Di-μ₂-methoxo-bis­[benz­yl(5-chloro-2-oxido­benzaldehyde thio­semicarbazonato)tin(IV)]

The centrosymmetric title compound, [Sn₂(C₇H₇)₂(C₈H₆ClN₃OS)₂(CH₃O)₂], displays octa­hedrally coordinated tin within a CNO₃S donor set. Mol­ecules aggregate via N—H...N hydrogen bonds, leading to a chain, and these bonds combined with N—H...π and C—H...π inter­actions lead to a three-dimensional array.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.050
• wR factor = 0.117
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1B    ...          ?

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.915
            Tmax scaled      0.915 Tmin scaled      0.744

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

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Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006); software used to prepare material for publication: SHELXL97.

Di-µ₂-methoxo-bis[benzyl(5-chloro-2-oxidobenzaldehyde thiosemicarbazonato)tin(IV)]

Crystal data

[Sn2(C7H7)2(C8H6ClN3OS)2(CH3O)2]	F(000) = 928
Mr = 937.04	Dx = 1.800 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 5633 reflections
a = 11.617 (7) Å	θ = 6.3–25.0°
b = 13.484 (4) Å	µ = 1.77 mm^−1
c = 12.430 (4) Å	T = 173 K
β = 117.367 (5)°	Prism, pale yellow
V = 1729.1 (13) Å^3	0.15 × 0.05 × 0.05 mm
Z = 2

