Bis(4-acetyl-anilinium) hexa-chlorido-stannate(IV).

In the title compound, (C(8)H(10)NO)(2)[SnCl(6)], the Sn(IV) atom exists in an octa-hedral coordination environment. In the crystal, inter-molecular N-H⋯O and N-H⋯Cl hydrogen bonds link the cations and anions into a three-dimensional framework.

Related literature

For general background to inorganic–organic hybrid compounds, see: Antonietti & Ozin (2004 ▶); Cong & Yu (2009 ▶); Descazo et al. (2006 ▶); Li et al. (2007 ▶); Sanchez et al. (2005 ▶).

Experimental

Crystal data

(C8H10NO)2[SnCl6]

M = 603.73

Monoclinic,

a = 7.2540 (8) Å

b = 12.6481 (13) Å

c = 24.438 (2) Å

β = 93.991 (1)°

V = 2236.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.87 mm−1

T = 298 K

0.48 × 0.44 × 0.43 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.467, T max = 0.500

10422 measured reflections

3929 independent reflections

2996 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 1.00

3929 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.83 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015546/ci5184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015546/ci5184Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C8H10NO)2[SnCl6]	F(000) = 1192
Mr = 603.73	Dx = 1.793 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3529 reflections
a = 7.2540 (8) Å	θ = 2.5–27.3°
b = 12.6481 (13) Å	µ = 1.87 mm−1
c = 24.438 (2) Å	T = 298 K
β = 93.991 (1)°	Block, yellow
V = 2236.7 (4) Å3	0.48 × 0.44 × 0.43 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3929 independent reflections
Radiation source: fine-focus sealed tube	2996 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.467, Tmax = 0.500	k = −15→14
10422 measured reflections	l = −23→29

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0414P)2 + 4.9089P] where P = (Fo2 + 2Fc2)/3
3929 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

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.

	x	y	z	Uiso*/Ueq
Sn1	0.26788 (5)	0.33553 (3)	0.392680 (15)	0.02996 (14)
Cl1	0.2381 (3)	0.19836 (12)	0.46029 (6)	0.0541 (5)
Cl2	0.2941 (3)	0.47370 (13)	0.32429 (7)	0.0631 (5)
Cl3	0.0010 (2)	0.26670 (12)	0.33926 (7)	0.0492 (4)
Cl4	0.4656 (3)	0.22042 (16)	0.34441 (7)	0.0645 (5)
Cl5	0.5344 (3)	0.40331 (15)	0.44385 (9)	0.0763 (6)
Cl6	0.0643 (3)	0.44692 (15)	0.43985 (8)	0.0706 (6)
N1	0.7808 (7)	0.3221 (4)	−0.04410 (19)	0.0425 (12)
H1A	0.8949	0.3038	−0.0516	0.064*
H1B	0.7532	0.3847	−0.0591	0.064*
H1C	0.7011	0.2739	−0.0578	0.064*
N2	0.2441 (7)	−0.0116 (4)	0.1716 (2)	0.0435 (13)
H2A	0.2336	−0.0262	0.2069	0.065*
H2B	0.3501	−0.0378	0.1612	0.065*
H2C	0.1501	−0.0406	0.1515	0.065*
O1	0.7432 (7)	0.4341 (3)	0.21126 (18)	0.0580 (13)
O2	0.2530 (7)	0.4680 (3)	0.08980 (18)	0.0539 (12)
C1	0.7034 (9)	0.2499 (5)	0.2194 (2)	0.0438 (15)
H1D	0.6742	0.2672	0.2560	0.066*
H1E	0.8139	0.2079	0.2207	0.066*
H1F	0.6032	0.2106	0.2015	0.066*
C2	0.7326 (8)	0.3483 (5)	0.1884 (2)	0.0367 (14)
C3	0.7471 (8)	0.3413 (4)	0.1275 (2)	0.0311 (12)
C4	0.7306 (9)	0.4318 (4)	0.0953 (2)	0.0418 (15)
H4	0.7124	0.4969	0.1117	0.050*
C5	0.7409 (9)	0.4261 (4)	0.0395 (2)	0.0409 (15)
H5	0.7288	0.4865	0.0179	0.049*
C6	0.7697 (8)	0.3287 (4)	0.0163 (2)	0.0323 (13)
C7	0.7890 (8)	0.2386 (4)	0.0465 (2)	0.0357 (14)
H7	0.8114	0.1742	0.0298	0.043*
C8	0.7747 (8)	0.2445 (4)	0.1024 (2)	0.0352 (13)
H8	0.7836	0.1833	0.1235	0.042*
C9	0.2098 (11)	0.5103 (5)	0.1816 (3)	0.060 (2)
H9A	0.2172	0.5817	0.1685	0.091*
H9B	0.3052	0.4986	0.2102	0.091*
H9C	0.0912	0.4990	0.1957	0.091*
C10	0.2339 (8)	0.4365 (4)	0.1361 (3)	0.0367 (14)
C11	0.2402 (7)	0.3190 (4)	0.1471 (2)	0.0291 (12)
C12	0.2097 (8)	0.2773 (4)	0.1983 (2)	0.0334 (13)
H12	0.1874	0.3226	0.2271	0.040*
C13	0.2122 (8)	0.1688 (4)	0.2070 (2)	0.0361 (13)
H13	0.1942	0.1407	0.2414	0.043*
C14	0.2417 (7)	0.1046 (4)	0.1635 (2)	0.0309 (13)
C15	0.2731 (9)	0.1431 (4)	0.1123 (2)	0.0393 (15)
H15	0.2941	0.0973	0.0836	0.047*
C16	0.2725 (8)	0.2515 (4)	0.1044 (2)	0.0368 (14)
H16	0.2939	0.2790	0.0701	0.044*

