N′-[(Z)-4-Methyl­benzyl­idene]-4-nitro­benzohydrazide monohydrate

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

doi:10.1107/S1600536808037008

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2338

doi:10.1107/S1600536808037008

Open

access

N′-[(Z)-4-Methylbenzylidene]-4-nitrobenzohydrazide monohydrate

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ K. V. Sujith ^b and B. Kalluraya ^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 4 November 2008; accepted 10 November 2008; online 13 November 2008)

In the title compound, C₁₅H₁₃N₃O₃·H₂O, the two benzene rings form a dihedral angle of 2.03 (2)°. In the crystal structure, adjacent hydrazide molecules are linked into dimers by water molecules; these dimers are then stacked along the b axis. Intermolecular O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds and a π–π stacking interaction between the nitrobenzene and tolyl rings with a centroid–centroid distance of 3.8208 (3) Å are observed. There is also a short O⋯N contact [2.6824 (7) Å].

Related literature

For related literature on hydrazones, see: Sridhar & Perumal (2003 ). For the biological applications of hydrazides/hydrazones, see: Bedia et al. (2006 ). For a related structure, see: Fun et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₃·H₂O
M_r = 301.30
Triclinic, $[P \overline 1]$
a = 6.5387 (1) Å
b = 6.9730 (1) Å
c = 15.9064 (3) Å
α = 80.524 (1)°
β = 82.628 (1)°
γ = 85.036 (1)°
V = 707.85 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100.0 (1) K
0.68 × 0.44 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.932, T_max = 0.976
31311 measured reflections
7380 independent reflections
6571 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.118
S = 1.05
7380 reflections
211 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1W	0.864 (8)	1.978 (9)	2.8191 (7)	164.4 (11)
O1W—H2W1⋯O1ⁱ	0.837 (9)	2.013 (9)	2.8327 (7)	166.1 (11)
O1W—H1W1⋯O1ⁱⁱ	0.851 (9)	2.258 (11)	2.9430 (6)	137.7 (10)
O1W—H1W1⋯N1ⁱⁱ	0.851 (9)	2.357 (9)	3.1287 (7)	151.0 (11)
C1—H1A⋯O1Wⁱⁱⁱ	0.93	2.50	3.4090 (7)	165
C4—H4A⋯O2^iv	0.93	2.58	3.4565 (8)	157
C7—H7A⋯O1W	0.93	2.55	3.2393 (7)	132
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x-1, y, z; (iii) x+1, y, z; (iv) x, y-1, z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037008/is2358sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037008/is2358Isup2.hkl

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 diformylation by the treatment with Vilsmeier reagent. A series of hydrazide-hydrazones were reported to possess good antituberculosis activity (Bedia et al., 2006). Prompted by these review and in continuation of our work (Fun et al., 2008), we here in report the crystal structure of the title compound, (I).

Bond lengths and angles in (I) (Fig. 1) are found to have normal values (Allen et al., 1987). The two benzene rings are essentially planar with the maximum deviation from planarity being -0.004 (1) Å for atom C6 and 0.002 (1) Å for atom C12, respectively. The dihedral angle formed by the benzene (C1—C6) and (C9—C14) rings is 2.03 (2)°.

The crystal packing is consolidated by O—H···O, O—H···N, C—H···O and N—H···O inter and intramolecular hydrogen bonding (Table 1). Furthermore, the packing is strengthened by π-π stacking interactions involving the benzene (C1—C6) (Cg1) and the symmetry related (C9—C14) ring (Cg2) [Cg1···Cg2ⁱ = 3.8208 (3) Å; symmetry code: (i) 2-x, 1-y, -z] together with O···N short contacts [2.6824 (7) Å]. In the crystal packing, adjacent molecules are linked into dimers by water molecules and the dimers were then stacked down the [010] direction (Fig. 2).

