Dimeth­yl[2-oxido-1-benzaldehyde (2-thienylcarbon­yl)hydrazonato]tin(IV)

In the title complex, [Sn(CH₃)₂(C₁₂H₈N₂O₂S)], the Sn atom is in a distorted trigonal-bipyramidal configuration, with Sn-O distances in the range 2.087 (3)-2.177 (3) Å. The Schiff base mol­ecule is coordinated to the Sn atom in a tridentate fashion via the azomethine N atom, the hydroxy O atom and the carbonyl O atom.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.029
• wR factor = 0.083
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Dimethyl[2-oxido-1-benzaldehyde (2-thienylcarbonyl)hydrazonato]tin(IV)

Crystal data

[Sn(CH3)2(C12H8N2O2S)]	F(000) = 1552
Mr = 393.02	Dx = 1.735 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4148 reflections
a = 25.644 (5) Å	θ = 2.3–28.1°
b = 9.701 (2) Å	µ = 1.84 mm^−1
c = 14.051 (3) Å	T = 298 K
β = 120.594 (2)°	Block, colourless
V = 3009.1 (11) Å^3	0.28 × 0.26 × 0.25 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer	2656 independent reflections
Radiation source: fine-focus sealed tube	2151 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→27
Tmin = 0.627, Tmax = 0.656	k = −11→7
7625 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.7212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.002
2656 reflections	Δρmax = 0.59 e Å^−3
182 parameters	Δρmin = −0.68 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (2)

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
Sn1	0.048315 (11)	0.27946 (3)	1.020054 (19)	0.03886 (14)
N1	0.01878 (12)	0.0950 (3)	0.9179 (2)	0.0349 (7)
N2	0.06107 (13)	−0.0095 (3)	0.9467 (2)	0.0376 (7)
O1	0.12024 (12)	0.1269 (3)	1.0986 (2)	0.0523 (7)
O2	−0.03879 (12)	0.3500 (3)	0.9082 (2)	0.0521 (7)
S1	0.15173 (5)	−0.22404 (11)	0.99530 (9)	0.0539 (3)
C1	0.11107 (16)	0.0181 (4)	1.0394 (3)	0.0370 (8)
C2	0.15988 (15)	−0.0829 (4)	1.0761 (3)	0.0391 (8)
C3	0.21560 (16)	−0.0837 (4)	1.1713 (3)	0.0467 (10)
H3	0.2285	−0.0161	1.2256	0.056*
C4	0.2510 (2)	−0.1982 (5)	1.1778 (4)	0.0616 (13)
H4	0.2899	−0.2146	1.2369	0.074*
C5	0.2225 (2)	−0.2813 (5)	1.0887 (5)	0.0607 (13)
H5	0.2395	−0.3610	1.0794	0.073*
C6	−0.03252 (16)	0.0748 (4)	0.8280 (3)	0.0370 (8)
H6	−0.0366	−0.0080	0.7916	0.044*
C7	−0.08356 (16)	0.1645 (4)	0.7783 (3)	0.0365 (8)
C8	−0.08526 (18)	0.2962 (4)	0.8193 (3)	0.0398 (9)
C9	−0.13876 (18)	0.3717 (4)	0.7621 (3)	0.0502 (10)
H9	−0.1407	0.4589	0.7876	0.060*
C10	−0.1884 (2)	0.3209 (5)	0.6696 (3)	0.0583 (12)
H10	−0.2233	0.3743	0.6331	0.070*
C11	−0.1875 (2)	0.1908 (5)	0.6295 (3)	0.0566 (12)
H11	−0.2216	0.1558	0.5673	0.068*
C12	−0.13538 (17)	0.1152 (4)	0.6835 (3)	0.0473 (10)
H12	−0.1342	0.0284	0.6566	0.057*
C13	0.0395 (2)	0.3048 (4)	1.1600 (3)	0.0551 (11)
H13A	0.0322	0.4001	1.1674	0.083*
H13B	0.0762	0.2756	1.2248	0.083*
H13C	0.0062	0.2502	1.1517	0.083*
C14	0.0958 (2)	0.4062 (4)	0.9684 (4)	0.0632 (12)
H14A	0.0804	0.3924	0.8910	0.095*
H14B	0.1380	0.3832	1.0093	0.095*
H14C	0.0905	0.5010	0.9815	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0461 (2)	0.02960 (19)	0.0389 (2)	−0.00223 (10)	0.02022 (14)	−0.00237 (10)
N1	0.0392 (16)	0.0290 (16)	0.0375 (16)	0.0007 (13)	0.0203 (14)	−0.0009 (12)
N2	0.0389 (16)	0.0310 (16)	0.0404 (16)	0.0027 (13)	0.0184 (14)	0.0010 (13)
O1	0.0495 (16)	0.0409 (17)	0.0490 (15)	0.0032 (12)	0.0124 (13)	−0.0057 (13)
O2	0.0526 (16)	0.0378 (15)	0.0509 (16)	0.0087 (13)	0.0154 (13)	−0.0069 (13)
S1	0.0624 (7)	0.0447 (7)	0.0555 (7)	0.0119 (5)	0.0307 (6)	0.0046 (5)
C1	0.044 (2)	0.030 (2)	0.043 (2)	−0.0012 (15)	0.0261 (18)	0.0026 (16)
C2	0.040 (2)	0.035 (2)	0.048 (2)	−0.0005 (15)	0.0257 (18)	0.0059 (16)
C3	0.036 (2)	0.044 (2)	0.055 (2)	−0.0024 (17)	0.0196 (19)	0.0060 (19)
C4	0.039 (2)	0.069 (3)	0.072 (3)	0.011 (2)	0.025 (2)	0.023 (3)
C5	0.059 (3)	0.055 (3)	0.078 (3)	0.021 (2)	0.042 (3)	0.021 (3)
C6	0.048 (2)	0.0289 (19)	0.042 (2)	0.0000 (16)	0.0286 (18)	−0.0014 (15)
C7	0.044 (2)	0.0347 (19)	0.0344 (18)	0.0024 (16)	0.0230 (16)	0.0011 (16)
C8	0.049 (2)	0.039 (2)	0.0352 (19)	0.0044 (17)	0.0243 (18)	0.0026 (16)
C9	0.059 (2)	0.045 (2)	0.045 (2)	0.0177 (19)	0.026 (2)	0.0014 (18)
C10	0.059 (3)	0.063 (3)	0.042 (2)	0.025 (2)	0.017 (2)	0.003 (2)
C11	0.052 (3)	0.069 (3)	0.035 (2)	0.010 (2)	0.0123 (19)	−0.004 (2)
C12	0.055 (2)	0.047 (2)	0.035 (2)	0.0077 (18)	0.0190 (18)	−0.0006 (17)
C13	0.078 (3)	0.045 (3)	0.049 (2)	0.001 (2)	0.037 (2)	−0.0020 (19)
C14	0.079 (3)	0.044 (3)	0.083 (3)	−0.011 (2)	0.053 (3)	−0.004 (2)

