2-Amino-4-(2,4-dichloro­phen­yl)-6-(naphthalen-1-yl)nicotinonitrile

Ye, Y.-F.; Wang, H.-Q.; Feng, Z.-Q.

doi:10.1107/S1600536810050609

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o71

https://doi.org/10.1107/S1600536810050609

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2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile

Yuan-Feng Ye,^a ^* Huai-Qing Wang ^a and Zhi-Qiang Feng ^a

^aSchool of Material Engineering, Jinling Institute of Technology, Nanjing 211169, People's Republic of China
^*Correspondence e-mail: dalantom@126.com

(Received 24 November 2010; accepted 2 December 2010; online 11 December 2010)

In the crystal structure of the title compound, C₂₂H₁₃Cl₂N₃, the molecules are connected via intermolecular C—H⋯N and N—H⋯N hydrogen bonds, forming a three-dimensional network. The dihedral angles between naphthyl ring system and the pyridyl and benzene rings are 55.04 (7) and 75.87 (7)°, respectively, whereas the pyridyl and benzene rings are oriented at a dihedral angle of 59.56 (8)°.

Related literature

For the synthetic procedure, see: Mantri et al. (2008 ). For the use of the title compound in the preparation of medicines, see: Mkhalid et al. (2006 ). For general background to this type of compound, see: Moreau & Huber (1999 ).

Experimental

Crystal data

C₂₂H₁₃Cl₂N₃
M_r = 390.25
Triclinic, $[P \overline 1]$
a = 9.5020 (19) Å
b = 10.054 (2) Å
c = 10.735 (2) Å
α = 72.78 (3)°
β = 89.17 (3)°
γ = 74.81 (3)°
V = 943.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Entaf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.901, T_max = 0.965
3686 measured reflections
3463 independent reflections
2648 reflections with I > 2σ(I)
R_int = 0.014
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.146
S = 1.00
3463 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.85 (3)	2.19 (3)	3.034 (3)	176 (2)
C4—H4A⋯N3ⁱⁱ	0.93	2.62	3.488 (4)	155
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x, -y, -z+2.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: https://doi.org/10.1107/S1600536810050609/bq2258sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050609/bq2258Isup2.hkl

checkCIF report

Comment top

The title compound, C₂₂H₁₃Cl₂N₃,(I), contains amino group, which can react with different groups to prepare various function organic compounds. It is a kind of aromatic organic intermediate which can be used for many fields such as medicine (Mantri et al., 2008). The molecular structure of (I) is shown in Fig. 1. In (I), the naphthyl and the two rings, pyridyl and phenyl are oriented with different dihedral angles; 55.04 (7) ° between naphthyl and pyridyl, 75.87 (7) ° between naphthyl and phenyl and 59.56 (8) ° between pyridyl and phenyl. In the crystal structure of the title compound, the molecules were connected together via N—H···N and C—H···N intermolecular hydrogen bonds to form a three dimensional network, which seems to be very effective in the stabilization of the crystal structure.

Related literature top

The title compound is an important organic synthesis intermediate. For the synthetic procedure, see: Mantri et al. (2008). For related literature [on what subject?], see: Mkhalid et al. (2006). For general background [to what?], see: Moreau & Huber (1999).

Experimental top

The title compound, (I) was prepared by the literature method (Mantri et al., 2008). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and evaporating the solvent slowly at room temperature for about 5 d.

Structure description top

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). C—H···N and N—H···N hydrogen bonds are shown by dashed lines.

2-Amino-4-(2,4-dichlorophenyl)-6-(naphthalen-1-yl)nicotinonitrile top

Crystal data top

C₂₂H₁₃Cl₂N₃	Z = 2
M_r = 390.25	F(000) = 400
Triclinic, P1	D_x = 1.374 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5020 (19) Å	Cell parameters from 25 reflections
b = 10.054 (2) Å	θ = 10–14°
c = 10.735 (2) Å	µ = 0.36 mm⁻¹
α = 72.78 (3)°	T = 293 K
β = 89.17 (3)°	Block, colourless
γ = 74.81 (3)°	0.30 × 0.10 × 0.10 mm
V = 943.1 (3) Å³

