(E)-N′-(5-Chloro-2-hydroxy­benzyl­idene)-4-(8-quinol­yloxy)butanohydrazide monohydrate

Zhang, J.; XiaHou, G.-L.; Zhang, S.-S.; Zeng, J.

doi:10.1107/S1600536809023733

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1695-o1696

doi:10.1107/S1600536809023733

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(E)-N′-(5-Chloro-2-hydroxybenzylidene)-4-(8-quinolyloxy)butanohydrazide monohydrate

Jian Zhang,^a Guo-Lun XiaHou,^a Sheng-Sen Zhang ^a and Jing Zeng ^a ^*

^aCollege of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000, People's Republic of China
^*Correspondence e-mail: zengjinggnmu@yahoo.cn

(Received 12 June 2009; accepted 20 June 2009; online 27 June 2009)

The crystal of the title Schiff base compound, C₂₀H₁₈ClN₃O₃·H₂O, was twinned by a twofold rotation about (100). The asymmetric unit contains two crystallographically independent molecules with similar conformations, and two water molecules. The C=N—N angles of 115.7 (6) and 116.2 (6)° are significantly smaller than the ideal value of 120° expected for sp²-hybridized N atoms and the dihedral angles between the benzene ring and quinoline ring system in the two molecules are 52.5 (7) and 53.9 (7)°. The molecules aggregate via C—Cl⋯π and π–π interactions [centroid–centroid distances = 3.696 (5)–3.892 (5) Å] and weak C—H⋯O interactions as parallel sheets, which are further linked by water molecules through N—H⋯O and O—H⋯O hydrogen bonds into a supramolecular two-dimensional network.

Related literature

For background to the rational construction of new matallosupramolecular architectures, see: Muraoka et al. (1998 ); Cai et al. (2003 ); Pallavicini et al. (2007 ). For the use of 8-hydroxyquinoline and its derivatives as ligands in this area, see: Chen et al. (2005 ); Park et al. (2006 ); Karmakar et al. (2007 ). For related structures, see: Xu et al. (2002 ); Zhang et al. (2005 ); Wen et al. (2005 ); Wei et al. (2004 ); Zheng, Li et al. (2008 ); Zheng, Wu, Lu et al., (2006 ); Zheng (2006 ); Zheng, Qiu et al. (2006 ); Zheng, Wu, Li et al. (2007 ); Xie et al. (2008 ); Chen & Li (2009 ). For comparative bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₈ClN₃O₃·H₂O
M_r = 401.84
Monoclinic, C c
a = 11.167 (3) Å
b = 11.150 (3) Å
c = 30.909 (10) Å
β = 96.970 (12)°
V = 3820 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.32 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.929, T_max = 0.977
17043 measured reflections
5912 independent reflections
3796 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.198
S = 1.02
5912 reflections
508 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983), 2525 Friedel pairs
Flack parameter: 0.08 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O7ⁱ	0.86	2.07	2.836 (9)	147
N5—H5⋯O8ⁱⁱ	0.86	2.05	2.820 (9)	149
O3—H3⋯N3	0.82	1.92	2.630 (8)	144
O6—H6⋯N6	0.82	1.91	2.633 (9)	147
O7—H29⋯N1	0.85	2.05	2.876 (8)	165
O7—H30⋯O5ⁱⁱⁱ	0.85	2.06	2.839 (9)	153
O8—H31⋯N4	0.85	2.04	2.872 (9)	166
O8—H32⋯O2^iv	0.85	1.99	2.845 (9)	180
C7—H7⋯O6ⁱⁱⁱ	0.93	2.53	3.267 (10)	137
C27—H27⋯O3^v	0.93	2.56	3.303 (10)	137
C19—Cl1⋯Cg5^vi	1.74 (1)	3.63 (1)	4.127 (9)	94 (1)
C39—Cl2⋯Cg1^vii	1.76 (1)	3.62 (1)	4.109 (9)	93 (1)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y, z+{\script{1\over 2}}]$ ; (v) $[x, -y, z+{\script{1\over 2}}]$ ; (vi) $[x, -y+1, z-{\script{1\over 2}}]$ ; (vii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the N1/C8/C7/C6/C5/C9 and N4/C28/C27/C26/C25/C29 rings, respectively.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023733/pk2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023733/pk2173Isup2.hkl

checkCIF report

Comment top

The rational construction of new matallosupramolecular architectures using logical combinations of rigid linear and angular components, has been the subject of much study during the last decade (Muraoka et al.,1998; Cai et al., 2003; Pallavicini et al., 2007). Most commonly, nitrogen heterocycles have been used to provide donors for coordination to metals within these assemblies, with pyridine rings being by far the most frequently used. More recently, flexible ligands have been employed to obtain access to topologies that are not available using more rigid ligands. Such flexibility can be introduced by means of combinations of methylene, ether, or thioether spacer groups between the donor sites, which permit the ligand to exist in various combinations as a result of rotations about single bonds. 8-Hydroxyquinoline and its derivatives are among the most extensively investigated ligands in this area (Xu et al., 2002; Cai et al., 2003; Chen et al., 2005; Park et al., 2006; Karmakar et al., 2007; Zhang et al., 2005; Wen et al., 2005, Wei et al., 2004; Zheng, Li et al., 2008). In this contribution, we present the synthesis and crystal structure of a new ligand, which contains oxygen and nitrogen donors and flexible aliphatic spacers.

