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The Sn atom of the title compound, [Sn(C6H5)2(C12H12ClNO3)], is in a distorted SnNC2O2 trigonal–bipyramidal geometry and forms five- and six-membered chelate rings with the tridentate ligand. One phenyl group is disordered over two positions with occupancy factors 0.58 (3):0.42 (3).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048647/hg2308sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048647/hg2308Isup2.hkl
Contains datablock I

CCDC reference: 667133

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.031
  • wR factor = 0.067
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.50 From the CIF: _reflns_number_total 4590 Count of symmetry unique reflns 2471 Completeness (_total/calc) 185.75% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2119 Fraction of Friedel pairs measured 0.858 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 19
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

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).

Experimental top

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).

Refinement top

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.

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. For phenyl group C19–C14, the minor disordered component has been omitted for clarity.
[N-(5-Chloro-2-oxidobenzylidene)-L-valinato-κ3O,N,O']diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C12H12ClNO3)]F(000) = 528
Mr = 526.57Dx = 1.543 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3681 reflections
a = 9.5105 (11) Åθ = 2.6–23.6°
b = 11.3594 (13) ŵ = 1.27 mm1
c = 10.4939 (12) ÅT = 295 K
β = 91.305 (2)°Block, yellow
V = 1133.4 (2) Å30.13 × 0.10 × 0.07 mm
Z = 2
Data collection top
Bruker SMART APEX area-detector
diffractometer
4590 independent reflections
Radiation source: fine-focus sealed tube4284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1111
Tmin = 0.852, Tmax = 0.916k = 1414
9180 measured reflectionsl = 1213
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-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 reflectionsΔρmax = 0.40 e Å3
289 parametersΔρmin = 0.45 e Å3
19 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (2)
Crystal data top
[Sn(C6H5)2(C12H12ClNO3)]V = 1133.4 (2) Å3
Mr = 526.57Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.5105 (11) ŵ = 1.27 mm1
b = 11.3594 (13) ÅT = 295 K
c = 10.4939 (12) Å0.13 × 0.10 × 0.07 mm
β = 91.305 (2)°
Data collection top
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 = 0.916Rint = 0.028
9180 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.067Δρmax = 0.40 e Å3
S = 1.02Δρmin = 0.45 e Å3
4590 reflectionsAbsolute structure: Flack (1983)
289 parametersAbsolute structure parameter: 0.03 (2)
19 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.70895 (2)0.99509 (4)0.831297 (19)0.03600 (8)
