N-(4-Methyl­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810023974

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1772

doi:10.1107/S1600536810023974

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N-(4-Methylbenzoyl)benzenesulfonamide

P. A. Suchetan,^a B. Thimme Gowda,^a ^* Sabine Foro ^b 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 18 June 2010; accepted 20 June 2010; online 26 June 2010)

In the title compound, C₁₄H₁₃NO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the S—N—C—O segment (r.m.s. deviation = 0.039 Å) is 77.1 (1)° and that between the sulfonyl and benzoyl benzene rings is 71.9 (1)°.

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 related structures, see: Gowda et al. (2009 ); Suchetan et al. (2009 , 2010 ).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M_r = 275.31
Triclinic, $[P \overline 1]$
a = 5.5519 (6) Å
b = 10.541 (1) Å
c = 11.105 (1) Å
α = 85.654 (9)°
β = 83.667 (9)°
γ = 81.949 (9)°
V = 638.36 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 299 K
0.40 × 0.32 × 0.16 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 = 0.904, T_max = 0.960
4293 measured reflections
2595 independent reflections
2207 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.08
2595 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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: 10.1107/S1600536810023974/ci5108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023974/ci5108Isup2.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., 2009; Suchetan et al., 2009, 2010), the crystal structure of N-(4-methylbenzoyl)benzenesulfonamide has been determined (Fig. 1). The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C═O bond, similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(benzoyl)-4-methylbenzenesulfonamide (III) (Suchetan et al., 2010) and N-(4-chlorobenzoyl)-benzenesulfonamide (IV) (Suchetan et al., 2009).

The molecules are twisted at the S—N bonds with the C—SO₂—NH—C torsional angle of 67.4 (1)°, compared to the values of -66.9 (3)° in (II), 73.2 (2)° in (III) and 69.4 (2)° in (IV).

The dihedral angle between the sulfonyl-bound benzene ring and the S—N—C—O segment (r.m.s. deviation 0.039 Å) is 77.1 (1)°, compared to the values of 86.5 (1)° in (II), 76.5 (1)° in (III) and 75.7 (1)° in (IV).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 71.9 (1)°, compared to the values of 80.3 (1) in (II), 79.4 (1)° in (III), and 68.6 (1)° in (IV).

Related literature top

Experimental top

The title compound was prepared by refluxing a mixture of 4-methylbenzoic acid, benzenesulfonamide 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 a sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized. Colourless needle-shaped single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.

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.

N-(4-Methylbenzoyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₃NO₃S	Z = 2
M_r = 275.31	F(000) = 288
Triclinic, P1	D_x = 1.432 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5519 (6) Å	Cell parameters from 2679 reflections
b = 10.541 (1) Å	θ = 2.6–27.7°
c = 11.105 (1) Å	µ = 0.26 mm⁻¹
α = 85.654 (9)°	T = 299 K
β = 83.667 (9)°	Needle, colourless
γ = 81.949 (9)°	0.40 × 0.32 × 0.16 mm
V = 638.36 (11) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2595 independent reflections
Radiation source: fine-focus sealed tube	2207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→6
T_min = 0.904, T_max = 0.960	k = −13→11
4293 measured reflections	l = −13→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0564P)² + 0.1768P] where P = (F_o² + 2F_c²)/3
2595 reflections	(Δ/σ)_max = 0.020
173 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₃NO₃S	γ = 81.949 (9)°
M_r = 275.31	V = 638.36 (11) Å³
Triclinic, P1	Z = 2
a = 5.5519 (6) Å	Mo Kα radiation
b = 10.541 (1) Å	µ = 0.26 mm⁻¹
c = 11.105 (1) Å	T = 299 K
α = 85.654 (9)°	0.40 × 0.32 × 0.16 mm
β = 83.667 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2595 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2207 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.960	R_int = 0.017
4293 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	Δρ_max = 0.24 e Å⁻³
2595 reflections	Δρ_min = −0.30 e Å⁻³
173 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	0.0535 (3)	0.17087 (15)	0.37945 (14)	0.0370 (3)
C2	0.2512 (3)	0.07861 (18)	0.39763 (17)	0.0491 (4)
H2	0.3709	0.0944	0.4448	0.059*
C3	0.2687 (4)	−0.03734 (19)	0.34486 (19)	0.0557 (5)
H3	0.4008	−0.1001	0.3567	0.067*
C4	0.0919 (4)	−0.06031 (17)	0.27507 (18)	0.0514 (5)
H4	0.1050	−0.1383	0.2394	0.062*
C5	−0.1047 (4)	0.03194 (19)	0.25778 (17)	0.0517 (5)
H5	−0.2241	0.0157	0.2106	0.062*
C6	−0.1262 (3)	0.14869 (17)	0.31001 (16)	0.0439 (4)
H6	−0.2592	0.2110	0.2985	0.053*
C7	0.1508 (3)	0.45512 (14)	0.24545 (14)	0.0362 (3)
C8	0.2982 (3)	0.55415 (14)	0.18611 (13)	0.0345 (3)
C9	0.4790 (3)	0.60283 (16)	0.23892 (15)	0.0393 (4)
H9	0.5113	0.5748	0.3177	0.047*
C10	0.6111 (3)	0.69266 (17)	0.17506 (15)	0.0429 (4)
H10	0.7328	0.7235	0.2113	0.051*
C11	0.5653 (3)	0.73765 (16)	0.05771 (15)	0.0403 (4)
C12	0.3825 (3)	0.69012 (18)	0.00681 (16)	0.0471 (4)
H12	0.3477	0.7197	−0.0712	0.056*
C13	0.2508 (3)	0.60001 (17)	0.06897 (15)	0.0451 (4)
H13	0.1291	0.5695	0.0324	0.054*
C14	0.7134 (4)	0.83301 (19)	−0.01353 (19)	0.0553 (5)
H14A	0.8409	0.7882	−0.0661	0.066*
H14B	0.7844	0.8795	0.0415	0.066*
H14C	0.6090	0.8920	−0.0613	0.066*
N1	0.2026 (3)	0.40757 (13)	0.36175 (13)	0.0466 (4)
H1N	0.3319	0.4262	0.3887	0.056*
O1	0.1439 (3)	0.29602 (14)	0.55935 (12)	0.0705 (5)
O2	−0.2229 (3)	0.37520 (13)	0.45410 (13)	0.0618 (4)
O3	−0.0051 (2)	0.41356 (12)	0.19791 (11)	0.0493 (3)
S1	0.02709 (9)	0.31703 (4)	0.45017 (4)	0.04709 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0466 (9)	0.0344 (8)	0.0314 (8)	−0.0135 (7)	−0.0018 (6)	0.0008 (6)
C2	0.0481 (10)	0.0518 (10)	0.0501 (10)	−0.0113 (8)	−0.0125 (8)	−0.0001 (8)
C3	0.0556 (11)	0.0452 (10)	0.0633 (12)	−0.0003 (8)	−0.0039 (9)	0.0008 (9)
C4	0.0641 (12)	0.0386 (9)	0.0524 (11)	−0.0164 (8)	0.0059 (9)	−0.0079 (8)
C5	0.0555 (11)	0.0545 (11)	0.0510 (11)	−0.0219 (9)	−0.0081 (8)	−0.0105 (8)
C6	0.0453 (9)	0.0427 (9)	0.0453 (9)	−0.0096 (7)	−0.0076 (7)	−0.0014 (7)
C7	0.0448 (9)	0.0310 (8)	0.0330 (8)	−0.0035 (6)	−0.0065 (6)	−0.0027 (6)
C8	0.0391 (8)	0.0319 (8)	0.0313 (8)	−0.0004 (6)	−0.0035 (6)	−0.0018 (6)
C9	0.0429 (9)	0.0439 (9)	0.0313 (8)	−0.0054 (7)	−0.0071 (6)	0.0016 (6)
C10	0.0417 (9)	0.0476 (9)	0.0408 (9)	−0.0092 (7)	−0.0061 (7)	−0.0030 (7)
C11	0.0419 (9)	0.0359 (8)	0.0397 (8)	0.0000 (7)	0.0026 (7)	−0.0005 (6)
C12	0.0571 (11)	0.0495 (10)	0.0342 (8)	−0.0070 (8)	−0.0097 (7)	0.0074 (7)
C13	0.0524 (10)	0.0494 (10)	0.0366 (9)	−0.0127 (8)	−0.0145 (7)	0.0030 (7)
C14	0.0585 (12)	0.0500 (11)	0.0552 (11)	−0.0114 (9)	0.0036 (9)	0.0053 (9)
N1	0.0680 (10)	0.0420 (8)	0.0359 (7)	−0.0246 (7)	−0.0154 (7)	0.0053 (6)
O1	0.1269 (14)	0.0621 (9)	0.0333 (7)	−0.0439 (9)	−0.0218 (7)	0.0059 (6)
O2	0.0745 (10)	0.0493 (8)	0.0565 (8)	−0.0036 (7)	0.0148 (7)	−0.0111 (6)
O3	0.0544 (7)	0.0519 (7)	0.0459 (7)	−0.0172 (6)	−0.0166 (6)	0.0056 (5)
S1	0.0756 (3)	0.0393 (2)	0.0295 (2)	−0.0204 (2)	−0.00330 (19)	−0.00178 (16)

