N-(3-Methyl­benzo­yl)benzene­sulfonamide

Suchetan, P.A.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812013931

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1327

doi:10.1107/S1600536812013931

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N-(3-Methylbenzoyl)benzenesulfonamide

P. A. Suchetan,^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 29 March 2012; accepted 30 March 2012; online 6 April 2012)

The asymmetric unit of the title compound, C₁₄H₁₃NO₃S, contains three independent molecules in which the dihedral angles between the sulfonyl and benzoyl benzene rings are 83.3 (2), 84.4 (2) and 87.6 (2)°. In the crystal, molecules are linked into chains running along the a axis via N—H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000 , 2007 ), on N-(substitutedbenzoyl)-arylsulfonamides, see: Gowda et al. (2009 ), on N-chloroarylamides, see: Jyothi & Gowda (2004 ) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M_r = 275.31
Monoclinic, P 2₁ /c
a = 11.6028 (8) Å
b = 35.100 (3) Å
c = 10.4886 (8) Å
β = 100.920 (7)°
V = 4194.2 (6) Å³
Z = 12
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.46 × 0.30 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a 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 = 0.900, T_max = 0.991
15537 measured reflections
7317 independent reflections
4440 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.097
wR(F²) = 0.146
S = 1.29
7317 reflections
526 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O7ⁱ	0.85 (2)	2.04 (2)	2.864 (5)	164 (5)
N2—H2N⋯O2ⁱⁱ	0.86 (2)	2.15 (3)	2.920 (5)	150 (5)
N3—H3N⋯O6	0.85 (2)	2.05 (2)	2.891 (5)	172 (5)
Symmetry codes: (i) x-1, y, z+1; (ii) x, y, z-1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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/S1600536812013931/bt5866sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013931/bt5866Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013931/bt5866Isup3.cml

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary and prostate) in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2007), N-(substitutedbenzoyl)-arylsulfonamides (Gowda et al., 2009), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-methylbenzoyl)benzenesulfonamide has been determined (Fig.1).

The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to that observed in N-(3-chlorobenzoyl)benzenesulfonamide (I)(Gowda et al., 2009).

In the title compound, the dihedral angles between the sulfonyl benzene rings and the —SO₂—NH—C—O segments are 76.6 (2)°, 82.2 (2)° and 78.4 (2)°, compared to the value of 79.6 (1)° in (I).

The dihedral angles between the sulfonyl and the benzoyl benzene rings are 83.3 (2)°, 84.4 (2)° and 87.6 (2)°, compared to the value of 89.3 (1)° in (I).

The packing of molecules linked by of N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000, 2007), on N-(substitutedbenzoyl)-arylsulfonamides, see: Gowda et al. (2009), on N-chloroarylamides, see: Jyothi & Gowda (2004) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental top

The title compound was prepared by refluxing a mixture of 3-methylbenzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point.

Plate like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of the solvent from its toluene solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (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. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-(3-Methylbenzoyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₃NO₃S	F(000) = 1728
M_r = 275.31	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3245 reflections
a = 11.6028 (8) Å	θ = 2.6–27.9°
b = 35.100 (3) Å	µ = 0.23 mm⁻¹
c = 10.4886 (8) Å	T = 293 K
β = 100.920 (7)°	Plate, colourless
V = 4194.2 (6) Å³	0.46 × 0.30 × 0.04 mm
Z = 12

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	7317 independent reflections
Radiation source: fine-focus sealed tube	4440 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Rotation method data acquisition using ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→13
T_min = 0.900, T_max = 0.991	k = −41→28
15537 measured reflections	l = −12→12

