Tetra­kis(4-chloro­anilinium) hexa­chlorido­stannate(IV) dichloride

Zhou, B.; Liu, H.

doi:10.1107/S1600536812021666

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m782

doi:10.1107/S1600536812021666

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Tetrakis(4-chloroanilinium) hexachloridostannate(IV) dichloride

Benhua Zhou ^a ^* and Hongxia Liu ^a

^aSchool of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224051, People's Republic of China
^*Correspondence e-mail: rongtao198806@163.com

(Received 23 April 2012; accepted 13 May 2012; online 19 May 2012)

The asymmetric unit of the title compound, (C₆H₇ClN)₄[SnCl₆]Cl₂, comprises two 4-chloroanilinium cations, half of an [SnCl₆]²⁻ anion and a Cl⁻ anion. The Sn^IV atom, located on a special position on a twofold rotation axis, exhibits an octahedral environment. In the crystal, molecules are linked by N—H⋯Cl hydrogen bonds between the 4-chloroanilinium cations, [SnCl₆]²⁻ anions and Cl⁻ anions.

Related literature

For general background to ferroelectric metal-organic frameworks, see: Ye et al. (2009 ); Fu et al. (2007 ). For phase transitions in ferroelectric materials, see: Zhang et al. (2008 ); Zhao et al. (2008 ); Ye et al. (2006 ).

Experimental

Crystal data

(C₆H₇ClN)₄[SnCl₆]Cl₂
M_r = 916.59
Monoclinic, C 2/c
a = 27.855 (6) Å
b = 7.2061 (14) Å
c = 21.895 (4) Å
β = 125.03 (3)°
V = 3598.8 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.63 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.715, T_max = 0.730
17870 measured reflections
4122 independent reflections
3581 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.067
S = 1.10
4122 reflections
188 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected bond lengths (Å)

Cl3—Sn1	2.4205 (11)
Cl4—Sn1	2.4076 (7)
Cl5—Sn1	2.4356 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl5ⁱ	0.89	2.64	3.522 (2)	172
N1—H1A⋯Cl3ⁱ	0.89	2.98	3.424 (2)	112
N1—H1B⋯Cl6ⁱⁱ	0.89	2.25	3.123 (3)	165
N1—H1C⋯Cl6ⁱⁱⁱ	0.89	2.26	3.120 (3)	162
N2—H2A⋯Cl3^iv	0.89	2.75	3.455 (2)	137
N2—H2A⋯Cl4^v	0.89	2.79	3.567 (2)	147
N2—H2A⋯Cl4^iv	0.89	2.92	3.344 (3)	111
N2—H2B⋯Cl6^vi	0.89	2.20	3.085 (3)	175
N2—H2C⋯Cl5^vii	0.89	2.61	3.424 (3)	153
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z; (iii) -x, -y+1, -z; (iv) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (vii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812021666/kp2409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021666/kp2409Isup2.hkl

checkCIF report

Comment top

The study of ferroelectric materials has received much attention; some of them have predominantly dielectric–ferroelectric performance (Ye et al., 2006; Fu et al., 2007; Zhao et al. 2008; Zhang et al., 2008; Ye et al., 2009). As a part of our work to obtain potential ferroelectric phase-transition material, we report herein on the crystal structure of title compound. Unluckily, the title compound has no dielectric anomalies in the temperature range 93–453 K, suggesting that it might be only a paraelectric.

The asymmetric unit of the title compound is shown in Fig. 1 and Sn-Cl bonds are listed in Table 1. The crystal packing (Fig. 2) is stabilised by intermolecular N—H···Cl hydrogen bonds between the [C₆H₇ClN]⁺cations and SnCl₆^2–anions and Cl^- anions (Table 2).

Related literature top

For general background to ferroelectric metal-organic frameworks, see: Ye et al. (2009); Fu et al. (2007). For phase transitions in ferroelectric materials, see: Zhang et al. (2008); Zhao et al. (2008); Ye et al. (2006).

