Tris(2-hydroxy­anilinium) hexa­chloro­stannate(IV) chloride trihydrate

Bouacida, S.; Merazig, H.; Benard-Rocherulle, P.; Rizzoli, C.

doi:10.1107/S160053680605656X

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Tris(2-hydroxyanilinium) hexachlorostannate(IV) chloride trihydrate

S. Bouacida, H. Merazig, P. Benard-Rocherulle and C. Rizzoli

In the title compound, (C₆H₈NO)₃[SnCl₆]Cl·3H₂O, the asymmetric unit contains three independent cations of protonated o-aminophenol, one hexachlorostannate(IV) and one chloride anion, and three molecules of water. The crystal structure can be described as double layers of [SnCl₆] octahedra and 2-hydroxyanilinium cations parallel to the (10 $\overline{1}$ ) plane, with the chloride ions and the water molecules sandwiched between the double layers. A myriad of hydrogen bonds, namely, cation-cation, cation-anion, cation-water and water-water, result in a complex network of intermolecular bonds reinforcing the cohesion of the ionic structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605656X/sa2039sup1.cif Contains datablocks Sn-Amino-Phenol, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680605656X/sa2039Isup2.hkl Contains datablock I

CCDC reference: 636798

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C)= 0.007 Å
R factor = 0.041
wR factor = 0.106
Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: Collect (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997)and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top

Crystal data top

3C₆H₈NO⁺·SnCl₆²⁻·Cl⁻·3H₂O	F(000) = 1504
M_r = 751.29	D_x = 1.696 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12121 reflections
a = 16.2653 (2) Å	θ = 3.0–27.5°
b = 7.1079 (1) Å	µ = 1.54 mm⁻¹
c = 25.4562 (5) Å	T = 296 K
β = 90.751 (1)°	Needle, white
V = 2942.79 (8) Å³	0.31 × 0.02 × 0.02 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	5218 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
φ scans, and ω scans with κ offsets	h = −20→21
20517 measured reflections	k = −9→9
6647 independent reflections	l = −32→32

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0293P)² + 1.3984P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.010
6647 reflections	Δρ_max = 1.01 e Å⁻³
341 parameters	Δρ_min = −0.77 e Å⁻³
7 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (2)

