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In the molecule of the title complex, [Sn(CH
3)
2(C
13H
10N
2O
3S)], the Sn atom is in a distorted trigonal–bipyramidal geometry. There are two molecules in the asymmetric unit. A centrosymmetric arrangement leads to an Sn
2O
2 core through weak Sn
O interactions and causes the formation of a dimer. Intermolecular C—H
O hydrogen bonds seem to be effective in the stabilization of the crystal structure.
Supporting information
CCDC reference: 608350
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.019 Å
- Disorder in main residue
- R factor = 0.067
- wR factor = 0.236
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.26
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 19
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C12 - C13 ... 1.38 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1996); cell refinement: SMART; data reduction: SAINT (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1996); software used to prepare material for publication: SHELXTL.
[3-Methoxy-2-oxidobenzaldehyde (2-thienylcarbonyl)hydrazonato]dimethyltin(IV)
top
Crystal data top
[Sn(CH3)2(C13H10N2O3S)] | F(000) = 1680 |
Mr = 423.08 | Dx = 1.727 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2678 reflections |
a = 25.777 (11) Å | θ = 2.3–23.3° |
b = 9.670 (4) Å | µ = 1.71 mm−1 |
c = 13.476 (6) Å | T = 298 K |
β = 104.318 (6)° | Block, colorless |
V = 3255 (2) Å3 | 0.48 × 0.23 × 0.07 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2858 independent reflections |
Radiation source: fine-focus sealed tube | 2074 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→30 |
Tmin = 0.494, Tmax = 0.890 | k = −11→11 |
8215 measured reflections | l = −16→12 |
Refinement top
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.236 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.145P)2 + 47.0333P] where P = (Fo2 + 2Fc2)/3 |
2858 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 2.02 e Å−3 |
6 restraints | Δρmin = −0.89 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Sn1 | 0.54243 (3) | 0.32300 (8) | 0.54843 (5) | 0.0490 (3) | |
N1 | 0.5130 (4) | 0.1323 (9) | 0.6067 (7) | 0.052 (2) | |
N2 | 0.5502 (4) | 0.0284 (10) | 0.6405 (7) | 0.056 (2) | |
O1 | 0.4604 (3) | 0.3862 (9) | 0.5292 (6) | 0.0568 (19) | |
O2 | 0.3683 (3) | 0.5291 (10) | 0.4933 (8) | 0.074 (3) | |
O3 | 0.6086 (4) | 0.1732 (8) | 0.5871 (8) | 0.066 (2) | |
S1 | 0.7036 (2) | −0.0047 (5) | 0.6673 (4) | 0.0808 (14) | 0.67 |
C11' | 0.7036 (2) | −0.0047 (5) | 0.6673 (4) | 0.0808 (14) | 0.33 |
H11' | 0.7198 | 0.0737 | 0.6486 | 0.097* | 0.33 |
C1 | 0.4661 (4) | 0.1053 (12) | 0.6170 (8) | 0.052 (3) | |
H1 | 0.4617 | 0.0196 | 0.6453 | 0.062* | |
C2 | 0.4191 (5) | 0.1919 (12) | 0.5901 (8) | 0.052 (3) | |
C3 | 0.4181 (4) | 0.3270 (11) | 0.5506 (7) | 0.046 (2) | |
C4 | 0.3679 (4) | 0.3984 (12) | 0.5314 (8) | 0.053 (3) | |
C5 | 0.3238 (5) | 0.3373 (14) | 0.5510 (10) | 0.064 (3) | |
H5 | 0.2918 | 0.3861 | 0.5387 | 0.077* | |
C6 | 0.3259 (5) | 0.2036 (15) | 0.5891 (11) | 0.070 (4) | |
