4-Methyl-N-phenyl­benzene­sulfonamide

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

doi:10.1107/S1600536809016377

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1219

doi:10.1107/S1600536809016377

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4-Methyl-N-phenylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 9 April 2009; accepted 30 April 2009; online 7 May 2009)

In the title compound, C₁₃H₁₃NO₂S, the dihedral angle between the aromatic rings is 68.4 (1)°. In the crystal, the molecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds. The unit cell of this compound was reported previously [Oh et al. (1985 ). Chung. Kwa. Yong. (Chung. J. Sci.), 12, 67] but no atomic coordinates were established in the earlier study.

Related literature

For related structures, see: Gelbrich et al. (2007 ); Gowda et al. (2005 , 2009 a ,b); Gowda, Foro, Nirmala, Terao & Fuess (2009); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₃H₁₃NO₂S
M_r = 247.30
Monoclinic, P 2₁ /c
a = 8.770 (2) Å
b = 9.768 (2) Å
c = 16.234 (5) Å
β = 113.200 (2)°
V = 1278.2 (6) Å³
Z = 4
Cu Kα radiation
μ = 2.17 mm⁻¹
T = 299 K
0.55 × 0.50 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.336, T_max = 0.420
3091 measured reflections
2278 independent reflections
2041 reflections with I > 2σ(I)
R_int = 0.096
3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.217
S = 1.10
2278 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.77 (4)	2.17 (5)	2.932 (4)	172 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S1600536809016377/bq2138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016377/bq2138Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of substituent on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009a, b, c), in the present work, the structure of 4-methyl-N-(phenyl)- benzenesulfonamide (I) has been determined. The conformations of the N—C bond in the C—SO₂—NH—C segment of the structure are "trans" and "gauche" with respect to the S══O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of -51.6 (3)°. The two benzene rings in (I) are tilted relative to each other by 68.4 (1)°. The other bond parameters in (I) are similar to those observed in 2,4-dimethyl-N-(phenyl)-benzenesulfonamide (Gowda et al., 2009 a), 4-chloro-2-methyl-N-(phenyl)benzenesulfonamide (Gowda et al., 2009 b), 4-methyl-N-(3,4-dimethylphenyl)- benzenesulfonamide (Gowda et al., 2009 c)) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The N—H···O hydrogen bonds (Table 1) pack the molecules into column like chains in the direction of a- axis (Fig. 2).

Related literature top

For background literature, see: Gelbrich et al. (2007); Gowda et al. (2005, 2009a,b); Gowda et al. (2009); Perlovich et al. (2006).

Experimental top

The purity of the commercial sample was checked and characterized by recording its infrared and NMR spectra (Gowda et al., 2005). 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 (I), showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

4-Methyl-N-phenylbenzenesulfonamide top

Crystal data top

C₁₃H₁₃NO₂S	F(000) = 520
M_r = 247.30	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.770 (2) Å	θ = 5.4–20.7°
b = 9.768 (2) Å	µ = 2.17 mm⁻¹
c = 16.234 (5) Å	T = 299 K
β = 113.200 (2)°	Prism, colourless
V = 1278.2 (6) Å³	0.55 × 0.50 × 0.40 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.096
Graphite monochromator	θ_max = 66.9°, θ_min = 5.4°
ω/2θ scans	h = −3→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→0
T_min = 0.336, T_max = 0.420	l = −19→19
3091 measured reflections	3 standard reflections every 120 min
2278 independent reflections	intensity decay: 2.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.217	w = 1/[σ²(F_o²) + (0.1256P)² + 0.4489P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.023
2278 reflections	Δρ_max = 0.47 e Å⁻³
159 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: (SHELXL97; Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.060 (5)

