1-(3,5-Di-meth-oxy-phen-yl)-4,5-dimethyl-2-phenyl-1H-imidazole.

In the title mol-ecule, C19H20N2O2, the imidazole ring makes dihedral angles of 57.29 (5) and 31.54 (5)° with the attached di-meth-oxy-phenyl residue and the phenyl ring, respectively. The dihedral angle between the di-meth-oxy-phenyl and phenyl rings is 61.15 (5)°. In the crystal, pairs of C-H⋯N hydrogen bonds connect the mol-ecules into inversion dimers.

Related literature

For the pharmacological activity of imidazole derivatives, see: Zala et al. (2012 ▶). For imidazole derivatives as ligands for Ir3+ complexes, see: Saravanan et al. (2011 ▶); Gayathri et al. (2010 ▶).

Experimental

Crystal data

C19H20N2O2

M = 308.37

Triclinic,

a = 8.363 (5) Å

b = 10.267 (5) Å

c = 10.481 (5) Å

α = 75.043 (5)°

β = 75.789 (5)°

γ = 74.576 (5)°

V = 822.9 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.912, T max = 0.984

16534 measured reflections

3780 independent reflections

2991 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.03

3780 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813023684/bt6926sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023684/bt6926Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023684/bt6926Isup3.cml

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

C19H20N2O2	Z = 2
Mr = 308.37	F(000) = 328
Triclinic, P1	Dx = 1.245 Mg m−3
Hall symbol: -P 1	Melting point: 396.15 K
a = 8.363 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.267 (5) Å	Cell parameters from 7500 reflections
c = 10.481 (5) Å	θ = 2.1–31.4°
α = 75.043 (5)°	µ = 0.08 mm−1
β = 75.789 (5)°	T = 295 K
γ = 74.576 (5)°	Block, colourless
V = 822.9 (7) Å3	0.35 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3780 independent reflections
Radiation source: fine-focus sealed tube	2991 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.912, Tmax = 0.984	k = −12→13
16534 measured reflections	l = −13→13

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.1449P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3780 reflections	Δρmax = 0.22 e Å−3
213 parameters	Δρmin = −0.17 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: 0.041 (5)

