Ethyl 1-sec-butyl-2-(4-fluoro-phen-yl)-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(20)H(21)FN(2)O(2), the benzene ring and the benzimidazole ring system are inclined at a dihedral angle of 44.40 (9)°. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds, forming a zigzag chain along the b-axis direction. An intra-molecular C-H⋯π inter-action is also observed.

Related literature

For the synthesis of the title compound and related structures, see: Arumugam, Abd Hamid et al. (2010 ▶); Arumugam, Abdul Rahim, Osman, Hemamalini & Fun (2010 ▶); Arumugam, Abdul Rahim, Osman, Quah & Fun (2010 ▶). For applications of benzimidazole derivatives, see: Spasov et al. (1999 ▶); Easmon et al. (2001 ▶); Özden et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H21FN2O2

M = 340.39

Monoclinic,

a = 10.2249 (16) Å

b = 12.3767 (18) Å

c = 14.149 (2) Å

β = 93.473 (2)°

V = 1787.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.37 × 0.20 × 0.11 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.990

10465 measured reflections

3130 independent reflections

2342 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.150

S = 1.05

3130 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041663/is2787sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041663/is2787Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041663/is2787Isup3.cml

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

C20H21FN2O2	F(000) = 720
Mr = 340.39	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2853 reflections
a = 10.2249 (16) Å	θ = 2.0–25.0°
b = 12.3767 (18) Å	µ = 0.09 mm−1
c = 14.149 (2) Å	T = 293 K
β = 93.473 (2)°	Block, colourless
V = 1787.3 (5) Å3	0.37 × 0.20 × 0.11 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.968, Tmax = 0.990	l = −16→16
10465 measured reflections

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) = 0.150	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0825P)2 + 0.313P] where P = (Fo2 + 2Fc2)/3
3130 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 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	1.45030 (16)	1.11874 (14)	0.07109 (13)	0.1053 (6)
O1	0.49279 (17)	0.52863 (13)	0.17567 (13)	0.0764 (5)
O2	0.65827 (16)	0.47066 (12)	0.09413 (12)	0.0696 (5)
N1	0.89771 (15)	0.92002 (12)	0.18887 (11)	0.0456 (4)
N2	0.98670 (15)	0.78337 (12)	0.10912 (11)	0.0468 (4)
C1	0.86373 (18)	0.75303 (14)	0.13674 (12)	0.0421 (4)
C2	0.79676 (19)	0.65643 (15)	0.12078 (13)	0.0458 (5)
H2	0.8334	0.6006	0.0872	0.055*
C3	0.67392 (19)	0.64541 (15)	0.15618 (13)	0.0467 (5)
C4	0.6195 (2)	0.73015 (17)	0.20597 (15)	0.0537 (5)
H4	0.5372	0.7208	0.2293	0.064*
C5	0.68326 (19)	0.82662 (17)	0.22166 (15)	0.0542 (5)
H5	0.6456	0.8827	0.2543	0.065*
C6	0.80724 (18)	0.83677 (15)	0.18631 (13)	0.0439 (5)
C7	1.00272 (18)	0.88255 (15)	0.14109 (12)	0.0428 (4)
C8	1.11991 (18)	0.94762 (15)	0.12502 (13)	0.0443 (5)
C9	1.1114 (2)	1.05455 (17)	0.09460 (14)	0.0557 (5)
H9	1.0297	1.0875	0.0865	0.067*
C10	1.2223 (3)	1.11195 (19)	0.07637 (16)	0.0658 (6)
H10	1.2166	1.1834	0.0561	0.079*
C11	1.3408 (2)	1.0617 (2)	0.08865 (17)	0.0672 (6)
C12	1.3540 (2)	0.9576 (2)	0.11717 (18)	0.0697 (7)
H12	1.4361	0.9253	0.1240	0.084*
C13	1.2422 (2)	0.90061 (18)	0.13581 (16)	0.0582 (6)
H13	1.2496	0.8293	0.1560	0.070*
C14	0.5983 (2)	0.54440 (17)	0.14437 (14)	0.0528 (5)
C15	0.5918 (3)	0.36793 (19)	0.0794 (2)	0.0798 (8)
H15A	0.5018	0.3795	0.0559	0.096*
H15B	0.5915	0.3282	0.1385	0.096*
C16	0.6626 (3)	0.3076 (2)	0.0104 (2)	0.0967 (10)
H16A	0.6615	0.3474	−0.0479	0.145*
H16B	0.6213	0.2387	−0.0007	0.145*
H16C	0.7515	0.2970	0.0342	0.145*
C17	0.8973 (2)	1.01576 (17)	0.25156 (16)	0.0608 (6)
H17	0.9825	1.0513	0.2477	0.073*
C18	0.8868 (3)	0.9822 (2)	0.35314 (18)	0.0803 (8)
H18A	0.8993	1.0451	0.3935	0.096*
H18B	0.7994	0.9545	0.3610	0.096*
C19	0.9833 (3)	0.8994 (3)	0.38342 (18)	0.0906 (9)
H19A	0.9644	0.8337	0.3492	0.136*
H19B	0.9789	0.8864	0.4500	0.136*
H19C	1.0696	0.9240	0.3708	0.136*
C20	0.7917 (3)	1.0977 (2)	0.2147 (3)	0.0974 (10)
H20A	0.7997	1.1099	0.1483	0.146*
H20B	0.8036	1.1647	0.2483	0.146*
H20C	0.7062	1.0693	0.2246	0.146*

