Ethyl 1-phenyl-2-[4-(trifluoro-meth-oxy)phen-yl]-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(23)H(17)F(3)N(2)O(3), an intra-molecular C-H⋯F hydrogen bond generates an S(6) ring motif. The essentially planar 1H-benzimidazole ring system [maximum deviation = 0.021 (2) Å] forms dihedral angles of 25.00 (10) and 62.53 (11)° with the trifluoro-meth-oxy-substituted benzene and phenyl rings, respectively. The twist of the ethyl acetate group from the least-squares plane of the 1H-benzimidazole ring system is defined by a C(=O)-O-C-C torsion angle of 79.5 (3)°. In the crystal, mol-ecules are linked into a two-dimensional network parallel to the bc plane by weak C-H⋯N and C-H⋯O hydrogen bonds. Weak C-H⋯π inter-actions also observed.

Related literature

For the biological activity of benzimidazoles, see: Lemura et al. (1986 ▶); Zhang et al. (2008 ▶). For related structures, see: Yoon et al. (2011 ▶, 2012a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H17F3N2O3

M = 426.39

Triclinic,

a = 8.0204 (4) Å

b = 10.8943 (6) Å

c = 11.4329 (7) Å

α = 76.706 (4)°

β = 83.269 (4)°

γ = 81.227 (4)°

V = 957.31 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.37 × 0.27 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.977

12437 measured reflections

4388 independent reflections

3028 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.206

S = 1.05

4388 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.42 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/S1600536812034903/lh5511sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034903/lh5511Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034903/lh5511Isup3.cml

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

C23H17F3N2O3	Z = 2
Mr = 426.39	F(000) = 440
Triclinic, P1	Dx = 1.479 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0204 (4) Å	Cell parameters from 2463 reflections
b = 10.8943 (6) Å	θ = 2.6–29.7°
c = 11.4329 (7) Å	µ = 0.12 mm−1
α = 76.706 (4)°	T = 100 K
β = 83.269 (4)°	Block, colourless
γ = 81.227 (4)°	0.37 × 0.27 × 0.20 mm
V = 957.31 (9) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4388 independent reflections
Radiation source: fine-focus sealed tube	3028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.957, Tmax = 0.977	k = −14→14
12437 measured reflections	l = −14→12