Crystal data top

C₁₃H₁₃NO₂S	V = 1278.2 (6) Å³
M_r = 247.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.770 (2) Å	µ = 2.17 mm⁻¹
b = 9.768 (2) Å	T = 299 K
c = 16.234 (5) Å	0.55 × 0.50 × 0.40 mm
β = 113.200 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2041 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.096
T_min = 0.336, T_max = 0.420	3 standard reflections every 120 min
3091 measured reflections	intensity decay: 2.0%
2278 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.217	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.47 e Å⁻³
2278 reflections	Δρ_min = −0.50 e Å⁻³
159 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
C1	0.3623 (4)	0.2024 (3)	0.4713 (2)	0.0641 (7)
C2	0.2930 (5)	0.0780 (4)	0.4369 (2)	0.0810 (9)
H2	0.2768	0.0535	0.3787	0.097*
C3	0.2480 (5)	−0.0098 (4)	0.4897 (3)	0.0929 (11)
H3	0.2037	−0.0949	0.4670	0.112*
C4	0.2669 (4)	0.0254 (4)	0.5752 (3)	0.0866 (11)
C5	0.3360 (5)	0.1527 (5)	0.6073 (3)	0.0881 (11)
H5	0.3495	0.1790	0.6648	0.106*
C6	0.3838 (4)	0.2390 (4)	0.5571 (2)	0.0799 (9)
H6	0.4313	0.3230	0.5804	0.096*
C7	0.1172 (4)	0.4284 (3)	0.3472 (2)	0.0708 (8)
C8	0.0374 (5)	0.3408 (4)	0.2771 (3)	0.0855 (10)
H8	0.0972	0.2892	0.2519	0.103*
C9	−0.1321 (5)	0.3311 (5)	0.2450 (3)	0.0982 (13)
H9	−0.1867	0.2712	0.1981	0.118*
C10	−0.2223 (5)	0.4065 (6)	0.2800 (4)	0.1095 (16)
H10	−0.3372	0.3987	0.2570	0.131*
C11	−0.1428 (6)	0.4932 (6)	0.3488 (4)	0.1133 (16)
H11	−0.2042	0.5457	0.3725	0.136*
C12	0.0292 (5)	0.5048 (4)	0.3844 (3)	0.0899 (11)
H12	0.0833	0.5631	0.4324	0.108*
C13	0.2197 (7)	−0.0689 (6)	0.6336 (4)	0.1236 (18)
H13A	0.1824	−0.1544	0.6032	0.148*
H13B	0.1322	−0.0283	0.6468	0.148*
H13C	0.3142	−0.0845	0.6884	0.148*
N1	0.2939 (3)	0.4457 (3)	0.3838 (2)	0.0762 (8)
H1N	0.318 (5)	0.497 (5)	0.423 (3)	0.091*
O1	0.5798 (3)	0.3739 (3)	0.45932 (19)	0.0863 (8)
O2	0.4014 (3)	0.2496 (3)	0.32444 (16)	0.0858 (8)
S1	0.42133 (9)	0.31592 (8)	0.40573 (5)	0.0689 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0670 (15)	0.0712 (17)	0.0583 (16)	0.0062 (12)	0.0292 (13)	−0.0007 (13)
C2	0.104 (2)	0.077 (2)	0.071 (2)	−0.0127 (17)	0.0435 (18)	−0.0128 (16)
C3	0.111 (3)	0.077 (2)	0.103 (3)	−0.0077 (19)	0.055 (2)	0.001 (2)
C4	0.091 (2)	0.095 (2)	0.091 (2)	0.029 (2)	0.054 (2)	0.029 (2)
C5	0.103 (2)	0.106 (3)	0.066 (2)	0.017 (2)	0.0442 (18)	0.0030 (19)
C6	0.095 (2)	0.086 (2)	0.0664 (19)	0.0000 (17)	0.0399 (17)	−0.0132 (16)
C7	0.0718 (17)	0.0718 (18)	0.0711 (18)	−0.0004 (13)	0.0305 (14)	0.0198 (14)
C8	0.089 (2)	0.091 (2)	0.076 (2)	−0.0102 (18)	0.0330 (18)	0.0057 (18)
C9	0.084 (2)	0.106 (3)	0.090 (3)	−0.013 (2)	0.019 (2)	0.019 (2)
C10	0.079 (2)	0.121 (4)	0.114 (4)	−0.003 (2)	0.023 (2)	0.038 (3)
C11	0.094 (3)	0.127 (4)	0.128 (4)	0.030 (3)	0.054 (3)	0.028 (3)
C12	0.090 (2)	0.088 (2)	0.095 (3)	0.0093 (18)	0.0404 (19)	0.008 (2)
C13	0.143 (4)	0.120 (4)	0.140 (4)	0.033 (3)	0.090 (3)	0.052 (3)
N1	0.0754 (16)	0.0734 (17)	0.0824 (19)	−0.0075 (12)	0.0341 (14)	−0.0006 (13)
O1	0.0727 (13)	0.0901 (16)	0.1026 (18)	−0.0101 (11)	0.0414 (12)	−0.0152 (14)
O2	0.1054 (17)	0.0989 (18)	0.0709 (14)	−0.0013 (14)	0.0541 (13)	−0.0068 (12)
S1	0.0721 (6)	0.0749 (6)	0.0691 (6)	−0.0036 (3)	0.0379 (4)	−0.0048 (3)

