1H-Benzimidazol-2-ylmethyl phenyl ether.

There are two mol-ecules in the asymmetric unit of the title compound, C(14)H(10)N(2)O: the dihedral angles between their aromatic ring planes are 47.4 (4) and 46.8 (3)°. In the crystal structure, mol-ecules are linked by N-H⋯N hydrogen bonds from the secondary nitro-gen N-H donor to the tertiary N-atom acceptor of a symmetry-related neighbour, resulting in hydrogen-bonded chains. The two independent chains both propagate in [100].

Related literature

For related phen­oxy-substituted N-heterocycles, see: Abdullah & Ng (2008 ▶); Hassan et al. (2008 ▶); Idris et al. (2009 ▶); Shah Bakhtiar et al. (2009 ▶).

Experimental

Crystal data

C14H12N2O

M = 224.26

Orthorhombic,

a = 10.0299 (5) Å

b = 8.5391 (4) Å

c = 27.000 (1) Å

V = 2312.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.40 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: none

15022 measured reflections

2699 independent reflections

1783 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.111

S = 1.00

2699 reflections

313 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007922/hb2923sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007922/hb2923Isup2.hkl

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

C14H12N2O	F(000) = 944
Mr = 224.26	Dx = 1.288 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1070 reflections
a = 10.0299 (5) Å	θ = 2.8–21.3°
b = 8.5391 (4) Å	µ = 0.08 mm−1
c = 27.000 (1) Å	T = 120 K
V = 2312.5 (2) Å3	Prism, colorless
Z = 8	0.40 × 0.10 × 0.03 mm

Bruker SMART APEX CCD diffractometer	1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.091
graphite	θmax = 27.5°, θmin = 2.4°
ω scans	h = −12→12
15022 measured reflections	k = −11→10
2699 independent reflections	l = −35→34

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3
2699 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 0.19 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.0484 (3)	1.2098 (3)	0.50009 (13)	0.0299 (7)
O2	0.2955 (3)	0.7163 (3)	0.31456 (13)	0.0325 (7)
N1	0.0514 (5)	0.9631 (5)	0.5645 (2)	0.0218 (10)
H1	−0.030 (2)	0.991 (4)	0.557 (2)	0.026*
N2	0.2729 (4)	0.9563 (5)	0.56067 (17)	0.0248 (9)
N3	0.2988 (6)	0.4652 (5)	0.2512 (2)	0.0232 (11)
H3	0.2154 (18)	0.496 (4)	0.254 (2)	0.028*
N4	0.5228 (4)	0.4592 (5)	0.25497 (16)	0.0228 (9)
C1	0.0158 (8)	1.3554 (8)	0.4819 (3)	0.0241 (15)
C2	−0.0889 (9)	1.3564 (10)	0.4484 (3)	0.038 (2)
H2	−0.1315	1.2614	0.4392	0.046*
C3	−0.1303 (13)	1.4968 (6)	0.4286 (5)	0.046 (3)
H3A	−0.2025	1.4980	0.4059	0.055*
C4	−0.0687 (9)	1.6364 (10)	0.4412 (3)	0.0363 (19)
H4	−0.0977	1.7326	0.4271	0.044*
C5	0.0356 (9)	1.6329 (9)	0.4745 (3)	0.036 (2)
H5	0.0789	1.7276	0.4835	0.043*
C6	0.0775 (12)	1.4931 (5)	0.4947 (4)	0.031 (3)
H6	0.1494	1.4920	0.5177	0.037*
C7	0.1627 (4)	1.1991 (5)	0.53097 (18)	0.0251 (10)
H7A	0.1569	1.2759	0.5584	0.030*
H7B	0.2446	1.2206	0.5117	0.030*
C8	0.1653 (6)	1.0354 (7)	0.5510 (2)	0.0227 (13)
C9	0.0880 (4)	0.8244 (5)	0.58670 (16)	0.0207 (10)
C10	0.0147 (4)	0.7057 (5)	0.60944 (17)	0.0241 (9)
H10	−0.0799	0.7088	0.6108	0.029*
C11	0.0864 (4)	0.5826 (6)	0.63004 (18)	0.0266 (11)
H11	0.0403	0.5013	0.6469	0.032*
C12	0.2252 (4)	0.5768 (5)	0.62635 (17)	0.0241 (10)
H12	0.2713	0.4901	0.6403	0.029*
C13	0.2976 (4)	0.6931 (5)	0.60308 (15)	0.0239 (9)
H13	0.3919	0.6867	0.6003	0.029*
C14	0.2276 (4)	0.8200 (5)	0.58383 (16)	0.0219 (9)
C15	0.2627 (8)	0.8623 (8)	0.3334 (3)	0.0249 (15)
C16	0.1578 (8)	0.8609 (10)	0.3667 (3)	0.0348 (19)
H16	0.1140	0.7654	0.3744	0.042*
C17	0.1170 (12)	0.9988 (5)	0.3886 (4)	0.035 (3)
H17	0.0473	0.9978	0.4124	0.042*
C18	0.1780 (9)	1.1382 (10)	0.3759 (3)	0.0333 (18)
H18	0.1481	1.2340	0.3899	0.040*
C19	0.2824 (9)	1.1375 (9)	0.3427 (3)	0.0334 (19)
H19	0.3246	1.2337	0.3346	0.040*
C20	0.3278 (12)	0.9996 (4)	0.3207 (4)	0.030 (3)
H20	0.4002	0.9999	0.2980	0.036*
C21	0.4121 (4)	0.7020 (6)	0.28515 (19)	0.0288 (11)
H21A	0.4927	0.7198	0.3055	0.035*
H21B	0.4110	0.7797	0.2579	0.035*
C22	0.4117 (5)	0.5409 (7)	0.2650 (2)	0.0211 (12)
C23	0.3366 (4)	0.3256 (5)	0.22992 (16)	0.0201 (10)
C24	0.2635 (4)	0.2077 (5)	0.20763 (16)	0.0241 (9)
H24	0.1689	0.2108	0.2062	0.029*
C25	0.3346 (4)	0.0861 (6)	0.18773 (18)	0.0262 (11)
H25	0.2881	0.0041	0.1714	0.031*
C26	0.4741 (4)	0.0791 (5)	0.19069 (18)	0.0286 (10)
H26	0.5197	−0.0077	0.1766	0.034*
