1-Benzyl-2-(4-chloro-phen-yl)-4,5-di-phenyl-1H-imidazole.

The mol-ecular conformation of the title compound, C(28)H(21)ClN(2), is stabilized by an intra-molecular C-H⋯N hydrogen bond. It has many pharmacological properties, such as being an inhibitor of P38 MAP Kinase, and can play an important role in biochemical processes.

Related literature

For related structures and properties, see: Balalaie et al. (2003 ▶); Nagarapu et al. (2007 ▶); Kidwai et al. (2007 ▶).

Experimental

Crystal data

C28H21ClN2

M = 420.92

Triclinic,

a = 7.4880 (11) Å

b = 9.2711 (16) Å

c = 16.049 (3) Å

α = 87.169 (13)°

β = 76.704 (12)°

γ = 87.842 (13)°

V = 1082.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 290 (2) K

0.3 × 0.2 × 0.2 mm

Data collection

STOE IPDS-II diffractometer

Absorption correction: none

8769 measured reflections

4246 independent reflections

2814 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.090

S = 0.94

4246 reflections

288 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.20 e Å−3

Data collection: X-AREA (Stoe & Cie, 1997 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, 1. DOI: 10.1107/S1600536808016802/bt2715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016802/bt2715Isup2.hkl

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

C28H21ClN2	Z = 2
Mr = 420.92	F000 = 440
Triclinic, P1	Dx = 1.291 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.4880 (11) Å	Cell parameters from 6987 reflections
b = 9.2711 (16) Å	θ = 1.2–29.8º
c = 16.049 (3) Å	µ = 0.19 mm−1
α = 87.169 (13)º	T = 290 (2) K
β = 76.704 (12)º	Block, colorless
γ = 87.842 (13)º	0.3 × 0.2 × 0.2 mm
V = 1082.6 (3) Å3

