4-Chloro-N'-(2-hy-droxy-4-meth-oxy-benzyl-idene)benzohydrazide methanol monosolvate.

The title compound, C(15)H(13)ClN(2)O(3)·CH(3)OH, was synthesized by the condensation reaction of 2-hy-droxy-4-meth-oxy-benzaldehyde with 4-chloro-benzohydrazide in methanol. The Schiff base mol-ecule displays a trans configuration with respect to the C=N and C-N bonds. The dihedral angle between the two benzene rings is 5.3 (2)°. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen-bond inter-actions into chains running parallel to the a axis. An intra-molecular O-H⋯N hydrogen bond is observed.

Related literature

For background to Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For their biological activity, see: Chen et al. (1997 ▶); Ren et al. (2002 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Zhi (2008 ▶, 2009 ▶); Zhi & Yang (2007 ▶).

Experimental

Crystal data

C15H13ClN2O3·CH4O

M = 336.77

Triclinic,

a = 6.570 (2) Å

b = 10.343 (3) Å

c = 12.707 (3) Å

α = 100.371 (2)°

β = 91.864 (2)°

γ = 101.663 (2)°

V = 829.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.971

5945 measured reflections

3022 independent reflections

1724 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.144

S = 1.01

3022 reflections

216 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039778/rz2644sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039778/rz2644Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039778/rz2644Isup3.cml

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

C15H13ClN2O3·CH4O	Z = 2
Mr = 336.77	F(000) = 352
Triclinic, P1	Dx = 1.348 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.570 (2) Å	Cell parameters from 1241 reflections
b = 10.343 (3) Å	θ = 2.3–24.5°
c = 12.707 (3) Å	µ = 0.25 mm−1
α = 100.371 (2)°	T = 298 K
β = 91.864 (2)°	Block, colorless
γ = 101.663 (2)°	0.17 × 0.13 × 0.12 mm
V = 829.7 (4) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3022 independent reflections
Radiation source: fine-focus sealed tube	1724 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.959, Tmax = 0.971	k = −12→12
5945 measured reflections	l = −15→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0633P)2] where P = (Fo2 + 2Fc2)/3
3022 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.45941 (17)	1.34163 (8)	0.04723 (7)	0.1057 (4)
N1	0.6218 (3)	0.69152 (19)	0.29276 (16)	0.0550 (6)
N2	0.5628 (3)	0.7970 (2)	0.25424 (18)	0.0544 (6)
O1	0.8829 (3)	0.55918 (18)	0.37185 (18)	0.0764 (6)
H1	0.8513	0.6186	0.3438	0.115*
O2	0.8950 (3)	0.91058 (17)	0.25849 (18)	0.0853 (7)
O3	0.5767 (3)	0.14043 (16)	0.46539 (16)	0.0715 (6)
O4	0.1182 (3)	0.72464 (19)	0.20964 (17)	0.0731 (6)
H4	0.0462	0.7810	0.2227	0.110*
C1	0.5106 (4)	0.4800 (2)	0.34710 (19)	0.0485 (6)
C2	0.7089 (4)	0.4662 (2)	0.3793 (2)	0.0506 (6)
C3	0.7361 (4)	0.3544 (2)	0.42035 (19)	0.0528 (7)
H3	0.8687	0.3472	0.4431	0.063*
C4	0.5660 (4)	0.2544 (2)	0.4272 (2)	0.0533 (7)
C5	0.3685 (4)	0.2649 (3)	0.3942 (2)	0.0652 (8)
H5	0.2542	0.1964	0.3976	0.078*
C6	0.3423 (4)	0.3768 (3)	0.3565 (2)	0.0634 (8)
H6	0.2084	0.3845	0.3366	0.076*
C7	0.4739 (4)	0.5964 (2)	0.30752 (19)	0.0538 (7)
H7	0.3371	0.6024	0.2921	0.065*
C8	0.7072 (4)	0.9011 (2)	0.2375 (2)	0.0565 (7)
C9	0.6350 (4)	1.0083 (2)	0.1913 (2)	0.0526 (7)
C10	0.7810 (5)	1.1221 (3)	0.1836 (2)	0.0669 (8)
H10	0.9185	1.1298	0.2084	0.080*
C11	0.7275 (5)	1.2247 (3)	0.1399 (2)	0.0759 (9)
H11	0.8277	1.3008	0.1355	0.091*
C12	0.5255 (5)	1.2130 (3)	0.1031 (2)	0.0680 (8)
C13	0.3780 (5)	1.1019 (3)	0.1095 (2)	0.0761 (9)
H13	0.2408	1.0951	0.0846	0.091*
C14	0.4322 (4)	0.9993 (3)	0.1531 (2)	0.0699 (8)
H14	0.3311	0.9233	0.1567	0.084*
C15	0.7748 (4)	0.1250 (3)	0.5037 (3)	0.0789 (9)
H15A	0.8623	0.1154	0.4449	0.118*
H15B	0.7574	0.0465	0.5356	0.118*
H15C	0.8382	0.2028	0.5563	0.118*
C16	0.0297 (6)	0.6290 (4)	0.1191 (3)	0.1093 (12)
H16A	0.0040	0.6737	0.0616	0.164*
H16B	−0.0994	0.5770	0.1358	0.164*
H16C	0.1236	0.5706	0.0978	0.164*
H2	0.4259 (18)	0.792 (3)	0.240 (2)	0.085 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.1478 (9)	0.0832 (6)	0.1065 (7)	0.0441 (6)	0.0043 (6)	0.0498 (5)
N1	0.0538 (13)	0.0482 (12)	0.0692 (14)	0.0191 (11)	−0.0014 (11)	0.0188 (10)
N2	0.0448 (13)	0.0522 (12)	0.0731 (15)	0.0169 (11)	−0.0001 (11)	0.0227 (11)
O1	0.0478 (11)	0.0667 (12)	0.1210 (17)	−0.0033 (9)	−0.0109 (11)	0.0546 (11)
O2	0.0489 (12)	0.0643 (12)	0.148 (2)	0.0151 (10)	−0.0058 (12)	0.0321 (12)
O3	0.0582 (12)	0.0592 (11)	0.1055 (15)	0.0078 (9)	0.0026 (11)	0.0437 (10)
O4	0.0475 (11)	0.0716 (12)	0.1049 (16)	0.0173 (9)	−0.0006 (11)	0.0252 (11)
C1	0.0453 (15)	0.0491 (13)	0.0541 (16)	0.0143 (12)	0.0040 (12)	0.0129 (12)
C2	0.0464 (16)	0.0455 (13)	0.0609 (16)	0.0059 (12)	0.0044 (12)	0.0169 (12)
C3	0.0424 (15)	0.0513 (14)	0.0698 (18)	0.0128 (12)	0.0006 (13)	0.0226 (12)
C4	0.0535 (17)	0.0463 (14)	0.0641 (17)	0.0096 (13)	0.0067 (13)	0.0217 (12)
C5	0.0448 (16)	0.0615 (16)	0.093 (2)	0.0056 (13)	0.0075 (15)	0.0307 (15)
C6	0.0418 (15)	0.0650 (17)	0.089 (2)	0.0121 (13)	0.0052 (14)	0.0290 (15)
C7	0.0476 (16)	0.0541 (15)	0.0650 (18)	0.0177 (13)	0.0027 (13)	0.0175 (13)
C8	0.0472 (17)	0.0488 (15)	0.0755 (19)	0.0152 (13)	0.0041 (14)	0.0113 (13)
C9	0.0525 (16)	0.0473 (14)	0.0616 (17)	0.0157 (12)	0.0072 (13)	0.0133 (12)
C10	0.0622 (18)	0.0604 (17)	0.077 (2)	0.0061 (15)	−0.0002 (15)	0.0198 (15)
C11	0.091 (2)	0.0552 (17)	0.081 (2)	0.0040 (16)	0.0001 (18)	0.0276 (15)
C12	0.096 (3)	0.0573 (17)	0.0602 (18)	0.0267 (17)	0.0105 (17)	0.0236 (14)
C13	0.0632 (19)	0.080 (2)	0.102 (2)	0.0287 (16)	0.0104 (17)	0.0439 (18)
C14	0.0574 (19)	0.0624 (17)	0.100 (2)	0.0135 (14)	0.0084 (16)	0.0408 (16)
C15	0.071 (2)	0.0640 (17)	0.110 (2)	0.0128 (16)	−0.0042 (18)	0.0434 (17)
C16	0.090 (3)	0.138 (3)	0.095 (3)	0.024 (2)	−0.001 (2)	0.012 (2)

