(E)-1-(2-Nitro­benzyl­idene)-2-phenyl­hydrazine

Shad, H.A.; Tahir, M.N.; Tariq, M.I.; Sarfraz, M.; Ahmad, S.

doi:10.1107/S1600536810025882

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1955

https://doi.org/10.1107/S1600536810025882

Open

access

(E)-1-(2-Nitrobenzylidene)-2-phenylhydrazine

Hazoor Ahmad Shad,^a M. Nawaz Tahir,^b ^* Muhammad Ilyas Tariq,^c Muhammad Sarfraz ^c and Shahbaz Ahmad ^c

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 28 June 2010; accepted 1 July 2010; online 7 July 2010)

The asymmetric unit of the title compound, C₁₃H₁₁N₃O₂, contains two molecules with slightly different conformations: the dihedral angle between the aromatic rings is 13.01 (10)° in one molecule and 14.05 (10)° in the other. Both molecules feature short intramolecular C—H⋯O contacts, which generate S(6) rings. In the crystal, both molecules form inversion dimers linked by pairs of N—H⋯O hydrogen bonds, thereby generating R₂²(16) rings.

Related literature

For background information on Schiff bases and related crystal structures, see: Mufakkar et al. (2010 ); Tahir et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₂
M_r = 241.25
Orthorhombic, P b c a
a = 19.4021 (13) Å
b = 12.1065 (7) Å
c = 20.0554 (11) Å
V = 4710.8 (5) Å³
Z = 16
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.32 × 0.28 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.972, T_max = 0.979
18932 measured reflections
4260 independent reflections
2577 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.117
S = 1.01
4260 reflections
325 parameters
H-atom parameters constrained
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
C7—H7⋯O1	0.93	2.24	2.773 (3)	116
C20—H20⋯O3	0.93	2.27	2.788 (3)	115
N1—H1⋯O3ⁱ	0.86	2.42	3.242 (2)	161
N4—H4A⋯O1ⁱⁱ	0.86	2.39	3.207 (2)	158
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810025882/hb5534sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025882/hb5534Isup2.hkl

checkCIF report

Comment top

We have reported crystal structures of Schiff bases containing phenylhydrazine (Mufakkar et al., 2010) and 2-nitrobenzaldehyde (Tahir et al., 2010) and as a part of this project, we report herein the structure and synthesis of the title compound (I, Fig. 1).

The title compound consists of two molecules in the crystallographic asymmetric unit which differ from each other geometrically. In one molecule, the phenylhydrazine A (C1—C6/N1/N2) and group B (C7—C13) of 2-nitrobenzaldehyde are planar with r. m. s deviation of 0.0228 and 0.0068 Å, respectively. The nitro group C (O1/N3/O2) is of course planar. The dihedral angle between A/B, A/C and B/C is 14.05 (10)°, 13.38 (32)° and 17.41 (30)°, respectively. In second molecule, the phenylhydrazine D (C1—C6/N1/N2) and group E (C7—C13) of 2-nitrobenzaldehyde are also planar with r. m. s deviation of 0.0054 and 0.0037 Å, respectively. The dihedral angle between D/E is 13.01 (10)°. The nitro group F (O3/N6/O4) of this molecule makes dihedral angle of 25.02 (27)° with group D, whereas it is oriented at 27.12 (27)° with group E. In each molecule there exist S(5) and S(6) ring motifs (Bernstein et al., 1995) due to intramolecular H-bonding of C—H···N and C—H···O type, respectively. The molecules are stabilized in the form of dimers due to N—H···O type of H-bondings with R₂²(16) ring motifs (Table 1, Fig. 2).

Related literature top

For background information on Schiff bases and related crystal structures, see: Mufakkar et al. (2010); Tahir et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Equimolar quantities of phenylhydrazine and 2-nitrobenzaldehyde were refluxed in methanol for 25 min resulting in a violet solution. The solution was kept at room temperature, which afforded violet prisms of (I) after 48 h.

Structure description top

For background information on Schiff bases and related crystal structures, see: Mufakkar et al. (2010); Tahir et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing of (I), which shows that molecules form dimers.

