6-(2-Fluoro-phen-yl)-5,6-dihydro-benzimidazolo[1,2-c]quinazoline.

In the title compound, C(20)H(14)FN(3), the pyrimidine ring adopts a half-chair conformation. The dihedral angle between the benzimidazole ring system and the fluoro-phenyl ring is 84.18 (10)°. In the crystal structure, mol-ecules 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 = 315.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.160

S = 1.06

3591 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H14FN3	F(000) = 656
Mr = 315.34	Dx = 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

Rigaku Weissenberg IP diffractometer	3591 independent reflections
Radiation source: sealed tube	2286 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	h = −11→11
Tmin = 0.899, Tmax = 0.991	k = −17→16
15171 measured reflections	l = −17→17

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(Fo2) + (0.0751P)2 + 0.2459P] where P = (Fo2 + 2Fc2)/3
3591 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .