N'-[(E)-1-(5-Chloro-2-hy-droxy-phen-yl)ethyl-idene]pyridine-3-carbohydrazide monohydrate.

In the title compound, C(14)H(12)ClN(3)O(2)·H(2)O, the benzene ring and the pyridine rings are oriented at a dihedral angle of 57.73 (12)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, the water mol-ecule forms O-H⋯O and O-H⋯N hydrogen bonds to the organic mol-ecule, leading to chains containing R(4) (4)(16) loops. In addition, weak aromatic π-π stacking inter-actions between the centroids of pyridine rings [at distance of 3.864 (2) and 4.013 (2) Å] and C-H⋯π inter-actions occur.

Related literature

For background to Schiff bases and for related structures, see: Shafiq et al. (2009a ▶,b ▶): For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12ClN3O2·H2O

M = 307.73

Triclinic,

a = 7.1693 (5) Å

b = 7.4964 (4) Å

c = 14.5966 (9) Å

α = 90.138 (2)°

β = 95.835 (1)°

γ = 115.755 (2)°

V = 701.94 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.28 × 0.18 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.959

10105 measured reflections

2491 independent reflections

2151 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.17

2491 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025213/hb5528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025213/hb5528Isup2.hkl

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

C14H12ClN3O2·H2O	Z = 2
Mr = 307.73	F(000) = 320
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1693 (5) Å	Cell parameters from 1770 reflections
b = 7.4964 (4) Å	θ = 2.6–28.4°
c = 14.5966 (9) Å	µ = 0.29 mm−1
α = 90.138 (2)°	T = 296 K
β = 95.835 (1)°	Needle, light brown
γ = 115.755 (2)°	0.28 × 0.18 × 0.14 mm
V = 701.94 (8) Å3

Bruker Kappa APEXII CCD diffractometer	2491 independent reflections
Radiation source: fine-focus sealed tube	2151 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 8.20 pixels mm-1	θmax = 25.3°, θmin = 2.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.942, Tmax = 0.959	l = −16→17
10105 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.8617P] where P = (Fo2 + 2Fc2)/3
2491 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.33027 (14)	0.26260 (13)	−0.24936 (5)	0.0523 (3)
O1	0.3445 (3)	0.2717 (4)	0.01706 (15)	0.0491 (8)
O2	0.4191 (3)	0.2364 (4)	0.25756 (15)	0.0544 (8)
N1	0.1131 (3)	0.2425 (3)	0.14368 (15)	0.0338 (7)
N2	0.0986 (4)	0.2273 (4)	0.23701 (15)	0.0347 (7)
N3	0.2974 (4)	0.0892 (5)	0.53373 (18)	0.0523 (10)
C1	−0.0064 (4)	0.2462 (4)	−0.01053 (18)	0.0311 (8)
C2	0.1854 (4)	0.2739 (4)	−0.04006 (19)	0.0365 (9)
C3	0.2156 (5)	0.3040 (5)	−0.1323 (2)	0.0505 (11)
C4	0.0595 (6)	0.3026 (5)	−0.1958 (2)	0.0502 (11)
C5	−0.1289 (5)	0.2703 (4)	−0.16794 (19)	0.0391 (9)
C6	−0.1630 (4)	0.2451 (4)	−0.07681 (19)	0.0347 (8)
C7	−0.0461 (4)	0.2199 (4)	0.08716 (18)	0.0306 (8)
C8	−0.2576 (5)	0.1709 (6)	0.1141 (2)	0.0476 (10)
C9	0.2671 (4)	0.2336 (4)	0.28988 (19)	0.0343 (9)
C10	0.2551 (4)	0.2337 (4)	0.39173 (18)	0.0341 (9)
C11	0.2132 (4)	0.3709 (5)	0.4384 (2)	0.0398 (9)
C12	0.2188 (5)	0.3679 (5)	0.5328 (2)	0.0500 (11)
C13	0.2599 (5)	0.2246 (6)	0.5769 (2)	0.0537 (13)
C14	0.2966 (5)	0.0971 (5)	0.4425 (2)	0.0421 (10)
O3	0.7770 (3)	0.2277 (4)	0.34221 (16)	0.0478 (8)
H1	0.31433	0.26059	0.07012	0.0736*
H2	−0.01187	0.21446	0.26025	0.0416*
H3	0.34320	0.32529	−0.15140	0.0608*
H4	0.08174	0.32343	−0.25733	0.0605*
H6	−0.29067	0.22721	−0.05904	0.0416*
H8A	−0.27145	0.29111	0.12362	0.0715*
H8B	−0.27573	0.10118	0.17002	0.0715*
H8C	−0.36158	0.08889	0.06588	0.0715*
H11	0.18180	0.46339	0.40644	0.0478*
H12	0.19538	0.46062	0.56616	0.0598*
H13	0.26161	0.22236	0.64064	0.0645*
H14	0.32550	0.00545	0.41125	0.0505*
H3A	0.657 (6)	0.217 (5)	0.314 (3)	0.0574*
H3B	0.735 (6)	0.139 (5)	0.387 (3)	0.0574*

