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

In the title compound, C(22)H(19)N(3)O(2), the phenol ring forms dihedral angles of 88.93 (10) and 87.95 (12)° with the benzimidazole system and the quinazoline benzene ring, respectively. In the crystal, mol-ecules are linked via O-H⋯N hydrogen bonds into infinite chains along [100]. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring.

Related literature

For a related structure, references to our previous structural studies of similar compounds and background references to benzimidazoles, see: Eltayeb et al. (2011 ▶).

Experimental

Crystal data

C22H19N3O2

M = 357.40

Triclinic,

a = 8.6935 (3) Å

b = 10.9167 (3) Å

c = 11.3401 (5) Å

α = 107.193 (2)°

β = 108.923 (2)°

γ = 104.723 (2)°

V = 896.66 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.25 × 0.2 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.614, T max = 0.746

7367 measured reflections

3505 independent reflections

2804 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.164

S = 1.00

3505 reflections

250 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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) I, global. DOI: 10.1107/S1600536811034714/hb6367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034714/hb6367Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034714/hb6367Isup3.cml

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

C22H19N3O2	Z = 2
Mr = 357.40	F(000) = 376
Triclinic, P1	Dx = 1.324 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6935 (3) Å	Cell parameters from 2997 reflections
b = 10.9167 (3) Å	θ = 2.6–28.3°
c = 11.3401 (5) Å	µ = 0.09 mm−1
α = 107.193 (2)°	T = 296 K
β = 108.923 (2)°	Block, yellow
γ = 104.723 (2)°	0.25 × 0.2 × 0.17 mm
V = 896.66 (6) Å3

Bruker SMART APEXII CCD diffractometer	3505 independent reflections
Radiation source: fine-focus sealed tube	2804 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.614, Tmax = 0.746	k = −13→13
7367 measured reflections	l = −13→13

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) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0842P)2 + 1.0545P] where P = (Fo2 + 2Fc2)/3
3505 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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
O2	0.2462 (2)	0.30314 (16)	0.30490 (16)	0.0186 (4)
O1	0.3194 (2)	0.36858 (17)	0.10937 (16)	0.0198 (4)
H1O1	0.2499	0.3974	0.1312	0.030*
N2	0.5360 (3)	0.3168 (2)	−0.0210 (2)	0.0212 (4)
N3	0.8203 (3)	0.4820 (2)	0.1277 (2)	0.0199 (4)
C22	0.0082 (3)	0.1800 (3)	0.3379 (3)	0.0300 (6)
H22A	−0.0427	0.2463	0.3258	0.045*
H22B	−0.0237	0.1461	0.3992	0.045*
H22C	−0.0350	0.1037	0.2510	0.045*
C21	0.2056 (3)	0.2487 (2)	0.3970 (2)	0.0207 (5)
H21A	0.2514	0.3232	0.4869	0.025*
H21B	0.2584	0.1816	0.4059	0.025*
C17	0.4186 (3)	0.3471 (2)	0.3259 (2)	0.0159 (5)
C16	0.4501 (3)	0.3791 (2)	0.2227 (2)	0.0156 (5)
C15	0.6199 (3)	0.4154 (2)	0.2305 (2)	0.0158 (5)
C14	0.6409 (3)	0.4416 (2)	0.1107 (2)	0.0177 (5)
H14	0.6012	0.5163	0.1025	0.021*
C13	0.6001 (3)	0.2101 (2)	−0.0438 (2)	0.0196 (5)
C8	0.7844 (3)	0.2458 (2)	0.0104 (2)	0.0210 (5)
C9	0.8501 (3)	0.1412 (3)	−0.0197 (3)	0.0235 (5)
H9	0.9712	0.1637	0.0156	0.028*
C10	0.7343 (3)	0.0051 (2)	−0.1018 (3)	0.0264 (6)
H10	0.7770	−0.0647	−0.1212	0.032*
C18	0.5574 (3)	0.3556 (2)	0.4365 (2)	0.0181 (5)
H18	0.5371	0.3364	0.5060	0.022*
C19	0.7260 (3)	0.3924 (2)	0.4435 (2)	0.0193 (5)
H19	0.8183	0.3978	0.5177	0.023*
C20	0.7578 (3)	0.4213 (2)	0.3406 (2)	0.0184 (5)
H20	0.8707	0.4444	0.3449	0.022*
C11	0.5555 (3)	−0.0273 (3)	−0.1549 (3)	0.0276 (6)
H11	0.4786	−0.1194	−0.2106	0.033*
C12	0.4880 (3)	0.0721 (2)	−0.1280 (2)	0.0243 (5)
H12	0.3665	0.0474	−0.1661	0.029*
C7	0.8974 (3)	0.3931 (2)	0.0916 (2)	0.0193 (5)
N1	1.0679 (3)	0.4543 (2)	0.1332 (2)	0.0214 (4)
C6	1.1063 (3)	0.5952 (2)	0.2058 (2)	0.0202 (5)
C5	1.2674 (3)	0.7073 (3)	0.2714 (2)	0.0228 (5)
H5	1.3691	0.6958	0.2695	0.027*
C4	1.2708 (3)	0.8375 (3)	0.3399 (3)	0.0312 (6)
H4	1.3767	0.9147	0.3855	0.037*
C3	1.1143 (4)	0.8535 (3)	0.3410 (3)	0.0303 (6)
H3	1.1197	0.9411	0.3890	0.036*
C2	0.9543 (3)	0.7420 (3)	0.2726 (3)	0.0257 (5)
H2	0.8510	0.7523	0.2717	0.031*
C1	0.9549 (3)	0.6149 (2)	0.2056 (2)	0.0222 (5)
H1N2	0.409 (4)	0.280 (3)	−0.035 (3)	0.043 (9)*

	U11	U22	U33	U12	U13	U23
O2	0.0157 (8)	0.0213 (8)	0.0235 (8)	0.0083 (6)	0.0111 (7)	0.0116 (7)
O1	0.0160 (8)	0.0301 (9)	0.0206 (8)	0.0148 (7)	0.0098 (7)	0.0129 (7)
N2	0.0169 (10)	0.0223 (10)	0.0212 (10)	0.0076 (8)	0.0073 (8)	0.0062 (8)
N3	0.0174 (10)	0.0228 (10)	0.0222 (10)	0.0087 (8)	0.0097 (8)	0.0110 (8)
C22	0.0255 (13)	0.0367 (15)	0.0420 (15)	0.0142 (11)	0.0213 (12)	0.0250 (12)
C21	0.0246 (12)	0.0199 (11)	0.0237 (12)	0.0095 (9)	0.0141 (10)	0.0117 (9)
C17	0.0167 (11)	0.0114 (10)	0.0186 (11)	0.0066 (8)	0.0074 (9)	0.0040 (8)
C16	0.0178 (11)	0.0137 (10)	0.0162 (11)	0.0091 (8)	0.0067 (9)	0.0056 (8)
C15	0.0173 (11)	0.0134 (10)	0.0181 (11)	0.0076 (8)	0.0079 (9)	0.0065 (8)
C14	0.0164 (11)	0.0216 (11)	0.0226 (11)	0.0121 (9)	0.0107 (9)	0.0122 (9)
C13	0.0242 (12)	0.0247 (12)	0.0168 (11)	0.0144 (10)	0.0113 (10)	0.0106 (9)
C8	0.0279 (13)	0.0161 (11)	0.0140 (10)	0.0047 (9)	0.0066 (10)	0.0061 (9)
C9	0.0192 (12)	0.0267 (12)	0.0294 (13)	0.0120 (10)	0.0109 (10)	0.0147 (10)
C10	0.0370 (15)	0.0177 (12)	0.0274 (13)	0.0126 (10)	0.0168 (11)	0.0081 (10)
C18	0.0211 (11)	0.0158 (10)	0.0169 (11)	0.0057 (9)	0.0081 (9)	0.0072 (9)
C19	0.0161 (11)	0.0187 (11)	0.0167 (11)	0.0052 (9)	0.0014 (9)	0.0066 (9)
C20	0.0134 (11)	0.0182 (11)	0.0211 (11)	0.0061 (9)	0.0059 (9)	0.0066 (9)
C11	0.0325 (14)	0.0195 (12)	0.0263 (13)	0.0055 (10)	0.0127 (11)	0.0073 (10)
C12	0.0203 (12)	0.0244 (12)	0.0220 (12)	0.0026 (10)	0.0094 (10)	0.0063 (10)
C7	0.0198 (11)	0.0271 (12)	0.0178 (11)	0.0139 (10)	0.0095 (9)	0.0125 (10)
N1	0.0182 (10)	0.0255 (10)	0.0226 (10)	0.0091 (8)	0.0087 (8)	0.0125 (8)
C6	0.0217 (12)	0.0210 (11)	0.0152 (11)	0.0044 (9)	0.0048 (9)	0.0107 (9)
C5	0.0185 (12)	0.0310 (13)	0.0195 (11)	0.0085 (10)	0.0064 (9)	0.0142 (10)
C4	0.0291 (14)	0.0238 (13)	0.0233 (12)	−0.0064 (10)	0.0030 (11)	0.0107 (10)
C3	0.0426 (16)	0.0178 (12)	0.0272 (13)	0.0100 (11)	0.0131 (12)	0.0085 (10)
C2	0.0251 (13)	0.0269 (13)	0.0275 (13)	0.0097 (10)	0.0119 (11)	0.0138 (11)
C1	0.0215 (12)	0.0228 (12)	0.0202 (11)	0.0040 (9)	0.0068 (10)	0.0126 (10)

O2—C17	1.367 (3)	C8—C7	1.461 (3)
O2—C21	1.438 (3)	C9—C10	1.379 (3)
O1—C16	1.362 (3)	C9—H9	0.9300
O1—H1O1	0.8200	C10—C11	1.375 (4)
N2—C13	1.407 (3)	C10—H10	0.9300
N2—C14	1.483 (3)	C18—C19	1.386 (3)
N2—H1N2	1.02 (3)	C18—H18	0.9300
N3—C7	1.354 (3)	C19—C20	1.386 (3)
N3—C1	1.401 (3)	C19—H19	0.9300
N3—C14	1.439 (3)	C20—H20	0.9300
C22—C21	1.503 (3)	C11—C12	1.364 (4)
C22—H22A	0.9600	C11—H11	0.9300
C22—H22B	0.9600	C12—H12	0.9300
C22—H22C	0.9600	C7—N1	1.312 (3)
C21—H21A	0.9700	N1—C6	1.403 (3)
C21—H21B	0.9700	C6—C1	1.385 (3)
C17—C18	1.389 (3)	C6—C5	1.389 (3)
C17—C16	1.402 (3)	C5—C4	1.391 (4)
C16—C15	1.394 (3)	C5—H5	0.9300
C15—C20	1.394 (3)	C4—C3	1.419 (4)
C15—C14	1.524 (3)	C4—H4	0.9300
C14—H14	0.9800	C3—C2	1.378 (4)
C13—C12	1.390 (3)	C3—H3	0.9300
C13—C8	1.414 (3)	C2—C1	1.373 (4)
C8—C9	1.404 (3)	C2—H2	0.9300
C17—O2—C21	116.69 (17)	C10—C9—H9	120.2
C16—O1—H1O1	109.5	C8—C9—H9	120.2
C13—N2—C14	117.46 (18)	C11—C10—C9	119.9 (2)
C13—N2—H1N2	111.6 (18)	C11—C10—H10	120.0
C14—N2—H1N2	109.0 (18)	C9—C10—H10	120.0
C7—N3—C1	106.87 (19)	C19—C18—C17	120.2 (2)
C7—N3—C14	125.18 (19)	C19—C18—H18	119.9
C1—N3—C14	126.96 (19)	C17—C18—H18	119.9
C21—C22—H22A	109.5	C20—C19—C18	120.4 (2)
C21—C22—H22B	109.5	C20—C19—H19	119.8
H22A—C22—H22B	109.5	C18—C19—H19	119.8
C21—C22—H22C	109.5	C19—C20—C15	119.7 (2)
H22A—C22—H22C	109.5	C19—C20—H20	120.1
H22B—C22—H22C	109.5	C15—C20—H20	120.1
O2—C21—C22	107.31 (19)	C12—C11—C10	121.7 (2)
O2—C21—H21A	110.3	C12—C11—H11	119.2
C22—C21—H21A	110.3	C10—C11—H11	119.2
O2—C21—H21B	110.3	C11—C12—C13	120.2 (2)
C22—C21—H21B	110.3	C11—C12—H12	119.9
H21A—C21—H21B	108.5	C13—C12—H12	119.9
O2—C17—C18	124.7 (2)	N1—C7—N3	113.7 (2)
O2—C17—C16	115.40 (19)	N1—C7—C8	128.5 (2)
C18—C17—C16	119.8 (2)	N3—C7—C8	117.8 (2)
O1—C16—C15	117.52 (19)	C7—N1—C6	104.17 (19)
O1—C16—C17	122.89 (19)	C1—C6—C5	120.5 (2)
C15—C16—C17	119.5 (2)	C1—C6—N1	110.7 (2)
C20—C15—C16	120.3 (2)	C5—C6—N1	128.8 (2)
C20—C15—C14	123.6 (2)	C6—C5—C4	117.4 (2)
C16—C15—C14	116.07 (19)	C6—C5—H5	121.3
N3—C14—N2	105.89 (17)	C4—C5—H5	121.3
N3—C14—C15	112.84 (18)	C5—C4—C3	120.6 (2)
N2—C14—C15	112.62 (18)	C5—C4—H4	119.7
N3—C14—H14	108.4	C3—C4—H4	119.7
N2—C14—H14	108.4	C2—C3—C4	121.4 (2)
