2,4-Dimethyl-N-phenyl­benzene­sulfonamide

Gowda, B.T.; Foro, S.; Nirmala, P.G.; Babitha, K.S.; Fuess, H.

doi:10.1107/S160053680900573X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o576

doi:10.1107/S160053680900573X

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2,4-Dimethyl-N-phenylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a K. S. Babitha ^a and Hartmut Fuess ^b

^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 16 January 2009; accepted 18 February 2009; online 21 February 2009)

The asymmetric unit of the crystal structure of the title compound, C₁₄H₁₅NO₂S, contains two molecules. The conformations of the N—C bonds in the C—SO₂—NH—C segments of the structure have trans and gauche torsion angles with the S=O bonds. Furthermore, the torsion angles of the C—SO₂—NH—C groups in the two molecules are 46.1 (3) (glide image of molecule 1) and 47.7 (3)° (molecule 2). The ortho-methyl groups in the sulfonyl benzene ring are oriented away from the S=O bonds. The two benzene rings are tilted relative to each other by 67.5 (1) and 72.9 (1)° in the two molecules. N—H⋯O and C—H⋯O hydrogen bonds pack the molecules into one-dimensional chains in different directions, resulting in a two-dimensional network.

Related literature

For related structures, see: Gelbrich et al. (2007 ); Gowda et al. (2008a ,b ,c ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 261.33
Orthorhombic, P c a 2₁
a = 19.113 (3) Å
b = 8.9290 (8) Å
c = 15.781 (1) Å
V = 2693.2 (5) Å³
Z = 8
Cu Kα radiation
μ = 2.09 mm⁻¹
T = 299 K
0.50 × 0.43 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.401, T_max = 0.593
4916 measured reflections
2505 independent reflections
2421 reflections with I > 2σ(I)
R_int = 0.050
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 1.09
2505 reflections
330 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), no Friedel pairs
Flack parameter: 0.008 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.86	2.41	3.164 (3)	147
N2—H2N⋯O1ⁱⁱ	0.86	2.22	3.056 (3)	164
C11—H11⋯O2ⁱⁱⁱ	0.93	2.50	3.227 (4)	135
C23—H23⋯O4ⁱⁱⁱ	0.93	2.50	3.316 (4)	147
Symmetry codes: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+1, z]$ ; (iii) x, y+1, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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/S160053680900573X/kj2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900573X/kj2115Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008a, b, c), in the present work, the structure of N-(phenyl)-2,4-dimethylbenzenesulfonamide has been determined . The asymmetric unit contains 2 molecules (Fig. 1). The conformations of the N—C bonds in the C—SO₂—NH—C segments of the structure have "trans" torsions and "gauche" torsions with the S═O bonds. Further, the torsion angles of the C—SO₂—NH—C groups in the two molecules are 46.1 (3)° (glide image of molecule 1) and 47.7 (3)° (molecule 2). The ortho-methyl groups in the sulfonyl benzene rings orient themselves away from the S═O bonds, but in the direction of N—H bonds. The two benzene rings in the title compound are tilted relative to each other by 67.5 (1)° in the molecule 1 and 72.9 (1)° in molecule 2. The other bond parameters in the title compound are similar to those observed in N-(2,6-dimethylphenyl)-benzenesulfonamide (Gowda et al., 2008a), N-(2-methylphenyl)-benzenesulfonamide (Gowda et al., 2008b)) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007; Gowda et al., 2008c). The N-H···O hydrogen bonds pack the molecules into a 1D chain in the direction of c- axis, while C-H···O hydrogen bonds pack them into a 1D chain in the direction of b-axis, resulting in a 2D network (Table 1, Fig. 2).

Related literature top

For related structures, see: Gelbrich et al. (2007); Gowda et al. (2008a,b,c); Perlovich et al. (2006).

Experimental top

A solution of 1,3-xylene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 273K. 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 aniline 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 N-(phenyl)-2,4-dimethylbenzenesulfonamide 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. The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines. H-atoms not involved in hydrogen bonding have been omitted.

