(E)-N′-(3,4-Dihy­droxy­benzyl­idene)-2,4-dimethyl­benzohydrazide monohydrate

Taha, M.; Ismail, N.H.; Jaafar, F.M.; Aziz, A.N.; Yousuf, S.

doi:10.1107/S1600536813005692

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o490

doi:10.1107/S1600536813005692

Open

access

(E)-N′-(3,4-Dihydroxybenzylidene)-2,4-dimethylbenzohydrazide monohydrate

Muhammad Taha,^a Nor Hadiani Ismail,^b Faridahanim Mohd Jaafar,^b Ahmad Nazif Aziz ^a,^c and Sammer Yousuf ^d ^*

^aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia, ^bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D. E., Malaysia, ^cDepartment of Chemical Sciences, Faculty of Science and Technology, University Malaysia Terengganu, 21030, Kuala Terengganu, Malaysia, and ^dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 18 February 2013; accepted 27 February 2013; online 6 March 2013)

In the title compound, C₁₆H₁₆N₂O₃·H₂O, the dihedral angle between the benzene rings is 30.27 (7)°. In the crystal, the components are linked by N—H⋯O, O—H⋯O and C—H⋯O interactions into a three-dimensional network.

Related literature

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012 ); Khan et al. (2012 ). For the crystal structures of related compounds, see: Taha et al. (2012 ); Baharudin et al. (2012 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₃·H₂O
M_r = 302.32
Monoclinic, P 2₁ /n
a = 8.1373 (3) Å
b = 13.9025 (5) Å
c = 13.7886 (5) Å
β = 92.913 (1)°
V = 1557.87 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.973, T_max = 0.991
9012 measured reflections
2897 independent reflections
2535 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.05
2897 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N2ⁱ	0.87 (2)	2.20 (2)	3.059 (2)	169 (2)
O1W—H2W1⋯O1	0.94 (2)	2.01 (2)	2.935 (2)	173 (2)
N1—H1A⋯O3ⁱⁱ	0.91 (2)	2.08 (2)	2.962 (2)	163 (2)
O2—H2A⋯O1ⁱ	0.88 (2)	1.94 (2)	2.791 (2)	162 (2)
O3—H3A⋯O1Wⁱⁱⁱ	0.85 (2)	1.79 (2)	2.629 (2)	172 (2)
C8—H8A⋯O3ⁱⁱ	0.93	2.58	3.382 (2)	145
C15—H15B⋯O2ⁱ	0.96	2.52	3.351 (2)	144
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005692/pv2622sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005692/pv2622Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005692/pv2622Isup3.cml

checkCIF report

Comment top

Structurally diverse range of benzohydrazides have been extensively studied in order to explore the structural features that may be responsible for different biological activities (Musharraf et al., 2012; Khan et al., 2012). The title compound is yet another benzohydrazide monohydrate, obtained as a part of our ongoing research that has been studied by X-ray crystallographic method and reported in this article.

In the title compound (Fig. 1) dimethyl and dihydroxy substituted benzene rings (C1–C6 and C9–C14, respectively) are each planner with a dihedral angle 30.27 (7)° between their mean-planes. The azomethine double bond, N2═C8 (1.2729 (19) Å) adopts an E configuration. The bond lengths and angle are similar to the corresponding bond lengths and angles reported in structurally related benzohydrazide derivatives (Taha et al., 2012; Baharudin et al., 2012). The crystal structure is stabilized by N1—H1A···N2, O2—H2A···O1, C8—H8A···O3 and C15—H15B···O2 intermolecular interactions. The ineteractions further extend the structure to a three dimentional network via O1W—H2W1···O1, O1W—H1A···O3 and O3—H3A···O1W interactions involving the water of hydration (Table 2 and Fig. 2).

Related literature top

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012); Khan et al. (2012). For the crystal structures of related compounds, see: Taha et al. (2012); Baharudin et al. (2012).

