N'-(2-Hy-droxy-4-meth-oxy-benzyl-idene)-3-nitro-benzohydrazide.

In the mol-ecule of the title compound, C(15)H(13)N(3)O(3), an intra-molecular O-H⋯N hydrogen bond influences the planarity of the conformation; the dihedral angle between the benzene rings is 11.4 (3)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains in [101].

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H13N3O5

M = 315.28

Monoclinic,

a = 6.0099 (12) Å

b = 33.575 (3) Å

c = 7.319 (2) Å

β = 94.235 (2)°

V = 1472.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.28 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.976

7720 measured reflections

3155 independent reflections

1786 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.140

S = 1.02

3155 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104178X/cv5171sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104178X/cv5171Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104178X/cv5171Isup3.cml

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

C15H13N3O5	F(000) = 656
Mr = 315.28	Dx = 1.422 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.0099 (12) Å	Cell parameters from 1287 reflections
b = 33.575 (3) Å	θ = 2.4–24.5°
c = 7.319 (2) Å	µ = 0.11 mm−1
β = 94.235 (2)°	T = 298 K
V = 1472.9 (5) Å3	Prism, yellow
Z = 4	0.28 × 0.23 × 0.22 mm

Bruker SMART CCD area-detector diffractometer	3155 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→5
Tmin = 0.970, Tmax = 0.976	k = −42→32
7720 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.3356P] where P = (Fo2 + 2Fc2)/3
3155 reflections	(Δ/σ)max = 0.001
214 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.19 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 > 2sigma(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	0.0936 (3)	0.21111 (6)	0.6779 (2)	0.0459 (5)
N2	0.2422 (3)	0.24250 (6)	0.7037 (3)	0.0472 (5)
N3	0.2828 (5)	0.42054 (7)	0.6691 (3)	0.0671 (7)
O1	−0.2996 (3)	0.18085 (5)	0.5833 (2)	0.0539 (5)
H1	−0.2073	0.1987	0.6014	0.081*
O2	−0.4045 (3)	0.04481 (5)	0.6539 (3)	0.0825 (7)
O3	0.0352 (3)	0.28027 (5)	0.5016 (2)	0.0612 (5)
O4	0.0861 (4)	0.42267 (6)	0.6147 (3)	0.0896 (7)
O5	0.3980 (4)	0.44949 (6)	0.7108 (4)	0.1024 (8)
C1	0.0134 (4)	0.14277 (7)	0.7182 (3)	0.0399 (5)
C2	−0.2087 (4)	0.14565 (7)	0.6411 (3)	0.0415 (6)
C3	−0.3392 (4)	0.11219 (7)	0.6220 (3)	0.0491 (6)
H3	−0.4853	0.1143	0.5714	0.059*
C4	−0.2565 (4)	0.07541 (7)	0.6771 (4)	0.0542 (7)
C5	−0.0387 (4)	0.07155 (8)	0.7520 (4)	0.0576 (7)
H5	0.0183	0.0468	0.7879	0.069*
C6	0.0911 (4)	0.10532 (7)	0.7716 (3)	0.0484 (6)
H6	0.2367	0.1029	0.8229	0.058*
C7	0.1574 (4)	0.17699 (7)	0.7403 (3)	0.0429 (6)
H7	0.2984	0.1743	0.8005	0.052*
C8	0.1974 (4)	0.27655 (7)	0.6130 (3)	0.0426 (6)
C9	0.3498 (4)	0.31068 (7)	0.6582 (3)	0.0402 (6)
C10	0.2601 (4)	0.34854 (7)	0.6341 (3)	0.0450 (6)
H10	0.1150	0.3519	0.5829	0.054*
C11	0.3873 (4)	0.38098 (7)	0.6867 (3)	0.0485 (6)
C12	0.6058 (4)	0.37744 (8)	0.7558 (3)	0.0571 (7)
H12	0.6903	0.3999	0.7886	0.069*
C13	0.6960 (4)	0.33984 (8)	0.7750 (3)	0.0555 (7)
H13	0.8436	0.3369	0.8208	0.067*
C14	0.5706 (4)	0.30664 (7)	0.7273 (3)	0.0471 (6)
H14	0.6336	0.2814	0.7413	0.057*
C15	−0.3370 (7)	0.00624 (8)	0.7178 (5)	0.1146 (14)
H15A	−0.2171	−0.0031	0.6495	0.172*
H15B	−0.4608	−0.0118	0.7015	0.172*
H15C	−0.2877	0.0077	0.8454	0.172*
H2	0.348 (3)	0.2395 (6)	0.796 (2)	0.051 (7)*

