N′-(2-Chloro­benzyl­idene)-2-hydr­oxy-3-methyl­benzohydrazide

Han, Y.-Y.; Zhao, Q.-R.

doi:10.1107/S1600536810012110

organic compounds

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Volume 66| Part 5| May 2010| Page o1025

https://doi.org/10.1107/S1600536810012110

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N′-(2-Chlorobenzylidene)-2-hydroxy-3-methylbenzohydrazide

You-Yue Han ^a ^* and Qiu-Rong Zhao ^a

^aDepartment of Chemistry and Life Science, Chuzhou University, Chuzhou, Anhui 239000, People's Republic of China
^*Correspondence e-mail: hanyouyue@126.com

(Received 30 March 2010; accepted 30 March 2010; online 2 April 2010)

In the title compound, C₁₅H₁₃ClN₂O₂, the dihedral angle between the two benzene rings is 3.4 (5)° and the molecule adopts an E configuration with respect to the C=N bond. There is an intramolecular O—H⋯O hydrogen bond in the molecule, which generates an S(6) loop. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming C(4) chains running along the a axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ); Cukurovali et al. (2006 ). For related structures, see: Mohd Lair et al. (2009 ); Lin & Sang (2009 ); Suleiman Gwaram et al. (2010 ); Li & Ban (2009 ); Lo & Ng (2009 ); Ning & Xu (2009 ); Zhu et al. (2009 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂
M_r = 288.72
Monoclinic, C c
a = 7.084 (2) Å
b = 27.010 (3) Å
c = 7.755 (2) Å
β = 111.229 (3)°
V = 1383.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.967, T_max = 0.973
3856 measured reflections
1981 independent reflections
1145 reflections with I > 2σ(I)
R_int = 0.151

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.220
S = 0.92
1981 reflections
183 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.45 e Å⁻³
Absolute structure: Flack (1983 ), 470 Friedel pairs
Flack parameter: 0.29 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.41	3.202 (7)	154
O2—H2⋯O1	0.82	1.92	2.641 (7)	146
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: 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: https://doi.org/10.1107/S1600536810012110/hb5388sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012110/hb5388Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). In the present work, the title new hydrazone compound is reported.

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 3.4 (5)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O–H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable with those in the similar compounds (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1) to form chains running along the a axis (Fig. 2).

Related literature top

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For related structures, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010); Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009). For reference bond-length values, see: Allen et al. (1987).

Experimental top

A mixture of 2-chlorobenzaldehyde (0.140 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in 50 ml me thanol was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, colourless blocks of (I) were formed.

Structure description top

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1) to form chains running along the a axis (Fig. 2).

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For related structures, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010); Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009). For reference bond-length values, see: Allen et al. (1987).

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 (I) with 30% probability displacement ellipsoids for non-H atoms. Intramolecular O–H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The packing of (I) viewed along the c axis. Hydrogen bonds are shown as dashed lines.

N'-(2-Chlorobenzylidene)-2-hydroxy-3-methylbenzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O₂	F(000) = 600
M_r = 288.72	D_x = 1.387 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 975 reflections
a = 7.084 (2) Å	θ = 2.6–24.5°
b = 27.010 (3) Å	µ = 0.28 mm⁻¹
c = 7.755 (2) Å	T = 298 K
β = 111.229 (3)°	Block, colorless
V = 1383.1 (6) Å³	0.12 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1981 independent reflections
Radiation source: fine-focus sealed tube	1145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.151
ω scans	θ_max = 27.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −4→9
T_min = 0.967, T_max = 0.973	k = −34→34
3856 measured reflections	l = −9→9

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)] = 0.083	H-atom parameters constrained
wR(F²) = 0.220	w = 1/[σ²(F_o²) + (0.1271P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max = 0.001
1981 reflections	Δρ_max = 0.39 e Å⁻³
183 parameters	Δρ_min = −0.45 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 470 Fridel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.29 (17)

Crystal data top

C₁₅H₁₃ClN₂O₂	V = 1383.1 (6) Å³
M_r = 288.72	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 7.084 (2) Å	µ = 0.28 mm⁻¹
b = 27.010 (3) Å	T = 298 K
c = 7.755 (2) Å	0.12 × 0.10 × 0.10 mm
β = 111.229 (3)°

Data collection top

Bruker SMART CCD diffractometer	1981 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1145 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.973	R_int = 0.151
3856 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	H-atom parameters constrained
wR(F²) = 0.220	Δρ_max = 0.39 e Å⁻³
S = 0.92	Δρ_min = −0.45 e Å⁻³
1981 reflections	Absolute structure: Flack (1983), 470 Fridel pairs
183 parameters	Absolute structure parameter: 0.29 (17)
2 restraints

