N-(4-Chloro-2-nitro­phen­yl)methane­sulfonamide

Zia-ur-Rehman, M.; Choudary, J.A.; Akbar, N.; Khan, I.U.; Nadeem Arshad, M.

doi:10.1107/S1600536808031048

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages o2034-o2035

doi:10.1107/S1600536808031048

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N-(4-Chloro-2-nitrophenyl)methanesulfonamide

Muhammad Zia-ur-Rehman,^a ^* Jamil Anwar Choudary,^b Nosheen Akbar,^c Islam Ullah Khan ^d and Muhammad Nadeem Arshad ^d

^aApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, ^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^cCentre for High Energy Physics, University of the Punjab, Lahore 54590, Pakistan, and ^dDepartment of Chemistry, Government College University, Lahore 54000, Pakistan
^*Correspondence e-mail: noshinakbar@yahoo.com

(Received 18 September 2008; accepted 25 September 2008; online 30 September 2008)

The title compound, C₇H₇ClN₂O₄S, is of interest as a precursor to biologically active substituted quinolines. Its structure resembles those of the previously reported N-phenylmethane sulfonamide and its 4-nitro, 4-fluoro and 4-bromo derivatives, with slightly different geometric parameters. An intramolecular N—H⋯O hydrogen bond gives rise to a six-membered ring. Intermolecular C—H⋯O contacts stabilize the crystal packing.

Related literature

For related literature, see: Ahn et al. (1997 ); Allen et al. (1987 ); Ozbek et al. (2007 ); Siddiqui et al. (2007 ); Gennarti et al. (1994 ); Gowda et al. (2007a ,b ,c ); Hanson et al. (1999 ); Moree et al. (1991 ); Oppolzer et al. (1991 ); Rough et al. (1998 ); Zia-ur-Rehman et al. (2005 , 2006 , 2007 , 2008 ).

Experimental

Crystal data

C₇H₇ClN₂O₄S
M_r = 250.67
Monoclinic, P 2₁ /n
a = 11.728 (3) Å
b = 4.9798 (13) Å
c = 17.988 (5) Å
β = 107.334 (8)°
V = 1002.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 296 (2) K
0.22 × 0.14 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
10700 measured reflections
2590 independent reflections
1199 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.147
S = 0.97
2556 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.80 (4)	2.03 (4)	2.631 (4)	131 (3)
C3—H3⋯O3ⁱ	0.93	2.59	3.417 (4)	148
C5—H5⋯O2ⁱⁱ	0.93	2.47	3.325 (5)	152
C6—H6⋯O2	0.93	2.27	2.951 (5)	130
C7—H8⋯O3ⁱⁱⁱ	0.96	2.53	3.394 (5)	150
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y, -z+2.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031048/bt2794sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031048/bt2794Isup2.hkl

checkCIF report

Comment top

Sulfonamides are familiar for their enormous potential as biologically active molecules (Hanson et al., 1999; Moree et al., 1991; Rough et al., 1998). They are being used as anti-microbial (Ozbek et al., 2007), anti-convulsant (Siddiqui et al., 2007), and for the treatment of inflammatory rheumatic and non-rheumatic processes including onsets and traumatologic lesions (Gennarti et al., 1994). Besides, these are known as compounds being used as agricultural agents and chiral auxiliaries (Ahn et al., 1997; Oppolzer et al., 1991). Among these, alkyl sulfonanilides are of special interest due to their stereochemistry with amide hydrogen on one side of the plane of benzene ring making it a good receptor site for biological reactions. In the present paper, the structure of N-(4-chloro-2-nitrophenyl)methanesulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2005, 2006, 2007, 2008). In the molecule of (I) (Fig. 1), bond lengths and bond angles are almost similar to those in the related molecules (Gowda et al., 2007a,b,c) and are within normal ranges (Allen et al., 1987). Intramolecular interaction [N1—H1···O3] is observed in the title molecule giving rise to six-membered hydrogen bonded ring. Each molecule is centrosymmetrically linked to its adjacent one through intermolecular [N1—H1···O1] hydrogen bonds on one side, and via [C5—H5···O2] hydrogen bonds on the other side, giving rise to a zigzag chain along a axis. Each molecule of a chain is further linked to the member of adjacent chain via [C3—H3···O3] hydrogen bonds along c giving rise to a three dimensional network.