Geometric parameters (Å, º) top

C1—C6	1.381 (2)	C9—C10	1.384 (2)
C1—C2	1.382 (3)	C9—H9	0.93
C1—S1	1.7626 (16)	C10—C11	1.391 (2)
C2—C3	1.382 (3)	C10—H10	0.93
C2—H2	0.93	C11—C12	1.383 (2)
C3—C4	1.373 (3)	C11—C14	1.510 (2)
C3—H3	0.93	C12—C13	1.377 (2)
C4—C5	1.376 (3)	C12—H12	0.93
C4—H4	0.93	C13—H13	0.93
C5—C6	1.385 (3)	C14—H14A	0.96
C5—H5	0.93	C14—H14B	0.96
C6—H6	0.93	C14—H14C	0.96
C7—O3	1.209 (2)	N1—S1	1.6529 (15)
C7—N1	1.395 (2)	N1—H1N	0.86
C7—C8	1.487 (2)	O1—S1	1.4257 (14)
C8—C9	1.391 (2)	O2—S1	1.4340 (15)
C8—C13	1.393 (2)

C6—C1—C2	121.09 (16)	C9—C10—C11	121.20 (16)
C6—C1—S1	119.75 (13)	C9—C10—H10	119.4
C2—C1—S1	119.13 (13)	C11—C10—H10	119.4
C3—C2—C1	119.19 (17)	C12—C11—C10	117.86 (15)
C3—C2—H2	120.4	C12—C11—C14	120.74 (16)
C1—C2—H2	120.4	C10—C11—C14	121.39 (16)
C4—C3—C2	120.29 (18)	C13—C12—C11	121.56 (16)
C4—C3—H3	119.9	C13—C12—H12	119.2
C2—C3—H3	119.9	C11—C12—H12	119.2
C3—C4—C5	120.12 (17)	C12—C13—C8	120.55 (16)
C3—C4—H4	119.9	C12—C13—H13	119.7
C5—C4—H4	119.9	C8—C13—H13	119.7
C4—C5—C6	120.56 (17)	C11—C14—H14A	109.5
C4—C5—H5	119.7	C11—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	109.5
C1—C6—C5	118.75 (17)	C11—C14—H14C	109.5
C1—C6—H6	120.6	H14A—C14—H14C	109.5
C5—C6—H6	120.6	H14B—C14—H14C	109.5
O3—C7—N1	119.51 (15)	C7—N1—S1	123.07 (12)
O3—C7—C8	123.77 (14)	C7—N1—H1N	118.5
N1—C7—C8	116.70 (14)	S1—N1—H1N	118.5
C9—C8—C13	118.37 (15)	O1—S1—O2	119.65 (10)
C9—C8—C7	124.69 (14)	O1—S1—N1	103.47 (8)
C13—C8—C7	116.93 (14)	O2—S1—N1	109.71 (8)
C10—C9—C8	120.45 (15)	O1—S1—C1	109.18 (9)
C10—C9—H9	119.8	O2—S1—C1	108.24 (8)
C8—C9—H9	119.8	N1—S1—C1	105.73 (8)

C6—C1—C2—C3	0.2 (3)	C10—C11—C12—C13	−0.7 (3)
S1—C1—C2—C3	178.30 (14)	C14—C11—C12—C13	177.89 (17)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C8	0.2 (3)
C2—C3—C4—C5	−0.3 (3)	C9—C8—C13—C12	0.8 (3)
C3—C4—C5—C6	0.2 (3)	C7—C8—C13—C12	−178.80 (16)
C2—C1—C6—C5	−0.4 (3)	O3—C7—N1—S1	−12.2 (2)
S1—C1—C6—C5	−178.42 (13)	C8—C7—N1—S1	168.97 (11)
C4—C5—C6—C1	0.2 (3)	C7—N1—S1—O1	−177.83 (14)
O3—C7—C8—C9	−179.72 (16)	C7—N1—S1—O2	−49.07 (16)
N1—C7—C8—C9	−0.9 (2)	C7—N1—S1—C1	67.44 (15)
O3—C7—C8—C13	−0.1 (2)	C6—C1—S1—O1	149.92 (14)
N1—C7—C8—C13	178.70 (15)	C2—C1—S1—O1	−28.17 (17)
C13—C8—C9—C10	−1.3 (2)	C6—C1—S1—O2	18.16 (16)
C7—C8—C9—C10	178.29 (15)	C2—C1—S1—O2	−159.93 (14)
C8—C9—C10—C11	0.8 (3)	C6—C1—S1—N1	−99.34 (14)
C9—C10—C11—C12	0.2 (3)	C2—C1—S1—N1	82.58 (15)
C9—C10—C11—C14	−178.37 (16)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₃S
M_r	275.31
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	5.5519 (6), 10.541 (1), 11.105 (1)
α, β, γ (°)	85.654 (9), 83.667 (9), 81.949 (9)
V (Å³)	638.36 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.40 × 0.32 × 0.16

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	0.904, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	4293, 2595, 2207
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.08
No. of reflections	2595
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

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

Acknowledgements

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

References

Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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