N′-[(E)-1-Phenyl­ethyl­idene]benzo­hydrazide

Fun, H.-K.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Chantrapromma, S.

doi:10.1107/S1600536808029218

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o1961-o1962

doi:10.1107/S1600536808029218

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N′-[(E)-1-Phenylethylidene]benzohydrazide

Hoong-Kun Fun,^a ^* K. V. Sujith,^b P. S. Patil,^c ‡ B. Kalluraya ^b and Suchada Chantrapromma ^d §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, ^cDepartment of Physics, K.L.E. Society's K.L.E. Institute of Technology, Gokul Road, Hubli 590 030, India, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 6 September 2008; accepted 11 September 2008; online 20 September 2008)

The title compound, C₁₅H₁₄N₂O, crystallized with two independent molecules in the asymmetric unit. Both molecules are non-planar and have an E configuration with respect to the C=N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in one molecule and 12.40 (19)° in the other. In the crystal structure, the molecules are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions into infinite one-dimensional chains along [1 0 0]. The crystal structure is further stabilized by N—H⋯O hydrogen bonds, weak C—H⋯O and very weak C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to the applications of hydrazone and benzohydrazide, see, for example: Bratenko et al. (1999 ); Raj et al. (2007 ); Rollas et al. (2002 ); Sridhar et al. (2003 ); Zhang et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₄N₂O
M_r = 238.28
Orthorhombic, P c a 2₁
a = 8.2237 (6) Å
b = 5.5938 (4) Å
c = 52.839 (4) Å
V = 2430.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100.0 (1) K
0.50 × 0.22 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.959, T_max = 0.996
23699 measured reflections
3572 independent reflections
2925 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.159
S = 1.08
3572 reflections
327 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2NA⋯O2Aⁱ	0.91	1.95	2.857 (4)	170
N2B—H2NB⋯O2Bⁱⁱ	0.73	2.17	2.866 (4)	161
C14A—H14A⋯O2Aⁱ	0.93	2.38	3.108 (5)	135
C14B—H14B⋯O2Bⁱⁱ	0.93	2.38	3.113 (5)	135
C15A—H15A⋯O2Aⁱ	0.96	2.58	3.053 (5)	110
C15B—H15D⋯O2Bⁱⁱ	0.96	2.44	3.038 (5)	120
C1A—H1AA⋯Cg1ⁱⁱ	0.93	2.96	3.729 (4)	141
C4A—H4AA⋯Cg1ⁱⁱⁱ	0.93	2.95	3.724 (5)	141
C1B—H1BA⋯Cg2ⁱ	0.93	2.88	3.726 (4)	141
C4B—H4BA⋯Cg2^iv	0.93	2.94	3.714 (4)	141
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+1, z]$ ; (iii) $[x-{\script{1\over 2}}, -y, z]$ ; (iv) $[x-{\script{1\over 2}}, -y+1, z]$ . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B phenyl rings, respectively.

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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029218/si2108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029218/si2108Isup2.hkl

checkCIF report

Comment top

Hydrazones are versatile intermediates and important building blocks. Hydrazones of aliphatic and aromatic methyl ketones yield pyrazole-4-carboxaldehyde upon diformylation on treatment with Vilsmeier reagent (Bratenko et al., 1999). Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar et al., 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Rollas et al., 2002). Hydrazones possessing an azometine -NHN=CH- proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as well as their metal complexes as target structures and evaluated their biological activities (Raj et al., 2007; Zhang et al., 2007). These observations guided us to synthesize the title compound and its crystal structure was reported here.

In the asymmetric unit of the title compound (Fig. 1), there are two independent molecules A and B. Bond lengths in molecules A and B are slightly different but all are in normal ranges (Allen et al., 1987). Both molecules are not planar and exist in the E configuration which respect to the C═N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in A and 12.40 (19)° in B. In molecule A, the interplanar angle between the mean plane through N2A/O2A/C8A/C9A and N1A/N2A/C6A/C7A/C15A planes = 20.8 (2)°. In molecule B atoms N1B, N2B, C7B and C15B lie on the same plane and this plane makes the dihedral angle with the mean plane through N2B/O2B/C8B/C9B = 20.4 (2)°.

Fig. 2 shows that the molecules are linked into chains along [1 0 0] through N—H···O hydrogen bonds and weak C—H···O and very weak C—H···π interactions (Table 1); Cg₁, Cg₂, Cg₃ and Cg₄ are the centroids of the C1A–C6A, C1B–C6B, C9A–C14A and C9B–C14B rings, respectively.

Related literature top

For bond-length data, see: Allen et al. (1987). For background to the applications of hydrazone and benzohydrazide, see, for example: Bratenko et al. (1999); Raj et al. (2007); Rollas et al. (2002); Sridhar et al. (2003); Zhang et al. (2007). Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B phenyl rings, respectively.

Experimental top

The title compound was obtained by refluxing phenyl hydrazide (0.01 mol) and acetophenone (0.01 mol) in ethanol (30 ml) by adding 3 drops of concentrated Sulfuric acid for 3 hr. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Colorless single crystals of the title compound suitable for x-ray structure determination were grown by slow evaporation of 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, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the major components of (I), viewed along the b axis showing that the molecules are linked in infinite one-dimensional chains along the a axis. Hydrogen bonds are drawn as dashed lines.

N'-[(E)-1-phenylethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₄N₂O	F(000) = 1008
M_r = 238.28	D_x = 1.302 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3572 reflections
a = 8.2237 (6) Å	θ = 0.8–30.0°
b = 5.5938 (4) Å	µ = 0.08 mm⁻¹
c = 52.839 (4) Å	T = 100 K
V = 2430.7 (3) Å³	Plate, colorless
Z = 8	0.50 × 0.22 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3572 independent reflections
Radiation source: fine-focus sealed tube	2925 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 0.8°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
T_min = 0.959, T_max = 0.996	l = −74→73
23699 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0598P)² + 2.0097P] where P = (F_o² + 2F_c²)/3
3572 reflections	(Δ/σ)_max < 0.001
327 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O	V = 2430.7 (3) Å³
M_r = 238.28	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.2237 (6) Å	µ = 0.08 mm⁻¹
b = 5.5938 (4) Å	T = 100 K
c = 52.839 (4) Å	0.50 × 0.22 × 0.05 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3572 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2925 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.996	R_int = 0.069
23699 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.159	H-atom parameters constrained
S = 1.08	Δρ_max = 0.29 e Å⁻³
3572 reflections	Δρ_min = −0.30 e Å⁻³
327 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
O2A	0.4444 (3)	−0.2422 (5)	0.28192 (5)	0.0225 (5)
N1A	0.5650 (4)	0.0608 (6)	0.24842 (6)	0.0211 (7)
N2A	0.6306 (4)	0.0417 (6)	0.27253 (6)	0.0201 (7)
H2NA	0.7358	0.0912	0.2746	0.024*
C1A	0.5851 (5)	0.4279 (7)	0.19173 (7)	0.0228 (8)
H1AA	0.6561	0.5481	0.1968	0.027*
C2A	0.5277 (5)	0.4246 (7)	0.16709 (7)	0.0248 (8)
H2AA	0.5604	0.5425	0.1558	0.030*
C3A	0.4219 (5)	0.2471 (7)	0.15916 (7)	0.0237 (8)
H3AA	0.3846	0.2445	0.1426	0.028*
C4A	0.3719 (6)	0.0726 (7)	0.17624 (8)	0.0259 (8)
H4AA	0.2996	−0.0457	0.1711	0.031*
C5A	0.4294 (5)	0.0744 (7)	0.20083 (7)	0.0221 (8)
H5AA	0.3959	−0.0440	0.2120	0.026*
C6A	0.5372 (5)	0.2515 (6)	0.20916 (7)	0.0183 (7)
C7A	0.6028 (4)	0.2496 (6)	0.23548 (7)	0.0186 (7)
C8A	0.5670 (5)	−0.1290 (6)	0.28767 (7)	0.0194 (7)
C9A	0.6454 (5)	−0.1709 (6)	0.31291 (7)	0.0192 (7)
C10A	0.6062 (5)	−0.3840 (7)	0.32523 (7)	0.0237 (8)
H10A	0.5381	−0.4942	0.3174	0.028*
C11A	0.6686 (6)	−0.4318 (7)	0.34912 (8)	0.0281 (9)
H11A	0.6405	−0.5727	0.3574	0.034*
C12A	0.7725 (5)	−0.2705 (7)	0.36069 (8)	0.0284 (9)
H12A	0.8161	−0.3045	0.3765	0.034*
C13A	0.8115 (5)	−0.0584 (7)	0.34857 (7)	0.0264 (8)
H13A	0.8798	0.0509	0.3565	0.032*
C14A	0.7494 (5)	−0.0079 (7)	0.32479 (7)	0.0223 (7)
H14A	0.7768	0.1343	0.3167	0.027*
C15A	0.7015 (5)	0.4561 (6)	0.24455 (8)	0.0240 (8)
H15A	0.6978	0.4627	0.2627	0.036*
H15B	0.6581	0.6016	0.2377	0.036*
H15C	0.8121	0.4370	0.2391	0.036*
O2B	0.7470 (3)	0.7474 (4)	0.48915 (5)	0.0219 (5)
N1B	0.8664 (4)	0.4422 (5)	0.52262 (6)	0.0191 (6)
N2B	0.9356 (4)	0.4640 (6)	0.49876 (6)	0.0217 (7)
H2NB	1.0056	0.4027	0.4934	0.026*
C1B	0.8836 (5)	0.0735 (7)	0.57897 (7)	0.0230 (8)
H1BA	0.9549	−0.0459	0.5738	0.028*
C2B	0.8256 (5)	0.0752 (7)	0.60357 (7)	0.0256 (8)
H2BA	0.8590	−0.0419	0.6149	0.031*
C3B	0.7171 (5)	0.2523 (7)	0.61138 (7)	0.0242 (8)
H3BA	0.6778	0.2529	0.6279	0.029*
C4B	0.6682 (5)	0.4275 (7)	0.59443 (7)	0.0233 (8)
H4BA	0.5953	0.5450	0.5996	0.028*
C5B	0.7273 (5)	0.4279 (6)	0.56996 (7)	0.0214 (8)
H5BA	0.6950	0.5472	0.5588	0.026*
C6B	0.8357 (5)	0.2499 (6)	0.56181 (7)	0.0178 (7)
C7B	0.9020 (5)	0.2528 (6)	0.53547 (7)	0.0181 (7)
C8B	0.8716 (5)	0.6352 (6)	0.48358 (7)	0.0191 (7)
C9B	0.9556 (5)	0.6867 (7)	0.45879 (7)	0.0200 (7)
C10B	0.9161 (5)	0.9028 (7)	0.44669 (8)	0.0239 (8)
H10B	0.8449	1.0098	0.4543	0.029*
C11B	0.9835 (5)	0.9560 (7)	0.42336 (7)	0.0248 (8)
H11B	0.9575	1.0990	0.4153	0.030*
C12B	1.0899 (5)	0.7967 (7)	0.41187 (7)	0.0258 (8)
H12B	1.1345	0.8333	0.3962	0.031*
C13B	1.1300 (5)	0.5833 (7)	0.42368 (7)	0.0249 (8)
H13B	1.2033	0.4785	0.4161	0.030*
C14B	1.0592 (5)	0.5268 (7)	0.44704 (7)	0.0228 (8)
H14B	1.0821	0.3809	0.4547	0.027*
C15B	1.0038 (5)	0.0472 (6)	0.52656 (7)	0.0215 (8)
H15D	1.0135	0.0531	0.5085	0.032*
H15E	0.9531	−0.1004	0.5314	0.032*
H15F	1.1099	0.0571	0.5341	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2A	0.0164 (13)	0.0242 (12)	0.0268 (13)	−0.0029 (11)	−0.0018 (11)	0.0001 (10)
N1A	0.0199 (17)	0.0221 (15)	0.0214 (15)	−0.0012 (12)	−0.0012 (13)	0.0022 (12)
N2A	0.0191 (17)	0.0198 (15)	0.0213 (16)	−0.0015 (12)	−0.0014 (13)	0.0019 (12)
C1A	0.023 (2)	0.0184 (16)	0.027 (2)	−0.0005 (14)	0.0004 (15)	0.0014 (14)
C2A	0.023 (2)	0.0258 (18)	0.0253 (19)	0.0017 (16)	−0.0004 (16)	0.0067 (15)
C3A	0.025 (2)	0.0271 (19)	0.0189 (17)	0.0047 (16)	−0.0020 (15)	0.0016 (14)
C4A	0.029 (2)	0.0225 (18)	0.0258 (18)	−0.0018 (16)	−0.0003 (16)	−0.0034 (15)
C5A	0.0199 (19)	0.0209 (17)	0.0254 (18)	−0.0009 (15)	0.0002 (15)	0.0020 (14)
C6A	0.0164 (17)	0.0182 (15)	0.0203 (16)	0.0023 (13)	0.0006 (13)	0.0000 (13)
C7A	0.0143 (17)	0.0199 (16)	0.0216 (17)	0.0029 (13)	−0.0002 (13)	−0.0012 (13)
C8A	0.0195 (18)	0.0158 (15)	0.0229 (18)	0.0009 (14)	0.0000 (15)	0.0001 (13)
C9A	0.0168 (18)	0.0188 (16)	0.0221 (17)	0.0005 (13)	0.0011 (14)	0.0027 (13)
C10A	0.025 (2)	0.0204 (17)	0.0261 (19)	0.0000 (15)	−0.0029 (16)	0.0017 (14)
C11A	0.028 (2)	0.0273 (19)	0.029 (2)	0.0009 (16)	0.0015 (17)	0.0061 (16)
C12A	0.028 (2)	0.034 (2)	0.0226 (18)	0.0027 (17)	−0.0020 (16)	0.0043 (16)
C13A	0.021 (2)	0.033 (2)	0.0253 (19)	−0.0016 (16)	0.0004 (16)	−0.0012 (15)
C14A	0.022 (2)	0.0233 (16)	0.0218 (18)	−0.0040 (16)	0.0001 (16)	0.0010 (14)
C15A	0.024 (2)	0.0192 (17)	0.029 (2)	0.0007 (15)	−0.0032 (16)	−0.0005 (14)
O2B	0.0192 (13)	0.0213 (12)	0.0253 (13)	0.0023 (11)	0.0021 (10)	0.0007 (10)
N1B	0.0182 (16)	0.0200 (14)	0.0193 (15)	−0.0017 (12)	0.0029 (12)	−0.0006 (11)
N2B	0.0213 (17)	0.0247 (15)	0.0190 (15)	0.0021 (13)	0.0058 (13)	−0.0008 (12)
C1B	0.0215 (19)	0.0189 (16)	0.028 (2)	0.0017 (14)	0.0004 (16)	0.0025 (15)
C2B	0.025 (2)	0.0252 (18)	0.027 (2)	0.0000 (16)	−0.0021 (17)	0.0070 (15)
C3B	0.022 (2)	0.0281 (18)	0.0221 (18)	−0.0019 (15)	0.0016 (15)	0.0002 (15)
C4B	0.024 (2)	0.0255 (18)	0.0210 (17)	0.0030 (16)	0.0015 (15)	−0.0030 (14)
C5B	0.026 (2)	0.0183 (15)	0.0205 (17)	0.0028 (14)	−0.0004 (15)	0.0012 (13)
C6B	0.0158 (17)	0.0142 (14)	0.0235 (16)	−0.0021 (13)	0.0002 (14)	0.0006 (12)
C7B	0.0155 (17)	0.0153 (16)	0.0237 (18)	−0.0002 (13)	−0.0012 (13)	−0.0028 (13)
C8B	0.0188 (18)	0.0181 (16)	0.0204 (17)	−0.0015 (14)	0.0005 (14)	−0.0018 (13)
C9B	0.0177 (18)	0.0219 (16)	0.0204 (16)	−0.0029 (14)	0.0015 (14)	−0.0035 (14)
C10B	0.0217 (19)	0.0229 (17)	0.027 (2)	0.0011 (15)	−0.0024 (15)	0.0000 (15)
C11B	0.028 (2)	0.0220 (18)	0.0240 (18)	−0.0030 (15)	−0.0011 (16)	0.0041 (14)
C12B	0.025 (2)	0.0319 (19)	0.0201 (17)	−0.0053 (16)	0.0006 (15)	0.0014 (15)
C13B	0.025 (2)	0.0270 (17)	0.0222 (18)	0.0012 (16)	0.0045 (16)	−0.0037 (14)
C14B	0.025 (2)	0.0201 (16)	0.0231 (18)	0.0018 (15)	−0.0015 (15)	−0.0001 (14)
C15B	0.0212 (19)	0.0185 (16)	0.0250 (18)	0.0035 (14)	0.0011 (15)	−0.0018 (14)

