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

In the title mol-ecule, C(21)H(24)N(2)O(3), the dihedral angle between the benzene and imidazole rings is 66.33 (13)°. The imidazole ring is essentially planar, with a maximum deviation of 0.004 (2) Å. In the crystal structure, mol-ecules are connected by weak C-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For the benzimidazole nucleus as a key building block for compounds showing biologically activity, see: Tanious et al. (2004 ▶). For the therapeutic properties of benzimidazole derivatives, see: Kohara et al. (1996 ▶); Mader et al. (2008 ▶). For 2-substituted-phen­ylbenzimidazoles with biological activity, see: Coburn et al. (1987 ▶); Roth et al. (1997 ▶).

Experimental

Crystal data

C21H24N2O3

M = 352.42

Monoclinic,

a = 10.5815 (3) Å

b = 12.1079 (3) Å

c = 15.1050 (3) Å

β = 93.678 (2)°

V = 1931.26 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.31 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.994

19216 measured reflections

4437 independent reflections

2266 reflections with I > 2s(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.150

S = 1.04

4437 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 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 datablocks global, I. DOI: 10.1107/S1600536810007634/tk2635sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007634/tk2635Isup2.hkl

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

C21H24N2O3	F(000) = 752
Mr = 352.42	Dx = 1.212 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1865 reflections
a = 10.5815 (3) Å	θ = 2.6–19.8°
b = 12.1079 (3) Å	µ = 0.08 mm−1
c = 15.1050 (3) Å	T = 296 K
β = 93.678 (2)°	Plate, colourless
V = 1931.26 (8) Å3	0.40 × 0.31 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4437 independent reflections
Radiation source: fine-focus sealed tube	2266 reflections with I > 2s(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.968, Tmax = 0.994	k = −15→15
19216 measured reflections	l = −19→19

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.4985P] where P = (Fo2 + 2Fc2)/3
4437 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.50185 (18)	0.95365 (16)	0.17576 (12)	0.0728 (6)
O2	0.34173 (18)	1.00924 (15)	0.08352 (13)	0.0735 (6)
O3	−0.47540 (19)	0.38119 (16)	0.08035 (13)	0.0761 (6)
N1	0.07745 (19)	0.58199 (16)	0.20122 (13)	0.0503 (5)
N2	0.00579 (19)	0.70718 (16)	0.10000 (13)	0.0532 (5)
C1	−0.2515 (2)	0.5992 (2)	0.15122 (17)	0.0587 (7)
H1A	−0.2505	0.6692	0.1767	0.070*
C2	−0.3657 (3)	0.5442 (2)	0.13763 (16)	0.0594 (7)
H2A	−0.4402	0.5765	0.1543	0.071*
C3	−0.3678 (3)	0.4410 (2)	0.09909 (16)	0.0570 (7)
C4	−0.2565 (3)	0.3940 (2)	0.07547 (19)	0.0696 (8)
H4A	−0.2578	0.3243	0.0495	0.084*
C5	−0.1438 (3)	0.4490 (2)	0.08990 (18)	0.0651 (8)
H5A	−0.0693	0.4159	0.0739	0.078*
C6	−0.1391 (2)	0.5534 (2)	0.12809 (15)	0.0491 (6)
C7	−0.0199 (2)	0.6160 (2)	0.14217 (16)	0.0481 (6)
C8	0.1732 (2)	0.65916 (19)	0.19625 (15)	0.0478 (6)
C9	0.2938 (2)	0.6692 (2)	0.23777 (17)	0.0598 (7)
H9A	0.3260	0.6164	0.2779	0.072*
C10	0.3633 (2)	0.7602 (2)	0.21706 (17)	0.0563 (7)
H10A	0.4438	0.7693	0.2445	0.068*
C11	0.3174 (2)	0.8402 (2)	0.15602 (15)	0.0485 (6)
C12	0.1987 (2)	0.8284 (2)	0.11322 (16)	0.0509 (6)
H12A	0.1677	0.8803	0.0720	0.061*
C13	0.1265 (2)	0.73630 (19)	0.13359 (15)	0.0452 (6)
C14	0.3975 (3)	0.9378 (2)	0.14099 (17)	0.0548 (7)
C15	0.4123 (3)	1.1098 (2)	0.0663 (2)	0.0797 (9)
H15A	0.4977	1.0918	0.0515	0.096*
H15B	0.4170	1.1571	0.1183	0.096*
C16	0.3432 (3)	1.1663 (3)	−0.0091 (2)	0.0928 (10)
H16A	0.3872	1.2328	−0.0229	0.139*
H16B	0.2592	1.1843	0.0067	0.139*
H16C	0.3385	1.1184	−0.0598	0.139*
C17	0.0678 (3)	0.4949 (2)	0.26963 (17)	0.0600 (7)
H17A	−0.0174	0.4634	0.2602	0.072*
C18	0.0755 (3)	0.5434 (3)	0.36209 (18)	0.0758 (9)
H18A	0.0617	0.4847	0.4041	0.091*
H18B	0.1605	0.5715	0.3751	0.091*
C19	−0.0167 (3)	0.6342 (3)	0.3763 (2)	0.0972 (11)
H19A	−0.0046	0.6609	0.4361	0.146*
H19B	−0.1015	0.6067	0.3662	0.146*
H19C	−0.0033	0.6934	0.3357	0.146*
C20	0.1589 (3)	0.4015 (2)	0.2570 (2)	0.0830 (10)
H20A	0.1475	0.3744	0.1973	0.124*
H20B	0.1432	0.3430	0.2977	0.124*
H20C	0.2442	0.4276	0.2678	0.124*
C21	−0.5922 (3)	0.4267 (3)	0.1060 (2)	0.0828 (10)
H21A	−0.6601	0.3767	0.0894	0.124*
H21B	−0.6072	0.4962	0.0766	0.124*
H21C	−0.5877	0.4376	0.1690	0.124*

