Literature DB >> 21587620

1-[(Biphenyl-4-yl)(phen-yl)meth-yl]-1H-imidazole (bifonazole).

Bernard Van Eerdenbrugh, Phillip E Fanwick, Lynne S Taylor.   

Abstract

In the title compound, C(22)H(18)N(2), the dihedral angles formed by the imidazole ring with the phenyl ring and the benzene ring of the biphenyl group are 87.02 (5) and 78.20 (4)°, respectively. In the crystal, mol-ecules inter-act through inter-molecular C-H⋯N hydrogen bonds, forming chains parallel to the b axis. These chains are further linked into a three-dimensional network by C-H⋯π stacking inter-actions.

Entities:  

Year:  2010        PMID： 21587620      PMCID： PMC2983152          DOI： 10.1107/S1600536810037876

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For a review of the anti­microbial activity of bifonazole and its therapeutic use in superficial mycoses, see: Lackner and Clissold (1989 ▶).

Experimental

Crystal data

C22H18N2 M = 310.40 Monoclinic, a = 7.9737 (7) Å b = 6.2591 (6) Å c = 33.265 (3) Å β = 93.805 (8)° V = 1656.5 (3) Å3 Z = 4 Cu Kα radiation μ = 0.56 mm−1 T = 150 K 0.20 × 0.20 × 0.04 mm

