9-Benzamido­acridinium chloride

Huang, K.; Liu, K.-Y.; Qin, D.-B.

doi:10.1107/S1600536809039439

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2622

https://doi.org/10.1107/S1600536809039439

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9-Benzamidoacridinium chloride

Kun Huang,^a Kun-Ying Liu ^a and Da-Bin Qin ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 31 August 2009; accepted 28 September 2009; online 3 October 2009)

In the title compound, C₂₀H₁₅N₂O⁺·Cl⁻, the dihedral angle between the fused-ring system and the benzene ring is 63.10 (7)°. In the crystal, N—H⋯Cl hydrogen bonds link the components and aromatic π–π stacking [shortest centroid–centroid distance = 3.6421 (12) Å] occurs.

Related literature

For background to acridine derivatives, see: Antonini (2002 ); Carvalho et al. (2005 ). For the synthesis, see: He et al. (2008 ); Chandregowda et al. (2009 ). For related structures, see: Sikorski et al. (2007 , 2008 ); Trzybiníski et al. (2009 ).

Experimental

Crystal data

C₂₀H₁₅N₂O⁺·Cl⁻
M_r = 334.79
Triclinic, $[P \overline 1]$
a = 8.9601 (17) Å
b = 9.0084 (17) Å
c = 10.8775 (18) Å
α = 79.168 (7)°
β = 65.855 (5)°
γ = 86.927 (7)°
V = 786.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 93 K
0.37 × 0.33 × 0.17 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.913, T_max = 0.959
4772 measured reflections
2955 independent reflections
2538 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.069
S = 1.00
2955 reflections
225 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1ⁱ	0.93 (2)	2.09 (2)	3.0167 (17)	168 (8)
N2—H2N⋯Cl1	0.90 (2)	2.37 (2)	3.2139 (17)	154 (4)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039439/hb5083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039439/hb5083Isup2.hkl

checkCIF report

Comment top

Acridine derivatives which show strong antiproliferative activities on human transformed cells, have been considered as promising agents for anticancer and antiparasitic therapy (Antonini et al., 2002) in recent years. Meanwhile Complexes containing acridine moiety are interesting in luminescence study (Carvalho et al., 2005). Therefore they attract more and more chemists' attention. Here we report the synthesis and crystal structure of the title compound (Fig. 1).

the bond lengths and angles characterizing the geometry of the acridinium moiety are typical of acridine-based derivatives (Sikorski et al., 2007, 2008). Atoms N2/C14/O1 which form dihedral angles with n1/c1/c6/c13/c12/c7 plane and c15 - c20 ring of 55.48 (1) Å and 6.82 (3) Å, respectively,are coplaner. The dihedral angle between the n1/c1/c6/c13/c12/c7 ring and c15 - c20 plane is 61.76 (6) Å.

In the crystal structure, weak Cl—H···N hydrogen bonds link the two cations and anions in ion pairs. π-π interactions between n1/c1/c6/c13/c12/c7 ring and c1-c6 ring are observed, with a Cg1···Cg2 distance of 3.6234 Å. [symmetry code: (i) –X,-1-Y,-Z] Where Cg1 and Cg2 are n1/c1/c6/c13/c12/c7 and c1-c6 centroid, respectively (Table 1).

Related literature top

For background to acridine derivatives, see: Antonini (2002); Carvalho et al. (2005). For the synthesis, see: He et al. (2008); Chandregowda et al. (2009). For related structures, see: Sikorski et al. (2007, 2008); Trzybiníski et al. (2009).

Experimental top

The title compound was prepared according to the reported procedure of He et al.. (2008) & Chandregowda et al.. (2009). Yellow chunks of (I) were obtained by recrystallization from methanol.

Structure description top

For background to acridine derivatives, see: Antonini (2002); Carvalho et al. (2005). For the synthesis, see: He et al. (2008); Chandregowda et al. (2009). For related structures, see: Sikorski et al. (2007, 2008); Trzybiníski et al. (2009).