Data collection top

Entaf–Nonius CAD-4 diffractometer	2648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 25.4°, θ_min = 2.0°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −11→12
T_min = 0.901, T_max = 0.965	l = −12→12
3686 measured reflections	3 standard reflections every 200 reflections
3463 independent reflections	intensity decay: 1%

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) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.095P)² + ] where P = (F_o² + 2F_c²)/3
3463 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₂H₁₃Cl₂N₃	γ = 74.81 (3)°
M_r = 390.25	V = 943.1 (3) Å³
Triclinic, P1	Z = 2
a = 9.5020 (19) Å	Mo Kα radiation
b = 10.054 (2) Å	µ = 0.36 mm⁻¹
c = 10.735 (2) Å	T = 293 K
α = 72.78 (3)°	0.30 × 0.10 × 0.10 mm
β = 89.17 (3)°

Data collection top

Entaf–Nonius CAD-4 diffractometer	2648 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.014
T_min = 0.901, T_max = 0.965	3 standard reflections every 200 reflections
3686 measured reflections	intensity decay: 1%
3463 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.18 e Å⁻³
3463 reflections	Δρ_min = −0.37 e Å⁻³
252 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	−0.37446 (8)	0.08316 (9)	0.92700 (9)	0.0687 (3)
N1	0.36411 (19)	0.4640 (2)	0.89712 (17)	0.0331 (4)
C1	−0.0992 (3)	0.2943 (3)	0.9925 (3)	0.0425 (6)
H1B	−0.0942	0.3531	1.0439	0.051*
Cl2	0.13996 (8)	0.12749 (9)	0.73801 (8)	0.0635 (3)
N2	0.4248 (2)	0.3529 (3)	1.1161 (2)	0.0414 (5)
H2A	0.480 (3)	0.408 (3)	1.110 (2)	0.044 (7)*
H2B	0.398 (3)	0.313 (3)	1.193 (3)	0.053 (8)*
C2	−0.2176 (3)	0.2375 (3)	0.9987 (3)	0.0477 (6)
H2C	−0.2919	0.2580	1.0532	0.057*
C3	−0.2235 (3)	0.1508 (3)	0.9234 (3)	0.0442 (6)
N3	0.1702 (3)	0.1711 (3)	1.2494 (2)	0.0542 (6)
C4	−0.1143 (3)	0.1165 (3)	0.8436 (2)	0.0426 (6)
H4A	−0.1192	0.0557	0.7942	0.051*
C5	0.0034 (3)	0.1752 (3)	0.8384 (2)	0.0390 (6)
C6	0.0130 (2)	0.2659 (2)	0.9114 (2)	0.0350 (5)
C7	0.1356 (2)	0.3340 (2)	0.9053 (2)	0.0347 (5)
C8	0.1657 (3)	0.4256 (3)	0.7898 (2)	0.0394 (6)
H8A	0.1114	0.4431	0.7125	0.047*
C9	0.2771 (2)	0.4911 (2)	0.7898 (2)	0.0353 (5)
C10	0.3364 (2)	0.3766 (2)	1.0103 (2)	0.0315 (5)
C11	0.2194 (2)	0.3119 (2)	1.0184 (2)	0.0327 (5)
C12	0.1897 (2)	0.2309 (3)	1.1454 (2)	0.0372 (5)
C13	0.3005 (2)	0.6054 (3)	0.6730 (2)	0.0364 (5)
C14	0.1836 (3)	0.7200 (3)	0.6165 (3)	0.0528 (7)
H14A	0.0907	0.7181	0.6441	0.063*
C15	0.2017 (4)	0.8417 (3)	0.5168 (3)	0.0660 (9)
H15A	0.1209	0.9184	0.4783	0.079*
C16	0.3370 (3)	0.8461 (3)	0.4774 (3)	0.0615 (8)
H16A	0.3486	0.9278	0.4140	0.074*
