1-Acetyl-3-[2-(2,3,5,6-tetra­fluoro­phen­yl)hydrazin-1-yl­idene]indolin-2-one

Pervez, H.; Yaqub, M.; Ahmed, M.; Tahir, M.N.; Akhtar, R.

doi:10.1107/S1600536810022580

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1686

doi:10.1107/S1600536810022580

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1-Acetyl-3-[2-(2,3,5,6-tetrafluorophenyl)hydrazin-1-ylidene]indolin-2-one

Humayun Pervez,^a Muhammad Yaqub,^a Maqbool Ahmad,^a M. Nawaz Tahir ^b ^* and Robina Akhtar ^a

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 11 June 2010; accepted 12 June 2010; online 16 June 2010)

In the title compound, C₁₆H₉F₄N₃O₂, the dihedral angle between the aromatic ring systems is 4.10 (14)° and a bifurcated intramolecular N—H⋯(O,F) hydrogen bond generates an S(6) ring for the O-atom acceptor and an S(5) ring for the F-atom acceptor. A short C—H⋯O conact also occurs. In the crystal, molecules are linked by C—H⋯O interactions.

Related literature

For background on related isatin derivatives, see: Pervez et al. (2007 , 2008 , 2010a ). For related structures, see: Abad et al. (2006 ); Pervez et al. (2010b ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₉F₄N₃O₂
M_r = 351.26
Monoclinic, P 2₁
a = 9.8993 (19) Å
b = 4.7740 (6) Å
c = 16.066 (3) Å
β = 104.807 (8)°
V = 734.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.942, T_max = 0.952
6095 measured reflections
1462 independent reflections
749 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.080
S = 0.96
1462 reflections
227 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	1.99	2.694 (5)	139
N2—H2⋯F1	0.86	2.29	2.658 (5)	106
C6—H6⋯O1	0.93	2.33	2.857 (8)	116
C14—H14⋯O1ⁱ	0.93	2.32	3.217 (7)	163
Symmetry code: (i) x+1, y-2, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022580/hb5498sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022580/hb5498Isup2.hkl

checkCIF report

Comment top

In continuation of our previous work on the synthesis of isatin derivatives having physiological properties (Pervez et al., 2007, 2008, 2010a, 2010b), we report herein the synthesis and crystal structure of the title compound (I), (Fig. 1).

The crystal structure of N-(2-chloropyrid-4-yl)-N^'-(2,3,5,6-tetrafluorophenyl)urea (Abad et al., 2006) has been published which contains the same flouro substituted phenyl group as in (I).

In (I), the 2-oxoindolin-3-hydrazono group A (N3/C1–C8/O2/N1/N2) and tetrafluorophenyl B (C11—C16/F1–F4) are planar with r. m. s. deviations of 0.0197 and 0.0121 Å, respectively. The dihedral angle between A/B is 4.10 (14)°. The acetyl moiety (O1/C9/C10) is oriented at 6.21 (83)° with its parent group A. One S(5) ring motif (Bernstein et al., 1995) is formed due to intramolecular H-bonding of N—H···F type, two S(6) ring motifs due to N—H···O and C—H···O interactions (Table 1, Fig. 1) are formed. The molecules are stabilized in the form of one dimensional polymeric chains extending along the a axis (Fig. 2).

Related literature top

For background on related isatin derivatives, see: Pervez et al. (2007, 2008, 2010a). For related structures, see: Abad et al. (2006); Pervez et al. 2010b). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A solution of 1-acetylisatin (0.95 g, 5.0 mmol) in ethanol (50 ml) was added to the solution of 2,3,5,6-tetrafluorophenyl hydrazine (0.90 g, 5.0 mmol) made in concentrated sulfuric acid (8 ml) and diluted with ethanol (50 ml). The reaction mixture was then refluxed for 30 min. The bright yellow crystalline solid formed during refluxing was collected by suction filtration. Thorough washing with hot ethanol furnished the desired compound (I) in pure form (0.40 g, 23%), m.p. 445 K. Bright yellow prisms of (I) were grown in chloroform by slow evaporation method at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. The dotted lines indicate the intra-molecular H-bondings.
	Fig. 2. The partial packing of (I), which shows that molecules form one-dimensional polymeric chains extending along the a axis.

