3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile

Abdel-Aziz, H.A.; Ghabbour, H.A.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812010938

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1095-o1096

doi:10.1107/S1600536812010938

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3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile

Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Suchada Chantrapromma ^b ‡ and Hoong-Kun Fun ^c ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 12 March 2012; accepted 13 March 2012; online 17 March 2012)

The title compound, C₁₈H₁₃N₃O, has a butterfly-like structure, in which the pyrazole ring forms dihedral angles of 59.31 (8) and 57.24 (8)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 64.03 (8)°. The pyrazole ring and the C—C=O plane of the acetyl group are twisted slightly, making a dihedral angle of 7.95 (18)°. In the crystal, molecules are linked through weak C—H⋯N and C—H⋯O interactions into a helical chain along the a-axis direction.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009 , 2010 ); Abdel-Wahab et al. (2009 ); Bharate et al. (2008 ); Dawood et al. (2003 ); Fu et al. (2010 ); Thumar & Patel (2011 ). For a related structure, see: Abdel-Aziz et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₃N₃O
M_r = 287.31
Orthorhombic, P b c a
a = 6.8322 (2) Å
b = 16.8974 (5) Å
c = 25.7968 (6) Å
V = 2978.15 (14) Å³
Z = 8
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 296 K
0.56 × 0.35 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.708, T_max = 0.863
10678 measured reflections
2782 independent reflections
2338 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.08
2782 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯N3ⁱ	0.93	2.53	3.432 (2)	165
C16—H16A⋯O1ⁱⁱ	0.93	2.59	3.3758 (19)	142
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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/S1600536812010938/is5091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010938/is5091Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010938/is5091Isup3.cml

checkCIF report

Comment top

Owing to the various biological properties of pyrazole derivatives such as anti-cancer (Fu et al., 2010), anti-inflammatory (Bharate et al., 2008) and antimicrobial activities (Thumar & Patel, 2011), we have during the course of our medicinal chemistry research reported the synthesis and bioactivity of pyrazole derivatives (Abdel-Aziz et al., 2009, 2010; Abdel-Wahab et al., 2009). The title compound (I) was synthesized and characterized in order to study the structure activity relationship of this class of compounds.

The molecule of (I), C₁₈H₁₃N₃O, has a butterfly-like structure. The pyrazole ring forms the dihedral angles of 59.31 (8) and 57.24 (8)°, respectively, with the C5–C10 and C11–C16 phenyl rings, whereas the dihedral angle between these two rings is 64.03 (8)°. The cabonitrile substituent lies on the same plane with the pyrazole ring with an r.m.s. 0.0027 (1) Å for the seven non-H atoms (C1–C4/N1–N3), whereas the acetyl group is slightly deviated with the torsion angles N2–C1–C17–C18 = 8.3 (2)° and N2–C1–C17–O1 = -171.47 (13)°. The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structure (Abdel-Aziz et al., 2011). The crystal packing of (I) is stabilized by weak C—H···N and C—H···O interactions (Table 1). Figure 2 shows the molecular a helical chain along the [1 0 0] linked by these interactions.

Related literature top

For bond-length data, see: Allen et al. (1987). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009, 2010); Abdel-Wahab et al. (2009); Bharate et al. (2008); Dawood et al. (2003); Fu et al. (2010); Thumar & Patel (2011). For a related structure, see: Abdel-Aziz et al. (2011).

Experimental top

The title compound was prepared according to the reported method (Dawood et al., 2003). Single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.

Structure description top

For bond-length data, see: Allen et al. (1987). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009, 2010); Abdel-Wahab et al. (2009); Bharate et al. (2008); Dawood et al. (2003); Fu et al. (2010); Thumar & Patel (2011). For a related structure, see: Abdel-Aziz 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 molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing diagram of the title compound viewed along the b axis, showing the helical chain along the [1 0 0]. C—H···N hydrogen bonds are shown as dashed lines.

