2-(3-Methyl­but-2-en-1-yl)-1,2-benziso­thia­zol-3(2H)-one 1,1-dioxide

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Bilal, M.H.; Mubashar-ur-Rehman, H.

doi:10.1107/S1600536809012021

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o986

doi:10.1107/S1600536809012021

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2-(3-Methylbut-2-en-1-yl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Muhammad Nadeem Arshad,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Humayun Bilal ^a and Hafiz Mubashar-ur-Rehman ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 28 March 2009; accepted 31 March 2009; online 8 April 2009)

In the title compound, C₁₂H₁₃NO₃S, a saccharin derivative, the dihedral angle between the aromatic and isothiazole rings is 2.91 (12)°. The planar 3,3-dimethylallyl group [maximum deviation = 0.0086 (16) Å] is oriented at dihedral angles of 71.86 (7) and 74.35 (7)° with respect to the aromatic and isothiazole rings, respectively. In the crystal structure, weak intermolecular C—H⋯O interactions link the molecules into chains along the c axis. A weak C—H⋯π interaction is also present.

Related literature

For the biological activity of saccharine derivatives, see: Primofiore et al. (1997 ). For related structures, see: Arshad et al. (2008 ); Kruszynski & Czestkowski (2001 ); Siddiqui et al. (2007 ); Yu et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₃NO₃S
M_r = 251.29
Orthorhombic, P n a 2₁
a = 9.4120 (5) Å
b = 19.4108 (11) Å
c = 6.5261 (4) Å
V = 1192.28 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.924, T_max = 0.946
7340 measured reflections
2525 independent reflections
2304 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.083
S = 1.05
2525 reflections
156 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 837 Friedel pairs
Flack parameter: 0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.56	3.391 (2)	149
C8—H8A⋯O2ⁱⁱ	0.97	2.51	3.436 (3)	160
C3—H3⋯Cg1ⁱⁱⁱ	0.93	2.89	3.664 (2)	141
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ . Cg1 is the centroid of the C1–C6 ring.

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 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012021/hk2656sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012021/hk2656Isup2.hkl

checkCIF report

Comment top

The sodium salt of 1,2-benzisothiazole-3(2H)-one-1,1-dioxide is commonly known as saccharine, a sweetener. The derivatives of this compound are biologically active (Primofiore et al., 1997) and used for the syntheses of various biologically active heterocyclic compounds. We report herein the crystal structure of the title compound, (I), as part of our ongoing studies on thiazine related heterocycles (Arshad et al., 2008).

The crystal structures of 3-methylbut-2-enyl)ammonium chloride, (II) (Kruszynski & Czestkowski, 2001), 2-(chloromethyl)-1,2-benzisothiazole-1,1,3(2H) -trione, (III) (Siddiqui et al., 2007) and 2-n-butyl-1,2-benziso- thiazol-3(2H)-one, (IV) (Yu et al., 2008) have been published.

In the molecule of (I) (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (S1/N1/C1/C6/C7) are, of course, planar and they are oriented at a dihedral angle of 2.91 (12)°. So, benzisothiazole ring system is nearly coplanar. The 3,3-dimethylallyl moiety C (C8-C12) is also planar with a maximum deviation of 0.0086 (16) Å for C10 atom, and it is oriented with respect to rings A and B at dihedral angles of A/C = 74.35 (7) and B/C = 71.86 (7) °. Atoms O1, O2 and O3 are 1.2007 (17), -1.2296 (19) and -0.0441 (27) Å away from the ring plane of B, respectively.

In the crystal structure, weak intermolecular C-H···O interactions (Table 1) link the molecules into chains along the c axis, in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction (Table 1).

Related literature top

For the biological activity of saccharine derivatives, see: Primofiore et al. (1997). For related structures, see: Arshad et al. (2008); Kruszynski & Czestkowski (2001); Siddiqui et al. (2007); Yu et al. (2008). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the C1–C6 ring.

