2-(3,4,5-Trimethoxy-phen-yl)-1H-benzimidazole.

In the title compound, C(16)H(16)N(2)O(3), the dihedral angle between the mean planes of the aromatic ring systems is 30.90 (15)°. In the crystal structure, the mol-ecules form [010] chains by way of N-H⋯N hydrogen bonds.

Related literature

For a related structure, see: Rashid et al. (2007 ▶). For background, see: Gupta et al. (2004 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Orthorhombic,

a = 8.2270 (16) Å

b = 9.5750 (19) Å

c = 37.375 (7) Å

V = 2944.2 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 (2) K

0.25 × 0.20 × 0.18 mm

Data collection

Enraf-Nonius CAD-4 diffractometer

Absorption correction: none

5421 measured reflections

2733 independent reflections

960 reflections with I > 2σ(I)

R int = 0.085

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.143

S = 0.94

2733 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014189/bt2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014189/bt2706Isup2.hkl

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

C16H16N2O3	F000 = 1200
Mr = 284.31	Dx = 1.283 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 8.2270 (16) Å	θ = 4–14º
b = 9.5750 (19) Å	µ = 0.09 mm−1
c = 37.375 (7) Å	T = 295 (2) K
V = 2944.2 (10) Å3	Block, colourless
Z = 8	0.25 × 0.20 × 0.18 mm

Enraf-Nonius CAD-4 diffractometer	Rint = 0.085
Radiation source: fine-focus sealed tube	θmax = 25.5º
Monochromator: graphite	θmin = 1.1º
T = 295(2) K	h = −9→0
ω scans	k = −11→0
Absorption correction: none	l = −44→44
5421 measured reflections	3 standard reflections
2733 independent reflections	every 100 reflections
960 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0483P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
2733 reflections	Δρmax = 0.21 e Å−3
190 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	1.2012 (3)	0.2286 (3)	0.03723 (7)	0.0646 (9)
O2	0.9428 (3)	0.3940 (3)	0.03507 (7)	0.0591 (9)
O3	1.2638 (3)	0.0641 (3)	0.09566 (8)	0.0609 (8)
N1	0.7160 (3)	0.0683 (3)	0.16552 (8)	0.0387 (8)
H1A	0.7705	−0.0074	0.1623	0.046*
N2	0.6374 (3)	0.2921 (3)	0.15868 (8)	0.0406 (8)
C1	1.3578 (5)	0.2888 (6)	0.04310 (12)	0.0800 (15)
H1B	1.4197	0.2852	0.0213	0.120*
H1C	1.4134	0.2375	0.0615	0.120*
H1D	1.3455	0.3843	0.0505	0.120*
C2	0.8079 (6)	0.4863 (5)	0.03285 (12)	0.0772 (15)
H2B	0.8153	0.5402	0.0112	0.116*
H2C	0.8083	0.5479	0.0531	0.116*
H2D	0.7089	0.4332	0.0327	0.116*
C3	1.3004 (5)	−0.0119 (5)	0.12749 (11)	0.0772 (15)
H3A	1.4032	−0.0581	0.1248	0.116*
H3B	1.2171	−0.0801	0.1317	0.116*
H3C	1.3055	0.0513	0.1474	0.116*
C4	1.1200 (5)	0.1366 (4)	0.09509 (12)	0.0446 (11)
C5	1.0041 (5)	0.1274 (4)	0.12166 (11)	0.0429 (10)
H5A	1.0203	0.0672	0.1409	0.052*
C6	0.8635 (4)	0.2074 (4)	0.11992 (10)	0.0368 (9)
C7	0.8382 (4)	0.2994 (4)	0.09110 (10)	0.0397 (10)
H7A	0.7448	0.3540	0.0901	0.048*
C8	0.9539 (5)	0.3074 (4)	0.06435 (11)	0.0422 (10)
C9	1.0951 (4)	0.2256 (4)	0.06576 (10)	0.0446 (11)
C10	0.7391 (5)	0.1932 (4)	0.14767 (9)	0.0374 (9)
C11	0.5910 (4)	0.0866 (4)	0.18929 (10)	0.0338 (9)
C12	0.5161 (5)	−0.0025 (4)	0.21332 (10)	0.0453 (11)
H12A	0.5493	−0.0948	0.2158	0.054*
C13	0.3906 (5)	0.0513 (4)	0.23340 (11)	0.0532 (11)
H13A	0.3387	−0.0055	0.2500	0.064*
C14	0.3390 (5)	0.1916 (5)	0.22919 (12)	0.0541 (11)
H14A	0.2522	0.2242	0.2428	0.065*
C15	0.4139 (4)	0.2808 (4)	0.20549 (10)	0.0508 (11)
H15A	0.3801	0.3730	0.2031	0.061*
C16	0.5427 (4)	0.2280 (4)	0.18510 (10)	0.0359 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0561 (19)	0.085 (2)	0.0526 (18)	−0.0022 (18)	0.0156 (16)	−0.0106 (18)
O2	0.061 (2)	0.068 (2)	0.048 (2)	0.0042 (18)	0.0086 (16)	0.0139 (18)
O3	0.0506 (18)	0.0599 (19)	0.072 (2)	0.0141 (17)	0.0108 (18)	0.0009 (18)
N1	0.0409 (19)	0.0233 (17)	0.052 (2)	0.0028 (16)	0.0007 (18)	0.0074 (17)
N2	0.044 (2)	0.0254 (17)	0.052 (2)	−0.0002 (18)	0.0067 (17)	−0.0009 (19)
C1	0.059 (3)	0.100 (4)	0.081 (3)	−0.011 (3)	0.019 (3)	−0.009 (3)
C2	0.085 (4)	0.074 (3)	0.073 (4)	0.019 (3)	0.007 (3)	0.029 (3)
C3	0.067 (3)	0.096 (4)	0.069 (3)	0.034 (3)	−0.013 (3)	−0.004 (3)
C4	0.034 (2)	0.042 (3)	0.057 (3)	0.004 (2)	0.004 (2)	−0.008 (2)
C5	0.042 (2)	0.031 (2)	0.056 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C6	0.038 (2)	0.030 (2)	0.042 (2)	−0.002 (2)	0.005 (2)	−0.001 (2)
C7	0.036 (2)	0.032 (2)	0.051 (3)	0.000 (2)	0.002 (2)	−0.003 (2)
C8	0.045 (3)	0.042 (2)	0.040 (2)	−0.003 (2)	−0.001 (2)	−0.003 (2)
C9	0.041 (3)	0.053 (3)	0.040 (2)	−0.006 (2)	0.007 (2)	−0.004 (2)
C10	0.038 (2)	0.027 (2)	0.047 (2)	−0.003 (2)	−0.006 (2)	0.003 (2)
C11	0.033 (2)	0.030 (2)	0.038 (2)	−0.0061 (18)	0.005 (2)	−0.003 (2)
C12	0.047 (3)	0.034 (2)	0.054 (3)	−0.007 (2)	−0.002 (2)	0.006 (2)
C13	0.054 (3)	0.053 (3)	0.053 (3)	−0.010 (2)	0.005 (2)	0.010 (3)
C14	0.050 (3)	0.051 (3)	0.062 (3)	−0.002 (3)	0.017 (2)	−0.005 (3)
C15	0.052 (3)	0.037 (3)	0.064 (3)	0.008 (2)	0.012 (2)	−0.004 (2)
C16	0.040 (2)	0.023 (2)	0.044 (2)	−0.0011 (19)	0.001 (2)	−0.001 (2)

