4-[(4-Amino-3-pyrid­yl)imino­meth­yl]benzonitrile

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

doi:10.1107/S1600536808037070

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2342

doi:10.1107/S1600536808037070

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4-[(4-Amino-3-pyridyl)iminomethyl]benzonitrile

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

^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 7 November 2008; accepted 10 November 2008; online 13 November 2008)

The asymmetric unit of the potential mono-Schiff base ligand title compound, C₁₃H₁₀N₄, contains two crystallographically independent molecules, A and B. In molecule A, the two rings are twisted from each other by 13.90 (18)°. By contrast, the dihedral angle between the two rings in molecule B is 0.67 (19)°. In the crystal structure, molecules are linked through intermolecular N—H⋯N interactions via R₄⁴(32) motifs, forming two-dimensional arrays. The short distances between the centroids of the six-membered rings indicate the existence of π–π interactions [centroid–centroid distances = 3.6880 (17)–3.7466 (15) Å].

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Li et al. (2005 ); Bomfim et al. (2005 ); Glidewell et al. (2005 , 2006 ); Sun et al. (2004 ); Fun et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₀N₄
M_r = 222.25
Monoclinic, P 2₁ /c
a = 13.5560 (8) Å
b = 12.3000 (7) Å
c = 15.7514 (8) Å
β = 124.651 (2)°
V = 2160.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100.0 (1) K
0.45 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.962, T_max = 0.994
18251 measured reflections
3810 independent reflections
2372 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.219
S = 1.03
3810 reflections
323 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3A—H2NA⋯N4Aⁱ	0.92 (4)	2.26 (4)	3.155 (4)	165 (3)
N3A—H1NA⋯N1Bⁱⁱ	0.89 (4)	2.33 (5)	3.080 (4)	143 (4)
N3B—H2NB⋯N1Aⁱⁱⁱ	0.89 (4)	2.42 (4)	3.112 (4)	136 (4)
N3B—H1NB⋯N4Bⁱ	0.90 (4)	2.36 (4)	3.220 (4)	159 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR2004 (Burla et al., 2003 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037070/tk2327sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037070/tk2327Isup2.hkl

checkCIF report

Comment top

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry and play an important role in the development of coordination chemistry (Fun et al., 2008). Structures of Schiff bases derived from substituted benzaldehydes have been reported previously (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2005, 2006; Sun et al., 2004; Fun et al., 2008).

Each imino (C ═N) functional group is co-planar with the adjacent benzene ring in (I), Fig. 1. Two independent molecules, A and B, comprise the crystallographic asymmetric unit. In molecule A, the two phenyl rings are twisted from each other by 13.90 (18)°. The dihedral angle between the two phenyl rings in molecule B is 0.67 (19)° which indicates the molecule is planar. In the crystal structure, molecules are linked together through intermolecular N—H···N interactions via R₄⁴(32) motifs to form 2-D arrays parallel to the ab-plane, Fig. 2 & Table 1. The short distances between the centroids of the six-membered rings prove the existence of π–π interactions [Cg1···Cg4ⁱ = 3.7466 (15) Å, (i) x, 1/2 - y, -1/2 + z; Cg2···Cg3ⁱ = 3.6894 (14) Å; Cg3···Cg4ⁱⁱ, (ii) 1 - x,-y, 1 - z; Cg1, Cg2, Cg3, and Cg4 are the centroids of the N1A/C1A–C5A, C7A–C12A, N1B/C1B–C5B, and C7B–C12B rings, respectively.

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Li et al. (2005); Bomfim et al. (2005); Glidewell et al. (2005, 2006); Sun et al. (2004); Fun et al. (2008).

Experimental top

The synthetic method has been described earlier (Fun et al., 2008). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution of (I) held at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR2004 (Burla et al., 2003); 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, 2003).

Figures top

	Fig. 1. The molecular structure of (I) with atom labels and 50% displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed down the c-axis showing a part of the 2-D array and R₄⁴(32) ring motifs. Intermolecular hydrogen bonds are shown as dashed lines.

