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

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

doi:10.1107/S1600536812022210

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1864-o1865

doi:10.1107/S1600536812022210

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Ethyl 1-phenyl-2-[4-(trifluoromethyl)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 7 May 2012; accepted 16 May 2012; online 23 May 2012)

The asymmetric unit of the title compound, C₂₃H₁₇F₃N₂O₂, contains two molecules. In one of the molecules, the phenyl and triflouromethyl-substituted benzene rings form dihedral angles of 52.05 (8) and 33.70 (8)°, respectively, with the benzimidazole ring system, while the dihedral angle between them is 58.24 (10)°. The corresponding values in the other molecule are 58.40 (8), 25.90 (8) and 60.83 (10)°, respectively. In the crystal, molecules are linked into chains along [100] by C—H⋯O and C—H⋯N hydrogen bonds. Aromatic π–π stacking interactions [centroid–centroid distance = 3.6700 (12) Å] also occur.

Related literature

For background to benzimidazole derivatives as drugs, see: Spasov et al. (1999 ); Grassmann et al. (2002 ); Demirayak et al. (2002 ); Evans et al. (1997 ). For related structures, see: Yoon et al. (2011 ); Kassim et al. (2012 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₃H₁₇F₃N₂O₂
M_r = 410.39
Monoclinic, P 2₁ /c
a = 9.8548 (2) Å
b = 25.0714 (6) Å
c = 16.0566 (4) Å
β = 107.023 (1)°
V = 3793.35 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.43 × 0.37 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.953, T_max = 0.969
36855 measured reflections
10921 independent reflections
5999 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.142
S = 1.03
10921 reflections
543 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22B—H22D⋯O2A	0.98	2.43	3.250 (3)	141
C17B—H17B⋯N1Bⁱ	0.95	2.62	3.524 (3)	159
C22A—H22A⋯O2Bⁱⁱ	0.98	2.43	3.250 (3)	141
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

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/S1600536812022210/hb6782sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022210/hb6782Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022210/hb6782Isup3.cml

checkCIF report

Comment top

The benzimidazole nucleus is an important pharmacophore in drug discovery (Spasov et al., 1999). They thus generate a lot of pharmacological interests (Grassmann et al., 2002; Demirayak et al., 2002; Evans et al., 1997). As part of our studies in this area, the crystal structure determination of the title compound was carried out and the results are presented here.

The asymmetric unit of the title compound (Fig 1), consists of two crystallographically independent molecules A and B. The benzimidazole ring system in both molecules, N1A/N2A/C1A—C7A and N1B/N2B/C1B—C7B, are essentially planar with a maximum deviation of 0.014 (2) Å at atom C7A and of 0.006 (2) Å at atom N2B, respectively. In molecule A, the benzimidazole ring (N1A/N2A/C1A—C7A) makes dihedral angles of 52.05 (8) and 33.70 (8)°, respectively with the phenyl ring (C14A–C19A) and the triflouromethyl-substituted phenyl ring (C8A–C13A). The corresponding dihedral angles in molecule B are 58.40 (8) and 25.90 (8)°.

In addition, the phenyl ring and the triflouromethyl-substituted phenyl ring form dihedral angles of 58.24 (10) and 60.83 (10)° in molecule A and B, respectively. Bond lengths and angles are within normal ranges and are comparable to related structure (Yoon et al., 2011; Kassim et al., 2012).

In the crystal (Fig. 2), C22B—H22D···O2A, C17B—H17B···N1B and C22A—H22A···O2B (Table 1) hydrogen bonds link the molecules into one-dimensional chains along a-axis. π–π interactions of Cg1···Cg2 = 3.6700 (12) Å (symmetry code: 1 - x,1 - y,2 - z) further stabilized the structure [Cg1 and Cg2 are the centroids of the N1A/N2A/C1A/C7A/C8A and C1B–C6B rings, respectively].

Related literature top

For background to benzimidazole derivatives as drugs, see: Spasov et al. (1999); Grassmann et al. (2002); Demirayak et al. (2002); Evans et al. (1997). For related structures, see: Yoon et al. (2011); Kassim et al. (2012). For 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 sodium metabisulfite adduct of trifluoromethyl benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C 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. The product was recrystallized from ethyl acetate as colourless blocks.

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

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

Crystal data top

C₂₃H₁₇F₃N₂O₂	F(000) = 1696
M_r = 410.39	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7502 reflections
a = 9.8548 (2) Å	θ = 2.2–29.0°
b = 25.0714 (6) Å	µ = 0.11 mm⁻¹
c = 16.0566 (4) Å	T = 100 K
β = 107.023 (1)°	Block, colourless
V = 3793.35 (15) Å³	0.43 × 0.37 × 0.28 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	10921 independent reflections
Radiation source: fine-focus sealed tube	5999 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→8
T_min = 0.953, T_max = 0.969	k = −35→28
36855 measured reflections	l = −17→22

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0497P)² + 1.1602P] where P = (F_o² + 2F_c²)/3
10921 reflections	(Δ/σ)_max = 0.001
543 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₃H₁₇F₃N₂O₂	V = 3793.35 (15) Å³
M_r = 410.39	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8548 (2) Å	µ = 0.11 mm⁻¹
b = 25.0714 (6) Å	T = 100 K
c = 16.0566 (4) Å	0.43 × 0.37 × 0.28 mm
β = 107.023 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	10921 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5999 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.969	R_int = 0.052
36855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
10921 reflections	Δρ_min = −0.35 e Å⁻³
543 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
F1A	0.76297 (13)	1.01889 (5)	0.89337 (9)	0.0404 (4)
F2A	0.55907 (13)	1.00949 (5)	0.79924 (8)	0.0359 (3)
F3A	0.57601 (14)	1.01271 (5)	0.93564 (9)	0.0386 (3)
O1A	1.05923 (15)	0.55832 (5)	0.88980 (10)	0.0290 (4)
O2A	0.89188 (16)	0.50085 (6)	0.90308 (10)	0.0341 (4)
N1A	0.82356 (17)	0.74226 (6)	0.88432 (11)	0.0218 (4)
N2A	0.59828 (16)	0.72851 (6)	0.88711 (11)	0.0206 (4)
C1A	0.6608 (2)	0.67850 (8)	0.89085 (13)	0.0212 (4)
C2A	0.6093 (2)	0.62721 (8)	0.89629 (13)	0.0238 (5)
H2AA	0.5148	0.6212	0.8976	0.029*
C3A	0.7023 (2)	0.58550 (8)	0.89961 (13)	0.0250 (5)
H3AA	0.6711	0.5500	0.9041	0.030*
C4A	0.8416 (2)	0.59399 (8)	0.89653 (14)	0.0242 (5)
C5A	0.8915 (2)	0.64522 (8)	0.89047 (13)	0.0227 (5)
H5AA	0.9856	0.6510	0.8882	0.027*
C6A	0.7995 (2)	0.68802 (8)	0.88787 (13)	0.0212 (4)
C7A	0.7031 (2)	0.76499 (8)	0.88416 (13)	0.0211 (4)
C8A	0.6837 (2)	0.82335 (8)	0.88447 (13)	0.0195 (4)
C9A	0.7566 (2)	0.85508 (8)	0.84015 (14)	0.0229 (5)
H9AA	0.8167	0.8389	0.8107	0.028*
C10A	0.7417 (2)	0.91004 (8)	0.83904 (14)	0.0239 (5)
H10A	0.7900	0.9314	0.8079	0.029*
C11A	0.6559 (2)	0.93399 (8)	0.88337 (14)	0.0218 (4)
C12A	0.5862 (2)	0.90302 (8)	0.92964 (13)	0.0240 (5)
H12A	0.5296	0.9195	0.9612	0.029*
C13A	0.5996 (2)	0.84796 (8)	0.92967 (13)	0.0220 (5)
H13A	0.5509	0.8268	0.9608	0.026*
C14A	0.4494 (2)	0.73733 (8)	0.87188 (13)	0.0198 (4)
C15A	0.3736 (2)	0.76759 (8)	0.80114 (13)	0.0226 (5)
H15A	0.4203	0.7830	0.7630	0.027*
C16A	0.2291 (2)	0.77507 (8)	0.78670 (14)	0.0250 (5)
H16A	0.1770	0.7961	0.7387	0.030*
C17A	0.1603 (2)	0.75224 (8)	0.84142 (15)	0.0265 (5)
H17A	0.0613	0.7575	0.8312	0.032*
C18A	0.2361 (2)	0.72168 (8)	0.91109 (14)	0.0256 (5)
H18A	0.1886	0.7055	0.9482	0.031*
C19A	0.3810 (2)	0.71448 (8)	0.92729 (14)	0.0234 (5)
H19A	0.4330	0.6940	0.9760	0.028*
C20A	0.9312 (2)	0.54611 (8)	0.89753 (14)	0.0260 (5)
C21A	1.1536 (2)	0.51374 (8)	0.89029 (16)	0.0330 (6)
H21A	1.1126	0.4903	0.8396	0.040*
H21B	1.1679	0.4925	0.9441	0.040*
C22A	1.2901 (3)	0.53614 (10)	0.8861 (2)	0.0666 (10)
H22A	1.3572	0.5071	0.8875	0.100*
H22B	1.3287	0.5598	0.9360	0.100*
H22C	1.2749	0.5564	0.8319	0.100*
C23A	0.6388 (2)	0.99321 (8)	0.87871 (15)	0.0263 (5)
F1B	0.26113 (14)	−0.10576 (5)	0.84724 (12)	0.0597 (5)
F2B	0.09026 (16)	−0.10489 (5)	0.90442 (10)	0.0471 (4)
F3B	0.04605 (15)	−0.09778 (5)	0.76703 (9)	0.0454 (4)
O1B	0.53146 (16)	0.35301 (6)	0.86297 (12)	0.0435 (5)
O2B	0.36752 (18)	0.41052 (6)	0.87921 (12)	0.0436 (4)
N1B	0.29935 (17)	0.16935 (6)	0.85506 (11)	0.0221 (4)
