5-(4-Fluoro­phen­yl)-2,6-dioxo-2,3,6,7,8,9-hexa­hydro-1H,5H-imidazo[1,2-a]quinoline-4-carbonitrile

Zhuang, Q.; Li, C.; Shao, Q.; Jiang, B.

doi:10.1107/S1600536807042110

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5-(4-Fluorophenyl)-2,6-dioxo-2,3,6,7,8,9-hexahydro-1H,5H-imidazo[1,2-a]quinoline-4-carbonitrile

Q. Zhuang, C. Li, Q. Shao and B. Jiang

In the molecule of the title compound, C₁₈H₁₄FN₃O₂, the imidazole and dihydropyridine rings are nearly coplanar with a dihedral angle of 2.46 (3)°, while the cyclohexene ring has an envelope conformation. The benzene ring is oriented with respect to the coplanar ring system at a dihedral angle of 81.45 (2)°. In the crystal structure, intermolecular N—H

N hydrogen bonds link the molecules into dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042110/hk2320sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042110/hk2320Isup2.hkl Contains datablock I

CCDC reference: 664192

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.112
Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C12     ..       5.05 su
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C12    ...       1.42 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         43
            C9  -C8  -C12 -N3    153.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         44
            C7  -C8  -C12 -N3    -23.00  7.00   1.555   1.555   1.555   1.555

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

1,4-Dihydropyridines (1,4-DHPs) are well known compounds because of their pharmacological profiles as calcium channel modulators (Stout & Meyers, 1982). With a 1,4-DHPs parent nucleus, imidazo[1,2-a]quinoline belongs to a class of compounds which are special not only because of their interesting chemical and physical properties, but also due to their immense utility in the pharmaceutical industries. The discovery of imidazo[1,2-a]quinoline including imidazo[1,2-a]- pyridine moiety, as new potential pharmacological molecules, may be of great significance. It is well established that the chemical modifications on the imidazo[1,2-a]pyridine skeletons may bring remarkable changes of biological activity (Gueiffier et al., 1996; Elhakmaoui et al., 1994). We report herein the crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).

Ring A (C1—C6) is not planar, having total puckering amplitude, Q_T, of 0.488 (3) Å, [φ = -64.74 (3)°, θ = 117.65 (3)°] (Cremer & Pople, 1975), and adopts an envelope conformation with atom C3 displaced by -0.663 (3) Å from the plane of the other ring atoms. Rings B (N1/C1/C6—C9), C (N1/N2/C9—C11) and D (C13—C18) are, of course, planar and rings B and D are also nearly coplanar with a dihedral angle of 2.46 (3)°. Ring D is oriented with respect to the coplanar ring system at a dihedral angle of 81.45 (2)°.

In the crystal structure, the intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into dimers (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Stout & Meyers (1982); Gueiffier et al. (1996); Elhakmaoui et al. (1994). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I), was prepared by the reaction of 4-fluorobenzaldehyde (124 mg, 1 mmol), 2-(3-oxocyclohex-1-enylamino)acetic acid (169 mg, 1 mmol) with malononitrile (66 mg, 1 mmol) in solvent of ethylene glycol (2.0 ml) at 393 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 5 min. Single crystals suitable for X-ray analysis were obtained from an ethanol solution (95%) by slow evaporation (yield; 284 mg, 88%, m.p. 559–560 K).

Structure description top

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987).

In the crystal structure, the intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into dimers (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

5-(4-Fluorophenyl)-2,6-dioxo-2,3,6,7,8,9-hexahydro-1H,5H- imidazo[1,2-a]quinoline-4-carbonitrile top

Crystal data top

C₁₈H₁₄FN₃O₂	F(000) = 672
M_r = 323.32	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 559–560 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.781 (3) Å	Cell parameters from 1113 reflections
b = 14.937 (4) Å	θ = 2.4–21.3°
c = 9.839 (3) Å	µ = 0.10 mm⁻¹
β = 106.270 (5)°	T = 298 K
V = 1521.0 (7) Å³	Block, colourless
Z = 4	0.36 × 0.33 × 0.19 mm

Data collection top

Bruker CCD area-detector diffractometer	2678 independent reflections
Radiation source: fine-focus sealed tube	1368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.964, T_max = 0.981	k = −17→17
7885 measured reflections	l = −11→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0328P)² + 0.3811P] where P = (F_o² + 2F_c²)/3
2678 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₄FN₃O₂	V = 1521.0 (7) Å³
M_r = 323.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.781 (3) Å	µ = 0.10 mm⁻¹
b = 14.937 (4) Å	T = 298 K
c = 9.839 (3) Å	0.36 × 0.33 × 0.19 mm
β = 106.270 (5)°

