2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)-5-meth-oxy-phenol.

In the title quinazoline derivative, C(21)H(17)N(3)O(2), the benzimidazole unit makes dihedral angles of 8.29 (5) and 81.79 (5)° with the benzene rings of the quinazoline and meth-oxy-phenol units, respectively. The nitro-gen-containing six-membered ring adopts a half-chair conformation. In the crystal, the mol-ecules are linked through O-H⋯N hydrogen bonds into screw chains along the b axis; adjacent chains are further connected by N-H⋯O hydrogen bonds, thereby forming a two-dimensional network lying parallel to the bc plane. Weak C-H⋯π and π⋯π inter-actions with centroid-centroid distances of 3.5258 (8) and 3.7184 (7) Å are present and N⋯O [2.6816 (15) and 3.0519 (15) Å] short contacts also occur.

Related literature

For background to benzoheterocyclic derivatives and their applications, see: Arienzo et al. (2007 ▶); Chassaing et al. (2008 ▶); Galarcei et al. (2008 ▶); Kumar & Rajput (2009 ▶); Kung et al. (2009 ▶); Podunavac-Kuzmanovic & Cvetkovic (2010 ▶); Via et al. (2001 ▶); Xue et al. (2011 ▶); Zhang et al. (2009 ▶). For related structures, see: Eltayeb et al. (2007 ▶, 2009 ▶, 2011a ▶,b ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H17N3O2

M = 343.38

Monoclinic,

a = 9.5408 (1) Å

b = 15.6503 (2) Å

c = 11.7609 (1) Å

β = 110.408 (1)°

V = 1645.87 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.28 × 0.25 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.974, T max = 0.980

31713 measured reflections

6610 independent reflections

4637 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.139

S = 1.05

6610 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034027/hb6371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034027/hb6371Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034027/hb6371Isup3.cml

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

C21H17N3O2	F(000) = 720
Mr = 343.38	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6610 reflections
a = 9.5408 (1) Å	θ = 2.3–33.8°
b = 15.6503 (2) Å	µ = 0.09 mm−1
c = 11.7609 (1) Å	T = 100 K
β = 110.408 (1)°	Block, pale yellow
V = 1645.87 (3) Å3	0.28 × 0.25 × 0.22 mm
Z = 4

Bruker APEXII CCD diffractometer	6610 independent reflections
Radiation source: sealed tube	4637 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 33.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.974, Tmax = 0.980	k = −24→22
31713 measured reflections	l = −18→18

