Chloro­dieth­yl[4-(4-nitro­phen­yl)piperazine-1-carbodithio­ato]tin(IV)

Zia-ur-Rahman; Ali, S.; Muhammad, N.; Meetsma, A.

doi:10.1107/S1600536806047611

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Chlorodiethyl[4-(4-nitrophenyl)piperazine-1-carbodithioato]tin(IV)

Zia-ur-Rahman, S. Ali, N. Muhammad and A. Meetsma

The molecule of the title compound, [Sn(C₂H₅)₂(C₁₁H₁₂N₃O₂S₂)Cl], features an asymmetrically chelating thiocarboxylate ligand. The Sn atom is five-coordinate within a C₂ClS₂ donor set that is best described as trigonal bipyramidal with S and Cl atoms in axial positions, defining a bond angle of 156.58 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047611/ng2151sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047611/ng2151Isup2.hkl Contains datablock I

CCDC reference: 630188

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.024
wR factor = 0.062
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       7.27 Ratio

Author Response: ...

  There are some methyl-hydrogen  which show larger displacement
  factors than the averge of the hydrogen Ueq, but one (H14') shows
  a bigger value, and is the one who make the high ratio.
   For us this is still reasonable.



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn     -   Cl      ..      16.15 su

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.20
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...         22
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.84 Ratio

   1 ALERT level A = In general: serious problem
   1 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
   3 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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: XPREP (Bruker, 2000); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Chlorodiethyl[4-(4-nitrophenyl)piperazine-1-carbodithioato]tin(IV) top

Crystal data top

[Sn(C₂H₅)₂(C₁₁H₁₂N₃O₂S₂)Cl]	F(000) = 992
M_r = 494.65	The final unit cell was obtained from the xyz centroids of 5242 reflections after integration using the SAINTPLUS software package (Bruker, 2000). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the finalatomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Monoclinic, P2₁/c	D_x = 1.735 Mg m⁻³
Hall symbol: -P 2y b c	Mo Kα radiation, λ = 0.71073 Å
a = 14.1638 (9) Å	Cell parameters from 5242 reflections
b = 10.5851 (7) Å	θ = 2.5–29.6°
c = 14.0247 (9) Å	µ = 1.73 mm⁻¹
β = 115.799 (1)°	T = 100 K
V = 1893.1 (2) Å³	Trianglar block, yellow
Z = 4	0.49 × 0.42 × 0.35 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4661 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	4332 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	R_int = 0.021
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θ_max = 28.3°, θ_min = 2.5°
φ and ω scans	h = −18→16
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	k = −14→14
T_min = 0.430, T_max = 0.549	l = −18→18
16982 measured reflections

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.024	Hydrogen site location: difference Fourier map
wR(F²) = 0.062	All H-atom parameters refined
S = 1.07	w = 1/[σ²(F_o²) + (0.0298P)² + 2.2398P] where P = (F_o² + 2F_c²)/3
4661 reflections	(Δ/σ)_max < 0.001
305 parameters	Δρ_max = 1.25 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Å²) top

	x	y	z	U_iso*/U_eq
Sn	0.06969 (1)	0.23293 (1)	0.29408 (1)	0.0143 (1)
Cl	−0.11109 (4)	0.19507 (5)	0.28215 (4)	0.0170 (1)
S1	0.08452 (4)	0.41066 (5)	0.41456 (4)	0.0168 (2)
S2	0.25528 (4)	0.35152 (5)	0.35415 (4)	0.0168 (2)
O1	0.36114 (14)	1.29089 (15)	0.64523 (14)	0.0231 (5)
O2	0.48872 (14)	1.27462 (15)	0.59962 (14)	0.0224 (5)
N1	0.42322 (16)	1.22714 (17)	0.62536 (14)	0.0168 (5)
N2	0.40698 (14)	0.69539 (17)	0.64976 (14)	0.0135 (5)
N3	0.26164 (14)	0.54391 (17)	0.48052 (14)	0.0142 (5)
C1	0.41949 (17)	1.09049 (19)	0.63219 (16)	0.0146 (5)
C2	0.49031 (17)	1.0166 (2)	0.61263 (16)	0.0150 (6)
C3	0.48520 (17)	0.8863 (2)	0.61714 (17)	0.0149 (6)
C4	0.40907 (16)	0.82616 (19)	0.64143 (15)	0.0127 (5)
C5	0.33951 (17)	0.9046 (2)	0.66236 (17)	0.0162 (6)
C6	0.34489 (17)	1.0344 (2)	0.65790 (17)	0.0165 (6)
C7	0.44451 (17)	0.6135 (2)	0.58890 (17)	0.0152 (6)
C8	0.35810 (17)	0.5924 (2)	0.47702 (17)	0.0166 (6)
C9	0.22677 (17)	0.6194 (2)	0.54797 (17)	0.0154 (6)
C10	0.31822 (17)	0.6341 (2)	0.65770 (16)	0.0144 (6)
C11	0.20862 (16)	0.4468 (2)	0.42303 (16)	0.0144 (6)
C12	0.0106 (2)	0.2682 (2)	0.12730 (19)	0.0205 (6)
C13	0.0752 (2)	0.3504 (3)	0.08976 (19)	0.0250 (7)
C14	0.1402 (2)	0.0587 (3)	0.3675 (2)	0.0274 (8)
C15	0.2238 (3)	0.0120 (3)	0.3377 (3)	0.0360 (10)
H2	0.540 (2)	1.056 (3)	0.596 (2)	0.019 (7)*
H3	0.533 (2)	0.842 (3)	0.608 (2)	0.015 (6)*
H5	0.289 (2)	0.874 (3)	0.677 (2)	0.027 (8)*
H6	0.302 (2)	1.083 (3)	0.670 (2)	0.015 (6)*
H7	0.4639 (19)	0.536 (2)	0.6239 (19)	0.011 (6)*
H7'	0.508 (2)	0.647 (3)	0.586 (2)	0.025 (7)*
H8	0.341 (2)	0.669 (3)	0.439 (2)	0.016 (6)*
H8'	0.378 (2)	0.534 (3)	0.438 (2)	0.023 (7)*
H9	0.171 (2)	0.580 (2)	0.555 (2)	0.015 (6)*
H9'	0.208 (2)	0.705 (3)	0.516 (2)	0.018 (7)*
H10	0.297 (2)	0.681 (3)	0.704 (2)	0.019 (7)*
H10'	0.344 (2)	0.549 (3)	0.689 (2)	0.015 (6)*
H12	0.008 (2)	0.184 (3)	0.101 (2)	0.027 (7)*
H12'	−0.061 (3)	0.303 (3)	0.111 (2)	0.032 (8)*
H13	0.089 (2)	0.436 (3)	0.123 (2)	0.030 (8)*
H13'	0.139 (2)	0.306 (3)	0.099 (2)	0.026 (7)*
H13"	0.034 (2)	0.365 (3)	0.012 (2)	0.028 (8)*
H14	0.157 (3)	0.067 (4)	0.436 (3)	0.051 (11)*
H14'	0.089 (4)	0.002 (4)	0.347 (4)	0.080 (15)*
H15	0.193 (4)	0.002 (4)	0.263 (4)	0.080 (15)*
H15'	0.251 (3)	−0.068 (4)	0.368 (3)	0.058 (11)*
H15"	0.273 (3)	0.076 (4)	0.351 (3)	0.059 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn	0.0125 (1)	0.0134 (1)	0.0166 (1)	−0.0018 (1)	0.0060 (1)	−0.0014 (1)
Cl	0.0100 (2)	0.0165 (2)	0.0264 (3)	−0.0034 (2)	0.0096 (2)	−0.0030 (2)
S1	0.0134 (3)	0.0156 (3)	0.0229 (3)	−0.0031 (2)	0.0092 (2)	−0.0043 (2)
S2	0.0145 (3)	0.0196 (3)	0.0177 (2)	−0.0043 (2)	0.0083 (2)	−0.0057 (2)
O1	0.0277 (9)	0.0153 (8)	0.0267 (9)	0.0041 (7)	0.0121 (8)	−0.0005 (6)
O2	0.0290 (10)	0.0164 (8)	0.0240 (8)	−0.0055 (7)	0.0135 (7)	0.0008 (6)
N1	0.0210 (10)	0.0122 (9)	0.0147 (8)	−0.0010 (7)	0.0055 (8)	−0.0002 (7)
N2	0.0134 (9)	0.0120 (8)	0.0154 (8)	−0.0012 (6)	0.0067 (7)	−0.0012 (6)
N3	0.0123 (8)	0.0163 (9)	0.0147 (8)	−0.0021 (7)	0.0065 (7)	−0.0016 (7)
C1	0.0172 (10)	0.0116 (9)	0.0135 (9)	−0.0006 (8)	0.0053 (8)	−0.0006 (7)
C2	0.0159 (10)	0.0166 (10)	0.0143 (9)	−0.0025 (8)	0.0082 (8)	−0.0011 (7)
C3	0.0141 (10)	0.0155 (10)	0.0168 (9)	0.0005 (8)	0.0084 (8)	−0.0014 (8)
C4	0.0125 (10)	0.0123 (9)	0.0114 (9)	−0.0001 (7)	0.0035 (8)	−0.0002 (7)
C5	0.0152 (10)	0.0170 (10)	0.0196 (10)	−0.0006 (8)	0.0107 (9)	−0.0001 (8)
C6	0.0157 (10)	0.0170 (10)	0.0183 (10)	0.0021 (8)	0.0088 (9)	−0.0011 (8)
C7	0.0115 (10)	0.0133 (10)	0.0200 (10)	0.0000 (8)	0.0060 (8)	−0.0028 (8)
C8	0.0153 (10)	0.0173 (10)	0.0189 (10)	−0.0048 (8)	0.0091 (9)	−0.0034 (8)
C9	0.0122 (10)	0.0156 (10)	0.0185 (10)	−0.0012 (8)	0.0067 (8)	−0.0028 (8)
C10	0.0149 (10)	0.0140 (10)	0.0155 (9)	−0.0030 (8)	0.0077 (8)	−0.0009 (7)
C11	0.0124 (10)	0.0165 (10)	0.0129 (9)	−0.0001 (8)	0.0043 (8)	0.0026 (7)
C12	0.0196 (12)	0.0204 (11)	0.0194 (10)	−0.0023 (9)	0.0065 (9)	−0.0036 (9)
C13	0.0273 (13)	0.0284 (13)	0.0189 (11)	−0.0049 (10)	0.0096 (10)	−0.0021 (9)
C14	0.0281 (14)	0.0227 (12)	0.0379 (14)	0.0073 (10)	0.0204 (12)	0.0082 (10)
C15	0.0340 (16)	0.0243 (14)	0.058 (2)	0.0075 (12)	0.0278 (15)	−0.0017 (13)