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.123P)2] where P = (Fo2 + 2Fc2)/3
4388 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.87 e Å−3
0 restraints	Δρmin = −0.42 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
F1	0.2469 (2)	1.38071 (15)	0.84048 (15)	0.0330 (4)
F2	0.3445 (2)	1.20231 (16)	0.94936 (15)	0.0353 (5)
F3	0.5165 (2)	1.32405 (16)	0.84269 (18)	0.0379 (5)
O1	1.3555 (2)	0.41546 (17)	0.33931 (16)	0.0229 (4)
O2	1.1298 (2)	0.50753 (18)	0.23637 (17)	0.0247 (4)
O3	0.3587 (2)	1.23201 (19)	0.74959 (18)	0.0296 (5)
N1	0.8708 (3)	0.8508 (2)	0.4871 (2)	0.0207 (5)
N2	1.0123 (3)	0.8059 (2)	0.65459 (19)	0.0194 (5)
C1	1.0871 (3)	0.7205 (2)	0.5846 (2)	0.0185 (5)
C2	1.2206 (3)	0.6226 (2)	0.6035 (2)	0.0204 (6)
H2A	1.2800	0.6048	0.6739	0.024*
C3	1.2633 (3)	0.5524 (2)	0.5155 (2)	0.0202 (6)
H3A	1.3536	0.4845	0.5254	0.024*
C4	1.1749 (3)	0.5801 (2)	0.4112 (2)	0.0198 (6)
C5	1.0430 (3)	0.6791 (2)	0.3917 (2)	0.0197 (5)
H5A	0.9847	0.6977	0.3207	0.024*
C6	0.9991 (3)	0.7504 (2)	0.4805 (2)	0.0192 (5)
C7	0.8817 (3)	0.8802 (2)	0.5908 (2)	0.0189 (5)
C8	0.7550 (3)	0.9748 (2)	0.6377 (2)	0.0191 (5)
C9	0.6588 (3)	1.0655 (2)	0.5555 (2)	0.0215 (6)
H9A	0.6823	1.0685	0.4716	0.026*
C10	0.5302 (3)	1.1510 (3)	0.5944 (2)	0.0230 (6)
H10A	0.4667	1.2129	0.5380	0.028*
C11	0.4958 (3)	1.1445 (2)	0.7171 (2)	0.0217 (6)
C12	0.5862 (3)	1.0553 (3)	0.8008 (2)	0.0246 (6)
H12A	0.5601	1.0519	0.8846	0.029*
C13	0.7156 (3)	0.9708 (3)	0.7609 (2)	0.0234 (6)
H13A	0.7784	0.9093	0.8181	0.028*
C14	1.0648 (3)	0.8116 (2)	0.7687 (2)	0.0192 (5)
C15	1.1250 (3)	0.9200 (3)	0.7822 (2)	0.0231 (6)
H15A	1.1384	0.9889	0.7151	0.028*
C16	1.1652 (4)	0.9260 (3)	0.8952 (3)	0.0276 (6)
H16A	1.2042	1.0003	0.9063	0.033*
C17	1.1488 (3)	0.8242 (3)	0.9922 (2)	0.0273 (6)
H17A	1.1755	0.8293	1.0695	0.033*
C18	1.0937 (3)	0.7152 (3)	0.9766 (3)	0.0270 (6)
H18A	1.0854	0.6449	1.0429	0.032*
C19	1.0505 (3)	0.7082 (3)	0.8650 (2)	0.0216 (6)
H19A	1.0116	0.6338	0.8542	0.026*
C20	1.2139 (3)	0.5004 (2)	0.3189 (2)	0.0191 (5)
C21	1.3934 (4)	0.3264 (3)	0.2602 (3)	0.0264 (6)
H21A	1.2869	0.2967	0.2490	0.032*
H21B	1.4691	0.2515	0.2994	0.032*
C22	1.4756 (4)	0.3817 (3)	0.1393 (3)	0.0314 (7)
H22A	1.5059	0.3153	0.0926	0.047*
H22B	1.5781	0.4155	0.1496	0.047*
H22C	1.3968	0.4504	0.0963	0.047*
C23	0.3683 (3)	1.2831 (3)	0.8431 (2)	0.0243 (6)