2,4-Dimethyl-N-phenylbenzenesulfonamide top

Crystal data top

C₁₄H₁₅NO₂S	F(000) = 1104
M_r = 261.33	D_x = 1.289 Mg m⁻³
Orthorhombic, Pca2₁	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 19.113 (3) Å	θ = 4.6–19.0°
b = 8.9290 (8) Å	µ = 2.09 mm⁻¹
c = 15.781 (1) Å	T = 299 K
V = 2693.2 (5) Å³	Prism, colourless
Z = 8	0.50 × 0.43 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 66.9°, θ_min = 4.6°
ω/2θ scans	h = −22→22
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
T_min = 0.401, T_max = 0.593	l = −18→0
4916 measured reflections	3 standard reflections every 120 min
2505 independent reflections	intensity decay: 1.0%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0565P)² + 0.1061P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max = 0.012
S = 1.09	Δρ_max = 0.26 e Å⁻³
2505 reflections	Δρ_min = −0.23 e Å⁻³
330 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
7 restraints	Extinction coefficient: 0.0032 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), no Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.008 (17)

Crystal data top

C₁₄H₁₅NO₂S	V = 2693.2 (5) Å³
M_r = 261.33	Z = 8
Orthorhombic, Pca2₁	Cu Kα radiation
a = 19.113 (3) Å	µ = 2.09 mm⁻¹
b = 8.9290 (8) Å	T = 299 K
c = 15.781 (1) Å	0.50 × 0.43 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2421 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.050
T_min = 0.401, T_max = 0.593	3 standard reflections every 120 min
4916 measured reflections	intensity decay: 1.0%
2505 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.26 e Å⁻³
S = 1.09	Δρ_min = −0.23 e Å⁻³
2505 reflections	Absolute structure: Flack (1983), no Friedel pairs
330 parameters	Absolute structure parameter: 0.008 (17)
7 restraints

