2,4-Dimethyl-N-(4-methyl­phen­yl)benzene­sulfonamide

Nirmala, P.G.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536810049627

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o6

https://doi.org/10.1107/S1600536810049627

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2,4-Dimethyl-N-(4-methylphenyl)benzenesulfonamide

P. G. Nirmala,^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 23 November 2010; accepted 27 November 2010; online 4 December 2010)

The asymmetric unit of the crystal of the title compound, C₁₅H₁₇NO₂S, contains two independent molecules, which are twisted at the S—N bonds with C—SO₂—NH—C torsion angles of 48.3 (2) (molecule 1) and −75.7 (3)° (molecule 2). The dihedral angles between the benzene rings are 72.0 (1) (molecule 1) and 78.3 (1)° (molecule 2). The crystal structure features inversion dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009 ); Nirmala et al. (2009 , 2010 ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.36
Monoclinic, P 2₁ /c
a = 10.623 (1) Å
b = 10.770 (1) Å
c = 25.513 (2) Å
β = 97.927 (6)°
V = 2891.0 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 299 K
0.40 × 0.30 × 0.20 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 = 0.917, T_max = 0.957
10876 measured reflections
5282 independent reflections
3743 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.03
5282 reflections
355 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.85 (1)	2.15 (1)	2.991 (2)	169 (2)
N2—H2N⋯O2ⁱⁱ	0.85 (1)	2.03 (1)	2.877 (2)	175 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810049627/bq2257sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049627/bq2257Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of substitutions on the structures of N-(aryl)-arylsulfonamides (Gowda et al. , 2009; Nirmala et al., 2009; 2010), in the present work, the structure of 2,4-dimethyl-N-(4-methylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit of (I) contains two independent molecules. The molecules are twisted at the S—N bonds with the C1—SO₂—NH—C7 torsion angles of -48.3 (2)° (molecule 1) and -75.7 (3)° (molecule 2), compared to the values of 71.6 (1)° in 2,4-dimethyl-N-(2-methylphenyl)benzenesulfonamide (II) (Nirmala et al., 2009), -58.4 (2)° in 2,4-dimethyl-N-(3-methylphenyl)benzenesulfonamide (III) (Nirmala et al., 2010) and -46.1 (3)° (molecule 1) & 47.7 (3)° (molecule 2) in the two molecules of 2,4-dimethyl-N-(phenyl)- benzenesulfonamide (IV)(Gowda et al., 2009).

The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 72.0 (1)° (molecule 1) and 78.3 (1)° (molecule 2), compared to the values of 47.0 (1)° in (II), 47.1 (1)° in (III), and 67.5 (1)° in molecule 1 and 72.9 (1)° in molecule 2 of (IV).

The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds (Table 1) is shown in Fig.2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (2009, 2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of 1,3-xylene (1,3-dimethylbenzene) (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dimethylbenzenesulfonylchloride was treated with p-toluidine in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid 2,4-dimethyl-N-(4-methylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006).

The prism like colourless single crystals used in x-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Structure description top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009); Nirmala et al. (2009, 2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

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 (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2,4-Dimethyl-N-(4-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₂S	F(000) = 1168
M_r = 275.36	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2957 reflections
a = 10.623 (1) Å	θ = 2.7–27.9°
b = 10.770 (1) Å	µ = 0.22 mm⁻¹
c = 25.513 (2) Å	T = 299 K
β = 97.927 (6)°	Prism, colourless
V = 2891.0 (4) Å³	0.40 × 0.30 × 0.20 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5282 independent reflections
Radiation source: fine-focus sealed tube	3743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Rotation method data acquisition using ω and phi scans	θ_max = 25.4°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→10
T_min = 0.917, T_max = 0.957	k = −12→11
10876 measured reflections	l = −26→30

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0588P)² + 0.5667P] where P = (F_o² + 2F_c²)/3
5282 reflections	(Δ/σ)_max = 0.009
355 parameters	Δρ_max = 0.20 e Å⁻³
3 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₇NO₂S	V = 2891.0 (4) Å³
M_r = 275.36	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.623 (1) Å	µ = 0.22 mm⁻¹
b = 10.770 (1) Å	T = 299 K
c = 25.513 (2) Å	0.40 × 0.30 × 0.20 mm
β = 97.927 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5282 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3743 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.957	R_int = 0.017
10876 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
5282 reflections	Δρ_min = −0.23 e Å⁻³
355 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
S1	0.16582 (5)	0.91378 (5)	0.253220 (19)	0.04951 (16)
O1	0.16198 (14)	1.03883 (14)	0.23457 (6)	0.0619 (4)
O2	0.09258 (13)	0.88329 (15)	0.29500 (5)	0.0625 (4)
N1	0.31153 (16)	0.87937 (18)	0.27751 (6)	0.0543 (5)
H1N	0.311 (2)	0.8300 (18)	0.3034 (7)	0.065*
C1	0.12183 (16)	0.81649 (19)	0.19825 (7)	0.0437 (5)
C2	0.12013 (18)	0.6871 (2)	0.20238 (8)	0.0520 (5)
C3	0.0833 (2)	0.6212 (2)	0.15577 (9)	0.0616 (6)
H3	0.0810	0.5350	0.1576	0.074*
C4	0.0500 (2)	0.6771 (2)	0.10694 (9)	0.0615 (6)
C5	0.0507 (2)	0.8053 (3)	0.10508 (8)	0.0639 (6)
H5	0.0264	0.8452	0.0729	0.077*
C6	0.08644 (19)	0.8752 (2)	0.14974 (8)	0.0538 (5)
H6	0.0870	0.9614	0.1476	0.065*
C7	0.41385 (18)	0.8671 (2)	0.24720 (7)	0.0472 (5)
C8	0.5031 (2)	0.7771 (2)	0.26186 (9)	0.0666 (6)
H8	0.4941	0.7249	0.2901	0.080*
C9	0.6063 (2)	0.7634 (3)	0.23492 (11)	0.0761 (7)
H9	0.6663	0.7025	0.2458	0.091*
C10	0.6230 (2)	0.8373 (2)	0.19238 (9)	0.0612 (6)
C11	0.5324 (2)	0.9270 (2)	0.17813 (9)	0.0611 (6)
H11	0.5413	0.9788	0.1497	0.073*
C12	0.4286 (2)	0.9428 (2)	0.20474 (9)	0.0582 (6)
H12	0.3689	1.0041	0.1941	0.070*
C13	0.1564 (3)	0.6158 (2)	0.25302 (10)	0.0769 (7)
H13A	0.1038	0.6417	0.2787	0.092*
H13B	0.2439	0.6316	0.2663	0.092*
H13C	0.1446	0.5286	0.2463	0.092*
C14	0.0177 (3)	0.5997 (3)	0.05741 (10)	0.0884 (9)
H14A	0.0130	0.5138	0.0669	0.106*
H14B	0.0824	0.6104	0.0350	0.106*
H14C	−0.0627	0.6258	0.0389	0.106*
C15	0.7355 (3)	0.8194 (3)	0.16271 (12)	0.0923 (9)
H15A	0.7062	0.7916	0.1274	0.111*
H15B	0.7919	0.7585	0.1806	0.111*
H15C	0.7798	0.8968	0.1613	0.111*
S2	0.75114 (5)	0.19437 (7)	0.08416 (2)	0.0658 (2)
O3	0.67144 (15)	0.23202 (19)	0.12238 (6)	0.0836 (6)
O4	0.75504 (17)	0.06565 (18)	0.07007 (6)	0.0795 (5)
N2	0.89188 (18)	0.2396 (2)	0.10928 (7)	0.0728 (6)
H2N	0.892 (2)	0.284 (2)	0.1371 (7)	0.087*
C16	0.70689 (18)	0.2795 (2)	0.02500 (8)	0.0569 (6)
C17	0.6886 (2)	0.4078 (3)	0.02402 (10)	0.0677 (7)
C18	0.6524 (2)	0.4629 (3)	−0.02539 (12)	0.0800 (8)
H18	0.6401	0.5484	−0.0268	0.096*
C19	0.6339 (2)	0.3966 (3)	−0.07224 (11)	0.0761 (7)
C20	0.6518 (2)	0.2702 (3)	−0.06978 (9)	0.0737 (7)
H20	0.6392	0.2236	−0.1007	0.088*
C21	0.6883 (2)	0.2111 (3)	−0.02178 (8)	0.0647 (6)
H21	0.7003	0.1256	−0.0208	0.078*
C22	1.00993 (19)	0.2099 (2)	0.09259 (8)	0.0547 (5)
C23	1.0219 (2)	0.1542 (3)	0.04490 (8)	0.0709 (7)
H23	0.9497	0.1309	0.0222	0.085*
C24	1.1411 (2)	0.1330 (3)	0.03075 (9)	0.0716 (7)
H24	1.1473	0.0951	−0.0016	0.086*
C25	1.2500 (2)	0.1658 (2)	0.06267 (11)	0.0655 (6)
C26	1.2360 (2)	0.2188 (2)	0.11096 (11)	0.0740 (7)
H26	1.3085	0.2403	0.1339	0.089*
C27	1.1183 (2)	0.2407 (2)	0.12624 (9)	0.0626 (6)
H27	1.1121	0.2761	0.1590	0.075*