C27	0.5464 (4)	0.1960 (5)	0.21372 (16)	0.0260 (10)
H27	0.6408	0.1905	0.2162	0.031*
C28	0.4760 (4)	0.3219 (5)	0.23303 (16)	0.0203 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0255 (17)	0.0259 (16)	0.0382 (17)	0.0004 (14)	−0.0086 (14)	0.0034 (14)
O2	0.0274 (17)	0.0236 (16)	0.0465 (18)	−0.0025 (13)	0.0146 (15)	−0.0054 (14)
N1	0.007 (2)	0.0248 (18)	0.033 (3)	0.005 (2)	−0.0012 (19)	−0.001 (3)
N2	0.017 (2)	0.0212 (18)	0.037 (2)	0.000 (2)	0.002 (2)	−0.002 (2)
N3	0.015 (3)	0.0226 (18)	0.032 (3)	−0.001 (2)	0.002 (2)	−0.001 (3)
N4	0.014 (2)	0.0246 (19)	0.029 (2)	0.004 (2)	0.0014 (18)	−0.006 (2)
C1	0.023 (3)	0.021 (3)	0.027 (3)	0.006 (2)	0.003 (2)	0.004 (2)
C2	0.029 (4)	0.033 (4)	0.052 (4)	0.002 (3)	−0.006 (3)	0.011 (3)
C3	0.026 (7)	0.053 (8)	0.059 (8)	0.005 (2)	−0.011 (6)	0.015 (3)
C4	0.038 (4)	0.033 (4)	0.039 (3)	0.010 (3)	0.011 (3)	0.013 (3)
C5	0.045 (5)	0.029 (4)	0.032 (3)	−0.002 (3)	−0.002 (3)	0.006 (3)
C6	0.042 (7)	0.034 (5)	0.016 (4)	0.001 (2)	−0.010 (4)	0.0036 (17)
C7	0.016 (2)	0.024 (3)	0.036 (3)	−0.0022 (16)	−0.0023 (17)	0.004 (2)
C8	0.021 (3)	0.021 (2)	0.026 (3)	−0.006 (2)	0.000 (2)	0.003 (3)
C9	0.015 (2)	0.023 (2)	0.024 (2)	−0.0020 (17)	−0.0003 (17)	−0.0032 (19)
C10	0.016 (2)	0.025 (2)	0.031 (2)	−0.0027 (18)	0.0027 (18)	−0.001 (2)
C11	0.032 (3)	0.022 (3)	0.026 (2)	−0.0074 (19)	0.0008 (19)	−0.002 (2)
C12	0.025 (3)	0.018 (2)	0.030 (2)	0.0031 (19)	−0.0003 (19)	−0.0006 (19)
C13	0.016 (2)	0.026 (2)	0.029 (2)	0.0034 (17)	0.0003 (18)	0.0000 (18)
C14	0.017 (2)	0.023 (2)	0.025 (2)	0.0029 (18)	0.0011 (17)	−0.0022 (17)
C15	0.025 (3)	0.024 (3)	0.025 (3)	0.000 (2)	0.000 (2)	−0.004 (2)
C16	0.028 (4)	0.036 (4)	0.040 (4)	−0.007 (3)	0.012 (3)	−0.010 (3)
C17	0.029 (6)	0.040 (6)	0.037 (6)	−0.0004 (19)	0.003 (5)	−0.012 (2)
C18	0.033 (4)	0.035 (4)	0.032 (3)	0.009 (3)	−0.002 (3)	−0.012 (3)
C19	0.044 (4)	0.025 (3)	0.031 (3)	0.001 (3)	−0.004 (3)	0.002 (3)
C20	0.029 (6)	0.023 (5)	0.038 (5)	0.0021 (17)	−0.006 (4)	−0.0012 (18)
C21	0.018 (3)	0.033 (3)	0.036 (3)	−0.0038 (18)	0.0055 (18)	−0.004 (2)
C22	0.010 (3)	0.025 (2)	0.029 (3)	0.002 (2)	0.0020 (19)	0.005 (3)
C23	0.019 (2)	0.020 (2)	0.021 (2)	0.0017 (17)	0.0031 (17)	0.0017 (19)
C24	0.019 (2)	0.026 (2)	0.028 (2)	−0.0038 (18)	−0.0001 (17)	0.003 (2)
C25	0.028 (3)	0.025 (3)	0.026 (2)	−0.0021 (19)	−0.0023 (19)	−0.005 (2)
C26	0.029 (3)	0.027 (3)	0.030 (2)	0.004 (2)	0.001 (2)	−0.003 (2)
C27	0.019 (2)	0.028 (2)	0.032 (2)	0.0029 (18)	0.0016 (18)	0.0038 (19)
C28	0.014 (2)	0.020 (2)	0.026 (2)	−0.0038 (17)	0.0009 (17)	0.0047 (17)

O1—C1	1.376 (8)	C10—H10	0.9500
O1—C7	1.421 (5)	C11—C12	1.397 (6)
O2—C15	1.386 (8)	C11—H11	0.9500
O2—C21	1.419 (5)	C12—C13	1.381 (6)
N1—C8	1.349 (8)	C12—H12	0.9500
N1—C9	1.377 (6)	C13—C14	1.392 (5)
N1—H1	0.880 (10)	C13—H13	0.9500
N2—C8	1.299 (7)	C15—C16	1.383 (11)
N2—C14	1.397 (6)	C15—C20	1.385 (11)
N3—C22	1.357 (8)	C16—C17	1.380 (11)
N3—C23	1.376 (6)	C16—H16	0.9500
N3—H3	0.881 (10)	C17—C18	1.382 (11)
N4—C22	1.342 (7)	C17—H17	0.9500
N4—C28	1.395 (6)	C18—C19	1.377 (13)
C1—C6	1.373 (10)	C18—H18	0.9500
C1—C2	1.386 (12)	C19—C20	1.396 (11)
C2—C3	1.377 (11)	C19—H19	0.9500
C2—H2	0.9500	C20—H20	0.9500
C3—C4	1.384 (12)	C21—C22	1.480 (8)
C3—H3A	0.9500	C21—H21A	0.9900
C4—C5	1.381 (13)	C21—H21B	0.9900
C4—H4	0.9500	C23—C24	1.383 (6)
C5—C6	1.379 (10)	C23—C28	1.402 (5)
C5—H5	0.9500	C24—C25	1.369 (6)
C6—H6	0.9500	C24—H24	0.9500
C7—C8	1.500 (7)	C25—C26	1.402 (6)
C7—H7A	0.9900	C25—H25	0.9500
C7—H7B	0.9900	C26—C27	1.382 (6)
C9—C10	1.394 (6)	C26—H26	0.9500
C9—C14	1.403 (5)	C27—C28	1.387 (6)
C10—C11	1.389 (6)	C27—H27	0.9500
C1—O1—C7	117.3 (4)	C12—C13—H13	121.2
C15—O2—C21	118.5 (4)	C14—C13—H13	121.2
C8—N1—C9	106.6 (5)	C13—C14—N2	130.7 (4)
C8—N1—H1	127 (3)	C13—C14—C9	120.2 (4)
C9—N1—H1	126 (3)	N2—C14—C9	109.1 (3)
C8—N2—C14	104.6 (5)	C16—C15—C20	121.8 (8)
C22—N3—C23	107.3 (5)	C16—C15—O2	114.3 (6)
C22—N3—H3	129 (3)	C20—C15—O2	124.0 (7)
C23—N3—H3	124 (3)	C17—C16—C15	119.8 (8)
C22—N4—C28	104.1 (4)	C17—C16—H16	120.1
C6—C1—O1	125.2 (7)	C15—C16—H16	120.1
C6—C1—C2	120.1 (8)	C16—C17—C18	119.7 (10)
O1—C1—C2	114.7 (7)	C16—C17—H17	120.1
C3—C2—C1	119.1 (9)	C18—C17—H17	120.1
C3—C2—H2	120.4	C19—C18—C17	119.7 (8)
C1—C2—H2	120.4	C19—C18—H18	120.2
C2—C3—C4	121.4 (11)	C17—C18—H18	120.2
C2—C3—H3A	119.3	C18—C19—C20	121.9 (9)
C4—C3—H3A	119.3	C18—C19—H19	119.0
C5—C4—C3	118.6 (8)	C20—C19—H19	119.0
C5—C4—H4	120.7	C15—C20—C19	117.0 (11)
C3—C4—H4	120.7	C15—C20—H20	121.5
C6—C5—C4	120.6 (9)	C19—C20—H20	121.5
C6—C5—H5	119.7	O2—C21—C22	106.5 (4)
C4—C5—H5	119.7	O2—C21—H21A	110.4
C1—C6—C5	120.2 (10)	C22—C21—H21A	110.4
C1—C6—H6	119.9	O2—C21—H21B	110.4
C5—C6—H6	119.9	C22—C21—H21B	110.4
O1—C7—C8	106.6 (4)	H21A—C21—H21B	108.6
O1—C7—H7A	110.4	N4—C22—N3	113.0 (5)
C8—C7—H7A	110.4	N4—C22—C21	123.7 (5)
O1—C7—H7B	110.4	N3—C22—C21	123.1 (5)
C8—C7—H7B	110.4	N3—C23—C24	131.8 (4)
H7A—C7—H7B	108.6	N3—C23—C28	105.7 (4)
N2—C8—N1	114.3 (5)	C24—C23—C28	122.5 (4)
N2—C8—C7	124.8 (5)	C25—C24—C23	116.6 (4)
N1—C8—C7	120.6 (5)	C25—C24—H24	121.7
N1—C9—C10	132.6 (4)	C23—C24—H24	121.7
N1—C9—C14	105.3 (4)	C24—C25—C26	122.0 (4)
C10—C9—C14	122.1 (4)	C24—C25—H25	119.0
C11—C10—C9	117.0 (4)	C26—C25—H25	119.0
C11—C10—H10	121.5	C27—C26—C25	121.2 (4)
C9—C10—H10	121.5	C27—C26—H26	119.4
C10—C11—C12	120.9 (4)	C25—C26—H26	119.4
C10—C11—H11	119.5	C26—C27—C28	117.5 (4)
C12—C11—H11	119.5	C26—C27—H27	121.3
C13—C12—C11	122.0 (4)	C28—C27—H27	121.3
C13—C12—H12	119.0	C27—C28—N4	129.8 (4)
C11—C12—H12	119.0	C27—C28—C23	120.2 (4)
C12—C13—C14	117.7 (4)	N4—C28—C23	110.0 (3)
C7—O1—C1—C6	−6.1 (11)	C21—O2—C15—C16	−172.0 (6)
C7—O1—C1—C2	174.2 (6)	C21—O2—C15—C20	7.9 (10)
C6—C1—C2—C3	−0.5 (15)	C20—C15—C16—C17	−0.9 (14)
O1—C1—C2—C3	179.1 (8)	O2—C15—C16—C17	179.0 (8)
C1—C2—C3—C4	0.6 (18)	C15—C16—C17—C18	2.4 (16)
C2—C3—C4—C5	−0.4 (18)	C16—C17—C18—C19	−2.4 (16)
C3—C4—C5—C6	0.0 (15)	C17—C18—C19—C20	1.1 (14)
O1—C1—C6—C5	−179.4 (6)	C16—C15—C20—C19	−0.4 (15)
C2—C1—C6—C5	0.2 (16)	O2—C15—C20—C19	179.6 (6)
C4—C5—C6—C1	0.1 (16)	C18—C19—C20—C15	0.4 (15)
C1—O1—C7—C8	172.5 (5)	C15—O2—C21—C22	−172.6 (5)
C14—N2—C8—N1	−1.5 (7)	C28—N4—C22—N3	0.2 (7)
C14—N2—C8—C7	173.1 (5)	C28—N4—C22—C21	−175.0 (5)
C9—N1—C8—N2	2.0 (8)	C23—N3—C22—N4	−1.0 (7)
C9—N1—C8—C7	−172.9 (5)	C23—N3—C22—C21	174.3 (5)
O1—C7—C8—N2	146.8 (6)	O2—C21—C22—N4	−149.1 (5)
O1—C7—C8—N1	−39.0 (7)	O2—C21—C22—N3	36.1 (7)
C8—N1—C9—C10	177.0 (5)	C22—N3—C23—C24	−176.6 (5)
C8—N1—C9—C14	−1.6 (6)	C22—N3—C23—C28	1.3 (6)
N1—C9—C10—C11	−177.4 (5)	N3—C23—C24—C25	176.7 (5)
C14—C9—C10—C11	1.0 (6)	C28—C23—C24—C25	−1.0 (6)
C9—C10—C11—C12	−2.2 (6)	C23—C24—C25—C26	1.5 (7)
C10—C11—C12—C13	1.2 (6)	C24—C25—C26—C27	−0.5 (7)
C11—C12—C13—C14	1.1 (6)	C25—C26—C27—C28	−1.1 (6)
C12—C13—C14—N2	176.8 (4)	C26—C27—C28—N4	−175.4 (4)
C12—C13—C14—C9	−2.3 (5)	C26—C27—C28—C23	1.5 (6)
C8—N2—C14—C13	−178.8 (5)	C22—N4—C28—C27	177.8 (5)
C8—N2—C14—C9	0.4 (6)	C22—N4—C28—C23	0.7 (5)
N1—C9—C14—C13	−179.9 (4)	N3—C23—C28—C27	−178.7 (4)
C10—C9—C14—C13	1.3 (6)	C24—C23—C28—C27	−0.5 (6)
N1—C9—C14—N2	0.7 (5)	N3—C23—C28—N4	−1.3 (5)
C10—C9—C14—N2	−178.0 (4)	C24—C23—C28—N4	176.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88 (1)	2.03 (2)	2.879 (7)	163 (6)
N3—H3···N4ii	0.88 (1)	1.97 (2)	2.845 (8)	172 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88 (1)	2.03 (2)	2.879 (7)	163 (6)
N3—H3⋯N4ii	0.88 (1)	1.97 (2)	2.845 (8)	172 (5)

Symmetry codes: (i) ; (ii) .