2-[2-(3-Chloro­phen­yl)-2-oxoeth­yl]-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

Khalid, Z.; Siddiqui, H.L.; Ahmad, M.; Bukhari, I.H.; Parvez, M.

doi:10.1107/S1600536810005428

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o617

doi:10.1107/S1600536810005428

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2-[2-(3-Chlorophenyl)-2-oxoethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Zunera Khalid,^a Hamid Latif Siddiqui,^a ^* Matloob Ahmad,^a Iftikhar Hussain Bukhari ^b and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, ^bDepartment of Chemistry, University of Sargodha, Sargodha 10400, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 1 February 2010; accepted 9 February 2010; online 13 February 2010)

In the title compound, C₁₅H₁₀ClNO₄S, the benzothiazole ring system is essentially planar [maximum deviation = 0.0382 (13) Å for the N atom] and forms a dihedral angle of 74.43 (6)° with the chloro-substituted benzene ring. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds form R₂²(10) and R₂²(16) ring motifs

Related literature

For the use of 1,2-benzisothiazoline-3-one 1,1-dioxide (saccharine) as an intermediate in the preparation of medicinally important molecules, see: Siddiqui et al. (2006 ); Zia-ur-Rehman et al. (2005 , 2009 ). For the biological activity of saccharine, see: Singh et al. (2007 ); Vaccarino et al. (2007 ); Kapui et al. (2003 ). For related structures, see: Ahmad et al. (2008 , 2009 ). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ). Zia-ur-Rehman, Choudary & Ahmad (2005).

Experimental

Crystal data

C₁₅H₁₀ClNO₄S
M_r = 335.75
Triclinic, $[P \overline 1]$
a = 7.7258 (4) Å
b = 9.0780 (4) Å
c = 10.0809 (5) Å
α = 83.884 (3)°
β = 85.092 (3)°
γ = 87.765 (3)°
V = 700.10 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 173 K
0.20 × 0.12 × 0.10 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.917, T_max = 0.957
5768 measured reflections
3157 independent reflections
2881 reflections with (I) > 2.0 σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.06
3157 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.95	2.40	3.249 (3)	148
C8—H8A⋯O1ⁱⁱ	0.99	2.45	3.378 (3)	156
C11—H11⋯O3ⁱⁱⁱ	0.95	2.44	3.382 (3)	173
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536810005428/lh2992sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005428/lh2992Isup2.hkl

checkCIF report

Comment top

1,2-Benzisothiazoline-3-one 1,1-dioxide (saccharine) is an important starting material for the synthesis of different heterocyclic compounds and plays a role as an intermediate for the preparation of medicinally important molecules (Siddiqui et al., 2006; Zia-ur-Rehman et al., 2005; Zia-ur-Rehman et al., 2009). Various derivatives of saccharin are known to be cyclooxygenase-2 (COX-2) inhibitors (Singh et al., 2007), analgesic (Vaccarino et al., 2007), human leucocyte elastase (HLE) inhibitors (Kapui et al., 2003) etc. In continuation of our research on the synthesis of potential biologically active derivatives of benzothiazines (Ahmad et al., 2008; Ahmad et al., 2009), we herein report the crystal structure of the title compound (I).

The molecular structure of the title compund is shown in (Fig. 1). The benzothiazole moiety (S1/N1/C1—C7) is essentially planar (maximum deviation = 0.0382 (13) Å for atom N1) and lies at an angle 74.43 (6) ° with respect to the C10—C15 benzene ring. The structure is devoid of any classical hydrogen bonds. However, non-classical hydrogen bonding interactions of the type C—H···O are present in the crystal structure resulting in ten and sixteen membered macrocyclic rings in R₂²(10) and R₂²(16) motifs (Bernstein et al., 1995) (Fig. 2 and Table 1).

Related literature top

For the use of 1,2-benzisothiazoline-3-one 1,1-dioxide (saccharine) as an intermediate in the preparation of medicinally important molecules, see: Siddiqui et al. (2006); Zia-ur-Rehman et al. (2005, 2009). For the biological activity of saccharine, see: Singh et al. (2007); Vaccarino et al. (2007); Kapui et al. (2003). For related structures, see: Ahmad et al. (2008, 2009). For hydrogen-bonding motifs, see: Bernstein et al. (1995). Zia-ur-Rehman, Choudary & Ahmad (2005).