The bond lengths and angles are in good agreement with expected values (Allen et al., 1987) and are comparable to those in the related compounds (Zheng, Wu, Lu et al., 2006; Zheng, 2006; Zheng, Wu, Li et al., 2007; Xie et al., 2008; Chen & Li, 2009). X-ray crystallography reveals that the title compound was twinned by a 2-fold rotation about (100). The crystals contain two crystallographically independent molecules with similar conformations, and two water molecules. The conformation along the C1—O1—C10—C11—C12—C13—N2—N3—C14—C15 and C21—O4—C30—C31—C32—C33—N5—N6—C34—C35 bond sequence are all trans (Fig.1). The C14—N3 and C34—N6 bond lengths of 1.290 (9) and 1.283 (9) Å respectively, indicate the presence of a typical C=N. The CN—N angle of 115.7 (6) and 116.2 (6)° are significantly smaller than the ideal value of 120° expected for sp²-hybridized N atoms and the dihedral angles between the benzene ring and quinoline ring system in the two molecules are 52.5 (7) and 53.9 (7)°. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N atom (Zheng, Qiu et al., 2006). All torsion angles involving non-H atoms are close to 180°, which indicates that the molecules are essentially planar with the C=N bond adjacent to the benzene ring and quinoline group adopting a trans configuration with respect to its substitution. In the crystal packing, intramolecular O—H···N hydrogen bonds produce S(6) ring motifs (Bernstein et al.,1995) and there are also significant π-stacking interactions between the planar sections associated with the benzene ring and quinoline group. The organic molecules aggregate via intermolecular weak C—Cl···π and π–π interactions between the benzene ring and quinoline rings [centroid-centroid distances in the range of 3.696 (5)–3.892 (5) Å] and weak C—H···O contacts into an array of parallel sheets, and these layers are further linked by water molecules via N—H···O and O—H···O hydrogen bonds into a supramolecular two dimensional network (Fig. 2 and Table 1).

Related literature top

For general background, see: Cai et al. (2003); Chen et al. (2005); Park et al. (2006); Karmakar et al. (2007); Muraoka et al. (1998); Pallavicini et al. (2007). For related structures, see: Xu et al. (2002); Zhang et al. (2005); Wen et al. (2005); Wei et al. (2004); Zheng, Li et al. (2008); Zheng, Wu, Lu et al., (2006); Zheng (2006); Zheng, Qiu et al. (2006); Zheng, Wu, Li et al. (2007); Xie et al. (2008); Chen & Li (2009). For comparative bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Reagents and solvents were of commercially available quality. The title complex was synthesized according to the method of Zheng, Li et al. 2008. 2-(quinolin-8-yloxy)butanehydrazide (0.01 mol), 5-chloro-2-hydroxybenzaldehyde (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask and refluxed for 6 h. After cooling to room temperature, the solid product was separated by filtration. Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a tetrahydrofuran solution over a period of 2 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure, with displacement ellipsoids at the 30% probability level.
	Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

(E)-N'-(5-Chloro-2-hydroxybenzylidene)-4-(8- quinolyloxy)butanohydrazide monohydrate top

Crystal data top

C₂₀H₁₈ClN₃O₃·H₂O	F(000) = 1680
M_r = 401.84	D_x = 1.397 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2234 reflections
a = 11.167 (3) Å	θ = 2.6–18.8°
b = 11.150 (3) Å	µ = 0.23 mm⁻¹
c = 30.909 (10) Å	T = 295 K
β = 96.970 (12)°	Block, yellow
V = 3820 (2) Å³	0.32 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5912 independent reflections
Radiation source: fine-focus sealed tube	3796 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.929, T_max = 0.977	k = −12→13
17043 measured reflections	l = −32→36

Refinement top

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)] = 0.079	H-atom parameters constrained
wR(F²) = 0.198	w = 1/[σ²(F_o²) + (0.08P)² + 4.5P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5912 reflections	Δρ_max = 0.34 e Å⁻³
508 parameters	Δρ_min = −0.32 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2525 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (13)

