N′-[(E)-3-Chloro-2-fluoro­benzyl­idene]-6-methyl­nicotinohydrazide monohydrate

Fun, H.-K.; Quah, C.K.; Shyma, P.C.; Kalluraya, B.; Vidyashree, J.H.S.

doi:10.1107/S1600536812026736

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2122

https://doi.org/10.1107/S1600536812026736

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N′-[(E)-3-Chloro-2-fluorobenzylidene]-6-methylnicotinohydrazide monohydrate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § P. C. Shyma,^b Balakrishna Kalluraya ^b and J. H. S. Vidyashree ^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 13 June 2012; online 16 June 2012)

The title compound, C₁₄H₁₁ClFN₃O·H₂O, exists in an E conformation with respect to the N=C bond. The pyridine ring forms a dihedral angle of 5.00 (9)° with the benzene ring. In the crystal, the ketone O atom accepts one O—H⋯O and one C—H⋯O hydrogen bond, the water O atom accepts one N—H⋯O and two C—H⋯O hydrogen bonds and the pyridine N atom accepts one O—H⋯N hydrogen bond, forming layers parallel to the ab plane.

Related literature

For general background to and the biological properties of hydrazone derivatives, see: Rollas & Kucukguzel (2007 ); Sondhi et al. (2009 ); Belskaya et al. (2010 ); Vijesh et al. (2011 ); Galil & Amr (2000 ). 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, Shetty et al. (2012 ); Fun, Quah, Nitinchandra et al. (2012 ).

Experimental

Crystal data

C₁₄H₁₁ClFN₃O·H₂O
M_r = 309.72
Monoclinic, P 2₁ /c
a = 9.7898 (12) Å
b = 6.4440 (8) Å
c = 23.121 (3) Å
β = 106.614 (5)°
V = 1397.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 K
0.47 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.874, T_max = 0.962
12000 measured reflections
3154 independent reflections
2625 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.05
3154 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O1ⁱ	0.78	2.11	2.8713 (18)	166
O1W—H1W1⋯N3ⁱⁱ	0.78	2.11	2.859 (2)	160
N2—H3⋯O1W	0.83	2.01	2.8104 (18)	162
C4—H4A⋯O1W	0.95	2.46	3.388 (2)	165
C7—H7A⋯O1W	0.95	2.39	3.1902 (19)	141
C12—H12A⋯O1ⁱⁱⁱ	0.95	2.46	3.230 (2)	138
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+1, -z; (iii) -x+1, -y-1, -z.

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/S1600536812026736/is5156sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026736/is5156Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812026736/is5156Isup3.cml

checkCIF report

Comment top

Hydrazones and their derivatives constitute a versatile class of compounds in organic chemistry. These compounds have showed varied biological properties, such as anti-inflammatory, analgesic, anticonvulsant, antituberculur, antitumor, anti-HIV and antimicrobial activity (Rollas & Kucukguzel, 2007; Sondhi et al., 2009; Belskaya et al.., 2010). Hydrazones are important compounds for drug design, as possible ligands for metal complexes, and also for the syntheses of large number of heterocyclic compounds. Further, substituted pyridines have showed significant biological activities (Vijesh et al., 2011; Galil & Amr, 2000). These reports prompted us to synthesize the novel derivative of 6-mthyl nicotinic acid hydrazide hydrazone to study its crystal structure.

The title compound (Fig. 1) consists of a N'-[(1E)-(3-chloro-2- fluorophenyl)methylidene]-6-methylnicotinohydrazide molecule and a water molecule in the asymmetric unit and exists in an E configuration with respect to the N1═C7 bond [1.279 (2) Å]. The pyridine ring (N3/C1–C5, r.m.s deviation = 0.008 Å) forms a dihedral angle of 5.00 (9)° with the benzene ring (C8–C13). 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, Shetty et al., 2012; Fun, Quah, Nitinchandra et al., 2012).

In the crystal (Fig.2), molecules are linked via intermolecular O1W—H2W1···O1, C12—H12A···O1 bifurcated acceptor bonds (Table 1) and N2—H3···O1W, C4—H4A···O1W, C7—H7A···O1W trifurcated acceptor bonds and together with O1W—H1W1···N3 hydrogen bonds to form two-dimensional layers parallel to (001).

Related literature top

For general background to and the biological properties of hydrazone derivatives, see: Rollas & Kucukguzel (2007); Sondhi et al. (2009); Belskaya et al. (2010); Vijesh et al. (2011); Galil & Amr (2000). 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, Shetty et al. (2012); Fun, Quah, Nitinchandra et al. (2012).