	U11	U22	U33	U12	U13	U23
N1	0.0437 (11)	0.0445 (12)	0.0478 (11)	−0.0099 (9)	−0.0071 (9)	0.0019 (9)
N2	0.0437 (12)	0.0440 (12)	0.0510 (12)	−0.0081 (9)	−0.0174 (10)	0.0054 (9)
N3	0.0820 (19)	0.0471 (15)	0.0735 (16)	−0.0082 (14)	0.0150 (14)	−0.0049 (12)
O1	0.0434 (10)	0.0495 (10)	0.0671 (11)	0.0005 (8)	−0.0078 (8)	0.0074 (9)
O2	0.0778 (15)	0.0504 (12)	0.1165 (18)	−0.0212 (10)	−0.0107 (12)	0.0072 (11)
O3	0.0612 (11)	0.0506 (10)	0.0663 (11)	−0.0004 (9)	−0.0333 (9)	0.0013 (9)
O4	0.0782 (16)	0.0575 (13)	0.132 (2)	0.0101 (11)	0.0040 (15)	−0.0009 (12)
O5	0.1152 (19)	0.0491 (12)	0.141 (2)	−0.0223 (13)	0.0003 (16)	−0.0134 (13)
C1	0.0397 (13)	0.0441 (14)	0.0359 (12)	−0.0019 (11)	0.0026 (10)	−0.0008 (10)
C2	0.0426 (14)	0.0422 (14)	0.0397 (12)	−0.0007 (11)	0.0028 (10)	0.0025 (10)
C3	0.0389 (14)	0.0531 (16)	0.0547 (15)	−0.0068 (12)	−0.0007 (11)	0.0025 (12)
C4	0.0579 (17)	0.0451 (15)	0.0595 (16)	−0.0141 (13)	0.0038 (13)	−0.0010 (12)
C5	0.0612 (18)	0.0455 (15)	0.0657 (17)	0.0033 (13)	0.0019 (14)	0.0053 (13)
C6	0.0414 (14)	0.0516 (15)	0.0518 (14)	0.0004 (12)	0.0008 (11)	0.0041 (12)
C7	0.0404 (13)	0.0491 (15)	0.0382 (12)	−0.0008 (11)	−0.0042 (10)	−0.0003 (11)
C8	0.0415 (13)	0.0453 (14)	0.0397 (12)	0.0023 (11)	−0.0055 (11)	−0.0004 (11)
C9	0.0390 (13)	0.0464 (14)	0.0345 (12)	−0.0073 (11)	−0.0015 (10)	−0.0002 (10)
C10	0.0434 (14)	0.0506 (15)	0.0409 (13)	−0.0033 (11)	0.0026 (11)	0.0033 (11)
C11	0.0557 (16)	0.0463 (15)	0.0447 (13)	−0.0066 (13)	0.0113 (12)	−0.0010 (11)
C12	0.0559 (17)	0.0647 (18)	0.0512 (15)	−0.0247 (14)	0.0071 (12)	−0.0048 (13)
C13	0.0415 (14)	0.0711 (19)	0.0534 (15)	−0.0141 (13)	−0.0004 (12)	0.0016 (13)
C14	0.0407 (14)	0.0562 (15)	0.0444 (13)	−0.0018 (11)	0.0034 (11)	0.0020 (11)
C15	0.138 (3)	0.0462 (19)	0.154 (3)	−0.029 (2)	−0.029 (3)	0.020 (2)