	U11	U22	U33	U12	U13	U23
F1	0.0832 (11)	0.1053 (12)	0.1309 (14)	−0.0492 (9)	0.0352 (10)	0.0009 (10)
O1	0.0610 (10)	0.0656 (11)	0.1054 (13)	−0.0198 (8)	0.0281 (9)	−0.0043 (9)
O2	0.0676 (10)	0.0470 (9)	0.0966 (11)	−0.0210 (7)	0.0245 (9)	−0.0150 (8)
N1	0.0434 (9)	0.0390 (9)	0.0552 (9)	−0.0022 (7)	0.0100 (7)	−0.0086 (7)
N2	0.0453 (9)	0.0410 (9)	0.0558 (9)	−0.0032 (7)	0.0156 (7)	−0.0043 (7)
C1	0.0423 (10)	0.0366 (10)	0.0481 (10)	−0.0005 (8)	0.0095 (8)	−0.0007 (8)
C2	0.0474 (10)	0.0364 (10)	0.0545 (11)	0.0001 (8)	0.0126 (9)	−0.0029 (8)
C3	0.0445 (10)	0.0431 (11)	0.0530 (11)	−0.0042 (8)	0.0072 (8)	0.0024 (8)
C4	0.0403 (10)	0.0556 (12)	0.0666 (12)	−0.0026 (9)	0.0145 (9)	−0.0033 (10)
C5	0.0450 (11)	0.0503 (12)	0.0686 (13)	0.0014 (9)	0.0146 (9)	−0.0131 (10)
C6	0.0419 (10)	0.0385 (10)	0.0519 (10)	0.0004 (8)	0.0072 (8)	−0.0039 (8)
C7	0.0449 (10)	0.0394 (10)	0.0448 (10)	−0.0021 (8)	0.0074 (8)	−0.0016 (8)
C8	0.0459 (10)	0.0433 (11)	0.0446 (9)	−0.0058 (8)	0.0095 (8)	−0.0043 (8)
C9	0.0587 (13)	0.0506 (12)	0.0579 (12)	−0.0065 (10)	0.0043 (10)	0.0044 (9)
C10	0.0820 (17)	0.0535 (13)	0.0625 (13)	−0.0223 (12)	0.0088 (12)	0.0089 (10)
C11	0.0623 (14)	0.0713 (16)	0.0702 (14)	−0.0285 (12)	0.0205 (11)	−0.0040 (12)
C12	0.0474 (13)	0.0732 (16)	0.0897 (17)	−0.0075 (11)	0.0139 (11)	−0.0017 (13)
C13	0.0524 (12)	0.0505 (12)	0.0731 (14)	−0.0045 (10)	0.0143 (10)	0.0022 (10)
C14	0.0500 (12)	0.0478 (12)	0.0613 (12)	−0.0066 (9)	0.0099 (10)	0.0027 (9)
C15	0.0873 (18)	0.0516 (14)	0.1029 (19)	−0.0304 (13)	0.0256 (15)	−0.0133 (13)
C16	0.109 (2)	0.0612 (16)	0.123 (2)	−0.0270 (16)	0.0293 (19)	−0.0215 (16)
C17	0.0572 (13)	0.0468 (12)	0.0804 (15)	−0.0078 (10)	0.0197 (11)	−0.0239 (11)
C18	0.0765 (18)	0.095 (2)	0.0720 (16)	−0.0237 (15)	0.0244 (13)	−0.0351 (14)
C19	0.098 (2)	0.114 (2)	0.0592 (15)	−0.0281 (19)	0.0050 (14)	0.0001 (15)
C20	0.0765 (18)	0.0528 (15)	0.165 (3)	0.0089 (13)	0.0213 (18)	−0.0266 (16)