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

9-Benzamidoacridinium chloride top

Crystal data top

C₂₀H₁₅N₂O⁺·Cl⁻	Z = 2
M_r = 334.79	F(000) = 348
Triclinic, P1	D_x = 1.413 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9601 (17) Å	Cell parameters from 2420 reflections
b = 9.0084 (17) Å	θ = 3.2–27.5°
c = 10.8775 (18) Å	µ = 0.25 mm⁻¹
α = 79.168 (7)°	T = 93 K
β = 65.855 (5)°	Chunk, yellow
γ = 86.927 (7)°	0.37 × 0.33 × 0.17 mm
V = 786.6 (2) Å³

Data collection top

Rigaku SPIDER diffractometer	2955 independent reflections
Radiation source: Rotating Anode	2538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 26.0°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
T_min = 0.913, T_max = 0.959	k = −10→11
4772 measured reflections	l = −12→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0136P)² + 0.516P] where P = (F_o² + 2F_c²)/3
2955 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₁₅N₂O⁺·Cl⁻	γ = 86.927 (7)°
M_r = 334.79	V = 786.6 (2) Å³
Triclinic, P1	Z = 2
a = 8.9601 (17) Å	Mo Kα radiation
b = 9.0084 (17) Å	µ = 0.25 mm⁻¹
c = 10.8775 (18) Å	T = 93 K
α = 79.168 (7)°	0.37 × 0.33 × 0.17 mm
β = 65.855 (5)°