4-[(4-Amino-3-pyridyl)iminomethyl]benzonitrile top

Crystal data top

C₁₃H₁₀N₄	F(000) = 928
M_r = 222.25	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1699 reflections
a = 13.5560 (8) Å	θ = 2.3–30.1°
b = 12.3000 (7) Å	µ = 0.09 mm⁻¹
c = 15.7514 (8) Å	T = 100 K
β = 124.651 (2)°	Needle, yellow
V = 2160.5 (2) Å³	0.45 × 0.09 × 0.07 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3810 independent reflections
Radiation source: fine-focus sealed tube	2372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
T_min = 0.962, T_max = 0.994	k = −14→13
18251 measured reflections	l = −18→18

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.219	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1298P)² + 0.1507P] where P = (F_o² + 2F_c²)/3
3810 reflections	(Δ/σ)_max < 0.001
323 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₁₀N₄	V = 2160.5 (2) Å³
M_r = 222.25	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5560 (8) Å	µ = 0.09 mm⁻¹
b = 12.3000 (7) Å	T = 100 K
c = 15.7514 (8) Å	0.45 × 0.09 × 0.07 mm
β = 124.651 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3810 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2372 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.994	R_int = 0.060
18251 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.219	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.63 e Å⁻³
3810 reflections	Δρ_min = −0.29 e Å⁻³
323 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
N1A	0.6639 (2)	0.12555 (19)	0.38263 (17)	0.0217 (6)
N2A	0.85668 (19)	0.33048 (19)	0.36498 (16)	0.0148 (6)
N3A	0.9556 (2)	0.1387 (2)	0.3572 (2)	0.0277 (7)
N4A	1.0578 (2)	0.9061 (2)	0.36363 (17)	0.0227 (6)
C1A	0.8618 (2)	0.1349 (2)	0.36579 (19)	0.0185 (7)
C2A	0.8126 (2)	0.0361 (2)	0.36880 (19)	0.0200 (7)
H2AA	0.8447	−0.0292	0.3654	0.024*
C3A	0.7163 (2)	0.0359 (2)	0.3769 (2)	0.0210 (7)
H3AA	0.6856	−0.0312	0.3784	0.025*
C4A	0.7119 (2)	0.2198 (2)	0.37969 (19)	0.0184 (7)
H4AA	0.6773	0.2833	0.3834	0.022*
C5A	0.8084 (2)	0.2316 (2)	0.37159 (19)	0.0156 (6)
C6A	0.8305 (2)	0.4207 (2)	0.38827 (19)	0.0173 (7)
H6AA	0.7799	0.4207	0.4104	0.021*
C7A	0.8790 (2)	0.5238 (2)	0.38050 (18)	0.0140 (6)
C8A	0.9575 (2)	0.5272 (2)	0.34913 (18)	0.0189 (7)
H8AA	0.9781	0.4632	0.3313	0.023*
C9A	1.0037 (2)	0.6245 (2)	0.34472 (19)	0.0203 (7)
H9AA	1.0551	0.6263	0.3234	0.024*
C10A	0.9739 (2)	0.7212 (2)	0.37224 (19)	0.0156 (6)
C11A	0.8961 (2)	0.7180 (2)	0.40366 (19)	0.0185 (7)
H11A	0.8755	0.7819	0.4217	0.022*
C12A	0.8499 (2)	0.6198 (2)	0.40791 (19)	0.0168 (7)
H12A	0.7987	0.6179	0.4294	0.020*
C13A	1.0218 (2)	0.8236 (2)	0.36773 (19)	0.0173 (6)
C3B	0.7831 (2)	−0.3515 (2)	0.62159 (19)	0.0202 (7)
H3BA	0.8150	−0.4183	0.6211	0.024*
N2B	0.63747 (19)	−0.05867 (19)	0.62738 (16)	0.0183 (6)
N3B	0.5661 (2)	−0.2465 (2)	0.66987 (19)	0.0236 (6)
N4B	0.4350 (2)	0.5212 (2)	0.62229 (18)	0.0269 (6)
C1B	0.6482 (2)	−0.2527 (2)	0.64597 (19)	0.0160 (7)
C2B	0.6988 (2)	−0.3504 (2)	0.6444 (2)	0.0191 (7)
H2BA	0.6757	−0.4152	0.6588	0.023*
N1B	0.8223 (2)	−0.26157 (19)	0.59977 (17)	0.0225 (6)
C4B	0.7739 (3)	−0.1680 (2)	0.6022 (2)	0.0232 (7)
H4BA	0.7994	−0.1047	0.5878	0.028*
C5B	0.6885 (2)	−0.1573 (2)	0.62439 (19)	0.0153 (6)
C6B	0.6661 (2)	0.0318 (2)	0.6087 (2)	0.0207 (7)
H6BA	0.7215	0.0325	0.5916	0.025*
C7B	0.6158 (2)	0.1352 (2)	0.61273 (19)	0.0156 (6)
C8B	0.5309 (2)	0.1391 (2)	0.63648 (19)	0.0177 (7)
H8BA	0.5058	0.0751	0.6501	0.021*
C9B	0.4837 (3)	0.2381 (2)	0.6398 (2)	0.0197 (7)
H9BA	0.4278	0.2407	0.6562	0.024*
C10B	0.5212 (2)	0.3334 (2)	0.6183 (2)	0.0183 (7)
C11B	0.6066 (3)	0.3310 (2)	0.5956 (2)	0.0219 (7)
H11B	0.6321	0.3950	0.5823	0.026*
C12B	0.6525 (3)	0.2323 (2)	0.5929 (2)	0.0242 (7)
H12B	0.7094	0.2303	0.5776	0.029*
C13B	0.4722 (3)	0.4381 (3)	0.6207 (2)	0.0222 (7)
H2NA	0.999 (3)	0.077 (3)	0.366 (2)	0.028 (9)*
H1NA	0.996 (3)	0.199 (3)	0.365 (3)	0.048 (12)*
H2NB	0.527 (3)	−0.184 (3)	0.654 (2)	0.044 (11)*
H1NB	0.538 (3)	−0.311 (3)	0.675 (2)	0.039 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0241 (14)	0.0159 (14)	0.0297 (13)	−0.0010 (11)	0.0180 (12)	0.0011 (11)
N2A	0.0128 (12)	0.0135 (14)	0.0182 (11)	0.0012 (10)	0.0089 (10)	0.0005 (9)
N3A	0.0293 (16)	0.0154 (17)	0.0494 (17)	0.0009 (13)	0.0290 (14)	−0.0006 (13)
N4A	0.0240 (14)	0.0166 (15)	0.0305 (13)	0.0020 (11)	0.0173 (12)	0.0021 (11)
C1A	0.0197 (15)	0.0196 (18)	0.0157 (13)	−0.0026 (12)	0.0097 (12)	−0.0022 (12)
C2A	0.0239 (16)	0.0113 (17)	0.0263 (15)	−0.0020 (13)	0.0152 (13)	0.0005 (12)
C3A	0.0225 (16)	0.0148 (17)	0.0260 (15)	−0.0034 (13)	0.0140 (13)	0.0002 (12)
C4A	0.0154 (15)	0.0197 (18)	0.0203 (14)	0.0019 (12)	0.0103 (13)	−0.0010 (12)
C5A	0.0153 (14)	0.0134 (16)	0.0165 (13)	0.0020 (12)	0.0082 (12)	−0.0009 (11)
C6A	0.0141 (14)	0.0202 (18)	0.0179 (13)	0.0025 (12)	0.0094 (12)	−0.0004 (12)
C7A	0.0119 (13)	0.0140 (16)	0.0130 (12)	−0.0016 (11)	0.0053 (11)	0.0002 (11)
C8A	0.0216 (15)	0.0155 (17)	0.0191 (14)	0.0006 (12)	0.0113 (13)	−0.0034 (12)
C9A	0.0213 (16)	0.0210 (18)	0.0226 (14)	−0.0014 (13)	0.0149 (13)	−0.0006 (12)
C10A	0.0147 (14)	0.0136 (16)	0.0161 (13)	0.0008 (12)	0.0073 (12)	0.0008 (11)
C11A	0.0171 (15)	0.0163 (17)	0.0209 (14)	0.0033 (12)	0.0101 (13)	−0.0015 (12)
C12A	0.0151 (14)	0.0175 (17)	0.0209 (14)	0.0008 (12)	0.0121 (12)	−0.0004 (12)
C13A	0.0169 (15)	0.0178 (17)	0.0178 (14)	0.0000 (13)	0.0102 (12)	0.0006 (12)
C3B	0.0184 (15)	0.0199 (18)	0.0216 (15)	−0.0007 (12)	0.0109 (13)	−0.0029 (12)
N2B	0.0195 (13)	0.0145 (15)	0.0220 (12)	0.0044 (10)	0.0124 (11)	0.0027 (10)
N3B	0.0266 (15)	0.0137 (17)	0.0392 (15)	0.0009 (13)	0.0239 (13)	0.0023 (12)
N4B	0.0262 (14)	0.0168 (16)	0.0405 (15)	0.0033 (12)	0.0206 (13)	0.0012 (12)
C1B	0.0094 (13)	0.0216 (18)	0.0130 (13)	−0.0003 (12)	0.0040 (11)	0.0003 (11)
C2B	0.0182 (15)	0.0154 (17)	0.0218 (14)	0.0008 (12)	0.0103 (13)	0.0033 (12)
N1B	0.0213 (14)	0.0181 (15)	0.0310 (13)	0.0015 (11)	0.0166 (12)	−0.0030 (11)
C4B	0.0260 (16)	0.0171 (18)	0.0287 (15)	−0.0014 (13)	0.0169 (14)	0.0023 (13)
C5B	0.0126 (14)	0.0164 (17)	0.0142 (13)	0.0026 (11)	0.0060 (11)	−0.0008 (11)
C6B	0.0220 (15)	0.0198 (18)	0.0285 (15)	0.0034 (13)	0.0193 (13)	0.0038 (13)
C7B	0.0137 (14)	0.0169 (17)	0.0163 (13)	−0.0002 (12)	0.0087 (12)	−0.0007 (11)
C8B	0.0206 (16)	0.0141 (17)	0.0195 (14)	−0.0015 (12)	0.0120 (13)	0.0015 (11)
C9B	0.0192 (15)	0.0211 (18)	0.0238 (14)	−0.0015 (13)	0.0152 (13)	0.0001 (12)
C10B	0.0188 (15)	0.0151 (17)	0.0168 (13)	0.0004 (12)	0.0077 (12)	−0.0021 (11)
C11B	0.0264 (16)	0.0172 (18)	0.0264 (15)	−0.0005 (13)	0.0175 (14)	−0.0001 (12)
C12B	0.0269 (17)	0.0200 (18)	0.0345 (17)	0.0018 (13)	0.0227 (15)	0.0034 (13)
C13B	0.0192 (15)	0.0229 (19)	0.0246 (15)	−0.0025 (14)	0.0124 (13)	0.0000 (13)