C15—C14—H14	108.4	C2—C3—H3	119.3
C12—C13—N2	121.8 (2)	C4—C3—H3	119.3
C12—C13—C8	118.9 (2)	C1—C2—C3	116.7 (2)
N2—C13—C8	119.0 (2)	C1—C2—H2	121.7
C9—C8—C13	119.6 (2)	C3—C2—H2	121.7
C9—C8—C7	123.3 (2)	C2—C1—C6	123.3 (2)
C13—C8—C7	117.1 (2)	C2—C1—N3	132.2 (2)
C10—C9—C8	119.7 (2)	C6—C1—N3	104.5 (2)
C17—O2—C21—C22	−168.25 (19)	C16—C15—C20—C19	−0.8 (3)
C21—O2—C17—C18	−6.7 (3)	C14—C15—C20—C19	−178.3 (2)
C21—O2—C17—C16	170.40 (18)	C9—C10—C11—C12	−0.4 (4)
O2—C17—C16—O1	0.5 (3)	C10—C11—C12—C13	−0.7 (4)
C18—C17—C16—O1	177.77 (19)	N2—C13—C12—C11	175.7 (2)
O2—C17—C16—C15	−175.55 (18)	C8—C13—C12—C11	1.5 (4)
C18—C17—C16—C15	1.7 (3)	C1—N3—C7—N1	−2.4 (3)
O1—C16—C15—C20	−176.86 (19)	C14—N3—C7—N1	−171.7 (2)
C17—C16—C15—C20	−0.6 (3)	C1—N3—C7—C8	179.14 (19)
O1—C16—C15—C14	0.8 (3)	C14—N3—C7—C8	9.9 (3)
C17—C16—C15—C14	177.08 (18)	C9—C8—C7—N1	9.6 (4)
C7—N3—C14—N2	−37.3 (3)	C13—C8—C7—N1	−167.8 (2)
C1—N3—C14—N2	155.6 (2)	C9—C8—C7—N3	−172.1 (2)
C7—N3—C14—C15	86.4 (3)	C13—C8—C7—N3	10.4 (3)
C1—N3—C14—C15	−80.8 (3)	N3—C7—N1—C6	1.5 (3)
C13—N2—C14—N3	48.0 (3)	C8—C7—N1—C6	179.8 (2)
C13—N2—C14—C15	−75.8 (2)	C7—N1—C6—C1	0.0 (3)
C20—C15—C14—N3	−3.9 (3)	C7—N1—C6—C5	−179.5 (2)
C16—C15—C14—N3	178.50 (18)	C1—C6—C5—C4	2.3 (3)
C20—C15—C14—N2	115.9 (2)	N1—C6—C5—C4	−178.3 (2)
C16—C15—C14—N2	−61.7 (2)	C6—C5—C4—C3	−0.5 (4)
C14—N2—C13—C12	152.2 (2)	C5—C4—C3—C2	−1.2 (4)
C14—N2—C13—C8	−33.6 (3)	C4—C3—C2—C1	1.1 (4)
C12—C13—C8—C9	−1.2 (3)	C3—C2—C1—C6	0.8 (4)
N2—C13—C8—C9	−175.5 (2)	C3—C2—C1—N3	179.8 (2)
C12—C13—C8—C7	176.4 (2)	C5—C6—C1—C2	−2.5 (4)
N2—C13—C8—C7	2.0 (3)	N1—C6—C1—C2	177.9 (2)
C13—C8—C9—C10	0.1 (4)	C5—C6—C1—N3	178.2 (2)
C7—C8—C9—C10	−177.3 (2)	N1—C6—C1—N3	−1.4 (2)
C8—C9—C10—C11	0.7 (4)	C7—N3—C1—C2	−177.0 (3)
O2—C17—C18—C19	175.5 (2)	C14—N3—C1—C2	−8.0 (4)
C16—C17—C18—C19	−1.5 (3)	C7—N3—C1—C6	2.2 (2)
C17—C18—C19—C20	0.1 (3)	C14—N3—C1—C6	171.2 (2)
C18—C19—C20—C15	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1i	0.82	1.85	2.646 (3)	165
N2—H1N2···O1	1.01 (4)	2.12 (3)	2.811 (3)	124 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1i	0.82	1.85	2.646 (3)	165
N2—H1N2⋯O1	1.01 (4)	2.12 (3)	2.811 (3)	124 (2)

Symmetry code: (i) .