	U11	U22	U33	U12	U13	U23
O1	0.0634 (13)	0.0789 (14)	0.0747 (13)	−0.0233 (11)	−0.0070 (11)	0.0058 (10)
O2	0.0746 (13)	0.0553 (12)	0.0884 (14)	−0.0213 (10)	−0.0109 (11)	0.0173 (10)
O3	0.0636 (13)	0.0762 (14)	0.0884 (14)	−0.0216 (11)	0.0039 (10)	−0.0165 (11)
N1	0.0537 (13)	0.0410 (12)	0.0558 (12)	−0.0019 (10)	−0.0002 (10)	0.0107 (9)
N2	0.0560 (14)	0.0466 (12)	0.0557 (13)	−0.0065 (10)	−0.0052 (10)	0.0079 (10)
C1	0.0655 (18)	0.0428 (15)	0.0685 (18)	−0.0067 (14)	0.0085 (14)	−0.0055 (12)
C2	0.0556 (17)	0.0565 (17)	0.0668 (17)	−0.0023 (14)	0.0091 (13)	−0.0005 (14)
C3	0.0616 (18)	0.0545 (17)	0.0547 (15)	−0.0136 (15)	0.0015 (13)	−0.0006 (13)
C4	0.0677 (19)	0.0530 (17)	0.088 (2)	−0.0092 (16)	0.0052 (16)	−0.0216 (15)
C5	0.0599 (18)	0.0529 (17)	0.083 (2)	−0.0005 (15)	0.0062 (15)	−0.0119 (15)
C6	0.0534 (16)	0.0412 (14)	0.0524 (14)	−0.0027 (13)	0.0010 (12)	0.0048 (12)
C7	0.0520 (15)	0.0425 (14)	0.0498 (14)	−0.0003 (12)	0.0039 (12)	0.0028 (11)
C8	0.0496 (15)	0.0411 (14)	0.0527 (14)	−0.0007 (12)	0.0032 (12)	0.0026 (11)
C9	0.0554 (17)	0.0533 (17)	0.0699 (18)	0.0026 (14)	−0.0035 (14)	0.0114 (13)
C10	0.0494 (16)	0.0539 (17)	0.0643 (17)	−0.0004 (13)	−0.0050 (13)	0.0020 (13)
C11	0.0500 (15)	0.0440 (14)	0.0516 (14)	−0.0031 (12)	0.0050 (12)	−0.0023 (11)
C12	0.0575 (16)	0.0440 (15)	0.0506 (14)	−0.0013 (13)	−0.0005 (12)	0.0055 (11)
C13	0.0492 (15)	0.0399 (14)	0.0462 (14)	0.0016 (12)	0.0002 (11)	0.0005 (11)
C14	0.0575 (17)	0.0539 (17)	0.0531 (16)	−0.0077 (14)	0.0042 (14)	−0.0047 (13)
C15	0.092 (2)	0.0582 (19)	0.087 (2)	−0.0277 (17)	−0.0076 (18)	0.0144 (16)
C16	0.111 (3)	0.072 (2)	0.095 (2)	−0.022 (2)	0.003 (2)	0.0107 (19)
C17	0.0638 (17)	0.0486 (15)	0.0672 (18)	−0.0039 (14)	0.0018 (14)	0.0196 (13)
C18	0.081 (2)	0.083 (2)	0.0640 (19)	−0.0050 (18)	0.0050 (16)	0.0213 (16)
C19	0.108 (3)	0.110 (3)	0.074 (2)	0.020 (2)	0.0124 (19)	−0.008 (2)
C20	0.079 (2)	0.0545 (18)	0.116 (3)	0.0092 (17)	0.0115 (19)	0.0259 (17)
C21	0.063 (2)	0.107 (3)	0.078 (2)	−0.0206 (19)	0.0052 (16)	−0.0121 (19)