STOE IPDS-II diffractometer	2814 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Monochromator: graphite	θmax = 26.0º
T = 290(2) K	θmin = 2.2º
Area detector – phi oscillation scans	h = −9→9
Absorption correction: none	k = −11→10
8769 measured reflections	l = −19→19
4246 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
4246 reflections	Δρmax = 0.13 e Å−3
288 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Cl1	0.17061 (7)	0.52946 (7)	0.32233 (4)	0.0741 (2)
N1	0.60096 (17)	0.82368 (15)	0.59681 (9)	0.0412 (3)
N2	0.36337 (17)	0.74456 (15)	0.69583 (8)	0.0403 (3)
C1	0.2919 (2)	0.56492 (19)	0.54889 (12)	0.0456 (4)
H1	0.2804	0.5096	0.5997	0.055*
C2	0.4446 (2)	0.75675 (17)	0.61039 (10)	0.0393 (4)
C3	0.9378 (2)	0.9430 (2)	0.61528 (12)	0.0476 (4)
H3	0.9370	0.8959	0.5656	0.057*
C4	0.7878 (2)	0.93196 (18)	0.68467 (11)	0.0413 (4)
C5	0.4409 (2)	0.80553 (19)	0.83352 (11)	0.0419 (4)
C6	0.2487 (2)	0.5939 (2)	0.40748 (12)	0.0492 (5)
C7	0.2308 (2)	0.5117 (2)	0.48201 (12)	0.0491 (4)
H7	0.1784	0.4213	0.4874	0.059*
C8	0.6244 (2)	0.85566 (17)	0.67670 (10)	0.0391 (4)
C9	0.4790 (2)	0.80756 (18)	0.73880 (11)	0.0398 (4)
C10	0.1795 (2)	0.55784 (19)	0.79077 (11)	0.0435 (4)
C11	0.3703 (2)	0.69955 (18)	0.54181 (11)	0.0399 (4)
C12	0.3880 (2)	0.77975 (19)	0.46497 (11)	0.0475 (4)
H12	0.4418	0.8696	0.4587	0.057*
C13	0.5348 (3)	0.7078 (2)	0.87682 (12)	0.0567 (5)
H13	0.6178	0.6416	0.8463	0.068*
C14	0.3263 (3)	0.7273 (2)	0.39788 (12)	0.0530 (5)
H14	0.3373	0.7817	0.3468	0.064*
C15	1.0919 (3)	1.0925 (2)	0.69172 (14)	0.0607 (5)
H15	1.1921	1.1472	0.6939	0.073*
C16	0.1802 (2)	0.6943 (2)	0.73629 (12)	0.0440 (4)
H16A	0.114 (2)	0.6806 (18)	0.6900 (11)	0.046 (5)*
H16B	0.114 (2)	0.7692 (19)	0.7710 (11)	0.046 (5)*
C17	1.0877 (2)	1.0226 (2)	0.61875 (13)	0.0550 (5)
H17	1.1863	1.0290	0.5715	0.066*
C18	0.0320 (3)	0.5323 (2)	0.85851 (13)	0.0625 (5)
H18	−0.0639	0.6003	0.8704	0.075*
C19	0.1645 (4)	0.3071 (3)	0.89254 (17)	0.0854 (8)
H19	0.1596	0.2226	0.9267	0.102*
C20	0.7963 (2)	1.0024 (2)	0.75824 (12)	0.0505 (4)
H20	0.6988	0.9963	0.8060	0.061*
C21	0.3165 (3)	0.9005 (2)	0.88092 (12)	0.0577 (5)
H21	0.2503	0.9662	0.8533	0.069*
C22	0.2891 (3)	0.8988 (3)	0.96904 (13)	0.0699 (6)
H22	0.2046	0.9633	1.0003	0.084*
C23	0.9463 (3)	1.0807 (2)	0.76139 (13)	0.0604 (5)
H23	0.9495	1.1263	0.8113	0.072*
C24	0.3199 (3)	0.4554 (2)	0.77506 (13)	0.0557 (5)
H24	0.4208	0.4706	0.7298	0.067*
C25	0.3117 (4)	0.3305 (3)	0.82608 (17)	0.0747 (6)
H25	0.4072	0.2621	0.8150	0.090*
C26	0.3851 (3)	0.8033 (3)	1.01068 (13)	0.0680 (6)
H26	0.3676	0.8037	1.0699	0.082*
C27	0.5065 (3)	0.7074 (3)	0.96484 (14)	0.0688 (6)
H27	0.5708	0.6412	0.9931	0.083*
C28	0.0251 (4)	0.4068 (3)	0.90890 (15)	0.0820 (7)
H28	−0.0755	0.3905	0.9542	0.098*

	U11	U22	U33	U12	U13	U23
Cl1	0.0667 (3)	0.1008 (5)	0.0631 (3)	−0.0114 (3)	−0.0247 (3)	−0.0313 (3)
N1	0.0440 (7)	0.0441 (8)	0.0370 (8)	−0.0063 (6)	−0.0110 (6)	−0.0032 (6)
N2	0.0392 (7)	0.0453 (8)	0.0374 (8)	−0.0061 (6)	−0.0101 (6)	−0.0014 (6)
C1	0.0421 (9)	0.0474 (11)	0.0493 (10)	−0.0038 (8)	−0.0142 (8)	−0.0024 (8)
C2	0.0399 (8)	0.0402 (10)	0.0396 (9)	−0.0009 (7)	−0.0126 (7)	−0.0028 (7)
C3	0.0473 (9)	0.0531 (11)	0.0429 (10)	−0.0051 (8)	−0.0102 (8)	−0.0057 (8)
C4	0.0445 (9)	0.0407 (10)	0.0407 (9)	−0.0038 (7)	−0.0136 (7)	−0.0021 (7)
C5	0.0408 (8)	0.0473 (10)	0.0383 (9)	−0.0095 (7)	−0.0096 (7)	0.0000 (8)
C6	0.0400 (9)	0.0621 (13)	0.0497 (11)	0.0020 (8)	−0.0156 (8)	−0.0205 (9)
C7	0.0400 (9)	0.0491 (11)	0.0598 (12)	−0.0063 (8)	−0.0124 (8)	−0.0105 (9)
C8	0.0427 (8)	0.0372 (9)	0.0384 (9)	−0.0002 (7)	−0.0109 (7)	−0.0040 (7)
C9	0.0401 (8)	0.0419 (9)	0.0394 (9)	−0.0012 (7)	−0.0128 (7)	−0.0033 (7)
C10	0.0417 (9)	0.0516 (11)	0.0402 (10)	−0.0117 (8)	−0.0136 (8)	−0.0035 (8)
C11	0.0366 (8)	0.0437 (10)	0.0404 (9)	0.0010 (7)	−0.0100 (7)	−0.0064 (8)
C12	0.0558 (10)	0.0434 (11)	0.0443 (10)	−0.0058 (8)	−0.0122 (8)	−0.0055 (8)
C13	0.0580 (11)	0.0655 (13)	0.0497 (12)	0.0048 (9)	−0.0196 (9)	−0.0046 (10)
C14	0.0636 (11)	0.0563 (12)	0.0419 (10)	0.0011 (9)	−0.0174 (9)	−0.0059 (9)
C15	0.0520 (10)	0.0654 (13)	0.0692 (14)	−0.0171 (9)	−0.0200 (10)	−0.0062 (11)
C16	0.0337 (8)	0.0529 (11)	0.0454 (10)	−0.0023 (8)	−0.0083 (8)	−0.0041 (9)
C17	0.0450 (10)	0.0636 (13)	0.0551 (12)	−0.0105 (9)	−0.0080 (9)	−0.0002 (10)
C18	0.0561 (11)	0.0763 (15)	0.0532 (12)	−0.0186 (10)	−0.0061 (9)	−0.0019 (11)
C19	0.140 (2)	0.0633 (16)	0.0644 (16)	−0.0376 (17)	−0.0452 (17)	0.0139 (13)
C20	0.0515 (10)	0.0560 (12)	0.0443 (10)	−0.0104 (8)	−0.0088 (8)	−0.0082 (9)
C21	0.0628 (11)	0.0599 (13)	0.0483 (11)	0.0059 (10)	−0.0092 (9)	−0.0034 (9)
C22	0.0746 (14)	0.0808 (16)	0.0480 (13)	0.0019 (12)	0.0005 (11)	−0.0138 (11)
C23	0.0634 (12)	0.0680 (13)	0.0554 (12)	−0.0141 (10)	−0.0206 (10)	−0.0166 (10)
C24	0.0565 (11)	0.0577 (13)	0.0543 (12)	−0.0039 (9)	−0.0161 (9)	0.0028 (10)
C25	0.0997 (17)	0.0578 (14)	0.0771 (16)	−0.0012 (12)	−0.0425 (14)	0.0001 (12)
C26	0.0800 (14)	0.0880 (17)	0.0359 (11)	−0.0195 (12)	−0.0106 (10)	0.0004 (11)
C27	0.0821 (14)	0.0792 (16)	0.0513 (13)	−0.0035 (12)	−0.0298 (11)	0.0076 (11)
C28	0.0988 (18)	0.092 (2)	0.0522 (14)	−0.0498 (16)	−0.0062 (12)	0.0070 (13)

Cl1—C6	1.7436 (17)	C13—C27	1.379 (3)
N1—C2	1.314 (2)	C13—H13	0.9300
N1—C8	1.381 (2)	C14—H14	0.9300
N2—C2	1.367 (2)	C15—C17	1.373 (3)
N2—C9	1.385 (2)	C15—C23	1.374 (3)
N2—C16	1.459 (2)	C15—H15	0.9300
C1—C7	1.378 (2)	C16—H16A	1.000 (18)
C1—C11	1.388 (2)	C16—H16B	0.960 (17)
C1—H1	0.9300	C17—H17	0.9300
C2—C11	1.471 (2)	C18—C28	1.379 (3)
C3—C17	1.380 (2)	C18—H18	0.9300
C3—C4	1.391 (2)	C19—C28	1.356 (4)
C3—H3	0.9300	C19—C25	1.362 (4)
C4—C20	1.392 (2)	C19—H19	0.9300
C4—C8	1.470 (2)	C20—C23	1.372 (3)
C5—C21	1.378 (2)	C20—H20	0.9300
C5—C13	1.383 (3)	C21—C22	1.381 (3)
C5—C9	1.480 (2)	C21—H21	0.9300
C6—C7	1.369 (3)	C22—C26	1.364 (3)
C6—C14	1.373 (3)	C22—H22	0.9300
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.368 (2)	C24—C25	1.380 (3)
C10—C24	1.377 (2)	C24—H24	0.9300
C10—C18	1.378 (3)	C25—H25	0.9300
C10—C16	1.501 (3)	C26—C27	1.362 (3)
C11—C12	1.390 (2)	C26—H26	0.9300
C12—C14	1.381 (2)	C27—H27	0.9300
C12—H12	0.9300	C28—H28	0.9300
C2—N1—C8	105.97 (13)	C17—C15—C23	119.26 (17)
C2—N2—C9	106.82 (13)	C17—C15—H15	120.4
C2—N2—C16	128.26 (14)	C23—C15—H15	120.4
C9—N2—C16	124.44 (14)	N2—C16—C10	114.03 (14)
C7—C1—C11	121.22 (18)	N2—C16—H16A	107.8 (10)
C7—C1—H1	119.4	C10—C16—H16A	110.3 (10)
C11—C1—H1	119.4	N2—C16—H16B	108.6 (10)
N1—C2—N2	111.47 (14)	C10—C16—H16B	109.0 (10)
N1—C2—C11	123.73 (15)	H16A—C16—H16B	106.7 (13)
N2—C2—C11	124.79 (14)	C15—C17—C3	120.22 (17)
C17—C3—C4	121.31 (16)	C15—C17—H17	119.9
C17—C3—H3	119.3	C3—C17—H17	119.9
C4—C3—H3	119.3	C10—C18—C28	120.7 (2)
C3—C4—C20	117.33 (16)	C10—C18—H18	119.7
C3—C4—C8	119.95 (15)	C28—C18—H18	119.7
C20—C4—C8	122.61 (15)	C28—C19—C25	120.0 (2)
C21—C5—C13	118.12 (17)	C28—C19—H19	120.0
C21—C5—C9	122.19 (16)	C25—C19—H19	120.0
C13—C5—C9	119.68 (15)	C23—C20—C4	121.03 (17)
C7—C6—C14	121.57 (17)	C23—C20—H20	119.5
C7—C6—Cl1	119.75 (15)	C4—C20—H20	119.5
C14—C6—Cl1	118.69 (16)	C5—C21—C22	120.6 (2)
C6—C7—C1	118.92 (17)	C5—C21—H21	119.7
C6—C7—H7	120.5	C22—C21—H21	119.7
C1—C7—H7	120.5	C26—C22—C21	120.6 (2)
C9—C8—N1	109.98 (14)	C26—C22—H22	119.7
C9—C8—C4	129.88 (15)	C21—C22—H22	119.7
N1—C8—C4	120.14 (14)	C20—C23—C15	120.83 (18)
C8—C9—N2	105.76 (14)	C20—C23—H23	119.6
C8—C9—C5	132.19 (15)	C15—C23—H23	119.6
N2—C9—C5	121.91 (14)	C10—C24—C25	120.4 (2)
C24—C10—C18	118.34 (19)	C10—C24—H24	119.8
C24—C10—C16	122.53 (16)	C25—C24—H24	119.8
C18—C10—C16	119.12 (17)	C19—C25—C24	120.3 (2)
C1—C11—C12	118.42 (16)	C19—C25—H25	119.8
C1—C11—C2	122.62 (16)	C24—C25—H25	119.8
C12—C11—C2	118.87 (15)	C27—C26—C22	119.51 (19)
C14—C12—C11	120.65 (17)	C27—C26—H26	120.2
C14—C12—H12	119.7	C22—C26—H26	120.2
C11—C12—H12	119.7	C26—C27—C13	120.5 (2)
C27—C13—C5	120.73 (19)	C26—C27—H27	119.8
C27—C13—H13	119.6	C13—C27—H27	119.8
C5—C13—H13	119.6	C19—C28—C18	120.2 (2)
C6—C14—C12	119.22 (18)	C19—C28—H28	119.9
C6—C14—H14	120.4	C18—C28—H28	119.9
C12—C14—H14	120.4
C8—N1—C2—N2	0.58 (18)	N1—C2—C11—C12	−39.5 (2)
C8—N1—C2—C11	−178.04 (15)	N2—C2—C11—C12	142.03 (17)
C9—N2—C2—N1	−0.62 (19)	C1—C11—C12—C14	0.9 (2)
C16—N2—C2—N1	171.59 (15)	C2—C11—C12—C14	177.51 (15)
C9—N2—C2—C11	177.97 (15)	C21—C5—C13—C27	−1.1 (3)
C16—N2—C2—C11	−9.8 (3)	C9—C5—C13—C27	177.59 (18)
C17—C3—C4—C20	−1.0 (3)	C7—C6—C14—C12	0.0 (3)
C17—C3—C4—C8	175.34 (17)	Cl1—C6—C14—C12	179.73 (13)
C14—C6—C7—C1	0.3 (3)	C11—C12—C14—C6	−0.6 (3)
Cl1—C6—C7—C1	−179.45 (12)	C2—N2—C16—C10	115.85 (19)
C11—C1—C7—C6	0.1 (2)	C9—N2—C16—C10	−73.2 (2)
C2—N1—C8—C9	−0.31 (18)	C24—C10—C16—N2	−28.4 (2)
C2—N1—C8—C4	−179.85 (15)	C18—C10—C16—N2	152.54 (16)
C3—C4—C8—C9	165.88 (18)	C23—C15—C17—C3	0.8 (3)
C20—C4—C8—C9	−17.9 (3)	C4—C3—C17—C15	0.3 (3)
C3—C4—C8—N1	−14.7 (2)	C24—C10—C18—C28	−0.3 (3)
C20—C4—C8—N1	161.51 (16)	C16—C10—C18—C28	178.75 (18)
N1—C8—C9—N2	−0.06 (18)	C3—C4—C20—C23	0.7 (3)
C4—C8—C9—N2	179.42 (16)	C8—C4—C20—C23	−175.60 (17)
N1—C8—C9—C5	175.61 (17)	C13—C5—C21—C22	0.9 (3)
C4—C8—C9—C5	−4.9 (3)	C9—C5—C21—C22	−177.70 (18)
C2—N2—C9—C8	0.40 (18)	C5—C21—C22—C26	0.1 (3)
C16—N2—C9—C8	−172.20 (15)	C4—C20—C23—C15	0.4 (3)
C2—N2—C9—C5	−175.82 (15)	C17—C15—C23—C20	−1.2 (3)
C16—N2—C9—C5	11.6 (2)	C18—C10—C24—C25	0.1 (3)
C21—C5—C9—C8	105.1 (2)	C16—C10—C24—C25	−178.92 (18)
C13—C5—C9—C8	−73.6 (3)	C28—C19—C25—C24	−0.1 (3)
C21—C5—C9—N2	−79.8 (2)	C10—C24—C25—C19	0.1 (3)
C13—C5—C9—N2	101.5 (2)	C21—C22—C26—C27	−1.1 (3)
C7—C1—C11—C12	−0.7 (2)	C22—C26—C27—C13	0.9 (3)
C7—C1—C11—C2	−177.10 (14)	C5—C13—C27—C26	0.2 (3)
N1—C2—C11—C1	136.88 (17)	C25—C19—C28—C18	−0.1 (4)
N2—C2—C11—C1	−41.5 (2)	C10—C18—C28—C19	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.56	2.874 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1	0.93	2.56	2.874 (2)	100