3-(2-Amino­ethyl)-2-(4-fluoroanilino)­quinazolin-4(3H)-one

Yang, X.-H.; Wu, M.-H.

doi:10.1107/S1600536808035058

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2240

doi:10.1107/S1600536808035058

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3-(2-Aminoethyl)-2-(4-fluoroanilino)quinazolin-4(3H)-one

Xu-Hong Yang ^a and Ming-Hu Wu ^a ^*

^aFaculty of Chemistry and Life Science, Xianning University, Xianning 437100, People's Republic of China
^*Correspondence e-mail: minghuwu@hotmail.com

(Received 20 October 2008; accepted 28 October 2008; online 31 October 2008)

In the title molecule, C₁₆H₁₅FN₄O, the dihedral angle between the fluoro-substituted benzene ring and the pyrimidinone ring is 52.34 (7)°, while the dihedral angle between the fused benzene ring and the pyrimidinone ring is 3.30 (6)°. An intramolecular N—H⋯N hydrogen bond may, in part, influence the conformation of the molecule. In the crystal structure, intermolecular N—H⋯N hydrogen bonds and weak C—H⋯π(arene) interactions link pairs of molecules into centrosymmetric dimers.

Related literature

For the biological properties of quinazolinones and their derivatives, see: Armarego (1963 ); Witt & Bergman (2003 ). For details of our ongoing heterocyclic synthesis and drug discovery project, see: Yang et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₅FN₄O
M_r = 298.32
Triclinic, $[P \overline 1]$
a = 8.2836 (8) Å
b = 9.3103 (10) Å
c = 9.4952 (10) Å
α = 89.36 (1)°
β = 80.537 (10)°
γ = 77.163 (10)°
V = 704.03 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 292 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.970, T_max = 0.990
4078 measured reflections
2726 independent reflections
2318 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.05
2726 reflections
209 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4	0.908 (17)	1.925 (17)	2.8049 (17)	162.8 (14)
N4—H4A⋯N2ⁱ	0.889 (16)	2.323 (16)	3.1321 (18)	151.4 (13)
C3—H3⋯Cgⁱ	0.93	2.77 (1)	3.4741 (15)	132 (1)
Symmetry code: (i) -x, -y+1, -z+1. Cg is the centroid of atoms N2/C7/N3/C14/C13/C8.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035058/lh2717sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035058/lh2717Isup2.hkl

checkCIF report

Comment top

Quinazolinones and their derivatives are now known to have a wide range of useful biological properties, such as hypnotic, sedative, analgesic, anti-convulsant, anti-tussive, anti-bacterial, anti-diabetic, anti-inflammatory and anti-tumor (Armarego, 1963; Witt & Bergman, 2003). In connection with our ongoing heterocyclic synthesis and drug discovery project (Yang et al., 2008), we have focused our research on the synthesis of quinazolinones and pyrazolo pyrimidinones. Herein, the title compound was synthesized and its crystal structure was determined.

In the molecule (Fig. 1), the dihedral angle between the fluorophenyl and pyrimidinone ring is 52.34 (7)°, and the dihedral angle between the fused benzene ring and pyrimidinone ring is 3.30 (6)°. The torsion angles of N2–C7–N1–C4 and N3–C7–N1–C4 are -4.7 (2) and 176.42 (11)°, respectively.

An intramolecular N-H···N hydrogen bond may, in part, influence the conformation of the molecule. In the crystal structure, intermolecular N-H···N hydrogen bonds and weak C–H···π(arene) interactions link pairs of molecules into centrosymmetric dimers (see Table 1 and Fig. 2).

Related literature top

For the biological properties of quinazolinones and their derivatives, see: Armarego (1963); Witt & Bergman (2003). For our ongoing heterocyclic synthesis and drugdiscovery project, see: Yang et al. (2008). Cg is the centroid of atoms N2/C7/N3/C14/C13/C8.