1-Acetyl-3-[2-(2,3,5,6-tetrafluorophenyl)hydrazin-1-ylidene]indolin-2-one top

Crystal data top

C₁₆H₉F₄N₃O₂	F(000) = 356
M_r = 351.26	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 749 reflections
a = 9.8993 (19) Å	θ = 2.6–25.3°
b = 4.7740 (6) Å	µ = 0.14 mm⁻¹
c = 16.066 (3) Å	T = 296 K
β = 104.807 (8)°	Prism, yellow
V = 734.0 (2) Å³	0.32 × 0.24 × 0.22 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1462 independent reflections
Radiation source: fine-focus sealed tube	749 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.1°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
T_min = 0.942, T_max = 0.952	l = −19→19
6095 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0218P)²] where P = (F_o² + 2F_c²)/3
1462 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₉F₄N₃O₂	V = 734.0 (2) Å³
M_r = 351.26	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.8993 (19) Å	µ = 0.14 mm⁻¹
b = 4.7740 (6) Å	T = 296 K
c = 16.066 (3) Å	0.32 × 0.24 × 0.22 mm
β = 104.807 (8)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1462 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	749 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.952	R_int = 0.087
6095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.080	H-atom parameters constrained
S = 0.96	Δρ_max = 0.14 e Å⁻³
1462 reflections	Δρ_min = −0.18 e Å⁻³
227 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
F1	0.3005 (3)	−0.4142 (6)	0.06872 (17)	0.0638 (12)
F2	0.4748 (3)	−0.8205 (7)	0.0458 (2)	0.0791 (16)
F3	0.7604 (3)	−0.6503 (7)	0.3236 (2)	0.0843 (14)
F4	0.5877 (3)	−0.2576 (8)	0.34942 (19)	0.0820 (14)
O1	−0.1264 (4)	0.8071 (9)	0.2007 (3)	0.0780 (17)
O2	0.1041 (3)	0.1514 (8)	0.1326 (2)	0.0613 (14)
N1	0.3432 (4)	0.0297 (9)	0.2843 (3)	0.0520 (17)
N2	0.3382 (4)	−0.1238 (9)	0.2140 (3)	0.0492 (17)
N3	0.0446 (4)	0.4800 (9)	0.2270 (3)	0.0472 (17)
C1	0.2424 (5)	0.2126 (11)	0.2794 (3)	0.045 (2)
C2	0.2254 (6)	0.3936 (11)	0.3472 (3)	0.048 (2)
C3	0.3062 (6)	0.4269 (12)	0.4321 (4)	0.067 (3)
C4	0.2608 (7)	0.6204 (15)	0.4832 (4)	0.085 (3)
C5	0.1400 (8)	0.7727 (13)	0.4520 (4)	0.082 (3)
C6	0.0581 (6)	0.7417 (12)	0.3682 (4)	0.064 (3)
C7	0.1054 (5)	0.5532 (10)	0.3168 (3)	0.046 (2)
C8	0.1251 (5)	0.2667 (11)	0.2034 (3)	0.047 (2)
C9	−0.0694 (6)	0.6214 (14)	0.1721 (4)	0.057 (2)
C10	−0.1145 (5)	0.5317 (13)	0.0791 (3)	0.078 (3)
C11	0.4358 (5)	−0.3222 (11)	0.2091 (3)	0.0415 (19)
C12	0.4162 (5)	−0.4726 (11)	0.1331 (3)	0.046 (2)
C13	0.5063 (6)	−0.6775 (12)	0.1212 (4)	0.055 (2)
C14	0.6244 (6)	−0.7476 (12)	0.1850 (4)	0.058 (3)
C15	0.6455 (6)	−0.5977 (13)	0.2589 (4)	0.055 (2)
C16	0.5565 (6)	−0.3921 (11)	0.2732 (3)	0.052 (2)
H2	0.26986	−0.09659	0.16945	0.0589*
H3	0.38710	0.32286	0.45329	0.0808*
H4	0.31279	0.64831	0.53964	0.1016*
H5	0.11238	0.90027	0.48823	0.0984*
H6	−0.02410	0.84251	0.34781	0.0768*
H10A	−0.19107	0.64643	0.04892	0.1164*
H10B	−0.14341	0.33917	0.07589	0.1164*
H10C	−0.03772	0.55230	0.05320	0.1164*
H14	0.68534	−0.88833	0.17772	0.0692*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.059 (2)	0.066 (2)	0.058 (2)	0.0084 (17)	−0.0006 (16)	0.0018 (17)
F2	0.096 (3)	0.066 (2)	0.078 (3)	0.010 (2)	0.027 (2)	−0.013 (2)
F3	0.062 (2)	0.101 (3)	0.083 (2)	0.018 (2)	0.006 (2)	0.024 (2)
F4	0.077 (2)	0.098 (3)	0.060 (2)	0.013 (2)	−0.0025 (19)	−0.010 (2)
O1	0.075 (3)	0.076 (3)	0.083 (3)	0.029 (3)	0.020 (2)	0.002 (2)
O2	0.061 (2)	0.070 (3)	0.052 (2)	0.010 (2)	0.013 (2)	−0.010 (2)
N1	0.062 (3)	0.047 (3)	0.048 (3)	−0.006 (3)	0.016 (2)	−0.002 (3)
N2	0.042 (3)	0.055 (3)	0.048 (3)	0.008 (2)	0.007 (2)	−0.001 (3)
N3	0.048 (3)	0.039 (3)	0.055 (3)	0.008 (2)	0.014 (3)	0.006 (2)
C1	0.048 (4)	0.038 (4)	0.051 (4)	0.003 (3)	0.015 (3)	0.008 (3)
C2	0.058 (4)	0.043 (4)	0.045 (4)	−0.004 (3)	0.018 (3)	0.002 (3)
C3	0.075 (4)	0.069 (5)	0.055 (4)	0.010 (4)	0.011 (4)	−0.004 (4)
C4	0.105 (6)	0.083 (6)	0.062 (5)	0.003 (5)	0.014 (4)	−0.015 (4)
C5	0.112 (6)	0.068 (5)	0.073 (5)	0.001 (5)	0.035 (4)	−0.020 (4)
C6	0.067 (4)	0.056 (4)	0.074 (5)	0.007 (3)	0.027 (4)	−0.003 (4)
C7	0.053 (4)	0.037 (4)	0.050 (4)	−0.004 (3)	0.016 (3)	−0.001 (3)
C8	0.049 (4)	0.042 (4)	0.051 (4)	−0.003 (3)	0.017 (3)	0.006 (3)
C9	0.051 (4)	0.057 (4)	0.066 (4)	0.005 (3)	0.022 (3)	0.008 (3)
C10	0.072 (4)	0.095 (5)	0.057 (4)	0.019 (4)	0.000 (3)	0.000 (4)
C11	0.040 (3)	0.037 (3)	0.051 (4)	−0.001 (3)	0.018 (3)	0.010 (3)
C12	0.046 (4)	0.040 (4)	0.052 (4)	0.006 (3)	0.013 (3)	0.006 (3)
C13	0.068 (4)	0.045 (4)	0.055 (4)	0.001 (3)	0.020 (4)	−0.002 (3)
C14	0.057 (4)	0.044 (4)	0.078 (5)	0.008 (3)	0.028 (4)	0.012 (4)
C15	0.044 (4)	0.057 (4)	0.064 (4)	0.009 (3)	0.012 (3)	0.021 (4)
C16	0.051 (4)	0.056 (4)	0.048 (4)	−0.009 (3)	0.013 (3)	−0.006 (3)

Geometric parameters (Å, º) top

F1—C12	1.362 (6)	C4—C5	1.380 (10)
F2—C13	1.356 (7)	C5—C6	1.391 (9)
F3—C15	1.354 (7)	C6—C7	1.382 (8)
F4—C16	1.347 (6)	C9—C10	1.508 (8)
O1—C9	1.203 (8)	C11—C16	1.404 (7)
O2—C8	1.233 (6)	C11—C12	1.387 (7)
N1—N2	1.337 (6)	C12—C13	1.370 (8)
N1—C1	1.313 (7)	C13—C14	1.385 (9)
N2—C11	1.370 (7)	C14—C15	1.356 (9)
N3—C7	1.457 (7)	C15—C16	1.377 (8)
N3—C8	1.404 (7)	C3—H3	0.9300
N3—C9	1.414 (8)	C4—H4	0.9300
N2—H2	0.8600	C5—H5	0.9300
C1—C8	1.477 (7)	C6—H6	0.9300
C1—C2	1.434 (7)	C10—H10A	0.9600
C2—C7	1.391 (8)	C10—H10B	0.9600
C2—C3	1.403 (8)	C10—H10C	0.9600
C3—C4	1.385 (9)	C14—H14	0.9300

N2—N1—C1	116.8 (4)	F1—C12—C13	119.4 (5)
N1—N2—C11	123.6 (4)	C11—C12—C13	122.9 (5)
C7—N3—C8	108.8 (4)	F1—C12—C11	117.7 (4)
C7—N3—C9	124.4 (4)	C12—C13—C14	121.7 (5)
C8—N3—C9	126.6 (5)	F2—C13—C12	118.4 (5)
N1—N2—H2	118.00	F2—C13—C14	119.9 (5)
C11—N2—H2	118.00	C13—C14—C15	115.6 (6)
N1—C1—C2	126.2 (5)	F3—C15—C16	116.9 (5)
N1—C1—C8	126.2 (5)	C14—C15—C16	124.1 (6)
C2—C1—C8	107.6 (4)	F3—C15—C14	119.1 (5)
C1—C2—C3	131.2 (5)	C11—C16—C15	120.5 (5)
C3—C2—C7	120.2 (5)	F4—C16—C11	120.5 (5)
C1—C2—C7	108.6 (4)	F4—C16—C15	118.9 (5)
C2—C3—C4	117.5 (6)	C2—C3—H3	121.00
C3—C4—C5	121.2 (6)	C4—C3—H3	121.00
C4—C5—C6	122.2 (6)	C3—C4—H4	119.00
C5—C6—C7	116.4 (6)	C5—C4—H4	119.00
C2—C7—C6	122.5 (5)	C4—C5—H5	119.00
N3—C7—C2	108.4 (4)	C6—C5—H5	119.00
N3—C7—C6	129.1 (5)	C5—C6—H6	122.00
N3—C8—C1	106.5 (4)	C7—C6—H6	122.00
O2—C8—N3	126.9 (5)	C9—C10—H10A	110.00
O2—C8—C1	126.6 (5)	C9—C10—H10B	109.00
O1—C9—N3	119.4 (6)	C9—C10—H10C	109.00
O1—C9—C10	122.6 (6)	H10A—C10—H10B	109.00
N3—C9—C10	118.0 (5)	H10A—C10—H10C	109.00
N2—C11—C12	117.8 (4)	H10B—C10—H10C	109.00
C12—C11—C16	115.1 (5)	C13—C14—H14	122.00
N2—C11—C16	127.1 (5)	C15—C14—H14	122.00

C1—N1—N2—C11	179.8 (5)	C1—C2—C7—C6	177.8 (5)
N2—N1—C1—C2	178.5 (5)	C3—C2—C7—N3	178.8 (5)
N2—N1—C1—C8	−0.7 (8)	C3—C2—C7—C6	−2.1 (8)
N1—N2—C11—C12	178.2 (5)	C2—C3—C4—C5	0.6 (10)
N1—N2—C11—C16	−2.2 (8)	C3—C4—C5—C6	−0.3 (11)
C8—N3—C7—C2	2.2 (6)	C4—C5—C6—C7	−1.2 (10)
C8—N3—C7—C6	−176.7 (5)	C5—C6—C7—N3	−178.8 (5)
C9—N3—C7—C2	−172.7 (5)	C5—C6—C7—C2	2.4 (8)
C9—N3—C7—C6	8.4 (8)	N2—C11—C12—F1	−0.5 (7)
C7—N3—C8—O2	179.4 (5)	N2—C11—C12—C13	−179.4 (5)
C7—N3—C8—C1	−2.2 (5)	C16—C11—C12—F1	179.8 (4)
C9—N3—C8—O2	−5.9 (9)	C16—C11—C12—C13	0.9 (8)
C9—N3—C8—C1	172.6 (5)	N2—C11—C16—F4	−0.6 (8)
C7—N3—C9—O1	−3.7 (9)	N2—C11—C16—C15	180.0 (5)
C7—N3—C9—C10	176.2 (5)	C12—C11—C16—F4	179.1 (5)
C8—N3—C9—O1	−177.7 (5)	C12—C11—C16—C15	−0.4 (8)
C8—N3—C9—C10	2.3 (8)	F1—C12—C13—F2	−1.6 (8)
N1—C1—C2—C3	0.5 (10)	F1—C12—C13—C14	−179.1 (5)
N1—C1—C2—C7	−179.4 (5)	C11—C12—C13—F2	177.3 (5)
C8—C1—C2—C3	179.8 (6)	C11—C12—C13—C14	−0.2 (9)
C8—C1—C2—C7	0.0 (6)	F2—C13—C14—C15	−178.4 (5)
N1—C1—C8—O2	−0.8 (9)	C12—C13—C14—C15	−0.9 (9)
N1—C1—C8—N3	−179.3 (5)	C13—C14—C15—F3	−178.6 (5)
C2—C1—C8—O2	179.9 (5)	C13—C14—C15—C16	1.5 (9)
C2—C1—C8—N3	1.4 (6)	F3—C15—C16—F4	−0.2 (8)
C1—C2—C3—C4	−179.3 (6)	F3—C15—C16—C11	179.3 (5)
C7—C2—C3—C4	0.6 (9)	C14—C15—C16—F4	179.7 (5)
C1—C2—C7—N3	−1.3 (6)	C14—C15—C16—C11	−0.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.99	2.694 (5)	139
N2—H2···F1	0.86	2.29	2.658 (5)	106
C6—H6···O1	0.93	2.33	2.857 (8)	116
C14—H14···O1ⁱ	0.93	2.32	3.217 (7)	163

Symmetry code: (i) x+1, y−2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₉F₄N₃O₂
M_r	351.26
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.8993 (19), 4.7740 (6), 16.066 (3)
β (°)	104.807 (8)
V (Å³)	734.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.942, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	6095, 1462, 749
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.080, 0.96
No. of reflections	1462
No. of parameters	227
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.99	2.694 (5)	139
N2—H2···F1	0.86	2.29	2.658 (5)	106
C6—H6···O1	0.93	2.33	2.857 (8)	116
C14—H14···O1ⁱ	0.93	2.32	3.217 (7)	163

Symmetry code: (i) x+1, y−2, z.

Acknowledgements

MA gratefully acknowledges the Higher Education Commission (HEC), Islamabad, Pakistan, for providing him with a Scholarship under the Indigenous PhD Program and also for partial funding of this research work.

References

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