Experimental top

The title compound was synthesized by reacting (0.328 g, 2 mmol) 2,4-dimethylbenzohydrazide and (0.276 g, 2 mmol) 3,4-dihydroxybenzaldehyde as starting meterial under the same conditions and solvents as described previously for the synthesis of benzohydrazides (Taha et al., 2012). The title compound was recrystalized by dissolving in methanol to obtain colorless needles (0.499 g, 88% yield). All chemicals were purchased by Sigma Aldrich Germany.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the title compound. Only hydrogen atoms involved in hydrogen bonding are shown.

(E)-N'-(3,4-Dihydroxybenzylidene)-2,4-dimethylbenzohydrazide monohydrate top

Crystal data top

C₁₆H₁₆N₂O₃·H₂O	F(000) = 640
M_r = 302.32	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4856 reflections
a = 8.1373 (3) Å	θ = 2.8–28.2°
b = 13.9025 (5) Å	µ = 0.09 mm⁻¹
c = 13.7886 (5) Å	T = 298 K
β = 92.913 (1)°	Block, brown
V = 1557.87 (10) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2535 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scan	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.973, T_max = 0.991	k = −16→16
9012 measured reflections	l = −16→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0596P)² + 0.3352P] where P = (F_o² + 2F_c²)/3
2897 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃·H₂O	V = 1557.87 (10) Å³
M_r = 302.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1373 (3) Å	µ = 0.09 mm⁻¹
b = 13.9025 (5) Å	T = 298 K
c = 13.7886 (5) Å	0.30 × 0.10 × 0.10 mm
β = 92.913 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2897 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2535 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.991	R_int = 0.016
9012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
2897 reflections	Δρ_min = −0.28 e Å⁻³
221 parameters

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
O1	0.15363 (13)	0.55077 (8)	−0.16328 (8)	0.0569 (3)
O1W	−0.12355 (15)	0.45259 (10)	−0.07769 (9)	0.0612 (3)
O2	−0.04800 (12)	0.26761 (9)	0.22605 (8)	0.0505 (3)
O3	0.16469 (13)	0.15980 (8)	0.32684 (7)	0.0460 (3)
N1	0.34634 (15)	0.43523 (9)	−0.14057 (9)	0.0454 (3)
N2	0.28104 (14)	0.40196 (9)	−0.05580 (8)	0.0435 (3)
C1	0.30375 (16)	0.56844 (10)	−0.36100 (10)	0.0395 (3)
C2	0.40413 (18)	0.60048 (11)	−0.43273 (10)	0.0446 (3)
H2C	0.3561	0.6153	−0.4935	0.054*
C3	0.57324 (17)	0.61142 (11)	−0.41767 (10)	0.0435 (3)
C4	0.64410 (17)	0.58608 (11)	−0.32796 (11)	0.0455 (4)
H4A	0.7574	0.5911	−0.3166	0.055*
C5	0.54846 (16)	0.55358 (10)	−0.25556 (10)	0.0423 (3)
H5A	0.5981	0.5371	−0.1956	0.051*
C6	0.37828 (16)	0.54484 (9)	−0.27016 (10)	0.0366 (3)
C7	0.28131 (16)	0.51150 (10)	−0.18789 (10)	0.0397 (3)
C8	0.35766 (18)	0.33077 (11)	−0.01702 (11)	0.0464 (4)
H8A	0.4495	0.3069	−0.0465	0.056*
C9	0.30656 (17)	0.28538 (10)	0.07190 (10)	0.0421 (3)
C10	0.41516 (19)	0.22570 (11)	0.12370 (12)	0.0514 (4)
H10A	0.5192	0.2145	0.1011	0.062*
C11	0.37047 (19)	0.18256 (11)	0.20869 (12)	0.0499 (4)
H11A	0.4448	0.1431	0.2432	0.060*
C12	0.21552 (16)	0.19792 (9)	0.24262 (10)	0.0390 (3)
C13	0.10379 (16)	0.25680 (10)	0.18973 (10)	0.0376 (3)
C14	0.14912 (16)	0.29972 (10)	0.10553 (10)	0.0392 (3)
H14A	0.0745	0.3387	0.0705	0.047*
C15	0.12199 (18)	0.55713 (14)	−0.38483 (12)	0.0571 (4)
H15A	0.1029	0.5506	−0.4538	0.086*
H15B	0.0648	0.6128	−0.3628	0.086*
H15C	0.0825	0.5008	−0.3531	0.086*
C16	0.6765 (2)	0.65068 (14)	−0.49624 (13)	0.0615 (5)
H16A	0.6324	0.6293	−0.5584	0.092*
H16B	0.7875	0.6280	−0.4863	0.092*
H16C	0.6755	0.7197	−0.4941	0.092*
H2A	−0.099 (3)	0.3180 (16)	0.1996 (15)	0.077 (6)*
H1A	0.436 (2)	0.4053 (13)	−0.1634 (13)	0.061 (5)*
H1W1	−0.165 (3)	0.4883 (17)	−0.0335 (16)	0.080 (7)*
H3A	0.239 (2)	0.1248 (15)	0.3533 (15)	0.071 (6)*
H2W1	−0.029 (3)	0.4798 (17)	−0.1022 (16)	0.091 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0495 (6)	0.0633 (7)	0.0601 (7)	0.0209 (5)	0.0261 (5)	0.0182 (5)
O1W	0.0486 (6)	0.0766 (9)	0.0595 (7)	−0.0124 (6)	0.0122 (5)	−0.0274 (6)
O2	0.0399 (5)	0.0578 (7)	0.0557 (7)	0.0085 (5)	0.0200 (5)	0.0140 (5)
O3	0.0453 (6)	0.0499 (6)	0.0442 (6)	0.0056 (5)	0.0153 (5)	0.0141 (5)
N1	0.0462 (6)	0.0506 (7)	0.0414 (7)	0.0134 (6)	0.0227 (5)	0.0112 (5)
N2	0.0453 (6)	0.0477 (7)	0.0393 (6)	0.0066 (5)	0.0194 (5)	0.0077 (5)
C1	0.0360 (7)	0.0429 (7)	0.0400 (7)	0.0004 (5)	0.0051 (6)	0.0011 (6)
C2	0.0478 (8)	0.0505 (8)	0.0358 (7)	0.0008 (6)	0.0041 (6)	0.0062 (6)
C3	0.0437 (7)	0.0430 (8)	0.0448 (8)	−0.0010 (6)	0.0136 (6)	0.0037 (6)
C4	0.0335 (7)	0.0506 (8)	0.0530 (9)	−0.0033 (6)	0.0068 (6)	0.0038 (7)
C5	0.0383 (7)	0.0488 (8)	0.0396 (7)	0.0023 (6)	0.0014 (6)	0.0048 (6)
C6	0.0360 (7)	0.0379 (7)	0.0367 (7)	0.0023 (5)	0.0085 (5)	0.0023 (5)
C7	0.0378 (7)	0.0434 (7)	0.0387 (7)	0.0050 (6)	0.0105 (6)	0.0030 (6)
C8	0.0484 (8)	0.0466 (8)	0.0463 (8)	0.0108 (7)	0.0218 (6)	0.0064 (7)
C9	0.0468 (8)	0.0393 (7)	0.0418 (7)	0.0055 (6)	0.0176 (6)	0.0046 (6)
C10	0.0468 (8)	0.0526 (9)	0.0572 (9)	0.0149 (7)	0.0263 (7)	0.0122 (7)
C11	0.0469 (8)	0.0496 (9)	0.0547 (9)	0.0156 (7)	0.0171 (7)	0.0154 (7)
C12	0.0441 (7)	0.0352 (7)	0.0388 (7)	0.0008 (6)	0.0145 (6)	0.0039 (5)
C13	0.0370 (7)	0.0365 (7)	0.0405 (7)	0.0007 (5)	0.0128 (5)	−0.0002 (5)
C14	0.0420 (7)	0.0361 (7)	0.0401 (7)	0.0036 (6)	0.0082 (6)	0.0034 (6)
C15	0.0401 (8)	0.0788 (12)	0.0521 (9)	−0.0036 (7)	−0.0010 (7)	0.0037 (8)
C16	0.0567 (9)	0.0699 (11)	0.0598 (10)	−0.0030 (8)	0.0225 (8)	0.0146 (9)