Experimental top

To a solution of 2-ethoxycarbonyliminophosphorane (1.27 g, 3 mmol) in 10 ml anhydrous THF, 4-chlorophenylisocyanate (0.46 g, 3 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter the above resulting solution was added dropwise to a solution of ethylenediamine (0.18 g, 3 mmol) in 5 ml anhydrous THF. After that, the reaction mixture was stirred overnight, the reaction mixture was cooled and the reaction product was recrystallized from CH₃OH—CH₂Cl₂ to give colorless crystals of the title compound in yield 85%, which were suitable for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title molecule with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound showing hydrogen bonds as dashed lines.

3-(2-Aminoethyl)-2-(4-fluoroanilino)quinazolin-4(3H)-one top

Crystal data top

C₁₆H₁₅FN₄O	Z = 2
M_r = 298.32	F(000) = 312
Triclinic, P1	D_x = 1.407 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2836 (8) Å	Cell parameters from 2276 reflections
b = 9.3103 (10) Å	θ = 2.2–28.9°
c = 9.4952 (10) Å	µ = 0.10 mm⁻¹
α = 89.36 (1)°	T = 292 K
β = 80.537 (10)°	Block, colourless
γ = 77.163 (10)°	0.20 × 0.10 × 0.10 mm
V = 704.03 (13) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2726 independent reflections
Radiation source: fine-focus sealed tube	2318 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
T_min = 0.970, T_max = 0.990	k = −11→11
4078 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0572P)² + 0.1074P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2726 reflections	Δρ_max = 0.16 e Å⁻³
209 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (5)

Crystal data top

C₁₆H₁₅FN₄O	γ = 77.163 (10)°
M_r = 298.32	V = 704.03 (13) Å³
Triclinic, P1	Z = 2
a = 8.2836 (8) Å	Mo Kα radiation
b = 9.3103 (10) Å	µ = 0.10 mm⁻¹
c = 9.4952 (10) Å	T = 292 K
α = 89.36 (1)°	0.20 × 0.10 × 0.10 mm
β = 80.537 (10)°

