6-Meth-oxy-2-methyl-1-m-tolyl-1H-benzimidazole hemihydrate.

The title compound, C(16)H(16)N(2)O·0.5H(2)O, is a substituted 1-phenyl-benzimidazole, which belongs to the class of ATP-site inhibitors of the platelet-derived growth-factor receptor. In the crystal, the components are linked by an O-H⋯N hydrogen bond.

Related literature

For related structures, see: Zhong (2004 ▶). For medicinal background, see: Palmer (1998 ▶).

Experimental

Crystal data

C16H16N2O·0.5H2O

M = 261.32

Orthorhombic,

a = 16.0752 (16) Å

b = 13.9140 (14) Å

c = 12.6450 (13) Å

V = 2828.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.983

13133 measured reflections

2720 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.155

S = 1.03

2720 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031060/aa2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031060/aa2011Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031060/aa2011Isup3.cml

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

C16H16N2O·0.5H2O	F(000) = 1112
Mr = 261.32	Dx = 1.227 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2720 reflections
a = 16.0752 (16) Å	θ = 2.4–28.0°
b = 13.9140 (14) Å	µ = 0.08 mm−1
c = 12.6450 (13) Å	T = 293 K
V = 2828.3 (5) Å3	Plate-like, colourless
Z = 8	0.25 × 0.23 × 0.21 mm

Bruker APEX CCD diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→19
Tmin = 0.980, Tmax = 0.983	k = −17→17
13133 measured reflections	l = −15→14

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)] = 0.081	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0196P)2 + 3.0292P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2720 reflections	Δρmax = 0.69 e Å−3
178 parameters	Δρmin = −0.20 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: 0.0037 (5)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.6204 (2)	0.6782 (2)	0.2566 (2)	0.0725 (8)
H1A	0.5851	0.6253	0.2539	0.087*
C2	0.6771 (2)	0.6930 (3)	0.1781 (3)	0.0851 (10)
H2A	0.6809	0.6497	0.1223	0.102*
C3	0.7285 (2)	0.7711 (3)	0.1814 (3)	0.0863 (11)
H3A	0.7671	0.7800	0.1274	0.104*
C4	0.72472 (19)	0.8370 (2)	0.2623 (3)	0.0789 (10)
C5	0.66713 (18)	0.8218 (2)	0.3437 (3)	0.0699 (8)
H5A	0.6636	0.8650	0.3996	0.084*
C6	0.61540 (17)	0.7422 (2)	0.3404 (2)	0.0624 (7)
C8	0.5560 (2)	0.6505 (2)	0.4939 (2)	0.0681 (8)
C9	0.6135 (2)	0.5667 (2)	0.4845 (3)	0.0848 (10)
H9A	0.6020	0.5215	0.5401	0.127*
H9B	0.6700	0.5884	0.4903	0.127*
H9C	0.6055	0.5361	0.4172	0.127*
C10	0.4610 (2)	0.7482 (2)	0.5473 (2)	0.0681 (8)
C11	0.3959 (2)	0.7953 (3)	0.5984 (3)	0.0819 (10)
H11A	0.3717	0.7687	0.6585	0.098*
C12	0.3683 (2)	0.8807 (3)	0.5596 (3)	0.0756 (9)
H12A	0.3245	0.9120	0.5932	0.091*
C13	0.40456 (18)	0.9223 (2)	0.4699 (2)	0.0677 (8)
C14	0.46999 (17)	0.8783 (2)	0.4176 (2)	0.0611 (7)
H14A	0.4946	0.9056	0.3583	0.073*
C15	0.49675 (18)	0.7910 (2)	0.4588 (2)	0.0592 (7)
C16	0.4029 (2)	1.0538 (3)	0.3480 (3)	0.0863 (10)
H16A	0.3731	1.1123	0.3341	0.129*
H16B	0.3979	1.0116	0.2883	0.129*
H16C	0.4605	1.0683	0.3601	0.129*
N1	0.55804 (15)	0.72736 (17)	0.42521 (18)	0.0628 (6)
N2	0.49971 (19)	0.66035 (18)	0.5677 (2)	0.0764 (7)
O1	0.36911 (13)	1.00859 (17)	0.43877 (19)	0.0811 (7)
O1W	0.5000	0.5327 (2)	0.7500	0.0961 (11)
H1W	0.4912	0.5668	0.6953	0.144*
C7	0.7786 (3)	0.9187 (3)	0.2623 (4)	0.1196 (16)
H7A	0.8138	0.9166	0.2011	0.179*
H7B	0.8123	0.9180	0.3250	0.179*
H7C	0.7459	0.9764	0.2609	0.179*