	U11	U22	U33	U12	U13	U23
Sn1	0.0358 (2)	0.0256 (2)	0.0283 (2)	−0.00138 (17)	0.00080 (15)	0.00247 (16)
Cl1	0.0862 (13)	0.0402 (9)	0.0365 (9)	−0.0050 (8)	0.0079 (8)	0.0140 (7)
Cl2	0.0919 (14)	0.0452 (10)	0.0497 (10)	−0.0193 (9)	−0.0122 (9)	0.0256 (8)
Cl3	0.0447 (9)	0.0490 (9)	0.0523 (10)	−0.0104 (7)	−0.0098 (8)	−0.0073 (7)
Cl4	0.0585 (12)	0.0893 (14)	0.0474 (10)	0.0312 (10)	0.0165 (8)	−0.0046 (9)
Cl5	0.0737 (14)	0.0646 (12)	0.0854 (15)	−0.0219 (10)	−0.0323 (11)	0.0147 (10)
Cl6	0.0885 (15)	0.0613 (11)	0.0630 (12)	0.0274 (10)	0.0125 (11)	−0.0232 (9)
N1	0.056 (3)	0.042 (3)	0.030 (3)	0.005 (2)	0.003 (2)	0.001 (2)
N2	0.054 (3)	0.028 (3)	0.049 (3)	−0.003 (2)	0.006 (3)	−0.002 (2)
O1	0.100 (4)	0.038 (3)	0.036 (3)	−0.001 (2)	0.012 (2)	−0.010 (2)
O2	0.086 (4)	0.035 (2)	0.042 (3)	0.006 (2)	0.013 (2)	0.012 (2)
C1	0.051 (4)	0.050 (4)	0.031 (3)	−0.007 (3)	0.005 (3)	0.001 (3)
C2	0.036 (3)	0.045 (4)	0.029 (3)	0.005 (3)	0.002 (3)	0.003 (3)
C3	0.033 (3)	0.032 (3)	0.028 (3)	−0.002 (2)	−0.001 (2)	−0.005 (2)
C4	0.066 (4)	0.021 (3)	0.038 (4)	0.005 (3)	0.005 (3)	−0.006 (2)
C5	0.063 (4)	0.024 (3)	0.036 (3)	0.001 (3)	0.004 (3)	0.000 (2)
C6	0.037 (3)	0.034 (3)	0.025 (3)	0.000 (3)	0.003 (2)	−0.005 (2)
C7	0.048 (4)	0.021 (3)	0.038 (3)	0.003 (2)	0.004 (3)	−0.004 (2)
C8	0.043 (4)	0.033 (3)	0.029 (3)	0.001 (3)	−0.002 (3)	0.001 (2)
C9	0.097 (6)	0.025 (3)	0.061 (5)	0.004 (3)	0.018 (4)	0.006 (3)
C10	0.039 (4)	0.030 (3)	0.040 (4)	0.005 (3)	0.001 (3)	0.004 (3)
C11	0.030 (3)	0.027 (3)	0.030 (3)	−0.001 (2)	0.000 (2)	0.001 (2)
C12	0.042 (3)	0.027 (3)	0.032 (3)	−0.002 (2)	0.006 (3)	−0.004 (2)
C13	0.044 (4)	0.034 (3)	0.031 (3)	−0.006 (3)	0.006 (3)	0.001 (3)
C14	0.030 (3)	0.025 (3)	0.038 (3)	−0.003 (2)	0.002 (3)	0.003 (2)
C15	0.053 (4)	0.031 (3)	0.035 (3)	−0.002 (3)	0.007 (3)	−0.009 (2)
C16	0.049 (4)	0.033 (3)	0.029 (3)	−0.001 (3)	0.006 (3)	0.003 (2)

