2-Hy­droxy-N′-(5-hy­droxy-2-nitro­benzyl­idene)-3-methyl­benzohydrazide

Zhu, Z.-F.; Shao, L.-J.; Shen, X.-H.

doi:10.1107/S1600536812002437

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o559

doi:10.1107/S1600536812002437

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2-Hydroxy-N′-(5-hydroxy-2-nitrobenzylidene)-3-methylbenzohydrazide

Zhao-Fu Zhu,^a Li-Juen Shao ^a and Xi-Hai Shen ^a ^*

^aDepartment of Chemistry, Hebei Normal University of Science and Technology, Qinhuangdao 066600, People's Republic of China
^*Correspondence e-mail: zhaofu_zhu@163.com

(Received 8 January 2012; accepted 19 January 2012; online 4 February 2012)

The title compound, C₁₅H₁₃N₃O₅, was prepared by condensing 5-hydroxy-2-nitrobenzaldehyde and 2-hydroxy-3-methylbenzohydrazide in methanol. The two benzene rings make a dihedral angle of 3.9 (3)°. An intramolecular O—H⋯O hydrogen bond is observed. The crystal structure is stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds, and C—H⋯O and π–π interactions [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_r = 315.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.132
S = 1.01
2942 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002437/su2366sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812002437/su2366Isup3.cml

checkCIF report

Comment top

In the last few years, the synthesis and crystal structures of a number of hydrazone compounds have been reported (Fun et al., 2011; Horkaew et al., 2011; Zhi et al., 2011; Huang & Wu, 2010). The compounds derived from 2-hydroxy-3-methylbenzohydrazide have seldom been reported As an extension of our work on such compounds (Shen et al., 2012; Zhu et al., 2012), we report herein on the crystal structure of the title compound.

In the molecule of the title compound there is an intramolecular O5—H5···O4 hydrogen bond (Table 1 and Fig. 1). The (C1—C6) and (C9—C14) benzene rings make a dihedral angle of 3.9 (3)°. All the bond values are within normal ranges and are comparable with those in similar compounds reported on by (Fun et al., 2011; Horkaew et al., 2011; Zhi et al., 2011; Huang & Wu, 2010; Shen et al., 2012; Zhu et al., 2012).

In the crystal molecules are linked by intermolecular O—H···O and N—H···O hydrogen bonds and C—H···O interactions (Table 1 and Fig. 2). Moreover, there are also π–π interactions present involving molecules related by inversion centers [Cg1—Cg1ⁱ 3.7989 (17) Å; Cg1—Cg2ⁱⁱ 3.5658 (17) Å; Cg2—Cg2ⁱⁱⁱ 3.9287 (19) Å; symmetry codes: (i) -x, -y + 1, -z + 1; (ii) -x + 1, -y, -z + 1; (iii) -x + 1, -y, -z + 2; where Cg1 and Cg2 are the centroids of the (C1—C6) and (C9—C14) benzene rings, respectively].

Related literature top

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 top

5-Hydroxy-2-nitrobenzaldehyde (167.1 mg, 1.0 mmol) and 2-hydroxy-3-methylbenzohydrazide (166.2 mg, 1.0 mmol) were mixed in methanol (60 ml). The mixture was refluxed for 30 min, then cooled to room temperature, yielding a colourless solution. Colourless block-like crystals of the title compound were formed when the solution was evaporated in air for several days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom numbering and displacement ellipsoids drawn at the 30% probability level. The intramolecular O—H···O hydrogen bond is drawn as a dashed line - see Table 1 for details.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines - see Table 1 for details.

2-Hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-3-methylbenzohydrazide top

Crystal data top

C₁₅H₁₃N₃O₅	Z = 2
M_r = 315.28	F(000) = 328
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	2942 independent reflections
Radiation source: fine-focus sealed tube	1788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.980, T_max = 0.985	k = −11→10
4694 measured reflections	l = −13→10

Refinement top

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(F_o²) + (0.0593P)²] where P = (F_o² + 2F_c²)/3
2942 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₅	γ = 77.479 (2)°
M_r = 315.28	V = 701.4 (4) Å³
Triclinic, P1	Z = 2
a = 7.643 (2) Å	Mo Kα radiation
b = 9.055 (3) Å	µ = 0.12 mm⁻¹
c = 10.876 (3) Å	T = 298 K
α = 84.865 (2)°	0.18 × 0.17 × 0.13 mm
β = 72.732 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2942 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1788 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.025
4694 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.21 e Å⁻³
2942 reflections	Δρ_min = −0.22 e Å⁻³
214 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₅
M_r	315.28
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.643 (2), 9.055 (3), 10.876 (3)
α, β, γ (°)	84.865 (2), 72.732 (2), 77.479 (2)
V (Å³)	701.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.18 × 0.17 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	4694, 2942, 1788
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.132, 1.01
No. of reflections	2942
No. of parameters	214
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)	0.21, −0.22

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4	0.82	1.830	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)	166.7 (17)
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) −x, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z+1.

References

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Volume 68| Part 3| March 2012| Page o559

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