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
O2A	0.29308 (19)	0.8007 (5)	0.13657 (13)	0.0555 (11)
N1A	0.2636 (2)	0.6619 (5)	0.03913 (14)	0.0438 (11)
C1A	0.3478 (2)	0.7092 (5)	0.05577 (16)	0.0366 (11)
C2A	0.3604 (3)	0.7802 (5)	0.10558 (16)	0.0389 (11)
C3A	0.4393 (3)	0.8296 (6)	0.12057 (19)	0.0511 (17)
C4A	0.5035 (3)	0.8091 (7)	0.0866 (2)	0.0574 (16)
C5A	0.4906 (3)	0.7397 (7)	0.0368 (2)	0.0566 (16)
C6A	0.4115 (3)	0.6870 (6)	0.02127 (18)	0.0494 (16)
O2B	0.3191 (2)	0.3097 (6)	0.15686 (15)	0.0708 (14)
N1B	0.3586 (2)	0.4662 (6)	0.25131 (14)	0.0523 (12)
C1B	0.4222 (2)	0.4230 (5)	0.21319 (16)	0.0403 (12)
C2B	0.3998 (3)	0.3472 (6)	0.16514 (17)	0.0444 (12)
C3B	0.4602 (3)	0.3108 (7)	0.1285 (2)	0.0573 (19)
C4B	0.5404 (3)	0.3532 (7)	0.1402 (3)	0.067 (2)
C5B	0.5617 (3)	0.4304 (7)	0.1870 (3)	0.063 (2)
C6B	0.5025 (3)	0.4655 (6)	0.2249 (2)	0.0520 (14)
O2C	0.50268 (17)	1.0049 (5)	0.31020 (13)	0.0546 (11)
N1C	0.6142 (2)	0.8395 (5)	0.37361 (13)	0.0441 (11)
C1C	0.6308 (2)	0.8545 (5)	0.31753 (15)	0.0359 (11)
C2C	0.5718 (2)	0.9407 (5)	0.28563 (16)	0.0384 (11)
C3C	0.5858 (3)	0.9571 (6)	0.23256 (17)	0.0478 (14)
C4C	0.6577 (3)	0.8864 (7)	0.21180 (18)	0.0539 (16)
C5C	0.7162 (3)	0.8014 (7)	0.2438 (2)	0.0549 (17)
C6C	0.7027 (3)	0.7864 (6)	0.29719 (18)	0.0464 (14)
Sn1	0.80594 (1)	0.83686 (3)	0.04616 (1)	0.0305 (1)
Cl1	0.71455 (6)	1.08187 (13)	0.07637 (4)	0.0387 (3)
Cl2	0.89954 (6)	0.59676 (14)	0.01653 (4)	0.0459 (3)
Cl3	0.89120 (6)	1.07867 (13)	0.00819 (4)	0.0427 (3)
Cl4	0.72617 (8)	0.82130 (15)	−0.03601 (4)	0.0525 (4)
Cl5	0.71930 (6)	0.59276 (14)	0.08185 (4)	0.0451 (3)
Cl6	0.87917 (6)	0.85394 (15)	0.13028 (4)	0.0454 (3)
O1W	0.1597 (2)	0.5159 (5)	0.11681 (13)	0.0530 (11)
O2W	0.0461 (2)	0.2118 (5)	0.09776 (13)	0.0532 (11)
O3W	0.0842 (2)	0.8573 (5)	0.14865 (14)	0.0573 (12)
Cl7	0.16140 (6)	0.41601 (18)	0.24774 (4)	0.0526 (3)
H2A	0.30743	0.84173	0.16536	0.0832*
H3A	0.44914	0.87730	0.15409	0.0615*
H4A	0.55640	0.84252	0.09737	0.0686*
H5A	0.53415	0.72808	0.01374	0.0679*
H6A	0.40189	0.63727	−0.01204	0.0590*
H11A	0.23720	0.60919	0.06579	0.0658*
H12A	0.26507	0.58157	0.01233	0.0658*
H13A	0.23733	0.76607	0.02917	0.0658*
H2B	0.31265	0.26215	0.12775	0.1061*
H3B	0.44627	0.25783	0.09617	0.0686*
H4B	0.58079	0.32862	0.11560	0.0807*
H5B	0.61646	0.46025	0.19398	0.0757*
H6B	0.51716	0.51661	0.25735	0.0627*
H11B	0.35081	0.59006	0.25250	0.0784*
H12B	0.37436	0.42511	0.28290	0.0784*
H13B	0.31190	0.40980	0.24177	0.0784*
H2C	0.46330	0.99920	0.28982	0.0816*
H3C	0.54709	1.01529	0.21080	0.0575*
H4C	0.66686	0.89624	0.17591	0.0646*
H5C	0.76433	0.75447	0.22945	0.0659*
H6C	0.74190	0.73064	0.31908	0.0553*
H11C	0.65227	0.76745	0.38893	0.0662*
H12C	0.56480	0.78824	0.37804	0.0662*
H13C	0.61524	0.95353	0.38802	0.0662*
H11	0.177 (3)	0.493 (7)	0.1469 (12)	0.0538*
