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Acta Cryst. (2009). E65, o733    [ doi:10.1107/S1600536809007922 ]

1H-Benzimidazol-2-ylmethyl phenyl ether

N. D. Hassan, H. A. Tajuddin, Z. Abdullah and S. W. Ng

Abstract top

There are two molecules in the asymmetric unit of the title compound, C14H10N2O: the dihedral angles between their aromatic ring planes are 47.4 (4) and 46.8 (3)°. In the crystal structure, molecules are linked by N-H...N hydrogen bonds from the secondary nitrogen 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 top

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

Experimental top

Phenol (1.88 g, 20 mmol) was mixed with sodium hydroxide (0.08 g, 20 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-(chloromethyl)benzimidazole 3.30 g, 20 mmol) at 423–433 K for 6 h. The product was dissolved in water and the solution extracted with chloroform. The chloroform phase was dried over sodium sulfate; the evaporation of the solvent a brown product; this was purified by column chromatography with an ethyl acetate/hexane mixture. Crystals were grown from this solvent system gave well shaped colorless crystals along with some unidentified brown material.

Refinement top

Anomalous dispersion was negligible and Friedel pairs were merged before refinement.

The C-bound H-atoms were placed in calculated positions (C—H 0.95–98 Å) and refined as riding with U(H) = 1.2Ueq(C). The N-bound H atoms were located in a difference map, and were refined with a restraint of N–H 0.88±0.01 Å; their Uiso values were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
1H-Benzimidazol-2-ylmethyl phenyl ether top
Crystal data top
C14H12N2OF(000) = 944
Mr = 224.26Dx = 1.288 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1070 reflections
a = 10.0299 (5) Åθ = 2.8–21.3°
b = 8.5391 (4) ŵ = 0.08 mm−1
c = 27.000 (1) ÅT = 120 K
V = 2312.5 (2) Å3Prism, colorless
Z = 80.40 × 0.10 × 0.03 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
graphiteθmax = 27.5°, θmin = 2.4°
ω scansh = −12→12
15022 measured reflectionsk = −11→10
2699 independent reflectionsl = −35→34
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H 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 parametersΔρmax = 0.19 e Å−3
3 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C14H12N2OV = 2312.5 (2) Å3
Mr = 224.26Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 10.0299 (5) ŵ = 0.08 mm−1
b = 8.5391 (4) ÅT = 120 K
c = 27.000 (1) Å0.40 × 0.10 × 0.03 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		1783 reflections with I > 2σ(I)
15022 measured reflectionsRint = 0.091
2699 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111Δρmax = 0.19 e Å−3
S = 1.00Δρmin = −0.23 e Å−3
2699 reflectionsAbsolute structure: ?
313 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0484 (3)1.2098 (3)0.50009 (13)0.0299 (7)
O20.2955 (3)0.7163 (3)0.31456 (13)0.0325 (7)
N10.0514 (5)0.9631 (5)0.5645 (2)0.0218 (10)
H1−0.030 (2)0.991 (4)0.557 (2)0.026*
N20.2729 (4)0.9563 (5)0.56067 (17)0.0248 (9)
N30.2988 (6)0.4652 (5)0.2512 (2)0.0232 (11)
H30.2154 (18)0.496 (4)0.254 (2)0.028*
N40.5228 (4)0.4592 (5)0.25497 (16)0.0228 (9)
C10.0158 (8)1.3554 (8)0.4819 (3)0.0241 (15)
C2−0.0889 (9)1.3564 (10)0.4484 (3)0.038 (2)
H2−0.13151.26140.43920.046*
C3−0.1303 (13)1.4968 (6)0.4286 (5)0.046 (3)
H3A−0.20251.49800.40590.055*
C4−0.0687 (9)1.6364 (10)0.4412 (3)0.0363 (19)
H4−0.09771.73260.42710.044*
C50.0356 (9)1.6329 (9)0.4745 (3)0.036 (2)
H50.07891.72760.48350.043*
C60.0775 (12)1.4931 (5)0.4947 (4)0.031 (3)
H60.14941.49200.51770.037*
C70.1627 (4)1.1991 (5)0.53097 (18)0.0251 (10)
H7A0.15691.27590.55840.030*
H7B0.24461.22060.51170.030*
C80.1653 (6)1.0354 (7)0.5510 (2)0.0227 (13)
C90.0880 (4)0.8244 (5)0.58670 (16)0.0207 (10)
C100.0147 (4)0.7057 (5)0.60944 (17)0.0241 (9)
H10−0.07990.70880.61080.029*
C110.0864 (4)0.5826 (6)0.63004 (18)0.0266 (11)
H110.04030.50130.64690.032*
C120.2252 (4)0.5768 (5)0.62635 (17)0.0241 (10)
H120.27130.49010.64030.029*
C130.2976 (4)0.6931 (5)0.60308 (15)0.0239 (9)
H130.39190.68670.60030.029*
C140.2276 (4)0.8200 (5)0.58383 (16)0.0219 (9)
C150.2627 (8)0.8623 (8)0.3334 (3)0.0249 (15)
C160.1578 (8)0.8609 (10)0.3667 (3)0.0348 (19)
H160.11400.76540.37440.042*
C170.1170 (12)0.9988 (5)0.3886 (4)0.035 (3)
H170.04730.99780.41240.042*
C180.1780 (9)1.1382 (10)0.3759 (3)0.0333 (18)
H180.14811.23400.38990.040*
C190.2824 (9)1.1375 (9)0.3427 (3)0.0334 (19)
H190.32461.23370.33460.040*
C200.3278 (12)0.9996 (4)0.3207 (4)0.030 (3)
H200.40020.99990.29800.036*
C210.4121 (4)0.7020 (6)0.28515 (19)0.0288 (11)
H21A0.49270.71980.30550.035*
H21B0.41100.77970.25790.035*
C220.4117 (5)0.5409 (7)0.2650 (2)0.0211 (12)
C230.3366 (4)0.3256 (5)0.22992 (16)0.0201 (10)
C240.2635 (4)0.2077 (5)0.20763 (16)0.0241 (9)
H240.16890.21080.20620.029*
C250.3346 (4)0.0861 (6)0.18773 (18)0.0262 (11)