C28	0.5989 (3)	0.4606 (4)	−0.12494 (13)	0.1115 (11)
H28A	0.6747	0.4790	−0.1400	0.134*
H28B	0.5545	0.5363	−0.1199	0.134*
H28C	0.5452	0.4071	−0.1484	0.134*
C29	0.7054 (3)	0.4885 (3)	0.07303 (12)	0.0962 (9)
H29A	0.7878	0.4738	0.0927	0.115*
H29B	0.6410	0.4686	0.0946	0.115*
H29C	0.6982	0.5743	0.0629	0.115*
C30	1.3795 (2)	0.1458 (3)	0.04557 (14)	0.0971 (10)
H30A	1.3696	0.1275	0.0084	0.117*
H30B	1.4212	0.0776	0.0650	0.117*
H30C	1.4297	0.2196	0.0525	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0446 (3)	0.0605 (4)	0.0442 (3)	0.0057 (2)	0.0088 (2)	0.0021 (2)
O1	0.0653 (9)	0.0528 (10)	0.0674 (9)	0.0038 (7)	0.0093 (7)	0.0006 (8)
O2	0.0517 (8)	0.0895 (12)	0.0494 (8)	0.0140 (8)	0.0179 (7)	0.0080 (8)
N1	0.0448 (9)	0.0755 (13)	0.0429 (9)	0.0036 (9)	0.0073 (8)	0.0052 (9)
C1	0.0367 (10)	0.0514 (13)	0.0438 (10)	0.0015 (8)	0.0084 (8)	0.0062 (9)
C2	0.0432 (11)	0.0571 (14)	0.0561 (12)	−0.0066 (9)	0.0086 (9)	0.0082 (11)
C3	0.0567 (13)	0.0556 (14)	0.0742 (15)	−0.0129 (10)	0.0148 (11)	−0.0024 (12)
C4	0.0527 (13)	0.0767 (18)	0.0567 (13)	−0.0161 (12)	0.0129 (10)	−0.0102 (12)
C5	0.0650 (14)	0.0832 (19)	0.0432 (12)	−0.0065 (12)	0.0069 (10)	0.0070 (12)
C6	0.0560 (12)	0.0585 (14)	0.0472 (11)	0.0020 (10)	0.0088 (9)	0.0088 (10)
C7	0.0419 (10)	0.0580 (13)	0.0412 (10)	−0.0027 (9)	0.0037 (8)	−0.0031 (9)
C8	0.0546 (13)	0.0815 (17)	0.0654 (14)	0.0116 (12)	0.0146 (11)	0.0223 (13)
C9	0.0589 (15)	0.0785 (18)	0.0937 (19)	0.0209 (12)	0.0208 (13)	0.0210 (15)
C10	0.0551 (13)	0.0620 (15)	0.0700 (14)	−0.0017 (11)	0.0209 (11)	−0.0031 (12)
C11	0.0640 (14)	0.0621 (15)	0.0606 (13)	−0.0046 (12)	0.0203 (11)	0.0076 (12)
C12	0.0543 (13)	0.0565 (14)	0.0655 (14)	0.0045 (10)	0.0137 (10)	0.0054 (11)
C13	0.0869 (18)	0.0626 (17)	0.0778 (17)	−0.0075 (13)	−0.0017 (14)	0.0199 (13)
C14	0.0858 (19)	0.109 (2)	0.0728 (17)	−0.0318 (16)	0.0184 (14)	−0.0272 (16)
C15	0.0802 (18)	0.095 (2)	0.112 (2)	0.0100 (16)	0.0499 (17)	0.0032 (18)
S2	0.0534 (3)	0.1010 (5)	0.0443 (3)	−0.0202 (3)	0.0115 (2)	−0.0084 (3)
O3	0.0596 (10)	0.1410 (17)	0.0543 (9)	−0.0271 (10)	0.0221 (7)	−0.0182 (10)
O4	0.0850 (11)	0.0914 (9)	0.0616 (10)	−0.0235 (9)	0.0085 (8)	0.0003 (9)
N2	0.0517 (11)	0.1221 (19)	0.0448 (10)	−0.0140 (11)	0.0076 (8)	−0.0212 (11)
C16	0.0397 (11)	0.0814 (18)	0.0505 (12)	−0.0113 (10)	0.0089 (9)	−0.0098 (11)
C17	0.0463 (12)	0.088 (2)	0.0709 (16)	−0.0035 (12)	0.0175 (11)	−0.0183 (14)
C18	0.0618 (15)	0.086 (2)	0.094 (2)	0.0098 (13)	0.0173 (14)	0.0046 (17)
C19	0.0522 (14)	0.106 (2)	0.0698 (16)	0.0003 (14)	0.0069 (12)	0.0066 (17)
C20	0.0617 (15)	0.107 (2)	0.0510 (13)	−0.0126 (14)	0.0024 (11)	−0.0092 (14)
C21	0.0571 (13)	0.0837 (18)	0.0520 (12)	−0.0119 (12)	0.0031 (10)	−0.0120 (12)
C22	0.0502 (12)	0.0702 (15)	0.0426 (11)	−0.0049 (10)	0.0026 (9)	0.0059 (10)
C23	0.0472 (13)	0.121 (2)	0.0422 (11)	−0.0032 (13)	−0.0024 (9)	−0.0094 (13)
C24	0.0551 (14)	0.103 (2)	0.0562 (13)	0.0078 (13)	0.0047 (11)	−0.0046 (13)
C25	0.0454 (12)	0.0638 (16)	0.0845 (17)	0.0013 (11)	−0.0013 (11)	0.0055 (13)
C26	0.0532 (14)	0.0749 (18)	0.0866 (18)	−0.0057 (12)	−0.0158 (12)	−0.0094 (15)
C27	0.0624 (14)	0.0667 (16)	0.0550 (13)	−0.0067 (11)	−0.0054 (11)	−0.0054 (11)
C28	0.086 (2)	0.155 (3)	0.093 (2)	0.019 (2)	0.0118 (17)	0.037 (2)
C29	0.087 (2)	0.102 (2)	0.104 (2)	−0.0038 (16)	0.0286 (16)	−0.0380 (19)
C30	0.0531 (15)	0.098 (2)	0.139 (3)	0.0041 (14)	0.0099 (16)	−0.015 (2)