Geometric parameters (Å, º) top

O2A—C8A	1.229 (5)	O2B—C8B	1.237 (5)
N1A—C7A	1.296 (5)	N1B—C7B	1.292 (5)
N1A—N2A	1.388 (4)	N1B—N2B	1.389 (4)
N2A—C8A	1.351 (5)	N2B—C8B	1.356 (5)
N2A—H2NA	0.9145	N2B—H2NB	0.7271
C1A—C2A	1.385 (5)	C1B—C2B	1.384 (5)
C1A—C6A	1.406 (5)	C1B—C6B	1.397 (5)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.385 (6)	C2B—C3B	1.395 (6)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.392 (6)	C3B—C4B	1.387 (5)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.382 (5)	C4B—C5B	1.381 (5)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.400 (5)	C5B—C6B	1.404 (5)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.492 (5)	C6B—C7B	1.495 (5)
C7A—C15A	1.491 (5)	C7B—C15B	1.498 (5)
C8A—C9A	1.499 (5)	C8B—C9B	1.509 (5)
C9A—C10A	1.396 (5)	C9B—C14B	1.382 (5)
C9A—C14A	1.399 (5)	C9B—C10B	1.406 (5)
C10A—C11A	1.388 (6)	C10B—C11B	1.384 (6)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.385 (6)	C11B—C12B	1.389 (6)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.386 (6)	C12B—C13B	1.387 (6)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.385 (5)	C13B—C14B	1.401 (5)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600

C7A—N1A—N2A	117.0 (3)	C7B—N1B—N2B	117.1 (3)
C8A—N2A—N1A	116.6 (3)	C8B—N2B—N1B	116.1 (3)
C8A—N2A—H2NA	120.6	C8B—N2B—H2NB	114.2
N1A—N2A—H2NA	117.0	N1B—N2B—H2NB	129.5
C2A—C1A—C6A	120.7 (4)	C2B—C1B—C6B	120.5 (4)
C2A—C1A—H1AA	119.6	C2B—C1B—H1BA	119.8
C6A—C1A—H1AA	119.6	C6B—C1B—H1BA	119.8
C3A—C2A—C1A	120.5 (4)	C1B—C2B—C3B	120.2 (4)
C3A—C2A—H2AA	119.7	C1B—C2B—H2BA	119.9
C1A—C2A—H2AA	119.7	C3B—C2B—H2BA	119.9
C2A—C3A—C4A	119.5 (4)	C4B—C3B—C2B	119.7 (4)
C2A—C3A—H3AA	120.3	C4B—C3B—H3BA	120.1
C4A—C3A—H3AA	120.3	C2B—C3B—H3BA	120.1
C5A—C4A—C3A	120.2 (4)	C5B—C4B—C3B	120.2 (4)
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.9
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.9
C4A—C5A—C6A	121.1 (4)	C4B—C5B—C6B	120.6 (3)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.7
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.7
C5A—C6A—C1A	117.9 (3)	C1B—C6B—C5B	118.8 (3)
C5A—C6A—C7A	121.1 (3)	C1B—C6B—C7B	120.6 (3)
C1A—C6A—C7A	121.0 (3)	C5B—C6B—C7B	120.6 (3)
N1A—C7A—C15A	126.3 (3)	N1B—C7B—C6B	114.5 (3)
N1A—C7A—C6A	114.3 (3)	N1B—C7B—C15B	126.2 (3)
C15A—C7A—C6A	119.4 (3)	C6B—C7B—C15B	119.2 (3)
O2A—C8A—N2A	122.4 (3)	O2B—C8B—N2B	122.6 (3)
O2A—C8A—C9A	119.5 (3)	O2B—C8B—C9B	119.3 (3)
N2A—C8A—C9A	118.1 (3)	N2B—C8B—C9B	118.1 (3)
C10A—C9A—C14A	119.2 (3)	C14B—C9B—C10B	119.7 (4)
C10A—C9A—C8A	116.7 (3)	C14B—C9B—C8B	123.3 (3)
C14A—C9A—C8A	124.1 (3)	C10B—C9B—C8B	116.9 (3)
C11A—C10A—C9A	120.2 (4)	C11B—C10B—C9B	119.8 (4)
C11A—C10A—H10A	119.9	C11B—C10B—H10B	120.1
C9A—C10A—H10A	119.9	C9B—C10B—H10B	120.1
C12A—C11A—C10A	120.2 (4)	C10B—C11B—C12B	120.3 (4)
C12A—C11A—H11A	119.9	C10B—C11B—H11B	119.9
C10A—C11A—H11A	119.9	C12B—C11B—H11B	119.9
C11A—C12A—C13A	119.7 (4)	C13B—C12B—C11B	120.4 (4)
C11A—C12A—H12A	120.1	C13B—C12B—H12B	119.8
C13A—C12A—H12A	120.1	C11B—C12B—H12B	119.8
C14A—C13A—C12A	120.6 (4)	C12B—C13B—C14B	119.4 (4)
C14A—C13A—H13A	119.7	C12B—C13B—H13B	120.3
C12A—C13A—H13A	119.7	C14B—C13B—H13B	120.3
C13A—C14A—C9A	120.0 (4)	C9B—C14B—C13B	120.4 (4)
C13A—C14A—H14A	120.0	C9B—C14B—H14B	119.8
C9A—C14A—H14A	120.0	C13B—C14B—H14B	119.8
C7A—C15A—H15A	109.5	C7B—C15B—H15D	109.5
C7A—C15A—H15B	109.5	C7B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C7A—C15A—H15C	109.5	C7B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5

C7A—N1A—N2A—C8A	167.6 (3)	C7B—N1B—N2B—C8B	166.7 (3)
C6A—C1A—C2A—C3A	0.0 (6)	C6B—C1B—C2B—C3B	0.7 (6)
C1A—C2A—C3A—C4A	0.7 (6)	C1B—C2B—C3B—C4B	−0.3 (6)
C2A—C3A—C4A—C5A	−1.0 (6)	C2B—C3B—C4B—C5B	−0.5 (6)
C3A—C4A—C5A—C6A	0.6 (6)	C3B—C4B—C5B—C6B	0.9 (6)
C4A—C5A—C6A—C1A	0.1 (6)	C2B—C1B—C6B—C5B	−0.3 (6)
C4A—C5A—C6A—C7A	−178.3 (3)	C2B—C1B—C6B—C7B	178.1 (4)
C2A—C1A—C6A—C5A	−0.4 (6)	C4B—C5B—C6B—C1B	−0.5 (6)
C2A—C1A—C6A—C7A	178.0 (3)	C4B—C5B—C6B—C7B	−178.9 (4)
N2A—N1A—C7A—C15A	−4.2 (6)	N2B—N1B—C7B—C6B	174.9 (3)
N2A—N1A—C7A—C6A	176.2 (3)	N2B—N1B—C7B—C15B	−3.6 (6)
C5A—C6A—C7A—N1A	6.8 (5)	C1B—C6B—C7B—N1B	−170.8 (3)
C1A—C6A—C7A—N1A	−171.5 (3)	C5B—C6B—C7B—N1B	7.6 (5)
C5A—C6A—C7A—C15A	−172.8 (4)	C1B—C6B—C7B—C15B	7.8 (5)
C1A—C6A—C7A—C15A	8.8 (5)	C5B—C6B—C7B—C15B	−173.8 (3)
N1A—N2A—C8A—O2A	−9.0 (5)	N1B—N2B—C8B—O2B	−8.4 (5)
N1A—N2A—C8A—C9A	174.2 (3)	N1B—N2B—C8B—C9B	172.6 (3)
O2A—C8A—C9A—C10A	19.1 (5)	O2B—C8B—C9B—C14B	−158.2 (4)
N2A—C8A—C9A—C10A	−164.0 (3)	N2B—C8B—C9B—C14B	20.9 (6)
O2A—C8A—C9A—C14A	−158.9 (4)	O2B—C8B—C9B—C10B	17.6 (5)
N2A—C8A—C9A—C14A	18.0 (5)	N2B—C8B—C9B—C10B	−163.3 (3)
C14A—C9A—C10A—C11A	0.6 (6)	C14B—C9B—C10B—C11B	−1.2 (6)
C8A—C9A—C10A—C11A	−177.4 (4)	C8B—C9B—C10B—C11B	−177.2 (4)
C9A—C10A—C11A—C12A	−1.2 (6)	C9B—C10B—C11B—C12B	0.0 (6)
C10A—C11A—C12A—C13A	1.4 (6)	C10B—C11B—C12B—C13B	−0.2 (6)
C11A—C12A—C13A—C14A	−1.1 (6)	C11B—C12B—C13B—C14B	1.5 (6)
C12A—C13A—C14A—C9A	0.5 (6)	C10B—C9B—C14B—C13B	2.6 (6)
C10A—C9A—C14A—C13A	−0.3 (6)	C8B—C9B—C14B—C13B	178.3 (4)
C8A—C9A—C14A—C13A	177.6 (4)	C12B—C13B—C14B—C9B	−2.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O2Aⁱ	0.91	1.95	2.857 (4)	170
N2B—H2NB···O2Bⁱⁱ	0.73	2.17	2.866 (4)	161
C14A—H14A···O2Aⁱ	0.93	2.38	3.108 (5)	135
C14B—H14B···O2Bⁱⁱ	0.93	2.38	3.113 (5)	135
C15A—H15A···N2A	0.96	2.47	2.811 (5)	100
C15A—H15A···O2Aⁱ	0.96	2.58	3.053 (5)	110
C15B—H15D···N2B	0.96	2.44	2.812 (5)	103
C15B—H15D···O2Bⁱⁱ	0.96	2.45	3.038 (5)	120
C1A—H1AA···Cg1ⁱⁱ	0.93	2.96	3.729 (4)	141
C4A—H4AA···Cg1ⁱⁱⁱ	0.93	2.95	3.724 (5)	141
C1B—H1BA···Cg2ⁱ	0.93	2.88	3.726 (4)	141
C10A—H10A···Cg3^iv	0.93	3.31	3.993 (4)	132
C10B—H10B···Cg4^v	0.93	3.16	3.847 (4)	132
C4B—H4BA···Cg2^vi	0.93	2.94	3.714 (4)	141
C13A—H13A···Cg3ⁱ	0.93	3.05	3.674 (4)	126
C13B—H13B···Cg4ⁱⁱ	0.93	3.07	3.755 (4)	132

