4-Chloro-N′-[(Z)-4-(dimethyl­amino)benzyl­idene]benzohydrazide mono­hydrate

Fun, H.-K.; Patil, P.S.; Jebas, S.R.; Sujith, K.V.; Kalluraya, B.

doi:10.1107/S1600536808022861

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1594-o1595

doi:10.1107/S1600536808022861

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4-Chloro-N′-[(Z)-4-(dimethylamino)benzylidene]benzohydrazide monohydrate

Hoong-Kun Fun,^a ^* P. S. Patil,^b Samuel Robinson Jebas,^a ‡ K. V. Sujith ^c and B. Kalluraya ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 July 2008; accepted 21 July 2008; online 26 July 2008)

In the title compound, C₁₆H₁₆ClN₃O·H₂O, the dihedral angle between the two aromatic rings is 44.58 (11)°. The N atom of the dimethylamino group adopts a pyramidal configuration. In the crystal structure, molecules are linked into a two-dimensional network parallel to the (001) plane by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds involving the water molecule and C—H⋯Cl hydrogen bonds. In addition, C—H⋯π interactions are observed.

Related literature

For the biological activities of hydrazones, see: Bedia et al. (2006 ); Rollas et al. (2002 ); Terzioglu & Gürsoy (2003 ); Duraisamy et al. (2008 ); Singh et al. (1992 ); Ergenç & Günay, (1998 ); Durgun et al. (1993 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₆ClN₃O·H₂O
M_r = 319.78
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.4418 (1) Å
b = 6.9344 (1) Å
c = 33.8083 (7) Å
V = 1510.22 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100.0 (1) K
0.32 × 0.16 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.921, T_max = 0.981
12336 measured reflections
4311 independent reflections
3301 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.114
S = 1.01
4311 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ), 1724 Friedel pairs
Flack parameter: −0.14 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N3ⁱ	0.84	2.28	3.045 (2)	152
N1—H1N1⋯O1W	0.86 (1)	2.00 (1)	2.843 (3)	169 (2)
O1W—H2W1⋯O1ⁱⁱ	0.84	2.02	2.790 (2)	152
O1W—H2W1⋯N2ⁱⁱ	0.84	2.59	3.240 (3)	135
C15—H15C⋯Cl1ⁱⁱⁱ	0.96	2.78	3.704 (2)	163
C1—H1⋯Cg1^iv	0.93	2.97	3.621 (2)	128
C4—H4⋯Cg1^v	0.93	2.89	3.565 (2)	130
C10—H10⋯Cg2^vi	0.93	2.87	3.589 (2)	135
C13—H13⋯Cg2^vii	0.93	2.81	3.497 (3)	131
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x-{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (vii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022861/ci2637sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022861/ci2637Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gürsoy, 2003). They are used as chromogenic receptors to show colorimetric responses and UV-Vis spectral changes in the presence of fluoride ions in organic solvents (Duraisamy et al., 2008). Hydrazide-hydrazone compounds are not only intermediates but they are also very effective organic compounds in their own right. When they are used as intermediates, coupling products can be synthesized by using the active hydrogen component of CONHNCH azometine group (Singh et al., 1992). N-Alkyl hydrazides can be synthesized by reduction of hydrazones with NaBH₄ (Ergenç & Günay, 1998) and substituted 1,3,4-oxadiazolines can be synthesized when hydrazones are heated in the presence of acetic anhydride (Durgun et al., 1993). Prompted by these reviews, the title compound was synthesized and its crystal structure reported.

The bond lengths and angles in the title molecule (Fig. 1) are found to have normal values (Allen et al., 1987). The dihedral angle between the two benzene rings (C1–C6 and C9–C14) is 44.58 (11)° indicating that the molecule is non-planar. Atom N3 adopts a pyramidal configuration.

The crystal packing (Fig. 2) shows that the molecules are linked into two-dimensional networks parallel to the (001) plane by intermolecular O—H···N, O—H···O and C—H···Cl hydrogen bonds. In addition, the packing is stabilized by C—H···π interactions.

Related literature top

For the biological activities of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002); Terzioglu & Gürsoy (2003); Duraisamy et al. (2008); Singh et al. (1992); Ergenç & Günay, (1998); Durgun et al. (1993). For bond-length data, see: Allen et al. (1987). Cg1 and Cg2 are centroids of the C1–C6 and C9–C14 rings, respectively.

Experimental top

The title compound was prepared by Schiff base condensation of 4-chlorophenyl hydrazide (0.01 mol) and 4-(dimethylamino)benzaldehyde (0.01 mol) in ethanol (30 ml) with 3 drops of concentrated H₂SO₄. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with water and dried. Single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation (yield 64%). Analysis % for C₁₆H₁₆N₃OCl found (calculated): C 63.62 (63.68), H 5.37 (5.3), N 13.88 (13.93).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis.

(I) top

Crystal data top

C₁₆H₁₆ClN₃O·H₂O	F(000) = 672
M_r = 319.78	D_x = 1.406 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1906 reflections
a = 6.4418 (1) Å	θ = 2.4–23.3°
b = 6.9344 (1) Å	µ = 0.26 mm⁻¹
c = 33.8083 (7) Å	T = 100 K
V = 1510.22 (4) Å³	Needle, colourless
Z = 4	0.32 × 0.16 × 0.07 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4311 independent reflections
Radiation source: fine-focus sealed tube	3301 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.921, T_max = 0.981	k = −9→6
12336 measured reflections	l = −47→37

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0492P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4311 reflections	Δρ_max = 0.34 e Å⁻³
205 parameters	Δρ_min = −0.34 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1724 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.14 (7)

Crystal data top

C₁₆H₁₆ClN₃O·H₂O	V = 1510.22 (4) Å³
M_r = 319.78	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.4418 (1) Å	µ = 0.26 mm⁻¹
b = 6.9344 (1) Å	T = 100 K
c = 33.8083 (7) Å	0.32 × 0.16 × 0.07 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4311 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3301 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.981	R_int = 0.056
12336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.114	Δρ_max = 0.34 e Å⁻³
S = 1.01	Δρ_min = −0.34 e Å⁻³
4311 reflections	Absolute structure: Flack (1983), 1724 Friedel pairs
205 parameters	Absolute structure parameter: −0.14 (7)
2 restraints

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.39865 (9)	0.50981 (9)	0.568340 (15)	0.02126 (14)
O1	−0.3268 (2)	0.4990 (2)	0.42597 (4)	0.0206 (3)
N1	−0.0370 (3)	0.4579 (3)	0.38853 (5)	0.0146 (4)
N2	−0.1527 (3)	0.4602 (3)	0.35420 (5)	0.0151 (4)
N3	−0.4409 (3)	0.4624 (3)	0.17091 (5)	0.0166 (4)
C1	−0.0827 (4)	0.4376 (3)	0.49549 (6)	0.0154 (5)
H1	−0.2199	0.3967	0.4971	0.018*
C2	0.0388 (4)	0.4421 (3)	0.52925 (6)	0.0173 (5)
H2	−0.0147	0.4008	0.5534	0.021*
C3	0.2405 (3)	0.5086 (4)	0.52666 (6)	0.0154 (4)
C4	0.3243 (4)	0.5704 (3)	0.49095 (6)	0.0157 (5)
H4	0.4595	0.6170	0.4897	0.019*
C5	0.2028 (3)	0.5613 (3)	0.45730 (7)	0.0153 (5)
H5	0.2578	0.6005	0.4332	0.018*
C6	−0.0002 (3)	0.4943 (4)	0.45901 (6)	0.0148 (4)
C7	−0.1372 (3)	0.4843 (3)	0.42347 (6)	0.0136 (4)
C8	−0.0579 (4)	0.4106 (3)	0.32251 (6)	0.0147 (5)
H8	0.0795	0.3699	0.3239	0.018*
C9	−0.1631 (4)	0.4172 (3)	0.28408 (6)	0.0135 (5)
C10	−0.0582 (4)	0.3550 (3)	0.25039 (7)	0.0158 (5)
H10	0.0757	0.3062	0.2527	0.019*
C11	−0.1513 (4)	0.3651 (3)	0.21331 (6)	0.0156 (5)
H11	−0.0797	0.3200	0.1913	0.019*
C12	−0.3506 (4)	0.4420 (3)	0.20852 (6)	0.0152 (5)
C13	−0.4564 (3)	0.5034 (4)	0.24292 (6)	0.0160 (4)
H13	−0.5897	0.5538	0.2408	0.019*
C14	−0.3643 (3)	0.4893 (3)	0.27960 (6)	0.0151 (4)
H14	−0.4376	0.5286	0.3019	0.018*
C15	−0.6672 (4)	0.4541 (4)	0.16837 (7)	0.0205 (5)
H15A	−0.7266	0.5409	0.1874	0.031*
H15B	−0.7132	0.3251	0.1738	0.031*
H15C	−0.7105	0.4907	0.1423	0.031*
C16	−0.3386 (4)	0.3595 (4)	0.13815 (7)	0.0245 (6)
H16A	−0.1993	0.4065	0.1352	0.037*
H16B	−0.4144	0.3811	0.1141	0.037*
H16C	−0.3354	0.2239	0.1438	0.037*
H1N1	0.0892 (19)	0.419 (3)	0.3882 (7)	0.028 (7)*
O1W	0.3779 (3)	0.3316 (2)	0.37632 (5)	0.0259 (4)
H1W1	0.4093	0.2594	0.3573	0.039*
H2W1	0.4830	0.3923	0.3837	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0253 (3)	0.0248 (3)	0.0137 (3)	−0.0021 (3)	−0.0051 (2)	0.0007 (3)
O1	0.0130 (7)	0.0297 (9)	0.0192 (8)	0.0003 (7)	−0.0006 (6)	−0.0030 (8)
N1	0.0122 (9)	0.0197 (11)	0.0120 (9)	0.0011 (8)	−0.0031 (7)	−0.0003 (8)
N2	0.0170 (9)	0.0155 (10)	0.0127 (9)	−0.0013 (7)	−0.0028 (7)	−0.0004 (7)
N3	0.0203 (10)	0.0189 (11)	0.0107 (9)	0.0014 (8)	−0.0012 (7)	−0.0007 (8)
C1	0.0170 (11)	0.0118 (11)	0.0174 (11)	0.0005 (8)	0.0039 (9)	−0.0007 (8)
C2	0.0236 (12)	0.0168 (12)	0.0117 (11)	−0.0016 (9)	0.0041 (9)	−0.0012 (9)
C3	0.0221 (11)	0.0160 (11)	0.0081 (10)	0.0016 (10)	−0.0016 (8)	−0.0010 (10)
C4	0.0149 (11)	0.0166 (12)	0.0155 (12)	−0.0004 (8)	0.0005 (9)	−0.0013 (9)
C5	0.0193 (12)	0.0157 (12)	0.0110 (11)	0.0009 (8)	0.0017 (9)	−0.0003 (9)
C6	0.0151 (10)	0.0148 (11)	0.0144 (10)	0.0012 (9)	−0.0001 (8)	−0.0042 (10)
C7	0.0170 (10)	0.0132 (11)	0.0108 (10)	−0.0012 (9)	0.0007 (8)	0.0003 (9)
C8	0.0124 (10)	0.0162 (11)	0.0155 (12)	−0.0015 (9)	−0.0007 (9)	0.0006 (9)
C9	0.0157 (11)	0.0128 (11)	0.0121 (11)	−0.0013 (8)	−0.0013 (9)	0.0004 (8)
C10	0.0131 (11)	0.0179 (12)	0.0164 (12)	−0.0009 (9)	0.0025 (9)	−0.0008 (9)
C11	0.0166 (11)	0.0191 (12)	0.0111 (11)	−0.0002 (9)	0.0025 (9)	−0.0030 (9)
C12	0.0192 (11)	0.0127 (11)	0.0136 (11)	−0.0016 (9)	−0.0013 (9)	0.0021 (8)
C13	0.0145 (10)	0.0169 (11)	0.0167 (11)	0.0024 (10)	0.0000 (8)	−0.0003 (10)
C14	0.0196 (10)	0.0142 (11)	0.0116 (10)	0.0002 (10)	0.0022 (8)	−0.0025 (9)
C15	0.0207 (12)	0.0222 (14)	0.0186 (12)	0.0021 (10)	−0.0054 (9)	0.0008 (10)
C16	0.0297 (14)	0.0304 (15)	0.0134 (12)	0.0070 (11)	−0.0010 (10)	−0.0015 (10)
O1W	0.0162 (9)	0.0304 (10)	0.0310 (10)	0.0004 (7)	−0.0004 (8)	−0.0137 (8)

Geometric parameters (Å, º) top

Cl1—C3	1.739 (2)	C8—C9	1.466 (3)
O1—C7	1.229 (2)	C8—H8	0.93
N1—C7	1.358 (3)	C9—C10	1.393 (3)
N1—N2	1.379 (2)	C9—C14	1.397 (3)
N1—H1N1	0.857 (10)	C10—C11	1.391 (3)
N2—C8	1.280 (3)	C10—H10	0.93
N3—C12	1.405 (3)	C11—C12	1.400 (3)
N3—C15	1.461 (3)	C11—H11	0.93
N3—C16	1.473 (3)	C12—C13	1.414 (3)
C1—C2	1.384 (3)	C13—C14	1.378 (3)
C1—C6	1.399 (3)	C13—H13	0.93
C1—H1	0.93	C14—H14	0.93
C2—C3	1.382 (3)	C15—H15A	0.96
C2—H2	0.93	C15—H15B	0.96
C3—C4	1.390 (3)	C15—H15C	0.96
C4—C5	1.382 (3)	C16—H16A	0.96
C4—H4	0.93	C16—H16B	0.96
C5—C6	1.389 (3)	C16—H16C	0.96
C5—H5	0.93	O1W—H1W1	0.84
C6—C7	1.493 (3)	O1W—H2W1	0.83

C7—N1—N2	118.25 (17)	C10—C9—C14	118.2 (2)
C7—N1—H1N1	120.4 (17)	C10—C9—C8	119.4 (2)
N2—N1—H1N1	120.3 (17)	C14—C9—C8	122.4 (2)
C8—N2—N1	116.33 (19)	C11—C10—C9	120.8 (2)
C12—N3—C15	117.51 (19)	C11—C10—H10	119.6
C12—N3—C16	116.49 (19)	C9—C10—H10	119.6
C15—N3—C16	112.54 (19)	C10—C11—C12	121.3 (2)
C2—C1—C6	120.4 (2)	C10—C11—H11	119.4
C2—C1—H1	119.8	C12—C11—H11	119.4
C6—C1—H1	119.8	C11—C12—N3	121.5 (2)
C3—C2—C1	119.1 (2)	C11—C12—C13	117.5 (2)
C3—C2—H2	120.4	N3—C12—C13	121.0 (2)
C1—C2—H2	120.4	C14—C13—C12	120.8 (2)
C2—C3—C4	121.5 (2)	C14—C13—H13	119.6
C2—C3—Cl1	120.08 (17)	C12—C13—H13	119.6
C4—C3—Cl1	118.36 (17)	C13—C14—C9	121.5 (2)
C5—C4—C3	118.8 (2)	C13—C14—H14	119.3
C5—C4—H4	120.6	C9—C14—H14	119.3
C3—C4—H4	120.6	N3—C15—H15A	109.5
C4—C5—C6	120.9 (2)	N3—C15—H15B	109.5
C4—C5—H5	119.5	H15A—C15—H15B	109.5
C6—C5—H5	119.5	N3—C15—H15C	109.5
C5—C6—C1	119.2 (2)	H15A—C15—H15C	109.5
C5—C6—C7	122.61 (19)	H15B—C15—H15C	109.5
C1—C6—C7	118.15 (19)	N3—C16—H16A	109.5
O1—C7—N1	122.92 (19)	N3—C16—H16B	109.5
O1—C7—C6	121.92 (18)	H16A—C16—H16B	109.5
N1—C7—C6	115.16 (18)	N3—C16—H16C	109.5
N2—C8—C9	120.9 (2)	H16A—C16—H16C	109.5
N2—C8—H8	119.6	H16B—C16—H16C	109.5
C9—C8—H8	119.6	H1W1—O1W—H2W1	109.6

C7—N1—N2—C8	−171.4 (2)	N1—N2—C8—C9	−176.96 (18)
C6—C1—C2—C3	1.9 (3)	N2—C8—C9—C10	−177.5 (2)
C1—C2—C3—C4	−0.2 (4)	N2—C8—C9—C14	4.5 (3)
C1—C2—C3—Cl1	−178.32 (17)	C14—C9—C10—C11	0.2 (3)
C2—C3—C4—C5	−1.1 (3)	C8—C9—C10—C11	−177.9 (2)
Cl1—C3—C4—C5	176.95 (17)	C9—C10—C11—C12	1.5 (3)
C3—C4—C5—C6	0.9 (3)	C10—C11—C12—N3	176.4 (2)
C4—C5—C6—C1	0.7 (3)	C10—C11—C12—C13	−1.9 (3)
C4—C5—C6—C7	179.3 (2)	C15—N3—C12—C11	151.7 (2)
C2—C1—C6—C5	−2.2 (3)	C16—N3—C12—C11	13.7 (3)
C2—C1—C6—C7	179.2 (2)	C15—N3—C12—C13	−30.0 (3)
N2—N1—C7—O1	4.3 (3)	C16—N3—C12—C13	−168.0 (2)
N2—N1—C7—C6	−175.69 (19)	C11—C12—C13—C14	0.7 (3)
C5—C6—C7—O1	−151.1 (2)	N3—C12—C13—C14	−177.7 (2)
C1—C6—C7—O1	27.4 (3)	C12—C13—C14—C9	1.0 (4)
C5—C6—C7—N1	28.8 (3)	C10—C9—C14—C13	−1.5 (3)
C1—C6—C7—N1	−152.6 (2)	C8—C9—C14—C13	176.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N3ⁱ	0.84	2.28	3.045 (2)	152
N1—H1N1···O1W	0.86 (1)	2.00 (1)	2.843 (3)	169 (2)
O1W—H2W1···O1ⁱⁱ	0.84	2.02	2.790 (2)	152
O1W—H2W1···N2ⁱⁱ	0.84	2.59	3.240 (3)	135
C15—H15C···Cl1ⁱⁱⁱ	0.96	2.78	3.704 (2)	163
C1—H1···Cg1^iv	0.93	2.97	3.621 (2)	128
C4—H4···Cg1^v	0.93	2.89	3.565 (2)	130
C10—H10···Cg2^vi	0.93	2.87	3.589 (2)	135
C13—H13···Cg2^vii	0.93	2.81	3.497 (3)	131

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x−1/2, −y+1, z−1/2; (iv) −x−1, y+1/2, −z+3/2; (v) −x, y+3/2, −z+3/2; (vi) x+1/2, −y−1/2, −z; (vii) x−1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClN₃O·H₂O
M_r	319.78
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.4418 (1), 6.9344 (1), 33.8083 (7)
V (Å³)	1510.22 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.32 × 0.16 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.921, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	12336, 4311, 3301
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.114, 1.01
No. of reflections	4311
No. of parameters	205
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.34
Absolute structure	Flack (1983), 1724 Friedel pairs
Absolute structure parameter	−0.14 (7)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N3ⁱ	0.84	2.28	3.045 (2)	152
N1—H1N1···O1W	0.86 (1)	2.00 (1)	2.843 (3)	169 (2)
O1W—H2W1···O1ⁱⁱ	0.84	2.02	2.790 (2)	152
O1W—H2W1···N2ⁱⁱ	0.84	2.59	3.240 (3)	135
C15—H15C···Cl1ⁱⁱⁱ	0.96	2.78	3.704 (2)	163
C1—H1···Cg1^iv	0.93	2.97	3.621 (2)	128
C4—H4···Cg1^v	0.93	2.89	3.565 (2)	130
C10—H10···Cg2^vi	0.93	2.87	3.589 (2)	135
C13—H13···Cg2^vii	0.93	2.81	3.497 (3)	131

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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