(E)-1-(3-Methoxy-phen-yl)ethanone 4-nitro-phenyl-hydrazone.

Crystals of the title compound, C(15)H(15)N(3)O(3), were obtained from a condensation reaction of 4-nitro-phenyl-hydrazine and 3-methoxy-acetophenone. In the crystal structure, the methoxy-phenyl ring is twisted slightly with respect to the nitro-phenyl-hydrazine plane, making a dihedral angle of 14.81 (8)°. The nitro and meth-oxy groups are each coplanar with the attached benzene rings. The nitro-phenyl and methoxy-phenyl groups are located on opposite sides of the C=N double bond, indicating an E configuration of the mol-ecule. Adjacent mol-ecules are linked together via N-H⋯O hydrogen bonding, forming chains along the [101] direction.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2003a ▶). For related structures, see: Shan et al. (2003b ▶, 2004 ▶, 2008 ▶).

Experimental

Crystal data

C15H15N3O3

M = 285.30

Monoclinic,

a = 4.2977 (17) Å

b = 24.709 (9) Å

c = 13.132 (5) Å

β = 96.332 (11)°

V = 1386.0 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.32 × 0.26 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

16470 measured reflections

3014 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.141

S = 1.03

3014 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018618/om2241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018618/om2241Isup2.hkl

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

C15H15N3O3	F000 = 600
Mr = 285.30	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4665 reflections
a = 4.2977 (17) Å	θ = 2.0–25.0º
b = 24.709 (9) Å	µ = 0.10 mm−1
c = 13.132 (5) Å	T = 295 (2) K
β = 96.332 (11)º	Prism, red
V = 1386.0 (9) Å3	0.32 × 0.26 × 0.22 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	3014 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
Detector resolution: 10.00 pixels mm-1	θmax = 27.0º
T = 295(2) K	θmin = 1.7º
ω scans	h = −5→5
Absorption correction: none	k = −30→31
16470 measured reflections	l = −16→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.02P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3014 reflections	Δρmax = 0.15 e Å−3
192 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.2858 (3)	0.59466 (6)	0.29114 (11)	0.0540 (4)
N2	0.4535 (3)	0.63991 (6)	0.27160 (11)	0.0573 (4)
H2	0.4405	0.6533	0.2109	0.069*
N3	1.2264 (4)	0.73954 (7)	0.58666 (13)	0.0656 (5)
O1	−0.4958 (3)	0.41329 (6)	0.10899 (10)	0.0775 (5)
O2	1.2533 (4)	0.71902 (6)	0.67268 (11)	0.0944 (6)
O3	1.3617 (4)	0.78225 (6)	0.56823 (11)	0.0865 (5)
C1	−0.0634 (4)	0.52365 (7)	0.24122 (12)	0.0507 (5)
C2	−0.2090 (4)	0.48991 (7)	0.16601 (13)	0.0563 (5)
H2A	−0.2011	0.4985	0.0974	0.068*
C3	−0.3663 (4)	0.44357 (8)	0.19125 (13)	0.0574 (5)
C4	−0.3852 (5)	0.43034 (8)	0.29148 (15)	0.0680 (6)
H4	−0.4900	0.3993	0.3087	0.082*
C5	−0.2442 (5)	0.46436 (9)	0.36672 (14)	0.0775 (7)
H5	−0.2576	0.4560	0.4351	0.093*
C6	−0.0856 (5)	0.51000 (8)	0.34328 (14)	0.0669 (6)
H6	0.0075	0.5319	0.3955	0.080*
C7	0.1106 (4)	0.57271 (7)	0.21575 (13)	0.0528 (5)
C8	0.0787 (5)	0.59459 (9)	0.10844 (15)	0.0818 (7)
H8A	0.0396	0.6328	0.1099	0.123*
H8B	−0.0926	0.5769	0.0686	0.123*
H8C	0.2686	0.5880	0.0782	0.123*
C9	−0.6460 (5)	0.36382 (8)	0.13053 (16)	0.0790 (7)
H9A	−0.5045	0.3419	0.1746	0.119*
H9B	−0.7058	0.3448	0.0677	0.119*
H9C	−0.8290	0.3715	0.1638	0.119*
C10	0.6430 (4)	0.66358 (7)	0.35048 (13)	0.0488 (4)
C11	0.6824 (4)	0.64122 (7)	0.44883 (14)	0.0574 (5)
H11	0.5794	0.6094	0.4625	0.069*
C12	0.8742 (4)	0.66645 (8)	0.52547 (14)	0.0582 (5)
H12	0.8993	0.6518	0.5911	0.070*
C13	1.0288 (4)	0.71338 (7)	0.50517 (13)	0.0520 (5)
C14	0.9974 (4)	0.73569 (7)	0.40765 (14)	0.0566 (5)
H14	1.1054	0.7670	0.3942	0.068*
C15	0.8043 (4)	0.71083 (7)	0.33116 (14)	0.0564 (5)
H15	0.7809	0.7257	0.2657	0.068*