C9—O1	1.379 (4)	C4—C5	1.379 (5)
C1—O1	1.428 (5)	C4—C9	1.403 (5)
C8—O2	1.377 (4)	C5—C6	1.389 (5)
C2—O2	1.422 (4)	C5—H5A	0.9300
C4—O3	1.372 (4)	C6—C7	1.407 (5)
C3—O3	1.427 (4)	C6—C10	1.464 (5)
N1—C11	1.371 (4)	C7—C8	1.383 (5)
N1—C10	1.383 (4)	C7—H7A	0.9300
N1—H1A	0.8600	C8—C9	1.401 (5)
N2—C10	1.329 (4)	C11—C12	1.383 (5)
N2—C16	1.400 (4)	C11—C16	1.419 (5)
C1—H1B	0.9600	C12—C13	1.376 (5)
C1—H1C	0.9600	C12—H12A	0.9300
C1—H1D	0.9600	C13—C14	1.418 (5)
C2—H2B	0.9600	C13—H13A	0.9300
C2—H2C	0.9600	C14—C15	1.376 (5)
C2—H2D	0.9600	C14—H14A	0.9300
C3—H3A	0.9600	C15—C16	1.400 (5)
C3—H3B	0.9600	C15—H15A	0.9300
C3—H3C	0.9600
C9—O1—C1	117.4 (3)	C5—C6—C10	119.9 (4)
C8—O2—C2	118.2 (3)	C7—C6—C10	119.8 (3)
C4—O3—C3	116.9 (3)	C8—C7—C6	119.1 (4)
C11—N1—C10	107.7 (3)	C8—C7—H7A	120.5
C11—N1—H1A	126.1	C6—C7—H7A	120.5
C10—N1—H1A	126.1	O2—C8—C7	124.2 (4)
C10—N2—C16	104.8 (3)	O2—C8—C9	114.9 (4)
O1—C1—H1B	109.5	C7—C8—C9	120.8 (4)
O1—C1—H1C	109.5	O1—C9—C8	118.9 (4)
H1B—C1—H1C	109.5	O1—C9—C4	121.6 (4)
O1—C1—H1D	109.5	C8—C9—C4	119.3 (4)
H1B—C1—H1D	109.5	N2—C10—N1	112.4 (3)
H1C—C1—H1D	109.5	N2—C10—C6	126.4 (3)
O2—C2—H2B	109.5	N1—C10—C6	121.2 (3)
O2—C2—H2C	109.5	N1—C11—C12	132.5 (4)
H2B—C2—H2C	109.5	N1—C11—C16	105.1 (3)
O2—C2—H2D	109.5	C12—C11—C16	122.4 (4)
H2B—C2—H2D	109.5	C13—C12—C11	117.2 (4)
H2C—C2—H2D	109.5	C13—C12—H12A	121.4
O3—C3—H3A	109.5	C11—C12—H12A	121.4
O3—C3—H3B	109.5	C12—C13—C14	121.3 (4)
H3A—C3—H3B	109.5	C12—C13—H13A	119.4
O3—C3—H3C	109.5	C14—C13—H13A	119.4
H3A—C3—H3C	109.5	C15—C14—C13	121.7 (4)
H3B—C3—H3C	109.5	C15—C14—H14A	119.2
O3—C4—C5	123.5 (4)	C13—C14—H14A	119.2
O3—C4—C9	116.4 (4)	C14—C15—C16	117.7 (4)
C5—C4—C9	120.0 (4)	C14—C15—H15A	121.1
C4—C5—C6	120.4 (4)	C16—C15—H15A	121.1
C4—C5—H5A	119.8	N2—C16—C15	130.3 (3)
C6—C5—H5A	119.8	N2—C16—C11	109.9 (3)
C5—C6—C7	120.3 (3)	C15—C16—C11	119.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.07	2.918 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.07	2.918 (4)	169

Symmetry code: (i) .