Geometric parameters (Å, º) top

Sn—Cl	2.5243 (7)	C12—C13	1.514 (4)
Sn—S1	2.4758 (6)	C14—C15	1.501 (5)
Sn—S2	2.6959 (6)	C2—H2	0.93 (3)
Sn—C12	2.146 (2)	C3—H3	0.88 (3)
Sn—C14	2.136 (3)	C5—H5	0.89 (3)
S1—C11	1.752 (3)	C6—H6	0.87 (3)
S2—C11	1.716 (2)	C7—H7	0.93 (2)
O1—N1	1.233 (3)	C7—H7'	0.98 (3)
O2—N1	1.239 (3)	C8—H8	0.94 (3)
N1—C1	1.452 (3)	C8—H8'	0.95 (3)
N2—C4	1.391 (3)	C9—H9	0.94 (3)
N2—C7	1.469 (3)	C9—H9'	0.99 (3)
N2—C10	1.461 (3)	C10—H10	0.96 (3)
N3—C8	1.480 (3)	C10—H10'	1.00 (3)
N3—C9	1.478 (3)	C12—H12	0.96 (3)
N3—C11	1.321 (3)	C12—H12'	1.01 (4)
C1—C2	1.390 (3)	C13—H13	1.00 (3)
C1—C6	1.390 (4)	C13—H13'	0.98 (3)
C2—C3	1.384 (3)	C13—H13"	1.00 (3)
C3—C4	1.416 (3)	C14—H14	0.89 (4)
C4—C5	1.414 (3)	C14—H14'	0.89 (5)
C5—C6	1.379 (3)	C15—H15	0.95 (5)
C7—C8	1.529 (3)	C15—H15'	0.95 (4)
C9—C10	1.528 (3)	C15—H15"	0.93 (5)

