N'-[1-(2-Hydroxy-phen-yl)ethyl-idene]-2-nitro-benzohydrazide methanol solvate.

In the title compound, C(15)H(13)N(3)O(4)·CH(3)OH, the dihedral angle between the two substituted benzene rings is 66.7 (2)°. An intra-molecular O-H⋯N hydrogen bond is observed in the Schiff base mol-ecule. In the crystal structure, the Schiff base and solvent mol-ecules are linked into chains running along the a axis by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazone compounds, see: Bedia et al. (2006 ▶). For complexes of hydrazone compounds, see: Iskander et al. (2001 ▶); Aggarwal et al. (1981 ▶); Aruffo et al. (1982 ▶). For related structures, see: Fun et al. (2008a ▶,b ▶); Butcher et al. (2007 ▶); Zhi & Yang (2007 ▶); Mohd Lair et al. (2009a ▶,b ▶); Yehye et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13N3O4·CH4O

M = 331.33

Triclinic,

a = 7.124 (2) Å

b = 8.066 (2) Å

c = 15.764 (3) Å

α = 101.950 (2)°

β = 92.972 (2)°

γ = 114.889 (2)°

V = 794.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.976, T max = 0.977

4659 measured reflections

3371 independent reflections

2660 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.05

3371 reflections

226 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 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/S160053680900508X/ci2770sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900508X/ci2770Isup2.hkl

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

C15H13N3O4·CH4O	Z = 2
Mr = 331.33	F(000) = 348
Triclinic, P1	Dx = 1.386 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.124 (2) Å	Cell parameters from 1968 reflections
b = 8.066 (2) Å	θ = 2.6–28.5°
c = 15.764 (3) Å	µ = 0.11 mm−1
α = 101.950 (2)°	T = 298 K
β = 92.972 (2)°	Block, colourless
γ = 114.889 (2)°	0.23 × 0.23 × 0.22 mm
V = 794.0 (3) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3371 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
Tmin = 0.976, Tmax = 0.977	k = −10→10
4659 measured reflections	l = −19→20

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.1607P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3371 reflections	Δρmax = 0.24 e Å−3
226 parameters	Δρmin = −0.23 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.066 (6)

