2-Phenyl-N′-(2-phenyl­acet­yl)acetohydrazide

Abdel-Aziz, H.A.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536812019861

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1680

doi:10.1107/S1600536812019861

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2-Phenyl-N′-(2-phenylacetyl)acetohydrazide

Hatem A. Abdel-Aziz,^a Ching Kheng Quah ^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 30 April 2012; accepted 3 May 2012; online 12 May 2012)

In the title compound, C₁₆H₁₆N₂O₂, the N′-acetylacetohydrazide group is approximately planar (r.m.s. deviation = 0.018 Å for the eight non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6)° with the terminal phenyl rings. The phenyl rings form a dihedral angle of 62.60 (7)°. In the crystal, molecules are linked into sheets lying parallel to (001) by N—H⋯O and C—H⋯O hydrogen bonds. One O atom accepts one N—H⋯O and one C—H⋯O hydrogen bond and the other O atom accepts one N—H⋯O and two C—H⋯O hydrogen bonds. The N—H⋯O hydrogen bonds lead to R₂²(8) loops and the C—H⋯O hydrogen bonds generate R₂¹(6) loops.

Related literature

For general background to and the pharmaceutical applications of hydrazine derivatives, see: Bredihhin & Mäeorg (2008 ); Ragnarsson (2001 ); Ling et al. (2001 ). For further synthesis details, see: Magedov & Smushkevich (1991 ). 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 hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₂
M_r = 268.31
Triclinic, $[P \overline 1]$
a = 5.4531 (6) Å
b = 7.9283 (9) Å
c = 15.1758 (17) Å
α = 94.271 (2)°
β = 92.613 (2)°
γ = 90.830 (2)°
V = 653.50 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.14 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.996
12991 measured reflections
3458 independent reflections
2428 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.134
S = 1.04
3458 reflections
245 parameters
All H-atom parameters refined
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.867 (16)	1.970 (16)	2.8076 (15)	162.4 (16)
C10—H10A⋯O1ⁱ	0.971 (16)	2.465 (16)	3.3103 (18)	145.3 (13)
N1—H1N1⋯O2ⁱⁱ	0.907 (16)	1.948 (16)	2.8283 (15)	163.2 (15)
C7—H7A⋯O2ⁱⁱ	0.973 (16)	2.479 (16)	3.3209 (18)	144.8 (13)
C7—H7B⋯O2ⁱⁱⁱ	1.00 (2)	2.56 (2)	3.4929 (19)	155.2 (13)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+2, -z; (iii) -x+1, -y+2, -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: 10.1107/S1600536812019861/hb6773sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019861/hb6773Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019861/hb6773Isup3.cml

checkCIF report

Comment top

Hydrazine derivatives are widely used in the pharmaceutical applications and also as precursors in organic synthesis (Bredihhin & Mäeorg, 2008). Several hydrazine derivatives were shown to be effective for treatment of tuberculosis, Parkinson's disease and hypertension (Ragnarsson, 2001). Moreover, some hydrazines possess neuroprotective activity and are used as antidepressant drugs (Ling et al., 2001).

In the title compound, Fig. 1, the N'-acetylacetohydrazide moiety (O1/O2/N1/N2/C7-C10) is approximately planar (r.m.s. deviation = 0.018 Å for the 8 non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6)° with the two terminal benzene rings (C1-C6 and C11-C16), respectively. The two benzene rings form a dihedral angle of 62.60 (7)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal (Fig.2), molecules are linked into planes parallel to the (001) via intermolecular N1–H1N1···O2, C7–H7A···O2 and C7–H7B···O2 trifurcated acceptor bonds (Table 1) and N2–H1N2···O1 and C10–H10A···O1 bifurcated acceptor bonds (Table 1), generating R₂¹(6) ring motifs (Bernstein et al., 1995).

