4-(4,5-Dihydro-1H-benzo[g]indazol-3-yl)pyridinium chloride dihydrate

Yang, L.-F.; Hou, H.-B.; Liu, Y.-M.

doi:10.1107/S160053681203019X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2366

https://doi.org/10.1107/S160053681203019X

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4-(4,5-Dihydro-1H-benzo[g]indazol-3-yl)pyridinium chloride dihydrate

Luan-Fang Yang,^a Hong-Bo Hou ^a ^* and Yi-Ming Liu ^a

^aDepartment of Biology and Chemistry, Bao Shan College, Bao Shan, Yunnan 678000, People's Republic of China
^*Correspondence e-mail: bsxyylf@163.com

(Received 19 June 2012; accepted 2 July 2012; online 7 July 2012)

In the cation of the title compound, C₁₆H₁₄N₃⁺·Cl⁻·2H₂O, the cyclohexa-1,3-diene ring displays a screw-boat conformation and the pyridine ring is slightly twisted with respect to the pyrazole ring with a dihedral angle of 4.56 (12)°. In the crystal, ions and water molecules are linked into a three-dimensional network by classical N—H⋯O, N—H⋯Cl, O—H⋯Cl and O—H⋯O hydrogen bonds and by π–π stacking interactions, with centroid–centroid distances of 3.7580 (14) and 3.7794 (14) Å.

Related literature

For background to the pharmacological properties of indazole derivatives, see: Bistochi et al. (1981 ); Keppler & Hartmann (1994 ); Gomtsyan et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₄N₃⁺·Cl⁻·2H₂O
M_r = 319.78
Triclinic, $[P \overline 1]$
a = 6.7977 (5) Å
b = 9.4406 (7) Å
c = 12.2691 (9) Å
α = 93.846 (3)°
β = 96.883 (3)°
γ = 93.490 (3)°
V = 778.04 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
8076 measured reflections
2710 independent reflections
2185 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.06
2710 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2Wⁱ	0.86	2.12	2.856 (2)	143
N3—H3⋯Cl1	0.86	2.32	3.1618 (19)	167
O1W—H1WA⋯Cl1ⁱⁱ	0.89	2.25	3.142 (2)	174
O1W—H1WB⋯Cl1ⁱⁱⁱ	0.87	2.37	3.237 (3)	178
O2W—H2WA⋯Cl1	0.89	2.29	3.139 (2)	158
O2W—H2WB⋯O1W	0.92	1.86	2.749 (3)	162
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681203019X/rz2781sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203019X/rz2781Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681203019X/rz2781Isup3.cml

checkCIF report

Comment top

Indazole derivatives exhibit a variety of pharmacological properties such as anti-inflammatory (Bistochi et al., 1981), antitumor (Keppler & Hartmann, 1994), anti-HIV and analgesic properties (Gomtsyan et al., 2008). Here, we present the crystal structure determination of the title compound.

The asymmetric unit of the title compound (Fig. 1) consists of an organic cation, a chloride anion a two lattice water molecules. In the cation, the cyclohexa-1,3-diene ring displays a screw-boat conformation, with atoms C8 and C10 displaced by -0.190 (3) and 0.283 (3) Å, respectively, from the C7/C9/C12/C11 mean plane, and the pyridine ring is twisted to the pyrazole ring by a dihedral angle of 4.56 (12)°. In the crystal structure, cations, anions and water molecule are linked into a three-dimensional network by classical N—H···O, N—H···Cl, O—H···Cl and O—H···O hydrogen bonds (Table 1). In addition, π–π stacking interactions [centroid-centroid distances of 3.7580 (14) and 3.7794 (14) Å] extending along the a axis are observed.

Related literature top

For background to the pharmacological properties of indazole derivatives, see: Bistochi et al. (1981); Keppler & Hartmann (1994); Gomtsyan et al. (2008).

Experimental top

A solution of 3,4-dihydronaphthalen-1(2H)-one (1.46 g, 0.01 mol) was added to a stirred solution of hydrazine (0.05 g, 0.01 mol) in dry tetrahydrofuran (50 ml) at 0°C for 3 h, then n-butyllithium (0.02 mol) was added at a fast dropwise rate during a 5 min period. The solution was stirred at 0°C for an additional 30 min, then methyl isonicotinate (1.37 g, 0.01 mol) dissolved in THF (40 ml) was added to the dilithiated intermediate, and the solution was stirred for 60 min at 0°C. Finally, 20 ml of 3 M hydrochloric acid was added, and the two phase mixture was well stirred and heated under reflux for 45 min. The mixture was then neutralized with solid sodium bicarbonate, and the layers were separated. The aqueous layer was extracted with ether and the organic fractions were combined, evaporated, and the crude product was dissolved in hydrochloric acid (2M, 20 ml). The solution was filtered and the filtrate was set aside for five weeks to obtain colourless crystals.

Structure description top

For background to the pharmacological properties of indazole derivatives, see: Bistochi et al. (1981); Keppler & Hartmann (1994); Gomtsyan et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of title compound showing displacement ellipsoids drawn at the 50% probability level.

4-(4,5-Dihydro-1H-benzo[g]indazol-3-yl)pyridinium chloride dihydrate top

Crystal data top

C₁₆H₁₄N₃⁺·Cl⁻·2H₂O	Z = 2
M_r = 319.78	F(000) = 336
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7977 (5) Å	Cell parameters from 2710 reflections
b = 9.4406 (7) Å	θ = 1.7–25.0°
c = 12.2691 (9) Å	µ = 0.26 mm⁻¹
α = 93.846 (3)°	T = 293 K
β = 96.883 (3)°	Block, colourless
γ = 93.490 (3)°	0.22 × 0.19 × 0.18 mm
V = 778.04 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
φ and ω scans	h = −8→7
8076 measured reflections	k = −10→11
2710 independent reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0498P)² + 0.5403P] where P = (F_o² + 2F_c²)/3
2710 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₄N₃⁺·Cl⁻·2H₂O	γ = 93.490 (3)°
M_r = 319.78	V = 778.04 (10) Å³
Triclinic, P1	Z = 2
a = 6.7977 (5) Å	Mo Kα radiation
b = 9.4406 (7) Å	µ = 0.26 mm⁻¹
c = 12.2691 (9) Å	T = 293 K
α = 93.846 (3)°	0.22 × 0.19 × 0.18 mm
β = 96.883 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2185 reflections with I > 2σ(I)
8076 measured reflections	R_int = 0.033
2710 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
2710 reflections	Δρ_min = −0.32 e Å⁻³
199 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	0.3584 (4)	0.6698 (3)	0.8547 (2)	0.0387 (6)
H1	0.3680	0.6302	0.9224	0.046*
C2	0.3132 (4)	0.5827 (3)	0.75906 (19)	0.0339 (6)
H2	0.2903	0.4850	0.7622	0.041*
C3	0.3018 (3)	0.6421 (2)	0.65730 (17)	0.0247 (5)
C4	0.3295 (3)	0.7899 (2)	0.65869 (18)	0.0286 (5)
H4	0.3181	0.8331	0.5925	0.034*
C5	0.3731 (3)	0.8721 (3)	0.75539 (19)	0.0318 (5)
H5	0.3921	0.9705	0.7551	0.038*
C6	0.2672 (3)	0.5559 (2)	0.55224 (17)	0.0230 (5)
