6-(2-Fluoro­phen­yl)-5,6-dihydro­benzimidazolo[1,2-c]quinazoline

Li, A.-K.; Chen, J.-X.; Zheng, L.-Q.; Zhu, M.-P.; Zhang, L.

doi:10.1107/S1600536808031875

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2097

doi:10.1107/S1600536808031875

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6-(2-Fluorophenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazoline

Ai-Ke Li,^a Jian-Xin Chen,^a ^* Li-Qun Zheng,^a Mei-Ping Zhu ^a and Li Zhang ^a

^aCollege of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, People's Republic of China
^*Correspondence e-mail: jxchen-1964@163.com

(Received 8 September 2008; accepted 3 October 2008; online 11 October 2008)

In the title compound, C₂₀H₁₄FN₃, the pyrimidine ring adopts a half-chair conformation. The dihedral angle between the benzimidazole ring system and the fluorophenyl ring is 84.18 (10)°. In the crystal structure, molecules are linked into a two-dimensional network parallel to the bc plane by N—H⋯N and C—H⋯F hydrogen bonds.

Related literature

For related structures, see: Elgemeie et al. (1998 ); Jayalakshmi et al. (2004 ); Low et al. (2003 ); Mahendra et al. (2005 ). For related literature, see: Alexandre et al. (2003 ); Bandurco et al. (1981 ); Chern et al. (1993 ); Fatmi et al. (1984 ).

Experimental

Crystal data

C₂₀H₁₄FN₃
M_r = 315.34
Monoclinic, P 2₁ /c
a = 8.7344 (17) Å
b = 13.623 (3) Å
c = 13.356 (3) Å
β = 99.78 (3)°
V = 1566.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.23 × 0.21 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998 ) T_min = 0.899, T_max = 0.991
15171 measured reflections
3591 independent reflections
2286 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.160
S = 1.06
3591 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3ⁱ	0.86	2.31	2.995 (2)	136
C11—H11A⋯F1ⁱⁱ	0.93	2.43	3.264 (3)	149
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031875/ci2668sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031875/ci2668Isup2.hkl

checkCIF report

Comment top

A variety of compounds containing the quinazoline skeleton has been found to exhibit antihypertensive, antimalarial and bronchodilator activities (Alexandre et al., 2003; Bandurco et al., 1981; Chern et al., 1993; Fatmi et al., 1984) and crystal structures of some of these compounds have been reported (Elgemeie et al., 1998; Low et al., 2003; Jayalakshmi et al., 2004; Mahendra et al., 2005). In view of the above importance, the title compound, (I), was prepared from ο-aminophenylbenzimidazole and ο-fluorobenzaldehyde and its crystal structure is reported here (Fig. 1).

Most of the bond lengths and angles have normal values and are comparable to those observed in related structures (Low et al., 2003; Mahendra et al., 2005). The benzimidazole ring system is planar. The pyrimidine ring adopts a half-chair conformation, with atoms N1 and C14 deviate from the N2/C1/C8/C9 plane by 0.178 (3) and -0.222 (3) Å, respectively. The dihedral angle between the benzimidazole ring system and the fluorophenyl ring is 84.18 (10)°.

In the crystal structure, the molecules are linked into a two-dimensional network parallel to the bc plane (Fig.2) by N—H···N and C—H···F hydrogen bonds (Table 1).

Related literature top

For related structures, see: Elgemeie et al. (1998); Jayalakshmi et al. (2004); Low et al. (2003); Mahendra et al. (2005). For related literature, see: Alexandre et al. (2003); Bandurco et al. (1981); Chern et al. (1993); Fatmi et al. (1984).