Geometric parameters (Å, º) top

N1A—C3A	1.343 (3)	C3B—N1B	1.354 (3)
N1A—C4A	1.343 (3)	C3B—C2B	1.379 (4)
N2A—C6A	1.281 (3)	C3B—H3BA	0.9300
N2A—C5A	1.413 (3)	N2B—C6B	1.267 (3)
N3A—C1A	1.354 (4)	N2B—C5B	1.411 (3)
N3A—H2NA	0.93 (3)	N3B—C1B	1.366 (4)
N3A—H1NA	0.88 (4)	N3B—H2NB	0.88 (4)
N4A—C13A	1.143 (3)	N3B—H1NB	0.90 (4)
C1A—C2A	1.399 (4)	N4B—C13B	1.147 (4)
C1A—C5A	1.422 (4)	C1B—C2B	1.391 (4)
C2A—C3A	1.381 (4)	C1B—C5B	1.415 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—H3AA	0.9300	N1B—C4B	1.336 (4)
C4A—C5A	1.392 (4)	C4B—C5B	1.393 (4)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C6A—C7A	1.466 (4)	C6B—C7B	1.461 (4)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C7A—C12A	1.389 (4)	C7B—C12B	1.396 (4)
C7A—C8A	1.406 (4)	C7B—C8B	1.399 (4)
C8A—C9A	1.370 (4)	C8B—C9B	1.390 (4)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.402 (4)	C9B—C10B	1.394 (4)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.398 (4)	C10B—C11B	1.393 (4)
C10A—C13A	1.437 (4)	C10B—C13B	1.458 (4)
C11A—C12A	1.379 (4)	C11B—C12B	1.375 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—H12A	0.9300	C12B—H12B	0.9300

C3A—N1A—C4A	114.9 (2)	N1B—C3B—C2B	124.1 (3)
C6A—N2A—C5A	120.6 (2)	N1B—C3B—H3BA	117.9
C1A—N3A—H2NA	121.2 (19)	C2B—C3B—H3BA	117.9
C1A—N3A—H1NA	123 (2)	C6B—N2B—C5B	121.8 (2)
H2NA—N3A—H1NA	112 (3)	C1B—N3B—H2NB	115 (2)
N3A—C1A—C2A	121.7 (3)	C1B—N3B—H1NB	115 (2)
N3A—C1A—C5A	121.2 (3)	H2NB—N3B—H1NB	125 (3)
C2A—C1A—C5A	117.0 (3)	N3B—C1B—C2B	122.7 (3)
C3A—C2A—C1A	119.9 (3)	N3B—C1B—C5B	120.4 (3)
C3A—C2A—H2AA	120.0	C2B—C1B—C5B	116.8 (3)
C1A—C2A—H2AA	120.0	C3B—C2B—C1B	120.2 (3)
N1A—C3A—C2A	124.6 (3)	C3B—C2B—H2BA	119.9
N1A—C3A—H3AA	117.7	C1B—C2B—H2BA	119.9
C2A—C3A—H3AA	117.7	C4B—N1B—C3B	115.3 (3)
N1A—C4A—C5A	126.3 (3)	N1B—C4B—C5B	125.4 (3)
N1A—C4A—H4AA	116.9	N1B—C4B—H4BA	117.3
C5A—C4A—H4AA	116.9	C5B—C4B—H4BA	117.3
C4A—C5A—N2A	126.5 (3)	C4B—C5B—N2B	125.6 (3)
C4A—C5A—C1A	117.2 (3)	C4B—C5B—C1B	118.2 (3)
N2A—C5A—C1A	116.2 (2)	N2B—C5B—C1B	116.2 (2)
N2A—C6A—C7A	121.0 (2)	N2B—C6B—C7B	122.8 (3)
N2A—C6A—H6AA	119.5	N2B—C6B—H6BA	118.6
C7A—C6A—H6AA	119.5	C7B—C6B—H6BA	118.6
C12A—C7A—C8A	119.3 (3)	C12B—C7B—C8B	118.8 (3)
C12A—C7A—C6A	119.3 (2)	C12B—C7B—C6B	120.0 (2)
C8A—C7A—C6A	121.3 (3)	C8B—C7B—C6B	121.2 (3)
C9A—C8A—C7A	120.2 (3)	C9B—C8B—C7B	120.4 (3)
C9A—C8A—H8AA	119.9	C9B—C8B—H8BA	119.8
C7A—C8A—H8AA	119.9	C7B—C8B—H8BA	119.8
C8A—C9A—C10A	120.3 (3)	C8B—C9B—C10B	119.2 (3)
C8A—C9A—H9AA	119.8	C8B—C9B—H9BA	120.4
C10A—C9A—H9AA	119.8	C10B—C9B—H9BA	120.4
C11A—C10A—C9A	119.6 (3)	C11B—C10B—C9B	121.0 (3)
C11A—C10A—C13A	119.7 (3)	C11B—C10B—C13B	118.9 (3)
C9A—C10A—C13A	120.7 (3)	C9B—C10B—C13B	120.1 (3)
C12A—C11A—C10A	119.8 (3)	C12B—C11B—C10B	118.9 (3)
C12A—C11A—H11A	120.1	C12B—C11B—H11B	120.5
C10A—C11A—H11A	120.1	C10B—C11B—H11B	120.5
C11A—C12A—C7A	120.8 (3)	C11B—C12B—C7B	121.6 (3)
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.2
C7A—C12A—H12A	119.6	C7B—C12B—H12B	119.2
N4A—C13A—C10A	178.6 (3)	N4B—C13B—C10B	178.8 (3)

N3A—C1A—C2A—C3A	−179.5 (3)	N1B—C3B—C2B—C1B	0.1 (4)
C5A—C1A—C2A—C3A	0.1 (4)	N3B—C1B—C2B—C3B	−178.8 (2)
C4A—N1A—C3A—C2A	0.2 (4)	C5B—C1B—C2B—C3B	−0.7 (4)
C1A—C2A—C3A—N1A	−0.3 (4)	C2B—C3B—N1B—C4B	0.4 (4)
C3A—N1A—C4A—C5A	−0.1 (4)	C3B—N1B—C4B—C5B	−0.3 (4)
N1A—C4A—C5A—N2A	177.7 (2)	N1B—C4B—C5B—N2B	179.8 (2)
N1A—C4A—C5A—C1A	0.0 (4)	N1B—C4B—C5B—C1B	−0.3 (4)
C6A—N2A—C5A—C4A	15.3 (4)	C6B—N2B—C5B—C4B	0.4 (4)
C6A—N2A—C5A—C1A	−167.0 (2)	C6B—N2B—C5B—C1B	−179.5 (2)
N3A—C1A—C5A—C4A	179.6 (2)	N3B—C1B—C5B—C4B	178.9 (2)
C2A—C1A—C5A—C4A	−0.1 (3)	C2B—C1B—C5B—C4B	0.7 (4)
N3A—C1A—C5A—N2A	1.7 (4)	N3B—C1B—C5B—N2B	−1.1 (4)
C2A—C1A—C5A—N2A	−178.0 (2)	C2B—C1B—C5B—N2B	−179.3 (2)
C5A—N2A—C6A—C7A	−179.3 (2)	C5B—N2B—C6B—C7B	−179.1 (2)
N2A—C6A—C7A—C12A	−179.0 (2)	N2B—C6B—C7B—C12B	178.9 (3)
N2A—C6A—C7A—C8A	−1.2 (4)	N2B—C6B—C7B—C8B	−0.9 (4)
C12A—C7A—C8A—C9A	−0.7 (4)	C12B—C7B—C8B—C9B	0.3 (4)
C6A—C7A—C8A—C9A	−178.5 (2)	C6B—C7B—C8B—C9B	−179.9 (2)
C7A—C8A—C9A—C10A	0.5 (4)	C7B—C8B—C9B—C10B	0.6 (4)
C8A—C9A—C10A—C11A	−0.4 (4)	C8B—C9B—C10B—C11B	−1.2 (4)
C8A—C9A—C10A—C13A	−179.9 (2)	C8B—C9B—C10B—C13B	179.5 (2)
C9A—C10A—C11A—C12A	0.4 (4)	C9B—C10B—C11B—C12B	1.0 (4)
C13A—C10A—C11A—C12A	179.9 (2)	C13B—C10B—C11B—C12B	−179.7 (2)
C10A—C11A—C12A—C7A	−0.5 (4)	C10B—C11B—C12B—C7B	−0.1 (4)
C8A—C7A—C12A—C11A	0.7 (4)	C8B—C7B—C12B—C11B	−0.5 (4)
C6A—C7A—C12A—C11A	178.6 (2)	C6B—C7B—C12B—C11B	179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H2NA···N4Aⁱ	0.92 (4)	2.26 (4)	3.155 (4)	165 (3)
N3A—H1NA···N1Bⁱⁱ	0.89 (4)	2.33 (5)	3.080 (4)	143 (4)
N3B—H2NB···N1Aⁱⁱⁱ	0.89 (4)	2.42 (4)	3.112 (4)	136 (4)
N3B—H1NB···N4Bⁱ	0.90 (4)	2.36 (4)	3.220 (4)	159 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₄
M_r	222.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.5560 (8), 12.3000 (7), 15.7514 (8)
β (°)	124.651 (2)
V (Å³)	2160.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.09 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.962, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	18251, 3810, 2372
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.219, 1.03
No. of reflections	3810
No. of parameters	323
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.29

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR2004 (Burla et al., 2003), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H2NA···N4Aⁱ	0.92 (4)	2.26 (4)	3.155 (4)	165 (3)
N3A—H1NA···N1Bⁱⁱ	0.89 (4)	2.33 (5)	3.080 (4)	143 (4)
N3B—H2NB···N1Aⁱⁱⁱ	0.89 (4)	2.42 (4)	3.112 (4)	136 (4)
N3B—H1NB···N4Bⁱ	0.90 (4)	2.36 (4)	3.220 (4)	159 (2)

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

Footnotes

‡Additional correspondence author, e-mail: hkargar@pnu.ac.ir.

Acknowledgements

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

References

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