2-Hy­droxy-N′-(4-hy­droxy­benzyl­idene)-3-methyl­benzohydrazide

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

doi:10.1107/S1600536811055930

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o297

doi:10.1107/S1600536811055930

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2-Hydroxy-N′-(4-hydroxybenzylidene)-3-methylbenzohydrazide

Xi-Hai Shen,^a Li-Xue Zhu,^a ^* Li-Juen Shao ^a and Zhao-Fu Zhu ^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 26 December 2011; accepted 27 December 2011; online 7 January 2012)

The title compound, C₁₅H₁₄N₂O₃, was prepared by condensing 4-hydroxybenzaldehyde and 2-hydroxy-3-methylbenzohydrazide in methanol. The two benzene rings make a dihedral angle of 19.03 (11)°. 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 interactions, which lead to the formation of a three-dimensional network.

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 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3872 (17) Å
b = 13.012 (2) Å
c = 13.592 (2) Å
V = 1306.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.981, T_max = 0.984
6296 measured reflections
2663 independent reflections
1953 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.103
S = 0.99
2663 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.86	2.575 (2)	146
O1—H1⋯O2ⁱ	0.82	2.00	2.809 (2)	167
N2—H2A⋯O1ⁱⁱ	0.86	2.36	3.067 (2)	139
C3—H3A⋯O2ⁱ	0.93	2.51	3.208 (2)	132
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ .

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/S1600536811055930/su2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055930/su2356Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055930/su2356Isup3.cml

checkCIF report

Comment top

In the last few years, the 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). As an extension of work on such compounds, we report herein on the synthesis and crystal structure of the title compound.

In the title molecule, Fig. 1, there is an intramolecular O3—H3···O2 hydrogen bond (Table 1). The benzene rings, (C1—C6) and (C9—C14), make a dihedral angle of 19.03 (11)°. All the geometrical parameters are within normal ranges and are comparable with those in similar compounds, mentioned above.

In the crystal, molecules are linked via O—H···O and N—H···O hydrogen bonds and C-H···O interactions, leading to the formation of a three-dimensional network (Table 1 and Fig. 2).

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).

Experimental top

4-Hydroxybenzaldehyde (122.1 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 crystals were formed when the solution was left to evaporate 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 atom numbering and displacement ellipsoids drawn at the 30% probability level. The intramolecular O—H···O hydrogen bond is drawn as a dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. The O-H···O and N-H···O hydrogen bonds are drawn as dashed lines.