Experimental top

All reagents were of AR grade available commercially and used without further purification. A solution of ο-aminophenylbenzimidazole (5 mmol) and ο-fluorobenzaldehyde (5 mmol) in ethanol (12 ml) was treated with acetic acid (0.2 ml) for 5 h. The resulting solution was concentrated under reduced pressure to a small volume to obtain a creamy compound. The solid was recrystallized from ethanol to give a brown crystalline compound (I) (yield 70%; m.p. 521 K). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

6-(2-Fluorophenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazoline top

Crystal data top

C₂₀H₁₄FN₃	F(000) = 656
M_r = 315.34	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3589 reflections
a = 8.7344 (17) Å	θ = 3.0–27.5°
b = 13.623 (3) Å	µ = 0.09 mm⁻¹
c = 13.356 (3) Å	T = 298 K
β = 99.78 (3)°	Chunk, brown
V = 1566.1 (6) Å³	0.23 × 0.21 × 0.15 mm
Z = 4

Data collection top

Rigaku Weissenberg IP diffractometer	3591 independent reflections
Radiation source: sealed tube	2286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	h = −11→11
T_min = 0.899, T_max = 0.991	k = −17→16
15171 measured reflections	l = −17→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0751P)² + 0.2459P] where P = (F_o² + 2F_c²)/3
3591 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₁₄FN₃	V = 1566.1 (6) Å³
M_r = 315.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7344 (17) Å	µ = 0.09 mm⁻¹
b = 13.623 (3) Å	T = 298 K
c = 13.356 (3) Å	0.23 × 0.21 × 0.15 mm
β = 99.78 (3)°