N2B	0.08626 (16)	0.18163 (6)	0.87819 (11)	0.0199 (4)
C1B	0.1461 (2)	0.23184 (8)	0.88029 (13)	0.0200 (4)
C2B	0.0975 (2)	0.28262 (8)	0.89265 (13)	0.0232 (5)
H2BA	0.0080	0.2878	0.9026	0.028*
C3B	0.1855 (2)	0.32487 (8)	0.88979 (13)	0.0248 (5)
H3BA	0.1562	0.3600	0.8982	0.030*
C4B	0.3183 (2)	0.31702 (8)	0.87455 (13)	0.0233 (5)
C5B	0.3658 (2)	0.26639 (8)	0.86268 (13)	0.0228 (5)
H5BA	0.4556	0.2612	0.8532	0.027*
C6B	0.2778 (2)	0.22339 (8)	0.86507 (13)	0.0213 (4)
C7B	0.1845 (2)	0.14569 (8)	0.86316 (13)	0.0200 (4)
C8B	0.1679 (2)	0.08739 (8)	0.86005 (13)	0.0200 (4)
C9B	0.2440 (2)	0.05866 (8)	0.81417 (14)	0.0239 (5)
H9BA	0.3029	0.0771	0.7862	0.029*
C10B	0.2346 (2)	0.00394 (8)	0.80904 (14)	0.0265 (5)
H10B	0.2856	−0.0152	0.7768	0.032*
C11B	0.1506 (2)	−0.02321 (8)	0.85099 (14)	0.0245 (5)
C12B	0.0767 (2)	0.00470 (8)	0.89859 (14)	0.0242 (5)
H12B	0.0205	−0.0139	0.9281	0.029*
C13B	0.0855 (2)	0.05993 (8)	0.90287 (14)	0.0228 (5)
H13B	0.0348	0.0791	0.9353	0.027*
C14B	−0.0593 (2)	0.17171 (7)	0.87440 (13)	0.0199 (4)
C15B	−0.1489 (2)	0.14730 (8)	0.80140 (14)	0.0226 (5)
H15B	−0.1146	0.1368	0.7544	0.027*
C16B	−0.2889 (2)	0.13850 (8)	0.79805 (15)	0.0257 (5)
H16B	−0.3506	0.1213	0.7487	0.031*
C17B	−0.3405 (2)	0.15442 (8)	0.86555 (15)	0.0281 (5)
H17B	−0.4370	0.1484	0.8626	0.034*
C18B	−0.2501 (2)	0.17911 (8)	0.93713 (16)	0.0303 (5)
H18B	−0.2852	0.1904	0.9834	0.036*
C19B	−0.1085 (2)	0.18781 (8)	0.94274 (14)	0.0258 (5)
H19B	−0.0466	0.2045	0.9926	0.031*
C20B	0.4053 (2)	0.36554 (9)	0.87282 (14)	0.0284 (5)
C21B	0.6254 (3)	0.39661 (10)	0.8563 (2)	0.0538 (8)
H21C	0.6017	0.4291	0.8842	0.065*
H21D	0.6146	0.4047	0.7943	0.065*
C22B	0.7715 (3)	0.37996 (10)	0.90028 (18)	0.0447 (7)
H22D	0.8378	0.4062	0.8891	0.067*
H22E	0.7892	0.3451	0.8781	0.067*
H22F	0.7851	0.3775	0.9631	0.067*
C23B	0.1376 (2)	−0.08240 (9)	0.84303 (16)	0.0308 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.0245 (7)	0.0212 (7)	0.0727 (11)	−0.0050 (5)	0.0097 (7)	−0.0006 (7)
F2A	0.0357 (8)	0.0293 (7)	0.0399 (8)	0.0048 (6)	0.0065 (6)	0.0090 (6)
F3A	0.0476 (9)	0.0257 (7)	0.0482 (9)	0.0051 (6)	0.0230 (7)	−0.0037 (6)
O1A	0.0285 (8)	0.0202 (7)	0.0400 (10)	0.0043 (6)	0.0125 (7)	0.0010 (7)
O2A	0.0340 (9)	0.0221 (8)	0.0438 (10)	−0.0001 (7)	0.0073 (8)	0.0012 (7)
N1A	0.0199 (9)	0.0203 (9)	0.0249 (10)	−0.0020 (7)	0.0059 (7)	−0.0009 (7)
N2A	0.0154 (8)	0.0194 (9)	0.0263 (10)	−0.0015 (7)	0.0051 (7)	0.0011 (7)
C1A	0.0211 (11)	0.0207 (10)	0.0200 (11)	−0.0026 (8)	0.0031 (8)	−0.0006 (9)
C2A	0.0190 (11)	0.0244 (11)	0.0263 (12)	−0.0040 (8)	0.0039 (9)	0.0015 (9)
C3A	0.0252 (11)	0.0204 (11)	0.0257 (12)	−0.0052 (9)	0.0015 (9)	0.0021 (9)
C4A	0.0230 (11)	0.0225 (11)	0.0245 (12)	0.0001 (9)	0.0030 (9)	0.0002 (9)
C5A	0.0210 (11)	0.0215 (11)	0.0246 (12)	−0.0020 (9)	0.0049 (9)	−0.0005 (9)
C6A	0.0198 (10)	0.0210 (10)	0.0213 (12)	−0.0036 (8)	0.0038 (8)	−0.0025 (9)
C7A	0.0175 (10)	0.0246 (11)	0.0203 (11)	−0.0035 (8)	0.0043 (8)	0.0001 (9)
C8A	0.0154 (10)	0.0219 (10)	0.0202 (11)	−0.0007 (8)	0.0036 (8)	−0.0023 (9)
C9A	0.0185 (10)	0.0257 (11)	0.0252 (12)	−0.0004 (8)	0.0075 (9)	−0.0009 (9)
C10A	0.0229 (11)	0.0223 (11)	0.0271 (12)	−0.0040 (9)	0.0082 (9)	0.0018 (9)
C11A	0.0185 (10)	0.0188 (10)	0.0254 (12)	−0.0016 (8)	0.0020 (9)	−0.0010 (9)
C12A	0.0199 (11)	0.0268 (11)	0.0249 (12)	−0.0002 (9)	0.0062 (9)	−0.0046 (9)
C13A	0.0193 (11)	0.0233 (11)	0.0233 (12)	−0.0042 (8)	0.0058 (9)	0.0005 (9)
C14A	0.0158 (10)	0.0197 (10)	0.0227 (11)	−0.0023 (8)	0.0039 (8)	−0.0036 (9)
C15A	0.0244 (11)	0.0205 (10)	0.0227 (12)	−0.0020 (8)	0.0064 (9)	−0.0021 (9)
C16A	0.0224 (11)	0.0200 (10)	0.0293 (12)	0.0022 (8)	0.0023 (9)	−0.0029 (9)
C17A	0.0193 (11)	0.0247 (11)	0.0359 (14)	−0.0019 (9)	0.0084 (10)	−0.0101 (10)
C18A	0.0234 (11)	0.0249 (11)	0.0308 (13)	−0.0076 (9)	0.0116 (10)	−0.0051 (10)
C19A	0.0226 (11)	0.0232 (11)	0.0231 (12)	−0.0051 (9)	0.0050 (9)	−0.0021 (9)
C20A	0.0252 (12)	0.0230 (12)	0.0268 (13)	−0.0010 (9)	0.0027 (9)	0.0011 (9)
C21A	0.0357 (13)	0.0208 (11)	0.0447 (15)	0.0066 (10)	0.0154 (11)	0.0002 (10)
C22A	0.061 (2)	0.0321 (15)	0.128 (3)	0.0102 (13)	0.062 (2)	0.0098 (17)
C23A	0.0204 (11)	0.0253 (11)	0.0330 (14)	0.0005 (9)	0.0072 (10)	−0.0014 (10)
F1B	0.0283 (8)	0.0248 (7)	0.1254 (15)	0.0052 (6)	0.0214 (9)	−0.0106 (8)
F2B	0.0639 (10)	0.0245 (7)	0.0554 (10)	−0.0010 (7)	0.0214 (8)	0.0070 (7)
F3B	0.0501 (9)	0.0302 (7)	0.0482 (9)	−0.0089 (6)	0.0025 (7)	−0.0122 (7)
O1B	0.0266 (9)	0.0250 (8)	0.0791 (14)	−0.0038 (7)	0.0159 (9)	0.0166 (9)
O2B	0.0593 (12)	0.0212 (9)	0.0592 (12)	−0.0064 (8)	0.0310 (10)	−0.0041 (8)
N1B	0.0210 (9)	0.0203 (9)	0.0251 (10)	0.0012 (7)	0.0070 (8)	0.0017 (7)
N2B	0.0164 (8)	0.0196 (9)	0.0235 (10)	0.0008 (7)	0.0056 (7)	−0.0013 (7)
C1B	0.0182 (10)	0.0203 (10)	0.0197 (11)	0.0001 (8)	0.0030 (8)	−0.0003 (9)
C2B	0.0202 (11)	0.0244 (11)	0.0226 (12)	0.0016 (9)	0.0027 (9)	−0.0007 (9)
C3B	0.0293 (12)	0.0185 (10)	0.0231 (12)	0.0021 (9)	0.0021 (9)	−0.0009 (9)
C4B	0.0256 (11)	0.0220 (11)	0.0195 (11)	−0.0035 (9)	0.0023 (9)	0.0016 (9)
C5B	0.0209 (11)	0.0240 (11)	0.0233 (12)	−0.0008 (9)	0.0062 (9)	0.0040 (9)
C6B	0.0210 (11)	0.0219 (11)	0.0205 (11)	0.0024 (8)	0.0052 (9)	0.0011 (9)
C7B	0.0168 (10)	0.0233 (11)	0.0198 (11)	0.0019 (8)	0.0053 (8)	0.0004 (9)
C8B	0.0160 (10)	0.0208 (10)	0.0213 (11)	0.0011 (8)	0.0025 (8)	−0.0009 (9)
C9B	0.0204 (11)	0.0254 (11)	0.0270 (12)	−0.0006 (9)	0.0085 (9)	−0.0021 (9)
C10B	0.0212 (11)	0.0276 (12)	0.0320 (13)	0.0026 (9)	0.0099 (10)	−0.0052 (10)
C11B	0.0176 (10)	0.0215 (11)	0.0299 (13)	0.0009 (8)	0.0000 (9)	−0.0009 (9)
C12B	0.0197 (11)	0.0225 (11)	0.0310 (13)	0.0007 (9)	0.0081 (9)	0.0031 (10)
C13B	0.0203 (11)	0.0218 (11)	0.0275 (12)	0.0019 (8)	0.0089 (9)	−0.0011 (9)
C14B	0.0148 (10)	0.0168 (10)	0.0277 (12)	0.0003 (8)	0.0056 (9)	0.0011 (9)
C15B	0.0230 (11)	0.0200 (10)	0.0239 (12)	0.0010 (8)	0.0053 (9)	0.0012 (9)
C16B	0.0191 (11)	0.0203 (11)	0.0330 (13)	0.0006 (8)	0.0004 (9)	0.0001 (9)
C17B	0.0167 (10)	0.0218 (11)	0.0458 (15)	0.0005 (9)	0.0090 (10)	−0.0009 (10)
C18B	0.0268 (12)	0.0275 (12)	0.0415 (15)	0.0017 (9)	0.0176 (11)	−0.0053 (11)
C19B	0.0208 (11)	0.0271 (11)	0.0299 (13)	−0.0008 (9)	0.0081 (9)	−0.0055 (10)
C20B	0.0344 (13)	0.0253 (12)	0.0227 (12)	−0.0038 (10)	0.0040 (10)	0.0037 (10)
C21B	0.0387 (16)	0.0342 (14)	0.086 (2)	−0.0119 (12)	0.0140 (15)	0.0244 (15)
C22B	0.0409 (16)	0.0299 (13)	0.0648 (19)	−0.0133 (11)	0.0179 (14)	−0.0055 (13)
C23B	0.0233 (12)	0.0237 (11)	0.0446 (16)	−0.0015 (9)	0.0090 (11)	−0.0025 (11)

Geometric parameters (Å, º) top

F1A—C23A	1.341 (2)	F1B—C23B	1.335 (2)
F2A—C23A	1.351 (2)	F2B—C23B	1.333 (3)
F3A—C23A	1.337 (2)	F3B—C23B	1.344 (3)
O1A—C20A	1.339 (2)	O1B—C20B	1.336 (3)
O1A—C21A	1.453 (2)	O1B—C21B	1.457 (3)
O2A—C20A	1.211 (2)	O2B—C20B	1.201 (3)
N1A—C7A	1.316 (2)	N1B—C7B	1.317 (2)
N1A—C6A	1.385 (2)	N1B—C6B	1.388 (2)
N2A—C1A	1.390 (2)	N2B—C1B	1.386 (2)
N2A—C7A	1.391 (2)	N2B—C7B	1.394 (2)
N2A—C14A	1.432 (2)	N2B—C14B	1.440 (2)
C1A—C2A	1.394 (3)	C1B—C2B	1.395 (3)
C1A—C6A	1.402 (3)	C1B—C6B	1.405 (3)
C2A—C3A	1.381 (3)	C2B—C3B	1.378 (3)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.404 (3)	C3B—C4B	1.414 (3)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.389 (3)	C4B—C5B	1.385 (3)
C4A—C20A	1.488 (3)	C4B—C20B	1.493 (3)
C5A—C6A	1.397 (3)	C5B—C6B	1.392 (3)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C7A—C8A	1.476 (3)	C7B—C8B	1.470 (3)
C8A—C13A	1.395 (3)	C8B—C13B	1.390 (3)
C8A—C9A	1.399 (3)	C8B—C9B	1.396 (3)
C9A—C10A	1.385 (3)	C9B—C10B	1.376 (3)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.390 (3)	C10B—C11B	1.389 (3)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.388 (3)	C11B—C12B	1.389 (3)
C11A—C23A	1.494 (3)	C11B—C23B	1.492 (3)
C12A—C13A	1.387 (3)	C12B—C13B	1.388 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C19A	1.388 (3)	C14B—C19B	1.383 (3)
C14A—C15A	1.388 (3)	C14B—C15B	1.386 (3)
C15A—C16A	1.387 (3)	C15B—C16B	1.382 (3)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.381 (3)	C16B—C17B	1.384 (3)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.381 (3)	C17B—C18B	1.378 (3)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.386 (3)	C18B—C19B	1.388 (3)
C18A—H18A	0.9500	C18B—H18B	0.9500
C19A—H19A	0.9500	C19B—H19B	0.9500
C21A—C22A	1.477 (3)	C21B—C22B	1.466 (4)
C21A—H21A	0.9900	C21B—H21C	0.9900
C21A—H21B	0.9900	C21B—H21D	0.9900
C22A—H22A	0.9800	C22B—H22D	0.9800
C22A—H22B	0.9800	C22B—H22E	0.9800
C22A—H22C	0.9800	C22B—H22F	0.9800

C20A—O1A—C21A	116.27 (16)	C20B—O1B—C21B	117.78 (18)
C7A—N1A—C6A	105.06 (16)	C7B—N1B—C6B	105.23 (16)
C1A—N2A—C7A	105.71 (15)	C1B—N2B—C7B	106.20 (15)
C1A—N2A—C14A	124.42 (16)	C1B—N2B—C14B	124.70 (16)
C7A—N2A—C14A	128.78 (16)	C7B—N2B—C14B	127.95 (16)
N2A—C1A—C2A	132.04 (18)	N2B—C1B—C2B	132.15 (18)
N2A—C1A—C6A	105.60 (16)	N2B—C1B—C6B	105.46 (16)
C2A—C1A—C6A	122.36 (18)	C2B—C1B—C6B	122.38 (18)
C3A—C2A—C1A	116.82 (19)	C3B—C2B—C1B	116.82 (19)
C3A—C2A—H2AA	121.6	C3B—C2B—H2BA	121.6
C1A—C2A—H2AA	121.6	C1B—C2B—H2BA	121.6
C2A—C3A—C4A	121.89 (19)	C2B—C3B—C4B	121.48 (19)
C2A—C3A—H3AA	119.1	C2B—C3B—H3BA	119.3
C4A—C3A—H3AA	119.1	C4B—C3B—H3BA	119.3
C5A—C4A—C3A	120.80 (19)	C5B—C4B—C3B	121.23 (18)
C5A—C4A—C20A	121.74 (19)	C5B—C4B—C20B	121.66 (19)
C3A—C4A—C20A	117.43 (18)	C3B—C4B—C20B	117.10 (19)
C4A—C5A—C6A	118.21 (19)	C4B—C5B—C6B	117.87 (19)
C4A—C5A—H5AA	120.9	C4B—C5B—H5BA	121.1
C6A—C5A—H5AA	120.9	C6B—C5B—H5BA	121.1
N1A—C6A—C5A	129.64 (18)	N1B—C6B—C5B	129.42 (18)
N1A—C6A—C1A	110.44 (17)	N1B—C6B—C1B	110.38 (17)
C5A—C6A—C1A	119.91 (18)	C5B—C6B—C1B	120.20 (18)
N1A—C7A—N2A	113.17 (17)	N1B—C7B—N2B	112.72 (17)
N1A—C7A—C8A	123.14 (17)	N1B—C7B—C8B	122.31 (17)
N2A—C7A—C8A	123.64 (17)	N2B—C7B—C8B	124.91 (17)
C13A—C8A—C9A	119.04 (18)	C13B—C8B—C9B	119.18 (18)
C13A—C8A—C7A	122.50 (18)	C13B—C8B—C7B	123.42 (18)
C9A—C8A—C7A	118.43 (17)	C9B—C8B—C7B	117.35 (18)
C10A—C9A—C8A	120.25 (19)	C10B—C9B—C8B	120.60 (19)
C10A—C9A—H9AA	119.9	C10B—C9B—H9BA	119.7
C8A—C9A—H9AA	119.9	C8B—C9B—H9BA	119.7
C9A—C10A—C11A	120.08 (19)	C9B—C10B—C11B	119.93 (19)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.0
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.0
C12A—C11A—C10A	120.19 (18)	C10B—C11B—C12B	120.19 (19)
C12A—C11A—C23A	121.10 (19)	C10B—C11B—C23B	119.67 (19)
C10A—C11A—C23A	118.71 (18)	C12B—C11B—C23B	120.13 (19)
C13A—C12A—C11A	119.70 (19)	C13B—C12B—C11B	119.65 (19)
C13A—C12A—H12A	120.2	C13B—C12B—H12B	120.2
C11A—C12A—H12A	120.2	C11B—C12B—H12B	120.2
C12A—C13A—C8A	120.71 (19)	C12B—C13B—C8B	120.42 (19)
C12A—C13A—H13A	119.6	C12B—C13B—H13B	119.8
C8A—C13A—H13A	119.6	C8B—C13B—H13B	119.8
C19A—C14A—C15A	120.24 (18)	C19B—C14B—C15B	121.01 (19)
C19A—C14A—N2A	119.52 (18)	C19B—C14B—N2B	119.50 (18)
C15A—C14A—N2A	120.22 (18)	C15B—C14B—N2B	119.47 (18)
C16A—C15A—C14A	119.41 (19)	C16B—C15B—C14B	119.0 (2)
C16A—C15A—H15A	120.3	C16B—C15B—H15B	120.5
C14A—C15A—H15A	120.3	C14B—C15B—H15B	120.5
C17A—C16A—C15A	120.6 (2)	C15B—C16B—C17B	121.0 (2)
C17A—C16A—H16A	119.7	C15B—C16B—H16B	119.5
C15A—C16A—H16A	119.7	C17B—C16B—H16B	119.5
C18A—C17A—C16A	119.7 (2)	C18B—C17B—C16B	119.1 (2)
C18A—C17A—H17A	120.2	C18B—C17B—H17B	120.4
C16A—C17A—H17A	120.2	C16B—C17B—H17B	120.4
C17A—C18A—C19A	120.5 (2)	C17B—C18B—C19B	121.1 (2)
C17A—C18A—H18A	119.7	C17B—C18B—H18B	119.4
C19A—C18A—H18A	119.7	C19B—C18B—H18B	119.4
C18A—C19A—C14A	119.6 (2)	C14B—C19B—C18B	118.8 (2)
C18A—C19A—H19A	120.2	C14B—C19B—H19B	120.6
C14A—C19A—H19A	120.2	C18B—C19B—H19B	120.6
O2A—C20A—O1A	123.51 (19)	O2B—C20B—O1B	123.6 (2)
O2A—C20A—C4A	123.71 (19)	O2B—C20B—C4B	124.7 (2)
O1A—C20A—C4A	112.77 (17)	O1B—C20B—C4B	111.72 (18)
O1A—C21A—C22A	107.29 (18)	O1B—C21B—C22B	107.8 (2)
O1A—C21A—H21A	110.3	O1B—C21B—H21C	110.1
C22A—C21A—H21A	110.3	C22B—C21B—H21C	110.1
O1A—C21A—H21B	110.3	O1B—C21B—H21D	110.1
C22A—C21A—H21B	110.3	C22B—C21B—H21D	110.1
H21A—C21A—H21B	108.5	H21C—C21B—H21D	108.5
C21A—C22A—H22A	109.5	C21B—C22B—H22D	109.5
C21A—C22A—H22B	109.5	C21B—C22B—H22E	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22E	109.5
C21A—C22A—H22C	109.5	C21B—C22B—H22F	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22F	109.5
H22B—C22A—H22C	109.5	H22E—C22B—H22F	109.5
F3A—C23A—F1A	106.59 (17)	F2B—C23B—F1B	106.76 (19)
F3A—C23A—F2A	106.13 (16)	F2B—C23B—F3B	105.26 (17)
F1A—C23A—F2A	105.61 (17)	F1B—C23B—F3B	106.24 (18)
F3A—C23A—C11A	113.40 (18)	F2B—C23B—C11B	113.44 (19)
F1A—C23A—C11A	112.59 (17)	F1B—C23B—C11B	112.17 (17)
F2A—C23A—C11A	111.94 (17)	F3B—C23B—C11B	112.42 (18)

C7A—N2A—C1A—C2A	178.8 (2)	C7B—N2B—C1B—C2B	179.8 (2)
C14A—N2A—C1A—C2A	−12.3 (3)	C14B—N2B—C1B—C2B	11.3 (3)
C7A—N2A—C1A—C6A	−1.3 (2)	C7B—N2B—C1B—C6B	0.8 (2)
C14A—N2A—C1A—C6A	167.61 (18)	C14B—N2B—C1B—C6B	−167.79 (18)
N2A—C1A—C2A—C3A	−179.5 (2)	N2B—C1B—C2B—C3B	−179.3 (2)
C6A—C1A—C2A—C3A	0.7 (3)	C6B—C1B—C2B—C3B	−0.3 (3)
C1A—C2A—C3A—C4A	−0.8 (3)	C1B—C2B—C3B—C4B	0.3 (3)
C2A—C3A—C4A—C5A	0.4 (3)	C2B—C3B—C4B—C5B	−0.6 (3)
C2A—C3A—C4A—C20A	−177.97 (19)	C2B—C3B—C4B—C20B	−179.96 (19)
C3A—C4A—C5A—C6A	0.2 (3)	C3B—C4B—C5B—C6B	0.8 (3)
C20A—C4A—C5A—C6A	178.52 (19)	C20B—C4B—C5B—C6B	−179.85 (19)
C7A—N1A—C6A—C5A	−179.2 (2)	C7B—N1B—C6B—C5B	179.8 (2)
C7A—N1A—C6A—C1A	−0.7 (2)	C7B—N1B—C6B—C1B	0.5 (2)
C4A—C5A—C6A—N1A	178.1 (2)	C4B—C5B—C6B—N1B	179.9 (2)
C4A—C5A—C6A—C1A	−0.4 (3)	C4B—C5B—C6B—C1B	−0.8 (3)
N2A—C1A—C6A—N1A	1.3 (2)	N2B—C1B—C6B—N1B	−0.8 (2)
C2A—C1A—C6A—N1A	−178.83 (18)	C2B—C1B—C6B—N1B	−179.96 (18)
N2A—C1A—C6A—C5A	−179.99 (18)	N2B—C1B—C6B—C5B	179.78 (18)
C2A—C1A—C6A—C5A	−0.1 (3)	C2B—C1B—C6B—C5B	0.6 (3)
C6A—N1A—C7A—N2A	−0.2 (2)	C6B—N1B—C7B—N2B	0.0 (2)
C6A—N1A—C7A—C8A	177.40 (18)	C6B—N1B—C7B—C8B	−177.55 (18)
C1A—N2A—C7A—N1A	1.0 (2)	C1B—N2B—C7B—N1B	−0.5 (2)
C14A—N2A—C7A—N1A	−167.28 (18)	C14B—N2B—C7B—N1B	167.55 (18)
C1A—N2A—C7A—C8A	−176.60 (18)	C1B—N2B—C7B—C8B	176.97 (18)
C14A—N2A—C7A—C8A	15.1 (3)	C14B—N2B—C7B—C8B	−15.0 (3)
N1A—C7A—C8A—C13A	−143.8 (2)	N1B—C7B—C8B—C13B	151.6 (2)
N2A—C7A—C8A—C13A	33.6 (3)	N2B—C7B—C8B—C13B	−25.7 (3)
N1A—C7A—C8A—C9A	34.0 (3)	N1B—C7B—C8B—C9B	−25.9 (3)
N2A—C7A—C8A—C9A	−148.65 (19)	N2B—C7B—C8B—C9B	156.83 (19)
C13A—C8A—C9A—C10A	−2.0 (3)	C13B—C8B—C9B—C10B	1.9 (3)
C7A—C8A—C9A—C10A	−179.83 (18)	C7B—C8B—C9B—C10B	179.48 (19)
C8A—C9A—C10A—C11A	1.2 (3)	C8B—C9B—C10B—C11B	−1.1 (3)
C9A—C10A—C11A—C12A	0.7 (3)	C9B—C10B—C11B—C12B	−0.4 (3)
C9A—C10A—C11A—C23A	−178.25 (19)	C9B—C10B—C11B—C23B	178.2 (2)
C10A—C11A—C12A—C13A	−1.6 (3)	C10B—C11B—C12B—C13B	1.0 (3)
C23A—C11A—C12A—C13A	177.27 (19)	C23B—C11B—C12B—C13B	−177.6 (2)
C11A—C12A—C13A—C8A	0.7 (3)	C11B—C12B—C13B—C8B	−0.2 (3)
C9A—C8A—C13A—C12A	1.1 (3)	C9B—C8B—C13B—C12B	−1.3 (3)
C7A—C8A—C13A—C12A	178.79 (18)	C7B—C8B—C13B—C12B	−178.71 (19)
C1A—N2A—C14A—C19A	57.5 (3)	C1B—N2B—C14B—C19B	−63.5 (3)
C7A—N2A—C14A—C19A	−136.2 (2)	C7B—N2B—C14B—C19B	130.5 (2)
C1A—N2A—C14A—C15A	−121.2 (2)	C1B—N2B—C14B—C15B	115.0 (2)
C7A—N2A—C14A—C15A	45.1 (3)	C7B—N2B—C14B—C15B	−51.0 (3)
C19A—C14A—C15A—C16A	0.4 (3)	C19B—C14B—C15B—C16B	−0.8 (3)
N2A—C14A—C15A—C16A	179.07 (17)	N2B—C14B—C15B—C16B	−179.30 (17)
C14A—C15A—C16A—C17A	−0.7 (3)	C14B—C15B—C16B—C17B	1.0 (3)
C15A—C16A—C17A—C18A	0.0 (3)	C15B—C16B—C17B—C18B	−0.4 (3)
C16A—C17A—C18A—C19A	1.1 (3)	C16B—C17B—C18B—C19B	−0.5 (3)
C17A—C18A—C19A—C14A	−1.3 (3)	C15B—C14B—C19B—C18B	0.0 (3)
C15A—C14A—C19A—C18A	0.6 (3)	N2B—C14B—C19B—C18B	178.46 (18)
N2A—C14A—C19A—C18A	−178.09 (17)	C17B—C18B—C19B—C14B	0.7 (3)
C21A—O1A—C20A—O2A	−1.4 (3)	C21B—O1B—C20B—O2B	−2.5 (3)
C21A—O1A—C20A—C4A	179.94 (18)	C21B—O1B—C20B—C4B	177.3 (2)
C5A—C4A—C20A—O2A	179.7 (2)	C5B—C4B—C20B—O2B	176.9 (2)
C3A—C4A—C20A—O2A	−2.0 (3)	C3B—C4B—C20B—O2B	−3.8 (3)
C5A—C4A—C20A—O1A	−1.6 (3)	C5B—C4B—C20B—O1B	−2.9 (3)
C3A—C4A—C20A—O1A	176.72 (18)	C3B—C4B—C20B—O1B	176.40 (18)
C20A—O1A—C21A—C22A	−176.9 (2)	C20B—O1B—C21B—C22B	144.2 (2)
C12A—C11A—C23A—F3A	12.5 (3)	C10B—C11B—C23B—F2B	161.60 (19)
C10A—C11A—C23A—F3A	−168.60 (18)	C12B—C11B—C23B—F2B	−19.8 (3)
C12A—C11A—C23A—F1A	133.6 (2)	C10B—C11B—C23B—F1B	40.5 (3)
C10A—C11A—C23A—F1A	−47.5 (3)	C12B—C11B—C23B—F1B	−140.8 (2)
C12A—C11A—C23A—F2A	−107.6 (2)	C10B—C11B—C23B—F3B	−79.1 (2)
C10A—C11A—C23A—F2A	71.4 (2)	C12B—C11B—C23B—F3B	99.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22B—H22D···O2A	0.98	2.43	3.250 (3)	141
C17B—H17B···N1Bⁱ	0.95	2.62	3.524 (3)	159
C22A—H22A···O2Bⁱⁱ	0.98	2.43	3.250 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇F₃N₂O₂
M_r	410.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.8548 (2), 25.0714 (6), 16.0566 (4)
β (°)	107.023 (1)
V (Å³)	3793.35 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.43 × 0.37 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.953, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	36855, 10921, 5999
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.142, 1.03
No. of reflections	10921
No. of parameters	543
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22B—H22D···O2A	0.98	2.43	3.250 (3)	141
C17B—H17B···N1Bⁱ	0.95	2.62	3.524 (3)	159
C22A—H22A···O2Bⁱⁱ	0.98	2.43	3.250 (3)	141

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

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

References

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Grassmann, S., Sadek, B., Ligneau, X., Elz, S., Ganellin, C. R., Arrang, J. M., Schwartz, J. C., Stark, H. & Schunack, W. (2002). Eur. J. Pharm. Sci. 15, 367–378. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 68| Part 6| June 2012| Pages o1864-o1865

doi:10.1107/S1600536812022210

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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