C17	0.4602 (3)	0.7293 (3)	0.5308 (2)	0.0459 (6)
C18	0.6025 (3)	0.7317 (4)	0.4896 (3)	0.0615 (8)
H18A	0.6156	0.8140	0.4280	0.074*
C19	0.7199 (3)	0.6162 (4)	0.5385 (3)	0.0623 (8)
H19A	0.8128	0.6208	0.5126	0.075*
C20	0.7004 (3)	0.4907 (3)	0.6275 (3)	0.0520 (7)
H20A	0.7801	0.4101	0.6576	0.062*
C21	0.5663 (3)	0.4846 (3)	0.6708 (2)	0.0411 (6)
H21A	0.5561	0.3999	0.7306	0.049*
C22	0.4431 (3)	0.6037 (3)	0.6270 (2)	0.0355 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0450 (4)	0.0707 (5)	0.1083 (7)	−0.0386 (4)	0.0167 (4)	−0.0338 (5)
N1	0.0318 (10)	0.0407 (11)	0.0316 (10)	−0.0177 (8)	0.0053 (8)	−0.0112 (8)
C1	0.0358 (13)	0.0445 (14)	0.0554 (15)	−0.0182 (11)	0.0083 (11)	−0.0211 (12)
Cl2	0.0653 (5)	0.0837 (5)	0.0692 (5)	−0.0447 (4)	0.0347 (4)	−0.0439 (4)
N2	0.0432 (12)	0.0565 (14)	0.0308 (11)	−0.0301 (11)	0.0007 (9)	−0.0078 (10)
C2	0.0350 (13)	0.0484 (15)	0.0667 (17)	−0.0175 (11)	0.0154 (12)	−0.0227 (13)
C3	0.0327 (13)	0.0409 (14)	0.0607 (16)	−0.0206 (11)	0.0027 (11)	−0.0083 (12)
N3	0.0611 (15)	0.0587 (14)	0.0428 (13)	−0.0297 (12)	0.0063 (11)	−0.0038 (11)
C4	0.0444 (14)	0.0422 (14)	0.0486 (14)	−0.0229 (12)	0.0031 (11)	−0.0148 (11)
C5	0.0370 (13)	0.0454 (14)	0.0371 (12)	−0.0202 (11)	0.0064 (10)	−0.0083 (11)
C6	0.0315 (12)	0.0369 (12)	0.0376 (12)	−0.0161 (10)	−0.0002 (10)	−0.0068 (10)
C7	0.0308 (11)	0.0372 (12)	0.0412 (13)	−0.0154 (10)	0.0055 (10)	−0.0141 (10)
C8	0.0367 (13)	0.0532 (15)	0.0345 (12)	−0.0242 (11)	0.0004 (10)	−0.0117 (11)
C9	0.0351 (12)	0.0412 (13)	0.0338 (12)	−0.0166 (10)	0.0067 (10)	−0.0124 (10)
C10	0.0307 (11)	0.0338 (12)	0.0339 (12)	−0.0131 (9)	0.0056 (9)	−0.0122 (9)
C11	0.0314 (11)	0.0344 (12)	0.0359 (12)	−0.0149 (9)	0.0062 (9)	−0.0110 (10)
C12	0.0361 (12)	0.0378 (13)	0.0418 (14)	−0.0186 (10)	0.0031 (10)	−0.0106 (11)
C13	0.0376 (13)	0.0434 (13)	0.0310 (12)	−0.0179 (11)	0.0030 (10)	−0.0092 (10)
C14	0.0411 (15)	0.0617 (18)	0.0483 (15)	−0.0126 (13)	0.0071 (12)	−0.0071 (13)
C15	0.0593 (19)	0.0566 (18)	0.0579 (18)	−0.0013 (15)	0.0045 (15)	0.0059 (14)
C16	0.0656 (19)	0.0498 (17)	0.0534 (17)	−0.0141 (15)	0.0135 (14)	0.0057 (13)
C17	0.0513 (15)	0.0503 (15)	0.0363 (13)	−0.0222 (13)	0.0078 (11)	−0.0062 (11)
C18	0.065 (2)	0.069 (2)	0.0523 (16)	−0.0370 (17)	0.0211 (14)	−0.0053 (15)
C19	0.0465 (16)	0.088 (2)	0.0569 (18)	−0.0307 (17)	0.0174 (14)	−0.0192 (16)
C20	0.0407 (14)	0.0675 (18)	0.0458 (15)	−0.0114 (13)	0.0085 (12)	−0.0174 (14)
C21	0.0445 (14)	0.0472 (14)	0.0315 (12)	−0.0153 (12)	0.0056 (10)	−0.0094 (11)
C22	0.0396 (13)	0.0437 (13)	0.0290 (11)	−0.0191 (11)	0.0039 (9)	−0.0125 (10)

Geometric parameters (Å, º) top

Cl1—C3	1.736 (2)	C9—C13	1.488 (3)
N1—C10	1.341 (3)	C10—C11	1.417 (3)
N1—C9	1.345 (3)	C11—C12	1.434 (3)
C1—C2	1.382 (3)	C13—C14	1.365 (4)
C1—C6	1.392 (3)	C13—C22	1.432 (3)
C1—H1B	0.9300	C14—C15	1.414 (4)
Cl2—C5	1.736 (2)	C14—H14A	0.9300
N2—C10	1.347 (3)	C15—C16	1.356 (4)
N2—H2A	0.84 (3)	C15—H15A	0.9300
N2—H2B	0.86 (3)	C16—C17	1.406 (4)
C2—C3	1.365 (4)	C16—H16A	0.9300
C2—H2C	0.9300	C17—C18	1.421 (4)
C3—C4	1.376 (3)	C17—C22	1.421 (3)
N3—C12	1.139 (3)	C18—C19	1.358 (4)
C4—C5	1.388 (3)	C18—H18A	0.9300
C4—H4A	0.9300	C19—C20	1.394 (4)
C5—C6	1.387 (3)	C19—H19A	0.9300
C6—C7	1.490 (3)	C20—C21	1.360 (4)
C7—C8	1.386 (3)	C20—H20A	0.9300
C7—C11	1.390 (3)	C21—C22	1.405 (3)
C8—C9	1.384 (3)	C21—H21A	0.9300
C8—H8A	0.9300

C10—N1—C9	118.57 (19)	C7—C11—C10	119.3 (2)
C2—C1—C6	121.8 (2)	C7—C11—C12	123.0 (2)
C2—C1—H1B	119.1	C10—C11—C12	117.6 (2)
C6—C1—H1B	119.1	N3—C12—C11	175.9 (3)
C10—N2—H2A	117.4 (17)	C14—C13—C22	120.1 (2)
C10—N2—H2B	118.6 (19)	C14—C13—C9	118.0 (2)
H2A—N2—H2B	118 (2)	C22—C13—C9	121.7 (2)
C3—C2—C1	118.7 (2)	C13—C14—C15	121.0 (3)
C3—C2—H2C	120.7	C13—C14—H14A	119.5
C1—C2—H2C	120.7	C15—C14—H14A	119.5
C2—C3—C4	122.0 (2)	C16—C15—C14	119.8 (3)
C2—C3—Cl1	119.0 (2)	C16—C15—H15A	120.1
C4—C3—Cl1	118.96 (19)	C14—C15—H15A	120.1
C3—C4—C5	118.3 (2)	C15—C16—C17	121.2 (3)
C3—C4—H4A	120.8	C15—C16—H16A	119.4
C5—C4—H4A	120.8	C17—C16—H16A	119.4
C6—C5—C4	121.7 (2)	C16—C17—C18	121.9 (3)
C6—C5—Cl2	121.38 (17)	C16—C17—C22	119.7 (2)
C4—C5—Cl2	116.88 (19)	C18—C17—C22	118.4 (2)
C5—C6—C1	117.4 (2)	C19—C18—C17	121.3 (3)
C5—C6—C7	123.1 (2)	C19—C18—H18A	119.3
C1—C6—C7	119.5 (2)	C17—C18—H18A	119.3
C8—C7—C11	118.0 (2)	C18—C19—C20	119.6 (3)
C8—C7—C6	121.8 (2)	C18—C19—H19A	120.2
C11—C7—C6	120.2 (2)	C20—C19—H19A	120.2
C9—C8—C7	119.8 (2)	C21—C20—C19	120.8 (3)
C9—C8—H8A	120.1	C21—C20—H20A	119.6
C7—C8—H8A	120.1	C19—C20—H20A	119.6
N1—C9—C8	122.7 (2)	C20—C21—C22	121.4 (2)
N1—C9—C13	115.38 (19)	C20—C21—H21A	119.3
C8—C9—C13	121.8 (2)	C22—C21—H21A	119.3
N1—C10—N2	117.0 (2)	C21—C22—C17	118.2 (2)
N1—C10—C11	121.53 (19)	C21—C22—C13	123.8 (2)
N2—C10—C11	121.4 (2)	C17—C22—C13	118.0 (2)

