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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o733.
Published online 2009 March 11. doi:  10.1107/S1600536809007922
PMCID: PMC2969076

1H-Benzimidazol-2-ylmethyl phenyl ether

Abstract

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

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

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Object name is e-65-0o733-scheme1.jpg

Experimental

Crystal data

  • C14H12N2O
  • M r = 224.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o733-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

C14H12N2OF(000) = 944
Mr = 224.26Dx = 1.288 Mg m3
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 mm1
c = 27.000 (1) ÅT = 120 K
V = 2312.5 (2) Å3Prism, colorless
Z = 80.40 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEX CCD diffractometer1783 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

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 = 1.00w = 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 Å3
3 restraintsΔρmin = −0.23 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2923).

References

  • Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165. [PMC free article] [PubMed]
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