4-[(2E)-2-(2-Hy­droxy­benzyl­idene)hydrazin-1-yl]benzonitrile

Mohamed, S.K.; Bogdanović, G.A.; Abdelhamid, A.A.; Novaković, S.B.; Potgeiter, H.

doi:10.1107/S1600536812037841

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages o2886-o2887

https://doi.org/10.1107/S1600536812037841

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4-[(2E)-2-(2-Hydroxybenzylidene)hydrazin-1-yl]benzonitrile

Shaaban K. Mohamed,^a ^* Goran A. Bogdanović,^b Antar A. Abdelhamid,^a Sladjana B. Novaković ^b and Herman Potgeiter ^c

^aManchester Metropolitan University, Chemistry and Environmental Division, Manchester M1 5GD, England, ^b'Vinča' Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia, and ^cSchool of Research, Enterprise & Innovation, Manchester Metropolitan University, Manchester M1 5GD, England
^*Correspondence e-mail: s.mohamed@mmu.ac.uk

(Received 28 August 2012; accepted 3 September 2012; online 8 September 2012)

The asymmetric unit of the title Schiff base, C₁₄H₁₁N₃O, contains two independent molecules which have similar conformations. The dihedral angles between the benzene rings are 4.19 (9) and 14.18 (9)° in the two molecules. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation of each molecules. The crystal packing is dominated by pairs of equivalent N—H⋯N and C—H⋯O hydrogen bonds which arrange the molecules into layers parallel to (-111).

Related literature

For azomethines, see: Archibald et al. (1994 ); Harada et al. (1999 ); Ogawa et al. (1998 ). For the biological properties of Schiff bases, see: Lozier et al. (1975 ); Dao et al. (2000 ). For their coordination chemistry, see: Kargar et al. (2009 ); Yeap et al. (2009 ). For the structure of related Schiff bases reported by our group, see: Mohamed, Abdelhamid et al. (2012 ); Mohamed, Akkurt et al. (2012 ).

Experimental

Crystal data

C₁₄H₁₁N₃O
M_r = 237.26
Triclinic, $[P \overline 1]$
a = 8.1917 (7) Å
b = 11.6406 (7) Å
c = 13.4445 (8) Å
α = 103.006 (5)°
β = 104.387 (6)°
γ = 96.426 (6)°
V = 1190.67 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 293 K
0.26 × 0.15 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.827, T_max = 1.000
7913 measured reflections
4592 independent reflections
3696 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.121
S = 1.05
4592 reflections
341 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N1A	0.98 (2)	1.77 (2)	2.654 (2)	149 (2)
O1B—H1OB⋯N1B	0.90 (2)	1.86 (2)	2.653 (2)	147 (2)
N2A—H1NA⋯N3Bⁱ	0.91 (2)	2.17 (2)	3.065 (2)	166 (2)
N2B—H1NB⋯N3Aⁱⁱ	0.89 (2)	2.25 (2)	3.098 (2)	158 (2)
C7A—H7A⋯O1Bⁱⁱⁱ	0.93	2.55	3.427 (2)	156
C7B—H7B⋯O1A^iv	0.93	2.49	3.413 (2)	172
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y, -z+1; (iv) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 )'; software used to prepare material for publication: WinGX (Farrugia, 1999 ), PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037841/rz2800sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037841/rz2800Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037841/rz2800Isup3.cml

checkCIF report

Comment top

Schiff bases have received much attention in recent years (Ogawa et al., 1998; Archibald et al., 1994; Harada et al., 1999) due to their various biological activities and metal chelating properties. In many cases, they were shown to have antibacterial, anticancer, anti- inflammatory and antitoxic properties (Lozier et al., 1975; Dao et al., 2000) and have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Yeap et al., 2009). Recently, we reported on the crystal structures of two new Schiff bases (Mohamed, Abdelhamid et al., 2012; Mohamed, Akkurt et al., 2012). As a further investigation of the structures of Schiff base compounds, herin we report the synthesis and crystal structure of the title compound (I) which was obtained unintentionally from the component reaction of cyclohexan-1,3-dione, salicylaldehyde and 4- hydrazinylbenzonitrile in ethanol.

