N′-(5-Chloro-2-hy­droxy­benzyl­idene)-2-meth­oxy­benzohydrazide

Hao, Y.-M.

doi:10.1107/S160053681002180X

organic compounds

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Volume 66| Part 7| July 2010| Page o1631

doi:10.1107/S160053681002180X

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N′-(5-Chloro-2-hydroxybenzylidene)-2-methoxybenzohydrazide

Yu-Mei Hao ^a ^*

^aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: jyxygzb@163.com

(Received 3 June 2010; accepted 7 June 2010; online 16 June 2010)

The title Schiff base compound, C₁₅H₁₃ClN₂O₃, was prepared by the reaction of equimolar quantities of 5-chloro-2-hydroxybenzaldehyde with 2-methoxybenzohydrazide in a methanol solution. The dihedral angle between the two benzene rings is 20.6 (3)°. An intramolecular O—H⋯N hydrogen bond may influence the molecular conformation. In the crystal structure, molecules form chains along the b direction via intermolecular N—H⋯O hydrogen bonds which are bifurcated involving an intramolecular N—H⋯O hydrogen bond.

Related literature

For the pharmaceutical and medicinal activities of Schiff bases, see: Sriram et al. (2006 ); Karthikeyan et al. (2006 ); Dao et al. (2000 ). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ); Kargar et al. (2009 ); Yeap et al. (2009 ). For the crystal structures of Schiff base compounds, see: Fun et al. (2009 ); Nadeem et al. (2009 ); Eltayeb et al. (2008 ). For the structures of related Schiff base compounds previously reported by the author, see: Hao (2009a ,b ,c ,d , 2010 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃
M_r = 304.72
Orthorhombic, P b c a
a = 15.392 (3) Å
b = 9.110 (2) Å
c = 20.128 (3) Å
V = 2822.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.920, T_max = 0.928
9958 measured reflections
3051 independent reflections
1463 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.150
S = 0.99
3051 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.93	2.649 (3)	145
N2—H2A⋯O2ⁱ	0.89 (1)	2.11 (2)	2.946 (3)	155 (3)
N2—H2A⋯O3	0.89 (1)	2.26 (3)	2.733 (3)	113 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002180X/lh5065sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002180X/lh5065Isup2.hkl

checkCIF report

Comment top

Schiff base compounds are a class of important materials used as pharmaceutical and medicinal fields (Sriram et al., 2006; Karthikeyan et al., 2006; Dao et al., 2000). Schiff bases have also been used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of a large number of Schiff base compounds bearing the hydrazone groups have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). As a continuous work (Hao, 2009a,b,c,d; Hao, 2010), in this paper, the title Schiff base compound, Fig. 1, is reported.

In the title compound, the dihedral angle between the two benzene rings is 20.6 (3)°. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the b direction (Fig. 2).

Related literature top

For the pharmaceutical and medicinal activities of Schiff bases, see: Sriram et al. (2006); Karthikeyan et al. (2006); Dao et al. (2000). For the coordination chemistry of Schiff bases, see: Ali et al. (2008); Kargar et al. (2009); Yeap et al. (2009). For the crystal structures of Schiff base compounds, see: Fun et al. (2009); Nadeem et al. (2009); Eltayeb et al. (2008). For the structures of related Schiff base compounds previously reported by the author, see: Hao (2009a,b,c,d, 2010). For standard bond-length data, see: Allen et al. (1987).

Experimental top

5-Chloro-2-hydroxybenzaldehyde (0.1 mmol, 15.6 mg) and 2-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear colorless solution. Colorless block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids. Intramolecular hydrogen bonds are drawn as dashed lines.
	Fig. 2. Molecular packing of the title compound with hydrogen bonds drawn as dashed lines.

N'-(5-Chloro-2-hydroxybenzylidene)-2-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O₃	F(000) = 1264
M_r = 304.72	D_x = 1.434 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 868 reflections
a = 15.392 (3) Å	θ = 2.4–24.5°
b = 9.110 (2) Å	µ = 0.28 mm⁻¹
c = 20.128 (3) Å	T = 298 K
V = 2822.4 (9) Å³	Block, colorless
Z = 8	0.30 × 0.30 × 0.27 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3051 independent reflections
Radiation source: fine-focus sealed tube	1463 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→9
T_min = 0.920, T_max = 0.928	k = −9→11
9958 measured reflections	l = −21→25

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.055P)²] where P = (F_o² + 2F_c²)/3
3051 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₃	V = 2822.4 (9) Å³
M_r = 304.72	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.392 (3) Å	µ = 0.28 mm⁻¹
b = 9.110 (2) Å	T = 298 K
c = 20.128 (3) Å	0.30 × 0.30 × 0.27 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3051 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1463 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.928	R_int = 0.067
9958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.17 e Å⁻³
3051 reflections	Δρ_min = −0.27 e Å⁻³
195 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
Cl1	1.23358 (6)	1.00596 (10)	0.43870 (5)	0.0931 (4)
N1	0.83185 (15)	1.0819 (2)	0.38838 (11)	0.0491 (6)
N2	0.76629 (15)	1.0034 (2)	0.35851 (13)	0.0532 (7)
O1	0.89608 (14)	1.2927 (2)	0.46463 (12)	0.0713 (7)
H1	0.8575	1.2452	0.4466	0.107*
O2	0.67478 (12)	1.1960 (2)	0.36350 (11)	0.0626 (6)
O3	0.71657 (13)	0.8451 (2)	0.24964 (11)	0.0675 (6)
C1	0.9728 (2)	1.2226 (3)	0.45691 (15)	0.0547 (8)
C2	1.0460 (2)	1.2825 (3)	0.48644 (16)	0.0670 (9)
H2	1.0410	1.3690	0.5107	0.080*
C3	1.1255 (2)	1.2168 (4)	0.48063 (16)	0.0710 (10)
H3	1.1741	1.2579	0.5007	0.085*
C4	1.13245 (19)	1.0896 (4)	0.44478 (16)	0.0600 (8)
C5	1.06147 (18)	1.0276 (3)	0.41535 (16)	0.0557 (8)
H5	1.0676	0.9407	0.3916	0.067*
C6	0.97993 (17)	1.0929 (3)	0.42047 (14)	0.0477 (7)
C7	0.90686 (18)	1.0219 (3)	0.38947 (14)	0.0487 (7)
H7	0.9144	0.9305	0.3698	0.058*
C8	0.68942 (18)	1.0680 (3)	0.34816 (13)	0.0467 (7)
C9	0.61993 (17)	0.9746 (3)	0.31858 (15)	0.0494 (7)
C10	0.53588 (19)	1.0005 (3)	0.34012 (16)	0.0573 (8)
H10	0.5259	1.0737	0.3714	0.069*
C11	0.4666 (2)	0.9204 (4)	0.31633 (18)	0.0675 (9)
H11	0.4108	0.9375	0.3322	0.081*
C12	0.4811 (2)	0.8159 (4)	0.26919 (19)	0.0721 (10)
H12	0.4346	0.7624	0.2524	0.086*
C13	0.5630 (2)	0.7886 (3)	0.24629 (17)	0.0654 (9)
H13	0.5716	0.7170	0.2140	0.078*
C14	0.63371 (19)	0.8664 (3)	0.27054 (15)	0.0519 (8)
C15	0.7318 (2)	0.7299 (4)	0.20290 (18)	0.0821 (11)
H15A	0.7109	0.6388	0.2208	0.123*
H15B	0.7930	0.7222	0.1943	0.123*
H15C	0.7018	0.7513	0.1622	0.123*
H2A	0.7748 (19)	0.9090 (14)	0.3487 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0545 (5)	0.1169 (8)	0.1077 (9)	−0.0004 (5)	−0.0070 (5)	0.0248 (6)
N1	0.0517 (14)	0.0446 (13)	0.0510 (16)	−0.0044 (11)	−0.0067 (12)	−0.0020 (12)
N2	0.0528 (14)	0.0403 (13)	0.0666 (18)	0.0001 (12)	−0.0152 (12)	−0.0101 (13)
O1	0.0792 (16)	0.0573 (13)	0.0775 (17)	0.0036 (11)	0.0003 (13)	−0.0150 (12)
O2	0.0662 (13)	0.0397 (11)	0.0821 (16)	0.0041 (9)	−0.0057 (11)	−0.0110 (11)
O3	0.0613 (13)	0.0702 (14)	0.0709 (15)	−0.0022 (10)	−0.0046 (12)	−0.0297 (12)
C1	0.070 (2)	0.0471 (18)	0.0470 (19)	−0.0062 (15)	0.0006 (16)	0.0012 (15)
C2	0.092 (3)	0.055 (2)	0.053 (2)	−0.0216 (18)	−0.0115 (18)	−0.0081 (17)
C3	0.068 (2)	0.084 (3)	0.062 (2)	−0.029 (2)	−0.0157 (18)	0.012 (2)
C4	0.0542 (18)	0.071 (2)	0.055 (2)	−0.0117 (16)	−0.0066 (16)	0.0146 (18)
C5	0.0583 (19)	0.0567 (18)	0.0521 (19)	−0.0077 (14)	−0.0017 (15)	0.0031 (16)
C6	0.0528 (17)	0.0460 (16)	0.0443 (18)	−0.0091 (13)	−0.0031 (14)	0.0041 (14)
C7	0.0556 (18)	0.0408 (16)	0.0497 (19)	−0.0043 (13)	0.0001 (14)	−0.0026 (14)
C8	0.0556 (18)	0.0415 (16)	0.0428 (18)	−0.0015 (13)	−0.0012 (14)	−0.0010 (14)
C9	0.0533 (17)	0.0428 (16)	0.0523 (19)	0.0023 (13)	−0.0116 (14)	0.0046 (15)
C10	0.060 (2)	0.0517 (18)	0.060 (2)	0.0040 (15)	−0.0089 (16)	0.0027 (15)
C11	0.0522 (19)	0.071 (2)	0.080 (3)	−0.0043 (16)	−0.0053 (18)	0.012 (2)
C12	0.063 (2)	0.070 (2)	0.082 (3)	−0.0143 (17)	−0.0148 (19)	0.006 (2)
C13	0.070 (2)	0.0587 (19)	0.068 (2)	−0.0113 (16)	−0.0126 (18)	−0.0106 (17)
C14	0.0526 (18)	0.0482 (17)	0.055 (2)	0.0008 (14)	−0.0085 (15)	−0.0001 (16)
C15	0.079 (2)	0.079 (2)	0.088 (3)	0.0057 (18)	−0.005 (2)	−0.033 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.737 (3)	C5—H5	0.9300
N1—C7	1.278 (3)	C6—C7	1.439 (4)
N1—N2	1.375 (3)	C7—H7	0.9300
N2—C8	1.338 (3)	C8—C9	1.491 (4)
N2—H2A	0.892 (10)	C9—C10	1.385 (4)
O1—C1	1.351 (3)	C9—C14	1.397 (4)
O1—H1	0.8200	C10—C11	1.377 (4)
O2—C8	1.227 (3)	C10—H10	0.9300
O3—C14	1.357 (3)	C11—C12	1.363 (5)
O3—C15	1.429 (3)	C11—H11	0.9300
C1—C2	1.386 (4)	C12—C13	1.365 (4)
C1—C6	1.395 (4)	C12—H12	0.9300
C2—C3	1.367 (5)	C13—C14	1.387 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.369 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.365 (4)	C15—H15C	0.9600
C5—C6	1.393 (4)