Experimental top

3-Chlorophenacyl bromide (5.60 g, 0.024 mol) was slowly added to a suspension of sodium saccharine (5 g, 0.024 mol) in dimethylformamide (15 ml) and the mixture was stirred at 383 K for 3 hours under anhydrous conditions. On completion of reaction (indicated by TLC), the mixture was poured on crushed ice and the precipitates formed were filtered and washed with excess of distilled water and cold ethanol respectively. The crystals of the title compound suitable for XRD were grown from a solution of chloroform-methanol (3:1).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level.
	Fig. 2. Unit cell packing of (I) showing non-classical hydrogen bonding interaction with dashed lines; H-atoms not involved in H-bonds have been excluded for clarity.

2-[2-(3-Chlorophenyl)-2-oxoethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide top

Crystal data top

C₁₅H₁₀ClNO₄S	Z = 2
M_r = 335.75	F(000) = 344
Triclinic, P1	D_x = 1.593 Mg m⁻³
Hall symbol: -P 1	Melting point: 488 K
a = 7.7258 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0780 (4) Å	Cell parameters from 2955 reflections
c = 10.0809 (5) Å	θ = 1.0–27.5°
α = 83.884 (3)°	µ = 0.44 mm⁻¹
β = 85.092 (3)°	T = 173 K
γ = 87.765 (3)°	Prism, white
V = 700.10 (6) Å³	0.20 × 0.12 × 0.10 mm

Data collection top

Nonius APEXII CCD diffractometer	3157 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with (I) > 2.0 σ(I)
Graphite monochromator	R_int = 0.025
ϕ & ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→9
T_min = 0.917, T_max = 0.957	k = −11→11
5768 measured reflections	l = −12→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0738P)² + 0.5259P] where P = (F_o² + 2F_c²)/3
3157 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₅H₁₀ClNO₄S	γ = 87.765 (3)°
M_r = 335.75	V = 700.10 (6) Å³
Triclinic, P1	Z = 2
a = 7.7258 (4) Å	Mo Kα radiation
b = 9.0780 (4) Å	µ = 0.44 mm⁻¹
c = 10.0809 (5) Å	T = 173 K
α = 83.884 (3)°	0.20 × 0.12 × 0.10 mm
β = 85.092 (3)°

Data collection top

Nonius APEXII CCD diffractometer	3157 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2881 reflections with (I) > 2.0 σ(I)
T_min = 0.917, T_max = 0.957	R_int = 0.025
5768 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
3157 reflections	Δρ_min = −0.40 e Å⁻³
199 parameters

Special details top

Experimental. IR (KBr): 1737, 1690, 1341, 1151 cm^-1, ¹H NMR: (DMSO-d₆) δ: 5.40 (s, 2H, CH₂), 7.43 (dd, 1H, J1 = 2.4 Hz, J2 = 8.4 Hz, Ar—H), 7.50 (t, 1H, J = 8.0 Hz, Ar—H), 7.58 (t, 1H, J = 2.4 Hz, Ar—H), 7.65 (d, 1H, J = 7.6 Hz, Ar—H), 8.05 (t, 1H, J = 7.6 Hz, Ar—H), 8.11 (t, 1H, J = 7.6 Hz, Ar—H), 8.17 (d, 1H, J = 7.6 Hz, Ar—H), 8.23 (d, 1H, J = 7.2 Hz, Ar—H). MS m/z: 335.8[M⁺].