Cl11.13466 (16)0.52770 (11)0.54971 (14)0.0832 (5)
O10.8224 (3)0.8460 (3)0.8791 (3)0.0450 (7)
O20.5607 (3)1.1018 (3)0.7298 (3)0.0493 (7)
O30.4190 (4)1.1202 (3)0.5617 (4)0.0694 (11)
N10.6499 (3)0.8924 (3)0.6661 (3)0.0338 (7)
C10.8890 (4)0.7729 (4)0.8023 (5)0.0398 (11)
C21.0045 (4)0.7085 (4)0.8506 (4)0.0466 (10)
H21.03270.71750.93550.056*
C31.0755 (5)0.6330 (4)0.7744 (5)0.0545 (12)
H31.15140.59050.80770.065*
C41.0353 (5)0.6191 (4)0.6476 (4)0.0494 (11)
C50.9224 (5)0.6768 (4)0.5986 (4)0.0471 (10)
H50.89460.66430.51410.056*
C60.8465 (4)0.7554 (3)0.6741 (4)0.0362 (8)
C70.7225 (4)0.8101 (3)0.6175 (4)0.0389 (9)
H70.69290.78250.53790.047*
C80.5227 (5)0.9352 (5)0.5940 (5)0.0399 (12)
H80.54010.92960.50250.048*
C90.4979 (5)1.0633 (4)0.6278 (5)0.0426 (13)
C100.3968 (5)0.8528 (5)0.6264 (5)0.0549 (13)
H100.42840.77160.61350.066*
C110.3545 (5)0.8629 (5)0.7628 (5)0.0758 (16)
H11A0.32390.94190.77930.114*
H11B0.43340.84430.81780.114*
H11C0.27910.80910.77860.114*
C120.2732 (6)0.8735 (6)0.5346 (6)0.101 (2)
H12A0.20160.81590.54920.151*
H12B0.30440.86700.44850.151*
H12C0.23570.95090.54800.151*
C130.5895 (3)0.9951 (6)0.9989 (3)0.0409 (7)
C140.5991 (5)0.9052 (4)1.0871 (4)0.0499 (11)
H140.65740.84131.07180.060*
C150.5231 (6)0.9088 (5)1.1980 (5)0.0666 (14)
H150.53110.84831.25750.080*
C160.4367 (5)1.0019 (8)1.2188 (4)0.0779 (14)
H160.38381.00411.29210.094*
C170.4268 (7)1.0916 (6)1.1336 (6)0.090 (2)
H170.36831.15531.14940.108*
C180.5042 (6)1.0885 (5)1.0227 (5)0.0669 (14)
H180.49761.15020.96470.080*
C190.8775 (4)1.1131 (4)0.8039 (4)0.0468 (10)
C200.849 (3)1.2326 (8)0.7949 (19)0.065 (4)0.58 (3)
H200.75471.25520.79780.077*0.58 (3)
C210.948 (3)1.321 (2)0.782 (2)0.089 (6)0.58 (3)
H210.92191.40010.78030.107*0.58 (3)
C221.086 (3)1.288 (2)0.771 (3)0.079 (6)0.58 (3)
H221.15581.34380.75810.094*0.58 (3)
C231.121 (2)1.1703 (19)0.7802 (19)0.062 (4)0.58 (3)
H231.21451.14770.77300.074*0.58 (3)
C241.0194 (9)1.085 (2)0.800 (2)0.056 (4)0.58 (3)
H241.04711.00710.81050.067*0.58 (3)
C20'0.846 (4)1.2225 (12)0.751 (2)0.065 (4)0.42 (3)
H20'0.75411.24560.73010.077*0.42 (3)
C21'0.961 (4)1.294 (3)0.733 (3)0.089 (6)0.42 (3)
H21'0.94911.37060.70250.107*0.42 (3)
C22'1.095 (5)1.252 (4)0.760 (4)0.079 (6)0.42 (3)
H22'1.17101.29910.73730.094*0.42 (3)
C23'1.124 (3)1.146 (3)0.818 (3)0.062 (4)0.42 (3)
H23'1.21521.12510.84410.074*0.42 (3)
C24'1.0109 (14)1.071 (3)0.836 (3)0.056 (4)0.42 (3)
H24'1.02380.99570.86810.067*0.42 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.03674 (12)0.03590 (12)0.03530 (12)0.00080 (17)0.00019 (8)0.00332 (18)
Cl10.1032 (10)0.0702 (12)0.0778 (8)0.0400 (8)0.0352 (7)0.0003 (6)
O10.0523 (17)0.0489 (17)0.0337 (15)0.0148 (14)0.0012 (13)0.0038 (13)
O20.0505 (17)0.0423 (16)0.0547 (19)0.0069 (13)0.0089 (15)0.0054 (14)
O30.068 (2)0.062 (2)0.076 (3)0.0115 (19)0.021 (2)0.018 (2)