Related literature top

For related literature, see: Ahn et al. (1997); Allen et al. (1987); Ozbek et al. (2007); Siddiqui et al. (2007); Gennarti et al. (1994); Gowda et al. (2007a,b,c); Hanson et al. (1999); Moree et al. (1991); Oppolzer et al. (1991); Rough et al. (1998); Zia-ur-Rehman et al. (2005, 2006, 2007, 2008).

Experimental top

A mixture of 4-chloro-2-nitroaniline (3.452 g; 20.0 mmoles) and mesyl chloride (2.52 g; 22.0 mmoles) and toluene (25.0 ml) was heated to reflux for half an hour. Solvent was then distilled off under reduced pressure and the resultant solids were washed with cold methanol. Crystals suitable for analysis were obtained by slow evaporation of methanolic solution over a period of two days.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Perspective view of the crystal packing showing hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

N-(4-Chloro-2-nitrophenyl)methanesulfonamide top

Crystal data top

C₇H₇ClN₂O₄S	F(000) = 512
M_r = 250.67	D_x = 1.660 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 388 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.728 (3) Å	Cell parameters from 1283 reflections
b = 4.9798 (13) Å	θ = 2.4–20.9°
c = 17.988 (5) Å	µ = 0.58 mm⁻¹
β = 107.334 (8)°	T = 296 K
V = 1002.8 (5) Å³	Needle, light yellow
Z = 4	0.22 × 0.14 × 0.07 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1199 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.081
Graphite monochromator	θ_max = 28.7°, θ_min = 1.9°
Detector resolution: 7.5 pixels mm^-1	h = −15→15
ϕ and ω scans	k = −6→6
10700 measured reflections	l = −23→24
2590 independent reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
2556 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₇H₇ClN₂O₄S	V = 1002.8 (5) Å³
M_r = 250.67	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.728 (3) Å	µ = 0.58 mm⁻¹
b = 4.9798 (13) Å	T = 296 K
c = 17.988 (5) Å	0.22 × 0.14 × 0.07 mm
β = 107.334 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1199 reflections with I > 2σ(I)
10700 measured reflections	R_int = 0.081
2590 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.25 e Å⁻³
2556 reflections	Δρ_min = −0.39 e Å⁻³
140 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
Cl1	0.36565 (9)	−0.3010 (2)	0.78879 (7)	0.0757 (4)
S1	0.82089 (9)	0.53780 (17)	1.02558 (6)	0.0499 (3)
O1	0.9148 (3)	0.7102 (5)	1.01960 (19)	0.0756 (9)
O2	0.7141 (2)	0.6562 (5)	1.03188 (16)	0.0647 (8)
O3	0.8855 (2)	0.1004 (5)	0.85222 (14)	0.0554 (7)
O4	0.8088 (2)	−0.2740 (5)	0.80406 (15)	0.0613 (7)
H1	0.852 (3)	0.324 (7)	0.938 (2)	0.047 (11)*
N1	0.7906 (3)	0.3571 (6)	0.94717 (19)	0.0509 (8)
N2	0.8034 (3)	−0.0641 (6)	0.83722 (16)	0.0441 (7)
C1	0.6920 (3)	0.1941 (6)	0.91264 (19)	0.0416 (8)
C2	0.6953 (3)	−0.0052 (6)	0.85865 (19)	0.0397 (8)
C3	0.5963 (3)	−0.1573 (7)	0.8216 (2)	0.0473 (9)
H3	0.6013	−0.2884	0.7859	0.057*
C4	0.4913 (3)	−0.1147 (7)	0.8376 (2)	0.0507 (9)
C5	0.4847 (3)	0.0733 (7)	0.8916 (2)	0.0559 (10)
H5	0.4136	0.0974	0.9037	0.067*
C6	0.5830 (4)	0.2266 (7)	0.9282 (2)	0.0556 (10)
H6	0.5767	0.3554	0.9642	0.067*
C7	0.8741 (4)	0.3148 (8)	1.1025 (3)	0.0756 (13)
H8	0.9413	0.2183	1.0959	0.113*
H9	0.8121	0.1903	1.1036	0.113*
H7	0.8984	0.4127	1.1507	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0495 (6)	0.0871 (8)	0.0875 (9)	−0.0078 (5)	0.0156 (6)	−0.0033 (6)
S1	0.0594 (6)	0.0414 (5)	0.0527 (6)	0.0081 (4)	0.0224 (5)	−0.0082 (4)
O1	0.083 (2)	0.0540 (15)	0.100 (2)	−0.0184 (14)	0.0431 (19)	−0.0276 (15)
O2	0.0700 (18)	0.0622 (16)	0.0661 (19)	0.0267 (13)	0.0267 (14)	−0.0096 (13)
O3	0.0468 (15)	0.0678 (16)	0.0571 (18)	−0.0027 (13)	0.0238 (13)	−0.0109 (13)
O4	0.0608 (17)	0.0650 (16)	0.0627 (19)	0.0092 (12)	0.0255 (14)	−0.0258 (13)
N1	0.050 (2)	0.0539 (18)	0.058 (2)	0.0022 (16)	0.0296 (17)	−0.0131 (14)
N2	0.0457 (18)	0.0526 (17)	0.0364 (17)	0.0107 (15)	0.0157 (13)	−0.0016 (13)
C1	0.048 (2)	0.0412 (18)	0.040 (2)	0.0068 (16)	0.0205 (17)	0.0032 (15)
C2	0.042 (2)	0.0445 (18)	0.0361 (19)	0.0112 (15)	0.0167 (16)	0.0071 (14)
C3	0.050 (2)	0.053 (2)	0.040 (2)	0.0066 (17)	0.0149 (17)	−0.0007 (16)
C4	0.042 (2)	0.058 (2)	0.053 (2)	0.0034 (17)	0.0137 (18)	0.0078 (18)
C5	0.044 (2)	0.061 (2)	0.071 (3)	0.0128 (19)	0.029 (2)	0.006 (2)
C6	0.060 (3)	0.053 (2)	0.063 (3)	0.0093 (19)	0.032 (2)	−0.0051 (18)
C7	0.086 (3)	0.075 (3)	0.058 (3)	0.021 (2)	0.010 (2)	0.003 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.741 (4)	C1—C6	1.397 (5)
S1—O2	1.419 (3)	C2—C3	1.380 (5)
S1—O1	1.426 (3)	C3—C4	1.363 (4)
S1—N1	1.621 (3)	C3—H3	0.9300
S1—C7	1.739 (4)	C4—C5	1.368 (5)
O3—N2	1.231 (3)	C5—C6	1.375 (5)
O4—N2	1.215 (3)	C5—H5	0.9300
N1—C1	1.397 (4)	C6—H6	0.9300
N1—H1	0.80 (3)	C7—H8	0.9600
N2—C2	1.461 (4)	C7—H9	0.9600
C1—C2	1.397 (4)	C7—H7	0.9600