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	0.25250 (4)	0.26684 (7)	0.22911 (5)	0.05031 (19)
O1	0.18269 (11)	0.3237 (2)	0.23659 (15)	0.0594 (5)
O2	0.26004 (13)	0.1099 (2)	0.21441 (18)	0.0702 (7)
N1	0.29100 (14)	0.3475 (3)	0.14888 (15)	0.0544 (5)
H1N	0.3002	0.2948	0.1046	0.065*
C1	0.29873 (15)	0.3238 (3)	0.32001 (19)	0.0520 (6)
C2	0.36811 (17)	0.2791 (4)	0.3346 (2)	0.0603 (7)
C3	0.39906 (19)	0.3302 (5)	0.4076 (3)	0.0763 (10)
H3	0.4448	0.3004	0.4188	0.092*
C4	0.36652 (19)	0.4232 (5)	0.4657 (2)	0.0767 (9)
C5	0.2984 (2)	0.4650 (4)	0.4490 (2)	0.0737 (9)
H5	0.2748	0.5266	0.4869	0.088*
C6	0.26517 (16)	0.4164 (3)	0.3769 (2)	0.0587 (6)
H6	0.2194	0.4464	0.3663	0.070*
C7	0.31002 (15)	0.5019 (3)	0.14938 (15)	0.0472 (5)
C8	0.37518 (17)	0.5411 (3)	0.11944 (17)	0.0559 (6)
H8	0.4067	0.4679	0.1022	0.067*
C9	0.3931 (2)	0.6918 (4)	0.1154 (2)	0.0679 (9)
H9	0.4363	0.7200	0.0935	0.081*
C10	0.3472 (2)	0.7996 (3)	0.1438 (2)	0.0693 (9)
H10	0.3596	0.9003	0.1414	0.083*
C11	0.2844 (2)	0.7591 (3)	0.1749 (3)	0.0706 (8)
H11	0.2539	0.8323	0.1947	0.085*
C12	0.26465 (19)	0.6103 (3)	0.1777 (2)	0.0633 (7)
H12	0.2209	0.5836	0.1987	0.076*
C13	0.4085 (2)	0.1767 (5)	0.2756 (3)	0.0844 (12)
H13A	0.4131	0.2237	0.2211	0.101*
H13B	0.3838	0.0837	0.2695	0.101*
H13C	0.4541	0.1579	0.2987	0.101*
C14	0.4032 (3)	0.4784 (9)	0.5438 (3)	0.1129 (18)
H14A	0.4524	0.4585	0.5392	0.135*
H14B	0.3848	0.4278	0.5927	0.135*
H14C	0.3959	0.5843	0.5497	0.135*
S2	0.58393 (3)	0.79647 (7)	0.45792 (4)	0.04598 (18)
O3	0.61521 (12)	0.8591 (3)	0.53213 (13)	0.0605 (5)
O4	0.59126 (13)	0.6383 (2)	0.44450 (15)	0.0665 (6)
N2	0.61782 (13)	0.8727 (3)	0.37433 (15)	0.0509 (5)
H2N	0.6431	0.8164	0.3424	0.061*
C15	0.49526 (13)	0.8489 (3)	0.45929 (17)	0.0496 (5)
C16	0.44843 (19)	0.7964 (4)	0.3987 (2)	0.0673 (9)
C17	0.3784 (2)	0.8473 (6)	0.4075 (3)	0.0906 (14)
H17	0.3454	0.8140	0.3684	0.109*
C18	0.35654 (19)	0.9422 (6)	0.4700 (3)	0.0949 (15)
C19	0.4042 (2)	0.9912 (6)	0.5270 (3)	0.0854 (12)
H19	0.3904	1.0567	0.5697	0.102*
C20	0.47306 (17)	0.9454 (4)	0.52259 (19)	0.0634 (8)
H20	0.5050	0.9797	0.5626	0.076*
C21	0.60945 (12)	1.0244 (3)	0.34916 (17)	0.0451 (5)
C22	0.60950 (17)	1.1394 (3)	0.4086 (2)	0.0569 (6)
H22	0.6138	1.1185	0.4660	0.068*
C23	0.6030 (2)	1.2854 (4)	0.3806 (3)	0.0678 (9)
H23	0.6019	1.3629	0.4199	0.081*
C24	0.5981 (2)	1.3182 (4)	0.2961 (3)	0.0686 (9)
H24	0.5945	1.4172	0.2782	0.082*
C25	0.5986 (2)	1.2031 (4)	0.2377 (3)	0.0692 (8)
H25	0.5956	1.2244	0.1801	0.083*
C26	0.60355 (16)	1.0569 (3)	0.26450 (18)	0.0555 (7)
H26	0.6029	0.9797	0.2250	0.067*
C27	0.4682 (3)	0.6917 (6)	0.3282 (3)	0.1016 (16)
H27A	0.4895	0.6034	0.3516	0.122*
H27B	0.5008	0.7405	0.2910	0.122*
H27C	0.4271	0.6641	0.2970	0.122*
C28	0.2808 (2)	0.9939 (10)	0.4738 (4)	0.136 (2)
H28A	0.2542	0.9255	0.5079	0.164*
H28B	0.2617	0.9966	0.4175	0.164*
H28C	0.2787	1.0922	0.4983	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0539 (3)	0.0320 (3)	0.0650 (4)	−0.0034 (3)	0.0112 (3)	0.0002 (3)
O1	0.0510 (9)	0.0539 (10)	0.0733 (12)	−0.0010 (9)	0.0070 (10)	0.0024 (11)
O2	0.0789 (14)	0.0290 (9)	0.1028 (18)	−0.0078 (10)	0.0143 (12)	−0.0020 (11)
N1	0.0726 (13)	0.0345 (10)	0.0562 (11)	−0.0029 (11)	0.0167 (11)	−0.0072 (9)
C1	0.0531 (13)	0.0439 (13)	0.0591 (14)	−0.0029 (12)	0.0083 (12)	0.0089 (11)
C2	0.0536 (14)	0.0536 (15)	0.0736 (18)	0.0048 (12)	0.0098 (13)	0.0140 (14)
C3	0.0591 (16)	0.086 (3)	0.084 (2)	−0.0040 (18)	−0.0014 (16)	0.021 (2)
C4	0.0737 (18)	0.087 (2)	0.0698 (18)	−0.0161 (18)	−0.0008 (17)	0.0115 (19)
C5	0.0827 (19)	0.073 (2)	0.0654 (17)	−0.0087 (18)	0.0111 (16)	−0.0025 (17)
C6	0.0586 (14)	0.0540 (15)	0.0634 (15)	−0.0009 (13)	0.0099 (12)	−0.0011 (13)
C7	0.0647 (14)	0.0334 (11)	0.0434 (10)	−0.0016 (11)	0.0072 (11)	−0.0012 (9)
C8	0.0702 (15)	0.0467 (15)	0.0509 (12)	−0.0030 (14)	0.0146 (12)	−0.0053 (11)
C9	0.084 (2)	0.0538 (18)	0.0657 (17)	−0.0167 (17)	0.0161 (17)	0.0060 (14)
C10	0.101 (2)	0.0387 (13)	0.0684 (17)	−0.0104 (15)	0.0068 (18)	0.0037 (13)
C11	0.094 (2)	0.0341 (13)	0.084 (2)	0.0069 (16)	0.0097 (19)	−0.0004 (14)
C12	0.0739 (18)	0.0386 (13)	0.0774 (19)	0.0019 (14)	0.0182 (15)	0.0022 (14)
C13	0.0657 (19)	0.079 (2)	0.109 (3)	0.023 (2)	0.0120 (19)	0.004 (2)
C14	0.118 (3)	0.141 (5)	0.080 (2)	−0.039 (4)	−0.019 (3)	0.003 (3)
S2	0.0532 (3)	0.0368 (3)	0.0479 (3)	0.0046 (2)	−0.0059 (2)	0.0046 (2)
O3	0.0603 (11)	0.0653 (13)	0.0561 (10)	0.0023 (10)	−0.0154 (9)	0.0038 (10)
O4	0.0918 (14)	0.0341 (9)	0.0735 (13)	0.0111 (10)	−0.0019 (11)	0.0091 (10)
N2	0.0620 (12)	0.0344 (10)	0.0564 (11)	0.0082 (10)	0.0091 (10)	−0.0013 (9)
C15	0.0500 (11)	0.0483 (12)	0.0505 (12)	−0.0020 (11)	−0.0022 (11)	0.0131 (11)
C16	0.0647 (17)	0.0704 (19)	0.0669 (17)	−0.0195 (16)	−0.0227 (15)	0.0204 (15)
C17	0.063 (2)	0.107 (3)	0.102 (3)	−0.021 (2)	−0.027 (2)	0.044 (3)
C18	0.0586 (17)	0.117 (4)	0.109 (3)	0.010 (2)	0.013 (2)	0.062 (3)
C19	0.073 (2)	0.097 (3)	0.086 (2)	0.021 (2)	0.0239 (19)	0.028 (2)
C20	0.0652 (17)	0.0663 (18)	0.0587 (15)	0.0104 (15)	0.0058 (12)	0.0105 (14)
C21	0.0425 (10)	0.0360 (12)	0.0569 (13)	0.0015 (10)	0.0081 (10)	0.0029 (10)
C22	0.0685 (16)	0.0403 (14)	0.0618 (14)	−0.0002 (13)	0.0056 (13)	−0.0040 (12)
C23	0.077 (2)	0.0372 (13)	0.089 (2)	−0.0024 (14)	0.0117 (18)	−0.0048 (15)
C24	0.0722 (18)	0.0446 (17)	0.089 (2)	−0.0011 (15)	0.0141 (18)	0.0130 (16)
C25	0.0773 (18)	0.0575 (19)	0.073 (2)	0.0020 (15)	0.0124 (17)	0.0208 (17)
C26	0.0635 (14)	0.0470 (15)	0.0559 (14)	0.0000 (13)	0.0099 (12)	0.0021 (12)
C27	0.125 (4)	0.095 (3)	0.084 (3)	−0.024 (3)	−0.038 (3)	−0.015 (2)
C28	0.065 (2)	0.177 (5)	0.167 (5)	0.019 (3)	0.018 (3)	0.071 (5)

Geometric parameters (Å, º) top

S1—O2	1.4278 (19)	S2—O3	1.429 (2)
S1—O1	1.433 (2)	S2—O4	1.435 (2)
S1—N1	1.632 (2)	S2—N2	1.619 (2)
S1—C1	1.760 (3)	S2—C15	1.758 (3)
N1—C7	1.426 (3)	N2—C21	1.421 (3)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.379 (4)	C15—C20	1.386 (4)
C1—C2	1.404 (4)	C15—C16	1.391 (4)
C2—C3	1.373 (6)	C16—C17	1.421 (6)
C2—C13	1.517 (5)	C16—C27	1.501 (6)
C3—C4	1.384 (6)	C17—C18	1.366 (8)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.380 (6)	C18—C19	1.354 (7)
C4—C14	1.502 (6)	C18—C28	1.520 (6)
C5—C6	1.373 (5)	C19—C20	1.379 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.374 (4)	C21—C26	1.372 (4)
C7—C8	1.377 (4)	C21—C22	1.390 (4)
C8—C9	1.390 (4)	C22—C23	1.382 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.377 (6)	C23—C24	1.367 (6)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.347 (6)	C24—C25	1.381 (6)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.382 (4)	C25—C26	1.375 (4)
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

O2—S1—O1	117.09 (14)	O3—S2—O4	117.71 (14)
O2—S1—N1	105.17 (14)	O3—S2—N2	109.64 (12)
O1—S1—N1	109.11 (13)	O4—S2—N2	104.73 (13)
O2—S1—C1	111.43 (15)	O3—S2—C15	106.81 (14)
O1—S1—C1	107.33 (13)	O4—S2—C15	110.97 (14)
N1—S1—C1	106.18 (12)	N2—S2—C15	106.48 (12)
C7—N1—S1	122.50 (18)	C21—N2—S2	125.67 (18)
C7—N1—H1N	118.7	C21—N2—H2N	117.2
S1—N1—H1N	118.7	S2—N2—H2N	117.2
C6—C1—C2	120.2 (3)	C20—C15—C16	120.5 (3)
C6—C1—S1	118.1 (2)	C20—C15—S2	118.0 (2)
C2—C1—S1	121.7 (2)	C16—C15—S2	121.5 (3)
C3—C2—C1	116.8 (3)	C15—C16—C17	115.6 (4)
C3—C2—C13	119.8 (3)	C15—C16—C27	123.8 (4)
C1—C2—C13	123.4 (3)	C17—C16—C27	120.6 (4)
C2—C3—C4	124.1 (3)	C18—C17—C16	123.8 (4)
C2—C3—H3	117.9	C18—C17—H17	118.1
C4—C3—H3	117.9	C16—C17—H17	118.1
C5—C4—C3	117.4 (4)	C19—C18—C17	118.4 (4)
C5—C4—C14	120.6 (4)	C19—C18—C28	121.1 (6)
C3—C4—C14	122.0 (4)	C17—C18—C28	120.5 (5)
C6—C5—C4	120.6 (4)	C18—C19—C20	120.9 (5)
C6—C5—H5	119.7	C18—C19—H19	119.6
C4—C5—H5	119.7	C20—C19—H19	119.6
C5—C6—C1	120.9 (3)	C19—C20—C15	120.8 (4)
C5—C6—H6	119.5	C19—C20—H20	119.6
C1—C6—H6	119.5	C15—C20—H20	119.6
C12—C7—C8	120.2 (3)	C26—C21—C22	120.0 (3)
C12—C7—N1	121.4 (3)	C26—C21—N2	118.9 (2)
C8—C7—N1	118.3 (2)	C22—C21—N2	121.0 (3)
C7—C8—C9	118.9 (3)	C23—C22—C21	118.8 (3)
C7—C8—H8	120.5	C23—C22—H22	120.6
C9—C8—H8	120.5	C21—C22—H22	120.6
C10—C9—C8	120.4 (3)	C24—C23—C22	121.3 (3)
C10—C9—H9	119.8	C24—C23—H23	119.3
C8—C9—H9	119.8	C22—C23—H23	119.3
C11—C10—C9	119.9 (3)	C23—C24—C25	119.4 (3)
C11—C10—H10	120.1	C23—C24—H24	120.3
C9—C10—H10	120.1	C25—C24—H24	120.3
C10—C11—C12	120.9 (3)	C26—C25—C24	120.1 (4)
C10—C11—H11	119.6	C26—C25—H25	120.0
C12—C11—H11	119.6	C24—C25—H25	120.0
C7—C12—C11	119.6 (3)	C21—C26—C25	120.4 (3)
C7—C12—H12	120.2	C21—C26—H26	119.8
C11—C12—H12	120.2	C25—C26—H26	119.8
C2—C13—H13A	109.5	C16—C27—H27A	109.5
C2—C13—H13B	109.5	C16—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C2—C13—H13C	109.5	C16—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C4—C14—H14A	109.5	C18—C28—H28A	109.5
C4—C14—H14B	109.5	C18—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C4—C14—H14C	109.5	C18—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5