Data collection

Rigaku RAPID II diffractometer Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.860, T max = 0.979 19391 measured reflections 3064 independent reflections 2801 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.107 S = 1.06 3064 reflections 218 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.20 e Å−3 Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and local programs. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037876/rz2487sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037876/rz2487Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H18N2F(000) = 656
Mr = 310.40Dx = 1.245 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 3380 reflections
a = 7.9737 (7) Åθ = 2–71°
b = 6.2591 (6) ŵ = 0.56 mm−1
c = 33.265 (3) ÅT = 150 K
β = 93.805 (8)°Plate, colourless
V = 1656.5 (3) Å30.20 × 0.20 × 0.04 mm
Z = 4
Rigaku Rapid II diffractometer2801 reflections with I > 2σ(I)
confocal opticsRint = 0.030
ω scansθmax = 71.8°, θmin = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)h = 0→9
Tmin = 0.860, Tmax = 0.979k = 0→7
19391 measured reflectionsl = −40→40
3064 independent reflections
Refinement on F2H-atom parameters constrained
Least-squares matrix: fullw = 1/[σ2(Fo2) + (0.0501P)2 + 0.7321P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.041(Δ/σ)max < 0.001
wR(F2) = 0.107Δρmax = 0.19 e Å−3
S = 1.06Δρmin = −0.20 e Å−3
3064 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008)
218 parametersExtinction coefficient: 0.20E-02
0 restraints
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. Outlier data were removed using a local program based on the method of Prince and Nicholson.Refinement on F2 for ALL reflections except for 0 with very negative F2 or 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.
xyzUiso*/Ueq
N10.15014 (12)0.10641 (19)0.07667 (3)0.0251 (3)
N20.26374 (14)−0.2162 (2)0.07143 (3)0.0316 (3)
C1−0.10284 (15)0.3342 (2)0.07936 (4)0.0247 (3)
C2−0.21816 (16)0.1678 (2)0.08086 (4)0.0277 (3)
C3−0.38706 (16)0.2022 (2)0.06900 (4)0.0313 (3)
C4−0.44051 (16)0.4013 (3)0.05515 (4)0.0322 (3)
C5−0.32601 (17)0.5661 (2)0.05271 (4)0.0324 (3)
C6−0.15719 (16)0.5331 (2)0.06485 (4)0.0291 (3)
C70.08225 (15)0.3066 (2)0.09321 (4)0.0247 (3)
C80.12033 (15)0.3155 (2)0.13881 (4)0.0245 (3)
C90.02747 (16)0.2044 (2)0.16633 (4)0.0288 (3)
C100.07544 (16)0.2074 (2)0.20723 (4)0.0290 (3)
C110.21664 (15)0.3221 (2)0.22243 (4)0.0262 (3)
C120.30588 (16)0.4380 (2)0.19481 (4)0.0288 (3)
C130.25869 (16)0.4334 (2)0.15381 (4)0.0276 (3)
C140.27240 (15)0.3177 (2)0.26618 (4)0.0266 (3)
C150.36722 (17)0.4845 (2)0.28421 (4)0.0318 (3)
C160.42239 (18)0.4754 (3)0.32482 (4)0.0350 (3)
C170.38402 (17)0.3018 (2)0.34818 (4)0.0319 (3)
C180.28887 (17)0.1358 (3)0.33100 (4)0.0342 (3)
C190.23430 (17)0.1436 (2)0.29038 (4)0.0324 (3)
C200.21208 (16)−0.0692 (2)0.09636 (4)0.0283 (3)
C210.23282 (16)−0.1299 (2)0.03361 (4)0.0316 (3)
C220.16304 (17)0.0681 (2)0.03627 (4)0.0314 (3)
H2−0.18170.03060.09000.033*
H3−0.46570.08880.07040.038*
H4−0.55580.42460.04730.039*
H5−0.36240.70180.04280.039*
H6−0.07890.64670.06320.035*
H70.14450.42770.08140.030*
H9−0.06940.12610.15690.035*
H100.01100.12990.22530.035*
H120.40020.52100.20420.035*
H130.32210.51230.13570.033*
H150.39420.60520.26860.038*
H160.48700.58960.33660.042*
H170.42250.29620.37580.038*
H180.26090.01670.34690.041*
H190.16990.02860.27890.039*
H200.2177−0.08490.12480.034*
H210.2567−0.19850.00920.038*
H220.13000.16090.01460.038*
U11U22U33U12U13U23
N10.0191 (5)0.0280 (6)0.0278 (5)0.0017 (4)−0.0006 (4)0.0008 (4)
N20.0282 (6)0.0301 (7)0.0369 (6)0.0021 (5)0.0042 (5)−0.0010 (5)
C10.0227 (6)0.0281 (8)0.0231 (6)0.0019 (5)0.0004 (5)−0.0019 (5)
C20.0263 (6)0.0274 (8)0.0293 (6)0.0016 (5)−0.0002 (5)0.0023 (5)
C30.0239 (6)0.0358 (9)0.0342 (7)−0.0037 (6)0.0024 (5)0.0001 (6)
C40.0217 (6)0.0417 (9)0.0331 (7)0.0063 (6)0.0002 (5)−0.0025 (6)
C50.0309 (7)0.0316 (9)0.0341 (7)0.0090 (6)−0.0016 (5)0.0006 (6)
C60.0277 (7)0.0270 (8)0.0324 (7)0.0007 (5)0.0003 (5)−0.0004 (6)
C70.0213 (6)0.0220 (7)0.0307 (7)−0.0002 (5)0.0012 (5)0.0004 (5)
C80.0213 (6)0.0229 (7)0.0293 (6)0.0039 (5)0.0006 (5)−0.0006 (5)
C90.0213 (6)0.0305 (8)0.0343 (7)−0.0044 (5)−0.0003 (5)−0.0015 (6)
C100.0233 (6)0.0326 (8)0.0314 (7)−0.0033 (5)0.0039 (5)0.0017 (6)
C110.0218 (6)0.0268 (8)0.0301 (7)0.0022 (5)0.0010 (5)−0.0013 (5)
C120.0239 (6)0.0290 (8)0.0330 (7)−0.0040 (5)−0.0015 (5)−0.0006 (5)
C130.0241 (6)0.0269 (8)0.0318 (7)−0.0017 (5)0.0019 (5)0.0028 (5)
C140.0197 (6)0.0308 (8)0.0296 (7)0.0012 (5)0.0026 (5)−0.0009 (5)
C150.0299 (7)0.0335 (8)0.0319 (7)−0.0032 (6)0.0011 (5)0.0007 (6)
C160.0327 (7)0.0381 (9)0.0337 (7)−0.0041 (6)−0.0016 (6)−0.0051 (6)
C170.0270 (6)0.0408 (9)0.0276 (7)0.0029 (6)−0.0001 (5)−0.0020 (6)
C180.0305 (7)0.0398 (9)0.0325 (7)−0.0019 (6)0.0041 (5)0.0055 (6)
C190.0281 (7)0.0360 (9)0.0328 (7)−0.0052 (6)0.0003 (5)−0.0006 (6)
C200.0255 (6)0.0288 (8)0.0306 (7)0.0018 (5)0.0007 (5)0.0020 (5)
C210.0281 (7)0.0359 (9)0.0308 (7)0.0006 (6)0.0031 (5)−0.0045 (6)
C220.0301 (7)0.0370 (9)0.0267 (6)0.0041 (6)−0.0003 (5)0.0005 (6)
N1—C201.3560 (17)C10—C111.4011 (18)
N1—C221.3758 (17)C10—H100.9500
N1—C71.4854 (17)C11—C121.4012 (19)
N2—C201.3226 (18)C11—C141.4935 (18)
N2—C211.3765 (18)C12—C131.3907 (18)
C1—C21.3921 (19)C12—H120.9500
C1—C61.3940 (19)C13—H130.9500
C1—C71.5263 (16)C14—C191.400 (2)
C2—C31.3947 (18)C14—C151.4005 (19)
C2—H20.9500C15—C161.3939 (19)
C3—C41.386 (2)C15—H150.9500
C3—H30.9500C16—C171.381 (2)
C4—C51.384 (2)C16—H160.9500
C4—H40.9500C17—C181.387 (2)
C5—C61.3949 (19)C17—H170.9500
C5—H50.9500C18—C191.3928 (19)
C6—H60.9500C18—H180.9500
C7—C81.5280 (17)C19—H190.9500
C7—H71.0000C20—H200.9500
C8—C131.3921 (18)C21—C221.364 (2)
C8—C91.4000 (19)C21—H210.9500
C9—C101.3887 (18)C22—H220.9500
C9—H90.9500
C20—N1—C22106.39 (11)C10—C11—C12117.35 (12)
C20—N1—C7129.43 (11)C10—C11—C14121.48 (12)
C22—N1—C7124.18 (11)C12—C11—C14121.16 (12)
C20—N2—C21104.82 (12)C13—C12—C11121.09 (12)
C2—C1—C6119.30 (11)C13—C12—H12119.50
C2—C1—C7122.18 (12)C11—C12—H12119.50
C6—C1—C7118.52 (12)C12—C13—C8121.25 (12)
C1—C2—C3120.16 (13)C12—C13—H13119.40
C1—C2—H2119.90C8—C13—H13119.40
C3—C2—H2119.90C19—C14—C15117.75 (12)
C4—C3—C2120.16 (13)C19—C14—C11120.86 (12)
C4—C3—H3119.90C15—C14—C11121.38 (12)
C2—C3—H3119.90C16—C15—C14120.74 (14)
C5—C4—C3120.03 (12)C16—C15—H15119.60
C5—C4—H4120.00C14—C15—H15119.60
C3—C4—H4120.00C17—C16—C15120.66 (14)
C4—C5—C6120.02 (13)C17—C16—H16119.70
C4—C5—H5120.00C15—C16—H16119.70
C6—C5—H5120.00C16—C17—C18119.52 (13)
C1—C6—C5120.30 (13)C16—C17—H17120.20
C1—C6—H6119.80C18—C17—H17120.20
C5—C6—H6119.80C17—C18—C19120.02 (14)
N1—C7—C1110.62 (10)C17—C18—H18120.00
N1—C7—C8110.18 (10)C19—C18—H18120.00
C1—C7—C8114.84 (10)C18—C19—C14121.31 (13)
N1—C7—H7106.90C18—C19—H19119.30
C1—C7—H7106.90C14—C19—H19119.30
C8—C7—H7106.90N2—C20—N1112.32 (12)
C13—C8—C9118.03 (12)N2—C20—H20123.80
C13—C8—C7118.39 (11)N1—C20—H20123.80
C9—C8—C7123.53 (11)C22—C21—N2110.27 (12)
C10—C9—C8120.71 (12)C22—C21—H21124.90
C10—C9—H9119.60N2—C21—H21124.90
C8—C9—H9119.60C21—C22—N1106.21 (12)
C9—C10—C11121.53 (12)C21—C22—H22126.90
C9—C10—H10119.20N1—C22—H22126.90
C11—C10—H10119.20
C6—C1—C2—C3−1.77 (19)C10—C11—C12—C13−1.9 (2)
C7—C1—C2—C3178.09 (12)C14—C11—C12—C13176.77 (12)
C1—C2—C3—C40.9 (2)C11—C12—C13—C80.6 (2)
C2—C3—C4—C50.6 (2)C9—C8—C13—C121.3 (2)
C3—C4—C5—C6−1.1 (2)C7—C8—C13—C12−176.27 (12)
C2—C1—C6—C51.24 (19)C10—C11—C14—C1925.82 (19)
C7—C1—C6—C5−178.63 (12)C12—C11—C14—C19−152.84 (13)
C4—C5—C6—C10.2 (2)C10—C11—C14—C15−155.53 (13)
C20—N1—C7—C1−116.94 (13)C12—C11—C14—C1525.82 (19)
C22—N1—C7—C163.98 (15)C19—C14—C15—C160.5 (2)
C20—N1—C7—C811.12 (17)C11—C14—C15—C16−178.19 (12)
C22—N1—C7—C8−167.95 (11)C14—C15—C16—C17−0.3 (2)
C2—C1—C7—N146.28 (16)C15—C16—C17—C18−0.3 (2)
C6—C1—C7—N1−133.85 (12)C16—C17—C18—C190.7 (2)
C2—C1—C7—C8−79.20 (15)C17—C18—C19—C14−0.5 (2)
C6—C1—C7—C8100.67 (14)C15—C14—C19—C18−0.1 (2)
N1—C7—C8—C1398.12 (14)C11—C14—C19—C18178.57 (12)
C1—C7—C8—C13−136.18 (12)C21—N2—C20—N1−0.11 (15)
N1—C7—C8—C9−79.26 (15)C22—N1—C20—N20.13 (15)
C1—C7—C8—C946.44 (18)C7—N1—C20—N2−179.07 (11)
C13—C8—C9—C10−1.8 (2)C20—N2—C21—C220.04 (15)
C7—C8—C9—C10175.57 (12)N2—C21—C22—N10.03 (15)
C8—C9—C10—C110.5 (2)C20—N1—C22—C21−0.09 (14)
C9—C10—C11—C121.4 (2)C7—N1—C22—C21179.16 (11)
C9—C10—C11—C14−177.33 (12)
Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C20–C22, C1–C6 and C14–C19 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7···N2i1.002.453.418 (2)161
C3—H3···Cg1ii0.952.763.609 (2)149
C6—H6···Cg1iii0.952.963.900 (3)171
C18—H18···Cg2iv0.953.013.797 (7)141
C21—H21···Cg2v0.952.763.694 (7)170
C12—H12···Cg3vi0.952.873.737 (5)153
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C20–C22, C1–C6 and C14–C19 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C7—H7⋯N2i1.002.453.418 (2)161
C3—H3⋯Cg1ii0.952.763.609 (2)149
C6—H6⋯Cg1iii0.952.963.900 (3)171
C18—H18⋯Cg2iv0.953.013.797 (7)141
C21—H21⋯Cg2v0.952.763.694 (7)170
C12—H12⋯Cg3vi0.952.873.737 (5)153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 2.  Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses.

Authors:  T E Lackner; S P Clissold
Journal:  Drugs       Date:  1989-08       Impact factor: 9.546

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total

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