Data collection top

Bruker SMART APEX CCD diffractometer	2726 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2318 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.990	R_int = 0.012
4078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.16 e Å⁻³
2726 reflections	Δρ_min = −0.15 e Å⁻³
209 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	0.26560 (18)	0.91647 (15)	0.45066 (18)	0.0596 (4)
C2	0.1522 (2)	0.87525 (15)	0.37986 (16)	0.0589 (4)
H2	0.1451	0.9031	0.2863	0.071*
C3	0.04783 (17)	0.79107 (14)	0.45047 (14)	0.0503 (3)
H3	−0.0308	0.7624	0.4040	0.060*
C4	0.05872 (15)	0.74874 (13)	0.58961 (14)	0.0449 (3)
C5	0.17665 (17)	0.79171 (15)	0.65820 (16)	0.0536 (3)
H5	0.1860	0.7632	0.7512	0.064*
C6	0.28049 (18)	0.87722 (16)	0.58782 (18)	0.0604 (4)
H6	0.3590	0.9074	0.6333	0.073*
C7	−0.02621 (15)	0.55612 (14)	0.74400 (13)	0.0424 (3)
C8	0.15458 (16)	0.37171 (14)	0.83809 (13)	0.0444 (3)
C9	0.31903 (18)	0.30166 (17)	0.85105 (16)	0.0573 (4)
H9	0.4075	0.3440	0.8121	0.069*
C10	0.3511 (2)	0.17169 (18)	0.92037 (17)	0.0670 (4)
H10	0.4613	0.1260	0.9272	0.080*
C11	0.2208 (2)	0.10669 (18)	0.98092 (18)	0.0690 (4)
H11	0.2438	0.0177	1.0271	0.083*
C12	0.0591 (2)	0.17479 (17)	0.97182 (16)	0.0587 (4)
H12	−0.0284	0.1326	1.0136	0.070*
C13	0.02374 (16)	0.30663 (14)	0.90063 (13)	0.0459 (3)
C14	−0.14830 (17)	0.37725 (15)	0.88772 (14)	0.0479 (3)
C15	−0.33989 (16)	0.58408 (16)	0.79762 (15)	0.0523 (3)
H15A	−0.3462	0.6893	0.8010	0.063*
H15B	−0.4153	0.5613	0.8799	0.063*
C16	−0.39955 (16)	0.54589 (16)	0.66308 (16)	0.0555 (4)
H16A	−0.3651	0.4403	0.6447	0.067*
H16B	−0.5212	0.5731	0.6772	0.067*
F1	0.36536 (13)	1.00298 (12)	0.38271 (13)	0.0901 (4)
N1	−0.06114 (14)	0.67357 (13)	0.65917 (13)	0.0496 (3)
H1	−0.151 (2)	0.6763 (17)	0.6150 (16)	0.060*
N2	0.12716 (13)	0.49763 (12)	0.75954 (11)	0.0459 (3)
H4A	−0.2947 (19)	0.5633 (17)	0.4621 (17)	0.055*
H4B	−0.411 (2)	0.6934 (17)	0.5178 (15)	0.055*
N3	−0.16619 (13)	0.50507 (12)	0.80814 (11)	0.0448 (3)
N4	−0.33145 (16)	0.62199 (16)	0.53930 (14)	0.0590 (3)
O1	−0.27139 (13)	0.33072 (12)	0.94041 (12)	0.0654 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0477 (8)	0.0456 (7)	0.0809 (10)	−0.0143 (6)	0.0073 (7)	0.0107 (7)
C2	0.0648 (9)	0.0473 (7)	0.0579 (8)	−0.0098 (7)	0.0053 (7)	0.0068 (6)
C3	0.0511 (8)	0.0419 (7)	0.0559 (8)	−0.0093 (6)	−0.0050 (6)	0.0015 (6)
C4	0.0364 (6)	0.0387 (6)	0.0566 (7)	−0.0069 (5)	−0.0015 (5)	0.0050 (5)
C5	0.0434 (7)	0.0536 (8)	0.0647 (8)	−0.0136 (6)	−0.0081 (6)	0.0092 (6)
C6	0.0413 (7)	0.0536 (8)	0.0880 (11)	−0.0148 (6)	−0.0097 (7)	0.0079 (7)
C7	0.0381 (7)	0.0470 (7)	0.0433 (6)	−0.0146 (5)	−0.0034 (5)	0.0022 (5)
C8	0.0434 (7)	0.0514 (7)	0.0409 (6)	−0.0159 (6)	−0.0071 (5)	0.0053 (5)
C9	0.0435 (8)	0.0697 (9)	0.0620 (8)	−0.0185 (7)	−0.0115 (6)	0.0179 (7)
C10	0.0518 (9)	0.0761 (10)	0.0731 (10)	−0.0097 (8)	−0.0183 (7)	0.0242 (8)
C11	0.0698 (10)	0.0655 (10)	0.0738 (10)	−0.0170 (8)	−0.0177 (8)	0.0287 (8)
C12	0.0584 (9)	0.0619 (9)	0.0592 (8)	−0.0235 (7)	−0.0063 (7)	0.0159 (7)
C13	0.0462 (7)	0.0517 (7)	0.0421 (6)	−0.0177 (6)	−0.0050 (5)	0.0039 (5)
C14	0.0447 (7)	0.0547 (7)	0.0460 (7)	−0.0201 (6)	−0.0007 (5)	0.0026 (6)
C15	0.0348 (7)	0.0582 (8)	0.0595 (8)	−0.0086 (6)	0.0028 (6)	0.0021 (6)
C16	0.0334 (7)	0.0580 (8)	0.0755 (9)	−0.0106 (6)	−0.0095 (6)	0.0043 (7)
F1	0.0763 (7)	0.0820 (7)	0.1149 (9)	−0.0407 (6)	0.0059 (6)	0.0289 (6)
N1	0.0379 (6)	0.0532 (7)	0.0607 (7)	−0.0154 (5)	−0.0099 (5)	0.0125 (5)
N2	0.0382 (6)	0.0514 (6)	0.0498 (6)	−0.0157 (5)	−0.0054 (4)	0.0094 (5)
N3	0.0353 (6)	0.0517 (6)	0.0476 (6)	−0.0142 (5)	−0.0013 (4)	0.0029 (5)
N4	0.0429 (7)	0.0710 (8)	0.0621 (8)	−0.0101 (6)	−0.0096 (6)	0.0019 (6)
O1	0.0476 (6)	0.0723 (7)	0.0788 (7)	−0.0275 (5)	0.0011 (5)	0.0166 (5)

