2-Hydr-oxy-N'-(2-hydr-oxy-3-meth-oxy-5-nitro-benzyl-idene)-3-methyl-benzo-hydrazide.

In the title compound, C(16)H(15)N(3)O(6), the dihedral angle between the two benzene rings is 0.9 (2)°. The mol-ecule adopts an E configuration with respect to the C=N bond. There are intra-molecular O-H⋯N and O-H⋯O hydrogen bonds in the mol-ecule. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds to form chains running along the c axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶). For the hydrazone compounds we reported recently, see: Han & Zhao (2010a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). For similar compounds, see: Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C16H15N3O6

M = 345.31

Monoclinic,

a = 7.482 (1) Å

b = 17.158 (1) Å

c = 12.250 (1) Å

β = 91.565 (1)°

V = 1572.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.10 × 0.07 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.989, T max = 0.994

14545 measured reflections

2612 independent reflections

2165 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.07

2612 reflections

233 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012912/hg2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012912/hg2671Isup2.hkl

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

C16H15N3O6	F(000) = 720
Mr = 345.31	Dx = 1.459 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6384 reflections
a = 7.482 (1) Å	θ = 2.4–28.1°
b = 17.158 (1) Å	µ = 0.11 mm−1
c = 12.250 (1) Å	T = 298 K
β = 91.565 (1)°	Block, colourless
V = 1572.0 (3) Å3	0.10 × 0.07 × 0.05 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2612 independent reflections
Radiation source: fine-focus sealed tube	2165 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.989, Tmax = 0.994	k = −20→19
14545 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2485P] where P = (Fo2 + 2Fc2)/3
2612 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.27 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	0.91330 (15)	0.99426 (5)	0.21838 (9)	0.0529 (3)
H1	0.8639	1.0075	0.1607	0.079*
O2	1.05158 (16)	0.93423 (6)	0.39521 (9)	0.0569 (3)
O3	0.67111 (17)	1.11702 (6)	0.00680 (9)	0.0596 (3)
O4	0.55183 (17)	1.23435 (6)	−0.09508 (10)	0.0633 (3)
H4	0.5986	1.2096	−0.0447	0.095*
O5	1.0371 (2)	0.63937 (6)	0.14205 (11)	0.0805 (4)
O6	1.13335 (17)	0.65067 (6)	0.30689 (10)	0.0654 (4)
N1	1.06881 (16)	0.67848 (7)	0.22311 (11)	0.0481 (3)
N2	0.78019 (15)	0.97366 (7)	0.02075 (10)	0.0428 (3)
N3	0.70013 (16)	1.00078 (6)	−0.07337 (10)	0.0434 (3)
C1	0.91165 (17)	0.87130 (8)	0.12358 (11)	0.0391 (3)
C2	0.94794 (18)	0.91768 (8)	0.21567 (12)	0.0397 (3)
C3	1.02423 (19)	0.88404 (8)	0.31098 (12)	0.0422 (3)
C4	1.06361 (18)	0.80575 (8)	0.31361 (12)	0.0425 (4)
H4A	1.1130	0.7830	0.3764	0.051*
C5	1.02806 (18)	0.76137 (8)	0.22055 (12)	0.0406 (3)
