Ethyl 1-[2-(morpholin-4-yl)eth-yl]-2-[4-(trifluoro-meth-yl)phen-yl]-1H-benzimid-azole-5-carboxyl-ate.

In the title compound, C(23)H(24)F(3)N(3)O(3), the morpholine ring adopts a chair conformation. The benzimidazole ring is approximately planar, with a maximum deviation of 0.028 (1) Å for one of the unsubstituted C atoms. The benzimidazole ring makes dihedral angles of 35.66 (4) and 75.45 (5)° with the attached phenyl and morpholine rings, respectively. In the crystal structure, adjacent mol-ecules are linked via C-H⋯F and C-H⋯O hydrogen bonds to form a two-dimensional network.

Related literature

For background to benzimidazoles, see: Boruah & Skibo (1994 ▶); Haugwitz (1982 ▶); Hisano (1982 ▶); Hubschwerlen (1992 ▶); Shi (1996 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H24F3N3O3

M = 447.45

Triclinic,

a = 10.1463 (2) Å

b = 10.5595 (2) Å

c = 11.5775 (2) Å

α = 96.868 (1)°

β = 109.638 (1)°

γ = 110.833 (1)°

V = 1050.83 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.51 × 0.33 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.945, T max = 0.979

22546 measured reflections

6122 independent reflections

5266 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.03

6122 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.26 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 datablocks global, I. DOI: 10.1107/S1600536811014619/hb5849sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014619/hb5849Isup2.hkl

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

C23H24F3N3O3	Z = 2
Mr = 447.45	F(000) = 468
Triclinic, P1	Dx = 1.414 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1463 (2) Å	Cell parameters from 9996 reflections
b = 10.5595 (2) Å	θ = 2.4–30.1°
c = 11.5775 (2) Å	µ = 0.11 mm−1
α = 96.868 (1)°	T = 100 K
β = 109.638 (1)°	Block, colourless
γ = 110.833 (1)°	0.51 × 0.33 × 0.19 mm
V = 1050.83 (3) Å3

Bruker SMART APEXII CCD diffractometer	6122 independent reflections
Radiation source: fine-focus sealed tube	5266 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.945, Tmax = 0.979	k = −14→14
22546 measured reflections	l = −16→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.2843P] where P = (Fo2 + 2Fc2)/3
6122 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.26 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 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
F1	0.57861 (8)	1.42374 (7)	0.30620 (7)	0.02777 (15)
F2	0.46917 (8)	1.29209 (7)	0.11309 (6)	0.02950 (16)
F3	0.71291 (8)	1.42604 (7)	0.19595 (7)	0.02843 (15)
O1	0.69592 (9)	0.47558 (8)	0.74341 (7)	0.02040 (15)
O2	0.85918 (10)	0.40173 (9)	0.69712 (8)	0.02932 (18)
O3	1.19661 (9)	0.84859 (9)	0.01681 (7)	0.02600 (17)
N1	0.83537 (9)	0.85327 (9)	0.38581 (8)	0.01618 (16)
N2	0.65751 (9)	0.82663 (9)	0.46835 (8)	0.01700 (16)
N3	0.98967 (9)	0.86116 (8)	0.13194 (7)	0.01548 (15)
C1	0.73153 (11)	0.74099 (10)	0.50627 (9)	0.01619 (17)
C2	0.71070 (11)	0.64983 (10)	0.58354 (9)	0.01726 (18)
H2A	0.6343	0.6359	0.6167	0.021*
C3	0.80658 (11)	0.58039 (10)	0.60970 (9)	0.01745 (18)
C4	0.92137 (11)	0.60204 (10)	0.56165 (9)	0.01902 (18)
H4A	0.9867	0.5550	0.5839	0.023*
C5	0.94156 (11)	0.68952 (10)	0.48328 (9)	0.01836 (18)
H5A	1.0176	0.7028	0.4498	0.022*
C6	0.84348 (11)	0.75739 (10)	0.45626 (9)	0.01645 (17)
C7	0.72211 (11)	0.89169 (10)	0.39757 (9)	0.01597 (17)
C8	0.68579 (11)	1.00214 (10)	0.34664 (9)	0.01626 (17)
C9	0.69019 (11)	1.02693 (10)	0.23121 (9)	0.01882 (18)
H9A	0.7115	0.9671	0.1792	0.023*
C10	0.66367 (11)	1.13828 (11)	0.19277 (9)	0.01912 (19)
H10A	0.6688	1.1559	0.1155	0.023*
C11	0.62940 (11)	1.22431 (10)	0.26810 (9)	0.01741 (18)
C12	0.61869 (11)	1.19837 (10)	0.38023 (9)	0.01806 (18)
H12A	0.5924	1.2558	0.4298	0.022*
C13	0.64690 (11)	1.08740 (10)	0.41914 (9)	0.01761 (18)
H13A	0.6397	1.0692	0.4957	0.021*
C14	0.59851 (12)	1.34179 (11)	0.22216 (10)	0.02011 (19)
C15	0.79184 (12)	0.47723 (11)	0.68685 (9)	0.01946 (19)
C16	0.67213 (13)	0.37082 (11)	0.81448 (10)	0.0224 (2)
H16A	0.7715	0.3881	0.8834	0.027*
H16B	0.6290	0.2752	0.7573	0.027*
C17	0.56154 (14)	0.38291 (12)	0.86957 (11)	0.0266 (2)
H17A	0.5412	0.3120	0.9164	0.040*
H17B	0.4645	0.3676	0.8006	0.040*
H17C	0.6065	0.4771	0.9277	0.040*
C18	0.94152 (11)	0.90747 (10)	0.32523 (9)	0.01693 (17)
H18A	1.0476	0.9268	0.3839	0.020*
H18B	0.9416	0.9972	0.3083	0.020*
C19	0.89489 (11)	0.80215 (10)	0.20000 (9)	0.01663 (17)
H19A	0.9059	0.7163	0.2182	0.020*
H19B	0.7850	0.7747	0.1453	0.020*
C20	1.15464 (11)	0.90256 (10)	0.20837 (9)	0.01811 (18)
H20A	1.1691	0.8211	0.2350	0.022*
H20B	1.1916	0.9786	0.2861	0.022*
C21	1.24758 (12)	0.95334 (12)	0.13135 (10)	0.0243 (2)
H21A	1.2383	1.0386	0.1099	0.029*
H21B	1.3579	0.9794	0.1835	0.029*
C22	1.03751 (13)	0.81211 (12)	−0.05885 (10)	0.0251 (2)
H22A	1.0017	0.7401	−0.1390	0.030*
H22B	1.0260	0.8964	−0.0811	0.030*
C23	0.93906 (12)	0.75531 (11)	0.01281 (9)	0.02070 (19)
H23A	0.8295	0.7302	−0.0411	0.025*
H23B	0.9475	0.6691	0.0324	0.025*

	U11	U22	U33	U12	U13	U23
F1	0.0374 (4)	0.0265 (3)	0.0319 (3)	0.0204 (3)	0.0199 (3)	0.0113 (3)
F2	0.0268 (3)	0.0292 (3)	0.0280 (3)	0.0123 (3)	0.0044 (3)	0.0108 (3)
F3	0.0285 (3)	0.0250 (3)	0.0394 (4)	0.0103 (3)	0.0210 (3)	0.0170 (3)
O1	0.0242 (4)	0.0216 (3)	0.0227 (3)	0.0115 (3)	0.0144 (3)	0.0110 (3)
O2	0.0365 (5)	0.0326 (4)	0.0379 (4)	0.0238 (4)	0.0239 (4)	0.0197 (4)
O3	0.0221 (4)	0.0328 (4)	0.0221 (4)	0.0077 (3)	0.0141 (3)	0.0018 (3)
N1	0.0163 (4)	0.0184 (4)	0.0177 (4)	0.0081 (3)	0.0103 (3)	0.0056 (3)
N2	0.0174 (4)	0.0192 (4)	0.0174 (4)	0.0086 (3)	0.0095 (3)	0.0057 (3)
N3	0.0150 (4)	0.0176 (4)	0.0145 (3)	0.0055 (3)	0.0083 (3)	0.0043 (3)
C1	0.0162 (4)	0.0176 (4)	0.0162 (4)	0.0076 (3)	0.0082 (3)	0.0034 (3)
C2	0.0175 (4)	0.0195 (4)	0.0176 (4)	0.0082 (3)	0.0098 (3)	0.0056 (3)
C3	0.0190 (4)	0.0182 (4)	0.0164 (4)	0.0080 (3)	0.0085 (3)	0.0049 (3)
C4	0.0198 (4)	0.0210 (4)	0.0199 (4)	0.0109 (4)	0.0099 (4)	0.0053 (3)
C5	0.0173 (4)	0.0210 (4)	0.0202 (4)	0.0089 (4)	0.0109 (3)	0.0050 (3)
C6	0.0167 (4)	0.0170 (4)	0.0161 (4)	0.0064 (3)	0.0085 (3)	0.0034 (3)
C7	0.0159 (4)	0.0180 (4)	0.0158 (4)	0.0074 (3)	0.0085 (3)	0.0039 (3)
C8	0.0151 (4)	0.0176 (4)	0.0170 (4)	0.0064 (3)	0.0081 (3)	0.0046 (3)
C9	0.0213 (5)	0.0213 (4)	0.0181 (4)	0.0102 (4)	0.0116 (4)	0.0056 (3)
C10	0.0198 (4)	0.0231 (5)	0.0197 (4)	0.0098 (4)	0.0125 (4)	0.0081 (4)
C11	0.0157 (4)	0.0178 (4)	0.0197 (4)	0.0067 (3)	0.0085 (3)	0.0061 (3)
C12	0.0181 (4)	0.0206 (4)	0.0170 (4)	0.0093 (4)	0.0081 (3)	0.0036 (3)
C13	0.0182 (4)	0.0213 (4)	0.0159 (4)	0.0091 (4)	0.0091 (3)	0.0053 (3)
C14	0.0195 (5)	0.0208 (4)	0.0223 (4)	0.0084 (4)	0.0106 (4)	0.0075 (4)
C15	0.0207 (5)	0.0205 (4)	0.0184 (4)	0.0088 (4)	0.0090 (4)	0.0059 (3)
C16	0.0252 (5)	0.0226 (5)	0.0237 (5)	0.0107 (4)	0.0121 (4)	0.0124 (4)
C17	0.0309 (6)	0.0267 (5)	0.0272 (5)	0.0115 (4)	0.0170 (4)	0.0111 (4)
C18	0.0164 (4)	0.0181 (4)	0.0180 (4)	0.0056 (3)	0.0110 (3)	0.0043 (3)
C19	0.0153 (4)	0.0173 (4)	0.0178 (4)	0.0049 (3)	0.0100 (3)	0.0036 (3)
C20	0.0151 (4)	0.0216 (4)	0.0170 (4)	0.0056 (3)	0.0086 (3)	0.0040 (3)
C21	0.0198 (5)	0.0266 (5)	0.0224 (5)	0.0028 (4)	0.0131 (4)	0.0022 (4)
C22	0.0242 (5)	0.0318 (5)	0.0175 (4)	0.0080 (4)	0.0115 (4)	0.0040 (4)
C23	0.0190 (4)	0.0230 (5)	0.0165 (4)	0.0050 (4)	0.0088 (3)	0.0011 (3)

F1—C14	1.3384 (12)	C9—H9A	0.9500
F2—C14	1.3528 (12)	C10—C11	1.3950 (13)
F3—C14	1.3407 (12)	C10—H10A	0.9500
O1—C15	1.3399 (12)	C11—C12	1.3895 (13)
O1—C16	1.4561 (12)	C11—C14	1.4975 (14)
O2—C15	1.2132 (13)	C12—C13	1.3915 (13)
O3—C21	1.4251 (13)	C12—H12A	0.9500
O3—C22	1.4311 (13)	C13—H13A	0.9500
N1—C6	1.3815 (12)	C16—C17	1.4986 (15)
N1—C7	1.3883 (12)	C16—H16A	0.9900
N1—C18	1.4646 (12)	C16—H16B	0.9900
N2—C7	1.3224 (12)	C17—H17A	0.9800
N2—C1	1.3896 (12)	C17—H17B	0.9800
N3—C19	1.4610 (12)	C17—H17C	0.9800
N3—C23	1.4704 (12)	C18—C19	1.5303 (13)
N3—C20	1.4722 (12)	C18—H18A	0.9900
C1—C2	1.4000 (13)	C18—H18B	0.9900
C1—C6	1.4077 (13)	C19—H19A	0.9900
C2—C3	1.3922 (13)	C19—H19B	0.9900
C2—H2A	0.9500	C20—C21	1.5139 (13)
C3—C4	1.4124 (13)	C20—H20A	0.9900
C3—C15	1.4878 (13)	C20—H20B	0.9900
C4—C5	1.3818 (14)	C21—H21A	0.9900
C4—H4A	0.9500	C21—H21B	0.9900
C5—C6	1.3977 (13)	C22—C23	1.5152 (14)
C5—H5A	0.9500	C22—H22A	0.9900
C7—C8	1.4724 (13)	C22—H22B	0.9900
C8—C13	1.4019 (13)	C23—H23A	0.9900
C8—C9	1.4042 (13)	C23—H23B	0.9900
C9—C10	1.3865 (14)
C15—O1—C16	114.83 (8)	F2—C14—C11	111.39 (8)
C21—O3—C22	109.12 (8)	O2—C15—O1	123.35 (9)
C6—N1—C7	106.10 (8)	O2—C15—C3	123.50 (9)
C6—N1—C18	123.21 (8)	O1—C15—C3	113.15 (8)
C7—N1—C18	130.41 (8)	O1—C16—C17	107.55 (8)
C7—N2—C1	105.02 (8)	O1—C16—H16A	110.2
C19—N3—C23	109.01 (7)	C17—C16—H16A	110.2
C19—N3—C20	111.75 (7)	O1—C16—H16B	110.2
C23—N3—C20	108.99 (7)	C17—C16—H16B	110.2
N2—C1—C2	129.84 (9)	H16A—C16—H16B	108.5
N2—C1—C6	109.97 (8)	C16—C17—H17A	109.5
C2—C1—C6	120.18 (9)	C16—C17—H17B	109.5
C3—C2—C1	117.21 (9)	H17A—C17—H17B	109.5
C3—C2—H2A	121.4	C16—C17—H17C	109.5
C1—C2—H2A	121.4	H17A—C17—H17C	109.5
C2—C3—C4	121.52 (9)	H17B—C17—H17C	109.5
C2—C3—C15	122.16 (9)	N1—C18—C19	111.25 (8)
C4—C3—C15	116.30 (9)	N1—C18—H18A	109.4
C5—C4—C3	122.02 (9)	C19—C18—H18A	109.4
C5—C4—H4A	119.0	N1—C18—H18B	109.4
C3—C4—H4A	119.0	C19—C18—H18B	109.4
C4—C5—C6	116.02 (9)	H18A—C18—H18B	108.0
C4—C5—H5A	122.0	N3—C19—C18	111.69 (7)
C6—C5—H5A	122.0	N3—C19—H19A	109.3
N1—C6—C5	131.06 (9)	C18—C19—H19A	109.3
N1—C6—C1	105.89 (8)	N3—C19—H19B	109.3
C5—C6—C1	122.99 (9)	C18—C19—H19B	109.3
N2—C7—N1	113.01 (8)	H19A—C19—H19B	107.9
N2—C7—C8	122.72 (8)	N3—C20—C21	110.18 (8)
N1—C7—C8	124.07 (8)	N3—C20—H20A	109.6
C13—C8—C9	118.97 (9)	C21—C20—H20A	109.6
C13—C8—C7	117.53 (8)	N3—C20—H20B	109.6
C9—C8—C7	123.49 (8)	C21—C20—H20B	109.6
C10—C9—C8	120.37 (9)	H20A—C20—H20B	108.1
C10—C9—H9A	119.8	O3—C21—C20	111.87 (8)
C8—C9—H9A	119.8	O3—C21—H21A	109.2
C9—C10—C11	119.71 (9)	C20—C21—H21A	109.2
C9—C10—H10A	120.1	O3—C21—H21B	109.2
C11—C10—H10A	120.1	C20—C21—H21B	109.2
C12—C11—C10	120.83 (9)	H21A—C21—H21B	107.9
C12—C11—C14	121.00 (9)	O3—C22—C23	110.72 (8)
C10—C11—C14	118.13 (9)	O3—C22—H22A	109.5
C11—C12—C13	119.28 (9)	C23—C22—H22A	109.5
C11—C12—H12A	120.4	O3—C22—H22B	109.5
C13—C12—H12A	120.4	C23—C22—H22B	109.5
C12—C13—C8	120.76 (9)	H22A—C22—H22B	108.1
C12—C13—H13A	119.6	N3—C23—C22	110.37 (8)
C8—C13—H13A	119.6	N3—C23—H23A	109.6
F1—C14—F3	107.03 (8)	C22—C23—H23A	109.6
F1—C14—F2	106.57 (8)	N3—C23—H23B	109.6
F3—C14—F2	106.04 (8)	C22—C23—H23B	109.6
F1—C14—C11	112.96 (8)	H23A—C23—H23B	108.1
F3—C14—C11	112.41 (8)
C7—N2—C1—C2	179.25 (10)	C9—C10—C11—C14	−178.85 (9)
C7—N2—C1—C6	0.28 (10)	C10—C11—C12—C13	1.81 (15)
N2—C1—C2—C3	−177.58 (9)	C14—C11—C12—C13	179.42 (9)
C6—C1—C2—C3	1.29 (14)	C11—C12—C13—C8	0.00 (15)
C1—C2—C3—C4	0.72 (14)	C9—C8—C13—C12	−2.40 (14)
C1—C2—C3—C15	−177.84 (9)	C7—C8—C13—C12	176.78 (9)
C2—C3—C4—C5	−2.01 (15)	C12—C11—C14—F1	7.10 (13)
C15—C3—C4—C5	176.62 (9)	C10—C11—C14—F1	−175.22 (9)
C3—C4—C5—C6	1.14 (14)	C12—C11—C14—F3	128.35 (10)
C7—N1—C6—C5	−176.49 (10)	C10—C11—C14—F3	−53.98 (12)
C18—N1—C6—C5	−1.98 (16)	C12—C11—C14—F2	−112.80 (10)
C7—N1—C6—C1	0.82 (10)	C10—C11—C14—F2	64.87 (12)
C18—N1—C6—C1	175.33 (8)	C16—O1—C15—O2	−2.71 (14)
C4—C5—C6—N1	177.86 (9)	C16—O1—C15—C3	176.96 (8)
C4—C5—C6—C1	0.94 (14)	C2—C3—C15—O2	169.88 (10)
N2—C1—C6—N1	−0.71 (10)	C4—C3—C15—O2	−8.74 (15)
C2—C1—C6—N1	−179.79 (8)	C2—C3—C15—O1	−9.78 (13)
N2—C1—C6—C5	176.88 (9)	C4—C3—C15—O1	171.59 (8)
C2—C1—C6—C5	−2.20 (14)	C15—O1—C16—C17	−179.41 (9)
C1—N2—C7—N1	0.27 (11)	C6—N1—C18—C19	79.90 (11)
C1—N2—C7—C8	−174.75 (8)	C7—N1—C18—C19	−107.04 (11)
C6—N1—C7—N2	−0.71 (11)	C23—N3—C19—C18	−179.88 (8)
C18—N1—C7—N2	−174.67 (9)	C20—N3—C19—C18	59.59 (10)
C6—N1—C7—C8	174.22 (8)	N1—C18—C19—N3	173.79 (8)
C18—N1—C7—C8	0.26 (15)	C19—N3—C20—C21	175.96 (8)
N2—C7—C8—C13	31.52 (13)	C23—N3—C20—C21	55.41 (10)
N1—C7—C8—C13	−142.93 (9)	C22—O3—C21—C20	59.43 (12)
N2—C7—C8—C9	−149.33 (10)	N3—C20—C21—O3	−58.04 (12)
N1—C7—C8—C9	36.21 (14)	C21—O3—C22—C23	−59.79 (11)
C13—C8—C9—C10	3.05 (15)	C19—N3—C23—C22	−178.76 (8)
C7—C8—C9—C10	−176.09 (9)	C20—N3—C23—C22	−56.55 (11)
C8—C9—C10—C11	−1.29 (15)	O3—C22—C23—N3	59.56 (12)
C9—C10—C11—C12	−1.17 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F1i	0.95	2.51	3.4617 (15)	175
C10—H10A···O3ii	0.95	2.38	3.1889 (14)	143
C20—H20A···O2iii	0.99	2.52	3.4878 (14)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F1i	0.95	2.51	3.4617 (15)	175
C10—H10A⋯O3ii	0.95	2.38	3.1889 (14)	143
C20—H20A⋯O2iii	0.99	2.52	3.4878 (14)	166

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