Data collection top

Rigaku SPIDER diffractometer	2955 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2538 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.959	R_int = 0.020
4772 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.27 e Å⁻³
2955 reflections	Δρ_min = −0.22 e Å⁻³
225 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
Cl1	0.78153 (5)	0.85506 (5)	−0.03376 (4)	0.01909 (12)
O1	0.39684 (14)	0.63975 (13)	0.49853 (12)	0.0187 (3)
N1	0.34182 (17)	0.35116 (16)	0.16256 (14)	0.0143 (3)
N2	0.54610 (18)	0.68607 (16)	0.26770 (15)	0.0153 (3)
C1	0.5768 (2)	0.46569 (18)	0.16353 (17)	0.0139 (4)
C2	0.7475 (2)	0.45912 (19)	0.13000 (17)	0.0161 (4)
H2	0.7988	0.5317	0.1541	0.019*
C3	0.8384 (2)	0.34982 (19)	0.06364 (18)	0.0178 (4)
H3	0.9524	0.3469	0.0422	0.021*
C4	0.7652 (2)	0.2403 (2)	0.02605 (18)	0.0185 (4)
H4	0.8306	0.1652	−0.0205	0.022*
C5	0.6021 (2)	0.24183 (19)	0.05601 (17)	0.0165 (4)
H5	0.5538	0.1687	0.0301	0.020*
C6	0.5053 (2)	0.35355 (18)	0.12623 (17)	0.0142 (4)
C7	0.2393 (2)	0.44990 (18)	0.23448 (17)	0.0140 (4)
C8	0.0696 (2)	0.4369 (2)	0.27045 (18)	0.0176 (4)
H8	0.0268	0.3567	0.2478	0.021*
C9	−0.0322 (2)	0.5401 (2)	0.33778 (18)	0.0194 (4)
H9	−0.1468	0.5297	0.3649	0.023*
C10	0.0313 (2)	0.6631 (2)	0.36779 (18)	0.0197 (4)
H10	−0.0406	0.7372	0.4106	0.024*
C11	0.1935 (2)	0.67615 (19)	0.33612 (18)	0.0172 (4)
H11	0.2338	0.7592	0.3571	0.021*
C12	0.3043 (2)	0.56678 (18)	0.27180 (17)	0.0141 (4)
C13	0.4735 (2)	0.57227 (18)	0.23643 (17)	0.0139 (4)
C14	0.5083 (2)	0.70877 (18)	0.39917 (18)	0.0145 (4)
C15	0.6172 (2)	0.82148 (18)	0.41153 (17)	0.0139 (4)
C16	0.7367 (2)	0.91166 (19)	0.30042 (18)	0.0175 (4)
H16	0.7528	0.9047	0.2098	0.021*
C17	0.8326 (2)	1.01193 (19)	0.32150 (19)	0.0198 (4)
H17	0.9140	1.0735	0.2453	0.024*
C18	0.8099 (2)	1.02228 (19)	0.45330 (19)	0.0187 (4)
H18	0.8765	1.0902	0.4674	0.022*
C19	0.6903 (2)	0.93372 (19)	0.56455 (19)	0.0190 (4)
H19	0.6746	0.9412	0.6550	0.023*
C20	0.5936 (2)	0.83416 (19)	0.54403 (18)	0.0165 (4)
H20	0.5109	0.7743	0.6206	0.020*
H1N	0.298 (2)	0.278 (2)	0.1340 (19)	0.023 (5)*
H2N	0.633 (2)	0.736 (2)	0.197 (2)	0.024 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0200 (2)	0.0198 (2)	0.0173 (2)	−0.00404 (17)	−0.00573 (19)	−0.00612 (18)
O1	0.0190 (7)	0.0196 (6)	0.0160 (7)	−0.0045 (5)	−0.0056 (6)	−0.0020 (5)
N1	0.0175 (8)	0.0134 (7)	0.0137 (8)	−0.0022 (6)	−0.0077 (6)	−0.0023 (6)
N2	0.0160 (8)	0.0165 (8)	0.0128 (8)	−0.0038 (6)	−0.0040 (7)	−0.0045 (6)
C1	0.0177 (9)	0.0131 (8)	0.0103 (9)	−0.0006 (7)	−0.0060 (7)	−0.0001 (7)
C2	0.0183 (9)	0.0165 (9)	0.0147 (9)	−0.0034 (7)	−0.0083 (8)	−0.0011 (7)
C3	0.0164 (10)	0.0183 (9)	0.0166 (10)	0.0015 (7)	−0.0058 (8)	−0.0008 (8)
C4	0.0230 (10)	0.0168 (9)	0.0139 (9)	0.0029 (7)	−0.0062 (8)	−0.0027 (7)
C5	0.0228 (10)	0.0141 (9)	0.0143 (9)	−0.0002 (7)	−0.0090 (8)	−0.0029 (7)
C6	0.0175 (10)	0.0143 (8)	0.0102 (9)	−0.0022 (7)	−0.0061 (7)	0.0010 (7)
C7	0.0175 (9)	0.0139 (8)	0.0104 (9)	−0.0008 (7)	−0.0061 (7)	−0.0004 (7)
C8	0.0194 (10)	0.0198 (9)	0.0155 (9)	−0.0030 (7)	−0.0094 (8)	−0.0018 (8)
C9	0.0144 (9)	0.0277 (10)	0.0166 (9)	−0.0007 (8)	−0.0074 (8)	−0.0028 (8)
C10	0.0203 (10)	0.0234 (10)	0.0159 (10)	0.0054 (8)	−0.0077 (8)	−0.0055 (8)
C11	0.0215 (10)	0.0169 (9)	0.0156 (9)	0.0009 (7)	−0.0096 (8)	−0.0039 (8)
C12	0.0170 (9)	0.0143 (8)	0.0109 (9)	−0.0013 (7)	−0.0060 (7)	−0.0007 (7)
C13	0.0188 (10)	0.0126 (8)	0.0101 (8)	−0.0030 (7)	−0.0064 (7)	0.0004 (7)
C14	0.0159 (9)	0.0130 (8)	0.0166 (9)	0.0033 (7)	−0.0085 (8)	−0.0040 (7)
C15	0.0148 (9)	0.0121 (8)	0.0169 (9)	0.0024 (7)	−0.0078 (8)	−0.0045 (7)
C16	0.0202 (10)	0.0186 (9)	0.0150 (9)	−0.0005 (7)	−0.0070 (8)	−0.0058 (8)
C17	0.0201 (10)	0.0181 (9)	0.0187 (10)	−0.0039 (8)	−0.0044 (8)	−0.0042 (8)
C18	0.0200 (10)	0.0164 (9)	0.0238 (10)	0.0003 (7)	−0.0118 (8)	−0.0064 (8)
C19	0.0261 (10)	0.0183 (9)	0.0171 (10)	0.0026 (8)	−0.0123 (8)	−0.0063 (8)
C20	0.0205 (10)	0.0141 (8)	0.0150 (9)	−0.0002 (7)	−0.0077 (8)	−0.0015 (7)

