2-Hy-droxy-N'-(5-hy-droxy-2-nitro-benzyl-idene)-3-methyl-benzohydrazide.

The title compound, C(15)H(13)N(3)O(5), was prepared by condensing 5-hy-droxy-2-nitro-benzaldehyde and 2-hy-droxy-3-methyl-benzohydrazide in methanol. The two benzene rings make a dihedral angle of 3.9 (3)°. An intra-molecular O-H⋯O hydrogen bond is observed. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, and C-H⋯O and π-π inter-actions [centroid-centroid distances = 3.5658 (17)-3.9287 (19) Å].

Related literature

For the crystal structures of similar hydrazone compounds, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Zhi et al. (2011 ▶); Huang & Wu (2010 ▶); Shen et al. (2012 ▶); Zhu et al. (2012 ▶).

Experimental

Crystal data

C15H13N3O5

M = 315.28

Triclinic,

a = 7.643 (2) Å

b = 9.055 (3) Å

c = 10.876 (3) Å

α = 84.865 (2)°

β = 72.732 (2)°

γ = 77.479 (2)°

V = 701.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.18 × 0.17 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.980, T max = 0.985

4694 measured reflections

2942 independent reflections

1788 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.132

S = 1.01

2942 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002437/su2366sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002437/su2366Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002437/su2366Isup3.cml

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

C15H13N3O5	Z = 2
Mr = 315.28	F(000) = 328
Triclinic, P1	Dx = 1.493 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.643 (2) Å	Cell parameters from 907 reflections
b = 9.055 (3) Å	θ = 2.3–26.3°
c = 10.876 (3) Å	µ = 0.12 mm−1
α = 84.865 (2)°	T = 298 K
β = 72.732 (2)°	Block, colourless
γ = 77.479 (2)°	0.18 × 0.17 × 0.13 mm
V = 701.4 (4) Å3

Bruker SMART CCD area-detector diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	1788 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.980, Tmax = 0.985	k = −11→10
4694 measured reflections	l = −13→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0593P)2] where P = (Fo2 + 2Fc2)/3
2942 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.22 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
N1	0.3407 (2)	0.5111 (2)	0.34762 (17)	0.0392 (4)
N2	0.3357 (2)	0.12755 (18)	0.60779 (16)	0.0378 (4)
N3	0.4581 (2)	0.09322 (19)	0.68114 (17)	0.0387 (5)
O1	0.4907 (2)	0.46271 (18)	0.36935 (16)	0.0566 (5)
O2	0.3020 (2)	0.63840 (17)	0.30078 (17)	0.0619 (5)
O3	−0.1905 (2)	0.15022 (17)	0.43917 (16)	0.0513 (5)
H3	−0.2328	0.1533	0.3778	0.077*
O4	0.35835 (19)	−0.12443 (16)	0.74968 (15)	0.0485 (4)
O5	0.4783 (2)	−0.29790 (17)	0.91796 (16)	0.0548 (5)
H5	0.4052	−0.2619	0.8761	0.082*
C1	0.2028 (2)	0.2941 (2)	0.46606 (19)	0.0313 (5)
C2	0.2020 (2)	0.4156 (2)	0.37541 (19)	0.0317 (5)
C3	0.0716 (3)	0.4480 (2)	0.3073 (2)	0.0377 (5)
H3A	0.0729	0.5299	0.2492	0.045*
C4	−0.0602 (3)	0.3606 (2)	0.3242 (2)	0.0390 (5)
H4	−0.1462	0.3816	0.2768	0.047*
C5	−0.0633 (3)	0.2405 (2)	0.4132 (2)	0.0351 (5)
C6	0.0654 (3)	0.2105 (2)	0.4831 (2)	0.0343 (5)
H6	0.0594	0.1312	0.5438	0.041*
C7	0.3329 (3)	0.2528 (2)	0.5452 (2)	0.0375 (5)
H7	0.4112	0.3167	0.5493	0.045*
C8	0.4651 (3)	−0.0391 (2)	0.7500 (2)	0.0352 (5)
C9	0.6023 (3)	−0.0770 (2)	0.8241 (2)	0.0349 (5)
C10	0.6006 (3)	−0.2070 (2)	0.9055 (2)	0.0371 (5)
C11	0.7307 (3)	−0.2501 (2)	0.9763 (2)	0.0427 (5)
C12	0.8620 (3)	−0.1626 (3)	0.9628 (2)	0.0536 (7)
H12	0.9497	−0.1900	1.0086	0.064*
C13	0.8668 (3)	−0.0341 (3)	0.8822 (3)	0.0577 (7)
H13	0.9573	0.0230	0.8743	0.069*
C14	0.7382 (3)	0.0073 (2)	0.8151 (2)	0.0470 (6)
H14	0.7413	0.0937	0.7620	0.056*
C15	0.7271 (4)	−0.3903 (3)	1.0606 (2)	0.0660 (8)
H15A	0.8153	−0.3978	1.1091	0.099*
H15B	0.7598	−0.4775	1.0081	0.099*
H15C	0.6039	−0.3856	1.1187	0.099*
H3B	0.538 (3)	0.152 (2)	0.679 (2)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0418 (10)	0.0344 (10)	0.0408 (11)	−0.0144 (8)	−0.0062 (9)	−0.0007 (8)
N2	0.0381 (9)	0.0390 (10)	0.0454 (12)	−0.0133 (8)	−0.0227 (9)	0.0031 (9)
N3	0.0425 (10)	0.0379 (10)	0.0477 (12)	−0.0160 (8)	−0.0279 (9)	0.0080 (9)
O1	0.0478 (9)	0.0662 (11)	0.0698 (13)	−0.0300 (8)	−0.0291 (9)	0.0142 (9)
O2	0.0599 (10)	0.0369 (9)	0.0838 (14)	−0.0183 (8)	−0.0116 (9)	0.0158 (9)
O3	0.0527 (9)	0.0545 (10)	0.0658 (12)	−0.0282 (8)	−0.0365 (8)	0.0104 (8)
O4	0.0516 (9)	0.0462 (9)	0.0647 (11)	−0.0263 (7)	−0.0348 (8)	0.0129 (8)
O5	0.0548 (10)	0.0532 (10)	0.0677 (13)	−0.0277 (8)	−0.0289 (9)	0.0199 (8)
C1	0.0320 (10)	0.0303 (11)	0.0356 (12)	−0.0080 (8)	−0.0134 (9)	−0.0050 (9)
C2	0.0308 (10)	0.0282 (10)	0.0359 (12)	−0.0093 (8)	−0.0067 (9)	−0.0015 (9)
C3	0.0411 (12)	0.0344 (12)	0.0371 (13)	−0.0061 (9)	−0.0130 (10)	0.0034 (9)
C4	0.0375 (11)	0.0436 (13)	0.0406 (14)	−0.0045 (10)	−0.0208 (10)	−0.0004 (10)
C5	0.0333 (10)	0.0344 (11)	0.0430 (14)	−0.0104 (9)	−0.0156 (10)	−0.0034 (10)
C6	0.0383 (11)	0.0307 (11)	0.0404 (13)	−0.0113 (9)	−0.0192 (10)	0.0031 (9)
C7	0.0386 (11)	0.0365 (12)	0.0460 (14)	−0.0168 (9)	−0.0191 (10)	0.0017 (10)
C8	0.0330 (11)	0.0368 (12)	0.0400 (13)	−0.0095 (9)	−0.0144 (10)	−0.0023 (10)
C9	0.0374 (11)	0.0325 (11)	0.0377 (13)	−0.0076 (9)	−0.0141 (10)	−0.0031 (9)
C10	0.0384 (11)	0.0371 (12)	0.0369 (13)	−0.0100 (9)	−0.0104 (10)	−0.0028 (10)
C11	0.0476 (13)	0.0452 (13)	0.0346 (13)	−0.0012 (10)	−0.0161 (10)	−0.0030 (10)
C12	0.0589 (14)	0.0553 (15)	0.0584 (17)	−0.0034 (12)	−0.0385 (13)	−0.0071 (13)
C13	0.0598 (15)	0.0497 (15)	0.083 (2)	−0.0193 (12)	−0.0432 (14)	−0.0026 (14)
C14	0.0536 (13)	0.0389 (13)	0.0619 (17)	−0.0181 (11)	−0.0322 (12)	0.0045 (11)
C15	0.0682 (16)	0.0716 (18)	0.0578 (18)	−0.0093 (14)	−0.0270 (14)	0.0207 (14)

