N′-(4-Hy­droxy­benzyl­idene)-2-methyl­benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536810035063

organic compounds

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Volume 66| Part 10| October 2010| Page o2482

doi:10.1107/S1600536810035063

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N′-(4-Hydroxybenzylidene)-2-methylbenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: tangchunbao@yahoo.com.cn

(Received 27 August 2010; accepted 31 August 2010; online 4 September 2010)

The title hydrazone compound, C₁₅H₁₄N₂O₂, was prepared by the condensation of 4-hydroxybenzaldehyde with 2-methylbenzohydrazide in methanol. The dihedral angle between the two benzene rings is 42.3 (2)°. In the crystal structure, molecules are linked by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ); Pyta et al. (2010 ); Angelusiu et al. (2010 ); Fun et al. (2008 ); Singh & Singh (2010 ); Ahmad et al. (2010 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M_r = 254.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6900 (15) Å
b = 11.701 (2) Å
c = 14.471 (3) Å
V = 1302.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.984
10755 measured reflections
1634 independent reflections
1502 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.12
1634 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 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
O1—H1⋯O2ⁱ	0.82	1.96	2.7657 (18)	166
O1—H1⋯N1ⁱ	0.82	2.52	2.995 (2)	118
N2—H2⋯O1ⁱⁱ	0.91 (1)	2.14 (1)	2.995 (2)	158 (2)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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/S1600536810035063/ci5176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035063/ci5176Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have been received much attention in biological chemistry and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the title new hydrazone compound (Fig. 1).

In the title molecule, the dihedral angle between the two benzene rings is 42.3 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8 and N1—N2—C8—C9 are 2.9 (2), 0.9 (2), and 0.2 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through O–H···O, O–H···N, and N–H···O intermolecular hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).

Related literature top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010); Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental top

4-Hydroxybenzaldehyde (0.1 mmol, 12.2 mg) and 3-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecular packing of the title compound, with hydrogen bonds shown as dashed lines.

