2-[(Cyclo-penta-1,3-dien-2-yl)diphenyl-meth-yl]-1-methyl-1H-imidazole.

The title compound, C(22)H(20)N(2), (Ib), forms along with 2-[(cyclo-penta-1,3-dien-1-yl)diphenyl-meth-yl]-1-methyl-1H-imid-azole, (Ia), which differs with respect to the position of the double-bonds in the C(5)H(5) ring, in an approximately 3:7 ratio (Ia:Ib; NMR spectroscopy data). However, in a single crystal, only compound (Ib) is present. H atoms of the CH(2) group (C(5)H(5) ring) were found from the difference Fourier synthesis and refined isotropically using the riding model. Hypothesis on possible presence of the (Ia) isomer in crystal lattice (model with a C(5)H(5) ring disordered between two positions) was especially checked and rejected due to its inconsistency. In the crystal structure, no significant hydrogen-bonding inter-actions between the CH(2) groups of the C(5)H(5) rings and nonsubstituted N-atoms of the imidazole rings were observed. Despite the fact that the chemically achiral compound (I) crystallizes in a chiral space group P2(1)2(1)2(1), neither the absolute structure determination nor assignment of the inversion twinning was possible in the absence of a heavy atom.

Related literature

For the structural parameters of mono-alkyl substituted cyclo­penta­dienes (organic structures only), see: Tacke et al. (2001 ▶); Liebling & Marsh (1965 ▶); Haumann et al.(1996 ▶); Deck et al. (2004 ▶); Malpass et al. (2004 ▶); Cheung et al. (2005 ▶); Bauer et al. (2001 ▶); Huerlander et al. (2002 ▶); Millelr & Bercaw (2004 ▶); Li et al. (2005 ▶); Brunner et al. (2004 ▶); Otero et al. (2007 ▶); Hutton et al. (2008 ▶). For the structural parameters of 1,2-dialkyl-1H-imidazoles (organic structures only, not bi- or oligocyclic, non-ionic), see: Bruijnincx et al. (2005 ▶); Aakeroy et al. (2006 ▶); Zhang et al. (2007 ▶); Upadhyaya et al. (1997 ▶); Braussaud et al. (2001 ▶); Peters et al. (2005 ▶); Laus et al. (2008 ▶). For the structural parameters of Li, Ti, and Zr complexes derived from 1H-imidazol(in)-2-yl side-chain-functionalized cyclo­penta­dienes, see: Krut’ko et al. (2006 ▶); Nie et al. (2008 ▶); Wang et al. (2009 ▶). For a description of the Cambridge Structural database, see: Allen (2002 ▶).

Experimental

Crystal data

C22H20N2

M = 312.40

Orthorhombic,

a = 10.563 (5) Å

b = 10.603 (5) Å

c = 15.185 (7) Å

V = 1700.6 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.20 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.986, T max = 0.996

8785 measured reflections

1922 independent reflections

1543 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.04

1922 reflections

218 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055561/dn2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055561/dn2523Isup2.hkl

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

C22H20N2	F(000) = 664
Mr = 312.40	Dx = 1.220 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5639 reflections
a = 10.563 (5) Å	θ = 2.3–28.0°
b = 10.603 (5) Å	µ = 0.07 mm−1
c = 15.185 (7) Å	T = 295 K
V = 1700.6 (14) Å3	Prism, colorless
Z = 4	0.20 × 0.05 × 0.05 mm

Bruker SMART APEXII diffractometer	1922 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 8.333 pixels mm-1	θmax = 26.0°, θmin = 2.3°
phi and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.986, Tmax = 0.996	l = −10→18
8785 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.110P] where P = (Fo2 + 2Fc2)/3
1922 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.27 e Å−3
5 restraints	Δρmin = −0.11 e Å−3

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	0.1464 (2)	0.6352 (2)	0.49551 (13)	0.0578 (6)
N2	0.2989 (2)	0.73895 (18)	0.56444 (14)	0.0588 (6)
C1	0.2381 (2)	0.6304 (2)	0.55926 (15)	0.0460 (5)
C2	0.1512 (3)	0.7552 (3)	0.4606 (2)	0.0725 (8)
H2	0.0996	0.7876	0.4164	0.087*
C3	0.2442 (3)	0.8160 (3)	0.5025 (2)	0.0756 (9)
H3	0.2685	0.8987	0.4914	0.091*
C4	0.0623 (3)	0.5371 (3)	0.4627 (2)	0.0785 (9)
H4C	0.0274	0.4912	0.5115	0.118*
H4A	0.1091	0.4805	0.4256	0.118*
H4B	−0.0050	0.5749	0.4294	0.118*
C5	0.2651 (2)	0.5151 (2)	0.61653 (14)	0.0412 (5)
C11	0.3890 (2)	0.5365 (2)	0.66661 (15)	0.0457 (5)
C12	0.4947 (2)	0.4661 (3)	0.66347 (17)	0.0561 (6)
H12	0.5063	0.3969	0.6267	0.067*
C13	0.5894 (3)	0.5134 (3)	0.7259 (2)	0.0778 (8)
H13A	0.6656	0.5395	0.6954	0.093*
H13B	0.6113	0.4489	0.7686	0.093*
C14	0.5283 (3)	0.6217 (3)	0.76939 (19)	0.0790 (8)
H14	0.5641	0.6719	0.8130	0.095*
C15	0.4055 (3)	0.6363 (2)	0.73309 (18)	0.0616 (6)
H15	0.3464	0.6974	0.7484	0.074*
C21	0.1592 (2)	0.4951 (2)	0.68599 (14)	0.0443 (5)
C22	0.0450 (2)	0.5593 (3)	0.68353 (18)	0.0580 (7)
H22	0.0312	0.6208	0.6409	0.070*
C23	−0.0488 (3)	0.5321 (3)	0.7443 (2)	0.0754 (9)
H23	−0.1253	0.5754	0.7420	0.090*
C24	−0.0307 (3)	0.4438 (3)	0.8067 (2)	0.0807 (10)
H24	−0.0959	0.4237	0.8453	0.097*
C25	0.0844 (3)	0.3828 (3)	0.81354 (18)	0.0688 (8)
H25	0.0980	0.3246	0.8584	0.083*
C26	0.1786 (3)	0.4083 (2)	0.75399 (16)	0.0562 (6)
H26	0.2562	0.3675	0.7589	0.067*
C31	0.2772 (2)	0.3977 (2)	0.55630 (14)	0.0430 (5)
C32	0.3568 (2)	0.4048 (2)	0.48296 (16)	0.0537 (6)
H32	0.4036	0.4777	0.4728	0.064*
C33	0.3665 (3)	0.3046 (3)	0.42553 (18)	0.0650 (7)
H33	0.4188	0.3112	0.3765	0.078*
C34	0.3004 (3)	0.1959 (3)	0.4395 (2)	0.0713 (8)
H34	0.3082	0.1288	0.4004	0.086*
C35	0.2234 (3)	0.1862 (3)	0.5106 (2)	0.0707 (8)
H35	0.1785	0.1120	0.5204	0.085*
C36	0.2110 (2)	0.2860 (2)	0.56874 (17)	0.0536 (6)
H36	0.1575	0.2780	0.6170	0.064*

	U11	U22	U33	U12	U13	U23
N1	0.0615 (14)	0.0586 (12)	0.0533 (11)	0.0116 (11)	−0.0076 (11)	0.0052 (11)
N2	0.0645 (14)	0.0426 (10)	0.0692 (13)	−0.0012 (10)	0.0033 (12)	0.0092 (10)
C1	0.0457 (13)	0.0445 (12)	0.0479 (11)	0.0063 (11)	0.0039 (10)	0.0027 (10)
C2	0.085 (2)	0.0667 (17)	0.0661 (16)	0.0255 (17)	−0.0024 (17)	0.0166 (16)
C3	0.090 (2)	0.0497 (14)	0.087 (2)	0.0101 (16)	0.0023 (19)	0.0205 (15)
C4	0.073 (2)	0.082 (2)	0.0800 (19)	0.0081 (17)	−0.0301 (17)	−0.0082 (18)
C5	0.0389 (11)	0.0402 (11)	0.0445 (11)	0.0008 (10)	0.0002 (9)	0.0015 (9)
C11	0.0440 (12)	0.0439 (12)	0.0491 (12)	−0.0060 (10)	0.0033 (10)	0.0054 (11)
C12	0.0452 (13)	0.0594 (14)	0.0638 (14)	0.0000 (12)	−0.0020 (11)	−0.0009 (12)
C13	0.0457 (13)	0.103 (2)	0.0843 (19)	−0.0100 (13)	−0.0138 (13)	0.0156 (17)
C14	0.0928 (19)	0.0814 (18)	0.0630 (16)	−0.0413 (15)	−0.0177 (15)	0.0016 (14)
C15	0.0736 (15)	0.0530 (13)	0.0584 (14)	−0.0067 (13)	0.0016 (13)	−0.0091 (14)
C21	0.0438 (12)	0.0425 (11)	0.0467 (11)	−0.0046 (10)	0.0029 (10)	−0.0078 (11)
C22	0.0454 (13)	0.0666 (16)	0.0621 (15)	0.0010 (12)	0.0014 (12)	−0.0066 (15)
C23	0.0467 (14)	0.095 (2)	0.085 (2)	−0.0048 (15)	0.0135 (15)	−0.017 (2)
C24	0.073 (2)	0.092 (2)	0.077 (2)	−0.0333 (19)	0.0245 (18)	−0.0198 (19)
C25	0.083 (2)	0.0648 (17)	0.0583 (15)	−0.0207 (16)	0.0146 (15)	0.0004 (14)
C26	0.0612 (15)	0.0536 (13)	0.0539 (13)	−0.0056 (12)	0.0048 (12)	−0.0029 (12)
C31	0.0394 (11)	0.0423 (11)	0.0474 (11)	0.0039 (10)	−0.0033 (10)	−0.0012 (9)
C32	0.0508 (14)	0.0553 (13)	0.0552 (13)	0.0013 (12)	0.0043 (12)	−0.0002 (12)
C33	0.0619 (16)	0.0782 (18)	0.0550 (14)	0.0102 (15)	0.0035 (13)	−0.0121 (15)
C34	0.0768 (19)	0.0639 (17)	0.0734 (18)	0.0084 (16)	−0.0021 (16)	−0.0177 (16)
C35	0.081 (2)	0.0531 (14)	0.0779 (18)	−0.0053 (15)	−0.0032 (18)	−0.0113 (14)
C36	0.0538 (14)	0.0488 (13)	0.0583 (14)	−0.0027 (11)	0.0019 (13)	−0.0059 (11)

N1—C1	1.370 (3)	C15—H15	0.9300
N1—C2	1.380 (3)	C21—C22	1.386 (3)
N1—C4	1.456 (4)	C21—C26	1.398 (3)
N2—C1	1.321 (3)	C22—C23	1.384 (4)
N2—C3	1.373 (3)	C22—H22	0.9300
C1—C5	1.527 (3)	C23—C24	1.346 (5)
C2—C3	1.336 (4)	C23—H23	0.9300
C2—H2	0.9300	C24—C25	1.381 (5)
C3—H3	0.9300	C24—H24	0.9300
C4—H4C	0.9600	C25—C26	1.372 (4)
C4—H4A	0.9600	C25—H25	0.9300
C4—H4B	0.9600	C26—H26	0.9300
C5—C11	1.530 (3)	C31—C36	1.388 (3)
C5—C31	1.550 (3)	C31—C32	1.398 (3)
C5—C21	1.552 (3)	C32—C33	1.378 (3)
C11—C12	1.344 (3)	C32—H32	0.9300
C11—C15	1.473 (3)	C33—C34	1.364 (4)
C12—C13	1.466 (4)	C33—H33	0.9300
C12—H12	0.9300	C34—C35	1.357 (4)
C13—C14	1.474 (5)	C34—H34	0.9300
C13—H13A	0.9700	C35—C36	1.384 (4)
C13—H13B	0.9700	C35—H35	0.9300
C14—C15	1.417 (4)	C36—H36	0.9300
C14—H14	0.9300
C1—N1—C2	106.3 (2)	C14—C15—C11	107.3 (3)
C1—N1—C4	130.2 (2)	C14—C15—H15	126.4
C2—N1—C4	123.4 (2)	C11—C15—H15	126.4
C1—N2—C3	105.8 (2)	C22—C21—C26	118.1 (2)
N2—C1—N1	110.7 (2)	C22—C21—C5	122.9 (2)
N2—C1—C5	124.9 (2)	C26—C21—C5	119.1 (2)
N1—C1—C5	124.4 (2)	C23—C22—C21	120.2 (3)
C3—C2—N1	106.8 (3)	C23—C22—H22	119.9
C3—C2—H2	126.6	C21—C22—H22	119.9
N1—C2—H2	126.6	C24—C23—C22	120.8 (3)
C2—C3—N2	110.5 (3)	C24—C23—H23	119.6
C2—C3—H3	124.8	C22—C23—H23	119.6
N2—C3—H3	124.8	C23—C24—C25	120.3 (3)
N1—C4—H4C	109.5	C23—C24—H24	119.8
N1—C4—H4A	109.5	C25—C24—H24	119.8
H4C—C4—H4A	109.5	C26—C25—C24	119.8 (3)
N1—C4—H4B	109.5	C26—C25—H25	120.1
H4C—C4—H4B	109.5	C24—C25—H25	120.1
H4A—C4—H4B	109.5	C25—C26—C21	120.7 (3)
C1—C5—C11	108.92 (18)	C25—C26—H26	119.7
C1—C5—C31	108.80 (16)	C21—C26—H26	119.7
C11—C5—C31	110.03 (17)	C36—C31—C32	117.2 (2)
C1—C5—C21	111.18 (18)	C36—C31—C5	124.3 (2)
C11—C5—C21	107.37 (17)	C32—C31—C5	118.42 (19)
C31—C5—C21	110.53 (17)	C33—C32—C31	120.4 (2)
C12—C11—C15	108.9 (2)	C33—C32—H32	119.8
C12—C11—C5	127.6 (2)	C31—C32—H32	119.8
C15—C11—C5	123.3 (2)	C34—C33—C32	121.0 (3)
C11—C12—C13	110.7 (3)	C34—C33—H33	119.5
C11—C12—H12	124.6	C32—C33—H33	119.5
C13—C12—H12	124.6	C35—C34—C33	119.7 (3)
C12—C13—C14	104.9 (2)	C35—C34—H34	120.2
C12—C13—H13A	110.8	C33—C34—H34	120.2
C14—C13—H13A	110.8	C34—C35—C36	120.4 (3)
C12—C13—H13B	110.8	C34—C35—H35	119.8
C14—C13—H13B	110.8	C36—C35—H35	119.8
H13A—C13—H13B	108.8	C35—C36—C31	121.2 (2)
C15—C14—C13	108.1 (2)	C35—C36—H36	119.4
C15—C14—H14	125.9	C31—C36—H36	119.4
C13—C14—H14	125.9
C3—N2—C1—N1	0.3 (3)	C1—C5—C21—C22	11.7 (3)
C3—N2—C1—C5	−179.4 (2)	C11—C5—C21—C22	130.7 (2)
C2—N1—C1—N2	−0.8 (3)	C31—C5—C21—C22	−109.2 (2)
C4—N1—C1—N2	175.5 (3)	C1—C5—C21—C26	−168.7 (2)
C2—N1—C1—C5	178.9 (2)	C11—C5—C21—C26	−49.7 (2)
C4—N1—C1—C5	−4.8 (4)	C31—C5—C21—C26	70.3 (2)
C1—N1—C2—C3	0.9 (3)	C26—C21—C22—C23	−3.4 (4)
C4—N1—C2—C3	−175.7 (3)	C5—C21—C22—C23	176.2 (2)
N1—C2—C3—N2	−0.7 (3)	C21—C22—C23—C24	0.2 (4)
C1—N2—C3—C2	0.2 (3)	C22—C23—C24—C25	3.0 (5)
N2—C1—C5—C11	−11.2 (3)	C23—C24—C25—C26	−3.0 (4)
N1—C1—C5—C11	169.1 (2)	C24—C25—C26—C21	−0.3 (4)
N2—C1—C5—C31	−131.2 (2)	C22—C21—C26—C25	3.5 (3)
N1—C1—C5—C31	49.2 (3)	C5—C21—C26—C25	−176.1 (2)
N2—C1—C5—C21	106.9 (3)	C1—C5—C31—C36	−128.3 (2)
N1—C1—C5—C21	−72.8 (2)	C11—C5—C31—C36	112.4 (2)
C1—C5—C11—C12	−120.6 (3)	C21—C5—C31—C36	−6.0 (3)
C31—C5—C11—C12	−1.5 (3)	C1—C5—C31—C32	49.8 (3)
C21—C5—C11—C12	118.9 (3)	C11—C5—C31—C32	−69.5 (2)
C1—C5—C11—C15	64.5 (3)	C21—C5—C31—C32	172.10 (19)
C31—C5—C11—C15	−176.32 (19)	C36—C31—C32—C33	0.9 (3)
C21—C5—C11—C15	−56.0 (3)	C5—C31—C32—C33	−177.3 (2)
C15—C11—C12—C13	−0.6 (3)	C31—C32—C33—C34	−1.0 (4)
C5—C11—C12—C13	−176.1 (2)	C32—C33—C34—C35	0.4 (5)
C11—C12—C13—C14	0.7 (3)	C33—C34—C35—C36	0.3 (5)
C12—C13—C14—C15	−0.5 (3)	C34—C35—C36—C31	−0.4 (4)
C13—C14—C15—C11	0.1 (3)	C32—C31—C36—C35	−0.2 (4)
C12—C11—C15—C14	0.3 (3)	C5—C31—C36—C35	177.9 (2)
C5—C11—C15—C14	176.0 (2)