(m-Phenyl­enedimethyl­ene)diammonium dichloride

Cheng, H.; Li, H.

doi:10.1107/S1600536808031334

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2060

doi:10.1107/S1600536808031334

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(m-Phenylenedimethylene)diammonium dichloride

Hua Cheng ^a ^* and Huisheng Li ^a

^aDepartment of Chemistry and Biology, Xiangfan University, Xiangfan 441053, People's Republic of China
^*Correspondence e-mail: chenghua510@yahoo.com.cn

(Received 22 September 2008; accepted 27 September 2008; online 4 October 2008)

The asymmetric unit of the title compound, C₈H₁₄N₂²⁺·2Cl⁻, contains one and a half of the dications and three chloride anions. The half molecule is completed by crystallographic twofold symmetry with two C atoms lying on the rotation axis. The two ammonium groups in each cation adopt a trans conformation with respect ot the benzene ring. The ammonium groups and chloride anions are involved in the formation of a three-dimensional N—H⋯Cl hydrogen-bonding network, which stabilizes the crystal packing.

Related literature

For general background and applications, see: Pasini & Zunino (1987 ); Otsuka et al. (1990 ); Michalson & Smuszkovicz (1989 ); Reedijk (1996 ); Blaser (1992 ); Soai & Niwa (1992 ); Jacobsen (1993 ); Kolb et al. (1994 ).

Experimental

Crystal data

C₈H₁₄N₂²⁺·2Cl⁻
M_r = 209.11
Monoclinic, C 2/c
a = 27.5859 (18) Å
b = 13.1594 (14) Å
c = 8.8324 (6) Å
β = 103.539 (1)°
V = 3117.2 (4) Å³
Z = 12
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.893, T_max = 0.945
14623 measured reflections
3066 independent reflections
2615 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.06
3066 reflections
191 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯Cl1	0.878 (16)	2.338 (16)	3.206 (2)	170 (2)
N2—H2C⋯Cl3	0.927 (16)	2.360 (17)	3.2453 (19)	160 (2)
N1—H1B⋯Cl2	0.869 (15)	2.276 (17)	3.1186 (18)	163 (2)
N3—H3C⋯Cl2ⁱ	0.880 (17)	2.343 (19)	3.171 (2)	157 (2)
N2—H2B⋯Cl1ⁱⁱ	0.860 (16)	2.58 (2)	3.189 (2)	129.0 (19)
N1—H1C⋯Cl3ⁱⁱⁱ	0.884 (15)	2.341 (17)	3.2071 (18)	166 (2)
N2—H2A⋯Cl2^iv	0.842 (16)	2.442 (18)	3.201 (2)	150 (2)
N1—H1A⋯Cl3^iv	0.858 (16)	2.506 (18)	3.2527 (17)	146.0 (19)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031334/cv2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031334/cv2456Isup2.hkl

checkCIF report

Comment top

The diamine compounds are important in biologically active natural products (Pasini & Zunino, 1987; Otsuka et al., 1990), in medicinal chemistry (Michalson & Smuszkovicz, 1989; Reedijk, 1996). They are also used as chiral auxiliaries and chiral ligands in asymmetric catalysis (Blaser, 1992; Soai & Niwa, 1992; Jacobsen, 1993; Kolb et al., 1994). Herewith we present the title diamine compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal. Two amino groups in the dications adopt trans-conformation and each amino group form three N—H···Cl hydrogen bonds (Table 1) to stabilize the crystal packing.

Related literature top

For related literature, see: Pasini & Zunino (1987); Otsuka et al. (1990); Michalson & Smuszkovicz (1989); Reedijk (1996); Blaser (1992); Soai & Niwa (1992); Jacobsen (1993); Kolb et al. (1994). [From the Section Editors: It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···." etc. Please revise this section as indicated.]

Experimental top

1,3-Phenylenedimethanamine was dissolved in ethanol, then 1N HCl was dropped to the solution. Colourless, block-like crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of ethanol at 283 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius.

(m-Phenylenedimethylene)diammonium dichloride top

Crystal data top

C₈H₁₄N₂²⁺·2Cl⁻	F(000) = 1320
M_r = 209.11	D_x = 1.337 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -c/2yc	Cell parameters from 6157 reflections
a = 27.5859 (18) Å	θ = 2.8–27.8°
b = 13.1594 (14) Å	µ = 0.58 mm⁻¹
c = 8.8324 (6) Å	T = 298 K
β = 103.539 (1)°	Block, colourless
V = 3117.2 (4) Å³	0.20 × 0.10 × 0.10 mm
Z = 12

