(E)-N′-(4-Isopropyl­benzyl­idene)isonicotinohydrazide monohydrate

Bhat, M.A.; Abdel-Aziz, H.A.; Ghabbour, H.A.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536812009099

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1002

doi:10.1107/S1600536812009099

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(E)-N′-(4-Isopropylbenzylidene)isonicotinohydrazide monohydrate

Mashooq A. Bhat,^a Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*‡

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 16 February 2012; accepted 29 February 2012; online 10 March 2012)

In the title compound, C₁₆H₁₇N₃O·H₂O, the isonicotinohydrazide molecule adopts an E conformation about the central C=N double bond. The dihedral angle between the pyridine and the benzene rings is 54.56 (15)°. In the crystal, molecules are connected via N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For details and the biological activity of isoniazide, see: Bloom & Murray (1992 ); Loenhout-Rooyackers & Veen (1998 ); Hearn et al. (2009 ); Tripathi et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₇N₃O·H₂O
M_r = 285.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.7503 (2) Å
b = 11.7894 (3) Å
c = 17.2820 (4) Å
V = 1579.08 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 296 K
0.89 × 0.19 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.594, T_max = 0.920
6473 measured reflections
2939 independent reflections
2499 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.145
S = 1.04
2939 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.22 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
N2—H1N1⋯O1W	0.85	1.90	2.757 (3)	176
O1W—H1W1⋯N1ⁱ	0.85	2.03	2.861 (3)	164
O1W—H2W1⋯O1ⁱⁱ	0.84	2.00	2.779 (3)	154
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536812009099/cv5248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009099/cv5248Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009099/cv5248Isup3.cml

checkCIF report

Comment top

In the last decade, tuberculosis (TB) has reemerged as one of the leading causes of death in the world, reaching nearly three million deaths annually (Bloom & Murray, 1992). Therefore, the search for new drugs for tuberculosis is of the utmost importance. Treatment regimens are based on a long-term and combined chemotherapy. The most used first-choice drug is isoniazid, a bactericidal drug that acts both intracellularly in the macrophages and extracellularly in the necrotic tissue (Loenhout-Rooyackers & Veen, 1998). The derivatives of isoniazid have been found to possess potential tuberculostatic activity (Hearn et al., 2009; Tripathi et al., 2011). Herein, we present the crystal structure of the title compound, (I).

The asymmetric unit of (I) contains one N'-(4-isopropylbenzylidene) isonicotinohydrazide molecule and one water molecule (Fig. 1). The molecule adopts an E configuration about the central C7═N3 double bond. The dihedral angle between the pyridine (N1/C1–C5) and the benzene (C8–C13) rings is 54.56 (15)°. The hydrazine group is twisted slightly, with a C5-C6-N2-N3 torsion angle of -178.9 (2)°.

In the crystal, the molecules are connected via N—H···O, O—H···N and O—H···O hydrogen bonds (Table 1), forming a three-dimensional networks (Fig. 2).

Related literature top

For details and the biological activity of isoniazide, see: Bloom & Murray (1992); Loenhout-Rooyackers & Veen (1998); Hearn et al. (2009); Tripathi et al. (2011).

Experimental top

The title compound was prepared by the reaction of 4-isopropyl benzaldehyde (0.15 g, 1 mmol) with isoniazid (0.14 g, 1 mmol) in EtOH (25 mL). After stirring for 3 h, at room temperature, the resulting mixture was concentrated. The precipitate was washed with EtOH to afford the title compound. Colourless blocks of the title compound suitable for X-ray structure determination were recrystallized from EtOH by the slow evaporation of the solvent at room temperature.

Structure description top

In the crystal, the molecules are connected via N—H···O, O—H···N and O—H···O hydrogen bonds (Table 1), forming a three-dimensional networks (Fig. 2).

For details and the biological activity of isoniazide, see: Bloom & Murray (1992); Loenhout-Rooyackers & Veen (1998); Hearn et al. (2009); Tripathi et al. (2011).

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 asymmetric unit of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids. Hydrogen bond is shown by dashed line.
	Fig. 2. A portion of the crystal packing showing hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding were omitted for clarity.