Experimental top

For the preparation of the title compound, sodium salt of saccharine (1 g, 4.88 mmol) was dissolved in dimethylformamide (5 ml) in a round bottom flask (25 ml) equipped with condenser. Then, 3,3-dimethylallyl bromide (0.73 g, 4.88 mmol) was added to the solution and stirred at 353-373 K for 3 h. The progress of the reaction was observed by TLC. At completion of reaction, the mixture was poured on ice, precipitates obtained were filtered, washed with distilled water and dried. The residue was recrystalized in methanol to obtain the suitable crystals of the title compound.

Computing details top

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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

2-(3-Methylbut-2-en-1-yl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide top

Crystal data top

C₁₂H₁₃NO₃S	F(000) = 528
M_r = 251.29	D_x = 1.400 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2818 reflections
a = 9.4120 (5) Å	θ = 2.4–28.8°
b = 19.4108 (11) Å	µ = 0.27 mm⁻¹
c = 6.5261 (4) Å	T = 296 K
V = 1192.28 (12) Å³	Rod, colorless
Z = 4	0.32 × 0.24 × 0.22 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2525 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.8°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
T_min = 0.924, T_max = 0.946	l = −8→4
7340 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.05P)² + 0.1276P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2525 reflections	Δρ_max = 0.28 e Å⁻³
156 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 837 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (8)

Crystal data top

C₁₂H₁₃NO₃S	V = 1192.28 (12) Å³
M_r = 251.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.4120 (5) Å	µ = 0.27 mm⁻¹
b = 19.4108 (11) Å	T = 296 K
c = 6.5261 (4) Å	0.32 × 0.24 × 0.22 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2525 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2304 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.946	R_int = 0.019
7340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.083	Δρ_max = 0.28 e Å⁻³
S = 1.05	Δρ_min = −0.20 e Å⁻³
2525 reflections	Absolute structure: Flack (1983), 837 Friedel pairs
156 parameters	Absolute structure parameter: 0.02 (8)
1 restraint

