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organic compounds
1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole (bifonazole)
aDepartment of Industrial and Physical Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, IN 47907, USA, bLaboratory for Pharmacotechnology and Biopharmacy, K.U. Leuven, Gasthuisberg O&N2, Herestraat 49, Box 921, 3000, Leuven, Belgium, and cDepartment of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
*Correspondence e-mail: lstaylor@purdue.edu
In the title compound, C22H18N2, 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, molecules interact through intermolecular 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 interactions
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
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Refinement
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Data collection: CrystalClear (Rigaku, 2001); cell 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.
Supporting information
10.1107/S1600536810037876/rz2487sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810037876/rz2487Isup2.hkl
A
of the title compound was prepared by adding an excess of powder to 20 ml of diethyl ether. Subsequent to stirring the suspension overnight, filtration was performed using a 0.2 µm PTFE syringe filter (13 mm, VWR International, LLC, West Chester, PA, USA). The solution was transferred into a 20 ml scintillation vial in 20 ml scintillation vials (Research Products International Corp., Mt. Prospect, IL, USA) and three holes were pierced in the cap of the vial to allow the solvent to slowly evaporate. After one week, all solvent had evaporated and crystals of the title compound were obtained.H atoms were placed in calculated positions and treated as riding on their parent atoms with C—H = 0.95 Å (aromatic), 1.00 Å (aliphatic) and with Uiso(H) = 1.2 Ueq(C).
Data collection: CrystalClear (Rigaku, 2001); cell
DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); 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 (Sheldrick, 2008) and local programs. ![]() | Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. H atoms are presented as small spheres of arbitrary radius. |
C22H18N2 | F(000) = 656 |
Mr = 310.40 | Dx = 1.245 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 3380 reflections |
a = 7.9737 (7) Å | θ = 2–71° |
b = 6.2591 (6) Å | µ = 0.56 mm−1 |
c = 33.265 (3) Å | T = 150 K |
β = 93.805 (8)° | Plate, colourless |
V = 1656.5 (3) Å3 | 0.20 × 0.20 × 0.04 mm |
Z = 4 |
Rigaku Rapid II diffractometer | 2801 reflections with I > 2σ(I) |
Confocal optics monochromator | Rint = 0.030 |
ω scans | θmax = 71.8°, θmin = 2.7° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = 0→9 |
Tmin = 0.860, Tmax = 0.979 | k = 0→7 |
19391 measured reflections | l = −40→40 |
3064 independent reflections |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 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) = 0.107 | Δρmax = 0.19 e Å−3 |
S = 1.06 | Δρmin = −0.20 e Å−3 |
3064 reflections | Extinction correction: SHELXL97 (Sheldrick, 2008) |
218 parameters | Extinction coefficient: 0.20E-02 |
0 restraints |
C22H18N2 | V = 1656.5 (3) Å3 |
Mr = 310.40 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 7.9737 (7) Å | µ = 0.56 mm−1 |
b = 6.2591 (6) Å | T = 150 K |
c = 33.265 (3) Å | 0.20 × 0.20 × 0.04 mm |
β = 93.805 (8)° |
Rigaku Rapid II diffractometer | 3064 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 2801 reflections with I > 2σ(I) |
Tmin = 0.860, Tmax = 0.979 | Rint = 0.030 |
19391 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.19 e Å−3 |
3064 reflections | Δρmin = −0.20 e Å−3 |
218 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.15014 (12) | 0.10641 (19) | 0.07667 (3) | 0.0251 (3) | |
N2 | 0.26374 (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) | |
C7 | 0.08225 (15) | 0.3066 (2) | 0.09321 (4) | 0.0247 (3) | |
C8 | 0.12033 (15) | 0.3155 (2) | 0.13881 (4) | 0.0245 (3) | |
C9 | 0.02747 (16) | 0.2044 (2) | 0.16633 (4) | 0.0288 (3) | |
C10 | 0.07544 (16) | 0.2074 (2) | 0.20723 (4) | 0.0290 (3) | |
C11 | 0.21664 (15) | 0.3221 (2) | 0.22243 (4) | 0.0262 (3) | |
C12 | 0.30588 (16) | 0.4380 (2) | 0.19481 (4) | 0.0288 (3) | |
C13 | 0.25869 (16) | 0.4334 (2) | 0.15381 (4) | 0.0276 (3) | |
C14 | 0.27240 (15) | 0.3177 (2) | 0.26618 (4) | 0.0266 (3) | |
C15 | 0.36722 (17) | 0.4845 (2) | 0.28421 (4) | 0.0318 (3) | |
C16 | 0.42239 (18) | 0.4754 (3) | 0.32482 (4) | 0.0350 (3) | |
C17 | 0.38402 (17) | 0.3018 (2) | 0.34818 (4) | 0.0319 (3) | |
C18 | 0.28887 (17) | 0.1358 (3) | 0.33100 (4) | 0.0342 (3) | |
C19 | 0.23430 (17) | 0.1436 (2) | 0.29038 (4) | 0.0324 (3) | |
C20 | 0.21208 (16) | −0.0692 (2) | 0.09636 (4) | 0.0283 (3) | |
C21 | 0.23282 (16) | −0.1299 (2) | 0.03361 (4) | 0.0316 (3) | |
C22 | 0.16304 (17) | 0.0681 (2) | 0.03627 (4) | 0.0314 (3) | |
H2 | −0.1817 | 0.0306 | 0.0900 | 0.033* | |
H3 | −0.4657 | 0.0888 | 0.0704 | 0.038* | |
H4 | −0.5558 | 0.4246 | 0.0473 | 0.039* | |
H5 | −0.3624 | 0.7018 | 0.0428 | 0.039* | |
H6 | −0.0789 | 0.6467 | 0.0632 | 0.035* | |
H7 | 0.1445 | 0.4277 | 0.0814 | 0.030* | |
H9 | −0.0694 | 0.1261 | 0.1569 | 0.035* | |
H10 | 0.0110 | 0.1299 | 0.2253 | 0.035* | |
H12 | 0.4002 | 0.5210 | 0.2042 | 0.035* | |
H13 | 0.3221 | 0.5123 | 0.1357 | 0.033* | |
H15 | 0.3942 | 0.6052 | 0.2686 | 0.038* | |
H16 | 0.4870 | 0.5896 | 0.3366 | 0.042* | |
H17 | 0.4225 | 0.2962 | 0.3758 | 0.038* | |
H18 | 0.2609 | 0.0167 | 0.3469 | 0.041* | |
H19 | 0.1699 | 0.0286 | 0.2789 | 0.039* | |
H20 | 0.2177 | −0.0849 | 0.1248 | 0.034* | |
H21 | 0.2567 | −0.1985 | 0.0092 | 0.038* | |
H22 | 0.1300 | 0.1609 | 0.0146 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0191 (5) | 0.0280 (6) | 0.0278 (5) | 0.0017 (4) | −0.0006 (4) | 0.0008 (4) |
N2 | 0.0282 (6) | 0.0301 (7) | 0.0369 (6) | 0.0021 (5) | 0.0042 (5) | −0.0010 (5) |
C1 | 0.0227 (6) | 0.0281 (8) | 0.0231 (6) | 0.0019 (5) | 0.0004 (5) | −0.0019 (5) |
C2 | 0.0263 (6) | 0.0274 (8) | 0.0293 (6) | 0.0016 (5) | −0.0002 (5) | 0.0023 (5) |
C3 | 0.0239 (6) | 0.0358 (9) | 0.0342 (7) | −0.0037 (6) | 0.0024 (5) | 0.0001 (6) |
C4 | 0.0217 (6) | 0.0417 (9) | 0.0331 (7) | 0.0063 (6) | 0.0002 (5) | −0.0025 (6) |
C5 | 0.0309 (7) | 0.0316 (9) | 0.0341 (7) | 0.0090 (6) | −0.0016 (5) | 0.0006 (6) |
C6 | 0.0277 (7) | 0.0270 (8) | 0.0324 (7) | 0.0007 (5) | 0.0003 (5) | −0.0004 (6) |
C7 | 0.0213 (6) | 0.0220 (7) | 0.0307 (7) | −0.0002 (5) | 0.0012 (5) | 0.0004 (5) |
C8 | 0.0213 (6) | 0.0229 (7) | 0.0293 (6) | 0.0039 (5) | 0.0006 (5) | −0.0006 (5) |
C9 | 0.0213 (6) | 0.0305 (8) | 0.0343 (7) | −0.0044 (5) | −0.0003 (5) | −0.0015 (6) |
C10 | 0.0233 (6) | 0.0326 (8) | 0.0314 (7) | −0.0033 (5) | 0.0039 (5) | 0.0017 (6) |
C11 | 0.0218 (6) | 0.0268 (8) | 0.0301 (7) | 0.0022 (5) | 0.0010 (5) | −0.0013 (5) |
C12 | 0.0239 (6) | 0.0290 (8) | 0.0330 (7) | −0.0040 (5) | −0.0015 (5) | −0.0006 (5) |
C13 | 0.0241 (6) | 0.0269 (8) | 0.0318 (7) | −0.0017 (5) | 0.0019 (5) | 0.0028 (5) |
C14 | 0.0197 (6) | 0.0308 (8) | 0.0296 (7) | 0.0012 (5) | 0.0026 (5) | −0.0009 (5) |
C15 | 0.0299 (7) | 0.0335 (8) | 0.0319 (7) | −0.0032 (6) | 0.0011 (5) | 0.0007 (6) |
C16 | 0.0327 (7) | 0.0381 (9) | 0.0337 (7) | −0.0041 (6) | −0.0016 (6) | −0.0051 (6) |
C17 | 0.0270 (6) | 0.0408 (9) | 0.0276 (7) | 0.0029 (6) | −0.0001 (5) | −0.0020 (6) |
C18 | 0.0305 (7) | 0.0398 (9) | 0.0325 (7) | −0.0019 (6) | 0.0041 (5) | 0.0055 (6) |
C19 | 0.0281 (7) | 0.0360 (9) | 0.0328 (7) | −0.0052 (6) | 0.0003 (5) | −0.0006 (6) |
C20 | 0.0255 (6) | 0.0288 (8) | 0.0306 (7) | 0.0018 (5) | 0.0007 (5) | 0.0020 (5) |
C21 | 0.0281 (7) | 0.0359 (9) | 0.0308 (7) | 0.0006 (6) | 0.0031 (5) | −0.0045 (6) |
C22 | 0.0301 (7) | 0.0370 (9) | 0.0267 (6) | 0.0041 (6) | −0.0003 (5) | 0.0005 (6) |
N1—C20 | 1.3560 (17) | C10—C11 | 1.4011 (18) |
N1—C22 | 1.3758 (17) | C10—H10 | 0.9500 |
N1—C7 | 1.4854 (17) | C11—C12 | 1.4012 (19) |
N2—C20 | 1.3226 (18) | C11—C14 | 1.4935 (18) |
N2—C21 | 1.3765 (18) | C12—C13 | 1.3907 (18) |
C1—C2 | 1.3921 (19) | C12—H12 | 0.9500 |
C1—C6 | 1.3940 (19) | C13—H13 | 0.9500 |
C1—C7 | 1.5263 (16) | C14—C19 | 1.400 (2) |
C2—C3 | 1.3947 (18) | C14—C15 | 1.4005 (19) |
C2—H2 | 0.9500 | C15—C16 | 1.3939 (19) |
C3—C4 | 1.386 (2) | C15—H15 | 0.9500 |
C3—H3 | 0.9500 | C16—C17 | 1.381 (2) |
C4—C5 | 1.384 (2) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C17—C18 | 1.387 (2) |
C5—C6 | 1.3949 (19) | C17—H17 | 0.9500 |
C5—H5 | 0.9500 | C18—C19 | 1.3928 (19) |
C6—H6 | 0.9500 | C18—H18 | 0.9500 |
C7—C8 | 1.5280 (17) | C19—H19 | 0.9500 |
C7—H7 | 1.0000 | C20—H20 | 0.9500 |
C8—C13 | 1.3921 (18) | C21—C22 | 1.364 (2) |
C8—C9 | 1.4000 (19) | C21—H21 | 0.9500 |
C9—C10 | 1.3887 (18) | C22—H22 | 0.9500 |
C9—H9 | 0.9500 | ||
C20—N1—C22 | 106.39 (11) | C10—C11—C12 | 117.35 (12) |
C20—N1—C7 | 129.43 (11) | C10—C11—C14 | 121.48 (12) |
C22—N1—C7 | 124.18 (11) | C12—C11—C14 | 121.16 (12) |
C20—N2—C21 | 104.82 (12) | C13—C12—C11 | 121.09 (12) |
C2—C1—C6 | 119.30 (11) | C13—C12—H12 | 119.50 |
C2—C1—C7 | 122.18 (12) | C11—C12—H12 | 119.50 |
C6—C1—C7 | 118.52 (12) | C12—C13—C8 | 121.25 (12) |
C1—C2—C3 | 120.16 (13) | C12—C13—H13 | 119.40 |
C1—C2—H2 | 119.90 | C8—C13—H13 | 119.40 |
C3—C2—H2 | 119.90 | C19—C14—C15 | 117.75 (12) |
C4—C3—C2 | 120.16 (13) | C19—C14—C11 | 120.86 (12) |
C4—C3—H3 | 119.90 | C15—C14—C11 | 121.38 (12) |
C2—C3—H3 | 119.90 | C16—C15—C14 | 120.74 (14) |
C5—C4—C3 | 120.03 (12) | C16—C15—H15 | 119.60 |
C5—C4—H4 | 120.00 | C14—C15—H15 | 119.60 |
C3—C4—H4 | 120.00 | C17—C16—C15 | 120.66 (14) |
C4—C5—C6 | 120.02 (13) | C17—C16—H16 | 119.70 |
C4—C5—H5 | 120.00 | C15—C16—H16 | 119.70 |
C6—C5—H5 | 120.00 | C16—C17—C18 | 119.52 (13) |
C1—C6—C5 | 120.30 (13) | C16—C17—H17 | 120.20 |
C1—C6—H6 | 119.80 | C18—C17—H17 | 120.20 |
C5—C6—H6 | 119.80 | C17—C18—C19 | 120.02 (14) |
N1—C7—C1 | 110.62 (10) | C17—C18—H18 | 120.00 |
N1—C7—C8 | 110.18 (10) | C19—C18—H18 | 120.00 |
C1—C7—C8 | 114.84 (10) | C18—C19—C14 | 121.31 (13) |
N1—C7—H7 | 106.90 | C18—C19—H19 | 119.30 |
C1—C7—H7 | 106.90 | C14—C19—H19 | 119.30 |
C8—C7—H7 | 106.90 | N2—C20—N1 | 112.32 (12) |
C13—C8—C9 | 118.03 (12) | N2—C20—H20 | 123.80 |
C13—C8—C7 | 118.39 (11) | N1—C20—H20 | 123.80 |
C9—C8—C7 | 123.53 (11) | C22—C21—N2 | 110.27 (12) |
C10—C9—C8 | 120.71 (12) | C22—C21—H21 | 124.90 |
C10—C9—H9 | 119.60 | N2—C21—H21 | 124.90 |
C8—C9—H9 | 119.60 | C21—C22—N1 | 106.21 (12) |
C9—C10—C11 | 121.53 (12) | C21—C22—H22 | 126.90 |
C9—C10—H10 | 119.20 | N1—C22—H22 | 126.90 |
C11—C10—H10 | 119.20 | ||
C6—C1—C2—C3 | −1.77 (19) | C10—C11—C12—C13 | −1.9 (2) |
C7—C1—C2—C3 | 178.09 (12) | C14—C11—C12—C13 | 176.77 (12) |
C1—C2—C3—C4 | 0.9 (2) | C11—C12—C13—C8 | 0.6 (2) |
C2—C3—C4—C5 | 0.6 (2) | C9—C8—C13—C12 | 1.3 (2) |
C3—C4—C5—C6 | −1.1 (2) | C7—C8—C13—C12 | −176.27 (12) |
C2—C1—C6—C5 | 1.24 (19) | C10—C11—C14—C19 | 25.82 (19) |
C7—C1—C6—C5 | −178.63 (12) | C12—C11—C14—C19 | −152.84 (13) |
C4—C5—C6—C1 | 0.2 (2) | C10—C11—C14—C15 | −155.53 (13) |
C20—N1—C7—C1 | −116.94 (13) | C12—C11—C14—C15 | 25.82 (19) |
C22—N1—C7—C1 | 63.98 (15) | C19—C14—C15—C16 | 0.5 (2) |
C20—N1—C7—C8 | 11.12 (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—N1 | 46.28 (16) | C15—C16—C17—C18 | −0.3 (2) |
C6—C1—C7—N1 | −133.85 (12) | C16—C17—C18—C19 | 0.7 (2) |
C2—C1—C7—C8 | −79.20 (15) | C17—C18—C19—C14 | −0.5 (2) |
C6—C1—C7—C8 | 100.67 (14) | C15—C14—C19—C18 | −0.1 (2) |
N1—C7—C8—C13 | 98.12 (14) | C11—C14—C19—C18 | 178.57 (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—N2 | 0.13 (15) |
C1—C7—C8—C9 | 46.44 (18) | C7—N1—C20—N2 | −179.07 (11) |
C13—C8—C9—C10 | −1.8 (2) | C20—N2—C21—C22 | 0.04 (15) |
C7—C8—C9—C10 | 175.57 (12) | N2—C21—C22—N1 | 0.03 (15) |
C8—C9—C10—C11 | 0.5 (2) | C20—N1—C22—C21 | −0.09 (14) |
C9—C10—C11—C12 | 1.4 (2) | C7—N1—C22—C21 | 179.16 (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···A | D—H | H···A | D···A | D—H···A |
C7—H7···N2i | 1.00 | 2.45 | 3.418 (2) | 161 |
C3—H3···Cg1ii | 0.95 | 2.76 | 3.609 (2) | 149 |
C6—H6···Cg1iii | 0.95 | 2.96 | 3.900 (3) | 171 |
C18—H18···Cg2iv | 0.95 | 3.01 | 3.797 (7) | 141 |
C21—H21···Cg2v | 0.95 | 2.76 | 3.694 (7) | 170 |
C12—H12···Cg3vi | 0.95 | 2.87 | 3.737 (5) | 153 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x, y+1/2, −z+1/2; (v) −x, −y, −z; (vi) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H18N2 |
Mr | 310.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 7.9737 (7), 6.2591 (6), 33.265 (3) |
β (°) | 93.805 (8) |
V (Å3) | 1656.5 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.20 × 0.20 × 0.04 |
Data collection | |
Diffractometer | Rigaku Rapid II diffractometer |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.860, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19391, 3064, 2801 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.107, 1.06 |
No. of reflections | 3064 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.20 |
Computer programs: CrystalClear (Rigaku, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), ORTEPII (Johnson, 1976) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and local programs.
Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C20–C22, C1–C6 and C14–C19 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···N2i | 1.00 | 2.45 | 3.418 (2) | 161 |
C3—H3···Cg1ii | 0.95 | 2.76 | 3.609 (2) | 149 |
C6—H6···Cg1iii | 0.95 | 2.96 | 3.900 (3) | 171 |
C18—H18···Cg2iv | 0.95 | 3.01 | 3.797 (7) | 141 |
C21—H21···Cg2v | 0.95 | 2.76 | 3.694 (7) | 170 |
C12—H12···Cg3vi | 0.95 | 2.87 | 3.737 (5) | 153 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x, y+1/2, −z+1/2; (v) −x, −y, −z; (vi) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors would like to thank the National Science Foundation Engineering Research Center for Structured Organic Particulate Systems for financial support (NSF ERC-SOPS)(EEC-0540855). The authors thank the National Science Foundation, Directorate for Mathematical & Physical Sciences, Division of Materials Research, for financial support (NSF MPS-DMR)(DMR-0804609). BVE is a Postdoctoral Researcher of the `Fonds voor Wetenschappelijk Onderzoek', Flanders, Belgium.
References
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Lackner, T. E. & Clissold, S. P. (1989). Drugs, 38, 204–225. CrossRef CAS PubMed Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rigaku (2001). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Bifonazole is a broad-spectrum antifungal agent, mainly used by topical application in the treatment of fungal skin infections, including nail infections (Lackner & Clissold, 1989). In the crystal structure of the racemate, layers of the R and S enantiomer alternate along the c axis. Figure 1 shows the S configuration of the chiral center at atom C7. The dihedral angles between the different rings are 26.17 (8)° for the two aromatic rings of the biphenyl group, 101.80 (4)° for the imidazole ring and the benzene ring of the biphenyl group, 62.34 (5)° for the phenyl ring and the benzene ring of the biphenyl group, and 92.98 (5)° for the imidazole ring and the phenyl ring. In the crystal structure, molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1) into chains running parallel to the b axis. The chains are further connected by C—H···π stacking interactions to form a three-dimensional network.