2-Amino-5-(1H-tetra­zol-5-yl)pyridinium chloride

Dai, J.; Wen, X.-C.

doi:10.1107/S1600536808031164

organic compounds

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Volume 64| Part 11| November 2008| Page o2232

doi:10.1107/S1600536808031164

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2-Amino-5-(1H-tetrazol-5-yl)pyridinium chloride

Jing Dai ^a and Xiao-Chun Wen ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 11 September 2008; accepted 26 September 2008; online 31 October 2008)

In the title salt, C₆H₇N₆⁺·Cl⁻, there are two organic cations with similar conformations and two chloride anions in the asymmetric unit. The pyridine and tetrazole rings are essentially coplanar in each cation, with dihedral angles of 4.94 (15) and 5.41 (14)°. The pyridine N atoms are protonated. The crystal packing is stabilized by N—H⋯N and N—H⋯Cl hydrogen bonds, forming an infinite sheets parallel to the (101).

Related literature

For uses of tetrazole derivatives, see: Dai & Fu (2008 ); Wang et al. (2005 ); Wen (2008 ); Xiong et al. (2002 ).

Experimental

Crystal data

C₆H₇N₆⁺·Cl⁻
M_r = 198.63
Monoclinic, P 2₁ /c
a = 14.043 (3) Å
b = 13.238 (3) Å
c = 9.5766 (19) Å
β = 109.35 (3)°
V = 1679.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 298 (2) K
0.45 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.859, T_max = 0.920
16820 measured reflections
3855 independent reflections
3123 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.125
S = 1.11
3855 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N5ⁱ	0.86	2.59	3.317 (2)	143
N1—H1⋯N6ⁱ	0.86	2.04	2.894 (2)	171
N2—H2A⋯N5ⁱ	0.86	2.15	2.972 (3)	160
N7—H7⋯N11ⁱⁱ	0.86	2.57	3.304 (2)	144
N7—H7⋯N12ⁱⁱ	0.86	2.06	2.913 (2)	169
N8—H8A⋯N11ⁱⁱ	0.86	2.20	3.024 (3)	160
N2—H2B⋯Cl1ⁱⁱⁱ	0.86	2.36	3.2187 (18)	177
N3—H3A⋯Cl2ⁱ	0.86	2.17	3.0047 (19)	165
N8—H8B⋯Cl2^iv	0.86	2.39	3.2432 (18)	172
N9—H9A⋯Cl1^v	0.86	2.18	3.0031 (18)	160
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031164/bh2196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031164/bh2196Isup2.hkl

checkCIF report

Comment top

Tetrazole derivatives have found a wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions, and for the construction of novel metal-organic frameworks (Wang et al., 2005; Xiong et al., 2002; Wen, 2008; Dai & Fu, 2008). We report here the crystal structure of the title salt (Fig. 1).

The title compound contains two organic cations with similar conformation and two Cl^- ions in the asymmetric unit. The pyridine N atoms are protonated. The pyridine rings and tetrazole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 4.94 (15) and 5.41 (14)°. The packing of ions is stabilized by N—H···N and N—H···Cl hydrogen bonds, to form an infinite two-dimensional layers parallel to the (1 0 1) plane in the crystal (Table 1 and Fig. 2).

Related literature top

For uses of tetrazole derivatives, see: Dai & Fu (2008); Wang et al. (2005); Wen (2008); Xiong et al. (2002).

Experimental top

2-Amino-5-cyanopyridine (30 mmol), NaN ₃ (45 mmol), NH₄Cl (33 mmol) and DMF (50 ml) were mixed in a flask under nitrogen atmosphere, and the mixture stirred at 383 K for 20 h. The resulting solution was then poured into ice-water (100 ml), and a white solid was obtained after adding hydrochloric acid (6 M) until pH=6. The precipitate was filtered and washed with distilled water. Colourless block-shaped crystals suitable for X-ray analysis were obtained from the crude product by slow evaporation of an ethanol/hydrochloric acid (50:1 v/v) solution.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the c axis, showing the two-dimensional hydrogen bonds network. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