Data collection top

Rigaku Weissenberg IP diffractometer	3591 independent reflections
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	2286 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.991	R_int = 0.035
15171 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
3591 reflections	Δρ_min = −0.31 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	0.22484 (19)	0.16127 (14)	0.15884 (10)	0.1072 (6)
N1	0.51477 (19)	0.25468 (13)	0.34079 (11)	0.0606 (5)
H1A	0.5498	0.2553	0.2844	0.073*
N2	0.41799 (18)	0.15511 (12)	0.45924 (10)	0.0519 (4)
N3	0.4822 (2)	0.16940 (12)	0.62780 (11)	0.0571 (4)
C1	0.4941 (2)	0.20758 (14)	0.53935 (12)	0.0500 (4)
C2	0.3860 (2)	0.08770 (15)	0.60402 (14)	0.0553 (5)
C3	0.3286 (3)	0.02189 (17)	0.66787 (16)	0.0698 (6)
H3B	0.3564	0.0268	0.7381	0.084*
C4	0.2299 (3)	−0.05068 (18)	0.62477 (19)	0.0769 (6)
H4A	0.1894	−0.0949	0.6664	0.092*
C5	0.1893 (3)	−0.05921 (18)	0.5196 (2)	0.0793 (7)
H5A	0.1232	−0.1095	0.4924	0.095*
C6	0.2453 (3)	0.00545 (16)	0.45505 (17)	0.0671 (6)
H6A	0.2180	0.0003	0.3848	0.081*
C7	0.3436 (2)	0.07804 (14)	0.49963 (14)	0.0541 (5)
C8	0.5723 (2)	0.29641 (14)	0.51872 (13)	0.0517 (4)
C9	0.5753 (2)	0.31982 (15)	0.41612 (13)	0.0523 (5)
C10	0.6471 (3)	0.40634 (17)	0.39484 (16)	0.0646 (6)
H10A	0.6476	0.4239	0.3276	0.077*
C11	0.7168 (3)	0.46590 (18)	0.47110 (19)	0.0747 (6)
H11A	0.7660	0.5230	0.4551	0.090*
C12	0.7158 (3)	0.44306 (17)	0.57132 (18)	0.0736 (6)
H12A	0.7646	0.4842	0.6225	0.088*
C13	0.6429 (3)	0.35968 (15)	0.59553 (15)	0.0621 (5)
H13A	0.6401	0.3450	0.6632	0.075*
C14	0.3936 (2)	0.18490 (15)	0.35345 (12)	0.0528 (5)
H14A	0.4050	0.1270	0.3119	0.063*
C15	0.2318 (2)	0.22592 (14)	0.32082 (13)	0.0522 (5)
C16	0.1535 (3)	0.21340 (17)	0.22401 (16)	0.0668 (6)
C17	0.0088 (3)	0.2507 (2)	0.1890 (2)	0.0894 (8)
H17A	−0.0400	0.2398	0.1224	0.107*
C18	−0.0614 (3)	0.3038 (2)	0.2538 (3)	0.0944 (8)
H18A	−0.1598	0.3297	0.2317	0.113*
C19	0.0113 (3)	0.3198 (2)	0.3516 (2)	0.0937 (8)
H19A	−0.0373	0.3570	0.3955	0.112*
C20	0.1567 (3)	0.28070 (19)	0.38496 (18)	0.0762 (7)
H20A	0.2051	0.2913	0.4517	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1146 (12)	0.1504 (14)	0.0498 (8)	0.0203 (11)	−0.0054 (7)	−0.0329 (8)
N1	0.0651 (10)	0.0853 (12)	0.0328 (7)	0.0036 (9)	0.0128 (7)	0.0029 (7)
N2	0.0612 (9)	0.0631 (9)	0.0304 (7)	0.0075 (8)	0.0047 (6)	0.0008 (6)
N3	0.0700 (10)	0.0691 (10)	0.0320 (8)	0.0019 (9)	0.0081 (7)	0.0012 (7)
C1	0.0579 (10)	0.0610 (11)	0.0305 (8)	0.0078 (9)	0.0056 (7)	−0.0013 (7)
C2	0.0646 (12)	0.0598 (11)	0.0414 (10)	0.0055 (10)	0.0088 (8)	0.0028 (8)
C3	0.0853 (15)	0.0752 (14)	0.0496 (11)	−0.0042 (12)	0.0131 (10)	0.0088 (10)
C4	0.0859 (16)	0.0714 (14)	0.0734 (15)	−0.0053 (13)	0.0136 (12)	0.0156 (12)
C5	0.0819 (16)	0.0672 (13)	0.0852 (18)	−0.0053 (12)	0.0033 (13)	−0.0018 (13)
C6	0.0759 (14)	0.0694 (13)	0.0521 (11)	0.0037 (11)	−0.0002 (10)	−0.0035 (10)
C7	0.0595 (11)	0.0560 (10)	0.0456 (10)	0.0079 (9)	0.0057 (8)	0.0000 (8)
C8	0.0566 (10)	0.0591 (11)	0.0406 (9)	0.0083 (9)	0.0113 (8)	0.0024 (8)
C9	0.0507 (10)	0.0679 (12)	0.0391 (9)	0.0131 (9)	0.0100 (8)	0.0030 (8)
C10	0.0688 (13)	0.0753 (13)	0.0530 (12)	0.0096 (11)	0.0205 (10)	0.0159 (10)
C11	0.0840 (16)	0.0704 (14)	0.0751 (15)	−0.0008 (12)	0.0290 (13)	0.0086 (12)
C12	0.0897 (16)	0.0698 (13)	0.0639 (14)	−0.0097 (13)	0.0202 (12)	−0.0090 (11)
C13	0.0754 (13)	0.0693 (13)	0.0427 (10)	−0.0020 (11)	0.0131 (9)	−0.0044 (9)
C14	0.0653 (11)	0.0648 (11)	0.0270 (8)	0.0133 (10)	0.0041 (7)	−0.0026 (8)
C15	0.0587 (11)	0.0567 (10)	0.0392 (9)	0.0054 (9)	0.0026 (8)	−0.0002 (8)
C16	0.0716 (14)	0.0800 (14)	0.0444 (10)	0.0017 (11)	−0.0027 (9)	−0.0029 (10)
C17	0.0748 (16)	0.114 (2)	0.0674 (15)	0.0012 (15)	−0.0206 (13)	0.0111 (15)
C18	0.0635 (15)	0.103 (2)	0.110 (2)	0.0173 (15)	−0.0057 (15)	0.0153 (18)
C19	0.0721 (16)	0.106 (2)	0.101 (2)	0.0296 (15)	0.0072 (15)	−0.0133 (16)
C20	0.0701 (14)	0.0927 (16)	0.0630 (14)	0.0226 (13)	0.0031 (11)	−0.0155 (12)