The title compound crystallizes with two independent molecules (A and B) in the asymmetric unit, Fig. 1. The molecules A and B have similar conformation and approximately planar form. In molecules A and B the dihedral angle between the corresponding aromatic rings is 4.19 (9) and 14.18 (9)°, respectively. The torsion angles C8—N2—N1—C1 and N2—N1—C1—C2, within the fragment which connects the rings, are 179.44 (14)/-179.93 (13) and 175.41 (13)/177.44 (12)°, in molecules A and B respectively. All these parameters suggest a somewhat higher planarity of molecule A in comparison to molecule B. The molecules of each type are stabilized by the cyclic intramolecular O1—H1o···N1 hydrogen bond (Table 1). In the crystal packing the A and B molecules mutually interact by the pairs of the strongest N2—H1n···N3 hydrogen bonds (Table 1) which engage the hydrazine donor and the nitirile acceptor from each type of molecule. The chains consisting of A and B molecules further interact by another pair of equivalent C7—H7···O1 interactions to give two dimensional lyres (Fig 2). The interaction between the parallel lyres towards the three-dimensional crystal packing is mostly based on weak van der Waals interactions.

Related literature top

For azomethines, see: Archibald et al. (1994); Harada et al. (1999); Ogawa et al. (1998). For the biological properties of Schiff bases, see: Lozier et al. (1975); Dao et al. (2000). For their coordination chemistry, see: Kargar et al. (2009); Yeap et al. (2009). For the structure of related Schiff bases reported by our group, see: Mohamed, Abdelhamid et al. (2012); Mohamed, Akkurt et al. (2012).

Experimental top

The title compound was prepared unintentionally as a major product from reaction of 112 mg (1 mmol) cyclohexane-1,3-dione, 133 mg (1 mmol) 4-hydrazinylbenzonitrile and 122 mg (1 mmol) salicylaldehyde in 50 ml ethanol. The reaction mixture was refluxed for 5 h. The excess solvent was evaporated under vacuum and the residual resins was triturated with cold acetone. The obtained solid was collected by filtration, dried and washed with acetone. Single crystals suitable for X-ray diffraction were grown from acetone solution of (I) using the slow evaporation method. M. p. 469 K.

Structure description top

For azomethines, see: Archibald et al. (1994); Harada et al. (1999); Ogawa et al. (1998). For the biological properties of Schiff bases, see: Lozier et al. (1975); Dao et al. (2000). For their coordination chemistry, see: Kargar et al. (2009); Yeap et al. (2009). For the structure of related Schiff bases reported by our group, see: Mohamed, Abdelhamid et al. (2012); Mohamed, Akkurt et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'; software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of (I) with atom numbering scheme. Displacement ellipsoids are drawn at the 35% probability level.
	Fig. 2. Two dimensional arrangement of A and B molecules via N—H···N and C—H···O hydrogen bonds.

4-[(2E)-2-(2-Hydroxybenzylidene)hydrazin-1-yl]benzonitrile top

Crystal data top

C₁₄H₁₁N₃O	Z = 4
M_r = 237.26	F(000) = 496
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 8.1917 (7) Å	Cell parameters from 3110 reflections
b = 11.6406 (7) Å	θ = 3.5–72.5°
c = 13.4445 (8) Å	µ = 0.70 mm⁻¹
α = 103.006 (5)°	T = 293 K
β = 104.387 (6)°	Prismatic, colorless
γ = 96.426 (6)°	0.26 × 0.15 × 0.14 mm
V = 1190.67 (14) Å³

Data collection top

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer	4592 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3696 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 16.3280 pixels mm^-1	θ_max = 72.6°, θ_min = 3.5°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→13
T_min = 0.827, T_max = 1.000	l = −16→14
7913 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0591P)² + 0.1257P] where P = (F_o² + 2F_c²)/3
4592 reflections	(Δ/σ)_max < 0.001
341 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O	γ = 96.426 (6)°
M_r = 237.26	V = 1190.67 (14) Å³
Triclinic, P1	Z = 4
a = 8.1917 (7) Å	Cu Kα radiation
b = 11.6406 (7) Å	µ = 0.70 mm⁻¹
c = 13.4445 (8) Å	T = 293 K
α = 103.006 (5)°	0.26 × 0.15 × 0.14 mm
β = 104.387 (6)°

Data collection top

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer	4592 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3696 reflections with I > 2σ(I)
T_min = 0.827, T_max = 1.000	R_int = 0.020
7913 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.16 e Å⁻³
4592 reflections	Δρ_min = −0.14 e Å⁻³
341 parameters

Special details top

Experimental. Absorption correction: Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 'CrysAlisPro (Oxford Diffraction, 2009)'

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

	x	y	z	U_iso*/U_eq
O1A	0.48536 (17)	0.59328 (11)	0.66183 (10)	0.0784 (4)
O1B	0.91964 (17)	−0.08146 (11)	0.25880 (10)	0.0774 (4)
N1A	0.22126 (15)	0.44483 (11)	0.51588 (9)	0.0526 (3)
N1B	0.93383 (15)	0.06285 (11)	0.13286 (9)	0.0522 (3)
N2A	0.09712 (17)	0.40478 (12)	0.42146 (10)	0.0596 (3)
N2B	0.87286 (17)	0.10497 (12)	0.04621 (10)	0.0602 (3)
N3A	−0.0385 (2)	0.69952 (14)	0.03913 (11)	0.0808 (5)
N3B	0.20536 (19)	−0.19989 (13)	−0.37048 (11)	0.0718 (4)
C1A	0.22866 (18)	0.37735 (12)	0.58006 (11)	0.0515 (3)
H1A	0.1506	0.3060	0.5593	0.062*
C1B	1.06978 (18)	0.12410 (12)	0.20323 (11)	0.0497 (3)
H1B	1.1242	0.1924	0.1917	0.060*
C2A	0.35367 (18)	0.40831 (12)	0.68322 (11)	0.0480 (3)
C2B	1.14175 (17)	0.09042 (12)	0.30040 (11)	0.0475 (3)
C3A	0.47572 (19)	0.51421 (13)	0.72128 (12)	0.0536 (3)
C3B	1.0654 (2)	−0.00961 (13)	0.32475 (12)	0.0549 (3)
C4A	0.5895 (2)	0.54087 (15)	0.82180 (13)	0.0662 (4)
H4A	0.6707	0.6109	0.8464	0.079*
C4B	1.1394 (2)	−0.03657 (15)	0.41970 (13)	0.0676 (4)
H4B	1.0883	−0.1025	0.4362	0.081*
C5A	0.5828 (2)	0.46422 (17)	0.88535 (13)	0.0706 (5)
H5A	0.6591	0.4832	0.9531	0.085*
C5B	1.2868 (2)	0.03347 (17)	0.48887 (13)	0.0735 (5)
H5B	1.3355	0.0142	0.5519	0.088*
C6A	0.4644 (2)	0.35943 (17)	0.84996 (13)	0.0703 (4)
H6A	0.4605	0.3079	0.8934	0.084*
C6B	1.3643 (2)	0.13218 (16)	0.46669 (13)	0.0695 (4)
H6B	1.4646	0.1793	0.5142	0.083*
C7A	0.3520 (2)	0.33197 (14)	0.74959 (12)	0.0600 (4)
H7A	0.2730	0.2608	0.7254	0.072*