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
S1	0.39059 (4)	0.43722 (2)	0.22028 (8)	0.0360 (1)
O1	0.47203 (15)	0.49780 (6)	0.1846 (2)	0.0527 (5)
O2	0.27683 (15)	0.44174 (7)	0.3626 (3)	0.0501 (5)
O3	0.34253 (18)	0.31180 (9)	−0.2062 (3)	0.0681 (6)
N1	0.32910 (16)	0.40665 (8)	−0.0015 (3)	0.0420 (5)
C1	0.47927 (19)	0.31849 (9)	0.1051 (3)	0.0430 (6)
C2	0.5491 (2)	0.25556 (10)	0.1123 (4)	0.0571 (7)
C3	0.6312 (2)	0.24143 (11)	0.2810 (5)	0.0643 (8)
C4	0.6463 (2)	0.28766 (11)	0.4407 (4)	0.0582 (8)
C5	0.5766 (2)	0.35100 (10)	0.4341 (4)	0.0474 (6)
C6	0.49541 (17)	0.36438 (8)	0.2640 (3)	0.0377 (5)
C7	0.37937 (19)	0.34237 (10)	−0.0545 (3)	0.0449 (6)
C8	0.2217 (2)	0.44531 (10)	−0.1171 (4)	0.0480 (6)
C9	0.0741 (2)	0.43125 (10)	−0.0398 (4)	0.0492 (7)
C10	−0.0319 (2)	0.40469 (9)	−0.1434 (4)	0.0476 (6)
C11	−0.0249 (3)	0.38285 (16)	−0.3615 (5)	0.0740 (10)
C12	−0.1738 (2)	0.39260 (14)	−0.0418 (5)	0.0718 (9)
H2	0.54056	0.22393	0.00600	0.0685*
H3	0.67821	0.19935	0.28810	0.0770*
H4	0.70306	0.27651	0.55253	0.0698*
H5	0.58470	0.38275	0.54021	0.0569*
H8A	0.22741	0.43275	−0.26069	0.0577*
H8B	0.24147	0.49421	−0.10592	0.0577*
H9	0.05601	0.44262	0.09618	0.0591*
H11A	0.06668	0.39430	−0.41673	0.1109*
H11B	−0.09740	0.40615	−0.43825	0.1109*
H11C	−0.03930	0.33398	−0.37040	0.1109*
H12A	−0.16911	0.40717	0.09857	0.1074*
H12B	−0.19663	0.34444	−0.04742	0.1074*
H12C	−0.24574	0.41849	−0.11203	0.1074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0419 (2)	0.0326 (2)	0.0335 (2)	−0.0031 (1)	−0.0001 (2)	−0.0011 (2)
O1	0.0694 (8)	0.0384 (5)	0.0503 (10)	−0.0151 (5)	−0.0077 (8)	0.0034 (6)
O2	0.0521 (8)	0.0565 (8)	0.0418 (9)	0.0060 (5)	0.0063 (7)	−0.0040 (7)
O3	0.0786 (10)	0.0716 (10)	0.0540 (10)	−0.0120 (8)	−0.0050 (9)	−0.0261 (8)
N1	0.0438 (8)	0.0479 (8)	0.0343 (9)	−0.0056 (6)	−0.0020 (7)	−0.0034 (7)
C1	0.0392 (9)	0.0402 (8)	0.0495 (12)	−0.0075 (6)	0.0084 (8)	−0.0088 (8)
C2	0.0494 (11)	0.0444 (9)	0.0775 (17)	−0.0011 (8)	0.0111 (11)	−0.0155 (11)
C3	0.0501 (11)	0.0438 (9)	0.099 (2)	0.0072 (8)	0.0129 (12)	0.0057 (12)
C4	0.0462 (10)	0.0532 (11)	0.0752 (18)	0.0057 (8)	−0.0045 (11)	0.0117 (11)
C5	0.0475 (10)	0.0434 (9)	0.0513 (14)	−0.0043 (7)	−0.0044 (9)	0.0014 (9)
C6	0.0352 (7)	0.0336 (6)	0.0442 (12)	−0.0041 (5)	0.0046 (7)	−0.0010 (7)
C7	0.0436 (9)	0.0482 (9)	0.0430 (12)	−0.0128 (7)	0.0093 (8)	−0.0107 (9)
C8	0.0458 (10)	0.0566 (10)	0.0417 (12)	−0.0100 (8)	−0.0051 (9)	0.0101 (9)
C9	0.0486 (10)	0.0525 (10)	0.0466 (14)	0.0003 (8)	0.0024 (9)	0.0071 (9)
C10	0.0421 (10)	0.0398 (8)	0.0609 (14)	0.0017 (7)	−0.0025 (10)	0.0120 (9)
C11	0.0618 (14)	0.0871 (17)	0.0730 (19)	−0.0177 (12)	−0.0137 (13)	−0.0061 (15)
C12	0.0427 (11)	0.0706 (14)	0.102 (2)	0.0039 (9)	0.0049 (13)	0.0159 (14)

Geometric parameters (Å, º) top

S1—O1	1.4229 (13)	C10—C11	1.487 (4)
S1—O2	1.4201 (17)	C10—C12	1.510 (3)
S1—N1	1.6679 (19)	C2—H2	0.9300
S1—C6	1.7475 (16)	C3—H3	0.9300
O3—C7	1.205 (3)	C4—H4	0.9300
N1—C7	1.379 (2)	C5—H5	0.9300
N1—C8	1.468 (3)	C8—H8A	0.9700
C1—C2	1.388 (3)	C8—H8B	0.9700
C1—C6	1.376 (3)	C9—H9	0.9300
C1—C7	1.478 (3)	C11—H11A	0.9600
C2—C3	1.373 (4)	C11—H11B	0.9600
C3—C4	1.383 (4)	C11—H11C	0.9600
C4—C5	1.394 (3)	C12—H12A	0.9600
C5—C6	1.373 (3)	C12—H12B	0.9600
C8—C9	1.503 (3)	C12—H12C	0.9600
C9—C10	1.311 (3)