Experimental top

For the preparation of the title compound, the water solution of the hydrochloric acid (10 mmol) was added to the ethanol solution of the 4-chlorobenzenamine(10 mmol), then the water solution of the SnCl₄(5 mmol) was added into a reaction mixture. The resulting precipitate was filtered. Colourless crystals suitable for X-ray analysis were formed after several weeks by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.[The suffix A denotes the symmetry code: 2-x y 1/2 - z.]
	Fig. 2. Crystal packing of the title compound. Dashed lines indicate hydrogen bonds.

Tetrakis(4-chloroanilinium) hexachloridostannate(IV) dichloride top

Crystal data top

(C₆H₇ClN)₄[SnCl₆]Cl₂	F(000) = 1816
M_r = 916.59	D_x = 1.692 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4122 reflections
a = 27.855 (6) Å	θ = 3.4–27.5°
b = 7.2061 (14) Å	µ = 1.63 mm⁻¹
c = 21.895 (4) Å	T = 293 K
β = 125.03 (3)°	Prism, colourless
V = 3598.8 (18) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	4122 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
CCD_Profile_fitting scans	h = −36→35
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.715, T_max = 0.730	l = −28→28
17870 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0236P)² + 4.0429P] where P = (F_o² + 2F_c²)/3
4122 reflections	(Δ/σ)_max = 0.002
188 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

(C₆H₇ClN)₄[SnCl₆]Cl₂	V = 3598.8 (18) Å³
M_r = 916.59	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 27.855 (6) Å	µ = 1.63 mm⁻¹
b = 7.2061 (14) Å	T = 293 K
c = 21.895 (4) Å	0.20 × 0.20 × 0.20 mm
β = 125.03 (3)°

