[3-Meth­oxy-2-oxidobenzaldehyde (2-thienylcarbon­yl)hydrazonato]dimethyl­tin(IV)

In the mol­ecule of the title complex, [Sn(CH₃)₂(C₁₃H₁₀N₂O₃S)], the Sn atom is in a distorted trigonal–bipyramidal geometry. There are two mol­ecules in the asymmetric unit. A centrosymmetric arrangement leads to an Sn₂O₂ 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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	0.48 × 0.23 × 0.07 mm
Z = 8

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.236	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.145P)^2 + 47.0333P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—O1^i	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—O1^i	77.3 (4)	H8B—C8—H8C	109.5
C15—Sn1—O1^i	78.0 (4)	O3—C9—N2	125.6 (11)
O1—Sn1—O1^i	75.7 (3)	O3—C9—C10	117.5 (11)
O3—Sn1—O1^i	130.7 (3)	N2—C9—C10	116.8 (10)
N1—Sn1—O1^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3^i	0.96	2.29	3.09 (2)	140

Symmetry code: (i) −x+1, −y+1, −z+1.