Lophine (2,4,5-triphenyl-1H-imidazole).

The title compound, C(21)H(16)N(2), has been known since 1877. Although the crystal structure of 36 derivatives of lophine are known, the structure of parent compound has remained unknown until now. The three phenyl rings bonded to the imidazole core are not coplanar with the latter, with dihedral angles of 21.4 (3), 24.7 (3), and 39.0 (3)°, respectively, between the phenyl ring planes in the 2-, 4- and 5-positions of the imidazole ring. The mol-ecules are packed in layers running perpendicular to the b axis. Although there are acceptor and donor atoms for hydrogen bonds, no such inter-actions are detected in the crystal in contrast to other lophine derivatives.

Related literature

For background on lophine and its derivatives, see: Fridman et al. (2008 ▶); Fridman, Kaftory & Speiser (2007 ▶); Fridman, Kaftory, Eichen & Speiser (2007 ▶); Kamidate et al. (1989 ▶); Liu et al. (2005 ▶); Nakashima (2003 ▶); Nakashima et al. (1995 ▶); Radziszewski (1877 ▶); Seethalakshmi et al. (2006 ▶); Thiruvalluvar et al. (2007 ▶); Thuer et al. (2004 ▶). For information about the Cambridge Database, see: Allen (2002 ▶). For related literature, see: Inouye & Sakaino (2000 ▶); Kaftory et al. (1998 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C21H16N2

M = 296.36

Orthorhombic,

a = 20.218 (4) Å

b = 7.538 (2) Å

c = 20.699 (4) Å

V = 3154.6 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.50 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

22192 measured reflections

2747 independent reflections

1036 reflections with I > 2σ(I)

R int = 0.143

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.245

S = 1.09

2747 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Nonius, 2006); cell refinement: DENZO HKL-2000 (Otwinowski & Minor, 1997 ▶); data reduction: DENZO HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006552/hb2915sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006552/hb2915Isup2.hkl

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

C21H16N2	F(000) = 1248
Mr = 296.36	Dx = 1.248 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 22192 reflections
a = 20.218 (4) Å	θ = 2.0–25.3°
b = 7.538 (2) Å	µ = 0.07 mm−1
c = 20.699 (4) Å	T = 293 K
V = 3154.6 (12) Å3	Plate, colorless
Z = 8	0.50 × 0.10 × 0.05 mm

Nonius KappaCCD diffractometer	1036 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.143
graphite	θmax = 25.3°, θmin = 2.0°
φ and ω scans	h = −23→22
22192 measured reflections	k = −8→8
2747 independent reflections	l = −24→23

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)] = 0.088	H-atom parameters constrained
wR(F2) = 0.245	w = 1/[σ2(Fo2) + (0.0863P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2747 reflections	Δρmax = 0.25 e Å−3
209 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0089 (18)

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
N1	0.6928 (2)	0.1996 (5)	0.14220 (18)	0.0556 (11)
H1	0.6809	0.1806	0.1029	0.067*
N2	0.7563 (2)	0.2458 (5)	0.2252 (2)	0.0668 (12)
C1	0.8110 (3)	0.1974 (7)	0.1209 (3)	0.0660 (14)
C2	0.8052 (3)	0.2208 (9)	0.0564 (3)	0.0928 (19)
H2	0.7620	0.2437	0.0390	0.111*
C3	0.8616 (4)	0.2073 (9)	0.0170 (3)	0.108 (2)
H3	0.8570	0.2267	−0.0286	0.129*
C4	0.9225 (3)	0.1634 (8)	0.0422 (3)	0.0890 (19)
H4	0.9611	0.1517	0.0155	0.107*
C5	0.9267 (3)	0.1408 (8)	0.1067 (4)	0.0902 (19)
H5	0.9694	0.1134	0.1244	0.108*
C6	0.8727 (3)	0.1565 (7)	0.1470 (3)	0.0822 (18)
H6	0.8778	0.1408	0.1927	0.099*
C7	0.7536 (3)	0.2141 (7)	0.1634 (3)	0.0767 (16)
C8	0.6519 (3)	0.2205 (6)	0.1946 (3)	0.0672 (14)
C9	0.6911 (3)	0.2496 (6)	0.2465 (3)	0.0690 (14)
C10	0.6777 (3)	0.2762 (7)	0.3158 (2)	0.0689 (15)
C11	0.6295 (3)	0.1845 (7)	0.3489 (3)	0.0771 (16)
H11	0.6028	0.1011	0.3255	0.093*
C12	0.6206 (3)	0.2137 (9)	0.4140 (3)	0.0876 (18)
H12	0.5870	0.1509	0.4375	0.105*
C13	0.6578 (4)	0.3288 (10)	0.4475 (3)	0.098 (2)
H13	0.6503	0.3469	0.4928	0.118*
C14	0.7082 (4)	0.4240 (10)	0.4148 (3)	0.098 (2)
H14	0.7355	0.5090	0.4367	0.118*
C15	0.7179 (3)	0.3959 (8)	0.3504 (3)	0.0841 (18)
H15	0.7531	0.4548	0.3279	0.101*
C16	0.5797 (3)	0.2127 (7)	0.1838 (2)	0.0673 (15)
C17	0.5352 (3)	0.3003 (7)	0.2245 (3)	0.0739 (16)
H17	0.5523	0.3636	0.2611	0.089*
C18	0.4681 (3)	0.2945 (8)	0.2130 (3)	0.0827 (17)
H18	0.4383	0.3568	0.2411	0.099*
C19	0.4436 (3)	0.2035 (9)	0.1613 (3)	0.0944 (19)
H19	0.3968	0.1983	0.1536	0.113*
C20	0.4872 (4)	0.1191 (8)	0.1199 (3)	0.095 (2)
H20	0.4697	0.0557	0.0835	0.114*
C21	0.5545 (3)	0.1206 (7)	0.1311 (3)	0.0805 (17)
H21	0.5846	0.0615	0.1024	0.097*

	U11	U22	U33	U12	U13	U23
N1	0.056 (3)	0.067 (2)	0.044 (2)	0.000 (2)	−0.008 (2)	−0.0054 (19)
N2	0.065 (3)	0.072 (3)	0.064 (3)	−0.005 (2)	0.003 (3)	0.005 (2)
C1	0.069 (4)	0.066 (3)	0.062 (4)	0.004 (3)	−0.003 (3)	0.001 (3)
C2	0.077 (5)	0.133 (5)	0.068 (4)	0.024 (4)	−0.010 (4)	−0.006 (4)
C3	0.120 (6)	0.138 (6)	0.065 (4)	0.011 (5)	0.008 (4)	−0.004 (4)
C4	0.076 (5)	0.097 (4)	0.094 (5)	0.009 (3)	0.005 (4)	0.007 (4)
C5	0.074 (5)	0.094 (4)	0.102 (5)	0.003 (3)	−0.003 (4)	0.018 (4)
C6	0.085 (5)	0.087 (4)	0.074 (4)	−0.016 (3)	−0.011 (4)	0.012 (3)
C7	0.094 (5)	0.068 (3)	0.068 (4)	−0.003 (3)	−0.002 (4)	0.008 (3)
C8	0.074 (4)	0.060 (3)	0.068 (4)	0.002 (3)	−0.005 (3)	0.003 (3)
C9	0.082 (4)	0.056 (3)	0.070 (4)	−0.004 (3)	−0.002 (3)	0.000 (3)
C10	0.066 (4)	0.072 (3)	0.068 (4)	−0.005 (3)	−0.006 (3)	0.000 (3)
C11	0.070 (4)	0.083 (4)	0.077 (4)	−0.011 (3)	0.000 (3)	0.008 (3)
C12	0.069 (4)	0.122 (5)	0.071 (4)	0.003 (4)	−0.003 (4)	0.021 (4)
C13	0.081 (5)	0.146 (6)	0.067 (4)	0.015 (4)	−0.006 (4)	−0.010 (4)
C14	0.102 (6)	0.108 (5)	0.084 (5)	−0.004 (4)	−0.012 (4)	−0.021 (4)
C15	0.086 (4)	0.090 (4)	0.077 (4)	−0.018 (3)	−0.001 (3)	0.000 (3)
C16	0.081 (4)	0.059 (3)	0.062 (3)	−0.008 (3)	−0.004 (3)	0.002 (3)
C17	0.086 (5)	0.067 (3)	0.068 (4)	0.006 (3)	−0.010 (3)	0.001 (3)
C18	0.075 (5)	0.083 (4)	0.090 (5)	0.003 (3)	−0.006 (4)	0.012 (4)
C19	0.075 (5)	0.104 (5)	0.105 (5)	−0.005 (4)	−0.012 (4)	0.020 (4)
C20	0.106 (6)	0.090 (4)	0.090 (5)	−0.016 (4)	−0.027 (5)	−0.004 (4)
C21	0.086 (5)	0.083 (4)	0.072 (4)	−0.009 (3)	−0.010 (4)	0.000 (3)

N1—C7	1.310 (7)	C10—C15	1.410 (7)
N1—C8	1.374 (6)	C11—C12	1.377 (7)
N1—H1	0.8600	C11—H11	0.9600
N2—C7	1.302 (6)	C12—C13	1.342 (8)
N2—C9	1.391 (6)	C12—H12	0.9600
C1—C2	1.353 (7)	C13—C14	1.419 (9)
C1—C6	1.392 (7)	C13—H13	0.9600
C1—C7	1.462 (7)	C14—C15	1.363 (7)
C2—C3	1.406 (8)	C14—H14	0.9600
C2—H2	0.9602	C15—H15	0.9599
C3—C4	1.378 (8)	C16—C17	1.398 (7)
C3—H3	0.9600	C16—C21	1.390 (7)
C4—C5	1.348 (7)	C17—C18	1.377 (7)
C4—H4	0.9600	C17—H17	0.9602
C5—C6	1.378 (7)	C18—C19	1.364 (8)
C5—H5	0.9600	C18—H18	0.9599
C6—H6	0.9602	C19—C20	1.384 (9)
C8—C9	1.353 (7)	C19—H19	0.9600
C8—C16	1.477 (7)	C20—C21	1.380 (8)
C9—C10	1.474 (7)	C20—H20	0.9601
C10—C11	1.377 (7)	C21—H21	0.9599
C7—N1—C8	107.0 (4)	C12—C11—C10	119.9 (6)
C7—N1—H1	126.5	C12—C11—H11	121.6
C8—N1—H1	126.5	C10—C11—H11	118.5
C7—N2—C9	106.0 (5)	C13—C12—C11	122.4 (6)
C2—C1—C6	119.3 (6)	C13—C12—H12	117.0
C2—C1—C7	120.9 (6)	C11—C12—H12	120.6
C6—C1—C7	119.8 (5)	C12—C13—C14	118.9 (6)
C1—C2—C3	119.5 (6)	C12—C13—H13	120.6
C1—C2—H2	118.3	C14—C13—H13	120.6
C3—C2—H2	122.2	C15—C14—C13	119.4 (6)
C4—C3—C2	121.5 (6)	C15—C14—H14	118.9
C4—C3—H3	119.7	C13—C14—H14	121.6
C2—C3—H3	118.8	C14—C15—C10	120.9 (6)
C5—C4—C3	117.5 (6)	C14—C15—H15	120.6
C5—C4—H4	120.5	C10—C15—H15	118.5
C3—C4—H4	122.0	C17—C16—C21	118.2 (5)
C4—C5—C6	122.5 (6)	C17—C16—C8	121.7 (5)
C4—C5—H5	117.4	C21—C16—C8	120.1 (5)
C6—C5—H5	120.0	C18—C17—C16	121.0 (5)
C5—C6—C1	119.6 (6)	C18—C17—H17	120.3
C5—C6—H6	120.0	C16—C17—H17	118.7
C1—C6—H6	120.4	C19—C18—C17	120.5 (6)
N1—C7—N2	112.5 (6)	C19—C18—H18	119.5
N1—C7—C1	122.4 (5)	C17—C18—H18	120.0
N2—C7—C1	125.0 (6)	C18—C19—C20	119.1 (6)
C9—C8—N1	107.0 (5)	C18—C19—H19	120.6
C9—C8—C16	134.8 (6)	C20—C19—H19	120.4
N1—C8—C16	118.1 (5)	C21—C20—C19	121.4 (6)
C8—C9—N2	107.5 (5)	C21—C20—H20	119.9
C8—C9—C10	133.5 (6)	C19—C20—H20	118.7
N2—C9—C10	119.0 (5)	C20—C21—C16	119.8 (6)
C11—C10—C15	118.5 (5)	C20—C21—H21	121.3
C11—C10—C9	123.1 (5)	C16—C21—H21	118.9
C15—C10—C9	118.4 (5)
C6—C1—C2—C3	−1.4 (9)	C8—C9—C10—C11	38.5 (8)
C7—C1—C2—C3	178.7 (6)	N2—C9—C10—C11	−139.1 (5)
C1—C2—C3—C4	2.7 (10)	C8—C9—C10—C15	−144.2 (6)
C2—C3—C4—C5	−2.6 (10)	N2—C9—C10—C15	38.2 (7)
C3—C4—C5—C6	1.3 (9)	C15—C10—C11—C12	1.4 (9)
C4—C5—C6—C1	−0.1 (9)	C9—C10—C11—C12	178.7 (5)
C2—C1—C6—C5	0.1 (8)	C10—C11—C12—C13	−0.5 (10)
C7—C1—C6—C5	180.0 (5)	C11—C12—C13—C14	0.0 (10)
C8—N1—C7—N2	−1.1 (6)	C12—C13—C14—C15	−0.3 (10)
C8—N1—C7—C1	179.4 (5)	C13—C14—C15—C10	1.2 (10)
C9—N2—C7—N1	1.0 (6)	C11—C10—C15—C14	−1.8 (9)
C9—N2—C7—C1	−179.5 (5)	C9—C10—C15—C14	−179.2 (6)
C2—C1—C7—N1	20.7 (8)	C9—C8—C16—C17	24.5 (9)
C6—C1—C7—N1	−159.2 (5)	N1—C8—C16—C17	−153.3 (5)
C2—C1—C7—N2	−158.7 (6)	C9—C8—C16—C21	−157.2 (5)
C6—C1—C7—N2	21.4 (8)	N1—C8—C16—C21	25.0 (7)
C7—N1—C8—C9	0.7 (5)	C21—C16—C17—C18	0.5 (8)
C7—N1—C8—C16	179.1 (4)	C8—C16—C17—C18	178.8 (4)
N1—C8—C9—N2	−0.1 (5)	C16—C17—C18—C19	−0.3 (8)
C16—C8—C9—N2	−178.1 (5)	C17—C18—C19—C20	−0.9 (9)
N1—C8—C9—C10	−177.9 (5)	C18—C19—C20—C21	2.0 (10)
C16—C8—C9—C10	4.1 (10)	C19—C20—C21—C16	−1.9 (9)
C7—N2—C9—C8	−0.5 (5)	C17—C16—C21—C20	0.6 (8)
C7—N2—C9—C10	177.6 (4)	C8—C16—C21—C20	−177.7 (5)