H12	0.129 (2)	0.425 (5)	0.1066 (18)	0.0538*
H21	0.038 (3)	0.207 (7)	0.0648 (11)	0.0538*
H22	0.063 (3)	0.113 (5)	0.1114 (19)	0.0538*
H31	0.1231 (19)	0.809 (6)	0.1347 (18)	0.0538*
H32	0.0392 (17)	0.806 (6)	0.1496 (19)	0.0538*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2A	0.0509 (18)	0.075 (2)	0.0406 (19)	−0.0071 (15)	0.0019 (14)	−0.0163 (16)
N1A	0.045 (2)	0.0473 (19)	0.039 (2)	0.0026 (15)	−0.0080 (15)	−0.0024 (16)
C1A	0.039 (2)	0.0326 (18)	0.038 (2)	−0.0002 (15)	−0.0056 (17)	0.0039 (16)
C2A	0.043 (2)	0.0355 (19)	0.038 (2)	0.0003 (16)	−0.0024 (18)	−0.0009 (16)
C3A	0.052 (3)	0.052 (3)	0.049 (3)	−0.007 (2)	−0.009 (2)	−0.006 (2)
C4A	0.042 (2)	0.064 (3)	0.066 (3)	−0.007 (2)	−0.009 (2)	−0.002 (2)
C5A	0.040 (2)	0.069 (3)	0.061 (3)	0.006 (2)	0.013 (2)	0.005 (3)
C6A	0.056 (3)	0.053 (3)	0.039 (2)	0.008 (2)	−0.001 (2)	−0.001 (2)
O2B	0.065 (2)	0.089 (3)	0.058 (2)	−0.0055 (19)	−0.0100 (18)	−0.013 (2)
N1B	0.043 (2)	0.069 (2)	0.045 (2)	−0.0043 (17)	0.0004 (17)	−0.0042 (19)
C1B	0.042 (2)	0.037 (2)	0.042 (2)	0.0013 (16)	0.0036 (18)	0.0044 (17)
C2B	0.047 (2)	0.045 (2)	0.041 (2)	0.0028 (18)	−0.0023 (19)	0.0060 (18)
C3B	0.076 (4)	0.050 (3)	0.046 (3)	0.009 (2)	0.010 (2)	0.003 (2)
C4B	0.073 (4)	0.049 (3)	0.081 (4)	0.015 (2)	0.035 (3)	0.011 (3)
C5B	0.041 (3)	0.049 (3)	0.099 (5)	0.000 (2)	0.013 (3)	0.012 (3)
C6B	0.043 (2)	0.047 (2)	0.066 (3)	−0.0067 (19)	−0.004 (2)	0.000 (2)
O2C	0.0384 (16)	0.068 (2)	0.057 (2)	0.0056 (15)	−0.0112 (14)	−0.0055 (16)
N1C	0.0451 (19)	0.051 (2)	0.036 (2)	−0.0010 (16)	−0.0053 (15)	0.0003 (16)
C1C	0.043 (2)	0.0325 (18)	0.032 (2)	−0.0057 (15)	−0.0043 (16)	0.0005 (15)
C2C	0.041 (2)	0.0351 (19)	0.039 (2)	−0.0044 (16)	−0.0077 (18)	−0.0023 (16)
C3C	0.063 (3)	0.042 (2)	0.038 (2)	−0.0111 (19)	−0.016 (2)	0.0057 (18)
C4C	0.074 (3)	0.054 (3)	0.034 (2)	−0.017 (2)	0.008 (2)	0.002 (2)
C5C	0.057 (3)	0.058 (3)	0.050 (3)	−0.003 (2)	0.013 (2)	−0.003 (2)
C6C	0.050 (2)	0.045 (2)	0.044 (3)	0.0053 (18)	−0.001 (2)	0.0024 (19)
Sn1	0.0332 (2)	0.0265 (1)	0.0318 (2)	0.0023 (1)	0.0005 (1)	−0.0001 (1)
Cl1	0.0409 (5)	0.0352 (4)	0.0402 (5)	0.0100 (4)	0.0033 (4)	−0.0031 (4)
Cl2	0.0522 (6)	0.0371 (5)	0.0488 (6)	0.0150 (4)	0.0134 (5)	0.0021 (4)
Cl3	0.0402 (5)	0.0365 (5)	0.0516 (6)	−0.0033 (4)	0.0079 (4)	0.0074 (4)
Cl4	0.0682 (7)	0.0493 (6)	0.0396 (6)	0.0086 (5)	−0.0182 (5)	−0.0072 (5)
Cl5	0.0419 (5)	0.0356 (5)	0.0579 (7)	−0.0075 (4)	0.0062 (5)	0.0047 (4)
Cl6	0.0464 (6)	0.0505 (6)	0.0389 (6)	0.0015 (4)	−0.0118 (4)	0.0031 (4)
O1W	0.0529 (19)	0.060 (2)	0.046 (2)	−0.0111 (15)	−0.0031 (15)	−0.0016 (16)
O2W	0.061 (2)	0.0579 (19)	0.0408 (19)	−0.0005 (16)	0.0047 (16)	−0.0037 (16)
O3W	0.052 (2)	0.062 (2)	0.058 (2)	0.0036 (16)	0.0051 (17)	−0.0066 (16)
Cl7	0.0394 (5)	0.0745 (7)	0.0438 (6)	−0.0012 (5)	−0.0024 (4)	0.0090 (5)

Geometric parameters (Å, º) top

Sn1—Cl6	2.4397 (10)	C1A—C6A	1.376 (6)
Sn1—Cl3	2.4180 (10)	C1A—C2A	1.378 (6)
Sn1—Cl1	2.4215 (10)	C2A—C3A	1.380 (7)
Sn1—Cl2	2.4144 (10)	C3A—C4A	1.372 (7)
Sn1—Cl4	2.4495 (11)	C4A—C5A	1.374 (7)
Sn1—Cl5	2.4198 (10)	C5A—C6A	1.392 (7)
O2A—C2A	1.366 (6)	C3A—H3A	0.9300
O2A—H2A	0.8200	C4A—H4A	0.9300
O2B—C2B	1.353 (6)	C5A—H5A	0.9300
O2B—H2B	0.8200	C6A—H6A	0.9300
O2C—C2C	1.372 (5)	C1B—C6B	1.370 (6)
O2C—H2C	0.8200	C1B—C2B	1.381 (6)
O1W—H12	0.86 (3)	C2B—C3B	1.388 (7)
O1W—H11	0.83 (3)	C3B—C4B	1.368 (7)
N1A—C1A	1.467 (5)	C4B—C5B	1.353 (10)
N1A—H11A	0.8900	C5B—C6B	1.395 (8)
N1A—H13A	0.8900	C3B—H3B	0.9300
N1A—H12A	0.8900	C4B—H4B	0.9300
O2W—H21	0.85 (3)	C5B—H5B	0.9300
O2W—H22	0.83 (4)	C6B—H6B	0.9300
N1B—C1B	1.460 (5)	C1C—C2C	1.391 (5)
N1B—H12B	0.8900	C1C—C6C	1.373 (6)
N1B—H11B	0.8900	C2C—C3C	1.378 (6)
N1B—H13B	0.8900	C3C—C4C	1.384 (7)
O3W—H32	0.82 (3)	C4C—C5C	1.383 (7)
O3W—H31	0.81 (4)	C5C—C6C	1.384 (7)
N1C—C1C	1.460 (5)	C3C—H3C	0.9300
N1C—H12C	0.8900	C4C—H4C	0.9300
N1C—H13C	0.8900	C5C—H5C	0.9300
N1C—H11C	0.8900	C6C—H6C	0.9300