2-Amino-5-(1H-tetrazol-5-yl)pyridinium chloride top

Crystal data top

C₆H₇N₆⁺·Cl⁻	F(000) = 816
M_r = 198.63	D_x = 1.571 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3690 reflections
a = 14.043 (3) Å	θ = 2.3–27.5°
b = 13.238 (3) Å	µ = 0.41 mm⁻¹
c = 9.5766 (19) Å	T = 298 K
β = 109.35 (3)°	Block, colorless
V = 1679.7 (6) Å³	0.45 × 0.25 × 0.20 mm
Z = 8

Data collection top

Rigaku Mercury2 diffractometer	3855 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
T_min = 0.859, T_max = 0.920	l = −12→12
16820 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0556P)² + 0.4684P] where P = (F_o² + 2F_c²)/3
3855 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₆H₇N₆⁺·Cl⁻	V = 1679.7 (6) Å³
M_r = 198.63	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.043 (3) Å	µ = 0.41 mm⁻¹
b = 13.238 (3) Å	T = 298 K
c = 9.5766 (19) Å	0.45 × 0.25 × 0.20 mm
β = 109.35 (3)°

Data collection top

Rigaku Mercury2 diffractometer	3855 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3123 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.920	R_int = 0.034
16820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.12	Δρ_max = 0.28 e Å⁻³
3855 reflections	Δρ_min = −0.23 e Å⁻³
235 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.56207 (12)	0.65987 (12)	0.17350 (18)	0.0344 (4)
H1	0.5639	0.7245	0.1662	0.041*
N3	0.36346 (13)	0.52444 (13)	0.37792 (19)	0.0368 (4)
H3A	0.3600	0.5892	0.3818	0.044*
C1	0.62505 (14)	0.60404 (14)	0.1236 (2)	0.0313 (4)
N2	0.68458 (13)	0.64965 (13)	0.0611 (2)	0.0413 (4)
H2A	0.6831	0.7143	0.0523	0.050*
H2B	0.7247	0.6146	0.0292	0.050*
N6	0.40734 (13)	0.37577 (12)	0.33322 (19)	0.0382 (4)
N4	0.31050 (14)	0.45963 (13)	0.4305 (2)	0.0428 (4)
C6	0.42266 (14)	0.47298 (14)	0.3184 (2)	0.0310 (4)
N5	0.33724 (14)	0.37053 (13)	0.4030 (2)	0.0430 (4)
C4	0.49237 (14)	0.51714 (13)	0.2516 (2)	0.0304 (4)
C2	0.62316 (14)	0.49827 (14)	0.1406 (2)	0.0333 (4)
H2	0.6657	0.4574	0.1086	0.040*
C3	0.55896 (15)	0.45611 (14)	0.2039 (2)	0.0336 (4)
H3	0.5587	0.3864	0.2160	0.040*
C5	0.49636 (15)	0.61909 (14)	0.2344 (2)	0.0337 (4)
H5	0.4537	0.6610	0.2646	0.040*
N7	0.92034 (13)	0.39582 (12)	0.30105 (18)	0.0364 (4)
H7	0.9131	0.4604	0.2998	0.044*
N9	1.13591 (12)	0.26242 (13)	0.12521 (19)	0.0367 (4)
H9A	1.1409	0.3272	0.1246	0.044*
N8	0.80738 (13)	0.38416 (13)	0.4302 (2)	0.0422 (4)
H8A	0.8043	0.4490	0.4319	0.051*
H8B	0.7726	0.3485	0.4708	0.051*
C7	0.86565 (14)	0.33931 (15)	0.3650 (2)	0.0329 (4)
N10	1.19013 (14)	0.19768 (13)	0.0747 (2)	0.0425 (4)
