N-(2,3-Dimethyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809002098

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o366

doi:10.1107/S1600536809002098

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N-(2,3-Dimethylphenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b 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 15 January 2009; accepted 16 January 2009; online 23 January 2009)

In the crystal structure of the title compound, C₁₄H₁₅NO₂S, the amino H atom is trans to one of the O atoms of the SO₂ group. Furthermore, the N—H bond is anti to the ortho- and meta-methyl groups of the aromatic ring. The two aromatic rings are tilted relative to each other by 64.8 (1)°. The molecules form zigzag chains along the a axis via intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Gelbrich et al. (2007 ); Gowda et al. (2005 ); Gowda et al. (2008a ,b ,c ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 261.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.3969 (5) Å
b = 8.8767 (6) Å
c = 23.082 (2) Å
V = 1310.67 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 299 (2) K
0.50 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.889, T_max = 0.958
5869 measured reflections
2611 independent reflections
2200 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.07
2611 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1060 Friedel pairs
Flack parameter: −0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (3)	2.10 (3)	2.936 (2)	176 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); 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, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002098/bt2853sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002098/bt2853Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008a, 2008b, 2008c), the structure of N-(2,3-dimethylphenyl)-benzenesulfonamide has been determined. The amino H atom is trans to one of the O atoms of the SO₂ group (Fig. 1), similar to that 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 two benzene rings are tilted relative to each other by 64.8 (1)°, compared with the values of 44.9 (1)° in N-(2,6-dimethylphenyl)- benzenesulfonamide and 61.5 (1)° in N-(2-methylphenyl)-benzenesulfonamide. The other bond parameters of the title compound are similar to those observed in other N-(aryl)-sulfonamides. The crystal packing is stabilized by intermolecular N—H···O hydrogen bonds forming zigzag chains along the a axis (Table 1, Fig. 2).

Related literature top

For related literature, see: Gelbrich et al. (2007); Gowda et al. (2005); Gowda et al. (2008a,b,c); Perlovich et al. (2006)

Experimental top

The solution of benzene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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 benzenesulfonylchloride was treated with 2,3-dimethylaniline 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 cc). The resultant solid N-(2,3-dimethylphenyl)-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 (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: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); 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.

N-(2,3-Dimethylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₅NO₂S	F(000) = 552
M_r = 261.33	D_x = 1.324 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2432 reflections
a = 6.3969 (5) Å	θ = 2.3–27.7°
b = 8.8767 (6) Å	µ = 0.24 mm⁻¹
c = 23.082 (2) Å	T = 299 K
V = 1310.67 (18) Å³	Rod, colourless
Z = 4	0.50 × 0.30 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2611 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −7→7
T_min = 0.889, T_max = 0.958	k = −5→11
5869 measured reflections	l = −13→28

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0525P)² + 0.1566P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.025
2611 reflections	Δρ_max = 0.20 e Å⁻³
168 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1060 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (9)

Crystal data top

C₁₄H₁₅NO₂S	V = 1310.67 (18) Å³
M_r = 261.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.3969 (5) Å	µ = 0.24 mm⁻¹
b = 8.8767 (6) Å	T = 299 K
c = 23.082 (2) Å	0.50 × 0.30 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2611 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2200 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.958	R_int = 0.014
5869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	Δρ_max = 0.20 e Å⁻³
S = 1.07	Δρ_min = −0.19 e Å⁻³
2611 reflections	Absolute structure: Flack (1983), 1060 Friedel pairs
168 parameters	Absolute structure parameter: −0.04 (9)
0 restraints