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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	w = 1/[σ²(F_o²) + (0.P)² + 7.5834P] where P = (F_o² + 2F_c²)/3
7317 reflections	(Δ/σ)_max < 0.001
526 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₄H₁₃NO₃S	V = 4194.2 (6) Å³
M_r = 275.31	Z = 12
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6028 (8) Å	µ = 0.23 mm⁻¹
b = 35.100 (3) Å	T = 293 K
c = 10.4886 (8) Å	0.46 × 0.30 × 0.04 mm
β = 100.920 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	7317 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	4440 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.991	R_int = 0.045
15537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.097	3 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	Δρ_max = 0.30 e Å⁻³
7317 reflections	Δρ_min = −0.33 e Å⁻³
526 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.1661 (4)	0.20368 (14)	0.9680 (5)	0.0404 (13)
C2	0.2356 (5)	0.23047 (17)	0.9252 (6)	0.0666 (18)
H2	0.3169	0.2286	0.9466	0.080*
C3	0.1831 (7)	0.2603 (2)	0.8495 (7)	0.089 (2)
H3	0.2294	0.2785	0.8192	0.107*
C4	0.0632 (7)	0.2631 (2)	0.8189 (7)	0.088 (2)
H4	0.0282	0.2833	0.7686	0.105*
C5	−0.0049 (6)	0.2361 (2)	0.8625 (7)	0.078 (2)
H5	−0.0863	0.2380	0.8410	0.094*
C6	0.0452 (5)	0.20613 (16)	0.9377 (6)	0.0565 (16)
H6	−0.0014	0.1879	0.9675	0.068*
C7	0.2962 (5)	0.12424 (15)	0.8764 (5)	0.0456 (14)
C8	0.2903 (4)	0.08623 (14)	0.8128 (5)	0.0398 (13)
C9	0.3140 (5)	0.08350 (17)	0.6894 (6)	0.0600 (17)
H9	0.3306	0.1055	0.6470	0.072*
C10	0.3136 (6)	0.04891 (19)	0.6271 (6)	0.0654 (18)
C11	0.2922 (5)	0.01670 (18)	0.6924 (7)	0.0638 (18)
H11	0.2939	−0.0069	0.6528	0.077*
C12	0.2686 (5)	0.01875 (17)	0.8150 (7)	0.0646 (18)
H12	0.2539	−0.0034	0.8579	0.078*
C13	0.2665 (5)	0.05358 (15)	0.8749 (6)	0.0518 (15)
H13	0.2488	0.0550	0.9576	0.062*
C14	0.3375 (9)	0.0467 (2)	0.4911 (7)	0.142 (4)
H14A	0.4206	0.0455	0.4943	0.170*
H14B	0.3059	0.0688	0.4432	0.170*
H14C	0.3011	0.0242	0.4492	0.170*
N1	0.2269 (4)	0.12842 (11)	0.9691 (4)	0.0408 (11)
H1N	0.172 (3)	0.1133 (11)	0.979 (5)	0.049*
O1	0.1566 (3)	0.15579 (10)	1.1538 (3)	0.0563 (10)
O2	0.3507 (3)	0.17572 (10)	1.1137 (4)	0.0588 (11)
O3	0.3556 (4)	0.15030 (11)	0.8490 (4)	0.0723 (13)