Geometric parameters (Å, º) top

C1—C2	1.362 (2)	C10—C11	1.392 (2)
C1—F1	1.3626 (16)	C10—H10	0.9300
C1—C6	1.366 (2)	C11—C12	1.365 (2)
C2—C3	1.3819 (19)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3914 (19)
C3—C4	1.3859 (19)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.4551 (19)
C4—C5	1.388 (2)	C14—O1	1.2254 (15)
C4—N1	1.4123 (16)	C14—N3	1.3955 (17)
C5—C6	1.3870 (19)	C15—N3	1.4821 (16)
C5—H5	0.9300	C15—C16	1.516 (2)
C6—H6	0.9300	C15—H15A	0.9700
C7—N2	1.2980 (16)	C15—H15B	0.9700
C7—N1	1.3581 (17)	C16—N4	1.464 (2)
C7—N3	1.3956 (15)	C16—H16A	0.9700
C8—N2	1.3785 (16)	C16—H16B	0.9700
C8—C9	1.3981 (19)	N1—H1	0.908 (17)
C8—C13	1.4023 (18)	N4—H4A	0.889 (16)
C9—C10	1.366 (2)	N4—H4B	0.872 (16)
C9—H9	0.9300

C2—C1—F1	118.49 (14)	C10—C11—H11	120.3
C2—C1—C6	122.61 (13)	C11—C12—C13	120.67 (14)
F1—C1—C6	118.88 (15)	C11—C12—H12	119.7
C1—C2—C3	118.37 (14)	C13—C12—H12	119.7
C1—C2—H2	120.8	C12—C13—C8	120.13 (13)
C3—C2—H2	120.8	C12—C13—C14	120.69 (12)
C2—C3—C4	120.93 (13)	C8—C13—C14	119.18 (12)
C2—C3—H3	119.5	O1—C14—N3	120.70 (12)
C4—C3—H3	119.5	O1—C14—C13	124.22 (13)
C3—C4—C5	119.19 (12)	N3—C14—C13	115.08 (11)
C3—C4—N1	117.79 (12)	N3—C15—C16	113.90 (11)
C5—C4—N1	122.81 (12)	N3—C15—H15A	108.8
C6—C5—C4	119.92 (14)	C16—C15—H15A	108.8
C6—C5—H5	120.0	N3—C15—H15B	108.8
C4—C5—H5	120.0	C16—C15—H15B	108.8
C1—C6—C5	118.98 (14)	H15A—C15—H15B	107.7
C1—C6—H6	120.5	N4—C16—C15	111.68 (12)
C5—C6—H6	120.5	N4—C16—H16A	109.3
N2—C7—N1	120.96 (11)	C15—C16—H16A	109.3
N2—C7—N3	124.41 (11)	N4—C16—H16B	109.3
N1—C7—N3	114.62 (11)	C15—C16—H16B	109.3
N2—C8—C9	119.28 (12)	H16A—C16—H16B	107.9
N2—C8—C13	122.38 (12)	C7—N1—C4	124.69 (11)
C9—C8—C13	118.27 (12)	C7—N1—H1	114.5 (10)
C10—C9—C8	120.65 (14)	C4—N1—H1	115.2 (10)
C10—C9—H9	119.7	C7—N2—C8	117.77 (11)
C8—C9—H9	119.7	C14—N3—C7	121.02 (11)
C9—C10—C11	120.84 (14)	C14—N3—C15	116.82 (11)
C9—C10—H10	119.6	C7—N3—C15	122.16 (11)
C11—C10—H10	119.6	C16—N4—H4A	112.6 (10)
C12—C11—C10	119.42 (14)	C16—N4—H4B	109.1 (10)
C12—C11—H11	120.3	H4A—N4—H4B	106.8 (14)

