Ethyl 1-tert-butyl-2-(4-hydr-oxy-3-methoxy-phen-yl)-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(21)H(24)N(2)O(4), the benzimidazole ring system is almost planar, with a maximum deviation of 0.047 (1) Å and makes a dihedral angle of 88.44 (5)° with the attached benzene ring. In the crystal, mol-ecules form infinite chains along the b axis by way of inter-molecular O-H⋯N and C-H⋯O inter-actions. Weak C-H⋯π also contribute to the stabilization of the crystal structure.

Related literature

For the biological properties of benzimidazole-based heterocyclic compounds, see: Townsend et al. (1970 ▶); Blythin et al. (1986 ▶); Lemura et al. (1986 ▶); Zhang et al. (2008 ▶); Bonfanti et al. (2008 ▶); Ozden et al. (2008 ▶). For related structures, see Arumugam, Abd Hamid et al. (2010 ▶); Arumugam, Abdul Rahim, Abd Hamid et al. (2010 ▶); Arumugam, Abdul Rahim, Osman et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H24N2O4

M = 368.42

Monoclinic,

a = 9.2610 (6) Å

b = 13.6096 (9) Å

c = 16.3200 (9) Å

β = 113.560 (3)°

V = 1885.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.38 × 0.23 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.967, T max = 0.986

21041 measured reflections

5484 independent reflections

4104 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.134

S = 1.07

5484 reflections

253 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536810011918/wn2380sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011918/wn2380Isup2.hkl

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

C21H24N2O4	F(000) = 784
Mr = 368.42	Dx = 1.298 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4617 reflections
a = 9.2610 (6) Å	θ = 2.4–30.0°
b = 13.6096 (9) Å	µ = 0.09 mm−1
c = 16.3200 (9) Å	T = 100 K
β = 113.560 (3)°	Block, colourless
V = 1885.5 (2) Å3	0.38 × 0.23 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5484 independent reflections
Radiation source: fine-focus sealed tube	4104 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.967, Tmax = 0.986	k = −16→19
21041 measured reflections	l = −22→22

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) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.3983P] where P = (Fo2 + 2Fc2)/3
5484 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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