C6	0.95409 (18)	0.79211 (8)	0.12723 (12)	0.0423 (3)
H6	0.9321	0.7606	0.0665	0.051*
C7	1.1154 (3)	0.90321 (10)	0.49667 (14)	0.0671 (5)
H7A	1.0319	0.8654	0.5224	0.101*
H7B	1.1281	0.9445	0.5491	0.101*
H7C	1.2293	0.8788	0.4870	0.101*
C8	0.8290 (2)	0.90257 (8)	0.02500 (12)	0.0444 (4)
H8	0.8113	0.8706	−0.0357	0.053*
C9	0.64676 (18)	1.07636 (8)	−0.07544 (12)	0.0398 (3)
C10	0.56400 (18)	1.10707 (8)	−0.17680 (12)	0.0393 (3)
C11	0.52198 (18)	1.18678 (8)	−0.18113 (12)	0.0433 (4)
C12	0.44698 (19)	1.22062 (9)	−0.27568 (13)	0.0486 (4)
C13	0.4115 (2)	1.17278 (10)	−0.36333 (14)	0.0566 (4)
H13	0.3604	1.1941	−0.4266	0.068*
C14	0.4493 (2)	1.09387 (10)	−0.36069 (14)	0.0587 (4)
H14	0.4230	1.0629	−0.4214	0.070*
C15	0.5255 (2)	1.06140 (9)	−0.26864 (13)	0.0493 (4)
H15	0.5519	1.0084	−0.2673	0.059*
C16	0.4079 (2)	1.30676 (10)	−0.27722 (16)	0.0659 (5)
H16A	0.3563	1.3210	−0.3470	0.099*
H16B	0.5169	1.3352	−0.2646	0.099*
H16C	0.3255	1.3190	−0.2210	0.099*
H3	0.686 (3)	0.9691 (10)	−0.1318 (12)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0724 (7)	0.0306 (5)	0.0552 (7)	0.0048 (4)	−0.0085 (5)	−0.0008 (4)
O2	0.0815 (8)	0.0413 (6)	0.0468 (7)	0.0050 (5)	−0.0152 (5)	−0.0065 (5)
O3	0.0876 (8)	0.0438 (6)	0.0464 (7)	0.0091 (5)	−0.0182 (6)	−0.0042 (5)
O4	0.0868 (8)	0.0393 (6)	0.0628 (8)	0.0129 (5)	−0.0201 (6)	−0.0052 (5)
O5	0.1370 (12)	0.0401 (6)	0.0630 (9)	0.0209 (7)	−0.0251 (8)	−0.0099 (6)
O6	0.0919 (9)	0.0429 (6)	0.0603 (8)	0.0125 (6)	−0.0219 (6)	0.0094 (5)
N1	0.0588 (8)	0.0361 (6)	0.0490 (9)	0.0068 (5)	−0.0062 (6)	0.0023 (6)
N2	0.0485 (7)	0.0384 (6)	0.0413 (8)	0.0007 (5)	−0.0027 (5)	0.0079 (5)
N3	0.0558 (7)	0.0357 (6)	0.0382 (8)	0.0026 (5)	−0.0060 (6)	0.0050 (5)
C1	0.0416 (7)	0.0353 (7)	0.0401 (9)	−0.0001 (5)	−0.0008 (6)	0.0039 (6)
C2	0.0417 (7)	0.0320 (7)	0.0455 (9)	0.0005 (5)	0.0009 (6)	0.0020 (6)
C3	0.0455 (8)	0.0390 (7)	0.0417 (9)	−0.0014 (6)	−0.0026 (6)	−0.0032 (6)
C4	0.0452 (8)	0.0398 (7)	0.0419 (9)	0.0021 (6)	−0.0059 (6)	0.0043 (6)
C5	0.0443 (7)	0.0320 (7)	0.0453 (9)	0.0034 (6)	−0.0022 (6)	0.0025 (6)
C6	0.0510 (8)	0.0359 (7)	0.0397 (9)	0.0019 (6)	−0.0029 (6)	−0.0019 (6)
C7	0.0994 (14)	0.0544 (10)	0.0465 (11)	0.0060 (9)	−0.0192 (9)	−0.0069 (8)
C8	0.0537 (9)	0.0385 (7)	0.0406 (9)	0.0015 (6)	−0.0034 (7)	0.0017 (6)
C9	0.0436 (8)	0.0359 (7)	0.0396 (9)	−0.0017 (6)	−0.0019 (6)	0.0019 (6)
C10	0.0418 (7)	0.0381 (7)	0.0381 (9)	−0.0014 (6)	0.0000 (6)	0.0051 (6)
C11	0.0434 (7)	0.0409 (7)	0.0454 (9)	0.0004 (6)	−0.0010 (6)	0.0033 (7)
C12	0.0448 (8)	0.0495 (8)	0.0514 (10)	0.0019 (6)	0.0005 (7)	0.0149 (7)
C13	0.0556 (9)	0.0691 (11)	0.0449 (10)	0.0022 (8)	−0.0037 (7)	0.0193 (8)
C14	0.0693 (11)	0.0656 (11)	0.0407 (10)	−0.0021 (8)	−0.0083 (8)	−0.0010 (8)
C15	0.0588 (9)	0.0442 (8)	0.0447 (10)	0.0004 (7)	−0.0039 (7)	0.0010 (7)
C16	0.0663 (11)	0.0524 (10)	0.0786 (13)	0.0071 (8)	−0.0083 (9)	0.0239 (9)