(E)-N'-(4-Isopropylbenzylidene)isonicotinohydrazide monohydrate top

Crystal data top

C₁₆H₁₇N₃O·H₂O	F(000) = 608
M_r = 285.34	D_x = 1.200 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1751 reflections
a = 7.7503 (2) Å	θ = 4.5–65.6°
b = 11.7894 (3) Å	µ = 0.65 mm⁻¹
c = 17.2820 (4) Å	T = 296 K
V = 1579.08 (7) Å³	Block, colourless
Z = 4	0.89 × 0.19 × 0.13 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2939 independent reflections
Radiation source: fine-focus sealed tube	2499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 71.8°, θ_min = 4.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→8
T_min = 0.594, T_max = 0.920	k = −13→10
6473 measured reflections	l = −20→21

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0715P)² + 0.3351P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.22 e Å⁻³
2939 reflections	Δρ_min = −0.28 e Å⁻³
193 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0045 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881, 1072 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.8 (4)

Crystal data top

C₁₆H₁₇N₃O·H₂O	V = 1579.08 (7) Å³
M_r = 285.34	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 7.7503 (2) Å	µ = 0.65 mm⁻¹
b = 11.7894 (3) Å	T = 296 K
c = 17.2820 (4) Å	0.89 × 0.19 × 0.13 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2939 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2499 reflections with I > 2σ(I)
T_min = 0.594, T_max = 0.920	R_int = 0.032
6473 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.145	Δρ_max = 0.22 e Å⁻³
S = 1.04	Δρ_min = −0.28 e Å⁻³
2939 reflections	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881, 1072 Friedel pairs
193 parameters	Absolute structure parameter: 0.8 (4)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.1044 (3)	−0.05606 (15)	0.18186 (11)	0.0761 (6)
N1	1.1036 (4)	0.1562 (2)	−0.06565 (14)	0.0839 (8)
H1N1	0.9718	0.1817	0.2093	0.101*
N2	1.0132 (3)	0.11714 (17)	0.22203 (11)	0.0573 (5)
N3	1.0056 (3)	0.08469 (18)	0.29864 (11)	0.0578 (5)
C1	1.1390 (4)	0.1925 (2)	0.06922 (16)	0.0666 (7)
H1A	1.1742	0.2420	0.1080	0.080*
C2	1.1526 (5)	0.2221 (3)	−0.00740 (18)	0.0785 (9)
H2A	1.1990	0.2927	−0.0192	0.094*
C3	1.0378 (5)	0.0560 (3)	−0.04701 (17)	0.0835 (9)
H3A	1.0012	0.0089	−0.0869	0.100*
C4	1.0204 (4)	0.0177 (2)	0.02743 (15)	0.0670 (7)
H4A	0.9750	−0.0538	0.0374	0.080*
C5	1.0715 (3)	0.0872 (2)	0.08717 (13)	0.0536 (5)
C6	1.0648 (3)	0.0424 (2)	0.16813 (14)	0.0555 (6)
C7	0.9297 (3)	0.1536 (2)	0.34324 (14)	0.0571 (6)
H7A	0.8811	0.2185	0.3217	0.069*
C8	0.9143 (3)	0.1369 (2)	0.42615 (13)	0.0515 (5)
C9	0.9887 (4)	0.0448 (2)	0.46475 (15)	0.0604 (6)
H9A	1.0450	−0.0113	0.4366	0.072*
C10	0.9792 (4)	0.0366 (2)	0.54362 (15)	0.0689 (7)
H10A	1.0299	−0.0253	0.5680	0.083*
C11	0.8961 (4)	0.1178 (2)	0.58831 (15)	0.0692 (7)
C12	0.8237 (4)	0.2085 (3)	0.54993 (16)	0.0699 (7)
H12A	0.7684	0.2649	0.5783	0.084*
C13	0.8312 (4)	0.2176 (2)	0.47065 (15)	0.0611 (6)
H13A	0.7793	0.2792	0.4465	0.073*
C14	0.8851 (9)	0.1105 (4)	0.67642 (19)	0.1318 (19)
H14A	0.7599	0.1151	0.6836	0.158*
C15	0.9192 (7)	−0.0015 (4)	0.7099 (2)	0.1196 (15)
H15A	0.8882	−0.0011	0.7637	0.179*
H15B	1.0396	−0.0190	0.7048	0.179*
H15C	0.8521	−0.0576	0.6832	0.179*
C16	0.9387 (9)	0.2120 (5)	0.7158 (2)	0.149 (2)
H16A	0.8925	0.2121	0.7674	0.223*
H16B	0.8968	0.2771	0.6883	0.223*
H16C	1.0624	0.2145	0.7181	0.223*
O1W	0.8651 (3)	0.32125 (15)	0.18150 (11)	0.0822 (7)
H1W1	0.7748	0.3209	0.1531	0.123*
H2W1	0.8803	0.3754	0.2127	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1132 (16)	0.0556 (10)	0.0594 (10)	0.0199 (10)	0.0095 (11)	0.0108 (9)
N1	0.114 (2)	0.0893 (18)	0.0484 (12)	0.0015 (16)	0.0134 (14)	0.0090 (12)
N2	0.0738 (13)	0.0546 (12)	0.0436 (10)	0.0047 (10)	0.0017 (9)	0.0057 (8)
N3	0.0726 (13)	0.0566 (12)	0.0443 (10)	0.0010 (10)	−0.0025 (9)	0.0063 (9)
C1	0.0849 (17)	0.0594 (15)	0.0555 (14)	−0.0062 (13)	0.0094 (13)	−0.0003 (12)
C2	0.107 (2)	0.0670 (18)	0.0617 (17)	−0.0041 (16)	0.0213 (16)	0.0106 (14)
C3	0.113 (3)	0.086 (2)	0.0525 (15)	−0.0043 (19)	−0.0001 (16)	−0.0066 (14)
C4	0.0819 (18)	0.0642 (16)	0.0547 (14)	−0.0060 (14)	0.0020 (13)	0.0000 (12)
C5	0.0623 (13)	0.0537 (13)	0.0448 (11)	0.0029 (11)	0.0079 (10)	0.0043 (10)
C6	0.0638 (13)	0.0541 (14)	0.0486 (12)	0.0022 (11)	0.0030 (11)	0.0030 (10)
C7	0.0697 (14)	0.0512 (13)	0.0504 (13)	0.0021 (12)	−0.0057 (11)	0.0055 (10)
C8	0.0559 (11)	0.0526 (13)	0.0462 (11)	0.0002 (10)	−0.0027 (10)	0.0009 (9)
C9	0.0750 (16)	0.0530 (13)	0.0531 (13)	0.0117 (12)	0.0005 (12)	0.0027 (10)
C10	0.0871 (19)	0.0657 (16)	0.0538 (14)	0.0139 (14)	−0.0047 (13)	0.0083 (12)
C11	0.0913 (19)	0.0708 (17)	0.0455 (13)	0.0007 (15)	0.0039 (13)	−0.0005 (12)
C12	0.0798 (18)	0.0674 (16)	0.0624 (16)	0.0095 (14)	0.0115 (13)	−0.0081 (14)
C13	0.0659 (15)	0.0567 (14)	0.0607 (14)	0.0118 (12)	−0.0004 (12)	0.0022 (11)
C14	0.238 (6)	0.108 (3)	0.0494 (18)	0.018 (4)	0.006 (3)	0.0001 (19)
C15	0.149 (4)	0.149 (4)	0.0615 (19)	−0.022 (3)	0.008 (2)	0.034 (2)
C16	0.204 (5)	0.180 (5)	0.062 (2)	−0.002 (5)	−0.027 (3)	−0.026 (3)
O1W	0.1251 (18)	0.0586 (11)	0.0628 (11)	0.0163 (11)	−0.0286 (12)	−0.0119 (9)

Geometric parameters (Å, º) top

O1—C6	1.224 (3)	C9—C10	1.368 (3)
N1—C3	1.326 (4)	C9—H9A	0.9300
N1—C2	1.327 (4)	C10—C11	1.389 (4)
N2—C6	1.343 (3)	C10—H10A	0.9300
N2—N3	1.379 (3)	C11—C12	1.377 (4)
N2—H1N1	0.8550	C11—C14	1.528 (4)
N3—C7	1.266 (3)	C12—C13	1.376 (4)
C1—C2	1.373 (4)	C12—H12A	0.9300
C1—C5	1.383 (4)	C13—H13A	0.9300
C1—H1A	0.9300	C14—C16	1.438 (6)
C2—H2A	0.9300	C14—C15	1.465 (6)
C3—C4	1.370 (4)	C14—H14A	0.9800
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.376 (4)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.496 (3)	C16—H16A	0.9600
C7—C8	1.451 (3)	C16—H16B	0.9600
C7—H7A	0.9300	C16—H16C	0.9600
C8—C13	1.382 (3)	O1W—H1W1	0.8541
C8—C9	1.398 (3)	O1W—H2W1	0.8437

C3—N1—C2	116.6 (3)	C9—C10—C11	122.0 (3)
C6—N2—N3	119.78 (19)	C9—C10—H10A	119.0
C6—N2—H1N1	121.2	C11—C10—H10A	119.0
N3—N2—H1N1	118.5	C12—C11—C10	117.1 (2)
C7—N3—N2	115.2 (2)	C12—C11—C14	120.1 (3)
C2—C1—C5	118.3 (3)	C10—C11—C14	122.7 (3)
C2—C1—H1A	120.9	C13—C12—C11	121.5 (3)
C5—C1—H1A	120.9	C13—C12—H12A	119.2
N1—C2—C1	124.1 (3)	C11—C12—H12A	119.2
N1—C2—H2A	117.9	C12—C13—C8	121.4 (3)
C1—C2—H2A	117.9	C12—C13—H13A	119.3
N1—C3—C4	124.0 (3)	C8—C13—H13A	119.3
N1—C3—H3A	118.0	C16—C14—C15	120.7 (4)
C4—C3—H3A	118.0	C16—C14—C11	114.1 (4)
C3—C4—C5	118.7 (3)	C15—C14—C11	115.8 (3)
C3—C4—H4A	120.7	C16—C14—H14A	100.3
C5—C4—H4A	120.7	C15—C14—H14A	100.3
C4—C5—C1	118.4 (2)	C11—C14—H14A	100.3
C4—C5—C6	118.8 (2)	C14—C15—H15A	109.5
C1—C5—C6	122.6 (2)	C14—C15—H15B	109.5
O1—C6—N2	124.2 (2)	H15A—C15—H15B	109.5
O1—C6—C5	120.5 (2)	C14—C15—H15C	109.5
N2—C6—C5	115.3 (2)	H15A—C15—H15C	109.5
N3—C7—C8	123.5 (2)	H15B—C15—H15C	109.5
N3—C7—H7A	118.2	C14—C16—H16A	109.5
C8—C7—H7A	118.2	C14—C16—H16B	109.5
C13—C8—C9	117.4 (2)	H16A—C16—H16B	109.5
C13—C8—C7	119.6 (2)	C14—C16—H16C	109.5
C9—C8—C7	122.9 (2)	H16A—C16—H16C	109.5
C10—C9—C8	120.5 (2)	H16B—C16—H16C	109.5
C10—C9—H9A	119.7	H1W1—O1W—H2W1	119.0
C8—C9—H9A	119.7

C6—N2—N3—C7	−169.0 (3)	N3—C7—C8—C13	179.0 (3)
C3—N1—C2—C1	0.0 (5)	N3—C7—C8—C9	2.7 (4)
C5—C1—C2—N1	0.6 (5)	C13—C8—C9—C10	−0.3 (4)
C2—N1—C3—C4	−0.9 (5)	C7—C8—C9—C10	176.0 (3)
N1—C3—C4—C5	1.0 (5)	C8—C9—C10—C11	0.2 (5)
C3—C4—C5—C1	−0.3 (4)	C9—C10—C11—C12	−0.4 (5)
C3—C4—C5—C6	−175.6 (3)	C9—C10—C11—C14	−179.6 (4)
C2—C1—C5—C4	−0.4 (4)	C10—C11—C12—C13	0.8 (5)
C2—C1—C5—C6	174.7 (3)	C14—C11—C12—C13	−179.9 (4)
N3—N2—C6—O1	1.3 (4)	C11—C12—C13—C8	−1.1 (5)
N3—N2—C6—C5	−178.9 (2)	C9—C8—C13—C12	0.8 (4)
C4—C5—C6—O1	38.5 (4)	C7—C8—C13—C12	−175.7 (3)
C1—C5—C6—O1	−136.6 (3)	C12—C11—C14—C16	−50.3 (7)
C4—C5—C6—N2	−141.4 (3)	C10—C11—C14—C16	128.9 (5)
C1—C5—C6—N2	43.6 (4)	C12—C11—C14—C15	162.9 (4)
N2—N3—C7—C8	−177.5 (2)	C10—C11—C14—C15	−17.9 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···O1W	0.85	1.90	2.757 (3)	176
O1W—H1W1···N1ⁱ	0.85	2.03	2.861 (3)	164
O1W—H2W1···O1ⁱⁱ	0.84	2.00	2.779 (3)	154

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O·H₂O
M_r	285.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.7503 (2), 11.7894 (3), 17.2820 (4)
V (Å³)	1579.08 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.89 × 0.19 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.594, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	6473, 2939, 2499
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.145, 1.04
No. of reflections	2939
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28
Absolute structure	Flack, H. D. (1983). Acta Cryst. A39, 876–881, 1072 Friedel pairs
Absolute structure parameter	0.8 (4)

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
N2—H1N1···O1W	0.85	1.90	2.757 (3)	176
O1W—H1W1···N1ⁱ	0.85	2.03	2.861 (3)	164
O1W—H2W1···O1ⁱⁱ	0.84	2.00	2.779 (3)	154

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

Footnotes

‡College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

MAB, HAA and HAG thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. MH and HFK thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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