Crystal data top

C₂₀H₁₈ClN₃O₃·H₂O	V = 3820 (2) Å³
M_r = 401.84	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 11.167 (3) Å	µ = 0.23 mm⁻¹
b = 11.150 (3) Å	T = 295 K
c = 30.909 (10) Å	0.32 × 0.15 × 0.10 mm
β = 96.970 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5912 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3796 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.977	R_int = 0.093
17043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	H-atom parameters constrained
wR(F²) = 0.198	Δρ_max = 0.34 e Å⁻³
S = 1.02	Δρ_min = −0.32 e Å⁻³
5912 reflections	Absolute structure: Flack (1983), 2525 Friedel pairs
508 parameters	Absolute structure parameter: 0.08 (13)
2 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.3021 (2)	0.92993 (19)	−0.10155 (8)	0.0771 (7)
Cl2	1.56704 (19)	0.7328 (2)	0.70372 (8)	0.0731 (7)
N1	1.1629 (5)	0.0908 (5)	0.18110 (18)	0.0446 (15)
N2	0.5924 (6)	0.4429 (6)	0.0353 (2)	0.0564 (17)
H2	0.5800	0.4886	0.0568	0.068*
N3	0.5489 (5)	0.4771 (6)	−0.0078 (2)	0.0513 (16)
N4	0.6334 (6)	−0.0301 (6)	0.4222 (2)	0.0503 (16)
N5	1.0354 (6)	0.4892 (6)	0.5686 (2)	0.0535 (17)
H5	1.0744	0.5082	0.5472	0.064*
N6	1.0823 (5)	0.5171 (6)	0.6110 (2)	0.0520 (17)
O1	0.9426 (4)	0.1745 (5)	0.16115 (17)	0.0575 (14)
O2	0.6701 (6)	0.2718 (6)	0.0137 (2)	0.0782 (19)
O3	0.4881 (6)	0.4409 (5)	−0.09162 (19)	0.0696 (17)
H3	0.5252	0.4267	−0.0676	0.084*
O4	0.7248 (5)	0.1826 (4)	0.44221 (16)	0.0518 (13)
O5	0.8704 (6)	0.4003 (6)	0.59010 (19)	0.079 (2)
O6	1.0749 (5)	0.5481 (6)	0.69511 (19)	0.0669 (16)
H6	1.0486	0.5333	0.6697	0.100*
O7	1.1208 (5)	0.1480 (5)	0.08981 (17)	0.0670 (16)
H29	1.1252	0.1199	0.1155	0.100*
H30	1.1950	0.1587	0.0878	0.100*
O8	0.7190 (5)	−0.0214 (6)	0.51354 (18)	0.0719 (17)
H31	0.6910	−0.0115	0.4869	0.108*
H32	0.7045	−0.0963	0.5137	0.108*
C1	0.9739 (7)	0.1482 (7)	0.2040 (2)	0.0491 (19)
C2	0.9014 (7)	0.1634 (7)	0.2365 (3)	0.052 (2)
H2A	0.8245	0.1956	0.2299	0.062*
C3	0.9426 (7)	0.1306 (7)	0.2795 (3)	0.0494 (19)
H3A	0.8926	0.1405	0.3012	0.059*
C4	1.0553 (7)	0.0845 (7)	0.2896 (2)	0.054 (2)
H4	1.0814	0.0616	0.3182	0.065*
C5	1.1329 (6)	0.0711 (7)	0.2572 (2)	0.0494 (19)
C6	1.2504 (7)	0.0246 (7)	0.2659 (3)	0.0471 (18)
H6A	1.2801	0.0017	0.2941	0.057*
C7	1.3212 (7)	0.0129 (7)	0.2331 (2)	0.050 (2)
H7	1.3993	−0.0172	0.2384	0.060*
C8	1.2709 (7)	0.0487 (7)	0.1908 (3)	0.053 (2)
H8	1.3189	0.0413	0.1683	0.064*
C9	1.0930 (6)	0.1029 (6)	0.2136 (2)	0.0402 (17)
C10	0.8271 (7)	0.2281 (7)	0.1500 (2)	0.0493 (19)
H10A	0.8222	0.3022	0.1661	0.059*
H10B	0.7647	0.1744	0.1577	0.059*
C11	0.8075 (7)	0.2541 (7)	0.1009 (2)	0.051 (2)
H11A	0.8709	0.3061	0.0930	0.061*
H11B	0.8095	0.1799	0.0847	0.061*
C12	0.6870 (7)	0.3139 (8)	0.0903 (2)	0.058 (2)
H12A	0.6257	0.2627	0.1003	0.070*
H12B	0.6876	0.3885	0.1065	0.070*
C13	0.6523 (7)	0.3405 (8)	0.0430 (3)	0.056 (2)
C14	0.4998 (7)	0.5818 (7)	−0.0120 (2)	0.0495 (19)
H14	0.4960	0.6297	0.0125	0.059*
C15	0.4508 (6)	0.6247 (6)	−0.0543 (2)	0.0401 (16)
C16	0.4452 (7)	0.5569 (7)	−0.0923 (3)	0.055 (2)
C17	0.3957 (8)	0.6009 (7)	−0.1314 (3)	0.055 (2)
H17	0.3913	0.5530	−0.1562	0.067*
C18	0.3512 (7)	0.7182 (8)	−0.1345 (3)	0.057 (2)
H18	0.3180	0.7498	−0.1611	0.068*
C19	0.3579 (6)	0.7847 (7)	−0.0974 (3)	0.0482 (19)
C20	0.4057 (7)	0.7447 (7)	−0.0576 (2)	0.0503 (19)
H20	0.4091	0.7938	−0.0331	0.060*
C21	0.6857 (6)	0.1661 (7)	0.3997 (2)	0.0416 (17)
C22	0.6908 (7)	0.2486 (7)	0.3667 (2)	0.0519 (19)
H22	0.7218	0.3249	0.3731	0.062*
C23	0.6492 (7)	0.2178 (8)	0.3234 (3)	0.052 (2)
H23	0.6553	0.2735	0.3014	0.063*
C24	0.6010 (7)	0.1103 (8)	0.3132 (3)	0.056 (2)
H24	0.5733	0.0922	0.2843	0.067*
C25	0.5925 (7)	0.0266 (7)	0.3452 (2)	0.0475 (18)
C26	0.5430 (7)	−0.0906 (7)	0.3365 (3)	0.0495 (19)
H26	0.5114	−0.1116	0.3083	0.059*
C27	0.5422 (8)	−0.1723 (7)	0.3701 (3)	0.055 (2)
H27	0.5105	−0.2488	0.3647	0.066*
C28	0.5896 (7)	−0.1386 (8)	0.4122 (3)	0.055 (2)
H28	0.5906	−0.1951	0.4344	0.066*
C29	0.6356 (6)	0.0495 (8)	0.3891 (2)	0.0471 (19)
C30	0.7820 (7)	0.2949 (7)	0.4533 (3)	0.054 (2)
H30A	0.7255	0.3599	0.4458	0.065*
H30B	0.8501	0.3055	0.4370	0.065*
C31	0.8249 (7)	0.2981 (7)	0.5017 (2)	0.0491 (19)
H31A	0.7567	0.2889	0.5181	0.059*
H31B	0.8805	0.2325	0.5093	0.059*
C32	0.8867 (8)	0.4158 (7)	0.5129 (3)	0.058 (2)
H32A	0.8319	0.4805	0.5031	0.070*
H32B	0.9564	0.4222	0.4971	0.070*
C33	0.9273 (7)	0.4315 (8)	0.5609 (3)	0.055 (2)
C34	1.1874 (7)	0.5652 (7)	0.6160 (2)	0.051 (2)
H34	1.2261	0.5797	0.5916	0.061*
C35	1.2463 (6)	0.5970 (6)	0.6576 (2)	0.0432 (17)
C36	1.1891 (7)	0.5900 (7)	0.6968 (2)	0.0480 (19)
C37	1.2494 (7)	0.6258 (8)	0.7354 (3)	0.057 (2)
H37	1.2118	0.6202	0.7606	0.068*
C38	1.3654 (7)	0.6702 (7)	0.7381 (2)	0.0488 (19)
H38	1.4055	0.6960	0.7646	0.059*
C39	1.4200 (7)	0.6753 (7)	0.7010 (3)	0.054 (2)
C40	1.3609 (7)	0.6448 (7)	0.6612 (3)	0.0502 (19)
H40	1.3985	0.6563	0.6363	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0964 (18)	0.0496 (12)	0.0808 (16)	0.0246 (13)	−0.0072 (13)	0.0021 (11)
Cl2	0.0459 (11)	0.0978 (17)	0.0739 (14)	−0.0247 (12)	0.0002 (10)	−0.0134 (13)
N1	0.045 (4)	0.049 (4)	0.038 (4)	0.004 (3)	0.000 (3)	0.001 (3)
N2	0.055 (4)	0.057 (4)	0.055 (4)	0.015 (3)	−0.004 (3)	0.001 (3)
N3	0.042 (4)	0.054 (4)	0.055 (4)	0.010 (3)	−0.003 (3)	0.008 (3)
N4	0.050 (4)	0.043 (4)	0.056 (4)	−0.008 (3)	0.000 (3)	−0.004 (3)
N5	0.059 (4)	0.057 (4)	0.044 (4)	−0.010 (3)	0.002 (3)	−0.017 (3)
N6	0.041 (4)	0.057 (4)	0.055 (4)	−0.016 (3)	−0.004 (3)	−0.007 (3)
O1	0.040 (3)	0.083 (4)	0.049 (3)	0.017 (3)	0.000 (2)	0.002 (3)
O2	0.108 (5)	0.067 (4)	0.057 (4)	0.024 (4)	−0.003 (4)	−0.006 (3)
O3	0.096 (5)	0.045 (3)	0.064 (4)	0.025 (3)	−0.007 (3)	−0.009 (3)
O4	0.065 (3)	0.043 (3)	0.045 (3)	−0.016 (3)	0.001 (3)	−0.005 (2)
O5	0.064 (4)	0.126 (6)	0.048 (4)	−0.026 (4)	0.008 (3)	−0.018 (4)
O6	0.048 (3)	0.082 (4)	0.070 (4)	−0.026 (3)	0.009 (3)	−0.002 (4)
O7	0.066 (4)	0.078 (4)	0.056 (4)	0.006 (3)	0.003 (3)	−0.004 (3)
O8	0.067 (4)	0.100 (5)	0.049 (3)	−0.013 (3)	0.007 (3)	−0.001 (3)
C1	0.046 (5)	0.057 (5)	0.044 (5)	−0.001 (4)	0.000 (4)	0.015 (4)
C2	0.047 (4)	0.051 (5)	0.058 (5)	0.004 (4)	0.009 (4)	−0.010 (4)
C3	0.045 (5)	0.055 (5)	0.049 (5)	0.008 (4)	0.010 (4)	−0.001 (4)
C4	0.058 (5)	0.070 (5)	0.034 (4)	0.005 (4)	0.006 (4)	−0.002 (4)
C5	0.037 (4)	0.063 (5)	0.048 (5)	−0.001 (4)	0.003 (3)	−0.004 (4)
C6	0.043 (4)	0.049 (5)	0.048 (5)	−0.002 (4)	0.000 (4)	0.003 (4)
C7	0.043 (4)	0.056 (5)	0.049 (5)	0.000 (4)	−0.001 (4)	−0.013 (4)
C8	0.049 (5)	0.044 (4)	0.068 (6)	0.000 (4)	0.011 (4)	−0.002 (4)
C9	0.045 (4)	0.036 (4)	0.039 (4)	0.001 (3)	0.003 (3)	0.002 (3)
C10	0.043 (4)	0.046 (4)	0.056 (5)	0.014 (4)	−0.002 (4)	0.001 (4)
C11	0.050 (5)	0.039 (4)	0.063 (5)	0.006 (4)	0.010 (4)	0.007 (4)
C12	0.060 (5)	0.062 (5)	0.048 (5)	0.005 (4)	−0.010 (4)	0.004 (4)
C13	0.058 (5)	0.048 (5)	0.058 (6)	0.005 (4)	−0.007 (4)	0.007 (4)
C14	0.051 (4)	0.054 (5)	0.042 (4)	0.002 (4)	0.001 (3)	−0.003 (4)
C15	0.032 (4)	0.045 (4)	0.042 (4)	0.006 (3)	0.001 (3)	−0.004 (3)
C16	0.051 (5)	0.047 (5)	0.066 (6)	0.010 (4)	0.006 (4)	−0.003 (4)
C17	0.065 (5)	0.059 (5)	0.042 (5)	0.008 (4)	0.006 (4)	−0.012 (4)
C18	0.045 (5)	0.070 (6)	0.052 (5)	0.006 (4)	−0.008 (4)	0.006 (4)
C19	0.041 (4)	0.050 (5)	0.053 (5)	0.000 (3)	0.001 (4)	0.000 (4)
C20	0.053 (5)	0.048 (4)	0.050 (5)	0.006 (4)	0.004 (4)	−0.002 (4)
C21	0.038 (4)	0.053 (5)	0.033 (4)	−0.001 (3)	0.003 (3)	−0.005 (4)
C22	0.055 (5)	0.051 (5)	0.046 (5)	−0.003 (4)	−0.007 (4)	−0.008 (4)
C23	0.054 (5)	0.052 (5)	0.052 (5)	−0.005 (4)	0.009 (4)	−0.007 (4)
C24	0.048 (4)	0.078 (6)	0.043 (5)	0.006 (4)	0.002 (3)	0.007 (4)
C25	0.045 (4)	0.050 (5)	0.046 (5)	0.001 (4)	−0.005 (3)	−0.004 (4)
C26	0.050 (5)	0.053 (5)	0.042 (4)	−0.002 (4)	−0.010 (3)	−0.007 (4)
C27	0.071 (6)	0.035 (4)	0.058 (6)	−0.005 (4)	0.006 (4)	−0.012 (4)
C28	0.061 (5)	0.062 (5)	0.043 (5)	0.001 (4)	0.009 (4)	0.006 (4)
C29	0.035 (4)	0.073 (6)	0.033 (4)	0.004 (4)	0.005 (3)	0.005 (4)
C30	0.042 (4)	0.043 (5)	0.078 (6)	0.000 (3)	0.012 (4)	0.001 (4)
C31	0.047 (4)	0.054 (5)	0.043 (5)	−0.006 (4)	−0.009 (3)	−0.008 (4)
C32	0.059 (5)	0.058 (5)	0.055 (5)	−0.012 (4)	−0.002 (4)	−0.014 (4)
C33	0.046 (5)	0.068 (6)	0.050 (5)	0.005 (4)	0.005 (4)	−0.014 (4)
C34	0.049 (5)	0.062 (5)	0.042 (5)	0.000 (4)	0.004 (4)	0.001 (4)
C35	0.044 (4)	0.038 (4)	0.047 (4)	−0.003 (3)	0.002 (3)	−0.003 (3)
C36	0.050 (5)	0.044 (4)	0.049 (5)	0.004 (3)	0.004 (4)	0.000 (4)
C37	0.057 (5)	0.074 (6)	0.040 (5)	−0.004 (4)	0.010 (4)	−0.003 (4)
C38	0.042 (4)	0.063 (5)	0.041 (4)	0.003 (4)	0.004 (3)	−0.002 (4)
C39	0.049 (5)	0.062 (5)	0.050 (5)	−0.006 (4)	0.007 (4)	0.000 (4)
C40	0.050 (5)	0.055 (5)	0.045 (5)	−0.010 (4)	0.002 (4)	0.004 (4)