Data collection

Rigaku AFC12K/SATURN724 diffractometer	3906 independent reflections
Radiation source: fine-focus sealed tube	3887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω scans	θmax = 27.6°, θmin = 6.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
Tmin = 0.813, Tmax = 1	k = −17→17
44284 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.22	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 5.0883P] where P = (Fo^2 + 2Fc^2)/3
3906 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.99 e Å^−3
0 restraints	Δρmin = −0.77 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
Sn	0.12263 (3)	0.07572 (2)	0.09858 (2)	0.03440 (12)
Cl1	−0.24644 (15)	0.11846 (13)	0.44193 (15)	0.0631 (4)
S1	0.30172 (12)	−0.04494 (12)	0.14315 (11)	0.0485 (3)
O1	−0.0153 (3)	0.1608 (3)	0.1130 (3)	0.0395 (7)
O2	0.0048 (3)	0.0455 (2)	−0.0866 (3)	0.0349 (7)
N1	0.4961 (4)	−0.0644 (4)	0.3605 (4)	0.0554 (13)
H1A	0.5392	−0.0585	0.4398	0.067*
H1B	0.5311	−0.0961	0.3208	0.067*
N2	0.3298 (3)	0.0213 (3)	0.3643 (3)	0.0383 (9)
N3	0.2059 (3)	0.0597 (3)	0.2982 (3)	0.0335 (8)
C1	0.3770 (4)	−0.0252 (4)	0.3001 (4)	0.0435 (11)
C2	0.1447 (4)	0.0804 (3)	0.3595 (4)	0.0372 (10)
H2	0.1914	0.0738	0.4450	0.045*
C3	0.0109 (4)	0.1126 (4)	0.3098 (4)	0.0371 (9)
C4	−0.0630 (4)	0.1475 (4)	0.1906 (4)	0.0377 (10)
C5	−0.1933 (5)	0.1740 (4)	0.1534 (5)	0.0445 (11)
H5	−0.2442	0.1978	0.0733	0.053*
C6	−0.2487 (5)	0.1665 (4)	0.2300 (5)	0.0469 (12)
H6	−0.3364	0.1855	0.2031	0.056*
C7	−0.1759 (5)	0.1312 (4)	0.3461 (5)	0.0465 (11)
C8	−0.0470 (5)	0.1054 (4)	0.3857 (4)	0.0417 (10)
H8	0.0027	0.0822	0.4662	0.050*
C9	0.2144 (5)	0.2094 (4)	0.0781 (4)	0.0430 (11)
H9A	0.2780	0.1915	0.0490	0.052*
H9B	0.1479	0.2527	0.0165	0.052*
C10	0.2819 (5)	0.2650 (4)	0.1949 (4)	0.0419 (10)
C11	0.4068 (5)	0.2391 (4)	0.2796 (5)	0.0521 (13)
H11	0.4500	0.1864	0.2624	0.063*
C12	0.4689 (6)	0.2889 (5)	0.3885 (6)	0.0655 (17)
H12	0.5529	0.2686	0.4467	0.079*
C13	0.4101 (7)	0.3672 (5)	0.4129 (6)	0.0647 (17)
H13	0.4543	0.4024	0.4870	0.078*
C14	0.2878 (7)	0.3948 (5)	0.3311 (6)	0.0620 (16)
H14	0.2469	0.4496	0.3476	0.074*
C15	0.2232 (6)	0.3422 (4)	0.2231 (5)	0.0513 (13)
H15	0.1368	0.3600	0.1678	0.062*
C16	−0.0346 (6)	0.1260 (4)	−0.1710 (5)	0.0534 (13)
H16A	−0.0828	0.1746	−0.1488	0.080*
H16B	−0.0902	0.1008	−0.2527	0.080*
H16C	0.0421	0.1577	−0.1693	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.02894 (17)	0.0410 (2)	0.02513 (17)	0.00197 (11)	0.00540 (12)	−0.00128 (11)
Cl1	0.0609 (9)	0.0708 (10)	0.0727 (10)	0.0122 (7)	0.0437 (8)	0.0107 (8)
S1	0.0373 (6)	0.0666 (8)	0.0315 (6)	0.0152 (6)	0.0072 (5)	−0.0067 (5)
O1	0.0342 (16)	0.0477 (19)	0.0319 (15)	0.0080 (14)	0.0111 (13)	0.0039 (14)
O2	0.0373 (16)	0.0350 (15)	0.0219 (13)	−0.0010 (13)	0.0046 (12)	0.0016 (12)
N1	0.034 (2)	0.083 (3)	0.038 (2)	0.022 (2)	0.0061 (18)	−0.005 (2)
N2	0.0225 (16)	0.053 (2)	0.0278 (17)	0.0067 (16)	0.0015 (14)	0.0021 (16)
N3	0.0255 (17)	0.044 (2)	0.0211 (16)	0.0049 (14)	0.0025 (13)	−0.0006 (14)
C1	0.029 (2)	0.061 (3)	0.033 (2)	0.001 (2)	0.0073 (18)	−0.002 (2)
C2	0.033 (2)	0.046 (3)	0.025 (2)	0.0052 (18)	0.0072 (17)	0.0001 (17)
C3	0.031 (2)	0.038 (2)	0.034 (2)	0.0034 (18)	0.0091 (17)	−0.0013 (18)
C4	0.032 (2)	0.040 (2)	0.035 (2)	0.0049 (18)	0.0102 (18)	−0.0023 (18)
C5	0.032 (2)	0.051 (3)	0.040 (2)	0.006 (2)	0.0072 (19)	0.000 (2)
C6	0.032 (2)	0.054 (3)	0.051 (3)	0.009 (2)	0.016 (2)	0.000 (2)
C7	0.047 (3)	0.044 (3)	0.054 (3)	0.003 (2)	0.028 (2)	−0.003 (2)
C8	0.038 (2)	0.046 (3)	0.036 (2)	0.004 (2)	0.0120 (19)	−0.001 (2)
C9	0.044 (3)	0.048 (3)	0.035 (2)	−0.006 (2)	0.016 (2)	−0.003 (2)
C10	0.040 (2)	0.045 (3)	0.039 (2)	−0.011 (2)	0.017 (2)	−0.005 (2)
C11	0.033 (2)	0.059 (3)	0.054 (3)	−0.008 (2)	0.011 (2)	−0.008 (3)
C12	0.037 (3)	0.081 (5)	0.060 (4)	−0.017 (3)	0.006 (3)	−0.003 (3)
C13	0.065 (4)	0.067 (4)	0.051 (3)	−0.027 (3)	0.017 (3)	−0.015 (3)
C14	0.091 (5)	0.044 (3)	0.056 (3)	−0.002 (3)	0.037 (3)	−0.005 (3)
C15	0.053 (3)	0.053 (3)	0.038 (3)	0.008 (2)	0.013 (2)	0.003 (2)
C16	0.059 (3)	0.050 (3)	0.034 (2)	0.000 (3)	0.007 (2)	0.007 (2)

Geometric parameters (Å, º)