O1—C2	1.3399 (16)	C5—C6	1.363 (2)
O1—H1	0.8200	C6—H6	0.9300
O2—C3	1.3553 (17)	C7—H7A	0.9600
O2—C7	1.423 (2)	C7—H7B	0.9600
O3—C9	1.2348 (17)	C7—H7C	0.9600
O4—C11	1.3469 (18)	C8—H8	0.9300
O4—H4	0.8200	C9—C10	1.470 (2)
O5—N1	1.2165 (16)	C10—C15	1.395 (2)
O6—N1	1.2195 (16)	C10—C11	1.4040 (19)
N1—C5	1.4547 (18)	C11—C12	1.399 (2)
N2—C8	1.2739 (18)	C12—C13	1.372 (2)
N2—N3	1.3664 (17)	C12—C16	1.507 (2)
N3—C9	1.3569 (18)	C13—C14	1.383 (2)
N3—H3	0.903 (9)	C13—H13	0.9300
C1—C6	1.3958 (18)	C14—C15	1.368 (2)
C1—C2	1.401 (2)	C14—H14	0.9300
C1—C8	1.445 (2)	C15—H15	0.9300
C2—C3	1.409 (2)	C16—H16A	0.9600
C3—C4	1.3754 (19)	C16—H16B	0.9600
C4—C5	1.391 (2)	C16—H16C	0.9600
C4—H4A	0.9300
C2—O1—H1	109.5	H7A—C7—H7C	109.5
C3—O2—C7	117.87 (12)	H7B—C7—H7C	109.5
C11—O4—H4	109.5	N2—C8—C1	120.36 (14)
O5—N1—O6	122.35 (12)	N2—C8—H8	119.8
O5—N1—C5	119.05 (12)	C1—C8—H8	119.8
O6—N1—C5	118.60 (13)	O3—C9—N3	119.19 (13)
C8—N2—N3	118.63 (13)	O3—C9—C10	122.42 (12)
C9—N3—N2	117.60 (12)	N3—C9—C10	118.38 (13)
C9—N3—H3	122.2 (13)	C15—C10—C11	118.41 (13)
N2—N3—H3	120.2 (13)	C15—C10—C9	123.57 (12)
C6—C1—C2	119.23 (13)	C11—C10—C9	118.02 (13)
C6—C1—C8	118.69 (13)	O4—C11—C12	116.78 (13)
C2—C1—C8	122.08 (12)	O4—C11—C10	121.90 (13)
O1—C2—C1	122.93 (13)	C12—C11—C10	121.31 (14)
O1—C2—C3	117.09 (13)	C13—C12—C11	117.67 (14)
C1—C2—C3	119.98 (12)	C13—C12—C16	122.95 (15)
O2—C3—C4	125.10 (14)	C11—C12—C16	119.39 (15)
O2—C3—C2	114.82 (12)	C12—C13—C14	122.16 (15)
C4—C3—C2	120.07 (13)	C12—C13—H13	118.9
C3—C4—C5	118.66 (13)	C14—C13—H13	118.9
C3—C4—H4A	120.7	C15—C14—C13	119.88 (16)
C5—C4—H4A	120.7	C15—C14—H14	120.1
C6—C5—C4	122.69 (12)	C13—C14—H14	120.1
C6—C5—N1	118.46 (13)	C14—C15—C10	120.55 (14)
C4—C5—N1	118.84 (13)	C14—C15—H15	119.7
C5—C6—C1	119.37 (13)	C10—C15—H15	119.7
C5—C6—H6	120.3	C12—C16—H16A	109.5
C1—C6—H6	120.3	C12—C16—H16B	109.5
O2—C7—H7A	109.5	H16A—C16—H16B	109.5
O2—C7—H7B	109.5	C12—C16—H16C	109.5
H7A—C7—H7B	109.5	H16A—C16—H16C	109.5
O2—C7—H7C	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6i	0.90 (1)	2.22 (1)	3.0190 (17)	147 (2)
O4—H4···O3	0.82	1.79	2.5192 (15)	148
O1—H1···N2	0.82	1.90	2.6166 (17)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O6i	0.90 (1)	2.22 (1)	3.0190 (17)	147 (2)
O4—H4⋯O3	0.82	1.79	2.5192 (15)	148
O1—H1⋯N2	0.82	1.90	2.6166 (17)	145

Symmetry code: (i) .