Geometric parameters (Å, º) top

O1—C14	1.218 (2)	C8—H8	0.9500
N1—C6	1.352 (2)	C9—C10	1.419 (2)
N1—C7	1.354 (2)	C9—H9	0.9500
N1—H1N	0.939 (19)	C10—C11	1.356 (2)
N2—C14	1.381 (2)	C10—H10	0.9500
N2—C13	1.405 (2)	C11—C12	1.425 (2)
N2—H2N	0.902 (19)	C11—H11	0.9500
C1—C13	1.414 (2)	C12—C13	1.404 (2)
C1—C2	1.421 (2)	C14—C15	1.505 (2)
C1—C6	1.425 (2)	C15—C16	1.390 (2)
C2—C3	1.362 (2)	C15—C20	1.395 (2)
C2—H2	0.9500	C16—C17	1.389 (2)
C3—C4	1.418 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.384 (2)
C4—C5	1.360 (2)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.385 (2)
C5—C6	1.415 (2)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.387 (2)
C7—C8	1.412 (2)	C19—H19	0.9500
C7—C12	1.426 (2)	C20—H20	0.9500
C8—C9	1.361 (2)

C6—N1—C7	123.57 (14)	C11—C10—C9	120.77 (16)
C6—N1—H1N	117.6 (11)	C11—C10—H10	119.6
C7—N1—H1N	118.8 (11)	C9—C10—H10	119.6
C14—N2—C13	124.05 (15)	C10—C11—C12	120.82 (16)
C14—N2—H2N	120.0 (12)	C10—C11—H11	119.6
C13—N2—H2N	115.3 (12)	C12—C11—H11	119.6
C13—C1—C2	123.94 (15)	C13—C12—C11	124.12 (15)
C13—C1—C6	118.42 (15)	C13—C12—C7	118.46 (15)
C2—C1—C6	117.58 (15)	C11—C12—C7	117.32 (15)
C3—C2—C1	120.64 (16)	C12—C13—N2	121.44 (15)
C3—C2—H2	119.7	C12—C13—C1	120.60 (15)
C1—C2—H2	119.7	N2—C13—C1	117.93 (15)
C2—C3—C4	120.88 (17)	O1—C14—N2	122.22 (15)
C2—C3—H3	119.6	O1—C14—C15	122.34 (15)
C4—C3—H3	119.6	N2—C14—C15	115.42 (15)
C5—C4—C3	120.67 (16)	C16—C15—C20	119.27 (15)
C5—C4—H4	119.7	C16—C15—C14	124.14 (15)
C3—C4—H4	119.7	C20—C15—C14	116.59 (15)
C4—C5—C6	119.29 (16)	C17—C16—C15	120.21 (16)
C4—C5—H5	120.4	C17—C16—H16	119.9
C6—C5—H5	120.4	C15—C16—H16	119.9
N1—C6—C5	119.64 (15)	C18—C17—C16	120.14 (17)
N1—C6—C1	119.40 (15)	C18—C17—H17	119.9
C5—C6—C1	120.93 (16)	C16—C17—H17	119.9
N1—C7—C8	119.67 (15)	C17—C18—C19	120.02 (16)
N1—C7—C12	119.52 (15)	C17—C18—H18	120.0
C8—C7—C12	120.81 (15)	C19—C18—H18	120.0
C9—C8—C7	119.44 (16)	C18—C19—C20	120.04 (16)
C9—C8—H8	120.3	C18—C19—H19	120.0
C7—C8—H8	120.3	C20—C19—H19	120.0
C8—C9—C10	120.61 (17)	C19—C20—C15	120.31 (16)
C8—C9—H9	119.7	C19—C20—H20	119.8
C10—C9—H9	119.7	C15—C20—H20	119.8