(E)-1-(2-Nitrobenzylidene)-2-phenylhydrazine top

Crystal data top

C₁₃H₁₁N₃O₂	F(000) = 2016
M_r = 241.25	D_x = 1.361 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2577 reflections
a = 19.4021 (13) Å	θ = 2.2–25.3°
b = 12.1065 (7) Å	µ = 0.10 mm⁻¹
c = 20.0554 (11) Å	T = 296 K
V = 4710.8 (5) Å³	Prism, violet
Z = 16	0.32 × 0.28 × 0.24 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4260 independent reflections
Radiation source: fine-focus sealed tube	2577 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.3°, θ_min = 2.2°
ω scans	h = −21→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→14
T_min = 0.972, T_max = 0.979	l = −24→24
18932 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0426P)² + 0.9743P] where P = (F_o² + 2F_c²)/3
4260 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₂	V = 4710.8 (5) Å³
M_r = 241.25	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 19.4021 (13) Å	µ = 0.10 mm⁻¹
b = 12.1065 (7) Å	T = 296 K
c = 20.0554 (11) Å	0.32 × 0.28 × 0.24 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4260 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2577 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.979	R_int = 0.041
18932 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
4260 reflections	Δρ_min = −0.14 e Å⁻³
325 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	−0.02767 (9)	0.48801 (15)	−0.11736 (8)	0.0811 (7)
O2	−0.03824 (10)	0.64989 (16)	−0.15815 (9)	0.0982 (8)
N1	0.12471 (9)	0.27574 (14)	−0.00241 (8)	0.0646 (7)
N2	0.12334 (8)	0.38691 (13)	0.00220 (8)	0.0546 (6)
N3	−0.01209 (9)	0.58595 (18)	−0.11891 (9)	0.0642 (7)
C1	0.15768 (10)	0.21311 (16)	0.04626 (10)	0.0519 (7)
C2	0.15290 (12)	0.09962 (17)	0.04246 (10)	0.0634 (8)
C3	0.18603 (12)	0.03400 (19)	0.08869 (12)	0.0709 (9)
C4	0.22378 (12)	0.0800 (2)	0.13901 (11)	0.0709 (10)
C5	0.22787 (12)	0.1929 (2)	0.14304 (11)	0.0716 (10)
C6	0.19503 (11)	0.26019 (18)	0.09740 (10)	0.0621 (8)
C7	0.08784 (11)	0.44017 (16)	−0.04126 (10)	0.0568 (8)
C8	0.08420 (10)	0.56020 (16)	−0.03663 (9)	0.0505 (7)
C9	0.03909 (11)	0.62879 (17)	−0.07170 (9)	0.0528 (7)
C10	0.03841 (13)	0.74245 (19)	−0.06341 (12)	0.0724 (9)
C11	0.08391 (15)	0.79155 (19)	−0.02040 (13)	0.0799 (10)
C12	0.12983 (13)	0.7266 (2)	0.01410 (12)	0.0764 (10)
C13	0.13014 (11)	0.61467 (18)	0.00641 (10)	0.0621 (8)
O3	0.53109 (9)	0.28838 (15)	0.13060 (9)	0.0901 (8)
O4	0.52867 (11)	0.44681 (16)	0.08338 (9)	0.1054 (8)
N4	0.37407 (9)	0.07450 (14)	0.24028 (8)	0.0580 (6)
N5	0.38069 (8)	0.18402 (13)	0.25032 (8)	0.0529 (6)
N6	0.51143 (10)	0.38409 (18)	0.12819 (9)	0.0680 (8)
C14	0.33940 (10)	0.00973 (16)	0.28709 (10)	0.0501 (7)
C15	0.30960 (11)	0.05488 (18)	0.34361 (10)	0.0608 (8)
C16	0.27540 (12)	−0.0131 (2)	0.38795 (11)	0.0713 (9)
C17	0.27064 (12)	−0.1249 (2)	0.37713 (12)	0.0723 (9)
C18	0.30009 (12)	−0.16936 (18)	0.32096 (12)	0.0706 (9)
C19	0.33432 (11)	−0.10272 (17)	0.27593 (11)	0.0610 (8)
C20	0.41511 (10)	0.23954 (16)	0.20722 (10)	0.0539 (7)
C21	0.42235 (10)	0.35828 (16)	0.21663 (9)	0.0487 (7)
C22	0.46637 (10)	0.42733 (17)	0.18061 (10)	0.0527 (7)
C23	0.47060 (12)	0.53979 (18)	0.19184 (11)	0.0642 (8)
C24	0.43038 (13)	0.58790 (19)	0.23970 (12)	0.0719 (9)
C25	0.38560 (12)	0.5228 (2)	0.27580 (11)	0.0678 (9)
C26	0.38167 (11)	0.41148 (18)	0.26445 (10)	0.0596 (8)
H1	0.10513	0.24344	−0.03557	0.0775*
H2	0.12723	0.06716	0.00856	0.0761*
H3	0.18261	−0.04244	0.08555	0.0851*
H4	0.24630	0.03560	0.16995	0.0851*
H5	0.25332	0.22489	0.17727	0.0858*
