N′-[(E)-1-(5-Chloro-2-hy­droxy­phen­yl)ethyl­idene]pyridine-3-carbohydrazide monohydrate

Hussain, A.; Shafiq, Z.; Tahir, M.N.; Yaqub, M.

doi:10.1107/S1600536810025213

organic compounds

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Volume 66| Part 7| July 2010| Page o1880

doi:10.1107/S1600536810025213

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N′-[(E)-1-(5-Chloro-2-hydroxyphenyl)ethylidene]pyridine-3-carbohydrazide monohydrate

Abid Hussain,^a Zahid Shafiq,^a M. Nawaz Tahir ^b ^* and Muhammad Yaqub ^a

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 26 June 2010; accepted 27 June 2010; online 30 June 2010)

In the title compound, C₁₄H₁₂ClN₃O₂·H₂O, the benzene ring and the pyridine rings are oriented at a dihedral angle of 57.73 (12)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, the water molecule forms O—H⋯O and O—H⋯N hydrogen bonds to the organic molecule, leading to chains containing R₄⁴(16) loops. In addition, weak aromatic π–π stacking interactions between the centroids of pyridine rings [at distance of 3.864 (2) and 4.013 (2) Å] and C—H⋯π interactions 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_r = 307.73
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.17
2491 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) x-1, y, z; (ii) -x+1, -y, -z+1; (iii) -x, -y+1, -z.

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.

Supporting information

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

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

checkCIF report

Comment top

We have reported crystal structures of Schiff bases containing pyridne (Shafiq et al., 2009a, 2009b) and as a part of this project, we report herein the structure and synthesis of the title compound (I, Fig. 1).

In (I) the group A (C1–C8/O1/CL1) of 5-chloro-2-hydroxyacetophenone, the central group B (N1/N2/C9/O2) and the pyridine ring C (C10—C14/N3) are planar with r. m. s. deviation of 0.0330, 0.0182 and 0.0082 Å, respectively. The dihedral angle between A/B, A/C and B/C is 6.62 (11), 58.08 (10) and 52.98 (14)°, respectively. There exist intramolecular H-bonding of O—H···N type forming an S(6) ring motif (Bernstein et al., 1995). The water molecule acts as donar as well as accepter and therefore interconnects three molecules. Due to intra as well as intermolecular H-bondings of O—H···O and O—H···N types (Table 1, Fig. 2), the title compound is stabilized in infinite one dimensional polymeric chains. In the polymeric chains R₄⁴(16) ring motifs are formed. The π–π interactions exist between the centroids of pyridine rings at distance of 3.864 (2) Å [symmetry: -x, -y, 1 - z] and at 4.013 (2) Å [symmetry: 1 - x, 1 - y, 1 - z]. The C—H···π interaction (Table 1) also plays an important role in stabilizing the structure.

Related literature top

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 top

To a hot stirred solution of 5-chloro-2-hydroxyacetophenone (1.71 g, 0.01 mole) in ethanol, 25 ml nicotinic acid hydrazide (1.37 g, 0.01 mol) was added. The resultant mixture was then heated under reflux for 7–8 h. The reaction was monitored through TLC. The precipitate were formed were collected by suction filteration. The resultant crude material was dried and recrystalized in 1,4-dioxan:ethanol(1:2) to affoard light brown needles of (I).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line shows the intramolecular H-bond.
	Fig. 2. The partial packing of (I), which shows that molecules form infinite one dimensional polymeric chains with different ring motifs.

N'-[(E)-1-(5-Chloro-2-hydroxyphenyl)ethylidene]pyridine-3- carbohydrazide monohydrate top

Crystal data top

C₁₄H₁₂ClN₃O₂·H₂O	Z = 2
M_r = 307.73	F(000) = 320
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0375P)² + 0.8617P] where P = (F_o² + 2F_c²)/3
2491 reflections	(Δ/σ)_max < 0.001
198 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₄H₁₂ClN₃O₂·H₂O	γ = 115.755 (2)°
M_r = 307.73	V = 701.94 (8) Å³
Triclinic, P1	Z = 2
a = 7.1693 (5) Å	Mo Kα radiation
b = 7.4964 (4) Å	µ = 0.29 mm⁻¹
c = 14.5966 (9) Å	T = 296 K
α = 90.138 (2)°	0.28 × 0.18 × 0.14 mm
β = 95.835 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2491 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2151 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.959	R_int = 0.027
10105 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.24 e Å⁻³
2491 reflections	Δρ_min = −0.35 e Å⁻³
198 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClN₃O₂·H₂O
M_r	307.73
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1693 (5), 7.4964 (4), 14.5966 (9)
α, β, γ (°)	90.138 (2), 95.835 (1), 115.755 (2)
V (Å³)	701.94 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.28 × 0.18 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	10105, 2491, 2151
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.17
No. of reflections	2491
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009a). Acta Cryst. E65, o2496. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009b). Acta Cryst. E65, o2899. Web of Science CrossRef IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(E)-1-(5-Chloro-2-hy­dr­oxy­phen­yl)ethyl­­idene]pyridine-3-carbohydrazide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

N′-[(E)-1-(5-Chloro-2-hydroxyphenyl)ethylidene]pyridine-3-carbohydrazide monohydrate