S1	0.23040 (12)	0.16583 (4)	1.06531 (14)	0.0439 (4)
C15	0.5844 (5)	0.12158 (15)	0.3849 (5)	0.0477 (14)
C16	0.4896 (5)	0.14058 (17)	0.4163 (6)	0.0617 (17)
H16	0.4226	0.1448	0.3536	0.074*
C17	0.4954 (7)	0.1532 (2)	0.5411 (8)	0.083 (2)
H17	0.4322	0.1662	0.5634	0.099*
C18	0.5945 (8)	0.1468 (2)	0.6327 (7)	0.095 (3)
H18	0.5977	0.1552	0.7174	0.113*
C19	0.6884 (7)	0.1283 (2)	0.6011 (7)	0.099 (3)
H19	0.7554	0.1242	0.6640	0.118*
C20	0.6843 (6)	0.11550 (19)	0.4757 (6)	0.074 (2)
H20	0.7482	0.1030	0.4533	0.089*
C21	0.6831 (4)	0.16510 (14)	0.1471 (5)	0.0372 (12)
C22	0.6719 (4)	0.19969 (14)	0.0646 (5)	0.0373 (12)
C23	0.5861 (4)	0.20471 (14)	−0.0453 (5)	0.0399 (13)
H23	0.5313	0.1855	−0.0707	0.048*
C24	0.5803 (5)	0.23784 (17)	−0.1181 (5)	0.0515 (15)
C25	0.6612 (6)	0.26632 (17)	−0.0762 (7)	0.0692 (19)
H25	0.6570	0.2891	−0.1223	0.083*
C26	0.7470 (7)	0.26166 (19)	0.0314 (7)	0.082 (2)
H26	0.8012	0.2810	0.0574	0.098*
C27	0.7531 (5)	0.22833 (17)	0.1012 (6)	0.0609 (17)
H27	0.8123	0.2250	0.1736	0.073*
C28	0.4903 (6)	0.2429 (2)	−0.2401 (6)	0.083 (2)
H28A	0.4304	0.2238	−0.2437	0.100*
H28B	0.5273	0.2403	−0.3142	0.100*
H28C	0.4556	0.2677	−0.2405	0.100*
N2	0.5845 (4)	0.14267 (12)	0.1351 (4)	0.0414 (11)
H2N	0.516 (2)	0.1500 (13)	0.099 (4)	0.050*
O4	0.4570 (3)	0.09120 (10)	0.1793 (4)	0.0667 (12)
O5	0.6724 (4)	0.08030 (10)	0.2222 (4)	0.0646 (12)
O6	0.7731 (3)	0.15704 (10)	0.2228 (3)	0.0512 (10)
S2	0.57382 (13)	0.10423 (4)	0.22610 (14)	0.0492 (4)
C29	0.8038 (4)	0.06031 (14)	−0.0737 (4)	0.0378 (13)
C30	0.8412 (5)	0.02571 (15)	−0.1099 (5)	0.0462 (14)
H30	0.9209	0.0204	−0.1005	0.055*
C31	0.7585 (6)	−0.00106 (17)	−0.1605 (5)	0.0592 (16)
H31	0.7826	−0.0246	−0.1867	0.071*
C32	0.6408 (6)	0.00656 (19)	−0.1728 (6)	0.0678 (19)
H32	0.5857	−0.0118	−0.2066	0.081*
C33	0.6045 (5)	0.04131 (19)	−0.1353 (6)	0.0711 (19)
H33	0.5247	0.0463	−0.1432	0.085*
C34	0.6850 (5)	0.06871 (17)	−0.0862 (5)	0.0548 (16)
H34	0.6607	0.0924	−0.0618	0.066*
C35	0.9608 (4)	0.06864 (16)	0.2280 (5)	0.0430 (14)
C36	0.9756 (4)	0.07833 (17)	0.3685 (5)	0.0479 (14)
C37	1.0054 (5)	0.11455 (18)	0.4134 (5)	0.0580 (17)
H37	1.0161	0.1336	0.3550	0.070*
C38	1.0198 (6)	0.1230 (2)	0.5453 (6)	0.076 (2)
C39	1.0025 (6)	0.0938 (3)	0.6276 (7)	0.090 (3)
H39	1.0115	0.0988	0.7160	0.108*
C40	0.9728 (6)	0.0580 (3)	0.5849 (7)	0.092 (3)
H40	0.9613	0.0391	0.6433	0.110*
C41	0.9598 (5)	0.04983 (19)	0.4545 (7)	0.0698 (19)
H41	0.9405	0.0253	0.4245	0.084*
C42	1.0549 (8)	0.1623 (2)	0.5946 (7)	0.138 (4)
H42A	1.0151	0.1809	0.5347	0.166*
H42B	1.1382	0.1653	0.6025	0.166*
H42C	1.0337	0.1659	0.6779	0.166*
N3	0.9179 (4)	0.09775 (12)	0.1442 (4)	0.0393 (10)
H3N	0.881 (4)	0.1165 (10)	0.167 (5)	0.047*
O7	1.0178 (3)	0.08427 (12)	−0.0409 (4)	0.0700 (13)
O8	0.8578 (4)	0.13197 (11)	−0.0578 (3)	0.0686 (12)
O9	0.9847 (4)	0.03767 (11)	0.1896 (4)	0.0700 (12)
S3	0.90607 (13)	0.09578 (4)	−0.01381 (13)	0.0471 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (3)	0.037 (3)	0.045 (3)	0.006 (3)	0.006 (3)	−0.006 (3)
C2	0.050 (4)	0.057 (4)	0.094 (5)	0.002 (3)	0.019 (4)	0.014 (4)
C3	0.078 (6)	0.070 (5)	0.123 (7)	0.004 (4)	0.030 (5)	0.046 (5)
C4	0.084 (6)	0.074 (5)	0.101 (6)	0.019 (4)	0.008 (5)	0.037 (5)
C5	0.058 (4)	0.079 (5)	0.092 (6)	0.016 (4)	−0.002 (4)	0.017 (4)
C6	0.051 (4)	0.051 (4)	0.066 (4)	0.001 (3)	0.008 (3)	0.007 (3)
C7	0.042 (3)	0.040 (3)	0.055 (4)	−0.005 (3)	0.011 (3)	−0.003 (3)
C8	0.030 (3)	0.037 (3)	0.052 (4)	−0.007 (2)	0.007 (3)	−0.006 (3)
C9	0.074 (4)	0.054 (4)	0.058 (4)	−0.011 (3)	0.028 (3)	−0.002 (3)
C10	0.082 (5)	0.066 (5)	0.052 (4)	−0.009 (4)	0.023 (4)	−0.022 (4)
C11	0.067 (4)	0.048 (4)	0.077 (5)	−0.009 (3)	0.014 (4)	−0.024 (4)
C12	0.077 (5)	0.039 (4)	0.082 (5)	−0.003 (3)	0.024 (4)	−0.004 (4)
C13	0.057 (4)	0.044 (4)	0.057 (4)	0.000 (3)	0.018 (3)	−0.003 (3)
C14	0.239 (11)	0.116 (7)	0.092 (7)	−0.016 (8)	0.085 (7)	−0.037 (6)
N1	0.038 (3)	0.034 (3)	0.052 (3)	−0.010 (2)	0.014 (2)	−0.008 (2)
O1	0.078 (3)	0.050 (2)	0.045 (2)	0.006 (2)	0.021 (2)	−0.0014 (19)
O2	0.046 (2)	0.048 (2)	0.072 (3)	0.0000 (19)	−0.015 (2)	−0.012 (2)
O3	0.078 (3)	0.047 (2)	0.104 (4)	−0.026 (2)	0.049 (3)	−0.018 (2)
S1	0.0458 (9)	0.0375 (8)	0.0454 (9)	0.0031 (7)	0.0012 (7)	−0.0060 (7)
C15	0.060 (4)	0.037 (3)	0.051 (4)	0.006 (3)	0.023 (3)	0.010 (3)
C16	0.068 (4)	0.063 (4)	0.057 (4)	0.006 (3)	0.020 (3)	0.006 (3)
C17	0.093 (6)	0.085 (5)	0.082 (6)	0.011 (5)	0.045 (5)	−0.002 (5)
C18	0.132 (7)	0.110 (7)	0.052 (5)	0.005 (6)	0.045 (5)	−0.006 (5)
