1-[(Biphenyl-4-yl)(phen­yl)meth­yl]-1H-imidazole (bifonazole)

Van Eerdenbrugh, B.; Fanwick, P.E.; Taylor, L.S.

doi:10.1107/S1600536810037876

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2649

doi:10.1107/S1600536810037876

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1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole (bifonazole)

Bernard Van Eerdenbrugh,^a,^b Phillip E. Fanwick ^c and Lynne S. Taylor ^a ^*

^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

(Received 8 September 2010; accepted 21 September 2010; online 30 September 2010)

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

C₂₂H₁₈N₂
M_r = 310.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.06
3064 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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⋯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⋯Cg2^iv	0.95	3.01	3.797 (7)	141
C21—H21⋯Cg2^v	0.95	2.76	3.694 (7)	170
C12—H12⋯Cg3^vi	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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y, -z; (vi) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037876/rz2487sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037876/rz2487Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For a review of the antimicrobial activity of bifonazole and its therapeutic use in superficial mycoses, see: Lackner and Clissold (1989). To date, no crystal structure of bifonazole has been published.

Experimental top

A saturated solution 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.

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: 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.

Figures top

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.

1-[(Biphenyl-4-yl)(phenyl)methyl]-1H-imidazole top

Crystal data top

C₂₂H₁₈N₂	F(000) = 656
M_r = 310.40	D_x = 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

Data collection top

Rigaku Rapid II diffractometer	2801 reflections with I > 2σ(I)
Confocal optics monochromator	R_int = 0.030
ω scans	θ_max = 71.8°, θ_min = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = 0→9
T_min = 0.860, T_max = 0.979	k = 0→7
19391 measured reflections	l = −40→40
3064 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0501P)² + 0.7321P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.107	Δρ_max = 0.19 e Å⁻³
S = 1.06	Δρ_min = −0.20 e Å⁻³
3064 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008)
218 parameters	Extinction coefficient: 0.20E-02
0 restraints

Crystal data top

C₂₂H₁₈N₂	V = 1656.5 (3) Å³
M_r = 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)°

Data collection top

Rigaku Rapid II diffractometer	3064 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2801 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.979	R_int = 0.030
19391 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
3064 reflections	Δρ_min = −0.20 e Å⁻³
218 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.95	3.01	3.797 (7)	141
C21—H21···Cg2^v	0.95	2.76	3.694 (7)	170
C12—H12···Cg3^vi	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
M_r	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)
T_min, T_max	0.860, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	19391, 3064, 2801
R_int	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
Δρ_max, Δρ_min (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.

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.95	3.01	3.797 (7)	141
C21—H21···Cg2^v	0.95	2.76	3.694 (7)	170
C12—H12···Cg3^vi	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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Volume 66| Part 10| October 2010| Page o2649

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