.0115 (19) | −0.021 (2) | 0.018 (2) |
N1 | 0.0320 (17) | 0.0361 (17) | 0.0331 (17) | −0.0016 (14) | −0.0021 (14) | 0.0023 (14) |
C1 | 0.033 (2) | 0.040 (2) | 0.046 (3) | −0.0046 (19) | 0.0032 (19) | 0.0066 (19) |
C2 | 0.047 (2) | 0.048 (2) | 0.045 (2) | 0.004 (2) | −0.004 (2) | 0.004 (2) |
C3 | 0.049 (3) | 0.046 (3) | 0.069 (3) | 0.011 (2) | 0.011 (2) | 0.010 (3) |
C4 | 0.052 (3) | 0.035 (2) | 0.062 (3) | 0.0059 (19) | 0.021 (2) | −0.002 (2) |
C5 | 0.058 (3) | 0.041 (2) | 0.043 (2) | 0.003 (2) | 0.010 (2) | −0.0047 (18) |
C6 | 0.036 (2) | 0.032 (2) | 0.041 (2) | −0.0061 (16) | 0.0053 (16) | −0.0026 (17) |
C7 | 0.043 (2) | 0.040 (2) | 0.033 (2) | −0.0080 (18) | −0.0002 (16) | −0.0005 (17) |
C8 | 0.029 (2) | 0.055 (3) | 0.035 (2) | −0.0020 (19) | −0.0040 (18) | 0.009 (2) |
C9 | 0.045 (3) | 0.044 (3) | 0.039 (3) | 0.004 (2) | 0.003 (2) | 0.013 (2) |
C10 | 0.036 (2) | 0.063 (3) | 0.065 (3) | −0.012 (2) | −0.011 (2) | 0.007 (3) |
C11 | 0.055 (3) | 0.090 (4) | 0.083 (4) | −0.025 (3) | 0.015 (3) | 0.008 (3) |
C12 | 0.060 (4) | 0.121 (6) | 0.119 (5) | −0.040 (4) | −0.042 (4) | 0.039 (4) |
C13 | 0.0453 (18) | 0.0398 (17) | 0.0377 (16) | −0.001 (3) | 0.0021 (13) | −0.007 (3) |
C14 | 0.053 (3) | 0.053 (3) | 0.044 (2) | 0.007 (2) | 0.001 (2) | −0.004 (2) |
C15 | 0.076 (4) | 0.073 (4) | 0.051 (3) | 0.001 (3) | 0.011 (3) | 0.014 (3) |
C16 | 0.082 (3) | 0.095 (4) | 0.058 (3) | 0.010 (5) | 0.031 (2) | −0.003 (5) |
C17 | 0.100 (5) | 0.093 (5) | 0.079 (4) | 0.043 (4) | 0.042 (4) | 0.001 (4) |
C18 | 0.085 (4) | 0.057 (3) | 0.060 (3) | 0.028 (3) | 0.023 (3) | 0.008 (2) |
C19 | 0.048 (3) | 0.054 (3) | 0.038 (2) | −0.017 (2) | −0.0024 (19) | −0.004 (2) |
C20 | 0.052 (4) | 0.067 (4) | 0.073 (11) | −0.025 (4) | −0.029 (8) | 0.019 (5) |
C21 | 0.091 (7) | 0.062 (11) | 0.115 (17) | −0.037 (8) | −0.033 (11) | 0.018 (9) |
C22 | 0.076 (6) | 0.080 (15) | 0.079 (7) | −0.042 (10) | −0.015 (5) | 0.014 (11) |
C23 | 0.054 (4) | 0.083 (11) | 0.049 (11) | −0.015 (5) | 0.006 (7) | 0.015 (7) |
C24 | 0.049 (3) | 0.057 (6) | 0.063 (12) | −0.008 (3) | 0.013 (4) | −0.008 (6) |
C20' | 0.052 (4) | 0.067 (4) | 0.073 (11) | −0.025 (4) | −0.029 (8) | 0.019 (5) |
C21' | 0.091 (7) | 0.062 (11) | 0.115 (17) | −0.037 (8) | −0.033 (11) | 0.018 (9) |
C22' | 0.076 (6) | 0.080 (15) | 0.079 (7) | −0.042 (10) | −0.015 (5) | 0.014 (11) |
C23' | 0.054 (4) | 0.083 (11) | 0.049 (11) | −0.015 (5) | 0.006 (7) | 0.015 (7) |
C24' | 0.049 (3) | 0.057 (6) | 0.063 (12) | −0.008 (3) | 0.013 (4) | −0.008 (6) |
Sn1—O1 | 2.064 (3) | C13—C18 | 1.362 (7) |
Sn1—C19 | 2.114 (4) | C13—C14 | 1.379 (7) |
Sn1—C13 | 2.115 (3) | C14—C15 | 1.384 (6) |
Sn1—O2 | 2.127 (3) | C14—H14 | 0.9300 |
Sn1—N1 | 2.153 (3) | C15—C16 | 1.360 (9) |
Cl1—C4 | 1.753 (4) | C15—H15 | 0.9300 |
O1—C1 | 1.327 (5) | C16—C17 | 1.357 (9) |
O2—C9 | 1.290 (6) | C16—H16 | 0.9300 |
O3—C9 | 1.200 (6) | C17—C18 | 1.392 (7) |
N1—C7 | 1.276 (5) | C17—H17 | 0.9300 |
N1—C8 | 1.494 (5) | C18—H18 | 0.9300 |
C1—C2 | 1.405 (6) | C19—C20 | 1.388 (8) |
C1—C6 | 1.410 (6) | C19—C24 | 1.388 (8) |
C2—C3 | 1.363 (6) | C19—C24' | 1.389 (9) |