C19	0.105 (6)	0.143 (8)	0.046 (5)	0.024 (6)	0.010 (4)	0.006 (5)
C20	0.075 (5)	0.099 (6)	0.047 (4)	0.021 (4)	0.009 (4)	0.014 (4)
C21	0.043 (3)	0.036 (3)	0.034 (3)	0.004 (3)	0.010 (3)	−0.008 (3)
C22	0.034 (3)	0.039 (3)	0.040 (3)	−0.003 (2)	0.010 (2)	−0.004 (3)
C23	0.046 (3)	0.031 (3)	0.045 (3)	−0.002 (3)	0.013 (3)	0.001 (3)
C24	0.054 (4)	0.053 (4)	0.051 (4)	0.013 (3)	0.020 (3)	0.013 (3)
C25	0.097 (6)	0.041 (4)	0.078 (5)	0.000 (4)	0.038 (4)	0.015 (4)
C26	0.095 (6)	0.064 (5)	0.089 (6)	−0.037 (4)	0.023 (5)	0.002 (4)
C27	0.054 (4)	0.064 (4)	0.063 (4)	−0.017 (3)	0.007 (3)	−0.006 (4)
C28	0.081 (5)	0.092 (5)	0.079 (5)	0.017 (4)	0.023 (4)	0.037 (4)
N2	0.041 (3)	0.037 (3)	0.044 (3)	0.004 (2)	0.001 (2)	0.007 (2)
O4	0.070 (3)	0.048 (2)	0.078 (3)	−0.019 (2)	0.004 (2)	0.006 (2)
O5	0.086 (3)	0.044 (2)	0.066 (3)	0.026 (2)	0.020 (2)	0.006 (2)
O6	0.043 (2)	0.056 (2)	0.048 (2)	0.0163 (19)	−0.0081 (19)	−0.0036 (19)
S2	0.0638 (10)	0.0343 (8)	0.0493 (9)	0.0036 (8)	0.0100 (7)	0.0068 (7)
C29	0.046 (3)	0.044 (3)	0.025 (3)	−0.002 (3)	0.010 (2)	−0.004 (2)
C30	0.047 (3)	0.054 (4)	0.038 (3)	0.002 (3)	0.008 (3)	−0.008 (3)
C31	0.078 (5)	0.050 (4)	0.049 (4)	0.000 (3)	0.008 (3)	−0.012 (3)
C32	0.065 (5)	0.063 (5)	0.071 (5)	−0.022 (4)	0.001 (4)	−0.017 (4)
C33	0.043 (4)	0.078 (5)	0.088 (5)	−0.001 (4)	0.000 (3)	−0.015 (4)
C34	0.054 (4)	0.052 (4)	0.057 (4)	0.004 (3)	0.006 (3)	−0.009 (3)
C35	0.035 (3)	0.050 (4)	0.043 (4)	0.005 (3)	0.006 (3)	−0.006 (3)
C36	0.039 (3)	0.057 (4)	0.046 (4)	0.012 (3)	0.002 (3)	0.007 (3)
C37	0.070 (4)	0.066 (4)	0.033 (3)	0.016 (3)	−0.003 (3)	0.004 (3)
C38	0.084 (5)	0.091 (5)	0.044 (4)	0.034 (4)	−0.013 (4)	−0.012 (4)
C39	0.075 (5)	0.157 (8)	0.032 (4)	0.044 (6)	−0.004 (4)	0.008 (5)
C40	0.081 (6)	0.142 (8)	0.049 (5)	0.012 (6)	0.006 (4)	0.038 (5)
C41	0.063 (4)	0.076 (5)	0.066 (5)	0.004 (4)	0.002 (4)	0.023 (4)
C42	0.194 (10)	0.126 (8)	0.072 (6)	0.045 (7)	−0.030 (6)	−0.040 (6)
N3	0.045 (3)	0.041 (3)	0.031 (2)	0.006 (2)	0.005 (2)	−0.002 (2)
O7	0.054 (3)	0.102 (3)	0.064 (3)	−0.032 (2)	0.036 (2)	−0.029 (2)
O8	0.109 (3)	0.049 (3)	0.042 (2)	−0.019 (2)	−0.001 (2)	0.012 (2)
O9	0.081 (3)	0.054 (3)	0.071 (3)	0.029 (2)	0.004 (2)	−0.009 (2)
S3	0.0568 (9)	0.0533 (9)	0.0331 (8)	−0.0165 (8)	0.0134 (7)	−0.0054 (7)