N12	1.08698 (13)	0.11357 (12)	0.15986 (19)	0.0374 (4)
C12	1.07262 (14)	0.21051 (14)	0.1769 (2)	0.0311 (4)
N11	1.16049 (14)	0.10833 (13)	0.0959 (2)	0.0429 (4)
C10	1.00037 (14)	0.25408 (14)	0.2397 (2)	0.0304 (4)
C9	0.94263 (15)	0.19202 (14)	0.3023 (2)	0.0339 (4)
H9	0.9504	0.1222	0.3025	0.041*
C11	0.98593 (16)	0.35597 (14)	0.2389 (2)	0.0363 (4)
H11	1.0211	0.3983	0.1957	0.044*
C8	0.87624 (15)	0.23312 (15)	0.3618 (2)	0.0337 (4)
H8	0.8378	0.1915	0.4004	0.040*
Cl1	0.84188 (4)	0.97883 (4)	0.45292 (7)	0.04632 (17)
Cl2	0.65611 (4)	0.24380 (4)	0.05567 (6)	0.04478 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0407 (9)	0.0214 (8)	0.0500 (10)	0.0034 (7)	0.0270 (8)	0.0030 (7)
N3	0.0440 (10)	0.0261 (8)	0.0491 (10)	−0.0020 (7)	0.0273 (8)	−0.0008 (7)
C1	0.0332 (10)	0.0274 (9)	0.0362 (10)	0.0024 (7)	0.0157 (8)	0.0009 (7)
N2	0.0483 (11)	0.0305 (9)	0.0589 (11)	0.0027 (7)	0.0363 (9)	0.0028 (8)
N6	0.0456 (10)	0.0267 (8)	0.0507 (10)	−0.0021 (7)	0.0270 (8)	0.0009 (7)
N4	0.0518 (11)	0.0327 (9)	0.0561 (11)	−0.0061 (8)	0.0343 (9)	−0.0012 (8)
C6	0.0334 (10)	0.0265 (9)	0.0358 (10)	−0.0001 (7)	0.0152 (8)	−0.0004 (7)
N5	0.0529 (11)	0.0299 (9)	0.0581 (11)	−0.0034 (8)	0.0346 (9)	−0.0008 (8)
C4	0.0313 (9)	0.0259 (9)	0.0368 (10)	−0.0001 (7)	0.0149 (8)	0.0011 (7)
C2	0.0341 (10)	0.0284 (9)	0.0419 (11)	0.0044 (8)	0.0186 (8)	−0.0002 (8)
C3	0.0368 (10)	0.0238 (9)	0.0422 (11)	0.0017 (7)	0.0158 (8)	−0.0001 (8)
C5	0.0358 (10)	0.0281 (9)	0.0437 (11)	0.0035 (8)	0.0218 (8)	0.0018 (8)
N7	0.0468 (10)	0.0227 (8)	0.0486 (10)	0.0051 (7)	0.0279 (8)	0.0046 (7)
N9	0.0410 (10)	0.0264 (8)	0.0510 (10)	0.0036 (7)	0.0265 (8)	0.0027 (7)
N8	0.0473 (11)	0.0334 (9)	0.0586 (11)	0.0043 (8)	0.0345 (9)	0.0034 (8)
C7	0.0328 (10)	0.0327 (10)	0.0353 (10)	0.0024 (8)	0.0143 (8)	0.0018 (8)
N10	0.0473 (11)	0.0343 (9)	0.0569 (11)	0.0066 (8)	0.0320 (9)	0.0036 (8)
N12	0.0431 (10)	0.0293 (8)	0.0477 (10)	0.0038 (7)	0.0256 (8)	0.0015 (7)
C12	0.0348 (10)	0.0266 (9)	0.0339 (9)	0.0021 (7)	0.0142 (8)	0.0033 (7)
N11	0.0489 (11)	0.0344 (10)	0.0560 (11)	0.0059 (8)	0.0316 (9)	0.0010 (8)
C10	0.0328 (10)	0.0282 (9)	0.0325 (9)	0.0027 (7)	0.0139 (8)	0.0015 (7)
C9	0.0375 (10)	0.0236 (9)	0.0431 (11)	0.0009 (7)	0.0168 (9)	0.0031 (8)
C11	0.0427 (11)	0.0296 (10)	0.0446 (11)	0.0017 (8)	0.0253 (9)	0.0037 (8)
C8	0.0344 (10)	0.0298 (10)	0.0409 (10)	−0.0010 (8)	0.0178 (8)	0.0040 (8)
Cl1	0.0567 (3)	0.0300 (3)	0.0626 (4)	−0.0067 (2)	0.0336 (3)	−0.0052 (2)
Cl2	0.0502 (3)	0.0282 (3)	0.0624 (4)	0.0046 (2)	0.0273 (3)	0.0040 (2)