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2007) 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	0.2823 (3)	−0.0378 (2)	0.43543 (9)	0.0389 (5)
C2	0.4720 (4)	−0.0422 (3)	0.46456 (11)	0.0507 (6)
H2	0.5124	0.0374	0.4882	0.061*
C3	0.5998 (4)	−0.1662 (3)	0.45797 (13)	0.0651 (7)
H3	0.7262	−0.1708	0.4778	0.078*
C4	0.5424 (5)	−0.2816 (3)	0.42263 (14)	0.0701 (9)
H4	0.6285	−0.3655	0.4189	0.084*
C5	0.3566 (6)	−0.2746 (3)	0.39226 (13)	0.0740 (9)
H5	0.3206	−0.3519	0.3670	0.089*
C6	0.2245 (5)	−0.1532 (3)	0.39934 (11)	0.0564 (6)
H6	0.0974	−0.1496	0.3798	0.068*
C7	0.2683 (4)	0.2922 (2)	0.36164 (9)	0.0419 (5)
C8	0.1257 (4)	0.3805 (2)	0.33190 (9)	0.0441 (5)
C9	0.1664 (4)	0.4088 (3)	0.27267 (10)	0.0536 (6)
C10	0.3383 (5)	0.3483 (3)	0.24667 (12)	0.0701 (8)
H10	0.3632	0.3679	0.2077	0.084*
C11	0.4762 (5)	0.2585 (3)	0.27715 (13)	0.0757 (9)
H11	0.5909	0.2167	0.2583	0.091*
C12	0.4452 (4)	0.2308 (3)	0.33475 (11)	0.0566 (7)
H12	0.5395	0.1724	0.3557	0.068*
C13	−0.0598 (4)	0.4452 (3)	0.36156 (12)	0.0601 (7)
H13A	−0.0457	0.5528	0.3637	0.072*
H13B	−0.0697	0.4045	0.4000	0.072*
H13C	−0.1837	0.4203	0.3402	0.072*
C14	0.0210 (6)	0.5071 (4)	0.23845 (14)	0.0840 (10)
H14A	0.0214	0.6070	0.2544	0.101*
H14B	−0.1179	0.4664	0.2402	0.101*
H14C	0.0665	0.5108	0.1988	0.101*
N1	0.2351 (3)	0.2670 (2)	0.42314 (7)	0.0413 (5)
H1N	0.337 (4)	0.290 (3)	0.4439 (10)	0.050*
O1	−0.0648 (3)	0.09633 (19)	0.41129 (7)	0.0567 (5)
O2	0.0967 (3)	0.13781 (18)	0.50761 (6)	0.0577 (5)
S1	0.11619 (8)	0.11797 (6)	0.44610 (2)	0.04071 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0474 (12)	0.0325 (11)	0.0367 (11)	−0.0028 (9)	0.0072 (10)	0.0039 (9)
C2	0.0512 (14)	0.0446 (13)	0.0562 (15)	0.0015 (11)	−0.0003 (11)	0.0037 (11)
C3	0.0525 (15)	0.0602 (15)	0.0826 (19)	0.0094 (13)	0.0059 (15)	0.0201 (14)
C4	0.074 (2)	0.0485 (16)	0.088 (2)	0.0167 (14)	0.0292 (17)	0.0089 (14)
C5	0.103 (3)	0.0439 (14)	0.0747 (19)	−0.0003 (17)	0.0165 (19)	−0.0139 (13)
C6	0.0650 (16)	0.0453 (14)	0.0588 (15)	−0.0036 (13)	0.0013 (12)	−0.0065 (11)
C7	0.0453 (13)	0.0366 (12)	0.0437 (12)	−0.0046 (10)	−0.0013 (10)	0.0016 (9)
C8	0.0463 (11)	0.0389 (11)	0.0471 (11)	−0.0040 (12)	−0.0060 (10)	−0.0038 (10)
C9	0.0728 (18)	0.0463 (13)	0.0418 (12)	−0.0153 (12)	−0.0039 (12)	0.0044 (10)
C10	0.095 (2)	0.0610 (17)	0.0545 (15)	−0.0060 (16)	0.0127 (16)	0.0077 (13)
C11	0.0747 (19)	0.0694 (19)	0.083 (2)	0.0123 (16)	0.0330 (17)	0.0058 (16)
C12	0.0488 (15)	0.0536 (15)	0.0674 (17)	0.0070 (12)	0.0105 (12)	0.0128 (12)
C13	0.0515 (16)	0.0658 (16)	0.0631 (16)	0.0125 (13)	0.0018 (12)	0.0035 (13)
C14	0.089 (2)	0.094 (2)	0.069 (2)	−0.002 (2)	−0.0176 (18)	0.0251 (17)
N1	0.0473 (11)	0.0380 (10)	0.0384 (10)	−0.0017 (9)	−0.0094 (9)	−0.0001 (8)
O1	0.0425 (10)	0.0555 (11)	0.0721 (11)	−0.0045 (8)	−0.0070 (7)	0.0018 (8)
O2	0.0708 (11)	0.0589 (10)	0.0432 (8)	0.0133 (10)	0.0158 (8)	0.0008 (7)
S1	0.0425 (3)	0.0397 (3)	0.0399 (3)	0.0026 (3)	0.0038 (2)	0.0009 (2)

Geometric parameters (Å, º) top

C1—C6	1.371 (3)	C9—C10	1.363 (4)
C1—C2	1.388 (3)	C9—C14	1.500 (4)
C1—S1	1.762 (2)	C10—C11	1.381 (4)
C2—C3	1.379 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.367 (4)
C3—C4	1.360 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.381 (5)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.380 (4)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.385 (3)	C14—H14C	0.9600
C7—C12	1.401 (3)	N1—S1	1.615 (2)
C7—N1	1.453 (3)	N1—H1N	0.84 (3)
C8—C9	1.414 (3)	O1—S1	1.4221 (17)
C8—C13	1.485 (3)	O2—S1	1.4362 (15)