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
C1	0.08801 (17)	0.29240 (15)	0.71332 (14)	0.0479 (3)
H1	0.0021	0.3676	0.7320	0.058*
C2	0.0765 (2)	0.16195 (16)	0.78664 (16)	0.0587 (4)
H2	−0.0169	0.1499	0.8546	0.070*
C3	0.2017 (2)	0.04936 (16)	0.76043 (17)	0.0612 (4)
H3	0.1928	−0.0388	0.8094	0.073*
C4	0.3409 (2)	0.06850 (15)	0.66055 (17)	0.0612 (4)
H4	0.4267	−0.0072	0.6430	0.073*
C5	0.35386 (18)	0.19854 (14)	0.58670 (14)	0.0504 (3)
H5	0.4483	0.2100	0.5197	0.061*
C6	0.22692 (15)	0.31286 (13)	0.61149 (12)	0.0397 (3)
C7	0.23601 (14)	0.45452 (13)	0.53985 (12)	0.0382 (3)
C8	0.21210 (16)	0.67461 (13)	0.49929 (14)	0.0445 (3)
C9	0.30117 (16)	0.63430 (13)	0.38368 (13)	0.0432 (3)
C10	0.37438 (15)	0.40978 (13)	0.30887 (12)	0.0382 (3)
C11	0.53844 (15)	0.40107 (13)	0.23697 (12)	0.0407 (3)
H11	0.6111	0.4461	0.2545	0.049*
C12	0.59090 (15)	0.32340 (13)	0.13838 (12)	0.0411 (3)
C13	0.48453 (16)	0.25187 (13)	0.11554 (12)	0.0426 (3)
H13	0.5220	0.1981	0.0505	0.051*
C14	0.32267 (16)	0.26149 (13)	0.19032 (13)	0.0423 (3)
C15	0.26457 (15)	0.34325 (14)	0.28630 (13)	0.0422 (3)
H15	0.1540	0.3527	0.3341	0.051*
C16	0.1535 (2)	0.81699 (16)	0.52697 (18)	0.0652 (4)
H16A	0.2035	0.8803	0.4532	0.098*
H16B	0.1866	0.8185	0.6079	0.098*
H16C	0.0327	0.8438	0.5376	0.098*
C17	0.3660 (2)	0.71515 (16)	0.25083 (15)	0.0583 (4)
H17A	0.3205	0.8118	0.2486	0.087*
H17B	0.3325	0.6887	0.1816	0.087*
H17C	0.4870	0.6973	0.2362	0.087*
C18	0.85043 (19)	0.39811 (18)	0.05943 (17)	0.0611 (4)
H18A	0.7898	0.4920	0.0379	0.092*
H18B	0.9524	0.3835	−0.0063	0.092*
H18C	0.8781	0.3800	0.1469	0.092*
C19	0.2569 (3)	0.1152 (2)	0.0769 (2)	0.0763 (5)
H19A	0.2843	0.1731	−0.0097	0.114*
H19B	0.1653	0.0749	0.0777	0.114*
H19C	0.3538	0.0433	0.0946	0.114*
N1	0.17293 (13)	0.56251 (11)	0.59607 (11)	0.0428 (3)
N2	0.31654 (13)	0.49237 (11)	0.40949 (10)	0.0390 (2)
O1	0.74810 (12)	0.30746 (11)	0.05912 (10)	0.0557 (3)
O2	0.20886 (13)	0.19468 (12)	0.17648 (11)	0.0618 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0455 (7)	0.0507 (8)	0.0442 (7)	−0.0079 (6)	−0.0041 (5)	−0.0107 (6)
C2	0.0587 (9)	0.0609 (9)	0.0518 (8)	−0.0199 (7)	−0.0041 (7)	−0.0024 (7)
C3	0.0789 (11)	0.0466 (8)	0.0578 (9)	−0.0183 (7)	−0.0165 (8)	−0.0018 (7)
C4	0.0733 (10)	0.0452 (8)	0.0600 (9)	0.0014 (7)	−0.0140 (8)	−0.0151 (7)
C5	0.0511 (8)	0.0486 (8)	0.0470 (7)	−0.0037 (6)	−0.0042 (6)	−0.0141 (6)
C6	0.0422 (6)	0.0438 (7)	0.0358 (6)	−0.0080 (5)	−0.0086 (5)	−0.0128 (5)
C7	0.0346 (6)	0.0447 (7)	0.0367 (6)	−0.0069 (5)	−0.0038 (4)	−0.0154 (5)
C8	0.0441 (7)	0.0427 (7)	0.0487 (7)	−0.0083 (5)	−0.0071 (5)	−0.0157 (6)
C9	0.0442 (7)	0.0433 (7)	0.0444 (7)	−0.0108 (5)	−0.0088 (5)	−0.0111 (5)
C10	0.0394 (6)	0.0423 (6)	0.0332 (6)	−0.0063 (5)	−0.0055 (5)	−0.0123 (5)
C11	0.0385 (6)	0.0472 (7)	0.0383 (6)	−0.0115 (5)	−0.0052 (5)	−0.0122 (5)
C12	0.0382 (6)	0.0464 (7)	0.0352 (6)	−0.0071 (5)	−0.0012 (5)	−0.0098 (5)
C13	0.0477 (7)	0.0447 (7)	0.0359 (6)	−0.0084 (5)	−0.0040 (5)	−0.0145 (5)
C14	0.0438 (7)	0.0469 (7)	0.0403 (6)	−0.0121 (5)	−0.0098 (5)	−0.0119 (5)
C15	0.0362 (6)	0.0507 (7)	0.0403 (6)	−0.0094 (5)	−0.0033 (5)	−0.0144 (5)
C16	0.0730 (10)	0.0463 (8)	0.0749 (11)	−0.0117 (7)	0.0002 (8)	−0.0246 (8)
C17	0.0707 (10)	0.0539 (8)	0.0492 (8)	−0.0213 (7)	−0.0061 (7)	−0.0058 (6)
C18	0.0447 (8)	0.0767 (10)	0.0622 (9)	−0.0230 (7)	0.0072 (6)	−0.0213 (8)
C19	0.0892 (13)	0.0834 (12)	0.0785 (12)	−0.0404 (10)	−0.0069 (10)	−0.0412 (10)
N1	0.0423 (6)	0.0448 (6)	0.0426 (6)	−0.0081 (4)	−0.0026 (4)	−0.0177 (5)
N2	0.0402 (5)	0.0421 (6)	0.0360 (5)	−0.0094 (4)	−0.0031 (4)	−0.0136 (4)
O1	0.0451 (5)	0.0676 (6)	0.0545 (6)	−0.0168 (4)	0.0107 (4)	−0.0274 (5)
O2	0.0558 (6)	0.0790 (7)	0.0669 (7)	−0.0278 (5)	−0.0044 (5)	−0.0364 (6)

C1—C2	1.377 (2)	C11—H11	0.9300
C1—C6	1.3922 (19)	C12—O1	1.3656 (16)
C1—H1	0.9300	C12—C13	1.3895 (19)
C2—C3	1.374 (2)	C13—C14	1.3800 (19)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.381 (2)	C14—O2	1.3653 (16)
C3—H3	0.9300	C14—C15	1.3898 (18)
C4—C5	1.377 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.3897 (19)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.4669 (19)	C17—H17A	0.9600
C7—N1	1.3147 (16)	C17—H17B	0.9600
C7—N2	1.3729 (16)	C17—H17C	0.9600
C8—C9	1.3587 (19)	C18—O1	1.4231 (19)
C8—N1	1.3768 (18)	C18—H18A	0.9600
C8—C16	1.493 (2)	C18—H18B	0.9600
C9—N2	1.3882 (18)	C18—H18C	0.9600
C9—C17	1.481 (2)	C19—O2	1.406 (2)
C10—C15	1.3746 (18)	C19—H19A	0.9600
C10—C11	1.3857 (18)	C19—H19B	0.9600
C10—N2	1.4346 (16)	C19—H19C	0.9600
C11—C12	1.3831 (18)
C2—C1—C6	120.68 (13)	C12—C13—H13	120.3
C2—C1—H1	119.7	O2—C14—C13	123.93 (12)
C6—C1—H1	119.7	O2—C14—C15	115.28 (11)
C3—C2—C1	120.60 (15)	C13—C14—C15	120.79 (12)
C3—C2—H2	119.7	C10—C15—C14	118.41 (11)
C1—C2—H2	119.7	C10—C15—H15	120.8
C2—C3—C4	119.25 (14)	C14—C15—H15	120.8
C2—C3—H3	120.4	C8—C16—H16A	109.5
C4—C3—H3	120.4	C8—C16—H16B	109.5
C5—C4—C3	120.64 (14)	H16A—C16—H16B	109.5
C5—C4—H4	119.7	C8—C16—H16C	109.5
C3—C4—H4	119.7	H16A—C16—H16C	109.5
C4—C5—C6	120.51 (14)	H16B—C16—H16C	109.5
C4—C5—H5	119.7	C9—C17—H17A	109.5
C6—C5—H5	119.7	C9—C17—H17B	109.5
C5—C6—C1	118.31 (13)	H17A—C17—H17B	109.5
C5—C6—C7	123.16 (12)	C9—C17—H17C	109.5
C1—C6—C7	118.47 (11)	H17A—C17—H17C	109.5
N1—C7—N2	110.87 (11)	H17B—C17—H17C	109.5
N1—C7—C6	123.45 (11)	O1—C18—H18A	109.5
N2—C7—C6	125.62 (11)	O1—C18—H18B	109.5
C9—C8—N1	110.47 (12)	H18A—C18—H18B	109.5
C9—C8—C16	128.66 (14)	O1—C18—H18C	109.5
N1—C8—C16	120.84 (13)	H18A—C18—H18C	109.5
C8—C9—N2	105.57 (12)	H18B—C18—H18C	109.5
C8—C9—C17	131.20 (13)	O2—C19—H19A	109.5
N2—C9—C17	123.15 (12)	O2—C19—H19B	109.5
C15—C10—C11	122.36 (12)	H19A—C19—H19B	109.5
C15—C10—N2	118.84 (11)	O2—C19—H19C	109.5
C11—C10—N2	118.80 (11)	H19A—C19—H19C	109.5
C12—C11—C10	118.02 (11)	H19B—C19—H19C	109.5
C12—C11—H11	121.0	C7—N1—C8	106.17 (11)
C10—C11—H11	121.0	C7—N2—C9	106.91 (10)
O1—C12—C11	124.12 (12)	C7—N2—C10	127.24 (11)
O1—C12—C13	114.83 (12)	C9—N2—C10	124.65 (11)
C11—C12—C13	121.03 (11)	C12—O1—C18	117.10 (11)
C14—C13—C12	119.32 (12)	C14—O2—C19	118.21 (12)
C14—C13—H13	120.3
C6—C1—C2—C3	−0.2 (2)	C11—C10—C15—C14	1.80 (19)
C1—C2—C3—C4	0.8 (3)	N2—C10—C15—C14	−178.86 (11)
C2—C3—C4—C5	−0.7 (3)	O2—C14—C15—C10	177.80 (11)
C3—C4—C5—C6	0.0 (2)	C13—C14—C15—C10	−2.6 (2)
C4—C5—C6—C1	0.6 (2)	N2—C7—N1—C8	0.50 (13)
C4—C5—C6—C7	177.69 (13)	C6—C7—N1—C8	177.69 (11)
C2—C1—C6—C5	−0.5 (2)	C9—C8—N1—C7	−0.61 (15)
C2—C1—C6—C7	−177.72 (12)	C16—C8—N1—C7	177.60 (13)
C5—C6—C7—N1	−145.49 (13)	N1—C7—N2—C9	−0.22 (13)
C1—C6—C7—N1	31.57 (18)	C6—C7—N2—C9	−177.33 (11)
C5—C6—C7—N2	31.27 (19)	N1—C7—N2—C10	−168.08 (11)
C1—C6—C7—N2	−151.66 (12)	C6—C7—N2—C10	14.80 (19)
N1—C8—C9—N2	0.47 (15)	C8—C9—N2—C7	−0.16 (13)
C16—C8—C9—N2	−177.56 (14)	C17—C9—N2—C7	−177.29 (12)
N1—C8—C9—C17	177.28 (14)	C8—C9—N2—C10	168.10 (11)
C16—C8—C9—C17	−0.8 (3)	C17—C9—N2—C10	−9.03 (19)
C15—C10—C11—C12	0.70 (19)	C15—C10—N2—C7	50.18 (17)
N2—C10—C11—C12	−178.64 (11)	C11—C10—N2—C7	−130.45 (13)
C10—C11—C12—O1	179.18 (12)	C15—C10—N2—C9	−115.66 (14)
C10—C11—C12—C13	−2.44 (19)	C11—C10—N2—C9	63.70 (16)
O1—C12—C13—C14	−179.85 (12)	C11—C12—O1—C18	−13.3 (2)
C11—C12—C13—C14	1.62 (19)	C13—C12—O1—C18	168.19 (13)
C12—C13—C14—O2	−179.50 (12)	C13—C14—O2—C19	−2.4 (2)
C12—C13—C14—C15	1.0 (2)	C15—C14—O2—C19	177.17 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1i	0.93	2.62	3.516 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N1i	0.93	2.62	3.516 (2)	162

Symmetry code: (i) .