Chloro­(1-isopropyl­idene-4-methyl-3-thio­semicarbazidato-κ²N³,S)diphenyl­tin(IV)

The Cl and imino N atoms occupy the axial sites of the cis-trigonal–bipyramidal environment of the Sn^IV atom in the title compound, [Sn(C₆H₅)₂(C₅H₁₀N₃S)Cl].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.029
• wR factor = 0.073
• Data-to-parameter ratio = 20.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

   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

   1 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
   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: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Chloro(1-isopropylidene-4-methyl-3-thiosemicarbazidato- κ²N³,S)diphenyltin(IV)

Crystal data

[Sn(C6H5)2(C5H10N3S)Cl]	F(000) = 904
Mr = 452.56	Dx = 1.542 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1011 reflections
a = 8.232 (1) Å	θ = 2.6–28.2°
b = 20.702 (2) Å	µ = 1.56 mm^−1
c = 12.011 (1) Å	T = 293 K
β = 107.785 (1)°	Block, colourless
V = 1949.1 (3) Å^3	0.4 × 0.3 × 0.2 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	4342 independent reflections
Radiation source: fine-focus sealed tube	3974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω and φ scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.575, Tmax = 0.746	k = −26→26
11555 measured reflections	l = −15→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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.5193P] where P = (Fo^2 + 2Fc^2)/3
4342 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.70654 (2)	0.621547 (8)	0.727125 (14)	0.04357 (7)
Cl1	0.94223 (9)	0.66790 (4)	0.65977 (7)	0.0656 (2)
S1	0.82164 (9)	0.68603 (4)	0.90080 (6)	0.05969 (18)
N1	0.5299 (3)	0.59249 (10)	0.83944 (17)	0.0461 (4)
N2	0.5684 (3)	0.61663 (10)	0.9527 (2)	0.0500 (5)
N3	0.7362 (3)	0.68208 (12)	1.0922 (2)	0.0609 (6)
H3N	0.8212	0.7082	1.1146	0.073*
C1	0.5094 (3)	0.66678 (11)	0.5915 (2)	0.0427 (5)
C2	0.5303 (3)	0.67803 (14)	0.4833 (2)	0.0555 (6)
H2	0.6257	0.6618	0.4668	0.067*
C3	0.4109 (4)	0.71302 (16)	0.3997 (3)	0.0663 (8)
H3	0.4254	0.7196	0.3268	0.080*
C4	0.2703 (4)	0.73829 (15)	0.4233 (3)	0.0648 (8)
H4	0.1919	0.7631	0.3675	0.078*
C5	0.2464 (4)	0.72663 (14)	0.5297 (3)	0.0614 (7)
H5	0.1504	0.7429	0.5454	0.074*
C6	0.3644 (3)	0.69081 (12)	0.6135 (2)	0.0500 (6)
H6	0.3468	0.6827	0.6851	0.060*
C7	0.7957 (3)	0.52520 (13)	0.7303 (2)	0.0522 (6)
C8	0.8335 (5)	0.49917 (16)	0.6353 (3)	0.0744 (9)
H8	0.8197	0.5242	0.5688	0.089*
C9	0.8920 (5)	0.4361 (2)	0.6378 (4)	0.0958 (13)
H9	0.9147	0.4187	0.5728	0.115*