Related literature top

For related literature on hydrazones, see: Sridhar & Perumal (2003). For the biological applications of hydrazides/hydrazones, see: Bedia et al. (2006). For a related structure, see: Fun et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, C₁₅H₁₅N₃O₄, was obtained by refluxing 4-nitrobenzhydrazide (0.01 mol) and 4-methylbenzaldehyde (0.01 mol) in ethanol (30 ml) by adding 3 drops of concentrated sulfuric acid for 3 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with water and dried. Crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

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 down the a axis, showing stacking of the dimers along the b axis.

N'-[(Z)-4-Methylbenzylidene]-4-nitrobenzohydrazide monohydrate top

Crystal data top

C₁₅H₁₃N₃O₃·H₂O	Z = 2
M_r = 301.30	F(000) = 316
Triclinic, P1	D_x = 1.414 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5387 (1) Å	Cell parameters from 9969 reflections
b = 6.9730 (1) Å	θ = 2.6–26.3°
c = 15.9064 (3) Å	µ = 0.11 mm⁻¹
α = 80.524 (1)°	T = 100 K
β = 82.628 (1)°	Block, colourless
γ = 85.036 (1)°	0.68 × 0.44 × 0.23 mm
V = 707.85 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7380 independent reflections
Radiation source: fine-focus sealed tube	6571 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 37.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.932, T_max = 0.976	k = −11→10
31311 measured reflections	l = −27→27

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0681P)² + 0.1283P] where P = (F_o² + 2F_c²)/3
7380 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.48 e Å⁻³
4 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₃·H₂O	γ = 85.036 (1)°
M_r = 301.30	V = 707.85 (2) Å³
Triclinic, P1	Z = 2
a = 6.5387 (1) Å	Mo Kα radiation
b = 6.9730 (1) Å	µ = 0.11 mm⁻¹
c = 15.9064 (3) Å	T = 100 K
α = 80.524 (1)°	0.68 × 0.44 × 0.23 mm
β = 82.628 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7380 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6571 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.976	R_int = 0.020
31311 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	4 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.48 e Å⁻³
7380 reflections	Δρ_min = −0.59 e Å⁻³
211 parameters