Geometric parameters (Å, º) top

F1—C16	1.354 (3)	C8—C9	1.412 (2)
N1—C9	1.378 (3)	C9—C10	1.387 (3)
N1—C14	1.454 (3)	C10—C11	1.362 (3)
N1—H1A	0.8600	C10—H10A	0.93
N2—C1	1.362 (2)	C11—C12	1.376 (3)
N2—C7	1.391 (2)	C11—H11A	0.93
N2—C14	1.451 (2)	C12—C13	1.368 (3)
N3—C1	1.311 (2)	C12—H12A	0.93
N3—C2	1.398 (3)	C13—H13A	0.93
C1—C8	1.439 (3)	C14—C15	1.514 (3)
C2—C7	1.387 (3)	C14—H14A	0.98
C2—C3	1.388 (3)	C15—C16	1.367 (3)
C3—C4	1.372 (3)	C15—C20	1.382 (3)
C3—H3B	0.93	C16—C17	1.369 (3)
C4—C5	1.394 (3)	C17—C18	1.352 (4)
C4—H4A	0.93	C17—H17A	0.93
C5—C6	1.378 (3)	C18—C19	1.370 (4)
C5—H5A	0.93	C18—H18A	0.93
C6—C7	1.377 (3)	C19—C20	1.380 (3)
C6—H6A	0.93	C19—H19A	0.93
C8—C13	1.400 (3)	C20—H20A	0.93

C9—N1—C14	122.21 (14)	C11—C10—H10A	119.6
C9—N1—H1A	118.9	C9—C10—H10A	119.6
C14—N1—H1A	118.9	C10—C11—C12	121.1 (2)
C1—N2—C7	106.81 (14)	C10—C11—H11A	119.4
C1—N2—C14	126.12 (16)	C12—C11—H11A	119.4
C7—N2—C14	126.01 (16)	C13—C12—C11	119.9 (2)
C1—N3—C2	104.34 (15)	C13—C12—H12A	120.1
N3—C1—N2	113.37 (17)	C11—C12—H12A	120.1
N3—C1—C8	128.24 (17)	C12—C13—C8	120.18 (19)
N2—C1—C8	118.36 (15)	C12—C13—H13A	119.9
C7—C2—C3	119.58 (19)	C8—C13—H13A	119.9
C7—C2—N3	110.58 (16)	N2—C14—N1	107.87 (15)
C3—C2—N3	129.82 (18)	N2—C14—C15	111.05 (14)
C4—C3—C2	118.3 (2)	N1—C14—C15	112.81 (16)
C4—C3—H3B	120.8	N2—C14—H14A	108.3
C2—C3—H3B	120.8	N1—C14—H14A	108.3
C3—C4—C5	121.1 (2)	C15—C14—H14A	108.3
C3—C4—H4A	119.4	C16—C15—C20	116.13 (19)
C5—C4—H4A	119.4	C16—C15—C14	121.23 (17)
C6—C5—C4	121.4 (2)	C20—C15—C14	122.60 (17)
C6—C5—H5A	119.3	F1—C16—C15	117.59 (19)
C4—C5—H5A	119.3	F1—C16—C17	118.3 (2)
C7—C6—C5	116.7 (2)	C15—C16—C17	124.1 (2)
C7—C6—H6A	121.6	C18—C17—C16	118.2 (2)
C5—C6—H6A	121.6	C18—C17—H17A	120.9
C6—C7—C2	122.92 (19)	C16—C17—H17A	120.9
C6—C7—N2	132.26 (18)	C17—C18—C19	120.6 (2)
C2—C7—N2	104.81 (17)	C17—C18—H18A	119.7
C13—C8—C9	119.59 (19)	C19—C18—H18A	119.7
C13—C8—C1	122.78 (16)	C18—C19—C20	119.9 (3)
C9—C8—C1	117.62 (17)	C18—C19—H19A	120.1
N1—C9—C10	121.90 (17)	C20—C19—H19A	120.1
N1—C9—C8	119.68 (18)	C19—C20—C15	121.1 (2)
C10—C9—C8	118.33 (19)	C19—C20—H20A	119.5
C11—C10—C9	120.87 (19)	C15—C20—H20A	119.5