2-Hydroxy-N'-(4-hydroxybenzylidene)-3-methylbenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₃	F(000) = 568
M_r = 270.28	D_x = 1.374 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1375 reflections
a = 7.3872 (17) Å	θ = 2.6–24.5°
b = 13.012 (2) Å	µ = 0.10 mm⁻¹
c = 13.592 (2) Å	T = 298 K
V = 1306.5 (4) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2663 independent reflections
Radiation source: fine-focus sealed tube	1953 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 26.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
T_min = 0.981, T_max = 0.984	k = −13→16
6296 measured reflections	l = −17→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0494P)²] where P = (F_o² + 2F_c²)/3
2663 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₃	V = 1306.5 (4) Å³
M_r = 270.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3872 (17) Å	µ = 0.10 mm⁻¹
b = 13.012 (2) Å	T = 298 K
c = 13.592 (2) Å	0.20 × 0.20 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2663 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1953 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.032
6296 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 0.99	Δρ_max = 0.13 e Å⁻³
2663 reflections	Δρ_min = −0.19 e Å⁻³
184 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	0.0995 (3)	0.79013 (12)	0.51891 (12)	0.0453 (5)
N2	0.1159 (3)	0.72214 (12)	0.44083 (12)	0.0455 (5)
H2A	0.1404	0.7437	0.3825	0.055*
O1	0.1126 (2)	1.18743 (10)	0.79368 (10)	0.0516 (4)
H1	0.0544	1.1672	0.8412	0.077*
O2	0.0499 (2)	0.59172 (10)	0.54350 (10)	0.0523 (5)
O3	0.1334 (3)	0.40715 (11)	0.49251 (11)	0.0600 (5)
H3	0.1016	0.4528	0.5303	0.090*
C1	0.1268 (3)	0.96163 (14)	0.57681 (14)	0.0376 (5)
C2	0.0866 (3)	0.93585 (16)	0.67358 (15)	0.0430 (6)
H2	0.0608	0.8679	0.6894	0.052*
C3	0.0846 (3)	1.00949 (16)	0.74632 (14)	0.0433 (6)
H3A	0.0602	0.9908	0.8110	0.052*
C4	0.1188 (3)	1.11133 (14)	0.72333 (15)	0.0395 (5)
C5	0.1604 (3)	1.13823 (17)	0.62779 (15)	0.0479 (6)
H5	0.1856	1.2063	0.6121	0.057*
C6	0.1646 (3)	1.06390 (16)	0.55602 (16)	0.0457 (6)
H6	0.1935	1.0826	0.4919	0.055*
C7	0.1324 (3)	0.88408 (15)	0.49972 (15)	0.0424 (5)
H7	0.1604	0.9034	0.4356	0.051*
C8	0.0922 (3)	0.62132 (15)	0.45912 (15)	0.0410 (5)
C9	0.1136 (3)	0.54807 (15)	0.37750 (14)	0.0393 (5)
C10	0.1344 (3)	0.44378 (16)	0.39901 (15)	0.0437 (5)
C11	0.1573 (3)	0.37050 (17)	0.32441 (17)	0.0487 (6)
C12	0.1510 (3)	0.40437 (19)	0.22839 (17)	0.0541 (6)
H12	0.1634	0.3569	0.1777	0.065*
C13	0.1266 (3)	0.50748 (19)	0.20530 (17)	0.0537 (6)
H13	0.1215	0.5281	0.1399	0.064*
C14	0.1101 (3)	0.57847 (17)	0.27877 (15)	0.0465 (5)
H14	0.0964	0.6476	0.2630	0.056*
C15	0.1874 (4)	0.26079 (17)	0.35184 (19)	0.0692 (8)
H15A	0.2038	0.2206	0.2933	0.104*
H15B	0.0842	0.2357	0.3875	0.104*
H15C	0.2934	0.2555	0.3924	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0612 (13)	0.0413 (10)	0.0334 (10)	0.0007 (9)	0.0050 (9)	−0.0060 (7)
N2	0.0655 (13)	0.0413 (10)	0.0297 (9)	0.0004 (9)	0.0056 (10)	−0.0025 (8)
O1	0.0721 (12)	0.0415 (8)	0.0411 (8)	−0.0051 (8)	0.0055 (8)	−0.0065 (7)
O2	0.0801 (12)	0.0455 (9)	0.0312 (8)	−0.0016 (8)	0.0081 (8)	0.0011 (7)
O3	0.0948 (13)	0.0435 (9)	0.0416 (9)	0.0010 (10)	0.0016 (10)	0.0033 (7)
C1	0.0427 (12)	0.0367 (11)	0.0335 (11)	0.0039 (10)	−0.0002 (10)	0.0008 (9)
C2	0.0518 (14)	0.0346 (11)	0.0427 (12)	−0.0004 (10)	0.0029 (11)	0.0039 (10)
C3	0.0576 (16)	0.0410 (12)	0.0313 (11)	0.0001 (10)	0.0038 (11)	0.0010 (9)
C4	0.0436 (13)	0.0366 (11)	0.0383 (12)	0.0026 (10)	0.0018 (11)	−0.0053 (9)
C5	0.0598 (15)	0.0362 (11)	0.0475 (14)	−0.0068 (10)	0.0091 (12)	0.0031 (10)
C6	0.0579 (15)	0.0453 (13)	0.0339 (11)	0.0019 (11)	0.0046 (12)	0.0053 (10)
C7	0.0469 (13)	0.0434 (13)	0.0368 (12)	0.0037 (11)	0.0051 (11)	−0.0005 (10)
C8	0.0458 (13)	0.0425 (12)	0.0347 (12)	−0.0010 (10)	−0.0004 (11)	0.0019 (9)
C9	0.0429 (12)	0.0411 (11)	0.0340 (11)	−0.0024 (10)	−0.0009 (11)	−0.0042 (9)
C10	0.0491 (14)	0.0453 (12)	0.0365 (12)	−0.0060 (11)	−0.0005 (11)	−0.0023 (10)
C11	0.0458 (14)	0.0508 (14)	0.0495 (14)	−0.0061 (11)	0.0031 (11)	−0.0102 (11)
C12	0.0519 (15)	0.0624 (16)	0.0481 (14)	−0.0065 (12)	0.0039 (12)	−0.0237 (12)
C13	0.0602 (16)	0.0687 (16)	0.0322 (12)	−0.0023 (14)	0.0010 (12)	−0.0033 (11)
C14	0.0520 (14)	0.0515 (13)	0.0360 (12)	0.0003 (11)	−0.0003 (11)	0.0011 (10)
C15	0.083 (2)	0.0445 (14)	0.0800 (19)	−0.0051 (13)	0.0022 (16)	−0.0157 (13)

Geometric parameters (Å, º) top

N1—C7	1.273 (2)	C5—H5	0.9300
N1—N2	1.387 (2)	C6—H6	0.9300
N2—C8	1.347 (2)	C7—H7	0.9300
N2—H2A	0.8600	C8—C9	1.471 (3)
O1—C4	1.377 (2)	C9—C10	1.397 (3)
O1—H1	0.8200	C9—C14	1.399 (3)
O2—C8	1.249 (2)	C10—C11	1.402 (3)
O3—C10	1.357 (2)	C11—C12	1.378 (3)
O3—H3	0.8200	C11—C15	1.492 (3)
C1—C6	1.389 (3)	C12—C13	1.390 (3)
C1—C2	1.389 (3)	C12—H12	0.9300
C1—C7	1.455 (3)	C13—C14	1.366 (3)
C2—C3	1.377 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.385 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.380 (3)	C15—H15C	0.9600
C5—C6	1.374 (3)

C7—N1—N2	116.04 (18)	O2—C8—N2	120.15 (18)
C8—N2—N1	117.96 (17)	O2—C8—C9	121.28 (18)
C8—N2—H2A	121.0	N2—C8—C9	118.56 (18)
N1—N2—H2A	121.0	C10—C9—C14	118.51 (19)
C4—O1—H1	109.5	C10—C9—C8	118.92 (18)
C10—O3—H3	109.5	C14—C9—C8	122.55 (18)
C6—C1—C2	117.84 (18)	O3—C10—C9	122.45 (19)
C6—C1—C7	120.81 (18)	O3—C10—C11	116.04 (19)
C2—C1—C7	121.34 (18)	C9—C10—C11	121.5 (2)
C3—C2—C1	120.93 (18)	C12—C11—C10	117.6 (2)
C3—C2—H2	119.5	C12—C11—C15	123.2 (2)
C1—C2—H2	119.5	C10—C11—C15	119.2 (2)
C2—C3—C4	120.13 (19)	C11—C12—C13	121.8 (2)
C2—C3—H3A	119.9	C11—C12—H12	119.1
C4—C3—H3A	119.9	C13—C12—H12	119.1
O1—C4—C5	118.58 (18)	C14—C13—C12	120.0 (2)
O1—C4—C3	121.69 (18)	C14—C13—H13	120.0
C5—C4—C3	119.73 (18)	C12—C13—H13	120.0
C6—C5—C4	119.64 (19)	C13—C14—C9	120.6 (2)
C6—C5—H5	120.2	C13—C14—H14	119.7
C4—C5—H5	120.2	C9—C14—H14	119.7
C5—C6—C1	121.70 (19)	C11—C15—H15A	109.5
C5—C6—H6	119.1	C11—C15—H15B	109.5
C1—C6—H6	119.1	H15A—C15—H15B	109.5
N1—C7—C1	120.85 (19)	C11—C15—H15C	109.5
N1—C7—H7	119.6	H15A—C15—H15C	109.5
C1—C7—H7	119.6	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.86	2.575 (2)	146
O1—H1···O2ⁱ	0.82	2.00	2.809 (2)	167
N2—H2A···O1ⁱⁱ	0.86	2.36	3.067 (2)	139
C3—H3A···O2ⁱ	0.93	2.51	3.208 (2)	132

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1/2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.3872 (17), 13.012 (2), 13.592 (2)
V (Å³)	1306.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	6296, 2663, 1953
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.103, 0.99
No. of reflections	2663
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.19

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
O3—H3···O2	0.82	1.86	2.575 (2)	146
O1—H1···O2ⁱ	0.82	2.00	2.809 (2)	167
N2—H2A···O1ⁱⁱ	0.86	2.36	3.067 (2)	139
C3—H3A···O2ⁱ	0.93	2.51	3.208 (2)	132

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1/2, −y+2, z−1/2.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644–o2645. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o2985. Web of Science CSD CrossRef IUCr Journals Google Scholar
Huang, H.-T. & Wu, H.-Y. (2010). Acta Cryst. E66, o2729–o2730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhi, F., Wang, R., Zhang, Y., Wang, Q. & Yang, Y.-L. (2011). Acta Cryst. E67, o2825. Web of Science CSD CrossRef IUCr Journals Google Scholar

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doi:10.1107/S1600536811055930

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