	U11	U22	U33	U12	U13	U23
Cl1	0.0600 (5)	0.0632 (5)	0.0309 (4)	0.0269 (4)	−0.0066 (3)	0.0055 (3)
O1	0.0391 (12)	0.0743 (16)	0.0436 (12)	0.0329 (12)	0.0093 (10)	0.0112 (12)
O2	0.0426 (12)	0.1011 (19)	0.0355 (12)	0.0456 (13)	0.0069 (10)	0.0129 (12)
N1	0.0346 (12)	0.0435 (14)	0.0252 (12)	0.0192 (11)	0.0011 (9)	0.0024 (10)
N2	0.0313 (12)	0.0509 (14)	0.0248 (12)	0.0209 (11)	0.0026 (9)	0.0032 (10)
N3	0.0568 (17)	0.079 (2)	0.0347 (14)	0.0416 (16)	0.0083 (12)	0.0156 (14)
C1	0.0344 (14)	0.0286 (14)	0.0287 (14)	0.0127 (12)	0.0015 (11)	0.0001 (11)
C2	0.0393 (16)	0.0394 (16)	0.0347 (15)	0.0204 (13)	0.0056 (12)	0.0032 (12)
C3	0.0509 (19)	0.069 (2)	0.0438 (18)	0.0342 (18)	0.0205 (15)	0.0110 (16)
C4	0.067 (2)	0.063 (2)	0.0297 (16)	0.0352 (19)	0.0135 (15)	0.0081 (14)
C5	0.0493 (18)	0.0391 (16)	0.0281 (14)	0.0199 (14)	−0.0012 (12)	0.0013 (12)
C6	0.0338 (14)	0.0366 (15)	0.0316 (15)	0.0141 (12)	0.0012 (11)	0.0001 (12)
C7	0.0314 (14)	0.0326 (14)	0.0282 (14)	0.0148 (12)	0.0015 (11)	0.0004 (11)
C8	0.0356 (16)	0.079 (2)	0.0296 (15)	0.0264 (16)	0.0031 (12)	0.0055 (15)
C9	0.0307 (14)	0.0450 (17)	0.0301 (14)	0.0197 (13)	0.0014 (11)	0.0039 (12)
C10	0.0270 (13)	0.0469 (17)	0.0267 (14)	0.0153 (12)	−0.0004 (11)	0.0020 (12)
C11	0.0356 (15)	0.0473 (17)	0.0368 (16)	0.0192 (14)	0.0000 (12)	0.0014 (13)
C12	0.0470 (18)	0.068 (2)	0.0382 (17)	0.0284 (17)	0.0032 (14)	−0.0074 (16)
C13	0.053 (2)	0.092 (3)	0.0261 (16)	0.041 (2)	0.0038 (14)	0.0042 (16)
C14	0.0458 (17)	0.057 (2)	0.0322 (16)	0.0302 (16)	0.0057 (13)	0.0064 (14)
O3	0.0364 (12)	0.0757 (17)	0.0380 (12)	0.0304 (12)	0.0052 (9)	0.0118 (11)