N'-(4-Hydroxybenzylidene)-2-methylbenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.28	D_x = 1.297 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4917 reflections
a = 7.6900 (15) Å	θ = 2.2–27.1°
b = 11.701 (2) Å	µ = 0.09 mm⁻¹
c = 14.471 (3) Å	T = 298 K
V = 1302.1 (4) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1634 independent reflections
Radiation source: fine-focus sealed tube	1502 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.983, T_max = 0.984	k = −14→14
10755 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0604P)² + 0.1042P] where P = (F_o² + 2F_c²)/3
1634 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₂	V = 1302.1 (4) Å³
M_r = 254.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.6900 (15) Å	µ = 0.09 mm⁻¹
b = 11.701 (2) Å	T = 298 K
c = 14.471 (3) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1634 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1502 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.984	R_int = 0.024
10755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.15 e Å⁻³
1634 reflections	Δρ_min = −0.23 e Å⁻³
177 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.1045 (2)	0.76789 (13)	0.47260 (10)	0.0442 (4)
N2	0.1260 (2)	0.70443 (13)	0.55210 (10)	0.0433 (4)
O1	0.1276 (2)	1.15917 (11)	0.16838 (8)	0.0439 (3)
H1	0.0660	1.1323	0.1275	0.066*
O2	0.0277 (2)	0.54745 (11)	0.47842 (8)	0.0480 (4)
C1	0.1310 (2)	0.94736 (15)	0.39752 (11)	0.0369 (4)
C2	0.0694 (2)	0.90743 (16)	0.31255 (12)	0.0397 (4)
H2A	0.0288	0.8328	0.3080	0.048*
C3	0.0675 (2)	0.97611 (15)	0.23590 (12)	0.0391 (4)
H3	0.0264	0.9482	0.1799	0.047*
C4	0.1276 (2)	1.08777 (15)	0.24249 (11)	0.0345 (4)
C5	0.1884 (3)	1.12934 (16)	0.32573 (13)	0.0416 (4)
H5	0.2283	1.2042	0.3300	0.050*
C6	0.1899 (3)	1.05962 (16)	0.40250 (12)	0.0427 (4)
H6	0.2309	1.0880	0.4584	0.051*
C7	0.1410 (3)	0.87360 (15)	0.47796 (12)	0.0402 (4)
H7	0.1747	0.9043	0.5345	0.048*
C8	0.0859 (2)	0.59215 (15)	0.54852 (11)	0.0375 (4)
C9	0.1113 (2)	0.52835 (15)	0.63685 (12)	0.0389 (4)
C10	0.1715 (3)	0.41533 (17)	0.63644 (15)	0.0483 (5)
C11	0.1871 (3)	0.3609 (2)	0.7213 (2)	0.0631 (7)
H11	0.2286	0.2863	0.7229	0.076*
C12	0.1439 (3)	0.4126 (3)	0.80218 (18)	0.0703 (8)
H12	0.1559	0.3732	0.8576	0.084*
C13	0.0828 (3)	0.5227 (2)	0.80235 (14)	0.0649 (7)
H13	0.0519	0.5579	0.8576	0.078*
C14	0.0678 (3)	0.5808 (2)	0.71959 (13)	0.0498 (5)
H14	0.0280	0.6559	0.7194	0.060*
C15	0.2224 (4)	0.3530 (2)	0.5498 (2)	0.0763 (8)
H15A	0.1196	0.3306	0.5167	0.114*
H15B	0.2886	0.2863	0.5656	0.114*
H15C	0.2915	0.4024	0.5116	0.114*
H2	0.190 (3)	0.733 (2)	0.5994 (13)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0618 (10)	0.0404 (8)	0.0303 (7)	−0.0046 (8)	−0.0064 (7)	0.0072 (6)
N2	0.0622 (10)	0.0384 (8)	0.0294 (7)	−0.0076 (8)	−0.0103 (7)	0.0068 (6)
O1	0.0610 (8)	0.0385 (6)	0.0322 (6)	−0.0012 (6)	−0.0033 (6)	0.0082 (5)
O2	0.0697 (9)	0.0413 (7)	0.0329 (6)	−0.0064 (7)	−0.0078 (6)	−0.0010 (6)
C1	0.0426 (9)	0.0353 (8)	0.0327 (8)	0.0014 (8)	−0.0021 (7)	0.0036 (7)
C2	0.0499 (10)	0.0322 (8)	0.0371 (9)	−0.0036 (8)	−0.0030 (8)	0.0023 (7)
C3	0.0485 (10)	0.0373 (9)	0.0316 (8)	0.0001 (8)	−0.0038 (7)	−0.0014 (7)
C4	0.0380 (8)	0.0335 (8)	0.0319 (8)	0.0054 (7)	0.0010 (7)	0.0054 (7)
C5	0.0537 (11)	0.0304 (8)	0.0407 (9)	−0.0019 (8)	−0.0045 (8)	0.0012 (7)
C6	0.0566 (11)	0.0393 (9)	0.0322 (8)	−0.0018 (9)	−0.0088 (8)	−0.0008 (8)
C7	0.0504 (10)	0.0396 (9)	0.0305 (8)	−0.0009 (8)	−0.0039 (8)	0.0016 (8)
C8	0.0437 (9)	0.0370 (8)	0.0317 (8)	−0.0007 (8)	−0.0010 (7)	0.0020 (7)
C9	0.0414 (9)	0.0390 (9)	0.0361 (8)	−0.0069 (8)	−0.0055 (8)	0.0068 (7)
C10	0.0468 (11)	0.0388 (9)	0.0592 (12)	−0.0054 (8)	−0.0076 (9)	0.0087 (9)
C11	0.0553 (13)	0.0510 (12)	0.0831 (17)	−0.0073 (10)	−0.0172 (13)	0.0303 (13)
C12	0.0643 (14)	0.0870 (18)	0.0594 (14)	−0.0195 (15)	−0.0179 (11)	0.0431 (14)
C13	0.0711 (15)	0.0877 (19)	0.0361 (10)	−0.0117 (14)	−0.0034 (10)	0.0141 (11)
C14	0.0590 (12)	0.0541 (11)	0.0364 (9)	−0.0040 (10)	−0.0023 (9)	0.0065 (9)
C15	0.092 (2)	0.0484 (12)	0.0880 (18)	0.0146 (14)	−0.0047 (17)	−0.0092 (14)