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 > 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
Cl1	0.05636 (8)	0.97635 (7)	0.83644 (5)	0.03594 (18)
S1	0.13366 (6)	0.50633 (5)	0.22038 (5)	0.02250 (15)
O1	0.57018 (19)	0.54728 (17)	0.34507 (15)	0.0275 (3)
O2	0.0709 (2)	0.62625 (18)	0.13199 (17)	0.0340 (4)
O3	0.0067 (2)	0.42357 (19)	0.30583 (17)	0.0341 (4)
O4	0.3503 (2)	0.85538 (18)	0.25316 (16)	0.0360 (4)
N1	0.2798 (2)	0.56575 (19)	0.31383 (17)	0.0237 (4)
C1	0.2881 (2)	0.3923 (2)	0.13935 (19)	0.0206 (4)
C2	0.2593 (3)	0.2980 (2)	0.0452 (2)	0.0259 (4)
H2	0.1469	0.2874	0.0166	0.031*
C3	0.4039 (3)	0.2192 (2)	−0.0055 (2)	0.0285 (4)
H3	0.3898	0.1525	−0.0700	0.034*
C4	0.5687 (3)	0.2356 (2)	0.0359 (2)	0.0279 (4)
H4	0.6648	0.1808	−0.0012	0.034*
C5	0.5948 (3)	0.3314 (2)	0.1312 (2)	0.0239 (4)
H5	0.7071	0.3424	0.1598	0.029*
C6	0.4518 (3)	0.4102 (2)	0.18287 (18)	0.0197 (4)
C7	0.4493 (3)	0.5143 (2)	0.28697 (19)	0.0207 (4)
C8	0.2318 (3)	0.6673 (2)	0.4143 (2)	0.0237 (4)
H8A	0.2891	0.6334	0.4968	0.028*
H8B	0.1046	0.6660	0.4367	0.028*
C9	0.2845 (3)	0.8255 (2)	0.3652 (2)	0.0232 (4)
C10	0.2549 (3)	0.9392 (2)	0.46202 (19)	0.0216 (4)
C11	0.1755 (3)	0.9062 (2)	0.5907 (2)	0.0219 (4)
H11	0.1351	0.8095	0.6193	0.026*
C12	0.1567 (3)	1.0164 (2)	0.6761 (2)	0.0237 (4)
C13	0.2149 (3)	1.1584 (2)	0.6376 (2)	0.0277 (4)
H13	0.2020	1.2324	0.6979	0.033*
C14	0.2926 (3)	1.1900 (2)	0.5085 (2)	0.0307 (5)
H14	0.3325	1.2868	0.4804	0.037*
C15	0.3124 (3)	1.0828 (2)	0.4209 (2)	0.0266 (4)
H15	0.3648	1.1062	0.3328	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0441 (3)	0.0384 (3)	0.0246 (3)	−0.0009 (2)	0.0080 (2)	−0.0084 (2)
S1	0.0185 (2)	0.0232 (3)	0.0262 (3)	0.00100 (18)	−0.00166 (18)	−0.00494 (19)
O1	0.0254 (7)	0.0312 (8)	0.0276 (8)	−0.0025 (6)	−0.0057 (6)	−0.0074 (6)
O2	0.0318 (8)	0.0319 (8)	0.0386 (9)	0.0082 (7)	−0.0110 (7)	−0.0020 (7)
O3	0.0245 (8)	0.0375 (9)	0.0398 (9)	−0.0060 (7)	0.0071 (7)	−0.0073 (7)
O4	0.0505 (10)	0.0325 (8)	0.0234 (8)	−0.0037 (7)	0.0081 (7)	−0.0037 (6)
N1	0.0221 (8)	0.0248 (8)	0.0252 (8)	0.0024 (7)	−0.0022 (6)	−0.0087 (7)
C1	0.0206 (9)	0.0200 (9)	0.0207 (9)	0.0005 (7)	0.0003 (7)	−0.0017 (7)
C2	0.0257 (10)	0.0271 (10)	0.0258 (10)	−0.0028 (8)	−0.0042 (8)	−0.0047 (8)
C3	0.0366 (12)	0.0261 (10)	0.0238 (10)	−0.0025 (8)	−0.0007 (8)	−0.0083 (8)
C4	0.0300 (10)	0.0279 (10)	0.0250 (10)	0.0041 (8)	0.0027 (8)	−0.0047 (8)
C5	0.0218 (9)	0.0254 (10)	0.0238 (10)	0.0007 (8)	0.0009 (7)	−0.0016 (8)
C6	0.0234 (9)	0.0185 (9)	0.0168 (8)	−0.0013 (7)	−0.0005 (7)	−0.0007 (7)
C7	0.0224 (9)	0.0182 (9)	0.0210 (9)	−0.0007 (7)	−0.0010 (7)	−0.0007 (7)
C8	0.0280 (10)	0.0216 (9)	0.0217 (9)	0.0010 (8)	0.0010 (8)	−0.0067 (7)
C9	0.0219 (9)	0.0258 (10)	0.0216 (9)	0.0011 (7)	−0.0014 (7)	−0.0025 (8)
C10	0.0217 (9)	0.0220 (9)	0.0215 (9)	0.0002 (7)	−0.0020 (7)	−0.0032 (7)
C11	0.0222 (9)	0.0209 (9)	0.0227 (9)	0.0007 (7)	−0.0007 (7)	−0.0031 (7)
C12	0.0252 (10)	0.0270 (10)	0.0193 (9)	0.0017 (8)	−0.0025 (7)	−0.0041 (7)
C13	0.0317 (11)	0.0244 (10)	0.0289 (11)	0.0010 (8)	−0.0073 (8)	−0.0076 (8)
C14	0.0390 (12)	0.0214 (10)	0.0319 (11)	−0.0038 (9)	−0.0053 (9)	−0.0007 (8)
C15	0.0325 (11)	0.0244 (10)	0.0228 (10)	−0.0032 (8)	−0.0024 (8)	−0.0003 (8)

