N′-(3-Hy­droxy­benzyl­idene)-4-methyl­benzohydrazide

Liu, J.-L.; Sun, M.-H.; Ma, J.-J.

doi:10.1107/S1600536812021897

organic compounds

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Volume 68| Part 6| June 2012| Page o1816

doi:10.1107/S1600536812021897

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N′-(3-Hydroxybenzylidene)-4-methylbenzohydrazide

Ji-Lai Liu,^a Ming-Hui Sun ^b and Jing-Jun Ma ^c ^*

^aHebei Changshan Biochemical Pharmaceutical Co. Ltd, Shijiazhuang Hebei 050800, People's Republic of China, ^bDepartment of Economics and Management, Hebei North University, Zhangjiakou Hebei 075000, People's Republic of China, and ^cHebei Key Laboratory of Bioinorganic Chemistry, College of Sciences, Agricultural University of Hebei, Baoding 071001, People's Republic of China
^*Correspondence e-mail: majingjun71@yahoo.cn

(Received 14 May 2012; accepted 15 May 2012; online 19 May 2012)

The title compound, C₁₅H₁₄N₂O₂, was obtained from the reaction of 3-hydroxybenzaldhyde and 4-methylbenzohydrazide in methanol. In the molecule, the benzene rings form a dihedral angle of 2.9 (3)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the molecules into layers parallel to (101). The crystal packing also exhibits π–π interactions between the aromatic rings [centroid–centroid distance = 3.686 (4) Å].

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ); Horiuchi et al. (2009 ). For benzohydrazide coordination compounds, see: El-Dissouky et al. (2010 ); Zhang et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010 ); Liu et al. (2011 ); Zhang et al. (2012 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M_r = 254.28
Monoclinic, P 2₁ /n
a = 11.5203 (14) Å
b = 8.7228 (12) Å
c = 13.5793 (19) Å
β = 106.889 (2)°
V = 1305.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.987
5767 measured reflections
2193 independent reflections
1013 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.160
S = 0.96
2193 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 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
N2—H2⋯O2ⁱ	0.90 (1)	2.10 (2)	2.926 (4)	152 (3)
O2—H2B⋯O1ⁱⁱ	0.82	1.91	2.713 (3)	166
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

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 I, global. DOI: 10.1107/S1600536812021897/cv5303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021897/cv5303Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021897/cv5303Isup3.cml

checkCIF report

Comment top

Benzohydrazide compounds are well known for their biological activities (El-Sayed et al., 2011; Horiuchi et al., 2009). In addition, benzohydrazide compounds have also been used as versatile ligands in coordination chemistry (El-Dissouky et al., 2010, Zhang et al., 2010). As a contribution to a structural study on hydrazone compounds, we present here the crystal structure of the title compound (I) obtained in the reaction of 3-hydroxybenzaldehyde with 4-methylbenzohydrazide in methanol.

In (I) (Fig. 1), two benzene rings form a dihedral angle of 2.9 (3)°. The bond lengths and angles are within normal ranges (Allen et al., 1987), and agree well with those reported for related compounds (Suleiman Gwaram et al., 2010; Liu et al., 2011; Zhang et al., 2012). Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to (101). The crystal packing exhibits π–π interactions between the aromatic rings [centroid-centroid distance = 3.686 (4) Å].

Related literature top

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011); Horiuchi et al. (2009). For benzohydrazide coordination compounds, see: El-Dissouky et al. (2010); Zhang et al. (2010). For standard bond lengths, see: Allen et al. (1987). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010); Liu et al. (2011); Zhang et al. (2012).

Experimental top

To a methanol solution (20 ml) of 3-hydroxybenzaldehyde (0.1 mmol, 12.2 mg) and 4-methylbenzohydrazide (0.1 mmol, 15.0 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Single crystals, suitable for X-ray diffraction, were obtained by slow evaporation of a methanol solution of the product in air.

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 (I), with the numbering scheme and displacement ellipsoids drawn at the 30% probability level.

N'-(3-Hydroxybenzylidene)-4-methylbenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.28	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.5203 (14) Å	Cell parameters from 1383 reflections
b = 8.7228 (12) Å	θ = 2.7–27.8°
c = 13.5793 (19) Å	µ = 0.09 mm⁻¹
β = 106.889 (2)°	T = 298 K
V = 1305.7 (3) Å³	Prism, colourless
Z = 4	0.17 × 0.15 × 0.15 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2193 independent reflections
Radiation source: fine-focus sealed tube	1013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ω scan	θ_max = 25.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→13
T_min = 0.985, T_max = 0.987	k = −10→10
5767 measured reflections	l = −16→11