Cl1—C12	1.736 (3)	C5—H5	0.9300
N1—C7	1.280 (3)	C6—H6	0.9300
N1—N2	1.390 (3)	C7—H7	0.9300
N2—C8	1.337 (3)	C8—C9	1.492 (3)
N2—H2	0.901 (10)	C9—C10	1.380 (3)
O1—C2	1.355 (3)	C9—C14	1.383 (4)
O1—H1	0.8200	C10—C11	1.382 (4)
O2—C8	1.235 (3)	C10—H10	0.9300
O3—C4	1.366 (3)	C11—C12	1.367 (4)
O3—C15	1.423 (3)	C11—H11	0.9300
O4—C16	1.398 (3)	C12—C13	1.362 (4)
O4—H4	0.8200	C13—C14	1.383 (4)
C1—C2	1.395 (3)	C13—H13	0.9300
C1—C6	1.397 (3)	C14—H14	0.9300
C1—C7	1.445 (3)	C15—H15A	0.9600
C2—C3	1.392 (3)	C15—H15B	0.9600
C3—C4	1.378 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.382 (4)	C16—H16B	0.9600
C5—C6	1.369 (3)	C16—H16C	0.9600
C7—N1—N2	116.3 (2)	C10—C9—C14	117.9 (2)
C8—N2—N1	120.2 (2)	C10—C9—C8	118.0 (2)
C8—N2—H2	121.7 (18)	C14—C9—C8	124.1 (2)
N1—N2—H2	118.1 (18)	C9—C10—C11	121.5 (3)
C2—O1—H1	109.5	C9—C10—H10	119.2
C4—O3—C15	118.4 (2)	C11—C10—H10	119.2
C16—O4—H4	109.5	C12—C11—C10	119.2 (3)
C2—C1—C6	117.5 (2)	C12—C11—H11	120.4
C2—C1—C7	122.8 (2)	C10—C11—H11	120.4
C6—C1—C7	119.7 (2)	C13—C12—C11	120.6 (3)
O1—C2—C3	116.9 (2)	C13—C12—Cl1	120.3 (3)
O1—C2—C1	122.3 (2)	C11—C12—Cl1	119.1 (2)
C3—C2—C1	120.8 (2)	C12—C13—C14	120.0 (3)
C4—C3—C2	119.7 (2)	C12—C13—H13	120.0
C4—C3—H3	120.1	C14—C13—H13	120.0
C2—C3—H3	120.1	C9—C14—C13	120.8 (3)
O3—C4—C3	124.1 (2)	C9—C14—H14	119.6
O3—C4—C5	115.4 (2)	C13—C14—H14	119.6
C3—C4—C5	120.4 (2)	O3—C15—H15A	109.5
C6—C5—C4	119.5 (2)	O3—C15—H15B	109.5
C6—C5—H5	120.3	H15A—C15—H15B	109.5
C4—C5—H5	120.3	O3—C15—H15C	109.5
C5—C6—C1	122.0 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.0	H15B—C15—H15C	109.5
C1—C6—H6	119.0	O4—C16—H16A	109.5
N1—C7—C1	122.7 (2)	O4—C16—H16B	109.5
N1—C7—H7	118.6	H16A—C16—H16B	109.5
C1—C7—H7	118.6	O4—C16—H16C	109.5
O2—C8—N2	122.4 (2)	H16A—C16—H16C	109.5
O2—C8—C9	119.8 (2)	H16B—C16—H16C	109.5
N2—C8—C9	117.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2i	0.82	1.83	2.646 (3)	177.
N2—H2···O4	0.90 (1)	2.00 (1)	2.876 (3)	163 (2)
O1—H1···N1	0.82	1.96	2.676 (3)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.82	1.83	2.646 (3)	177
N2—H2⋯O4	0.90 (1)	2.00 (1)	2.876 (3)	163 (2)
O1—H1⋯N1	0.82	1.96	2.676 (3)	146

Symmetry code: (i) .