Cl1—C5	1.755 (4)	C5—C6	1.376 (4)
O1—C2	1.349 (4)	C7—C8	1.492 (5)
O2—C9	1.223 (4)	C9—C10	1.498 (4)
O1—H1	0.8200	C10—C11	1.385 (4)
O3—H3A	0.89 (5)	C10—C14	1.382 (4)
O3—H3B	0.91 (4)	C11—C12	1.375 (4)
N1—N2	1.378 (3)	C12—C13	1.377 (5)
N1—C7	1.285 (4)	C3—H3	0.9300
N2—C9	1.348 (4)	C4—H4	0.9300
N3—C14	1.333 (4)	C6—H6	0.9300
N3—C13	1.330 (5)	C8—H8C	0.9600
N2—H2	0.8600	C8—H8A	0.9600
C1—C7	1.479 (4)	C8—H8B	0.9600
C1—C6	1.403 (4)	C11—H11	0.9300
C1—C2	1.412 (4)	C12—H12	0.9300
C2—C3	1.389 (4)	C13—H13	0.9300
C3—C4	1.375 (5)	C14—H14	0.9300
C4—C5	1.370 (6)
C2—O1—H1	109.00	C9—C10—C14	119.0 (3)
H3A—O3—H3B	102 (4)	C9—C10—C11	122.9 (3)
N2—N1—C7	120.6 (3)	C10—C11—C12	118.8 (3)
N1—N2—C9	116.3 (3)	C11—C12—C13	118.5 (3)
C13—N3—C14	116.9 (3)	N3—C13—C12	123.9 (3)
N1—N2—H2	122.00	N3—C14—C10	123.7 (3)
C9—N2—H2	122.00	C2—C3—H3	120.00
C2—C1—C6	118.2 (2)	C4—C3—H3	120.00
C2—C1—C7	122.3 (3)	C5—C4—H4	120.00
C6—C1—C7	119.5 (3)	C3—C4—H4	120.00
C1—C2—C3	119.6 (3)	C1—C6—H6	120.00
O1—C2—C3	117.1 (3)	C5—C6—H6	120.00
O1—C2—C1	123.3 (3)	C7—C8—H8B	109.00
C2—C3—C4	120.9 (3)	C7—C8—H8C	109.00
C3—C4—C5	119.7 (3)	H8A—C8—H8B	110.00
Cl1—C5—C6	119.2 (3)	H8A—C8—H8C	109.00
Cl1—C5—C4	119.7 (2)	H8B—C8—H8C	109.00
C4—C5—C6	121.1 (3)	C7—C8—H8A	109.00
C1—C6—C5	120.4 (3)	C10—C11—H11	121.00
N1—C7—C8	124.7 (2)	C12—C11—H11	121.00
C1—C7—C8	120.6 (3)	C13—C12—H12	121.00
N1—C7—C1	114.7 (3)	C11—C12—H12	121.00
O2—C9—N2	122.8 (3)	N3—C13—H13	118.00
O2—C9—C10	121.7 (3)	C12—C13—H13	118.00
N2—C9—C10	115.5 (3)	N3—C14—H14	118.00
C11—C10—C14	118.1 (3)	C10—C14—H14	118.00
C7—N1—N2—C9	173.6 (3)	O1—C2—C3—C4	178.1 (3)
N2—N1—C7—C1	178.2 (2)	C1—C2—C3—C4	−1.5 (5)
N2—N1—C7—C8	−1.8 (4)	C2—C3—C4—C5	−0.3 (5)
N1—N2—C9—O2	−5.8 (4)	C3—C4—C5—Cl1	−178.5 (3)
N1—N2—C9—C10	175.2 (2)	C3—C4—C5—C6	2.0 (5)
C14—N3—C13—C12	0.8 (6)	Cl1—C5—C6—C1	178.6 (2)
C13—N3—C14—C10	−1.4 (6)	C4—C5—C6—C1	−1.9 (4)
C6—C1—C2—O1	−178.0 (3)	O2—C9—C10—C11	126.3 (3)
C6—C1—C2—C3	1.6 (4)	O2—C9—C10—C14	−50.7 (4)
C7—C1—C2—O1	2.4 (4)	N2—C9—C10—C11	−54.6 (4)
C7—C1—C2—C3	−178.0 (3)	N2—C9—C10—C14	128.4 (3)
C2—C1—C6—C5	0.1 (4)	C9—C10—C11—C12	−175.7 (3)
C7—C1—C6—C5	179.7 (3)	C14—C10—C11—C12	1.3 (5)
C2—C1—C7—N1	6.1 (4)	C9—C10—C14—N3	177.6 (3)
C2—C1—C7—C8	−173.9 (3)	C11—C10—C14—N3	0.4 (5)
C6—C1—C7—N1	−173.5 (2)	C10—C11—C12—C13	−1.9 (5)
C6—C1—C7—C8	6.6 (4)	C11—C12—C13—N3	0.9 (6)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.555 (3)	144
N2—H2···O3i	0.86	2.06	2.898 (4)	166
O3—H3A···O2	0.89 (5)	1.88 (5)	2.760 (4)	171 (3)
O3—H3B···N3ii	0.91 (4)	2.01 (4)	2.885 (4)	161 (4)
C8—H8A···Cg2iii	0.96	2.99	3.763 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.555 (3)	144
N2—H2⋯O3i	0.86	2.06	2.898 (4)	166
O3—H3A⋯O2	0.89 (5)	1.88 (5)	2.760 (4)	171 (3)
O3—H3B⋯N3ii	0.91 (4)	2.01 (4)	2.885 (4)	161 (4)
C8—H8A⋯Cg2iii	0.96	2.99	3.763 (4)	139

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