Sn1—Cl5	2.3873 (18)	C4—C5	1.373 (8)
Sn1—Cl6	2.3938 (17)	C4—H4	0.93
Sn1—Cl4	2.4090 (17)	C5—C6	1.378 (7)
Sn1—Cl1	2.4158 (15)	C5—H5	0.93
Sn1—Cl3	2.4206 (15)	C6—C7	1.360 (7)
Sn1—Cl2	2.4346 (15)	C7—C8	1.379 (8)
N1—C6	1.486 (7)	C7—H7	0.93
N1—H1A	0.89	C8—H8	0.93
N1—H1B	0.89	C9—C10	1.471 (9)
N1—H1C	0.89	C9—H9A	0.96
N2—C14	1.482 (7)	C9—H9B	0.96
N2—H2A	0.89	C9—H9C	0.96
N2—H2B	0.89	C10—C11	1.509 (7)
N2—H2C	0.89	C11—C16	1.381 (8)
O1—C2	1.220 (7)	C11—C12	1.390 (8)
O2—C10	1.217 (7)	C12—C13	1.389 (7)
C1—C2	1.480 (8)	C12—H12	0.93
C1—H1D	0.96	C13—C14	1.365 (8)
C1—H1E	0.96	C13—H13	0.93
C1—H1F	0.96	C14—C15	1.378 (8)
C2—C3	1.502 (8)	C15—C16	1.384 (8)
C3—C4	1.389 (8)	C15—H15	0.93
C3—C8	1.390 (7)	C16—H16	0.93
Cl5—Sn1—Cl6	92.32 (8)	C3—C4—H4	119.6
Cl5—Sn1—Cl4	89.17 (8)	C4—C5—C6	118.4 (5)
Cl6—Sn1—Cl4	178.43 (8)	C4—C5—H5	120.8
Cl5—Sn1—Cl1	90.42 (7)	C6—C5—H5	120.8
Cl6—Sn1—Cl1	90.34 (7)	C7—C6—C5	122.5 (5)
Cl4—Sn1—Cl1	89.16 (7)	C7—C6—N1	118.8 (5)
Cl5—Sn1—Cl3	178.91 (8)	C5—C6—N1	118.6 (5)
Cl6—Sn1—Cl3	88.53 (7)	C6—C7—C8	118.7 (5)
Cl4—Sn1—Cl3	89.98 (7)	C6—C7—H7	120.6
Cl1—Sn1—Cl3	90.25 (6)	C8—C7—H7	120.6
Cl5—Sn1—Cl2	90.16 (7)	C7—C8—C3	120.5 (5)
Cl6—Sn1—Cl2	89.33 (7)	C7—C8—H8	119.7
Cl4—Sn1—Cl2	91.16 (7)	C3—C8—H8	119.7
Cl1—Sn1—Cl2	179.35 (7)	C10—C9—H9A	109.5
Cl3—Sn1—Cl2	89.18 (6)	C10—C9—H9B	109.5
C6—N1—H1A	109.5	H9A—C9—H9B	109.5
C6—N1—H1B	109.5	C10—C9—H9C	109.5
H1A—N1—H1B	109.5	H9A—C9—H9C	109.5
C6—N1—H1C	109.5	H9B—C9—H9C	109.5
