(Acetone 4-phenyl­thio­semicarbazonato-κ²N,S)chloro­diphenyl­tin(IV) ethanol solvate

The Sn^IV atom in the title compound, [Sn(C₆H₅)₂(C₁₀H₁₂N₃S)Cl]·C₂H₅OH, exists in a cis-trigonal–bipyramidal geometry. The Cl and imino N atoms occupy the axial sites.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.112
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C23
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C23    -   C24    ...       1.42 Ang.

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
   3 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
   2 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
   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.

(Acetone-4-phenylthiosemicarbazonato-κ²N,S)chlorodiphenyltin(IV) ethanol solvate

Crystal data

[Sn(C6H5)2(C10H12N3S)Cl]·C2H6O	F(000) = 1136
Mr = 560.69	Dx = 1.440 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 934 reflections
a = 8.110 (1) Å	θ = 2.9–26.3°
b = 12.195 (1) Å	µ = 1.19 mm^−1
c = 26.144 (3) Å	T = 293 K
β = 90.146 (1)°	Block, colourless
V = 2585.7 (5) Å^3	0.34 × 0.14 × 0.11 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	5817 independent reflections
Radiation source: fine-focus sealed tube	4918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.687, Tmax = 0.880	k = −15→9
15470 measured reflections	l = −33→32

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.7047P] where P = (Fo^2 + 2Fc^2)/3
5817 reflections	(Δ/σ)max = 0.001
285 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.64 e Å^−3