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0672P)²] where P = (F_o² + 2F_c²)/3
2193 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₂	V = 1305.7 (3) Å³
M_r = 254.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5203 (14) Å	µ = 0.09 mm⁻¹
b = 8.7228 (12) Å	T = 298 K
c = 13.5793 (19) Å	0.17 × 0.15 × 0.15 mm
β = 106.889 (2)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2193 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1013 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.987	R_int = 0.070
5767 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.19 e Å⁻³
2193 reflections	Δρ_min = −0.19 e Å⁻³
176 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	0.0696 (3)	0.2934 (3)	1.0157 (2)	0.0449 (8)
N2	0.0285 (3)	0.3619 (3)	0.9196 (2)	0.0443 (8)
O1	0.2096 (3)	0.4735 (3)	0.93581 (19)	0.0626 (8)
O2	0.2664 (2)	0.0955 (3)	1.37553 (19)	0.0625 (8)
H2B	0.2708	0.0441	1.4271	0.094*
C1	0.0236 (3)	0.1217 (4)	1.1365 (3)	0.0392 (9)
C2	0.1324 (3)	0.1476 (4)	1.2118 (3)	0.0434 (10)
H2A	0.1869	0.2198	1.2012	0.052*
C3	0.1591 (4)	0.0654 (4)	1.3023 (3)	0.0437 (10)
C4	0.0790 (4)	−0.0422 (4)	1.3187 (3)	0.0509 (10)
H4	0.0979	−0.0978	1.3797	0.061*
C5	−0.0290 (4)	−0.0666 (4)	1.2441 (3)	0.0565 (11)
H5	−0.0833	−0.1390	1.2548	0.068*
C6	−0.0575 (3)	0.0154 (4)	1.1533 (3)	0.0506 (10)
H6	−0.1312	−0.0009	1.1034	0.061*
C7	−0.0067 (3)	0.2051 (4)	1.0389 (3)	0.0451 (10)
H7	−0.0835	0.1934	0.9927	0.054*
C8	0.1044 (4)	0.4477 (4)	0.8839 (3)	0.0427 (10)
C9	0.0544 (4)	0.5105 (3)	0.7790 (3)	0.0410 (9)
C10	0.1221 (4)	0.6163 (4)	0.7431 (3)	0.0578 (11)
H10	0.1989	0.6433	0.7844	0.069*
C11	0.0779 (5)	0.6825 (4)	0.6472 (3)	0.0640 (12)
H11	0.1259	0.7524	0.6251	0.077*
C12	−0.0351 (4)	0.6480 (4)	0.5838 (3)	0.0557 (11)
C13	−0.1021 (4)	0.5414 (4)	0.6183 (3)	0.0566 (11)
H13	−0.1784	0.5141	0.5762	0.068*
C14	−0.0587 (4)	0.4735 (4)	0.7144 (3)	0.0520 (11)
H14	−0.1064	0.4021	0.7356	0.062*
C15	−0.0846 (4)	0.7240 (5)	0.4805 (3)	0.0806 (14)
H15A	−0.1681	0.7508	0.4704	0.121*
H15B	−0.0787	0.6547	0.4273	0.121*
H15C	−0.0387	0.8150	0.4780	0.121*
H2	−0.0506 (13)	0.367 (4)	0.884 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.052 (2)	0.0353 (16)	0.0438 (19)	0.0031 (16)	0.0086 (17)	0.0024 (14)
N2	0.050 (2)	0.0366 (16)	0.0432 (19)	0.0005 (17)	0.0079 (17)	0.0067 (15)
O1	0.059 (2)	0.0708 (19)	0.0540 (17)	−0.0164 (15)	0.0102 (16)	−0.0015 (14)
O2	0.057 (2)	0.0703 (19)	0.0532 (17)	−0.0046 (15)	0.0047 (16)	0.0127 (14)
C1	0.045 (3)	0.0292 (18)	0.042 (2)	0.0046 (17)	0.010 (2)	−0.0003 (17)
C2	0.051 (3)	0.0307 (19)	0.051 (2)	−0.0002 (17)	0.018 (2)	−0.0006 (18)
C3	0.048 (3)	0.038 (2)	0.044 (2)	0.0030 (19)	0.012 (2)	0.0028 (18)
C4	0.063 (3)	0.038 (2)	0.051 (2)	0.000 (2)	0.017 (2)	0.0076 (19)
C5	0.071 (3)	0.039 (2)	0.062 (3)	−0.015 (2)	0.023 (3)	0.002 (2)
C6	0.054 (3)	0.038 (2)	0.055 (3)	−0.0064 (19)	0.008 (2)	−0.0009 (19)
C7	0.051 (3)	0.0312 (19)	0.049 (2)	0.0020 (19)	0.007 (2)	−0.0005 (18)
C8	0.052 (3)	0.0309 (19)	0.046 (2)	−0.0014 (19)	0.015 (2)	−0.0078 (18)
C9	0.053 (3)	0.0257 (18)	0.046 (2)	−0.0005 (18)	0.018 (2)	−0.0020 (17)
C10	0.062 (3)	0.052 (2)	0.061 (3)	−0.011 (2)	0.021 (2)	−0.003 (2)
C11	0.091 (4)	0.046 (2)	0.068 (3)	−0.011 (2)	0.043 (3)	0.010 (2)
C12	0.076 (3)	0.038 (2)	0.061 (3)	0.018 (2)	0.033 (3)	0.005 (2)
C13	0.062 (3)	0.052 (2)	0.054 (3)	0.002 (2)	0.015 (2)	0.005 (2)
C14	0.063 (3)	0.040 (2)	0.054 (3)	−0.003 (2)	0.018 (2)	0.0041 (19)
C15	0.114 (4)	0.066 (3)	0.068 (3)	0.029 (3)	0.037 (3)	0.026 (2)

