(E)-1-(3-Nitro-phen-yl)ethanone (2-methyl-phen-yl)hydrazone.

In the title Schiff base compound, C(15)H(15)N(3)O(2), the azomethine double bond adopts an E configuration. The dihedral angle between the two aromatic rings is 13.4 (12)°. In the crystal, mol-ecules are arranged in wave-like layers parallel to (100) without any classical hydrogen bonding.

Related literature

For the biological activit of Schiff bases, see: Khan et al. (2009 ▶); Gerdemann et al. (2002 ▶); Mallikarjun & Sangamesh (1997 ▶); Solomon & Lowery (1993 ▶). For the role of Schiff bases and Amadori products in the process of glycation, see: Ahmad et al. (2007 ▶); Ahmed (2005) ▶. For the crystal structures of closely related compounds see: Fun et al. (2008 ▶); Tezcan et al. (2004 ▶).

Experimental

Crystal data

C15H15N3O2

M = 269.30

Monoclinic,

a = 7.4763 (18) Å

b = 25.742 (6) Å

c = 7.6564 (19) Å

β = 110.485 (5)°

V = 1380.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.51 × 0.46 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.956, T max = 0.993

7958 measured reflections

2535 independent reflections

1746 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.176

S = 1.04

2535 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037846/rz2637sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037846/rz2637Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037846/rz2637Isup3.cml

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

C15H15N3O2	F(000) = 568
Mr = 269.30	Dx = 1.296 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2070 reflections
a = 7.4763 (18) Å	θ = 3.0–24.4°
b = 25.742 (6) Å	µ = 0.09 mm−1
c = 7.6564 (19) Å	T = 273 K
β = 110.485 (5)°	Plate, yellow
V = 1380.3 (6) Å3	0.51 × 0.46 × 0.08 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2535 independent reflections
Radiation source: fine-focus sealed tube	1746 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.956, Tmax = 0.993	k = −31→29
7958 measured reflections	l = −9→9

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0991P)2 + 0.0824P] where P = (Fo2 + 2Fc2)/3
2535 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	−0.0105 (4)	0.25761 (8)	0.7851 (3)	0.1120 (8)
O2	−0.0998 (3)	0.30826 (7)	0.5495 (3)	0.0983 (6)
N1	0.2485 (3)	0.00558 (7)	0.5057 (3)	0.0652 (5)
N2	0.1857 (2)	0.05385 (7)	0.4420 (2)	0.0600 (5)
N3	−0.0373 (3)	0.26679 (8)	0.6232 (3)	0.0753 (6)
C1	0.0995 (4)	0.15320 (9)	0.3011 (3)	0.0716 (6)
H1B	0.1320	0.1284	0.2290	0.086*
C2	0.0380 (4)	0.20121 (10)	0.2255 (3)	0.0780 (7)
H2B	0.0275	0.2082	0.1032	0.094*
C3	−0.0082 (3)	0.23888 (9)	0.3293 (3)	0.0705 (6)
H3A	−0.0495	0.2716	0.2797	0.085*
C4	0.0086 (3)	0.22673 (8)	0.5084 (3)	0.0603 (5)
C5	0.0684 (3)	0.17883 (8)	0.5874 (3)	0.0581 (5)
H5A	0.0778	0.1722	0.7097	0.070*
C6	0.1147 (3)	0.14059 (8)	0.4826 (3)	0.0557 (5)
C7	0.1796 (3)	0.08832 (8)	0.5615 (3)	0.0548 (5)
C8	0.3256 (3)	−0.08197 (8)	0.4538 (3)	0.0619 (6)
C9	0.3307 (3)	−0.12021 (9)	0.3286 (4)	0.0759 (7)
H9A	0.3731	−0.1533	0.3731	0.091*
C10	0.2748 (4)	−0.11080 (11)	0.1401 (4)	0.0856 (8)
H10A	0.2791	−0.1372	0.0588	0.103*
C11	0.2130 (4)	−0.06233 (11)	0.0734 (3)	0.0821 (7)
H11A	0.1747	−0.0558	−0.0539	0.099*
C12	0.2068 (3)	−0.02331 (9)	0.1923 (3)	0.0691 (6)
H12A	0.1665	0.0097	0.1456	0.083*
C13	0.2604 (3)	−0.03265 (8)	0.3823 (3)	0.0576 (5)
C14	0.3872 (4)	−0.09290 (10)	0.6573 (3)	0.0836 (7)
H14A	0.4376	−0.1275	0.6814	0.125*
H14B	0.2796	−0.0898	0.6976	0.125*
H14C	0.4840	−0.0685	0.7242	0.125*
C15	0.2345 (4)	0.07845 (9)	0.7658 (3)	0.0728 (6)
H15A	0.3563	0.0614	0.8110	0.109*
H15B	0.1401	0.0567	0.7877	0.109*
H15C	0.2422	0.1109	0.8299	0.109*
H1N1	0.285 (4)	−0.0027 (9)	0.622 (4)	0.079 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.164 (2)	0.0973 (14)	0.0794 (12)	0.0453 (13)	0.0483 (12)	0.0098 (10)
O2	0.1248 (17)	0.0622 (11)	0.0986 (13)	0.0146 (10)	0.0274 (11)	0.0023 (9)
N1	0.0681 (13)	0.0615 (11)	0.0611 (11)	0.0066 (9)	0.0163 (9)	0.0031 (9)
N2	0.0516 (11)	0.0601 (11)	0.0647 (10)	0.0009 (8)	0.0160 (8)	0.0015 (8)
N3	0.0795 (14)	0.0627 (12)	0.0776 (13)	0.0076 (10)	0.0199 (10)	0.0030 (10)
C1	0.0782 (16)	0.0720 (15)	0.0702 (14)	0.0032 (11)	0.0332 (12)	0.0025 (11)
C2	0.0897 (19)	0.0802 (17)	0.0677 (14)	0.0014 (13)	0.0320 (13)	0.0129 (12)
C3	0.0662 (15)	0.0631 (14)	0.0774 (15)	−0.0015 (11)	0.0192 (11)	0.0118 (11)
C4	0.0520 (13)	0.0586 (12)	0.0665 (12)	−0.0038 (9)	0.0161 (10)	0.0011 (10)
C5	0.0509 (12)	0.0613 (13)	0.0574 (11)	−0.0066 (9)	0.0130 (9)	0.0002 (9)
C6	0.0431 (12)	0.0613 (12)	0.0592 (11)	−0.0076 (9)	0.0134 (9)	−0.0007 (9)
C7	0.0432 (11)	0.0590 (12)	0.0593 (11)	−0.0054 (9)	0.0144 (9)	−0.0009 (9)
C8	0.0457 (12)	0.0651 (13)	0.0742 (13)	−0.0017 (9)	0.0200 (10)	0.0006 (10)
C9	0.0613 (15)	0.0673 (15)	0.1014 (18)	0.0070 (11)	0.0315 (13)	−0.0033 (12)
C10	0.0767 (18)	0.095 (2)	0.0891 (18)	0.0090 (14)	0.0334 (14)	−0.0222 (14)
C11	0.0724 (17)	0.106 (2)	0.0678 (14)	0.0161 (14)	0.0244 (12)	−0.0065 (14)
C12	0.0586 (14)	0.0786 (15)	0.0685 (13)	0.0098 (11)	0.0202 (11)	0.0034 (11)
C13	0.0413 (11)	0.0634 (13)	0.0673 (13)	−0.0017 (9)	0.0180 (9)	−0.0010 (10)
C14	0.0877 (19)	0.0762 (16)	0.0867 (17)	0.0121 (13)	0.0302 (14)	0.0189 (13)
C15	0.0769 (17)	0.0654 (14)	0.0697 (14)	0.0015 (11)	0.0180 (12)	0.0036 (10)

O1—N3	1.207 (2)	C7—C15	1.493 (3)
O2—N3	1.222 (2)	C8—C9	1.384 (3)
N1—N2	1.357 (2)	C8—C13	1.401 (3)
N1—C13	1.389 (3)	C8—C14	1.489 (3)
N1—H1N1	0.86 (2)	C9—C10	1.376 (3)
N2—C7	1.286 (2)	C9—H9A	0.9300
N3—C4	1.471 (3)	C10—C11	1.366 (4)
C1—C2	1.374 (3)	C10—H10A	0.9300
C1—C6	1.392 (3)	C11—C12	1.367 (3)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.372 (3)	C12—C13	1.388 (3)
C2—H2B	0.9300	C12—H12A	0.9300
C3—C4	1.369 (3)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.377 (3)	C14—H14C	0.9600
C5—C6	1.388 (3)	C15—H15A	0.9600
C5—H5A	0.9300	C15—H15B	0.9600
C6—C7	1.485 (3)	C15—H15C	0.9600
N2—N1—C13	120.06 (18)	C9—C8—C14	121.1 (2)
N2—N1—H1N1	122.9 (16)	C13—C8—C14	121.22 (19)
C13—N1—H1N1	117.0 (16)	C10—C9—C8	122.0 (2)
C7—N2—N1	118.04 (17)	C10—C9—H9A	119.0
O1—N3—O2	123.0 (2)	C8—C9—H9A	119.0
O1—N3—C4	119.10 (19)	C11—C10—C9	119.4 (2)
O2—N3—C4	117.9 (2)	C11—C10—H10A	120.3
C2—C1—C6	121.9 (2)	C9—C10—H10A	120.3
C2—C1—H1B	119.1	C10—C11—C12	120.6 (2)
C6—C1—H1B	119.1	C10—C11—H11A	119.7
C3—C2—C1	120.5 (2)	C12—C11—H11A	119.7
C3—C2—H2B	119.8	C11—C12—C13	120.4 (2)
C1—C2—H2B	119.8	C11—C12—H12A	119.8
C4—C3—C2	117.7 (2)	C13—C12—H12A	119.8
C4—C3—H3A	121.1	C12—C13—N1	121.79 (19)
C2—C3—H3A	121.1	C12—C13—C8	120.01 (19)
C3—C4—C5	123.11 (19)	N1—C13—C8	118.19 (19)
C3—C4—N3	118.66 (19)	C8—C14—H14A	109.5
C5—C4—N3	118.24 (19)	C8—C14—H14B	109.5
C4—C5—C6	119.32 (19)	H14A—C14—H14B	109.5
C4—C5—H5A	120.3	C8—C14—H14C	109.5
C6—C5—H5A	120.3	H14A—C14—H14C	109.5
C5—C6—C1	117.51 (19)	H14B—C14—H14C	109.5
C5—C6—C7	121.31 (18)	C7—C15—H15A	109.5
C1—C6—C7	121.17 (18)	C7—C15—H15B	109.5
N2—C7—C6	115.08 (17)	H15A—C15—H15B	109.5
N2—C7—C15	124.21 (18)	C7—C15—H15C	109.5
C6—C7—C15	120.72 (17)	H15A—C15—H15C	109.5
C9—C8—C13	117.6 (2)	H15B—C15—H15C	109.5
C13—N1—N2—C7	−178.96 (16)	C5—C6—C7—N2	168.33 (17)
C6—C1—C2—C3	1.0 (4)	C1—C6—C7—N2	−12.2 (3)
C1—C2—C3—C4	−0.3 (4)	C5—C6—C7—C15	−12.3 (3)
C2—C3—C4—C5	−0.2 (3)	C1—C6—C7—C15	167.1 (2)
C2—C3—C4—N3	179.1 (2)	C13—C8—C9—C10	0.2 (3)
O1—N3—C4—C3	−175.0 (2)	C14—C8—C9—C10	−179.8 (2)
O2—N3—C4—C3	4.4 (3)	C8—C9—C10—C11	0.2 (4)
O1—N3—C4—C5	4.4 (3)	C9—C10—C11—C12	0.2 (4)
O2—N3—C4—C5	−176.2 (2)	C10—C11—C12—C13	−1.1 (4)
C3—C4—C5—C6	0.1 (3)	C11—C12—C13—N1	−177.4 (2)
N3—C4—C5—C6	−179.27 (18)	C11—C12—C13—C8	1.6 (3)
C4—C5—C6—C1	0.6 (3)	N2—N1—C13—C12	−1.0 (3)
C4—C5—C6—C7	−179.92 (18)	N2—N1—C13—C8	−179.92 (17)
C2—C1—C6—C5	−1.2 (3)	C9—C8—C13—C12	−1.1 (3)
C2—C1—C6—C7	179.4 (2)	C14—C8—C13—C12	179.0 (2)
N1—N2—C7—C6	178.38 (16)	C9—C8—C13—N1	177.85 (18)
N1—N2—C7—C15	−1.0 (3)	C14—C8—C13—N1	−2.1 (3)