N1—C7	1.281 (3)	C5—C6	1.378 (3)
N1—N2	1.386 (2)	C5—H5	0.9300
N2—C8	1.339 (3)	C6—H6	0.9300
N2—H2	0.900 (9)	C7—H7	0.9300
N3—O5	1.219 (3)	C8—C9	1.489 (3)
N3—O4	1.221 (3)	C9—C10	1.387 (3)
N3—C11	1.471 (3)	C9—C14	1.392 (3)
O1—C2	1.357 (2)	C10—C11	1.369 (3)
O1—H1	0.8200	C10—H10	0.9300
O2—C4	1.361 (3)	C11—C12	1.377 (3)
O2—C15	1.426 (3)	C12—C13	1.377 (3)
O3—C8	1.230 (2)	C12—H12	0.9300
C1—C6	1.387 (3)	C13—C14	1.376 (3)
C1—C2	1.414 (3)	C13—H13	0.9300
C1—C7	1.440 (3)	C14—H14	0.9300
C2—C3	1.372 (3)	C15—H15A	0.9600
C3—C4	1.380 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.388 (3)
C7—N1—N2	117.28 (18)	C1—C7—H7	119.6
C8—N2—N1	118.54 (17)	O3—C8—N2	122.4 (2)
C8—N2—H2	125.0 (14)	O3—C8—C9	120.9 (2)
N1—N2—H2	115.5 (14)	N2—C8—C9	116.69 (18)
O5—N3—O4	123.6 (3)	C10—C9—C14	119.1 (2)
O5—N3—C11	117.9 (3)	C10—C9—C8	116.77 (19)
O4—N3—C11	118.6 (2)	C14—C9—C8	124.1 (2)
C2—O1—H1	109.5	C11—C10—C9	119.3 (2)
C4—O2—C15	118.5 (2)	C11—C10—H10	120.3
C6—C1—C2	117.5 (2)	C9—C10—H10	120.3
C6—C1—C7	120.3 (2)	C10—C11—C12	122.1 (2)
C2—C1—C7	122.1 (2)	C10—C11—N3	117.9 (2)
O1—C2—C3	117.9 (2)	C12—C11—N3	120.0 (2)
O1—C2—C1	122.1 (2)	C13—C12—C11	118.3 (2)
C3—C2—C1	120.1 (2)	C13—C12—H12	120.8
C2—C3—C4	120.8 (2)	C11—C12—H12	120.8
C2—C3—H3	119.6	C14—C13—C12	120.8 (2)
C4—C3—H3	119.6	C14—C13—H13	119.6
O2—C4—C3	114.9 (2)	C12—C13—H13	119.6
O2—C4—C5	124.6 (2)	C13—C14—C9	120.2 (2)
C3—C4—C5	120.5 (2)	C13—C14—H14	119.9
C6—C5—C4	118.3 (2)	C9—C14—H14	119.9
C6—C5—H5	120.8	O2—C15—H15A	109.5
C4—C5—H5	120.8	O2—C15—H15B	109.5
C5—C6—C1	122.7 (2)	H15A—C15—H15B	109.5
C5—C6—H6	118.6	O2—C15—H15C	109.5
C1—C6—H6	118.6	H15A—C15—H15C	109.5
N1—C7—C1	120.8 (2)	H15B—C15—H15C	109.5
N1—C7—H7	119.6

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.618 (2)	146.
N2—H2···O3i	0.90 (1)	1.93 (1)	2.806 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.618 (2)	146
N2—H2⋯O3i	0.90 (1)	1.93 (1)	2.806 (2)	165 (2)

Symmetry code: (i) .