Geometric parameters (Å, º) top

O1—C7	1.2364 (16)	C5—C6	1.3945 (19)
O1W—H1W1	0.87 (2)	C5—H5A	0.9300
O1W—H2W1	0.94 (2)	C6—C7	1.4884 (18)
O2—C13	1.3645 (15)	C8—C9	1.4581 (19)
O2—H2A	0.88 (2)	C8—H8A	0.9300
O3—C12	1.3599 (16)	C9—C10	1.384 (2)
O3—H3A	0.85 (2)	C9—C14	1.3988 (19)
N1—C7	1.3398 (18)	C10—C11	1.382 (2)
N1—N2	1.3877 (15)	C10—H10A	0.9300
N1—H1A	0.913 (19)	C11—C12	1.3835 (19)
N2—C8	1.2729 (19)	C11—H11A	0.9300
C1—C2	1.3878 (19)	C12—C13	1.4004 (19)
C1—C6	1.4026 (19)	C13—C14	1.3725 (19)
C1—C15	1.5069 (19)	C14—H14A	0.9300
C2—C3	1.390 (2)	C15—H15A	0.9600
C2—H2C	0.9300	C15—H15B	0.9600
C3—C4	1.384 (2)	C15—H15C	0.9600
C3—C16	1.507 (2)	C16—H16A	0.9600
C4—C5	1.373 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600

H1W1—O1W—H2W1	112 (2)	C10—C9—C14	119.07 (13)
C13—O2—H2A	110.5 (13)	C10—C9—C8	119.44 (12)
C12—O3—H3A	110.4 (13)	C14—C9—C8	121.48 (13)
C7—N1—N2	121.02 (11)	C11—C10—C9	120.62 (13)
C7—N1—H1A	119.8 (11)	C11—C10—H10A	119.7
N2—N1—H1A	119.2 (11)	C9—C10—H10A	119.7
C8—N2—N1	114.37 (11)	C10—C11—C12	120.24 (14)
C2—C1—C6	117.91 (12)	C10—C11—H11A	119.9
C2—C1—C15	119.00 (13)	C12—C11—H11A	119.9
C6—C1—C15	123.05 (12)	O3—C12—C11	123.41 (13)
C1—C2—C3	122.88 (13)	O3—C12—C13	117.06 (11)
C1—C2—H2C	118.6	C11—C12—C13	119.52 (12)
C3—C2—H2C	118.6	O2—C13—C14	123.35 (12)
C4—C3—C2	118.05 (13)	O2—C13—C12	116.69 (12)
C4—C3—C16	120.85 (13)	C14—C13—C12	119.96 (12)
C2—C3—C16	121.10 (13)	C13—C14—C9	120.57 (13)
C5—C4—C3	120.53 (13)	C13—C14—H14A	119.7
C5—C4—H4A	119.7	C9—C14—H14A	119.7
C3—C4—H4A	119.7	C1—C15—H15A	109.5
C4—C5—C6	121.27 (13)	C1—C15—H15B	109.5
C4—C5—H5A	119.4	H15A—C15—H15B	109.5
C6—C5—H5A	119.4	C1—C15—H15C	109.5
C5—C6—C1	119.32 (12)	H15A—C15—H15C	109.5
C5—C6—C7	118.57 (12)	H15B—C15—H15C	109.5
C1—C6—C7	122.11 (12)	C3—C16—H16A	109.5
O1—C7—N1	122.17 (12)	C3—C16—H16B	109.5
O1—C7—C6	123.86 (12)	H16A—C16—H16B	109.5
N1—C7—C6	113.96 (11)	C3—C16—H16C	109.5
N2—C8—C9	122.36 (12)	H16A—C16—H16C	109.5
N2—C8—H8A	118.8	H16B—C16—H16C	109.5
C9—C8—H8A	118.8

