1H-Benzimidazol-2-ylmethyl phenyl ether

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

doi:10.1107/S1600536809007922

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o733

doi:10.1107/S1600536809007922

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1H-Benzimidazol-2-ylmethyl phenyl ether

Noor Doha Hassan,^a Hairul Anuar Tajuddin,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^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 ); Hassan et al. (2008 ); Idris et al. (2009 ); Shah Bakhtiar et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₂N₂O
M_r = 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)
R_int = 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
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+2, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, z]$ .

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 ).

Supporting information

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

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

checkCIF report

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.

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

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

C₁₄H₁₂N₂O	F(000) = 944
M_r = 224.26	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0497P)² + 0.1971P] where P = (F_o² + 2F_c²)/3
2699 reflections	(Δ/σ)_max = 0.001
313 parameters	Δρ_max = 0.19 e Å⁻³
3 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O	V = 2312.5 (2) Å³
M_r = 224.26	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 10.0299 (5) Å	µ = 0.08 mm⁻¹
b = 8.5391 (4) Å	T = 120 K
c = 27.000 (1) Å	0.40 × 0.10 × 0.03 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1783 reflections with I > 2σ(I)
15022 measured reflections	R_int = 0.091
2699 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.19 e Å⁻³
2699 reflections	Δρ_min = −0.23 e Å⁻³
313 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+2, z; (ii) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O
M_r	224.26
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	120
a, b, c (Å)	10.0299 (5), 8.5391 (4), 27.000 (1)
V (Å³)	2312.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.10 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15022, 2699, 1783
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.111, 1.00
No. of reflections	2699
No. of parameters	313
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···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) x−1/2, −y+2, z; (ii) x−1/2, −y+1, z.

Acknowledgements

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

References

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