C7	0.2449 (3)	0.4070 (2)	0.52895 (17)	0.0240 (5)
C8	0.2336 (4)	0.2806 (2)	0.5973 (2)	0.0322 (6)
H8A	0.1014	0.2683	0.6190	0.039*
H8B	0.3274	0.2978	0.6636	0.039*
C9	0.2217 (3)	0.3888 (2)	0.41550 (18)	0.0240 (5)
C10	0.2804 (4)	0.1448 (3)	0.5328 (2)	0.0364 (6)
H10A	0.4234	0.1391	0.5418	0.044*
H10B	0.2237	0.0638	0.5659	0.044*
C11	0.2075 (3)	0.1303 (2)	0.4108 (2)	0.0312 (5)
C12	0.1880 (3)	0.2522 (2)	0.35072 (19)	0.0271 (5)
C13	0.1380 (3)	0.2384 (3)	0.2367 (2)	0.0315 (5)
H13	0.1258	0.3190	0.1975	0.038*
C14	0.1064 (4)	0.1042 (3)	0.1821 (2)	0.0403 (6)
H14	0.0743	0.0949	0.1060	0.048*
C15	0.1224 (4)	−0.0156 (3)	0.2399 (2)	0.0437 (7)
H15	0.0997	−0.1054	0.2028	0.052*
C16	0.1723 (4)	−0.0027 (3)	0.3532 (2)	0.0395 (6)
H16	0.1824	−0.0843	0.3914	0.047*
N1	0.3885 (3)	0.8098 (2)	0.85102 (16)	0.0349 (5)
H1N	0.4187	0.8619	0.9116	0.042*
N2	0.2606 (3)	0.62466 (19)	0.45875 (14)	0.0249 (4)
N3	0.2321 (3)	0.52067 (19)	0.37761 (14)	0.0248 (4)
H3	0.2214	0.5357	0.3089	0.030*
O1W	0.8185 (3)	0.6654 (3)	0.04112 (19)	0.0691 (7)
H1WA	0.9413	0.6435	0.0647	0.083*
H1WB	0.7964	0.5906	−0.0050	0.083*
O2W	0.5429 (3)	0.85870 (19)	0.07832 (14)	0.0399 (5)
H2WA	0.4837	0.7898	0.1118	0.048*
H2WB	0.6532	0.8085	0.0732	0.048*
Cl1	0.25495 (10)	0.60918 (7)	0.13519 (5)	0.0441 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (15)	0.0472 (17)	0.0268 (12)	0.0083 (12)	0.0023 (10)	0.0076 (11)
C2	0.0393 (14)	0.0321 (14)	0.0313 (12)	0.0048 (11)	0.0043 (10)	0.0078 (11)
C3	0.0193 (11)	0.0282 (13)	0.0277 (11)	0.0045 (9)	0.0045 (8)	0.0048 (9)
C4	0.0290 (12)	0.0281 (13)	0.0299 (12)	0.0040 (10)	0.0061 (9)	0.0043 (10)
C5	0.0298 (13)	0.0295 (13)	0.0362 (13)	0.0028 (10)	0.0062 (10)	−0.0008 (11)
C6	0.0206 (11)	0.0237 (12)	0.0259 (11)	0.0022 (9)	0.0043 (8)	0.0069 (9)
C7	0.0185 (11)	0.0239 (12)	0.0308 (11)	0.0033 (9)	0.0044 (9)	0.0057 (9)
C8	0.0338 (13)	0.0265 (13)	0.0383 (13)	0.0043 (10)	0.0067 (10)	0.0114 (11)
C9	0.0202 (11)	0.0216 (12)	0.0314 (12)	0.0028 (9)	0.0053 (9)	0.0062 (9)
C10	0.0356 (14)	0.0262 (14)	0.0503 (15)	0.0063 (10)	0.0094 (11)	0.0122 (12)
C11	0.0221 (12)	0.0234 (13)	0.0496 (14)	0.0024 (9)	0.0100 (10)	0.0042 (11)
C12	0.0200 (11)	0.0247 (13)	0.0372 (12)	0.0011 (9)	0.0080 (9)	0.0001 (10)
C13	0.0238 (12)	0.0305 (14)	0.0412 (13)	0.0021 (10)	0.0088 (10)	0.0005 (11)
C14	0.0342 (14)	0.0385 (16)	0.0463 (15)	−0.0001 (11)	0.0064 (11)	−0.0101 (13)
C15	0.0367 (15)	0.0264 (14)	0.0659 (18)	−0.0017 (11)	0.0103 (13)	−0.0144 (13)
C16	0.0321 (14)	0.0236 (13)	0.0637 (18)	0.0008 (10)	0.0104 (12)	0.0032 (12)
N1	0.0318 (11)	0.0424 (14)	0.0292 (10)	0.0034 (9)	0.0020 (8)	−0.0063 (9)
N2	0.0266 (10)	0.0214 (10)	0.0270 (9)	0.0023 (8)	0.0035 (7)	0.0033 (8)
N3	0.0286 (10)	0.0227 (10)	0.0232 (9)	0.0024 (8)	0.0030 (7)	0.0021 (8)
O1W	0.0588 (14)	0.0699 (16)	0.0761 (15)	0.0245 (12)	−0.0030 (11)	−0.0103 (12)
O2W	0.0382 (10)	0.0376 (11)	0.0409 (10)	0.0052 (8)	0.0003 (8)	−0.0142 (8)
Cl1	0.0570 (4)	0.0417 (4)	0.0343 (3)	0.0068 (3)	0.0048 (3)	0.0064 (3)