Geometric parameters (Å, º) top

S1—O1	1.4271 (15)	S2—O4	1.434 (2)
S1—O2	1.4415 (14)	S2—O3	1.4352 (16)
S1—N1	1.6287 (17)	S2—N2	1.6184 (19)
S1—C1	1.761 (2)	S2—C16	1.773 (2)
N1—C7	1.424 (2)	N2—C22	1.416 (3)
N1—H1N	0.849 (9)	N2—H2N	0.852 (10)
C1—C6	1.394 (3)	C16—C21	1.393 (3)
C1—C2	1.398 (3)	C16—C17	1.395 (3)
C2—C3	1.394 (3)	C17—C18	1.398 (4)
C2—C13	1.507 (3)	C17—C29	1.513 (3)
C3—C4	1.384 (3)	C18—C19	1.383 (4)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.382 (3)	C19—C20	1.375 (4)
C4—C14	1.513 (3)	C19—C28	1.511 (4)
C5—C6	1.374 (3)	C20—C21	1.387 (3)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.372 (3)	C22—C27	1.378 (3)
C7—C12	1.382 (3)	C22—C23	1.378 (3)
C8—C9	1.379 (3)	C23—C24	1.382 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.377 (3)	C24—C25	1.366 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.377 (3)	C25—C26	1.384 (4)
C10—C15	1.513 (3)	C25—C30	1.514 (3)
C11—C12	1.383 (3)	C26—C27	1.381 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—H12	0.9300	C27—H27	0.9300
C13—H13A	0.9600	C28—H28A	0.9600
C13—H13B	0.9600	C28—H28B	0.9600
C13—H13C	0.9600	C28—H28C	0.9600
C14—H14A	0.9600	C29—H29A	0.9600
C14—H14B	0.9600	C29—H29B	0.9600
C14—H14C	0.9600	C29—H29C	0.9600
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600

