(E)-N′-(4-Chloro­benzyl­idene)-1-benzofuran-2-carbohydrazide monohydrate

Fun, H.-K.; Quah, C.K.; Nitinchandra; Kalluraya, B.; Babu, M.

doi:10.1107/S1600536812027523

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2163

https://doi.org/10.1107/S1600536812027523

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(E)-N′-(4-Chlorobenzylidene)-1-benzofuran-2-carbohydrazide monohydrate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Nitinchandra,^b Balakrishna Kalluraya ^b and M. Babu ^b

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

(Received 11 June 2012; accepted 18 June 2012; online 23 June 2012)

The title compound, C₁₆H₁₁ClN₂O₂·H₂O, exists in an E conformation with respect to the N=C bond. The benzofuran ring system forms a dihedral angle of 1.26 (4)° with the benzene ring. In the crystal, molecules are linked via (N,C)—H⋯O bifurcated acceptor hydrogen bonds and (O,O,C)—H⋯O trifurcated acceptor hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For general background to hydrazone derivatives, see: Sridhar & Perumal (2003 ); Vijayakumar et al. (2011 ). For standard bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For related structures, see: Fun, Quah & Abdel-Aziz (2012 ); Fun, Quah, Nitinchandra et al. (2012 ); Fun, Quah, Shyma et al. (2012 ).

Experimental

Crystal data

C₁₆H₁₁ClN₂O₂·H₂O
M_r = 316.73
Monoclinic, C c
a = 24.6121 (15) Å
b = 4.6625 (3) Å
c = 12.6570 (8) Å
β = 99.294 (1)°
V = 1433.37 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 100 K
0.57 × 0.34 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.856, T_max = 0.975
7338 measured reflections
4620 independent reflections
4511 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.04
4620 reflections
211 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 2025 Friedel pairs
Flack parameter: 0.03 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2	0.855 (19)	2.040 (19)	2.8815 (11)	168.1 (18)
O1W—H2W1⋯O2ⁱ	0.75 (2)	2.06 (2)	2.8045 (11)	173 (2)
N1—H1N1⋯O1Wⁱⁱ	0.909 (19)	1.952 (19)	2.8083 (12)	156.2 (18)
C2—H2A⋯O2ⁱⁱ	0.95	2.57	3.3710 (14)	142
C10—H10A⋯O1Wⁱⁱ	0.95	2.54	3.3067 (13)	138
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027523/is5157sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027523/is5157Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027523/is5157Isup3.cml

checkCIF report

Comment top

Hydrazones are versatile intermediates and important building blocks. Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar & Perumal, 2003). Hydrazones of aliphatic and aromatic methyl ketones yield pyrazole-4-carboxaldehyde on formylation by treatment with Vilsmeier reagent. Hydrazones derived from anisaldehyde and 4-nitro-5-ethoxycarbonyl phenylhydrazine showed excellent NLO property (Vijayakumar et al., 2011). Prompted by these observations, the title compound was synthesized and its crystal structure is reported.

The title compound (Fig. 1) consists of a N'-[4-chlorophenyl)methylidene]-1-benzofuran-2-carbohydrazide molecule and a water molecule in the asymmetric unit and exists in an E configuration with respect to the N2═C10 bond [1.2848 (13) Å]. The benzofuran ring system (O1/C1-C8, r.m.s deviation = 0.012 Å) forms a dihedral angle of 1.26 (4)° with the benzene ring (C11–C16). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun, Quah & Abdel-Aziz, 2012; Fun, Quah, Nitinchandra et al., 2012; Fun, Quah, Shyma et al., 2012).

In the crystal (Fig. 2), molecules are linked via intermolecular N1—H1N1···O1W, C10—H10A···O1W bifurcated acceptor hydrogen bonds and O1W—H2W1···O2, O1W—H2W1···O2, C2—H2A···O2 trifurcated acceptor hydrogen bonds (Table 1) to form two-dimensional layers parallel to (100).

Related literature top

For general background to hydrazone derivatives, see: Sridhar & Perumal (2003); Vijayakumar et al. (2011). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For related structures, see: Fun, Quah & Abdel-Aziz (2012); Fun, Quah, Nitinchandra et al. (2012); Fun, Quah, Shyma et al. (2012).

Experimental top

The title compound was obtained by refluxing a mixture of 1-benzofuran-2-carbohydrazide (0.01 mol), 4-chlorobenzaldehyde (0.01 mol) in ethanol (30 ml) and 3 drops of concentrated sulfuric acid for 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol-N,N-dimethylformamide (DMF) (3:1) solution.

Structure description top

For general background to hydrazone derivatives, see: Sridhar & Perumal (2003); Vijayakumar et al. (2011). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For related structures, see: Fun, Quah & Abdel-Aziz (2012); Fun, Quah, Nitinchandra et al. (2012); Fun, Quah, Shyma et al. (2012).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

(E)-N'-(4-Chlorobenzylidene)-1-benzofuran-2-carbohydrazide monohydrate top

Crystal data top

C₁₆H₁₁ClN₂O₂·H₂O	F(000) = 656
M_r = 316.73	D_x = 1.468 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5261 reflections
a = 24.6121 (15) Å	θ = 3.3–32.6°
b = 4.6625 (3) Å	µ = 0.28 mm⁻¹
c = 12.6570 (8) Å	T = 100 K
β = 99.294 (1)°	Plate, yellow
V = 1433.37 (16) Å³	0.57 × 0.34 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4620 independent reflections
Radiation source: fine-focus sealed tube	4511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 32.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −35→36
T_min = 0.856, T_max = 0.975	k = −6→7
7338 measured reflections	l = −19→18

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0441P)² + 0.2352P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
4620 reflections	Δρ_max = 0.34 e Å⁻³
211 parameters	Δρ_min = −0.19 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2025 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (3)