Geometric parameters (Å, º) top

C1—C2	1.369 (7)	C23—C24	1.386 (7)
C1—C6	1.381 (7)	C23—H23	0.9300
C1—S1	1.754 (5)	C24—C25	1.384 (8)
C2—C3	1.383 (8)	C24—C28	1.501 (8)
C2—H2	0.9300	C25—C26	1.366 (9)
C3—C4	1.371 (9)	C25—H25	0.9300
C3—H3	0.9300	C26—C27	1.374 (8)
C4—C5	1.367 (9)	C26—H26	0.9300
C4—H4	0.9300	C27—H27	0.9300
C5—C6	1.375 (8)	C28—H28A	0.9600
C5—H5	0.9300	C28—H28B	0.9600
C6—H6	0.9300	C28—H28C	0.9600
C7—O3	1.212 (6)	N2—S2	1.671 (4)
C7—N1	1.381 (6)	N2—H2N	0.857 (19)
C7—C8	1.487 (7)	O4—S2	1.426 (4)
C8—C13	1.372 (7)	O5—S2	1.426 (4)
C8—C9	1.377 (7)	C29—C30	1.367 (7)
C9—C10	1.378 (8)	C29—C34	1.391 (7)
C9—H9	0.9300	C29—S3	1.753 (5)
C10—C11	1.369 (8)	C30—C31	1.376 (7)
C10—C14	1.505 (8)	C30—H30	0.9300
C11—C12	1.367 (8)	C31—C32	1.374 (8)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.377 (7)	C32—C33	1.372 (8)
C12—H12	0.9300	C32—H32	0.9300
C13—H13	0.9300	C33—C34	1.371 (7)
C14—H14A	0.9600	C33—H33	0.9300
C14—H14B	0.9600	C34—H34	0.9300
C14—H14C	0.9600	C35—O9	1.209 (6)
N1—S1	1.652 (4)	C35—N3	1.378 (6)
N1—H1N	0.849 (19)	C35—C36	1.491 (7)
O1—S1	1.422 (4)	C36—C37	1.377 (7)
O2—S1	1.435 (3)	C36—C41	1.382 (7)
C15—C20	1.370 (7)	C37—C38	1.394 (8)
C15—C16	1.379 (7)	C37—H37	0.9300
C15—S2	1.756 (6)	C38—C39	1.381 (10)
C16—C17	1.372 (8)	C38—C42	1.502 (9)
C16—H16	0.9300	C39—C40	1.355 (10)
C17—C18	1.370 (9)	C39—H39	0.9300
C17—H17	0.9300	C40—C41	1.378 (9)
C18—C19	1.363 (9)	C40—H40	0.9300
C18—H18	0.9300	C41—H41	0.9300
C19—C20	1.382 (8)	C42—H42A	0.9600
C19—H19	0.9300	C42—H42B	0.9600
C20—H20	0.9300	C42—H42C	0.9600
C21—O6	1.220 (5)	N3—S3	1.638 (4)
C21—N2	1.375 (6)	N3—H3N	0.846 (19)
C21—C22	1.482 (7)	O7—S3	1.437 (4)
C22—C27	1.382 (7)	O8—S3	1.429 (4)
C22—C23	1.384 (6)

C2—C1—C6	121.2 (5)	C25—C24—C23	118.2 (5)
C2—C1—S1	119.9 (4)	C25—C24—C28	120.4 (6)
C6—C1—S1	118.9 (4)	C23—C24—C28	121.4 (6)
C1—C2—C3	119.0 (6)	C26—C25—C24	121.3 (6)
C1—C2—H2	120.5	C26—C25—H25	119.4
C3—C2—H2	120.5	C24—C25—H25	119.4
C4—C3—C2	120.4 (6)	C25—C26—C27	119.9 (6)
C4—C3—H3	119.8	C25—C26—H26	120.1
C2—C3—H3	119.8	C27—C26—H26	120.1
C5—C4—C3	119.8 (6)	C26—C27—C22	120.5 (6)
C5—C4—H4	120.1	C26—C27—H27	119.7
C3—C4—H4	120.1	C22—C27—H27	119.7
C4—C5—C6	120.9 (6)	C24—C28—H28A	109.5
C4—C5—H5	119.5	C24—C28—H28B	109.5
C6—C5—H5	119.5	H28A—C28—H28B	109.5
C5—C6—C1	118.7 (6)	C24—C28—H28C	109.5
C5—C6—H6	120.7	H28A—C28—H28C	109.5
C1—C6—H6	120.7	H28B—C28—H28C	109.5
O3—C7—N1	121.3 (5)	C21—N2—S2	124.1 (3)
O3—C7—C8	123.4 (5)	C21—N2—H2N	124 (3)
N1—C7—C8	115.3 (5)	S2—N2—H2N	109 (3)
C13—C8—C9	118.8 (5)	O5—S2—O4	121.1 (2)
C13—C8—C7	122.2 (5)	O5—S2—N2	108.2 (2)
C9—C8—C7	118.9 (5)	O4—S2—N2	103.4 (2)
C8—C9—C10	121.6 (6)	O5—S2—C15	108.6 (3)
C8—C9—H9	119.2	O4—S2—C15	109.2 (3)
C10—C9—H9	119.2	N2—S2—C15	105.2 (2)
C11—C10—C9	118.3 (6)	C30—C29—C34	121.5 (5)
C11—C10—C14	120.9 (6)	C30—C29—S3	120.1 (4)
C9—C10—C14	120.7 (6)	C34—C29—S3	118.3 (4)
C12—C11—C10	121.0 (6)	C29—C30—C31	118.6 (5)
C12—C11—H11	119.5	C29—C30—H30	120.7
C10—C11—H11	119.5	C31—C30—H30	120.7
C11—C12—C13	120.0 (6)	C32—C31—C30	120.8 (6)
C11—C12—H12	120.0	C32—C31—H31	119.6
C13—C12—H12	120.0	C30—C31—H31	119.6
C8—C13—C12	120.2 (6)	C33—C32—C31	120.0 (6)
C8—C13—H13	119.9	C33—C32—H32	120.0
C12—C13—H13	119.9	C31—C32—H32	120.0
C10—C14—H14A	109.5	C34—C33—C32	120.5 (6)
C10—C14—H14B	109.5	C34—C33—H33	119.8
H14A—C14—H14B	109.5	C32—C33—H33	119.8
C10—C14—H14C	109.5	C33—C34—C29	118.6 (5)
H14A—C14—H14C	109.5	C33—C34—H34	120.7
H14B—C14—H14C	109.5	C29—C34—H34	120.7
C7—N1—S1	124.4 (4)	O9—C35—N3	122.2 (5)
C7—N1—H1N	125 (3)	O9—C35—C36	122.9 (5)
S1—N1—H1N	111 (3)	N3—C35—C36	114.9 (5)
O1—S1—O2	119.7 (2)	C37—C36—C41	120.1 (6)
O1—S1—N1	104.7 (2)	C37—C36—C35	121.5 (5)
O2—S1—N1	108.5 (2)	C41—C36—C35	118.4 (6)
O1—S1—C1	109.0 (2)	C36—C37—C38	120.8 (6)
O2—S1—C1	107.5 (2)	C36—C37—H37	119.6
N1—S1—C1	106.7 (2)	C38—C37—H37	119.6
C20—C15—C16	121.2 (6)	C39—C38—C37	117.3 (7)
C20—C15—S2	120.2 (5)	C39—C38—C42	122.0 (7)
C16—C15—S2	118.6 (5)	C37—C38—C42	120.8 (7)
C17—C16—C15	119.1 (6)	C40—C39—C38	122.7 (7)
C17—C16—H16	120.4	C40—C39—H39	118.7
C15—C16—H16	120.4	C38—C39—H39	118.7
C18—C17—C16	120.0 (7)	C39—C40—C41	119.7 (7)
C18—C17—H17	120.0	C39—C40—H40	120.2
C16—C17—H17	120.0	C41—C40—H40	120.2
C19—C18—C17	120.7 (7)	C40—C41—C36	119.6 (7)
C19—C18—H18	119.7	C40—C41—H41	120.2
C17—C18—H18	119.7	C36—C41—H41	120.2
C18—C19—C20	120.1 (7)	C38—C42—H42A	109.5
C18—C19—H19	119.9	C38—C42—H42B	109.5
C20—C19—H19	119.9	H42A—C42—H42B	109.5
C15—C20—C19	118.9 (6)	C38—C42—H42C	109.5
C15—C20—H20	120.6	H42A—C42—H42C	109.5
C19—C20—H20	120.6	H42B—C42—H42C	109.5
O6—C21—N2	121.4 (5)	C35—N3—S3	124.4 (4)
O6—C21—C22	122.7 (5)	C35—N3—H3N	123 (3)
N2—C21—C22	115.8 (4)	S3—N3—H3N	111 (3)
C27—C22—C23	119.0 (5)	O8—S3—O7	119.9 (3)
C27—C22—C21	117.0 (5)	O8—S3—N3	104.0 (2)
C23—C22—C21	124.1 (4)	O7—S3—N3	107.8 (2)
C22—C23—C24	121.2 (5)	O8—S3—C29	108.6 (2)
C22—C23—H23	119.4	O7—S3—C29	107.7 (2)
C24—C23—H23	119.4	N3—S3—C29	108.3 (2)

