2-Amino-4-(2-chloro­phen­yl)-6-(naph­thalen-1-yl)pyridine-3-carbonitrile

Wei, H.-X.; Zhu, J.; Li, M.; Wang, J.; Guo, C.

doi:10.1107/S1600536812020909

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1839

doi:10.1107/S1600536812020909

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2-Amino-4-(2-chlorophenyl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile

Hong-Xia Wei,^a Jing Zhu,^a Ming Li,^a Jian-qiang Wang ^a and Cheng Guo ^b ^*

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 21 April 2012; accepted 8 May 2012; online 23 May 2012)

In the title compound, C₂₂H₁₄ClN₃, prepared by a one-pot reaction under microwave irradiation, the dihedral angles between the central pyridine ring and the pendant naphthyl and chlorobenzene ring systems are 49.2 (2) and 58.2 (3)°, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R₂²(8) loops. The pyridine N atom is the acceptor.

Related literature

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983 ). For the synthesis, see: Mantri et al. (2008 ). For related structures, see: Mkhalid et al. (2006 ).

Experimental

Crystal data

C₂₂H₁₄ClN₃
M_r = 355.81
Monoclinic, P 2₁ /n
a = 12.275 (3) Å
b = 4.6490 (9) Å
c = 30.887 (6) Å
β = 90.18 (3)°
V = 1762.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.956, T_max = 0.978
3397 measured reflections
3236 independent reflections
1558 reflections with I > 2σ(I)
R_int = 0.057
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.185
S = 1.00
3236 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.23	3.086 (5)	176
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812020909/hb6750sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020909/hb6750Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020909/hb6750Isup3.cml

checkCIF report

Comment top

The title compound, C₂₂H₁₄ClN₃(1), is an intermediate in the synthesis of biologically active molecules (Shishoo et al., 1983; Mantri et al. 2008). Herein we report its crystal structure. The molecular structure of (I) is shown in Fig. 1, and the selected geometric parameters are given in Table 1. In the molecules,the naphthyl (C13—C22) and phenyl ring planes (C1—C6) form torsion angles 49.2 and 58.2 °, respectively, with the middle pyridyl ring plane. In the crystal, there are N—H···N hydrogen bonds, which connect the independent molecules into dimers (Fig. 2 and Tab. 1).

Related literature top

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983). For the synthesis, see: Mantri et al. (2008). For related structures, see: Mkhalid et al. (2006).

Experimental top

For the prepartion of the title compound (1),a mixture of 2-chlorobenzaldehyde (2 mmol), malononitrile (2 mmol), 1-naphthal-dehyde (2 mmol) and ammonium acetate (16 mmol) was refluxed under microwave irradiation (6 min, WF-4000M microwave reaction system). After cooling to room temperature, the resulting solid product was filtered off and recrystallized from methanol to give the title compound. Colourless needles were obtained by dissolving the title compound (0.5 g) in methanol (20 ml) and slowly evaporating the solvent at room temperature for a period of about two weeks.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-Amino-4-(2-chlorophenyl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile top

Crystal data top

C₂₂H₁₄ClN₃	F(000) = 736
M_r = 355.81	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 421 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.275 (3) Å	Cell parameters from 25 reflections
b = 4.6490 (9) Å	θ = 9–12°
c = 30.887 (6) Å	µ = 0.23 mm⁻¹
β = 90.18 (3)°	T = 293 K
V = 1762.6 (6) Å³	Needle, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1558 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 25.5°, θ_min = 1.3°
ω/2θ scans	h = −14→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→5
T_min = 0.956, T_max = 0.978	l = −37→37
3397 measured reflections	3 standard reflections every 200 reflections
3236 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.050P)² + 1.9P] where P = (F_o² + 2F_c²)/3
3236 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₁₄ClN₃	V = 1762.6 (6) Å³
M_r = 355.81	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.275 (3) Å	µ = 0.23 mm⁻¹
b = 4.6490 (9) Å	T = 293 K
c = 30.887 (6) Å	0.20 × 0.10 × 0.10 mm
β = 90.18 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1558 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.057
T_min = 0.956, T_max = 0.978	3 standard reflections every 200 reflections
3397 measured reflections	intensity decay: 1%
3236 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
3236 reflections	Δρ_min = −0.19 e Å⁻³
235 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
Cl	0.31710 (12)	0.7045 (4)	0.20602 (4)	0.0872 (5)
N1	0.4498 (3)	0.3780 (9)	0.05627 (11)	0.0550 (10)
C1	0.6080 (4)	0.3185 (13)	0.20923 (15)	0.0773 (16)
H1B	0.6571	0.2335	0.1903	0.093*
N2	0.6054 (3)	0.6314 (10)	0.04127 (11)	0.0763 (14)
H2A	0.5897	0.6189	0.0142	0.092*
H2B	0.6635	0.7198	0.0494	0.092*
C2	0.6330 (5)	0.3305 (14)	0.25299 (16)	0.0863 (18)
H2C	0.6981	0.2532	0.2632	0.104*
N3	0.7314 (4)	0.8313 (12)	0.13555 (14)	0.0968 (17)
C3	0.5613 (5)	0.4568 (15)	0.28131 (17)	0.090 (2)
H3A	0.5779	0.4680	0.3107	0.109*
C4	0.4654 (5)	0.5656 (13)	0.26593 (15)	0.0814 (17)
H4A	0.4162	0.6475	0.2851	0.098*
C5	0.4402 (4)	0.5563 (11)	0.22255 (14)	0.0634 (13)
C6	0.5115 (4)	0.4305 (11)	0.19312 (13)	0.0578 (13)
C7	0.4887 (4)	0.4158 (11)	0.14580 (14)	0.0579 (13)
C8	0.3990 (4)	0.2782 (11)	0.12958 (13)	0.0597 (13)
H8A	0.3499	0.1926	0.1485	0.072*
C9	0.3800 (3)	0.2645 (10)	0.08536 (13)	0.0507 (11)
C10	0.5383 (4)	0.5115 (11)	0.07123 (14)	0.0542 (12)
C11	0.5606 (3)	0.5421 (11)	0.11589 (14)	0.0568 (12)
C12	0.6549 (4)	0.7022 (13)	0.12856 (14)	0.0673 (15)
C13	0.2812 (4)	0.1290 (10)	0.06732 (14)	0.0533 (12)
C14	0.1748 (4)	0.1886 (11)	0.08349 (14)	0.0577 (13)
C15	0.1539 (4)	0.3973 (12)	0.11570 (15)	0.0682 (14)
H15A	0.2113	0.5015	0.1276	0.082*
C16	0.0499 (5)	0.4471 (14)	0.12953 (18)	0.0842 (17)
H16A	0.0379	0.5848	0.1508	0.101*
C17	−0.0383 (5)	0.2979 (16)	0.11261 (19)	0.090 (2)
H17A	−0.1083	0.3344	0.1226	0.108*
C18	−0.0217 (4)	0.0997 (14)	0.08151 (19)	0.0807 (17)
H18A	−0.0808	−0.0007	0.0702	0.097*
C19	0.0835 (4)	0.0418 (12)	0.06576 (16)	0.0629 (13)
C20	0.1015 (4)	−0.1567 (12)	0.03181 (17)	0.0735 (15)
H20A	0.0425	−0.2559	0.0202	0.088*
C21	0.2025 (4)	−0.2061 (11)	0.01577 (15)	0.0679 (14)
H21A	0.2118	−0.3334	−0.0071	0.082*
C22	0.2927 (4)	−0.0649 (11)	0.03379 (15)	0.0613 (13)
H22A	0.3618	−0.1027	0.0229	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0919 (10)	0.1025 (12)	0.0674 (9)	0.0187 (9)	0.0206 (7)	−0.0003 (8)
N1	0.057 (2)	0.066 (3)	0.042 (2)	0.005 (2)	0.0057 (17)	0.003 (2)
C1	0.086 (4)	0.095 (4)	0.051 (3)	0.012 (3)	−0.004 (3)	−0.004 (3)
N2	0.065 (3)	0.118 (4)	0.046 (2)	−0.017 (3)	0.0128 (19)	−0.002 (3)
C2	0.100 (4)	0.106 (5)	0.052 (3)	−0.009 (4)	−0.012 (3)	0.006 (4)
N3	0.075 (3)	0.137 (5)	0.079 (3)	−0.029 (3)	0.009 (3)	−0.024 (3)
C3	0.100 (5)	0.123 (6)	0.049 (3)	−0.024 (4)	−0.007 (3)	0.008 (4)
C4	0.105 (4)	0.100 (5)	0.039 (3)	−0.011 (4)	0.013 (3)	−0.007 (3)
C5	0.073 (3)	0.072 (4)	0.045 (3)	−0.006 (3)	0.011 (2)	0.002 (3)
C6	0.073 (3)	0.064 (3)	0.036 (2)	−0.002 (3)	0.006 (2)	0.001 (2)
C7	0.064 (3)	0.066 (3)	0.043 (3)	0.009 (3)	0.003 (2)	0.000 (2)
C8	0.069 (3)	0.072 (3)	0.038 (2)	−0.004 (3)	0.009 (2)	0.002 (3)
C9	0.057 (3)	0.053 (3)	0.042 (2)	0.006 (2)	0.009 (2)	0.008 (2)
C10	0.050 (3)	0.069 (3)	0.044 (3)	0.006 (3)	0.007 (2)	0.000 (2)
C11	0.051 (3)	0.074 (3)	0.046 (3)	0.006 (3)	0.006 (2)	−0.008 (3)
C12	0.066 (3)	0.094 (4)	0.041 (3)	−0.001 (3)	0.007 (2)	−0.012 (3)
C13	0.060 (3)	0.057 (3)	0.042 (2)	0.004 (3)	0.000 (2)	0.011 (2)
C14	0.057 (3)	0.066 (3)	0.050 (3)	0.005 (3)	0.011 (2)	0.021 (3)
C15	0.069 (3)	0.080 (4)	0.056 (3)	0.003 (3)	0.010 (2)	0.015 (3)
C16	0.083 (4)	0.100 (5)	0.069 (4)	0.020 (4)	0.016 (3)	0.009 (3)
C17	0.067 (4)	0.121 (6)	0.083 (4)	0.021 (4)	0.019 (3)	0.031 (4)
C18	0.058 (3)	0.092 (5)	0.092 (4)	0.000 (3)	0.004 (3)	0.027 (4)
C19	0.062 (3)	0.062 (3)	0.064 (3)	−0.001 (3)	−0.001 (2)	0.018 (3)
C20	0.070 (3)	0.071 (4)	0.080 (4)	−0.001 (3)	−0.014 (3)	0.007 (3)
C21	0.090 (4)	0.063 (3)	0.051 (3)	0.007 (3)	−0.004 (3)	−0.003 (3)
C22	0.063 (3)	0.063 (3)	0.058 (3)	0.001 (3)	−0.007 (2)	0.007 (3)

Geometric parameters (Å, º) top

Cl—C5	1.736 (5)	C9—C13	1.475 (6)
N1—C10	1.332 (5)	C10—C11	1.413 (6)
N1—C9	1.351 (5)	C11—C12	1.429 (7)
C1—C6	1.385 (6)	C13—C22	1.380 (6)
C1—C2	1.386 (6)	C13—C14	1.427 (6)
C1—H1B	0.9300	C14—C15	1.414 (7)
N2—C10	1.360 (5)	C14—C19	1.421 (6)
N2—H2A	0.8600	C15—C16	1.367 (6)
N2—H2B	0.8600	C15—H15A	0.9300
C2—C3	1.375 (7)	C16—C17	1.386 (8)
C2—H2C	0.9300	C16—H16A	0.9300
N3—C12	1.134 (6)	C17—C18	1.347 (8)
C3—C4	1.365 (7)	C17—H17A	0.9300
C3—H3A	0.9300	C18—C19	1.407 (6)
C4—C5	1.375 (6)	C18—H18A	0.9300
C4—H4A	0.9300	C19—C20	1.414 (7)
C5—C6	1.392 (6)	C20—C21	1.356 (6)
C6—C7	1.489 (6)	C20—H20A	0.9300
C7—C8	1.367 (6)	C21—C22	1.401 (6)
C7—C11	1.408 (6)	C21—H21A	0.9300
C8—C9	1.386 (5)	C22—H22A	0.9300
C8—H8A	0.9300

C10—N1—C9	118.0 (4)	C7—C11—C10	118.6 (4)
C6—C1—C2	121.4 (5)	C7—C11—C12	123.1 (4)
C6—C1—H1B	119.3	C10—C11—C12	118.3 (4)
C2—C1—H1B	119.3	N3—C12—C11	175.1 (5)
C10—N2—H2A	120.0	C22—C13—C14	119.0 (4)
C10—N2—H2B	120.0	C22—C13—C9	118.5 (4)
H2A—N2—H2B	120.0	C14—C13—C9	122.5 (4)
C3—C2—C1	119.8 (5)	C15—C14—C19	117.1 (4)
C3—C2—H2C	120.1	C15—C14—C13	123.2 (5)
C1—C2—H2C	120.1	C19—C14—C13	119.6 (5)
C4—C3—C2	119.3 (5)	C16—C15—C14	120.5 (5)
C4—C3—H3A	120.3	C16—C15—H15A	119.7
C2—C3—H3A	120.3	C14—C15—H15A	119.7
C3—C4—C5	121.3 (5)	C15—C16—C17	121.7 (6)
C3—C4—H4A	119.4	C15—C16—H16A	119.1
C5—C4—H4A	119.4	C17—C16—H16A	119.1
C4—C5—C6	120.6 (5)	C18—C17—C16	119.4 (5)
C4—C5—Cl	117.8 (4)	C18—C17—H17A	120.3
C6—C5—Cl	121.5 (4)	C16—C17—H17A	120.3
C1—C6—C5	117.5 (4)	C17—C18—C19	121.2 (6)
C1—C6—C7	119.5 (4)	C17—C18—H18A	119.4
C5—C6—C7	122.9 (4)	C19—C18—H18A	119.4
C8—C7—C11	117.4 (4)	C18—C19—C20	121.8 (5)
C8—C7—C6	122.0 (4)	C18—C19—C14	119.9 (5)
C11—C7—C6	120.6 (4)	C20—C19—C14	118.3 (5)
C7—C8—C9	121.0 (4)	C21—C20—C19	121.8 (5)
C7—C8—H8A	119.5	C21—C20—H20A	119.1
C9—C8—H8A	119.5	C19—C20—H20A	119.1
N1—C9—C8	122.2 (4)	C20—C21—C22	119.9 (5)
N1—C9—C13	116.0 (4)	C20—C21—H21A	120.1
C8—C9—C13	121.8 (4)	C22—C21—H21A	120.1
N1—C10—N2	116.7 (4)	C13—C22—C21	121.4 (5)
N1—C10—C11	122.8 (4)	C13—C22—H22A	119.3
N2—C10—C11	120.5 (4)	C21—C22—H22A	119.3

C6—C1—C2—C3	−0.3 (9)	N1—C10—C11—C12	−176.8 (5)
C1—C2—C3—C4	0.9 (9)	N2—C10—C11—C12	0.1 (7)
C2—C3—C4—C5	−1.3 (10)	C7—C11—C12—N3	178 (7)
C3—C4—C5—C6	1.1 (9)	C10—C11—C12—N3	−3 (7)
C3—C4—C5—Cl	−179.2 (5)	N1—C9—C13—C22	48.9 (6)
C2—C1—C6—C5	0.1 (8)	C8—C9—C13—C22	−132.1 (5)
C2—C1—C6—C7	179.3 (5)	N1—C9—C13—C14	−131.7 (4)
C4—C5—C6—C1	−0.5 (8)	C8—C9—C13—C14	47.3 (6)
Cl—C5—C6—C1	179.8 (4)	C22—C13—C14—C15	−175.7 (4)
C4—C5—C6—C7	−179.6 (5)	C9—C13—C14—C15	5.0 (7)
Cl—C5—C6—C7	0.7 (7)	C22—C13—C14—C19	1.8 (6)
C1—C6—C7—C8	121.2 (6)	C9—C13—C14—C19	−177.5 (4)
C5—C6—C7—C8	−59.7 (7)	C19—C14—C15—C16	1.6 (7)
C1—C6—C7—C11	−58.1 (7)	C13—C14—C15—C16	179.2 (4)
C5—C6—C7—C11	121.1 (5)	C14—C15—C16—C17	−0.3 (8)
C11—C7—C8—C9	0.0 (7)	C15—C16—C17—C18	−0.5 (9)
C6—C7—C8—C9	−179.3 (4)	C16—C17—C18—C19	−0.2 (9)
C10—N1—C9—C8	−1.3 (7)	C17—C18—C19—C20	−177.2 (5)
C10—N1—C9—C13	177.7 (4)	C17—C18—C19—C14	1.6 (8)
C7—C8—C9—N1	1.8 (7)	C15—C14—C19—C18	−2.2 (7)
C7—C8—C9—C13	−177.1 (5)	C13—C14—C19—C18	−179.9 (4)
C9—N1—C10—N2	−178.0 (4)	C15—C14—C19—C20	176.6 (4)
C9—N1—C10—C11	−1.0 (7)	C13—C14—C19—C20	−1.1 (7)
C8—C7—C11—C10	−2.1 (7)	C18—C19—C20—C21	178.0 (5)
C6—C7—C11—C10	177.1 (4)	C14—C19—C20—C21	−0.8 (7)
C8—C7—C11—C12	177.4 (5)	C19—C20—C21—C22	1.9 (8)
C6—C7—C11—C12	−3.4 (7)	C14—C13—C22—C21	−0.7 (7)
N1—C10—C11—C7	2.7 (7)	C9—C13—C22—C21	178.6 (4)
N2—C10—C11—C7	179.6 (4)	C20—C21—C22—C13	−1.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.23	3.086 (5)	176

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄ClN₃
M_r	355.81
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.275 (3), 4.6490 (9), 30.887 (6)
β (°)	90.18 (3)
V (Å³)	1762.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.956, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	3397, 3236, 1558
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.185, 1.00
No. of reflections	3236
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.23	3.086 (5)	176

Symmetry code: (i) −x+1, −y+1, −z.

References

Enraf–Nonius (1994). CAD-4 XPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Mantri, M., Graaf, O., Veldhoven, J. & IJzerman, A. P. (2008). J. Med. Chem. 51, 4449–4455. Web of Science CrossRef PubMed CAS Google Scholar
Mkhalid, I. A. I., Coventry, D. N., Albesa-Jove, D., Batsanov, A. S., Howard, J. A. K. & Marder, T. B. (2006). Angew. Chem. Int. Ed. 45, 489–491. Web of Science CSD CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shishoo, C. J., Devani, M. B., Bhadti, V. S., Ananthan, S. & Ullas, G. V. (1983). Tetrahedron Lett. pp. 4611–4612. CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1839

doi:10.1107/S1600536812020909

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