Data collection top

Bruker SMART CCD area-detector diffractometer	3066 independent reflections
Radiation source: fine-focus sealed tube	2615 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −33→33
T_min = 0.894, T_max = 0.945	k = −14→16
14623 measured reflections	l = −10→10

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0717P)²] where P = (F_o² + 2F_c²)/3
3066 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.36 e Å⁻³
9 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₈H₁₄N₂²⁺·2Cl⁻	V = 3117.2 (4) Å³
M_r = 209.11	Z = 12
Monoclinic, C2/c	Mo Kα radiation
a = 27.5859 (18) Å	µ = 0.58 mm⁻¹
b = 13.1594 (14) Å	T = 298 K
c = 8.8324 (6) Å	0.20 × 0.10 × 0.10 mm
β = 103.539 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3066 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2615 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.945	R_int = 0.103
14623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	9 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.36 e Å⁻³
3066 reflections	Δρ_min = −0.31 e Å⁻³
191 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.27771 (7)	0.50258 (14)	−0.0022 (2)	0.0355 (4)
C2	0.26673 (7)	0.60114 (16)	0.0327 (2)	0.0414 (5)
H2	0.2856	0.6547	0.0089	0.050*
C3	0.22778 (7)	0.62046 (16)	0.1031 (2)	0.0438 (5)
H3	0.2206	0.6870	0.1261	0.053*
C4	0.19964 (7)	0.54155 (16)	0.1392 (2)	0.0398 (5)
H4	0.1735	0.5549	0.1865	0.048*
C5	0.21012 (6)	0.44213 (14)	0.1052 (2)	0.0341 (4)
C6	0.24907 (7)	0.42332 (14)	0.0342 (2)	0.0355 (4)
H6	0.2561	0.3569	0.0106	0.043*
C7	0.31958 (8)	0.48207 (17)	−0.0814 (2)	0.0447 (5)
H7A	0.3118	0.4215	−0.1450	0.054*
H7B	0.3220	0.5384	−0.1500	0.054*
C8	0.18156 (7)	0.35486 (16)	0.1535 (3)	0.0458 (5)
H8A	0.1995	0.2922	0.1469	0.055*
H8B	0.1802	0.3642	0.2613	0.055*
C9	0.00722 (7)	0.23186 (15)	0.6209 (2)	0.0349 (4)
C10	0.00730 (8)	0.12695 (16)	0.6221 (3)	0.0466 (5)
H10	0.0123	0.0915	0.5360	0.056*
C11	0.0000	0.0741 (2)	0.7500	0.0553 (8)
H11	0.0000	0.0034	0.7500	0.066*
C12	0.0000	0.2839 (2)	0.7500	0.0349 (6)
H12	0.0000	0.3546	0.7500	0.042*
C13	0.01564 (8)	0.28914 (19)	0.4806 (3)	0.0483 (5)
H13A	0.0100	0.2439	0.3915	0.058*
H13B	−0.0081	0.3446	0.4561	0.058*
Cl1	0.08043 (2)	0.50782 (4)	0.76455 (6)	0.04504 (18)
Cl2	0.35181 (2)	0.28315 (4)	0.23278 (6)	0.04852 (19)
Cl3	0.094656 (19)	0.15614 (4)	0.24153 (6)	0.04295 (18)
N1	0.36851 (6)	0.46791 (14)	0.0298 (2)	0.0375 (4)
H1C	0.3787 (8)	0.5257 (13)	0.078 (3)	0.045*
H1A	0.3894 (7)	0.4518 (17)	−0.025 (2)	0.045*
H1B	0.3683 (8)	0.4230 (15)	0.102 (2)	0.045*
N2	0.13028 (7)	0.34496 (14)	0.0574 (2)	0.0433 (4)
H2A	0.1269 (9)	0.3278 (17)	−0.036 (2)	0.052*
H2B	0.1123 (8)	0.3989 (15)	0.050 (3)	0.052*
H2C	0.1129 (8)	0.2921 (15)	0.090 (3)	0.052*
N3	0.06651 (7)	0.32989 (15)	0.5100 (2)	0.0433 (4)
H3C	0.0906 (7)	0.2890 (16)	0.557 (3)	0.052*
H3A	0.0729 (8)	0.3619 (17)	0.430 (2)	0.052*
H3B	0.0690 (8)	0.3733 (16)	0.587 (2)	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0337 (10)	0.0412 (11)	0.0320 (10)	0.0014 (8)	0.0086 (8)	0.0026 (8)
C2	0.0419 (11)	0.0340 (11)	0.0477 (11)	−0.0020 (9)	0.0093 (9)	0.0080 (9)
C3	0.0437 (11)	0.0300 (11)	0.0564 (13)	0.0065 (9)	0.0093 (10)	0.0010 (9)
C4	0.0348 (10)	0.0394 (11)	0.0465 (11)	0.0074 (8)	0.0121 (9)	0.0002 (9)
C5	0.0312 (9)	0.0350 (11)	0.0351 (10)	−0.0009 (8)	0.0060 (8)	0.0031 (8)
C6	0.0383 (10)	0.0304 (10)	0.0373 (10)	0.0049 (8)	0.0080 (8)	−0.0016 (8)
C7	0.0441 (12)	0.0572 (14)	0.0357 (11)	0.0029 (10)	0.0155 (10)	0.0038 (9)
C8	0.0410 (11)	0.0424 (12)	0.0537 (13)	−0.0015 (9)	0.0106 (10)	0.0110 (10)
C9	0.0297 (9)	0.0420 (12)	0.0345 (10)	−0.0004 (8)	0.0103 (8)	0.0021 (8)
C10	0.0534 (12)	0.0404 (13)	0.0487 (13)	0.0014 (10)	0.0174 (10)	−0.0118 (10)
C11	0.070 (2)	0.0306 (16)	0.067 (2)	0.000	0.0181 (18)	0.000
C12	0.0321 (13)	0.0293 (14)	0.0460 (16)	0.000	0.0148 (12)	0.000
C13	0.0415 (11)	0.0678 (16)	0.0373 (11)	−0.0028 (10)	0.0126 (9)	0.0077 (10)
Cl1	0.0547 (3)	0.0370 (3)	0.0492 (3)	−0.0046 (2)	0.0237 (3)	−0.0082 (2)
Cl2	0.0507 (3)	0.0449 (3)	0.0514 (3)	0.0066 (2)	0.0148 (3)	0.0119 (2)
Cl3	0.0483 (3)	0.0368 (3)	0.0480 (3)	0.0090 (2)	0.0199 (3)	0.0070 (2)
N1	0.0371 (9)	0.0345 (9)	0.0450 (10)	−0.0037 (7)	0.0179 (8)	−0.0048 (7)
N2	0.0414 (10)	0.0364 (10)	0.0530 (11)	−0.0058 (8)	0.0132 (9)	0.0012 (8)
N3	0.0455 (10)	0.0417 (11)	0.0438 (11)	−0.0037 (8)	0.0130 (9)	0.0101 (8)

Geometric parameters (Å, º) top

C1—C2	1.383 (3)	C9—C13	1.514 (3)
C1—C6	1.391 (3)	C10—C11	1.381 (3)
C1—C7	1.508 (3)	C10—H10	0.9300
C2—C3	1.385 (3)	C11—C10ⁱ	1.381 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.378 (3)	C12—C9ⁱ	1.384 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.388 (3)	C13—N3	1.468 (3)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.387 (2)	C13—H13B	0.9700
C5—C8	1.510 (3)	N1—H1C	0.884 (15)
C6—H6	0.9300	N1—H1A	0.858 (16)
C7—N1	1.483 (3)	N1—H1B	0.869 (15)
C7—H7A	0.9700	N2—H2A	0.842 (16)
C7—H7B	0.9700	N2—H2B	0.860 (16)
C8—N2	1.475 (3)	N2—H2C	0.927 (16)
C8—H8A	0.9700	N3—H3C	0.880 (17)
C8—H8B	0.9700	N3—H3A	0.877 (16)
C9—C10	1.381 (3)	N3—H3B	0.878 (16)
C9—C12	1.384 (2)

C2—C1—C6	119.05 (17)	C9—C10—C11	120.7 (2)
C2—C1—C7	120.19 (17)	C9—C10—H10	119.7
C6—C1—C7	120.75 (17)	C11—C10—H10	119.7
C1—C2—C3	120.39 (18)	C10—C11—C10ⁱ	119.5 (3)
C1—C2—H2	119.8	C10—C11—H11	120.2
C3—C2—H2	119.8	C10ⁱ—C11—H11	120.2
C4—C3—C2	120.25 (19)	C9—C12—C9ⁱ	120.6 (3)
C4—C3—H3	119.9	C9—C12—H12	119.7
C2—C3—H3	119.9	C9ⁱ—C12—H12	119.7
C3—C4—C5	120.21 (17)	N3—C13—C9	111.14 (18)
C3—C4—H4	119.9	N3—C13—H13A	109.4
C5—C4—H4	119.9	C9—C13—H13A	109.4
C6—C5—C4	119.26 (17)	N3—C13—H13B	109.4
C6—C5—C8	120.17 (17)	C9—C13—H13B	109.4
C4—C5—C8	120.46 (17)	H13A—C13—H13B	108.0
C5—C6—C1	120.85 (17)	C7—N1—H1C	110.3 (15)
C5—C6—H6	119.6	C7—N1—H1A	106.6 (15)
C1—C6—H6	119.6	H1C—N1—H1A	108 (2)
N1—C7—C1	113.13 (16)	C7—N1—H1B	114.1 (14)
N1—C7—H7A	109.0	H1C—N1—H1B	107 (2)
C1—C7—H7A	109.0	H1A—N1—H1B	111 (2)
N1—C7—H7B	109.0	C8—N2—H2A	117.4 (18)
C1—C7—H7B	109.0	C8—N2—H2B	115.4 (16)
H7A—C7—H7B	107.8	H2A—N2—H2B	103 (2)
N2—C8—C5	113.48 (17)	C8—N2—H2C	112.6 (15)
N2—C8—H8A	108.9	H2A—N2—H2C	99 (2)
C5—C8—H8A	108.9	H2B—N2—H2C	108 (2)
N2—C8—H8B	108.9	C13—N3—H3C	116.4 (16)
C5—C8—H8B	108.9	C13—N3—H3A	113.4 (16)
H8A—C8—H8B	107.7	H3C—N3—H3A	114 (2)
C10—C9—C12	119.27 (18)	C13—N3—H3B	105.8 (15)
C10—C9—C13	120.27 (18)	H3C—N3—H3B	97 (2)
C12—C9—C13	120.5 (2)	H3A—N3—H3B	109 (2)