Sn—S1	2.4945 (16)	C5—H5	0.9500
Sn—N3	2.221 (4)	C6—C7	1.380 (7)
Sn—O1	2.045 (3)	C6—H6	0.9500
Sn—O2	2.108 (3)	C7—C8	1.388 (7)
Sn—C9	2.168 (5)	C8—H8	0.9500
Sn—O2^i	2.164 (3)	C9—C10	1.495 (6)
Cl1—C7	1.737 (5)	C9—H9A	0.9900
S1—C1	1.753 (5)	C9—H9B	0.9900
O1—C4	1.326 (6)	C10—C15	1.375 (7)
O2—C16	1.430 (6)	C10—C11	1.389 (7)
O2—Sn^i	2.164 (3)	C11—C12	1.380 (8)
N1—C1	1.343 (6)	C11—H11	0.9500
N1—H1A	0.8800	C12—C13	1.364 (10)
N1—H1B	0.8800	C12—H12	0.9500
N2—N3	1.388 (5)	C13—C14	1.366 (10)
N2—C1	1.317 (6)	C13—H13	0.9500
N3—C2	1.289 (6)	C14—C15	1.394 (8)
C2—C3	1.450 (6)	C14—H14	0.9500
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.409 (6)	C16—H16A	0.9800
C3—C8	1.391 (7)	C16—H16B	0.9800
C4—C5	1.410 (6)	C16—H16C	0.9800
C5—C6	1.377 (7)
S1—Sn—O1	162.51 (9)	C6—C5—H5	119.1
S1—Sn—O2	99.97 (10)	C7—C6—C5	119.5 (5)
S1—Sn—N3	78.35 (10)	C7—C6—H6	120.3
S1—Sn—C9	99.41 (15)	C5—C6—H6	120.3
S1—Sn—O2^i	89.82 (10)	C6—C7—C8	120.0 (5)
O1—Sn—O2	93.59 (13)	C6—C7—Cl1	119.7 (4)
O1—Sn—N3	85.00 (13)	C8—C7—Cl1	120.3 (4)
O1—Sn—C9	89.49 (17)	C7—C8—C3	121.4 (5)
O1—Sn—O2^i	83.75 (14)	C7—C8—H8	119.3
O2—Sn—N3	158.79 (14)	C3—C8—H8	119.3
O2—Sn—C9	98.05 (15)	C10—C9—Sn	111.7 (3)
O2—Sn—O2^i	72.46 (13)	C10—C9—H9A	109.3
C9—Sn—O2^i	167.90 (16)	Sn—C9—H9A	109.3
C9—Sn—N3	103.09 (16)	C10—C9—H9B	109.3
N3—Sn—O2^i	86.36 (13)	Sn—C9—H9B	109.3
Sn—S1—C1	94.97 (18)	H9A—C9—H9B	107.9
Sn—O1—C4	126.4 (3)	C15—C10—C11	117.6 (5)
Sn—O2—C16	118.9 (3)	C15—C10—C9	121.8 (5)
Sn^i—O2—C16	123.0 (3)	C11—C10—C9	120.6 (5)
Sn—O2—Sn^i	107.54 (13)	C12—C11—C10	121.0 (6)
C1—N1—H1A	120.0	C12—C11—H11	119.5
C1—N1—H1B	120.0	C10—C11—H11	119.5
H1A—N1—H1B	120.0	C11—C12—C13	120.3 (6)
C1—N2—N3	115.2 (4)	C11—C12—H12	119.8
C2—N3—N2	115.7 (4)	C13—C12—H12	119.8
Sn—N3—N2	119.9 (3)	C12—C13—C14	120.1 (6)
Sn—N3—C2	124.3 (3)	C12—C13—H13	120.0
N2—C1—N1	117.2 (4)	C14—C13—H13	120.0
N2—C1—S1	127.8 (4)	C15—C14—C13	119.6 (6)
N1—C1—S1	114.9 (4)	C15—C14—H14	120.2
N3—C2—C3	126.0 (4)	C13—C14—H14	120.2
N3—C2—H2	117.0	C14—C15—C10	121.4 (5)
C3—C2—H2	117.0	C14—C15—H15	119.3
C4—C3—C8	119.1 (4)	C10—C15—H15	119.3
C4—C3—C2	124.3 (4)	O2—C16—H16A	109.5
C8—C3—C2	116.6 (4)	O2—C16—H16B	109.5
O1—C4—C5	118.1 (4)	H16A—C16—H16B	109.5
O1—C4—C3	123.6 (4)	O2—C16—H16C	109.5
C5—C4—C3	118.2 (4)	H16A—C16—H16C	109.5
C4—C5—C6	121.8 (5)	H16B—C16—H16C	109.5
C4—C5—H5	119.1

Symmetry code: (i) −x, −y, −z.