O1···C5ⁱ	3.391 (2)	C11···H8A	2.6500
O1···C8ⁱⁱ	3.347 (2)	C12···H2^viii	3.0500
O2···C9	3.253 (3)	H2···O3	2.8800
O2···C12ⁱⁱⁱ	3.416 (3)	H2···C9^vii	3.0400
O3···C5^iv	3.308 (3)	H2···C10^vii	2.7700
O1···H8B	2.8800	H2···C12^vii	3.0500
O1···H5ⁱ	2.5600	H3···C1^vii	3.0900
O2···H9	2.7100	H3···C7^vii	3.0400
O2···H8A^v	2.5100	H4···O3^x	2.6700
O2···H12Cⁱⁱⁱ	2.7300	H5···O1ⁱⁱ	2.5600
O2···H11A^v	2.6100	H8A···O2^iv	2.5100
O3···H2	2.8800	H8A···O3	2.6100
O3···H8A	2.6100	H8A···C11	2.6500
O3···H4^vi	2.6700	H8A···H11A	1.9700
C3···C7^vii	3.591 (3)	H8B···O1	2.8800
C5···O1ⁱⁱ	3.391 (2)	H9···O2	2.7100
C5···O3^v	3.308 (3)	H9···H12A	2.2300
C7···C3^viii	3.591 (3)	H11A···O2^iv	2.6100
C8···O1ⁱ	3.347 (2)	H11A···C8	2.6300
C9···O2	3.253 (3)	H11A···H8A	1.9700
C12···O2^ix	3.416 (3)	H11B···H12C	2.5600
C1···H3^viii	3.0900	H11C···H12B	2.5800
C7···H3^viii	3.0400	H12A···H9	2.2300
C8···H11A	2.6300	H12B···H11C	2.5800
C9···H2^viii	3.0400	H12C···H11B	2.5600
C10···H2^viii	2.7700	H12C···O2^ix	2.7300

O1—S1—O2	117.53 (8)	C1—C2—H2	121.00
O1—S1—N1	109.81 (8)	C3—C2—H2	121.00
O1—S1—C6	113.03 (8)	C2—C3—H3	119.00
O2—S1—N1	109.14 (9)	C4—C3—H3	119.00
O2—S1—C6	111.65 (9)	C3—C4—H4	120.00
N1—S1—C6	92.85 (8)	C5—C4—H4	120.00
S1—N1—C7	114.88 (14)	C4—C5—H5	122.00
S1—N1—C8	120.21 (14)	C6—C5—H5	121.00
C7—N1—C8	124.76 (18)	N1—C8—H8A	109.00
C2—C1—C6	119.48 (18)	N1—C8—H8B	109.00
C2—C1—C7	126.96 (18)	C9—C8—H8A	109.00
C6—C1—C7	113.49 (16)	C9—C8—H8B	109.00
C1—C2—C3	118.0 (2)	H8A—C8—H8B	108.00
C2—C3—C4	122.2 (2)	C8—C9—H9	117.00
C3—C4—C5	120.1 (2)	C10—C9—H9	116.00
C4—C5—C6	117.0 (2)	C10—C11—H11A	109.00
S1—C6—C1	109.79 (14)	C10—C11—H11B	109.00
S1—C6—C5	126.83 (15)	C10—C11—H11C	109.00
C1—C6—C5	123.28 (16)	H11A—C11—H11B	109.00
O3—C7—N1	123.57 (19)	H11A—C11—H11C	109.00
O3—C7—C1	127.42 (18)	H11B—C11—H11C	109.00
N1—C7—C1	108.99 (16)	C10—C12—H12A	109.00
N1—C8—C9	111.79 (19)	C10—C12—H12B	109.00
C8—C9—C10	127.0 (2)	C10—C12—H12C	109.00
C9—C10—C11	124.9 (2)	H12A—C12—H12B	109.00
C9—C10—C12	120.5 (2)	H12A—C12—H12C	110.00
C11—C10—C12	114.6 (2)	H12B—C12—H12C	109.00