C6—C1—C2—C3	0.0 (3)	C6—C1—C7—N1	−92.2 (2)
C7—C1—C2—C3	178.93 (19)	C6—C5—C8—N2	−109.5 (2)
C1—C2—C3—C4	0.1 (3)	C4—C5—C8—N2	74.2 (2)
C2—C3—C4—C5	0.0 (3)	C12—C9—C10—C11	0.4 (3)
C3—C4—C5—C6	−0.2 (3)	C13—C9—C10—C11	179.56 (17)
C3—C4—C5—C8	176.14 (19)	C9—C10—C11—C10ⁱ	−0.18 (13)
C4—C5—C6—C1	0.4 (3)	C10—C9—C12—C9ⁱ	−0.18 (13)
C8—C5—C6—C1	−175.99 (18)	C13—C9—C12—C9ⁱ	−179.4 (2)
C2—C1—C6—C5	−0.3 (3)	C10—C9—C13—N3	−103.1 (2)
C7—C1—C6—C5	−179.17 (18)	C12—C9—C13—N3	76.1 (2)
C2—C1—C7—N1	88.9 (2)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl1	0.88 (2)	2.34 (2)	3.206 (2)	170 (2)
N2—H2C···Cl3	0.93 (2)	2.36 (2)	3.2453 (19)	160 (2)
N1—H1B···Cl2	0.87 (2)	2.28 (2)	3.1186 (18)	163 (2)
N3—H3C···Cl2ⁱⁱ	0.88 (2)	2.34 (2)	3.171 (2)	157 (2)
N2—H2B···Cl1ⁱⁱⁱ	0.86 (2)	2.58 (2)	3.189 (2)	129 (2)
N1—H1C···Cl3^iv	0.88 (2)	2.34 (2)	3.2071 (18)	166 (2)
N2—H2A···Cl2^v	0.84 (2)	2.44 (2)	3.201 (2)	150 (2)
N1—H1A···Cl3^v	0.86 (2)	2.51 (2)	3.2527 (17)	146 (2)

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

Experimental details

Crystal data
Chemical formula	C₈H₁₄N₂²⁺·2Cl⁻
M_r	209.11
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	27.5859 (18), 13.1594 (14), 8.8324 (6)
β (°)	103.539 (1)
V (Å³)	3117.2 (4)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.894, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	14623, 3066, 2615
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 1.06
No. of reflections	3066
No. of parameters	191
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl1	0.878 (16)	2.338 (16)	3.206 (2)	170 (2)
N2—H2C···Cl3	0.927 (16)	2.360 (17)	3.2453 (19)	160 (2)
N1—H1B···Cl2	0.869 (15)	2.276 (17)	3.1186 (18)	163 (2)
N3—H3C···Cl2ⁱ	0.880 (17)	2.343 (19)	3.171 (2)	157 (2)
N2—H2B···Cl1ⁱⁱ	0.860 (16)	2.58 (2)	3.189 (2)	129.0 (19)
N1—H1C···Cl3ⁱⁱⁱ	0.884 (15)	2.341 (17)	3.2071 (18)	166 (2)
N2—H2A···Cl2^iv	0.842 (16)	2.442 (18)	3.201 (2)	150 (2)
N1—H1A···Cl3^iv	0.858 (16)	2.506 (18)	3.2527 (17)	146.0 (19)

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

Acknowledgements

The authors are grateful to Xiangfan University for financial support.

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