Experimental top

6-Methylnicotinohydrazide (1 g, 0.006 mol) and 3-chloro-2-flourobenzaldehyde (1.05 g, 0.006 mol) are refluxed for 1hr in ethanol(10 ml) by adding few drops of acetic acid. The solid separated on cooling was filtered, washed with chilled ethanol and dried. The crude material is recrystallized from hot ethanol(1.5 g, 78% ). M.p. : 457-458 °C. The crystals of appropriate size were obtained by the slow evaporation of the ethanolic solution of the compound.

Structure description top

For general background to and the biological properties of hydrazone derivatives, see: Rollas & Kucukguzel (2007); Sondhi et al. (2009); Belskaya et al. (2010); Vijesh et al. (2011); Galil & Amr (2000). 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, Shetty et al. (2012); Fun, Quah, Nitinchandra 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.

N'-[(E)-3-Chloro-2-fluorobenzylidene]-6- methylnicotinohydrazide monohydrate top

Crystal data top

C₁₄H₁₁ClFN₃O·H₂O	F(000) = 640
M_r = 309.72	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5275 reflections
a = 9.7898 (12) Å	θ = 3.2–30.0°
b = 6.4440 (8) Å	µ = 0.29 mm⁻¹
c = 23.121 (3) Å	T = 100 K
β = 106.614 (5)°	Block, colourless
V = 1397.7 (3) Å³	0.47 × 0.24 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3154 independent reflections
Radiation source: fine-focus sealed tube	2625 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.874, T_max = 0.962	k = −8→8
12000 measured reflections	l = −30→30

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0777P)² + 0.8539P] where P = (F_o² + 2F_c²)/3
3154 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₄H₁₁ClFN₃O·H₂O	V = 1397.7 (3) Å³
M_r = 309.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7898 (12) Å	µ = 0.29 mm⁻¹
b = 6.4440 (8) Å	T = 100 K
c = 23.121 (3) Å	0.47 × 0.24 × 0.13 mm
β = 106.614 (5)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3154 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2625 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.962	R_int = 0.031
12000 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
3154 reflections	Δρ_min = −0.63 e Å⁻³
191 parameters

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	0.13433 (5)	0.04401 (12)	−0.22498 (2)	0.0433 (2)
F1	0.41013 (12)	0.18849 (16)	−0.14979 (5)	0.0253 (3)
O1	0.90720 (13)	−0.28353 (18)	0.07189 (6)	0.0216 (3)
N1	0.69521 (15)	−0.1028 (2)	−0.01138 (6)	0.0147 (3)
N2	0.81273 (15)	0.0080 (2)	0.02094 (6)	0.0140 (3)
H3	0.8209	0.1329	0.0139	0.017*
N3	1.18040 (16)	0.3394 (2)	0.11873 (7)	0.0175 (3)
C1	1.1389 (2)	−0.0710 (3)	0.14649 (8)	0.0213 (4)
H1A	1.1260	−0.2118	0.1559	0.026*
C2	1.2558 (2)	0.0394 (3)	0.17998 (8)	0.0224 (4)
H2A	1.3235	−0.0246	0.2130	0.027*
C3	1.27378 (18)	0.2453 (3)	0.16504 (8)	0.0158 (3)
C4	1.06603 (18)	0.2327 (3)	0.08720 (8)	0.0164 (3)
H4A	0.9987	0.3015	0.0551	0.020*
C5	1.04020 (18)	0.0268 (2)	0.09874 (7)	0.0134 (3)
C6	0.91479 (18)	−0.0965 (2)	0.06299 (7)	0.0144 (3)
C7	0.60432 (18)	−0.0013 (2)	−0.05240 (7)	0.0145 (3)
H7A	0.6211	0.1397	−0.0602	0.017*
C8	0.47374 (17)	−0.1065 (3)	−0.08721 (7)	0.0146 (3)
C9	0.37845 (19)	−0.0051 (3)	−0.13481 (8)	0.0182 (4)
C10	0.25093 (19)	−0.0955 (3)	−0.16783 (8)	0.0243 (4)
C11	0.2185 (2)	−0.2941 (3)	−0.15368 (9)	0.0276 (4)
H11A	0.1321	−0.3580	−0.1760	0.033*
C12	0.3126 (2)	−0.3998 (3)	−0.10675 (9)	0.0254 (4)
H12A	0.2903	−0.5365	−0.0970	0.030*
C13	0.43891 (19)	−0.3077 (3)	−0.07395 (8)	0.0191 (4)
H13A	0.5027	−0.3824	−0.0420	0.023*
C14	1.4001 (2)	0.3715 (3)	0.19936 (8)	0.0216 (4)
H14A	1.3685	0.5111	0.2064	0.032*
H14B	1.4689	0.3811	0.1759	0.032*
H14C	1.4453	0.3046	0.2382	0.032*
O1W	0.78116 (14)	0.41994 (18)	−0.02068 (6)	0.0207 (3)
H2W1	0.8016	0.5100	0.0026	0.031*
H1W1	0.7882	0.4580	−0.0518	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0185 (3)	0.0809 (5)	0.0264 (3)	0.0020 (3)	−0.00018 (19)	0.0134 (3)
F1	0.0256 (6)	0.0188 (5)	0.0300 (6)	0.0021 (4)	0.0052 (4)	0.0078 (4)
O1	0.0211 (7)	0.0072 (6)	0.0320 (7)	−0.0027 (5)	0.0004 (5)	0.0036 (5)
N1	0.0146 (7)	0.0096 (6)	0.0195 (7)	−0.0031 (5)	0.0040 (5)	−0.0031 (5)
N2	0.0149 (7)	0.0062 (6)	0.0194 (7)	−0.0033 (5)	0.0025 (5)	−0.0010 (5)
N3	0.0166 (7)	0.0121 (7)	0.0221 (7)	−0.0031 (5)	0.0027 (6)	−0.0012 (5)
C1	0.0214 (9)	0.0125 (8)	0.0270 (9)	−0.0021 (7)	0.0024 (7)	0.0045 (7)
C2	0.0175 (9)	0.0190 (9)	0.0257 (9)	−0.0014 (7)	−0.0018 (7)	0.0053 (7)
C3	0.0149 (8)	0.0142 (8)	0.0186 (8)	−0.0015 (6)	0.0053 (6)	−0.0020 (6)
C4	0.0162 (8)	0.0109 (7)	0.0198 (8)	−0.0018 (6)	0.0018 (6)	0.0015 (6)
C5	0.0135 (8)	0.0094 (7)	0.0181 (8)	−0.0016 (6)	0.0057 (6)	−0.0014 (6)
C6	0.0149 (8)	0.0091 (7)	0.0197 (8)	−0.0022 (6)	0.0058 (6)	−0.0006 (6)
C7	0.0164 (8)	0.0088 (7)	0.0182 (8)	−0.0014 (6)	0.0050 (6)	−0.0011 (6)
C8	0.0142 (8)	0.0122 (7)	0.0185 (7)	−0.0025 (6)	0.0065 (6)	−0.0040 (6)
C9	0.0177 (8)	0.0181 (8)	0.0199 (8)	−0.0011 (7)	0.0070 (6)	−0.0010 (6)
C10	0.0139 (8)	0.0409 (11)	0.0181 (8)	−0.0028 (8)	0.0045 (6)	−0.0038 (8)
C11	0.0173 (9)	0.0395 (12)	0.0276 (10)	−0.0127 (8)	0.0090 (7)	−0.0136 (8)
C12	0.0251 (10)	0.0204 (9)	0.0348 (10)	−0.0109 (8)	0.0153 (8)	−0.0099 (8)
C13	0.0204 (9)	0.0130 (8)	0.0251 (9)	−0.0035 (7)	0.0088 (7)	−0.0024 (6)
C14	0.0182 (9)	0.0209 (9)	0.0235 (8)	−0.0044 (7)	0.0023 (7)	−0.0033 (7)
O1W	0.0282 (7)	0.0081 (5)	0.0244 (6)	−0.0042 (5)	0.0052 (5)	0.0019 (5)

Geometric parameters (Å, º) top

Cl1—C10	1.731 (2)	C5—C6	1.497 (2)
F1—C9	1.354 (2)	C7—C8	1.467 (2)
O1—C6	1.228 (2)	C7—H7A	0.9500
N1—C7	1.279 (2)	C8—C9	1.386 (2)
N1—N2	1.3786 (18)	C8—C13	1.397 (2)
N2—C6	1.357 (2)	C9—C10	1.391 (2)
N2—H3	0.8295	C10—C11	1.380 (3)
N3—C3	1.338 (2)	C11—C12	1.385 (3)
N3—C4	1.338 (2)	C11—H11A	0.9500
C1—C2	1.381 (2)	C12—C13	1.386 (2)
C1—C5	1.393 (2)	C12—H12A	0.9500
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.395 (2)	C14—H14A	0.9800
C2—H2A	0.9500	C14—H14B	0.9800
C3—C14	1.503 (2)	C14—H14C	0.9800
C4—C5	1.391 (2)	O1W—H2W1	0.7778
C4—H4A	0.9500	O1W—H1W1	0.7815