Geometric parameters (Å, º) top

Cl1—C19	1.735 (8)	C12—C13	1.495 (11)
Cl2—C39	1.756 (8)	C12—H12A	0.9700
N1—C8	1.295 (9)	C12—H12B	0.9700
N1—C9	1.352 (8)	C14—C15	1.439 (10)
N2—C13	1.329 (10)	C14—H14	0.9300
N2—N3	1.414 (9)	C15—C16	1.392 (10)
N2—H2	0.8600	C15—C20	1.428 (10)
N3—C14	1.290 (9)	C16—C17	1.358 (11)
N4—C28	1.328 (10)	C17—C18	1.398 (11)
N4—C29	1.357 (9)	C17—H17	0.9300
N5—C33	1.363 (10)	C18—C19	1.360 (11)
N5—N6	1.389 (8)	C18—H18	0.9300
N5—H5	0.8600	C19—C20	1.357 (10)
N6—C34	1.283 (9)	C20—H20	0.9300
O1—C1	1.359 (9)	C21—C22	1.380 (10)
O1—C10	1.426 (8)	C21—C29	1.438 (11)
O2—C13	1.221 (10)	C22—C23	1.403 (11)
O3—C16	1.378 (9)	C22—H22	0.9300
O3—H3	0.8200	C23—C24	1.336 (12)
O4—C21	1.346 (8)	C23—H23	0.9300
O4—C30	1.429 (9)	C24—C25	1.374 (11)
O5—C33	1.214 (9)	C24—H24	0.9300
O6—C36	1.353 (9)	C25—C29	1.405 (10)
O6—H6	0.8200	C25—C26	1.431 (11)
O7—H29	0.8498	C26—C27	1.383 (11)
O7—H30	0.8474	C26—H26	0.9300
O8—H31	0.8522	C27—C28	1.395 (11)
O8—H32	0.8505	C27—H27	0.9300
C1—C2	1.375 (10)	C28—H28	0.9300
C1—C9	1.420 (10)	C30—C31	1.514 (11)
C2—C3	1.401 (11)	C30—H30A	0.9700
C2—H2A	0.9300	C30—H30B	0.9700
C3—C4	1.361 (11)	C31—C32	1.504 (11)
C3—H3A	0.9300	C31—H31A	0.9700
C4—C5	1.410 (10)	C31—H31B	0.9700
C4—H4	0.9300	C32—C33	1.509 (11)
C5—C6	1.407 (10)	C32—H32A	0.9700
C5—C9	1.412 (9)	C32—H32B	0.9700
C6—C7	1.365 (10)	C34—C35	1.414 (10)
C6—H6A	0.9300	C34—H34	0.9300
C7—C8	1.418 (11)	C35—C40	1.377 (10)
C7—H7	0.9300	C35—C36	1.440 (10)
C8—H8	0.9300	C36—C37	1.359 (11)
C10—C11	1.534 (10)	C37—C38	1.380 (11)
C10—H10A	0.9700	C37—H37	0.9300
C10—H10B	0.9700	C38—C39	1.364 (11)
C11—C12	1.502 (10)	C38—H38	0.9300
C11—H11A	0.9700	C39—C40	1.367 (11)
C11—H11B	0.9700	C40—H40	0.9300