F1—C11	1.359 (2)	C10—C11	1.363 (4)
O1—C14	1.207 (2)	C10—H10	0.9300
O2—C14	1.329 (3)	C11—C12	1.355 (4)
O2—C15	1.451 (3)	C12—C13	1.382 (3)
N1—C7	1.383 (2)	C12—H12	0.9300
N1—C6	1.384 (2)	C13—H13	0.9300
N1—C17	1.480 (2)	C15—C16	1.456 (4)
N2—C7	1.315 (2)	C15—H15A	0.9700
N2—C1	1.391 (2)	C15—H15B	0.9700
C1—C2	1.390 (3)	C16—H16A	0.9600
C1—C6	1.396 (2)	C16—H16B	0.9600
C2—C3	1.387 (3)	C16—H16C	0.9600
C2—H2	0.9300	C17—C18	1.506 (4)
C3—C4	1.397 (3)	C17—C20	1.549 (4)
C3—C14	1.474 (3)	C17—H17	0.9800
C4—C5	1.372 (3)	C18—C19	1.468 (4)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.396 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C7—C8	1.473 (3)	C19—H19B	0.9600
C8—C13	1.379 (3)	C19—H19C	0.9600
C8—C9	1.393 (3)	C20—H20A	0.9600
C9—C10	1.376 (3)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C14—O2—C15	116.83 (18)	C8—C13—H13	119.4
C7—N1—C6	105.97 (14)	C12—C13—H13	119.4
C7—N1—C17	126.27 (16)	O1—C14—O2	122.46 (19)
C6—N1—C17	125.85 (16)	O1—C14—C3	124.7 (2)
C7—N2—C1	104.55 (15)	O2—C14—C3	112.79 (17)
C2—C1—N2	129.17 (16)	O2—C15—C16	107.4 (2)
C2—C1—C6	120.37 (17)	O2—C15—H15A	110.2
N2—C1—C6	110.45 (15)	C16—C15—H15A	110.2
C3—C2—C1	118.30 (17)	O2—C15—H15B	110.2
C3—C2—H2	120.8	C16—C15—H15B	110.2
C1—C2—H2	120.9	H15A—C15—H15B	108.5
C2—C3—C4	120.33 (18)	C15—C16—H16A	109.5
C2—C3—C14	121.51 (18)	C15—C16—H16B	109.5
C4—C3—C14	118.15 (18)	H16A—C16—H16B	109.5
C5—C4—C3	122.36 (19)	C15—C16—H16C	109.5
C5—C4—H4	118.8	H16A—C16—H16C	109.5
C3—C4—H4	118.8	H16B—C16—H16C	109.5
C4—C5—C6	116.93 (18)	N1—C17—C18	110.73 (18)
C4—C5—H5	121.5	N1—C17—C20	110.4 (2)
C6—C5—H5	121.5	C18—C17—C20	114.4 (2)
N1—C6—C1	105.64 (16)	N1—C17—H17	106.9
N1—C6—C5	132.65 (17)	C18—C17—H17	106.9
C1—C6—C5	121.70 (17)	C20—C17—H17	106.9
N2—C7—N1	113.38 (16)	C19—C18—C17	112.7 (2)
N2—C7—C8	122.88 (16)	C19—C18—H18A	109.1
N1—C7—C8	123.72 (16)	C17—C18—H18A	109.1
C13—C8—C9	118.32 (18)	C19—C18—H18B	109.1
C13—C8—C7	119.53 (18)	C17—C18—H18B	109.1
C9—C8—C7	122.07 (18)	H18A—C18—H18B	107.8
C10—C9—C8	120.8 (2)	C18—C19—H19A	109.5
C10—C9—H9	119.6	C18—C19—H19B	109.5
