2-Amino-4-(2-fluoro­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbonitrile

Wang, W.; Tang, S.; Guo, C.; Luan, C.; Du, R.

doi:10.1107/S1600536810050695

organic compounds

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Volume 67| Part 1| January 2011| Page o96

https://doi.org/10.1107/S1600536810050695

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2-Amino-4-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile

Wei Wang,^a Shi-gui Tang,^b Cheng Guo,^c ^* 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, ^bDepartment of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^cCollege of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 19 November 2010; accepted 3 December 2010; online 11 December 2010)

In the title compound, C₂₀H₁₄FN₃, the F atom of the fluoro-substituted benzene ring in the 4-position of the 5,6-dihydrobenzo[h]quinoline system is disordered over two positions (0.80 and 0.20 occupancy). The dihedral angle between the pyridine and fluorobenzene rings is 73.2 (2) Å. The crystal structure is established by intermolecular N—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For use of the title compound as an intermediate, see Shi et al. (2005 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₄FN₃
M_r = 315.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9690 (14) Å
b = 12.716 (3) Å
c = 17.379 (4) Å
V = 1540.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1998 ) T_min = 0.973, T_max = 0.982
1641 measured reflections
1641 independent reflections
1231 reflections with I > 2σ(I)
R_int = 0.0315
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.161
S = 1.02
1641 reflections
226 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3ⁱ	0.86	2.45	3.215 (5)	150
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810050695/im2252sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050695/im2252Isup2.hkl

checkCIF report

Comment top

The title compound, C₂₀H₁₄F₁N₃, (I), is an important intermediate in the preparation of heterocyclic compounds (Shi et al., 2005). Thus, it's crystal structure is reported herein.

The fundamental buliding unit of I is composed of one fluorine substituted benzene ring attached to a 5,6-dihydrobenzo[h]quinoline ring in 4-position. In addition, there is an amino group in 2-position and a nitrile function in 3-position (Fig 1). The o-fluoro-phenyl group is disordered over two positions. Bond lengths and angles of the compound are within normal ranges (Allen et al., 1987). The crystal structure of the title compound is established by intermolecular N—H···N hydrogen bonds forming a three dimensional network (Fig 2).

Related literature top

For use of the title compound as an intermediate, see Shi et al. (2005). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared under microwave irradiation, an environmentally friendly method. 2 mmol of 2-fluorobenzaldehyde, 2 mmol of malononitrile, 16 mmol of ammonium acetate and 2 mmol of 1,2,3,4-tetrahydronaphthalen-1-one were dissolved in 3 mL absolute ethanol. The reaction mixture was stirred at 90°C additionally irradiating the mixture with microwaves (400 W, 6 h). After cooling down to room temperature pure (I) was obtained directly from the solution. Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and slowly evaporating the solvent at the room temperature for about 7 days.

Structure description top

The title compound, C₂₀H₁₄F₁N₃, (I), is an important intermediate in the preparation of heterocyclic compounds (Shi et al., 2005). Thus, it's crystal structure is reported herein.

For use of the title compound as an intermediate, see Shi et al. (2005). For standard bond lengths, see: Allen et al. (1987).

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. Molecular structure of (I), with the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. Packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-Amino-4-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile top

Crystal data top

C₂₀H₁₄FN₃	D_x = 1.360 Mg m⁻³
M_r = 315.34	Melting point: 438.15 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.9690 (14) Å	θ = 9–13°
b = 12.716 (3) Å	µ = 0.09 mm⁻¹
c = 17.379 (4) Å	T = 293 K
V = 1540.1 (5) Å³	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 656