Geometric parameters (Å, º) top

Cl1—C12	1.740 (2)	C5—C6	1.387 (3)
S1—O2	1.4285 (16)	C5—H5	0.9500
S1—O3	1.4297 (16)	C6—C7	1.483 (3)
S1—N1	1.6707 (18)	C8—C9	1.528 (3)
S1—C1	1.755 (2)	C8—H8A	0.9900
O1—C7	1.207 (2)	C8—H8B	0.9900
O4—C9	1.206 (3)	C9—C10	1.493 (3)
N1—C7	1.388 (3)	C10—C11	1.395 (3)
N1—C8	1.456 (2)	C10—C15	1.403 (3)
C1—C2	1.381 (3)	C11—C12	1.384 (3)
C1—C6	1.394 (3)	C11—H11	0.9500
C2—C3	1.393 (3)	C12—C13	1.387 (3)
C2—H2	0.9500	C13—C14	1.391 (3)
C3—C4	1.392 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.377 (3)
C4—C5	1.394 (3)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500

O2—S1—O3	116.98 (10)	N1—C7—C6	108.78 (17)
O2—S1—N1	110.34 (9)	N1—C8—C9	111.68 (16)
O3—S1—N1	108.98 (10)	N1—C8—H8A	109.3
O2—S1—C1	112.54 (10)	C9—C8—H8A	109.3
O3—S1—C1	112.63 (10)	N1—C8—H8B	109.3
N1—S1—C1	92.62 (9)	C9—C8—H8B	109.3
C7—N1—C8	122.70 (17)	H8A—C8—H8B	107.9
C7—N1—S1	115.44 (14)	O4—C9—C10	121.91 (19)
C8—N1—S1	121.85 (14)	O4—C9—C8	120.72 (19)
C2—C1—C6	122.96 (18)	C10—C9—C8	117.36 (17)
C2—C1—S1	127.13 (16)	C11—C10—C15	119.82 (19)
C6—C1—S1	109.90 (14)	C11—C10—C9	122.23 (18)
C1—C2—C3	116.44 (19)	C15—C10—C9	117.94 (18)
C1—C2—H2	121.8	C12—C11—C10	118.92 (18)
C3—C2—H2	121.8	C12—C11—H11	120.5
C4—C3—C2	121.64 (19)	C10—C11—H11	120.5
C4—C3—H3	119.2	C11—C12—C13	121.94 (19)
C2—C3—H3	119.2	C11—C12—Cl1	119.16 (16)
C3—C4—C5	120.9 (2)	C13—C12—Cl1	118.90 (16)
C3—C4—H4	119.5	C12—C13—C14	118.45 (19)
C5—C4—H4	119.5	C12—C13—H13	120.8
C6—C5—C4	118.02 (19)	C14—C13—H13	120.8
C6—C5—H5	121.0	C15—C14—C13	121.0 (2)
C4—C5—H5	121.0	C15—C14—H14	119.5
C5—C6—C1	119.99 (18)	C13—C14—H14	119.5
C5—C6—C7	126.87 (18)	C14—C15—C10	119.9 (2)
C1—C6—C7	113.12 (17)	C14—C15—H15	120.1
O1—C7—N1	123.66 (18)	C10—C15—H15	120.1
O1—C7—C6	127.50 (18)