3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile top

Crystal data top

C₁₈H₁₃N₃O	F(000) = 1200
M_r = 287.31	D_x = 1.282 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2782 reflections
a = 6.8322 (2) Å	θ = 3.4–69.9°
b = 16.8974 (5) Å	µ = 0.66 mm⁻¹
c = 25.7968 (6) Å	T = 296 K
V = 2978.15 (14) Å³	Block, colorless
Z = 8	0.56 × 0.35 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2782 independent reflections
Radiation source: sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 69.9°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→8
T_min = 0.708, T_max = 0.863	k = −20→20
10678 measured reflections	l = −31→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0586P)² + 0.4109P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2782 reflections	Δρ_max = 0.18 e Å⁻³
201 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (2)

Crystal data top

C₁₈H₁₃N₃O	V = 2978.15 (14) Å³
M_r = 287.31	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 6.8322 (2) Å	µ = 0.66 mm⁻¹
b = 16.8974 (5) Å	T = 296 K
c = 25.7968 (6) Å	0.56 × 0.35 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2782 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2338 reflections with I > 2σ(I)
T_min = 0.708, T_max = 0.863	R_int = 0.026
10678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.08	Δρ_max = 0.18 e Å⁻³
2782 reflections	Δρ_min = −0.17 e Å⁻³
201 parameters

Special details top

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
N1	0.04907 (16)	0.77988 (6)	0.34667 (4)	0.0461 (3)
N2	0.03430 (17)	0.83315 (7)	0.30758 (4)	0.0501 (3)
N3	0.1596 (2)	0.59304 (10)	0.21580 (6)	0.0737 (4)
O1	0.05198 (19)	0.78631 (8)	0.17444 (4)	0.0747 (4)
C1	0.06117 (18)	0.79131 (8)	0.26452 (5)	0.0480 (3)
C2	0.09573 (19)	0.71052 (8)	0.27627 (5)	0.0463 (3)
C3	0.08526 (18)	0.70532 (8)	0.32961 (5)	0.0441 (3)
C4	0.1299 (2)	0.64619 (10)	0.24210 (5)	0.0536 (4)
C5	0.0947 (2)	0.63535 (8)	0.36354 (5)	0.0458 (3)
C6	0.2582 (2)	0.58729 (10)	0.36412 (6)	0.0628 (4)
H6A	0.3661	0.5995	0.3436	0.075*
C7	0.2603 (3)	0.52048 (10)	0.39553 (8)	0.0783 (5)
H7A	0.3702	0.4880	0.3961	0.094*
C8	0.1016 (4)	0.50213 (10)	0.42561 (7)	0.0785 (6)
H8A	0.1043	0.4575	0.4467	0.094*
C9	−0.0597 (3)	0.54911 (10)	0.42477 (7)	0.0741 (5)
H9A	−0.1675	0.5363	0.4451	0.089*
C10	−0.0647 (2)	0.61553 (9)	0.39400 (6)	0.0580 (4)
H10A	−0.1758	0.6473	0.3937	0.070*