O1—S1—N1—C7	116.40 (14)	C6—C1—C2—C3	0.6 (3)
O1—S1—N1—C8	−67.88 (16)	C7—C1—C2—C3	−176.00 (19)
O2—S1—N1—C7	−113.44 (14)	C2—C1—C6—S1	−177.54 (15)
O2—S1—N1—C8	62.29 (17)	C2—C1—C6—C5	−0.9 (3)
C6—S1—N1—C7	0.66 (15)	C7—C1—C6—S1	−0.5 (2)
C6—S1—N1—C8	176.38 (15)	C7—C1—C6—C5	176.15 (17)
O1—S1—C6—C1	−113.04 (13)	C2—C1—C7—O3	−0.8 (3)
O1—S1—C6—C5	70.51 (19)	C2—C1—C7—N1	177.73 (19)
O2—S1—C6—C1	111.81 (14)	C6—C1—C7—O3	−177.6 (2)
O2—S1—C6—C5	−64.64 (19)	C6—C1—C7—N1	0.9 (2)
N1—S1—C6—C1	−0.09 (14)	C1—C2—C3—C4	−0.3 (3)
N1—S1—C6—C5	−176.54 (17)	C2—C3—C4—C5	0.2 (3)
S1—N1—C7—O3	177.61 (17)	C3—C4—C5—C6	−0.4 (3)
S1—N1—C7—C1	−1.0 (2)	C4—C5—C6—S1	176.81 (15)
C8—N1—C7—O3	2.1 (3)	C4—C5—C6—C1	0.8 (3)
C8—N1—C7—C1	−176.49 (17)	N1—C8—C9—C10	−119.5 (2)
S1—N1—C8—C9	−83.37 (19)	C8—C9—C10—C11	0.3 (3)
C7—N1—C8—C9	91.9 (2)	C8—C9—C10—C12	178.9 (2)

Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) −x+1, −y+1, z+1/2; (iii) −x, −y+1, z+1/2; (iv) x, y, z−1; (v) x, y, z+1; (vi) x−1/2, −y+1/2, z−1; (vii) x+1/2, −y+1/2, z; (viii) x−1/2, −y+1/2, z; (ix) −x, −y+1, z−1/2; (x) x+1/2, −y+1/2, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱⁱ	0.93	2.56	3.391 (2)	149
C8—H8A···O2^iv	0.97	2.51	3.436 (3)	160
C3—H3···Cg1^vii	0.93	2.89	3.664 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃NO₃S
M_r	251.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	9.4120 (5), 19.4108 (11), 6.5261 (4)
V (Å³)	1192.28 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.924, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	7340, 2525, 2304
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.083, 1.05
No. of reflections	2525
No. of parameters	156
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20
Absolute structure	Flack (1983), 837 Friedel pairs
Absolute structure parameter	0.02 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.56	3.391 (2)	149
C8—H8A···O2ⁱⁱ	0.97	2.51	3.436 (3)	160
C3—H3···Cg1ⁱⁱⁱ	0.93	2.89	3.664 (2)	141

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

Acknowledgements

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2–183).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kruszynski, R. & Czestkowski, W. (2001). Acta Cryst. E57, o516–o518. Web of Science CSD CrossRef IUCr Journals Google Scholar
Primofiore, G., Da Settimo, F., La Motta, C., Simorini, F., Minutolo, A. & Boldrini, E. (1997). Farmaco, 52, 583–588. Web of Science CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Parvez, M. (2007). Acta Cryst. E63, o4116. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, G.-P., Xu, Z.-J., Xu, L.-Z. & Aisa, H. A. (2008). Acta Cryst. E64, o805. Web of Science CSD CrossRef IUCr Journals Google Scholar