H250.28810.00410.17140.031*
C260.4741 (4)0.0791 (5)0.19069 (18)0.0286 (10)
H260.5197−0.00770.17660.034*
C270.5464 (4)0.1960 (5)0.21372 (16)0.0260 (10)
H270.64080.19050.21620.031*
C280.4760 (4)0.3219 (5)0.23303 (16)0.0203 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0255 (17)0.0259 (16)0.0382 (17)0.0004 (14)−0.0086 (14)0.0034 (14)
O20.0274 (17)0.0236 (16)0.0465 (18)−0.0025 (13)0.0146 (15)−0.0054 (14)
N10.007 (2)0.0248 (18)0.033 (3)0.005 (2)−0.0012 (19)−0.001 (3)
N20.017 (2)0.0212 (18)0.037 (2)0.000 (2)0.002 (2)−0.002 (2)
N30.015 (3)0.0226 (18)0.032 (3)−0.001 (2)0.002 (2)−0.001 (3)
N40.014 (2)0.0246 (19)0.029 (2)0.004 (2)0.0014 (18)−0.006 (2)
C10.023 (3)0.021 (3)0.027 (3)0.006 (2)0.003 (2)0.004 (2)
C20.029 (4)0.033 (4)0.052 (4)0.002 (3)−0.006 (3)0.011 (3)
C30.026 (7)0.053 (8)0.059 (8)0.005 (2)−0.011 (6)0.015 (3)
C40.038 (4)0.033 (4)0.039 (3)0.010 (3)0.011 (3)0.013 (3)
C50.045 (5)0.029 (4)0.032 (3)−0.002 (3)−0.002 (3)0.006 (3)
C60.042 (7)0.034 (5)0.016 (4)0.001 (2)−0.010 (4)0.0036 (17)
C70.016 (2)0.024 (3)0.036 (3)−0.0022 (16)−0.0023 (17)0.004 (2)
C80.021 (3)0.021 (2)0.026 (3)−0.006 (2)0.000 (2)0.003 (3)
C90.015 (2)0.023 (2)0.024 (2)−0.0020 (17)−0.0003 (17)−0.0032 (19)
C100.016 (2)0.025 (2)0.031 (2)−0.0027 (18)0.0027 (18)−0.001 (2)
C110.032 (3)0.022 (3)0.026 (2)−0.0074 (19)0.0008 (19)−0.002 (2)
C120.025 (3)0.018 (2)0.030 (2)0.0031 (19)−0.0003 (19)−0.0006 (19)
C130.016 (2)0.026 (2)0.029 (2)0.0034 (17)0.0003 (18)0.0000 (18)
C140.017 (2)0.023 (2)0.025 (2)0.0029 (18)0.0011 (17)−0.0022 (17)
C150.025 (3)0.024 (3)0.025 (3)0.000 (2)0.000 (2)−0.004 (2)
C160.028 (4)0.036 (4)0.040 (4)−0.007 (3)0.012 (3)−0.010 (3)
C170.029 (6)0.040 (6)0.037 (6)−0.0004 (19)0.003 (5)−0.012 (2)
C180.033 (4)0.035 (4)0.032 (3)0.009 (3)−0.002 (3)−0.012 (3)
C190.044 (4)0.025 (3)0.031 (3)0.001 (3)−0.004 (3)0.002 (3)
C200.029 (6)0.023 (5)0.038 (5)0.0021 (17)−0.006 (4)−0.0012 (18)
C210.018 (3)0.033 (3)0.036 (3)−0.0038 (18)0.0055 (18)−0.004 (2)
C220.010 (3)0.025 (2)0.029 (3)0.002 (2)0.0020 (19)0.005 (3)
C230.019 (2)0.020 (2)0.021 (2)0.0017 (17)0.0031 (17)0.0017 (19)
C240.019 (2)0.026 (2)0.028 (2)−0.0038 (18)−0.0001 (17)0.003 (2)
C250.028 (3)0.025 (3)0.026 (2)−0.0021 (19)−0.0023 (19)−0.005 (2)
C260.029 (3)0.027 (3)0.030 (2)0.004 (2)0.001 (2)−0.003 (2)
C270.019 (2)0.028 (2)0.032 (2)0.0029 (18)0.0016 (18)0.0038 (19)
C280.014 (2)0.020 (2)0.026 (2)−0.0038 (17)0.0009 (17)0.0047 (17)
Geometric parameters (Å, °) top
O1—C11.376 (8)C10—H100.9500
O1—C71.421 (5)C11—C121.397 (6)
O2—C151.386 (8)C11—H110.9500
O2—C211.419 (5)C12—C131.381 (6)
N1—C81.349 (8)C12—H120.9500
N1—C91.377 (6)C13—C141.392 (5)
N1—H10.880 (10)C13—H130.9500
N2—C81.299 (7)C15—C161.383 (11)
N2—C141.397 (6)C15—C201.385 (11)
N3—C221.357 (8)C16—C171.380 (11)
N3—C231.376 (6)C16—H160.9500
N3—H30.881 (10)C17—C181.382 (11)
N4—C221.342 (7)C17—H170.9500
N4—C281.395 (6)C18—C191.377 (13)
C1—C61.373 (10)C18—H180.9500
C1—C21.386 (12)C19—C201.396 (11)
C2—C31.377 (11)C19—H190.9500
C2—H20.9500C20—H200.9500
C3—C41.384 (12)C21—C221.480 (8)
C3—H3A0.9500C21—H21A0.9900
C4—C51.381 (13)C21—H21B0.9900
C4—H40.9500C23—C241.383 (6)
C5—C61.379 (10)C23—C281.402 (5)
C5—H50.9500C24—C251.369 (6)
C6—H60.9500C24—H240.9500
C7—C81.500 (7)C25—C261.402 (6)
C7—H7A0.9900C25—H250.9500
C7—H7B0.9900C26—C271.382 (6)
C9—C101.394 (6)C26—H260.9500
C9—C141.403 (5)C27—C281.387 (6)
C10—C111.389 (6)C27—H270.9500
C1—O1—C7117.3 (4)C12—C13—H13121.2
C15—O2—C21118.5 (4)C14—C13—H13121.2
C8—N1—C9106.6 (5)C13—C14—N2130.7 (4)
C8—N1—H1127 (3)C13—C14—C9120.2 (4)
C9—N1—H1126 (3)N2—C14—C9109.1 (3)
C8—N2—C14104.6 (5)C16—C15—C20121.8 (8)
C22—N3—C23107.3 (5)C16—C15—O2114.3 (6)
C22—N3—H3129 (3)C20—C15—O2124.0 (7)
C23—N3—H3124 (3)C17—C16—C15119.8 (8)
C22—N4—C28104.1 (4)C17—C16—H16120.1
C6—C1—O1125.2 (7)C15—C16—H16120.1
C6—C1—C2120.1 (8)C16—C17—C18119.7 (10)
O1—C1—C2114.7 (7)C16—C17—H17120.1
C3—C2—C1119.1 (9)C18—C17—H17120.1
C3—C2—H2120.4C19—C18—C17119.7 (8)
C1—C2—H2120.4C19—C18—H18120.2
C2—C3—C4121.4 (11)C17—C18—H18120.2
C2—C3—H3A119.3C18—C19—C20121.9 (9)
C4—C3—H3A119.3C18—C19—H19119.0
C5—C4—C3118.6 (8)C20—C19—H19119.0
C5—C4—H4120.7C15—C20—C19117.0 (11)
C3—C4—H4120.7C15—C20—H20121.5
C6—C5—C4120.6 (9)C19—C20—H20121.5
C6—C5—H5119.7O2—C21—C22106.5 (4)
C4—C5—H5119.7O2—C21—H21A110.4
C1—C6—C5120.2 (10)C22—C21—H21A110.4
C1—C6—H6119.9O2—C21—H21B110.4
C5—C6—H6119.9C22—C21—H21B110.4
O1—C7—C8106.6 (4)H21A—C21—H21B108.6
O1—C7—H7A110.4N4—C22—N3113.0 (5)
C8—C7—H7A110.4N4—C22—C21123.7 (5)
O1—C7—H7B110.4N3—C22—C21123.1 (5)
C8—C7—H7B110.4N3—C23—C24131.8 (4)
H7A—C7—H7B108.6N3—C23—C28105.7 (4)
N2—C8—N1114.3 (5)C24—C23—C28122.5 (4)
N2—C8—C7124.8 (5)C25—C24—C23116.6 (4)
N1—C8—C7120.6 (5)C25—C24—H24121.7
N1—C9—C10132.6 (4)C23—C24—H24121.7
N1—C9—C14105.3 (4)C24—C25—C26122.0 (4)
C10—C9—C14122.1 (4)C24—C25—H25119.0
C11—C10—C9117.0 (4)C26—C25—H25119.0
C11—C10—H10121.5C27—C26—C25121.2 (4)
C9—C10—H10121.5C27—C26—H26119.4
C10—C11—C12120.9 (4)C25—C26—H26119.4
C10—C11—H11119.5C26—C27—C28117.5 (4)
C12—C11—H11119.5C26—C27—H27121.3
C13—C12—C11122.0 (4)C28—C27—H27121.3
C13—C12—H12119.0C27—C28—N4129.8 (4)
C11—C12—H12119.0C27—C28—C23120.2 (4)
C12—C13—C14117.7 (4)N4—C28—C23110.0 (3)
C7—O1—C1—C6−6.1 (11)C21—O2—C15—C16−172.0 (6)
C7—O1—C1—C2174.2 (6)C21—O2—C15—C207.9 (10)
C6—C1—C2—C3−0.5 (15)C20—C15—C16—C17−0.9 (14)
O1—C1—C2—C3179.1 (8)O2—C15—C16—C17179.0 (8)
C1—C2—C3—C40.6 (18)C15—C16—C17—C182.4 (16)
C2—C3—C4—C5−0.4 (18)C16—C17—C18—C19−2.4 (16)
C3—C4—C5—C60.0 (15)C17—C18—C19—C201.1 (14)
O1—C1—C6—C5−179.4 (6)C16—C15—C20—C19−0.4 (15)
C2—C1—C6—C50.2 (16)O2—C15—C20—C19179.6 (6)
C4—C5—C6—C10.1 (16)C18—C19—C20—C150.4 (15)
C1—O1—C7—C8172.5 (5)C15—O2—C21—C22−172.6 (5)
C14—N2—C8—N1−1.5 (7)C28—N4—C22—N30.2 (7)
C14—N2—C8—C7173.1 (5)C28—N4—C22—C21−175.0 (5)
C9—N1—C8—N22.0 (8)C23—N3—C22—N4−1.0 (7)
C9—N1—C8—C7−172.9 (5)C23—N3—C22—C21174.3 (5)
O1—C7—C8—N2146.8 (6)O2—C21—C22—N4−149.1 (5)
O1—C7—C8—N1−39.0 (7)O2—C21—C22—N336.1 (7)
C8—N1—C9—C10177.0 (5)C22—N3—C23—C24−176.6 (5)
C8—N1—C9—C14−1.6 (6)C22—N3—C23—C281.3 (6)
N1—C9—C10—C11−177.4 (5)N3—C23—C24—C25176.7 (5)
C14—C9—C10—C111.0 (6)C28—C23—C24—C25−1.0 (6)
C9—C10—C11—C12−2.2 (6)C23—C24—C25—C261.5 (7)
C10—C11—C12—C131.2 (6)C24—C25—C26—C27−0.5 (7)
C11—C12—C13—C141.1 (6)C25—C26—C27—C28−1.1 (6)
C12—C13—C14—N2176.8 (4)C26—C27—C28—N4−175.4 (4)
C12—C13—C14—C9−2.3 (5)C26—C27—C28—C231.5 (6)
C8—N2—C14—C13−178.8 (5)C22—N4—C28—C27177.8 (5)
C8—N2—C14—C90.4 (6)C22—N4—C28—C230.7 (5)
N1—C9—C14—C13−179.9 (4)N3—C23—C28—C27−178.7 (4)
C10—C9—C14—C131.3 (6)C24—C23—C28—C27−0.5 (6)
N1—C9—C14—N20.7 (5)N3—C23—C28—N4−1.3 (5)
C10—C9—C14—N2−178.0 (4)C24—C23—C28—N4176.9 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.88 (1)2.03 (2)2.879 (7)163 (6)
N3—H3···N4ii0.88 (1)1.97 (2)2.845 (8)172 (5)
Symmetry codes: (i) x−1/2, −y+2, z; (ii) x−1/2, −y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.88 (1)2.03 (2)2.879 (7)163 (6)
N3—H3···N4ii0.88 (1)1.97 (2)2.845 (8)172 (5)
Symmetry codes: (i) x−1/2, −y+2, z; (ii) x−1/2, −y+1, z.
Acknowledgements top

We thank the University of Malaya for supporting this study (FS358/2008 A).

references
References top

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Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820.

Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7.

Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.