H6 | 0.2955 | 0.1626 | 0.6013 | 0.084* | |
C7 | 0.3726 (5) | 0.1338 (14) | 0.6083 (10) | 0.064 (3) | |
H7 | 0.3740 | 0.0445 | 0.6344 | 0.076* | |
C8 | 0.3209 (7) | 0.604 (2) | 0.4789 (16) | 0.112 (6) | |
H8A | 0.3258 | 0.6940 | 0.4522 | 0.168* | |
H8B | 0.3116 | 0.6142 | 0.5432 | 0.168* | |
H8C | 0.2928 | 0.5564 | 0.4314 | 0.168* | |
C9 | 0.5970 (5) | 0.0603 (12) | 0.6262 (8) | 0.053 (3) | |
C10 | 0.6412 (5) | −0.0417 (13) | 0.6634 (8) | 0.060 (3) | |
C11 | 0.6321 (4) | −0.1834 (7) | 0.7080 (7) | 0.084 (2) | 0.67 |
H11 | 0.6009 | −0.2231 | 0.7178 | 0.101* | 0.67 |
S1' | 0.6321 (4) | −0.1834 (7) | 0.7080 (7) | 0.084 (2) | 0.33 |
C12 | 0.6874 (8) | −0.2383 (18) | 0.7309 (13) | 0.097 (5) | |
H12 | 0.6953 | −0.3278 | 0.7551 | 0.116* | |
C13 | 0.7270 (7) | −0.151 (2) | 0.7145 (14) | 0.095 (5) | |
H13 | 0.7631 | −0.1737 | 0.7293 | 0.115* | |
C14 | 0.5347 (6) | 0.2951 (13) | 0.3925 (9) | 0.061 (3) | |
H14A | 0.5127 | 0.2157 | 0.3694 | 0.092* | |
H14B | 0.5695 | 0.2813 | 0.3802 | 0.092* | |
H14C | 0.5184 | 0.3756 | 0.3560 | 0.092* | |
C15 | 0.5735 (6) | 0.4344 (13) | 0.6838 (9) | 0.067 (3) | |
H15A | 0.5619 | 0.3922 | 0.7392 | 0.101* | |
H15B | 0.5608 | 0.5280 | 0.6752 | 0.101* | |
H15C | 0.6119 | 0.4338 | 0.6990 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0432 (5) | 0.0561 (5) | 0.0476 (5) | 0.0052 (3) | 0.0112 (3) | 0.0007 (3) |
N1 | 0.056 (6) | 0.046 (5) | 0.052 (5) | 0.002 (4) | 0.012 (4) | 0.003 (4) |
N2 | 0.065 (6) | 0.052 (5) | 0.050 (5) | 0.006 (5) | 0.010 (4) | 0.003 (4) |
O1 | 0.028 (4) | 0.071 (5) | 0.074 (5) | 0.002 (3) | 0.017 (3) | 0.023 (4) |
O2 | 0.045 (5) | 0.079 (6) | 0.102 (7) | 0.014 (4) | 0.024 (5) | 0.031 (5) |
O3 | 0.059 (5) | 0.055 (5) | 0.089 (6) | 0.011 (4) | 0.027 (5) | 0.013 (4) |
S1 | 0.058 (3) | 0.087 (4) | 0.097 (4) | 0.008 (2) | 0.018 (2) | −0.002 (3) |
C11' | 0.058 (3) | 0.087 (4) | 0.097 (4) | 0.008 (2) | 0.018 (2) | −0.002 (3) |
C1 | 0.055 (7) | 0.051 (6) | 0.052 (6) | 0.000 (5) | 0.020 (5) | 0.001 (5) |
C2 | 0.053 (7) | 0.066 (7) | 0.039 (5) | 0.002 (5) | 0.013 (5) | −0.003 (5) |
C3 | 0.042 (6) | 0.060 (7) | 0.035 (5) | 0.005 (5) | 0.005 (4) | −0.004 (4) |
C4 | 0.052 (6) | 0.063 (7) | 0.044 (6) | −0.005 (5) | 0.012 (5) | 0.001 (5) |
C5 | 0.049 (7) | 0.079 (9) | 0.063 (7) | 0.005 (6) | 0.013 (6) | 0.002 (6) |
C6 | 0.043 (7) | 0.081 (9) | 0.083 (9) | −0.017 (6) | 0.011 (6) | 0.009 (7) |
C7 | 0.061 (8) | 0.068 (7) | 0.065 (7) | −0.006 (6) | 0.021 (6) | −0.003 (6) |
C8 | 0.092 (9) | 0.110 (9) | 0.138 (10) | −0.003 (7) | 0.037 (8) | 0.032 (8) |
C9 | 0.057 (7) | 0.050 (7) | 0.055 (6) | 0.008 (5) | 0.020 (5) | −0.001 (5) |
C10 | 0.058 (7) | 0.070 (7) | 0.049 (6) | 0.026 (6) | 0.006 (5) | 0.002 (5) |
C11 | 0.088 (6) | 0.061 (4) | 0.100 (6) | 0.014 (4) | 0.015 (5) | 0.006 (3) |
S1' | 0.088 (6) | 0.061 (4) | 0.100 (6) | 0.014 (4) | 0.015 (5) | 0.006 (3) |
C12 | 0.123 (15) | 0.074 (10) | 0.090 (11) | 0.046 (11) | 0.020 (10) | 0.015 (8) |
C13 | 0.060 (9) | 0.124 (14) | 0.098 (12) | 0.023 (9) | 0.011 (8) | −0.017 (10) |
