3,5-Dihydr-oxy-N'-(2-hydroxy-benzyl-idene)benzohydrazide monohydrate.

The title potential anti-bacterial compound, C(14)H(12)N(2)O(4)·H(2)O, is a Schiff base which has an intra-molecular O-H⋯N hydrogen bond and crystallizes with one uncoordinated water mol-ecule, which links three symmetry-related mol-ecules through two O-H⋯O and one N-H⋯O hydrogen bond. In the crystal structure, further inter-molecular O-H⋯O hydrogen bonds link symmetry-related mol-ecules, forming layers parallel to the bc plane.

Related literature

For related structures, see: Ali et al. (2005 ▶); Diao (2007 ▶); Diao, Li et al. (2007 ▶); Diao, Shu et al. (2007 ▶); Diao, Wang et al. (2007 ▶); Jing et al. (2006 ▶); Qiu et al. (2006 ▶); Wang et al. (2007 ▶); Yang (2007 ▶).

Experimental

Crystal data

C14H12N2O4·H2O

M = 290.27

Monoclinic,

a = 7.773 (2) Å

b = 13.411 (3) Å

c = 13.084 (3) Å

β = 100.52 (3)°

V = 1341.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (2) K

0.33 × 0.32 × 0.32 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.965

17195 measured reflections

2918 independent reflections

2062 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.03

2918 reflections

202 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067177/su2036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067177/su2036Isup2.hkl

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

C14H12N2O4·H2O	F000 = 608
Mr = 290.27	Dx = 1.438 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybc	Cell parameters from 2799 reflections
a = 7.773 (2) Å	θ = 2.2–24.5º
b = 13.411 (3) Å	µ = 0.11 mm−1
c = 13.084 (3) Å	T = 293 (2) K
β = 100.52 (3)º	Block, yellow
V = 1341.0 (5) Å3	0.33 × 0.32 × 0.32 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	2918 independent reflections
Radiation source: fine-focus sealed tube	2062 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
T = 293(2) K	θmax = 27.0º
ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.964, Tmax = 0.965	k = −16→17
17195 measured reflections	l = −16→16

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4645P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2918 reflections	Δρmax = 0.56 e Å−3
202 parameters	Δρmin = −0.21 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
N1	0.82125 (17)	0.06536 (10)	0.52477 (11)	0.0340 (3)
N2	0.89934 (18)	0.14758 (10)	0.48954 (11)	0.0329 (3)
O1	0.7166 (2)	−0.03870 (11)	0.66833 (10)	0.0593 (4)
H1	0.7590	0.0093	0.6430	0.089*
O2	0.96488 (18)	0.20688 (9)	0.65336 (9)	0.0452 (3)
O3	1.1037 (3)	0.43849 (11)	0.28345 (10)	0.0700 (5)
H3	1.0537	0.3942	0.2462	0.105*
O4	1.3445 (2)	0.50690 (11)	0.63155 (11)	0.0577 (4)
H4	1.3389	0.4896	0.6910	0.087*
O5	0.8486 (2)	0.36158 (10)	0.76830 (11)	0.0606 (4)
C1	0.6575 (2)	−0.08377 (12)	0.48772 (14)	0.0369 (4)
C2	0.5775 (2)	−0.15150 (14)	0.41236 (17)	0.0508 (5)
H2	0.5807	−0.1397	0.3427	0.061*
C3	0.4943 (3)	−0.23513 (15)	0.4397 (2)	0.0613 (6)
H3A	0.4418	−0.2794	0.3887	0.074*
C4	0.4886 (3)	−0.25336 (15)	0.5423 (2)	0.0635 (7)
H4A	0.4340	−0.3106	0.5607	0.076*
C5	0.5630 (3)	−0.18744 (16)	0.61818 (19)	0.0579 (6)
H5	0.5571	−0.1997	0.6874	0.070*
C6	0.6470 (2)	−0.10272 (13)	0.59157 (15)	0.0424 (4)
C7	0.7438 (2)	0.00390 (12)	0.45641 (14)	0.0363 (4)
H7	0.7431	0.0157	0.3863	0.044*
C8	0.9672 (2)	0.21721 (12)	0.55913 (12)	0.0319 (4)
C9	1.0484 (2)	0.30675 (11)	0.51996 (12)	0.0315 (4)
C10	1.0290 (2)	0.33013 (13)	0.41515 (13)	0.0399 (4)
H10	0.9576	0.2916	0.3656	0.048*
C11	1.1174 (3)	0.41156 (13)	0.38544 (14)	0.0431 (4)
C12	1.2233 (3)	0.46968 (13)	0.45862 (14)	0.0424 (4)
H12	1.2839	0.5235	0.4378	0.051*
C13	1.2382 (2)	0.44731 (13)	0.56219 (13)	0.0385 (4)
C14	1.1516 (2)	0.36597 (12)	0.59365 (13)	0.0354 (4)
H14	1.1625	0.3511	0.6640	0.042*
H2A	0.894 (3)	0.1496 (18)	0.4203 (8)	0.080*
H5A	0.876 (3)	0.4197 (9)	0.7493 (18)	0.080*
H5B	0.885 (3)	0.3199 (13)	0.7274 (16)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0361 (7)	0.0282 (7)	0.0391 (8)	−0.0005 (6)	0.0105 (6)	0.0015 (6)
N2	0.0397 (8)	0.0282 (7)	0.0319 (7)	−0.0035 (6)	0.0099 (6)	−0.0004 (6)
O1	0.0736 (10)	0.0606 (9)	0.0411 (8)	−0.0153 (8)	0.0033 (7)	0.0109 (7)
O2	0.0685 (9)	0.0388 (7)	0.0287 (7)	−0.0058 (6)	0.0104 (6)	0.0020 (5)
O3	0.1327 (15)	0.0443 (8)	0.0319 (7)	−0.0293 (9)	0.0125 (8)	0.0041 (6)
O4	0.0694 (9)	0.0560 (9)	0.0443 (8)	−0.0272 (7)	0.0015 (7)	−0.0049 (7)
O5	0.1062 (13)	0.0392 (8)	0.0432 (8)	0.0067 (8)	0.0312 (8)	0.0064 (6)
C1	0.0316 (8)	0.0285 (8)	0.0517 (11)	0.0031 (7)	0.0101 (8)	−0.0023 (7)
C2	0.0445 (10)	0.0444 (11)	0.0654 (13)	−0.0034 (9)	0.0149 (9)	−0.0156 (10)
C3	0.0442 (11)	0.0385 (11)	0.102 (2)	−0.0061 (9)	0.0148 (12)	−0.0205 (12)
C4	0.0443 (11)	0.0326 (10)	0.115 (2)	−0.0027 (9)	0.0177 (12)	0.0101 (12)
C5	0.0530 (12)	0.0481 (12)	0.0726 (15)	−0.0013 (10)	0.0110 (11)	0.0226 (11)
C6	0.0397 (10)	0.0336 (9)	0.0524 (12)	0.0017 (7)	0.0043 (8)	0.0086 (8)
C7	0.0385 (9)	0.0353 (9)	0.0371 (10)	0.0010 (7)	0.0117 (7)	−0.0017 (7)
C8	0.0366 (9)	0.0299 (8)	0.0292 (9)	0.0037 (7)	0.0061 (7)	0.0010 (7)
C9	0.0375 (9)	0.0271 (8)	0.0303 (9)	0.0026 (7)	0.0071 (7)	−0.0004 (6)
C10	0.0586 (11)	0.0287 (8)	0.0304 (9)	−0.0043 (8)	0.0030 (8)	−0.0008 (7)
C11	0.0684 (12)	0.0312 (9)	0.0305 (9)	−0.0030 (8)	0.0108 (8)	0.0017 (7)
C12	0.0562 (11)	0.0305 (9)	0.0418 (11)	−0.0067 (8)	0.0121 (8)	0.0011 (8)
C13	0.0425 (10)	0.0340 (9)	0.0382 (10)	−0.0030 (7)	0.0056 (8)	−0.0044 (7)
C14	0.0423 (9)	0.0356 (9)	0.0281 (9)	0.0000 (7)	0.0057 (7)	−0.0004 (7)

N1—C7	1.283 (2)	C3—C4	1.373 (3)
N1—N2	1.3780 (19)	C3—H3A	0.9300
N2—C8	1.343 (2)	C4—C5	1.375 (3)
N2—H2A	0.899 (10)	C4—H4A	0.9300
O1—C6	1.357 (2)	C5—C6	1.386 (3)
O1—H1	0.8200	C5—H5	0.9300
O2—C8	1.244 (2)	C7—H7	0.9300
O3—C11	1.368 (2)	C8—C9	1.490 (2)
O3—H3	0.8200	C9—C14	1.386 (2)
O4—C13	1.368 (2)	C9—C10	1.388 (2)
O4—H4	0.8200	C10—C11	1.383 (2)
O5—H5A	0.856 (9)	C10—H10	0.9300
O5—H5B	0.857 (9)	C11—C12	1.383 (3)
C1—C6	1.399 (3)	C12—C13	1.372 (3)
C1—C2	1.400 (3)	C12—H12	0.9300
C1—C7	1.450 (2)	C13—C14	1.383 (2)
C2—C3	1.374 (3)	C14—H14	0.9300
C2—H2	0.9300
C7—N1—N2	117.40 (14)	C5—C6—C1	120.43 (19)
C8—N2—N1	118.17 (13)	N1—C7—C1	120.45 (16)
C8—N2—H2A	126.9 (16)	N1—C7—H7	119.8
N1—N2—H2A	114.8 (16)	C1—C7—H7	119.8
C6—O1—H1	109.5	O2—C8—N2	121.30 (15)
C11—O3—H3	109.5	O2—C8—C9	120.94 (15)
C13—O4—H4	109.5	N2—C8—C9	117.75 (14)
H5A—O5—H5B	106.6 (18)	C14—C9—C10	120.16 (15)
C6—C1—C2	117.96 (17)	C14—C9—C8	116.75 (15)
C6—C1—C7	122.26 (16)	C10—C9—C8	123.06 (15)
C2—C1—C7	119.75 (17)	C11—C10—C9	119.09 (16)
C3—C2—C1	121.0 (2)	C11—C10—H10	120.5
C3—C2—H2	119.5	C9—C10—H10	120.5
C1—C2—H2	119.5	O3—C11—C10	121.91 (17)
C4—C3—C2	120.1 (2)	O3—C11—C12	117.19 (16)
C4—C3—H3A	120.0	C10—C11—C12	120.90 (17)
C2—C3—H3A	120.0	C13—C12—C11	119.52 (17)
C3—C4—C5	120.4 (2)	C13—C12—H12	120.2
C3—C4—H4A	119.8	C11—C12—H12	120.2
C5—C4—H4A	119.8	O4—C13—C12	117.35 (16)
C4—C5—C6	120.1 (2)	O4—C13—C14	122.08 (16)
C4—C5—H5	120.0	C12—C13—C14	120.54 (16)
C6—C5—H5	120.0	C13—C14—C9	119.75 (16)
O1—C6—C5	118.38 (18)	C13—C14—H14	120.1
O1—C6—C1	121.19 (16)	C9—C14—H14	120.1

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.587 (2)	147
O5—H5B···O2	0.857 (9)	1.96 (1)	2.807 (2)	170 (2)
O5—H5A···O3i	0.856 (9)	1.96 (1)	2.806 (2)	168 (2)
N2—H2A···O5ii	0.899 (10)	1.96 (1)	2.852 (2)	170 (2)
O3—H3···O2ii	0.82	1.87	2.682 (2)	173
O4—H4···O1iii	0.82	2.00	2.813 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.587 (2)	147
O5—H5B⋯O2	0.857 (9)	1.96 (1)	2.807 (2)	170 (2)
O5—H5A⋯O3i	0.856 (9)	1.96 (1)	2.806 (2)	168 (2)
N2—H2A⋯O5ii	0.899 (10)	1.96 (1)	2.852 (2)	170 (2)
O3—H3⋯O2ii	0.82	1.87	2.682 (2)	173
O4—H4⋯O1iii	0.82	2.00	2.813 (2)	169

Symmetry codes: (i) ; (ii) ; (iii) .