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.6883P] where P = (Fo2 + 2Fc2)/3
6610 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.14755 (11)	0.22525 (6)	0.27396 (8)	0.0225 (2)
O2	0.48793 (10)	0.20256 (6)	0.67860 (8)	0.01967 (19)
N1	0.09967 (11)	0.45602 (7)	0.26995 (9)	0.0155 (2)
N2	−0.06837 (12)	0.56241 (7)	0.21091 (10)	0.0195 (2)
N3	0.32315 (12)	0.45264 (7)	0.22680 (10)	0.0181 (2)
C1	−0.00334 (14)	0.44114 (8)	0.32723 (11)	0.0169 (2)
C2	−0.01453 (15)	0.37959 (9)	0.40964 (12)	0.0214 (3)
H2A	0.0559	0.3344	0.4361	0.026*
C3	−0.13327 (16)	0.38755 (9)	0.45104 (13)	0.0261 (3)
H3A	−0.1438	0.3471	0.5078	0.031*
C4	−0.23825 (16)	0.45360 (10)	0.41148 (14)	0.0276 (3)
H4A	−0.3193	0.4562	0.4407	0.033*
C5	−0.22662 (15)	0.51499 (9)	0.33108 (13)	0.0251 (3)
H5A	−0.2975	0.5600	0.3051	0.030*
C6	−0.10683 (14)	0.50852 (8)	0.28924 (11)	0.0185 (2)
C7	0.05266 (14)	0.52788 (8)	0.19987 (11)	0.0165 (2)
C8	0.13443 (14)	0.55651 (8)	0.12348 (11)	0.0170 (2)
C9	0.08353 (15)	0.62216 (8)	0.03824 (11)	0.0206 (3)
H9A	−0.0070	0.6510	0.0303	0.025*
C10	0.16415 (16)	0.64543 (9)	−0.03470 (11)	0.0230 (3)
H10A	0.1282	0.6894	−0.0935	0.028*
C11	0.29812 (16)	0.60404 (9)	−0.02133 (11)	0.0233 (3)
H11A	0.3534	0.6199	−0.0713	0.028*
C12	0.35181 (16)	0.53980 (9)	0.06425 (11)	0.0209 (3)
H12A	0.4444	0.5128	0.0737	0.025*
C13	0.26941 (14)	0.51475 (8)	0.13664 (11)	0.0171 (2)
C14	0.21403 (13)	0.39827 (8)	0.25378 (10)	0.0157 (2)
H14A	0.1659	0.3593	0.1836	0.019*
C15	0.29119 (13)	0.34584 (8)	0.36554 (10)	0.0148 (2)
C16	0.25404 (13)	0.25964 (8)	0.37158 (11)	0.0159 (2)
C17	0.32374 (13)	0.21322 (8)	0.47774 (10)	0.0162 (2)
H17A	0.2994	0.1547	0.4821	0.019*
C18	0.42921 (13)	0.25281 (8)	0.57752 (10)	0.0154 (2)
C19	0.46985 (14)	0.33780 (8)	0.57194 (11)	0.0171 (2)
H19A	0.5438	0.3643	0.6389	0.021*
C20	0.39884 (13)	0.38268 (8)	0.46523 (11)	0.0163 (2)
H20A	0.4251	0.4408	0.4605	0.020*
C21	0.57945 (16)	0.24524 (10)	0.78736 (12)	0.0258 (3)
H21A	0.6014	0.2060	0.8563	0.039*
H21B	0.5261	0.2953	0.8016	0.039*
H21C	0.6733	0.2635	0.7783	0.039*
H1N3	0.3958 (19)	0.4194 (12)	0.2166 (15)	0.028 (4)*
H1O1	0.126 (2)	0.1665 (15)	0.291 (2)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0248 (5)	0.0166 (5)	0.0191 (4)	−0.0058 (4)	−0.0014 (4)	0.0006 (3)
O2	0.0217 (4)	0.0185 (4)	0.0154 (4)	−0.0019 (4)	0.0021 (3)	0.0027 (3)
N1	0.0152 (5)	0.0139 (5)	0.0175 (4)	0.0018 (4)	0.0059 (4)	0.0019 (4)
N2	0.0190 (5)	0.0167 (5)	0.0214 (5)	0.0031 (4)	0.0054 (4)	0.0003 (4)
N3	0.0185 (5)	0.0166 (5)	0.0214 (5)	0.0033 (4)	0.0098 (4)	0.0042 (4)
C1	0.0155 (5)	0.0172 (6)	0.0180 (5)	−0.0007 (4)	0.0057 (4)	−0.0019 (4)
C2	0.0211 (6)	0.0196 (6)	0.0253 (6)	0.0019 (5)	0.0103 (5)	0.0025 (5)
C3	0.0277 (7)	0.0241 (7)	0.0316 (7)	−0.0024 (6)	0.0166 (6)	0.0014 (5)
C4	0.0239 (7)	0.0271 (7)	0.0378 (8)	−0.0020 (6)	0.0184 (6)	−0.0052 (6)
C5	0.0201 (6)	0.0220 (7)	0.0345 (7)	0.0032 (5)	0.0113 (5)	−0.0031 (5)
C6	0.0168 (6)	0.0164 (6)	0.0214 (5)	0.0010 (5)	0.0054 (4)	−0.0025 (4)
C7	0.0175 (5)	0.0130 (5)	0.0165 (5)	0.0007 (4)	0.0028 (4)	−0.0004 (4)
C8	0.0203 (6)	0.0133 (5)	0.0160 (5)	−0.0011 (4)	0.0048 (4)	−0.0005 (4)
C9	0.0243 (6)	0.0156 (6)	0.0185 (5)	−0.0002 (5)	0.0031 (5)	0.0011 (4)
C10	0.0311 (7)	0.0169 (6)	0.0169 (5)	−0.0034 (5)	0.0034 (5)	0.0021 (4)
C11	0.0313 (7)	0.0207 (6)	0.0181 (5)	−0.0069 (5)	0.0091 (5)	−0.0005 (5)
C12	0.0244 (6)	0.0194 (6)	0.0201 (6)	−0.0012 (5)	0.0094 (5)	−0.0002 (5)
C13	0.0215 (6)	0.0134 (5)	0.0160 (5)	−0.0015 (4)	0.0061 (4)	−0.0002 (4)
C14	0.0170 (5)	0.0134 (5)	0.0170 (5)	0.0017 (4)	0.0063 (4)	0.0006 (4)
C15	0.0150 (5)	0.0127 (5)	0.0173 (5)	0.0009 (4)	0.0064 (4)	0.0009 (4)
C16	0.0144 (5)	0.0154 (5)	0.0166 (5)	0.0001 (4)	0.0039 (4)	−0.0002 (4)
C17	0.0173 (5)	0.0126 (5)	0.0181 (5)	−0.0005 (4)	0.0056 (4)	0.0010 (4)
C18	0.0145 (5)	0.0162 (6)	0.0155 (5)	0.0014 (4)	0.0053 (4)	0.0013 (4)
C19	0.0169 (5)	0.0164 (6)	0.0173 (5)	−0.0027 (4)	0.0049 (4)	−0.0024 (4)
C20	0.0171 (5)	0.0124 (5)	0.0202 (5)	−0.0012 (4)	0.0077 (4)	−0.0003 (4)
C21	0.0268 (7)	0.0277 (7)	0.0165 (5)	−0.0066 (6)	−0.0005 (5)	0.0030 (5)

O1—C16	1.3516 (14)	C8—C13	1.4038 (18)
O1—H1O1	0.98 (2)	C9—C10	1.386 (2)
O2—C18	1.3716 (14)	C9—H9A	0.9500
O2—C21	1.4373 (15)	C10—C11	1.392 (2)
N1—C7	1.3739 (15)	C10—H10A	0.9500
N1—C1	1.3913 (16)	C11—C12	1.3880 (18)
N1—C14	1.4793 (15)	C11—H11A	0.9500
N2—C7	1.3217 (17)	C12—C13	1.4012 (18)
N2—C6	1.3894 (17)	C12—H12A	0.9500
N3—C13	1.3974 (16)	C14—C15	1.5060 (16)
N3—C14	1.4626 (16)	C14—H14A	1.0000
N3—H1N3	0.908 (18)	C15—C20	1.3863 (16)
C1—C2	1.3967 (18)	C15—C16	1.4030 (17)
C1—C6	1.4067 (18)	C16—C17	1.3964 (16)
C2—C3	1.3859 (19)	C17—C18	1.3964 (17)
C2—H2A	0.9500	C17—H17A	0.9500
C3—C4	1.401 (2)	C18—C19	1.3934 (17)
C3—H3A	0.9500	C19—C20	1.3909 (17)
C4—C5	1.379 (2)	C19—H19A	0.9500
C4—H4A	0.9500	C20—H20A	0.9500
C5—C6	1.3967 (19)	C21—H21A	0.9800
C5—H5A	0.9500	C21—H21B	0.9800
C7—C8	1.4509 (18)	C21—H21C	0.9800
C8—C9	1.3989 (17)
C16—O1—H1O1	110.2 (13)	C12—C11—C10	120.74 (13)
C18—O2—C21	116.28 (10)	C12—C11—H11A	119.6
C7—N1—C1	106.83 (10)	C10—C11—H11A	119.6
C7—N1—C14	121.61 (10)	C11—C12—C13	119.99 (13)
C1—N1—C14	129.58 (10)	C11—C12—H12A	120.0
C7—N2—C6	105.00 (10)	C13—C12—H12A	120.0
C13—N3—C14	117.95 (10)	N3—C13—C12	121.37 (12)
C13—N3—H1N3	113.2 (11)	N3—C13—C8	119.16 (11)
C14—N3—H1N3	109.2 (11)	C12—C13—C8	119.36 (11)
N1—C1—C2	133.57 (12)	N3—C14—N1	106.57 (10)
N1—C1—C6	104.88 (11)	N3—C14—C15	109.75 (10)
C2—C1—C6	121.49 (12)	N1—C14—C15	112.25 (9)
C3—C2—C1	116.84 (12)	N3—C14—H14A	109.4
C3—C2—H2A	121.6	N1—C14—H14A	109.4
C1—C2—H2A	121.6	C15—C14—H14A	109.4
C2—C3—C4	121.79 (13)	C20—C15—C16	118.87 (11)
C2—C3—H3A	119.1	C20—C15—C14	120.27 (11)
C4—C3—H3A	119.1	C16—C15—C14	120.85 (10)
C5—C4—C3	121.50 (13)	O1—C16—C17	122.33 (11)
C5—C4—H4A	119.3	O1—C16—C15	117.93 (11)
C3—C4—H4A	119.3	C17—C16—C15	119.71 (11)
C4—C5—C6	117.53 (13)	C16—C17—C18	119.96 (11)
C4—C5—H5A	121.2	C16—C17—H17A	120.0
C6—C5—H5A	121.2	C18—C17—H17A	120.0
N2—C6—C5	128.86 (12)	O2—C18—C19	123.50 (11)
N2—C6—C1	110.31 (11)	O2—C18—C17	115.52 (11)
C5—C6—C1	120.83 (12)	C19—C18—C17	120.98 (11)
N2—C7—N1	112.91 (11)	C20—C19—C18	117.94 (11)
N2—C7—C8	127.69 (11)	C20—C19—H19A	121.0
N1—C7—C8	119.39 (11)	C18—C19—H19A	121.0
C9—C8—C13	119.79 (12)	C15—C20—C19	122.49 (11)
C9—C8—C7	122.91 (12)	C15—C20—H20A	118.8
C13—C8—C7	117.30 (11)	C19—C20—H20A	118.8
C10—C9—C8	120.52 (13)	O2—C21—H21A	109.5