N10.0320 (17)0.0361 (17)0.0331 (17)0.0016 (14)0.0021 (14)0.0023 (14)
C10.033 (2)0.040 (2)0.046 (3)0.0046 (19)0.0032 (19)0.0066 (19)
C20.047 (2)0.048 (2)0.045 (2)0.004 (2)0.004 (2)0.004 (2)
C30.049 (3)0.046 (3)0.069 (3)0.011 (2)0.011 (2)0.010 (3)
C40.052 (3)0.035 (2)0.062 (3)0.0059 (19)0.021 (2)0.002 (2)
C50.058 (3)0.041 (2)0.043 (2)0.003 (2)0.010 (2)0.0047 (18)
C60.036 (2)0.032 (2)0.041 (2)0.0061 (16)0.0053 (16)0.0026 (17)
C70.043 (2)0.040 (2)0.033 (2)0.0080 (18)0.0002 (16)0.0005 (17)
C80.029 (2)0.055 (3)0.035 (2)0.0020 (19)0.0040 (18)0.009 (2)
C90.045 (3)0.044 (3)0.039 (3)0.004 (2)0.003 (2)0.013 (2)
C100.036 (2)0.063 (3)0.065 (3)0.012 (2)0.011 (2)0.007 (3)
C110.055 (3)0.090 (4)0.083 (4)0.025 (3)0.015 (3)0.008 (3)
C120.060 (4)0.121 (6)0.119 (5)0.040 (4)0.042 (4)0.039 (4)
C130.0453 (18)0.0398 (17)0.0377 (16)0.001 (3)0.0021 (13)0.007 (3)
C140.053 (3)0.053 (3)0.044 (2)0.007 (2)0.001 (2)0.004 (2)
C150.076 (4)0.073 (4)0.051 (3)0.001 (3)0.011 (3)0.014 (3)
C160.082 (3)0.095 (4)0.058 (3)0.010 (5)0.031 (2)0.003 (5)
C170.100 (5)0.093 (5)0.079 (4)0.043 (4)0.042 (4)0.001 (4)
C180.085 (4)0.057 (3)0.060 (3)0.028 (3)0.023 (3)0.008 (2)
C190.048 (3)0.054 (3)0.038 (2)0.017 (2)0.0024 (19)0.004 (2)
C200.052 (4)0.067 (4)0.073 (11)0.025 (4)0.029 (8)0.019 (5)
C210.091 (7)0.062 (11)0.115 (17)0.037 (8)0.033 (11)0.018 (9)
C220.076 (6)0.080 (15)0.079 (7)0.042 (10)0.015 (5)0.014 (11)
C230.054 (4)0.083 (11)0.049 (11)0.015 (5)0.006 (7)0.015 (7)
C240.049 (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)
Geometric parameters (Å, º) top
Sn1—O12.064 (3)C13—C181.362 (7)
Sn1—C192.114 (4)C13—C141.379 (7)
Sn1—C132.115 (3)C14—C151.384 (6)
Sn1—O22.127 (3)C14—H140.9300
Sn1—N12.153 (3)C15—C161.360 (9)
Cl1—C41.753 (4)C15—H150.9300
O1—C11.327 (5)C16—C171.357 (9)
O2—C91.290 (6)C16—H160.9300
O3—C91.200 (6)C17—C181.392 (7)
N1—C71.276 (5)C17—H170.9300
N1—C81.494 (5)C18—H180.9300
C1—C21.405 (6)C19—C201.388 (8)
C1—C61.410 (6)C19—C241.388 (8)
C2—C31.363 (6)C19—C24'1.389 (9)
C2—H20.9300C19—C20'1.391 (9)
C3—C41.385 (7)C20—C211.389 (8)
C3—H30.9300C20—H200.9300
C4—C51.350 (6)C21—C221.379 (9)
C5—C61.405 (6)C21—H210.9300
C5—H50.9300C22—C231.375 (9)
C6—C71.449 (6)C22—H220.9300
C7—H70.9300C23—C241.387 (8)
C8—C91.517 (6)C23—H230.9300
C8—C101.564 (6)C24—H240.9300
C8—H80.9800C20'—C21'1.389 (10)
C10—C111.500 (7)C20'—H20'0.9300
C10—C121.521 (7)C21'—C22'1.383 (10)
C10—H100.9800C21'—H21'0.9300
C11—H11A0.9600C22'—C23'1.380 (10)
C11—H11B0.9600C22'—H22'0.9300
C11—H11C0.9600C23'—C24'1.387 (9)
C12—H12A0.9600C23'—H23'0.9300
C12—H12B0.9600C24'—H24'0.9300
C12—H12C0.9600
O1—Sn1—C1999.17 (14)C10—C12—H12C109.5
O1—Sn1—C1394.91 (19)H12A—C12—H12C109.5
C19—Sn1—C13122.44 (19)H12B—C12—H12C109.5
O1—Sn1—O2157.87 (11)C18—C13—C14118.9 (4)
C19—Sn1—O293.82 (14)C18—C13—Sn1119.1 (4)
C13—Sn1—O293.10 (16)C14—C13—Sn1122.0 (4)
O1—Sn1—N182.92 (11)C13—C14—C15121.0 (4)
C19—Sn1—N1114.73 (14)C13—C14—H14119.5
C13—Sn1—N1122.29 (16)C15—C14—H14119.5
O2—Sn1—N175.37 (11)C16—C15—C14119.1 (5)
C1—O1—Sn1128.3 (3)C16—C15—H15120.5
C9—O2—Sn1120.8 (3)C14—C15—H15120.5
C7—N1—C8118.4 (3)C17—C16—C15120.8 (4)
C7—N1—Sn1125.8 (3)C17—C16—H16119.6
C8—N1—Sn1115.2 (3)C15—C16—H16119.6
O1—C1—C2119.1 (4)C16—C17—C18120.1 (5)
O1—C1—C6122.5 (4)C16—C17—H17120.0
C2—C1—C6118.4 (4)C18—C17—H17120.0
C3—C2—C1120.7 (4)C13—C18—C17120.1 (5)
C3—C2—H2119.7C13—C18—H18119.9
C1—C2—H2119.7C17—C18—H18119.9
C2—C3—C4120.4 (4)C20—C19—C24114.5 (15)
C2—C3—H3119.8C20—C19—C24'122.0 (18)
C4—C3—H3119.8C24—C19—C20'113.4 (17)
C5—C4—C3120.7 (4)C24'—C19—C20'126 (2)
C5—C4—Cl1119.9 (4)C20—C19—Sn1118.6 (11)
C3—C4—Cl1119.3 (4)C24—C19—Sn1126.8 (10)
C4—C5—C6120.5 (4)C24'—C19—Sn1116.2 (13)
C4—C5—H5119.7C20'—C19—Sn1117.4 (15)
C6—C5—H5119.7C19—C20—C21125 (2)
C5—C6—C1119.2 (4)C19—C20—H20117.3
C5—C6—C7117.7 (4)C21—C20—H20117.3
C1—C6—C7122.9 (4)C22—C21—C20117 (3)
N1—C7—C6126.4 (4)C22—C21—H21121.3
N1—C7—H7116.8C20—C21—H21121.3
C6—C7—H7116.8C23—C22—C21119 (3)
N1—C8—C9108.8 (4)C23—C22—H22120.4
N1—C8—C10108.1 (4)C21—C22—H22120.4
C9—C8—C10113.6 (4)C22—C23—C24121 (2)
N1—C8—H8108.8C22—C23—H23119.3
C9—C8—H8108.8C24—C23—H23119.3
C10—C8—H8108.8C23—C24—C19121.7 (18)
O3—C9—O2124.7 (5)C23—C24—H24119.2
O3—C9—C8118.7 (5)C19—C24—H24119.2
O2—C9—C8116.6 (5)C21'—C20'—C19114 (3)
C11—C10—C12111.9 (5)C21'—C20'—H20'122.8
C11—C10—C8112.6 (4)C19—C20'—H20'122.8
C12—C10—C8110.7 (4)C22'—C21'—C20'120 (4)
C11—C10—H10107.1C22'—C21'—H21'120.0
C12—C10—H10107.1C20'—C21'—H21'120.0
C8—C10—H10107.1C23'—C22'—C21'125 (4)
C10—C11—H11A109.5C23'—C22'—H22'117.7
C10—C11—H11B109.5C21'—C22'—H22'117.7
H11A—C11—H11B109.5C22'—C23'—C24'116 (3)
C10—C11—H11C109.5C22'—C23'—H23'121.8
H11A—C11—H11C109.5C24'—C23'—H23'121.8
H11B—C11—H11C109.5C23'—C24'—C19118 (2)
C10—C12—H12A109.5C23'—C24'—H24'121.1
C10—C12—H12B109.5C19—C24'—H24'121.1
H12A—C12—H12B109.5

Experimental details

Crystal data
Chemical formula[Sn(C6H5)2(C12H12ClNO3)]
Mr526.57
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)9.5105 (11), 11.3594 (13), 10.4939 (12)
β (°) 91.305 (2)
V3)1133.4 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.27
Crystal size (mm)0.13 × 0.10 × 0.07
Data collection
DiffractometerBruker SMART APEX area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.852, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
9180, 4590, 4284
Rint0.028
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.067, 1.02
No. of reflections4590
No. of parameters289
No. of restraints19
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.45
Absolute structureFlack (1983)
Absolute structure parameter0.03 (2)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).

 

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