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	0.07059 (12)	−0.06665 (7)	0.77515 (6)	0.0237 (2)
O2	−0.19758 (11)	0.02786 (7)	0.67345 (6)	0.0254 (2)
O3	0.35717 (13)	0.74808 (8)	0.53807 (7)	0.0364 (3)
O4	0.36828 (12)	0.71957 (7)	0.67609 (7)	0.0287 (2)
N1	0.14388 (13)	0.37334 (8)	0.65777 (7)	0.0217 (2)
N2	0.14885 (12)	0.29733 (8)	0.53582 (7)	0.0188 (2)
C1	0.18878 (14)	0.44031 (9)	0.60878 (8)	0.0197 (2)
C2	0.23604 (15)	0.53759 (9)	0.63023 (9)	0.0216 (3)
H2A	0.2337	0.5669	0.6812	0.026*
C3	0.28664 (15)	0.58934 (10)	0.57327 (9)	0.0226 (3)
C4	0.28918 (17)	0.54393 (11)	0.49670 (9)	0.0280 (3)
H4A	0.3209	0.5803	0.4586	0.034*
C5	0.24598 (17)	0.44675 (11)	0.47600 (9)	0.0266 (3)
H5A	0.2513	0.4171	0.4259	0.032*
C6	0.19403 (14)	0.39470 (9)	0.53306 (8)	0.0189 (2)
C7	0.12336 (15)	0.28957 (9)	0.61386 (8)	0.0191 (2)
C8	0.10037 (15)	0.19642 (9)	0.65461 (8)	0.0200 (2)
C9	0.23493 (16)	0.14552 (10)	0.70872 (9)	0.0230 (3)
H9A	0.3338	0.1700	0.7176	0.028*
C10	0.22263 (15)	0.05846 (10)	0.74952 (8)	0.0225 (3)
H10A	0.3135	0.0253	0.7859	0.027*
C11	0.07666 (15)	0.02047 (9)	0.73664 (8)	0.0200 (2)
C12	−0.05955 (14)	0.07243 (9)	0.68283 (8)	0.0194 (2)
C13	−0.04751 (15)	0.16086 (9)	0.64290 (8)	0.0208 (2)
H13A	−0.1378	0.1959	0.6086	0.025*
C14	0.34014 (15)	0.69310 (10)	0.59183 (10)	0.0259 (3)
C15	0.42106 (18)	0.82010 (11)	0.70149 (11)	0.0345 (3)
H15A	0.3440	0.8664	0.6631	0.041*
H15B	0.5206	0.8316	0.6966	0.041*
C16	0.43956 (19)	0.83178 (12)	0.79658 (12)	0.0391 (4)
H16A	0.4813	0.8958	0.8179	0.059*
H16B	0.5104	0.7825	0.8330	0.059*
H16C	0.3388	0.8245	0.7998	0.059*
C17	0.13687 (15)	0.22114 (10)	0.46624 (8)	0.0216 (3)
C18	0.03674 (17)	0.26257 (11)	0.37384 (9)	0.0288 (3)
H18A	0.0878	0.3193	0.3627	0.043*
H18B	−0.0649	0.2809	0.3715	0.043*
H18C	0.0244	0.2135	0.3292	0.043*
C19	0.30259 (19)	0.19690 (15)	0.47440 (12)	0.0442 (4)
H19A	0.3547	0.2562	0.4694	0.066*
H19B	0.2968	0.1524	0.4276	0.066*
H19C	0.3608	0.1669	0.5314	0.066*
C20	0.0556 (2)	0.12740 (11)	0.47674 (10)	0.0371 (4)
H20A	−0.0449	0.1436	0.4774	0.056*
H20B	0.1198	0.0956	0.5318	0.056*
H20C	0.0406	0.0840	0.4276	0.056*
C21	−0.34028 (17)	0.07449 (12)	0.61686 (11)	0.0351 (3)
