N-Acetyl-4-(benzene­sulfonamido)benzene­sulfonamide

Ashfaq, M.; Tahir, M.N.; Khan, I.U.; Arshad, M.N.; Saeed-ul-Hassan, S.

doi:10.1107/S1600536809015876

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1180

doi:10.1107/S1600536809015876

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N-Acetyl-4-(benzenesulfonamido)benzenesulfonamide

Muhammad Ashfaq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Nadeem Arshad ^a and Syed Saeed-ul-Hassan ^c

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

(Received 26 April 2009; accepted 28 April 2009; online 30 April 2009)

In the molecule of the title compound, C₁₄H₁₄N₂O₅S₂, the dihedral angle between the aromatic rings is 77.75 (9)°. The acetamide group is planar [maximum deviation = 0.002 (3) Å] and oriented at dihedral angles of 13.49 (21) and 73.94 (10)° with respect to the aromatic rings. An intramolecular C—H⋯O interaction results in the formation of a six-membered ring. In the crystal structure, intermolecular N—H⋯O and C—H⋯O interactions link the molecules into a three-dimensional network, forming R₂²(20) ring motifs.

Related literature

For related structures, see: Chohan et al. (2008 , 2009 ); Deng & Mani (2006 ); Ellingboe et al. (1992 ); Shad et al. (2009 ); Tahir et al. (2008 ). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₅S₂
M_r = 354.39
Monoclinic, P 2₁ /n
a = 9.9316 (9) Å
b = 9.4828 (8) Å
c = 17.6490 (17) Å
β = 103.169 (5)°
V = 1618.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.909, T_max = 0.940
17674 measured reflections
4034 independent reflections
2423 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.128
S = 1.02
4034 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5ⁱ	0.86	2.25	2.839 (3)	126
N2—H2N⋯O1ⁱⁱ	0.86	2.14	2.922 (3)	151
C8—H8⋯O2	0.93	2.49	3.116 (3)	125
C9—H9⋯O4ⁱⁱⁱ	0.93	2.60	3.237 (3)	126
C14—H14A⋯O2^iv	0.96	2.56	3.401 (4)	147
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x-1, y, 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 for Windows (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/S1600536809015876/hk2676sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015876/hk2676Isup2.hkl

checkCIF report

Comment top

Sulfonamides have attracted much attention, due to their extensive use in medicine. We have reported the syntheses and crystal structures of sulfonamides, which have the central portion of title compound as common (Chohan et al., 2008, 2009; Shad et al., 2009; Tahir et al., 2008). Similarly, the crystal structure of N-Methyl-N-(2-(methyl(1-methyl-1H-benzimidazol-2-yl)amino)- ethyl)-4-((methylsulfonyl)amino)-benzenesulfonamide (Ellingboe et al., 1992) has been reported, which also has a central portion as in the title compound.

In the molecule of the title compound (Fig 1), rings A (C1-C6) and B (C7-C12) are, of course, planar. The acetamide moiety C (N2/O5/C13/C14) is also planar with a maximum deviation of 0.002 (3) Å for atom C13. The diheadral angles between them are A/B = 77.75 (9), A/C = 13.49 (21) and B/C = 73.94 (10) °. The SO₂ groups are oriented at a dihedral angle of 71.02 (15)°. Intramolecular C-H···O interaction (Table 1) results in the formation of a six-membered ring D (S1/O2/N1/C7/C8/H8) having twisted conformation.

In the crystal structure, intermolecular N-H···O and C-H···O interactions (Table 1) link the molecules into a three-dimensional network forming R₂²(20) ring motifs (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure.

Related literature top

For related structures, see: Chohan et al. (2008, 2009); Deng & Mani (2006); Ellingboe et al. (1992); Shad et al. (2009); Tahir et al. (2008). For ring-motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized according to a literature method (Deng & Mani, 2006). For the preparation of the title compound, phenylglycine (2 g, 5.3 mmol) was dissolved in distilled water, and then benzene sulfonyl chloride (0.93 g, 5.3 mmol) was added. It was stirred at room temperature. During the reaction pH was maintained at 8-9, strictly using Na₂CO₃ (1 M), since HCl was produced as a byproduct, which lowers the pH. The completion of reaction was observed by the consumption of the oily drops of benzene sulfonyl chloride. On completion, pH was adjusted to 2-3 using HCl (2 N). The precipitate formed was filtered, washed with distilled water and recrystalyzed from methanol.

