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

In the title compound, C(20)H(21)BrN(2)O(2), the bromo-phenyl ring is twisted by 40.13 (8)° from the benzimidazole mean plane and the Br atom deviates by 0.753 (1) Å from that plane. The sec-butyl group is disordered over two conformations in a 0.898 (5):0.102 (5) ratio. In the crystal, mol-ecules related by translation along [[Formula: see text]10] are linked into chains via weak C-H⋯Br hydrogen bonds.

Related literature

For the synthesis and closely related structures, see: Arumugam et al. (2010 ▶, 2011 ▶); Navarrete-Vazquez et al. (2006 ▶). For therapeutic properties of benzimidazole derivatives, see: Vitale et al. (2008 ▶, 2009 ▶); Arienti et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H21BrN2O2

M = 401.30

Monoclinic,

a = 10.5187 (2) Å

b = 12.7525 (2) Å

c = 13.7444 (2) Å

β = 98.101 (1)°

V = 1825.27 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.27 mm−1

T = 100 K

0.39 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.471, T max = 0.666

24453 measured reflections

3221 independent reflections

3073 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.056

S = 1.08

3221 reflections

248 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.24 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/S1600536811048999/cv5201sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048999/cv5201Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048999/cv5201Isup3.cml

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

C20H21BrN2O2	F(000) = 824
Mr = 401.30	Dx = 1.460 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15956 reflections
a = 10.5187 (2) Å	θ = 1.9–25.0°
b = 12.7525 (2) Å	µ = 2.27 mm−1
c = 13.7444 (2) Å	T = 100 K
β = 98.101 (1)°	Block, colourless
V = 1825.27 (5) Å3	0.39 × 0.39 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3221 independent reflections
Radiation source: fine-focus sealed tube	3073 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 1.9°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
Tmin = 0.471, Tmax = 0.666	l = −16→16
24453 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0253P)2 + 1.2079P] where P = (Fo2 + 2Fc2)/3
3221 reflections	(Δ/σ)max < 0.001
248 parameters	Δρmax = 0.30 e Å−3
12 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open=flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
Br1	1.437653 (17)	−0.132336 (14)	0.052952 (13)	0.02810 (7)
O1	0.49686 (12)	0.48183 (10)	0.16898 (9)	0.0271 (3)
O2	0.66303 (12)	0.53232 (9)	0.09400 (9)	0.0257 (3)
N1	0.97007 (13)	0.22220 (11)	0.12388 (10)	0.0189 (3)
N2	0.87714 (13)	0.08790 (11)	0.19561 (10)	0.0196 (3)
C1	1.21317 (17)	0.10333 (14)	0.14588 (12)	0.0216 (4)
H1A	1.2249	0.1737	0.1680	0.026*
C2	1.31726 (17)	0.04696 (14)	0.12213 (12)	0.0224 (4)
H2A	1.4001	0.0780	0.1278	0.027*
C3	1.29818 (16)	−0.05549 (14)	0.08999 (12)	0.0212 (4)
C4	1.17921 (17)	−0.10309 (14)	0.08218 (12)	0.0222 (4)
H4A	1.1684	−0.1738	0.0608	0.027*
C5	1.07572 (17)	−0.04590 (13)	0.10604 (12)	0.0211 (4)
H5A	0.9933	−0.0777	0.1008	0.025*
C6	1.09155 (16)	0.05814 (13)	0.13774 (11)	0.0190 (3)
C7	0.98140 (16)	0.12428 (13)	0.15413 (12)	0.0187 (3)
C8	0.79159 (16)	0.17113 (13)	0.19091 (12)	0.0191 (3)
C9	0.67050 (16)	0.18299 (14)	0.22094 (12)	0.0212 (4)
H9A	0.6311	0.1276	0.2520	0.025*
C10	0.61127 (16)	0.27893 (14)	0.20317 (12)	0.0204 (3)
H10A	0.5289	0.2896	0.2223	0.024*
C11	0.66927 (16)	0.36167 (13)	0.15738 (12)	0.0189 (3)
C12	0.78936 (16)	0.34958 (13)	0.12819 (12)	0.0185 (3)
H12A	0.8283	0.4051	0.0970	0.022*
C13	0.85105 (16)	0.25334 (13)	0.14619 (12)	0.0178 (3)
C14	0.59928 (16)	0.46288 (13)	0.14229 (12)	0.0204 (4)
C15	0.60340 (19)	0.63412 (14)	0.07495 (14)	0.0282 (4)
H15A	0.6069	0.6746	0.1367	0.034*
H15B	0.5124	0.6260	0.0457	0.034*
C16	0.6779 (2)	0.68923 (16)	0.00444 (17)	0.0381 (5)
H16A	0.6410	0.7589	−0.0107	0.057*
H16B	0.6736	0.6482	−0.0563	0.057*
H16C	0.7677	0.6965	0.0343	0.057*
C17A	0.8740 (2)	−0.00625 (16)	0.25876 (16)	0.0213 (5)	0.898 (5)
H17A	0.9573	−0.0439	0.2583	0.026*	0.898 (5)
C18A	0.8681 (3)	0.0262 (2)	0.36369 (17)	0.0287 (6)	0.898 (5)
H18A	0.8781	−0.0366	0.4065	0.034*	0.898 (5)
H18B	0.7829	0.0574	0.3683	0.034*	0.898 (5)
C19A	0.9724 (2)	0.10532 (19)	0.39981 (15)	0.0306 (6)	0.898 (5)
H19A	0.9687	0.1218	0.4690	0.046*	0.898 (5)
H19B	0.9591	0.1695	0.3605	0.046*	0.898 (5)
H19C	1.0567	0.0756	0.3932	0.046*	0.898 (5)
C20A	0.7673 (2)	−0.08225 (17)	0.21800 (19)	0.0308 (6)	0.898 (5)
H20A	0.7736	−0.0974	0.1489	0.046*	0.898 (5)
H20B	0.6836	−0.0505	0.2230	0.046*	0.898 (5)
H20C	0.7762	−0.1475	0.2559	0.046*	0.898 (5)
C17B	0.9167 (17)	0.0113 (12)	0.2755 (10)	0.065 (13)*	0.102 (5)
H17B	0.9988	−0.0258	0.2688	0.077*	0.102 (5)