Geometric parameters (Å, º) top

N1—C7	1.271 (2)	C6—H6	0.93
N1—N2	1.379 (2)	C7—H7	0.93
N2—C8	1.350 (2)	C8—C9	1.493 (2)
N2—H2	0.907 (10)	C9—C14	1.387 (3)
O1—C4	1.3594 (19)	C9—C10	1.401 (3)
O1—H1	0.82	C10—C11	1.389 (3)
O2—C8	1.226 (2)	C10—C15	1.503 (3)
C1—C6	1.391 (3)	C11—C12	1.358 (4)
C1—C2	1.398 (2)	C11—H11	0.93
C1—C7	1.451 (2)	C12—C13	1.371 (4)
C2—C3	1.370 (2)	C12—H12	0.93
C2—H2A	0.93	C13—C14	1.382 (3)
C3—C4	1.389 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C4—C5	1.381 (2)	C15—H15A	0.96
C5—C6	1.378 (2)	C15—H15B	0.96
C5—H5	0.93	C15—H15C	0.96

C7—N1—N2	116.54 (15)	O2—C8—C9	122.87 (16)
C8—N2—N1	117.68 (14)	N2—C8—C9	115.07 (15)
C8—N2—H2	120.6 (17)	C14—C9—C10	120.08 (17)
N1—N2—H2	119.9 (17)	C14—C9—C8	119.10 (17)
C4—O1—H1	109.5	C10—C9—C8	120.77 (17)
C6—C1—C2	118.12 (15)	C11—C10—C9	117.2 (2)
C6—C1—C7	120.18 (16)	C11—C10—C15	119.6 (2)
C2—C1—C7	121.65 (16)	C9—C10—C15	123.19 (19)
C3—C2—C1	121.31 (16)	C12—C11—C10	122.5 (2)
C3—C2—H2A	119.3	C12—C11—H11	118.8
C1—C2—H2A	119.3	C10—C11—H11	118.8
C2—C3—C4	119.52 (16)	C11—C12—C13	120.2 (2)
C2—C3—H3	120.2	C11—C12—H12	119.9
C4—C3—H3	120.2	C13—C12—H12	119.9
O1—C4—C5	118.15 (16)	C12—C13—C14	119.3 (2)
O1—C4—C3	121.59 (15)	C12—C13—H13	120.3
C5—C4—C3	120.26 (15)	C14—C13—H13	120.3
C6—C5—C4	119.83 (16)	C13—C14—C9	120.7 (2)
C6—C5—H5	120.1	C13—C14—H14	119.7
C4—C5—H5	120.1	C9—C14—H14	119.7
C5—C6—C1	120.96 (16)	C10—C15—H15A	109.5
C5—C6—H6	119.5	C10—C15—H15B	109.5
C1—C6—H6	119.5	H15A—C15—H15B	109.5
N1—C7—C1	121.21 (16)	C10—C15—H15C	109.5
N1—C7—H7	119.4	H15A—C15—H15C	109.5
C1—C7—H7	119.4	H15B—C15—H15C	109.5
O2—C8—N2	122.01 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.96	2.7657 (18)	166
O1—H1···N1ⁱ	0.82	2.52	2.995 (2)	118
N2—H2···O1ⁱⁱ	0.91 (1)	2.14 (1)	2.995 (2)	158 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂
M_r	254.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.6900 (15), 11.701 (2), 14.471 (3)
V (Å³)	1302.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10755, 1634, 1502
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.12
No. of reflections	1634
No. of parameters	177
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)	0.15, −0.23

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O1—H1···O2ⁱ	0.82	1.96	2.7657 (18)	166
O1—H1···N1ⁱ	0.82	2.52	2.995 (2)	118
N2—H2···O1ⁱⁱ	0.91 (1)	2.14 (1)	2.995 (2)	158 (2)

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

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976. Web of Science CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055–2062. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Sujith, K. V., Patil, P. S., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1961–o1962. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pyta, K., Przybylski, P., Huczynski, A., Hoser, A., Wozniak, K., Schilf, W., Kamienski, B., Grech, E. & Brzezinski, B. (2010). J. Mol. Struct. 970, 147–154. Web of Science CSD CrossRef CAS Google Scholar
Rasras, A. J. M., Al-Tel, T. H., Al-Aboudi, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307–2313. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172. Web of Science CSD CrossRef IUCr Journals Google Scholar