Sn1···H12Aⁱ	3.5100	N1A···O1W	2.816 (5)
Sn1···H13Aⁱⁱ	3.4800	N1A···Cl1ⁱⁱ	3.481 (4)
Sn1···H11Cⁱⁱⁱ	3.5400	N1A···O2A	2.706 (5)
Sn1···H13C^iv	3.4400	N1B···Cl7	3.227 (3)
Cl1···Cl3	3.3763 (14)	N1B···O3W^ix	2.809 (5)
Cl1···Cl5^v	3.6348 (14)	N1B···Cl7^xi	3.214 (4)
Cl1···Cl4	3.4153 (14)	N1B···O2B	2.719 (5)
Cl1···Cl5	3.4802 (14)	N1C···O2W^xi	2.864 (5)
Cl1···C6Aⁱⁱ	3.598 (5)	N1C···Cl6^iv	3.455 (4)
Cl1···N1Aⁱⁱ	3.481 (4)	N1C···Cl2ⁱⁱⁱ	3.351 (4)
Cl1···Cl6	3.4031 (14)	N1C···Cl5ⁱⁱⁱ	3.432 (3)
Cl2···Cl5	3.3894 (14)	N1C···O2C	2.684 (5)
Cl2···Cl6	3.4440 (14)	C1A···Cl4ⁱⁱ	3.581 (4)
Cl2···N1C^iv	3.351 (4)	C2A···C2B	3.487 (6)
Cl2···Cl4	3.4913 (16)	C2A···Cl4ⁱⁱ	3.616 (4)
Cl2···Cl3^vi	3.6910 (14)	C2B···C2A	3.487 (6)
Cl2···Cl3	3.4345 (14)	C3A···C3B^v	3.443 (7)
Cl2···Cl2^vii	3.6541 (14)	C3B···C3A^vi	3.443 (7)
Cl2···O2Wⁱ	3.342 (3)	C3C···C5B^v	3.578 (7)
Cl3···Cl1	3.3763 (14)	C4A···C4B	3.564 (7)
Cl3···Cl4	3.4262 (15)	C4B···C4A	3.564 (7)
Cl3···Cl2^v	3.6910 (14)	C5B···C3C^vi	3.578 (7)
Cl3···N1Aⁱⁱ	3.333 (4)	C6A···Cl1ⁱⁱ	3.598 (5)
Cl3···Cl2	3.4345 (14)	C3C···H3A	3.0200
Cl3···Cl6	3.5022 (14)	C4B···H3C^vi	3.0000
Cl4···Cl5	3.4149 (14)	C4C···H6Cⁱⁱⁱ	3.0500
Cl4···C2Aⁱⁱ	3.616 (4)	C5B···H3C^vi	3.0200
Cl4···O2Bⁱ	3.289 (4)	H2A···H3A	2.3400
Cl4···Cl3	3.4262 (15)	H2A···Cl7^xi	2.3200
Cl4···Cl2	3.4913 (16)	H2B···H3B	2.3300
Cl4···N1Aⁱ	3.440 (4)	H2B···Cl4ⁱ	2.4800
Cl4···C1Aⁱⁱ	3.581 (4)	H2C···Cl7^xi	2.3100
Cl4···Cl1	3.4153 (14)	H2C···H3C	2.4500
Cl5···Cl4	3.4149 (14)	H3A···H2A	2.3400
Cl5···Cl2	3.3894 (14)	H3A···Cl7^xi	3.1100
Cl5···Cl1^vi	3.6348 (14)	H3A···C3C	3.0200
Cl5···N1C^iv	3.432 (3)	H3A···H3C	2.3500
Cl5···Cl1	3.4802 (14)	H3B···H2B	2.3300
Cl5···Cl6	3.4123 (14)	H3C···H2C	2.4500
Cl6···N1Cⁱⁱⁱ	3.455 (4)	H3C···C4B^v	3.0000
Cl6···O3W^viii	3.362 (3)	H3C···H3A	2.3500
Cl6···Cl3	3.5022 (14)	H3C···C5B^v	3.0200
Cl6···Cl5	3.4123 (14)	H4A···Cl1	3.1400
Cl6···Cl1	3.4031 (14)	H4B···Cl1^vi	2.9800
Cl6···Cl2	3.4440 (14)	H4B···Cl5	3.0600
Cl7···N1B	3.227 (3)	H4C···Cl1	2.9700
Cl7···O1W	3.408 (3)	H6A···H12A	2.3500
Cl7···O2C^ix	3.097 (3)	H6A···Cl5ⁱ	3.1000
Cl1···H4A	3.1400	H6B···H12B	2.5100
Cl1···H11Cⁱⁱⁱ	2.6800	H6C···Cl1^iv	2.9400
Cl1···H4C	2.9700	H6C···C4C^iv	3.0500
Cl1···H13Aⁱⁱ	3.0100	H6C···H11C	2.3300
Cl1···H6Cⁱⁱⁱ	2.9400	H11···H31	2.43 (6)
Cl1···H4B^v	2.9800	H11···Cl7	2.64 (3)
Cl2···H21ⁱ	2.71 (4)	H11···O2B	2.66 (5)
Cl2···H12Aⁱ	3.0400	H11···O2A	2.90 (5)
Cl2···H13C^iv	2.6500	H11···H11A	2.4400
Cl3···H21^x	2.92 (5)	H11A···O2A	2.4300
Cl3···H21ⁱ	2.99 (4)	H11A···O1W	1.9400
Cl3···H11Cⁱⁱⁱ	3.0300	H11A···H11	2.4400
Cl3···H13Aⁱⁱ	2.5400	H11A···H12	2.4400
Cl4···H13Aⁱⁱ	3.0000	H11B···Cl7^xi	2.3300
Cl4···H12Aⁱ	2.9300	H11C···H6C	2.3300
Cl4···H2Bⁱ	2.4800	H11C···Cl1^iv	2.6800
Cl5···H13C^iv	2.9600	H11C···Cl3^iv	3.0300
Cl5···H6Aⁱ	3.1000	H11C···Cl6^iv	3.0200
Cl5···H12Aⁱ	2.7100	H11C···Sn1^iv	3.5400
Cl5···H4B	3.0600	H12···H11A	2.4400
Cl6···H32^viii	2.67 (3)	H12···O2W	2.04 (3)
Cl6···H11Cⁱⁱⁱ	3.0200	H12···H21	2.38 (6)
Cl6···H13C^iv	2.8900	H12···H22	2.47 (5)
Cl7···H2C^ix	2.3100	H12A···Cl2ⁱ	3.0400
Cl7···H13B	2.4600	H12A···H6A	2.3500
Cl7···H11	2.64 (3)	H12A···Cl5ⁱ	2.7100
O1W···O3W	2.843 (5)	H12A···Sn1ⁱ	3.5100
O1W···O2A	3.005 (5)	H12A···Cl4ⁱ	2.9300
O1W···Cl7	3.408 (3)	H12B···H31^ix	2.2500
O1W···O2B	3.137 (5)	H12B···O3W^ix	1.9200
O1W···O2W	2.881 (5)	H12B···H32^ix	2.3600
O1W···N1A	2.816 (5)	H12B···H6B	2.5100
O2A···N1A	2.706 (5)	H12C···H22^xi	2.4400
O2A···O1W	3.005 (5)	H12C···O2W^xi	1.9900
O2A···Cl7^xi	3.136 (3)	H12C···O2C	2.5200
O2B···N1B	2.719 (5)	H12C···H21^xi	2.3000
O2B···Cl4ⁱ	3.289 (4)	H13A···Cl4ⁱⁱ	3.0000
O2B···O1W	3.137 (5)	H13A···Cl1ⁱⁱ	3.0100
O2C···Cl7^xi	3.097 (3)	H13A···Sn1ⁱⁱ	3.4800
O2C···O3W^xi	3.067 (5)	H13A···Cl3ⁱⁱ	2.5400
O2C···N1C	2.684 (5)	H13A···O2A	2.8800
O2W···O1W	2.881 (5)	H13B···Cl7	2.4600
O2W···N1C^ix	2.864 (5)	H13B···O2B	2.2800
O2W···O3W^vi	2.897 (5)	H13C···Cl5ⁱⁱⁱ	2.9600
O2W···Cl2ⁱ	3.342 (3)	H13C···Cl6ⁱⁱⁱ	2.8900
O3W···O2C^ix	3.067 (5)	H13C···Cl2ⁱⁱⁱ	2.6500
O3W···Cl6^xii	3.362 (3)	H13C···Sn1ⁱⁱⁱ	3.4400
O3W···O1W	2.843 (5)	H13C···O2C	2.7000
O1W···H11A	1.9400	H21···H12C^ix	2.3000
O1W···H31	2.22 (4)	H21···Cl3^xiii	2.92 (5)
O2A···H31	2.77 (3)	H21···H12	2.38 (6)
O2A···H11A	2.4300	H21···Cl2ⁱ	2.71 (4)
O2A···H13A	2.8800	H21···Cl3ⁱ	2.99 (4)
O2A···H11	2.90 (5)	H22···H12	2.47 (5)
O2B···H13B	2.2800	H22···H12C^ix	2.4400
O2B···H11	2.66 (5)	H22···O3W^vi	2.08 (4)
O2C···H12C	2.5200	H22···H31^vi	2.44 (6)
O2C···H13C	2.7000	H22···H32^vi	2.42 (6)
O2C···H32^xi	2.47 (4)	H31···O1W	2.22 (4)
O2W···H12C^ix	1.9900	H31···O2A	2.77 (3)
O2W···H12	2.04 (3)	H31···H11	2.43 (6)
N1A···Cl3ⁱⁱ	3.333 (4)	H32···O2C^ix	2.47 (4)
N1A···Cl4ⁱ	3.440 (4)	H32···Cl6^xii	2.67 (3)