C10—C9—H9A	119.7	O2—C21—H21B	109.5
C8—C9—H9A	119.7	H21A—C21—H21B	109.5
C9—C10—C11	119.58 (12)	O2—C21—H21C	109.5
C9—C10—H10A	120.2	H21A—C21—H21C	109.5
C11—C10—H10A	120.2	H21B—C21—H21C	109.5
C7—N1—C1—C2	−178.82 (14)	C14—N3—C13—C8	35.42 (16)
C14—N1—C1—C2	17.3 (2)	C11—C12—C13—N3	−177.47 (12)
C7—N1—C1—C6	−1.59 (13)	C11—C12—C13—C8	−1.42 (19)
C14—N1—C1—C6	−165.47 (11)	C9—C8—C13—N3	176.42 (11)
N1—C1—C2—C3	177.56 (13)	C7—C8—C13—N3	−4.28 (17)
C6—C1—C2—C3	0.70 (19)	C9—C8—C13—C12	0.28 (18)
C1—C2—C3—C4	0.6 (2)	C7—C8—C13—C12	179.57 (11)
C2—C3—C4—C5	−1.3 (2)	C13—N3—C14—N1	−49.22 (13)
C3—C4—C5—C6	0.7 (2)	C13—N3—C14—C15	−171.00 (10)
C7—N2—C6—C5	−179.60 (13)	C7—N1—C14—N3	37.49 (14)
C7—N2—C6—C1	1.18 (14)	C1—N1—C14—N3	−160.71 (11)
C4—C5—C6—N2	−178.49 (13)	C7—N1—C14—C15	157.67 (11)
C4—C5—C6—C1	0.6 (2)	C1—N1—C14—C15	−40.53 (16)
N1—C1—C6—N2	0.28 (14)	N3—C14—C15—C20	42.18 (15)
C2—C1—C6—N2	177.93 (11)	N1—C14—C15—C20	−76.13 (14)
N1—C1—C6—C5	−179.00 (11)	N3—C14—C15—C16	−138.89 (12)
C2—C1—C6—C5	−1.36 (19)	N1—C14—C15—C16	102.80 (13)
C6—N2—C7—N1	−2.29 (14)	C20—C15—C16—O1	179.23 (11)
C6—N2—C7—C8	176.73 (12)	C14—C15—C16—O1	0.28 (17)
C1—N1—C7—N2	2.53 (14)	C20—C15—C16—C17	1.05 (18)
C14—N1—C7—N2	167.97 (10)	C14—C15—C16—C17	−177.90 (11)
C1—N1—C7—C8	−176.58 (10)	O1—C16—C17—C18	−177.68 (11)
C14—N1—C7—C8	−11.14 (17)	C15—C16—C17—C18	0.42 (18)
N2—C7—C8—C9	−7.4 (2)	C21—O2—C18—C19	8.93 (17)
N1—C7—C8—C9	171.60 (11)	C21—O2—C18—C17	−171.12 (11)
N2—C7—C8—C13	173.36 (12)	C16—C17—C18—O2	178.11 (11)
N1—C7—C8—C13	−7.68 (17)	C16—C17—C18—C19	−1.94 (18)
C13—C8—C9—C10	1.00 (19)	O2—C18—C19—C20	−178.13 (11)
C7—C8—C9—C10	−178.26 (12)	C17—C18—C19—C20	1.92 (18)
C8—C9—C10—C11	−1.12 (19)	C16—C15—C20—C19	−1.06 (18)
C9—C10—C11—C12	0.0 (2)	C14—C15—C20—C19	177.89 (11)
C10—C11—C12—C13	1.3 (2)	C18—C19—C20—C15	−0.41 (18)
C14—N3—C13—C12	−148.52 (12)

Cg4 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2i	0.907 (19)	2.211 (19)	3.0519 (15)	153.8 (17)
O1—H1O1···N2ii	0.98 (2)	1.72 (2)	2.6816 (15)	168 (2)
C2—H2A···Cg4	0.95	2.85	3.6277 (16)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O2i	0.907 (19)	2.211 (19)	3.0519 (15)	153.8 (17)
O1—H1O1⋯N2ii	0.98 (2)	1.72 (2)	2.6816 (15)	168 (2)
C2—H2A⋯Cg4	0.95	2.85	3.6277 (16)	140

Symmetry codes: (i) ; (ii) .