H6	0.19807	0.33661	0.10112	0.0746*
H7	0.06484	0.40278	−0.07511	0.0682*
H10	0.00707	0.78539	−0.08706	0.0868*
H11	0.08374	0.86777	−0.01461	0.0959*
H12	0.16112	0.75952	0.04309	0.0917*
H13	0.16181	0.57300	0.03047	0.0745*
H4A	0.39117	0.04455	0.20509	0.0696*
H15	0.31260	0.13038	0.35166	0.0729*
H16	0.25524	0.01739	0.42579	0.0856*
H17	0.24775	−0.16993	0.40748	0.0868*
H18	0.29697	−0.24492	0.31318	0.0848*
H19	0.35401	−0.13356	0.23798	0.0732*
H20	0.43505	0.20467	0.17068	0.0647*
H23	0.50081	0.58273	0.16684	0.0770*
H24	0.43318	0.66341	0.24777	0.0862*
H25	0.35776	0.55483	0.30822	0.0814*
H26	0.35083	0.36969	0.28943	0.0716*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0805 (12)	0.0809 (12)	0.0818 (12)	−0.0026 (10)	−0.0189 (9)	−0.0115 (9)
O2	0.0928 (14)	0.1218 (15)	0.0801 (12)	0.0250 (12)	−0.0258 (10)	0.0245 (11)
N1	0.0801 (14)	0.0509 (11)	0.0628 (11)	0.0090 (9)	−0.0199 (10)	−0.0048 (8)
N2	0.0537 (11)	0.0525 (11)	0.0575 (10)	0.0061 (8)	−0.0015 (9)	−0.0006 (8)
N3	0.0593 (12)	0.0829 (14)	0.0504 (11)	0.0128 (11)	0.0009 (9)	0.0032 (10)
C1	0.0478 (12)	0.0550 (13)	0.0530 (12)	0.0077 (10)	−0.0007 (10)	0.0004 (10)
C2	0.0649 (15)	0.0613 (14)	0.0640 (14)	0.0058 (12)	−0.0117 (11)	−0.0015 (11)
C3	0.0731 (16)	0.0616 (14)	0.0781 (16)	0.0093 (12)	−0.0048 (14)	0.0072 (12)
C4	0.0629 (16)	0.0837 (19)	0.0660 (15)	0.0187 (13)	−0.0016 (12)	0.0156 (12)
C5	0.0583 (15)	0.097 (2)	0.0595 (14)	0.0071 (13)	−0.0102 (11)	−0.0014 (13)
C6	0.0562 (14)	0.0670 (14)	0.0632 (14)	0.0044 (11)	−0.0053 (11)	−0.0060 (11)
C7	0.0614 (14)	0.0557 (14)	0.0533 (12)	0.0019 (11)	−0.0049 (11)	−0.0015 (10)
C8	0.0495 (13)	0.0528 (13)	0.0492 (11)	−0.0008 (10)	0.0046 (10)	0.0046 (9)
C9	0.0532 (13)	0.0572 (13)	0.0479 (12)	−0.0021 (10)	0.0013 (10)	0.0052 (9)
C10	0.0797 (18)	0.0590 (15)	0.0784 (16)	0.0070 (13)	0.0002 (14)	0.0158 (12)
C11	0.098 (2)	0.0505 (14)	0.0912 (18)	−0.0078 (14)	0.0007 (16)	0.0030 (13)
C12	0.0789 (18)	0.0650 (16)	0.0854 (17)	−0.0130 (14)	−0.0085 (14)	−0.0043 (13)
C13	0.0575 (14)	0.0613 (14)	0.0674 (14)	−0.0010 (11)	−0.0072 (12)	0.0035 (11)
O3	0.0841 (13)	0.0784 (12)	0.1079 (14)	−0.0043 (10)	0.0345 (10)	−0.0129 (10)
O4	0.1200 (16)	0.1156 (15)	0.0807 (12)	−0.0243 (12)	0.0354 (11)	0.0206 (11)
N4	0.0609 (12)	0.0537 (11)	0.0593 (10)	−0.0076 (9)	0.0082 (9)	0.0003 (8)
N5	0.0471 (10)	0.0521 (11)	0.0596 (10)	−0.0030 (8)	−0.0027 (8)	0.0050 (8)
N6	0.0617 (13)	0.0785 (14)	0.0639 (12)	−0.0201 (11)	0.0049 (10)	0.0003 (11)
C14	0.0411 (11)	0.0551 (13)	0.0540 (12)	−0.0017 (10)	−0.0054 (10)	0.0088 (10)
C15	0.0600 (14)	0.0611 (14)	0.0612 (13)	0.0017 (11)	−0.0018 (11)	0.0040 (11)
C16	0.0699 (16)	0.0852 (18)	0.0588 (14)	0.0048 (14)	0.0074 (12)	0.0083 (13)
C17	0.0656 (16)	0.0809 (18)	0.0705 (15)	−0.0069 (13)	0.0057 (13)	0.0224 (13)
C18	0.0674 (16)	0.0575 (14)	0.0870 (17)	−0.0081 (12)	0.0041 (14)	0.0106 (12)
C19	0.0576 (14)	0.0597 (14)	0.0657 (13)	−0.0019 (11)	0.0077 (11)	0.0022 (10)
C20	0.0495 (13)	0.0569 (13)	0.0554 (12)	−0.0045 (10)	0.0039 (10)	0.0017 (10)
C21	0.0440 (12)	0.0529 (12)	0.0493 (11)	−0.0018 (10)	−0.0045 (10)	0.0055 (9)
C22	0.0500 (12)	0.0585 (13)	0.0497 (12)	−0.0034 (10)	−0.0035 (10)	0.0027 (10)
C23	0.0676 (15)	0.0598 (15)	0.0653 (14)	−0.0136 (12)	−0.0092 (12)	0.0119 (11)
C24	0.0839 (18)	0.0525 (14)	0.0793 (16)	0.0009 (13)	−0.0142 (14)	−0.0009 (12)
C25	0.0714 (16)	0.0646 (16)	0.0675 (14)	0.0105 (12)	0.0007 (13)	−0.0037 (12)
C26	0.0556 (14)	0.0627 (15)	0.0606 (13)	0.0006 (11)	0.0033 (11)	0.0041 (10)