C2—H2 | 0.9300 | C19—C20' | 1.391 (9) |
C3—C4 | 1.385 (7) | C20—C21 | 1.389 (8) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.350 (6) | C21—C22 | 1.379 (9) |
C5—C6 | 1.405 (6) | C21—H21 | 0.9300 |
C5—H5 | 0.9300 | C22—C23 | 1.375 (9) |
C6—C7 | 1.449 (6) | C22—H22 | 0.9300 |
C7—H7 | 0.9300 | C23—C24 | 1.387 (8) |
C8—C9 | 1.517 (6) | C23—H23 | 0.9300 |
C8—C10 | 1.564 (6) | C24—H24 | 0.9300 |
C8—H8 | 0.9800 | C20'—C21' | 1.389 (10) |
C10—C11 | 1.500 (7) | C20'—H20' | 0.9300 |
C10—C12 | 1.521 (7) | C21'—C22' | 1.383 (10) |
C10—H10 | 0.9800 | C21'—H21' | 0.9300 |
C11—H11A | 0.9600 | C22'—C23' | 1.380 (10) |
C11—H11B | 0.9600 | C22'—H22' | 0.9300 |
C11—H11C | 0.9600 | C23'—C24' | 1.387 (9) |
C12—H12A | 0.9600 | C23'—H23' | 0.9300 |
C12—H12B | 0.9600 | C24'—H24' | 0.9300 |
C12—H12C | 0.9600 | ||
O1—Sn1—C19 | 99.17 (14) | C10—C12—H12C | 109.5 |
O1—Sn1—C13 | 94.91 (19) | H12A—C12—H12C | 109.5 |
C19—Sn1—C13 | 122.44 (19) | H12B—C12—H12C | 109.5 |
O1—Sn1—O2 | 157.87 (11) | C18—C13—C14 | 118.9 (4) |
C19—Sn1—O2 | 93.82 (14) | C18—C13—Sn1 | 119.1 (4) |
C13—Sn1—O2 | 93.10 (16) | C14—C13—Sn1 | 122.0 (4) |
O1—Sn1—N1 | 82.92 (11) | C13—C14—C15 | 121.0 (4) |
C19—Sn1—N1 | 114.73 (14) | C13—C14—H14 | 119.5 |
C13—Sn1—N1 | 122.29 (16) | C15—C14—H14 | 119.5 |
O2—Sn1—N1 | 75.37 (11) | C16—C15—C14 | 119.1 (5) |
C1—O1—Sn1 | 128.3 (3) | C16—C15—H15 | 120.5 |
C9—O2—Sn1 | 120.8 (3) | C14—C15—H15 | 120.5 |
C7—N1—C8 | 118.4 (3) | C17—C16—C15 | 120.8 (4) |
C7—N1—Sn1 | 125.8 (3) | C17—C16—H16 | 119.6 |
C8—N1—Sn1 | 115.2 (3) | C15—C16—H16 | 119.6 |
O1—C1—C2 | 119.1 (4) | C16—C17—C18 | 120.1 (5) |
O1—C1—C6 | 122.5 (4) | C16—C17—H17 | 120.0 |
C2—C1—C6 | 118.4 (4) | C18—C17—H17 | 120.0 |
C3—C2—C1 | 120.7 (4) | C13—C18—C17 | 120.1 (5) |
C3—C2—H2 | 119.7 | C13—C18—H18 | 119.9 |
C1—C2—H2 | 119.7 | C17—C18—H18 | 119.9 |
C2—C3—C4 | 120.4 (4) | C20—C19—C24 | 114.5 (15) |
C2—C3—H3 | 119.8 | C20—C19—C24' | 122.0 (18) |
C4—C3—H3 | 119.8 | C24—C19—C20' | 113.4 (17) |
C5—C4—C3 | 120.7 (4) | C24'—C19—C20' | 126 (2) |
C5—C4—Cl1 | 119.9 (4) | C20—C19—Sn1 | 118.6 (11) |
C3—C4—Cl1 | 119.3 (4) | C24—C19—Sn1 | 126.8 (10) |
C4—C5—C6 | 120.5 (4) | C24'—C19—Sn1 | 116.2 (13) |
C4—C5—H5 | 119.7 | C20'—C19—Sn1 | 117.4 (15) |
C6—C5—H5 | 119.7 | C19—C20—C21 | 125 (2) |
C5—C6—C1 | 119.2 (4) | C19—C20—H20 | 117.3 |
C5—C6—C7 | 117.7 (4) | C21—C20—H20 | 117.3 |
C1—C6—C7 | 122.9 (4) | C22—C21—C20 | 117 (3) |
N1—C7—C6 | 126.4 (4) | C22—C21—H21 | 121.3 |
N1—C7—H7 | 116.8 | C20—C21—H21 | 121.3 |
C6—C7—H7 | 116.8 | C23—C22—C21 | 119 (3) |
N1—C8—C9 | 108.8 (4) | C23—C22—H22 | 120.4 |
N1—C8—C10 | 108.1 (4) | C21—C22—H22 | 120.4 |
C9—C8—C10 | 113.6 (4) | C22—C23—C24 | 121 (2) |
N1—C8—H8 | 108.8 | C22—C23—H23 | 119.3 |
C9—C8—H8 | 108.8 | C24—C23—H23 | 119.3 |
C10—C8—H8 | 108.8 | C23—C24—C19 | 121.7 (18) |
O3—C9—O2 | 124.7 (5) | C23—C24—H24 | 119.2 |
O3—C9—C8 | 118.7 (5) | C19—C24—H24 | 119.2 |
O2—C9—C8 | 116.6 (5) | C21'—C20'—C19 | 114 (3) |
C11—C10—C12 | 111.9 (5) | C21'—C20'—H20' | 122.8 |
C11—C10—C8 | 112.6 (4) | C19—C20'—H20' | 122.8 |