Geometric parameters (Å, º) top

N1—C7	1.276 (4)	C6—H6	0.9300
N1—N2	1.388 (4)	C7—H7	0.9300
N2—C8	1.344 (4)	C8—C9	1.478 (5)
N2—H2	0.898 (10)	C9—C14	1.381 (4)
O1—C8	1.233 (4)	C9—C10	1.385 (5)
O2—C3	1.368 (4)	C10—C11	1.379 (5)
O2—H2B	0.8200	C10—H10	0.9300
C1—C6	1.380 (4)	C11—C12	1.369 (5)
C1—C2	1.386 (4)	C11—H11	0.9300
C1—C7	1.463 (4)	C12—C13	1.374 (5)
C2—C3	1.378 (4)	C12—C15	1.506 (5)
C2—H2A	0.9300	C13—C14	1.388 (4)
C3—C4	1.379 (4)	C13—H13	0.9300
C4—C5	1.374 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.381 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600

C7—N1—N2	114.9 (3)	O1—C8—C9	121.8 (4)
C8—N2—N1	119.9 (3)	N2—C8—C9	116.2 (4)
C8—N2—H2	117 (3)	C14—C9—C10	117.1 (3)
N1—N2—H2	122 (3)	C14—C9—C8	123.8 (3)
C3—O2—H2B	109.5	C10—C9—C8	119.0 (4)
C6—C1—C2	119.9 (3)	C11—C10—C9	121.3 (4)
C6—C1—C7	119.2 (4)	C11—C10—H10	119.3
C2—C1—C7	120.9 (3)	C9—C10—H10	119.3
C3—C2—C1	119.5 (3)	C12—C11—C10	121.6 (4)
C3—C2—H2A	120.2	C12—C11—H11	119.2
C1—C2—H2A	120.2	C10—C11—H11	119.2
O2—C3—C2	118.0 (3)	C11—C12—C13	117.4 (4)
O2—C3—C4	121.3 (3)	C11—C12—C15	121.5 (4)
C2—C3—C4	120.7 (4)	C13—C12—C15	121.1 (4)
C5—C4—C3	119.5 (4)	C12—C13—C14	121.6 (4)
C5—C4—H4	120.3	C12—C13—H13	119.2
C3—C4—H4	120.3	C14—C13—H13	119.2
C4—C5—C6	120.5 (4)	C9—C14—C13	120.9 (4)
C4—C5—H5	119.7	C9—C14—H14	119.6
C6—C5—H5	119.7	C13—C14—H14	119.6
C1—C6—C5	119.9 (4)	C12—C15—H15A	109.5
C1—C6—H6	120.1	C12—C15—H15B	109.5
C5—C6—H6	120.1	H15A—C15—H15B	109.5
N1—C7—C1	121.6 (4)	C12—C15—H15C	109.5
N1—C7—H7	119.2	H15A—C15—H15C	109.5
C1—C7—H7	119.2	H15B—C15—H15C	109.5
O1—C8—N2	122.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.10 (2)	2.926 (4)	152 (3)
O2—H2B···O1ⁱⁱ	0.82	1.91	2.713 (3)	166

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂
M_r	254.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.5203 (14), 8.7228 (12), 13.5793 (19)
β (°)	106.889 (2)
V (Å³)	1305.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	5767, 2193, 1013
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.160, 0.96
No. of reflections	2193
No. of parameters	176
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)	0.19, −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
N2—H2···O2ⁱ	0.898 (10)	2.10 (2)	2.926 (4)	152 (3)
O2—H2B···O1ⁱⁱ	0.82	1.91	2.713 (3)	165.5

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1/2, y−1/2, −z+5/2.

Acknowledgements

This project was sponsored by the Natural Development Foundation of Hebei Province (grant No. B2011204051), the Development Foundation of the Department of Education of Hebei Province (grant No. 2010137) and the Research Development Foundation of the Agricultural University of Hebei.

References

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