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
O1	0.46363 (18)	0.2874 (2)	0.22886 (7)	0.0558 (3)
O2	0.2215 (3)	0.7197 (2)	0.41556 (13)	0.0902 (5)
O3	0.4022 (2)	0.65556 (18)	0.32038 (9)	0.0639 (4)
O4	0.3900 (2)	0.2749 (2)	−0.00437 (8)	0.0597 (4)
H4	0.3625	0.2787	0.0457	0.089*
O5	0.81043 (17)	0.27761 (18)	0.30757 (8)	0.0522 (3)
H5	0.7158	0.2968	0.2867	0.078*
N1	0.13992 (19)	0.27191 (19)	0.20210 (8)	0.0396 (3)
N2	0.1602 (2)	0.27247 (19)	0.11548 (8)	0.0403 (3)
N3	0.2967 (2)	0.61957 (19)	0.37848 (10)	0.0495 (4)
C1	0.2777 (2)	0.2991 (2)	0.34961 (9)	0.0336 (3)
C2	0.2633 (2)	0.4482 (2)	0.40702 (9)	0.0363 (3)
C3	0.2296 (2)	0.4472 (2)	0.49259 (10)	0.0441 (4)
H3	0.2163	0.5472	0.5288	0.053*
C4	0.2163 (2)	0.2946 (2)	0.52303 (10)	0.0472 (4)
H4A	0.1947	0.2917	0.5805	0.057*
C5	0.2348 (2)	0.1460 (2)	0.46837 (11)	0.0450 (4)
H5A	0.2286	0.0448	0.4896	0.054*
C6	0.2625 (2)	0.1475 (2)	0.38232 (10)	0.0386 (3)
H6	0.2712	0.0453	0.3458	0.046*
C7	0.3056 (2)	0.2892 (2)	0.25478 (9)	0.0375 (3)
C8	0.0013 (2)	0.2459 (2)	0.06163 (9)	0.0383 (3)
C9	−0.2106 (3)	0.2077 (3)	0.08602 (11)	0.0564 (5)
H9A	−0.2363	0.1373	0.1298	0.085*
H9B	−0.3155	0.1361	0.0350	0.085*
H9C	−0.2160	0.3253	0.1089	0.085*
C10	0.0411 (3)	0.2564 (2)	−0.02863 (9)	0.0412 (4)
C11	0.2322 (3)	0.2729 (2)	−0.05640 (10)	0.0468 (4)
C12	0.2639 (4)	0.2882 (3)	−0.14152 (12)	0.0639 (5)
H12	0.3905	0.3006	−0.1595	0.077*
C13	0.1107 (4)	0.2853 (3)	−0.19919 (12)	0.0712 (6)
H13	0.1341	0.2953	−0.2558	0.085*
C14	−0.0770 (4)	0.2676 (3)	−0.17371 (12)	0.0678 (6)
H14	−0.1808	0.2648	−0.2131	0.081*
C15	−0.1110 (3)	0.2540 (3)	−0.08957 (11)	0.0543 (4)
H15	−0.2382	0.2429	−0.0728	0.065*
C16	0.7246 (3)	0.1002 (3)	0.32738 (15)	0.0637 (5)
H16A	0.8322	0.0598	0.3340	0.096*
H16B	0.6154	0.0097	0.2806	0.096*
H16C	0.6675	0.1103	0.3810	0.096*
H1	0.030 (2)	0.277 (3)	0.2252 (11)	0.052 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0432 (7)	0.0981 (10)	0.0467 (6)	0.0446 (7)	0.0145 (5)	0.0297 (6)
O2	0.1112 (14)	0.0669 (9)	0.1256 (14)	0.0645 (10)	0.0392 (11)	0.0317 (9)
O3	0.0749 (9)	0.0548 (7)	0.0645 (8)	0.0235 (7)	0.0108 (7)	0.0313 (6)
O4	0.0544 (8)	0.0912 (9)	0.0469 (7)	0.0439 (7)	0.0126 (6)	0.0183 (7)
O5	0.0372 (6)	0.0664 (7)	0.0588 (7)	0.0265 (6)	0.0036 (5)	0.0209 (6)
N1	0.0333 (7)	0.0574 (8)	0.0337 (6)	0.0243 (6)	0.0058 (5)	0.0135 (6)
N2	0.0391 (7)	0.0543 (7)	0.0329 (6)	0.0252 (6)	0.0042 (5)	0.0123 (5)
N3	0.0477 (8)	0.0415 (7)	0.0602 (9)	0.0216 (6)	−0.0014 (7)	0.0133 (6)
C1	0.0243 (6)	0.0407 (7)	0.0365 (7)	0.0144 (6)	0.0020 (5)	0.0115 (6)
C2	0.0294 (7)	0.0382 (7)	0.0420 (8)	0.0157 (6)	0.0004 (6)	0.0111 (6)
C3	0.0368 (8)	0.0516 (9)	0.0412 (8)	0.0209 (7)	0.0040 (6)	0.0038 (7)
C4	0.0399 (8)	0.0664 (10)	0.0351 (8)	0.0206 (8)	0.0087 (6)	0.0184 (7)
C5	0.0402 (8)	0.0495 (9)	0.0501 (9)	0.0180 (7)	0.0088 (7)	0.0258 (7)
C6	0.0345 (8)	0.0390 (7)	0.0443 (8)	0.0174 (6)	0.0056 (6)	0.0120 (6)
C7	0.0315 (7)	0.0471 (8)	0.0391 (8)	0.0204 (6)	0.0062 (6)	0.0146 (6)
C8	0.0388 (8)	0.0385 (7)	0.0379 (8)	0.0202 (6)	−0.0001 (6)	0.0050 (6)
C9	0.0400 (9)	0.0804 (12)	0.0470 (9)	0.0277 (9)	−0.0005 (7)	0.0123 (9)
C10	0.0492 (9)	0.0390 (7)	0.0340 (7)	0.0215 (7)	−0.0019 (6)	0.0039 (6)
C11	0.0557 (10)	0.0477 (9)	0.0377 (8)	0.0264 (8)	0.0039 (7)	0.0053 (7)
C12	0.0784 (14)	0.0734 (13)	0.0419 (9)	0.0364 (11)	0.0161 (9)	0.0110 (9)
C13	0.1033 (18)	0.0730 (13)	0.0326 (9)	0.0357 (12)	0.0059 (10)	0.0119 (9)
C14	0.0875 (15)	0.0701 (12)	0.0408 (10)	0.0355 (11)	−0.0158 (9)	0.0084 (9)
C15	0.0589 (11)	0.0597 (10)	0.0424 (9)	0.0286 (9)	−0.0080 (7)	0.0077 (8)
C16	0.0495 (11)	0.0652 (12)	0.0875 (14)	0.0311 (9)	0.0180 (10)	0.0274 (10)

O1—C7	1.2218 (18)	C5—H5A	0.93
O2—N3	1.2172 (19)	C6—H6	0.93
O3—N3	1.2192 (19)	C8—C10	1.478 (2)
O4—C11	1.349 (2)	C8—C9	1.497 (2)
O4—H4	0.82	C9—H9A	0.96
O5—C16	1.410 (2)	C9—H9B	0.96
O5—H5	0.82	C9—H9C	0.96
N1—C7	1.3472 (18)	C10—C15	1.401 (2)
N1—N2	1.3812 (17)	C10—C11	1.412 (2)
N1—H1	0.893 (9)	C11—C12	1.394 (2)
N2—C8	1.2916 (19)	C12—C13	1.373 (3)
N3—C2	1.4705 (19)	C12—H12	0.93
C1—C6	1.389 (2)	C13—C14	1.374 (3)
C1—C2	1.392 (2)	C13—H13	0.93
C1—C7	1.5083 (19)	C14—C15	1.379 (3)
C2—C3	1.383 (2)	C14—H14	0.93
C3—C4	1.380 (2)	C15—H15	0.93
C3—H3	0.93	C16—H16A	0.96
C4—C5	1.384 (2)	C16—H16B	0.96
C4—H4A	0.93	C16—H16C	0.96
C5—C6	1.383 (2)
C11—O4—H4	109.5	C10—C8—C9	120.59 (13)
C16—O5—H5	109.5	C8—C9—H9A	109.5
C7—N1—N2	117.46 (12)	C8—C9—H9B	109.5
C7—N1—H1	119.7 (12)	H9A—C9—H9B	109.5
N2—N1—H1	122.2 (12)	C8—C9—H9C	109.5
C8—N2—N1	119.43 (12)	H9A—C9—H9C	109.5
O2—N3—O3	123.74 (15)	H9B—C9—H9C	109.5
O2—N3—C2	118.16 (15)	C15—C10—C11	117.60 (15)
O3—N3—C2	118.08 (14)	C15—C10—C8	120.27 (15)
C6—C1—C2	117.14 (13)	C11—C10—C8	122.11 (14)
C6—C1—C7	117.87 (13)	O4—C11—C12	116.92 (16)
C2—C1—C7	124.98 (13)	O4—C11—C10	123.35 (14)
C3—C2—C1	122.71 (14)	C12—C11—C10	119.73 (16)
C3—C2—N3	117.65 (14)	C13—C12—C11	120.8 (2)
C1—C2—N3	119.55 (13)	C13—C12—H12	119.6
C4—C3—C2	118.57 (15)	C11—C12—H12	119.6
C4—C3—H3	120.7	C12—C13—C14	120.37 (18)
C2—C3—H3	120.7	C12—C13—H13	119.8
C3—C4—C5	120.24 (14)	C14—C13—H13	119.8
C3—C4—H4A	119.9	C13—C14—C15	119.77 (18)
C5—C4—H4A	119.9	C13—C14—H14	120.1
C6—C5—C4	120.21 (14)	C15—C14—H14	120.1
C6—C5—H5A	119.9	C14—C15—C10	121.72 (19)
C4—C5—H5A	119.9	C14—C15—H15	119.1
C5—C6—C1	121.08 (14)	C10—C15—H15	119.1
C5—C6—H6	119.5	O5—C16—H16A	109.5
C1—C6—H6	119.5	O5—C16—H16B	109.5
O1—C7—N1	123.95 (14)	H16A—C16—H16B	109.5
O1—C7—C1	121.23 (13)	O5—C16—H16C	109.5
N1—C7—C1	114.72 (12)	H16A—C16—H16C	109.5
N2—C8—C10	115.28 (13)	H16B—C16—H16C	109.5
N2—C8—C9	124.13 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.89 (1)	2.08 (1)	2.9563 (17)	165 (2)
O5—H5···O1	0.82	1.94	2.7451 (16)	168
O4—H4···N2	0.82	1.85	2.5612 (17)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.893 (9)	2.08 (1)	2.9563 (17)	165 (2)
O5—H5⋯O1	0.82	1.94	2.7451 (16)	168
O4—H4⋯N2	0.82	1.85	2.5612 (17)	144

Symmetry code: (i) .