	U11	U22	U33	U12	U13	U23
F1	0.0296 (9)	0.0283 (9)	0.0357 (10)	0.0098 (7)	0.0045 (7)	−0.0080 (7)
F2	0.0390 (10)	0.0321 (10)	0.0271 (9)	0.0045 (8)	0.0087 (7)	−0.0028 (7)
F3	0.0253 (9)	0.0341 (10)	0.0577 (12)	−0.0051 (7)	0.0036 (8)	−0.0194 (9)
O1	0.0208 (9)	0.0244 (10)	0.0220 (10)	0.0033 (7)	0.0008 (7)	−0.0077 (8)
O2	0.0235 (10)	0.0285 (11)	0.0222 (10)	−0.0004 (8)	−0.0027 (8)	−0.0071 (8)
O3	0.0225 (10)	0.0368 (12)	0.0281 (11)	0.0106 (8)	−0.0037 (8)	−0.0125 (9)
N1	0.0180 (10)	0.0213 (12)	0.0201 (11)	−0.0009 (9)	0.0020 (9)	−0.0022 (9)
N2	0.0175 (10)	0.0197 (11)	0.0190 (11)	0.0012 (8)	0.0008 (8)	−0.0035 (9)
C1	0.0163 (12)	0.0209 (13)	0.0185 (13)	−0.0044 (10)	0.0022 (10)	−0.0054 (10)
C2	0.0190 (12)	0.0238 (14)	0.0175 (13)	−0.0027 (10)	−0.0020 (10)	−0.0026 (10)
C3	0.0162 (12)	0.0216 (14)	0.0208 (13)	−0.0012 (10)	0.0025 (10)	−0.0033 (11)
C4	0.0191 (12)	0.0185 (13)	0.0204 (13)	−0.0054 (10)	0.0057 (10)	−0.0034 (10)
C5	0.0184 (12)	0.0231 (14)	0.0165 (13)	−0.0027 (10)	−0.0011 (10)	−0.0022 (10)
C6	0.0147 (11)	0.0202 (13)	0.0206 (13)	−0.0012 (10)	0.0032 (10)	−0.0034 (10)
C7	0.0165 (12)	0.0202 (13)	0.0183 (13)	−0.0034 (10)	−0.0013 (10)	−0.0003 (10)
C8	0.0172 (12)	0.0185 (13)	0.0213 (13)	−0.0033 (10)	−0.0003 (10)	−0.0042 (10)
C9	0.0214 (13)	0.0257 (14)	0.0159 (13)	−0.0037 (10)	0.0016 (10)	−0.0030 (11)
C10	0.0196 (13)	0.0245 (14)	0.0228 (14)	−0.0003 (10)	−0.0038 (10)	−0.0016 (11)
C11	0.0163 (12)	0.0238 (14)	0.0243 (14)	0.0020 (10)	0.0016 (10)	−0.0086 (11)
C12	0.0211 (13)	0.0319 (16)	0.0185 (13)	0.0013 (11)	0.0008 (10)	−0.0054 (11)
C13	0.0213 (13)	0.0242 (14)	0.0211 (14)	0.0010 (11)	−0.0018 (10)	−0.0004 (11)
C14	0.0143 (12)	0.0242 (14)	0.0172 (13)	0.0028 (10)	0.0005 (10)	−0.0050 (10)
C15	0.0196 (13)	0.0245 (14)	0.0235 (14)	−0.0021 (10)	0.0030 (10)	−0.0046 (11)
C16	0.0237 (14)	0.0324 (16)	0.0289 (15)	−0.0056 (12)	0.0002 (11)	−0.0112 (13)
C17	0.0203 (13)	0.0425 (18)	0.0198 (14)	0.0028 (12)	−0.0029 (11)	−0.0121 (12)
C18	0.0198 (13)	0.0331 (16)	0.0230 (14)	0.0011 (11)	0.0012 (11)	−0.0001 (12)
C19	0.0161 (12)	0.0214 (13)	0.0249 (14)	0.0021 (10)	0.0009 (10)	−0.0047 (11)
C20	0.0174 (12)	0.0199 (13)	0.0178 (13)	−0.0028 (10)	0.0034 (10)	−0.0015 (10)
C21	0.0267 (14)	0.0229 (15)	0.0302 (15)	0.0027 (11)	−0.0028 (12)	−0.0109 (12)
C22	0.0265 (15)	0.0397 (18)	0.0287 (16)	−0.0009 (13)	0.0022 (12)	−0.0132 (13)
C23	0.0212 (13)	0.0245 (14)	0.0249 (14)	0.0000 (10)	0.0001 (11)	−0.0035 (11)

