(E)-N'-(5-Chloro-2-hy-droxy-benzyl-idene)-2,4-dihy-droxybenzohydrazide methanol monosolvate.

In the title compound, C(14)H(11)ClN(2)O(4)·CH(3)OH, the mol-ecule adopts an E conformation about the C=N bond. The compound is in the enamine-keto form. The two terminal benzene rings make a dihedral angle of 10.53 (9)°. Intra-mol-ecular O-H⋯O and O-H⋯N hydrogen bonding stabilizes the mol-ecular structure. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules, forming chains running along the b axis.

Related literature

For general background to the bioactivity of Schiff bases in the pharmaceutical and agrochemical fields, see: Bernardino et al. (2006 ▶); Zhang et al. (2008 ▶). For related compounds, see: Huang et al. (2008 ▶); Zhang et al. (2007 ▶). For a related structure, see: Deng et al. (2009 ▶).

Experimental

Crystal data

C14H11ClN2O4·CH4O

M = 338.74

Monoclinic,

a = 7.5438 (11) Å

b = 13.1623 (19) Å

c = 15.903 (2) Å

β = 103.251 (3)°

V = 1537.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.20 × 0.12 × 0.10 mm

Data collection

Brucker SMART 1000 CCD diffractometer

14496 measured reflections

3808 independent reflections

2407 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.01

3808 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009178/xu5474sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009178/xu5474Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009178/xu5474Isup3.cml

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

C14H11ClN2O4·CH4O	F(000) = 704
Mr = 338.74	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2195 reflections
a = 7.5438 (11) Å	θ = 3.1–26.4°
b = 13.1623 (19) Å	µ = 0.28 mm−1
c = 15.903 (2) Å	T = 296 K
β = 103.251 (3)°	Rod, yellow
V = 1537.0 (4) Å3	0.20 × 0.12 × 0.10 mm
Z = 4

Brucker SMART 1000 CCD diffractometer	2407 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 28.3°, θmin = 2.0°
ω scans	h = −10→10
14496 measured reflections	k = −17→17
3808 independent reflections	l = −20→21

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.2991P] where P = (Fo2 + 2Fc2)/3
3808 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.29 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
C1	0.2107 (2)	0.06032 (14)	−0.02905 (10)	0.0381 (4)
H1	0.2103	0.1310	−0.0285	0.046*
C2	0.0958 (2)	0.00413 (13)	−0.09970 (10)	0.0350 (4)
C3	0.0877 (2)	−0.10217 (14)	−0.09981 (11)	0.0393 (4)
C4	−0.0226 (3)	−0.15334 (16)	−0.16831 (13)	0.0504 (5)
H4	−0.0283	−0.2239	−0.1679	0.060*
C5	−0.1240 (3)	−0.09963 (17)	−0.23709 (13)	0.0529 (5)
H5	−0.1971	−0.1341	−0.2833	0.063*
C6	−0.1173 (3)	0.00494 (17)	−0.23758 (12)	0.0464 (5)
C7	−0.0092 (2)	0.05704 (15)	−0.16963 (11)	0.0424 (4)
H7	−0.0064	0.1277	−0.1704	0.051*
C8	0.5164 (2)	−0.00088 (13)	0.16440 (11)	0.0361 (4)
C9	0.6206 (2)	0.04621 (12)	0.24364 (10)	0.0335 (4)
C10	0.7254 (2)	−0.01654 (12)	0.30783 (11)	0.0361 (4)
C11	0.8242 (3)	0.02260 (14)	0.38451 (11)	0.0431 (4)
H11	0.8948	−0.0201	0.4255	0.052*
C12	0.8181 (3)	0.12552 (14)	0.40030 (11)	0.0412 (4)
C13	0.7145 (3)	0.19012 (13)	0.33873 (11)	0.0419 (4)
H13	0.7100	0.2594	0.3496	0.050*
C14	0.6194 (2)	0.15036 (13)	0.26201 (11)	0.0386 (4)
H14	0.5518	0.1939	0.2208	0.046*
C15	0.4082 (4)	0.3243 (2)	−0.00103 (16)	0.0741 (7)
H15A	0.3001	0.3588	−0.0311	0.111*
H15B	0.4478	0.2781	−0.0397	0.111*
H15C	0.5025	0.3732	0.0199	0.111*
Cl1	−0.24386 (8)	0.07252 (5)	−0.32463 (4)	0.0732 (2)
N1	0.31182 (19)	0.01011 (11)	0.03204 (8)	0.0374 (3)
N2	0.4195 (2)	0.05913 (11)	0.10084 (9)	0.0390 (3)
H2	0.4254	0.1243	0.1037	0.047*
O1	0.18685 (19)	−0.15812 (10)	−0.03310 (8)	0.0525 (4)
H1A	0.2464	−0.1199	0.0034	0.079*
O2	0.51353 (19)	−0.09463 (9)	0.15379 (8)	0.0459 (3)
O3	0.73109 (19)	−0.11901 (9)	0.29692 (8)	0.0478 (3)
H3	0.6682	−0.1344	0.2494	0.072*
O4	0.9180 (2)	0.15923 (11)	0.47749 (9)	0.0637 (4)
H4A	0.9057	0.2209	0.4808	0.096*
O5	0.3709 (2)	0.27020 (11)	0.06876 (10)	0.0668 (5)
H5A	0.3405	0.3099	0.1026	0.100*

	U11	U22	U33	U12	U13	U23
C1	0.0412 (10)	0.0383 (9)	0.0348 (9)	0.0007 (8)	0.0088 (8)	−0.0010 (7)
C2	0.0332 (9)	0.0423 (10)	0.0307 (8)	−0.0003 (7)	0.0095 (7)	0.0008 (7)
C3	0.0393 (10)	0.0418 (10)	0.0367 (9)	−0.0017 (8)	0.0084 (8)	0.0029 (8)
C4	0.0501 (12)	0.0474 (11)	0.0518 (11)	−0.0101 (9)	0.0080 (10)	−0.0052 (9)
C5	0.0449 (12)	0.0689 (15)	0.0416 (10)	−0.0118 (10)	0.0030 (9)	−0.0095 (10)
C6	0.0369 (10)	0.0652 (13)	0.0350 (9)	0.0005 (9)	0.0039 (8)	0.0061 (9)
C7	0.0406 (10)	0.0473 (11)	0.0392 (9)	0.0026 (8)	0.0090 (8)	0.0055 (8)
C8	0.0392 (10)	0.0365 (10)	0.0334 (8)	−0.0019 (8)	0.0104 (7)	0.0019 (7)
C9	0.0364 (9)	0.0333 (9)	0.0310 (8)	−0.0008 (7)	0.0082 (7)	0.0012 (7)
C10	0.0417 (10)	0.0291 (9)	0.0375 (9)	0.0018 (7)	0.0095 (8)	0.0025 (7)
C11	0.0486 (11)	0.0393 (10)	0.0370 (9)	0.0080 (8)	0.0004 (8)	0.0031 (8)
C12	0.0420 (10)	0.0414 (10)	0.0360 (9)	0.0044 (8)	0.0004 (8)	−0.0053 (8)
C13	0.0493 (11)	0.0312 (9)	0.0425 (10)	0.0036 (8)	0.0049 (8)	−0.0052 (7)
C14	0.0443 (10)	0.0330 (9)	0.0363 (9)	0.0059 (8)	0.0049 (8)	0.0029 (7)
C15	0.0878 (19)	0.0742 (17)	0.0599 (15)	−0.0097 (14)	0.0158 (14)	0.0039 (12)
Cl1	0.0588 (4)	0.1009 (5)	0.0494 (3)	0.0050 (3)	−0.0089 (3)	0.0195 (3)
N1	0.0392 (8)	0.0417 (8)	0.0310 (7)	−0.0023 (7)	0.0073 (6)	−0.0023 (6)
N2	0.0483 (9)	0.0352 (8)	0.0309 (7)	−0.0009 (7)	0.0035 (6)	−0.0020 (6)
O1	0.0621 (9)	0.0389 (7)	0.0491 (8)	−0.0038 (6)	−0.0025 (7)	0.0075 (6)
O2	0.0591 (9)	0.0321 (7)	0.0428 (7)	−0.0057 (6)	0.0037 (6)	−0.0020 (5)
O3	0.0663 (9)	0.0286 (6)	0.0439 (7)	0.0034 (6)	0.0026 (6)	0.0018 (5)
O4	0.0773 (11)	0.0503 (8)	0.0474 (8)	0.0148 (7)	−0.0187 (7)	−0.0138 (6)
O5	0.1037 (13)	0.0446 (8)	0.0534 (8)	0.0176 (8)	0.0206 (9)	0.0007 (7)

C1—N1	1.274 (2)	C10—O3	1.362 (2)
C1—C2	1.454 (2)	C10—C11	1.375 (2)
C1—H1	0.9300	C11—C12	1.380 (3)
C2—C7	1.395 (2)	C11—H11	0.9300
C2—C3	1.400 (3)	C12—O4	1.359 (2)
C3—O1	1.365 (2)	C12—C13	1.393 (2)
C3—C4	1.385 (3)	C13—C14	1.370 (2)
C4—C5	1.377 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.377 (3)	C15—O5	1.401 (3)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.378 (3)	C15—H15B	0.9600
C6—Cl1	1.7360 (19)	C15—H15C	0.9600
C7—H7	0.9300	N1—N2	1.3658 (18)
C8—O2	1.245 (2)	N2—H2	0.8600
C8—N2	1.357 (2)	O1—H1A	0.8200
C8—C9	1.461 (2)	O3—H3	0.8200
C9—C14	1.402 (2)	O4—H4A	0.8200
C9—C10	1.407 (2)	O5—H5A	0.8200
N1—C1—C2	118.17 (16)	O3—C10—C9	121.19 (15)
N1—C1—H1	120.9	C11—C10—C9	121.57 (16)
C2—C1—H1	120.9	C10—C11—C12	119.67 (16)
C7—C2—C3	118.76 (16)	C10—C11—H11	120.2
C7—C2—C1	119.42 (16)	C12—C11—H11	120.2
C3—C2—C1	121.83 (16)	O4—C12—C11	116.74 (16)
O1—C3—C4	118.19 (16)	O4—C12—C13	122.75 (16)
O1—C3—C2	121.47 (16)	C11—C12—C13	120.51 (16)
C4—C3—C2	120.34 (17)	C14—C13—C12	119.19 (16)
C5—C4—C3	119.95 (18)	C14—C13—H13	120.4
C5—C4—H4	120.0	C12—C13—H13	120.4
C3—C4—H4	120.0	C13—C14—C9	122.15 (16)
C6—C5—C4	120.20 (18)	C13—C14—H14	118.9
C6—C5—H5	119.9	C9—C14—H14	118.9
C4—C5—H5	119.9	O5—C15—H15A	109.5
C5—C6—C7	120.58 (18)	O5—C15—H15B	109.5
C5—C6—Cl1	120.16 (15)	H15A—C15—H15B	109.5
C7—C6—Cl1	119.26 (16)	O5—C15—H15C	109.5
C6—C7—C2	120.17 (18)	H15A—C15—H15C	109.5
C6—C7—H7	119.9	H15B—C15—H15C	109.5
C2—C7—H7	119.9	C1—N1—N2	120.53 (15)
O2—C8—N2	119.10 (15)	C8—N2—N1	116.21 (14)
O2—C8—C9	121.77 (15)	C8—N2—H2	121.9
N2—C8—C9	119.14 (15)	N1—N2—H2	121.9
C14—C9—C10	116.89 (15)	C3—O1—H1A	109.5
C14—C9—C8	124.50 (15)	C10—O3—H3	109.5
C10—C9—C8	118.58 (15)	C12—O4—H4A	109.5
O3—C10—C11	117.23 (15)	C15—O5—H5A	109.5
N1—C1—C2—C7	−176.71 (16)	N2—C8—C9—C10	−177.89 (15)
N1—C1—C2—C3	3.2 (3)	C14—C9—C10—O3	178.17 (16)
C7—C2—C3—O1	−179.78 (16)	C8—C9—C10—O3	0.2 (2)
C1—C2—C3—O1	0.4 (3)	C14—C9—C10—C11	−0.9 (3)
C7—C2—C3—C4	0.1 (3)	C8—C9—C10—C11	−178.90 (16)
C1—C2—C3—C4	−179.76 (16)	O3—C10—C11—C12	−177.66 (17)
O1—C3—C4—C5	−179.61 (18)	C9—C10—C11—C12	1.5 (3)
C2—C3—C4—C5	0.5 (3)	C10—C11—C12—O4	179.64 (17)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—C13	−0.8 (3)
C4—C5—C6—C7	0.1 (3)	O4—C12—C13—C14	179.18 (18)
C4—C5—C6—Cl1	179.57 (16)	C11—C12—C13—C14	−0.3 (3)
C5—C6—C7—C2	0.5 (3)	C12—C13—C14—C9	0.9 (3)
Cl1—C6—C7—C2	−178.96 (13)	C10—C9—C14—C13	−0.3 (3)
C3—C2—C7—C6	−0.6 (3)	C8—C9—C14—C13	177.58 (17)
C1—C2—C7—C6	179.28 (16)	C2—C1—N1—N2	−178.63 (14)
O2—C8—C9—C14	−175.36 (17)	O2—C8—N2—N1	5.6 (2)
N2—C8—C9—C14	4.3 (3)	C9—C8—N2—N1	−174.10 (14)
O2—C8—C9—C10	2.5 (3)	C1—N1—N2—C8	177.27 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.86	2.01	2.833 (2)	159
O1—H1A···N1	0.82	1.81	2.5333 (19)	146
O3—H3···O2	0.82	1.77	2.5030 (18)	148
O4—H4A···O1i	0.82	2.00	2.7401 (19)	151
O5—H5A···O3i	0.82	2.03	2.8346 (19)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.86	2.01	2.833 (2)	159
O1—H1A⋯N1	0.82	1.81	2.5333 (19)	146
O3—H3⋯O2	0.82	1.77	2.5030 (18)	148
O4—H4A⋯O1i	0.82	2.00	2.7401 (19)	151
O5—H5A⋯O3i	0.82	2.03	2.8346 (19)	168

Symmetry code: (i) .