F1—C1—C2—C3	−178.16 (12)	C8—C13—C14—O1	−178.72 (13)
C6—C1—C2—C3	0.4 (2)	C12—C13—C14—N3	−177.09 (12)
C1—C2—C3—C4	−0.4 (2)	C8—C13—C14—N3	1.78 (18)
C2—C3—C4—C5	−0.1 (2)	N3—C15—C16—N4	−78.30 (15)
C2—C3—C4—N1	174.74 (12)	N2—C7—N1—C4	−4.7 (2)
C3—C4—C5—C6	0.7 (2)	N3—C7—N1—C4	176.42 (11)
N1—C4—C5—C6	−173.93 (12)	C3—C4—N1—C7	138.77 (13)
C2—C1—C6—C5	0.2 (2)	C5—C4—N1—C7	−46.58 (19)
F1—C1—C6—C5	178.68 (12)	N1—C7—N2—C8	−174.97 (11)
C4—C5—C6—C1	−0.7 (2)	N3—C7—N2—C8	3.84 (19)
N2—C8—C9—C10	−175.78 (14)	C9—C8—N2—C7	176.85 (12)
C13—C8—C9—C10	1.3 (2)	C13—C8—N2—C7	−0.13 (19)
C8—C9—C10—C11	−0.6 (3)	O1—C14—N3—C7	−177.93 (12)
C9—C10—C11—C12	−0.6 (3)	C13—C14—N3—C7	1.58 (17)
C10—C11—C12—C13	1.2 (3)	O1—C14—N3—C15	3.07 (19)
C11—C12—C13—C8	−0.5 (2)	C13—C14—N3—C15	−177.42 (11)
C11—C12—C13—C14	178.40 (13)	N2—C7—N3—C14	−4.69 (19)
N2—C8—C13—C12	176.23 (12)	N1—C7—N3—C14	174.18 (11)
C9—C8—C13—C12	−0.8 (2)	N2—C7—N3—C15	174.25 (12)
N2—C8—C13—C14	−2.65 (19)	N1—C7—N3—C15	−6.87 (17)
C9—C8—C13—C14	−179.65 (12)	C16—C15—N3—C14	−96.27 (14)
C12—C13—C14—O1	2.4 (2)	C16—C15—N3—C7	84.75 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.908 (17)	1.925 (17)	2.8049 (17)	162.8 (14)
N4—H4A···N2ⁱ	0.889 (16)	2.323 (16)	3.1321 (18)	151.4 (13)
C3—H3···Cgⁱ	0.93	2.77 (1)	3.4741 (15)	132 (1)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅FN₄O
M_r	298.32
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.2836 (8), 9.3103 (10), 9.4952 (10)
α, β, γ (°)	89.36 (1), 80.537 (10), 77.163 (10)
V (Å³)	704.03 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	4078, 2726, 2318
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.05
No. of reflections	2726
No. of parameters	209
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.908 (17)	1.925 (17)	2.8049 (17)	162.8 (14)
N4—H4A···N2ⁱ	0.889 (16)	2.323 (16)	3.1321 (18)	151.4 (13)
C3—H3···Cgⁱ	0.93000	2.769 (12)	3.4741 (15)	132.0 (10)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

We gratefully acknowledge financial support of this work by the the Natural Science Foundation of Hubei Province (grant No. 2006ABA334).

References

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