1-(3,5-Di­meth­oxy­phen­yl)-4,5-dimethyl-2-phenyl-1H-imidazole

Divya, G.; Saravanan, K.; Santhiya, S.; Chandralekha, K.; Lakshmi, S.

doi:10.1107/S1600536813023684

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1502

doi:10.1107/S1600536813023684

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1-(3,5-Dimethoxyphenyl)-4,5-dimethyl-2-phenyl-1H-imidazole

G. Divya,^a K. Saravanan,^b S. Santhiya,^a K. Chandralekha ^a and S. Lakshmi ^a ^*

^aResearch Department of Physics, SDNB Vaishnav College for Women, Chennai 600 044, India, and ^bDepartment of Chemistry, Easwari Engineering College, Chennai, India
^*Correspondence e-mail: crystallographyvaishnav2012@gmail.com

(Received 5 August 2013; accepted 22 August 2013; online 4 September 2013)

In the title molecule, C₁₉H₂₀N₂O₂, the imidazole ring makes dihedral angles of 57.29 (5) and 31.54 (5)° with the attached dimethoxyphenyl residue and the phenyl ring, respectively. The dihedral angle between the dimethoxyphenyl and phenyl rings is 61.15 (5)°. In the crystal, pairs of C—H⋯N hydrogen bonds connect the molecules 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_r = 308.37
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.126
S = 1.03
3780 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) -x, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813023684/bt6926sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813023684/bt6926Isup3.cml

checkCIF report

Comment top

The title compound was synthesized in an attempt to develop highly sensitive chemosensors for transition metal ions. Similar compounds have the potential to be used as a ligand for synthesizing Ir³⁺ complexes (Saravanan et al., 2011; Gayathri et al., 2010). Imidazole derivatives are found to have diverse activities like anti-inflammatory and antimicrobial activity (Zala et al., 2012).

In the title molecule (Fig.1), the imidazole ring makes dihedral angles of 57.29 (5)° and 31.54 (5)° with the attached dimethoxyphenyl residue and the phenyl ring, respectively. The dihedral angle between the benzene and phenyl rings is 61.15 (5)°. Two inversion related molecules (Table 1) connected by C–H···N hydrogen bonds form a centrosymmetric dimer (Fig. 2).

Related literature top

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 top

To pure biacetyl (1.48 g, 15 mmol) in ethanol (10 ml), 3,5 dimethoxyaniline (2.30 g,15 mmol), ammonium acetate(7.0 g, 15 mmol) and benzaldehyde (1.5 g 15 mmol) were added for a period of about one hour by maintaining the temperature at 333 K. The reaction mixture was refluxed for five days and extracted with dichloromethane. The solid which separated was purified by column chromatography using hexane:ethyl acetate as the eluent. Yield: 2.1 g (45%).

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of the title compound,with displacement ellipsoids drawn at the 50% probability level·H atoms are shown as small sphere of arbitrary radius.
	Fig. 2. The packing of the title compound,viewed down the c axis; dashed lines indicates hydrogen bonds.

1-(3,5-Dimethoxyphenyl)-4,5-dimethyl-2-phenyl-1H-imidazole top

Crystal data top

C₁₉H₂₀N₂O₂	Z = 2
M_r = 308.37	F(000) = 328
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0645P)² + 0.1449P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3780 reflections	Δρ_max = 0.22 e Å⁻³
213 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₂₀N₂O₂	γ = 74.576 (5)°
M_r = 308.37	V = 822.9 (7) Å³
Triclinic, P1	Z = 2
a = 8.363 (5) Å	Mo Kα radiation
b = 10.267 (5) Å	µ = 0.08 mm⁻¹
c = 10.481 (5) Å	T = 295 K
α = 75.043 (5)°	0.35 × 0.25 × 0.20 mm
β = 75.789 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3780 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2991 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.984	R_int = 0.028
16534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
3780 reflections	Δρ_min = −0.17 e Å⁻³
213 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. 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1ⁱ	0.930	2.617	3.516 (2)	162

Symmetry code: (i) −x, −y+1, −z+1.

References

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