O1—S1—O2	117.90 (9)	O4—S2—O3	118.92 (11)
O1—S1—N1	108.88 (10)	O4—S2—N2	109.47 (12)
O2—S1—N1	104.38 (9)	O3—S2—N2	104.20 (10)
O1—S1—C1	107.68 (9)	O4—S2—C16	107.45 (11)
O2—S1—C1	110.01 (9)	O3—S2—C16	108.68 (11)
N1—S1—C1	107.55 (9)	N2—S2—C16	107.65 (10)
C7—N1—S1	124.81 (13)	C22—N2—S2	128.39 (16)
C7—N1—H1N	116.7 (16)	C22—N2—H2N	118.2 (18)
S1—N1—H1N	109.5 (15)	S2—N2—H2N	113.3 (18)
C6—C1—C2	120.94 (19)	C21—C16—C17	120.3 (2)
C6—C1—S1	116.52 (16)	C21—C16—S2	116.5 (2)
C2—C1—S1	122.53 (15)	C17—C16—S2	123.18 (18)
C3—C2—C1	116.63 (19)	C16—C17—C18	117.1 (2)
C3—C2—C13	118.7 (2)	C16—C17—C29	123.6 (3)
C1—C2—C13	124.6 (2)	C18—C17—C29	119.2 (3)
C4—C3—C2	123.6 (2)	C19—C18—C17	123.3 (3)
C4—C3—H3	118.2	C19—C18—H18	118.4
C2—C3—H3	118.2	C17—C18—H18	118.4
C5—C4—C3	117.6 (2)	C20—C19—C18	118.0 (3)
C5—C4—C14	121.6 (2)	C20—C19—C28	120.5 (3)
C3—C4—C14	120.8 (2)	C18—C19—C28	121.4 (3)
C6—C5—C4	121.4 (2)	C19—C20—C21	121.0 (2)
C6—C5—H5	119.3	C19—C20—H20	119.5
C4—C5—H5	119.3	C21—C20—H20	119.5
C5—C6—C1	119.8 (2)	C20—C21—C16	120.2 (3)
C5—C6—H6	120.1	C20—C21—H21	119.9
C1—C6—H6	120.1	C16—C21—H21	119.9
C8—C7—C12	118.81 (19)	C27—C22—C23	118.9 (2)
C8—C7—N1	117.91 (18)	C27—C22—N2	117.2 (2)
C12—C7—N1	123.26 (19)	C23—C22—N2	123.90 (19)
C7—C8—C9	120.4 (2)	C22—C23—C24	120.1 (2)
C7—C8—H8	119.8	C22—C23—H23	119.9
C9—C8—H8	119.8	C24—C23—H23	119.9
C10—C9—C8	121.9 (2)	C25—C24—C23	122.2 (2)
C10—C9—H9	119.0	C25—C24—H24	118.9
C8—C9—H9	119.0	C23—C24—H24	118.9
C11—C10—C9	116.9 (2)	C24—C25—C26	116.8 (2)
C11—C10—C15	121.9 (2)	C24—C25—C30	121.3 (2)
C9—C10—C15	121.1 (2)	C26—C25—C30	121.9 (2)
C10—C11—C12	122.2 (2)	C27—C26—C25	122.3 (2)
C10—C11—H11	118.9	C27—C26—H26	118.9
C12—C11—H11	118.9	C25—C26—H26	118.9
C7—C12—C11	119.8 (2)	C22—C27—C26	119.6 (2)
C7—C12—H12	120.1	C22—C27—H27	120.2
C11—C12—H12	120.1	C26—C27—H27	120.2
C2—C13—H13A	109.5	C19—C28—H28A	109.5
C2—C13—H13B	109.5	C19—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28B	109.5
C2—C13—H13C	109.5	C19—C28—H28C	109.5
H13A—C13—H13C	109.5	H28A—C28—H28C	109.5
H13B—C13—H13C	109.5	H28B—C28—H28C	109.5
C4—C14—H14A	109.5	C17—C29—H29A	109.5
C4—C14—H14B	109.5	C17—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C4—C14—H14C	109.5	C17—C29—H29C	109.5
H14A—C14—H14C	109.5	H29A—C29—H29C	109.5
H14B—C14—H14C	109.5	H29B—C29—H29C	109.5
C10—C15—H15A	109.5	C25—C30—H30A	109.5
C10—C15—H15B	109.5	C25—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C10—C15—H15C	109.5	C25—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5