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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (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. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

N-Acetyl-4-(benzenesulfonamido)benzenesulfonamide top

Crystal data top

C₁₄H₁₄N₂O₅S₂	F(000) = 736
M_r = 354.39	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4034 reflections
a = 9.9316 (9) Å	θ = 2.4–28.3°
b = 9.4828 (8) Å	µ = 0.36 mm⁻¹
c = 17.6490 (17) Å	T = 296 K
β = 103.169 (5)°	Prism, colorless
V = 1618.5 (3) Å³	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4034 independent reflections
Radiation source: fine-focus sealed tube	2423 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.4°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→12
T_min = 0.909, T_max = 0.940	l = −22→23
17674 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.052P)² + 0.3831P] where P = (F_o² + 2F_c²)/3
4034 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₅S₂	V = 1618.5 (3) Å³
M_r = 354.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9316 (9) Å	µ = 0.36 mm⁻¹
b = 9.4828 (8) Å	T = 296 K
c = 17.6490 (17) Å	0.28 × 0.22 × 0.18 mm
β = 103.169 (5)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4034 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2423 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.940	R_int = 0.060
17674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
4034 reflections	Δρ_min = −0.36 e Å⁻³
209 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
S1	0.90183 (7)	0.28463 (8)	−0.04571 (4)	0.0407 (3)
S2	0.58491 (7)	0.45284 (7)	0.26062 (4)	0.0374 (2)
O1	0.9231 (2)	0.3308 (2)	−0.11946 (11)	0.0530 (7)
O2	1.01569 (19)	0.2335 (2)	0.01166 (11)	0.0546 (7)
O3	0.68083 (19)	0.4029 (2)	0.32790 (10)	0.0564 (7)
O4	0.5257 (2)	0.58953 (19)	0.26098 (11)	0.0510 (7)
O5	0.3371 (2)	0.4255 (2)	0.13539 (11)	0.0560 (7)
N1	0.8361 (2)	0.4215 (2)	−0.01260 (12)	0.0384 (7)
N2	0.4595 (2)	0.3347 (2)	0.24701 (12)	0.0387 (7)
C1	0.7705 (3)	0.1563 (3)	−0.06104 (15)	0.0396 (9)
C2	0.6519 (3)	0.1794 (3)	−0.11844 (17)	0.0518 (11)
C3	0.5482 (3)	0.0815 (4)	−0.1295 (2)	0.0703 (14)
C4	0.5621 (4)	−0.0385 (4)	−0.0833 (3)	0.0759 (17)
C5	0.6797 (4)	−0.0586 (3)	−0.0265 (2)	0.0729 (16)
C6	0.7849 (3)	0.0381 (3)	−0.01472 (18)	0.0545 (11)
C7	0.7799 (2)	0.4241 (3)	0.05379 (14)	0.0315 (8)
C8	0.8129 (3)	0.3261 (3)	0.11352 (15)	0.0417 (9)
C9	0.7502 (3)	0.3347 (3)	0.17563 (14)	0.0389 (9)
C10	0.6584 (3)	0.4411 (3)	0.17997 (14)	0.0321 (8)
