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ISSN: 2056-9890

1H-Benzimidazol-2-ylmethyl phenyl ether

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 2 March 2009; accepted 4 March 2009; online 11 March 2009)

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[Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165.]); Hassan et al. (2008[Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820.]); Idris et al. (2009[Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7.]); Shah Bakhtiar et al. (2009[Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2O

  • Mr = 224.26

  • Orthorhombic, P c a 21

  • 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)

  • Rint = 0.091

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [x-{\script{1\over 2}}, -y+2, z]; (ii) [x-{\script{1\over 2}}, -y+1, z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 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 top
Bruker SMART APEX CCD
diffractometer
1783 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
ω scansh = 1212
15022 measured reflectionsk = 1110
2699 independent reflectionsl = 3534
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 Å3
3 restraintsΔρmin = 0.23 e Å3
Crystal data top
C14H12N2OV = 2312.5 (2) Å3
Mr = 224.26Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 10.0299 (5) ŵ = 0.08 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0463 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.19 e Å3
2699 reflectionsΔρmin = 0.23 e Å3
313 parameters
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)
H10.030 (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)
C20.0889 (9)1.3564 (10)0.4484 (3)0.038 (2)
H20.13151.26140.43920.046*
C30.1303 (13)1.4968 (6)0.4286 (5)0.046 (3)
H3A0.20251.49800.40590.055*
C40.0687 (9)1.6364 (10)0.4412 (3)0.0363 (19)
H40.09771.73260.42710.044*
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)
H100.07990.70880.61080.029*
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)
H260.51970.00770.17660.034*
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, º) 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—C66.1 (11)C21—O2—C15—C16172.0 (6)
C7—O1—C1—C2174.2 (6)C21—O2—C15—C207.9 (10)
C6—C1—C2—C30.5 (15)C20—C15—C16—C170.9 (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—C50.4 (18)C16—C17—C18—C192.4 (16)
C3—C4—C5—C60.0 (15)C17—C18—C19—C201.1 (14)
O1—C1—C6—C5179.4 (6)C16—C15—C20—C190.4 (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—C22172.6 (5)
C14—N2—C8—N11.5 (7)C28—N4—C22—N30.2 (7)
C14—N2—C8—C7173.1 (5)C28—N4—C22—C21175.0 (5)
C9—N1—C8—N22.0 (8)C23—N3—C22—N41.0 (7)
C9—N1—C8—C7172.9 (5)C23—N3—C22—C21174.3 (5)
O1—C7—C8—N2146.8 (6)O2—C21—C22—N4149.1 (5)
O1—C7—C8—N139.0 (7)O2—C21—C22—N336.1 (7)
C8—N1—C9—C10177.0 (5)C22—N3—C23—C24176.6 (5)
C8—N1—C9—C141.6 (6)C22—N3—C23—C281.3 (6)
N1—C9—C10—C11177.4 (5)N3—C23—C24—C25176.7 (5)
C14—C9—C10—C111.0 (6)C28—C23—C24—C251.0 (6)
C9—C10—C11—C122.2 (6)C23—C24—C25—C261.5 (7)
C10—C11—C12—C131.2 (6)C24—C25—C26—C270.5 (7)
C11—C12—C13—C141.1 (6)C25—C26—C27—C281.1 (6)
C12—C13—C14—N2176.8 (4)C26—C27—C28—N4175.4 (4)
C12—C13—C14—C92.3 (5)C26—C27—C28—C231.5 (6)
C8—N2—C14—C13178.8 (5)C22—N4—C28—C27177.8 (5)
C8—N2—C14—C90.4 (6)C22—N4—C28—C230.7 (5)
N1—C9—C14—C13179.9 (4)N3—C23—C28—C27178.7 (4)
C10—C9—C14—C131.3 (6)C24—C23—C28—C270.5 (6)
N1—C9—C14—N20.7 (5)N3—C23—C28—N41.3 (5)
C10—C9—C14—N2178.0 (4)C24—C23—C28—N4176.9 (4)
Hydrogen-bond geometry (Å, º) 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) x1/2, y+2, z; (ii) x1/2, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H12N2O
Mr224.26
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)120
a, b, c (Å)10.0299 (5), 8.5391 (4), 27.000 (1)
V3)2312.5 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.10 × 0.03
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15022, 2699, 1783
Rint0.091
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.111, 1.00
No. of reflections2699
No. of parameters313
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) 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) x1/2, y+2, z; (ii) x1/2, y+1, z.
 

Acknowledgements

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

References

First citationAbdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165.  Web of Science CSD CrossRef IUCr Journals
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820.  Web of Science CSD CrossRef IUCr Journals
First citationIdris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7.  Web of Science CSD CrossRef IUCr Journals
First citationShah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2009). publCIF. In preparation.

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