N'-(5-Chloro-2-hy-droxy-benzyl-idene)-2-meth-oxy-benzohydrazide.

The title Schiff base compound, C(15)H(13)ClN(2)O(3), was prepared by the reaction of equimolar quanti-ties of 5-chloro-2-hy-droxy-benzaldehyde with 2-meth-oxy-benzohydrazide in a methanol solution. The dihedral angle between the two benzene rings is 20.6 (3)°. An intra-molecular O-H⋯N hydrogen bond may influence the mol-ecular conformation. In the crystal structure, mol-ecules form chains along the b direction via inter-molecular N-H⋯O hydrogen bonds which are bifurcated involving an intra-molecular 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 ▶,2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13ClN2O3

M = 304.72

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.150

S = 0.99

3051 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.27 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H13ClN2O3	F(000) = 1264
Mr = 304.72	Dx = 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

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

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(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
3051 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) .