Sn···H14'ⁱ	3.63 (5)	C2···H2^ix	2.87 (3)
Sn···H13"ⁱⁱ	3.47 (3)	C3···H2^ix	2.92 (3)
Cl···S1	3.4430 (8)	C3···H7'	2.61 (3)
Cl···C12	3.398 (3)	C4···H9'	2.91 (3)
Cl···C14	3.532 (3)	C4···H8	3.06 (3)
Cl···H12'	3.01 (3)	C5···H10	2.57 (3)
Cl···H13ⁱⁱⁱ	3.00 (3)	C5···H9'	2.97 (3)
Cl···H5^iv	2.91 (3)	C6···H7^viii	3.08 (3)
Cl···H10^iv	3.02 (3)	C7···H3	2.68 (3)
Cl···H13"ⁱⁱ	3.04 (3)	C8···H10'	3.10 (3)
S1···Cl	3.4430 (8)	C10···H5	2.61 (3)
S1···S2	2.9569 (9)	C12···H9'ⁱⁱⁱ	2.94 (3)
S2···C12	3.649 (3)	C12···H14'ⁱ	2.95 (5)
S2···C13	3.467 (3)	C13···H14^xiii	2.99 (4)
S2···S1	2.9569 (9)	C13···H6^v	2.99 (3)
S2···C15	3.616 (3)	C14···H12'ⁱⁱⁱ	3.00 (3)
S2···C14	3.545 (3)	H2···O2	2.43 (3)
S2···C6^v	3.699 (2)	H2···C2^ix	2.87 (3)
S1···H12ⁱ	3.14 (3)	H2···C3^ix	2.92 (3)
S1···H9	2.55 (2)	H3···C7	2.68 (3)
S2···H8'	2.52 (3)	H3···H7'	2.09 (4)
S2···H15"	2.93 (4)	H5···C10	2.61 (3)
S2···H7'^vi	3.08 (3)	H5···H10	2.07 (4)
S2···H13	3.20 (3)	H5···Cl^iv	2.91 (3)
S2···H6^v	3.01 (3)	H6···O1	2.43 (3)
O1···C11^vii	3.353 (3)	H6···S2^xi	3.01 (3)
O1···C4^viii	3.348 (3)	H6···C13^xi	2.99 (3)
O1···C3^viii	3.248 (3)	H6···H13'^xi	2.39 (4)
O2···C8^ix	3.142 (3)	H7···O2^xii	2.83 (2)
O2···C7^ix	3.386 (3)	H7···H10'	2.26 (4)
O2···C4^viii	3.318 (3)	H7···C6^x	3.08 (3)
O1···H6	2.43 (3)	H7'···C3	2.61 (3)
O1···H10'^vii	2.83 (3)	H7'···H3	2.09 (4)
O2···H2	2.43 (3)	H7'···S2^vi	3.08 (3)
O2···H7^vii	2.83 (2)	H7'···O2^ix	2.75 (3)
O2···H7'^ix	2.75 (3)	H8···C4	3.06 (3)
O2···H8^ix	2.76 (3)	H8···H9'	2.58 (4)
N1···N2^viii	3.040 (3)	H8···O2^ix	2.76 (3)
N1···C4^viii	3.267 (3)	H8'···S2	2.52 (3)
N2···N3	2.862 (3)	H9···S1	2.55 (2)
N2···N1^x	3.040 (3)	H9'···C4	2.91 (3)
N2···C1^x	3.175 (3)	H9'···C5	2.97 (3)
N3···N2	2.862 (3)	H9'···H8	2.58 (4)
C1···N2^viii	3.175 (3)	H9'···C12ⁱ	2.94 (3)
C1···C7^viii	3.537 (3)	H9'···H12'ⁱ	2.31 (4)
C2···C10^viii	3.417 (3)	H10···C5	2.57 (3)
C2···C2^ix	3.307 (3)	H10···H5	2.07 (4)
C2···C3^ix	3.540 (3)	H10···Cl^iv	3.02 (3)
C3···C2^ix	3.540 (3)	H10'···O1^xii	2.83 (3)
C3···O1^x	3.248 (3)	H10'···C8	3.10 (3)
C4···O1^x	3.348 (3)	H10'···H7	2.26 (4)
C4···O2^x	3.318 (3)	H10'···C2^x	2.77 (3)
C4···N1^x	3.267 (3)	H12···S1ⁱⁱⁱ	3.14 (3)
C5···C9	3.465 (3)	H12'···C14ⁱ	3.00 (3)
C6···S2^xi	3.699 (2)	H12'···H9'ⁱⁱⁱ	2.31 (4)
C7···C1^x	3.537 (3)	H12'···H14'ⁱ	2.27 (6)
C7···O2^ix	3.386 (3)	H13···S2	3.20 (3)
C8···O2^ix	3.142 (3)	H13···Clⁱ	3.00 (3)
C9···C12ⁱ	3.554 (4)	H13'···H6^v	2.39 (4)
C9···C5	3.465 (3)	H13"···Sn^xiii	3.47 (3)
C10···C2^x	3.417 (3)	H13"···Cl^xiii	3.04 (3)
C11···O1^xii	3.353 (3)	H13"···H14^xiii	2.51 (5)
C12···C9ⁱⁱⁱ	3.554 (4)	H14···C13ⁱⁱ	2.99 (4)
C12···S2	3.649 (3)	H14···H13"ⁱⁱ	2.51 (5)
C12···Cl	3.398 (3)	H14'···Snⁱⁱⁱ	3.63 (5)
C14···S2	3.545 (3)	H14'···C12ⁱⁱⁱ	2.95 (5)
C14···Cl	3.532 (3)	H14'···H12'ⁱⁱⁱ	2.27 (6)
C2···H10'^viii	2.77 (3)	H15"···S2	2.93 (4)