C11	0.6272 (3)	0.5403 (3)	0.12140 (17)	0.0472 (10)
C12	0.6873 (3)	0.5305 (3)	0.05858 (16)	0.0446 (10)
C13	0.3439 (3)	0.3407 (3)	0.18721 (15)	0.0393 (9)
C14	0.2314 (3)	0.2385 (4)	0.19149 (18)	0.0655 (13)
H1N	0.83546	0.49926	−0.03774	0.0461*
H2	0.64289	0.26019	−0.14902	0.0622*
H2N	0.46714	0.26548	0.27920	0.0464*
H3	0.46813	0.09538	−0.16798	0.0843*
H4	0.49166	−0.10523	−0.09098	0.0910*
H5	0.68825	−0.13877	0.00460	0.0874*
H6	0.86471	0.02409	0.02393	0.0655*
H8	0.87684	0.25522	0.11176	0.0501*
H9	0.77038	0.26763	0.21503	0.0467*
H11	0.56602	0.61331	0.12432	0.0566*
H12	0.66522	0.59658	0.01874	0.0536*
H14A	0.19294	0.20141	0.14056	0.0984*
H14B	0.16038	0.28576	0.21067	0.0984*
H14C	0.26868	0.16277	0.22601	0.0984*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0359 (4)	0.0556 (5)	0.0317 (4)	0.0099 (3)	0.0102 (3)	−0.0074 (3)
S2	0.0349 (4)	0.0507 (4)	0.0281 (3)	−0.0047 (3)	0.0104 (3)	−0.0067 (3)
O1	0.0571 (13)	0.0707 (14)	0.0371 (11)	0.0023 (11)	0.0232 (10)	−0.0102 (10)
O2	0.0387 (11)	0.0718 (14)	0.0482 (12)	0.0218 (10)	−0.0006 (10)	−0.0091 (10)
O3	0.0407 (11)	0.0984 (16)	0.0271 (10)	−0.0047 (11)	0.0013 (9)	−0.0017 (10)
O4	0.0557 (12)	0.0467 (11)	0.0586 (13)	−0.0019 (10)	0.0294 (10)	−0.0167 (10)
O5	0.0474 (12)	0.0781 (15)	0.0391 (11)	−0.0021 (11)	0.0025 (10)	0.0205 (11)
N1	0.0451 (13)	0.0396 (12)	0.0341 (12)	0.0070 (10)	0.0163 (10)	0.0013 (10)
N2	0.0379 (12)	0.0473 (13)	0.0291 (12)	−0.0050 (10)	0.0042 (10)	0.0113 (10)
C1	0.0409 (15)	0.0424 (15)	0.0356 (15)	0.0128 (13)	0.0089 (12)	−0.0048 (12)
C2	0.0467 (18)	0.0586 (19)	0.0480 (18)	0.0087 (15)	0.0062 (15)	0.0005 (15)
C3	0.046 (2)	0.085 (3)	0.074 (2)	0.000 (2)	0.0015 (18)	−0.008 (2)
C4	0.072 (3)	0.066 (3)	0.095 (3)	−0.016 (2)	0.030 (2)	−0.021 (2)
C5	0.093 (3)	0.046 (2)	0.082 (3)	0.002 (2)	0.025 (2)	0.0040 (18)
C6	0.063 (2)	0.0479 (18)	0.0515 (19)	0.0132 (16)	0.0109 (16)	−0.0028 (15)
C7	0.0290 (13)	0.0378 (14)	0.0279 (13)	−0.0014 (11)	0.0067 (10)	−0.0040 (11)
C8	0.0456 (16)	0.0467 (16)	0.0347 (15)	0.0180 (13)	0.0130 (13)	0.0028 (12)
C9	0.0460 (16)	0.0421 (15)	0.0291 (14)	0.0109 (13)	0.0095 (12)	0.0051 (12)
C10	0.0313 (13)	0.0358 (14)	0.0306 (13)	0.0013 (11)	0.0098 (11)	−0.0013 (11)
C11	0.0574 (18)	0.0407 (16)	0.0517 (18)	0.0180 (14)	0.0298 (15)	0.0084 (13)
C12	0.0578 (18)	0.0403 (16)	0.0420 (16)	0.0159 (14)	0.0242 (14)	0.0124 (12)
C13	0.0376 (15)	0.0549 (17)	0.0272 (14)	−0.0049 (13)	0.0109 (12)	0.0006 (12)
C14	0.0526 (19)	0.100 (3)	0.0427 (18)	−0.0311 (19)	0.0083 (15)	0.0000 (17)

