2-(4-Chloro-phen-yl)-1-pentyl-4,5-di-phenyl-1H-imidazole.

In the title compound, C26H25ClN2, the phenyl rings and the 2-(4-chloro-phen-yl) group make dihedral angles of 30.03 (11), 67.49 (12) and 41.56 (11)°, respectively, with the imidazole ring. In the crystal, the mol-ecules inter-act with each other via very weak C-H⋯π contacts, forming layers parallel to (110).

Related literature

For biological applications of imidazole derivatives, see: Shalini et al. (2011 ▶); Ramesh et al. (2012 ▶); Wolkenberg et al. (2004 ▶). For related structures, see: Simpson et al. (2013 ▶); Akkurt et al. (2013 ▶).

Experimental

Crystal data

C26H25ClN2

M = 400.93

Monoclinic,

a = 10.471 (2) Å

b = 9.7798 (19) Å

c = 21.682 (4) Å

β = 91.080 (4)°

V = 2219.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 150 K

0.36 × 0.14 × 0.11 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.969, T max = 0.980

16940 measured reflections

4346 independent reflections

2593 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.110

S = 0.89

4346 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018229/yk2095sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018229/yk2095Isup2.hkl

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

C26H25ClN2	F(000) = 848
Mr = 400.93	Dx = 1.200 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 811 reflections
a = 10.471 (2) Å	θ = 2.8–23.3°
b = 9.7798 (19) Å	µ = 0.19 mm−1
c = 21.682 (4) Å	T = 150 K
β = 91.080 (4)°	Block, colourless
V = 2219.9 (7) Å3	0.36 × 0.14 × 0.11 mm
Z = 4

Bruker APEX 2000 CCD area-detector diffractometer	4346 independent reflections
Radiation source: fine-focus sealed tube	2593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.969, Tmax = 0.980	k = −12→11
16940 measured reflections	l = −26→26

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.110	W = 1/[Σ2(FO2) + (0.0377P)2] WHERE P = (FO2 + 2FC2)/3
S = 0.89	(Δ/σ)max = 0.001
4346 reflections	Δρmax = 0.26 e Å−3
263 parameters	Δρmin = −0.31 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All s.u.'s are estimated from the variances of the (full) variance-covariance matrix. The cell s.u.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.48467 (6)	0.57406 (7)	1.11900 (3)	0.0565 (3)
N1	0.95325 (15)	0.25818 (17)	0.95080 (7)	0.0286 (6)
N3	1.02899 (16)	0.24351 (18)	1.04691 (7)	0.0308 (6)
C2	0.9371 (2)	0.2951 (2)	1.01115 (9)	0.0286 (7)
C4	1.10784 (19)	0.1722 (2)	1.00835 (9)	0.0295 (7)
C5	1.06275 (19)	0.1789 (2)	0.94862 (9)	0.0288 (7)
C6	0.87851 (19)	0.3032 (2)	0.89685 (9)	0.0304 (7)
C7	0.94069 (19)	0.4250 (2)	0.86571 (9)	0.0338 (8)
C8	0.8550 (2)	0.4923 (2)	0.81788 (10)	0.0373 (8)
C9	0.9151 (2)	0.6130 (3)	0.78703 (11)	0.0500 (9)
C10	0.8260 (2)	0.6845 (3)	0.74173 (11)	0.0629 (11)
C11	0.82661 (19)	0.3684 (2)	1.03559 (9)	0.0293 (7)
C12	0.7711 (2)	0.4823 (2)	1.00771 (10)	0.0358 (8)
C13	0.6648 (2)	0.5448 (2)	1.03269 (10)	0.0393 (8)
C14	0.6155 (2)	0.4937 (3)	1.08642 (10)	0.0384 (8)
C15	0.6700 (2)	0.3823 (2)	1.11571 (10)	0.0381 (8)
C16	0.7750 (2)	0.3207 (2)	1.09032 (9)	0.0336 (8)
C17	1.22136 (19)	0.1012 (2)	1.03386 (9)	0.0304 (7)
C18	1.2830 (2)	0.1515 (3)	1.08647 (10)	0.0429 (9)
C19	1.3879 (2)	0.0841 (3)	1.11173 (11)	0.0534 (10)
C20	1.4320 (2)	−0.0343 (3)	1.08535 (12)	0.0519 (10)
C21	1.3724 (2)	−0.0846 (3)	1.03348 (11)	0.0462 (9)
C22	1.2677 (2)	−0.0180 (2)	1.00781 (10)	0.0366 (8)
C23	1.1111 (2)	0.1239 (2)	0.88975 (9)	0.0304 (8)
C24	1.2243 (2)	0.1728 (3)	0.86639 (10)	0.0445 (9)
C25	1.2713 (2)	0.1218 (3)	0.81166 (11)	0.0564 (10)
C26	1.2062 (3)	0.0227 (3)	0.77984 (11)	0.0522 (10)
C27	1.0928 (3)	−0.0263 (3)	0.80242 (10)	0.0509 (10)
C28	1.0457 (2)	0.0242 (2)	0.85709 (10)	0.0401 (8)
H6A	0.79150	0.32870	0.90970	0.0360*
H6B	0.87070	0.22690	0.86700	0.0360*
H7A	0.96480	0.49340	0.89750	0.0410*
H7B	1.02000	0.39420	0.84580	0.0410*
H8A	0.83120	0.42380	0.78600	0.0450*
H8B	0.77550	0.52250	0.83790	0.0450*
H9A	0.99180	0.58190	0.76500	0.0600*
H9B	0.94330	0.67920	0.81900	0.0600*
H10A	0.79660	0.61930	0.71020	0.0950*
H10B	0.87130	0.75990	0.72200	0.0950*
H10C	0.75220	0.72050	0.76360	0.0950*
H12	0.80650	0.51800	0.97100	0.0430*
H13	0.62660	0.62170	1.01300	0.0470*
H15	0.63550	0.34850	1.15290	0.0460*
H16	0.81290	0.24420	1.11050	0.0400*
H18	1.25280	0.23280	1.10530	0.0510*
H19	1.42970	0.11990	1.14750	0.0640*
H20	1.50340	−0.08080	1.10310	0.0620*
H21	1.40310	−0.16590	1.01500	0.0550*
H22	1.22700	−0.05430	0.97190	0.0440*
H24	1.27040	0.24200	0.88810	0.0530*
H25	1.34940	0.15600	0.79620	0.0680*
H26	1.23870	−0.01230	0.74240	0.0630*
H27	1.04690	−0.09500	0.78040	0.0610*
H28	0.96750	−0.01010	0.87230	0.0480*

	U11	U22	U33	U12	U13	U23
Cl1	0.0404 (4)	0.0733 (5)	0.0562 (4)	0.0153 (3)	0.0123 (3)	−0.0120 (4)
N1	0.0299 (10)	0.0311 (11)	0.0249 (10)	0.0013 (9)	0.0005 (8)	0.0005 (8)
N3	0.0310 (10)	0.0337 (12)	0.0279 (10)	0.0011 (9)	0.0048 (8)	−0.0006 (9)
C2	0.0315 (13)	0.0272 (13)	0.0273 (12)	−0.0010 (10)	0.0035 (10)	−0.0005 (10)
C4	0.0312 (12)	0.0274 (13)	0.0301 (12)	0.0002 (10)	0.0042 (10)	0.0013 (10)
C5	0.0292 (12)	0.0275 (13)	0.0298 (12)	0.0013 (10)	0.0029 (10)	0.0007 (10)
C6	0.0263 (12)	0.0357 (14)	0.0290 (12)	0.0025 (10)	−0.0025 (10)	−0.0003 (10)
C7	0.0326 (13)	0.0381 (15)	0.0309 (12)	−0.0019 (11)	0.0025 (10)	0.0019 (11)
C8	0.0393 (14)	0.0359 (15)	0.0366 (13)	−0.0003 (11)	0.0021 (11)	0.0027 (11)
C9	0.0488 (15)	0.0581 (19)	0.0432 (15)	0.0014 (14)	0.0070 (12)	0.0190 (14)
C10	0.071 (2)	0.063 (2)	0.0550 (18)	0.0116 (16)	0.0071 (15)	0.0256 (15)
C11	0.0298 (12)	0.0291 (14)	0.0291 (12)	−0.0025 (10)	0.0013 (10)	−0.0034 (10)
C12	0.0378 (14)	0.0355 (15)	0.0344 (13)	−0.0015 (11)	0.0081 (11)	−0.0004 (11)
C13	0.0353 (14)	0.0414 (16)	0.0412 (14)	0.0057 (11)	0.0010 (11)	−0.0024 (12)
C14	0.0317 (13)	0.0453 (16)	0.0383 (14)	0.0041 (12)	0.0053 (11)	−0.0108 (12)
C15	0.0401 (14)	0.0449 (16)	0.0295 (13)	−0.0035 (12)	0.0099 (11)	−0.0039 (12)
C16	0.0365 (13)	0.0327 (14)	0.0317 (13)	0.0019 (11)	0.0028 (11)	−0.0014 (11)
C17	0.0300 (12)	0.0316 (14)	0.0299 (12)	−0.0008 (11)	0.0056 (10)	0.0064 (11)
C18	0.0434 (15)	0.0466 (17)	0.0385 (14)	0.0065 (12)	−0.0032 (12)	−0.0010 (12)
C19	0.0455 (16)	0.070 (2)	0.0441 (15)	0.0057 (15)	−0.0117 (13)	0.0017 (15)
C20	0.0370 (15)	0.065 (2)	0.0537 (17)	0.0133 (14)	−0.0014 (13)	0.0149 (15)
C21	0.0429 (15)	0.0426 (17)	0.0533 (16)	0.0119 (13)	0.0082 (13)	0.0090 (14)
C22	0.0373 (14)	0.0348 (15)	0.0378 (13)	0.0022 (11)	0.0018 (11)	0.0057 (11)
C23	0.0344 (13)	0.0294 (14)	0.0275 (12)	0.0072 (11)	0.0003 (10)	0.0017 (10)
C24	0.0357 (14)	0.0588 (18)	0.0391 (14)	−0.0044 (12)	0.0073 (11)	−0.0100 (13)
C25	0.0418 (15)	0.082 (2)	0.0458 (16)	0.0031 (15)	0.0155 (13)	−0.0067 (16)
C26	0.0646 (19)	0.062 (2)	0.0304 (14)	0.0183 (15)	0.0098 (13)	−0.0049 (14)
C27	0.078 (2)	0.0425 (17)	0.0323 (14)	−0.0033 (15)	0.0013 (13)	−0.0064 (12)
C28	0.0503 (15)	0.0360 (15)	0.0341 (13)	−0.0045 (12)	0.0049 (12)	0.0016 (11)

Cl1—C14	1.741 (2)	C25—C26	1.365 (4)
N1—C2	1.371 (2)	C26—C27	1.379 (4)
N1—C5	1.386 (3)	C27—C28	1.384 (3)
N1—C6	1.463 (3)	C6—H6A	0.9900
N3—C2	1.324 (3)	C6—H6B	0.9900
N3—C4	1.376 (3)	C7—H7A	0.9900
C2—C11	1.468 (3)	C7—H7B	0.9900
C4—C5	1.372 (3)	C8—H8A	0.9900
C4—C17	1.475 (3)	C8—H8B	0.9900
C5—C23	1.483 (3)	C9—H9A	0.9900
C6—C7	1.522 (3)	C9—H9B	0.9900
C7—C8	1.510 (3)	C10—H10A	0.9800
C8—C9	1.501 (3)	C10—H10B	0.9800
C9—C10	1.513 (3)	C10—H10C	0.9800
C11—C12	1.390 (3)	C12—H12	0.9500
C11—C16	1.394 (3)	C13—H13	0.9500
C12—C13	1.389 (3)	C15—H15	0.9500
C13—C14	1.377 (3)	C16—H16	0.9500
C14—C15	1.379 (3)	C18—H18	0.9500
C15—C16	1.378 (3)	C19—H19	0.9500
C17—C18	1.390 (3)	C20—H20	0.9500
C17—C22	1.387 (3)	C21—H21	0.9500
C18—C19	1.385 (3)	C22—H22	0.9500
C19—C20	1.375 (4)	C24—H24	0.9500
C20—C21	1.367 (4)	C25—H25	0.9500
C21—C22	1.383 (3)	C26—H26	0.9500
C23—C24	1.383 (3)	C27—H27	0.9500
C23—C28	1.379 (3)	C28—H28	0.9500
C24—C25	1.386 (3)
C2—N1—C5	107.28 (16)	C6—C7—H7B	109.00
C2—N1—C6	127.60 (16)	C8—C7—H7A	109.00
C5—N1—C6	124.87 (16)	C8—C7—H7B	109.00
C2—N3—C4	105.97 (16)	H7A—C7—H7B	108.00
N1—C2—N3	110.93 (17)	C7—C8—H8A	109.00
N1—C2—C11	125.82 (18)	C7—C8—H8B	109.00
N3—C2—C11	122.92 (17)	C9—C8—H8A	109.00
N3—C4—C5	110.47 (17)	C9—C8—H8B	109.00
N3—C4—C17	119.95 (17)	H8A—C8—H8B	108.00
C5—C4—C17	129.58 (18)	C8—C9—H9A	109.00
N1—C5—C4	105.36 (17)	C8—C9—H9B	109.00
N1—C5—C23	121.90 (17)	C10—C9—H9A	109.00
C4—C5—C23	132.71 (19)	C10—C9—H9B	109.00
N1—C6—C7	111.31 (16)	H9A—C9—H9B	108.00
C6—C7—C8	113.10 (16)	C9—C10—H10A	109.00
C7—C8—C9	113.60 (17)	C9—C10—H10B	109.00
C8—C9—C10	113.21 (19)	C9—C10—H10C	110.00
C2—C11—C12	124.08 (18)	H10A—C10—H10B	109.00
C2—C11—C16	117.69 (18)	H10A—C10—H10C	109.00
C12—C11—C16	118.23 (18)	H10B—C10—H10C	109.00
C11—C12—C13	120.99 (19)	C11—C12—H12	119.00
C12—C13—C14	119.1 (2)	C13—C12—H12	120.00
Cl1—C14—C13	119.34 (19)	C12—C13—H13	120.00
Cl1—C14—C15	119.46 (17)	C14—C13—H13	120.00
C13—C14—C15	121.2 (2)	C14—C15—H15	120.00
C14—C15—C16	119.20 (19)	C16—C15—H15	120.00
C11—C16—C15	121.28 (19)	C11—C16—H16	119.00
C4—C17—C18	119.97 (19)	C15—C16—H16	119.00
C4—C17—C22	121.91 (18)	C17—C18—H18	120.00
C18—C17—C22	118.1 (2)	C19—C18—H18	120.00
C17—C18—C19	120.6 (2)	C18—C19—H19	120.00
C18—C19—C20	120.4 (2)	C20—C19—H19	120.00
C19—C20—C21	119.6 (2)	C19—C20—H20	120.00
C20—C21—C22	120.5 (2)	C21—C20—H20	120.00
C17—C22—C21	120.8 (2)	C20—C21—H21	120.00
C5—C23—C24	119.91 (19)	C22—C21—H21	120.00
C5—C23—C28	121.60 (19)	C17—C22—H22	120.00
C24—C23—C28	118.5 (2)	C21—C22—H22	120.00
C23—C24—C25	120.6 (2)	C23—C24—H24	120.00
C24—C25—C26	120.4 (2)	C25—C24—H24	120.00
C25—C26—C27	119.5 (2)	C24—C25—H25	120.00
C26—C27—C28	120.2 (2)	C26—C25—H25	120.00
C23—C28—C27	120.7 (2)	C25—C26—H26	120.00
N1—C6—H6A	109.00	C27—C26—H26	120.00
N1—C6—H6B	109.00	C26—C27—H27	120.00
C7—C6—H6A	109.00	C28—C27—H27	120.00
C7—C6—H6B	109.00	C23—C28—H28	120.00
H6A—C6—H6B	108.00	C27—C28—H28	120.00
C6—C7—H7A	109.00
C5—N1—C2—N3	−0.3 (2)	N1—C6—C7—C8	−168.61 (16)
C5—N1—C2—C11	−173.78 (19)	C6—C7—C8—C9	179.75 (18)
C6—N1—C2—N3	−174.66 (18)	C7—C8—C9—C10	−176.82 (19)
C6—N1—C2—C11	11.9 (3)	C2—C11—C12—C13	178.54 (19)
C2—N1—C5—C4	−0.2 (2)	C16—C11—C12—C13	−1.8 (3)
C2—N1—C5—C23	−178.41 (18)	C2—C11—C16—C15	−178.87 (19)
C6—N1—C5—C4	174.38 (17)	C12—C11—C16—C15	1.4 (3)
C6—N1—C5—C23	−3.9 (3)	C11—C12—C13—C14	1.0 (3)
C2—N1—C6—C7	94.4 (2)	C12—C13—C14—Cl1	178.44 (17)
C5—N1—C6—C7	−79.0 (2)	C12—C13—C14—C15	0.2 (3)
C4—N3—C2—N1	0.7 (2)	Cl1—C14—C15—C16	−178.79 (17)
C4—N3—C2—C11	174.34 (18)	C13—C14—C15—C16	−0.5 (3)
C2—N3—C4—C5	−0.8 (2)	C14—C15—C16—C11	−0.3 (3)
C2—N3—C4—C17	179.98 (19)	C4—C17—C18—C19	178.5 (2)
N1—C2—C11—C12	−45.1 (3)	C22—C17—C18—C19	0.2 (3)
N1—C2—C11—C16	135.2 (2)	C4—C17—C22—C21	−178.4 (2)
N3—C2—C11—C12	142.2 (2)	C18—C17—C22—C21	−0.1 (3)
N3—C2—C11—C16	−37.5 (3)	C17—C18—C19—C20	−0.5 (4)
N3—C4—C5—N1	0.6 (2)	C18—C19—C20—C21	0.7 (4)
N3—C4—C5—C23	178.6 (2)	C19—C20—C21—C22	−0.6 (4)
C17—C4—C5—N1	179.72 (19)	C20—C21—C22—C17	0.3 (4)
C17—C4—C5—C23	−2.3 (4)	C5—C23—C24—C25	179.5 (2)
N3—C4—C17—C18	−29.6 (3)	C28—C23—C24—C25	−0.5 (3)
N3—C4—C17—C22	148.7 (2)	C5—C23—C28—C27	−179.6 (2)
C5—C4—C17—C18	151.4 (2)	C24—C23—C28—C27	0.4 (3)
C5—C4—C17—C22	−30.4 (3)	C23—C24—C25—C26	0.2 (4)
N1—C5—C23—C24	111.6 (2)	C24—C25—C26—C27	0.2 (4)
N1—C5—C23—C28	−68.3 (3)	C25—C26—C27—C28	−0.3 (4)
C4—C5—C23—C24	−66.1 (3)	C26—C27—C28—C23	0.0 (4)
C4—C5—C23—C28	114.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···C25i	0.95	3.00	3.887 (3)	157
C24—H24···C13ii	0.95	2.78	3.697 (3)	163
C28—H28···N3iii	0.95	2.88	3.444 (3)	119
C28—H28···C17iii	0.95	3.00	3.894 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯C25i	0.95	3.00	3.887 (3)	157
C24—H24⋯C13ii	0.95	2.78	3.697 (3)	163
C28—H28⋯N3iii	0.95	2.88	3.444 (3)	119
C28—H28⋯C17iii	0.95	3.00	3.894 (3)	158

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