	U11	U22	U33	U12	U13	U23
N1	0.0518 (9)	0.0552 (9)	0.0533 (9)	0.0029 (7)	−0.0015 (7)	−0.0024 (7)
N2	0.0604 (10)	0.0626 (10)	0.0466 (9)	−0.0004 (8)	−0.0039 (7)	0.0005 (7)
N3	0.0698 (11)	0.0610 (11)	0.0636 (11)	0.0079 (9)	−0.0042 (8)	−0.0123 (9)
O1	0.1001 (11)	0.0751 (9)	0.0548 (8)	−0.0272 (8)	−0.0025 (7)	−0.0045 (7)
O2	0.1219 (14)	0.1013 (12)	0.0540 (9)	−0.0124 (10)	−0.0175 (9)	−0.0037 (8)
O3	0.1030 (12)	0.0664 (10)	0.0860 (11)	−0.0165 (9)	−0.0083 (9)	−0.0133 (8)
C1	0.0511 (11)	0.0553 (11)	0.0446 (10)	0.0082 (9)	0.0000 (8)	−0.0006 (8)
C2	0.0628 (12)	0.0616 (12)	0.0435 (10)	0.0016 (9)	0.0011 (9)	−0.0009 (8)
C3	0.0604 (12)	0.0628 (12)	0.0472 (11)	0.0002 (10)	−0.0021 (9)	−0.0039 (9)
C4	0.0795 (15)	0.0695 (13)	0.0539 (12)	−0.0123 (11)	0.0031 (10)	0.0044 (10)
C5	0.1069 (18)	0.0822 (16)	0.0425 (11)	−0.0145 (13)	0.0039 (11)	0.0070 (10)
C6	0.0812 (15)	0.0711 (13)	0.0454 (11)	−0.0056 (11)	−0.0058 (10)	−0.0020 (9)
C7	0.0540 (11)	0.0578 (11)	0.0456 (11)	0.0077 (9)	0.0014 (9)	−0.0020 (8)
C8	0.0992 (17)	0.0880 (16)	0.0542 (12)	−0.0295 (13)	−0.0098 (11)	0.0072 (10)
C9	0.0948 (16)	0.0627 (13)	0.0760 (15)	−0.0158 (12)	−0.0063 (12)	−0.0003 (11)
C10	0.0459 (10)	0.0516 (11)	0.0481 (10)	0.0075 (8)	0.0014 (8)	−0.0032 (8)
C11	0.0610 (12)	0.0545 (11)	0.0557 (12)	−0.0037 (9)	0.0027 (9)	0.0008 (9)
C12	0.0644 (12)	0.0630 (12)	0.0465 (11)	0.0042 (10)	0.0019 (9)	0.0022 (9)
C13	0.0518 (11)	0.0514 (11)	0.0511 (11)	0.0084 (9)	−0.0020 (8)	−0.0077 (8)
C14	0.0564 (12)	0.0496 (11)	0.0625 (12)	0.0029 (9)	0.0001 (9)	−0.0003 (9)
C15	0.0601 (12)	0.0566 (11)	0.0509 (11)	0.0044 (9)	−0.0013 (9)	0.0055 (9)

N1—C7	1.295 (2)	C6—H6	0.9300
N1—N2	1.3699 (19)	C7—C8	1.501 (3)
N2—C10	1.376 (2)	C8—H8A	0.9600
N2—H2	0.8600	C8—H8B	0.9600
N3—O2	1.232 (2)	C8—H8C	0.9600
N3—O3	1.242 (2)	C9—H9A	0.9600
N3—C13	1.443 (2)	C9—H9B	0.9600
O1—C3	1.380 (2)	C9—H9C	0.9600
O1—C9	1.425 (2)	C10—C15	1.395 (2)
C1—C2	1.388 (2)	C10—C11	1.398 (3)
C1—C6	1.395 (2)	C11—C12	1.378 (2)
C1—C7	1.482 (2)	C11—H11	0.9300
C2—C3	1.388 (2)	C12—C13	1.377 (3)
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.367 (3)	C13—C14	1.387 (2)
C4—C5	1.385 (3)	C14—C15	1.375 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.370 (3)	C15—H15	0.9300
C5—H5	0.9300
C7—N1—N2	118.18 (15)	C7—C8—H8B	109.5
N1—N2—C10	119.09 (14)	H8A—C8—H8B	109.5
N1—N2—H2	120.5	C7—C8—H8C	109.5
C10—N2—H2	120.5	H8A—C8—H8C	109.5
O2—N3—O3	121.99 (17)	H8B—C8—H8C	109.5
O2—N3—C13	118.92 (18)	O1—C9—H9A	109.5
O3—N3—C13	119.08 (17)	O1—C9—H9B	109.5
C3—O1—C9	117.53 (15)	H9A—C9—H9B	109.5
C2—C1—C6	117.71 (18)	O1—C9—H9C	109.5
C2—C1—C7	122.00 (16)	H9A—C9—H9C	109.5
C6—C1—C7	120.29 (16)	H9B—C9—H9C	109.5
C1—C2—C3	121.26 (17)	N2—C10—C15	118.92 (16)
C1—C2—H2A	119.4	N2—C10—C11	121.93 (16)
C3—C2—H2A	119.4	C15—C10—C11	119.14 (16)
C4—C3—O1	124.23 (18)	C12—C11—C10	119.85 (17)
C4—C3—C2	120.60 (17)	C12—C11—H11	120.1
O1—C3—C2	115.17 (16)	C10—C11—H11	120.1
C3—C4—C5	118.30 (19)	C13—C12—C11	120.15 (17)
C3—C4—H4	120.8	C13—C12—H12	119.9
C5—C4—H4	120.8	C11—C12—H12	119.9
C6—C5—C4	121.90 (18)	C12—C13—C14	120.89 (16)
C6—C5—H5	119.0	C12—C13—N3	119.38 (17)
C4—C5—H5	119.0	C14—C13—N3	119.73 (18)
C5—C6—C1	120.22 (18)	C15—C14—C13	119.09 (18)
C5—C6—H6	119.9	C15—C14—H14	120.5
C1—C6—H6	119.9	C13—C14—H14	120.5
N1—C7—C1	115.80 (16)	C14—C15—C10	120.86 (17)
N1—C7—C8	123.50 (18)	C14—C15—H15	119.6
C1—C7—C8	120.69 (16)	C10—C15—H15	119.6
C7—C8—H8A	109.5
C7—N1—N2—C10	−179.48 (14)	C6—C1—C7—C8	−166.53 (19)
C6—C1—C2—C3	−1.2 (3)	N1—N2—C10—C15	−177.60 (15)
C7—C1—C2—C3	178.84 (16)	N1—N2—C10—C11	3.4 (2)
C9—O1—C3—C4	−3.0 (3)	N2—C10—C11—C12	−179.86 (15)
C9—O1—C3—C2	176.82 (17)	C15—C10—C11—C12	1.2 (3)
C1—C2—C3—C4	0.9 (3)	C10—C11—C12—C13	−0.5 (3)
C1—C2—C3—O1	−178.98 (16)	C11—C12—C13—C14	−0.7 (3)
O1—C3—C4—C5	179.96 (18)	C11—C12—C13—N3	179.40 (16)
C2—C3—C4—C5	0.1 (3)	O2—N3—C13—C12	0.4 (3)
C3—C4—C5—C6	−0.7 (3)	O3—N3—C13—C12	−179.01 (17)
C4—C5—C6—C1	0.3 (3)	O2—N3—C13—C14	−179.54 (17)
C2—C1—C6—C5	0.7 (3)	O3—N3—C13—C14	1.1 (3)
C7—C1—C6—C5	−179.42 (18)	C12—C13—C14—C15	1.2 (3)
N2—N1—C7—C1	179.54 (13)	N3—C13—C14—C15	−178.92 (16)
N2—N1—C7—C8	−0.8 (3)	C13—C14—C15—C10	−0.5 (3)
C2—C1—C7—N1	−166.90 (16)	N2—C10—C15—C14	−179.69 (15)
C6—C1—C7—N1	13.2 (2)	C11—C10—C15—C14	−0.7 (3)
C2—C1—C7—C8	13.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.86	2.45	3.279 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.86	2.45	3.279 (2)	161

Symmetry code: (i) .