Geometric parameters (Å, º) top

O1—N3	1.224 (3)	C5—H5	0.9300
O2—N3	1.215 (3)	C6—H6	0.9300
O3—N6	1.221 (3)	C7—H7	0.9300
O4—N6	1.223 (3)	C10—H10	0.9300
N1—C1	1.392 (3)	C11—H11	0.9300
N1—N2	1.349 (2)	C12—H12	0.9300
N2—C7	1.285 (3)	C13—H13	0.9300
N3—C9	1.467 (3)	C14—C19	1.383 (3)
N1—H1	0.8600	C14—C15	1.385 (3)
N4—N5	1.347 (2)	C15—C16	1.382 (3)
N4—C14	1.396 (3)	C16—C17	1.374 (3)
N5—C20	1.283 (3)	C17—C18	1.373 (3)
N6—C22	1.464 (3)	C18—C19	1.381 (3)
N4—H4A	0.8600	C20—C21	1.457 (3)
C1—C2	1.379 (3)	C21—C26	1.399 (3)
C1—C6	1.379 (3)	C21—C22	1.397 (3)
C2—C3	1.380 (3)	C22—C23	1.382 (3)
C3—C4	1.366 (3)	C23—C24	1.367 (3)
C4—C5	1.372 (3)	C24—C25	1.379 (3)
C5—C6	1.381 (3)	C25—C26	1.369 (3)
C7—C8	1.458 (3)	C15—H15	0.9300
C8—C9	1.397 (3)	C16—H16	0.9300
C8—C13	1.405 (3)	C17—H17	0.9300
C9—C10	1.386 (3)	C18—H18	0.9300
C10—C11	1.370 (4)	C19—H19	0.9300
C11—C12	1.375 (4)	C20—H20	0.9300
C12—C13	1.364 (3)	C23—H23	0.9300
C2—H2	0.9300	C24—H24	0.9300
C3—H3	0.9300	C25—H25	0.9300
C4—H4	0.9300	C26—H26	0.9300

N2—N1—C1	120.29 (16)	C11—C10—H10	120.00
N1—N2—C7	117.70 (16)	C10—C11—H11	120.00
O1—N3—O2	122.04 (19)	C12—C11—H11	120.00
O1—N3—C9	119.56 (18)	C13—C12—H12	120.00
O2—N3—C9	118.4 (2)	C11—C12—H12	119.00
N2—N1—H1	120.00	C12—C13—H13	119.00
C1—N1—H1	120.00	C8—C13—H13	119.00
N5—N4—C14	119.88 (16)	N4—C14—C15	122.00 (18)
N4—N5—C20	117.69 (16)	N4—C14—C19	118.58 (18)
O4—N6—C22	118.0 (2)	C15—C14—C19	119.42 (19)
O3—N6—C22	119.83 (19)	C14—C15—C16	119.5 (2)
O3—N6—O4	122.2 (2)	C15—C16—C17	121.2 (2)
C14—N4—H4A	120.00	C16—C17—C18	119.2 (2)
N5—N4—H4A	120.00	C17—C18—C19	120.5 (2)
N1—C1—C6	122.54 (18)	C14—C19—C18	120.2 (2)
N1—C1—C2	118.24 (18)	N5—C20—C21	118.69 (18)
C2—C1—C6	119.22 (19)	C22—C21—C26	115.09 (18)
C1—C2—C3	120.3 (2)	C20—C21—C22	125.64 (18)
C2—C3—C4	120.8 (2)	C20—C21—C26	119.26 (18)
C3—C4—C5	118.8 (2)	C21—C22—C23	122.79 (19)
C4—C5—C6	121.5 (2)	N6—C22—C21	121.51 (18)
C1—C6—C5	119.4 (2)	N6—C22—C23	115.70 (19)
N2—C7—C8	118.89 (18)	C22—C23—C24	120.0 (2)
C7—C8—C9	126.23 (18)	C23—C24—C25	119.0 (2)
C9—C8—C13	115.33 (18)	C24—C25—C26	120.7 (2)
C7—C8—C13	118.44 (18)	C21—C26—C25	122.4 (2)
C8—C9—C10	122.40 (19)	C14—C15—H15	120.00
N3—C9—C10	114.96 (19)	C16—C15—H15	120.00
N3—C9—C8	122.63 (18)	C15—C16—H16	119.00
C9—C10—C11	120.0 (2)	C17—C16—H16	119.00
C10—C11—C12	119.1 (2)	C16—C17—H17	120.00
C11—C12—C13	120.9 (2)	C18—C17—H17	120.00
C8—C13—C12	122.2 (2)	C17—C18—H18	120.00
C3—C2—H2	120.00	C19—C18—H18	120.00
C1—C2—H2	120.00	C14—C19—H19	120.00
C4—C3—H3	120.00	C18—C19—H19	120.00
C2—C3—H3	120.00	N5—C20—H20	121.00
C3—C4—H4	121.00	C21—C20—H20	121.00
C5—C4—H4	121.00	C22—C23—H23	120.00
C6—C5—H5	119.00	C24—C23—H23	120.00
C4—C5—H5	119.00	C23—C24—H24	121.00
C5—C6—H6	120.00	C25—C24—H24	120.00
C1—C6—H6	120.00	C24—C25—H25	120.00
C8—C7—H7	121.00	C26—C25—H25	120.00
N2—C7—H7	121.00	C21—C26—H26	119.00
C9—C10—H10	120.00	C25—C26—H26	119.00

