4-[1-(4-Cyano­benz­yl)-1H-benzimidazol-2-yl]benzonitrile

Kia, R.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809006989

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o660-o661

doi:10.1107/S1600536809006989

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4-[1-(4-Cyanobenzyl)-1H-benzimidazol-2-yl]benzonitrile

Reza Kia,^a Hoong-Kun Fun ^a ^* and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 15 January 2009; accepted 25 February 2009; online 6 March 2009)

In the title compound, C₂₂H₁₄N₄, a new substituted benzimidazole, three intermolecular C—H⋯N interactions link neighbouring molecules into different dimers with R₂²(12), R₂²(8) and R₂²(24) ring motifs. A fourth C—H⋯N interaction links neighbouring molecules along the c axis. There is also a short intermolecular contact between the azomethine (C=N) segment of the benzimidazole ring and one of the C atoms of a neighbouring benzene ring [N⋯C = 3.191 (5), C⋯C = 3.364 (6) Å], which links the molecules along the a axis. The two cyanobenzene rings are almost perpendicular to each other, with an interplanar angle of 87.70 (7)°. The dihedral angles between the mean planes of the benzimidazole ring and the two outer benzene rings are 36.27 (16) and 86.70 (16)°. In the crystal structure, molecules are stacked down the a axis with centroid–centroid distances of 3.906 (2)–3.912 (2) Å and interplanar distances of 3.5040 (17) and 3.6235 (17) Å.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For benzimidazole chemistry, reaction mechanisms and their bioactivity, see, for example: Latif et al. (1983 ); Craigo et al. (1999 ); Gudmundsson et al. (2000 ); Trivedi et al. (2006); Kim et al. (1996 ); Ramla et al. (2006 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₄N₄
M_r = 334.37
Monoclinic, P 2₁ /n
a = 5.0553 (4) Å
b = 17.3437 (10) Å
c = 19.6339 (14) Å
β = 97.653 (5)°
V = 1706.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.45 × 0.09 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.965, T_max = 0.997
15641 measured reflections
2906 independent reflections
1490 reflections with I > 2σ(I)
R_int = 0.153

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.169
S = 1.07
2906 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯N1ⁱ	0.93	2.62	3.425 (5)	146
C19—H19A⋯N4ⁱⁱ	0.93	2.57	3.502 (6)	175
C9—H9A⋯N4ⁱⁱⁱ	0.93	2.71	3.361 (5)	128
C14—H14A⋯N3^iv	0.97	2.57	3.502 (5)	162
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x, -y, -z; (iii) -x+1, -y, -z; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006989/zl2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006989/zl2173Isup2.hkl

checkCIF report

Comment top

Benzimidazoles are used widely in biological applications and as pharmaceutical agents (Craigo et al., 1999; Gudmundsson et al., 2000; Trivedi et al., 2006). They are also used as topoisomerase I inhibitors (Kim et al., 1996) and for antitumor activity (Ramla et al., 2006). Due to these important applications, many synthetic routes towards benzimidazoles have been developed. They can, for example, be synthesized by the reaction of phenolic aldehydes with o-phenylenediamine (Latif et al., 1983). Based on this route the title compound was synthesized and its crystal structure is reported here.

The title compound, Fig.1, comprises a single molecule in the asymmetric unit. Three intermolecular C—H···N interactions link neighbouring molecules into different dimers with R₂²(12), R₂²(8) and R₂²(24) ring motifs (Bernstein et al., 1995). A fourth C—H···N interaction links neighbouring molecules along the c axis. The two cyanobenzene rings are almost perpendicular to each other, with an interplanar angle of 87.70 (7)°. The dihedral angles between the the mean planes of the benzimidazole ring and the two outer benzene rings are 36.27 (16) and 86.70 (16)°. There is also a short intermolecular contact between the azomethine (C1═N1) segment of the benzimidazole ring and one of the carbon atoms (C13) of the neighbouring benzene rings which links the molecules along the a axis (N1···C13^v = 3.191 (5) C1···C13^v = 3.364 (6), symmetry code: (v) x-1, y, z). In the crystal structure, the molecules are stacked down the a axis with centroid to centroid distances of 3.906 (2)–3.912 (2) Å and interplanar distances of 3.5040 (17) and 3.6235 (17) Å [Cg1···Cg2^vi = 3.906 (2); (vi) 1 + x, y, z and Cg1···Cg3^vii = 3.912 (2) Å; (vii) -1 + x, y, z: Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6/N2/C7, C1–C6, and C8–C13 benzene rings] (Fig. 2).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For benzimidazole chemistry, reaction mechanisms and their bioactivity, see, for example: Latif et al. (1983); Craigo et al. (1999); Gudmundsson et al. (2000); Trivedi et al. (2006); Kim et al. (1996); Ramla et al. (2006). For the stability of the temperature controller, see: Cosier & Glazer (1986).

Experimental top

An ethanolic solution (50 ml) of 4-cyanobenzaldehyde (2 mmol, 263 mg) was added to 1,2-phenylenediamine (1 mmol, 217 mg). The mixture was refluxed for 2 h, and cooled to room temperature. The resulting colourless powder was filtered, washed with cooled ethanol and dried in vacuo. Single crystals suitable for X-ray diffraction were obtained from an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed down the a-axis showing infinite stacks of molecules along the a-axis and also linking of molecules through C—H···N interactions along the c-axis. Intermolecular hydrogen bonds are shown as dashed lines.

4-[1-(4-Cyanobenzyl)-1H-benzimidazol-2-yl]benzonitrile top

Crystal data top

C₂₂H₁₄N₄	F(000) = 696
M_r = 334.37	D_x = 1.302 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3931 reflections
a = 5.0553 (4) Å	θ = 2.4–30.2°
b = 17.3437 (10) Å	µ = 0.08 mm⁻¹
c = 19.6339 (14) Å	T = 100 K
β = 97.653 (5)°	Needle, colourless
V = 1706.1 (2) Å³	0.45 × 0.09 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2906 independent reflections
Radiation source: fine-focus sealed tube	1490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.153
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
T_min = 0.965, T_max = 0.997	k = −20→20
15641 measured reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.079	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.0473P)² + 1.9898P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2906 reflections	Δρ_max = 0.26 e Å⁻³
236 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (18)

Crystal data top

C₂₂H₁₄N₄	V = 1706.1 (2) Å³
M_r = 334.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.0553 (4) Å	µ = 0.08 mm⁻¹
b = 17.3437 (10) Å	T = 100 K
c = 19.6339 (14) Å	0.45 × 0.09 × 0.04 mm
β = 97.653 (5)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2906 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1490 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.997	R_int = 0.153
15641 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.07	Δρ_max = 0.26 e Å⁻³
2906 reflections	Δρ_min = −0.35 e Å⁻³
236 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
N1	0.7041 (7)	0.41520 (18)	0.10705 (18)	0.0222 (9)
N2	0.8001 (6)	0.29462 (17)	0.14467 (17)	0.0196 (9)
N3	1.5730 (8)	0.3343 (2)	−0.1704 (2)	0.0366 (11)
N4	0.1768 (8)	−0.0990 (2)	0.05749 (19)	0.0328 (10)
C1	0.5702 (8)	0.3997 (2)	0.1633 (2)	0.0205 (10)
C2	0.3933 (8)	0.4456 (2)	0.1943 (2)	0.0250 (11)
H2A	0.3510	0.4953	0.1787	0.030*
C3	0.2841 (8)	0.4148 (2)	0.2487 (2)	0.0271 (11)
H3A	0.1639	0.4441	0.2697	0.033*
C4	0.3485 (8)	0.3408 (2)	0.2733 (2)	0.0272 (11)
H4A	0.2719	0.3223	0.3105	0.033*
C5	0.5240 (8)	0.2944 (2)	0.2434 (2)	0.0240 (11)
H5A	0.5681	0.2451	0.2597	0.029*
C6	0.6310 (8)	0.3255 (2)	0.1876 (2)	0.0197 (10)
C7	0.8349 (8)	0.3516 (2)	0.0971 (2)	0.0196 (10)
C8	0.9937 (8)	0.3425 (2)	0.0400 (2)	0.0183 (10)
C9	1.0085 (8)	0.2747 (2)	0.0032 (2)	0.0206 (11)
H9A	0.9193	0.2310	0.0153	0.025*
C10	1.1554 (8)	0.2718 (2)	−0.0515 (2)	0.0248 (11)
H10A	1.1656	0.2262	−0.0758	0.030*
C11	1.2870 (8)	0.3372 (2)	−0.0697 (2)	0.0207 (11)
C12	1.2703 (8)	0.4059 (2)	−0.0344 (2)	0.0228 (11)
H12A	1.3561	0.4499	−0.0473	0.027*
C13	1.1248 (8)	0.4079 (2)	0.0200 (2)	0.0229 (11)
H13A	1.1135	0.4538	0.0439	0.027*
C14	0.9363 (8)	0.2212 (2)	0.1570 (2)	0.0221 (11)
H14A	0.9987	0.2167	0.2057	0.026*
H14B	1.0918	0.2209	0.1329	0.026*
C15	0.7667 (8)	0.1513 (2)	0.1346 (2)	0.0193 (10)
C16	0.8439 (8)	0.0795 (2)	0.1615 (2)	0.0232 (11)
H16A	0.9962	0.0751	0.1935	0.028*
C17	0.6958 (8)	0.0145 (2)	0.1410 (2)	0.0256 (11)
H17A	0.7492	−0.0336	0.1589	0.031*
C18	0.4669 (8)	0.0212 (2)	0.0936 (2)	0.0217 (11)
C19	0.3883 (8)	0.0931 (2)	0.0667 (2)	0.0228 (11)
H19A	0.2349	0.0978	0.0351	0.027*
C20	0.5388 (8)	0.1572 (2)	0.0871 (2)	0.0208 (10)
H20A	0.4869	0.2052	0.0687	0.025*
C21	1.4437 (9)	0.3350 (2)	−0.1261 (3)	0.0281 (12)
C22	0.3071 (9)	−0.0458 (2)	0.0734 (2)	0.0256 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.028 (2)	0.016 (2)	0.023 (2)	0.0017 (16)	0.0025 (19)	−0.0006 (16)
N2	0.026 (2)	0.0127 (19)	0.019 (2)	0.0003 (15)	0.0024 (18)	−0.0026 (16)
N3	0.043 (3)	0.031 (2)	0.036 (3)	−0.0030 (19)	0.006 (2)	−0.001 (2)
N4	0.045 (3)	0.027 (2)	0.027 (2)	−0.006 (2)	0.006 (2)	−0.0006 (18)
C1	0.026 (2)	0.016 (3)	0.019 (3)	−0.0022 (19)	0.003 (2)	−0.003 (2)
C2	0.029 (3)	0.015 (2)	0.030 (3)	0.003 (2)	0.000 (2)	−0.006 (2)
C3	0.025 (2)	0.031 (3)	0.027 (3)	−0.004 (2)	0.007 (2)	−0.006 (2)
C4	0.032 (3)	0.026 (3)	0.026 (3)	−0.008 (2)	0.008 (2)	−0.006 (2)
C5	0.028 (3)	0.019 (2)	0.024 (3)	−0.003 (2)	−0.002 (2)	−0.003 (2)
C6	0.024 (2)	0.016 (2)	0.018 (3)	−0.0035 (19)	0.001 (2)	−0.005 (2)
C7	0.021 (2)	0.017 (2)	0.019 (3)	−0.0054 (19)	−0.005 (2)	0.000 (2)
C8	0.021 (2)	0.015 (2)	0.019 (3)	0.0019 (18)	0.001 (2)	0.003 (2)
C9	0.023 (2)	0.016 (3)	0.023 (3)	−0.0008 (18)	0.003 (2)	0.004 (2)
C10	0.032 (3)	0.022 (3)	0.019 (3)	0.002 (2)	−0.001 (2)	−0.001 (2)
C11	0.022 (2)	0.021 (3)	0.020 (3)	0.0000 (19)	0.004 (2)	0.005 (2)
C12	0.031 (3)	0.017 (3)	0.021 (3)	−0.0037 (19)	0.004 (2)	−0.002 (2)
C13	0.031 (3)	0.015 (2)	0.022 (3)	0.002 (2)	0.002 (2)	−0.002 (2)
C14	0.023 (2)	0.021 (2)	0.023 (3)	0.0009 (19)	0.003 (2)	0.0011 (19)
C15	0.023 (3)	0.016 (2)	0.019 (3)	0.0013 (18)	0.005 (2)	−0.0030 (19)
C16	0.026 (2)	0.020 (2)	0.024 (3)	−0.001 (2)	0.004 (2)	0.001 (2)
C17	0.026 (3)	0.019 (2)	0.032 (3)	0.003 (2)	0.004 (3)	0.001 (2)
C18	0.026 (3)	0.017 (2)	0.024 (3)	−0.0035 (19)	0.010 (2)	−0.004 (2)
C19	0.021 (2)	0.024 (3)	0.022 (3)	0.000 (2)	0.001 (2)	0.001 (2)
C20	0.027 (3)	0.015 (2)	0.021 (3)	0.0006 (19)	0.004 (2)	−0.0002 (19)
C21	0.035 (3)	0.019 (3)	0.030 (3)	−0.003 (2)	0.003 (3)	0.000 (2)
C22	0.033 (3)	0.023 (3)	0.022 (3)	−0.001 (2)	0.007 (2)	0.002 (2)

Geometric parameters (Å, º) top

N1—C7	1.314 (5)	C10—C11	1.385 (5)
N1—C1	1.397 (5)	C10—H10A	0.9300
N2—C6	1.385 (5)	C11—C12	1.387 (5)
N2—C7	1.387 (5)	C11—C21	1.446 (6)
N2—C14	1.453 (5)	C12—C13	1.376 (5)
N3—C21	1.155 (5)	C12—H12A	0.9300
N4—C22	1.152 (5)	C13—H13A	0.9300
C1—C6	1.391 (5)	C14—C15	1.515 (5)
C1—C2	1.397 (5)	C14—H14A	0.9700
C2—C3	1.375 (6)	C14—H14B	0.9700
C2—H2A	0.9300	C15—C20	1.386 (5)
C3—C4	1.393 (6)	C15—C16	1.388 (5)
C3—H3A	0.9300	C16—C17	1.384 (5)
C4—C5	1.385 (6)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.390 (5)
C5—C6	1.394 (6)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.391 (5)
C7—C8	1.472 (6)	C18—C22	1.440 (6)
C8—C9	1.387 (5)	C19—C20	1.377 (5)
C8—C13	1.397 (5)	C19—H19A	0.9300
C9—C10	1.385 (5)	C20—H20A	0.9300
C9—H9A	0.9300

C7—N1—C1	105.2 (3)	C10—C11—C21	120.6 (4)
C6—N2—C7	106.1 (3)	C12—C11—C21	118.8 (4)
C6—N2—C14	123.7 (3)	C13—C12—C11	119.0 (4)
C7—N2—C14	129.6 (3)	C13—C12—H12A	120.5
C6—C1—C2	120.2 (4)	C11—C12—H12A	120.5
C6—C1—N1	109.9 (4)	C12—C13—C8	121.3 (4)
C2—C1—N1	129.8 (4)	C12—C13—H13A	119.3
C3—C2—C1	117.6 (4)	C8—C13—H13A	119.3
C3—C2—H2A	121.2	N2—C14—C15	114.6 (3)
C1—C2—H2A	121.2	N2—C14—H14A	108.6
C2—C3—C4	121.8 (4)	C15—C14—H14A	108.6
C2—C3—H3A	119.1	N2—C14—H14B	108.6
C4—C3—H3A	119.1	C15—C14—H14B	108.6
C5—C4—C3	121.5 (4)	H14A—C14—H14B	107.6
C5—C4—H4A	119.3	C20—C15—C16	119.3 (4)
C3—C4—H4A	119.3	C20—C15—C14	121.6 (3)
C4—C5—C6	116.4 (4)	C16—C15—C14	119.2 (4)
C4—C5—H5A	121.8	C17—C16—C15	120.4 (4)
C6—C5—H5A	121.8	C17—C16—H16A	119.8
N2—C6—C1	106.0 (4)	C15—C16—H16A	119.8
N2—C6—C5	131.6 (4)	C16—C17—C18	119.7 (4)
C1—C6—C5	122.4 (4)	C16—C17—H17A	120.1
N1—C7—N2	112.7 (4)	C18—C17—H17A	120.1
N1—C7—C8	122.6 (4)	C17—C18—C19	120.0 (4)
N2—C7—C8	124.6 (4)	C17—C18—C22	120.2 (4)
C9—C8—C13	118.8 (4)	C19—C18—C22	119.8 (4)
C9—C8—C7	124.0 (4)	C20—C19—C18	119.6 (4)
C13—C8—C7	117.1 (4)	C20—C19—H19A	120.2
C10—C9—C8	120.4 (4)	C18—C19—H19A	120.2
C10—C9—H9A	119.8	C19—C20—C15	120.9 (4)
C8—C9—H9A	119.8	C19—C20—H20A	119.6
C9—C10—C11	119.8 (4)	C15—C20—H20A	119.6
C9—C10—H10A	120.1	N3—C21—C11	178.5 (5)
C11—C10—H10A	120.1	N4—C22—C18	179.2 (5)
C10—C11—C12	120.7 (4)

C7—N1—C1—C6	1.5 (4)	N2—C7—C8—C13	−147.4 (4)
C7—N1—C1—C2	−177.1 (4)	C13—C8—C9—C10	1.3 (6)
C6—C1—C2—C3	−0.1 (6)	C7—C8—C9—C10	177.7 (4)
N1—C1—C2—C3	178.4 (4)	C8—C9—C10—C11	−0.3 (6)
C1—C2—C3—C4	0.9 (6)	C9—C10—C11—C12	−0.9 (6)
C2—C3—C4—C5	−0.7 (6)	C9—C10—C11—C21	179.3 (4)
C3—C4—C5—C6	−0.3 (6)	C10—C11—C12—C13	1.2 (6)
C7—N2—C6—C1	0.4 (4)	C21—C11—C12—C13	−179.0 (4)
C14—N2—C6—C1	172.4 (3)	C11—C12—C13—C8	−0.2 (6)
C7—N2—C6—C5	178.7 (4)	C9—C8—C13—C12	−1.0 (6)
C14—N2—C6—C5	−9.3 (6)	C7—C8—C13—C12	−177.7 (4)
C2—C1—C6—N2	177.5 (3)	C6—N2—C14—C15	81.2 (5)
N1—C1—C6—N2	−1.2 (4)	C7—N2—C14—C15	−108.9 (4)
C2—C1—C6—C5	−1.0 (6)	N2—C14—C15—C20	20.2 (5)
N1—C1—C6—C5	−179.7 (4)	N2—C14—C15—C16	−160.9 (4)
C4—C5—C6—N2	−177.0 (4)	C20—C15—C16—C17	0.2 (6)
C4—C5—C6—C1	1.1 (6)	C14—C15—C16—C17	−178.7 (4)
C1—N1—C7—N2	−1.3 (4)	C15—C16—C17—C18	−0.6 (6)
C1—N1—C7—C8	177.1 (3)	C16—C17—C18—C19	0.4 (6)
C6—N2—C7—N1	0.5 (4)	C16—C17—C18—C22	−178.2 (4)
C14—N2—C7—N1	−170.8 (4)	C17—C18—C19—C20	0.2 (6)
C6—N2—C7—C8	−177.8 (4)	C22—C18—C19—C20	178.7 (4)
C14—N2—C7—C8	10.9 (6)	C18—C19—C20—C15	−0.6 (6)
N1—C7—C8—C9	−142.1 (4)	C16—C15—C20—C19	0.3 (6)
N2—C7—C8—C9	36.1 (6)	C14—C15—C20—C19	179.3 (4)
N1—C7—C8—C13	34.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1ⁱ	0.93	2.62	3.425 (5)	146
C19—H19A···N4ⁱⁱ	0.93	2.57	3.502 (6)	175
C9—H9A···N4ⁱⁱⁱ	0.93	2.71	3.361 (5)	128
C14—H14A···N3^iv	0.97	2.57	3.502 (5)	162

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄N₄
M_r	334.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	5.0553 (4), 17.3437 (10), 19.6339 (14)
β (°)	97.653 (5)
V (Å³)	1706.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.09 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.965, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	15641, 2906, 1490
R_int	0.153
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.169, 1.07
No. of reflections	2906
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.35

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1ⁱ	0.9300	2.6200	3.425 (5)	146.00
C19—H19A···N4ⁱⁱ	0.9300	2.5700	3.502 (6)	175.00
C9—H9A···N4ⁱⁱⁱ	0.9300	2.7100	3.361 (5)	128.00
C14—H14A···N3^iv	0.9700	2.5700	3.502 (5)	162.00

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) x−1/2, −y+1/2, z+1/2.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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