C7B	1.29124 (19)	0.16031 (14)	0.37294 (12)	0.0574 (4)
H7B	1.3429	0.2272	0.3580	0.069*
C8A	0.07493 (18)	0.46900 (12)	0.34649 (11)	0.0511 (3)
C8B	0.73501 (18)	0.04005 (13)	−0.03593 (11)	0.0507 (3)
C9A	0.1698 (2)	0.58289 (14)	0.36363 (12)	0.0589 (4)
H9A	0.2530	0.6184	0.4279	0.071*
C9B	0.66057 (19)	−0.07671 (13)	−0.04234 (12)	0.0549 (3)
H9B	0.7039	−0.1134	0.0108	0.066*
C10A	0.1391 (2)	0.64216 (14)	0.28470 (12)	0.0622 (4)
H10A	0.2015	0.7182	0.2965	0.075*
C10B	0.5233 (2)	−0.13687 (13)	−0.12740 (12)	0.0571 (4)
H10B	0.4750	−0.2146	−0.1314	0.068*
C11A	0.0169 (2)	0.59024 (13)	0.18796 (12)	0.0558 (4)
C11B	0.45513 (19)	−0.08366 (13)	−0.20774 (11)	0.0539 (3)
C12A	−0.0775 (2)	0.47666 (14)	0.17121 (12)	0.0587 (4)
H12A	−0.1604	0.4412	0.1068	0.070*
C12B	0.5284 (2)	0.03318 (14)	−0.20013 (12)	0.0595 (4)
H12B	0.4834	0.0704	−0.2526	0.071*
C13A	−0.0485 (2)	0.41730 (13)	0.24934 (11)	0.0575 (4)
H13A	−0.1118	0.3416	0.2374	0.069*
C13B	0.6654 (2)	0.09324 (13)	−0.11637 (12)	0.0582 (4)
H13B	0.7134	0.1709	−0.1127	0.070*
C14A	−0.0144 (2)	0.65174 (15)	0.10526 (13)	0.0638 (4)
C14B	0.3157 (2)	−0.14810 (14)	−0.29808 (13)	0.0587 (4)
H1NA	0.021 (2)	0.3362 (16)	0.4094 (14)	0.077 (5)*
H1NB	0.934 (2)	0.1706 (16)	0.0406 (13)	0.072 (5)*
H1OA	0.397 (3)	0.559 (2)	0.5941 (17)	0.103 (7)*
H1OB	0.886 (3)	−0.0526 (18)	0.2020 (16)	0.090 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0813 (8)	0.0629 (7)	0.0783 (8)	−0.0142 (6)	−0.0038 (7)	0.0360 (6)
O1B	0.0827 (8)	0.0657 (7)	0.0713 (7)	−0.0186 (6)	0.0021 (6)	0.0304 (6)
N1A	0.0542 (7)	0.0505 (6)	0.0489 (6)	0.0056 (5)	0.0068 (5)	0.0149 (5)
N1B	0.0551 (7)	0.0543 (7)	0.0490 (6)	0.0068 (5)	0.0130 (5)	0.0201 (5)
N2A	0.0620 (8)	0.0531 (7)	0.0537 (7)	−0.0011 (6)	−0.0009 (6)	0.0186 (6)
N2B	0.0639 (8)	0.0588 (7)	0.0542 (7)	−0.0017 (6)	0.0061 (6)	0.0255 (6)
N3A	0.0952 (11)	0.0772 (10)	0.0642 (8)	−0.0075 (8)	0.0078 (8)	0.0344 (8)
N3B	0.0674 (9)	0.0678 (9)	0.0666 (8)	−0.0049 (7)	0.0042 (7)	0.0149 (7)
C1A	0.0532 (8)	0.0452 (7)	0.0546 (8)	0.0044 (6)	0.0127 (6)	0.0150 (6)
C1B	0.0511 (7)	0.0469 (7)	0.0535 (7)	0.0052 (6)	0.0171 (6)	0.0170 (6)
C2A	0.0508 (7)	0.0456 (7)	0.0499 (7)	0.0109 (6)	0.0147 (6)	0.0154 (6)
C2B	0.0489 (7)	0.0467 (7)	0.0487 (7)	0.0097 (6)	0.0160 (6)	0.0131 (6)
C3A	0.0546 (8)	0.0493 (7)	0.0563 (8)	0.0079 (6)	0.0107 (6)	0.0190 (6)
C3B	0.0598 (8)	0.0494 (8)	0.0547 (8)	0.0055 (6)	0.0142 (7)	0.0165 (6)
C4A	0.0608 (9)	0.0606 (9)	0.0655 (10)	0.0049 (7)	0.0017 (7)	0.0142 (8)
C4B	0.0817 (11)	0.0636 (10)	0.0624 (9)	0.0119 (8)	0.0186 (8)	0.0291 (8)
C5A	0.0726 (11)	0.0796 (11)	0.0534 (9)	0.0201 (9)	0.0019 (8)	0.0198 (8)
C5B	0.0836 (12)	0.0823 (12)	0.0557 (9)	0.0239 (10)	0.0102 (8)	0.0265 (9)
C6A	0.0845 (12)	0.0761 (11)	0.0603 (9)	0.0232 (9)	0.0188 (8)	0.0351 (8)
C6B	0.0619 (9)	0.0756 (11)	0.0581 (9)	0.0098 (8)	0.0015 (7)	0.0103 (8)
C7A	0.0683 (9)	0.0538 (8)	0.0617 (9)	0.0086 (7)	0.0180 (7)	0.0242 (7)
C7B	0.0532 (8)	0.0548 (8)	0.0602 (8)	0.0051 (6)	0.0139 (7)	0.0116 (7)
C8A	0.0539 (8)	0.0500 (7)	0.0495 (7)	0.0119 (6)	0.0120 (6)	0.0150 (6)
C8B	0.0521 (8)	0.0523 (8)	0.0488 (7)	0.0081 (6)	0.0152 (6)	0.0151 (6)
C9A	0.0634 (9)	0.0555 (8)	0.0499 (8)	0.0006 (7)	0.0058 (7)	0.0140 (6)
C9B	0.0594 (8)	0.0542 (8)	0.0547 (8)	0.0100 (6)	0.0156 (7)	0.0226 (6)
C10A	0.0691 (10)	0.0536 (8)	0.0599 (9)	−0.0006 (7)	0.0134 (7)	0.0180 (7)
C10B	0.0604 (9)	0.0495 (8)	0.0625 (9)	0.0053 (6)	0.0192 (7)	0.0173 (7)
C11A	0.0605 (9)	0.0572 (8)	0.0527 (8)	0.0104 (7)	0.0152 (7)	0.0211 (7)
C11B	0.0520 (8)	0.0563 (8)	0.0518 (8)	0.0065 (6)	0.0147 (6)	0.0128 (6)
C12A	0.0597 (9)	0.0593 (9)	0.0510 (8)	0.0072 (7)	0.0049 (7)	0.0160 (7)
C12B	0.0637 (9)	0.0586 (9)	0.0551 (8)	0.0080 (7)	0.0093 (7)	0.0226 (7)
C13A	0.0608 (9)	0.0486 (8)	0.0558 (8)	0.0032 (6)	0.0058 (7)	0.0140 (6)
C13B	0.0629 (9)	0.0515 (8)	0.0578 (8)	0.0025 (7)	0.0094 (7)	0.0218 (7)
C14A	0.0679 (10)	0.0624 (9)	0.0581 (9)	0.0013 (7)	0.0112 (7)	0.0219 (7)
C14B	0.0591 (9)	0.0559 (8)	0.0608 (9)	0.0058 (7)	0.0169 (7)	0.0171 (7)

Geometric parameters (Å, º) top

O1A—C3A	1.3559 (17)	C5B—C6B	1.377 (3)
O1A—H1OA	0.98 (2)	C5B—H5B	0.9300
O1B—C3B	1.3520 (18)	C6A—C7A	1.376 (2)
O1B—H1OB	0.90 (2)	C6A—H6A	0.9300
N1A—C1A	1.2865 (17)	C6B—C7B	1.382 (2)
N1A—N2A	1.3597 (16)	C6B—H6B	0.9300
N1B—C1B	1.2801 (18)	C7A—H7A	0.9300
N1B—N2B	1.3674 (16)	C7B—H7B	0.9300
N2A—C8A	1.3734 (18)	C8A—C13A	1.3943 (19)
N2A—H1NA	0.914 (18)	C8A—C9A	1.399 (2)
N2B—C8B	1.3709 (18)	C8B—C13B	1.397 (2)
N2B—H1NB	0.894 (18)	C8B—C9B	1.4008 (19)
N3A—C14A	1.140 (2)	C9A—C10A	1.379 (2)
N3B—C14B	1.142 (2)	C9A—H9A	0.9300
C1A—C2A	1.4453 (19)	C9B—C10B	1.374 (2)
C1A—H1A	0.9300	C9B—H9B	0.9300
C1B—C2B	1.4517 (19)	C10A—C11A	1.387 (2)
C1B—H1B	0.9300	C10A—H10A	0.9300
C2A—C7A	1.3951 (19)	C10B—C11B	1.393 (2)
C2A—C3A	1.402 (2)	C10B—H10B	0.9300
C2B—C7B	1.3925 (19)	C11A—C12A	1.395 (2)
C2B—C3B	1.4017 (19)	C11A—C14A	1.439 (2)
C3A—C4A	1.383 (2)	C11B—C12B	1.394 (2)
C3B—C4B	1.391 (2)	C11B—C14B	1.432 (2)
C4A—C5A	1.373 (2)	C12A—C13A	1.370 (2)
C4A—H4A	0.9300	C12A—H12A	0.9300
C4B—C5B	1.367 (3)	C12B—C13B	1.363 (2)
C4B—H4B	0.9300	C12B—H12B	0.9300
C5A—C6A	1.378 (3)	C13A—H13A	0.9300
C5A—H5A	0.9300	C13B—H13B	0.9300

C3A—O1A—H1OA	106.5 (13)	C7B—C6B—H6B	120.4
C3B—O1B—H1OB	108.4 (13)	C6A—C7A—C2A	121.60 (15)
C1A—N1A—N2A	116.26 (12)	C6A—C7A—H7A	119.2
C1B—N1B—N2B	117.48 (12)	C2A—C7A—H7A	119.2
N1A—N2A—C8A	121.92 (12)	C6B—C7B—C2B	121.27 (15)
N1A—N2A—H1NA	119.3 (11)	C6B—C7B—H7B	119.4
C8A—N2A—H1NA	118.6 (11)	C2B—C7B—H7B	119.4
N1B—N2B—C8B	120.79 (12)	N2A—C8A—C13A	117.82 (13)
N1B—N2B—H1NB	117.9 (11)	N2A—C8A—C9A	123.00 (13)
C8B—N2B—H1NB	120.8 (11)	C13A—C8A—C9A	119.18 (13)
N1A—C1A—C2A	122.47 (13)	N2B—C8B—C13B	118.37 (13)
N1A—C1A—H1A	118.8	N2B—C8B—C9B	122.92 (13)
C2A—C1A—H1A	118.8	C13B—C8B—C9B	118.71 (13)
N1B—C1B—C2B	122.14 (12)	C10A—C9A—C8A	119.59 (14)
N1B—C1B—H1B	118.9	C10A—C9A—H9A	120.2
C2B—C1B—H1B	118.9	C8A—C9A—H9A	120.2
C7A—C2A—C3A	117.93 (13)	C10B—C9B—C8B	119.81 (13)
C7A—C2A—C1A	119.35 (13)	C10B—C9B—H9B	120.1
C3A—C2A—C1A	122.70 (13)	C8B—C9B—H9B	120.1
C7B—C2B—C3B	118.45 (13)	C9A—C10A—C11A	121.09 (14)
C7B—C2B—C1B	119.12 (13)	C9A—C10A—H10A	119.5
C3B—C2B—C1B	122.43 (13)	C11A—C10A—H10A	119.5
O1A—C3A—C4A	118.18 (14)	C9B—C10B—C11B	121.24 (13)
O1A—C3A—C2A	121.55 (13)	C9B—C10B—H10B	119.4
C4A—C3A—C2A	120.27 (14)	C11B—C10B—H10B	119.4
O1B—C3B—C4B	118.20 (14)	C10A—C11A—C12A	119.13 (13)
O1B—C3B—C2B	122.02 (13)	C10A—C11A—C14A	121.12 (14)
C4B—C3B—C2B	119.78 (15)	C12A—C11A—C14A	119.75 (14)
C5A—C4A—C3A	120.18 (16)	C10B—C11B—C12B	118.66 (14)
C5A—C4A—H4A	119.9	C10B—C11B—C14B	121.05 (14)
C3A—C4A—H4A	119.9	C12B—C11B—C14B	120.26 (14)
C5B—C4B—C3B	120.29 (16)	C13A—C12A—C11A	120.19 (14)
C5B—C4B—H4B	119.9	C13A—C12A—H12A	119.9
C3B—C4B—H4B	119.9	C11A—C12A—H12A	119.9
C4A—C5A—C6A	120.81 (15)	C13B—C12B—C11B	120.49 (14)
C4A—C5A—H5A	119.6	C13B—C12B—H12B	119.8
C6A—C5A—H5A	119.6	C11B—C12B—H12B	119.8
C4B—C5B—C6B	121.02 (15)	C12A—C13A—C8A	120.82 (14)
C4B—C5B—H5B	119.5	C12A—C13A—H13A	119.6
C6B—C5B—H5B	119.5	C8A—C13A—H13A	119.6
C7A—C6A—C5A	119.21 (15)	C12B—C13B—C8B	121.09 (14)
C7A—C6A—H6A	120.4	C12B—C13B—H13B	119.5
C5A—C6A—H6A	120.4	C8B—C13B—H13B	119.5
C5B—C6B—C7B	119.19 (16)	N3A—C14A—C11A	179.3 (2)
C5B—C6B—H6B	120.4	N3B—C14B—C11B	179.48 (19)

C13A—C8A—N2A—N1A	175.98 (13)	C13B—C8B—N2B—N1B	172.55 (13)
C8A—N2A—N1A—C1A	179.44 (14)	C8B—N2B—N1B—C1B	175.41 (13)
N2A—N1A—C1A—C2A	−179.93 (13)	N2B—N1B—C1B—C2B	177.44 (12)
N1A—C1A—C2A—C3A	0.2 (2)	N1B—C1B—C2B—C3B	−1.4 (2)
C1A—C2A—C3A—O1A	−1.3 (2)	C1B—C2B—C3B—O1B	0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N1A	0.98 (2)	1.77 (2)	2.654 (2)	149 (2)
O1B—H1OB···N1B	0.90 (2)	1.86 (2)	2.653 (2)	147 (2)
N2A—H1NA···N3Bⁱ	0.91 (2)	2.17 (2)	3.065 (2)	166 (2)
N2B—H1NB···N3Aⁱⁱ	0.89 (2)	2.25 (2)	3.098 (2)	158 (2)
C7A—H7A···O1Bⁱⁱⁱ	0.93	2.55	3.427 (2)	156
C7B—H7B···O1A^iv	0.93	2.49	3.413 (2)	172

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O
M_r	237.26
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1917 (7), 11.6406 (7), 13.4445 (8)
α, β, γ (°)	103.006 (5), 104.387 (6), 96.426 (6)
V (Å³)	1190.67 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.26 × 0.15 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Sapphire3, Gemini)
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.827, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7913, 4592, 3696
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.121, 1.05
No. of reflections	4592
No. of parameters	341
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)', WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N1A	0.98 (2)	1.77 (2)	2.654 (2)	149 (2)
O1B—H1OB···N1B	0.90 (2)	1.86 (2)	2.653 (2)	147 (2)
N2A—H1NA···N3Bⁱ	0.91 (2)	2.17 (2)	3.065 (2)	166 (2)
N2B—H1NB···N3Aⁱⁱ	0.89 (2)	2.25 (2)	3.098 (2)	158 (2)
C7A—H7A···O1Bⁱⁱⁱ	0.93	2.55	3.427 (2)	156
C7B—H7B···O1A^iv	0.93	2.49	3.413 (2)	172

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

Acknowledgements

We thank Manchester Metropolitan University for providing X-ray analysis and data refinement facilities. SBN and GAB thank the Ministry of Education, Science and Technological Development of the Republic of Serbia for financial support (projects 172014 and 172035).

References

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