Geometric parameters (Å, º) top

N1—C1	1.355 (2)	N7—C7	1.355 (2)
N1—C5	1.356 (2)	N7—C11	1.358 (2)
N1—H1	0.8600	N7—H7	0.8600
N3—N4	1.338 (2)	N9—N10	1.339 (2)
N3—C6	1.340 (2)	N9—C12	1.341 (2)
N3—H3A	0.8600	N9—H9A	0.8600
C1—N2	1.325 (2)	N8—C7	1.323 (2)
C1—C2	1.411 (3)	N8—H8A	0.8600
N2—H2A	0.8600	N8—H8B	0.8600
N2—H2B	0.8600	C7—C8	1.415 (3)
N6—C6	1.320 (2)	N10—N11	1.292 (2)
N6—N5	1.362 (2)	N12—C12	1.318 (2)
N4—N5	1.291 (2)	N12—N11	1.365 (2)
C6—C4	1.457 (2)	C12—C10	1.459 (2)
C4—C5	1.363 (3)	C10—C11	1.364 (3)
C4—C3	1.421 (3)	C10—C9	1.419 (3)
C2—C3	1.361 (3)	C9—C8	1.357 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—H3	0.9300	C11—H11	0.9300
C5—H5	0.9300	C8—H8	0.9300

C1—N1—C5	123.42 (16)	C7—N7—C11	123.49 (17)
C1—N1—H1	118.3	C7—N7—H7	118.3
C5—N1—H1	118.3	C11—N7—H7	118.3
N4—N3—C6	109.55 (16)	N10—N9—C12	109.34 (16)
N4—N3—H3A	125.2	N10—N9—H9A	125.3
C6—N3—H3A	125.2	C12—N9—H9A	125.3
N2—C1—N1	119.62 (17)	C7—N8—H8A	120.0
N2—C1—C2	122.91 (17)	C7—N8—H8B	120.0
N1—C1—C2	117.47 (16)	H8A—N8—H8B	120.0
C1—N2—H2A	120.0	N8—C7—N7	119.82 (18)
C1—N2—H2B	120.0	N8—C7—C8	122.80 (18)
H2A—N2—H2B	120.0	N7—C7—C8	117.36 (17)
C6—N6—N5	105.81 (16)	N11—N10—N9	106.13 (15)
N5—N4—N3	105.89 (15)	C12—N12—N11	105.95 (16)
N6—C6—N3	107.67 (16)	N12—C12—N9	107.80 (16)
N6—C6—C4	126.56 (17)	N12—C12—C10	126.32 (17)
N3—C6—C4	125.76 (17)	N9—C12—C10	125.87 (17)
N4—N5—N6	111.08 (16)	N10—N11—N12	110.78 (16)
C5—C4—C3	117.77 (17)	C11—C10—C9	118.05 (17)
C5—C4—C6	120.74 (17)	C11—C10—C12	120.76 (17)
C3—C4—C6	121.49 (16)	C9—C10—C12	121.19 (17)
C3—C2—C1	119.91 (17)	C8—C9—C10	120.89 (17)
C3—C2—H2	120.0	C8—C9—H9	119.6
C1—C2—H2	120.0	C10—C9—H9	119.6
C2—C3—C4	120.90 (17)	N7—C11—C10	120.20 (17)
C2—C3—H3	119.5	N7—C11—H11	119.9
C4—C3—H3	119.5	C10—C11—H11	119.9
N1—C5—C4	120.49 (17)	C9—C8—C7	119.93 (17)
N1—C5—H5	119.8	C9—C8—H8	120.0
C4—C5—H5	119.8	C7—C8—H8	120.0

C5—N1—C1—N2	177.74 (19)	C11—N7—C7—N8	176.37 (19)
C5—N1—C1—C2	−1.8 (3)	C11—N7—C7—C8	−1.9 (3)
C6—N3—N4—N5	0.0 (2)	C12—N9—N10—N11	−0.2 (2)
N5—N6—C6—N3	0.1 (2)	N11—N12—C12—N9	−0.2 (2)
N5—N6—C6—C4	179.20 (18)	N11—N12—C12—C10	179.35 (18)
N4—N3—C6—N6	0.0 (2)	N10—N9—C12—N12	0.3 (2)
N4—N3—C6—C4	−179.15 (19)	N10—N9—C12—C10	−179.30 (18)
N3—N4—N5—N6	0.1 (2)	N9—N10—N11—N12	0.1 (2)
C6—N6—N5—N4	−0.1 (2)	C12—N12—N11—N10	0.1 (2)
N6—C6—C4—C5	175.7 (2)	N12—C12—C10—C11	−173.8 (2)
N3—C6—C4—C5	−5.4 (3)	N9—C12—C10—C11	5.6 (3)
N6—C6—C4—C3	−4.9 (3)	N12—C12—C10—C9	5.7 (3)
N3—C6—C4—C3	173.99 (19)	N9—C12—C10—C9	−174.82 (19)
N2—C1—C2—C3	−178.97 (19)	C11—C10—C9—C8	−1.1 (3)
N1—C1—C2—C3	0.6 (3)	C12—C10—C9—C8	179.35 (18)
C1—C2—C3—C4	0.9 (3)	C7—N7—C11—C10	−0.6 (3)
C5—C4—C3—C2	−1.2 (3)	C9—C10—C11—N7	2.1 (3)
C6—C4—C3—C2	179.48 (19)	C12—C10—C11—N7	−178.31 (18)
C1—N1—C5—C4	1.6 (3)	C10—C9—C8—C7	−1.4 (3)
C3—C4—C5—N1	0.0 (3)	N8—C7—C8—C9	−175.3 (2)
C6—C4—C5—N1	179.36 (18)	N7—C7—C8—C9	2.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5ⁱ	0.86	2.59	3.317 (2)	143
N1—H1···N6ⁱ	0.86	2.04	2.894 (2)	171
N2—H2A···N5ⁱ	0.86	2.15	2.972 (3)	160
N7—H7···N11ⁱⁱ	0.86	2.57	3.304 (2)	144
N7—H7···N12ⁱⁱ	0.86	2.06	2.913 (2)	169
N8—H8A···N11ⁱⁱ	0.86	2.20	3.024 (3)	160
N2—H2B···Cl1ⁱⁱⁱ	0.86	2.36	3.2187 (18)	177
N3—H3A···Cl2ⁱ	0.86	2.17	3.0047 (19)	165
N8—H8B···Cl2^iv	0.86	2.39	3.2432 (18)	172
N9—H9A···Cl1^v	0.86	2.18	3.0031 (18)	160

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

Experimental details

Crystal data
Chemical formula	C₆H₇N₆⁺·Cl⁻
M_r	198.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.043 (3), 13.238 (3), 9.5766 (19)
β (°)	109.35 (3)
V (Å³)	1679.7 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.45 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.859, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	16820, 3855, 3123
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.125, 1.12
No. of reflections	3855
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.23

Computer programs: CrystalClear (Rigaku, 2005), 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
N1—H1···N5ⁱ	0.86	2.59	3.317 (2)	142.8
N1—H1···N6ⁱ	0.86	2.04	2.894 (2)	170.7
N2—H2A···N5ⁱ	0.86	2.15	2.972 (3)	159.8
N7—H7···N11ⁱⁱ	0.86	2.57	3.304 (2)	144.4
N7—H7···N12ⁱⁱ	0.86	2.06	2.913 (2)	168.7
N8—H8A···N11ⁱⁱ	0.86	2.20	3.024 (3)	159.8
N2—H2B···Cl1ⁱⁱⁱ	0.86	2.36	3.2187 (18)	177.0
N3—H3A···Cl2ⁱ	0.86	2.17	3.0047 (19)	165.1
N8—H8B···Cl2^iv	0.86	2.39	3.2432 (18)	172.1
N9—H9A···Cl1^v	0.86	2.18	3.0031 (18)	159.7

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

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

References

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