C11	0.0388 (2)	0.80605 (8)	0.39950 (5)	0.0466 (3)
C12	0.1957 (2)	0.79135 (9)	0.43180 (6)	0.0566 (4)
H12A	0.3064	0.7656	0.4194	0.068*
C13	0.1858 (3)	0.81549 (10)	0.48280 (6)	0.0650 (4)
H13A	0.2901	0.8055	0.5050	0.078*
C14	0.0225 (3)	0.85426 (9)	0.50097 (6)	0.0658 (4)
H14A	0.0164	0.8703	0.5354	0.079*
C15	−0.1319 (3)	0.86926 (10)	0.46807 (6)	0.0662 (4)
H15A	−0.2414	0.8961	0.4803	0.079*
C16	−0.1254 (2)	0.84480 (9)	0.41697 (6)	0.0576 (4)
H16A	−0.2302	0.8544	0.3948	0.069*
C17	0.0492 (2)	0.82851 (10)	0.21251 (5)	0.0568 (4)
C18	0.0336 (3)	0.91591 (11)	0.20952 (7)	0.0755 (5)
H18A	−0.0431	0.9303	0.1798	0.113*
H18C	0.1621	0.9384	0.2065	0.113*
H18D	−0.0284	0.9356	0.2403	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0550 (6)	0.0450 (6)	0.0383 (5)	−0.0011 (5)	−0.0011 (4)	0.0056 (4)
N2	0.0541 (6)	0.0525 (6)	0.0438 (6)	−0.0019 (5)	−0.0021 (5)	0.0112 (5)
N3	0.0732 (9)	0.0852 (10)	0.0626 (8)	0.0025 (8)	0.0026 (7)	−0.0182 (8)
O1	0.0859 (8)	0.0965 (9)	0.0417 (6)	−0.0136 (7)	−0.0014 (5)	0.0109 (6)
C1	0.0429 (6)	0.0603 (8)	0.0407 (7)	−0.0073 (6)	−0.0012 (5)	0.0096 (6)
C2	0.0429 (6)	0.0566 (8)	0.0395 (6)	−0.0071 (6)	0.0003 (5)	0.0014 (6)
C3	0.0446 (6)	0.0474 (7)	0.0404 (6)	−0.0036 (5)	0.0002 (5)	0.0014 (5)
C4	0.0479 (7)	0.0701 (9)	0.0429 (7)	−0.0050 (7)	0.0009 (6)	−0.0026 (7)
C5	0.0579 (7)	0.0430 (7)	0.0363 (6)	−0.0014 (6)	−0.0021 (5)	−0.0020 (5)
C6	0.0642 (9)	0.0621 (9)	0.0622 (9)	0.0079 (7)	−0.0024 (7)	−0.0025 (7)
C7	0.0960 (13)	0.0558 (9)	0.0832 (12)	0.0250 (9)	−0.0237 (11)	−0.0051 (9)
C8	0.1315 (17)	0.0486 (9)	0.0554 (9)	0.0027 (10)	−0.0064 (10)	0.0067 (7)
C9	0.1125 (14)	0.0530 (9)	0.0568 (9)	−0.0034 (9)	0.0177 (9)	0.0085 (7)
C10	0.0738 (9)	0.0493 (8)	0.0508 (8)	0.0007 (7)	0.0113 (7)	0.0040 (6)
C11	0.0603 (7)	0.0395 (6)	0.0400 (6)	−0.0025 (6)	−0.0011 (6)	0.0034 (5)
C12	0.0651 (9)	0.0520 (8)	0.0526 (8)	0.0055 (7)	−0.0077 (6)	−0.0043 (6)
C13	0.0863 (11)	0.0575 (9)	0.0511 (8)	0.0016 (8)	−0.0186 (8)	−0.0037 (7)
C14	0.0962 (12)	0.0568 (9)	0.0445 (8)	−0.0048 (8)	−0.0002 (8)	−0.0051 (7)
C15	0.0801 (10)	0.0616 (9)	0.0571 (9)	0.0084 (8)	0.0100 (8)	−0.0040 (7)
C16	0.0650 (9)	0.0580 (8)	0.0499 (8)	0.0069 (7)	−0.0005 (6)	0.0038 (7)
C17	0.0460 (7)	0.0792 (10)	0.0451 (8)	−0.0084 (7)	−0.0012 (6)	0.0152 (7)
C18	0.0816 (11)	0.0821 (12)	0.0627 (10)	0.0030 (9)	0.0005 (8)	0.0291 (9)

Geometric parameters (Å, º) top

N1—N2	1.3555 (15)	C9—C10	1.375 (2)
N1—C3	1.3572 (17)	C9—H9A	0.9300
N1—C11	1.4346 (17)	C10—H10A	0.9300
N2—C1	1.3294 (18)	C11—C16	1.375 (2)
N3—C4	1.144 (2)	C11—C12	1.380 (2)
O1—C17	1.214 (2)	C12—C13	1.379 (2)
C1—C2	1.418 (2)	C12—H12A	0.9300
C1—C17	1.4840 (18)	C13—C14	1.376 (3)
C2—C3	1.3807 (18)	C13—H13A	0.9300
C2—C4	1.419 (2)	C14—C15	1.378 (2)
C3—C5	1.4724 (18)	C14—H14A	0.9300
C5—C6	1.381 (2)	C15—C16	1.382 (2)
C5—C10	1.384 (2)	C15—H15A	0.9300
C6—C7	1.390 (2)	C16—H16A	0.9300
C6—H6A	0.9300	C17—C18	1.483 (2)
C7—C8	1.369 (3)	C18—H18A	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.359 (3)	C18—H18D	0.9600
C8—H8A	0.9300

N2—N1—C3	112.88 (11)	C9—C10—H10A	119.8
N2—N1—C11	119.90 (10)	C5—C10—H10A	119.8
C3—N1—C11	127.08 (11)	C16—C11—C12	121.44 (13)
C1—N2—N1	104.96 (11)	C16—C11—N1	119.87 (12)
N2—C1—C2	110.88 (11)	C12—C11—N1	118.69 (12)
N2—C1—C17	121.50 (13)	C13—C12—C11	118.99 (15)
C2—C1—C17	127.60 (13)	C13—C12—H12A	120.5
C3—C2—C1	105.40 (12)	C11—C12—H12A	120.5
C3—C2—C4	125.39 (13)	C14—C13—C12	120.36 (15)
C1—C2—C4	129.20 (13)	C14—C13—H13A	119.8
N1—C3—C2	105.88 (11)	C12—C13—H13A	119.8
N1—C3—C5	124.11 (11)	C13—C14—C15	119.91 (14)
C2—C3—C5	129.87 (12)	C13—C14—H14A	120.0
N3—C4—C2	177.90 (16)	C15—C14—H14A	120.0
C6—C5—C10	119.21 (14)	C14—C15—C16	120.54 (15)
C6—C5—C3	120.93 (13)	C14—C15—H15A	119.7
C10—C5—C3	119.83 (12)	C16—C15—H15A	119.7
C5—C6—C7	119.48 (16)	C11—C16—C15	118.75 (15)
C5—C6—H6A	120.3	C11—C16—H16A	120.6
C7—C6—H6A	120.3	C15—C16—H16A	120.6
C8—C7—C6	120.43 (17)	O1—C17—C18	122.97 (14)
C8—C7—H7A	119.8	O1—C17—C1	118.81 (15)
C6—C7—H7A	119.8	C18—C17—C1	118.22 (14)
C9—C8—C7	120.07 (16)	C17—C18—H18A	109.5
C9—C8—H8A	120.0	C17—C18—H18C	109.5
C7—C8—H8A	120.0	H18A—C18—H18C	109.5
C8—C9—C10	120.41 (18)	C17—C18—H18D	109.5
C8—C9—H9A	119.8	H18A—C18—H18D	109.5
C10—C9—H9A	119.8	H18C—C18—H18D	109.5
C9—C10—C5	120.39 (16)

C3—N1—N2—C1	0.20 (14)	C5—C6—C7—C8	0.2 (3)
C11—N1—N2—C1	176.31 (11)	C6—C7—C8—C9	0.3 (3)
N1—N2—C1—C2	−0.67 (14)	C7—C8—C9—C10	−0.4 (3)
N1—N2—C1—C17	177.93 (11)	C8—C9—C10—C5	0.0 (3)
N2—C1—C2—C3	0.89 (15)	C6—C5—C10—C9	0.5 (2)
C17—C1—C2—C3	−177.61 (12)	C3—C5—C10—C9	178.21 (14)
N2—C1—C2—C4	179.54 (13)	N2—N1—C11—C16	59.51 (17)
C17—C1—C2—C4	1.0 (2)	C3—N1—C11—C16	−124.99 (15)
N2—N1—C3—C2	0.34 (14)	N2—N1—C11—C12	−120.59 (14)
C11—N1—C3—C2	−175.42 (12)	C3—N1—C11—C12	54.91 (19)
N2—N1—C3—C5	−175.66 (11)	C16—C11—C12—C13	0.7 (2)
C11—N1—C3—C5	8.6 (2)	N1—C11—C12—C13	−179.21 (13)
C1—C2—C3—N1	−0.71 (14)	C11—C12—C13—C14	−0.6 (2)
C4—C2—C3—N1	−179.43 (12)	C12—C13—C14—C15	−0.1 (3)
C1—C2—C3—C5	174.97 (13)	C13—C14—C15—C16	0.8 (3)
C4—C2—C3—C5	−3.7 (2)	C12—C11—C16—C15	0.0 (2)
N1—C3—C5—C6	−124.42 (15)	N1—C11—C16—C15	179.86 (14)
C2—C3—C5—C6	60.6 (2)	C14—C15—C16—C11	−0.7 (3)
N1—C3—C5—C10	57.90 (18)	N2—C1—C17—O1	−171.47 (13)
C2—C3—C5—C10	−117.09 (16)	C2—C1—C17—O1	6.9 (2)
C10—C5—C6—C7	−0.5 (2)	N2—C1—C17—C18	8.3 (2)
C3—C5—C6—C7	−178.24 (14)	C2—C1—C17—C18	−173.32 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N3ⁱ	0.93	2.53	3.432 (2)	165
C16—H16A···O1ⁱⁱ	0.93	2.59	3.3758 (19)	142

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃N₃O
M_r	287.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	6.8322 (2), 16.8974 (5), 25.7968 (6)
V (Å³)	2978.15 (14)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.56 × 0.35 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.708, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	10678, 2782, 2338
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.08
No. of reflections	2782
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

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
C6—H6A···N3ⁱ	0.93	2.53	3.432 (2)	165
C16—H16A···O1ⁱⁱ	0.93	2.59	3.3758 (19)	142

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

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

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

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