H1A—N1—H1C	109.5	O2—C10—C9	121.4 (5)
H1B—N1—H1C	109.5	O2—C10—C11	118.9 (5)
C14—N2—H2A	109.5	C9—C10—C11	119.7 (5)
C14—N2—H2B	109.5	C16—C11—C12	119.4 (5)
H2A—N2—H2B	109.5	C16—C11—C10	118.7 (5)
C14—N2—H2C	109.5	C12—C11—C10	121.9 (5)
H2A—N2—H2C	109.5	C13—C12—C11	120.8 (5)
H2B—N2—H2C	109.5	C13—C12—H12	119.6
C2—C1—H1D	109.5	C11—C12—H12	119.6
C2—C1—H1E	109.5	C14—C13—C12	118.1 (5)
H1D—C1—H1E	109.5	C14—C13—H13	121.0
C2—C1—H1F	109.5	C12—C13—H13	121.0
H1D—C1—H1F	109.5	C13—C14—C15	122.8 (5)
H1E—C1—H1F	109.5	C13—C14—N2	119.2 (5)
O1—C2—C1	121.4 (5)	C15—C14—N2	118.0 (5)
O1—C2—C3	120.0 (5)	C14—C15—C16	118.5 (5)
C1—C2—C3	118.6 (5)	C14—C15—H15	120.7
C4—C3—C8	119.0 (5)	C16—C15—H15	120.7
C4—C3—C2	120.3 (5)	C11—C16—C15	120.5 (5)
C8—C3—C2	120.8 (5)	C11—C16—H16	119.8
C5—C4—C3	120.7 (5)	C15—C16—H16	119.8
C5—C4—H4	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.89	2.06	2.939 (7)	170
N1—H1B···O2ii	0.89	2.01	2.884 (6)	168
N1—H1A···Cl1iii	0.89	2.49	3.322 (6)	156
N2—H2B···Cl2i	0.89	2.59	3.350 (6)	144
N2—H2C···Cl3iv	0.89	2.69	3.321 (5)	129
N1—H1C···Cl5v	0.89	2.55	3.367 (5)	153
N2—H2C···Cl6iv	0.89	2.64	3.442 (5)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.89	2.06	2.939 (7)	170
N1—H1B⋯O2ii	0.89	2.01	2.884 (6)	168
N1—H1A⋯Cl1iii	0.89	2.49	3.322 (6)	156
N2—H2B⋯Cl2i	0.89	2.59	3.350 (6)	144
N2—H2C⋯Cl3iv	0.89	2.69	3.321 (5)	129
N1—H1C⋯Cl5v	0.89	2.55	3.367 (5)	153
N2—H2C⋯Cl6iv	0.89	2.64	3.442 (5)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .