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

Mao, W.; Guo, C.; Wang, W.; Luan, C.; Du, R.

doi:10.1107/S1600536811002765

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o853

doi:10.1107/S1600536811002765

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

Wei Mao,^a Cheng Guo,^a ^* Wei Wang,^a Chang-jun Luan ^a and Ren-jun Du ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 15 December 2010; accepted 20 January 2011; online 12 March 2011)

In the title compound, C₂₂H₁₅N₃, the naphthyl ring system makes dihedral angles of 67.40 (2) and 59.80 (3)° with the pyridyl and phenyl rings, respectively. In the crystal, the molecules are connected via intermolecular N—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthetic procedure, see: Mantri et al. (2008 ). For related structures, see: Mkhalid et al. (2006 ). For general background, see: Moreau et al. (1999 ).

Experimental

Crystal data

C₂₂H₁₅N₃
M_r = 321.37
Monoclinic, C 2/c
a = 11.799 (2) Å
b = 17.284 (3) Å
c = 17.492 (4) Å
β = 98.26 (3)°
V = 3530.2 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.979, T_max = 0.993
3367 measured reflections
3240 independent reflections
1717 reflections with I > 2σ(I)
R_int = 0.030
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.180
S = 1.01
3240 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 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	2.34	3.180 (4)	165
N2—H2B⋯N3ⁱⁱ	0.86	2.34	3.138 (4)	154
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+1.

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002765/bv2172sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002765/bv2172Isup2.hkl

checkCIF report

Comment top

The title compound, (I), contains an 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). 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. The bond lengths and angles are within normal ranges. The torsion angle between the naphthyl (C12—C21) and phenyl planes (C1 to C6) is 67.40 (2)° and 59.80 (3)°, respectively. In the crystal of the title compound, (I) was connected together via N—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

For the synthetic procedure, see: Mantri et al. (2008). For related structures, see: Mkhalid et al. (2006). For general background, see: Moreau et al. (1999).

Experimental top

The title compound, (I) was prepared by the literature method (Mantri, et al., 2008). Malononitrile (20 mmol) was dissolved in EtOH (40 ml), added benzalaldehyde (20 mmol) followed by 2 drops of piperidine, the reaction mixture was refluxed for 1 h. The precipitate formed upon cooling the reaction mixture to room temperature. The crude product was filtered, and it was pure enough to carry out the further reactions. To a solution of previously synthesized benzylidene malononitrile (3 mmol, 1 equiv) in toluene was added 1-(naphthalen-1-yl)ethanone (3 mmol, 1 equiv) and ammonium acetate (4.5 mmol, 1.5 equiv). The mixture was heated in a microwave at 120° for 1 h. The reaction mixture was purified by column chromatography using dichloromethane-methanol solvent system. 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 7 d.

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: 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). N—H···N hydrogen bonds are shown by dashed lines.

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

Crystal data top

C₂₂H₁₅N₃	F(000) = 1344
M_r = 321.37	D_x = 1.209 Mg m⁻³
Monoclinic, C2/c	Melting point: 438 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.799 (2) Å	Cell parameters from 25 reflections
b = 17.284 (3) Å	θ = 9–12°
c = 17.492 (4) Å	µ = 0.07 mm⁻¹
β = 98.26 (3)°	T = 293 K
V = 3530.2 (12) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1717 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 25.4°, θ_min = 2.1°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
T_min = 0.979, T_max = 0.993	l = −21→20
3367 measured reflections	3 standard reflections every 200 reflections
3240 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.050P)² + 3.8P] where P = (F_o² + 2F_c²)/3
3240 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₂H₁₅N₃	V = 3530.2 (12) Å³
M_r = 321.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.799 (2) Å	µ = 0.07 mm⁻¹
b = 17.284 (3) Å	T = 293 K
c = 17.492 (4) Å	0.30 × 0.20 × 0.10 mm
β = 98.26 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1717 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.030
T_min = 0.979, T_max = 0.993	3 standard reflections every 200 reflections
3367 measured reflections	intensity decay: 1%
3240 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	1 restraint
wR(F²) = 0.180	H-atom parameters constrained
S = 1.01	Δρ_max = 0.13 e Å⁻³
3240 reflections	Δρ_min = −0.13 e Å⁻³
208 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
N1	0.3542 (2)	0.1427 (2)	0.69970 (17)	0.1156 (13)
C1	0.0883 (3)	0.0618 (2)	0.4510 (2)	0.1035 (13)
H1B	0.1191	0.0169	0.4749	0.124*
N2	0.4951 (2)	0.08860 (18)	0.64401 (14)	0.1002 (10)
H2A	0.5373	0.0942	0.6880	0.120*
H2B	0.5231	0.0682	0.6060	0.120*
C2	0.0113 (4)	0.0532 (3)	0.3842 (3)	0.1361 (17)
H2C	−0.0090	0.0049	0.3630	0.163*
N3	0.3832 (3)	0.0285 (2)	0.45458 (14)	0.1147 (13)
C3	−0.0341 (4)	0.1219 (4)	0.3506 (3)	0.1341 (17)
H3A	−0.0854	0.1198	0.3050	0.161*
C4	−0.0050 (5)	0.1915 (4)	0.3830 (3)	0.1376 (17)
H4A	−0.0356	0.2367	0.3596	0.165*
C5	0.0720 (4)	0.1953 (3)	0.4525 (3)	0.1277 (16)
H5A	0.0882	0.2428	0.4765	0.153*
C6	0.1229 (3)	0.1301 (3)	0.4846 (2)	0.0905 (11)
C7	0.2017 (3)	0.1324 (2)	0.55800 (18)	0.0783 (9)
C8	0.1731 (3)	0.1668 (2)	0.6244 (2)	0.0958 (12)
H8A	0.1027	0.1917	0.6214	0.115*
C9	0.2443 (3)	0.1661 (3)	0.6957 (2)	0.1076 (13)
C10	0.3872 (3)	0.1114 (2)	0.63484 (18)	0.0819 (10)
C11	0.3122 (3)	0.10289 (18)	0.56551 (16)	0.0704 (8)
C12	0.2128 (3)	0.1874 (3)	0.7756 (3)	0.1025 (13)
C13	0.1864 (3)	0.2620 (3)	0.7827 (2)	0.0940 (12)
C14	0.1949 (4)	0.3212 (3)	0.7187 (2)	0.1173 (15)
H14A	0.2117	0.3065	0.6704	0.141*
C15	0.1767 (4)	0.3959 (3)	0.7358 (3)	0.115
H15A	0.1869	0.4339	0.6999	0.138*
C16	0.1480 (4)	0.4143 (3)	0.7956 (3)	0.114
H16A	0.1390	0.4673	0.8020	0.137*
C17	0.1279 (3)	0.3736 (2)	0.8516 (2)	0.092
H17A	0.0958	0.3958	0.8918	0.110*
C18	0.1548 (3)	0.2920 (2)	0.8532 (2)	0.0879 (11)
C19	0.1452 (3)	0.2408 (3)	0.9156 (3)	0.1128 (14)
H19A	0.1199	0.2579	0.9607	0.135*
C20	0.1769 (4)	0.1602 (3)	0.9057 (3)	0.1198 (14)
H20A	0.1759	0.1232	0.9442	0.144*
C21	0.2098 (4)	0.1426 (3)	0.8311 (3)	0.1124 (14)
H21A	0.2313	0.0916	0.8237	0.135*
C22	0.3531 (3)	0.0621 (2)	0.50320 (16)	0.0783 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0609 (18)	0.192 (3)	0.099 (2)	−0.014 (2)	0.0263 (16)	−0.087 (2)
C1	0.109 (3)	0.111 (3)	0.077 (2)	0.000 (2)	−0.035 (2)	0.003 (2)
N2	0.0698 (19)	0.171 (3)	0.0560 (16)	0.0290 (19)	−0.0046 (13)	−0.0224 (17)
C2	0.162 (5)	0.141 (4)	0.092 (3)	−0.015 (4)	−0.026 (3)	−0.030 (3)
N3	0.134 (3)	0.167 (3)	0.0374 (15)	0.083 (2)	−0.0051 (16)	−0.0141 (17)
C3	0.124 (4)	0.165 (5)	0.099 (3)	0.035 (4)	−0.032 (3)	−0.007 (4)
C4	0.121 (4)	0.136 (5)	0.151 (5)	0.008 (3)	0.002 (4)	0.031 (4)
C5	0.103 (3)	0.123 (4)	0.150 (4)	0.016 (3)	−0.004 (3)	−0.015 (3)
C6	0.067 (2)	0.117 (3)	0.084 (2)	0.024 (2)	0.0001 (18)	−0.036 (2)
C7	0.060 (2)	0.102 (3)	0.072 (2)	0.0134 (18)	0.0038 (16)	−0.0270 (18)
C8	0.074 (2)	0.117 (3)	0.094 (3)	0.028 (2)	0.005 (2)	−0.040 (2)
C9	0.084 (3)	0.140 (4)	0.101 (3)	0.011 (2)	0.023 (2)	−0.042 (3)
C10	0.069 (2)	0.114 (3)	0.0649 (19)	0.007 (2)	0.0169 (15)	−0.0229 (19)
C11	0.075 (2)	0.081 (2)	0.0555 (17)	0.0086 (17)	0.0104 (14)	−0.0132 (15)
C12	0.080 (3)	0.119 (4)	0.105 (3)	−0.004 (3)	0.006 (2)	−0.028 (3)
C13	0.067 (2)	0.119 (3)	0.092 (3)	0.002 (2)	−0.0036 (19)	−0.042 (3)
C14	0.112 (3)	0.154 (4)	0.077 (3)	0.022 (3)	−0.016 (2)	−0.032 (3)
C15	0.115	0.115	0.115	0.000	0.016	0.000
C16	0.114	0.114	0.114	0.000	0.016	0.000
C17	0.092	0.092	0.092	0.000	0.013	0.000
C18	0.0534 (19)	0.123 (3)	0.081 (2)	0.0281 (19)	−0.0125 (17)	−0.038 (2)
C19	0.083 (3)	0.151 (4)	0.107 (3)	−0.019 (3)	0.020 (2)	−0.023 (3)
C20	0.114 (3)	0.131 (4)	0.114 (4)	−0.032 (3)	0.016 (3)	0.014 (3)
C21	0.095 (3)	0.133 (4)	0.113 (4)	−0.024 (3)	0.026 (3)	−0.028 (3)
C22	0.082 (2)	0.120 (3)	0.0287 (14)	0.030 (2)	−0.0034 (14)	0.0008 (17)

Geometric parameters (Å, º) top

N1—C9	1.351 (4)	C9—C12	1.542 (5)
N1—C10	1.363 (4)	C10—C11	1.403 (4)
C1—C6	1.356 (5)	C11—C22	1.439 (4)
C1—C2	1.382 (5)	C12—C21	1.247 (5)
C1—H1B	0.9300	C12—C13	1.337 (5)
N2—C10	1.320 (4)	C13—C18	1.435 (5)
N2—H2A	0.8600	C13—C14	1.532 (6)
N2—H2B	0.8600	C14—C15	1.349 (5)
C2—C3	1.397 (6)	C14—H14A	0.9300
C2—H2C	0.9300	C15—C16	1.189 (5)
N3—C22	1.128 (4)	C15—H15A	0.9300
C3—C4	1.353 (6)	C16—C17	1.255 (5)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.410 (6)	C17—C18	1.444 (5)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.359 (5)	C18—C19	1.422 (5)
C5—H5A	0.9300	C19—C20	1.459 (6)
C6—C7	1.473 (5)	C19—H19A	0.9300
C7—C11	1.389 (4)	C20—C21	1.446 (6)
C7—C8	1.389 (4)	C20—H20A	0.9300
C8—C9	1.399 (5)	C21—H21A	0.9300
C8—H8A	0.9300

C9—N1—C10	117.5 (3)	C7—C11—C10	120.7 (3)
C6—C1—C2	125.6 (4)	C7—C11—C22	121.4 (3)
C6—C1—H1B	117.2	C10—C11—C22	117.9 (3)
C2—C1—H1B	117.2	C21—C12—C13	119.6 (5)
C10—N2—H2A	120.0	C21—C12—C9	126.5 (5)
C10—N2—H2B	120.0	C13—C12—C9	113.9 (5)
H2A—N2—H2B	120.0	C12—C13—C18	121.4 (5)
C1—C2—C3	115.4 (4)	C12—C13—C14	122.4 (4)
C1—C2—H2C	122.3	C18—C13—C14	116.1 (4)
C3—C2—H2C	122.3	C15—C14—C13	116.6 (4)
C4—C3—C2	121.4 (4)	C15—C14—H14A	121.7
C4—C3—H3A	119.3	C13—C14—H14A	121.7
C2—C3—H3A	119.3	C16—C15—C14	121.8 (5)
C3—C4—C5	119.7 (5)	C16—C15—H15A	119.1
C3—C4—H4A	120.2	C14—C15—H15A	119.1
C5—C4—H4A	120.2	C15—C16—C17	130.1 (5)
C6—C5—C4	120.7 (5)	C15—C16—H16A	114.9
C6—C5—H5A	119.7	C17—C16—H16A	114.9
C4—C5—H5A	119.7	C16—C17—C18	119.9 (4)
C1—C6—C5	117.0 (4)	C16—C17—H17A	120.1
C1—C6—C7	121.0 (4)	C18—C17—H17A	120.1
C5—C6—C7	121.6 (4)	C19—C18—C13	119.6 (4)
C11—C7—C8	114.5 (3)	C19—C18—C17	125.5 (4)
C11—C7—C6	122.6 (3)	C13—C18—C17	114.7 (4)
C8—C7—C6	122.8 (3)	C18—C19—C20	116.9 (4)
C7—C8—C9	123.7 (3)	C18—C19—H19A	121.5
C7—C8—H8A	118.2	C20—C19—H19A	121.5
C9—C8—H8A	118.2	C21—C20—C19	114.6 (4)
N1—C9—C8	119.9 (3)	C21—C20—H20A	122.7
N1—C9—C12	112.2 (4)	C19—C20—H20A	122.7
C8—C9—C12	127.9 (3)	C12—C21—C20	127.8 (5)
N2—C10—N1	113.8 (3)	C12—C21—H21A	116.1
N2—C10—C11	123.5 (3)	C20—C21—H21A	116.1
N1—C10—C11	122.8 (3)	N3—C22—C11	178.1 (4)

C6—C1—C2—C3	−0.8 (7)	N1—C9—C12—C21	−64.7 (6)
C1—C2—C3—C4	−1.1 (8)	C8—C9—C12—C21	113.5 (6)
C2—C3—C4—C5	−0.5 (9)	N1—C9—C12—C13	115.7 (4)
C3—C4—C5—C6	4.2 (8)	C8—C9—C12—C13	−66.2 (6)
C2—C1—C6—C5	4.3 (7)	C21—C12—C13—C18	0.2 (6)
C2—C1—C6—C7	177.2 (4)	C9—C12—C13—C18	179.9 (3)
C4—C5—C6—C1	−5.9 (7)	C21—C12—C13—C14	176.4 (4)
C4—C5—C6—C7	−178.7 (4)	C9—C12—C13—C14	−3.9 (5)
C1—C6—C7—C11	62.2 (5)	C12—C13—C14—C15	−173.7 (4)
C5—C6—C7—C11	−125.2 (4)	C18—C13—C14—C15	2.7 (5)
C1—C6—C7—C8	−120.2 (4)	C13—C14—C15—C16	−4.9 (7)
C5—C6—C7—C8	52.3 (6)	C14—C15—C16—C17	−1.0 (8)
C11—C7—C8—C9	−5.7 (6)	C15—C16—C17—C18	8.9 (8)
C6—C7—C8—C9	176.6 (4)	C12—C13—C18—C19	−3.5 (5)
C10—N1—C9—C8	−7.9 (6)	C14—C13—C18—C19	−179.9 (3)
C10—N1—C9—C12	170.4 (4)	C12—C13—C18—C17	−179.6 (3)
C7—C8—C9—N1	11.3 (7)	C14—C13—C18—C17	4.0 (4)
C7—C8—C9—C12	−166.7 (4)	C16—C17—C18—C19	174.6 (4)
C9—N1—C10—N2	−178.7 (4)	C16—C17—C18—C13	−9.6 (5)
C9—N1—C10—C11	−0.1 (6)	C13—C18—C19—C20	4.4 (5)
C8—C7—C11—C10	−2.5 (5)	C17—C18—C19—C20	−179.9 (3)
C6—C7—C11—C10	175.2 (4)	C18—C19—C20—C21	−2.5 (5)
C8—C7—C11—C22	176.9 (3)	C13—C12—C21—C20	2.0 (7)
C6—C7—C11—C22	−5.4 (5)	C9—C12—C21—C20	−177.7 (4)
N2—C10—C11—C7	−176.0 (3)	C19—C20—C21—C12	−0.8 (7)
N1—C10—C11—C7	5.5 (6)	C7—C11—C22—N3	−68 (11)
N2—C10—C11—C22	4.7 (5)	C10—C11—C22—N3	111 (11)
N1—C10—C11—C22	−173.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.34	3.180 (4)	165
N2—H2B···N3ⁱⁱ	0.86	2.34	3.138 (4)	154

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅N₃
M_r	321.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	11.799 (2), 17.284 (3), 17.492 (4)
β (°)	98.26 (3)
V (Å³)	3530.2 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.979, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	3367, 3240, 1717
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.180, 1.01
No. of reflections	3240
No. of parameters	208
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), 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	0.86	2.34	3.180 (4)	165
N2—H2B···N3ⁱⁱ	0.86	2.34	3.138 (4)	154

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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