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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1233.
Published online 2008 June 7. doi:  10.1107/S1600536808016802
PMCID: PMC2961831

1-Benzyl-2-(4-chloro­phen­yl)-4,5-di­phenyl-1H-imidazole

Abstract

The mol­ecular conformation of the title compound, C28H21ClN2, is stabilized by an intra­molecular 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 [triangle]); Nagarapu et al. (2007 [triangle]); Kidwai et al. (2007 [triangle]).

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Object name is e-64-o1233-scheme1.jpg

Experimental

Crystal data

  • C28H21ClN2
  • M r = 420.92
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1233-efi1.jpg
  • 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 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2001 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported by a grant from the University of Tehran and the University of Alzahra.

supplementary crystallographic information

Comment

The synthesis, reactions and biological properties of substituted imidazole constitutes a significant part of modern heterocyclic chemistry. Compounds containing an imidazole ring system have many pharmacological properties and play important roles in biochemical processes. Many of substituted diaryl imidazoles are known as inhibitors of P38 MAP Kinase (Balalaie, et al., 2003; Nagarapu, et al., 2007; Kidwai, et al., 2007).

The molecular structure of the title compound and the atom-numbering scheme are shown in Fig. 1. The phenyl rings attached at C2, N2, C9 and C8 enclose dihedral angles of 40.74 (8)°, 85.60 (7)°, 77.10 (6)°, 16.55 (11)°, respectively, with the imidazole ring. An intramolecular hydrogen bond stabilises the molecular conformation. Dipole-dipole and van der Waals interactions are effective in the molecular packing.

Experimental

A mixture of benzil (2.5 mmol), 4-chlorobenzaldehyde (2.5 mmol), benzylamine (2.5 mmol), ammonium acetate (5 mmol) and activated SBA-sulfonic acid (0.02 g) was heated at 140°C for 6 minutes. The progress of reaction was monitored by TLC. After cooling to room temperature, the mixture was dissolved in hot ethylacetate and the catalyst was removed by filtration. The filtrate was left for crystallization.

Refinement

Aromatic H atoms were placed in calculated positions (C—H = 0.93 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). Methylene H atoms were located in difference density maps and their coordinates and isotropic displacement parameters were refined freely.

Figures

Fig. 1.
Molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are shown as circles of arbitrary radii.

Crystal data

C28H21ClN2Z = 2
Mr = 420.92F000 = 440
Triclinic, P1Dx = 1.291 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.4880 (11) ÅCell parameters from 6987 reflections
b = 9.2711 (16) Åθ = 1.2–29.8º
c = 16.049 (3) ŵ = 0.19 mm1
α = 87.169 (13)ºT = 290 (2) K
β = 76.704 (12)ºBlock, colorless
γ = 87.842 (13)º0.3 × 0.2 × 0.2 mm
V = 1082.6 (3) Å3

Data collection

STOE IPDS-II diffractometer2814 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Monochromator: graphiteθmax = 26.0º
T = 290(2) Kθmin = 2.2º
Area detector – phi oscillation scansh = −9→9
Absorption correction: nonek = −11→10
8769 measured reflectionsl = −19→19
4246 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H 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 reflectionsΔρmax = 0.13 e Å3
288 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Cl10.17061 (7)0.52946 (7)0.32233 (4)0.0741 (2)
N10.60096 (17)0.82368 (15)0.59681 (9)0.0412 (3)
N20.36337 (17)0.74456 (15)0.69583 (8)0.0403 (3)
C10.2919 (2)0.56492 (19)0.54889 (12)0.0456 (4)
H10.28040.50960.59970.055*
C20.4446 (2)0.75675 (17)0.61039 (10)0.0393 (4)
C30.9378 (2)0.9430 (2)0.61528 (12)0.0476 (4)
H30.93700.89590.56560.057*
C40.7878 (2)0.93196 (18)0.68467 (11)0.0413 (4)
C50.4409 (2)0.80553 (19)0.83352 (11)0.0419 (4)
C60.2487 (2)0.5939 (2)0.40748 (12)0.0492 (5)
C70.2308 (2)0.5117 (2)0.48201 (12)0.0491 (4)
H70.17840.42130.48740.059*
C80.6244 (2)0.85566 (17)0.67670 (10)0.0391 (4)
C90.4790 (2)0.80756 (18)0.73880 (11)0.0398 (4)
C100.1795 (2)0.55784 (19)0.79077 (11)0.0435 (4)
C110.3703 (2)0.69955 (18)0.54181 (11)0.0399 (4)
C120.3880 (2)0.77975 (19)0.46497 (11)0.0475 (4)
H120.44180.86960.45870.057*
C130.5348 (3)0.7078 (2)0.87682 (12)0.0567 (5)
H130.61780.64160.84630.068*
C140.3263 (3)0.7273 (2)0.39788 (12)0.0530 (5)
H140.33730.78170.34680.064*
C151.0919 (3)1.0925 (2)0.69172 (14)0.0607 (5)
H151.19211.14720.69390.073*
C160.1802 (2)0.6943 (2)0.73629 (12)0.0440 (4)
H16A0.114 (2)0.6806 (18)0.6900 (11)0.046 (5)*
H16B0.114 (2)0.7692 (19)0.7710 (11)0.046 (5)*
C171.0877 (2)1.0226 (2)0.61875 (13)0.0550 (5)
H171.18631.02900.57150.066*
C180.0320 (3)0.5323 (2)0.85851 (13)0.0625 (5)
H18−0.06390.60030.87040.075*
C190.1645 (4)0.3071 (3)0.89254 (17)0.0854 (8)
H190.15960.22260.92670.102*
C200.7963 (2)1.0024 (2)0.75824 (12)0.0505 (4)
H200.69880.99630.80600.061*
C210.3165 (3)0.9005 (2)0.88092 (12)0.0577 (5)
H210.25030.96620.85330.069*
C220.2891 (3)0.8988 (3)0.96904 (13)0.0699 (6)
H220.20460.96331.00030.084*
C230.9463 (3)1.0807 (2)0.76139 (13)0.0604 (5)
H230.94951.12630.81130.072*
C240.3199 (3)0.4554 (2)0.77506 (13)0.0557 (5)
H240.42080.47060.72980.067*
C250.3117 (4)0.3305 (3)0.82608 (17)0.0747 (6)
H250.40720.26210.81500.090*
C260.3851 (3)0.8033 (3)1.01068 (13)0.0680 (6)