C10	0.9159 (5)	0.39994 (18)	0.7358 (5)	0.0974 (14)
H10	0.9553	0.3577	0.7376	0.117*
C11	0.8824 (5)	0.42509 (18)	0.8324 (4)	0.0921 (12)
H11	0.9007	0.4002	0.8996	0.111*
C12	0.8211 (4)	0.48777 (16)	0.8294 (3)	0.0718 (8)
H12	0.7972	0.5046	0.8944	0.086*
C13	0.6419 (5)	0.66528 (17)	1.1725 (3)	0.0772 (9)
H13A	0.5242	0.6769	1.1387	0.116*
H13B	0.6887	0.6882	1.2447	0.116*
H13C	0.6506	0.6196	1.1873	0.116*
C14	0.6931 (3)	0.65761 (12)	0.9837 (2)	0.0482 (6)
C15	0.3453 (4)	0.52604 (16)	0.6878 (3)	0.0741 (9)
H15A	0.4193	0.5412	0.6452	0.111*
H15B	0.2297	0.5378	0.6467	0.111*
H15C	0.3538	0.4799	0.6951	0.111*
C16	0.3968 (3)	0.55598 (13)	0.8068 (2)	0.0542 (6)
C17	0.2891 (4)	0.54129 (18)	0.8831 (3)	0.0748 (9)
H17A	0.3551	0.5176	0.9505	0.112*
H17B	0.1928	0.5158	0.8403	0.112*
H17C	0.2500	0.5809	0.9076	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03650 (10)	0.05018 (11)	0.04320 (11)	−0.00218 (6)	0.01093 (7)	0.00819 (6)
Cl1	0.0436 (3)	0.0821 (5)	0.0763 (5)	−0.0049 (3)	0.0259 (3)	0.0197 (4)
S1	0.0526 (4)	0.0713 (4)	0.0520 (4)	−0.0201 (3)	0.0113 (3)	−0.0026 (3)
N1	0.0430 (11)	0.0523 (11)	0.0429 (11)	−0.0023 (9)	0.0126 (9)	0.0091 (9)
N2	0.0503 (12)	0.0562 (12)	0.0456 (12)	0.0026 (9)	0.0178 (10)	0.0079 (9)
N3	0.0688 (15)	0.0629 (14)	0.0474 (13)	0.0048 (12)	0.0124 (11)	−0.0010 (10)
C1	0.0383 (12)	0.0464 (12)	0.0417 (12)	−0.0024 (10)	0.0098 (9)	0.0056 (9)
C2	0.0466 (14)	0.0689 (17)	0.0528 (15)	0.0009 (12)	0.0179 (12)	0.0084 (12)
C3	0.0614 (18)	0.089 (2)	0.0462 (15)	−0.0065 (16)	0.0127 (13)	0.0186 (14)
C4	0.0505 (16)	0.0695 (18)	0.0659 (18)	−0.0001 (13)	0.0051 (13)	0.0233 (14)
C5	0.0448 (15)	0.0636 (16)	0.076 (2)	0.0071 (12)	0.0184 (13)	0.0135 (14)
C6	0.0471 (14)	0.0547 (14)	0.0503 (14)	−0.0003 (11)	0.0182 (11)	0.0064 (11)
C7	0.0422 (14)	0.0531 (14)	0.0570 (15)	0.0011 (11)	0.0087 (11)	0.0059 (12)
C8	0.080 (2)	0.073 (2)	0.0609 (19)	0.0096 (17)	0.0071 (16)	−0.0057 (15)
C9	0.093 (3)	0.087 (3)	0.088 (3)	0.021 (2)	0.000 (2)	−0.027 (2)
C10	0.074 (2)	0.062 (2)	0.127 (4)	0.0153 (18)	−0.012 (2)	−0.006 (2)
C11	0.081 (2)	0.072 (2)	0.113 (3)	0.0136 (19)	0.013 (2)	0.037 (2)
C12	0.069 (2)	0.072 (2)	0.075 (2)	0.0118 (16)	0.0232 (16)	0.0212 (16)
C13	0.101 (3)	0.079 (2)	0.0582 (19)	0.0153 (19)	0.0343 (18)	−0.0021 (16)
C14	0.0484 (14)	0.0494 (13)	0.0444 (13)	0.0072 (11)	0.0106 (11)	0.0074 (10)
C15	0.072 (2)	0.082 (2)	0.0632 (19)	−0.0322 (17)	0.0119 (15)	0.0017 (16)
C16	0.0462 (14)	0.0594 (15)	0.0556 (15)	−0.0067 (12)	0.0137 (11)	0.0140 (12)
C17	0.0526 (17)	0.098 (2)	0.079 (2)	−0.0168 (16)	0.0283 (16)	0.0182 (18)