Data collection top

Bruker CCD area-detector diffractometer	2678 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1368 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.981	R_int = 0.058
7885 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
2678 reflections	Δρ_min = −0.17 e Å⁻³
217 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
F1	0.9987 (2)	−0.14960 (16)	0.7379 (2)	0.1056 (8)
N1	0.6362 (2)	0.12725 (14)	0.1016 (2)	0.0360 (6)
N2	0.7956 (2)	0.13795 (15)	0.0009 (2)	0.0395 (6)
H2	0.8621	0.1239	−0.0266	0.047*
N3	0.9607 (3)	−0.08486 (18)	0.0697 (3)	0.0617 (8)
O1	0.48004 (19)	−0.12894 (13)	0.2715 (2)	0.0531 (6)
O2	0.7643 (2)	0.28153 (14)	−0.0880 (2)	0.0619 (6)
C1	0.5553 (2)	0.08620 (19)	0.1683 (3)	0.0339 (7)
C2	0.4489 (3)	0.14201 (18)	0.1931 (3)	0.0414 (8)
H2A	0.3764	0.1426	0.1084	0.050*
H2B	0.4787	0.2031	0.2137	0.050*
C3	0.4061 (3)	0.10459 (19)	0.3161 (3)	0.0489 (8)
H3A	0.4749	0.1121	0.4033	0.059*
H3B	0.3312	0.1374	0.3251	0.059*
C4	0.3728 (3)	0.00648 (19)	0.2935 (3)	0.0464 (8)
H4A	0.3567	−0.0176	0.3785	0.056*
H4B	0.2940	0.0004	0.2169	0.056*
C5	0.4778 (3)	−0.0473 (2)	0.2589 (3)	0.0385 (7)
C6	0.5737 (3)	−0.00083 (18)	0.2071 (3)	0.0328 (7)
C7	0.6892 (3)	−0.05532 (17)	0.1965 (3)	0.0334 (7)
H7	0.6569	−0.1104	0.1445	0.040*
C8	0.7650 (3)	−0.00414 (18)	0.1131 (3)	0.0346 (7)
C9	0.7373 (3)	0.08079 (18)	0.0738 (3)	0.0341 (7)
C10	0.7359 (3)	0.2201 (2)	−0.0233 (3)	0.0419 (8)
C11	0.6280 (3)	0.21783 (17)	0.0460 (3)	0.0425 (8)
H11A	0.6414	0.2618	0.1213	0.051*
H11B	0.5450	0.2286	−0.0223	0.051*
C12	0.8730 (3)	−0.04756 (19)	0.0866 (3)	0.0418 (8)
C13	0.7743 (3)	−0.08156 (19)	0.3424 (3)	0.0355 (7)
C14	0.8134 (3)	−0.0171 (2)	0.4468 (3)	0.0450 (8)
H14	0.7881	0.0421	0.4268	0.054*
C15	0.8894 (3)	−0.0398 (3)	0.5800 (3)	0.0555 (9)
H15	0.9154	0.0035	0.6503	0.067*
C16	0.9252 (3)	−0.1262 (3)	0.6059 (4)	0.0638 (10)
C17	0.8917 (3)	−0.1908 (3)	0.5061 (4)	0.0716 (11)
H17	0.9197	−0.2494	0.5265	0.086*
C18	0.8151 (3)	−0.1678 (2)	0.3734 (4)	0.0554 (9)
H18	0.7907	−0.2117	0.3039	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0817 (15)	0.149 (2)	0.0675 (14)	0.0011 (15)	−0.0098 (12)	0.0457 (15)
N1	0.0427 (15)	0.0250 (13)	0.0445 (14)	0.0032 (12)	0.0189 (12)	0.0039 (11)
N2	0.0443 (15)	0.0360 (15)	0.0431 (15)	0.0017 (12)	0.0200 (12)	0.0053 (12)
N3	0.066 (2)	0.0445 (17)	0.089 (2)	0.0114 (15)	0.0466 (17)	0.0115 (16)
O1	0.0565 (14)	0.0360 (13)	0.0746 (16)	−0.0037 (11)	0.0311 (12)	0.0067 (12)
O2	0.0741 (16)	0.0412 (14)	0.0792 (16)	−0.0040 (12)	0.0361 (13)	0.0171 (12)
C1	0.0312 (16)	0.0373 (19)	0.0341 (17)	−0.0034 (14)	0.0104 (14)	−0.0040 (14)
C2	0.0454 (19)	0.0345 (18)	0.0479 (18)	0.0059 (15)	0.0191 (15)	0.0012 (15)
C3	0.056 (2)	0.045 (2)	0.055 (2)	0.0035 (16)	0.0294 (17)	−0.0027 (16)
C4	0.0434 (19)	0.048 (2)	0.053 (2)	0.0015 (16)	0.0234 (16)	0.0006 (16)
C5	0.0411 (19)	0.0371 (19)	0.0381 (17)	−0.0010 (16)	0.0126 (14)	0.0020 (15)
C6	0.0383 (17)	0.0283 (17)	0.0341 (16)	−0.0029 (14)	0.0143 (13)	−0.0023 (14)
C7	0.0407 (17)	0.0215 (15)	0.0401 (17)	−0.0001 (13)	0.0148 (14)	0.0011 (13)
C8	0.0379 (17)	0.0302 (18)	0.0401 (17)	0.0022 (14)	0.0181 (14)	0.0029 (14)
C9	0.0386 (17)	0.0331 (18)	0.0338 (16)	−0.0011 (14)	0.0153 (14)	0.0002 (14)
C10	0.049 (2)	0.0305 (18)	0.0471 (19)	−0.0030 (16)	0.0150 (16)	0.0051 (15)
C11	0.056 (2)	0.0264 (17)	0.0498 (18)	0.0045 (15)	0.0221 (16)	0.0050 (14)
C12	0.051 (2)	0.0280 (17)	0.0518 (19)	−0.0019 (16)	0.0232 (16)	0.0047 (15)
C13	0.0349 (17)	0.0298 (17)	0.0450 (18)	0.0016 (14)	0.0165 (14)	0.0066 (15)
C14	0.0413 (19)	0.046 (2)	0.047 (2)	0.0040 (15)	0.0130 (16)	0.0029 (16)
C15	0.045 (2)	0.077 (3)	0.046 (2)	−0.0005 (19)	0.0137 (17)	−0.0024 (19)
C16	0.045 (2)	0.089 (3)	0.052 (2)	−0.002 (2)	0.0055 (18)	0.024 (2)
C17	0.069 (3)	0.053 (3)	0.082 (3)	0.011 (2)	0.004 (2)	0.031 (2)
C18	0.060 (2)	0.034 (2)	0.067 (2)	0.0042 (17)	0.0087 (19)	0.0070 (17)