C1—N1—N2—C7	−174.85 (18)	C7—C8—C13—C12	−179.5 (2)
N2—N1—C1—C2	174.72 (18)	C9—C8—C13—C12	1.0 (3)
N2—N1—C1—C6	−5.8 (3)	C13—C8—C9—C10	−1.6 (3)
N1—N2—C7—C8	178.67 (17)	N3—C9—C10—C11	179.9 (2)
O1—N3—C9—C8	17.2 (3)	C8—C9—C10—C11	1.2 (3)
O1—N3—C9—C10	−161.6 (2)	C9—C10—C11—C12	0.0 (4)
O2—N3—C9—C8	−163.5 (2)	C10—C11—C12—C13	−0.6 (4)
O2—N3—C9—C10	17.8 (3)	C11—C12—C13—C8	0.0 (4)
N5—N4—C14—C15	1.6 (3)	N4—C14—C15—C16	179.44 (19)
N5—N4—C14—C19	−179.04 (18)	C19—C14—C15—C16	0.1 (3)
C14—N4—N5—C20	177.50 (18)	N4—C14—C19—C18	−179.7 (2)
N4—N5—C20—C21	179.35 (17)	C15—C14—C19—C18	−0.3 (3)
O3—N6—C22—C23	152.6 (2)	C14—C15—C16—C17	0.3 (3)
O4—N6—C22—C21	153.5 (2)	C15—C16—C17—C18	−0.4 (4)
O3—N6—C22—C21	−27.2 (3)	C16—C17—C18—C19	0.2 (4)
O4—N6—C22—C23	−26.7 (3)	C17—C18—C19—C14	0.1 (3)
C6—C1—C2—C3	−1.0 (3)	N5—C20—C21—C22	169.55 (19)
N1—C1—C6—C5	−178.38 (19)	N5—C20—C21—C26	−11.8 (3)
N1—C1—C2—C3	178.5 (2)	C20—C21—C22—N6	−0.5 (3)
C2—C1—C6—C5	1.1 (3)	C20—C21—C22—C23	179.7 (2)
C1—C2—C3—C4	0.3 (3)	C26—C21—C22—N6	−179.12 (18)
C2—C3—C4—C5	0.4 (3)	C26—C21—C22—C23	1.1 (3)
C3—C4—C5—C6	−0.3 (3)	C20—C21—C26—C25	−179.8 (2)
C4—C5—C6—C1	−0.5 (3)	C22—C21—C26—C25	−1.0 (3)
N2—C7—C8—C9	−167.98 (19)	N6—C22—C23—C24	179.8 (2)
N2—C7—C8—C13	12.6 (3)	C21—C22—C23—C24	−0.3 (3)
C7—C8—C9—N3	0.3 (3)	C22—C23—C24—C25	−0.5 (3)
C7—C8—C9—C10	178.9 (2)	C23—C24—C25—C26	0.5 (4)
C13—C8—C9—N3	179.78 (18)	C24—C25—C26—C21	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.24	2.773 (3)	116
C20—H20···O3	0.93	2.27	2.788 (3)	115
N1—H1···O3ⁱ	0.86	2.42	3.242 (2)	161
N4—H4A···O1ⁱⁱ	0.86	2.39	3.207 (2)	158

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₂
M_r	241.25
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	19.4021 (13), 12.1065 (7), 20.0554 (11)
V (Å³)	4710.8 (5)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.28 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.972, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	18932, 4260, 2577
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.117, 1.01
No. of reflections	4260
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.24	2.773 (3)	116
C20—H20···O3	0.93	2.27	2.788 (3)	115
N1—H1···O3ⁱ	0.86	2.42	3.242 (2)	161
N4—H4A···O1ⁱⁱ	0.86	2.39	3.207 (2)	158

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Mufakkar, M., Tahir, M. N., Tariq, M. I., Ahmad, S. & Sarfraz, M. (2010). Acta Cryst. E66, o1887. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010). Acta Cryst. E66, o1817. Web of Science CSD CrossRef IUCr Journals Google Scholar