C7—N1—N2	115.64 (14)	C9—C8—C13	117.44 (15)
C6—N2—N1	117.43 (13)	C9—C8—C7	120.04 (15)
C6—N2—H3	122.0	C13—C8—C7	122.51 (15)
N1—N2—H3	120.6	F1—C9—C8	119.08 (15)
C3—N3—C4	118.47 (15)	F1—C9—C10	118.73 (16)
C2—C1—C5	119.13 (16)	C8—C9—C10	122.19 (17)
C2—C1—H1A	120.4	C11—C10—C9	119.29 (18)
C5—C1—H1A	120.4	C11—C10—Cl1	121.11 (15)
C1—C2—C3	119.62 (16)	C9—C10—Cl1	119.59 (16)
C1—C2—H2A	120.2	C10—C11—C12	119.69 (17)
C3—C2—H2A	120.2	C10—C11—H11A	120.2
N3—C3—C2	121.56 (15)	C12—C11—H11A	120.2
N3—C3—C14	116.62 (15)	C11—C12—C13	120.50 (18)
C2—C3—C14	121.81 (16)	C11—C12—H12A	119.8
N3—C4—C5	123.74 (15)	C13—C12—H12A	119.8
N3—C4—H4A	118.1	C12—C13—C8	120.87 (17)
C5—C4—H4A	118.1	C12—C13—H13A	119.6
C4—C5—C1	117.45 (15)	C8—C13—H13A	119.6
C4—C5—C6	124.46 (15)	C3—C14—H14A	109.5
C1—C5—C6	118.08 (15)	C3—C14—H14B	109.5
O1—C6—N2	122.65 (15)	H14A—C14—H14B	109.5
O1—C6—C5	120.50 (15)	C3—C14—H14C	109.5
N2—C6—C5	116.85 (14)	H14A—C14—H14C	109.5
N1—C7—C8	118.86 (15)	H14B—C14—H14C	109.5
N1—C7—H7A	120.6	H2W1—O1W—H1W1	109.3
C8—C7—H7A	120.6

C7—N1—N2—C6	−177.06 (15)	N2—N1—C7—C8	−177.73 (13)
C5—C1—C2—C3	−0.7 (3)	N1—C7—C8—C9	−175.30 (16)
C4—N3—C3—C2	1.4 (3)	N1—C7—C8—C13	5.6 (3)
C4—N3—C3—C14	−179.66 (15)	C13—C8—C9—F1	−178.62 (15)
C1—C2—C3—N3	−0.1 (3)	C7—C8—C9—F1	2.2 (2)
C1—C2—C3—C14	−179.06 (18)	C13—C8—C9—C10	1.4 (3)
C3—N3—C4—C5	−1.8 (3)	C7—C8—C9—C10	−177.74 (16)
N3—C4—C5—C1	0.9 (3)	F1—C9—C10—C11	178.90 (16)
N3—C4—C5—C6	−178.41 (16)	C8—C9—C10—C11	−1.1 (3)
C2—C1—C5—C4	0.4 (3)	F1—C9—C10—Cl1	−2.2 (2)
C2—C1—C5—C6	179.74 (16)	C8—C9—C10—Cl1	177.77 (14)
N1—N2—C6—O1	1.7 (3)	C9—C10—C11—C12	0.4 (3)
N1—N2—C6—C5	−178.62 (13)	Cl1—C10—C11—C12	−178.47 (15)
C4—C5—C6—O1	172.25 (17)	C10—C11—C12—C13	0.0 (3)
C1—C5—C6—O1	−7.1 (3)	C11—C12—C13—C8	0.4 (3)
C4—C5—C6—N2	−7.4 (2)	C9—C8—C13—C12	−1.0 (3)
C1—C5—C6—N2	173.25 (15)	C7—C8—C13—C12	178.11 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O1ⁱ	0.78	2.11	2.8713 (18)	166
O1W—H1W1···N3ⁱⁱ	0.78	2.11	2.859 (2)	160
N2—H3···O1W	0.83	2.01	2.8104 (18)	162
C4—H4A···O1W	0.95	2.46	3.388 (2)	165
C7—H7A···O1W	0.95	2.39	3.1902 (19)	141
C12—H12A···O1ⁱⁱⁱ	0.95	2.46	3.230 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClFN₃O·H₂O
M_r	309.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.7898 (12), 6.4440 (8), 23.121 (3)
β (°)	106.614 (5)
V (Å³)	1397.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.47 × 0.24 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.874, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	12000, 3154, 2625
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.05
No. of reflections	3154
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.63

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—H2W1···O1ⁱ	0.78	2.11	2.8713 (18)	166
O1W—H1W1···N3ⁱⁱ	0.78	2.11	2.859 (2)	160
N2—H3···O1W	0.83	2.01	2.8104 (18)	162
C4—H4A···O1W	0.95	2.46	3.388 (2)	165
C7—H7A···O1W	0.95	2.39	3.1902 (19)	141
C12—H12A···O1ⁱⁱⁱ	0.95	2.46	3.230 (2)	138

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

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 also thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

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