Geometric parameters (Å, º)

Sn1—C7	2.122 (3)	C7—C8	1.381 (4)
Sn1—C1	2.133 (2)	C7—C12	1.381 (4)
Sn1—N1	2.344 (2)	C8—C9	1.389 (5)
Sn1—S1	2.413 (1)	C8—H8	0.93
Sn1—Cl1	2.510 (1)	C9—C10	1.357 (6)
S1—C14	1.761 (3)	C9—H9	0.93
N1—C16	1.290 (3)	C10—C11	1.374 (6)
N1—N2	1.392 (3)	C10—H10	0.93
N2—C14	1.296 (3)	C11—C12	1.389 (5)
N3—C14	1.340 (3)	C11—H11	0.93
N3—C13	1.454 (4)	C12—H12	0.93
N3—H3N	0.86	C13—H13A	0.96
C1—C2	1.381 (3)	C13—H13B	0.96
C1—C6	1.391 (3)	C13—H13C	0.96
C2—C3	1.377 (4)	C15—C16	1.496 (4)
C2—H2	0.93	C15—H15A	0.96
C3—C4	1.377 (4)	C15—H15B	0.96
C3—H3	0.93	C15—H15C	0.96
C4—C5	1.372 (4)	C16—C17	1.487 (4)
C4—H4	0.93	C17—H17A	0.96
C5—C6	1.382 (4)	C17—H17B	0.96
C5—H5	0.93	C17—H17C	0.96
C6—H6	0.93
C1—Sn1—C7	127.2 (1)	C7—C8—C9	120.9 (3)
C1—Sn1—N1	95.3 (1)	C7—C8—H8	119.6
C1—Sn1—S1	115.1 (1)	C9—C8—H8	119.6
C1—Sn1—Cl1	93.9 (1)	C10—C9—C8	119.7 (4)
C7—Sn1—N1	91.2 (1)	C10—C9—H9	120.2
C7—Sn1—S1	117.5 (1)	C8—C9—H9	120.2
C7—Sn1—Cl1	93.9 (1)	C9—C10—C11	120.7 (4)
N1—Sn1—S1	78.1 (1)	C9—C10—H10	119.7
N1—Sn1—Cl1	163.8 (1)	C11—C10—H10	119.7
S1—Sn1—Cl1	85.93 (3)	C10—C11—C12	119.8 (4)
C14—S1—Sn1	99.15 (9)	C10—C11—H11	120.1
C16—N1—N2	115.2 (2)	C12—C11—H11	120.1
C16—N1—Sn1	126.48 (18)	C11—C12—C7	120.3 (4)
N2—N1—Sn1	118.30 (15)	C11—C12—H12	119.8
C14—N2—N1	116.1 (2)	C7—C12—H12	119.8
C14—N3—C13	121.2 (3)	N3—C13—H13A	109.5
C14—N3—H3N	119.4	N3—C13—H13B	109.5
C13—N3—H3N	119.4	H13A—C13—H13B	109.5
C2—C1—C6	118.6 (2)	N3—C13—H13C	109.5
C2—C1—Sn1	120.57 (18)	H13A—C13—H13C	109.5
C6—C1—Sn1	120.57 (18)	H13B—C13—H13C	109.5
C3—C2—C1	120.6 (3)	N2—C14—N3	118.6 (2)
C3—C2—H2	119.7	N2—C14—S1	128.0 (2)
C1—C2—H2	119.7	N3—C14—S1	113.4 (2)
C2—C3—C4	120.5 (3)	C16—C15—H15A	109.5
C2—C3—H3	119.7	C16—C15—H15B	109.5
C4—C3—H3	119.7	H15A—C15—H15B	109.5