Data collection top

Enraf–Nonius CAD-4 diffractometer	1231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1998)	k = 0→15
T_min = 0.973, T_max = 0.982	l = 0→20
1641 measured reflections	3 standard reflections every 200 reflections
1641 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.109P)²] where P = (F_o² + 2F_c²)/3
1641 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.19 e Å⁻³
12 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₀H₁₄FN₃	V = 1540.1 (5) Å³
M_r = 315.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9690 (14) Å	µ = 0.09 mm⁻¹
b = 12.716 (3) Å	T = 293 K
c = 17.379 (4) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1231 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1998)	R_int = 0.032
T_min = 0.973, T_max = 0.982	3 standard reflections every 200 reflections
1641 measured reflections	intensity decay: 1%
1641 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	12 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
1641 reflections	Δρ_min = −0.17 e Å⁻³
226 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	Occ. (<1)
C1	0.9531 (6)	0.0831 (3)	0.49848 (19)	0.0426 (9)
N1	0.9958 (5)	0.2550 (2)	0.55568 (16)	0.0401 (8)
N2	1.0177 (6)	0.2774 (2)	0.68616 (17)	0.0522 (9)
H2A	1.0349	0.3435	0.6784	0.063*
H2B	1.0166	0.2530	0.7323	0.063*
N3	0.9601 (7)	0.0234 (3)	0.77208 (18)	0.0676 (12)
C2	0.9338 (9)	0.0206 (3)	0.4259 (2)	0.0649 (13)
H2C	0.8013	0.0217	0.4089	0.078*
H2D	0.9695	−0.0519	0.4356	0.078*
C3	1.0620 (9)	0.0662 (3)	0.3634 (2)	0.0734 (16)
H3A	1.1955	0.0561	0.3773	0.088*
H3B	1.0389	0.0294	0.3154	0.088*
C4	1.0233 (7)	0.1807 (3)	0.3527 (2)	0.0518 (11)
C5	1.0325 (8)	0.2273 (3)	0.2808 (2)	0.0642 (13)
H5A	1.0595	0.1862	0.2378	0.077*
C6	1.0010 (7)	0.3334 (3)	0.2722 (2)	0.0590 (11)
H6A	1.0047	0.3636	0.2235	0.071*
C7	0.9642 (7)	0.3947 (3)	0.3356 (2)	0.0557 (11)
H7A	0.9440	0.4666	0.3299	0.067*
C8	0.9571 (6)	0.3495 (3)	0.4076 (2)	0.0449 (9)
H8A	0.9324	0.3914	0.4503	0.054*
C9	0.9862 (6)	0.2430 (3)	0.41728 (19)	0.0407 (9)
C10	0.9766 (5)	0.1922 (3)	0.49386 (19)	0.0390 (8)
C11	0.9925 (6)	0.2118 (3)	0.62584 (19)	0.0382 (8)
C12	0.9689 (6)	0.1031 (3)	0.63549 (19)	0.0382 (8)
C13	0.9470 (6)	0.0380 (3)	0.5712 (2)	0.0398 (9)
C14	0.9174 (6)	−0.0773 (3)	0.5810 (2)	0.0446 (10)
C15	0.7404 (8)	−0.1240 (4)	0.5688 (3)	0.0615 (12)
H15	0.6394	−0.0781	0.5591	0.074*	0.80
C16	0.7092 (9)	−0.2297 (4)	0.5788 (3)	0.0739 (16)
H16A	0.5881	−0.2583	0.5705	0.089*
C17	0.8575 (10)	−0.2917 (4)	0.6009 (2)	0.0757 (17)
H17A	0.8376	−0.3633	0.6084	0.091*
C18	1.0355 (9)	−0.2501 (3)	0.6122 (2)	0.0641 (14)
H18A	1.1378	−0.2934	0.6255	0.077*
C19	1.0625 (8)	−0.1438 (3)	0.6038 (2)	0.0557 (12)
H19	1.1833	−0.1153	0.6130	0.067*	0.20
C20	0.9635 (7)	0.0585 (3)	0.7116 (2)	0.0479 (10)
F1	0.610 (2)	−0.0743 (11)	0.5394 (10)	0.083 (4)	0.21
F1'	1.2344 (6)	−0.1074 (3)	0.6101 (3)	0.0917 (13)	0.80

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (2)	0.0301 (17)	0.0443 (18)	−0.0026 (18)	−0.0015 (19)	−0.0052 (15)
N1	0.0467 (19)	0.0329 (14)	0.0408 (15)	−0.0002 (15)	0.0006 (15)	−0.0022 (13)
N2	0.077 (3)	0.0393 (16)	0.0398 (16)	−0.0077 (19)	0.0009 (17)	−0.0049 (13)
N3	0.115 (3)	0.0460 (18)	0.0422 (18)	−0.006 (2)	−0.004 (2)	0.0062 (15)
C2	0.115 (4)	0.039 (2)	0.0409 (19)	−0.004 (3)	−0.002 (2)	0.0032 (17)
C3	0.126 (5)	0.043 (2)	0.052 (2)	0.006 (3)	0.014 (3)	−0.003 (2)
C4	0.076 (3)	0.0390 (19)	0.0403 (19)	0.002 (2)	0.004 (2)	0.0021 (16)
C5	0.099 (4)	0.052 (2)	0.041 (2)	−0.005 (3)	0.008 (3)	−0.0039 (19)
C6	0.076 (3)	0.052 (2)	0.050 (2)	−0.003 (3)	−0.001 (2)	0.0174 (19)
C7	0.064 (3)	0.043 (2)	0.061 (2)	0.000 (2)	0.003 (2)	0.0166 (19)
C8	0.049 (2)	0.0356 (19)	0.050 (2)	0.0020 (19)	0.003 (2)	0.0013 (16)
C9	0.045 (2)	0.0386 (18)	0.0385 (18)	0.0020 (19)	0.0000 (17)	0.0019 (15)
C10	0.044 (2)	0.0339 (18)	0.0386 (17)	−0.0025 (18)	0.0015 (18)	0.0023 (15)
C11	0.042 (2)	0.0331 (16)	0.0397 (17)	−0.0027 (17)	0.0033 (17)	−0.0017 (15)
C12	0.041 (2)	0.0346 (17)	0.0391 (17)	−0.0020 (17)	0.0015 (18)	0.0003 (15)
C13	0.050 (2)	0.0295 (17)	0.0399 (17)	−0.0002 (18)	−0.0013 (19)	−0.0017 (14)
C14	0.066 (3)	0.0326 (19)	0.0353 (19)	−0.005 (2)	−0.0021 (19)	0.0018 (16)
C15	0.076 (3)	0.047 (2)	0.061 (3)	−0.007 (2)	−0.010 (3)	0.003 (2)
C16	0.100 (4)	0.052 (3)	0.069 (3)	−0.030 (3)	−0.013 (3)	0.013 (2)
C17	0.135 (5)	0.040 (2)	0.052 (3)	−0.022 (3)	−0.003 (3)	0.011 (2)
C18	0.102 (4)	0.038 (2)	0.052 (2)	0.017 (3)	−0.001 (3)	0.0077 (19)
C19	0.079 (3)	0.034 (2)	0.054 (2)	0.004 (2)	0.000 (2)	0.0033 (18)
C20	0.067 (3)	0.0336 (17)	0.043 (2)	−0.002 (2)	−0.004 (2)	−0.0037 (17)
F1	0.062 (8)	0.058 (8)	0.130 (12)	−0.007 (7)	−0.034 (8)	−0.002 (8)
F1'	0.071 (2)	0.056 (2)	0.148 (4)	0.002 (2)	−0.024 (2)	0.010 (2)

Geometric parameters (Å, º) top

C1—C13	1.389 (5)	C7—C8	1.378 (5)
C1—C10	1.399 (5)	C7—H7A	0.9300
C1—C2	1.496 (5)	C8—C9	1.380 (5)
N1—C11	1.338 (4)	C8—H8A	0.9300
N1—C10	1.345 (4)	C9—C10	1.481 (4)
N2—C11	1.351 (4)	C11—C12	1.401 (5)
N2—H2A	0.8600	C12—C13	1.398 (5)
N2—H2B	0.8600	C12—C20	1.439 (5)
N3—C20	1.143 (4)	C13—C14	1.490 (5)
C2—C3	1.522 (7)	C14—C19	1.376 (6)
C2—H2C	0.9700	C14—C15	1.385 (6)
C2—H2D	0.9700	C15—F1	1.217 (14)
C3—C4	1.492 (6)	C15—C16	1.373 (6)
C3—H3A	0.9700	C15—H15	0.9300
C3—H3B	0.9700	C16—C17	1.356 (8)
C4—C5	1.386 (5)	C16—H16A	0.9300
C4—C9	1.397 (5)	C17—C18	1.362 (8)
C5—C6	1.374 (6)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.373 (6)
C6—C7	1.374 (6)	C18—H18A	0.9300
C6—H6A	0.9300	C19—F1'	1.289 (6)

C13—C1—C10	117.7 (3)	C4—C9—C10	118.9 (3)
C13—C1—C2	123.0 (3)	N1—C10—C1	123.6 (3)
C10—C1—C2	119.2 (3)	N1—C10—C9	117.1 (3)
C11—N1—C10	118.9 (3)	C1—C10—C9	119.3 (3)
C11—N2—H2A	120.0	N1—C11—N2	116.8 (3)
C11—N2—H2B	120.0	N1—C11—C12	121.1 (3)
H2A—N2—H2B	120.0	N2—C11—C12	122.1 (3)
C1—C2—C3	110.3 (4)	C13—C12—C11	120.1 (3)
C1—C2—H2C	109.6	C13—C12—C20	119.8 (3)
C3—C2—H2C	109.6	C11—C12—C20	120.1 (3)
C1—C2—H2D	109.6	C1—C13—C12	118.6 (3)
C3—C2—H2D	109.6	C1—C13—C14	120.9 (3)
H2C—C2—H2D	108.1	C12—C13—C14	120.5 (3)
C4—C3—C2	110.7 (4)	C19—C14—C15	115.8 (4)
C4—C3—H3A	109.5	C19—C14—C13	122.4 (4)
C2—C3—H3A	109.5	C15—C14—C13	121.8 (4)
C4—C3—H3B	109.5	F1—C15—C16	116.3 (8)
C2—C3—H3B	109.5	F1—C15—C14	120.3 (8)
H3A—C3—H3B	108.1	C16—C15—C14	122.8 (5)
C5—C4—C9	119.4 (3)	C16—C15—H15	121.2
C5—C4—C3	121.4 (3)	C14—C15—H15	115.6
C9—C4—C3	119.1 (3)	C17—C16—C15	119.0 (6)
C6—C5—C4	120.6 (4)	C17—C16—H16A	120.5
C6—C5—H5A	119.8	C15—C16—H16A	120.5
C4—C5—H5A	119.5	C16—C17—C18	120.6 (4)
C5—C6—C7	120.1 (3)	C16—C17—H17A	119.7
C5—C6—H6A	120.0	C18—C17—H17A	119.7
C7—C6—H6A	120.0	C17—C18—C19	119.4 (5)
C6—C7—C8	119.8 (3)	C17—C18—H18A	120.3
C6—C7—H7A	120.1	C19—C18—H18A	120.3
C8—C7—H7A	120.1	F1'—C19—C18	118.1 (5)
C7—C8—C9	121.0 (3)	F1'—C19—C14	119.2 (4)
C7—C8—H8A	119.5	C18—C19—C14	122.3 (5)
C9—C8—H8A	119.5	C18—C19—H19	119.3
C8—C9—C4	119.1 (3)	C14—C19—H19	118.3
C8—C9—C10	122.1 (3)	N3—C20—C12	179.6 (5)