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

	x	y	z	Uiso*/Ueq
Sn1	0.65958 (3)	0.65338 (2)	0.638688 (9)	0.04038 (10)
Cl1	0.38412 (13)	0.68585 (11)	0.67883 (4)	0.0616 (3)
S1	0.61306 (13)	0.46426 (9)	0.66021 (4)	0.0569 (3)
O1	0.4676 (5)	0.6918 (4)	0.80383 (15)	0.0964 (12)
H1O	0.4660	0.6898	0.7713	0.116*
N1	0.7819 (4)	0.2930 (3)	0.63489 (12)	0.0489 (8)
H1N	0.7080	0.2683	0.6548	0.059 (13)*
N2	0.9022 (4)	0.4521 (2)	0.60526 (12)	0.0438 (7)
N3	0.8934 (4)	0.5665 (2)	0.60337 (11)	0.0395 (7)
C1	0.8833 (5)	0.2124 (3)	0.61206 (15)	0.0464 (9)
C2	0.8509 (7)	0.1072 (4)	0.6275 (2)	0.0774 (15)
H2	0.7719	0.0938	0.6525	0.093*
C3	0.9364 (8)	0.0214 (4)	0.6058 (3)	0.102 (2)
H3	0.9156	−0.0498	0.6168	0.122*
C4	1.0514 (8)	0.0389 (4)	0.5685 (2)	0.0883 (17)
H4	1.1042	−0.0199	0.5528	0.106*
C5	1.0869 (7)	0.1440 (4)	0.5546 (2)	0.0725 (14)
H5	1.1683	0.1573	0.5304	0.087*
C6	1.0031 (6)	0.2308 (4)	0.57630 (17)	0.0596 (11)
H6	1.0281	0.3022	0.5665	0.072*
C7	0.7844 (5)	0.4041 (3)	0.62982 (14)	0.0429 (8)
C8	1.0164 (5)	0.6123 (3)	0.58131 (14)	0.0437 (8)
C9	1.1585 (6)	0.5500 (4)	0.5603 (2)	0.0701 (14)
H9A	1.2065	0.5060	0.5869	0.105*
H9B	1.2395	0.6004	0.5476	0.105*
H9C	1.1212	0.5035	0.5330	0.105*
C10	1.0238 (5)	0.7334 (3)	0.57600 (17)	0.0578 (11)
H10A	0.9172	0.7641	0.5830	0.087*
H10B	1.0562	0.7520	0.5418	0.087*
H10C	1.1028	0.7625	0.5998	0.087*
C11	0.7893 (5)	0.7567 (3)	0.69048 (13)	0.0431 (8)
C12	0.9487 (5)	0.7355 (4)	0.70626 (15)	0.0553 (10)
H12	1.0032	0.6738	0.6940	0.066*
C13	1.0280 (6)	0.8045 (5)	0.74003 (18)	0.0725 (14)
H13	1.1347	0.7886	0.7509	0.087*
C14	0.9498 (7)	0.8964 (5)	0.75756 (19)	0.0780 (15)
H14	1.0046	0.9434	0.7799	0.094*
C15	0.7927 (7)	0.9199 (4)	0.74265 (18)	0.0699 (13)
H15	0.7402	0.9826	0.7547	0.084*
C16	0.7116 (6)	0.8496 (3)	0.70940 (17)	0.0571 (11)
H16	0.6036	0.8649	0.6996	0.069*
C17	0.5804 (4)	0.7092 (3)	0.56581 (14)	0.0456 (9)
C18	0.5019 (6)	0.8090 (4)	0.56081 (18)	0.0643 (12)
H18	0.4869	0.8529	0.5895	0.077*
C19	0.4450 (7)	0.8449 (5)	0.5137 (2)	0.0862 (18)
H19	0.3941	0.9129	0.5107	0.103*
C20	0.4641 (6)	0.7797 (6)	0.4717 (2)	0.0863 (18)
H20	0.4256	0.8035	0.4401	0.104*
C21	0.5390 (7)	0.6802 (5)	0.47576 (19)	0.0780 (15)
H21	0.5508	0.6360	0.4470	0.094*
C22	0.5971 (6)	0.6452 (4)	0.52235 (16)	0.0592 (11)
H22	0.6486	0.5772	0.5248	0.071*
C23	0.6293 (9)	0.6696 (6)	0.8216 (3)	0.098 (2)
H23A	0.6350	0.6832	0.8581	0.118*
H23B	0.7064	0.7186	0.8049	0.118*
C24	0.6754 (11)	0.5594 (7)	0.8116 (3)	0.154 (4)
H24A	0.6127	0.5112	0.8331	0.231*
H24B	0.7908	0.5502	0.8187	0.231*
H24C	0.6540	0.5425	0.7764	0.231*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03785 (15)	0.04149 (16)	0.04183 (16)	0.00353 (11)	0.00393 (10)	−0.00566 (12)
Cl1	0.0401 (5)	0.0809 (8)	0.0639 (6)	0.0084 (5)	0.0125 (5)	−0.0087 (6)
S1	0.0559 (6)	0.0459 (6)	0.0690 (7)	−0.0016 (5)	0.0253 (5)	−0.0021 (5)
O1	0.092 (3)	0.122 (3)	0.075 (2)	0.029 (3)	0.024 (2)	−0.003 (3)
N1	0.055 (2)	0.0376 (19)	0.055 (2)	−0.0014 (15)	0.0123 (16)	−0.0006 (16)
N2	0.0425 (17)	0.0331 (16)	0.0557 (19)	0.0020 (13)	0.0049 (14)	−0.0041 (14)
N3	0.0385 (16)	0.0359 (17)	0.0439 (16)	0.0019 (13)	0.0052 (13)	−0.0052 (13)
C1	0.053 (2)	0.037 (2)	0.050 (2)	0.0019 (17)	−0.0007 (18)	−0.0001 (17)
C2	0.087 (4)	0.038 (2)	0.107 (4)	0.006 (2)	0.027 (3)	0.009 (3)
C3	0.120 (5)	0.034 (3)	0.152 (6)	0.011 (3)	0.052 (4)	0.003 (3)
C4	0.107 (4)	0.045 (3)	0.113 (5)	0.015 (3)	0.021 (4)	−0.016 (3)
C5	0.077 (3)	0.061 (3)	0.079 (3)	0.012 (2)	0.020 (3)	−0.011 (3)
C6	0.069 (3)	0.043 (2)	0.067 (3)	0.006 (2)	0.014 (2)	−0.002 (2)
C7	0.045 (2)	0.042 (2)	0.042 (2)	0.0000 (17)	−0.0013 (16)	−0.0054 (17)
C8	0.038 (2)	0.045 (2)	0.048 (2)	0.0000 (17)	0.0029 (16)	−0.0055 (18)
C9	0.056 (3)	0.055 (3)	0.099 (4)	0.001 (2)	0.031 (3)	−0.015 (3)
C10	0.061 (3)	0.042 (2)	0.070 (3)	−0.003 (2)	0.015 (2)	0.003 (2)
C11	0.045 (2)	0.045 (2)	0.0394 (19)	0.0032 (17)	0.0035 (16)	−0.0049 (16)
C12	0.047 (2)	0.068 (3)	0.050 (2)	0.012 (2)	−0.0005 (18)	−0.012 (2)
C13	0.047 (3)	0.107 (4)	0.063 (3)	0.004 (3)	−0.012 (2)	−0.025 (3)
C14	0.080 (4)	0.087 (4)	0.067 (3)	−0.010 (3)	−0.010 (3)	−0.031 (3)
C15	0.083 (4)	0.053 (3)	0.074 (3)	0.006 (2)	0.004 (3)	−0.023 (2)
C16	0.053 (3)	0.055 (3)	0.064 (3)	0.010 (2)	−0.003 (2)	−0.010 (2)
C17	0.038 (2)	0.051 (2)	0.048 (2)	−0.0006 (17)	0.0020 (16)	−0.0007 (18)
C18	0.065 (3)	0.065 (3)	0.063 (3)	0.015 (2)	0.002 (2)	0.001 (2)
C19	0.069 (4)	0.090 (4)	0.099 (4)	0.018 (3)	−0.002 (3)	0.033 (4)
C20	0.063 (3)	0.134 (6)	0.062 (3)	−0.002 (3)	−0.008 (3)	0.023 (4)
C21	0.082 (4)	0.102 (4)	0.050 (3)	−0.006 (3)	−0.006 (3)	−0.005 (3)
C22	0.054 (3)	0.070 (3)	0.053 (2)	0.000 (2)	0.003 (2)	−0.008 (2)
C23	0.103 (5)	0.105 (5)	0.088 (4)	−0.008 (4)	0.018 (4)	0.001 (4)
C24	0.158 (8)	0.133 (8)	0.170 (8)	0.026 (6)	−0.047 (7)	−0.008 (7)

