4-Methyl-N-(2-methyl­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810019513

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1502

https://doi.org/10.1107/S1600536810019513

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4-Methyl-N-(2-methylbenzoyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^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 21 May 2010; accepted 24 May 2010; online 29 May 2010)

In the title compound, C₁₅H₁₅NO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. Further, the conformation of the C=O bond is syn to the ortho-methyl group in the benzoyl ring. The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 87.1 (1)° and that between the sulfonyl and the benzoyl benzene rings is 58.2 (1)°. In the crystal structure, molecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming inversion dimers.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2010a ,b ); Suchetan et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₅NO₃S
M_r = 289.34
Triclinic, $[P \overline 1]$
a = 6.4097 (8) Å
b = 10.433 (1) Å
c = 11.258 (1) Å
α = 79.17 (1)°
β = 74.34 (1)°
γ = 85.15 (2)°
V = 711.54 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 K
0.30 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, ngland.]$ ) T_min = 0.933, T_max = 0.959
4725 measured reflections
2872 independent reflections
2387 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.06
2872 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.85 (1)	2.08 (1)	2.917 (2)	167 (2)
Symmetry code: (i) -x+2, -y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, ngland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, ngland.]$ ); 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/S1600536810019513/bq2213sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019513/bq2213Isup2.hkl

checkCIF report

Comment top

As a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2010a,b; Suchetan et al., 2010), the structure of N-(2-methylbenzoyl)-4-methylbenzenesulfonamide (I) has been determined. 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 those observed in N-(2-chlorobenzoyl)-4-chlorobenzenesulfonamide (II) (Gowda et al., 2010b), N-(4-methylbenzoyl)-2-methylbenzenesulfonamide (III) (Gowda et al., 2010a) and N-(benzoyl)-4-methylbenzenesulfonamide (IV) (Suchetan et al., 2010).

Further, the conformation of the C=O bond in the C—SO₂—NH—C(O) segment of (I) is syn to the ortho-methyl group in the benzoyl ring, similar to that observed between the C=O bond and the ortho-Cl in (II). The molecules are twisted at the S atom with the torsional angle of 67.7 (2)°, compared to those of 65.7 (2)° in (II), -53.1 (2)° and 61.2 (2)°, in the two independent molecules of (III) and 73.2 (2)° in (IV). The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 87.1 (1)°, compared to the values of 88.5 (1)° in (II), 86.0 (1)° and 87.9 (1)° in the two molecules of (III) and 76.5 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°, compared to the values of 58.2 (1)° in (II), 88.1 (1)° (molecule 1) and 83.5 (1)° (molecule 2) in (III) and 79.4 (1)° in (IV). The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

Experimental top

The title compound was prepared by refluxing a mixture of 2-methylbenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxy chloride for 3 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. It was filtered, dried and recrystallized. Rod like colorless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.

Structure description top

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.