Crystal data top

C₁₆H₁₁ClN₂O₂·H₂O	V = 1433.37 (16) Å³
M_r = 316.73	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 24.6121 (15) Å	µ = 0.28 mm⁻¹
b = 4.6625 (3) Å	T = 100 K
c = 12.6570 (8) Å	0.57 × 0.34 × 0.09 mm
β = 99.294 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4620 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4511 reflections with I > 2σ(I)
T_min = 0.856, T_max = 0.975	R_int = 0.019
7338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.073	Δρ_max = 0.34 e Å⁻³
S = 1.04	Δρ_min = −0.19 e Å⁻³
4620 reflections	Absolute structure: Flack (1983), 2025 Friedel pairs
211 parameters	Absolute structure parameter: 0.03 (3)
2 restraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.362378 (12)	2.08150 (5)	0.62418 (2)	0.02405 (7)
O1	0.66851 (3)	0.45040 (16)	0.85030 (6)	0.01364 (14)
O2	0.61809 (3)	0.76090 (16)	0.59506 (6)	0.01549 (14)
N1	0.59805 (4)	0.87204 (18)	0.76135 (7)	0.01207 (15)
N2	0.56127 (4)	1.07881 (18)	0.71696 (7)	0.01267 (15)
C1	0.70999 (4)	0.2512 (2)	0.87293 (8)	0.01263 (16)
C2	0.72801 (5)	0.1294 (2)	0.97208 (8)	0.01605 (18)
H2A	0.7119	0.1758	1.0332	0.019*
C3	0.77114 (5)	−0.0650 (2)	0.97685 (9)	0.0174 (2)
H3A	0.7851	−0.1537	1.0433	0.021*
C4	0.79475 (5)	−0.1341 (2)	0.88576 (9)	0.01846 (19)
H4A	0.8245	−0.2663	0.8922	0.022*
C5	0.77532 (5)	−0.0121 (2)	0.78699 (9)	0.01828 (19)
H5A	0.7911	−0.0607	0.7256	0.022*
C6	0.73181 (4)	0.1849 (2)	0.77992 (8)	0.01348 (17)
C7	0.70075 (4)	0.3521 (2)	0.69570 (8)	0.01474 (17)
H7A	0.7049	0.3542	0.6224	0.018*
C8	0.66431 (4)	0.5062 (2)	0.74233 (8)	0.01243 (16)
C9	0.62453 (4)	0.7225 (2)	0.69371 (8)	0.01223 (17)
C10	0.53404 (4)	1.2045 (2)	0.78210 (8)	0.01311 (17)
H10A	0.5403	1.1551	0.8559	0.016*
C11	0.49318 (4)	1.4248 (2)	0.74216 (8)	0.01304 (17)
C12	0.46196 (5)	1.5490 (2)	0.81314 (9)	0.01721 (19)
H12A	0.4686	1.4950	0.8865	0.021*
C13	0.42134 (5)	1.7509 (2)	0.77787 (10)	0.0192 (2)
H13A	0.3998	1.8321	0.8261	0.023*
C14	0.41298 (4)	1.8308 (2)	0.67104 (10)	0.01754 (19)
C15	0.44432 (5)	1.7160 (2)	0.59957 (9)	0.0181 (2)
H15A	0.4386	1.7771	0.5270	0.022*
C16	0.48413 (4)	1.5106 (2)	0.63496 (8)	0.01574 (18)
H16A	0.5052	1.4284	0.5861	0.019*
O1W	0.58492 (4)	0.25083 (19)	0.47297 (6)	0.01780 (15)
H1W1	0.5989 (8)	0.402 (4)	0.5046 (15)	0.026 (5)*
H2W1	0.5934 (10)	0.127 (5)	0.510 (2)	0.044 (6)*
H1N1	0.6041 (8)	0.820 (4)	0.8315 (15)	0.021 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01451 (11)	0.01539 (10)	0.03983 (16)	0.00472 (8)	−0.00296 (10)	−0.00640 (11)
O1	0.0150 (3)	0.0136 (3)	0.0126 (3)	0.0039 (2)	0.0033 (3)	0.0011 (2)
O2	0.0206 (4)	0.0144 (3)	0.0122 (3)	0.0019 (3)	0.0046 (3)	0.0009 (3)
N1	0.0125 (4)	0.0121 (3)	0.0117 (3)	0.0020 (3)	0.0019 (3)	0.0011 (3)
N2	0.0120 (4)	0.0116 (3)	0.0144 (4)	0.0009 (3)	0.0018 (3)	0.0008 (3)
C1	0.0126 (4)	0.0109 (4)	0.0144 (4)	0.0010 (3)	0.0024 (3)	−0.0005 (3)
C2	0.0175 (5)	0.0169 (4)	0.0137 (4)	0.0026 (4)	0.0024 (4)	0.0009 (3)
C3	0.0179 (5)	0.0170 (4)	0.0164 (5)	0.0023 (3)	0.0004 (4)	0.0019 (3)
C4	0.0165 (5)	0.0183 (4)	0.0207 (5)	0.0060 (4)	0.0034 (4)	0.0012 (4)
C5	0.0186 (5)	0.0187 (4)	0.0185 (5)	0.0062 (4)	0.0060 (4)	−0.0003 (4)
C6	0.0140 (4)	0.0130 (4)	0.0140 (4)	0.0017 (3)	0.0040 (3)	0.0003 (3)
C7	0.0165 (4)	0.0147 (4)	0.0135 (4)	0.0023 (3)	0.0038 (3)	0.0009 (3)
C8	0.0134 (4)	0.0120 (4)	0.0121 (4)	0.0012 (3)	0.0026 (3)	0.0009 (3)
C9	0.0134 (4)	0.0106 (4)	0.0131 (4)	−0.0003 (3)	0.0034 (3)	0.0003 (3)
C10	0.0140 (4)	0.0127 (4)	0.0129 (4)	0.0007 (3)	0.0029 (3)	0.0007 (3)
C11	0.0124 (4)	0.0122 (4)	0.0150 (4)	0.0002 (3)	0.0039 (3)	−0.0022 (3)
C12	0.0193 (5)	0.0159 (4)	0.0180 (4)	0.0011 (4)	0.0077 (4)	−0.0020 (4)
C13	0.0169 (5)	0.0166 (4)	0.0257 (5)	0.0017 (4)	0.0080 (4)	−0.0050 (4)
C14	0.0116 (4)	0.0119 (4)	0.0284 (5)	0.0014 (3)	0.0009 (4)	−0.0040 (4)
C15	0.0175 (5)	0.0170 (4)	0.0187 (5)	0.0039 (3)	0.0000 (4)	−0.0012 (4)
C16	0.0153 (4)	0.0166 (4)	0.0155 (4)	0.0044 (3)	0.0028 (3)	−0.0007 (3)
O1W	0.0256 (4)	0.0159 (3)	0.0116 (3)	−0.0015 (3)	0.0022 (3)	0.0006 (3)

Geometric parameters (Å, º) top

Cl1—C14	1.7407 (11)	C6—C7	1.4371 (14)
O1—C1	1.3757 (12)	C7—C8	1.3566 (14)
O1—C8	1.3785 (12)	C7—H7A	0.9500
O2—C9	1.2459 (12)	C8—C9	1.4696 (13)
N1—C9	1.3505 (12)	C10—C11	1.4690 (14)
N1—N2	1.3785 (12)	C10—H10A	0.9500
N1—H1N1	0.909 (18)	C11—C16	1.3975 (14)
N2—C10	1.2848 (13)	C11—C12	1.3984 (14)
C1—C2	1.3837 (14)	C12—C13	1.3931 (16)
C1—C6	1.4049 (13)	C12—H12A	0.9500
C2—C3	1.3896 (15)	C13—C14	1.3856 (18)
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.4097 (16)	C14—C15	1.3876 (16)
C3—H3A	0.9500	C15—C16	1.3916 (15)
C4—C5	1.3863 (16)	C15—H15A	0.9500
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.4025 (14)	O1W—H1W1	0.857 (19)
C5—H5A	0.9500	O1W—H2W1	0.75 (3)

C1—O1—C8	105.55 (8)	C7—C8—C9	128.60 (9)
C9—N1—N2	117.07 (8)	O1—C8—C9	118.87 (8)
C9—N1—H1N1	117.6 (12)	O2—C9—N1	124.39 (9)
N2—N1—H1N1	125.2 (12)	O2—C9—C8	119.11 (9)
C10—N2—N1	115.70 (9)	N1—C9—C8	116.48 (8)
O1—C1—C2	125.76 (9)	N2—C10—C11	119.81 (9)
O1—C1—C6	110.21 (8)	N2—C10—H10A	120.1
C2—C1—C6	124.03 (9)	C11—C10—H10A	120.1
C1—C2—C3	115.97 (10)	C16—C11—C12	119.16 (10)
C1—C2—H2A	122.0	C16—C11—C10	121.81 (9)
C3—C2—H2A	122.0	C12—C11—C10	119.02 (9)
C2—C3—C4	121.76 (10)	C13—C12—C11	120.95 (10)
C2—C3—H3A	119.1	C13—C12—H12A	119.5
C4—C3—H3A	119.1	C11—C12—H12A	119.5
C5—C4—C3	121.07 (10)	C14—C13—C12	118.71 (10)
C5—C4—H4A	119.5	C14—C13—H13A	120.6
C3—C4—H4A	119.5	C12—C13—H13A	120.6
C4—C5—C6	118.35 (10)	C13—C14—C15	121.45 (10)
C4—C5—H5A	120.8	C13—C14—Cl1	119.90 (8)
C6—C5—H5A	120.8	C15—C14—Cl1	118.65 (9)
C5—C6—C1	118.81 (9)	C14—C15—C16	119.50 (10)
C5—C6—C7	135.37 (10)	C14—C15—H15A	120.2
C1—C6—C7	105.81 (9)	C16—C15—H15A	120.2
C8—C7—C6	105.94 (9)	C15—C16—C11	120.20 (10)
C8—C7—H7A	127.0	C15—C16—H16A	119.9
C6—C7—H7A	127.0	C11—C16—H16A	119.9
C7—C8—O1	112.48 (9)	H1W1—O1W—H2W1	107 (2)

C9—N1—N2—C10	175.60 (9)	N2—N1—C9—O2	0.48 (14)
C8—O1—C1—C2	−179.09 (10)	N2—N1—C9—C8	179.00 (8)
C8—O1—C1—C6	0.46 (11)	C7—C8—C9—O2	7.15 (16)
O1—C1—C2—C3	−179.16 (10)	O1—C8—C9—O2	−175.52 (9)
C6—C1—C2—C3	1.35 (16)	C7—C8—C9—N1	−171.45 (10)
C1—C2—C3—C4	−0.30 (16)	O1—C8—C9—N1	5.88 (13)
C2—C3—C4—C5	−0.69 (18)	N1—N2—C10—C11	−179.00 (8)
C3—C4—C5—C6	0.67 (17)	N2—C10—C11—C16	−2.28 (15)
C4—C5—C6—C1	0.32 (16)	N2—C10—C11—C12	176.82 (10)
C4—C5—C6—C7	−179.70 (12)	C16—C11—C12—C13	1.54 (16)
O1—C1—C6—C5	179.05 (9)	C10—C11—C12—C13	−177.59 (10)
C2—C1—C6—C5	−1.38 (16)	C11—C12—C13—C14	−1.15 (16)
O1—C1—C6—C7	−0.94 (11)	C12—C13—C14—C15	−0.46 (17)
C2—C1—C6—C7	178.62 (10)	C12—C13—C14—Cl1	179.76 (8)
C5—C6—C7—C8	−178.95 (12)	C13—C14—C15—C16	1.64 (17)
C1—C6—C7—C8	1.04 (11)	Cl1—C14—C15—C16	−178.57 (9)
C6—C7—C8—O1	−0.81 (12)	C14—C15—C16—C11	−1.23 (16)
C6—C7—C8—C9	176.66 (10)	C12—C11—C16—C15	−0.34 (16)
C1—O1—C8—C7	0.24 (11)	C10—C11—C16—C15	178.77 (10)
C1—O1—C8—C9	−177.51 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.855 (19)	2.040 (19)	2.8815 (11)	168.1 (18)
O1W—H2W1···O2ⁱ	0.75 (2)	2.06 (2)	2.8045 (11)	173 (2)
N1—H1N1···O1Wⁱⁱ	0.909 (19)	1.952 (19)	2.8083 (12)	156.2 (18)
C2—H2A···O2ⁱⁱ	0.95	2.57	3.3710 (14)	142
C10—H10A···O1Wⁱⁱ	0.95	2.54	3.3067 (13)	138

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁ClN₂O₂·H₂O
M_r	316.73
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	24.6121 (15), 4.6625 (3), 12.6570 (8)
β (°)	99.294 (1)
V (Å³)	1433.37 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.57 × 0.34 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.856, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	7338, 4620, 4511
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.04
No. of reflections	4620
No. of parameters	211
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, −0.19
Absolute structure	Flack (1983), 2025 Friedel pairs
Absolute structure parameter	0.03 (3)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.855 (19)	2.040 (19)	2.8815 (11)	168.1 (18)
O1W—H2W1···O2ⁱ	0.75 (2)	2.06 (2)	2.8045 (11)	173 (2)
N1—H1N1···O1Wⁱⁱ	0.909 (19)	1.952 (19)	2.8083 (12)	156.2 (18)
C2—H2A···O2ⁱⁱ	0.95	2.57	3.3710 (14)	142
C10—H10A···O1Wⁱⁱ	0.95	2.54	3.3067 (13)	138

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant. BK thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

References

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