H21A	−0.4283	0.0351	0.6138	0.053*
H21B	−0.3418	0.0818	0.5580	0.053*
H21C	−0.3470	0.1381	0.6406	0.053*
H1O1	−0.017 (2)	−0.0742 (15)	0.7803 (13)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0303 (5)	0.0185 (5)	0.0257 (5)	0.0017 (4)	0.0147 (4)	0.0052 (4)
O2	0.0234 (4)	0.0252 (5)	0.0272 (5)	−0.0011 (4)	0.0097 (4)	0.0039 (4)
O3	0.0399 (6)	0.0290 (6)	0.0354 (6)	−0.0100 (4)	0.0098 (5)	0.0102 (4)
O4	0.0335 (5)	0.0167 (5)	0.0321 (5)	−0.0054 (4)	0.0090 (4)	−0.0001 (4)
N1	0.0333 (6)	0.0147 (5)	0.0223 (5)	−0.0016 (4)	0.0165 (4)	−0.0007 (4)
N2	0.0254 (5)	0.0159 (5)	0.0167 (5)	0.0003 (4)	0.0102 (4)	−0.0001 (4)
C1	0.0244 (6)	0.0160 (6)	0.0209 (6)	0.0017 (4)	0.0113 (5)	0.0014 (4)
C2	0.0278 (6)	0.0160 (6)	0.0233 (6)	0.0006 (5)	0.0127 (5)	0.0007 (5)
C3	0.0225 (6)	0.0192 (6)	0.0248 (6)	−0.0014 (5)	0.0082 (5)	0.0035 (5)
C4	0.0327 (7)	0.0291 (7)	0.0236 (6)	−0.0071 (6)	0.0129 (5)	0.0047 (5)
C5	0.0345 (7)	0.0286 (7)	0.0198 (6)	−0.0048 (6)	0.0141 (5)	0.0004 (5)
C6	0.0211 (5)	0.0180 (6)	0.0181 (5)	0.0006 (4)	0.0084 (4)	0.0019 (4)
C7	0.0257 (6)	0.0158 (6)	0.0180 (5)	0.0010 (5)	0.0109 (5)	−0.0001 (4)
C8	0.0308 (6)	0.0139 (5)	0.0175 (5)	−0.0014 (5)	0.0121 (5)	−0.0018 (4)
C9	0.0269 (6)	0.0194 (6)	0.0239 (6)	−0.0012 (5)	0.0115 (5)	0.0002 (5)
C10	0.0254 (6)	0.0199 (6)	0.0221 (6)	0.0022 (5)	0.0096 (5)	0.0019 (5)
C11	0.0292 (6)	0.0156 (6)	0.0170 (5)	0.0004 (5)	0.0112 (5)	−0.0009 (4)
C12	0.0246 (6)	0.0179 (6)	0.0171 (5)	−0.0007 (5)	0.0096 (4)	−0.0017 (4)
C13	0.0278 (6)	0.0174 (6)	0.0174 (5)	0.0010 (5)	0.0093 (5)	−0.0001 (4)
C14	0.0224 (6)	0.0209 (6)	0.0305 (7)	−0.0021 (5)	0.0066 (5)	0.0057 (5)
C15	0.0337 (7)	0.0170 (6)	0.0434 (9)	−0.0045 (5)	0.0055 (6)	0.0015 (6)
C16	0.0315 (7)	0.0257 (8)	0.0512 (10)	0.0000 (6)	0.0072 (7)	−0.0070 (7)
C17	0.0282 (6)	0.0203 (6)	0.0174 (5)	0.0023 (5)	0.0102 (5)	−0.0032 (5)
C18	0.0363 (7)	0.0271 (7)	0.0188 (6)	−0.0016 (6)	0.0066 (5)	−0.0020 (5)
C19	0.0322 (8)	0.0571 (11)	0.0409 (9)	0.0112 (7)	0.0119 (7)	−0.0200 (8)
C20	0.0704 (11)	0.0197 (7)	0.0252 (7)	−0.0065 (7)	0.0235 (7)	−0.0064 (5)
C21	0.0242 (6)	0.0335 (8)	0.0437 (9)	0.0012 (6)	0.0095 (6)	0.0084 (7)