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 > 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
Cl1	0.3375 (3)	0.43050 (6)	0.8129 (3)	0.0785 (7)
N1	0.2710 (8)	0.24748 (18)	0.8198 (7)	0.0526 (14)
H1	0.3490	0.2572	0.9277	0.063*
N2	0.2275 (8)	0.2780 (2)	0.6677 (6)	0.0503 (13)
O1	0.0826 (8)	0.18614 (19)	0.6388 (6)	0.0704 (15)
O2	0.1832 (8)	0.09660 (18)	0.7787 (7)	0.0666 (14)
H2	0.1443	0.1174	0.6964	0.100*
C1	0.2311 (9)	0.1713 (2)	0.9627 (8)	0.0462 (15)
C2	0.2276 (10)	0.1188 (2)	0.9446 (8)	0.0505 (16)
C3	0.2680 (10)	0.0889 (3)	1.1021 (10)	0.0599 (19)
C4	0.3049 (11)	0.1111 (3)	1.2688 (9)	0.065 (2)
H4	0.3328	0.0912	1.3730	0.078*
C5	0.3026 (12)	0.1623 (3)	1.2901 (11)	0.067 (2)
H5	0.3253	0.1762	1.4055	0.081*
C6	0.2661 (9)	0.1919 (3)	1.1361 (8)	0.0550 (17)
H6	0.2648	0.2262	1.1484	0.066*
C7	0.1867 (9)	0.2013 (2)	0.7943 (8)	0.0489 (16)
C8	0.2946 (10)	0.3218 (3)	0.7035 (9)	0.0485 (15)
H8	0.3665	0.3312	0.8251	0.058*
C9	0.2591 (9)	0.3575 (2)	0.5540 (8)	0.0445 (14)
C10	0.2758 (10)	0.4085 (2)	0.5897 (9)	0.0548 (18)
C11	0.2424 (13)	0.4419 (3)	0.4451 (12)	0.070 (2)
H11	0.2509	0.4757	0.4689	0.084*
C12	0.1983 (14)	0.4256 (3)	0.2722 (13)	0.078 (2)
H12	0.1778	0.4485	0.1775	0.093*
C13	0.1823 (11)	0.3753 (3)	0.2297 (9)	0.066 (2)
H13	0.1523	0.3645	0.1087	0.079*
C14	0.2122 (10)	0.3417 (3)	0.3723 (9)	0.0555 (18)
H14	0.2008	0.3080	0.3462	0.067*
C15	0.2730 (15)	0.0336 (3)	1.0799 (14)	0.085 (3)
H15A	0.3750	0.0251	1.0306	0.127*
H15B	0.1433	0.0224	0.9969	0.127*
H15C	0.3037	0.0180	1.1982	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1018 (16)	0.0557 (10)	0.0756 (12)	−0.0051 (12)	0.0294 (10)	−0.0184 (10)
N1	0.063 (3)	0.044 (3)	0.035 (2)	−0.005 (3)	−0.001 (2)	0.005 (2)
N2	0.056 (3)	0.049 (3)	0.034 (2)	−0.002 (3)	0.002 (2)	0.002 (2)
O1	0.100 (4)	0.057 (3)	0.034 (2)	−0.024 (3)	0.001 (2)	−0.001 (2)
O2	0.087 (4)	0.049 (3)	0.058 (3)	−0.002 (3)	0.020 (3)	−0.005 (2)
C1	0.042 (3)	0.046 (3)	0.039 (3)	−0.001 (3)	0.001 (3)	0.001 (3)
C2	0.050 (4)	0.049 (3)	0.043 (3)	−0.003 (3)	0.005 (3)	0.006 (3)
C3	0.052 (4)	0.056 (4)	0.062 (5)	0.001 (3)	0.009 (3)	0.015 (3)
C4	0.063 (5)	0.075 (5)	0.050 (4)	−0.001 (4)	0.012 (4)	0.025 (4)
C5	0.066 (5)	0.089 (6)	0.043 (3)	−0.008 (4)	0.015 (3)	−0.003 (4)
C6	0.059 (4)	0.059 (4)	0.038 (3)	−0.007 (3)	0.007 (3)	0.001 (3)
C7	0.051 (4)	0.049 (3)	0.034 (3)	−0.005 (3)	0.001 (3)	−0.003 (3)
C8	0.048 (4)	0.049 (4)	0.039 (3)	−0.007 (3)	0.003 (2)	0.001 (3)
C9	0.046 (3)	0.043 (3)	0.041 (3)	0.002 (3)	0.011 (3)	0.003 (3)
C10	0.058 (4)	0.044 (3)	0.060 (4)	−0.003 (3)	0.018 (3)	−0.005 (3)
C11	0.078 (5)	0.047 (4)	0.082 (6)	0.009 (4)	0.024 (4)	0.012 (4)
C12	0.085 (6)	0.071 (5)	0.074 (5)	0.010 (5)	0.024 (4)	0.032 (5)
C13	0.066 (5)	0.082 (5)	0.038 (3)	0.001 (4)	0.006 (3)	0.012 (3)
C14	0.051 (4)	0.061 (4)	0.048 (4)	−0.004 (3)	0.011 (3)	0.008 (3)
C15	0.093 (6)	0.057 (4)	0.100 (7)	0.006 (5)	0.028 (5)	0.024 (5)