O1—C14	1.208 (3)	C10—H10A	0.9300
O2—C14	1.335 (3)	C11—C12	1.383 (3)
O2—C15	1.461 (3)	C11—C14	1.481 (3)
O3—C3	1.363 (3)	C12—C13	1.396 (3)
O3—C21	1.429 (3)	C12—H12A	0.9300
N1—C7	1.381 (3)	C15—C16	1.480 (4)
N1—C8	1.384 (3)	C15—H15A	0.9700
N1—C17	1.485 (3)	C15—H15B	0.9700
N2—C7	1.312 (3)	C16—H16A	0.9600
N2—C13	1.389 (3)	C16—H16B	0.9600
C1—C6	1.377 (3)	C16—H16C	0.9600
C1—C2	1.384 (3)	C17—C20	1.507 (4)
C1—H1A	0.9300	C17—C18	1.512 (4)
C2—C3	1.379 (4)	C17—H17A	0.9800
C2—H2A	0.9300	C18—C19	1.495 (4)
C3—C4	1.375 (4)	C18—H18A	0.9700
C4—C5	1.372 (4)	C18—H18B	0.9700
C4—H4A	0.9300	C19—H19A	0.9600
C5—C6	1.389 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.475 (3)	C20—H20A	0.9600
C8—C9	1.391 (3)	C20—H20B	0.9600
C8—C13	1.397 (3)	C20—H20C	0.9600
C9—C10	1.373 (3)	C21—H21A	0.9600
C9—H9A	0.9300	C21—H21B	0.9600
C10—C11	1.402 (3)	C21—H21C	0.9600
C14—O2—C15	116.5 (2)	O1—C14—O2	122.2 (2)
C3—O3—C21	117.7 (2)	O1—C14—C11	125.2 (3)
C7—N1—C8	106.39 (19)	O2—C14—C11	112.6 (2)
C7—N1—C17	125.4 (2)	O2—C15—C16	106.8 (2)
C8—N1—C17	126.9 (2)	O2—C15—H15A	110.4
C7—N2—C13	104.5 (2)	C16—C15—H15A	110.4
C6—C1—C2	121.9 (2)	O2—C15—H15B	110.4
C6—C1—H1A	119.0	C16—C15—H15B	110.4
C2—C1—H1A	119.0	H15A—C15—H15B	108.6
C3—C2—C1	119.3 (2)	C15—C16—H16A	109.5
C3—C2—H2A	120.3	C15—C16—H16B	109.5
C1—C2—H2A	120.3	H16A—C16—H16B	109.5
O3—C3—C4	116.4 (2)	C15—C16—H16C	109.5
O3—C3—C2	124.0 (3)	H16A—C16—H16C	109.5
C4—C3—C2	119.6 (3)	H16B—C16—H16C	109.5
C5—C4—C3	120.5 (3)	N1—C17—C20	111.8 (2)
C5—C4—H4A	119.7	N1—C17—C18	111.4 (2)
C3—C4—H4A	119.7	C20—C17—C18	114.3 (2)
C4—C5—C6	121.0 (3)	N1—C17—H17A	106.2
C4—C5—H5A	119.5	C20—C17—H17A	106.2
C6—C5—H5A	119.5	C18—C17—H17A	106.2
C1—C6—C5	117.6 (2)	C19—C18—C17	114.9 (2)
C1—C6—C7	120.1 (2)	C19—C18—H18A	108.5
C5—C6—C7	122.3 (2)	C17—C18—H18A	108.5
N2—C7—N1	113.3 (2)	C19—C18—H18B	108.5
N2—C7—C6	124.3 (2)	C17—C18—H18B	108.5
N1—C7—C6	122.4 (2)	H18A—C18—H18B	107.5
N1—C8—C9	133.5 (2)	C18—C19—H19A	109.5
N1—C8—C13	105.1 (2)	C18—C19—H19B	109.5
C9—C8—C13	121.4 (2)	H19A—C19—H19B	109.5
C10—C9—C8	117.2 (2)	C18—C19—H19C	109.5
C10—C9—H9A	121.4	H19A—C19—H19C	109.5
C8—C9—H9A	121.4	H19B—C19—H19C	109.5
C9—C10—C11	122.4 (2)	C17—C20—H20A	109.5
C9—C10—H10A	118.8	C17—C20—H20B	109.5
C11—C10—H10A	118.8	H20A—C20—H20B	109.5
C12—C11—C10	120.2 (2)	C17—C20—H20C	109.5
C12—C11—C14	121.5 (2)	H20A—C20—H20C	109.5
C10—C11—C14	118.3 (2)	H20B—C20—H20C	109.5
C11—C12—C13	118.2 (2)	O3—C21—H21A	109.5
C11—C12—H12A	120.9	O3—C21—H21B	109.5
C13—C12—H12A	120.9	H21A—C21—H21B	109.5
N2—C13—C12	128.7 (2)	O3—C21—H21C	109.5
N2—C13—C8	110.8 (2)	H21A—C21—H21C	109.5
C12—C13—C8	120.5 (2)	H21B—C21—H21C	109.5
C6—C1—C2—C3	−0.6 (4)	C13—C8—C9—C10	2.4 (4)
C21—O3—C3—C4	178.6 (2)	C8—C9—C10—C11	−0.8 (4)
C21—O3—C3—C2	−2.9 (4)	C9—C10—C11—C12	−0.8 (4)
C1—C2—C3—O3	−178.0 (2)	C9—C10—C11—C14	177.5 (2)
C1—C2—C3—C4	0.5 (4)	C10—C11—C12—C13	0.9 (3)
O3—C3—C4—C5	178.6 (3)	C14—C11—C12—C13	−177.3 (2)
C2—C3—C4—C5	0.0 (4)	C7—N2—C13—C12	−178.3 (2)
C3—C4—C5—C6	−0.4 (4)	C7—N2—C13—C8	0.8 (3)
C2—C1—C6—C5	0.2 (4)	C11—C12—C13—N2	179.7 (2)
C2—C1—C6—C7	178.8 (2)	C11—C12—C13—C8	0.6 (3)
C4—C5—C6—C1	0.3 (4)	N1—C8—C13—N2	−0.6 (3)
C4—C5—C6—C7	−178.3 (3)	C9—C8—C13—N2	178.5 (2)
C13—N2—C7—N1	−0.7 (3)	N1—C8—C13—C12	178.6 (2)
C13—N2—C7—C6	−179.7 (2)	C9—C8—C13—C12	−2.3 (4)
C8—N1—C7—N2	0.3 (3)	C15—O2—C14—O1	−1.6 (4)
C17—N1—C7—N2	168.1 (2)	C15—O2—C14—C11	178.4 (2)
C8—N1—C7—C6	179.4 (2)	C12—C11—C14—O1	−179.9 (2)
C17—N1—C7—C6	−12.9 (4)	C10—C11—C14—O1	1.9 (4)
C1—C6—C7—N2	−66.1 (3)	C12—C11—C14—O2	0.1 (3)
C5—C6—C7—N2	112.4 (3)	C10—C11—C14—O2	−178.1 (2)
C1—C6—C7—N1	114.9 (3)	C14—O2—C15—C16	170.8 (2)
C5—C6—C7—N1	−66.5 (3)	C7—N1—C17—C20	120.4 (3)
C7—N1—C8—C9	−178.8 (3)	C8—N1—C17—C20	−74.4 (3)
C17—N1—C8—C9	13.8 (4)	C7—N1—C17—C18	−110.3 (3)
C7—N1—C8—C13	0.2 (2)	C8—N1—C17—C18	54.9 (3)
C17—N1—C8—C13	−167.3 (2)	N1—C17—C18—C19	53.6 (3)
N1—C8—C9—C10	−178.9 (2)	C20—C17—C18—C19	−178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21C···O1i	0.96	2.47	3.389 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21C⋯O1i	0.96	2.47	3.389 (4)	161

Symmetry code: (i) .