C5—C4—C3	119.6 (3)	C16—C15—H15C	109.5
C5—C4—H4	120.2	H15A—C15—H15C	109.5
C3—C4—H4	120.2	H15B—C15—H15C	109.5
C4—C5—C6	120.3 (3)	N1—C16—C17	122.9 (3)
C4—C5—H5	119.9	N1—C16—C15	120.0 (2)
C6—C5—H5	119.9	C17—C16—C15	117.1 (3)
C5—C6—C1	120.4 (2)	C16—C17—H17A	109.5
C5—C6—H6	119.8	C16—C17—H17B	109.5
C1—C6—H6	119.8	H17A—C17—H17B	109.5
C8—C7—C12	118.7 (3)	C16—C17—H17C	109.5
C8—C7—Sn1	121.1 (2)	H17A—C17—H17C	109.5
C12—C7—Sn1	120.2 (2)	H17B—C17—H17C	109.5
C7—Sn1—S1—C14	−81.22 (12)	C2—C1—C6—C5	−1.7 (4)
C1—Sn1—S1—C14	94.05 (11)	Sn1—C1—C6—C5	172.5 (2)
N1—Sn1—S1—C14	3.80 (10)	C1—Sn1—C7—C8	47.5 (3)
Cl1—Sn1—S1—C14	−173.51 (9)	N1—Sn1—C7—C8	145.0 (2)
C7—Sn1—N1—C16	−68.1 (2)	S1—Sn1—C7—C8	−137.9 (2)
C1—Sn1—N1—C16	59.5 (2)	Cl1—Sn1—C7—C8	−50.4 (2)
S1—Sn1—N1—C16	174.0 (2)	C1—Sn1—C7—C12	−134.2 (2)
Cl1—Sn1—N1—C16	−176.34 (17)	N1—Sn1—C7—C12	−36.7 (3)
C7—Sn1—N1—N2	112.45 (17)	S1—Sn1—C7—C12	40.4 (3)
C1—Sn1—N1—N2	−120.01 (17)	Cl1—Sn1—C7—C12	127.9 (2)
S1—Sn1—N1—N2	−5.47 (15)	C12—C7—C8—C9	1.6 (5)
Cl1—Sn1—N1—N2	4.2 (3)	Sn1—C7—C8—C9	179.9 (3)
C16—N1—N2—C14	−174.5 (2)	C7—C8—C9—C10	−1.4 (6)
Sn1—N1—N2—C14	5.0 (3)	C8—C9—C10—C11	0.1 (7)
C7—Sn1—C1—C2	−66.5 (2)	C9—C10—C11—C12	1.0 (6)
N1—Sn1—C1—C2	−161.9 (2)	C10—C11—C12—C7	−0.8 (6)
S1—Sn1—C1—C2	118.8 (2)	C8—C7—C12—C11	−0.5 (5)
Cl1—Sn1—C1—C2	31.5 (2)	Sn1—C7—C12—C11	−178.8 (3)
C7—Sn1—C1—C6	119.5 (2)	N1—N2—C14—N3	−179.6 (2)
N1—Sn1—C1—C6	24.0 (2)	N1—N2—C14—S1	−0.7 (3)
S1—Sn1—C1—C6	−55.3 (2)	C13—N3—C14—N2	−2.3 (4)
Cl1—Sn1—C1—C6	−142.61 (19)	C13—N3—C14—S1	178.6 (2)
C6—C1—C2—C3	0.8 (4)	Sn1—S1—C14—N2	−3.5 (2)
Sn1—C1—C2—C3	−173.3 (2)	Sn1—S1—C14—N3	175.52 (17)
C1—C2—C3—C4	1.1 (5)	N2—N1—C16—C17	1.1 (4)
C2—C3—C4—C5	−2.2 (5)	Sn1—N1—C16—C17	−178.4 (2)
C3—C4—C5—C6	1.3 (5)	N2—N1—C16—C15	−178.6 (2)
C4—C5—C6—C1	0.7 (4)	Sn1—N1—C16—C15	1.9 (4)