Geometric parameters (Å, º) top

C1—C2	1.374 (5)	C8—H8	0.9300
C1—C6	1.378 (4)	C9—C10	1.358 (7)
C1—S1	1.750 (3)	C9—H9	0.9300
C2—C3	1.375 (5)	C10—C11	1.355 (8)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.375 (6)	C11—C12	1.391 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.392 (6)	C12—H12	0.9300
C4—C13	1.492 (5)	C13—H13A	0.9600
C5—C6	1.349 (5)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.633 (3)
C7—C12	1.373 (5)	N1—H1N	0.77 (4)
C7—C8	1.375 (5)	O1—S1	1.434 (2)
C7—N1	1.434 (4)	O2—S1	1.418 (2)
C8—C9	1.371 (5)

C2—C1—C6	120.1 (3)	C8—C9—H9	119.1
C2—C1—S1	120.2 (2)	C11—C10—C9	119.2 (4)
C6—C1—S1	119.7 (3)	C11—C10—H10	120.4
C1—C2—C3	119.2 (3)	C9—C10—H10	120.4
C1—C2—H2	120.4	C10—C11—C12	121.0 (5)
C3—C2—H2	120.4	C10—C11—H11	119.5
C2—C3—C4	121.5 (4)	C12—C11—H11	119.5
C2—C3—H3	119.2	C7—C12—C11	118.6 (4)
C4—C3—H3	119.2	C7—C12—H12	120.7
C3—C4—C5	117.6 (3)	C11—C12—H12	120.7
C3—C4—C13	122.3 (5)	C4—C13—H13A	109.5
C5—C4—C13	120.1 (4)	C4—C13—H13B	109.5
C6—C5—C4	121.7 (3)	H13A—C13—H13B	109.5
C6—C5—H5	119.2	C4—C13—H13C	109.5
C4—C5—H5	119.2	H13A—C13—H13C	109.5
C5—C6—C1	119.9 (4)	H13B—C13—H13C	109.5
C5—C6—H6	120.1	C7—N1—S1	122.3 (2)
C1—C6—H6	120.1	C7—N1—H1N	109 (3)
C12—C7—C8	120.7 (3)	S1—N1—H1N	113 (3)
C12—C7—N1	117.2 (3)	O2—S1—O1	118.69 (15)
C8—C7—N1	122.0 (3)	O2—S1—N1	109.20 (17)
C9—C8—C7	118.7 (4)	O1—S1—N1	104.00 (16)
C9—C8—H8	120.7	O2—S1—C1	108.57 (15)
C7—C8—H8	120.7	O1—S1—C1	109.23 (16)
C10—C9—C8	121.8 (5)	N1—S1—C1	106.47 (14)
C10—C9—H9	119.1

C6—C1—C2—C3	−0.9 (5)	C8—C7—C12—C11	−0.9 (6)
S1—C1—C2—C3	179.8 (3)	N1—C7—C12—C11	178.3 (4)
C1—C2—C3—C4	1.6 (6)	C10—C11—C12—C7	1.3 (7)
C2—C3—C4—C5	−1.0 (6)	C12—C7—N1—S1	135.5 (3)
C2—C3—C4—C13	−179.6 (4)	C8—C7—N1—S1	−45.3 (4)
C3—C4—C5—C6	−0.3 (5)	C7—N1—S1—O2	65.5 (3)
C13—C4—C5—C6	178.3 (4)	C7—N1—S1—O1	−166.9 (3)
C4—C5—C6—C1	1.0 (6)	C7—N1—S1—C1	−51.6 (3)
C2—C1—C6—C5	−0.3 (5)	C2—C1—S1—O2	−6.3 (3)
S1—C1—C6—C5	178.9 (3)	C6—C1—S1—O2	174.5 (2)
C12—C7—C8—C9	−0.1 (5)	C2—C1—S1—O1	−137.1 (3)
N1—C7—C8—C9	−179.2 (3)	C6—C1—S1—O1	43.7 (3)
C7—C8—C9—C10	0.7 (6)	C2—C1—S1—N1	111.2 (3)
C8—C9—C10—C11	−0.4 (7)	C6—C1—S1—N1	−68.0 (3)
C9—C10—C11—C12	−0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.77 (4)	2.17 (5)	2.932 (4)	172 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₂S
M_r	247.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	8.770 (2), 9.768 (2), 16.234 (5)
β (°)	113.200 (2)
V (Å³)	1278.2 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.17
Crystal size (mm)	0.55 × 0.50 × 0.40

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.336, 0.420
No. of measured, independent and observed [I > 2σ(I)] reflections	3091, 2278, 2041
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.217, 1.10
No. of reflections	2278
No. of parameters	159
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.50

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···O1ⁱ	0.77 (4)	2.17 (5)	2.932 (4)	172 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

References

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