Cl1—Sn1—Cl5	91.92 (3)	C4A—C5A—C6A	119.2 (5)
Cl1—Sn1—Cl6	88.86 (3)	C1A—C6A—C5A	119.3 (4)
Cl2—Sn1—Cl3	90.59 (3)	C4A—C3A—H3A	120.00
Cl2—Sn1—Cl4	91.74 (4)	C2A—C3A—H3A	120.00
Cl2—Sn1—Cl5	89.04 (3)	C5A—C4A—H4A	120.00
Cl2—Sn1—Cl6	90.39 (3)	C3A—C4A—H4A	120.00
Cl3—Sn1—Cl4	89.48 (4)	C6A—C5A—H5A	120.00
Cl3—Sn1—Cl5	178.48 (4)	C4A—C5A—H5A	120.00
Cl3—Sn1—Cl6	92.27 (3)	C5A—C6A—H6A	120.00
Cl4—Sn1—Cl5	89.07 (4)	C1A—C6A—H6A	120.00
Cl4—Sn1—Cl6	177.23 (4)	N1B—C1B—C6B	119.4 (4)
Cl5—Sn1—Cl6	89.21 (3)	N1B—C1B—C2B	119.3 (3)
Cl1—Sn1—Cl2	178.78 (3)	C2B—C1B—C6B	121.2 (4)
Cl1—Sn1—Cl3	88.48 (3)	C1B—C2B—C3B	119.2 (4)
Cl1—Sn1—Cl4	89.04 (4)	O2B—C2B—C3B	123.5 (4)
C2A—O2A—H2A	109.00	O2B—C2B—C1B	117.3 (4)
C2B—O2B—H2B	110.00	C2B—C3B—C4B	119.6 (5)
C2C—O2C—H2C	109.00	C3B—C4B—C5B	120.9 (6)
H11—O1W—H12	109 (5)	C4B—C5B—C6B	120.7 (5)
H11A—N1A—H12A	109.00	C1B—C6B—C5B	118.4 (5)
H11A—N1A—H13A	109.00	C4B—C3B—H3B	120.00
C1A—N1A—H13A	110.00	C2B—C3B—H3B	120.00
C1A—N1A—H12A	110.00	C3B—C4B—H4B	119.00
H12A—N1A—H13A	109.00	C5B—C4B—H4B	120.00
C1A—N1A—H11A	110.00	C4B—C5B—H5B	120.00
H21—O2W—H22	115 (5)	C6B—C5B—H5B	120.00
H11B—N1B—H13B	109.00	C5B—C6B—H6B	121.00
C1B—N1B—H11B	109.00	C1B—C6B—H6B	121.00
C1B—N1B—H12B	109.00	N1C—C1C—C6C	120.8 (3)
C1B—N1B—H13B	109.00	N1C—C1C—C2C	117.9 (3)
H11B—N1B—H12B	109.00	C2C—C1C—C6C	121.3 (4)
H12B—N1B—H13B	109.00	O2C—C2C—C1C	116.3 (4)
H31—O3W—H32	122 (4)	C1C—C2C—C3C	119.2 (3)
H11C—N1C—H13C	110.00	O2C—C2C—C3C	124.5 (4)
H12C—N1C—H13C	109.00	C2C—C3C—C4C	119.7 (4)
C1C—N1C—H13C	109.00	C3C—C4C—C5C	120.8 (4)
C1C—N1C—H12C	109.00	C4C—C5C—C6C	119.7 (4)
H11C—N1C—H12C	109.00	C1C—C6C—C5C	119.3 (4)
C1C—N1C—H11C	110.00	C2C—C3C—H3C	120.00
C2A—C1A—C6A	121.7 (4)	C4C—C3C—H3C	120.00
N1A—C1A—C6A	119.8 (4)	C5C—C4C—H4C	120.00
N1A—C1A—C2A	118.5 (3)	C3C—C4C—H4C	120.00
O2A—C2A—C3A	124.3 (4)	C4C—C5C—H5C	120.00
C1A—C2A—C3A	118.3 (4)	C6C—C5C—H5C	120.00
O2A—C2A—C1A	117.4 (4)	C1C—C6C—H6C	120.00
C2A—C3A—C4A	120.8 (4)	C5C—C6C—H6C	120.00
C3A—C4A—C5A	120.8 (5)

N1A—C1A—C2A—O2A	0.5 (5)	O2B—C2B—C3B—C4B	−180.0 (5)
N1A—C1A—C2A—C3A	−178.2 (4)	C1B—C2B—C3B—C4B	−1.0 (7)
C6A—C1A—C2A—O2A	178.7 (4)	C2B—C3B—C4B—C5B	−0.1 (8)
C6A—C1A—C2A—C3A	0.0 (6)	C3B—C4B—C5B—C6B	1.2 (8)
N1A—C1A—C6A—C5A	177.4 (4)	C4B—C5B—C6B—C1B	−1.1 (7)
C2A—C1A—C6A—C5A	−0.8 (6)	N1C—C1C—C2C—O2C	0.2 (5)
O2A—C2A—C3A—C4A	−178.3 (4)	N1C—C1C—C2C—C3C	179.9 (3)
C1A—C2A—C3A—C4A	0.2 (6)	C6C—C1C—C2C—O2C	−179.5 (4)
C2A—C3A—C4A—C5A	0.3 (7)	C6C—C1C—C2C—C3C	0.3 (6)
C3A—C4A—C5A—C6A	−1.1 (7)	N1C—C1C—C6C—C5C	179.4 (4)
C4A—C5A—C6A—C1A	1.3 (7)	C2C—C1C—C6C—C5C	−0.9 (6)
N1B—C1B—C2B—O2B	−2.6 (6)	O2C—C2C—C3C—C4C	−179.7 (4)
N1B—C1B—C2B—C3B	178.4 (4)	C1C—C2C—C3C—C4C	0.6 (6)
C6B—C1B—C2B—O2B	−179.9 (4)	C2C—C3C—C4C—C5C	−0.8 (7)
C6B—C1B—C2B—C3B	1.1 (6)	C3C—C4C—C5C—C6C	0.1 (7)
N1B—C1B—C6B—C5B	−177.3 (4)	C4C—C5C—C6C—C1C	0.7 (7)
C2B—C1B—C6B—C5B	0.0 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···Cl7^xi	0.8200	2.3200	3.136 (3)	171.00
O2B—H2B···Cl4ⁱ	0.8200	2.4800	3.289 (4)	168.00
O2C—H2C···Cl7^xi	0.8200	2.3100	3.097 (3)	162.00
N1A—H11A···O1W	0.8900	1.9400	2.816 (5)	168.00
N1B—H11B···Cl7^xi	0.8900	2.3300	3.214 (4)	176.00
N1C—H11C···Cl1^iv	0.8900	2.6800	3.555 (3)	170.00
N1A—H12A···Cl5ⁱ	0.8900	2.7100	3.586 (4)	167.00
N1B—H12B···O3W^ix	0.8900	1.9200	2.809 (5)	174.00
N1C—H12C···O2W^xi	0.8900	1.9900	2.864 (5)	167.00
N1A—H13A···Cl3ⁱⁱ	0.8900	2.5400	3.333 (4)	149.00
N1B—H13B···Cl7	0.8900	2.4600	3.227 (3)	145.00
N1B—H13B···O2B	0.8900	2.2800	2.719 (5)	110.00
N1C—H13C···Cl2ⁱⁱⁱ	0.8900	2.6500	3.351 (4)	137.00
O1W—H12···O2W	0.86 (3)	2.04 (3)	2.881 (5)	168 (4)
O1W—H11···Cl7	0.83 (3)	2.64 (3)	3.408 (3)	155 (4)
O2W—H21···Cl2ⁱ	0.85 (3)	2.71 (4)	3.342 (3)	133 (4)
O2W—H22···O3W^vi	0.83 (4)	2.08 (4)	2.897 (5)	170 (5)
O3W—H31···O1W	0.81 (4)	2.22 (4)	2.843 (5)	135 (4)
O3W—H32···Cl6^xii	0.82 (3)	2.67 (3)	3.362 (3)	144 (4)
O3W—H32···O2C^ix	0.82 (3)	2.47 (4)	3.067 (5)	131 (3)

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

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