C18B	0.9091 (19)	0.0503 (16)	0.3795 (13)	0.017 (5)*	0.102 (5)
H18C	0.9461	−0.0025	0.4271	0.025*	0.102 (5)
H18D	0.8191	0.0623	0.3873	0.025*	0.102 (5)
H18E	0.9572	0.1160	0.3909	0.025*	0.102 (5)
C19B	0.8038 (18)	−0.0613 (15)	0.2757 (13)	0.032 (5)*	0.102 (5)
H19D	0.7256	−0.0199	0.2814	0.038*	0.102 (5)
H19E	0.8194	−0.1090	0.3329	0.038*	0.102 (5)
C20B	0.784 (2)	−0.1251 (15)	0.1810 (12)	0.029 (5)*	0.102 (5)
H20D	0.7084	−0.1703	0.1806	0.043*	0.102 (5)
H20E	0.8599	−0.1685	0.1771	0.043*	0.102 (5)
H20F	0.7704	−0.0776	0.1245	0.043*	0.102 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.02917 (11)	0.02848 (11)	0.02913 (11)	0.01432 (7)	0.01271 (8)	0.00389 (7)
O1	0.0221 (6)	0.0268 (7)	0.0341 (7)	0.0081 (5)	0.0097 (5)	0.0009 (5)
O2	0.0261 (7)	0.0199 (6)	0.0332 (7)	0.0098 (5)	0.0111 (5)	0.0060 (5)
N1	0.0185 (7)	0.0185 (7)	0.0205 (7)	0.0036 (6)	0.0059 (6)	0.0023 (6)
N2	0.0205 (7)	0.0177 (7)	0.0221 (7)	0.0038 (6)	0.0079 (6)	0.0056 (6)
C1	0.0252 (9)	0.0180 (8)	0.0225 (8)	0.0037 (7)	0.0061 (7)	0.0018 (7)
C2	0.0200 (8)	0.0245 (9)	0.0235 (9)	0.0033 (7)	0.0056 (7)	0.0042 (7)
C3	0.0230 (9)	0.0240 (9)	0.0178 (8)	0.0111 (7)	0.0073 (7)	0.0044 (7)
C4	0.0292 (9)	0.0183 (8)	0.0193 (8)	0.0050 (7)	0.0044 (7)	0.0015 (7)
C5	0.0219 (9)	0.0207 (8)	0.0208 (8)	0.0020 (7)	0.0038 (7)	0.0034 (7)
C6	0.0210 (8)	0.0207 (8)	0.0163 (8)	0.0050 (7)	0.0060 (6)	0.0054 (6)
C7	0.0190 (8)	0.0199 (9)	0.0177 (8)	0.0024 (7)	0.0045 (6)	0.0017 (6)
C8	0.0202 (8)	0.0193 (8)	0.0181 (8)	0.0032 (7)	0.0039 (6)	0.0017 (6)
C9	0.0211 (9)	0.0226 (9)	0.0212 (8)	0.0008 (7)	0.0072 (7)	0.0030 (7)
C10	0.0172 (8)	0.0264 (9)	0.0184 (8)	0.0031 (7)	0.0054 (6)	−0.0002 (7)
C11	0.0204 (8)	0.0198 (8)	0.0162 (8)	0.0033 (7)	0.0017 (6)	−0.0015 (6)
C12	0.0200 (8)	0.0178 (8)	0.0182 (8)	0.0013 (6)	0.0041 (6)	0.0008 (6)
C13	0.0178 (8)	0.0196 (8)	0.0164 (8)	0.0021 (7)	0.0033 (6)	0.0002 (6)
C14	0.0207 (9)	0.0225 (9)	0.0178 (8)	0.0037 (7)	0.0018 (7)	−0.0018 (7)
C15	0.0311 (10)	0.0209 (9)	0.0341 (10)	0.0121 (7)	0.0099 (8)	0.0054 (7)
C16	0.0394 (12)	0.0276 (11)	0.0508 (13)	0.0134 (9)	0.0183 (10)	0.0105 (9)
C17A	0.0196 (12)	0.0163 (10)	0.0300 (11)	0.0046 (9)	0.0106 (9)	0.0119 (8)
C18A	0.0251 (13)	0.0367 (14)	0.0253 (11)	0.0060 (11)	0.0067 (10)	0.0112 (10)
C19A	0.0321 (12)	0.0402 (13)	0.0197 (10)	0.0122 (10)	0.0039 (8)	0.0018 (9)
C20A	0.0260 (11)	0.0210 (11)	0.0469 (15)	−0.0032 (9)	0.0106 (10)	0.0020 (11)