4-Methyl-N-(2-methylbenzoyl)benzenesulfonamide top

Crystal data top

C₁₅H₁₅NO₃S	Z = 2
M_r = 289.34	F(000) = 304
Triclinic, P1	D_x = 1.350 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4097 (8) Å	Cell parameters from 2355 reflections
b = 10.433 (1) Å	θ = 2.5–27.8°
c = 11.258 (1) Å	µ = 0.23 mm⁻¹
α = 79.17 (1)°	T = 299 K
β = 74.34 (1)°	Rod, colorless
γ = 85.15 (2)°	0.30 × 0.20 × 0.18 mm
V = 711.54 (13) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2872 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→7
T_min = 0.933, T_max = 0.959	k = −9→13
4725 measured reflections	l = −13→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0434P)² + 0.3252P] where P = (F_o² + 2F_c²)/3
2872 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₅H₁₅NO₃S	γ = 85.15 (2)°
M_r = 289.34	V = 711.54 (13) Å³
Triclinic, P1	Z = 2
a = 6.4097 (8) Å	Mo Kα radiation
b = 10.433 (1) Å	µ = 0.23 mm⁻¹
c = 11.258 (1) Å	T = 299 K
α = 79.17 (1)°	0.30 × 0.20 × 0.18 mm
β = 74.34 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2872 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2387 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.959	R_int = 0.013
4725 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
2872 reflections	Δρ_min = −0.35 e Å⁻³
186 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	0.72322 (8)	0.15911 (5)	0.01004 (4)	0.04175 (15)
O1	0.9097 (2)	0.12090 (14)	−0.08160 (13)	0.0543 (4)
O2	0.5303 (2)	0.20184 (15)	−0.02716 (14)	0.0562 (4)
O3	0.3654 (2)	0.09970 (16)	0.24228 (16)	0.0646 (5)
N1	0.6788 (3)	0.02815 (15)	0.12042 (15)	0.0412 (4)
H1N	0.786 (2)	−0.0260 (17)	0.113 (2)	0.049*
C1	0.7964 (3)	0.27802 (18)	0.08116 (17)	0.0394 (4)
C2	0.6662 (3)	0.38915 (19)	0.0973 (2)	0.0487 (5)
H2	0.5389	0.4012	0.0714	0.058*
C3	0.7279 (4)	0.4821 (2)	0.1526 (2)	0.0589 (6)
H3	0.6434	0.5584	0.1612	0.071*
C4	0.9127 (4)	0.4638 (2)	0.1953 (2)	0.0548 (6)
C5	1.0396 (4)	0.3503 (2)	0.1788 (2)	0.0570 (6)
H5	1.1642	0.3365	0.2074	0.068*
C6	0.9848 (3)	0.2584 (2)	0.1211 (2)	0.0508 (5)
H6	1.0728	0.1840	0.1089	0.061*
C7	0.5092 (3)	0.01727 (19)	0.22766 (18)	0.0402 (4)
C8	0.5191 (3)	−0.10252 (19)	0.32282 (18)	0.0415 (4)
C9	0.6634 (3)	−0.1125 (2)	0.39775 (19)	0.0473 (5)