C6—C1—C2—C3	−0.4 (9)	C28—C24—C25—C26	−177.1 (6)
S1—C1—C2—C3	−179.4 (5)	C24—C25—C26—C27	−0.8 (11)
C1—C2—C3—C4	0.6 (11)	C25—C26—C27—C22	−1.1 (10)
C2—C3—C4—C5	−0.6 (12)	C23—C22—C27—C26	1.6 (9)
C3—C4—C5—C6	0.5 (12)	C21—C22—C27—C26	−178.5 (5)
C4—C5—C6—C1	−0.3 (10)	O6—C21—N2—S2	3.6 (7)
C2—C1—C6—C5	0.3 (9)	C22—C21—N2—S2	−175.3 (3)
S1—C1—C6—C5	179.3 (5)	C21—N2—S2—O5	−51.1 (5)
O3—C7—C8—C13	152.1 (6)	C21—N2—S2—O4	179.3 (4)
N1—C7—C8—C13	−28.9 (7)	C21—N2—S2—C15	64.8 (5)
O3—C7—C8—C9	−25.4 (8)	C20—C15—S2—O5	8.5 (6)
N1—C7—C8—C9	153.6 (5)	C16—C15—S2—O5	−170.1 (4)
C13—C8—C9—C10	0.3 (9)	C20—C15—S2—O4	142.5 (5)
C7—C8—C9—C10	177.9 (5)	C16—C15—S2—O4	−36.2 (5)
C8—C9—C10—C11	−1.9 (9)	C20—C15—S2—N2	−107.2 (5)
C8—C9—C10—C14	178.9 (6)	C16—C15—S2—N2	74.2 (5)
C9—C10—C11—C12	1.9 (10)	C34—C29—C30—C31	0.4 (8)
C14—C10—C11—C12	−178.9 (7)	S3—C29—C30—C31	−177.9 (4)
C10—C11—C12—C13	−0.3 (10)	C29—C30—C31—C32	−0.9 (8)
C9—C8—C13—C12	1.2 (8)	C30—C31—C32—C33	0.5 (10)
C7—C8—C13—C12	−176.3 (5)	C31—C32—C33—C34	0.4 (10)
C11—C12—C13—C8	−1.3 (9)	C32—C33—C34—C29	−0.9 (9)
O3—C7—N1—S1	−8.8 (8)	C30—C29—C34—C33	0.4 (8)
C8—C7—N1—S1	172.2 (4)	S3—C29—C34—C33	178.8 (5)
C7—N1—S1—O1	−173.1 (4)	O9—C35—C36—C37	147.1 (6)
C7—N1—S1—O2	−44.2 (5)	N3—C35—C36—C37	−32.8 (7)
C7—N1—S1—C1	71.4 (5)	O9—C35—C36—C41	−32.2 (8)
C2—C1—S1—O1	147.0 (5)	N3—C35—C36—C41	147.9 (5)
C6—C1—S1—O1	−31.9 (5)	C41—C36—C37—C38	−0.1 (9)
C2—C1—S1—O2	15.9 (5)	C35—C36—C37—C38	−179.5 (5)
C6—C1—S1—O2	−163.1 (4)	C36—C37—C38—C39	−0.3 (9)
C2—C1—S1—N1	−100.4 (5)	C36—C37—C38—C42	178.7 (6)
C6—C1—S1—N1	80.6 (5)	C37—C38—C39—C40	0.1 (11)
C20—C15—C16—C17	−0.7 (9)	C42—C38—C39—C40	−178.8 (7)
S2—C15—C16—C17	178.0 (5)	C38—C39—C40—C41	0.4 (12)
C15—C16—C17—C18	−0.2 (10)	C39—C40—C41—C36	−0.9 (11)
C16—C17—C18—C19	0.7 (12)	C37—C36—C41—C40	0.7 (9)
C17—C18—C19—C20	−0.4 (13)	C35—C36—C41—C40	−179.9 (5)
C16—C15—C20—C19	0.9 (10)	O9—C35—N3—S3	−6.2 (8)
S2—C15—C20—C19	−177.7 (5)	C36—C35—N3—S3	173.7 (4)
C18—C19—C20—C15	−0.4 (12)	C35—N3—S3—O8	179.9 (4)
O6—C21—C22—C27	−18.3 (7)	C35—N3—S3—O7	−51.8 (5)
N2—C21—C22—C27	160.5 (5)	C35—N3—S3—C29	64.5 (5)
O6—C21—C22—C23	161.6 (5)	C30—C29—S3—O8	144.2 (4)
N2—C21—C22—C23	−19.6 (7)	C34—C29—S3—O8	−34.2 (5)
C27—C22—C23—C24	−0.3 (8)	C30—C29—S3—O7	13.0 (5)
C21—C22—C23—C24	179.9 (5)	C34—C29—S3—O7	−165.4 (4)
C22—C23—C24—C25	−1.5 (8)	C30—C29—S3—N3	−103.4 (4)
C22—C23—C24—C28	177.7 (5)	C34—C29—S3—N3	78.2 (5)
C23—C24—C25—C26	2.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O7ⁱ	0.85 (2)	2.04 (2)	2.864 (5)	164 (5)
N2—H2N···O2ⁱⁱ	0.86 (2)	2.15 (3)	2.920 (5)	150 (5)
N3—H3N···O6	0.85 (2)	2.05 (2)	2.891 (5)	172 (5)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₃S
M_r	275.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.6028 (8), 35.100 (3), 10.4886 (8)
β (°)	100.920 (7)
V (Å³)	4194.2 (6)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.46 × 0.30 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.900, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	15537, 7317, 4440
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.097, 0.146, 1.29
No. of reflections	7317
No. of parameters	526
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.33

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···O7ⁱ	0.849 (19)	2.04 (2)	2.864 (5)	164 (5)
N2—H2N···O2ⁱⁱ	0.857 (19)	2.15 (3)	2.920 (5)	150 (5)
N3—H3N···O6	0.846 (19)	2.05 (2)	2.891 (5)	172 (5)

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

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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