C8—C9—H9	119.6	H19A—C19—H19B	109.5
C11—C10—C9	118.5 (2)	C18—C19—H19C	109.5
C11—C10—H10	120.8	H19A—C19—H19C	109.5
C9—C10—H10	120.8	H19B—C19—H19C	109.5
C12—C11—F1	118.7 (2)	C17—C20—H20A	109.5
C12—C11—C10	122.9 (2)	C17—C20—H20B	109.5
F1—C11—C10	118.4 (2)	H20A—C20—H20B	109.5
C11—C12—C13	118.3 (2)	C17—C20—H20C	109.5
C11—C12—H12	120.9	H20A—C20—H20C	109.5
C13—C12—H12	120.9	H20B—C20—H20C	109.5
C8—C13—C12	121.2 (2)
C7—N2—C1—C2	179.31 (19)	N1—C7—C8—C13	138.2 (2)
C7—N2—C1—C6	−0.2 (2)	N2—C7—C8—C9	133.3 (2)
N2—C1—C2—C3	179.81 (18)	N1—C7—C8—C9	−45.0 (3)
C6—C1—C2—C3	−0.7 (3)	C13—C8—C9—C10	−0.4 (3)
C1—C2—C3—C4	0.4 (3)	C7—C8—C9—C10	−177.26 (18)
C1—C2—C3—C14	−178.35 (17)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	0.6 (4)
C14—C3—C4—C5	179.11 (19)	C9—C10—C11—F1	−179.65 (19)
C3—C4—C5—C6	−0.7 (3)	F1—C11—C12—C13	179.3 (2)
C7—N1—C6—C1	0.10 (19)	C10—C11—C12—C13	−0.9 (4)
C17—N1—C6—C1	−164.91 (18)	C9—C8—C13—C12	0.1 (3)
C7—N1—C6—C5	−179.7 (2)	C7—C8—C13—C12	176.99 (19)
C17—N1—C6—C5	15.3 (3)	C11—C12—C13—C8	0.6 (3)
C2—C1—C6—N1	−179.50 (16)	C15—O2—C14—O1	−1.0 (3)
N2—C1—C6—N1	0.1 (2)	C15—O2—C14—C3	179.5 (2)
C2—C1—C6—C5	0.3 (3)	C2—C3—C14—O1	177.9 (2)
N2—C1—C6—C5	179.88 (18)	C4—C3—C14—O1	−1.0 (3)
C4—C5—C6—N1	−179.9 (2)	C2—C3—C14—O2	−2.6 (3)
C4—C5—C6—C1	0.4 (3)	C4—C3—C14—O2	178.55 (18)
C1—N2—C7—N1	0.3 (2)	C14—O2—C15—C16	170.5 (2)
C1—N2—C7—C8	−178.22 (16)	C7—N1—C17—C18	−110.7 (2)
C6—N1—C7—N2	−0.2 (2)	C6—N1—C17—C18	51.3 (3)
C17—N1—C7—N2	164.68 (18)	C7—N1—C17—C20	121.5 (2)
C6—N1—C7—C8	178.24 (17)	C6—N1—C17—C20	−76.5 (3)
C17—N1—C7—C8	−16.8 (3)	N1—C17—C18—C19	50.7 (3)
N2—C7—C8—C13	−43.5 (3)	C20—C17—C18—C19	176.3 (2)

Cg1 is the centroid of the N1/C7/N2/C1/C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.53	3.452 (3)	169
C20—H20C···O1i	0.96	2.59	3.485 (4)	154
C19—H19A···Cg1	0.96	2.82	3.400 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/N2/C1/C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.53	3.452 (3)	169
C20—H20C⋯O1i	0.96	2.59	3.485 (4)	154
C19—H19A⋯Cg1	0.96	2.82	3.400 (3)	121

Symmetry code: (i) .