(E)-1-(2-Nitro-benzyl-idene)-2-phenyl-hydrazine.

The asymmetric unit of the title compound, C(13)H(11)N(3)O(2), contains two mol-ecules with slightly different conformations: the dihedral angle between the aromatic rings is 13.01 (10)° in one mol-ecule and 14.05 (10)° in the other. Both mol-ecules feature short intra-molecular C-H⋯O contacts, which generate S(6) rings. In the crystal, both mol-ecules form inversion dimers linked by pairs of N-H⋯O hydrogen bonds, thereby generating R(2) (2)(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 = 241.25

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.01

4260 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025882/hb5534Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H11N3O2	F(000) = 2016
Mr = 241.25	Dx = 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

Bruker Kappa APEXII CCD diffractometer	4260 independent reflections
Radiation source: fine-focus sealed tube	2577 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 8.20 pixels mm-1	θmax = 25.3°, θmin = 2.2°
ω scans	h = −21→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→14
Tmin = 0.972, Tmax = 0.979	l = −24→24
18932 measured reflections

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(Fo2) + (0.0426P)2 + 0.9743P] where P = (Fo2 + 2Fc2)/3
4260 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .