N-Saccharinylmethyl ether

Siddiqui, W.A.; Akhtar, Y.; Akmal, M.; Siddiqui, H.L.; Parvez, M.

doi:10.1107/S1600536810010317

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o929

doi:10.1107/S1600536810010317

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N-Saccharinylmethyl ether

Waseeq Ahmad Siddiqui,^a ^* Yasmeen Akhtar,^a Muhammad Akmal,^a Hamid Latif Siddiqui ^b and Masood Parvez ^c

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, ^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: waseeqsiddiqui@gmail.com

(Received 16 March 2010; accepted 19 March 2010; online 27 March 2010)

In the title molecule [systematic name: 1,1,1′,1′-tetraoxo-2,2′-(oxydimethylene)bi(1,2-benzothiazol-3-one)], C₁₆H₁₂N₂O₇S₂, the benzisothiazole ring systems are individually planar [maximum deviations of 0.0497 (13) and 0.0195 (19) Å] and their mean planes are inclined at a dihedral angle of 62.76 (4)°. The crystal structure is stabilized by weak intermolecular C—H⋯O interactions. Two O atoms bonded to two S atoms and four aryl H atoms belonging to two symmetry-related molecules lying about an inversion center form a hydrogen-bonded 10-membered ring with graph-set notation R₄²(10).

Related literature

For the biological activity of saccharin derivatives, see: Plath et al. (1998 ); Salzburg et al. (1987 ); Kapui et al. (2003 ). For the synthesis of saccharin derivatives, see: Ahmad et al. (2010 ); Siddiqui et al. (2010 ). For related structures, see: Ahmad et al. (2009 ); Gul et al. (2010 ); Khalid et al. (2010 ); Siddiqui et al. (2007 , 2008 ). For the graph-set notation of hydrogen-bonding patterns, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₇S₂
M_r = 408.40
Monoclinic, P 2₁ /n
a = 8.9317 (4) Å
b = 18.3681 (6) Å
c = 10.1942 (5) Å
β = 93.517 (2)°
V = 1669.29 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 200 K
0.08 × 0.06 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.971, T_max = 0.986
6489 measured reflections
3756 independent reflections
3052 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.112
S = 1.09
3756 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4ⁱ	0.95	2.39	3.307 (4)	162
C2—H2⋯O4ⁱⁱ	0.95	2.53	3.293 (3)	138
C8—H8B⋯O4ⁱⁱⁱ	0.99	2.52	3.027 (3)	111
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y, z-1; (iii) -x+1, -y, -z+1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: 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/S1600536810010317/lh5013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010317/lh5013Isup2.hkl

checkCIF report

Comment top

The derivatives of saccharin have found applications as bioactive substances (Plath et al., 1998; Salzburg et al., 1987). They are considered to be the most potent orally active human leucocyte elastase (HLE) inhibitors for the treatment of asthma and other inflammatory diseases (Kapui et al., 2003). Continuing our investigations in the synthesis and development of new saccharin derivatives (Ahmad et al., 2010; Siddiqui et al., 2010) with medicinal potentials, we now report the crystal structure of a novel compound in this paper.

The title compound is presented in Fig. 1. The benzisothiazole ring systems are individually planar with maximum deviations being 0.0497 (13) and 0.0195 (19) Å for S1 and C15 atoms from the mean-planes S1/N1/C1—C7 and S2/N2/C9—C15, respectively; the mean-planes are inclined at 62.76 (4)° with respect to each other. The structure is devoid of classical hydrogen bonds. However, intramolecular and intermolecular interactions of the type C—H···O are present in the structure. Two oxygen atoms bonded to two S atoms and four aryl hydrogen atoms belonging to two symmetry related molecules lying about inversion center form a hydrogen bonded ten membered ring which may be described in the graph set notation as R₄²(10) (Bernstein et al., 1995); details have been given in Tab. 1 and Fig. 2.

The bond distances and angles in the title molecule agree well with the cortresponding bond distances and angles reported in closely related compounds (Ahmad et al., 2009; Gul et al., 2010; Khalid et al., 2010; Siddiqui et al., 2007; 2008).

Related literature top

For biological activity of saccharin derivatives, see: Plath et al. (1998); Salzburg et al. (1987); Kapui et al. (2003). For the synthesis of saccharin derivatives, see: Ahmad et al. (2010); Siddiqui et al. (2010). For related structures, see: Ahmad et al. (2009); Gul et al. (2010); Khalid et al. (2010); Siddiqui et al. (2007, 2008). For the graph-set notation of hydrogen-bonding patterns, see: Bernstein et al. (1995).

Experimental top

The synthesis of the title compound will be reported in a future paper. Suitable crystals of the title compound were grown from a solution of CHCl₃ by slow evaporation at room temperature.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: 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. The title molecule with the displacement ellipsoids plotted at 50% probability level (Farrugia, 1997).
	Fig. 2. Unit cell packing of the title compound showing hydrogen bonds by dashed lines; the H-atoms not involved in H-bonds have been excluded for clarity.

1,1,1',1'-tetraoxo-2,2'-(oxydimethylene)bi(1,2-benzothiazol-3-one) top

Crystal data top

C₁₆H₁₂N₂O₇S₂	F(000) = 840
M_r = 408.40	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3299 reflections
a = 8.9317 (4) Å	θ = 1.0–27.4°
b = 18.3681 (6) Å	µ = 0.37 mm⁻¹
c = 10.1942 (5) Å	T = 200 K
β = 93.517 (2)°	Block, colorless
V = 1669.29 (12) Å³	0.08 × 0.06 × 0.04 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3756 independent reflections
Radiation source: fine-focus sealed tube	3052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 27.4°, θ_min = 2.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
T_min = 0.971, T_max = 0.986	k = −23→18
6489 measured reflections	l = −13→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0212P)² + 2.3993P] where P = (F_o² + 2F_c²)/3
3756 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₁₂N₂O₇S₂	V = 1669.29 (12) Å³
M_r = 408.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9317 (4) Å	µ = 0.37 mm⁻¹
b = 18.3681 (6) Å	T = 200 K
c = 10.1942 (5) Å	0.08 × 0.06 × 0.04 mm
β = 93.517 (2)°

Data collection top

Nonius KappaCCD diffractometer	3756 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3052 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.986	R_int = 0.033
6489 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.09	Δρ_max = 0.30 e Å⁻³
3756 reflections	Δρ_min = −0.42 e Å⁻³
244 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 > 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	0.16733 (7)	0.13166 (4)	0.14038 (7)	0.03295 (17)
S2	0.38728 (7)	0.12529 (3)	0.66150 (6)	0.02728 (15)
O1	0.2772 (2)	0.12845 (12)	0.0444 (2)	0.0478 (5)
O2	0.1836 (2)	0.18787 (11)	0.2374 (2)	0.0429 (5)
O3	−0.0103 (2)	−0.04351 (11)	0.2382 (2)	0.0442 (5)
O4	0.4221 (2)	0.07537 (10)	0.76644 (19)	0.0359 (4)
O5	0.5094 (2)	0.14955 (11)	0.5886 (2)	0.0398 (5)
O6	0.0076 (2)	0.11239 (11)	0.48394 (19)	0.0383 (5)
O7	0.3567 (2)	0.03938 (11)	0.37697 (18)	0.0383 (5)
N1	0.1573 (2)	0.04988 (12)	0.2123 (2)	0.0310 (5)
N2	0.2511 (2)	0.09045 (12)	0.5604 (2)	0.0290 (5)
C1	−0.2366 (3)	0.05097 (15)	0.0789 (3)	0.0346 (6)
H1	−0.2855	0.0083	0.1071	0.042*
C2	−0.3127 (3)	0.10214 (17)	0.0004 (3)	0.0411 (7)
H2	−0.4159	0.0948	−0.0245	0.049*
C3	−0.2408 (4)	0.16386 (17)	−0.0425 (3)	0.0438 (7)
H3	−0.2948	0.1972	−0.0988	0.053*
C4	−0.0923 (3)	0.17795 (15)	−0.0053 (3)	0.0383 (6)
H4	−0.0437	0.2208	−0.0328	0.046*
C5	−0.0177 (3)	0.12689 (14)	0.0738 (3)	0.0291 (5)
C6	−0.0865 (3)	0.06398 (13)	0.1153 (3)	0.0278 (5)
C7	0.0161 (3)	0.01604 (14)	0.1959 (3)	0.0302 (5)
C8	0.2930 (3)	0.01150 (16)	0.2583 (3)	0.0381 (7)
H8A	0.2690	−0.0406	0.2702	0.046*
H8B	0.3673	0.0149	0.1904	0.046*
C9	0.0236 (3)	0.24265 (15)	0.6728 (3)	0.0340 (6)
H9	−0.0741	0.2401	0.6307	0.041*
C10	0.0619 (3)	0.29787 (15)	0.7627 (3)	0.0381 (6)
H10	−0.0114	0.3329	0.7828	0.046*
C11	0.2047 (3)	0.30251 (15)	0.8233 (3)	0.0358 (6)
H11	0.2281	0.3411	0.8831	0.043*
C12	0.3143 (3)	0.25158 (14)	0.7980 (3)	0.0342 (6)
H12	0.4124	0.2543	0.8393	0.041*
C13	0.2738 (3)	0.19682 (14)	0.7098 (3)	0.0281 (5)
C14	0.1321 (3)	0.19172 (14)	0.6466 (2)	0.0282 (5)
C15	0.1155 (3)	0.12903 (14)	0.5542 (2)	0.0284 (5)
C16	0.2762 (3)	0.02374 (14)	0.4899 (3)	0.0331 (6)
H16A	0.3342	−0.0108	0.5477	0.040*
H16B	0.1788	0.0009	0.4628	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0283 (3)	0.0322 (3)	0.0387 (4)	−0.0050 (3)	0.0046 (3)	−0.0050 (3)
S2	0.0211 (3)	0.0322 (3)	0.0282 (3)	0.0023 (2)	−0.0006 (2)	−0.0019 (3)
O1	0.0381 (11)	0.0540 (13)	0.0533 (14)	−0.0084 (10)	0.0177 (10)	−0.0029 (11)
O2	0.0383 (11)	0.0362 (10)	0.0539 (13)	−0.0069 (9)	0.0005 (10)	−0.0149 (10)
O3	0.0501 (12)	0.0346 (10)	0.0474 (13)	−0.0041 (9)	−0.0018 (10)	0.0132 (9)
O4	0.0347 (10)	0.0398 (10)	0.0324 (10)	0.0094 (8)	−0.0047 (8)	0.0011 (8)
O5	0.0256 (9)	0.0499 (12)	0.0447 (12)	−0.0026 (8)	0.0081 (8)	−0.0036 (10)
O6	0.0296 (9)	0.0494 (11)	0.0347 (11)	0.0017 (8)	−0.0086 (8)	0.0000 (9)
O7	0.0296 (10)	0.0552 (12)	0.0295 (10)	0.0028 (9)	−0.0031 (8)	−0.0124 (9)
N1	0.0264 (11)	0.0316 (11)	0.0342 (12)	0.0032 (9)	−0.0036 (9)	−0.0028 (10)
N2	0.0243 (10)	0.0346 (11)	0.0274 (11)	0.0034 (9)	−0.0029 (8)	−0.0040 (9)
C1	0.0313 (13)	0.0371 (14)	0.0348 (15)	−0.0031 (11)	−0.0024 (11)	−0.0061 (12)
C2	0.0336 (14)	0.0521 (17)	0.0358 (15)	0.0082 (13)	−0.0112 (12)	−0.0132 (13)
C3	0.0567 (19)	0.0400 (16)	0.0335 (16)	0.0168 (14)	−0.0064 (14)	−0.0013 (13)
C4	0.0509 (17)	0.0316 (13)	0.0327 (15)	0.0032 (12)	0.0043 (13)	0.0036 (12)
C5	0.0295 (13)	0.0292 (12)	0.0287 (13)	0.0000 (10)	0.0025 (10)	−0.0010 (10)
C6	0.0274 (12)	0.0270 (12)	0.0285 (13)	0.0005 (10)	−0.0008 (10)	−0.0029 (10)
C7	0.0335 (13)	0.0297 (12)	0.0270 (13)	0.0009 (11)	−0.0023 (11)	−0.0024 (11)
C8	0.0315 (14)	0.0471 (16)	0.0345 (15)	0.0121 (12)	−0.0083 (12)	−0.0124 (13)
C9	0.0281 (13)	0.0375 (14)	0.0366 (15)	0.0058 (11)	0.0047 (11)	0.0064 (12)
C10	0.0405 (15)	0.0341 (14)	0.0406 (16)	0.0108 (12)	0.0090 (13)	0.0031 (12)
C11	0.0431 (15)	0.0312 (13)	0.0339 (14)	0.0012 (11)	0.0081 (12)	−0.0028 (11)
C12	0.0340 (14)	0.0346 (13)	0.0341 (15)	−0.0026 (11)	0.0041 (12)	−0.0026 (12)
C13	0.0229 (11)	0.0323 (12)	0.0296 (13)	0.0021 (10)	0.0046 (10)	0.0020 (11)
C14	0.0272 (12)	0.0311 (12)	0.0266 (13)	0.0007 (10)	0.0036 (10)	0.0073 (10)
C15	0.0255 (12)	0.0341 (13)	0.0256 (12)	0.0022 (10)	0.0019 (10)	0.0060 (11)
C16	0.0328 (13)	0.0329 (13)	0.0332 (14)	−0.0004 (11)	−0.0017 (11)	−0.0032 (11)

Geometric parameters (Å, º) top

S1—O1	1.429 (2)	C3—C4	1.382 (4)
S1—O2	1.431 (2)	C3—H3	0.9500
S1—N1	1.676 (2)	C4—C5	1.381 (4)
S1—C5	1.750 (3)	C4—H4	0.9500
S2—O5	1.4280 (19)	C5—C6	1.387 (3)
S2—O4	1.4287 (19)	C6—C7	1.482 (3)
S2—N2	1.673 (2)	C8—H8A	0.9900
S2—C13	1.748 (2)	C8—H8B	0.9900
O3—C7	1.205 (3)	C9—C14	1.384 (3)
O6—C15	1.205 (3)	C9—C10	1.396 (4)
O7—C8	1.402 (3)	C9—H9	0.9500
O7—C16	1.424 (3)	C10—C11	1.385 (4)
N1—C7	1.407 (3)	C10—H10	0.9500
N1—C8	1.454 (3)	C11—C12	1.390 (4)
N2—C15	1.401 (3)	C11—H11	0.9500
N2—C16	1.445 (3)	C12—C13	1.382 (4)
C1—C2	1.386 (4)	C12—H12	0.9500
C1—C6	1.390 (3)	C13—C14	1.388 (3)
C1—H1	0.9500	C14—C15	1.489 (4)
C2—C3	1.387 (5)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900

O1—S1—O2	117.27 (13)	O3—C7—N1	123.5 (2)
O1—S1—N1	108.66 (12)	O3—C7—C6	127.6 (2)
O2—S1—N1	110.47 (12)	N1—C7—C6	108.8 (2)
O1—S1—C5	113.86 (13)	O7—C8—N1	112.8 (2)
O2—S1—C5	110.97 (12)	O7—C8—H8A	109.0
N1—S1—C5	92.88 (11)	N1—C8—H8A	109.0
O5—S2—O4	116.83 (12)	O7—C8—H8B	109.0
O5—S2—N2	110.41 (12)	N1—C8—H8B	109.0
O4—S2—N2	109.43 (12)	H8A—C8—H8B	107.8
O5—S2—C13	112.74 (12)	C14—C9—C10	118.1 (3)
O4—S2—C13	112.00 (12)	C14—C9—H9	120.9
N2—S2—C13	92.81 (11)	C10—C9—H9	120.9
C8—O7—C16	115.2 (2)	C11—C10—C9	121.3 (3)
C7—N1—C8	123.2 (2)	C11—C10—H10	119.4
C7—N1—S1	114.55 (17)	C9—C10—H10	119.4
C8—N1—S1	120.62 (19)	C10—C11—C12	121.0 (3)
C15—N2—C16	124.5 (2)	C10—C11—H11	119.5
C15—N2—S2	115.34 (17)	C12—C11—H11	119.5
C16—N2—S2	120.12 (17)	C13—C12—C11	116.8 (3)
C2—C1—C6	117.9 (3)	C13—C12—H12	121.6
C2—C1—H1	121.0	C11—C12—H12	121.6
C6—C1—H1	121.0	C12—C13—C14	123.1 (2)
C1—C2—C3	121.1 (3)	C12—C13—S2	126.7 (2)
C1—C2—H2	119.5	C14—C13—S2	110.25 (19)
C3—C2—H2	119.5	C9—C14—C13	119.6 (2)
C4—C3—C2	121.5 (3)	C9—C14—C15	126.9 (2)
C4—C3—H3	119.3	C13—C14—C15	113.5 (2)
C2—C3—H3	119.3	O6—C15—N2	123.8 (2)
C5—C4—C3	117.0 (3)	O6—C15—C14	128.1 (2)
C5—C4—H4	121.5	N2—C15—C14	108.1 (2)
C3—C4—H4	121.5	O7—C16—N2	109.4 (2)
C4—C5—C6	122.5 (2)	O7—C16—H16A	109.8
C4—C5—S1	127.1 (2)	N2—C16—H16A	109.8
C6—C5—S1	110.41 (19)	O7—C16—H16B	109.8
C5—C6—C1	120.0 (2)	N2—C16—H16B	109.8
C5—C6—C7	113.2 (2)	H16A—C16—H16B	108.2
C1—C6—C7	126.8 (2)