Related literature top

For general background to and the pharmaceutical applications of hydrazine derivatives, see: Bredihhin & Mäeorg (2008); Ragnarsson (2001); Ling et al. (2001). For further synthesis details, see: Magedov & Smushkevich (1991). 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 hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by the reaction of 2-phenylacetyl chloride with 2-phenylacetohydrazide in the presence of sodium carbonate in water at 5-10 °C (Magedov & Smushkevich, 1991).

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 a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

2-Phenyl-N'-(2-phenylacetyl)acetohydrazide top

Crystal data top

C₁₆H₁₆N₂O₂	Z = 2
M_r = 268.31	F(000) = 284
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4531 (6) Å	Cell parameters from 3410 reflections
b = 7.9283 (9) Å	θ = 4.0–30.0°
c = 15.1758 (17) Å	µ = 0.09 mm⁻¹
α = 94.271 (2)°	T = 100 K
β = 92.613 (2)°	Needle, colourless
γ = 90.830 (2)°	0.35 × 0.14 × 0.05 mm
V = 653.50 (13) Å³

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3458 independent reflections
Radiation source: fine-focus sealed tube	2428 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 29.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.968, T_max = 0.996	k = −10→10
12991 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0709P)² + 0.1901P] where P = (F_o² + 2F_c²)/3
3458 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₂	γ = 90.830 (2)°
M_r = 268.31	V = 653.50 (13) Å³
Triclinic, P1	Z = 2
a = 5.4531 (6) Å	Mo Kα radiation
b = 7.9283 (9) Å	µ = 0.09 mm⁻¹
c = 15.1758 (17) Å	T = 100 K
α = 94.271 (2)°	0.35 × 0.14 × 0.05 mm
β = 92.613 (2)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	3458 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2428 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.996	R_int = 0.030
12991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.134	All H-atom parameters refined
S = 1.04	Δρ_max = 0.38 e Å⁻³
3458 reflections	Δρ_min = −0.29 e Å⁻³
245 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
O1	0.40065 (18)	0.64320 (12)	0.06665 (6)	0.0165 (2)
O2	1.08994 (18)	0.85895 (12)	−0.07188 (6)	0.0166 (2)
N1	0.7067 (2)	0.81353 (14)	0.02864 (7)	0.0131 (2)
N2	0.7869 (2)	0.68791 (14)	−0.03185 (7)	0.0136 (2)
C1	0.2796 (3)	0.94134 (17)	0.29275 (9)	0.0154 (3)
C2	0.3026 (3)	0.90738 (18)	0.38118 (9)	0.0185 (3)
C3	0.4978 (3)	0.81340 (18)	0.41175 (9)	0.0184 (3)
C4	0.6710 (3)	0.75379 (18)	0.35344 (9)	0.0180 (3)
C5	0.6502 (2)	0.78955 (17)	0.26515 (9)	0.0153 (3)
C6	0.4540 (2)	0.88282 (16)	0.23362 (8)	0.0127 (3)
C7	0.4336 (3)	0.92581 (17)	0.13786 (8)	0.0129 (3)
C8	0.5093 (2)	0.78171 (16)	0.07486 (8)	0.0120 (3)
C9	0.9839 (2)	0.71983 (16)	−0.07846 (8)	0.0120 (3)
C10	1.0630 (3)	0.57244 (17)	−0.13972 (8)	0.0137 (3)
C11	1.0445 (2)	0.61346 (16)	−0.23584 (8)	0.0127 (3)
C12	1.2278 (3)	0.70965 (18)	−0.27062 (9)	0.0162 (3)
C13	1.2100 (3)	0.74792 (18)	−0.35846 (9)	0.0186 (3)
C14	1.0109 (3)	0.68811 (19)	−0.41296 (9)	0.0200 (3)
C15	0.8286 (3)	0.59203 (19)	−0.37894 (9)	0.0196 (3)
C16	0.8446 (3)	0.55437 (17)	−0.29055 (9)	0.0161 (3)
H1N1	0.787 (3)	0.915 (2)	0.0321 (11)	0.023 (5)*
H1N2	0.705 (3)	0.593 (2)	−0.0350 (11)	0.017 (4)*
H1A	0.148 (3)	1.007 (2)	0.2720 (11)	0.022 (4)*
H2A	0.175 (3)	0.951 (2)	0.4219 (10)	0.017 (4)*
H3A	0.519 (4)	0.786 (2)	0.4710 (13)	0.031 (5)*
H4A	0.809 (3)	0.686 (2)	0.3727 (11)	0.021 (4)*
H5A	0.775 (3)	0.747 (2)	0.2245 (11)	0.018 (4)*
H7A	0.529 (3)	1.028 (2)	0.1304 (10)	0.018 (4)*
H7B	0.259 (4)	0.953 (2)	0.1223 (12)	0.027 (5)*
H10A	0.967 (3)	0.471 (2)	−0.1318 (10)	0.016 (4)*
H10B	1.240 (3)	0.554 (2)	−0.1200 (11)	0.021 (4)*
H12A	1.373 (3)	0.757 (2)	−0.2322 (11)	0.022 (4)*
H13A	1.339 (3)	0.814 (2)	−0.3815 (12)	0.029 (5)*
H14A	1.002 (3)	0.713 (2)	−0.4733 (12)	0.028 (5)*
H16A	0.720 (3)	0.489 (2)	−0.2662 (12)	0.029 (5)*
H15A	0.692 (3)	0.549 (2)	−0.4190 (11)	0.017 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0172 (5)	0.0123 (5)	0.0198 (5)	−0.0052 (4)	0.0047 (4)	−0.0010 (4)
O2	0.0172 (5)	0.0119 (5)	0.0206 (5)	−0.0033 (4)	0.0051 (4)	−0.0013 (4)
N1	0.0151 (6)	0.0101 (5)	0.0141 (5)	−0.0019 (4)	0.0042 (4)	−0.0016 (4)
N2	0.0156 (6)	0.0100 (5)	0.0150 (5)	−0.0023 (4)	0.0052 (4)	−0.0021 (4)
C1	0.0137 (6)	0.0143 (6)	0.0184 (6)	−0.0001 (5)	0.0029 (5)	0.0002 (5)
C2	0.0195 (7)	0.0175 (7)	0.0185 (7)	−0.0024 (5)	0.0059 (5)	−0.0006 (5)
C3	0.0235 (8)	0.0176 (7)	0.0143 (6)	−0.0031 (6)	0.0014 (5)	0.0021 (5)
C4	0.0170 (7)	0.0173 (7)	0.0191 (7)	0.0005 (5)	−0.0028 (5)	0.0005 (5)
C5	0.0142 (6)	0.0146 (6)	0.0169 (6)	0.0002 (5)	0.0022 (5)	−0.0011 (5)
C6	0.0128 (6)	0.0107 (6)	0.0143 (6)	−0.0038 (5)	0.0017 (5)	−0.0007 (5)
C7	0.0139 (6)	0.0106 (6)	0.0143 (6)	0.0000 (5)	0.0028 (5)	−0.0003 (5)
C8	0.0124 (6)	0.0114 (6)	0.0121 (6)	−0.0005 (5)	−0.0006 (5)	0.0013 (4)
C9	0.0134 (6)	0.0112 (6)	0.0115 (6)	−0.0001 (5)	0.0012 (5)	0.0013 (4)
C10	0.0156 (7)	0.0107 (6)	0.0149 (6)	−0.0003 (5)	0.0039 (5)	0.0007 (5)
C11	0.0132 (6)	0.0090 (6)	0.0161 (6)	0.0016 (5)	0.0037 (5)	−0.0008 (5)
C12	0.0148 (7)	0.0155 (6)	0.0179 (6)	−0.0020 (5)	0.0026 (5)	−0.0013 (5)
C13	0.0211 (7)	0.0169 (7)	0.0182 (7)	−0.0019 (5)	0.0060 (5)	0.0009 (5)
C14	0.0254 (8)	0.0191 (7)	0.0155 (6)	0.0040 (6)	0.0016 (6)	0.0016 (5)
C15	0.0185 (7)	0.0185 (7)	0.0210 (7)	0.0010 (6)	−0.0043 (6)	−0.0005 (5)
C16	0.0131 (6)	0.0140 (6)	0.0212 (7)	−0.0018 (5)	0.0020 (5)	0.0012 (5)

Geometric parameters (Å, º) top

O1—C8	1.2355 (16)	C7—C8	1.5089 (18)
O2—C9	1.2332 (16)	C7—H7A	0.975 (18)
N1—C8	1.3426 (16)	C7—H7B	1.002 (19)
N1—N2	1.3922 (14)	C9—C10	1.5183 (18)
N1—H1N1	0.908 (19)	C10—C11	1.5172 (18)
N2—C9	1.3443 (16)	C10—H10A	0.972 (17)
N2—H1N2	0.869 (18)	C10—H10B	1.013 (18)
C1—C2	1.3888 (19)	C11—C16	1.3934 (19)
C1—C6	1.3977 (18)	C11—C12	1.3951 (18)
C1—H1A	0.950 (18)	C12—C13	1.3884 (19)
C2—C3	1.390 (2)	C12—H12A	1.009 (18)
C2—H2A	1.000 (16)	C13—C14	1.390 (2)
C3—C4	1.388 (2)	C13—H13A	0.963 (19)
C3—H3A	0.942 (19)	C14—C15	1.385 (2)
C4—C5	1.3899 (19)	C14—H14A	0.949 (18)
C4—H4A	0.977 (17)	C15—C16	1.3948 (19)
C5—C6	1.3960 (18)	C15—H15A	0.980 (17)
C5—H5A	0.986 (17)	C16—H16A	0.954 (19)
C6—C7	1.5167 (18)

C8—N1—N2	118.83 (11)	O1—C8—N1	121.88 (12)
C8—N1—H1N1	123.8 (11)	O1—C8—C7	122.94 (12)
N2—N1—H1N1	117.2 (11)	N1—C8—C7	115.18 (11)
C9—N2—N1	118.90 (11)	O2—C9—N2	122.08 (12)
C9—N2—H1N2	125.2 (11)	O2—C9—C10	123.08 (12)
N1—N2—H1N2	115.9 (11)	N2—C9—C10	114.84 (11)
C2—C1—C6	120.35 (13)	C11—C10—C9	111.62 (11)
C2—C1—H1A	120.4 (10)	C11—C10—H10A	110.1 (9)
C6—C1—H1A	119.2 (10)	C9—C10—H10A	111.1 (10)
C1—C2—C3	120.42 (13)	C11—C10—H10B	110.7 (10)
C1—C2—H2A	118.5 (9)	C9—C10—H10B	104.3 (10)
C3—C2—H2A	121.0 (9)	H10A—C10—H10B	108.8 (14)
C4—C3—C2	119.67 (13)	C16—C11—C12	119.24 (12)
C4—C3—H3A	117.1 (12)	C16—C11—C10	120.29 (12)
C2—C3—H3A	123.2 (12)	C12—C11—C10	120.47 (12)
C3—C4—C5	120.00 (13)	C13—C12—C11	120.42 (14)
C3—C4—H4A	121.6 (10)	C13—C12—H12A	118.5 (10)
C5—C4—H4A	118.4 (10)	C11—C12—H12A	121.0 (10)
C4—C5—C6	120.81 (12)	C12—C13—C14	120.18 (13)
C4—C5—H5A	119.2 (9)	C12—C13—H13A	119.3 (11)
C6—C5—H5A	120.0 (9)	C14—C13—H13A	120.5 (11)
C5—C6—C1	118.74 (12)	C15—C14—C13	119.70 (13)
C5—C6—C7	121.05 (11)	C15—C14—H14A	120.6 (12)
C1—C6—C7	120.17 (12)	C13—C14—H14A	119.7 (12)
C8—C7—C6	112.43 (11)	C14—C15—C16	120.35 (14)
C8—C7—H7A	111.1 (10)	C14—C15—H15A	118.1 (10)
C6—C7—H7A	110.0 (9)	C16—C15—H15A	121.5 (10)
C8—C7—H7B	108.1 (11)	C11—C16—C15	120.10 (13)
C6—C7—H7B	108.9 (10)	C11—C16—H16A	118.7 (11)
H7A—C7—H7B	105.9 (14)	C15—C16—H16A	121.2 (11)

C8—N1—N2—C9	179.72 (11)	N1—N2—C9—O2	−2.93 (19)
C6—C1—C2—C3	−0.6 (2)	N1—N2—C9—C10	177.53 (11)
C1—C2—C3—C4	0.2 (2)	O2—C9—C10—C11	−61.91 (17)
C2—C3—C4—C5	0.6 (2)	N2—C9—C10—C11	117.63 (13)
C3—C4—C5—C6	−1.1 (2)	C9—C10—C11—C16	−100.39 (15)
C4—C5—C6—C1	0.6 (2)	C9—C10—C11—C12	80.05 (15)
C4—C5—C6—C7	178.53 (13)	C16—C11—C12—C13	0.8 (2)
C2—C1—C6—C5	0.2 (2)	C10—C11—C12—C13	−179.64 (12)
C2—C1—C6—C7	−177.69 (13)	C11—C12—C13—C14	−1.1 (2)
C5—C6—C7—C8	39.28 (18)	C12—C13—C14—C15	0.9 (2)
C1—C6—C7—C8	−142.87 (13)	C13—C14—C15—C16	−0.3 (2)
N2—N1—C8—O1	1.69 (19)	C12—C11—C16—C15	−0.3 (2)
N2—N1—C8—C7	−179.17 (11)	C10—C11—C16—C15	−179.84 (12)
C6—C7—C8—O1	62.54 (17)	C14—C15—C16—C11	0.1 (2)
C6—C7—C8—N1	−116.59 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.867 (16)	1.970 (16)	2.8076 (15)	162.4 (16)
C10—H10A···O1ⁱ	0.971 (16)	2.465 (16)	3.3103 (18)	145.3 (13)
N1—H1N1···O2ⁱⁱ	0.907 (16)	1.948 (16)	2.8283 (15)	163.2 (15)
C7—H7A···O2ⁱⁱ	0.973 (16)	2.479 (16)	3.3209 (18)	144.8 (13)
C7—H7B···O2ⁱⁱⁱ	1.00 (2)	2.56 (2)	3.4929 (19)	155.2 (13)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₂
M_r	268.31
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.4531 (6), 7.9283 (9), 15.1758 (17)
α, β, γ (°)	94.271 (2), 92.613 (2), 90.830 (2)
V (Å³)	653.50 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.14 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	12991, 3458, 2428
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.134, 1.04
No. of reflections	3458
No. of parameters	245
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.29

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—H1N2···O1ⁱ	0.867 (16)	1.970 (16)	2.8076 (15)	162.4 (16)
C10—H10A···O1ⁱ	0.971 (16)	2.465 (16)	3.3103 (18)	145.3 (13)
N1—H1N1···O2ⁱⁱ	0.907 (16)	1.948 (16)	2.8283 (15)	163.2 (15)
C7—H7A···O2ⁱⁱ	0.973 (16)	2.479 (16)	3.3209 (18)	144.8 (13)
C7—H7B···O2ⁱⁱⁱ	1.00 (2)	2.56 (2)	3.4929 (19)	155.2 (13)

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

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160) and the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.

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