N-(2,3-Dimethyl­phen­yl)-2-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812042845

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3188

doi:10.1107/S1600536812042845

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N-(2,3-Dimethylphenyl)-2-nitrobenzenesulfonamide

U. Chaithanya,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 11 October 2012; accepted 13 October 2012; online 20 October 2012)

There are two independent molecules in the asymmetric unit of the title compound, C₁₄H₁₄N₂O₄S. The N—H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to the methyl groups in the aniline benzene rings. The molecules are twisted at the S—N bonds with torsion angles of −60.4 (3) and 58.8 (3)° in the two molecules. The dihedral angles between the planes of the sulfonyl and the anilino benzene rings are 53.67 (8) and 56.99 (9)°. The amide H atoms of both molecules are involved in an intramolecular hydrogen bond, generating an S(7) motif. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link like molecules into inversion dimers.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011 ); Bowes et al. (2003 ); Gowda et al. (1994 ); Saeed et al. (2010 ); Shahwar et al. (2012 ), of N-arylsulfonamides, see: Chaithanya et al. (2012 ); Gowda et al. (2002 ) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004 ); Shetty & Gowda (2004 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M_r = 306.33
Triclinic, $[P \overline 1]$
a = 8.0248 (9) Å
b = 12.633 (1) Å
c = 14.711 (1) Å
α = 88.205 (9)°
β = 80.818 (9)°
γ = 82.323 (9)°
V = 1459.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.44 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.902, T_max = 0.945
10389 measured reflections
5936 independent reflections
3935 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.164
S = 1.02
5936 reflections
389 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5ⁱ	0.83 (2)	2.36 (3)	3.056 (4)	142 (3)
N1—H1N⋯O7	0.83 (2)	2.45 (3)	3.011 (4)	126 (3)
N3—H3N⋯O3	0.85 (2)	2.40 (3)	3.012 (4)	129 (3)
N3—H3N⋯O1ⁱⁱ	0.85 (2)	2.41 (3)	3.070 (4)	135 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042845/sj5271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042845/sj5271Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042845/sj5271Isup3.cml

checkCIF report

Comment top

As a part of studying the effect of substituents on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda et al., 1994; Saeed et al., 2010; Shahwar et al., 2012), N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2-methylphenyl)-2-nitrobenzenesulfonamide (I) has been determined (Fig. 1).

The asymmetric unit of the structure contains two independent molecules. The conformation of the N—H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to both the ortho- and meta-methyl groups in the anilino rings, compared to a syn conformation between the N—H bonds and the ortho-nitro groups in the sulfonyl benzene rings or the ortho-methyl group in the anilino ring observed in N-(2-methylphenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012). In (I) the molecules are twisted at the S—N bonds with the torsional angles of -60.37 (30) and 58.81 (34)°, compared to the value of 73.90 (26)° in (II). The dihedral angles between the sulfonyl and anilino rings are 53.67 (8) and 56.99 (9)°, compared to the value of 53.44 (14)° in (II).

The amide H-atoms each form intramolecular H-bonds with the O3 and O7 atoms of the ortho-nitro groups in the sulfonyl benzene rings, generating S(7) motifs (Bernstein et al., 1995). Intermolecular H-bonds from amide H-atoms to sulfonyl oxygen atoms of a similar neighbouring molecule, generate R²₂(8) inversion dimers (Table 1, Fig. 2.)

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Bowes et al. (2003); Gowda et al. (1994); Saeed et al. (2010); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylsulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 2,3-dimethylaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(2,3-dimethylphenyl)-2-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point (138° C) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectrum.

Prism like light pink single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level and intramolecular hydrogen bonds drawn as dashed lines..
	Fig. 2. Crystal packing of the title compound with hydrogen bonds shown as dashed lines.

N-(2,3-Dimethylphenyl)-2-nitrobenzenesulfonamide top

Crystal data top

C₁₄H₁₄N₂O₄S	Z = 4
M_r = 306.33	F(000) = 640
Triclinic, P1	D_x = 1.395 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0248 (9) Å	Cell parameters from 2511 reflections
b = 12.633 (1) Å	θ = 2.6–27.8°
c = 14.711 (1) Å	µ = 0.24 mm⁻¹
α = 88.205 (9)°	T = 293 K
β = 80.818 (9)°	Prism, light pink
γ = 82.323 (9)°	0.44 × 0.40 × 0.24 mm
V = 1459.0 (2) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5936 independent reflections
Radiation source: fine-focus sealed tube	3935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Rotation method data acquisition using ω scans.	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→10
T_min = 0.902, T_max = 0.945	k = −15→15
10389 measured reflections	l = −18→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0599P)² + 1.4896P] where P = (F_o² + 2F_c²)/3
5936 reflections	(Δ/σ)_max = 0.007
389 parameters	Δρ_max = 0.73 e Å⁻³
18 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₄S	γ = 82.323 (9)°
M_r = 306.33	V = 1459.0 (2) Å³
Triclinic, P1	Z = 4
a = 8.0248 (9) Å	Mo Kα radiation
b = 12.633 (1) Å	µ = 0.24 mm⁻¹
c = 14.711 (1) Å	T = 293 K
α = 88.205 (9)°	0.44 × 0.40 × 0.24 mm
β = 80.818 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5936 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3935 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.945	R_int = 0.018
10389 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	18 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.73 e Å⁻³
5936 reflections	Δρ_min = −0.32 e Å⁻³
389 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.59078 (10)	0.35977 (6)	0.38703 (6)	0.0426 (2)
O5	0.5488 (3)	0.47186 (18)	0.37132 (17)	0.0537 (6)
O6	0.5067 (3)	0.2854 (2)	0.34621 (17)	0.0561 (6)
O7	0.8170 (3)	0.4954 (2)	0.47995 (19)	0.0637 (7)
O8	0.9658 (5)	0.5631 (2)	0.3634 (2)	0.0896 (10)
N1	0.5588 (4)	0.3406 (2)	0.49664 (19)	0.0454 (7)
H1N	0.581 (5)	0.391 (2)	0.526 (2)	0.055*
N2	0.9020 (4)	0.4890 (2)	0.4036 (2)	0.0523 (7)
C1	0.8118 (4)	0.3235 (2)	0.3470 (2)	0.0372 (7)
C2	0.9393 (4)	0.3844 (2)	0.3586 (2)	0.0399 (7)
C3	1.1079 (4)	0.3496 (3)	0.3287 (2)	0.0488 (8)
H3	1.1912	0.3911	0.3378	0.059*
C4	1.1527 (4)	0.2528 (3)	0.2851 (3)	0.0533 (9)
H4	1.2668	0.2281	0.2654	0.064*
C5	1.0292 (4)	0.1927 (3)	0.2706 (2)	0.0503 (9)
H5	1.0599	0.1279	0.2402	0.060*
C6	0.8602 (4)	0.2276 (3)	0.3009 (2)	0.0437 (8)
H6	0.7776	0.1864	0.2904	0.052*
C7	0.5971 (5)	0.2352 (3)	0.5374 (2)	0.0476 (8)
C8	0.4693 (5)	0.1718 (3)	0.5629 (2)	0.0523 (9)
C9	0.5109 (6)	0.0721 (3)	0.6048 (2)	0.0582 (10)
C10	0.6782 (7)	0.0421 (3)	0.6172 (3)	0.0748 (13)
H10	0.7065	−0.0243	0.6438	0.090*
C11	0.8033 (6)	0.1053 (4)	0.5925 (3)	0.0781 (13)
H11	0.9138	0.0822	0.6028	0.094*
C12	0.7653 (5)	0.2033 (3)	0.5522 (3)	0.0620 (10)
H12	0.8491	0.2475	0.5351	0.074*
C13	0.2916 (5)	0.2082 (3)	0.5485 (3)	0.0708 (12)
H13A	0.2840	0.2797	0.5239	0.106*
H13B	0.2167	0.2069	0.6063	0.106*
H13C	0.2591	0.1615	0.5061	0.106*
C14	0.3784 (7)	0.0013 (3)	0.6390 (3)	0.0865 (15)
H14A	0.2969	0.0369	0.6869	0.130*
H14B	0.4316	−0.0640	0.6627	0.130*
H14C	0.3218	−0.0142	0.5892	0.130*
S2	0.02193 (11)	0.85930 (7)	0.11713 (6)	0.0481 (2)
O1	−0.0211 (3)	0.97056 (19)	0.13593 (18)	0.0594 (7)
O2	−0.0880 (3)	0.7857 (2)	0.15857 (19)	0.0648 (7)
O3	0.3080 (3)	0.9908 (2)	0.0211 (2)	0.0657 (7)
O4	0.3890 (4)	1.0547 (2)	0.1388 (2)	0.0822 (9)
N3	0.0419 (4)	0.8477 (2)	0.0069 (2)	0.0509 (7)
H3N	0.091 (4)	0.897 (2)	−0.022 (2)	0.061*
N4	0.3487 (4)	0.9821 (2)	0.0977 (2)	0.0534 (8)
C15	0.2213 (4)	0.8163 (3)	0.1527 (2)	0.0434 (8)
C16	0.3568 (4)	0.8767 (3)	0.1430 (2)	0.0447 (8)
C17	0.5065 (5)	0.8400 (3)	0.1742 (3)	0.0572 (10)
H17	0.5952	0.8815	0.1671	0.069*
C18	0.5242 (5)	0.7411 (3)	0.2163 (3)	0.0650 (11)
H18	0.6259	0.7152	0.2368	0.078*
C19	0.3936 (6)	0.6811 (3)	0.2282 (3)	0.0643 (11)
H19	0.4065	0.6146	0.2570	0.077*
C20	0.2406 (5)	0.7184 (3)	0.1975 (2)	0.0543 (9)
H20	0.1511	0.6774	0.2071	0.065*
C21	0.0992 (6)	0.7447 (3)	−0.0398 (3)	0.0652 (8)
C22	−0.0109 (7)	0.6796 (3)	−0.0580 (3)	0.0756 (10)
C23	0.0528 (8)	0.5828 (3)	−0.1033 (3)	0.0824 (11)
C24	0.2297 (9)	0.5572 (4)	−0.1317 (3)	0.1028 (14)
H24	0.2724	0.4932	−0.1617	0.123*
C25	0.3376 (9)	0.6261 (5)	−0.1152 (4)	0.1085 (16)
H25	0.4535	0.6084	−0.1358	0.130*
C26	0.2839 (7)	0.7197 (4)	−0.0697 (3)	0.0804 (10)
H26	0.3598	0.7654	−0.0583	0.096*
C27	−0.1925 (7)	0.7109 (4)	−0.0284 (3)	0.0878 (12)
H27A	−0.2364	0.6588	0.0146	0.132*
H27B	−0.2505	0.7151	−0.0809	0.132*
H27C	−0.2102	0.7794	0.0006	0.132*
C28	−0.0634 (10)	0.5087 (4)	−0.1236 (4)	0.124 (2)
H28A	−0.1409	0.5443	−0.1616	0.186*
H28B	−0.1265	0.4858	−0.0670	0.186*
H28C	0.0015	0.4477	−0.1554	0.186*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0351 (4)	0.0445 (5)	0.0468 (5)	0.0025 (3)	−0.0089 (3)	0.0013 (4)
O5	0.0494 (14)	0.0469 (14)	0.0596 (16)	0.0113 (11)	−0.0094 (11)	0.0082 (11)
O6	0.0397 (13)	0.0690 (16)	0.0628 (16)	−0.0087 (12)	−0.0150 (11)	−0.0083 (13)
O7	0.0597 (16)	0.0675 (18)	0.0631 (18)	−0.0091 (13)	−0.0023 (14)	−0.0225 (14)
O8	0.121 (3)	0.0455 (16)	0.096 (2)	−0.0205 (17)	0.009 (2)	−0.0026 (16)
N1	0.0487 (16)	0.0413 (16)	0.0442 (17)	−0.0036 (13)	−0.0029 (13)	−0.0016 (12)
N2	0.0528 (18)	0.0457 (18)	0.059 (2)	−0.0038 (14)	−0.0128 (16)	−0.0060 (15)
C1	0.0358 (16)	0.0378 (17)	0.0368 (17)	0.0033 (13)	−0.0091 (13)	0.0014 (13)
C2	0.0436 (18)	0.0376 (17)	0.0385 (18)	−0.0004 (14)	−0.0108 (14)	−0.0010 (13)
C3	0.0368 (18)	0.054 (2)	0.058 (2)	−0.0060 (15)	−0.0127 (16)	−0.0012 (17)
C4	0.0373 (19)	0.059 (2)	0.060 (2)	0.0084 (16)	−0.0090 (16)	−0.0070 (18)
C5	0.050 (2)	0.044 (2)	0.054 (2)	0.0068 (16)	−0.0076 (17)	−0.0082 (16)
C6	0.0427 (18)	0.0430 (19)	0.0464 (19)	−0.0058 (15)	−0.0099 (15)	−0.0005 (15)
C7	0.060 (2)	0.0387 (18)	0.0400 (19)	−0.0022 (16)	0.0001 (16)	−0.0016 (14)
C8	0.058 (2)	0.048 (2)	0.046 (2)	−0.0024 (17)	0.0030 (17)	−0.0060 (16)
C9	0.084 (3)	0.045 (2)	0.042 (2)	−0.005 (2)	−0.0016 (19)	−0.0009 (16)
C10	0.102 (4)	0.060 (3)	0.056 (3)	0.001 (3)	−0.003 (2)	0.006 (2)
C11	0.072 (3)	0.086 (3)	0.070 (3)	0.012 (3)	−0.015 (2)	0.013 (2)
C12	0.066 (3)	0.064 (3)	0.051 (2)	0.005 (2)	−0.0094 (19)	0.0092 (19)
C13	0.062 (3)	0.067 (3)	0.082 (3)	−0.011 (2)	−0.006 (2)	−0.003 (2)
C14	0.123 (4)	0.060 (3)	0.075 (3)	−0.030 (3)	0.001 (3)	0.004 (2)
S2	0.0398 (5)	0.0510 (5)	0.0532 (5)	−0.0027 (4)	−0.0099 (4)	0.0027 (4)
O1	0.0505 (15)	0.0545 (15)	0.0684 (17)	0.0094 (12)	−0.0072 (12)	−0.0072 (13)
O2	0.0489 (15)	0.0765 (18)	0.0721 (18)	−0.0202 (13)	−0.0129 (13)	0.0186 (14)
O3	0.0609 (17)	0.0663 (18)	0.0726 (19)	−0.0141 (13)	−0.0165 (15)	0.0145 (14)
O4	0.096 (2)	0.0583 (18)	0.093 (2)	−0.0181 (16)	−0.0072 (18)	−0.0174 (16)
N3	0.0561 (19)	0.0487 (15)	0.0506 (18)	−0.0072 (13)	−0.0181 (15)	0.0080 (12)
N4	0.0405 (17)	0.0504 (19)	0.066 (2)	−0.0044 (14)	0.0013 (15)	−0.0054 (16)
C15	0.0411 (18)	0.0443 (19)	0.0436 (19)	0.0023 (15)	−0.0087 (14)	−0.0044 (15)
C16	0.0402 (18)	0.0479 (19)	0.0440 (19)	0.0029 (15)	−0.0058 (14)	−0.0096 (15)
C17	0.041 (2)	0.065 (2)	0.064 (2)	0.0031 (17)	−0.0093 (17)	−0.017 (2)
C18	0.056 (2)	0.077 (3)	0.059 (2)	0.014 (2)	−0.021 (2)	−0.009 (2)
C19	0.075 (3)	0.056 (2)	0.060 (3)	0.012 (2)	−0.022 (2)	0.0044 (19)
C20	0.060 (2)	0.052 (2)	0.051 (2)	−0.0042 (18)	−0.0131 (18)	0.0023 (17)
C21	0.0985 (19)	0.0527 (17)	0.047 (2)	−0.0022 (15)	−0.0262 (19)	0.0070 (15)
C22	0.1152 (19)	0.056 (2)	0.060 (3)	−0.0115 (17)	−0.027 (2)	0.0067 (16)
C23	0.160 (3)	0.0523 (19)	0.038 (2)	−0.012 (2)	−0.030 (2)	0.0094 (15)
C24	0.167 (4)	0.073 (3)	0.061 (3)	0.011 (2)	−0.017 (3)	−0.002 (2)
C25	0.130 (3)	0.100 (4)	0.084 (4)	0.018 (2)	−0.008 (3)	−0.019 (3)
C26	0.0994 (19)	0.082 (3)	0.056 (3)	0.011 (2)	−0.019 (2)	0.000 (2)
C27	0.1075 (19)	0.092 (3)	0.068 (3)	−0.023 (2)	−0.019 (2)	0.019 (2)
C28	0.210 (7)	0.094 (4)	0.077 (4)	−0.045 (4)	−0.030 (4)	0.016 (3)

Geometric parameters (Å, º) top

S1—O6	1.426 (2)	S2—O2	1.424 (3)
S1—O5	1.431 (2)	S2—O1	1.427 (2)
S1—N1	1.608 (3)	S2—N3	1.613 (3)
S1—C1	1.780 (3)	S2—C15	1.774 (3)
O7—N2	1.216 (4)	O3—N4	1.220 (4)
O8—N2	1.218 (4)	O4—N4	1.219 (4)
N1—C7	1.458 (4)	N3—C21	1.474 (5)
N1—H1N	0.829 (18)	N3—H3N	0.846 (18)
N2—C2	1.470 (4)	N4—C16	1.469 (4)
C1—C6	1.385 (4)	C15—C20	1.385 (5)
C1—C2	1.394 (4)	C15—C16	1.396 (5)
C2—C3	1.371 (4)	C16—C17	1.372 (5)
C3—C4	1.377 (5)	C17—C18	1.377 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.373 (5)	C18—C19	1.360 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.375 (5)	C19—C20	1.394 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.382 (5)	C21—C22	1.346 (6)
C7—C12	1.405 (5)	C21—C26	1.472 (7)
C8—C9	1.409 (5)	C22—C23	1.406 (6)
C8—C13	1.485 (5)	C22—C27	1.457 (7)
C9—C10	1.384 (6)	C23—C24	1.411 (8)
C9—C14	1.495 (6)	C23—C28	1.475 (7)
C10—C11	1.363 (6)	C24—C25	1.360 (8)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.374 (5)	C25—C26	1.361 (6)
C11—H11	0.9300	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600

O6—S1—O5	119.75 (15)	O2—S2—O1	119.82 (16)
O6—S1—N1	107.92 (16)	O2—S2—N3	107.96 (17)
O5—S1—N1	106.93 (14)	O1—S2—N3	106.38 (16)
O6—S1—C1	105.38 (14)	O2—S2—C15	105.30 (16)
O5—S1—C1	108.58 (15)	O1—S2—C15	108.09 (15)
N1—S1—C1	107.78 (15)	N3—S2—C15	108.98 (16)
C7—N1—S1	121.6 (2)	C21—N3—S2	122.4 (2)
C7—N1—H1N	114 (3)	C21—N3—H3N	111 (3)
S1—N1—H1N	113 (3)	S2—N3—H3N	112 (3)
O7—N2—O8	124.1 (3)	O4—N4—O3	124.5 (3)
O7—N2—C2	118.5 (3)	O4—N4—C16	116.9 (3)
O8—N2—C2	117.3 (3)	O3—N4—C16	118.5 (3)
C6—C1—C2	117.7 (3)	C20—C15—C16	117.8 (3)
C6—C1—S1	117.5 (2)	C20—C15—S2	117.6 (3)
C2—C1—S1	124.8 (2)	C16—C15—S2	124.5 (3)
C3—C2—C1	121.6 (3)	C17—C16—C15	121.7 (3)
C3—C2—N2	116.0 (3)	C17—C16—N4	116.2 (3)
C1—C2—N2	122.4 (3)	C15—C16—N4	122.1 (3)
C2—C3—C4	119.4 (3)	C16—C17—C18	119.4 (4)
C2—C3—H3	120.3	C16—C17—H17	120.3
C4—C3—H3	120.3	C18—C17—H17	120.3
C5—C4—C3	120.1 (3)	C19—C18—C17	120.3 (4)
C5—C4—H4	120.0	C19—C18—H18	119.8
C3—C4—H4	120.0	C17—C18—H18	119.8
C4—C5—C6	120.4 (3)	C18—C19—C20	120.6 (4)
C4—C5—H5	119.8	C18—C19—H19	119.7
C6—C5—H5	119.8	C20—C19—H19	119.7
C5—C6—C1	120.8 (3)	C15—C20—C19	120.2 (4)
C5—C6—H6	119.6	C15—C20—H20	119.9
C1—C6—H6	119.6	C19—C20—H20	119.9
C8—C7—C12	122.1 (3)	C22—C21—C26	121.8 (4)
C8—C7—N1	120.2 (3)	C22—C21—N3	122.2 (4)
C12—C7—N1	117.6 (3)	C26—C21—N3	115.9 (4)
C7—C8—C9	118.3 (4)	C21—C22—C23	119.1 (5)
C7—C8—C13	121.3 (3)	C21—C22—C27	118.8 (4)
C9—C8—C13	120.4 (4)	C23—C22—C27	122.0 (5)
C10—C9—C8	118.2 (4)	C22—C23—C24	119.7 (5)
C10—C9—C14	120.1 (4)	C22—C23—C28	120.8 (6)
C8—C9—C14	121.6 (4)	C24—C23—C28	119.4 (5)
C11—C10—C9	123.2 (4)	C25—C24—C23	119.9 (5)
C11—C10—H10	118.4	C25—C24—H24	120.0
C9—C10—H10	118.4	C23—C24—H24	120.0
C10—C11—C12	119.6 (4)	C24—C25—C26	123.0 (6)
C10—C11—H11	120.2	C24—C25—H25	118.5
C12—C11—H11	120.2	C26—C25—H25	118.5
C11—C12—C7	118.6 (4)	C25—C26—C21	116.3 (5)
C11—C12—H12	120.7	C25—C26—H26	121.8
C7—C12—H12	120.7	C21—C26—H26	121.8
C8—C13—H13A	109.5	C22—C27—H27A	109.5
C8—C13—H13B	109.5	C22—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C8—C13—H13C	109.5	C22—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C9—C14—H14A	109.5	C23—C28—H28A	109.5
C9—C14—H14B	109.5	C23—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C9—C14—H14C	109.5	C23—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5

O6—S1—N1—C7	53.0 (3)	O2—S2—N3—C21	−55.1 (3)
O5—S1—N1—C7	−177.0 (3)	O1—S2—N3—C21	175.1 (3)
C1—S1—N1—C7	−60.4 (3)	C15—S2—N3—C21	58.8 (3)
O6—S1—C1—C6	−10.1 (3)	O2—S2—C15—C20	9.5 (3)
O5—S1—C1—C6	−139.6 (2)	O1—S2—C15—C20	138.7 (3)
N1—S1—C1—C6	104.9 (3)	N3—S2—C15—C20	−106.1 (3)
O6—S1—C1—C2	169.9 (3)	O2—S2—C15—C16	−166.9 (3)
O5—S1—C1—C2	40.5 (3)	O1—S2—C15—C16	−37.7 (3)
N1—S1—C1—C2	−75.0 (3)	N3—S2—C15—C16	77.5 (3)
C6—C1—C2—C3	−2.3 (5)	C20—C15—C16—C17	1.8 (5)
S1—C1—C2—C3	177.7 (3)	S2—C15—C16—C17	178.2 (3)
C6—C1—C2—N2	177.9 (3)	C20—C15—C16—N4	−179.2 (3)
S1—C1—C2—N2	−2.1 (4)	S2—C15—C16—N4	−2.8 (5)
O7—N2—C2—C3	−126.1 (3)	O4—N4—C16—C17	−50.8 (4)
O8—N2—C2—C3	50.4 (4)	O3—N4—C16—C17	126.9 (3)
O7—N2—C2—C1	53.8 (4)	O4—N4—C16—C15	130.2 (3)
O8—N2—C2—C1	−129.7 (4)	O3—N4—C16—C15	−52.2 (4)
C1—C2—C3—C4	0.7 (5)	C15—C16—C17—C18	0.0 (5)
N2—C2—C3—C4	−179.4 (3)	N4—C16—C17—C18	−179.1 (3)
C2—C3—C4—C5	1.0 (5)	C16—C17—C18—C19	−1.1 (6)
C3—C4—C5—C6	−1.1 (6)	C17—C18—C19—C20	0.4 (6)
C4—C5—C6—C1	−0.4 (5)	C16—C15—C20—C19	−2.4 (5)
C2—C1—C6—C5	2.1 (5)	S2—C15—C20—C19	−179.1 (3)
S1—C1—C6—C5	−177.9 (3)	C18—C19—C20—C15	1.4 (6)
S1—N1—C7—C8	−97.5 (3)	S2—N3—C21—C22	92.1 (4)
S1—N1—C7—C12	84.6 (4)	S2—N3—C21—C26	−90.9 (4)
C12—C7—C8—C9	−0.1 (5)	C26—C21—C22—C23	2.8 (6)
N1—C7—C8—C9	−177.9 (3)	N3—C21—C22—C23	179.6 (3)
C12—C7—C8—C13	178.6 (3)	C26—C21—C22—C27	−178.3 (4)
N1—C7—C8—C13	0.8 (5)	N3—C21—C22—C27	−1.6 (6)
C7—C8—C9—C10	−0.9 (5)	C21—C22—C23—C24	−2.1 (6)
C13—C8—C9—C10	−179.6 (4)	C27—C22—C23—C24	179.1 (4)
C7—C8—C9—C14	176.7 (3)	C21—C22—C23—C28	179.3 (4)
C13—C8—C9—C14	−2.0 (6)	C27—C22—C23—C28	0.5 (6)
C8—C9—C10—C11	1.3 (6)	C22—C23—C24—C25	0.0 (7)
C14—C9—C10—C11	−176.3 (4)	C28—C23—C24—C25	178.6 (5)
C9—C10—C11—C12	−0.8 (7)	C23—C24—C25—C26	1.6 (8)
C10—C11—C12—C7	−0.2 (6)	C24—C25—C26—C21	−0.9 (8)
C8—C7—C12—C11	0.6 (6)	C22—C21—C26—C25	−1.3 (6)
N1—C7—C12—C11	178.5 (3)	N3—C21—C26—C25	−178.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5ⁱ	0.83 (2)	2.36 (3)	3.056 (4)	142 (3)
N1—H1N···O7	0.83 (2)	2.45 (3)	3.011 (4)	126 (3)
N3—H3N···O3	0.85 (2)	2.40 (3)	3.012 (4)	129 (3)
N3—H3N···O1ⁱⁱ	0.85 (2)	2.41 (3)	3.070 (4)	135 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₄S
M_r	306.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.0248 (9), 12.633 (1), 14.711 (1)
α, β, γ (°)	88.205 (9), 80.818 (9), 82.323 (9)
V (Å³)	1459.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.44 × 0.40 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.902, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	10389, 5936, 3935
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.164, 1.02
No. of reflections	5936
No. of parameters	389
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5ⁱ	0.829 (18)	2.36 (3)	3.056 (4)	142 (3)
N1—H1N···O7	0.829 (18)	2.45 (3)	3.011 (4)	126 (3)
N3—H3N···O3	0.846 (18)	2.40 (3)	3.012 (4)	129 (3)
N3—H3N···O1ⁱⁱ	0.846 (18)	2.41 (3)	3.070 (4)	135 (3)

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

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to Faculty.

References

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