C13—C1—C2—C3	177.69 (17)	C8—C7—C12—C11	−5.1 (2)
C6—C1—C2—C3	0.5 (3)	C11—C12—C13—N2	2.5 (3)
C1—C2—C3—C4	0.2 (3)	C7—C12—C13—N2	178.76 (16)
C2—C3—C4—C5	−0.2 (3)	C11—C12—C13—C1	−175.20 (17)
C3—C4—C5—C6	−0.4 (3)	C7—C12—C13—C1	1.0 (2)
C7—N1—C6—C5	177.34 (16)	C14—N2—C13—C12	61.0 (2)
C7—N1—C6—C1	−0.5 (2)	C14—N2—C13—C1	−121.22 (18)
C4—C5—C6—N1	−176.64 (16)	C2—C1—C13—C12	−176.74 (16)
C4—C5—C6—C1	1.2 (3)	C6—C1—C13—C12	0.4 (2)
C13—C1—C6—N1	−0.7 (2)	C2—C1—C13—N2	5.4 (3)
C2—C1—C6—N1	176.61 (16)	C6—C1—C13—N2	−177.42 (15)
C13—C1—C6—C5	−178.53 (16)	C13—N2—C14—O1	−7.0 (3)
C2—C1—C6—C5	−1.2 (2)	C13—N2—C14—C15	171.42 (15)
C6—N1—C7—C8	−178.65 (16)	O1—C14—C15—C16	−174.41 (17)
C6—N1—C7—C12	2.0 (3)	N2—C14—C15—C16	7.1 (2)
N1—C7—C8—C9	−177.30 (17)	O1—C14—C15—C20	5.4 (2)
C12—C7—C8—C9	2.1 (3)	N2—C14—C15—C20	−173.03 (15)
C7—C8—C9—C10	2.2 (3)	C20—C15—C16—C17	0.7 (3)
C8—C9—C10—C11	−3.3 (3)	C14—C15—C16—C17	−179.45 (16)
C9—C10—C11—C12	0.1 (3)	C15—C16—C17—C18	0.2 (3)
C10—C11—C12—C13	−179.75 (17)	C16—C17—C18—C19	−0.7 (3)
C10—C11—C12—C7	4.0 (3)	C17—C18—C19—C20	0.2 (3)
N1—C7—C12—C13	−2.2 (2)	C18—C19—C20—C15	0.6 (3)
C8—C7—C12—C13	178.44 (16)	C16—C15—C20—C19	−1.1 (3)
N1—C7—C12—C11	174.28 (15)	C14—C15—C20—C19	179.04 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1ⁱ	0.93 (2)	2.09 (2)	3.0167 (17)	168 (8)
N2—H2N···Cl1	0.90 (2)	2.37 (2)	3.2139 (17)	154 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₂O⁺·Cl⁻
M_r	334.79
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	8.9601 (17), 9.0084 (17), 10.8775 (18)
α, β, γ (°)	79.168 (7), 65.855 (5), 86.927 (7)
V (Å³)	786.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.37 × 0.33 × 0.17

Data collection
Diffractometer	Rigaku SPIDER
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.913, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	4772, 2955, 2538
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.069, 1.00
No. of reflections	2955
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), 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—H1N···Cl1ⁱ	0.93 (2)	2.09 (2)	3.0167 (17)	168 (8)
N2—H2N···Cl1	0.90 (2)	2.37 (2)	3.2139 (17)	154 (4)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of the Sichuan Education Department (grant No. 2006B039).

References

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