H260.36760.80371.06990.082*
C270.5065 (3)0.7074 (3)0.96484 (14)0.0688 (6)
H270.57080.64120.99310.083*
C280.0251 (4)0.4068 (3)0.90890 (15)0.0820 (7)
H28−0.07550.39050.95420.098*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0667 (3)0.1008 (5)0.0631 (3)−0.0114 (3)−0.0247 (3)−0.0313 (3)
N10.0440 (7)0.0441 (8)0.0370 (8)−0.0063 (6)−0.0110 (6)−0.0032 (6)
N20.0392 (7)0.0453 (8)0.0374 (8)−0.0061 (6)−0.0101 (6)−0.0014 (6)
C10.0421 (9)0.0474 (11)0.0493 (10)−0.0038 (8)−0.0142 (8)−0.0024 (8)
C20.0399 (8)0.0402 (10)0.0396 (9)−0.0009 (7)−0.0126 (7)−0.0028 (7)
C30.0473 (9)0.0531 (11)0.0429 (10)−0.0051 (8)−0.0102 (8)−0.0057 (8)
C40.0445 (9)0.0407 (10)0.0407 (9)−0.0038 (7)−0.0136 (7)−0.0021 (7)
C50.0408 (8)0.0473 (10)0.0383 (9)−0.0095 (7)−0.0096 (7)0.0000 (8)
C60.0400 (9)0.0621 (13)0.0497 (11)0.0020 (8)−0.0156 (8)−0.0205 (9)
C70.0400 (9)0.0491 (11)0.0598 (12)−0.0063 (8)−0.0124 (8)−0.0105 (9)
C80.0427 (8)0.0372 (9)0.0384 (9)−0.0002 (7)−0.0109 (7)−0.0040 (7)
C90.0401 (8)0.0419 (9)0.0394 (9)−0.0012 (7)−0.0128 (7)−0.0033 (7)
C100.0417 (9)0.0516 (11)0.0402 (10)−0.0117 (8)−0.0136 (8)−0.0035 (8)
C110.0366 (8)0.0437 (10)0.0404 (9)0.0010 (7)−0.0100 (7)−0.0064 (8)
C120.0558 (10)0.0434 (11)0.0443 (10)−0.0058 (8)−0.0122 (8)−0.0055 (8)
C130.0580 (11)0.0655 (13)0.0497 (12)0.0048 (9)−0.0196 (9)−0.0046 (10)
C140.0636 (11)0.0563 (12)0.0419 (10)0.0011 (9)−0.0174 (9)−0.0059 (9)
C150.0520 (10)0.0654 (13)0.0692 (14)−0.0171 (9)−0.0200 (10)−0.0062 (11)
C160.0337 (8)0.0529 (11)0.0454 (10)−0.0023 (8)−0.0083 (8)−0.0041 (9)
C170.0450 (10)0.0636 (13)0.0551 (12)−0.0105 (9)−0.0080 (9)−0.0002 (10)
C180.0561 (11)0.0763 (15)0.0532 (12)−0.0186 (10)−0.0061 (9)−0.0019 (11)
C190.140 (2)0.0633 (16)0.0644 (16)−0.0376 (17)−0.0452 (17)0.0139 (13)
C200.0515 (10)0.0560 (12)0.0443 (10)−0.0104 (8)−0.0088 (8)−0.0082 (9)
C210.0628 (11)0.0599 (13)0.0483 (11)0.0059 (10)−0.0092 (9)−0.0034 (9)
C220.0746 (14)0.0808 (16)0.0480 (13)0.0019 (12)0.0005 (11)−0.0138 (11)
C230.0634 (12)0.0680 (13)0.0554 (12)−0.0141 (10)−0.0206 (10)−0.0166 (10)
C240.0565 (11)0.0577 (13)0.0543 (12)−0.0039 (9)−0.0161 (9)0.0028 (10)
C250.0997 (17)0.0578 (14)0.0771 (16)−0.0012 (12)−0.0425 (14)0.0001 (12)
C260.0800 (14)0.0880 (17)0.0359 (11)−0.0195 (12)−0.0106 (10)0.0004 (11)
C270.0821 (14)0.0792 (16)0.0513 (13)−0.0035 (12)−0.0298 (11)0.0076 (11)
C280.0988 (18)0.092 (2)0.0522 (14)−0.0498 (16)−0.0062 (12)0.0070 (13)

Geometric parameters (Å, °)

Cl1—C61.7436 (17)C13—C271.379 (3)
N1—C21.314 (2)C13—H130.9300
N1—C81.381 (2)C14—H140.9300
N2—C21.367 (2)C15—C171.373 (3)
N2—C91.385 (2)C15—C231.374 (3)
N2—C161.459 (2)C15—H150.9300
C1—C71.378 (2)C16—H16A1.000 (18)
C1—C111.388 (2)C16—H16B0.960 (17)
C1—H10.9300C17—H170.9300
C2—C111.471 (2)C18—C281.379 (3)
C3—C171.380 (2)C18—H180.9300
C3—C41.391 (2)C19—C281.356 (4)
C3—H30.9300C19—C251.362 (4)
C4—C201.392 (2)C19—H190.9300
C4—C81.470 (2)C20—C231.372 (3)
C5—C211.378 (2)C20—H200.9300
C5—C131.383 (3)C21—C221.381 (3)
C5—C91.480 (2)C21—H210.9300
C6—C71.369 (3)C22—C261.364 (3)
C6—C141.373 (3)C22—H220.9300
C7—H70.9300C23—H230.9300
C8—C91.368 (2)C24—C251.380 (3)
C10—C241.377 (2)C24—H240.9300
C10—C181.378 (3)C25—H250.9300
C10—C161.501 (3)C26—C271.362 (3)
C11—C121.390 (2)C26—H260.9300
C12—C141.381 (2)C27—H270.9300
C12—H120.9300C28—H280.9300
C2—N1—C8105.97 (13)C17—C15—C23119.26 (17)
C2—N2—C9106.82 (13)C17—C15—H15120.4
C2—N2—C16128.26 (14)C23—C15—H15120.4
C9—N2—C16124.44 (14)N2—C16—C10114.03 (14)
C7—C1—C11121.22 (18)N2—C16—H16A107.8 (10)
C7—C1—H1119.4C10—C16—H16A110.3 (10)
C11—C1—H1119.4N2—C16—H16B108.6 (10)
N1—C2—N2111.47 (14)C10—C16—H16B109.0 (10)
N1—C2—C11123.73 (15)H16A—C16—H16B106.7 (13)
N2—C2—C11124.79 (14)C15—C17—C3120.22 (17)
C17—C3—C4121.31 (16)C15—C17—H17119.9
C17—C3—H3119.3C3—C17—H17119.9
C4—C3—H3119.3C10—C18—C28120.7 (2)
C3—C4—C20117.33 (16)C10—C18—H18119.7
C3—C4—C8119.95 (15)C28—C18—H18119.7
C20—C4—C8122.61 (15)C28—C19—C25120.0 (2)
C21—C5—C13118.12 (17)C28—C19—H19120.0
C21—C5—C9122.19 (16)C25—C19—H19120.0
C13—C5—C9119.68 (15)C23—C20—C4121.03 (17)
C7—C6—C14121.57 (17)C23—C20—H20119.5
C7—C6—Cl1119.75 (15)C4—C20—H20119.5
C14—C6—Cl1118.69 (16)C5—C21—C22120.6 (2)
C6—C7—C1118.92 (17)C5—C21—H21119.7
C6—C7—H7120.5C22—C21—H21119.7
C1—C7—H7120.5C26—C22—C21120.6 (2)
C9—C8—N1109.98 (14)C26—C22—H22119.7
C9—C8—C4129.88 (15)C21—C22—H22119.7
N1—C8—C4120.14 (14)C20—C23—C15120.83 (18)
C8—C9—N2105.76 (14)C20—C23—H23119.6
C8—C9—C5132.19 (15)C15—C23—H23119.6
N2—C9—C5121.91 (14)C10—C24—C25120.4 (2)
C24—C10—C18118.34 (19)C10—C24—H24119.8
C24—C10—C16122.53 (16)C25—C24—H24119.8
C18—C10—C16119.12 (17)C19—C25—C24120.3 (2)
C1—C11—C12118.42 (16)C19—C25—H25119.8
C1—C11—C2122.62 (16)C24—C25—H25119.8
C12—C11—C2118.87 (15)C27—C26—C22119.51 (19)
C14—C12—C11120.65 (17)C27—C26—H26120.2
C14—C12—H12119.7C22—C26—H26120.2
C11—C12—H12119.7C26—C27—C13120.5 (2)
C27—C13—C5120.73 (19)C26—C27—H27119.8
C27—C13—H13119.6C13—C27—H27119.8
C5—C13—H13119.6C19—C28—C18120.2 (2)
C6—C14—C12119.22 (18)C19—C28—H28119.9
C6—C14—H14120.4C18—C28—H28119.9
C12—C14—H14120.4
C8—N1—C2—N20.58 (18)N1—C2—C11—C12−39.5 (2)
C8—N1—C2—C11−178.04 (15)N2—C2—C11—C12142.03 (17)
C9—N2—C2—N1−0.62 (19)C1—C11—C12—C140.9 (2)
C16—N2—C2—N1171.59 (15)C2—C11—C12—C14177.51 (15)
C9—N2—C2—C11177.97 (15)C21—C5—C13—C27−1.1 (3)
C16—N2—C2—C11−9.8 (3)C9—C5—C13—C27177.59 (18)
C17—C3—C4—C20−1.0 (3)C7—C6—C14—C120.0 (3)
C17—C3—C4—C8175.34 (17)Cl1—C6—C14—C12179.73 (13)
C14—C6—C7—C10.3 (3)C11—C12—C14—C6−0.6 (3)
Cl1—C6—C7—C1−179.45 (12)C2—N2—C16—C10115.85 (19)
C11—C1—C7—C60.1 (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—N2152.54 (16)
C3—C4—C8—C9165.88 (18)C23—C15—C17—C30.8 (3)
C20—C4—C8—C9−17.9 (3)C4—C3—C17—C150.3 (3)
C3—C4—C8—N1−14.7 (2)C24—C10—C18—C28−0.3 (3)
C20—C4—C8—N1161.51 (16)C16—C10—C18—C28178.75 (18)
N1—C8—C9—N2−0.06 (18)C3—C4—C20—C230.7 (3)
C4—C8—C9—N2179.42 (16)C8—C4—C20—C23−175.60 (17)
N1—C8—C9—C5175.61 (17)C13—C5—C21—C220.9 (3)
C4—C8—C9—C5−4.9 (3)C9—C5—C21—C22−177.70 (18)
C2—N2—C9—C80.40 (18)C5—C21—C22—C260.1 (3)
C16—N2—C9—C8−172.20 (15)C4—C20—C23—C150.4 (3)
C2—N2—C9—C5−175.82 (15)C17—C15—C23—C20−1.2 (3)
C16—N2—C9—C511.6 (2)C18—C10—C24—C250.1 (3)
C21—C5—C9—C8105.1 (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—C190.1 (3)
C13—C5—C9—N2101.5 (2)C21—C22—C26—C27−1.1 (3)
C7—C1—C11—C12−0.7 (2)C22—C26—C27—C130.9 (3)
C7—C1—C11—C2−177.10 (14)C5—C13—C27—C260.2 (3)
N1—C2—C11—C1136.88 (17)C25—C19—C28—C18−0.1 (4)
N2—C2—C11—C1−41.5 (2)C10—C18—C28—C190.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···N10.932.562.874 (2)100

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2715).

References

  • Balalaie, S., Hashemi, M. M. & Akhbari, M. (2003). Tetrahedron Lett.44, 1709–1711.
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