Geometric parameters (Å, º) top

F1—C16	1.363 (4)	C5—C6	1.451 (4)
N1—C1	1.374 (3)	C6—C7	1.516 (3)
N1—C9	1.383 (3)	C7—C8	1.517 (3)
N1—C11	1.453 (3)	C7—C13	1.522 (4)
N2—C9	1.375 (3)	C7—H7	0.9800
N2—C10	1.375 (3)	C8—C9	1.335 (3)
N2—H2	0.8600	C8—C12	1.420 (4)
N3—C12	1.149 (3)	C10—C11	1.504 (4)
O1—C5	1.225 (3)	C11—H11A	0.9700
O2—C10	1.204 (3)	C11—H11B	0.9700
C1—C6	1.354 (4)	C13—C18	1.368 (4)
C1—C2	1.492 (3)	C13—C14	1.384 (4)
C2—C3	1.518 (4)	C14—C15	1.379 (4)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C16	1.351 (5)
C3—C4	1.510 (4)	C15—H15	0.9300
C3—H3A	0.9700	C16—C17	1.352 (5)
C3—H3B	0.9700	C17—C18	1.378 (4)
C4—C5	1.502 (4)	C17—H17	0.9300
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700

C1—N1—C9	120.8 (2)	C8—C7—H7	107.9
C1—N1—C11	128.0 (2)	C13—C7—H7	107.9
C9—N1—C11	111.2 (2)	C9—C8—C12	120.6 (3)
C9—N2—C10	112.6 (2)	C9—C8—C7	121.7 (2)
C9—N2—H2	123.7	C12—C8—C7	117.6 (2)
C10—N2—H2	123.7	C8—C9—N2	130.1 (3)
C6—C1—N1	120.1 (2)	C8—C9—N1	122.9 (2)
C6—C1—C2	123.3 (2)	N2—C9—N1	107.0 (2)
N1—C1—C2	116.7 (2)	O2—C10—N2	126.5 (3)
C1—C2—C3	110.1 (2)	O2—C10—C11	126.9 (3)
C1—C2—H2A	109.6	N2—C10—C11	106.6 (2)
C3—C2—H2A	109.6	N1—C11—C10	102.6 (2)
C1—C2—H2B	109.6	N1—C11—H11A	111.2
C3—C2—H2B	109.6	C10—C11—H11A	111.2
H2A—C2—H2B	108.1	N1—C11—H11B	111.2
C4—C3—C2	110.6 (2)	C10—C11—H11B	111.2
C4—C3—H3A	109.5	H11A—C11—H11B	109.2
C2—C3—H3A	109.5	N3—C12—C8	177.3 (3)
C4—C3—H3B	109.5	C18—C13—C14	118.5 (3)
C2—C3—H3B	109.5	C18—C13—C7	121.6 (3)
H3A—C3—H3B	108.1	C14—C13—C7	119.9 (2)
C5—C4—C3	112.9 (2)	C15—C14—C13	120.8 (3)
C5—C4—H4A	109.0	C15—C14—H14	119.6
C3—C4—H4A	109.0	C13—C14—H14	119.6
C5—C4—H4B	109.0	C16—C15—C14	118.4 (3)
C3—C4—H4B	109.0	C16—C15—H15	120.8
H4A—C4—H4B	107.8	C14—C15—H15	120.8
O1—C5—C6	121.1 (3)	C15—C16—C17	122.7 (3)
O1—C5—C4	120.3 (3)	C15—C16—F1	119.0 (4)
C6—C5—C4	118.7 (3)	C17—C16—F1	118.3 (4)
C1—C6—C5	119.8 (3)	C16—C17—C18	118.5 (3)
C1—C6—C7	123.7 (2)	C16—C17—H17	120.7
C5—C6—C7	116.6 (2)	C18—C17—H17	120.7
C6—C7—C8	110.1 (2)	C13—C18—C17	121.0 (3)
C6—C7—C13	111.3 (2)	C13—C18—H18	119.5
C8—C7—C13	111.5 (2)	C17—C18—H18	119.5
C6—C7—H7	107.9

C9—N1—C1—C6	−0.3 (4)	C7—C8—C9—N1	−2.2 (4)
C11—N1—C1—C6	176.6 (3)	C10—N2—C9—C8	178.1 (3)
C9—N1—C1—C2	−179.8 (2)	C10—N2—C9—N1	−1.1 (3)
C11—N1—C1—C2	−3.0 (4)	C1—N1—C9—C8	−2.2 (4)
C6—C1—C2—C3	24.5 (4)	C11—N1—C9—C8	−179.6 (3)
N1—C1—C2—C3	−156.0 (2)	C1—N1—C9—N2	177.0 (2)
C1—C2—C3—C4	−53.2 (3)	C11—N1—C9—N2	−0.3 (3)
C2—C3—C4—C5	51.4 (3)	C9—N2—C10—O2	−177.6 (3)
C3—C4—C5—O1	162.2 (3)	C9—N2—C10—C11	2.0 (3)
C3—C4—C5—C6	−19.4 (4)	C1—N1—C11—C10	−175.7 (2)
N1—C1—C6—C5	−171.3 (2)	C9—N1—C11—C10	1.4 (3)
C2—C1—C6—C5	8.3 (4)	O2—C10—C11—N1	177.6 (3)
N1—C1—C6—C7	7.2 (4)	N2—C10—C11—N1	−2.0 (3)
C2—C1—C6—C7	−173.3 (2)	C9—C8—C12—N3	153 (7)
O1—C5—C6—C1	167.3 (3)	C7—C8—C12—N3	−23 (7)
C4—C5—C6—C1	−11.1 (4)	C6—C7—C13—C18	130.9 (3)
O1—C5—C6—C7	−11.2 (4)	C8—C7—C13—C18	−105.8 (3)
C4—C5—C6—C7	170.3 (2)	C6—C7—C13—C14	−49.9 (3)
C1—C6—C7—C8	−10.3 (4)	C8—C7—C13—C14	73.4 (3)
C5—C6—C7—C8	168.2 (2)	C18—C13—C14—C15	−1.4 (4)
C1—C6—C7—C13	113.9 (3)	C7—C13—C14—C15	179.4 (2)
C5—C6—C7—C13	−67.7 (3)	C13—C14—C15—C16	0.3 (4)
C6—C7—C8—C9	7.7 (4)	C14—C15—C16—C17	1.3 (5)
C13—C7—C8—C9	−116.4 (3)	C14—C15—C16—F1	−179.0 (2)
C6—C7—C8—C12	−176.8 (2)	C15—C16—C17—C18	−1.7 (5)
C13—C7—C8—C12	59.2 (3)	F1—C16—C17—C18	178.6 (3)
C12—C8—C9—N2	3.4 (5)	C14—C13—C18—C17	1.0 (4)
C7—C8—C9—N2	178.8 (3)	C7—C13—C18—C17	−179.8 (3)
C12—C8—C9—N1	−177.6 (2)	C16—C17—C18—C13	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86	2.15	3.006 (4)	173

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄FN₃O₂
M_r	323.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.781 (3), 14.937 (4), 9.839 (3)
β (°)	106.270 (5)
V (Å³)	1521.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.33 × 0.19

Data collection
Diffractometer	Bruker CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	7885, 2678, 1368
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.112, 1.01
No. of reflections	2678
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86	2.15	3.006 (4)	173.3

Symmetry code: (i) −x+2, −y, −z.

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