N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]-2-nitro­benzohydrazide methanol solvate

Xiao, G.-J.; Wei, C.

doi:10.1107/S160053680900508X

organic compounds

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Volume 65| Part 3| March 2009| Page o585

doi:10.1107/S160053680900508X

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N′-[1-(2-Hydroxyphenyl)ethylidene]-2-nitrobenzohydrazide methanol solvate

Ge-Jiang Xiao ^a ^* and Chao Wei ^a

^aSchool of Chemistry and Biological Engineering, Changsha University of Science and Technology, Changsha, Hunan 410004, People's Republic of China
^*Correspondence e-mail: gejiangxiaowc@163.com

(Received 10 February 2009; accepted 12 February 2009; online 25 February 2009)

In the title compound, C₁₅H₁₃N₃O₄·CH₃OH, the dihedral angle between the two substituted benzene rings is 66.7 (2)°. An intramolecular O—H⋯N hydrogen bond is observed in the Schiff base molecule. In the crystal structure, the Schiff base and solvent molecules are linked into chains running along the a axis by intermolecular 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_r = 331.33
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.05
3371 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900508X/ci2770sup1.cif

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

checkCIF report

Comment top

Hydrazone compounds have been demonstrated to possess biological properties, such as antimicrobial, antitubercular, anticancer and antitumor (Bedia et al., 2006). Moreover, these compounds are good ligands in the coordination chemistry (Iskander et al., 2001; Aggarwal et al., 1981; Aruffo et al., 1982). Recently, a large number of hydrazone compounds have been reported (Fun et al., 2008b; Butcher et al., 2007; Zhi & Yang, 2007). In this paper, a new hydrazone compound (Fig. 1), derived from 1-(2-hydroxyphenyl)ethanone and 2-nitrobenzohydrazide is reported.

The asymmetric unit of the title compound contains a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two substituted benzene rings is 66.7 (2)°, indicating that the Schiff base molecule is twisted. The dihedral angle between the C1-C6 and O2/O3/N3/C2 planes is 26.0 (1)°. All bond lengths in the compound are typical (Allen et al., 1987) and comparable to those observed in similar hydrazone compounds (Fun et al., 2008a; Mohd Lair et al., 2009a,b; Yehye et al., 2008). An intramolecular O—H···N hydrogen bond is observed in the Schiff base molecule.

In the crystal structure, the Schiff base and methanol molecules are linked through O–H···O and N–H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).

Related literature top

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 top

1-(2-Hydroxyphenyl)ethanone (1.0 mmol, 136.2 mg) and 2-nitrobenzohydrazide (1.0 mmol, 197.2 mg) were stirred at room temperature for 3 h. The filtrate was kept in air for a few days to obtain colourless block-shaped crystals of the title compound.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Hydrogen-bonded (dashed lines) chains in the title compound, viewed along the b axis. H atoms not involved in the interactions have been omitted for clarity.

N'-[1-(2-Hydroxyphenyl)ethylidene]-2-nitrobenzohydrazide methanol solvate top

Crystal data top

C₁₅H₁₃N₃O₄·CH₄O	Z = 2
M_r = 331.33	F(000) = 348
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0585P)² + 0.1607P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3371 reflections	Δρ_max = 0.24 e Å⁻³
226 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₃N₃O₄·CH₄O	γ = 114.889 (2)°
M_r = 331.33	V = 794.0 (3) Å³
Triclinic, P1	Z = 2
a = 7.124 (2) Å	Mo Kα radiation
b = 8.066 (2) Å	µ = 0.11 mm⁻¹
c = 15.764 (3) Å	T = 298 K
α = 101.950 (2)°	0.23 × 0.23 × 0.22 mm
β = 92.972 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3371 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2660 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.977	R_int = 0.014
4659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
3371 reflections	Δρ_min = −0.23 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₄·CH₄O
M_r	331.33
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.124 (2), 8.066 (2), 15.764 (3)
α, β, γ (°)	101.950 (2), 92.972 (2), 114.889 (2)
V (Å³)	794.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.23 × 0.23 × 0.22

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.976, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	4659, 3371, 2660
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.05
No. of reflections	3371
No. of parameters	226
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Acknowledgements

This work was supported by Changsha University of Science and Technology (Project No. 1004091).

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