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O
M_r	238.28
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	100
a, b, c (Å)	8.2237 (6), 5.5938 (4), 52.839 (4)
V (Å³)	2430.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.22 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.959, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	23699, 3572, 2925
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.159, 1.08
No. of reflections	3572
No. of parameters	327
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N2A—H2NA···O2Aⁱ	0.91	1.9509	2.857 (4)	170
N2B—H2NB···O2Bⁱⁱ	0.73	2.1671	2.866 (4)	161
C14A—H14A···O2Aⁱ	0.93	2.3751	3.108 (5)	135
C14B—H14B···O2Bⁱⁱ	0.93	2.3807	3.113 (5)	135
C15A—H15A···N2A	0.96	2.4741	2.811 (5)	100
C15A—H15A···O2Aⁱ	0.96	2.5817	3.053 (5)	110
C15B—H15D···N2B	0.96	2.4410	2.812 (5)	103
C15B—H15D···O2Bⁱⁱ	0.96	2.4450	3.038 (5)	120
C1A—H1AA···Cg1ⁱⁱ	0.93	2.9634	3.729 (4)	141
C4A—H4AA···Cg1ⁱⁱⁱ	0.93	2.9537	3.724 (5)	141
C1B—H1BA···Cg2ⁱ	0.93	2.884	3.726 (4)	141
C4B—H4BA···Cg2^iv	0.93	2.9417	3.714 (4)	141

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

Footnotes

‡Previous address: Department of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India.

§Additional correspondence author, email: suchada.c@psu.ac.th.

Acknowledgements

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bratenko, M. K., Chornous, V. A., Voloshin, N. P. & Vovk, M. V. (1999). Chem. Heterocycl. Compd, 35, 1075–1077. CrossRef CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS Google Scholar
Rollas, S., Gülerman, N. & Erdeniz, H. (2002). Farmaco, 57, 171–174. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridhar, R. & Perumal, P. T. (2003). Syn. Commun. 33, 1483–1488. Web of Science CrossRef CAS Google Scholar
Zhang, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774–3777. Web of Science PubMed Google Scholar