Geometric parameters (Å, º) top

C1—N1	1.330 (3)	C10—C11	1.514 (4)
C1—C2	1.378 (3)	C10—H10A	0.9700
C1—H1	0.9300	C10—H10B	0.9700
C2—C3	1.398 (3)	C11—C16	1.392 (3)
C2—H2	0.9300	C11—C12	1.413 (3)
C3—C4	1.395 (3)	C12—C13	1.395 (3)
C3—C6	1.464 (3)	C13—C14	1.385 (3)
C4—C5	1.365 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.378 (4)
C5—N1	1.344 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.386 (4)
C6—N2	1.353 (3)	C15—H15	0.9300
C6—C7	1.411 (3)	C16—H16	0.9300
C7—C9	1.380 (3)	N1—H1N	0.8600
C7—C8	1.507 (3)	N2—N3	1.339 (2)
C8—C10	1.532 (3)	N3—H3	0.8600
C8—H8A	0.9700	O1W—H1WA	0.8917
C8—H8B	0.9700	O1W—H1WB	0.8693
C9—N3	1.359 (3)	O2W—H2WA	0.8928
C9—C12	1.459 (3)	O2W—H2WB	0.9171

N1—C1—C2	120.6 (2)	C8—C10—H10A	108.1
N1—C1—H1	119.7	C11—C10—H10B	108.1
C2—C1—H1	119.7	C8—C10—H10B	108.1
C1—C2—C3	119.6 (2)	H10A—C10—H10B	107.3
C1—C2—H2	120.2	C16—C11—C12	118.1 (2)
C3—C2—H2	120.2	C16—C11—C10	121.2 (2)
C4—C3—C2	117.2 (2)	C12—C11—C10	120.5 (2)
C4—C3—C6	120.0 (2)	C13—C12—C11	120.4 (2)
C2—C3—C6	122.8 (2)	C13—C12—C9	123.8 (2)
C5—C4—C3	121.2 (2)	C11—C12—C9	115.8 (2)
C5—C4—H4	119.4	C14—C13—C12	119.8 (2)
C3—C4—H4	119.4	C14—C13—H13	120.1
N1—C5—C4	119.4 (2)	C12—C13—H13	120.1
N1—C5—H5	120.3	C15—C14—C13	120.4 (3)
C4—C5—H5	120.3	C15—C14—H14	119.8
N2—C6—C7	111.32 (19)	C13—C14—H14	119.8
N2—C6—C3	117.73 (19)	C14—C15—C16	120.2 (2)
C7—C6—C3	130.9 (2)	C14—C15—H15	119.9
C9—C7—C6	104.38 (19)	C16—C15—H15	119.9
C9—C7—C8	120.7 (2)	C15—C16—C11	121.1 (2)
C6—C7—C8	134.9 (2)	C15—C16—H16	119.4
C7—C8—C10	111.05 (19)	C11—C16—H16	119.4
C7—C8—H8A	109.4	C1—N1—C5	121.9 (2)
C10—C8—H8A	109.4	C1—N1—H1N	119.0
C7—C8—H8B	109.4	C5—N1—H1N	119.0
C10—C8—H8B	109.4	N3—N2—C6	104.52 (17)
H8A—C8—H8B	108.0	N2—N3—C9	112.78 (17)
N3—C9—C7	106.99 (19)	N2—N3—H3	123.6
N3—C9—C12	127.6 (2)	C9—N3—H3	123.6
C7—C9—C12	125.4 (2)	H1WA—O1W—H1WB	93.0
C11—C10—C8	116.6 (2)	H2WA—O2W—H2WB	92.1
C11—C10—H10A	108.1

N1—C1—C2—C3	1.0 (4)	C16—C11—C12—C13	−1.0 (3)
C1—C2—C3—C4	−2.6 (3)	C10—C11—C12—C13	174.2 (2)
C1—C2—C3—C6	176.0 (2)	C16—C11—C12—C9	178.5 (2)
C2—C3—C4—C5	2.4 (3)	C10—C11—C12—C9	−6.2 (3)
C6—C3—C4—C5	−176.3 (2)	N3—C9—C12—C13	−7.7 (4)
C3—C4—C5—N1	−0.4 (3)	C7—C9—C12—C13	170.8 (2)
C4—C3—C6—N2	−0.9 (3)	N3—C9—C12—C11	172.8 (2)
C2—C3—C6—N2	−179.5 (2)	C7—C9—C12—C11	−8.8 (3)
C4—C3—C6—C7	176.5 (2)	C11—C12—C13—C14	0.3 (3)
C2—C3—C6—C7	−2.0 (4)	C9—C12—C13—C14	−179.2 (2)
N2—C6—C7—C9	−0.7 (2)	C12—C13—C14—C15	0.6 (4)
C3—C6—C7—C9	−178.3 (2)	C13—C14—C15—C16	−0.7 (4)
N2—C6—C7—C8	−177.6 (2)	C14—C15—C16—C11	−0.1 (4)
C3—C6—C7—C8	4.8 (4)	C12—C11—C16—C15	0.9 (3)
C9—C7—C8—C10	23.2 (3)	C10—C11—C16—C15	−174.3 (2)
C6—C7—C8—C10	−160.4 (2)	C2—C1—N1—C5	1.1 (4)
C6—C7—C9—N3	0.4 (2)	C4—C5—N1—C1	−1.4 (3)
C8—C7—C9—N3	177.81 (19)	C7—C6—N2—N3	0.7 (2)
C6—C7—C9—C12	−178.3 (2)	C3—C6—N2—N3	178.68 (17)
C8—C7—C9—C12	−0.9 (3)	C6—N2—N3—C9	−0.5 (2)
C7—C8—C10—C11	−36.3 (3)	C7—C9—N3—N2	0.0 (2)
C8—C10—C11—C16	−155.3 (2)	C12—C9—N3—N2	178.70 (19)
C8—C10—C11—C12	29.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2Wⁱ	0.86	2.12	2.856 (2)	143
N3—H3···Cl1	0.86	2.32	3.1618 (19)	167
O1W—H1WA···Cl1ⁱⁱ	0.89	2.25	3.142 (2)	174
O1W—H1WB···Cl1ⁱⁱⁱ	0.87	2.37	3.237 (3)	178
O2W—H2WA···Cl1	0.89	2.29	3.139 (2)	158
O2W—H2WB···O1W	0.92	1.86	2.749 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₃⁺·Cl⁻·2H₂O
M_r	319.78
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.7977 (5), 9.4406 (7), 12.2691 (9)
α, β, γ (°)	93.846 (3), 96.883 (3), 93.490 (3)
V (Å³)	778.04 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.22 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8076, 2710, 2185
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.119, 1.06
No. of reflections	2710
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.32

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2Wⁱ	0.86	2.12	2.856 (2)	143.4
N3—H3···Cl1	0.86	2.32	3.1618 (19)	167.4
O1W—H1WA···Cl1ⁱⁱ	0.89	2.25	3.142 (2)	174.1
O1W—H1WB···Cl1ⁱⁱⁱ	0.87	2.37	3.237 (3)	177.7
O2W—H2WA···Cl1	0.89	2.29	3.139 (2)	158.1
O2W—H2WB···O1W	0.92	1.86	2.749 (3)	162.4

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

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of Bao Shan College (grant No. 09B001K) for financial support.

References

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