N1—O1	1.219 (2)	C4—H4	0.9300
N1—O2	1.230 (2)	C5—C6	1.382 (3)
N1—C2	1.457 (2)	C6—H6	0.9300
N2—C7	1.269 (2)	C7—H7	0.9300
N2—N3	1.372 (2)	C8—C9	1.471 (3)
N3—C8	1.354 (3)	C9—C14	1.393 (3)
N3—H3B	0.889 (10)	C9—C10	1.408 (3)
O3—C5	1.354 (2)	C10—C11	1.402 (3)
O3—H3	0.8200	C11—C12	1.376 (3)
O4—C8	1.240 (2)	C11—C15	1.499 (3)
O5—C10	1.344 (2)	C12—C13	1.392 (3)
O5—H5	0.8200	C12—H12	0.9300
C1—C6	1.384 (2)	C13—C14	1.363 (3)
C1—C2	1.410 (3)	C13—H13	0.9300
C1—C7	1.470 (3)	C14—H14	0.9300
C2—C3	1.379 (3)	C15—H15A	0.9600
C3—C4	1.372 (3)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.389 (3)
O1—N1—O2	122.22 (18)	C1—C7—H7	120.9
O1—N1—C2	119.73 (17)	O4—C8—N3	120.40 (18)
O2—N1—C2	118.04 (18)	O4—C8—C9	121.74 (19)
C7—N2—N3	116.56 (16)	N3—C8—C9	117.87 (17)
C8—N3—N2	118.53 (16)	C14—C9—C10	118.08 (19)
C8—N3—H3B	120.2 (16)	C14—C9—C8	123.11 (19)
N2—N3—H3B	121.0 (16)	C10—C9—C8	118.78 (18)
C5—O3—H3	109.5	O5—C10—C11	116.37 (19)
C10—O5—H5	109.5	O5—C10—C9	122.50 (18)
C6—C1—C2	116.38 (17)	C11—C10—C9	121.12 (19)
C6—C1—C7	118.11 (18)	C12—C11—C10	118.0 (2)
C2—C1—C7	125.49 (17)	C12—C11—C15	122.0 (2)
C3—C2—C1	121.46 (17)	C10—C11—C15	119.9 (2)
C3—C2—N1	116.86 (17)	C11—C12—C13	121.7 (2)
C1—C2—N1	121.67 (17)	C11—C12—H12	119.1
C4—C3—C2	120.70 (19)	C13—C12—H12	119.1
C4—C3—H3A	119.6	C14—C13—C12	119.6 (2)
C2—C3—H3A	119.6	C14—C13—H13	120.2
C3—C4—C5	119.12 (19)	C12—C13—H13	120.2
C3—C4—H4	120.4	C13—C14—C9	121.4 (2)
C5—C4—H4	120.4	C13—C14—H14	119.3
O3—C5—C6	116.53 (18)	C9—C14—H14	119.3
O3—C5—C4	123.56 (18)	C11—C15—H15A	109.5
C6—C5—C4	119.89 (18)	C11—C15—H15B	109.5
C5—C6—C1	122.41 (18)	H15A—C15—H15B	109.5
C5—C6—H6	118.8	C11—C15—H15C	109.5
C1—C6—H6	118.8	H15A—C15—H15C	109.5
N2—C7—C1	118.21 (18)	H15B—C15—H15C	109.5
N2—C7—H7	120.9

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.82	1.83	2.552 (2)	146
O3—H3···O4i	0.82	1.97	2.775 (2)	168
N3—H3B···O2ii	0.89 (2)	2.53 (2)	3.397 (3)	167 (2)
C6—H6···O3i	0.93	2.54	3.306 (3)	140
C7—H7···O1ii	0.93	2.59	3.464 (3)	157
C14—H14···O2ii	0.93	2.44	3.325 (3)	159
C15—H15C···O2iii	0.96	2.54	3.488 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4	0.82	1.83	2.552 (2)	146
O3—H3⋯O4i	0.82	1.97	2.775 (2)	168
N3—H3B⋯O2ii	0.89 (2)	2.53 (2)	3.397 (3)	167 (2)
C6—H6⋯O3i	0.93	2.54	3.306 (3)	140
C7—H7⋯O1ii	0.93	2.59	3.464 (3)	157
C14—H14⋯O2ii	0.93	2.44	3.325 (3)	159
C15—H15C⋯O2iii	0.96	2.54	3.488 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) .