C14 | 0.071 (8) | 0.061 (7) | 0.058 (7) | 0.016 (6) | 0.026 (6) | 0.011 (5) |
C15 | 0.073 (8) | 0.065 (8) | 0.057 (7) | −0.004 (6) | 0.005 (6) | 0.008 (6) |
Geometric parameters (Å, º) top
Sn1—C14 | 2.078 (12) | C5—C6 | 1.387 (18) |
Sn1—C15 | 2.099 (12) | C5—H5 | 0.9300 |
Sn1—O1 | 2.153 (7) | C6—C7 | 1.349 (19) |
Sn1—O3 | 2.200 (8) | C6—H6 | 0.9300 |
Sn1—N1 | 2.210 (9) | C7—H7 | 0.9300 |
Sn1—O1i | 2.995 (8) | C8—H8A | 0.9600 |
N1—C1 | 1.279 (14) | C8—H8B | 0.9600 |
N1—N2 | 1.385 (13) | C8—H8C | 0.9600 |
N2—C9 | 1.303 (15) | C9—C10 | 1.497 (16) |
O1—C3 | 1.326 (13) | C10—C11 | 1.538 (15) |
O2—C4 | 1.365 (14) | C11—C12 | 1.481 (19) |
O2—C8 | 1.39 (2) | C11—H11 | 0.9300 |
O3—C9 | 1.281 (14) | C12—C13 | 1.39 (3) |
S1—C13 | 1.603 (19) | C12—H12 | 0.9300 |
S1—C10 | 1.635 (14) | C13—H13 | 0.9300 |
C1—C2 | 1.443 (16) | C14—H14A | 0.9600 |
C1—H1 | 0.9300 | C14—H14B | 0.9600 |
C2—C7 | 1.399 (17) | C14—H14C | 0.9600 |
C2—C3 | 1.408 (15) | C15—H15A | 0.9600 |
C3—C4 | 1.434 (16) | C15—H15B | 0.9600 |
C4—C5 | 1.363 (17) | C15—H15C | 0.9600 |
| | | |
C14—Sn1—C15 | 150.0 (5) | C7—C6—H6 | 120.3 |
C14—Sn1—O1 | 94.0 (4) | C5—C6—H6 | 120.3 |
C15—Sn1—O1 | 96.4 (5) | C6—C7—C2 | 121.9 (13) |
C14—Sn1—O3 | 91.6 (4) | C6—C7—H7 | 119.1 |
C15—Sn1—O3 | 91.5 (5) | C2—C7—H7 | 119.1 |
O1—Sn1—O3 | 153.6 (3) | O2—C8—H8A | 109.5 |
C14—Sn1—N1 | 107.2 (4) | O2—C8—H8B | 109.5 |
C15—Sn1—N1 | 102.1 (4) | H8A—C8—H8B | 109.5 |
O1—Sn1—N1 | 82.4 (3) | O2—C8—H8C | 109.5 |
O3—Sn1—N1 | 71.4 (3) | H8A—C8—H8C | 109.5 |
C14—Sn1—O1i | 77.3 (4) | H8B—C8—H8C | 109.5 |
C15—Sn1—O1i | 78.0 (4) | O3—C9—N2 | 125.6 (11) |
O1—Sn1—O1i | 75.7 (3) | O3—C9—C10 | 117.5 (11) |
O3—Sn1—O1i | 130.7 (3) | N2—C9—C10 | 116.8 (10) |
N1—Sn1—O1i | 157.9 (3) | C9—C10—C11 | 122.6 (11) |
C1—N1—N2 | 114.3 (9) | C9—C10—S1 | 121.9 (10) |
C1—N1—Sn1 | 128.8 (8) | C11—C10—S1 | 115.3 (8) |
N2—N1—Sn1 | 116.9 (7) | C12—C11—C10 | 99.7 (10) |
C9—N2—N1 | 111.7 (9) | C12—C11—H11 | 130.2 |
C3—O1—Sn1 | 133.4 (7) | C10—C11—H11 | 130.2 |
C4—O2—C8 | 116.6 (11) | C13—C12—C11 | 117.1 (13) |
C9—O3—Sn1 | 114.3 (7) | C13—C12—H12 | 121.4 |
C13—S1—C10 | 95.2 (8) | C11—C12—H12 | 121.4 |
N1—C1—C2 | 127.7 (11) | C12—C13—S1 | 112.5 (13) |
N1—C1—H1 | 116.2 | C12—C13—H13 | 123.7 |
C2—C1—H1 | 116.2 | S1—C13—H13 | 123.7 |
C7—C2—C3 | 120.1 (11) | Sn1—C14—H14A | 109.5 |
C7—C2—C1 | 115.1 (11) | Sn1—C14—H14B | 109.5 |
C3—C2—C1 | 124.8 (11) | H14A—C14—H14B | 109.5 |
O1—C3—C2 | 122.9 (10) | Sn1—C14—H14C | 109.5 |
O1—C3—C4 | 120.5 (9) | H14A—C14—H14C | 109.5 |
C2—C3—C4 | 116.6 (10) | H14B—C14—H14C | 109.5 |
O2—C4—C5 | 124.0 (11) | Sn1—C15—H15A | 109.5 |
O2—C4—C3 | 115.1 (10) | Sn1—C15—H15B | 109.5 |
C5—C4—C3 | 121.0 (11) | H15A—C15—H15B | 109.5 |
C4—C5—C6 | 121.1 (12) | Sn1—C15—H15C | 109.5 |
C4—C5—H5 | 119.4 | H15A—C15—H15C | 109.5 |
C6—C5—H5 | 119.4 | H15B—C15—H15C | 109.5 |
C7—C6—C5 | 119.3 (12) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O3i | 0.96 | 2.29 | 3.09 (2) | 140 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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