Data collection top

Rigaku SCXmini diffractometer	4122 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3581 reflections with I > 2σ(I)
T_min = 0.715, T_max = 0.730	R_int = 0.031
17870 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.10	Δρ_max = 0.44 e Å⁻³
4122 reflections	Δρ_min = −0.46 e Å⁻³
188 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
C1	0.12061 (12)	0.1500 (4)	0.12876 (15)	0.0503 (6)
C2	0.13487 (13)	0.0639 (4)	0.08532 (16)	0.0540 (7)
H2	0.1066	−0.0001	0.0425	0.065*
C3	0.19188 (13)	0.0738 (4)	0.10633 (16)	0.0535 (7)
H3	0.2025	0.0155	0.0779	0.064*
C4	0.23257 (12)	0.1696 (4)	0.16906 (17)	0.0507 (7)
C5	0.21803 (13)	0.2551 (5)	0.21162 (17)	0.0632 (8)
H5	0.2463	0.3194	0.2544	0.076*
C6	0.16093 (14)	0.2459 (5)	0.19102 (17)	0.0661 (9)
H6	0.1503	0.3047	0.2195	0.079*
C7	0.39010 (11)	0.0792 (3)	0.05568 (13)	0.0401 (5)
C8	0.38139 (12)	−0.0100 (3)	−0.00526 (14)	0.0470 (6)
H8	0.4121	−0.0253	−0.0103	0.056*
C9	0.32612 (14)	−0.0767 (4)	−0.05904 (15)	0.0556 (7)
H9	0.3192	−0.1366	−0.1010	0.067*
C10	0.28179 (12)	−0.0544 (4)	−0.05054 (16)	0.0554 (7)
C11	0.29063 (13)	0.0384 (5)	0.00988 (18)	0.0634 (8)
H11	0.2597	0.0554	0.0144	0.076*
C12	0.34538 (13)	0.1062 (4)	0.06368 (16)	0.0559 (7)
H12	0.3519	0.1694	0.1049	0.067*
Cl1	0.21316 (4)	−0.14614 (15)	−0.11590 (6)	0.0983 (3)
Cl2	0.30443 (4)	0.17986 (14)	0.19641 (6)	0.0843 (3)
Cl3	0.94108 (3)	0.11974 (9)	0.11503 (3)	0.04947 (16)
Cl4	1.06231 (3)	−0.11341 (9)	0.25190 (4)	0.04712 (15)
Cl5	1.06027 (3)	0.36499 (8)	0.24919 (4)	0.04846 (15)
Cl6	0.02508 (4)	0.72478 (14)	0.05762 (5)	0.0808 (3)
N1	0.05994 (11)	0.1377 (4)	0.10653 (15)	0.0707 (8)
H1A	0.0577	0.1853	0.1423	0.106*
H1B	0.0488	0.0193	0.0993	0.106*
H1C	0.0365	0.2010	0.0645	0.106*
N2	0.44908 (10)	0.1413 (3)	0.11539 (12)	0.0525 (5)
H2A	0.4466	0.2420	0.1370	0.079*
H2B	0.4692	0.1682	0.0964	0.079*
H2C	0.4674	0.0515	0.1492	0.079*
Sn1	1.0000	0.12149 (3)	0.2500	0.03220 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0478 (15)	0.0652 (17)	0.0503 (15)	−0.0127 (13)	0.0353 (13)	−0.0134 (13)
C2	0.0628 (18)	0.0596 (17)	0.0540 (16)	−0.0140 (14)	0.0419 (15)	−0.0158 (13)
C3	0.0664 (18)	0.0497 (15)	0.0680 (18)	−0.0019 (13)	0.0524 (17)	−0.0038 (13)
C4	0.0492 (15)	0.0470 (15)	0.0678 (18)	0.0016 (12)	0.0405 (15)	0.0108 (13)
C5	0.0535 (17)	0.075 (2)	0.0566 (17)	−0.0164 (15)	0.0292 (15)	−0.0175 (15)
C6	0.0631 (19)	0.086 (2)	0.0632 (19)	−0.0188 (17)	0.0446 (17)	−0.0322 (17)
C7	0.0448 (13)	0.0332 (12)	0.0393 (12)	0.0021 (10)	0.0223 (11)	0.0041 (9)
C8	0.0551 (16)	0.0395 (13)	0.0508 (15)	0.0061 (11)	0.0329 (13)	0.0027 (11)
C9	0.072 (2)	0.0416 (14)	0.0429 (14)	−0.0030 (13)	0.0270 (15)	−0.0031 (11)
C10	0.0507 (16)	0.0471 (15)	0.0483 (15)	−0.0062 (12)	0.0167 (13)	0.0083 (12)
C11	0.0526 (17)	0.074 (2)	0.071 (2)	0.0020 (15)	0.0404 (17)	0.0082 (17)
C12	0.0602 (18)	0.0636 (18)	0.0546 (16)	0.0014 (14)	0.0392 (15)	−0.0034 (14)
Cl1	0.0635 (5)	0.0962 (7)	0.0859 (7)	−0.0256 (5)	0.0140 (5)	0.0026 (5)
Cl2	0.0541 (5)	0.0922 (6)	0.1164 (8)	0.0013 (4)	0.0548 (5)	0.0153 (6)
Cl3	0.0565 (4)	0.0537 (4)	0.0338 (3)	0.0105 (3)	0.0233 (3)	0.0055 (3)
Cl4	0.0442 (3)	0.0433 (3)	0.0505 (3)	0.0109 (3)	0.0252 (3)	−0.0019 (3)
Cl5	0.0575 (4)	0.0401 (3)	0.0623 (4)	−0.0089 (3)	0.0428 (3)	−0.0001 (3)
Cl6	0.0672 (5)	0.1076 (7)	0.0878 (6)	−0.0289 (5)	0.0563 (5)	−0.0438 (5)
N1	0.0547 (15)	0.110 (2)	0.0647 (16)	−0.0254 (14)	0.0443 (14)	−0.0329 (15)
N2	0.0499 (13)	0.0521 (13)	0.0477 (12)	0.0004 (10)	0.0234 (11)	−0.0010 (10)
Sn1	0.04091 (13)	0.02673 (11)	0.03437 (12)	0.000	0.02476 (10)	0.000

