Bis(4-acetyl­anilinium) hexa­chlorido­stannate(IV)

Song, X.-W.; Xue, R.-T.; Chen, S.-G.; Yin, Y.-S.

doi:10.1107/S1600536811015546

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m653

doi:10.1107/S1600536811015546

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Bis(4-acetylanilinium) hexachloridostannate(IV)

Xian-Wang Song,^a Rui-Ting Xue,^a Shou-Gang Chen ^a ^* and Yan-Sheng Yin ^a

^aInstitute of Materials Science and Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
^*Correspondence e-mail: xuert@163.com

(Received 2 April 2011; accepted 25 April 2011; online 29 April 2011)

In the title compound, (C₈H₁₀NO)₂[SnCl₆], the Sn^IV atom exists in an octahedral coordination environment. In the crystal, intermolecular 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_r = 603.73
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 1.00
3929 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.83 e Å⁻³

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⋯Cl3^iv	0.89	2.69	3.321 (5)	129
N1—H1C⋯Cl5^v	0.89	2.55	3.367 (5)	153
N2—H2C⋯Cl6^iv	0.89	2.64	3.442 (5)	151
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Inorganic-organic hybrid materials have received much attention due to their potential applications in many areas such as gas storage, separation, catalysis, magnetism, optics as well as in electrical conductivity (Descazo et al., 2006; Li et al., 2007; Sanchez et al., 2005). Recently, we have prepared the title compound and here its crystal structure is reported.

This title compound contains SnC1₆ inorganic anions and organic cations. The SnCl₆ inorganic anion adopts a regular octahedral geometry, with average Sn—Cl distance of 2.4102 Å. In the organic cations, the diangle between the methyl ketone and the phenyl ring is 14.9 (3)° or 3.1 (2)°.

In the crystal structure, intermolecular N—H···O and N—H···Cl hydrogen bonds link cations and anions into a three-dimensioal framework.

Related literature top

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 top

p-Aminoacetophenone (10 mmol) was dissolved in methanol (10 ml). Ten minutes later, a methanol solution (10 ml) of tin tetrachloride (5 mmol) was added with stirring. The reaction mixture was stirred for 4 h. The solution was held at room temperature for about two weeks, whereupon yellow crystals suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Bis(4-acetylanilinium) hexachloridostannate(IV) top

Crystal data top

(C₈H₁₀NO)₂[SnCl₆]	F(000) = 1192
M_r = 603.73	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0414P)² + 4.9089P] where P = (F_o² + 2F_c²)/3
3929 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

(C₈H₁₀NO)₂[SnCl₆]	V = 2236.7 (4) Å³
M_r = 603.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2540 (8) Å	µ = 1.87 mm⁻¹
b = 12.6481 (13) Å	T = 298 K
c = 24.438 (2) Å	0.48 × 0.44 × 0.43 mm
β = 93.991 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3929 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2996 reflections with I > 2σ(I)
T_min = 0.467, T_max = 0.500	R_int = 0.058
10422 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.00	Δρ_max = 0.84 e Å⁻³
3929 reflections	Δρ_min = −0.83 e Å⁻³
248 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···Cl3^iv	0.89	2.69	3.321 (5)	129
N1—H1C···Cl5^v	0.89	2.55	3.367 (5)	153
N2—H2C···Cl6^iv	0.89	2.64	3.442 (5)	151

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1, −y+1/2, z−1/2; (iv) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	(C₈H₁₀NO)₂[SnCl₆]
M_r	603.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.2540 (8), 12.6481 (13), 24.438 (2)
β (°)	93.991 (1)
V (Å³)	2236.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.48 × 0.44 × 0.43

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.467, 0.500
No. of measured, independent and observed [I > 2σ(I)] reflections	10422, 3929, 2996
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 1.00
No. of reflections	3929
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.83

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···Cl3^iv	0.89	2.69	3.321 (5)	129
N1—H1C···Cl5^v	0.89	2.55	3.367 (5)	153
N2—H2C···Cl6^iv	0.89	2.64	3.442 (5)	151

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1, −y+1/2, z−1/2; (iv) −x, y−1/2, −z+1/2; (v) x, −y+1/2, z−1/2.

Acknowledgements

The authors acknowledge the National Science Foundation of China for financial support of this project (grant Nos. 51072188 and 50702053).

References

Antonietti, M. & Ozin, G. A. (2004). Chem. Eur. J. 10, 28–41. CrossRef PubMed CAS Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cong, H. P. & Yu, S. H. (2009). Curr. Opin. Colloid Interface Sci. 14, 71–80. CrossRef CAS Google Scholar
Descazo, A. B., Martinez-Manez, R., Sancenón, F., Hoffmann, K. & Rurack, K. (2006). Angew. Chem. Int. Ed. 45, 5924–5948. Google Scholar
Li, Y. Y., Zheng, G. L., Lin, C. K. & Lin, J. (2007). Solid State Sci. 9, 855–861. Web of Science CSD CrossRef Google Scholar
Sanchez, C., Julián, B., Belleville, P. & Popall, M. (2005). J. Mater. Chem. 15, 3559–3592. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar