N-{4-[(3-Methyl­phen­yl)sulfamo­yl]phen­yl}acetamide

Farrukh, M.A.; Qureshi, F.A.; Adnan, A.; Türktekin, S.; Akkurt, M.

doi:10.1107/S1600536812001274

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o437

doi:10.1107/S1600536812001274

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N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}acetamide

Muhammad Akhyar Farrukh,^a ‡ Fahim Ashraf Qureshi,^a Ahmad Adnan,^a Sevim Türktekin ^b and Mehmet Akkurt ^b ^*

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 30 December 2011; accepted 11 January 2012; online 18 January 2012)

In the title compound, C₁₅H₁₆N₂O₃S, the central C—S(=O)₂N(H)—C unit is twisted, with a C—S—N—C torsion angle of −56.4 (2)°. The benzene rings form a dihedral angle of 49.65 (15)° with each other. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to sulfonamides, see: Ahmad et al. (2011a ,b ); Faryal et al. (2011 ); Pandya et al. (2003 ); Singh & Bansal (2004 ). For the crystal structure of the isomeric compound, N–{4–[(4–methylphenyl)sulfamoyl]phenyl}acetamide, see: John et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₃S
M_r = 304.37
Orthorhombic, P b c a
a = 12.4072 (4) Å
b = 9.8528 (4) Å
c = 24.7872 (10) Å
V = 3030.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.13 × 0.10 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
27585 measured reflections
3766 independent reflections
2018 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.146
S = 1.02
3766 reflections
200 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86 (2)	2.09 (2)	2.938 (3)	171 (2)
N2—H2N⋯O3ⁱⁱ	0.84 (2)	2.05 (2)	2.878 (3)	173 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001274/lx2224sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001274/lx2224Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001274/lx2224Isup3.cml

checkCIF report

Comment top

Sulfonamides are a diverse group of compounds having considerable medical importance (Pandya et al., 2003). They are the very important class of compounds in the pharmaceutical industry, being widely used as anticancer, anti-inflammatory and antiviral agents. They have been the center of drug structures as this group is quite stable and well tolerated in human beings (Singh & Bansal 2004). Compounds bearing sulfonate group increases their hydrophilicity and have become useful pharmacological tool. In continuation of on–going structural studies of sulfonamide derivatives (Faryal et al., 2011; Ahmad et al., 2011a,b), the crystal structure of title sulfonamide N–{4–[(3–methylphenyl)sulfamoyl]phenyl}acetamide is described herein.

The title compound, (Fig. 1) is a isomer of the compound, N–{4–[(4–methylphenyl)sulfamoyl]phenyl}acetamide, reported by John et al. (2010). The title compound crystallizes in the orthorhombic space group P bca with Z=8, while its mentioned-isomer crystallizes in triclinic space group P-1 with Z=2. The values of the geometric properties of both compounds are similar. The dihedral angle between the C3–C8 and C9–C14 benzene rings is 49.65 (15) °. In the central C—S(═O)₂N(H)—C unit of title compound, the C6—S1—N1—C9 torsion angle of -56.4 (2)° indicates a twist in the molecule. The amide group is not co–planar with the benzene ring to which it is attached [C2—N2—C3—C8 = 27.5 (5) °]. In the crystal structure, molecules are connected via N—H···O hydrogen bonds, generating a three–dimensional network (Table 1, Fig. 2).

Related literature top

For background to sulfonamides, see: Ahmad et al. (2011a,b); Faryal et al. (2011); Pandya et al. (2003); Singh & Bansal (2004). For the crystal structure of the isomeric compound, N–{4–[(4–methylphenyl)sulfamoyl]phenyl}acetamide, see: John et al. (2010).

Experimental top

5 mmol of m–toluidine was dissolved in 20 ml of distilled water then 5 mmol of 4–acetamidobenzenesulfonyl chloride was added. The reaction mixture was stirred for about 2–3 h while the pH of the reaction mixture was maintained between 8–10 using 3% Na₂CO₃. The reaction was monitored by TLC. The precipitate formed was filtered, washed with distilled water, dried and recrystallized by using methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the N—H···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non–participating in hydrogen- bonding were omitted for clarity. [Symmetry codes: (i) - x + 3/2, y - 1/2, z; (ii) - x + 1/2, y + 1/2, z; (iii) - x + 3/2, y + 1/2, z; (iv) - x + 1/2, y - 1/2, z.]

N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}acetamide top

Crystal data top

C₁₅H₁₆N₂O₃S	F(000) = 1280
M_r = 304.37	D_x = 1.334 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2598 reflections
a = 12.4072 (4) Å	θ = 2.8–26.1°
b = 9.8528 (4) Å	µ = 0.23 mm⁻¹
c = 24.7872 (10) Å	T = 296 K
V = 3030.1 (2) Å³	Plates, colourless
Z = 8	0.13 × 0.10 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	2018 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.089
Graphite monochromator	θ_max = 28.3°, θ_min = 2.8°
ϕ and ω scans	h = −16→15
27585 measured reflections	k = −13→13
3766 independent reflections	l = −32→32

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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0559P)² + 1.2606P] where P = (F_o² + 2F_c²)/3
3766 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.44 e Å⁻³
2 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₃S	V = 3030.1 (2) Å³
M_r = 304.37	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.4072 (4) Å	µ = 0.23 mm⁻¹
b = 9.8528 (4) Å	T = 296 K
c = 24.7872 (10) Å	0.13 × 0.10 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	2018 reflections with I > 2σ(I)
27585 measured reflections	R_int = 0.089
3766 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	2 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.44 e Å⁻³
3766 reflections	Δρ_min = −0.34 e Å⁻³
200 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	0.75972 (5)	0.46076 (6)	0.12164 (3)	0.0386 (2)
O1	0.82358 (15)	0.3853 (2)	0.08468 (9)	0.0510 (7)
O2	0.79502 (15)	0.59357 (18)	0.13737 (9)	0.0477 (7)
O3	0.25638 (16)	0.27762 (18)	0.04342 (10)	0.0573 (8)
N1	0.75422 (19)	0.3683 (2)	0.17624 (10)	0.0407 (8)
N2	0.30625 (19)	0.4969 (2)	0.05052 (11)	0.0424 (8)
C1	0.1211 (2)	0.4459 (3)	0.03050 (14)	0.0536 (10)
C2	0.2336 (2)	0.3979 (3)	0.04182 (11)	0.0400 (9)
C3	0.4142 (2)	0.4837 (2)	0.06584 (11)	0.0362 (9)
C4	0.4594 (2)	0.5905 (3)	0.09375 (13)	0.0505 (12)
C5	0.5659 (2)	0.5860 (3)	0.10976 (13)	0.0501 (10)
C6	0.6270 (2)	0.4738 (3)	0.09778 (11)	0.0362 (9)
C7	0.5827 (2)	0.3668 (3)	0.06968 (12)	0.0448 (10)
C8	0.4762 (2)	0.3707 (3)	0.05379 (12)	0.0442 (10)
C9	0.6853 (2)	0.4104 (3)	0.21957 (12)	0.0425 (10)
C10	0.7132 (2)	0.5202 (3)	0.25144 (13)	0.0494 (11)
C11	0.6485 (3)	0.5624 (4)	0.29349 (13)	0.0593 (12)
C12	0.5563 (3)	0.4898 (4)	0.30367 (16)	0.0723 (16)
C13	0.5285 (3)	0.3793 (4)	0.27305 (18)	0.0780 (16)
C14	0.5919 (2)	0.3389 (3)	0.23047 (15)	0.0596 (13)
C15	0.6791 (4)	0.6837 (4)	0.32666 (16)	0.0900 (19)
H1A	0.10860	0.44510	−0.00770	0.0800*
H1B	0.11240	0.53650	0.04400	0.0800*
H1C	0.07050	0.38670	0.04790	0.0800*
H1N	0.746 (2)	0.2849 (18)	0.1672 (10)	0.034 (7)*
H2N	0.283 (2)	0.5766 (19)	0.0497 (11)	0.041 (8)*
H4	0.41780	0.66630	0.10190	0.0610*
H5	0.59610	0.65850	0.12850	0.0600*
H7	0.62490	0.29160	0.06140	0.0540*
H8	0.44620	0.29800	0.03510	0.0530*
H10	0.77690	0.56660	0.24440	0.0590*
H12	0.51180	0.51610	0.33200	0.0870*
H13	0.46600	0.33130	0.28110	0.0930*
H14	0.57240	0.26480	0.20940	0.0710*
H15A	0.65440	0.76480	0.30910	0.1350*
H15B	0.75610	0.68710	0.33050	0.1350*
H15C	0.64650	0.67700	0.36170	0.1350*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0279 (3)	0.0296 (3)	0.0582 (5)	0.0008 (3)	0.0013 (3)	−0.0014 (3)
O1	0.0385 (11)	0.0465 (12)	0.0679 (14)	0.0097 (10)	0.0113 (10)	−0.0046 (10)
O2	0.0364 (10)	0.0307 (10)	0.0759 (15)	−0.0076 (9)	−0.0033 (10)	−0.0003 (10)
O3	0.0501 (13)	0.0258 (11)	0.0960 (18)	−0.0051 (10)	−0.0081 (12)	0.0021 (10)
N1	0.0356 (13)	0.0279 (12)	0.0586 (16)	0.0013 (11)	0.0000 (12)	−0.0011 (11)
N2	0.0339 (13)	0.0240 (12)	0.0694 (17)	0.0010 (10)	−0.0097 (12)	0.0005 (11)
C1	0.0382 (16)	0.0475 (18)	0.075 (2)	−0.0051 (15)	−0.0110 (16)	0.0012 (16)
C2	0.0397 (16)	0.0319 (15)	0.0485 (18)	−0.0043 (13)	−0.0039 (13)	0.0016 (13)
C3	0.0316 (15)	0.0260 (13)	0.0509 (18)	−0.0009 (12)	−0.0003 (13)	0.0017 (12)
C4	0.0342 (16)	0.0254 (14)	0.092 (3)	0.0053 (13)	−0.0061 (16)	−0.0113 (15)
C5	0.0397 (16)	0.0277 (14)	0.083 (2)	−0.0017 (13)	−0.0079 (15)	−0.0133 (14)
C6	0.0267 (13)	0.0298 (14)	0.0521 (18)	0.0010 (12)	0.0003 (12)	0.0001 (12)
C7	0.0384 (17)	0.0301 (14)	0.066 (2)	0.0063 (13)	−0.0031 (15)	−0.0093 (13)
C8	0.0412 (16)	0.0304 (14)	0.061 (2)	0.0004 (13)	−0.0070 (14)	−0.0103 (13)
C9	0.0302 (15)	0.0436 (16)	0.0537 (19)	0.0049 (13)	−0.0024 (13)	0.0037 (14)
C10	0.0444 (18)	0.0487 (18)	0.055 (2)	0.0035 (15)	−0.0033 (15)	0.0024 (16)
C11	0.062 (2)	0.066 (2)	0.050 (2)	0.0162 (19)	−0.0014 (17)	−0.0035 (17)
C12	0.058 (2)	0.096 (3)	0.063 (3)	0.015 (2)	0.0167 (19)	0.002 (2)
C13	0.045 (2)	0.091 (3)	0.098 (3)	−0.004 (2)	0.019 (2)	0.006 (3)
C14	0.0399 (18)	0.058 (2)	0.081 (3)	−0.0041 (16)	0.0054 (18)	−0.0009 (18)
C15	0.107 (4)	0.100 (3)	0.063 (3)	0.016 (3)	−0.001 (2)	−0.022 (2)

Geometric parameters (Å, º) top

S1—O1	1.421 (2)	C10—C11	1.380 (5)
S1—O2	1.4339 (19)	C11—C12	1.373 (5)
S1—N1	1.633 (2)	C11—C15	1.500 (5)
S1—C6	1.754 (3)	C12—C13	1.371 (6)
O3—C2	1.219 (3)	C13—C14	1.375 (5)
N1—C9	1.434 (4)	C1—H1A	0.9600
N2—C2	1.346 (4)	C1—H1B	0.9600
N2—C3	1.398 (3)	C1—H1C	0.9600
N1—H1N	0.858 (18)	C4—H4	0.9300
N2—H2N	0.84 (2)	C5—H5	0.9300
C1—C2	1.500 (4)	C7—H7	0.9300
C3—C8	1.386 (4)	C8—H8	0.9300
C3—C4	1.379 (4)	C10—H10	0.9300
C4—C5	1.380 (4)	C12—H12	0.9300
C5—C6	1.373 (4)	C13—H13	0.9300
C6—C7	1.378 (4)	C14—H14	0.9300
C7—C8	1.379 (4)	C15—H15A	0.9600
C9—C14	1.383 (4)	C15—H15B	0.9600
C9—C10	1.384 (4)	C15—H15C	0.9600

O1—S1—O2	118.84 (12)	C11—C12—C13	121.4 (4)
O1—S1—N1	105.41 (12)	C12—C13—C14	120.7 (3)
O1—S1—C6	110.14 (13)	C9—C14—C13	118.8 (3)
O2—S1—N1	107.25 (12)	C2—C1—H1A	109.00
O2—S1—C6	108.15 (13)	C2—C1—H1B	109.00
N1—S1—C6	106.32 (13)	C2—C1—H1C	109.00
S1—N1—C9	118.97 (18)	H1A—C1—H1B	109.00
C2—N2—C3	128.2 (2)	H1A—C1—H1C	109.00
S1—N1—H1N	108.8 (17)	H1B—C1—H1C	110.00
C9—N1—H1N	113.7 (17)	C3—C4—H4	120.00
C2—N2—H2N	116.5 (17)	C5—C4—H4	120.00
C3—N2—H2N	115.1 (17)	C4—C5—H5	120.00
O3—C2—N2	123.0 (2)	C6—C5—H5	120.00
O3—C2—C1	121.9 (2)	C6—C7—H7	120.00
N2—C2—C1	115.1 (2)	C8—C7—H7	120.00
N2—C3—C4	117.1 (2)	C3—C8—H8	120.00
C4—C3—C8	119.7 (2)	C7—C8—H8	120.00
N2—C3—C8	123.2 (2)	C9—C10—H10	119.00
C3—C4—C5	120.6 (3)	C11—C10—H10	119.00
C4—C5—C6	119.5 (3)	C11—C12—H12	119.00
C5—C6—C7	120.3 (2)	C13—C12—H12	119.00
S1—C6—C5	120.3 (2)	C12—C13—H13	120.00
S1—C6—C7	119.3 (2)	C14—C13—H13	120.00
C6—C7—C8	120.3 (3)	C9—C14—H14	121.00
C3—C8—C7	119.5 (3)	C13—C14—H14	121.00
N1—C9—C14	119.9 (3)	C11—C15—H15A	110.00
C10—C9—C14	119.8 (3)	C11—C15—H15B	110.00
N1—C9—C10	120.3 (2)	C11—C15—H15C	110.00
C9—C10—C11	121.4 (3)	H15A—C15—H15B	109.00
C10—C11—C12	117.8 (3)	H15A—C15—H15C	109.00
C10—C11—C15	120.5 (3)	H15B—C15—H15C	109.00
C12—C11—C15	121.7 (3)

O1—S1—N1—C9	−173.3 (2)	C8—C3—C4—C5	0.1 (4)
O2—S1—N1—C9	59.1 (2)	C3—C4—C5—C6	−0.1 (5)
C6—S1—N1—C9	−56.4 (2)	C4—C5—C6—C7	0.4 (4)
O2—S1—C6—C7	166.2 (2)	C4—C5—C6—S1	−175.7 (2)
N1—S1—C6—C7	−78.9 (2)	S1—C6—C7—C8	175.5 (2)
O2—S1—C6—C5	−17.6 (3)	C5—C6—C7—C8	−0.7 (4)
N1—S1—C6—C5	97.3 (3)	C6—C7—C8—C3	0.6 (4)
O1—S1—C6—C5	−149.0 (2)	N1—C9—C10—C11	−179.8 (3)
O1—S1—C6—C7	34.9 (3)	C14—C9—C10—C11	−1.4 (5)
S1—N1—C9—C10	−73.2 (3)	N1—C9—C14—C13	178.4 (3)
S1—N1—C9—C14	108.4 (3)	C10—C9—C14—C13	0.1 (5)
C2—N2—C3—C4	−153.2 (3)	C9—C10—C11—C12	1.5 (5)
C3—N2—C2—O3	−4.5 (5)	C9—C10—C11—C15	−178.6 (3)
C2—N2—C3—C8	27.5 (5)	C10—C11—C12—C13	−0.4 (6)
C3—N2—C2—C1	174.8 (3)	C15—C11—C12—C13	179.7 (4)
N2—C3—C4—C5	−179.2 (3)	C11—C12—C13—C14	−0.9 (6)
C4—C3—C8—C7	−0.3 (4)	C12—C13—C14—C9	1.1 (5)
N2—C3—C8—C7	179.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86 (2)	2.09 (2)	2.938 (3)	171 (2)
N2—H2N···O3ⁱⁱ	0.84 (2)	2.05 (2)	2.878 (3)	173 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₃S
M_r	304.37
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.4072 (4), 9.8528 (4), 24.7872 (10)
V (Å³)	3030.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.13 × 0.10 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27585, 3766, 2018
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.146, 1.02
No. of reflections	3766
No. of parameters	200
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.858 (18)	2.088 (19)	2.938 (3)	171 (2)
N2—H2N···O3ⁱⁱ	0.84 (2)	2.046 (19)	2.878 (3)	173 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+1/2, y+1/2, z.

Footnotes

‡Additional correspondence author, e-mail: akhyar100@gmail.com.

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University Lahore.

References

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