O1—S1—N1—C7	−118.8 (2)	C1—C6—C7—O3	3.8 (5)
O2—S1—N1—C7	111.19 (19)	C5—C6—C7—N1	2.2 (3)
C5—S1—N1—C7	−2.5 (2)	C1—C6—C7—N1	−178.7 (2)
O1—S1—N1—C8	47.0 (2)	C16—O7—C8—N1	71.9 (3)
O2—S1—N1—C8	−83.0 (2)	C7—N1—C8—O7	−118.3 (3)
C5—S1—N1—C8	163.4 (2)	S1—N1—C8—O7	77.1 (3)
O5—S2—N2—C15	−114.79 (19)	C14—C9—C10—C11	0.8 (4)
O4—S2—N2—C15	115.27 (19)	C9—C10—C11—C12	−1.0 (4)
C13—S2—N2—C15	0.8 (2)	C10—C11—C12—C13	0.2 (4)
O5—S2—N2—C16	67.1 (2)	C11—C12—C13—C14	0.8 (4)
O4—S2—N2—C16	−62.9 (2)	C11—C12—C13—S2	−179.1 (2)
C13—S2—N2—C16	−177.4 (2)	O5—S2—C13—C12	−66.3 (3)
C6—C1—C2—C3	1.1 (4)	O4—S2—C13—C12	67.9 (3)
C1—C2—C3—C4	−2.2 (4)	N2—S2—C13—C12	−179.8 (2)
C2—C3—C4—C5	1.6 (4)	O5—S2—C13—C14	113.83 (19)
C3—C4—C5—C6	−0.1 (4)	O4—S2—C13—C14	−111.97 (19)
C3—C4—C5—S1	−177.6 (2)	N2—S2—C13—C14	0.3 (2)
O1—S1—C5—C4	−66.8 (3)	C10—C9—C14—C13	0.1 (4)
O2—S1—C5—C4	68.1 (3)	C10—C9—C14—C15	−179.7 (2)
N1—S1—C5—C4	−178.6 (3)	C12—C13—C14—C9	−0.9 (4)
O1—S1—C5—C6	115.5 (2)	S2—C13—C14—C9	179.0 (2)
O2—S1—C5—C6	−109.6 (2)	C12—C13—C14—C15	178.9 (2)
N1—S1—C5—C6	3.7 (2)	S2—C13—C14—C15	−1.2 (3)
C4—C5—C6—C1	−0.9 (4)	C16—N2—C15—O6	−3.9 (4)
S1—C5—C6—C1	176.9 (2)	S2—N2—C15—O6	178.1 (2)
C4—C5—C6—C7	178.2 (2)	C16—N2—C15—C14	176.5 (2)
S1—C5—C6—C7	−3.9 (3)	S2—N2—C15—C14	−1.5 (3)
C2—C1—C6—C5	0.4 (4)	C9—C14—C15—O6	2.0 (4)
C2—C1—C6—C7	−178.6 (3)	C13—C14—C15—O6	−177.8 (3)
C8—N1—C7—O3	12.8 (4)	C9—C14—C15—N2	−178.5 (2)
S1—N1—C7—O3	178.2 (2)	C13—C14—C15—N2	1.7 (3)
C8—N1—C7—C6	−164.8 (2)	C8—O7—C16—N2	−128.4 (2)
S1—N1—C7—C6	0.6 (3)	C15—N2—C16—O7	101.2 (3)
C5—C6—C7—O3	−175.2 (3)	S2—N2—C16—O7	−80.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.95	2.39	3.307 (4)	162
C2—H2···O4ⁱⁱ	0.95	2.53	3.293 (3)	138
C8—H8B···O4ⁱⁱⁱ	0.99	2.52	3.027 (3)	111
C8—H8A···O3	0.99	2.50	2.887 (4)	103

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₇S₂
M_r	408.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	8.9317 (4), 18.3681 (6), 10.1942 (5)
β (°)	93.517 (2)
V (Å³)	1669.29 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.08 × 0.06 × 0.04

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.971, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	6489, 3756, 3052
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.112, 1.09
No. of reflections	3756
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.42

Computer programs: COLLECT (Hooft, 1998), 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
C1—H1···O4ⁱ	0.95	2.39	3.307 (4)	162.4
C2—H2···O4ⁱⁱ	0.95	2.53	3.293 (3)	137.8
C8—H8B···O4ⁱⁱⁱ	0.99	2.52	3.027 (3)	111.2
C8—H8A···O3	0.99	2.50	2.887 (4)	103.1

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

Acknowledgements

HLS is grateful to the Institute of Chemistry, University of the Punjab, for financial support.

References

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