Br1—C3	1.8927 (16)	C15—C16	1.504 (3)
O1—C14	1.210 (2)	C15—H15A	0.9900
O2—C14	1.342 (2)	C15—H15B	0.9900
O2—C15	1.450 (2)	C16—H16A	0.9800
N1—C7	1.316 (2)	C16—H16B	0.9800
N1—C13	1.388 (2)	C16—H16C	0.9800
N2—C7	1.385 (2)	C17A—C18A	1.510 (3)
N2—C8	1.387 (2)	C17A—C20A	1.528 (4)
N2—C17B	1.484 (5)	C17A—H17A	1.0000
N2—C17A	1.485 (2)	C18A—C19A	1.522 (4)
C1—C2	1.387 (2)	C18A—H18A	0.9900
C1—C6	1.393 (2)	C18A—H18B	0.9900
C1—H1A	0.9500	C19A—H19A	0.9800
C2—C3	1.385 (3)	C19A—H19B	0.9800
C2—H2A	0.9500	C19A—H19C	0.9800
C3—C4	1.381 (3)	C20A—H20A	0.9800
C4—C5	1.387 (2)	C20A—H20B	0.9800
C4—H4A	0.9500	C20A—H20C	0.9800
C5—C6	1.399 (2)	C17B—C19B	1.507 (6)
C5—H5A	0.9500	C17B—C18B	1.526 (6)
C6—C7	1.476 (2)	C17B—H17B	1.0000
C8—C9	1.401 (2)	C18B—H18C	0.9800
C8—C13	1.406 (2)	C18B—H18D	0.9800
C9—C10	1.379 (2)	C18B—H18E	0.9800
C9—H9A	0.9500	C19B—C20B	1.524 (6)
C10—C11	1.411 (2)	C19B—H19D	0.9900
C10—H10A	0.9500	C19B—H19E	0.9900
C11—C12	1.387 (2)	C20B—H20D	0.9800
C11—C14	1.486 (2)	C20B—H20E	0.9800
C12—C13	1.394 (2)	C20B—H20F	0.9800
C12—H12A	0.9500
C14—O2—C15	116.53 (13)	O2—C14—C11	111.71 (14)
C7—N1—C13	104.23 (14)	O2—C15—C16	106.46 (14)
C7—N2—C8	105.69 (13)	O2—C15—H15A	110.4
C7—N2—C17B	111.6 (7)	C16—C15—H15A	110.4
C8—N2—C17B	130.6 (7)	O2—C15—H15B	110.4
C7—N2—C17A	126.56 (15)	C16—C15—H15B	110.4
C8—N2—C17A	125.33 (14)	H15A—C15—H15B	108.6
C17B—N2—C17A	20.4 (7)	C15—C16—H16A	109.5
C2—C1—C6	120.87 (16)	C15—C16—H16B	109.5
C2—C1—H1A	119.6	H16A—C16—H16B	109.5
C6—C1—H1A	119.6	C15—C16—H16C	109.5
C3—C2—C1	118.72 (16)	H16A—C16—H16C	109.5
C3—C2—H2A	120.6	H16B—C16—H16C	109.5
C1—C2—H2A	120.6	N2—C17A—C18A	110.12 (18)
C4—C3—C2	121.90 (16)	N2—C17A—C20A	111.97 (19)
C4—C3—Br1	118.66 (13)	C18A—C17A—C20A	113.38 (19)
C2—C3—Br1	119.43 (13)	N2—C17A—H17A	107.0
C3—C4—C5	118.88 (16)	C18A—C17A—H17A	107.0
C3—C4—H4A	120.6	C20A—C17A—H17A	107.0
C5—C4—H4A	120.6	C17A—C18A—C19A	111.61 (19)
C4—C5—C6	120.61 (16)	C17A—C18A—H18A	109.3
C4—C5—H5A	119.7	C19A—C18A—H18A	109.3
C6—C5—H5A	119.7	C17A—C18A—H18B	109.3
C1—C6—C5	119.01 (15)	C19A—C18A—H18B	109.3
C1—C6—C7	118.89 (15)	H18A—C18A—H18B	108.0
C5—C6—C7	121.87 (15)	N2—C17B—C19B	105.4 (13)
N1—C7—N2	113.96 (14)	N2—C17B—C18B	115.6 (14)
N1—C7—C6	122.14 (15)	C19B—C17B—C18B	93.0 (3)
N2—C7—C6	123.74 (14)	N2—C17B—H17B	113.6
N2—C8—C9	132.80 (16)	C19B—C17B—H17B	113.6
N2—C8—C13	105.39 (14)	C18B—C17B—H17B	113.6
C9—C8—C13	121.81 (15)	C17B—C18B—H18C	109.5
C10—C9—C8	116.76 (15)	C17B—C18B—H18D	109.5
C10—C9—H9A	121.6	H18C—C18B—H18D	109.5
