Bromo­(N,N-dimethyl­dithio­carbamato-κ²S,S′)­diphenyl­tin(IV)

The Sn atom in the title compound, [SnBr(C₆H₅)₂(C₃H₆NS₂)], adopts a distorted SnBrC₂S₂ trigonal–bipyramidal environment.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.042
• wR factor = 0.094
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Bromo(N,N-dimethyldithiocarbamato-κ²S,S')diphenyltin(IV)

Crystal data

[SnBr(C6H5)2(C3H6NS2)]	F(000) = 1840
Mr = 473.01	Dx = 1.795 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1999 reflections
a = 17.560 (8) Å	θ = 2.3–23.0°
b = 9.133 (3) Å	µ = 3.97 mm^−1
c = 21.838 (10) Å	T = 295 K
β = 91.772 (6)°	Block, colorless
V = 3501 (3) Å^3	0.14 × 0.10 × 0.10 mm
Z = 8

Data collection

Bruker APEX area-detector diffractometer	3634 independent reflections
Radiation source: fine-focus sealed tube	2687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→21
Tmin = 0.606, Tmax = 0.692	k = −9→11
9614 measured reflections	l = −27→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 3.0728P] where P = (Fo^2 + 2Fc^2)/3
3634 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.64 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
Sn1	0.106187 (19)	0.98099 (4)	0.409303 (16)	0.04355 (13)
Br1	0.18451 (3)	1.02641 (7)	0.51104 (3)	0.06259 (19)
S1	0.03072 (8)	0.80477 (17)	0.46671 (6)	0.0548 (4)
S2	−0.01164 (8)	0.88752 (18)	0.33986 (7)	0.0632 (4)
C1	−0.0287 (3)	0.7814 (5)	0.4020 (2)	0.0472 (13)
C10	0.1938 (3)	0.8825 (6)	0.3586 (2)	0.0477 (13)
N1	−0.0840 (3)	0.6836 (5)	0.4021 (2)	0.0578 (12)
C9	0.1477 (3)	1.3036 (6)	0.3980 (2)	0.0546 (14)
H9	0.1906	1.2731	0.4205	0.066*
C11	0.2501 (3)	0.7984 (6)	0.3851 (3)	0.0606 (15)
H11	0.2489	0.7789	0.4269	0.073*
C4	0.0894 (3)	1.2050 (6)	0.3849 (2)	0.0454 (12)
C15	0.1972 (4)	0.9102 (8)	0.2967 (3)	0.0739 (18)
H15	0.1586	0.9644	0.2774	0.089*
C2	−0.0963 (4)	0.5866 (7)	0.4545 (3)	0.081 (2)
H2A	−0.0775	0.4905	0.4455	0.121*
H2B	−0.1498	0.5813	0.4621	0.121*
H2C	−0.0696	0.6245	0.4901	0.121*
C5	0.0271 (3)	1.2537 (6)	0.3522 (3)	0.0653 (17)
H5	−0.0126	1.1893	0.3428	0.078*
C13	0.3113 (4)	0.7752 (9)	0.2900 (4)	0.095 (3)
H13	0.3510	0.7399	0.2669	0.114*
C12	0.3092 (4)	0.7412 (8)	0.3514 (4)	0.088 (2)
H12	0.3463	0.6816	0.3698	0.106*
C3	−0.1374 (3)	0.6701 (8)	0.3503 (3)	0.079 (2)
H3A	−0.1806	0.7321	0.3566	0.118*
H3B	−0.1541	0.5702	0.3467	0.118*
H3C	−0.1130	0.6989	0.3135	0.118*
C14	0.2564 (4)	0.8594 (10)	0.2628 (3)	0.096 (3)
H14	0.2588	0.8827	0.2214	0.115*
C7	0.0810 (5)	1.4930 (7)	0.3456 (3)	0.0733 (19)
H7	0.0784	1.5894	0.3319	0.088*
C8	0.1425 (4)	1.4459 (7)	0.3782 (3)	0.0690 (17)
H8	0.1820	1.5107	0.3874	0.083*
C6	0.0221 (4)	1.3977 (7)	0.3326 (3)	0.082 (2)
H6	−0.0210	1.4299	0.3108	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0375 (2)	0.0426 (2)	0.0506 (2)	−0.00720 (16)	0.00163 (15)	0.00101 (16)
Br1	0.0577 (4)	0.0694 (4)	0.0597 (4)	−0.0069 (3)	−0.0131 (3)	−0.0030 (3)
S1	0.0548 (8)	0.0615 (9)	0.0485 (8)	−0.0200 (7)	0.0063 (6)	0.0003 (7)
S2	0.0581 (9)	0.0628 (10)	0.0677 (10)	−0.0171 (7)	−0.0151 (7)	0.0101 (8)
C1	0.040 (3)	0.041 (3)	0.061 (3)	−0.001 (2)	0.010 (2)	−0.009 (2)
C10	0.048 (3)	0.044 (3)	0.052 (3)	−0.013 (2)	0.012 (2)	−0.004 (2)
N1	0.050 (3)	0.051 (3)	0.073 (3)	−0.011 (2)	0.005 (2)	−0.009 (2)
C9	0.056 (3)	0.052 (4)	0.056 (3)	−0.014 (3)	0.001 (3)	0.004 (3)
C11	0.054 (4)	0.053 (4)	0.076 (4)	−0.004 (3)	0.017 (3)	0.008 (3)
C4	0.041 (3)	0.047 (3)	0.048 (3)	0.003 (2)	0.007 (2)	−0.003 (2)
C15	0.063 (4)	0.098 (5)	0.061 (4)	−0.013 (4)	0.000 (3)	−0.006 (4)
C2	0.076 (5)	0.075 (5)	0.092 (5)	−0.030 (4)	0.019 (4)	−0.004 (4)
C5	0.053 (4)	0.049 (4)	0.094 (5)	0.003 (3)	−0.001 (3)	0.002 (3)
C13	0.065 (5)	0.093 (6)	0.129 (8)	−0.020 (4)	0.042 (5)	−0.053 (5)
C12	0.055 (4)	0.070 (5)	0.142 (8)	−0.007 (3)	0.033 (5)	−0.007 (5)
C3	0.058 (4)	0.077 (5)	0.101 (5)	−0.021 (3)	−0.011 (4)	−0.004 (4)
C14	0.070 (5)	0.147 (8)	0.072 (5)	−0.034 (5)	0.029 (4)	−0.036 (5)
C7	0.103 (5)	0.046 (4)	0.071 (4)	0.004 (4)	0.017 (4)	0.000 (3)
C8	0.077 (4)	0.060 (4)	0.071 (4)	−0.017 (3)	0.012 (4)	−0.004 (3)
C6	0.074 (5)	0.060 (5)	0.111 (6)	0.015 (4)	−0.007 (4)	0.010 (4)