	U11	U22	U33	U12	U13	U23
C1	0.077 (2)	0.076 (2)	0.0645 (18)	0.0169 (17)	0.0040 (16)	0.0042 (16)
C2	0.092 (2)	0.093 (3)	0.070 (2)	0.029 (2)	0.0057 (19)	0.0060 (19)
C3	0.081 (2)	0.104 (3)	0.074 (2)	0.038 (2)	0.0189 (18)	0.019 (2)
C4	0.0568 (18)	0.074 (2)	0.106 (3)	0.0035 (16)	0.0035 (18)	0.033 (2)
C5	0.0636 (18)	0.0701 (19)	0.076 (2)	0.0092 (16)	0.0030 (15)	0.0106 (16)
C6	0.0602 (17)	0.0685 (18)	0.0584 (16)	0.0054 (15)	0.0027 (13)	0.0111 (14)
C8	0.083 (2)	0.0562 (17)	0.0649 (18)	−0.0107 (16)	0.0003 (16)	0.0009 (14)
C9	0.110 (3)	0.066 (2)	0.079 (2)	0.0055 (19)	−0.004 (2)	0.0036 (17)
C10	0.077 (2)	0.0635 (18)	0.0634 (17)	−0.0187 (16)	0.0101 (15)	−0.0055 (14)
C11	0.083 (2)	0.089 (2)	0.074 (2)	−0.025 (2)	0.0264 (18)	−0.0117 (18)
C12	0.0671 (19)	0.079 (2)	0.081 (2)	−0.0068 (17)	0.0137 (17)	−0.0201 (18)
C13	0.0566 (17)	0.075 (2)	0.0714 (19)	−0.0066 (15)	−0.0019 (15)	−0.0158 (16)
C14	0.0597 (16)	0.0658 (17)	0.0579 (16)	−0.0049 (14)	0.0025 (13)	−0.0022 (14)
C15	0.0563 (15)	0.0632 (17)	0.0582 (15)	−0.0087 (14)	0.0045 (13)	−0.0069 (13)
C16	0.090 (2)	0.081 (2)	0.088 (2)	0.011 (2)	−0.005 (2)	0.0008 (19)
N1	0.0676 (15)	0.0610 (14)	0.0599 (13)	−0.0022 (12)	0.0055 (12)	0.0042 (11)
N2	0.0991 (19)	0.0625 (15)	0.0677 (16)	−0.0165 (15)	0.0114 (15)	0.0024 (13)
O1	0.0725 (13)	0.0838 (15)	0.0870 (16)	0.0143 (12)	−0.0013 (12)	−0.0094 (13)
O1W	0.144 (3)	0.0619 (19)	0.082 (2)	0.000	0.002 (2)	0.000
C7	0.100 (3)	0.097 (3)	0.163 (4)	−0.008 (2)	0.008 (3)	0.013 (3)

C1—C2	1.363 (5)	C10—C11	1.394 (4)
C1—C6	1.387 (4)	C10—N2	1.395 (4)
C1—H1A	0.9300	C11—C12	1.359 (5)
C2—C3	1.366 (5)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.401 (4)
C3—C4	1.375 (5)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.385 (4)
C4—C5	1.400 (4)	C13—O1	1.386 (4)
C4—C7	1.429 (5)	C14—C15	1.389 (4)
C5—C6	1.385 (4)	C14—H14A	0.9300
C5—H5A	0.9300	C15—N1	1.391 (4)
C6—N1	1.429 (3)	C16—O1	1.417 (4)
C8—N2	1.307 (4)	C16—H16A	0.9600
C8—N1	1.378 (4)	C16—H16B	0.9600
C8—C9	1.492 (4)	C16—H16C	0.9600
C9—H9A	0.9600	O1W—H1W	0.8500
C9—H9B	0.9600	C7—H7A	0.9600
C9—H9C	0.9600	C7—H7B	0.9600
C10—C15	1.392 (4)	C7—H7C	0.9600
C2—C1—C6	119.9 (3)	C12—C11—H11A	120.4
C2—C1—H1A	120.1	C10—C11—H11A	120.4
C6—C1—H1A	120.1	C11—C12—C13	121.2 (3)
C1—C2—C3	120.2 (4)	C11—C12—H12A	119.4
C1—C2—H2A	119.9	C13—C12—H12A	119.4
C3—C2—H2A	119.9	C14—C13—O1	124.1 (3)
C2—C3—C4	121.7 (3)	C14—C13—C12	121.3 (3)
C2—C3—H3A	119.1	O1—C13—C12	114.7 (3)
C4—C3—H3A	119.1	C13—C14—C15	116.3 (3)
C3—C4—C5	118.4 (3)	C13—C14—H14A	121.9
C3—C4—C7	120.2 (4)	C15—C14—H14A	121.9
C5—C4—C7	121.4 (4)	C14—C15—N1	131.4 (3)
C6—C5—C4	119.7 (3)	C14—C15—C10	123.2 (3)
C6—C5—H5A	120.1	N1—C15—C10	105.4 (3)
C4—C5—H5A	120.1	O1—C16—H16A	109.5
C5—C6—C1	120.1 (3)	O1—C16—H16B	109.5
C5—C6—N1	118.8 (3)	H16A—C16—H16B	109.5
C1—C6—N1	121.2 (3)	O1—C16—H16C	109.5
N2—C8—N1	112.6 (3)	H16A—C16—H16C	109.5
N2—C8—C9	124.6 (3)	H16B—C16—H16C	109.5
N1—C8—C9	122.8 (3)	C8—N1—C15	106.6 (2)
C8—C9—H9A	109.5	C8—N1—C6	126.9 (3)
C8—C9—H9B	109.5	C15—N1—C6	126.4 (2)
H9A—C9—H9B	109.5	C8—N2—C10	105.7 (3)
C8—C9—H9C	109.5	C13—O1—C16	117.2 (2)
H9A—C9—H9C	109.5	C4—C7—H7A	109.5
H9B—C9—H9C	109.5	C4—C7—H7B	109.5
C15—C10—C11	118.8 (3)	H7A—C7—H7B	109.5
C15—C10—N2	109.8 (3)	C4—C7—H7C	109.5
C11—C10—N2	131.4 (3)	H7A—C7—H7C	109.5
C12—C11—C10	119.2 (3)	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N2	0.85	2.08	2.911 (3)	166.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N2	0.85	2.08	2.911 (3)	166