C12—C10—C8 | 110.7 (4) | C22'—C21'—C20' | 120 (4) |
C11—C10—H10 | 107.1 | C22'—C21'—H21' | 120.0 |
C12—C10—H10 | 107.1 | C20'—C21'—H21' | 120.0 |
C8—C10—H10 | 107.1 | C23'—C22'—C21' | 125 (4) |
C10—C11—H11A | 109.5 | C23'—C22'—H22' | 117.7 |
C10—C11—H11B | 109.5 | C21'—C22'—H22' | 117.7 |
H11A—C11—H11B | 109.5 | C22'—C23'—C24' | 116 (3) |
C10—C11—H11C | 109.5 | C22'—C23'—H23' | 121.8 |
H11A—C11—H11C | 109.5 | C24'—C23'—H23' | 121.8 |
H11B—C11—H11C | 109.5 | C23'—C24'—C19 | 118 (2) |
C10—C12—H12A | 109.5 | C23'—C24'—H24' | 121.1 |
C10—C12—H12B | 109.5 | C19—C24'—H24' | 121.1 |
H12A—C12—H12B | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)2(C12H12ClNO3)] |
Mr | 526.57 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 295 |
a, b, c (Å) | 9.5105 (11), 11.3594 (13), 10.4939 (12) |
β (°) | 91.305 (2) |
V (Å3) | 1133.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.27 |
Crystal size (mm) | 0.13 × 0.10 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART APEX area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.852, 0.916 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9180, 4590, 4284 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.067, 1.02 |
No. of reflections | 4590 |
No. of parameters | 289 |
No. of restraints | 19 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.45 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.03 (2) |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).
The structural chemistry of diorganotin complexes with Schiff bases derived from α-amino acids receives attention since their antitumour activities and the quadratic nonlinear optical properties (Beltran et al., 2003; Dakternieks et al., 1998; Tian et al., 2005, 2006, 2007; Rivera et al., 2006). The structures of several diorganotin complexes with the Schiff base ligand, [N-(2-oxidohydroxyphenylmethylene)valine, such as [N-(2-oxidophenylmethylene)valinato]dibutyltin(IV), [N-(2-oxidophenylmethylene)valinato]diphenyltin(IV) (Beltran et al., 2003), [N-(4-diethylamino-2-oxidophenylmethylene)valinato]diphenyltin(IV) (Rivera et al., 2006), [N-(2-oxidophenylmethylene)valinato]di-t-butyltin(IV) (Ding et al., 2006), [N-(5-bromo-2-oxidophenylmethylene)valinato]diphenyltin(IV), [N-(3,5-dibromo-2-oxidophenylmethylene)valinato]diphenyltin(IV) and [N-(3,5-dibromo-2-oxidophenylmethylene)valinato]dibutyltin(IV) (Tian et al., 2005, 2006, 2007) have been reported.
The coordination geometry about the tin atom in the title compound, (I), is that of a distorted trigonal bipyramid with two phenyl groups and the imino N1 atom occupying the equatorial positions and the axial positions being occupied by a unidentate carboxylate O1 atom and phenoxide O2 atom (Fig. 1). The bond length of Sn—O2 was longer than that of Sn—O1 and the bond angle O1—Sn—O2 was 157.87 (11)°. The monodentate mode of coordination of carboxylate is reflected in the disparate C9—O2 and C9—O3 bond lengths of 1.290 (6) and 1.200 (6) Å, respectively. The distances of bonds around the tin atom were comparable to those observed in the diphenyltin complexes mentioned above.