C13—C1—C2—C3	−144.0 (4)	N2—C11—C12—C13	−178.8 (4)
C10—C1—C2—C3	36.6 (6)	N1—C11—C12—C20	−179.3 (4)
C1—C2—C3—C4	−53.6 (6)	N2—C11—C12—C20	2.5 (7)
C2—C3—C4—C5	−144.6 (5)	C10—C1—C13—C12	−1.5 (6)
C2—C3—C4—C9	38.6 (7)	C2—C1—C13—C12	179.2 (4)
C9—C4—C5—C6	−1.5 (8)	C10—C1—C13—C14	178.5 (4)
C3—C4—C5—C6	−178.4 (5)	C2—C1—C13—C14	−0.9 (6)
C4—C5—C6—C7	1.4 (8)	C11—C12—C13—C1	1.3 (6)
C5—C6—C7—C8	−0.6 (8)	C20—C12—C13—C1	−179.9 (4)
C6—C7—C8—C9	−0.1 (7)	C11—C12—C13—C14	−178.6 (4)
C7—C8—C9—C4	0.0 (7)	C20—C12—C13—C14	0.2 (6)
C7—C8—C9—C10	−179.1 (4)	C1—C13—C14—C19	107.6 (5)
C5—C4—C9—C8	0.8 (7)	C12—C13—C14—C19	−72.5 (5)
C3—C4—C9—C8	177.7 (5)	C1—C13—C14—C15	−73.7 (5)
C5—C4—C9—C10	180.0 (4)	C12—C13—C14—C15	106.3 (5)
C3—C4—C9—C10	−3.1 (7)	C19—C14—C15—F1	−170.7 (10)
C11—N1—C10—C1	0.0 (6)	C13—C14—C15—F1	10.5 (12)
C11—N1—C10—C9	−178.4 (3)	C19—C14—C15—C16	0.0 (7)
C13—C1—C10—N1	0.9 (6)	C13—C14—C15—C16	−178.8 (4)
C2—C1—C10—N1	−179.8 (4)	F1—C15—C16—C17	170.6 (10)
C13—C1—C10—C9	179.3 (3)	C14—C15—C16—C17	−0.5 (8)
C2—C1—C10—C9	−1.4 (6)	C15—C16—C17—C18	−0.8 (8)
C8—C9—C10—N1	−19.4 (6)	C16—C17—C18—C19	2.4 (8)
C4—C9—C10—N1	161.5 (4)	C17—C18—C19—F1'	−175.7 (4)
C8—C9—C10—C1	162.1 (4)	C17—C18—C19—C14	−2.9 (7)
C4—C9—C10—C1	−17.0 (6)	C15—C14—C19—F1'	174.4 (4)
C10—N1—C11—N2	178.2 (3)	C13—C14—C19—F1'	−6.8 (6)
C10—N1—C11—C12	−0.2 (6)	C15—C14—C19—C18	1.7 (6)
N1—C11—C12—C13	−0.5 (6)	C13—C14—C19—C18	−179.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3ⁱ	0.86	2.45	3.215 (5)	150

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄FN₃
M_r	315.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.9690 (14), 12.716 (3), 17.379 (4)
V (Å³)	1540.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1998)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	1641, 1641, 1231
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.161, 1.02
No. of reflections	1641
No. of parameters	226
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

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···N3ⁱ	0.86	2.45	3.215 (5)	150

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

Acknowledgements

We gratefully acknowledge the Analysis Center of Nanjing University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. 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
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