O1—S1—N1—C7	−68.1 (2)	O4—S2—N2—C22	40.9 (2)
O2—S1—N1—C7	165.14 (18)	O3—S2—N2—C22	169.1 (2)
C1—S1—N1—C7	48.3 (2)	C16—S2—N2—C22	−75.6 (2)
O1—S1—C1—C6	−3.23 (17)	O4—S2—C16—C21	−1.54 (19)
O2—S1—C1—C6	126.48 (15)	O3—S2—C16—C21	−131.43 (17)
N1—S1—C1—C6	−120.42 (15)	N2—S2—C16—C21	116.28 (17)
O1—S1—C1—C2	177.66 (15)	O4—S2—C16—C17	177.29 (17)
O2—S1—C1—C2	−52.64 (18)	O3—S2—C16—C17	47.4 (2)
N1—S1—C1—C2	60.47 (18)	N2—S2—C16—C17	−64.9 (2)
C6—C1—C2—C3	0.9 (3)	C21—C16—C17—C18	−0.5 (3)
S1—C1—C2—C3	179.96 (14)	S2—C16—C17—C18	−179.28 (16)
C6—C1—C2—C13	−179.9 (2)	C21—C16—C17—C29	179.3 (2)
S1—C1—C2—C13	−0.8 (3)	S2—C16—C17—C29	0.5 (3)
C1—C2—C3—C4	0.3 (3)	C16—C17—C18—C19	0.3 (4)
C13—C2—C3—C4	−179.0 (2)	C29—C17—C18—C19	−179.5 (2)
C2—C3—C4—C5	−1.7 (3)	C17—C18—C19—C20	0.2 (4)
C2—C3—C4—C14	176.7 (2)	C17—C18—C19—C28	−178.0 (2)
C3—C4—C5—C6	1.8 (3)	C18—C19—C20—C21	−0.5 (4)
C14—C4—C5—C6	−176.6 (2)	C28—C19—C20—C21	177.7 (2)
C4—C5—C6—C1	−0.6 (3)	C19—C20—C21—C16	0.3 (3)
C2—C1—C6—C5	−0.8 (3)	C17—C16—C21—C20	0.2 (3)
S1—C1—C6—C5	−179.88 (16)	S2—C16—C21—C20	179.10 (17)
S1—N1—C7—C8	−143.38 (19)	S2—N2—C22—C27	−168.06 (19)
S1—N1—C7—C12	38.0 (3)	S2—N2—C22—C23	12.9 (4)
C12—C7—C8—C9	0.6 (3)	C27—C22—C23—C24	−1.7 (4)
N1—C7—C8—C9	−178.1 (2)	N2—C22—C23—C24	177.3 (2)
C7—C8—C9—C10	−0.9 (4)	C22—C23—C24—C25	−0.1 (4)
C8—C9—C10—C11	0.7 (4)	C23—C24—C25—C26	1.7 (4)
C8—C9—C10—C15	−178.9 (3)	C23—C24—C25—C30	−177.8 (3)
C9—C10—C11—C12	−0.4 (4)	C24—C25—C26—C27	−1.5 (4)
C15—C10—C11—C12	179.2 (2)	C30—C25—C26—C27	178.0 (2)
C8—C7—C12—C11	−0.3 (3)	C23—C22—C27—C26	1.9 (4)
N1—C7—C12—C11	178.3 (2)	N2—C22—C27—C26	−177.2 (2)
C10—C11—C12—C7	0.2 (3)	C25—C26—C27—C22	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.85 (1)	2.15 (1)	2.991 (2)	169 (2)
N2—H2N···O2ⁱⁱ	0.85 (1)	2.03 (1)	2.877 (2)	175 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₂S
M_r	275.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	10.623 (1), 10.770 (1), 25.513 (2)
β (°)	97.927 (6)
V (Å³)	2891.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.30 × 0.20

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	0.917, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	10876, 5282, 3743
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.03
No. of reflections	5282
No. of parameters	355
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)	0.20, −0.23

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.849 (9)	2.153 (11)	2.991 (2)	169 (2)
N2—H2N···O2ⁱⁱ	0.852 (10)	2.026 (10)	2.877 (2)	175 (3)

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

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3210. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o989. Web of Science CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600–606. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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