C6—C1—C2	120.6 (2)	C11—C10—H10	119.4
C6—C1—S1	120.57 (19)	C12—C11—C10	120.4 (3)
C2—C1—S1	118.80 (16)	C12—C11—H11	119.8
C3—C2—C1	119.2 (2)	C10—C11—H11	119.8
C3—C2—H2	120.4	C11—C12—C7	118.6 (3)
C1—C2—H2	120.4	C11—C12—H12	120.7
C4—C3—C2	120.4 (3)	C7—C12—H12	120.7
C4—C3—H3	119.8	C8—C13—H13A	109.5
C2—C3—H3	119.8	C8—C13—H13B	109.5
C3—C4—C5	120.2 (3)	H13A—C13—H13B	109.5
C3—C4—H4	119.9	C8—C13—H13C	109.5
C5—C4—H4	119.9	H13A—C13—H13C	109.5
C6—C5—C4	120.1 (3)	H13B—C13—H13C	109.5
C6—C5—H5	119.9	C9—C14—H14A	109.5
C4—C5—H5	119.9	C9—C14—H14B	109.5
C1—C6—C5	119.4 (3)	H14A—C14—H14B	109.5
C1—C6—H6	120.3	C9—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C8—C7—C12	122.2 (2)	H14B—C14—H14C	109.5
C8—C7—N1	118.4 (2)	C7—N1—S1	121.07 (14)
C12—C7—N1	119.4 (2)	C7—N1—H1N	114.0 (17)
C7—C8—C9	117.3 (2)	S1—N1—H1N	112.4 (17)
C7—C8—C13	121.1 (2)	O1—S1—O2	120.28 (11)
C9—C8—C13	121.6 (2)	O1—S1—N1	107.97 (10)
C10—C9—C8	120.3 (2)	O2—S1—N1	105.37 (10)
C10—C9—C14	119.8 (2)	O1—S1—C1	107.82 (10)
C8—C9—C14	119.9 (2)	O2—S1—C1	106.68 (10)
C9—C10—C11	121.2 (3)	N1—S1—C1	108.24 (9)
C9—C10—H10	119.4

C6—C1—C2—C3	−1.7 (3)	C14—C9—C10—C11	179.4 (3)
S1—C1—C2—C3	177.83 (19)	C9—C10—C11—C12	−1.4 (5)
C1—C2—C3—C4	1.1 (4)	C10—C11—C12—C7	1.6 (4)
C2—C3—C4—C5	1.0 (4)	C8—C7—C12—C11	−0.5 (4)
C3—C4—C5—C6	−2.5 (4)	N1—C7—C12—C11	−178.6 (2)
C2—C1—C6—C5	0.2 (4)	C8—C7—N1—S1	95.3 (2)
S1—C1—C6—C5	−179.3 (2)	C12—C7—N1—S1	−86.4 (2)
C4—C5—C6—C1	1.9 (4)	C7—N1—S1—O1	−45.5 (2)
C12—C7—C8—C9	−0.8 (3)	C7—N1—S1—O2	−175.20 (17)
N1—C7—C8—C9	177.31 (19)	C7—N1—S1—C1	70.97 (19)
C12—C7—C8—C13	−179.5 (2)	C6—C1—S1—O1	−1.1 (2)
N1—C7—C8—C13	−1.4 (3)	C2—C1—S1—O1	179.35 (17)
C7—C8—C9—C10	1.1 (3)	C6—C1—S1—O2	129.3 (2)
C13—C8—C9—C10	179.7 (2)	C2—C1—S1—O2	−50.2 (2)
C7—C8—C9—C14	−178.3 (2)	C6—C1—S1—N1	−117.7 (2)
C13—C8—C9—C14	0.3 (3)	C2—C1—S1—N1	62.79 (19)
C8—C9—C10—C11	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (3)	2.10 (3)	2.936 (2)	176 (2)

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₂S
M_r	261.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	299
a, b, c (Å)	6.3969 (5), 8.8767 (6), 23.082 (2)
V (Å³)	1310.67 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.30 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.889, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	5869, 2611, 2200
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.07
No. of reflections	2611
No. of parameters	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19
Absolute structure	Flack (1983), 1060 Friedel pairs
Absolute structure parameter	−0.04 (9)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (3)	2.10 (3)	2.936 (2)	176 (2)

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

Acknowledgements

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

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
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