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
O1	1.27580 (6)	0.77076 (7)	−0.04714 (3)	0.01642 (8)
O2	0.75581 (8)	1.18850 (8)	−0.38841 (3)	0.02159 (10)
O3	0.46360 (8)	1.16591 (9)	−0.30724 (3)	0.02477 (11)
N1	1.08155 (7)	0.62939 (7)	0.10666 (3)	0.01228 (8)
N2	0.97488 (7)	0.71707 (7)	0.03900 (3)	0.01180 (8)
N3	0.65301 (8)	1.14188 (7)	−0.31919 (3)	0.01517 (9)
C1	1.25937 (9)	0.43357 (8)	0.25978 (3)	0.01394 (9)
H1A	1.3528	0.4556	0.2105	0.017*
C2	1.32689 (9)	0.33958 (9)	0.33630 (4)	0.01558 (9)
H2A	1.4660	0.2992	0.3375	0.019*
C3	1.19044 (10)	0.30421 (9)	0.41173 (4)	0.01618 (10)
C4	0.98236 (10)	0.36711 (9)	0.40850 (4)	0.01732 (10)
H4A	0.8891	0.3455	0.4579	0.021*
C5	0.91322 (9)	0.46166 (9)	0.33225 (4)	0.01511 (9)
H5A	0.7744	0.5032	0.3313	0.018*
C6	1.05015 (8)	0.49509 (8)	0.25695 (3)	0.01205 (8)
C7	0.96681 (8)	0.59124 (8)	0.17866 (3)	0.01265 (9)
H7A	0.8259	0.6261	0.1809	0.015*
C8	1.08418 (8)	0.78209 (7)	−0.03665 (3)	0.01124 (8)
C9	0.96283 (8)	0.87393 (7)	−0.10826 (3)	0.01078 (8)
C10	0.74981 (8)	0.92155 (8)	−0.09685 (3)	0.01259 (9)
H10A	0.6760	0.8932	−0.0428	0.015*
C11	0.64812 (8)	1.01101 (8)	−0.16601 (3)	0.01320 (9)
H11A	0.5067	1.0435	−0.1589	0.016*
C12	0.76204 (8)	1.05088 (8)	−0.24589 (3)	0.01220 (8)
C13	0.97361 (9)	1.00639 (8)	−0.25947 (3)	0.01340 (9)
H13A	1.0465	1.0355	−0.3137	0.016*
C14	1.07314 (8)	0.91711 (8)	−0.18969 (3)	0.01269 (9)
H14A	1.2148	0.8857	−0.1972	0.015*
C15	1.26554 (12)	0.20102 (11)	0.49388 (4)	0.02473 (13)
H15A	1.1517	0.1899	0.5386	0.037*
H15B	1.3687	0.2740	0.5096	0.037*
H15C	1.3242	0.0733	0.4859	0.037*
O1W	0.56488 (7)	0.60570 (7)	0.07749 (3)	0.01669 (8)
H1N2	0.8430 (12)	0.7058 (17)	0.0471 (8)	0.027 (3)*
H2W1	0.5907 (17)	0.4907 (12)	0.0684 (8)	0.031 (3)*
H1W1	0.4410 (13)	0.6364 (17)	0.0668 (8)	0.035 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.00972 (15)	0.0221 (2)	0.01583 (17)	0.00035 (13)	−0.00227 (13)	0.00155 (14)
O2	0.0250 (2)	0.0269 (2)	0.01076 (17)	−0.00148 (17)	−0.00275 (15)	0.00358 (15)
O3	0.01615 (19)	0.0361 (3)	0.0199 (2)	0.00133 (18)	−0.00737 (16)	0.00461 (19)
N1	0.01330 (18)	0.01250 (17)	0.01075 (17)	−0.00018 (13)	−0.00421 (13)	0.00081 (13)
N2	0.01085 (17)	0.01426 (18)	0.00977 (16)	−0.00046 (13)	−0.00339 (13)	0.00113 (13)
N3	0.0174 (2)	0.01585 (19)	0.01215 (18)	−0.00094 (15)	−0.00535 (15)	0.00083 (14)
C1	0.0137 (2)	0.0152 (2)	0.01227 (19)	−0.00081 (16)	−0.00285 (15)	0.00066 (15)
C2	0.0155 (2)	0.0166 (2)	0.0143 (2)	0.00085 (17)	−0.00481 (16)	−0.00018 (16)
C3	0.0208 (2)	0.0158 (2)	0.01158 (19)	0.00194 (17)	−0.00496 (17)	−0.00040 (16)
C4	0.0199 (2)	0.0196 (2)	0.01066 (19)	0.00142 (18)	−0.00093 (17)	0.00081 (16)
C5	0.0148 (2)	0.0174 (2)	0.01210 (19)	0.00041 (16)	−0.00163 (16)	−0.00002 (16)
C6	0.01369 (19)	0.01192 (19)	0.01037 (18)	−0.00115 (15)	−0.00323 (14)	0.00030 (14)
C7	0.01325 (19)	0.0133 (2)	0.01122 (18)	−0.00088 (15)	−0.00333 (15)	0.00004 (15)
C8	0.01101 (18)	0.01159 (18)	0.01084 (18)	0.00006 (14)	−0.00243 (14)	−0.00044 (14)
C9	0.01090 (18)	0.01125 (18)	0.00998 (17)	−0.00020 (14)	−0.00238 (14)	−0.00045 (14)
C10	0.01106 (18)	0.0154 (2)	0.01048 (18)	0.00026 (15)	−0.00182 (14)	0.00036 (15)
C11	0.01170 (19)	0.0154 (2)	0.01187 (19)	0.00029 (15)	−0.00297 (15)	0.00029 (15)
C12	0.01382 (19)	0.01256 (19)	0.01019 (18)	−0.00090 (15)	−0.00400 (15)	0.00040 (14)
C13	0.0141 (2)	0.0151 (2)	0.01041 (18)	−0.00143 (16)	−0.00148 (15)	−0.00005 (15)
C14	0.01159 (19)	0.0146 (2)	0.01130 (18)	−0.00053 (15)	−0.00128 (14)	−0.00060 (15)
C15	0.0321 (3)	0.0271 (3)	0.0134 (2)	0.0068 (2)	−0.0081 (2)	0.0011 (2)
O1W	0.01130 (16)	0.0212 (2)	0.01725 (18)	−0.00029 (13)	−0.00349 (13)	−0.00109 (14)

Geometric parameters (Å, º) top

O1—C8	1.2400 (6)	C6—C7	1.4605 (7)
O2—N3	1.2246 (7)	C7—H7A	0.9300
O3—N3	1.2298 (7)	C8—C9	1.4970 (7)
N1—C7	1.2881 (7)	C9—C14	1.3994 (7)
N1—N2	1.3859 (6)	C9—C10	1.3994 (7)
N2—C8	1.3491 (7)	C10—C11	1.3898 (7)
N2—H1N2	0.864 (8)	C10—H10A	0.9300
N3—C12	1.4703 (7)	C11—C12	1.3867 (7)
C1—C2	1.3896 (8)	C11—H11A	0.9300
C1—C6	1.4019 (8)	C12—C13	1.3884 (8)
C1—H1A	0.9300	C13—C14	1.3895 (7)
C2—C3	1.4008 (8)	C13—H13A	0.9300
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.3977 (9)	C15—H15A	0.9600
C3—C15	1.5035 (8)	C15—H15B	0.9600
C4—C5	1.3913 (8)	C15—H15C	0.9600
C4—H4A	0.9300	O1W—H2W1	0.837 (8)
C5—C6	1.3999 (8)	O1W—H1W1	0.851 (8)
C5—H5A	0.9300

C7—N1—N2	114.21 (4)	O1—C8—N2	122.52 (5)
C8—N2—N1	118.48 (4)	O1—C8—C9	120.74 (5)
C8—N2—H1N2	125.4 (8)	N2—C8—C9	116.74 (4)
N1—N2—H1N2	115.2 (8)	C14—C9—C10	119.65 (5)
O2—N3—O3	123.96 (5)	C14—C9—C8	116.93 (4)
O2—N3—C12	118.18 (5)	C10—C9—C8	123.40 (5)
O3—N3—C12	117.85 (5)	C11—C10—C9	120.23 (5)
C2—C1—C6	119.91 (5)	C11—C10—H10A	119.9
C2—C1—H1A	120.0	C9—C10—H10A	119.9
C6—C1—H1A	120.0	C12—C11—C10	118.60 (5)
C1—C2—C3	121.56 (5)	C12—C11—H11A	120.7
C1—C2—H2A	119.2	C10—C11—H11A	120.7
C3—C2—H2A	119.2	C11—C12—C13	122.73 (5)
C4—C3—C2	118.18 (5)	C11—C12—N3	118.38 (5)
C4—C3—C15	120.88 (6)	C13—C12—N3	118.89 (5)
C2—C3—C15	120.95 (6)	C12—C13—C14	118.01 (5)
C5—C4—C3	120.72 (5)	C12—C13—H13A	121.0
C5—C4—H4A	119.6	C14—C13—H13A	121.0
C3—C4—H4A	119.6	C13—C14—C9	120.79 (5)
C4—C5—C6	120.80 (5)	C13—C14—H14A	119.6
C4—C5—H5A	119.6	C9—C14—H14A	119.6
C6—C5—H5A	119.6	C3—C15—H15A	109.5
C5—C6—C1	118.83 (5)	C3—C15—H15B	109.5
C5—C6—C7	118.05 (5)	H15A—C15—H15B	109.5
C1—C6—C7	123.11 (5)	C3—C15—H15C	109.5
N1—C7—C6	122.33 (5)	H15A—C15—H15C	109.5
N1—C7—H7A	118.8	H15B—C15—H15C	109.5
C6—C7—H7A	118.8	H2W1—O1W—H1W1	106.0 (10)