O2—S1—N1—C7	−164.3 (2)	O3—S2—N2—C21	−67.5 (3)
O1—S1—N1—C7	69.3 (3)	O4—S2—N2—C21	165.3 (2)
C1—S1—N1—C7	−46.1 (3)	C15—S2—N2—C21	47.7 (3)
O2—S1—C1—C6	−133.9 (2)	O3—S2—C15—C20	5.2 (3)
O1—S1—C1—C6	−4.5 (3)	O4—S2—C15—C20	134.7 (2)
N1—S1—C1—C6	112.1 (2)	N2—S2—C15—C20	−111.9 (2)
O2—S1—C1—C2	47.0 (3)	O3—S2—C15—C16	−175.1 (2)
O1—S1—C1—C2	176.5 (2)	O4—S2—C15—C16	−45.6 (3)
N1—S1—C1—C2	−67.0 (3)	N2—S2—C15—C16	67.8 (3)
C6—C1—C2—C3	1.0 (4)	C20—C15—C16—C17	−0.5 (4)
S1—C1—C2—C3	−180.0 (3)	S2—C15—C16—C17	179.8 (2)
C6—C1—C2—C13	179.5 (3)	C20—C15—C16—C27	−180.0 (3)
S1—C1—C2—C13	−1.4 (4)	S2—C15—C16—C27	0.4 (5)
C1—C2—C3—C4	−1.0 (5)	C15—C16—C17—C18	0.4 (6)
C13—C2—C3—C4	−179.6 (4)	C27—C16—C17—C18	179.9 (4)
C2—C3—C4—C5	0.8 (6)	C16—C17—C18—C19	0.1 (6)
C2—C3—C4—C14	−178.8 (4)	C16—C17—C18—C28	178.7 (4)
C3—C4—C5—C6	−0.6 (5)	C17—C18—C19—C20	−0.6 (6)
C14—C4—C5—C6	179.0 (4)	C28—C18—C19—C20	−179.2 (4)
C4—C5—C6—C1	0.6 (5)	C18—C19—C20—C15	0.5 (6)
C2—C1—C6—C5	−0.8 (5)	C16—C15—C20—C19	0.1 (5)
S1—C1—C6—C5	−179.9 (3)	S2—C15—C20—C19	179.8 (3)
S1—N1—C7—C12	−45.2 (4)	S2—N2—C21—C26	−142.9 (2)
S1—N1—C7—C8	135.7 (2)	S2—N2—C21—C22	39.2 (4)
C12—C7—C8—C9	−2.4 (5)	C26—C21—C22—C23	0.5 (4)
N1—C7—C8—C9	176.7 (3)	N2—C21—C22—C23	178.4 (3)
C7—C8—C9—C10	2.2 (5)	C21—C22—C23—C24	−1.5 (6)
C8—C9—C10—C11	−0.5 (6)	C22—C23—C24—C25	1.0 (6)
C9—C10—C11—C12	−1.0 (6)	C23—C24—C25—C26	0.4 (6)
C8—C7—C12—C11	1.0 (5)	C22—C21—C26—C25	0.9 (4)
N1—C7—C12—C11	−178.1 (3)	N2—C21—C26—C25	−177.0 (3)
C10—C11—C12—C7	0.8 (6)	C24—C25—C26—C21	−1.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86	2.41	3.164 (3)	147
N2—H2N···O1ⁱⁱ	0.86	2.22	3.056 (3)	164
C11—H11···O2ⁱⁱⁱ	0.93	2.50	3.227 (4)	135
C23—H23···O4ⁱⁱⁱ	0.93	2.50	3.316 (4)	147

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₂S
M_r	261.33
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	299
a, b, c (Å)	19.113 (3), 8.9290 (8), 15.781 (1)
V (Å³)	2693.2 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.09
Crystal size (mm)	0.50 × 0.43 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.401, 0.593
No. of measured, independent and observed [I > 2σ(I)] reflections	4916, 2505, 2421
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 1.09
No. of reflections	2505
No. of parameters	330
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23
Absolute structure	Flack (1983), no Friedel pairs
Absolute structure parameter	0.008 (17)

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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···O3ⁱ	0.86	2.41	3.164 (3)	146.5
N2—H2N···O1ⁱⁱ	0.86	2.22	3.056 (3)	164.1
C11—H11···O2ⁱⁱⁱ	0.93	2.50	3.227 (4)	135.1
C23—H23···O4ⁱⁱⁱ	0.93	2.50	3.316 (4)	146.9

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

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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