C8—N1—C9	118.1 (6)	C19—C18—H18	121.0
C13—N2—N3	120.5 (7)	C17—C18—H18	121.0
C13—N2—H2	119.7	C20—C19—C18	124.2 (7)
N3—N2—H2	119.7	C20—C19—Cl1	118.2 (6)
C14—N3—N2	115.7 (6)	C18—C19—Cl1	117.6 (6)
C28—N4—C29	117.4 (7)	C19—C20—C15	117.9 (7)
C33—N5—N6	119.6 (6)	C19—C20—H20	121.0
C33—N5—H5	120.2	C15—C20—H20	121.0
N6—N5—H5	120.2	O4—C21—C22	126.4 (7)
C34—N6—N5	116.2 (6)	O4—C21—C29	114.7 (6)
C1—O1—C10	116.4 (6)	C22—C21—C29	118.9 (7)
C16—O3—H3	109.5	C21—C22—C23	120.2 (7)
C21—O4—C30	115.9 (6)	C21—C22—H22	119.9
C36—O6—H6	109.5	C23—C22—H22	119.9
H29—O7—H30	100.0	C24—C23—C22	121.5 (8)
H31—O8—H32	95.0	C24—C23—H23	119.2
O1—C1—C2	125.5 (7)	C22—C23—H23	119.2
O1—C1—C9	113.9 (6)	C23—C24—C25	120.0 (8)
C2—C1—C9	120.6 (7)	C23—C24—H24	120.0
C1—C2—C3	120.4 (7)	C25—C24—H24	120.0
C1—C2—H2A	119.8	C24—C25—C29	121.8 (8)
C3—C2—H2A	119.8	C24—C25—C26	122.9 (7)
C4—C3—C2	120.4 (7)	C29—C25—C26	115.3 (7)
C4—C3—H3A	119.8	C27—C26—C25	119.8 (7)
C2—C3—H3A	119.8	C27—C26—H26	120.1
C3—C4—C5	120.5 (7)	C25—C26—H26	120.1
C3—C4—H4	119.8	C26—C27—C28	119.1 (7)
C5—C4—H4	119.8	C26—C27—H27	120.4
C6—C5—C4	122.9 (7)	C28—C27—H27	120.4
C6—C5—C9	117.0 (6)	N4—C28—C27	123.4 (7)
C4—C5—C9	120.1 (7)	N4—C28—H28	118.3
C7—C6—C5	120.3 (7)	C27—C28—H28	118.3
C7—C6—H6A	119.9	N4—C29—C25	124.9 (7)
C5—C6—H6A	119.9	N4—C29—C21	117.5 (6)
C6—C7—C8	117.3 (7)	C25—C29—C21	117.6 (7)
C6—C7—H7	121.4	O4—C30—C31	109.6 (6)
C8—C7—H7	121.4	O4—C30—H30A	109.7
N1—C8—C7	124.7 (7)	C31—C30—H30A	109.7
N1—C8—H8	117.7	O4—C30—H30B	109.7
C7—C8—H8	117.7	C31—C30—H30B	109.7
N1—C9—C5	122.7 (6)	H30A—C30—H30B	108.2
N1—C9—C1	119.3 (6)	C32—C31—C30	109.2 (6)
C5—C9—C1	118.0 (6)	C32—C31—H31A	109.8
O1—C10—C11	109.6 (6)	C30—C31—H31A	109.8
O1—C10—H10A	109.8	C32—C31—H31B	109.8
C11—C10—H10A	109.8	C30—C31—H31B	109.8
O1—C10—H10B	109.8	H31A—C31—H31B	108.3
C11—C10—H10B	109.8	C31—C32—C33	113.7 (7)
H10A—C10—H10B	108.2	C31—C32—H32A	108.8
C12—C11—C10	108.5 (6)	C33—C32—H32A	108.8
C12—C11—H11A	110.0	C31—C32—H32B	108.8
C10—C11—H11A	110.0	C33—C32—H32B	108.8
C12—C11—H11B	110.0	H32A—C32—H32B	107.7
C10—C11—H11B	110.0	O5—C33—N5	122.6 (7)
H11A—C11—H11B	108.4	O5—C33—C32	125.1 (7)
C13—C12—C11	114.9 (7)	N5—C33—C32	112.2 (7)
C13—C12—H12A	108.5	N6—C34—C35	122.2 (7)
C11—C12—H12A	108.5	N6—C34—H34	118.9
C13—C12—H12B	108.5	C35—C34—H34	118.9
C11—C12—H12B	108.5	C40—C35—C34	119.8 (7)
H12A—C12—H12B	107.5	C40—C35—C36	117.1 (7)
O2—C13—N2	122.0 (8)	C34—C35—C36	123.0 (7)
O2—C13—C12	123.7 (7)	O6—C36—C37	120.0 (7)
N2—C13—C12	114.2 (8)	O6—C36—C35	119.9 (7)
N3—C14—C15	120.2 (7)	C37—C36—C35	120.1 (7)
N3—C14—H14	119.9	C36—C37—C38	121.3 (7)
C15—C14—H14	119.9	C36—C37—H37	119.3
C16—C15—C20	118.1 (7)	C38—C37—H37	119.3
C16—C15—C14	124.1 (7)	C39—C38—C37	118.4 (8)
C20—C15—C14	117.8 (6)	C39—C38—H38	120.8
C17—C16—O3	117.2 (7)	C37—C38—H38	120.8
C17—C16—C15	121.7 (7)	C38—C39—C40	122.0 (7)
O3—C16—C15	121.1 (7)	C38—C39—Cl2	119.1 (6)
C16—C17—C18	120.1 (7)	C40—C39—Cl2	118.7 (6)
C16—C17—H17	119.9	C39—C40—C35	120.8 (7)
C18—C17—H17	119.9	C39—C40—H40	119.6
C19—C18—C17	118.0 (7)	C35—C40—H40	119.6

C13—N2—N3—C14	−175.2 (7)	C14—C15—C20—C19	−179.0 (7)
C33—N5—N6—C34	176.2 (7)	C30—O4—C21—C22	−3.2 (10)
C10—O1—C1—C2	3.4 (11)	C30—O4—C21—C29	176.2 (6)
C10—O1—C1—C9	−175.8 (6)	O4—C21—C22—C23	178.3 (7)
O1—C1—C2—C3	178.7 (7)	C29—C21—C22—C23	−1.0 (11)
C9—C1—C2—C3	−2.1 (11)	C21—C22—C23—C24	1.9 (12)
C1—C2—C3—C4	0.7 (12)	C22—C23—C24—C25	−0.7 (12)
C2—C3—C4—C5	1.2 (12)	C23—C24—C25—C29	−1.3 (12)
C3—C4—C5—C6	179.6 (7)	C23—C24—C25—C26	−179.4 (7)
C3—C4—C5—C9	−1.5 (12)	C24—C25—C26—C27	177.0 (8)
C4—C5—C6—C7	179.5 (7)	C29—C25—C26—C27	−1.2 (11)
C9—C5—C6—C7	0.7 (11)	C25—C26—C27—C28	0.2 (12)
C5—C6—C7—C8	−0.3 (11)	C29—N4—C28—C27	−2.6 (12)
C9—N1—C8—C7	0.6 (11)	C26—C27—C28—N4	1.7 (13)
C6—C7—C8—N1	−0.4 (12)	C28—N4—C29—C25	1.5 (11)
C8—N1—C9—C5	−0.3 (10)	C28—N4—C29—C21	−178.5 (7)
C8—N1—C9—C1	−179.6 (7)	C24—C25—C29—N4	−177.9 (7)
C6—C5—C9—N1	−0.4 (11)	C26—C25—C29—N4	0.3 (11)
C4—C5—C9—N1	−179.3 (7)	C24—C25—C29—C21	2.1 (11)
C6—C5—C9—C1	179.0 (7)	C26—C25—C29—C21	−179.7 (7)
C4—C5—C9—C1	0.1 (11)	O4—C21—C29—N4	−0.3 (9)
O1—C1—C9—N1	0.4 (10)	C22—C21—C29—N4	179.1 (6)
C2—C1—C9—N1	−178.9 (7)	O4—C21—C29—C25	179.7 (6)
O1—C1—C9—C5	−179.0 (6)	C22—C21—C29—C25	−0.9 (10)
C2—C1—C9—C5	1.7 (11)	C21—O4—C30—C31	−177.9 (6)
C1—O1—C10—C11	178.9 (6)	O4—C30—C31—C32	179.1 (6)
O1—C10—C11—C12	−178.3 (7)	C30—C31—C32—C33	176.8 (7)
C10—C11—C12—C13	−177.6 (7)	N6—N5—C33—O5	−1.8 (12)
N3—N2—C13—O2	−1.4 (12)	N6—N5—C33—C32	176.2 (7)
N3—N2—C13—C12	−177.1 (7)	C31—C32—C33—O5	−39.6 (12)
C11—C12—C13—O2	40.8 (12)	C31—C32—C33—N5	142.4 (7)
C11—C12—C13—N2	−143.5 (8)	N5—N6—C34—C35	−179.3 (7)
N2—N3—C14—C15	−179.0 (6)	N6—C34—C35—C40	177.8 (7)
N3—C14—C15—C16	4.3 (11)	N6—C34—C35—C36	−6.8 (12)
N3—C14—C15—C20	−175.3 (7)	C40—C35—C36—O6	177.6 (7)
C20—C15—C16—C17	−1.8 (11)	C34—C35—C36—O6	2.1 (11)
C14—C15—C16—C17	178.6 (8)	C40—C35—C36—C37	−2.2 (10)
C20—C15—C16—O3	179.4 (7)	C34—C35—C36—C37	−177.8 (7)
C14—C15—C16—O3	−0.3 (11)	O6—C36—C37—C38	−179.3 (7)
O3—C16—C17—C18	−179.5 (7)	C35—C36—C37—C38	0.6 (12)
C15—C16—C17—C18	1.6 (13)	C36—C37—C38—C39	−1.4 (12)
C16—C17—C18—C19	−0.9 (12)	C37—C38—C39—C40	4.0 (12)
C17—C18—C19—C20	0.5 (12)	C37—C38—C39—Cl2	179.4 (6)
C17—C18—C19—Cl1	−179.8 (6)	C38—C39—C40—C35	−5.9 (12)
C18—C19—C20—C15	−0.7 (12)	Cl2—C39—C40—C35	178.7 (6)
Cl1—C19—C20—C15	179.6 (5)	C34—C35—C40—C39	−179.5 (7)
C16—C15—C20—C19	1.3 (10)	C36—C35—C40—C39	4.8 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7ⁱ	0.86	2.07	2.836 (9)	147
N5—H5···O8ⁱⁱ	0.86	2.05	2.820 (9)	149
O3—H3···N3	0.82	1.92	2.630 (8)	144
O6—H6···N6	0.82	1.91	2.633 (9)	147
O7—H29···N1	0.85	2.05	2.876 (8)	165
O7—H30···O5ⁱⁱⁱ	0.85	2.06	2.839 (9)	153
O8—H31···N4	0.85	2.04	2.872 (9)	166
O8—H32···O2^iv	0.85	1.99	2.845 (9)	180
C7—H7···O6ⁱⁱⁱ	0.93	2.53	3.267 (10)	137
C27—H27···O3^iv	0.93	2.56	3.303 (10)	137
C19—Cl1···Cg5^v	1.74 (1)	3.63 (1)	4.127 (9)	94 (1)
C39—Cl2···Cg1^vi	1.76 (1)	3.62 (1)	4.109 (9)	93 (1)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) x, −y, z+1/2; (v) x, −y+1, z−1/2; (vi) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClN₃O₃·H₂O
M_r	401.84
Crystal system, space group	Monoclinic, Cc
Temperature (K)	295
a, b, c (Å)	11.167 (3), 11.150 (3), 30.909 (10)
β (°)	96.970 (12)
V (Å³)	3820 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.32 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.929, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	17043, 5912, 3796
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.198, 1.02
No. of reflections	5912
No. of parameters	508
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.32
Absolute structure	Flack (1983), 2525 Friedel pairs
Absolute structure parameter	0.08 (13)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7ⁱ	0.86	2.07	2.836 (9)	147.3
N5—H5···O8ⁱⁱ	0.86	2.05	2.820 (9)	148.5
O3—H3···N3	0.82	1.92	2.630 (8)	144.0
O6—H6···N6	0.82	1.91	2.633 (9)	147.1
O7—H29···N1	0.85	2.05	2.876 (8)	165.1
O7—H30···O5ⁱⁱⁱ	0.85	2.06	2.839 (9)	152.6
O8—H31···N4	0.85	2.04	2.872 (9)	166.3
O8—H32···O2^iv	0.85	1.99	2.845 (9)	179.6
C7—H7···O6ⁱⁱⁱ	0.93	2.53	3.267 (10)	137
C27—H27···O3^iv	0.93	2.56	3.303 (10)	137
C19—Cl1···Cg5^v	1.735 (8)	3.632 (4)	4.127 (9)	93.8 (3)
C39—Cl2···Cg1^vi	1.756 (8)	3.616 (4)	4.109 (9)	93.3 (3)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) x, −y, z+1/2; (v) x, −y+1, z−1/2; (vi) x+1/2, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the Key Laboratory for Research and Development of Natural Drugs of Jiangxi Province.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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 (2007). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, Y. P., Zhang, L., Shi, J. L., Zhang, H. X. & Kang, B. S. (2003). Chin. J. Struct. Chem. 22, 587–590. Google Scholar
Chen, C. L., Goforth, A. M., Smith, M. D., Gemmill, W. R., Su, C. Y. & Loye, H. C. (2005). J. Cluster Sci. 16, 477–487. Web of Science CSD CrossRef CAS Google Scholar
Chen, M.-E. & Li, J.-M. (2009). Acta Cryst. E65, o295. Web of Science CSD CrossRef IUCr Journals Google Scholar
Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). CrystEngComm, 9, 379–389. Web of Science CSD CrossRef CAS Google Scholar
Muraoka, M., Ueda, A., Zhang, W., Kida, T., Nakatsuji, Y., Ikeda, I., Kanehisa, N. & Kai, Y. (1998). Tetrahedron Lett. 39, 9493–9496. Web of Science CSD CrossRef CAS Google Scholar
Pallavicini, P., Boiocchi, M., Dacarroa, G. & Mangano, C. (2007). New J. Chem. 31, 927–935. Web of Science CSD CrossRef CAS Google Scholar
Park, K. M., Moon, S. T., Kang, Y. J., Kim, H. J., Seo, J. & Lee, S. S. (2006). Inorg. Chem. Commun. 9, 671–674. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, T.-B., Zhou, Y.-Q., Zhang, Y.-M. & Zong, G.-Q. (2004). Acta Cryst. E60, o678–o680. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045–o2046. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, H., Meng, S.-M., Fan, Y.-Q. & Yang, G.-C. (2008). Acta Cryst. E64, o2114. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xu, A.-W., Cai, Y.-P., Zhang, L.-Z., Su, C.-Y. & Kang, B.-S. (2002). Acta Cryst. E58, m770–m771. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, S.-S., Wen, Y.-H., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o3682–o3683. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B. (2006). Acta Cryst. E62, o5146–o5147. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Li, J.-K., Sun, Y.-F. & Wu, R.-T. (2008). Acta Cryst. E64, o297. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, P.-W., Qiu, Q.-M., Lin, Y.-Y. & Liu, K.-F. (2006). Acta Cryst. E62, o1913–o1914. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Wu, R.-T., Li, J.-K. & Lu, J.-R. (2007). Acta Cryst. E63, o3284. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Z.-B., Wu, R.-T., Lu, J.-R. & Sun, Y.-F. (2006). Acta Cryst. E62, o4293–o4295. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 7| July 2009| Pages o1695-o1696

doi:10.1107/S1600536809023733

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-(5-Chloro-2-hy­droxy­benzyl­­idene)-4-(8-quinol­yl­oxy)butanohydrazide monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-(5-Chloro-2-hydroxybenzylidene)-4-(8-quinolyloxy)butanohydrazide monohydrate