Geometric parameters (Å, º)

Sn1—O2	2.087 (3)	C6—C7	1.424 (5)
Sn1—C14	2.102 (4)	C6—H6	0.93
Sn1—C13	2.105 (4)	C7—C12	1.403 (5)
Sn1—N1	2.175 (3)	C7—C8	1.410 (5)
Sn1—O1	2.177 (3)	C8—C9	1.394 (5)
N1—C6	1.293 (4)	C9—C10	1.367 (6)
N1—N2	1.386 (4)	C9—H9	0.93
N2—C1	1.309 (4)	C10—C11	1.388 (6)
O1—C1	1.290 (4)	C10—H10	0.93
O2—C8	1.318 (5)	C11—C12	1.367 (6)
S1—C5	1.702 (5)	C11—H11	0.93
S1—C2	1.722 (4)	C12—H12	0.93
C1—C2	1.461 (5)	C13—H13A	0.96
C2—C3	1.374 (5)	C13—H13B	0.96
C3—C4	1.409 (6)	C13—H13C	0.96
C3—H3	0.93	C14—H14A	0.96
C4—C5	1.349 (7)	C14—H14B	0.96
C4—H4	0.93	C14—H14C	0.96
C5—H5	0.93
O2—Sn1—C14	97.69 (16)	N1—C6—H6	116.2
O2—Sn1—C13	94.77 (15)	C7—C6—H6	116.2
C14—Sn1—C13	127.60 (18)	C12—C7—C8	119.0 (3)
O2—Sn1—N1	83.86 (10)	C12—C7—C6	116.6 (3)
C14—Sn1—N1	108.79 (15)	C8—C7—C6	124.4 (3)
C13—Sn1—N1	123.08 (14)	O2—C8—C9	119.2 (3)
O2—Sn1—O1	155.62 (10)	O2—C8—C7	123.0 (3)
C14—Sn1—O1	94.76 (16)	C9—C8—C7	117.8 (3)
C13—Sn1—O1	94.09 (14)	C10—C9—C8	121.8 (4)
N1—Sn1—O1	72.29 (10)	C10—C9—H9	119.1
C6—N1—N2	115.5 (3)	C8—C9—H9	119.1
C6—N1—Sn1	127.5 (2)	C9—C10—C11	120.9 (4)
N2—N1—Sn1	116.8 (2)	C9—C10—H10	119.6
C1—N2—N1	111.5 (3)	C11—C10—H10	119.6
C1—O1—Sn1	113.6 (2)	C12—C11—C10	118.4 (4)
C8—O2—Sn1	133.5 (2)	C12—C11—H11	120.8
C5—S1—C2	91.5 (2)	C10—C11—H11	120.8
O1—C1—N2	125.0 (3)	C11—C12—C7	122.1 (4)
O1—C1—C2	118.6 (3)	C11—C12—H12	119.0
N2—C1—C2	116.3 (3)	C7—C12—H12	119.0
C3—C2—C1	128.8 (4)	Sn1—C13—H13A	109.5
C3—C2—S1	110.8 (3)	Sn1—C13—H13B	109.5
C1—C2—S1	120.4 (3)	H13A—C13—H13B	109.5
C2—C3—C4	112.6 (4)	Sn1—C13—H13C	109.5
C2—C3—H3	123.7	H13A—C13—H13C	109.5
C4—C3—H3	123.7	H13B—C13—H13C	109.5
C5—C4—C3	112.5 (4)	Sn1—C14—H14A	109.5
C5—C4—H4	123.7	Sn1—C14—H14B	109.5
C3—C4—H4	123.7	H14A—C14—H14B	109.5
C4—C5—S1	112.5 (3)	Sn1—C14—H14C	109.5
C4—C5—H5	123.7	H14A—C14—H14C	109.5
S1—C5—H5	123.7	H14B—C14—H14C	109.5
N1—C6—C7	127.6 (3)