Ethyl 1-phenyl-2-[4-(trifluoro­meth­oxy)phen­yl]-1H-benzimidazole-5-carboxyl­ate

Yoon, Y.K.; Ali, M.A.; Choon, T.S.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812034903

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2715-o2716

doi:10.1107/S1600536812034903

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Ethyl 1-phenyl-2-[4-(trifluoromethoxy)phenyl]-1H-benzimidazole-5-carboxylate

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Suhana Arshad ^b and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 31 July 2012; accepted 7 August 2012; online 15 August 2012)

In the title compound, C₂₃H₁₇F₃N₂O₃, an intramolecular 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 trifluoromethoxy-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, molecules 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 interactions 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_r = 426.39
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.075
wR(F²) = 0.206
S = 1.05
4388 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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) -x+2, -y+2, -z+1; (ii) x, y, z+1; (iii) -x+2, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034903/lh5511sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812034903/lh5511Isup3.cml

checkCIF report

Comment top

Benzimidazole-based heterocycles are of wide interest because of their diverse biological activities and various clinical applications. Among various applications, they are known to exhibit antihistamine (Lemura et al., 1986) and immunosuppressive (Zhang et al., 2008) activities. As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we report the structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths and angles are within normal ranges and are comparable to related structures (Yoon et al., 2012a,b,c). An intramolecular C12—H12A···F2 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The essentially planar 1H-benzimidazole ring system [N1/N2/C1–C7, with a maximum deviation of 0.021 (2) Å at atoms C6 and C7] is inclined to the trifluoromethoxy-substituted benzene ring (C8–C13) and the pendant phenyl ring (C14–C19), making dihedral angles of 25.00 (10) and 62.53 (11)°, respectively. The ethyl acetate group (O1/O2/C20–C22) is twisted away from the least-square plane of the 1H-benzimidazole ring at the O1–C21 bond, as indicated by the torsion angle C20—O1—C21—C22 = 79.5 (3)°.

The crystal packing is shown in Fig. 2. Weak intermolecular C15—H15A···N1ⁱ, C18—H18A···O2ⁱⁱ and C19—H19A···O2ⁱⁱⁱ (Table 1) hydrogen bonds link the molecules into a two-dimensional network parallel to the bc-plane. The crystal structure is further stabilized by weak intermolecular C13—H13A···Cg1 and C21—H21A···Cg2 (Table 1) interactions (Cg1 and Cg2 are the centroids of C14–C19 and N1/N2/C1/C6/C7 rings, respectively).

Related literature top

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 top

Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and the sodium metabisulfite adduct of trifluoromethoxy benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed at 403K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and the evaporated in vacuo to yield the product. Crystals were obtained from a solution of the title compound in ethyl acetate.

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a weak hydrogen bond.

Fig. 2. The crystal packing of the title compound viewed along the c-axis. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Ethyl 1-phenyl-2-[4-(trifluoromethoxy)phenyl]-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₃H₁₇F₃N₂O₃	Z = 2
M_r = 426.39	F(000) = 440
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.123P)²] where P = (F_o² + 2F_c²)/3
4388 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₃H₁₇F₃N₂O₃	γ = 81.227 (4)°
M_r = 426.39	V = 957.31 (9) Å³
Triclinic, P1	Z = 2
a = 8.0204 (4) Å	Mo Kα radiation
b = 10.8943 (6) Å	µ = 0.12 mm⁻¹
c = 11.4329 (7) Å	T = 100 K
α = 76.706 (4)°	0.37 × 0.27 × 0.20 mm
β = 83.269 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4388 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3028 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.977	R_int = 0.065
12437 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.206	H-atom parameters constrained
S = 1.05	Δρ_max = 0.87 e Å⁻³
4388 reflections	Δρ_min = −0.42 e Å⁻³
281 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z+1; (ii) x, y, z+1; (iii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇F₃N₂O₃
M_r	426.39
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.0204 (4), 10.8943 (6), 11.4329 (7)
α, β, γ (°)	76.706 (4), 83.269 (4), 81.227 (4)
V (Å³)	957.31 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.37 × 0.27 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.957, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	12437, 4388, 3028
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.206, 1.05
No. of reflections	4388
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.9500	2.37	2.956 (3)	120
C15—H15A···N1ⁱ	0.9500	2.56	3.490 (3)	167
C18—H18A···O2ⁱⁱ	0.9500	2.40	3.307 (4)	160
C19—H19A···O2ⁱⁱⁱ	0.9500	2.50	3.412 (3)	160
C13—H13A···Cg1	0.9500	2.79	3.592 (3)	142
C21—H21A···Cg2ⁱⁱⁱ	0.9900	2.95	3.634 (3)	127

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x, y, z+1; (iii) −x+2, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University grants Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme fellowship (ASTS).

References

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Volume 68| Part 9| September 2012| Pages o2715-o2716

doi:10.1107/S1600536812034903

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-phenyl-2-[4-(tri­fluoro­meth­­oxy)phen­yl]-1H-benzimidazole-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

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organic compounds

Ethyl 1-phenyl-2-[4-(trifluoromethoxy)phenyl]-1H-benzimidazole-5-carboxylate