Cl—Sn—S1	87.03 (2)	C6—C5—H5	116 (2)
Cl—Sn—S2	156.58 (2)	C1—C6—H6	118 (2)
Cl—Sn—C12	92.99 (8)	C5—C6—H6	122 (2)
Cl—Sn—C14	98.21 (8)	N2—C7—H7	108.1 (16)
S1—Sn—S2	69.59 (2)	N2—C7—H7'	112.3 (17)
S1—Sn—C12	119.25 (6)	C8—C7—H7	109.4 (15)
S1—Sn—C14	116.36 (7)	C8—C7—H7'	110.4 (15)
S2—Sn—C12	97.14 (8)	H7—C7—H7'	106 (3)
S2—Sn—C14	93.65 (8)	N3—C8—H8	107.7 (19)
C12—Sn—C14	123.66 (9)	N3—C8—H8'	107.7 (19)
Sn—S1—C11	89.82 (7)	C7—C8—H8	110.4 (17)
Sn—S2—C11	83.54 (8)	C7—C8—H8'	112.5 (17)
O1—N1—O2	122.82 (19)	H8—C8—H8'	108 (2)
O1—N1—C1	118.7 (2)	N3—C9—H9	111.1 (15)
O2—N1—C1	118.5 (2)	N3—C9—H9'	107.6 (16)
C4—N2—C7	120.82 (19)	C10—C9—H9	108.9 (16)
C4—N2—C10	119.9 (2)	C10—C9—H9'	107.7 (16)
C7—N2—C10	108.86 (17)	H9—C9—H9'	112 (2)
C8—N3—C9	113.84 (17)	N2—C10—H10	110.7 (19)
C8—N3—C11	122.52 (19)	N2—C10—H10'	105.8 (18)
C9—N3—C11	123.5 (2)	C9—C10—H10	110.8 (17)
N1—C1—C2	119.8 (2)	C9—C10—H10'	109.8 (16)
N1—C1—C6	119.8 (2)	H10—C10—H10'	109 (2)
C2—C1—C6	120.42 (19)	Sn—C12—H12	100.9 (16)
C1—C2—C3	119.7 (2)	Sn—C12—H12'	100.8 (16)
C2—C3—C4	121.3 (2)	C13—C12—H12	109.2 (18)
N2—C4—C3	120.9 (2)	C13—C12—H12'	114.3 (19)
N2—C4—C5	121.7 (2)	H12—C12—H12'	113 (3)
C3—C4—C5	117.30 (19)	C12—C13—H13	112.6 (17)
C4—C5—C6	121.2 (2)	C12—C13—H13'	110.0 (18)
C1—C6—C5	120.1 (2)	C12—C13—H13"	108.3 (18)
N2—C7—C8	110.6 (2)	H13—C13—H13'	113 (3)
N3—C8—C7	110.78 (18)	H13—C13—H13"	106 (2)
N3—C9—C10	109.1 (2)	H13'—C13—H13"	107 (2)
N2—C10—C9	110.41 (18)	Sn—C14—H14	107 (3)
S1—C11—S2	117.04 (12)	Sn—C14—H14'	106 (3)
S1—C11—N3	119.91 (18)	C15—C14—H14	118 (3)
S2—C11—N3	123.05 (19)	C15—C14—H14'	109 (4)
Sn—C12—C13	118.10 (17)	H14—C14—H14'	102 (4)
Sn—C14—C15	114.2 (2)	C14—C15—H15	108 (4)
C1—C2—H2	119.1 (19)	C14—C15—H15'	113 (3)
C3—C2—H2	121.2 (19)	C14—C15—H15"	109 (3)
C2—C3—H3	118 (2)	H15—C15—H15'	107 (4)
C4—C3—H3	121 (2)	H15—C15—H15"	104 (4)
C4—C5—H5	123 (2)	H15'—C15—H15"	116 (4)