Geometric parameters (Å, º) top

S1—O1	1.434 (2)	C7—C12	1.381 (4)
S1—O2	1.420 (2)	C7—C8	1.387 (4)
S1—N1	1.621 (2)	C8—C9	1.381 (4)
S1—C1	1.759 (3)	C9—C10	1.374 (4)
S2—O3	1.4235 (19)	C10—C11	1.380 (4)
S2—O4	1.424 (2)	C11—C12	1.377 (4)
S2—N2	1.652 (2)	C13—C14	1.494 (5)
S2—C10	1.745 (3)	C2—H2	0.9300
O5—C13	1.208 (3)	C3—H3	0.9300
N1—C7	1.408 (3)	C4—H4	0.9300
N2—C13	1.372 (3)	C5—H5	0.9300
N1—H1N	0.8600	C6—H6	0.9300
N2—H2N	0.8600	C8—H8	0.9300
C1—C6	1.375 (4)	C9—H9	0.9300
C1—C2	1.385 (4)	C11—H11	0.9300
C2—C3	1.367 (5)	C12—H12	0.9300
C3—C4	1.388 (6)	C14—H14A	0.9600
C4—C5	1.368 (6)	C14—H14B	0.9600
C5—C6	1.370 (5)	C14—H14C	0.9600

S1···H8	2.8600	C8···C6	3.517 (4)
O1···N2ⁱ	2.922 (3)	C9···O4^xi	3.237 (3)
O2···C6ⁱⁱ	3.242 (4)	C10···O5	3.111 (4)
O2···C5ⁱⁱ	3.407 (4)	C11···O5	3.142 (4)
O2···C8	3.116 (3)	C12···O5^vi	3.402 (3)
O2···C14ⁱⁱⁱ	3.401 (4)	C14···O4^xii	3.193 (4)
O4···O5	2.992 (3)	C14···O2^xiii	3.401 (4)
O4···C8^iv	3.300 (3)	C2···H14Bⁱ	3.0500
O4···C9^iv	3.237 (3)	C2···H11^vi	2.9100
O4···C14^v	3.193 (4)	C5···H14A^x	2.9400
O5···C11	3.142 (4)	C6···H8	3.0200
O5···N1^vi	2.839 (3)	H1N···H12	2.3400
O5···O4	2.992 (3)	H1N···O2^vii	2.9200
O5···C12^vi	3.402 (3)	H1N···O5^vi	2.2500
O5···C10	3.111 (4)	H2···O1	2.7900
O1···H14Cⁱ	2.8100	H2···O4^vi	2.6900
O1···H2	2.7900	H2···H11^vi	2.5200
O1···H2Nⁱ	2.1400	H2···H14Bⁱ	2.5600
O2···H8	2.4900	H2N···H14C	2.2100
O2···H6ⁱⁱ	2.8500	H2N···O1^ix	2.1400
O2···H6	2.5300	H3···O3^xiv	2.8400
O2···H1N^vii	2.9200	H5···H12^xv	2.5400
O2···H14Aⁱⁱⁱ	2.5600	H6···O2	2.5300
O3···H3^viii	2.8400	H6···O2ⁱⁱ	2.8500
O3···H9	2.6900	H8···S1	2.8600
O4···H11	2.5400	H8···O2	2.4900
O4···H14B^v	2.7500	H8···C6	3.0200
O4···H2^vi	2.6900	H8···O4^xi	2.7300
O4···H8^iv	2.7300	H9···O3	2.6900
O4···H9^iv	2.6000	H9···O4^xi	2.6000
O5···H1N^vi	2.2500	H11···O4	2.5400
O5···H12^vi	2.7200	H11···C2^vi	2.9100
N1···O5^vi	2.839 (3)	H11···H2^vi	2.5200
N2···O1^ix	2.922 (3)	H12···H1N	2.3400
C1···C8	3.416 (4)	H12···H5^xvi	2.5400
C4···C5^x	3.534 (6)	H12···O5^vi	2.7200
C4···C4^x	3.515 (7)	H14A···O2^xiii	2.5600
C5···O2ⁱⁱ	3.407 (4)	H14A···C5^x	2.9400
C5···C4^x	3.534 (6)	H14B···O4^xii	2.7500
C6···C8	3.517 (4)	H14B···C2^ix	3.0500
C6···O2ⁱⁱ	3.242 (4)	H14B···H2^ix	2.5600
C8···O2	3.116 (3)	H14C···H2N	2.2100
C8···C1	3.416 (4)	H14C···O1^ix	2.8100
C8···O4^xi	3.300 (3)

O1—S1—O2	119.56 (12)	S2—C10—C11	120.2 (2)
O1—S1—N1	103.74 (11)	C9—C10—C11	119.9 (3)
O1—S1—C1	109.21 (12)	C10—C11—C12	119.5 (3)
O2—S1—N1	109.70 (11)	C7—C12—C11	121.0 (3)
O2—S1—C1	108.39 (13)	O5—C13—C14	123.8 (3)
N1—S1—C1	105.31 (12)	N2—C13—C14	116.0 (2)
O3—S2—O4	119.85 (12)	O5—C13—N2	120.2 (3)
O3—S2—N2	103.58 (11)	C1—C2—H2	121.00
O3—S2—C10	109.54 (13)	C3—C2—H2	120.00
O4—S2—N2	108.64 (11)	C2—C3—H3	120.00
O4—S2—C10	108.16 (13)	C4—C3—H3	120.00
N2—S2—C10	106.25 (12)	C3—C4—H4	120.00
S1—N1—C7	125.64 (18)	C5—C4—H4	120.00
S2—N2—C13	123.70 (18)	C4—C5—H5	120.00
C7—N1—H1N	117.00	C6—C5—H5	120.00
S1—N1—H1N	117.00	C1—C6—H6	121.00
S2—N2—H2N	118.00	C5—C6—H6	121.00
C13—N2—H2N	118.00	C7—C8—H8	120.00
S1—C1—C2	118.7 (2)	C9—C8—H8	120.00
S1—C1—C6	120.0 (2)	C8—C9—H9	120.00
C2—C1—C6	121.3 (3)	C10—C9—H9	120.00
C1—C2—C3	119.0 (3)	C10—C11—H11	120.00
C2—C3—C4	120.1 (3)	C12—C11—H11	120.00
C3—C4—C5	119.9 (3)	C7—C12—H12	119.00
C4—C5—C6	120.8 (3)	C11—C12—H12	120.00
C1—C6—C5	118.9 (3)	C13—C14—H14A	109.00
C8—C7—C12	119.2 (2)	C13—C14—H14B	109.00
N1—C7—C8	123.4 (2)	C13—C14—H14C	109.00
N1—C7—C12	117.4 (2)	H14A—C14—H14B	109.00
C7—C8—C9	119.5 (3)	H14A—C14—H14C	110.00
C8—C9—C10	120.8 (2)	H14B—C14—H14C	109.00
S2—C10—C9	119.9 (2)

O1—S1—N1—C7	171.1 (2)	S2—N2—C13—O5	9.3 (4)
O2—S1—N1—C7	−60.1 (2)	S2—N2—C13—C14	−170.4 (2)
C1—S1—N1—C7	56.4 (2)	S1—C1—C2—C3	−178.6 (2)
O1—S1—C1—C2	−44.2 (3)	C6—C1—C2—C3	−0.8 (4)
O1—S1—C1—C6	137.9 (2)	S1—C1—C6—C5	178.4 (2)
O2—S1—C1—C2	−176.0 (2)	C2—C1—C6—C5	0.5 (5)
O2—S1—C1—C6	6.1 (3)	C1—C2—C3—C4	0.4 (5)
N1—S1—C1—C2	66.7 (3)	C2—C3—C4—C5	0.1 (6)
N1—S1—C1—C6	−111.2 (2)	C3—C4—C5—C6	−0.4 (6)
O3—S2—N2—C13	−179.6 (2)	C4—C5—C6—C1	0.0 (5)
O4—S2—N2—C13	52.0 (2)	N1—C7—C8—C9	−178.4 (2)
C10—S2—N2—C13	−64.2 (2)	C12—C7—C8—C9	1.5 (4)
O3—S2—C10—C9	32.2 (3)	N1—C7—C12—C11	179.7 (3)
O3—S2—C10—C11	−146.2 (2)	C8—C7—C12—C11	−0.2 (4)
O4—S2—C10—C9	164.5 (2)	C7—C8—C9—C10	−1.7 (4)
O4—S2—C10—C11	−14.0 (3)	C8—C9—C10—S2	−177.9 (2)
N2—S2—C10—C9	−79.1 (3)	C8—C9—C10—C11	0.5 (4)
N2—S2—C10—C11	102.5 (2)	S2—C10—C11—C12	179.2 (2)
S1—N1—C7—C8	22.2 (3)	C9—C10—C11—C12	0.8 (4)
S1—N1—C7—C12	−157.8 (2)	C10—C11—C12—C7	−1.0 (4)

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+2, −y, −z; (iii) x+1, y, z; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x+1, −y+1, −z; (vii) −x+2, −y+1, −z; (viii) x+1/2, −y+1/2, z+1/2; (ix) x−1/2, −y+1/2, z+1/2; (x) −x+1, −y, −z; (xi) −x+3/2, y−1/2, −z+1/2; (xii) −x+1/2, y−1/2, −z+1/2; (xiii) x−1, y, z; (xiv) x−1/2, −y+1/2, z−1/2; (xv) x, y−1, z; (xvi) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5^vi	0.86	2.25	2.839 (3)	126
N2—H2N···O1^ix	0.86	2.14	2.922 (3)	151
C8—H8···O2	0.93	2.49	3.116 (3)	125
C9—H9···O4^xi	0.93	2.60	3.237 (3)	126
C14—H14A···O2^xiii	0.96	2.56	3.401 (4)	147

Symmetry codes: (vi) −x+1, −y+1, −z; (ix) x−1/2, −y+1/2, z+1/2; (xi) −x+3/2, y−1/2, −z+1/2; (xiii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₅S₂
M_r	354.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.9316 (9), 9.4828 (8), 17.6490 (17)
β (°)	103.169 (5)
V (Å³)	1618.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.909, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	17674, 4034, 2423
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.128, 1.02
No. of reflections	4034
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (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
N1—H1N···O5ⁱ	0.86	2.25	2.839 (3)	126
N2—H2N···O1ⁱⁱ	0.86	2.14	2.922 (3)	151
C8—H8···O2	0.93	2.49	3.116 (3)	125
C9—H9···O4ⁱⁱⁱ	0.93	2.60	3.237 (3)	126
C14—H14A···O2^iv	0.96	2.56	3.401 (4)	147

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x−1, y, z.

Acknowledgements

MA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042-120556-PS2-275).

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