1-{2-Benz-yloxy-2-[4-(morpholin-4-yl)phen-yl]eth-yl}-1H-benzimidazole.

In the title compound, C26H27N3O2, the morpholine ring adopts a chair conformation. The benzene and phenyl rings are inclined to the benzimidazole mean plane by 7.28 (6) and 61.45 (4)°, respectively. In the crystal, pairs of weak C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers. These dimers are further connected via weak C-H⋯N hydrogen bonds. A weak C-H⋯π inter-action is also observed.

Related literature

For general background to the biological activity of benzimidazole derivatives, see: Özel Güven et al. (2007a ▶,b ▶). For related structures, see: Caira et al. (2004 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2008a ▶,b ▶,c ▶); Peeters et al. (1979a ▶,b ▶, 1996 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H27N3O2

M = 413.51

Triclinic,

a = 9.4719 (3) Å

b = 10.5057 (3) Å

c = 11.8110 (4) Å

α = 96.824 (3)°

β = 108.953 (4)°

γ = 98.312 (3)°

V = 1082.51 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.32 × 0.25 × 0.22 mm

Data collection

Rigaku Saturn724+ diffractometer

13756 measured reflections

4972 independent reflections

3736 reflections with I > 2σ(I)

R int = 0.043

3 standard reflections every 2 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.135

S = 1.06

4972 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051306/cv5371sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051306/cv5371Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051306/cv5371Isup3.cml

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

C26H27N3O2	Z = 2
Mr = 413.51	F(000) = 440
Triclinic, P1	Dx = 1.269 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4719 (3) Å	Cell parameters from 11428 reflections
b = 10.5057 (3) Å	θ = 3.0–27.6°
c = 11.8110 (4) Å	µ = 0.08 mm−1
α = 96.824 (3)°	T = 100 K
β = 108.953 (4)°	Prism, colourless
γ = 98.312 (3)°	0.32 × 0.25 × 0.22 mm
V = 1082.51 (7) Å3

Rigaku Saturn724+ diffractometer	Rint = 0.043
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 3.1°
Graphite monochromator	h = −12→12
profile data from ω–scans	k = −13→13
13756 measured reflections	l = −15→15
4972 independent reflections	3 standard reflections every 2 min
3736 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.355P] where P = (Fo2 + 2Fc2)/3
4972 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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	0.28084 (13)	0.57424 (10)	0.27381 (10)	0.0245 (3)
O2	−0.08746 (15)	−0.09871 (11)	−0.38295 (11)	0.0336 (3)
N1	0.18512 (16)	0.52783 (12)	0.47120 (12)	0.0239 (3)
N2	0.28757 (19)	0.70971 (13)	0.61301 (13)	0.0312 (3)
N3	0.03315 (15)	0.10262 (12)	−0.17348 (11)	0.0203 (3)
C1	0.24066 (19)	0.44368 (15)	0.28999 (14)	0.0240 (3)
H1	0.3308	0.4185	0.3444	0.029*
C2	0.12280 (19)	0.44506 (15)	0.35127 (14)	0.0243 (3)
H2A	0.0368	0.4768	0.3008	0.029*
H2B	0.0864	0.3566	0.3593	0.029*
C3	0.2357 (2)	0.65983 (15)	0.49714 (15)	0.0296 (4)
H3	0.2334	0.7103	0.4372	0.036*
C4	0.20304 (18)	0.48813 (15)	0.58148 (13)	0.0211 (3)
C5	0.16909 (19)	0.36691 (15)	0.61283 (14)	0.0240 (3)
H5	0.1268	0.2914	0.5544	0.029*
C6	0.2014 (2)	0.36446 (16)	0.73509 (15)	0.0288 (4)
H6	0.1793	0.2854	0.7596	0.035*
C7	0.2668 (2)	0.47816 (17)	0.82337 (15)	0.0303 (4)
H7	0.2874	0.4726	0.9050	0.036*
C8	0.3011 (2)	0.59754 (16)	0.79188 (15)	0.0298 (4)
H8	0.3452	0.6724	0.8509	0.036*
C9	0.26797 (19)	0.60318 (15)	0.66909 (15)	0.0244 (3)
C10	0.4207 (2)	0.59640 (17)	0.25038 (18)	0.0319 (4)
H10A	0.4128	0.5376	0.1778	0.038*
H10B	0.5034	0.5810	0.3182	0.038*
C11	0.45016 (18)	0.73490 (16)	0.23337 (15)	0.0253 (3)
C12	0.5176 (2)	0.83670 (17)	0.33221 (16)	0.0313 (4)
H12	0.5461	0.8184	0.4108	0.038*
C13	0.5426 (2)	0.96468 (17)	0.31489 (16)	0.0317 (4)
H13	0.5868	1.0319	0.3817	0.038*
C14	0.5024 (2)	0.99292 (17)	0.19901 (16)	0.0293 (4)
H14	0.5206	1.0789	0.1874	0.035*
C15	0.4350 (2)	0.89280 (18)	0.10032 (16)	0.0320 (4)
H15	0.4065	0.9114	0.0219	0.038*
C16	0.4096 (2)	0.76504 (17)	0.11782 (16)	0.0303 (4)
H16	0.3645	0.6982	0.0507	0.036*
C17	0.18236 (19)	0.34981 (15)	0.17011 (14)	0.0224 (3)
C18	0.0535 (2)	0.36116 (17)	0.07608 (16)	0.0307 (4)
H18	−0.0005	0.4254	0.0888	0.037*
C19	0.0033 (2)	0.27977 (17)	−0.03558 (15)	0.0296 (4)
H19	−0.0826	0.2910	−0.0968	0.036*
C20	0.07978 (18)	0.18079 (14)	−0.05807 (13)	0.0199 (3)
C21	0.2087 (2)	0.16989 (17)	0.03657 (16)	0.0326 (4)
H21	0.2625	0.1051	0.0250	0.039*
C22	0.2586 (2)	0.25367 (17)	0.14774 (15)	0.0320 (4)
H22	0.3459	0.2444	0.2087	0.038*
C23	−0.1301 (2)	0.06684 (18)	−0.24194 (16)	0.0332 (4)
H23A	−0.1756	0.1436	−0.2386	0.040*
H23B	−0.1772	0.0031	−0.2055	0.040*
C24	−0.1588 (2)	0.0102 (2)	−0.37283 (17)	0.0406 (5)
H24A	−0.2675	−0.0169	−0.4157	0.049*
H24B	−0.1206	0.0772	−0.4112	0.049*
C25	0.0716 (2)	−0.05690 (18)	−0.32175 (16)	0.0332 (4)
H25A	0.1098	0.0112	−0.3590	0.040*
H25B	0.1220	−0.1297	−0.3305	0.040*
C26	0.1096 (2)	−0.00560 (17)	−0.18839 (15)	0.0296 (4)
H26A	0.0774	−0.0750	−0.1495	0.036*
H26B	0.2187	0.0238	−0.1497	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0256 (6)	0.0211 (6)	0.0273 (6)	0.0030 (5)	0.0113 (5)	0.0010 (5)
O2	0.0349 (7)	0.0277 (6)	0.0291 (7)	0.0044 (5)	0.0054 (5)	−0.0115 (5)
N1	0.0350 (8)	0.0173 (6)	0.0204 (7)	0.0025 (5)	0.0133 (6)	−0.0004 (5)
N2	0.0486 (10)	0.0190 (7)	0.0279 (8)	0.0018 (6)	0.0198 (7)	−0.0012 (6)
N3	0.0219 (7)	0.0198 (6)	0.0177 (6)	0.0028 (5)	0.0071 (5)	−0.0013 (5)
C1	0.0287 (9)	0.0198 (8)	0.0213 (8)	0.0024 (6)	0.0085 (6)	−0.0009 (6)
C2	0.0298 (9)	0.0210 (8)	0.0210 (8)	0.0004 (6)	0.0110 (7)	−0.0011 (6)
C3	0.0475 (11)	0.0171 (8)	0.0273 (9)	0.0044 (7)	0.0188 (8)	0.0010 (6)
C4	0.0234 (8)	0.0207 (7)	0.0199 (7)	0.0027 (6)	0.0108 (6)	−0.0006 (6)
C5	0.0273 (9)	0.0186 (7)	0.0249 (8)	−0.0005 (6)	0.0116 (7)	−0.0013 (6)
C6	0.0368 (10)	0.0241 (8)	0.0286 (9)	0.0022 (7)	0.0164 (7)	0.0058 (7)
C7	0.0373 (10)	0.0336 (9)	0.0202 (8)	0.0032 (8)	0.0127 (7)	0.0023 (7)
C8	0.0371 (10)	0.0252 (8)	0.0238 (8)	−0.0011 (7)	0.0129 (7)	−0.0056 (7)
C9	0.0285 (9)	0.0186 (8)	0.0263 (8)	0.0003 (6)	0.0136 (7)	−0.0019 (6)
C10	0.0268 (9)	0.0280 (9)	0.0419 (10)	0.0021 (7)	0.0153 (8)	0.0044 (7)
C11	0.0181 (8)	0.0262 (8)	0.0312 (9)	0.0023 (6)	0.0099 (6)	0.0019 (7)
C12	0.0299 (9)	0.0330 (9)	0.0247 (9)	0.0044 (7)	0.0030 (7)	0.0025 (7)
C13	0.0273 (9)	0.0262 (9)	0.0334 (9)	0.0015 (7)	0.0044 (7)	−0.0040 (7)
C14	0.0246 (9)	0.0249 (8)	0.0403 (10)	0.0046 (7)	0.0134 (7)	0.0067 (7)
C15	0.0344 (10)	0.0351 (10)	0.0295 (9)	0.0070 (8)	0.0145 (8)	0.0070 (7)
C16	0.0308 (10)	0.0303 (9)	0.0277 (9)	−0.0011 (7)	0.0135 (7)	−0.0041 (7)
C17	0.0260 (8)	0.0205 (7)	0.0200 (8)	−0.0010 (6)	0.0109 (6)	−0.0007 (6)
C18	0.0289 (9)	0.0310 (9)	0.0301 (9)	0.0102 (7)	0.0097 (7)	−0.0063 (7)
C19	0.0247 (9)	0.0345 (9)	0.0258 (9)	0.0096 (7)	0.0054 (7)	−0.0044 (7)
C20	0.0229 (8)	0.0178 (7)	0.0186 (7)	0.0002 (6)	0.0093 (6)	0.0004 (6)
C21	0.0371 (10)	0.0304 (9)	0.0267 (9)	0.0168 (8)	0.0050 (7)	−0.0036 (7)
C22	0.0345 (10)	0.0326 (9)	0.0221 (8)	0.0122 (8)	0.0010 (7)	−0.0023 (7)
C23	0.0263 (9)	0.0376 (10)	0.0288 (9)	0.0067 (8)	0.0055 (7)	−0.0090 (7)
C24	0.0395 (11)	0.0433 (11)	0.0270 (9)	0.0153 (9)	−0.0011 (8)	−0.0123 (8)
C25	0.0326 (10)	0.0333 (9)	0.0296 (9)	0.0076 (8)	0.0102 (7)	−0.0097 (7)
C26	0.0302 (9)	0.0279 (9)	0.0265 (9)	0.0099 (7)	0.0061 (7)	−0.0057 (7)

O1—C1	1.4218 (19)	C11—C12	1.391 (2)
O1—C10	1.432 (2)	C12—H12	0.9300
O2—C24	1.423 (2)	C13—C12	1.382 (2)
O2—C25	1.418 (2)	C13—H13	0.9300
N1—C2	1.4584 (19)	C14—C13	1.377 (3)
N1—C3	1.363 (2)	C14—C15	1.380 (2)
N1—C4	1.380 (2)	C14—H14	0.9300
N2—C3	1.307 (2)	C15—H15	0.9300
N2—C9	1.386 (2)	C16—C11	1.381 (2)
N3—C20	1.4020 (18)	C16—C15	1.381 (2)
N3—C23	1.461 (2)	C16—H16	0.9300
N3—C26	1.4562 (19)	C17—C18	1.389 (2)
C1—C2	1.516 (2)	C17—C22	1.372 (2)
C1—C17	1.512 (2)	C18—H18	0.9300
C1—H1	0.9800	C19—C18	1.380 (2)
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C20—C19	1.398 (2)
C3—H3	0.9300	C20—C21	1.392 (2)
C5—C4	1.390 (2)	C21—H21	0.9300
C5—C6	1.380 (2)	C22—C21	1.387 (2)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.510 (2)
C7—C6	1.403 (2)	C23—H23A	0.9700
C7—H7	0.9300	C23—H23B	0.9700
C8—C7	1.374 (2)	C24—H24A	0.9700
C8—C9	1.391 (2)	C24—H24B	0.9700
C8—H8	0.9300	C25—H25A	0.9700
C9—C4	1.409 (2)	C25—H25B	0.9700
C10—H10A	0.9700	C26—C25	1.508 (2)
C10—H10B	0.9700	C26—H26A	0.9700
C11—C10	1.491 (2)	C26—H26B	0.9700
C1—O1—C10	112.15 (12)	C12—C13—H13	119.9
C25—O2—C24	108.49 (13)	C14—C13—C12	120.23 (16)
C3—N1—C2	127.13 (14)	C14—C13—H13	119.9
C3—N1—C4	106.11 (13)	C13—C14—C15	119.58 (16)
C4—N1—C2	126.76 (13)	C13—C14—H14	120.2
C3—N2—C9	104.06 (13)	C15—C14—H14	120.2
C20—N3—C23	117.52 (12)	C14—C15—C16	120.10 (16)
C20—N3—C26	118.08 (13)	C14—C15—H15	119.9
C26—N3—C23	111.50 (13)	C16—C15—H15	119.9
O1—C1—C2	106.14 (12)	C11—C16—H16	119.5
O1—C1—C17	111.26 (12)	C15—C16—C11	121.07 (16)
O1—C1—H1	108.9	C15—C16—H16	119.5
C2—C1—H1	108.9	C18—C17—C1	121.39 (14)
C17—C1—C2	112.51 (13)	C22—C17—C1	121.31 (15)
C17—C1—H1	108.9	C22—C17—C18	117.24 (14)
N1—C2—C1	111.66 (13)	C17—C18—H18	119.1
N1—C2—H2A	109.3	C19—C18—C17	121.85 (15)
N1—C2—H2B	109.3	C19—C18—H18	119.1
C1—C2—H2A	109.3	C18—C19—C20	120.98 (16)
C1—C2—H2B	109.3	C18—C19—H19	119.5
H2A—C2—H2B	107.9	C20—C19—H19	119.5
N1—C3—H3	122.7	C19—C20—N3	120.82 (14)
N2—C3—N1	114.56 (15)	C21—C20—N3	122.19 (14)
N2—C3—H3	122.7	C21—C20—C19	116.86 (14)
N1—C4—C5	132.71 (14)	C20—C21—H21	119.3
N1—C4—C9	104.98 (13)	C22—C21—C20	121.35 (15)
C5—C4—C9	122.31 (14)	C22—C21—H21	119.3
C4—C5—H5	121.7	C17—C22—C21	121.70 (16)
C6—C5—C4	116.56 (14)	C17—C22—H22	119.1
C6—C5—H5	121.7	C21—C22—H22	119.1
C5—C6—C7	121.73 (16)	N3—C23—C24	110.50 (14)
C5—C6—H6	119.1	N3—C23—H23A	109.5
C7—C6—H6	119.1	N3—C23—H23B	109.5
C6—C7—H7	119.3	C24—C23—H23A	109.5
C8—C7—C6	121.44 (15)	C24—C23—H23B	109.5
C8—C7—H7	119.3	H23A—C23—H23B	108.1
C7—C8—C9	118.07 (15)	O2—C24—C23	112.00 (15)
C7—C8—H8	121.0	O2—C24—H24A	109.2
C9—C8—H8	121.0	O2—C24—H24B	109.2
N2—C9—C4	110.28 (14)	C23—C24—H24A	109.2
N2—C9—C8	129.83 (15)	C23—C24—H24B	109.2
C8—C9—C4	119.89 (15)	H24A—C24—H24B	107.9
O1—C10—C11	107.45 (13)	O2—C25—C26	111.75 (14)
O1—C10—H10A	110.2	O2—C25—H25A	109.3
O1—C10—H10B	110.2	O2—C25—H25B	109.3
C11—C10—H10A	110.2	C26—C25—H25A	109.3
C11—C10—H10B	110.2	C26—C25—H25B	109.3
H10A—C10—H10B	108.5	H25A—C25—H25B	107.9
C12—C11—C10	121.43 (16)	N3—C26—C25	110.05 (14)
C16—C11—C10	120.25 (15)	N3—C26—H26A	109.6
C16—C11—C12	118.32 (16)	N3—C26—H26B	109.6
C11—C12—H12	119.7	C25—C26—H26A	109.6
C13—C12—C11	120.70 (16)	C25—C26—H26B	109.7
C13—C12—H12	119.7	H26A—C26—H26B	108.2
C10—O1—C1—C2	162.84 (13)	C4—C5—C6—C7	−0.7 (3)
C10—O1—C1—C17	−74.46 (17)	C8—C7—C6—C5	0.3 (3)
C1—O1—C10—C11	179.24 (13)	C9—C8—C7—C6	0.5 (3)
C25—O2—C24—C23	−59.9 (2)	C7—C8—C9—N2	178.51 (17)
C24—O2—C25—C26	60.96 (19)	C7—C8—C9—C4	−0.8 (3)
C3—N1—C2—C1	64.8 (2)	N2—C9—C4—N1	0.47 (18)
C4—N1—C2—C1	−116.02 (17)	N2—C9—C4—C5	−179.06 (15)
C2—N1—C3—N2	−179.33 (16)	C8—C9—C4—N1	179.93 (15)
C4—N1—C3—N2	1.4 (2)	C8—C9—C4—C5	0.4 (2)
C2—N1—C4—C5	−0.9 (3)	C12—C11—C10—O1	82.65 (19)
C2—N1—C4—C9	179.66 (15)	C16—C11—C10—O1	−96.93 (18)
C3—N1—C4—C5	178.42 (18)	C10—C11—C12—C13	−179.33 (16)
C3—N1—C4—C9	−1.04 (17)	C16—C11—C12—C13	0.3 (3)
C9—N2—C3—N1	−1.0 (2)	C14—C13—C12—C11	−0.7 (3)
C3—N2—C9—C4	0.32 (19)	C15—C14—C13—C12	0.9 (3)
C3—N2—C9—C8	−179.07 (18)	C13—C14—C15—C16	−0.7 (3)
C23—N3—C20—C19	−36.8 (2)	C15—C16—C11—C10	179.54 (16)
C23—N3—C20—C21	147.48 (17)	C15—C16—C11—C12	0.0 (3)
C26—N3—C20—C19	−175.07 (15)	C11—C16—C15—C14	0.3 (3)
C26—N3—C20—C21	9.2 (2)	C1—C17—C18—C19	176.97 (16)
C20—N3—C23—C24	167.07 (14)	C22—C17—C18—C19	−0.1 (3)
C26—N3—C23—C24	−52.07 (19)	C1—C17—C22—C21	−177.82 (17)
C20—N3—C26—C25	−166.46 (14)	C18—C17—C22—C21	−0.8 (3)
C23—N3—C26—C25	52.92 (19)	C20—C19—C18—C17	0.9 (3)
O1—C1—C2—N1	−62.84 (16)	N3—C20—C19—C18	−176.71 (16)
C17—C1—C2—N1	175.25 (13)	C21—C20—C19—C18	−0.8 (3)
O1—C1—C17—C18	−60.9 (2)	N3—C20—C21—C22	175.82 (16)
O1—C1—C17—C22	116.07 (17)	C19—C20—C21—C22	−0.1 (3)
C2—C1—C17—C18	58.1 (2)	C17—C22—C21—C20	0.8 (3)
C2—C1—C17—C22	−124.97 (17)	N3—C23—C24—O2	56.1 (2)
C6—C5—C4—N1	−179.01 (17)	N3—C26—C25—O2	−58.1 (2)
C6—C5—C4—C9	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.58	3.478 (2)	163
C6—H6···N3ii	0.93	2.56	3.439 (2)	159
C2—H2A···Cgiii	0.97	2.66	3.451 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.58	3.478 (2)	163
C6—H6⋯N3ii	0.93	2.56	3.439 (2)	159
C2—H2A⋯Cg iii	0.97	2.66	3.451 (2)	139

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