C7—N1—N2—C8	172.77 (5)	N2—C8—C9—C14	−171.45 (5)
C6—C1—C2—C3	−0.09 (9)	O1—C8—C9—C10	−168.59 (5)
C1—C2—C3—C4	−0.32 (9)	N2—C8—C9—C10	10.18 (8)
C1—C2—C3—C15	179.55 (6)	C14—C9—C10—C11	0.09 (8)
C2—C3—C4—C5	0.20 (9)	C8—C9—C10—C11	178.42 (5)
C15—C3—C4—C5	−179.67 (6)	C9—C10—C11—C12	0.20 (8)
C3—C4—C5—C6	0.33 (9)	C10—C11—C12—C13	−0.47 (8)
C4—C5—C6—C1	−0.73 (9)	C10—C11—C12—N3	178.76 (5)
C4—C5—C6—C7	178.66 (5)	O2—N3—C12—C11	175.31 (5)
C2—C1—C6—C5	0.61 (8)	O3—N3—C12—C11	−4.94 (8)
C2—C1—C6—C7	−178.75 (5)	O2—N3—C12—C13	−5.43 (8)
N2—N1—C7—C6	178.63 (5)	O3—N3—C12—C13	174.32 (6)
C5—C6—C7—N1	179.37 (5)	C11—C12—C13—C14	0.42 (8)
C1—C6—C7—N1	−1.26 (9)	N3—C12—C13—C14	−178.81 (5)
N1—N2—C8—O1	−1.88 (8)	C12—C13—C14—C9	−0.10 (8)
N1—N2—C8—C9	179.38 (4)	C10—C9—C14—C13	−0.14 (8)
O1—C8—C9—C14	9.78 (8)	C8—C9—C14—C13	−178.58 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1W	0.86 (1)	1.98 (1)	2.8191 (7)	164 (1)
O1W—H2W1···O1ⁱ	0.84 (1)	2.01 (1)	2.8327 (7)	166 (1)
O1W—H1W1···O1ⁱⁱ	0.85 (1)	2.26 (1)	2.9430 (6)	138 (1)
O1W—H1W1···N1ⁱⁱ	0.85 (1)	2.36 (1)	3.1287 (7)	151 (1)
C1—H1A···O1Wⁱⁱⁱ	0.93	2.50	3.4090 (7)	165
C4—H4A···O2^iv	0.93	2.58	3.4565 (8)	157
C7—H7A···O1W	0.93	2.55	3.2393 (7)	132

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₃·H₂O
M_r	301.30
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.5387 (1), 6.9730 (1), 15.9064 (3)
α, β, γ (°)	80.524 (1), 82.628 (1), 85.036 (1)
V (Å³)	707.85 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.68 × 0.44 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.932, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	31311, 7380, 6571
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.119, 1.05
No. of reflections	7380
No. of parameters	211
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.59

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
N2—H1N2···O1W	0.864 (8)	1.978 (9)	2.8191 (7)	164.4 (11)
O1W—H2W1···O1ⁱ	0.837 (9)	2.013 (9)	2.8327 (7)	166.1 (11)
O1W—H1W1···O1ⁱⁱ	0.851 (9)	2.258 (11)	2.9430 (6)	137.7 (10)
O1W—H1W1···N1ⁱⁱ	0.851 (9)	2.357 (9)	3.1287 (7)	151.0 (11)
C1—H1A···O1Wⁱⁱⁱ	0.93	2.50	3.4090 (7)	165
C4—H4A···O2^iv	0.93	2.58	3.4565 (8)	157
C7—H7A···O1W	0.93	2.55	3.2393 (7)	132

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

Footnotes

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

Acknowledgements

FHK 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

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
Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483–1488. Web of Science CrossRef CAS Google Scholar