C10	0.6505 (4)	−0.2220 (3)	0.4924 (2)	0.0663 (7)
H10	0.7442	−0.2313	0.5440	0.080*
C11	0.5017 (5)	−0.3158 (3)	0.5106 (2)	0.0767 (8)
H11	0.4960	−0.3878	0.5741	0.092*
C12	0.3617 (5)	−0.3045 (3)	0.4360 (3)	0.0758 (8)
H12	0.2620	−0.3687	0.4486	0.091*
C13	0.3690 (4)	−0.1980 (2)	0.3425 (2)	0.0575 (6)
H13	0.2732	−0.1898	0.2923	0.069*
C14	0.9773 (5)	0.5629 (3)	0.2596 (3)	0.0849 (9)
H14A	0.8955	0.6432	0.2458	0.102*
H14B	1.1292	0.5782	0.2262	0.102*
H14C	0.9482	0.5302	0.3479	0.102*
C15	0.8194 (4)	−0.0075 (3)	0.3825 (2)	0.0658 (7)
H15A	0.9429	−0.0169	0.3136	0.079*
H15B	0.8659	−0.0150	0.4578	0.079*
H15C	0.7492	0.0765	0.3663	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0464 (3)	0.0408 (3)	0.0362 (3)	0.00360 (19)	−0.0112 (2)	−0.00359 (19)
O1	0.0642 (9)	0.0521 (8)	0.0364 (7)	0.0070 (7)	−0.0004 (7)	−0.0051 (6)
O2	0.0581 (9)	0.0609 (9)	0.0542 (9)	0.0045 (7)	−0.0287 (7)	−0.0036 (7)
O3	0.0505 (9)	0.0703 (11)	0.0600 (10)	0.0194 (8)	−0.0056 (8)	−0.0015 (8)
N1	0.0450 (9)	0.0362 (8)	0.0394 (9)	0.0031 (7)	−0.0082 (7)	−0.0052 (7)
C1	0.0388 (9)	0.0361 (9)	0.0386 (10)	0.0007 (7)	−0.0070 (8)	−0.0005 (8)
C2	0.0494 (11)	0.0409 (11)	0.0511 (12)	0.0089 (9)	−0.0124 (9)	−0.0017 (9)
C3	0.0708 (15)	0.0391 (11)	0.0573 (14)	0.0089 (10)	−0.0047 (12)	−0.0073 (10)
C4	0.0679 (14)	0.0458 (11)	0.0440 (12)	−0.0166 (10)	−0.0018 (10)	−0.0031 (9)
C5	0.0492 (12)	0.0588 (13)	0.0636 (14)	−0.0106 (10)	−0.0162 (11)	−0.0059 (11)
C6	0.0417 (11)	0.0451 (11)	0.0648 (14)	0.0037 (9)	−0.0139 (10)	−0.0101 (10)
C7	0.0387 (10)	0.0450 (10)	0.0393 (10)	−0.0024 (8)	−0.0130 (8)	−0.0083 (8)
C8	0.0446 (10)	0.0440 (10)	0.0345 (9)	0.0009 (8)	−0.0067 (8)	−0.0094 (8)
C9	0.0470 (11)	0.0563 (12)	0.0385 (10)	0.0101 (9)	−0.0110 (9)	−0.0129 (9)
C10	0.0794 (17)	0.0770 (17)	0.0417 (12)	0.0211 (14)	−0.0220 (12)	−0.0096 (11)
C11	0.111 (2)	0.0579 (15)	0.0474 (14)	0.0018 (15)	−0.0091 (15)	0.0068 (11)
C12	0.100 (2)	0.0588 (15)	0.0610 (16)	−0.0226 (14)	−0.0091 (15)	−0.0003 (12)
C13	0.0670 (14)	0.0553 (13)	0.0506 (13)	−0.0135 (11)	−0.0145 (11)	−0.0060 (10)
C14	0.115 (2)	0.0692 (17)	0.0694 (18)	−0.0326 (16)	−0.0078 (17)	−0.0204 (14)
C15	0.0528 (13)	0.0923 (19)	0.0612 (15)	−0.0041 (12)	−0.0248 (12)	−0.0202 (13)

Geometric parameters (Å, º) top

S1—O2	1.4210 (15)	C7—C8	1.495 (3)
S1—O1	1.4351 (15)	C8—C13	1.390 (3)
S1—N1	1.6519 (17)	C8—C9	1.396 (3)
S1—C1	1.754 (2)	C9—C10	1.400 (3)
O3—C7	1.206 (2)	C9—C15	1.500 (3)
N1—C7	1.383 (2)	C10—C11	1.374 (4)
N1—H1N	0.849 (9)	C10—H10	0.9300
C1—C2	1.381 (3)	C11—C12	1.369 (4)
C1—C6	1.385 (3)	C11—H11	0.9300
C2—C3	1.381 (3)	C12—C13	1.374 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.381 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.392 (3)	C14—H14B	0.9600
C4—C14	1.509 (3)	C14—H14C	0.9600
C5—C6	1.371 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600

O2—S1—O1	118.80 (9)	C13—C8—C9	120.8 (2)
O2—S1—N1	110.35 (9)	C13—C8—C7	118.47 (18)
O1—S1—N1	103.52 (8)	C9—C8—C7	120.44 (18)
O2—S1—C1	109.33 (9)	C8—C9—C10	117.4 (2)
O1—S1—C1	109.09 (9)	C8—C9—C15	121.8 (2)
N1—S1—C1	104.75 (9)	C10—C9—C15	120.7 (2)
C7—N1—S1	124.66 (14)	C11—C10—C9	121.2 (2)
C7—N1—H1N	121.5 (15)	C11—C10—H10	119.4
S1—N1—H1N	112.5 (15)	C9—C10—H10	119.4
C2—C1—C6	120.86 (19)	C12—C11—C10	120.6 (2)
C2—C1—S1	119.99 (16)	C12—C11—H11	119.7
C6—C1—S1	119.15 (15)	C10—C11—H11	119.7
C3—C2—C1	119.0 (2)	C11—C12—C13	119.8 (3)
C3—C2—H2	120.5	C11—C12—H12	120.1
C1—C2—H2	120.5	C13—C12—H12	120.1
C4—C3—C2	121.3 (2)	C12—C13—C8	120.2 (2)
C4—C3—H3	119.4	C12—C13—H13	119.9
C2—C3—H3	119.4	C8—C13—H13	119.9
C3—C4—C5	118.4 (2)	C4—C14—H14A	109.5
C3—C4—C14	121.6 (2)	C4—C14—H14B	109.5
C5—C4—C14	120.0 (2)	H14A—C14—H14B	109.5
C6—C5—C4	121.4 (2)	C4—C14—H14C	109.5
C6—C5—H5	119.3	H14A—C14—H14C	109.5
C4—C5—H5	119.3	H14B—C14—H14C	109.5
C5—C6—C1	119.06 (19)	C9—C15—H15A	109.5
C5—C6—H6	120.5	C9—C15—H15B	109.5
C1—C6—H6	120.5	H15A—C15—H15B	109.5
O3—C7—N1	121.68 (18)	C9—C15—H15C	109.5
O3—C7—C8	123.12 (18)	H15A—C15—H15C	109.5
N1—C7—C8	115.21 (16)	H15B—C15—H15C	109.5

O2—S1—N1—C7	−49.84 (18)	S1—C1—C6—C5	−178.79 (17)
O1—S1—N1—C7	−177.98 (16)	S1—N1—C7—O3	8.0 (3)
C1—S1—N1—C7	67.73 (17)	S1—N1—C7—C8	−171.57 (13)
O2—S1—C1—C2	2.47 (19)	O3—C7—C8—C13	70.2 (3)
O1—S1—C1—C2	133.91 (16)	N1—C7—C8—C13	−110.2 (2)
N1—S1—C1—C2	−115.79 (17)	O3—C7—C8—C9	−104.1 (2)
O2—S1—C1—C6	−177.85 (16)	N1—C7—C8—C9	75.4 (2)
O1—S1—C1—C6	−46.42 (18)	C13—C8—C9—C10	0.1 (3)
N1—S1—C1—C6	63.89 (18)	C7—C8—C9—C10	174.35 (18)
C6—C1—C2—C3	0.9 (3)	C13—C8—C9—C15	−176.9 (2)
S1—C1—C2—C3	−179.44 (16)	C7—C8—C9—C15	−2.7 (3)
C1—C2—C3—C4	−2.1 (3)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	1.5 (3)	C15—C9—C10—C11	177.2 (2)
C2—C3—C4—C14	−177.9 (2)	C9—C10—C11—C12	0.0 (4)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—C13	−0.3 (4)
C14—C4—C5—C6	179.8 (2)	C11—C12—C13—C8	0.6 (4)
C4—C5—C6—C1	−1.5 (3)	C9—C8—C13—C12	−0.5 (3)
C2—C1—C6—C5	0.9 (3)	C7—C8—C13—C12	−174.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (1)	2.08 (1)	2.917 (2)	167 (2)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₃S
M_r	289.34
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	6.4097 (8), 10.433 (1), 11.258 (1)
α, β, γ (°)	79.17 (1), 74.34 (1), 85.15 (2)
V (Å³)	711.54 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.30 × 0.20 × 0.18

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	0.933, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	4725, 2872, 2387
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.06
No. of reflections	2872
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.35

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···O1ⁱ	0.849 (9)	2.083 (11)	2.917 (2)	167 (2)

Symmetry code: (i) −x+2, −y, −z.

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

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