O1—C11	1.3536 (15)	C10—C11	1.3827 (18)
O1—H1O1	0.857 (19)	C10—H10A	0.9300
O2—C12	1.3672 (15)	C11—C12	1.4060 (17)
O2—C21	1.4235 (17)	C12—C13	1.3941 (17)
O3—C14	1.2104 (17)	C13—H13A	0.9300
O4—C14	1.3424 (18)	C15—C16	1.500 (2)
O4—C15	1.4563 (17)	C15—H15A	0.9700
N1—C7	1.3193 (16)	C15—H15B	0.9700
N1—C1	1.3815 (16)	C16—H16A	0.9600
N2—C7	1.3890 (16)	C16—H16B	0.9600
N2—C6	1.3958 (16)	C16—H16C	0.9600
N2—C17	1.5086 (16)	C17—C19	1.523 (2)
C1—C2	1.3945 (17)	C17—C20	1.525 (2)
C1—C6	1.4010 (17)	C17—C18	1.5278 (18)
C2—C3	1.3885 (18)	C18—H18A	0.9600
C2—H2A	0.9300	C18—H18B	0.9600
C3—C4	1.4027 (19)	C18—H18C	0.9600
C3—C14	1.4871 (19)	C19—H19A	0.9600
C4—C5	1.384 (2)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
C5—C6	1.3995 (18)	C20—H20A	0.9600
C5—H5A	0.9300	C20—H20B	0.9600
C7—C8	1.4858 (17)	C20—H20C	0.9600
C8—C9	1.3903 (18)	C21—H21A	0.9600
C8—C13	1.3918 (18)	C21—H21B	0.9600
C9—C10	1.3860 (18)	C21—H21C	0.9600
C9—H9A	0.9300
C11—O1—H1O1	111.5 (13)	O3—C14—O4	123.26 (13)
C12—O2—C21	117.31 (11)	O3—C14—C3	124.66 (14)
C14—O4—C15	116.70 (11)	O4—C14—C3	112.08 (11)
C7—N1—C1	105.49 (10)	O4—C15—C16	106.30 (12)
C7—N2—C6	105.36 (10)	O4—C15—H15A	110.5
C7—N2—C17	130.51 (11)	C16—C15—H15A	110.5
C6—N2—C17	124.12 (10)	O4—C15—H15B	110.5
N1—C1—C2	128.17 (12)	C16—C15—H15B	110.5
N1—C1—C6	110.05 (11)	H15A—C15—H15B	108.7
C2—C1—C6	121.60 (12)	C15—C16—H16A	109.5
C3—C2—C1	118.01 (12)	C15—C16—H16B	109.5
C3—C2—H2A	121.0	H16A—C16—H16B	109.5
C1—C2—H2A	121.0	C15—C16—H16C	109.5
C2—C3—C4	120.21 (12)	H16A—C16—H16C	109.5
C2—C3—C14	121.30 (12)	H16B—C16—H16C	109.5
C4—C3—C14	118.49 (12)	N2—C17—C19	108.35 (11)
C5—C4—C3	122.17 (13)	N2—C17—C20	112.42 (10)
C5—C4—H4A	118.9	C19—C17—C20	109.53 (13)
C3—C4—H4A	118.9	N2—C17—C18	108.80 (11)
C4—C5—C6	117.65 (13)	C19—C17—C18	111.05 (12)
C4—C5—H5A	121.2	C20—C17—C18	106.70 (11)
C6—C5—H5A	121.2	C17—C18—H18A	109.5
N2—C6—C5	133.58 (12)	C17—C18—H18B	109.5
N2—C6—C1	105.99 (10)	H18A—C18—H18B	109.5
C5—C6—C1	120.33 (12)	C17—C18—H18C	109.5
N1—C7—N2	113.08 (11)	H18A—C18—H18C	109.5
N1—C7—C8	120.63 (11)	H18B—C18—H18C	109.5
N2—C7—C8	125.63 (11)	C17—C19—H19A	109.5
C9—C8—C13	119.80 (12)	C17—C19—H19B	109.5
C9—C8—C7	117.19 (11)	H19A—C19—H19B	109.5
C13—C8—C7	122.98 (11)	C17—C19—H19C	109.5
C10—C9—C8	120.41 (12)	H19A—C19—H19C	109.5
C10—C9—H9A	119.8	H19B—C19—H19C	109.5
C8—C9—H9A	119.8	C17—C20—H20A	109.5
C11—C10—C9	120.65 (12)	C17—C20—H20B	109.5
C11—C10—H10A	119.7	H20A—C20—H20B	109.5
C9—C10—H10A	119.7	C17—C20—H20C	109.5
O1—C11—C10	118.45 (11)	H20A—C20—H20C	109.5