Geometric parameters (Å, º) top

C1—C6	1.356 (4)	C9—H9	0.9300
C1—C2	1.372 (4)	C10—C11	1.373 (4)
C1—N1	1.468 (3)	C10—Cl1	1.732 (3)
C2—C3	1.378 (4)	C11—C12	1.374 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.364 (4)	C12—H12	0.9300
C3—H3	0.9300	Cl3—Sn1	2.4205 (11)
C4—C5	1.359 (4)	Cl4—Sn1	2.4076 (7)
C4—Cl2	1.731 (3)	Cl5—Sn1	2.4356 (7)
C5—C6	1.383 (4)	N1—H1A	0.8900
C5—H5	0.9300	N1—H1B	0.8900
C6—H6	0.9300	N1—H1C	0.8900
C7—C12	1.368 (4)	N2—H2A	0.8900
C7—C8	1.371 (3)	N2—H2B	0.8900
C7—N2	1.464 (3)	N2—H2C	0.8900
C8—C9	1.381 (4)	Sn1—Cl4ⁱ	2.4076 (7)
C8—H8	0.9300	Sn1—Cl3ⁱ	2.4205 (11)
C9—C10	1.360 (4)	Sn1—Cl5ⁱ	2.4356 (7)

C6—C1—C2	121.7 (3)	C12—C11—H11	120.1
C6—C1—N1	119.7 (2)	C7—C12—C11	118.9 (3)
C2—C1—N1	118.6 (2)	C7—C12—H12	120.5
C1—C2—C3	118.8 (3)	C11—C12—H12	120.5
C1—C2—H2	120.6	C1—N1—H1A	109.5
C3—C2—H2	120.6	C1—N1—H1B	109.5
C4—C3—C2	119.6 (3)	H1A—N1—H1B	109.5
C4—C3—H3	120.2	C1—N1—H1C	109.5
C2—C3—H3	120.2	H1A—N1—H1C	109.5
C5—C4—C3	121.2 (3)	H1B—N1—H1C	109.5
C5—C4—Cl2	119.0 (2)	C7—N2—H2A	109.5
C3—C4—Cl2	119.9 (2)	C7—N2—H2B	109.5
C4—C5—C6	119.6 (3)	H2A—N2—H2B	109.5
C4—C5—H5	120.2	C7—N2—H2C	109.5
C6—C5—H5	120.2	H2A—N2—H2C	109.5
C1—C6—C5	119.1 (3)	H2B—N2—H2C	109.5
C1—C6—H6	120.5	Cl4ⁱ—Sn1—Cl4	90.65 (4)
C5—C6—H6	120.5	Cl4ⁱ—Sn1—Cl3	89.91 (3)
C12—C7—C8	121.7 (2)	Cl4—Sn1—Cl3	89.67 (3)
C12—C7—N2	118.7 (2)	Cl4ⁱ—Sn1—Cl3ⁱ	89.67 (3)
C8—C7—N2	119.6 (2)	Cl4—Sn1—Cl3ⁱ	89.91 (3)
C7—C8—C9	118.7 (3)	Cl3—Sn1—Cl3ⁱ	179.40 (3)
C7—C8—H8	120.6	Cl4ⁱ—Sn1—Cl5	178.18 (2)
C9—C8—H8	120.6	Cl4—Sn1—Cl5	90.77 (3)
C10—C9—C8	119.9 (3)	Cl3—Sn1—Cl5	88.97 (3)
C10—C9—H9	120.1	Cl3ⁱ—Sn1—Cl5	91.46 (3)
C8—C9—H9	120.1	Cl4ⁱ—Sn1—Cl5ⁱ	90.77 (3)
C9—C10—C11	121.0 (3)	Cl4—Sn1—Cl5ⁱ	178.18 (2)
C9—C10—Cl1	120.0 (2)	Cl3—Sn1—Cl5ⁱ	91.46 (3)
C11—C10—Cl1	119.0 (3)	Cl3ⁱ—Sn1—Cl5ⁱ	88.97 (3)
C10—C11—C12	119.7 (3)	Cl5—Sn1—Cl5ⁱ	87.82 (4)
C10—C11—H11	120.1

C6—C1—C2—C3	0.8 (5)	C12—C7—C8—C9	−1.1 (4)
N1—C1—C2—C3	−179.5 (3)	N2—C7—C8—C9	176.5 (2)
C1—C2—C3—C4	−0.5 (4)	C7—C8—C9—C10	−0.5 (4)
C2—C3—C4—C5	0.3 (5)	C8—C9—C10—C11	1.9 (4)
C2—C3—C4—Cl2	179.1 (2)	C8—C9—C10—Cl1	−177.3 (2)
C3—C4—C5—C6	−0.3 (5)	C9—C10—C11—C12	−1.6 (5)
Cl2—C4—C5—C6	−179.1 (3)	Cl1—C10—C11—C12	177.6 (2)
C2—C1—C6—C5	−0.8 (5)	C8—C7—C12—C11	1.4 (4)
N1—C1—C6—C5	179.5 (3)	N2—C7—C12—C11	−176.2 (3)
C4—C5—C6—C1	0.5 (5)	C10—C11—C12—C7	0.0 (5)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl5ⁱⁱ	0.89	2.64	3.522 (2)	172
N1—H1A···Cl3ⁱⁱ	0.89	2.98	3.424 (2)	112
N1—H1B···Cl6ⁱⁱⁱ	0.89	2.25	3.123 (3)	165
N1—H1C···Cl6^iv	0.89	2.26	3.120 (3)	162
N2—H2A···Cl3^v	0.89	2.75	3.455 (2)	137
N2—H2A···Cl4^vi	0.89	2.79	3.567 (2)	147
N2—H2A···Cl4^v	0.89	2.92	3.344 (3)	111
N2—H2B···Cl6^vii	0.89	2.20	3.085 (3)	175
N2—H2C···Cl5^viii	0.89	2.61	3.424 (3)	153

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

Experimental details

Crystal data
Chemical formula	(C₆H₇ClN)₄[SnCl₆]Cl₂
M_r	916.59
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.855 (6), 7.2061 (14), 21.895 (4)
β (°)	125.03 (3)
V (Å³)	3598.8 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.63
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.715, 0.730
No. of measured, independent and observed [I > 2σ(I)] reflections	17870, 4122, 3581
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.067, 1.10
No. of reflections	4122
No. of parameters	188
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.46

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Selected bond lengths (Å) top

Cl3—Sn1	2.4205 (11)	Cl5—Sn1	2.4356 (7)
Cl4—Sn1	2.4076 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl5ⁱ	0.89	2.64	3.522 (2)	171.9
N1—H1A···Cl3ⁱ	0.89	2.98	3.424 (2)	112.4
N1—H1B···Cl6ⁱⁱ	0.89	2.25	3.123 (3)	164.9
N1—H1C···Cl6ⁱⁱⁱ	0.89	2.26	3.120 (3)	162.3
N2—H2A···Cl3^iv	0.89	2.75	3.455 (2)	136.6
N2—H2A···Cl4^v	0.89	2.79	3.567 (2)	147.4
N2—H2A···Cl4^iv	0.89	2.92	3.344 (3)	111.4
N2—H2B···Cl6^vi	0.89	2.20	3.085 (3)	175.3
N2—H2C···Cl5^vii	0.89	2.61	3.424 (3)	153.1

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

Acknowledgements

The authors are grateful to the starter fund of Southeast University, Nanjing, People's Republic of China.

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