C6—C1—C2—C3	0.3 (4)	N2—C10—C11—C7	−176.9 (2)
C1—C2—C3—C4	1.1 (4)	N1—C10—C11—C12	−174.4 (2)
C1—C2—C3—Cl1	−178.1 (2)	N2—C10—C11—C12	5.6 (3)
C2—C3—C4—C5	−1.3 (4)	C7—C11—C12—N3	−155 (4)
Cl1—C3—C4—C5	177.91 (18)	C10—C11—C12—N3	22 (4)
C3—C4—C5—C6	0.1 (4)	N1—C9—C13—C14	−123.8 (2)
C3—C4—C5—Cl2	179.22 (19)	C8—C9—C13—C14	51.5 (3)
C4—C5—C6—C1	1.2 (4)	N1—C9—C13—C22	50.6 (3)
Cl2—C5—C6—C1	−177.86 (18)	C8—C9—C13—C22	−134.1 (2)
C4—C5—C6—C7	−178.2 (2)	C22—C13—C14—C15	−3.2 (4)
Cl2—C5—C6—C7	2.7 (3)	C9—C13—C14—C15	171.4 (3)
C2—C1—C6—C5	−1.4 (4)	C13—C14—C15—C16	−0.9 (5)
C2—C1—C6—C7	178.0 (2)	C14—C15—C16—C17	2.3 (5)
C5—C6—C7—C8	59.9 (3)	C15—C16—C17—C18	179.4 (3)
C1—C6—C7—C8	−119.5 (3)	C15—C16—C17—C22	0.4 (5)
C5—C6—C7—C11	−123.1 (3)	C16—C17—C18—C19	−177.6 (3)
C1—C6—C7—C11	57.5 (3)	C22—C17—C18—C19	1.3 (4)
C11—C7—C8—C9	0.3 (4)	C17—C18—C19—C20	2.2 (5)
C6—C7—C8—C9	177.4 (2)	C18—C19—C20—C21	−3.1 (4)
C10—N1—C9—C8	−4.0 (3)	C19—C20—C21—C22	0.4 (4)
C10—N1—C9—C13	171.27 (19)	C20—C21—C22—C17	3.1 (4)
C7—C8—C9—N1	3.5 (4)	C20—C21—C22—C13	−177.5 (2)
C7—C8—C9—C13	−171.4 (2)	C16—C17—C22—C21	175.1 (2)
C9—N1—C10—N2	−179.4 (2)	C18—C17—C22—C21	−3.9 (4)
C9—N1—C10—C11	0.7 (3)	C16—C17—C22—C13	−4.4 (4)
C8—C7—C11—C10	−3.4 (3)	C18—C17—C22—C13	176.7 (2)
C6—C7—C11—C10	179.4 (2)	C14—C13—C22—C21	−173.7 (2)
C8—C7—C11—C12	173.9 (2)	C9—C13—C22—C21	12.0 (3)
C6—C7—C11—C12	−3.3 (3)	C14—C13—C22—C17	5.7 (3)
N1—C10—C11—C7	3.1 (3)	C9—C13—C22—C17	−168.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.85 (3)	2.19 (3)	3.034 (3)	176 (2)
C4—H4A···N3ⁱⁱ	0.93	2.62	3.488 (4)	155

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₃Cl₂N₃
M_r	390.25
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.5020 (19), 10.054 (2), 10.735 (2)
α, β, γ (°)	72.78 (3), 89.17 (3), 74.81 (3)
V (Å³)	943.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Entaf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.901, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	3686, 3463, 2648
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.00
No. of reflections	3463
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.37

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), 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
N2—H2A···N1ⁱ	0.85 (3)	2.19 (3)	3.034 (3)	176 (2)
C4—H4A···N3ⁱⁱ	0.93	2.62	3.488 (4)	155

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, and the fund of Jinling Institute of Technology (jit-n-2009–017) for support..

References

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