F1—C23	1.326 (3)	C9—C10	1.385 (4)
F2—C23	1.339 (3)	C9—H9A	0.9500
F3—C23	1.331 (3)	C10—C11	1.385 (4)
O1—C20	1.357 (3)	C10—H10A	0.9500
O1—C21	1.449 (3)	C11—C12	1.380 (4)
O2—C20	1.205 (3)	C12—C13	1.386 (4)
O3—C23	1.328 (3)	C12—H12A	0.9500
O3—C11	1.416 (3)	C13—H13A	0.9500
N1—C7	1.314 (3)	C14—C15	1.388 (4)
N1—C6	1.392 (3)	C14—C19	1.390 (4)
N2—C1	1.388 (3)	C15—C16	1.386 (4)
N2—C7	1.390 (3)	C15—H15A	0.9500
N2—C14	1.434 (3)	C16—C17	1.386 (4)
C1—C2	1.389 (4)	C16—H16A	0.9500
C1—C6	1.403 (4)	C17—C18	1.383 (4)
C2—C3	1.381 (4)	C17—H17A	0.9500
C2—H2A	0.9500	C18—C19	1.383 (4)
C3—C4	1.408 (4)	C18—H18A	0.9500
C3—H3A	0.9500	C19—H19A	0.9500
C4—C5	1.389 (4)	C21—C22	1.494 (4)
C4—C20	1.491 (3)	C21—H21A	0.9900
C5—C6	1.398 (3)	C21—H21B	0.9900
C5—H5A	0.9500	C22—H22A	0.9800
C7—C8	1.479 (3)	C22—H22B	0.9800
C8—C13	1.400 (4)	C22—H22C	0.9800
C8—C9	1.402 (4)
C20—O1—C21	115.6 (2)	C12—C13—C8	121.0 (2)
C23—O3—C11	118.9 (2)	C12—C13—H13A	119.5
C7—N1—C6	105.1 (2)	C8—C13—H13A	119.5
C1—N2—C7	105.7 (2)	C15—C14—C19	121.2 (2)
C1—N2—C14	124.9 (2)	C15—C14—N2	120.0 (2)
C7—N2—C14	129.3 (2)	C19—C14—N2	118.8 (2)
N2—C1—C2	131.5 (2)	C16—C15—C14	118.8 (3)
N2—C1—C6	105.9 (2)	C16—C15—H15A	120.6
C2—C1—C6	122.6 (2)	C14—C15—H15A	120.6
C3—C2—C1	117.1 (2)	C17—C16—C15	120.4 (3)
C3—C2—H2A	121.4	C17—C16—H16A	119.8
C1—C2—H2A	121.4	C15—C16—H16A	119.8
C2—C3—C4	121.0 (2)	C18—C17—C16	120.2 (3)
C2—C3—H3A	119.5	C18—C17—H17A	119.9
C4—C3—H3A	119.5	C16—C17—H17A	119.9
C5—C4—C3	121.8 (2)	C19—C18—C17	120.2 (3)
C5—C4—C20	116.9 (2)	C19—C18—H18A	119.9
C3—C4—C20	121.3 (2)	C17—C18—H18A	119.9
C4—C5—C6	117.5 (2)	C18—C19—C14	119.1 (3)
C4—C5—H5A	121.2	C18—C19—H19A	120.4
C6—C5—H5A	121.2	C14—C19—H19A	120.4
N1—C6—C5	130.0 (2)	O2—C20—O1	122.9 (2)
N1—C6—C1	110.0 (2)	O2—C20—C4	124.9 (2)
C5—C6—C1	120.0 (2)	O1—C20—C4	112.2 (2)
N1—C7—N2	113.3 (2)	O1—C21—C22	113.5 (2)
N1—C7—C8	121.9 (2)	O1—C21—H21A	108.9
N2—C7—C8	124.5 (2)	C22—C21—H21A	108.9
C13—C8—C9	118.2 (2)	O1—C21—H21B	108.9
C13—C8—C7	123.1 (2)	C22—C21—H21B	108.9
C9—C8—C7	118.4 (2)	H21A—C21—H21B	107.7
C10—C9—C8	121.2 (2)	C21—C22—H22A	109.5
C10—C9—H9A	119.4	C21—C22—H22B	109.5
C8—C9—H9A	119.4	H22A—C22—H22B	109.5
C11—C10—C9	118.8 (2)	C21—C22—H22C	109.5
C11—C10—H10A	120.6	H22A—C22—H22C	109.5
C9—C10—H10A	120.6	H22B—C22—H22C	109.5
C12—C11—C10	121.7 (2)	F1—C23—O3	108.2 (2)
C12—C11—O3	123.0 (2)	F1—C23—F3	108.7 (2)