C2—N3—C1—N2	−2.4 (2)	C13—C8—C9—C10	−0.8 (3)
C2—N3—C1—C8	176.00 (18)	C1—C8—C9—C10	178.52 (16)
C7—N2—C1—N3	3.0 (2)	N1—C9—C10—C11	−174.8 (2)
C14—N2—C1—N3	171.79 (16)	C8—C9—C10—C11	1.8 (3)
C7—N2—C1—C8	−175.55 (15)	C9—C10—C11—C12	−1.2 (4)
C14—N2—C1—C8	−6.8 (3)	C10—C11—C12—C13	−0.5 (4)
C1—N3—C2—C7	0.9 (2)	C11—C12—C13—C8	1.4 (3)
C1—N3—C2—C3	−177.1 (2)	C9—C8—C13—C12	−0.8 (3)
C7—C2—C3—C4	−0.5 (3)	C1—C8—C13—C12	179.9 (2)
N3—C2—C3—C4	177.4 (2)	C1—N2—C14—N1	24.3 (2)
C2—C3—C4—C5	0.8 (4)	C7—N2—C14—N1	−168.98 (16)
C3—C4—C5—C6	−0.7 (4)	C1—N2—C14—C15	−99.8 (2)
C4—C5—C6—C7	0.4 (3)	C7—N2—C14—C15	66.9 (2)
C5—C6—C7—C2	−0.2 (3)	C9—N1—C14—N2	−33.8 (2)
C5—C6—C7—N2	−178.7 (2)	C9—N1—C14—C15	89.2 (2)
C3—C2—C7—C6	0.2 (3)	N2—C14—C15—C16	−146.77 (19)
N3—C2—C7—C6	−178.02 (19)	N1—C14—C15—C16	92.0 (2)
C3—C2—C7—N2	179.11 (18)	N2—C14—C15—C20	35.6 (3)
N3—C2—C7—N2	0.9 (2)	N1—C14—C15—C20	−85.7 (2)
C1—N2—C7—C6	176.5 (2)	C20—C15—C16—F1	179.1 (2)
C14—N2—C7—C6	7.7 (3)	C14—C15—C16—F1	1.3 (3)
C1—N2—C7—C2	−2.2 (2)	C20—C15—C16—C17	−0.5 (4)
C14—N2—C7—C2	−171.00 (16)	C14—C15—C16—C17	−178.3 (2)
N3—C1—C8—C13	−3.7 (3)	F1—C16—C17—C18	−179.1 (2)
N2—C1—C8—C13	174.62 (18)	C15—C16—C17—C18	0.4 (4)
N3—C1—C8—C9	176.94 (18)	C16—C17—C18—C19	0.2 (4)
N2—C1—C8—C9	−4.7 (3)	C17—C18—C19—C20	−0.7 (5)
C14—N1—C9—C10	−157.02 (18)	C18—C19—C20—C15	0.6 (4)
C14—N1—C9—C8	26.4 (3)	C16—C15—C20—C19	0.0 (4)
C13—C8—C9—N1	175.87 (18)	C14—C15—C20—C19	177.7 (2)
C1—C8—C9—N1	−4.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.31	2.995 (2)	136
C11—H11A···F1ⁱⁱ	0.93	2.43	3.264 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄FN₃
M_r	315.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.7344 (17), 13.623 (3), 13.356 (3)
β (°)	99.78 (3)
V (Å³)	1566.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.21 × 0.15

Data collection
Diffractometer	Rigaku Weissenberg IP diffractometer
Absorption correction	Multi-scan (RAPID-AUTO; Rigaku, 1998)
T_min, T_max	0.899, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	15171, 3591, 2286
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.160, 1.06
No. of reflections	3591
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.31	2.995 (2)	136
C11—H11A···F1ⁱⁱ	0.93	2.43	3.264 (3)	149

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

Acknowledgements

The authors are grateful to the Natural Science Foundation of Fujian Province, China (grant Nos. 2007 J0216 and U0750004), the Ministry of Education of China (grant No. 208066), the Education Department of Fujian Province, China (grant No. JA07029) and the State Key Laboratory of Structural Chemistry, China (grant No. 20080053), for financial support.

References

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