Geometric parameters (Å, º)

Sn1—C11	2.126 (4)	C10—H10B	0.96
Sn1—C17	2.121 (4)	C10—H10C	0.96
Sn1—N3	2.362 (3)	C11—C12	1.380 (5)
Sn1—S1	2.404 (1)	C11—C16	1.388 (5)
Sn1—Cl1	2.502 (1)	C12—C13	1.379 (6)
S1—C7	1.763 (4)	C12—H12	0.93
O1—C23	1.416 (8)	C13—C14	1.368 (7)
O1—H1O	0.85	C13—H13	0.93
N1—C7	1.361 (5)	C14—C15	1.362 (7)
N1—C1	1.415 (5)	C14—H14	0.93
N1—H1N	0.85	C15—C16	1.385 (6)
N2—C7	1.292 (5)	C15—H15	0.93
N2—N3	1.398 (4)	C16—H16	0.93
N3—C8	1.282 (5)	C17—C18	1.380 (6)
C1—C6	1.369 (6)	C17—C22	1.386 (5)
C1—C2	1.370 (6)	C18—C19	1.384 (7)
C2—C3	1.378 (7)	C18—H18	0.93
C2—H2	0.93	C19—C20	1.365 (8)
C3—C4	1.369 (8)	C19—H19	0.93
C3—H3	0.93	C20—C21	1.361 (8)
C4—C5	1.363 (7)	C20—H20	0.93
C4—H4	0.93	C21—C22	1.373 (7)
C5—C6	1.381 (6)	C21—H21	0.93
C5—H5	0.93	C22—H22	0.93
C6—H6	0.93	C23—C24	1.418 (9)
C8—C10	1.485 (6)	C23—H23A	0.97
C8—C9	1.486 (5)	C23—H23B	0.97
C9—H9A	0.96	C24—H24A	0.96
C9—H9B	0.96	C24—H24B	0.96
C9—H9C	0.96	C24—H24C	0.96
C10—H10A	0.96
C11—Sn1—C17	122.0 (2)	C8—C10—H10C	109.5
C11—Sn1—N3	96.8 (1)	H10A—C10—H10C	109.5
C11—Sn1—S1	119.8 (1)	H10B—C10—H10C	109.5
C11—Sn1—Cl1	94.6 (1)	C12—C11—C16	118.2 (4)
C17—Sn1—N3	92.0 (1)	C12—C11—Sn1	122.7 (3)
C17—Sn1—S1	118.1 (1)	C16—C11—Sn1	119.1 (3)
C17—Sn1—Cl1	93.3 (1)	C13—C12—C11	120.8 (4)
N3—Sn1—S1	77.75 (8)	C13—C12—H12	119.6
N3—Sn1—Cl1	162.44 (8)	C11—C12—H12	119.6
S1—Sn1—Cl1	85.00 (4)	C14—C13—C12	120.0 (4)
C7—S1—Sn1	99.75 (14)	C14—C13—H13	120.0
C23—O1—H1O	109.5	C12—C13—H13	120.0
C7—N1—C1	129.9 (3)	C15—C14—C13	120.7 (4)
C7—N1—H1N	115.0	C15—C14—H14	119.7
C1—N1—H1N	115.0	C13—C14—H14	119.7
C7—N2—N3	115.6 (3)	C14—C15—C16	119.5 (4)
C8—N3—N2	114.3 (3)	C14—C15—H15	120.3
C8—N3—Sn1	127.4 (3)	C16—C15—H15	120.3
N2—N3—Sn1	118.3 (2)	C15—C16—C11	120.9 (4)
C6—C1—C2	119.5 (4)	C15—C16—H16	119.6
C6—C1—N1	126.0 (4)	C11—C16—H16	119.6
C2—C1—N1	114.5 (4)	C18—C17—C22	117.7 (4)
C3—C2—C1	119.5 (5)	C18—C17—Sn1	120.5 (3)
C3—C2—H2	120.3	C22—C17—Sn1	121.7 (3)
C1—C2—H2	120.3	C17—C18—C19	121.0 (5)
C4—C3—C2	121.3 (5)	C17—C18—H18	119.5
C4—C3—H3	119.3	C19—C18—H18	119.5
C2—C3—H3	119.3	C20—C19—C18	119.6 (5)
C3—C4—C5	118.7 (5)	C20—C19—H19	120.2
C3—C4—H4	120.6	C18—C19—H19	120.2
C5—C4—H4	120.6	C21—C20—C19	120.5 (5)
C4—C5—C6	120.5 (5)	C21—C20—H20	119.7
C4—C5—H5	119.7	C19—C20—H20	119.7
C6—C5—H5	119.7	C20—C21—C22	119.9 (5)
C1—C6—C5	120.3 (4)	C20—C21—H21	120.0
C1—C6—H6	119.8	C22—C21—H21	120.0
C5—C6—H6	119.8	C21—C22—C17	121.2 (5)
N2—C7—N1	120.7 (3)	C21—C22—H22	119.4
N2—C7—S1	128.3 (3)	C17—C22—H22	119.4
N1—C7—S1	111.0 (3)	O1—C23—C24	111.5 (6)
N3—C8—C10	120.5 (3)	O1—C23—H23A	109.3
N3—C8—C9	123.3 (4)	C24—C23—H23A	109.3
C10—C8—C9	116.2 (3)	O1—C23—H23B	109.3
C8—C9—H9A	109.5	C24—C23—H23B	109.3
C8—C9—H9B	109.5	H23A—C23—H23B	108.0
H9A—C9—H9B	109.5	C23—C24—H24A	109.5
C8—C9—H9C	109.5	C23—C24—H24B	109.5
H9A—C9—H9C	109.5	H24A—C24—H24B	109.5
H9B—C9—H9C	109.5	C23—C24—H24C	109.5
C8—C10—H10A	109.5	H24A—C24—H24C	109.5
C8—C10—H10B	109.5	H24B—C24—H24C	109.5
H10A—C10—H10B	109.5
C17—Sn1—S1—C7	82.48 (17)	Sn1—N3—C8—C9	179.8 (3)
C11—Sn1—S1—C7	−94.04 (17)	C17—Sn1—C11—C12	−117.0 (3)
N3—Sn1—S1—C7	−3.16 (15)	N3—Sn1—C11—C12	−20.3 (4)
Cl1—Sn1—S1—C7	173.54 (13)	S1—Sn1—C11—C12	59.4 (4)
C7—N2—N3—C8	176.2 (3)	Cl1—Sn1—C11—C12	146.3 (3)
C7—N2—N3—Sn1	−4.7 (4)	C17—Sn1—C11—C16	63.0 (4)
C17—Sn1—N3—C8	65.4 (3)	N3—Sn1—C11—C16	159.6 (3)
C11—Sn1—N3—C8	−57.1 (3)	S1—Sn1—C11—C16	−120.6 (3)
S1—Sn1—N3—C8	−176.3 (3)	Cl1—Sn1—C11—C16	−33.8 (3)
Cl1—Sn1—N3—C8	172.8 (2)	C16—C11—C12—C13	0.2 (6)
C17—Sn1—N3—N2	−113.5 (3)	Sn1—C11—C12—C13	−179.8 (4)
C11—Sn1—N3—N2	123.9 (3)	C11—C12—C13—C14	−1.2 (8)
S1—Sn1—N3—N2	4.8 (2)	C12—C13—C14—C15	1.1 (9)
Cl1—Sn1—N3—N2	−6.1 (4)	C13—C14—C15—C16	0.0 (9)
C7—N1—C1—C6	−4.4 (7)	C14—C15—C16—C11	−1.0 (8)
C7—N1—C1—C2	177.3 (4)	C12—C11—C16—C15	0.9 (6)
C6—C1—C2—C3	−1.7 (8)	Sn1—C11—C16—C15	−179.1 (4)
N1—C1—C2—C3	176.7 (5)	C11—Sn1—C17—C18	−46.4 (4)
C1—C2—C3—C4	−1.1 (10)	N3—Sn1—C17—C18	−145.7 (4)
C2—C3—C4—C5	3.4 (11)	S1—Sn1—C17—C18	137.1 (3)
C3—C4—C5—C6	−2.9 (10)	Cl1—Sn1—C17—C18	51.0 (4)
C2—C1—C6—C5	2.2 (7)	C11—Sn1—C17—C22	137.1 (3)
N1—C1—C6—C5	−176.0 (4)	N3—Sn1—C17—C22	37.8 (3)
C4—C5—C6—C1	0.2 (9)	S1—Sn1—C17—C22	−39.4 (4)
N3—N2—C7—N1	−178.8 (3)	Cl1—Sn1—C17—C22	−125.4 (3)
N3—N2—C7—S1	1.1 (5)	C22—C17—C18—C19	−1.4 (7)
C1—N1—C7—N2	−7.9 (6)	Sn1—C17—C18—C19	−178.0 (4)
C1—N1—C7—S1	172.1 (3)	C17—C18—C19—C20	1.2 (8)
Sn1—S1—C7—N2	2.6 (4)	C18—C19—C20—C21	−0.3 (9)
Sn1—S1—C7—N1	−177.4 (2)	C19—C20—C21—C22	−0.5 (9)
N2—N3—C8—C10	179.5 (3)	C20—C21—C22—C17	0.3 (8)
Sn1—N3—C8—C10	0.5 (5)	C18—C17—C22—C21	0.6 (7)
N2—N3—C8—C9	−1.2 (6)	Sn1—C17—C22—C21	177.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1	0.85	2.51	3.336 (4)	166
N1—H1N···O1^i	0.85	2.02	2.863 (5)	172

Symmetry code: (i) −x+1, y−1/2, −z+3/2.