Cl—Sn—S1—C11	−177.91 (7)	C10—N2—C4—C3	−170.05 (18)
S2—Sn—S1—C11	0.63 (7)	C10—N2—C4—C5	13.5 (3)
C12—Sn—S1—C11	−86.14 (12)	C4—N2—C7—C8	−84.0 (2)
C14—Sn—S1—C11	84.39 (12)	C10—N2—C7—C8	60.9 (2)
Cl—Sn—S2—C11	3.03 (9)	C4—N2—C10—C9	81.7 (2)
S1—Sn—S2—C11	−0.64 (7)	C7—N2—C10—C9	−63.5 (2)
C12—Sn—S2—C11	117.96 (10)	C9—N3—C8—C7	51.0 (2)
C14—Sn—S2—C11	−117.45 (10)	C11—N3—C8—C7	−133.0 (2)
Cl—Sn—C12—C13	154.18 (19)	C8—N3—C9—C10	−52.7 (2)
S1—Sn—C12—C13	65.9 (2)	C11—N3—C9—C10	131.4 (2)
S2—Sn—C12—C13	−4.7 (2)	C8—N3—C11—S1	−169.60 (15)
C14—Sn—C12—C13	−103.9 (2)	C8—N3—C11—S2	10.3 (3)
Cl—Sn—C14—C15	148.7 (2)	C9—N3—C11—S1	6.0 (3)
S1—Sn—C14—C15	−120.6 (2)	C9—N3—C11—S2	−174.15 (16)
S2—Sn—C14—C15	−51.6 (2)	N1—C1—C2—C3	−178.72 (19)
C12—Sn—C14—C15	49.5 (3)	C6—C1—C2—C3	1.1 (3)
Sn—S1—C11—S2	−1.04 (11)	N1—C1—C6—C5	178.65 (19)
Sn—S1—C11—N3	178.87 (17)	C2—C1—C6—C5	−1.1 (3)
Sn—S2—C11—S1	0.96 (11)	C1—C2—C3—C4	0.0 (3)
Sn—S2—C11—N3	−178.95 (18)	C2—C3—C4—N2	−177.54 (19)
O1—N1—C1—C2	−178.47 (19)	C2—C3—C4—C5	−0.9 (3)
O1—N1—C1—C6	1.7 (3)	N2—C4—C5—C6	177.4 (2)
O2—N1—C1—C2	1.6 (3)	C3—C4—C5—C6	0.8 (3)
O2—N1—C1—C6	−178.2 (2)	C4—C5—C6—C1	0.2 (3)
C7—N2—C4—C3	−29.0 (3)	N2—C7—C8—N3	−54.2 (2)
C7—N2—C4—C5	154.5 (2)	N3—C9—C10—N2	58.6 (2)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) x, −y+3/2, z−1/2; (vi) −x+1, −y+1, −z+1; (vii) x, y+1, z; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+1, −y+2, −z+1; (x) −x+1, y−1/2, −z+3/2; (xi) x, −y+3/2, z+1/2; (xii) x, y−1, z; (xiii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.87 (3)	2.43 (3)	2.737 (3)	101 (2)
C8—H8′···S2	0.95 (3)	2.52 (3)	3.067 (2)	117 (2)
C9—H9···S1	0.94 (3)	2.55 (2)	3.027 (2)	112.1 (19)

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