C7—N1—N2—C8	−178.10 (14)	C5—C6—C7—N1	−45.73 (18)
C6—C1—C2—C3	−1.1 (2)	C1—C6—C7—N1	134.90 (14)
C15—C1—C2—C3	−178.87 (15)	N1—N2—C8—C9	−179.45 (13)
C1—C2—C3—C4	2.2 (2)	N2—C8—C9—C10	−163.72 (16)
C1—C2—C3—C16	−177.21 (15)	N2—C8—C9—C14	17.1 (2)
C2—C3—C4—C5	−1.7 (2)	C14—C9—C10—C11	−1.5 (2)
C16—C3—C4—C5	177.66 (15)	C8—C9—C10—C11	179.34 (15)
C3—C4—C5—C6	0.2 (2)	C9—C10—C11—C12	0.6 (3)
C4—C5—C6—C1	0.9 (2)	C10—C11—C12—O3	−178.29 (14)
C4—C5—C6—C7	−178.49 (13)	C10—C11—C12—C13	0.6 (2)
C2—C1—C6—C5	−0.5 (2)	O3—C12—C13—O2	−2.27 (19)
C15—C1—C6—C5	177.23 (14)	C11—C12—C13—O2	178.79 (14)
C2—C1—C6—C7	178.88 (13)	O3—C12—C13—C14	178.14 (12)
C15—C1—C6—C7	−3.4 (2)	C11—C12—C13—C14	−0.8 (2)
N2—N1—C7—O1	−5.9 (2)	O2—C13—C14—C9	−179.69 (13)
N2—N1—C7—C6	172.84 (12)	C12—C13—C14—C9	−0.1 (2)
C5—C6—C7—O1	133.03 (16)	C10—C9—C14—C13	1.3 (2)
C1—C6—C7—O1	−46.3 (2)	C8—C9—C14—C13	−179.59 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N2ⁱ	0.87 (2)	2.20 (2)	3.059 (2)	169 (2)
N1—H1A···O3ⁱⁱ	0.91 (2)	2.08 (2)	2.962 (2)	163 (2)
O1W—H2W1···O1	0.94 (2)	2.01 (2)	2.935 (2)	173 (2)
O2—H2A···O1ⁱ	0.88 (2)	1.94 (2)	2.791 (2)	162 (2)
O3—H3A···O1Wⁱⁱⁱ	0.85 (2)	1.79 (2)	2.629 (2)	172 (2)
C8—H8A···O3ⁱⁱ	0.93	2.58	3.382 (2)	145
C15—H15B···O2ⁱ	0.96	2.52	3.351 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃·H₂O
M_r	302.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.1373 (3), 13.9025 (5), 13.7886 (5)
β (°)	92.913 (1)
V (Å³)	1557.87 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	9012, 2897, 2535
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.05
No. of reflections	2897
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.28

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N2ⁱ	0.87 (2)	2.20 (2)	3.059 (2)	169 (2)
N1—H1A···O3ⁱⁱ	0.91 (2)	2.08 (2)	2.962 (2)	163 (2)
O1W—H2W1···O1	0.94 (2)	2.01 (2)	2.935 (2)	173 (2)
O2—H2A···O1ⁱ	0.88 (2)	1.94 (2)	2.791 (2)	162 (2)
O3—H3A···O1Wⁱⁱⁱ	0.85 (2)	1.79 (2)	2.629 (2)	172 (2)
C8—H8A···O3ⁱⁱ	0.9300	2.5800	3.382 (2)	145
C15—H15B···O2ⁱ	0.9600	2.5200	3.351 (2)	144

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

Acknowledgements

The authors thank the Research Management Institute of UiTM for financial support under the Dana Kecemerlangan Grant Scheme [grant No. 600-RMI/DANA 5/3 RIF (143/2012)].

References

Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255. CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khan, K. M., Taha, M., Naz, F., Siddiqui, S., Rahim, F., Perveen, S. & Choudhary, M. I. (2012). Med. Chem. 8, 705–710. Web of Science CAS PubMed Google Scholar
Musharraf, S. G., Bibi, A., Shahid, N., Najam-ul-Haq, M., Khan, M., Taha, M., Mughal, U. R. & Khan, K. M. (2012). Am. J. Anal. Chem. 3, 779-789. CrossRef CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. 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. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Sammer, Y. (2012). Acta Cryst. E68, o2778. CSD CrossRef IUCr Journals Google Scholar