C7—N1—N2	116.6 (2)	O2—C8—N2	122.8 (2)
C8—N2—N1	119.2 (2)	O2—C8—C9	120.8 (2)
C8—N2—H2A	121 (2)	N2—C8—C9	116.5 (2)
N1—N2—H2A	119 (2)	C10—C9—C14	118.6 (3)
C1—O1—H1	109.5	C10—C9—C8	116.6 (3)
C14—O3—C15	117.6 (2)	C14—C9—C8	124.8 (3)
O1—C1—C2	118.4 (3)	C11—C10—C9	121.6 (3)
O1—C1—C6	122.0 (3)	C11—C10—H10	119.2
C2—C1—C6	119.6 (3)	C9—C10—H10	119.2
C3—C2—C1	121.3 (3)	C12—C11—C10	119.1 (3)
C3—C2—H2	119.4	C12—C11—H11	120.5
C1—C2—H2	119.4	C10—C11—H11	120.5
C2—C3—C4	119.0 (3)	C11—C12—C13	120.9 (3)
C2—C3—H3	120.5	C11—C12—H12	119.6
C4—C3—H3	120.5	C13—C12—H12	119.6
C5—C4—C3	121.1 (3)	C12—C13—C14	120.8 (3)
C5—C4—Cl1	120.4 (3)	C12—C13—H13	119.6
C3—C4—Cl1	118.6 (3)	C14—C13—H13	119.6
C4—C5—C6	120.9 (3)	O3—C14—C13	123.7 (3)
C4—C5—H5	119.6	O3—C14—C9	117.3 (2)
C6—C5—H5	119.6	C13—C14—C9	119.0 (3)
C5—C6—C1	118.1 (3)	O3—C15—H15A	109.5
C5—C6—C7	118.7 (3)	O3—C15—H15B	109.5
C1—C6—C7	123.1 (3)	H15A—C15—H15B	109.5
N1—C7—C6	121.4 (3)	O3—C15—H15C	109.5
N1—C7—H7	119.3	H15A—C15—H15C	109.5
C6—C7—H7	119.3	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.93	2.649 (3)	145
N2—H2A···O2ⁱ	0.89 (1)	2.11 (2)	2.946 (3)	155 (3)
N2—H2A···O3	0.89 (1)	2.26 (3)	2.733 (3)	113 (2)

Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₃
M_r	304.72
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	15.392 (3), 9.110 (2), 20.128 (3)
V (Å³)	2822.4 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.30 × 0.30 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.920, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections	9958, 3051, 1463
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.150, 0.99
No. of reflections	3051
No. of parameters	195
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)	0.17, −0.27

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···N1	0.82	1.93	2.649 (3)	145.3
N2—H2A···O2ⁱ	0.892 (10)	2.111 (16)	2.946 (3)	155 (3)
N2—H2A···O3	0.892 (10)	2.26 (3)	2.733 (3)	113 (2)

Symmetry code: (i) −x+3/2, y−1/2, z.

References

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1631

doi:10.1107/S160053681002180X

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