Geometric parameters (Å, º)

Sn1—C10	2.124 (5)	C15—H15	0.9300
Sn1—C4	2.132 (5)	C2—H2A	0.9600
Sn1—S1	2.4537 (15)	C2—H2B	0.9600
Sn1—Br1	2.6098 (11)	C2—H2C	0.9600
Sn1—S2	2.6674 (16)	C5—C6	1.385 (8)
C1—S1	1.744 (5)	C5—H5	0.9300
C1—S2	1.701 (6)	C13—C14	1.356 (10)
C1—N1	1.319 (6)	C13—C12	1.378 (11)
C10—C11	1.366 (7)	C13—H13	0.9300
C10—C15	1.378 (8)	C12—H12	0.9300
N1—C3	1.453 (7)	C3—H3A	0.9600
N1—C2	1.468 (7)	C3—H3B	0.9600
C9—C8	1.372 (8)	C3—H3C	0.9600
C9—C4	1.386 (7)	C14—H14	0.9300
C9—H9	0.9300	C7—C8	1.344 (9)
C11—C12	1.393 (8)	C7—C6	1.375 (9)
C11—H11	0.9300	C7—H7	0.9300
C4—C5	1.363 (7)	C8—H8	0.9300
C15—C14	1.376 (9)	C6—H6	0.9300
C10—Sn1—C4	111.87 (19)	N1—C2—H2A	109.5
C10—Sn1—S1	113.58 (14)	N1—C2—H2B	109.5
C4—Sn1—S1	133.21 (14)	H2A—C2—H2B	109.5
C10—Sn1—Br1	98.05 (15)	N1—C2—H2C	109.5
C4—Sn1—Br1	97.21 (14)	H2A—C2—H2C	109.5
S1—Sn1—Br1	87.02 (5)	H2B—C2—H2C	109.5
C10—Sn1—S2	97.45 (15)	C4—C5—C6	120.9 (6)
C4—Sn1—S2	93.80 (14)	C4—C5—H5	119.5
S1—Sn1—S2	70.05 (5)	C6—C5—H5	119.5
Br1—Sn1—S2	156.05 (4)	C14—C13—C12	120.9 (7)
C1—S1—Sn1	89.13 (18)	C14—C13—H13	119.5
C1—S2—Sn1	83.20 (18)	C12—C13—H13	119.5
N1—C1—S2	122.4 (4)	C13—C12—C11	118.3 (7)
N1—C1—S1	120.2 (4)	C13—C12—H12	120.9
S2—C1—S1	117.5 (3)	C11—C12—H12	120.9
C11—C10—C15	117.9 (5)	N1—C3—H3A	109.5
C11—C10—Sn1	122.9 (4)	N1—C3—H3B	109.5
C15—C10—Sn1	119.2 (5)	H3A—C3—H3B	109.5
C1—N1—C3	120.9 (5)	N1—C3—H3C	109.5
C1—N1—C2	122.5 (5)	H3A—C3—H3C	109.5
C3—N1—C2	116.6 (5)	H3B—C3—H3C	109.5
C8—C9—C4	120.6 (6)	C13—C14—C15	119.7 (8)
C8—C9—H9	119.7	C13—C14—H14	120.2
C4—C9—H9	119.7	C15—C14—H14	120.2
C10—C11—C12	121.8 (6)	C8—C7—C6	119.5 (6)
C10—C11—H11	119.1	C8—C7—H7	120.2
C12—C11—H11	119.1	C6—C7—H7	120.2
C5—C4—C9	118.1 (5)	C7—C8—C9	121.0 (6)
C5—C4—Sn1	123.1 (4)	C7—C8—H8	119.5
C9—C4—Sn1	118.5 (4)	C9—C8—H8	119.5
C14—C15—C10	121.4 (7)	C7—C6—C5	119.9 (6)
C14—C15—H15	119.3	C7—C6—H6	120.1
C10—C15—H15	119.3	C5—C6—H6	120.1
C10—Sn1—S1—C1	−87.3 (2)	C15—C10—C11—C12	−0.3 (9)
C4—Sn1—S1—C1	78.2 (3)	Sn1—C10—C11—C12	−176.6 (4)
Br1—Sn1—S1—C1	175.25 (17)	C8—C9—C4—C5	−0.4 (8)
S2—Sn1—S1—C1	2.29 (17)	C8—C9—C4—Sn1	173.9 (4)
C10—Sn1—S2—C1	110.1 (2)	C10—Sn1—C4—C5	108.3 (5)
C4—Sn1—S2—C1	−137.3 (2)	S1—Sn1—C4—C5	−57.3 (5)
S1—Sn1—S2—C1	−2.36 (17)	Br1—Sn1—C4—C5	−150.0 (5)
Br1—Sn1—S2—C1	−19.9 (2)	S2—Sn1—C4—C5	8.7 (5)
Sn1—S2—C1—N1	−175.9 (4)	C10—Sn1—C4—C9	−65.7 (4)
Sn1—S2—C1—S1	3.5 (3)	S1—Sn1—C4—C9	128.7 (3)
Sn1—S1—C1—N1	175.7 (4)	Br1—Sn1—C4—C9	36.0 (4)
Sn1—S1—C1—S2	−3.8 (3)	S2—Sn1—C4—C9	−165.3 (4)
C4—Sn1—C10—C11	133.4 (4)	C11—C10—C15—C14	−2.1 (9)
S1—Sn1—C10—C11	−58.0 (5)	Sn1—C10—C15—C14	174.4 (5)
Br1—Sn1—C10—C11	32.2 (4)	C9—C4—C5—C6	0.0 (9)
S2—Sn1—C10—C11	−129.5 (4)	Sn1—C4—C5—C6	−174.0 (5)
C4—Sn1—C10—C15	−42.9 (5)	C14—C13—C12—C11	−1.5 (11)
S1—Sn1—C10—C15	125.7 (4)	C10—C11—C12—C13	2.0 (10)
Br1—Sn1—C10—C15	−144.1 (4)	C12—C13—C14—C15	−0.8 (11)
S2—Sn1—C10—C15	54.2 (4)	C10—C15—C14—C13	2.7 (11)
S2—C1—N1—C3	−5.1 (7)	C6—C7—C8—C9	0.9 (10)
S1—C1—N1—C3	175.5 (4)	C4—C9—C8—C7	0.0 (9)
S2—C1—N1—C2	176.7 (4)	C8—C7—C6—C5	−1.3 (11)
S1—C1—N1—C2	−2.7 (7)	C4—C5—C6—C7	0.8 (11)