C10—C11—O3	115.2 (2)	O3—C23—F3	113.3 (2)
C11—C12—C13	119.1 (2)	F1—C23—F2	107.1 (2)
C11—C12—H12A	120.4	O3—C23—F2	113.0 (2)
C13—C12—H12A	120.4	F3—C23—F2	106.4 (2)
C7—N2—C1—C2	−178.7 (3)	C9—C10—C11—C12	−0.1 (4)
C14—N2—C1—C2	1.3 (4)	C9—C10—C11—O3	−177.8 (2)
C7—N2—C1—C6	1.3 (3)	C23—O3—C11—C12	38.5 (4)
C14—N2—C1—C6	−178.7 (2)	C23—O3—C11—C10	−143.8 (3)
N2—C1—C2—C3	178.9 (2)	C10—C11—C12—C13	0.5 (4)
C6—C1—C2—C3	−1.1 (4)	O3—C11—C12—C13	178.1 (2)
C1—C2—C3—C4	0.3 (4)	C11—C12—C13—C8	−0.1 (4)
C2—C3—C4—C5	0.6 (4)	C9—C8—C13—C12	−0.8 (4)
C2—C3—C4—C20	−176.7 (2)	C7—C8—C13—C12	−174.7 (2)
C3—C4—C5—C6	−0.7 (4)	C1—N2—C14—C15	117.3 (3)
C20—C4—C5—C6	176.8 (2)	C7—N2—C14—C15	−62.7 (4)
C7—N1—C6—C5	177.8 (3)	C1—N2—C14—C19	−64.2 (3)
C7—N1—C6—C1	0.2 (3)	C7—N2—C14—C19	115.8 (3)
C4—C5—C6—N1	−177.7 (3)	C19—C14—C15—C16	−2.4 (4)
C4—C5—C6—C1	−0.2 (4)	N2—C14—C15—C16	176.1 (2)
N2—C1—C6—N1	−1.0 (3)	C14—C15—C16—C17	1.3 (4)
C2—C1—C6—N1	179.1 (2)	C15—C16—C17—C18	0.6 (4)
N2—C1—C6—C5	−178.9 (2)	C16—C17—C18—C19	−1.6 (4)
C2—C1—C6—C5	1.1 (4)	C17—C18—C19—C14	0.6 (4)
C6—N1—C7—N2	0.8 (3)	C15—C14—C19—C18	1.4 (4)
C6—N1—C7—C8	−173.6 (2)	N2—C14—C19—C18	−177.1 (2)
C1—N2—C7—N1	−1.4 (3)	C21—O1—C20—O2	−4.3 (4)
C14—N2—C7—N1	178.6 (2)	C21—O1—C20—C4	174.5 (2)
C1—N2—C7—C8	172.8 (2)	C5—C4—C20—O2	−7.8 (4)
C14—N2—C7—C8	−7.2 (4)	C3—C4—C20—O2	169.6 (3)
N1—C7—C8—C13	151.2 (3)	C5—C4—C20—O1	173.4 (2)
N2—C7—C8—C13	−22.5 (4)	C3—C4—C20—O1	−9.2 (3)
N1—C7—C8—C9	−22.7 (4)	C20—O1—C21—C22	79.5 (3)
N2—C7—C8—C9	163.6 (2)	C11—O3—C23—F1	166.4 (2)
C13—C8—C9—C10	1.3 (4)	C11—O3—C23—F3	45.8 (3)
C7—C8—C9—C10	175.5 (2)	C11—O3—C23—F2	−75.2 (3)
C8—C9—C10—C11	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···F2	0.95	2.37	2.956 (3)	120
C15—H15A···N1i	0.95	2.56	3.490 (3)	167
C18—H18A···O2ii	0.95	2.40	3.307 (4)	160
C19—H19A···O2iii	0.95	2.50	3.412 (3)	160
C13—H13A···Cg1	0.95	2.79	3.592 (3)	142
C21—H21A···Cg2iii	0.99	2.95	3.634 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14–C19 and N1/N2/C1/C6/C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯F2	0.95	2.37	2.956 (3)	120
C15—H15A⋯N1i	0.95	2.56	3.490 (3)	167
C18—H18A⋯O2ii	0.95	2.40	3.307 (4)	160
C19—H19A⋯O2iii	0.95	2.50	3.412 (3)	160
C13—H13A⋯Cg1	0.95	2.79	3.592 (3)	142
C21—H21A⋯Cg2iii	0.99	2.95	3.634 (3)	127

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