O2—S1—N1—C7	−111.61 (16)	C8—N1—C7—C6	178.35 (16)
O3—S1—N1—C7	118.65 (15)	S1—N1—C7—C6	−3.0 (2)
C1—S1—N1—C7	3.62 (16)	C5—C6—C7—O1	−0.6 (3)
O2—S1—N1—C8	67.08 (18)	C1—C6—C7—O1	177.71 (19)
O3—S1—N1—C8	−62.65 (18)	C5—C6—C7—N1	−177.90 (19)
C1—S1—N1—C8	−177.68 (16)	C1—C6—C7—N1	0.5 (2)
O2—S1—C1—C2	−69.4 (2)	C7—N1—C8—C9	75.9 (2)
O3—S1—C1—C2	65.5 (2)	S1—N1—C8—C9	−102.69 (18)
N1—S1—C1—C2	177.32 (19)	N1—C8—C9—O4	3.1 (3)
O2—S1—C1—C6	110.17 (15)	N1—C8—C9—C10	−175.59 (17)
O3—S1—C1—C6	−114.98 (15)	O4—C9—C10—C11	178.6 (2)
N1—S1—C1—C6	−3.15 (15)	C8—C9—C10—C11	−2.8 (3)
C6—C1—C2—C3	0.1 (3)	O4—C9—C10—C15	−2.4 (3)
S1—C1—C2—C3	179.62 (16)	C8—C9—C10—C15	176.20 (18)
C1—C2—C3—C4	−0.4 (3)	C15—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	0.5 (3)	C9—C10—C11—C12	178.30 (18)
C3—C4—C5—C6	−0.3 (3)	C10—C11—C12—C13	−0.2 (3)
C4—C5—C6—C1	0.0 (3)	C10—C11—C12—Cl1	179.53 (15)
C4—C5—C6—C7	178.24 (18)	C11—C12—C13—C14	0.7 (3)
C2—C1—C6—C5	0.1 (3)	Cl1—C12—C13—C14	−179.03 (17)
S1—C1—C6—C5	−179.49 (15)	C12—C13—C14—C15	−0.3 (3)
C2—C1—C6—C7	−178.41 (18)	C13—C14—C15—C10	−0.5 (3)
S1—C1—C6—C7	2.0 (2)	C11—C10—C15—C14	1.0 (3)
C8—N1—C7—O1	1.0 (3)	C9—C10—C15—C14	−178.0 (2)
S1—N1—C7—O1	179.65 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.40	3.249 (3)	148
C8—H8A···O1ⁱⁱ	0.99	2.45	3.378 (3)	156
C11—H11···O3ⁱⁱⁱ	0.95	2.44	3.382 (3)	173

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClNO₄S
M_r	335.75
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.7258 (4), 9.0780 (4), 10.0809 (5)
α, β, γ (°)	83.884 (3), 85.092 (3), 87.765 (3)
V (Å³)	700.10 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Nonius APEXII CCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.917, 0.957
No. of measured, independent and observed [(I) > 2.0 σ(I)] reflections	5768, 3157, 2881
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.06
No. of reflections	3157
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.40

Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.40	3.249 (3)	148
C8—H8A···O1ⁱⁱ	0.99	2.45	3.378 (3)	156
C11—H11···O3ⁱⁱⁱ	0.95	2.44	3.382 (3)	173

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

Acknowledgements

The authors thank the Higher Education Commission of Pakistan for financial support of this research.

References

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