C8—C9—H9A	121.6	C17B—C18B—H18E	109.5
C9—C10—C11	121.99 (15)	H18C—C18B—H18E	109.5
C9—C10—H10A	119.0	H18D—C18B—H18E	109.5
C11—C10—H10A	119.0	C17B—C19B—C20B	109.9 (15)
C12—C11—C10	120.98 (15)	C17B—C19B—H19D	109.7
C12—C11—C14	120.65 (15)	C20B—C19B—H19D	109.7
C10—C11—C14	118.37 (15)	C17B—C19B—H19E	109.7
C11—C12—C13	117.83 (15)	C20B—C19B—H19E	109.7
C11—C12—H12A	121.1	H19D—C19B—H19E	108.2
C13—C12—H12A	121.1	C19B—C20B—H20D	109.5
N1—C13—C12	128.63 (15)	C19B—C20B—H20E	109.5
N1—C13—C8	110.73 (14)	H20D—C20B—H20E	109.5
C12—C13—C8	120.63 (15)	C19B—C20B—H20F	109.5
O1—C14—O2	123.13 (15)	H20D—C20B—H20F	109.5
O1—C14—C11	125.15 (16)	H20E—C20B—H20F	109.5
C6—C1—C2—C3	0.0 (3)	C10—C11—C12—C13	−0.4 (2)
C1—C2—C3—C4	−0.8 (3)	C14—C11—C12—C13	178.76 (15)
C1—C2—C3—Br1	177.88 (12)	C7—N1—C13—C12	−178.63 (17)
C2—C3—C4—C5	0.9 (3)	C7—N1—C13—C8	0.12 (18)
Br1—C3—C4—C5	−177.81 (12)	C11—C12—C13—N1	179.76 (16)
C3—C4—C5—C6	−0.2 (2)	C11—C12—C13—C8	1.1 (2)
C2—C1—C6—C5	0.6 (2)	N2—C8—C13—N1	−0.08 (18)
C2—C1—C6—C7	−173.87 (15)	C9—C8—C13—N1	179.70 (15)
C4—C5—C6—C1	−0.6 (2)	N2—C8—C13—C12	178.78 (15)
C4—C5—C6—C7	173.78 (15)	C9—C8—C13—C12	−1.4 (3)
C13—N1—C7—N2	−0.12 (19)	C15—O2—C14—O1	0.4 (2)
C13—N1—C7—C6	175.47 (15)	C15—O2—C14—C11	179.89 (14)
C8—N2—C7—N1	0.07 (19)	C12—C11—C14—O1	−176.80 (16)
C17B—N2—C7—N1	−146.9 (8)	C10—C11—C14—O1	2.4 (3)
C17A—N2—C7—N1	−162.89 (18)	C12—C11—C14—O2	3.7 (2)
C8—N2—C7—C6	−175.44 (15)	C10—C11—C14—O2	−177.09 (14)
C17B—N2—C7—C6	37.6 (8)	C14—O2—C15—C16	−169.26 (16)
C17A—N2—C7—C6	21.6 (3)	C7—N2—C17A—C18A	108.4 (2)
C1—C6—C7—N1	38.2 (2)	C8—N2—C17A—C18A	−51.4 (3)
C5—C6—C7—N1	−136.19 (17)	C17B—N2—C17A—C18A	61 (2)
C1—C6—C7—N2	−146.68 (16)	C7—N2—C17A—C20A	−124.5 (2)
C5—C6—C7—N2	39.0 (2)	C8—N2—C17A—C20A	75.7 (2)
C7—N2—C8—C9	−179.74 (18)	C17B—N2—C17A—C20A	−172 (2)
C17B—N2—C8—C9	−41.6 (10)	N2—C17A—C18A—C19A	−51.2 (2)
C17A—N2—C8—C9	−16.5 (3)	C20A—C17A—C18A—C19A	−177.58 (17)
C7—N2—C8—C13	0.01 (17)	C7—N2—C17B—C19B	−150.3 (8)
C17B—N2—C8—C13	138.2 (10)	C8—N2—C17B—C19B	73.4 (14)
C17A—N2—C8—C13	163.24 (19)	C17A—N2—C17B—C19B	−9.8 (15)
N2—C8—C9—C10	−179.33 (17)	C7—N2—C17B—C18B	108.5 (9)
C13—C8—C9—C10	1.0 (2)	C8—N2—C17B—C18B	−27.8 (16)
C8—C9—C10—C11	−0.2 (2)	C17A—N2—C17B—C18B	−111 (2)
C9—C10—C11—C12	0.0 (3)	N2—C17B—C19B—C20B	66.5 (18)
C9—C10—C11—C14	−179.21 (15)	C18B—C17B—C19B—C20B	−175.9 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Br1i	0.98	2.79	3.533 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Br1i	0.98	2.79	3.533 (2)	133

Symmetry code: (i) .