O1—C11—C12	122.49 (11)	H20B—C20—H20C	109.5
C10—C11—C12	119.04 (12)	O2—C21—H21A	109.5
O2—C12—C13	125.21 (11)	O2—C21—H21B	109.5
O2—C12—C11	114.33 (11)	H21A—C21—H21B	109.5
C13—C12—C11	120.45 (12)	O2—C21—H21C	109.5
C8—C13—C12	119.62 (12)	H21A—C21—H21C	109.5
C8—C13—H13A	120.2	H21B—C21—H21C	109.5
C12—C13—H13A	120.2
C7—N1—C1—C2	−174.69 (13)	C13—C8—C9—C10	1.40 (19)
C7—N1—C1—C6	0.37 (14)	C7—C8—C9—C10	179.51 (11)
N1—C1—C2—C3	175.59 (12)	C8—C9—C10—C11	0.46 (19)
C6—C1—C2—C3	1.04 (19)	C9—C10—C11—O1	177.51 (11)
C1—C2—C3—C4	0.06 (19)	C9—C10—C11—C12	−1.22 (19)
C1—C2—C3—C14	−179.51 (11)	C21—O2—C12—C13	1.43 (19)
C2—C3—C4—C5	−1.6 (2)	C21—O2—C12—C11	−177.52 (12)
C14—C3—C4—C5	177.98 (13)	O1—C11—C12—O2	0.46 (17)
C3—C4—C5—C6	2.0 (2)	C10—C11—C12—O2	179.14 (11)
C7—N2—C6—C5	174.74 (14)	O1—C11—C12—C13	−178.54 (11)
C17—N2—C6—C5	−4.1 (2)	C10—C11—C12—C13	0.14 (18)
C7—N2—C6—C1	−1.55 (13)	C9—C8—C13—C12	−2.46 (18)
C17—N2—C6—C1	179.58 (11)	C7—C8—C13—C12	179.55 (11)
C4—C5—C6—N2	−176.68 (13)	O2—C12—C13—C8	−177.19 (11)
C4—C5—C6—C1	−0.82 (19)	C11—C12—C13—C8	1.70 (18)
N1—C1—C6—N2	0.77 (14)	C15—O4—C14—O3	0.3 (2)
C2—C1—C6—N2	176.21 (11)	C15—O4—C14—C3	−179.85 (11)
N1—C1—C6—C5	−176.11 (12)	C2—C3—C14—O3	−165.35 (13)
C2—C1—C6—C5	−0.67 (19)	C4—C3—C14—O3	15.1 (2)
C1—N1—C7—N2	−1.44 (14)	C2—C3—C14—O4	14.78 (18)
C1—N1—C7—C8	169.72 (11)	C4—C3—C14—O4	−164.80 (12)
C6—N2—C7—N1	1.92 (14)	C14—O4—C15—C16	178.47 (12)
C17—N2—C7—N1	−179.30 (11)	C7—N2—C17—C19	−108.89 (16)
C6—N2—C7—C8	−168.71 (12)	C6—N2—C17—C19	69.69 (16)
C17—N2—C7—C8	10.1 (2)	C7—N2—C17—C20	12.30 (18)
N1—C7—C8—C9	−86.62 (15)	C6—N2—C17—C20	−169.12 (12)
N2—C7—C8—C9	83.36 (16)	C7—N2—C17—C18	130.27 (13)
N1—C7—C8—C13	91.42 (16)	C6—N2—C17—C18	−51.15 (16)
N2—C7—C8—C13	−98.60 (16)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1i	0.85 (2)	1.97 (2)	2.7475 (17)	151.7 (19)
C2—H2A···O2ii	0.93	2.58	3.3648 (17)	142
C13—H13A···O3iii	0.93	2.56	3.4223 (17)	154
C18—H18B···O4iii	0.96	2.60	3.514 (2)	160
C18—H18C···O1iv	0.96	2.54	3.4753 (17)	163
C18—H18A···Cg1v	0.96	2.89	3.5798 (16)	129
C20—H20B···Cg1	0.96	2.81	3.4764 (17)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1i	0.85 (2)	1.97 (2)	2.7475 (17)	151.7 (19)
C2—H2A⋯O2ii	0.93	2.58	3.3648 (17)	142
C13—H13A⋯O3iii	0.93	2.56	3.4223 (17)	154
C18—H18B⋯O4iii	0.96	2.60	3.514 (2)	160
C18—H18C⋯O1iv	0.96	2.54	3.4753 (17)	163
C18—H18A⋯Cg1v	0.96	2.89	3.5798 (16)	129
C20—H20B⋯Cg1	0.96	2.81	3.4764 (17)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .