Methyl 2-meth-oxy-4-{[2-(4-nitro-phen-yl)hydrazinyl-idene]meth-yl}benzoate.

The mol-ecule of the title Schiff base compound, C(16)H(15)N(3)O(5), obtained from a condensation reaction of 4-acet-oxy-3-meth-oxy-benzaldehyde and 4-nitro-phenyl-hydrazine, adopts an E geometry with respect to the C=N double bond. The mol-ecule is roughly planar, with the two benzene rings twisted slightly with respect to each other by a dihedral angle of 6.90 (9)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link centrosymmetrically related pairs of mol-ecules, forming dimers of R(2) (2)(22) graph-set motif. The dimers are further connected through slipped π-π inter-actions between symmetry-related benzene rings [centroid-centroid distance of 3.646 (1) Å, offset angle of 15.4°].

Related literature

For potential applications of hydrazone derivatives, see: Okabe et al. (1993 ▶). For related structures, see: Szczesna & Urbanczyk-Lipkowska (2002 ▶); Zhen & Han (2005 ▶); Kuleshova et al. (2003 ▶); Baughman et al. (2004 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1994 ▶).

Experimental

Crystal data

C16H15N3O5

M = 329.31

Monoclinic,

a = 8.5983 (7) Å

b = 14.6982 (9) Å

c = 13.2096 (10) Å

β = 107.860 (9)°

V = 1589.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.23 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.971, T max = 0.976

6773 measured reflections

3255 independent reflections

1397 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.072

S = 0.72

3255 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003802X/dn2604sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003802X/dn2604Isup2.hkl

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

C16H15N3O5	F(000) = 688
Mr = 329.31	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1694 reflections
a = 8.5983 (7) Å	θ = 3.2–26.3°
b = 14.6982 (9) Å	µ = 0.10 mm−1
c = 13.2096 (10) Å	T = 293 K
β = 107.860 (9)°	Block, red
V = 1589.0 (2) Å3	0.23 × 0.20 × 0.19 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3255 independent reflections
Radiation source: fine-focus sealed tube	1397 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.971, Tmax = 0.976	k = −15→18
6773 measured reflections	l = −16→10

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 0.72	w = 1/[σ2(Fo2) + (0.032P)2] where P = (Fo2 + 2Fc2)/3
3255 reflections	(Δ/σ)max = 0.007
219 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.3583 (2)	0.28271 (10)	0.40773 (12)	0.0934 (5)
O2	0.41338 (19)	0.17034 (10)	0.51701 (12)	0.0912 (5)
O3	0.94760 (16)	−0.07061 (8)	−0.28742 (9)	0.0600 (4)
O4	0.84502 (16)	0.09303 (8)	−0.37261 (9)	0.0560 (4)
O5	1.10849 (17)	0.12748 (8)	−0.29655 (11)	0.0628 (4)
N1	0.66329 (16)	0.00919 (9)	0.15774 (11)	0.0493 (4)
H1	0.6925	−0.0461	0.1750	0.059*
N2	0.68044 (17)	0.04452 (9)	0.06596 (11)	0.0451 (4)
N3	0.4121 (2)	0.20643 (13)	0.43252 (14)	0.0649 (5)
C1	0.6057 (2)	0.02353 (12)	0.32125 (14)	0.0522 (5)
H1B	0.6504	−0.0339	0.3408	0.063*
C2	0.5452 (2)	0.07193 (13)	0.38904 (14)	0.0553 (5)
H2B	0.5495	0.0478	0.4549	0.066*
C3	0.4777 (2)	0.15662 (12)	0.35965 (15)	0.0468 (5)
C4	0.4691 (2)	0.19305 (11)	0.26147 (14)	0.0495 (5)
H4A	0.4215	0.2498	0.2416	0.059*
C5	0.5311 (2)	0.14503 (11)	0.19376 (14)	0.0468 (5)
H5A	0.5266	0.1696	0.1280	0.056*
C6	0.6006 (2)	0.06010 (12)	0.22253 (14)	0.0417 (4)
C7	0.7483 (2)	−0.00733 (11)	0.01437 (13)	0.0452 (5)
H7A	0.7806	−0.0654	0.0403	0.054*
C8	0.7767 (2)	0.02182 (11)	−0.08375 (13)	0.0403 (4)
C9	0.85046 (19)	−0.03850 (11)	−0.13560 (13)	0.0434 (5)
H9A	0.8822	−0.0956	−0.1061	0.052*
C10	0.8777 (2)	−0.01552 (11)	−0.23029 (14)	0.0434 (5)
C11	0.8294 (2)	0.06963 (12)	−0.27239 (13)	0.0449 (5)
C12	0.7565 (2)	0.13013 (11)	−0.22286 (15)	0.0518 (5)
H12A	0.7246	0.1870	−0.2528	0.062*
C13	0.7300 (2)	0.10665 (11)	−0.12796 (15)	0.0516 (5)
H13A	0.6809	0.1479	−0.0939	0.062*
C14	0.9936 (2)	−0.15954 (11)	−0.24715 (14)	0.0632 (6)
H14A	1.0419	−0.1913	−0.2935	0.095*
H14B	0.8987	−0.1920	−0.2433	0.095*
H14C	1.0714	−0.1554	−0.1774	0.095*
C15	0.9935 (3)	0.12176 (12)	−0.37443 (17)	0.0507 (5)
C16	0.9907 (3)	0.14511 (15)	−0.48491 (15)	0.0823 (7)
H16A	0.9030	0.1868	−0.5155	0.123*
H16B	0.9748	0.0907	−0.5271	0.123*
H16C	1.0927	0.1728	−0.4832	0.123*

	U11	U22	U33	U12	U13	U23
O1	0.1226 (15)	0.0764 (11)	0.0863 (11)	0.0205 (11)	0.0397 (10)	−0.0154 (10)
O2	0.1189 (14)	0.1058 (12)	0.0648 (10)	−0.0012 (10)	0.0517 (10)	−0.0052 (9)
O3	0.0790 (10)	0.0505 (7)	0.0600 (9)	0.0083 (7)	0.0352 (8)	0.0004 (7)
O4	0.0524 (9)	0.0728 (9)	0.0439 (8)	−0.0030 (8)	0.0165 (7)	0.0089 (7)
O5	0.0551 (9)	0.0710 (9)	0.0609 (9)	−0.0025 (8)	0.0159 (8)	0.0054 (8)
N1	0.0584 (11)	0.0466 (9)	0.0481 (10)	0.0032 (8)	0.0239 (9)	0.0052 (8)
N2	0.0454 (10)	0.0511 (9)	0.0398 (9)	−0.0051 (8)	0.0144 (8)	0.0022 (8)
N3	0.0633 (13)	0.0740 (13)	0.0596 (13)	−0.0106 (11)	0.0220 (11)	−0.0172 (11)
C1	0.0561 (14)	0.0545 (11)	0.0498 (12)	0.0049 (10)	0.0219 (11)	0.0108 (10)
C2	0.0574 (14)	0.0680 (13)	0.0445 (12)	−0.0063 (11)	0.0214 (11)	0.0074 (11)
C3	0.0452 (13)	0.0533 (12)	0.0450 (12)	−0.0092 (10)	0.0186 (10)	−0.0085 (10)
C4	0.0509 (14)	0.0436 (11)	0.0530 (12)	−0.0085 (10)	0.0145 (11)	−0.0036 (10)
C5	0.0546 (13)	0.0444 (11)	0.0428 (11)	−0.0092 (10)	0.0172 (10)	0.0019 (9)
C6	0.0398 (11)	0.0472 (11)	0.0379 (11)	−0.0100 (9)	0.0117 (9)	−0.0017 (9)
C7	0.0427 (13)	0.0459 (11)	0.0464 (12)	−0.0054 (10)	0.0131 (10)	−0.0006 (9)
C8	0.0397 (12)	0.0405 (10)	0.0408 (11)	−0.0068 (9)	0.0124 (10)	−0.0009 (9)
C9	0.0434 (13)	0.0392 (10)	0.0472 (12)	−0.0011 (9)	0.0131 (10)	−0.0007 (9)
C10	0.0409 (12)	0.0441 (11)	0.0458 (12)	−0.0023 (10)	0.0144 (10)	−0.0066 (10)
C11	0.0417 (12)	0.0540 (12)	0.0386 (11)	−0.0017 (10)	0.0117 (10)	0.0044 (10)
C12	0.0548 (13)	0.0447 (11)	0.0599 (13)	0.0036 (10)	0.0238 (11)	0.0082 (10)
C13	0.0561 (13)	0.0457 (11)	0.0592 (13)	0.0017 (10)	0.0268 (11)	−0.0035 (10)
C14	0.0789 (16)	0.0483 (11)	0.0683 (14)	0.0097 (11)	0.0316 (13)	−0.0045 (11)
C15	0.0583 (14)	0.0454 (11)	0.0525 (13)	0.0064 (11)	0.0232 (12)	0.0019 (10)
C16	0.0886 (18)	0.1103 (17)	0.0573 (14)	−0.0082 (15)	0.0361 (13)	0.0100 (13)

O1—N3	1.2188 (18)	C5—C6	1.386 (2)
O2—N3	1.2326 (18)	C5—H5A	0.9300
O3—C10	1.3655 (18)	C7—C8	1.455 (2)
O3—C14	1.4210 (18)	C7—H7A	0.9300
O4—C15	1.352 (2)	C8—C13	1.383 (2)
O4—C11	1.4135 (18)	C8—C9	1.387 (2)
O5—C15	1.191 (2)	C9—C10	1.383 (2)
N1—C6	1.3663 (18)	C9—H9A	0.9300
N1—N2	1.3678 (16)	C10—C11	1.381 (2)
N1—H1	0.8600	C11—C12	1.365 (2)
N2—C7	1.2766 (18)	C12—C13	1.385 (2)
N3—C3	1.454 (2)	C12—H12A	0.9300
C1—C2	1.366 (2)	C13—H13A	0.9300
C1—C6	1.399 (2)	C14—H14A	0.9600
C1—H1B	0.9300	C14—H14B	0.9600
C2—C3	1.378 (2)	C14—H14C	0.9600
C2—H2B	0.9300	C15—C16	1.492 (2)
C3—C4	1.384 (2)	C16—H16A	0.9600
C4—C5	1.369 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C10—O3—C14	117.25 (13)	C9—C8—C7	118.60 (16)
C15—O4—C11	117.01 (14)	C10—C9—C8	121.35 (16)
C6—N1—N2	121.19 (14)	C10—C9—H9A	119.3
C6—N1—H1	119.4	C8—C9—H9A	119.3
N2—N1—H1	119.4	O3—C10—C11	116.35 (16)
C7—N2—N1	115.96 (14)	O3—C10—C9	125.47 (16)
O1—N3—O2	122.44 (18)	C11—C10—C9	118.18 (16)
O1—N3—C3	118.54 (18)	C12—C11—C10	121.53 (17)
O2—N3—C3	119.02 (19)	C12—C11—O4	118.68 (16)
C2—C1—C6	120.11 (17)	C10—C11—O4	119.64 (16)
C2—C1—H1B	119.9	C11—C12—C13	119.91 (16)
C6—C1—H1B	119.9	C11—C12—H12A	120.0
C1—C2—C3	119.87 (17)	C13—C12—H12A	120.0
C1—C2—H2B	120.1	C8—C13—C12	120.00 (16)
C3—C2—H2B	120.1	C8—C13—H13A	120.0
C2—C3—C4	120.70 (17)	C12—C13—H13A	120.0
C2—C3—N3	118.93 (18)	O3—C14—H14A	109.5
C4—C3—N3	120.36 (18)	O3—C14—H14B	109.5
C5—C4—C3	119.54 (17)	H14A—C14—H14B	109.5
C5—C4—H4A	120.2	O3—C14—H14C	109.5
C3—C4—H4A	120.2	H14A—C14—H14C	109.5
C4—C5—C6	120.43 (16)	H14B—C14—H14C	109.5
C4—C5—H5A	119.8	O5—C15—O4	123.01 (18)
C6—C5—H5A	119.8	O5—C15—C16	126.1 (2)
N1—C6—C5	122.77 (16)	O4—C15—C16	110.93 (19)
N1—C6—C1	117.89 (16)	C15—C16—H16A	109.5
C5—C6—C1	119.33 (17)	C15—C16—H16B	109.5
N2—C7—C8	121.93 (16)	H16A—C16—H16B	109.5
N2—C7—H7A	119.0	C15—C16—H16C	109.5
C8—C7—H7A	119.0	H16A—C16—H16C	109.5
C13—C8—C9	119.02 (16)	H16B—C16—H16C	109.5
C13—C8—C7	122.37 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.86	2.29	3.0068 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.86	2.29	3.0068 (19)	141

Symmetry code: (i) .