Geometric parameters (Å, º) top

Cl1—C10	1.730 (7)	C5—H5	0.9300
N1—C7	1.365 (8)	C6—H6	0.9300
N1—N2	1.379 (7)	C8—C9	1.458 (9)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.268 (8)	C9—C14	1.392 (10)
O1—C7	1.234 (7)	C9—C10	1.400 (8)
O2—C2	1.350 (8)	C10—C11	1.392 (10)
O2—H2	0.8200	C11—C12	1.336 (12)
C1—C6	1.392 (9)	C11—H11	0.9300
C1—C2	1.423 (8)	C12—C13	1.392 (12)
C1—C7	1.472 (9)	C12—H12	0.9300
C2—C3	1.405 (9)	C13—C14	1.387 (10)
C3—C4	1.362 (10)	C13—H13	0.9300
C3—C15	1.506 (12)	C14—H14	0.9300
C4—C5	1.394 (11)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.382 (10)	C15—H15C	0.9600

C7—N1—N2	118.1 (4)	N2—C8—H8	120.0
C7—N1—H1	121.0	C9—C8—H8	120.0
N2—N1—H1	121.0	C14—C9—C10	118.3 (6)
C8—N2—N1	114.9 (5)	C14—C9—C8	120.7 (6)
C2—O2—H2	109.5	C10—C9—C8	121.0 (6)
C6—C1—C2	119.0 (6)	C11—C10—C9	120.0 (6)
C6—C1—C7	122.8 (6)	C11—C10—Cl1	119.4 (5)
C2—C1—C7	118.1 (5)	C9—C10—Cl1	120.6 (5)
O2—C2—C3	118.4 (6)	C12—C11—C10	120.3 (7)
O2—C2—C1	121.8 (5)	C12—C11—H11	119.8
C3—C2—C1	119.8 (6)	C10—C11—H11	119.8
C4—C3—C2	118.7 (7)	C11—C12—C13	121.9 (7)
C4—C3—C15	122.7 (7)	C11—C12—H12	119.1
C2—C3—C15	118.5 (7)	C13—C12—H12	119.1
C3—C4—C5	122.9 (7)	C14—C13—C12	118.3 (7)
C3—C4—H4	118.6	C14—C13—H13	120.9
C5—C4—H4	118.6	C12—C13—H13	120.9
C6—C5—C4	118.6 (7)	C13—C14—C9	121.2 (7)
C6—C5—H5	120.7	C13—C14—H14	119.4
C4—C5—H5	120.7	C9—C14—H14	119.4
C5—C6—C1	121.0 (7)	C3—C15—H15A	109.5
C5—C6—H6	119.5	C3—C15—H15B	109.5
C1—C6—H6	119.5	H15A—C15—H15B	109.5
O1—C7—N1	121.4 (6)	C3—C15—H15C	109.5
O1—C7—C1	122.9 (6)	H15A—C15—H15C	109.5
N1—C7—C1	115.7 (5)	H15B—C15—H15C	109.5
N2—C8—C9	120.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.41	3.202 (7)	154
O2—H2···O1	0.82	1.92	2.641 (7)	146

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₂
M_r	288.72
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	7.084 (2), 27.010 (3), 7.755 (2)
β (°)	111.229 (3)
V (Å³)	1383.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.12 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.967, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	3856, 1981, 1145
R_int	0.151
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.220, 0.92
No. of reflections	1981
No. of parameters	183
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.45
Absolute structure	Flack (1983), 470 Fridel pairs
Absolute structure parameter	0.29 (17)

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···O1ⁱ	0.86	2.41	3.202 (7)	154
O2—H2···O1	0.82	1.92	2.641 (7)	146

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the Applied Chemistry Key Subject of Anhui Province (No. 200802187 C). The authors thank Mr Gang Wu of Chuzhou University for his help with growing the crystals.

References

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