O2—S1—O1	118.43 (17)	C4—C3—C2	119.7 (3)
O2—S1—N1	109.28 (17)	C4—C3—H3	120.1
O1—S1—N1	104.05 (17)	C2—C3—H3	120.1
O2—S1—C7	108.5 (2)	C3—C4—C5	120.2 (3)
O1—S1—C7	110.0 (2)	C3—C4—Cl1	119.5 (3)
N1—S1—C7	105.77 (19)	C5—C4—Cl1	120.3 (3)
C1—N1—S1	130.3 (3)	C4—C5—C6	120.2 (3)
C1—N1—H1	118 (3)	C4—C5—H5	119.9
S1—N1—H1	108 (3)	C6—C5—H5	119.9
O4—N2—O3	121.9 (3)	C5—C6—C1	121.8 (3)
O4—N2—C2	118.6 (3)	C5—C6—H6	119.1
O3—N2—C2	119.5 (3)	C1—C6—H6	119.1
C2—C1—C6	116.0 (3)	S1—C7—H8	109.5
C2—C1—N1	122.1 (3)	S1—C7—H9	109.5
C6—C1—N1	121.9 (3)	H8—C7—H9	109.5
C3—C2—C1	122.1 (3)	S1—C7—H7	109.5
C3—C2—N2	115.7 (3)	H8—C7—H7	109.5
C1—C2—N2	122.2 (3)	H9—C7—H7	109.5

O2—S1—N1—C1	−37.6 (4)	O4—N2—C2—C1	163.9 (3)
O1—S1—N1—C1	−165.0 (3)	O3—N2—C2—C1	−17.0 (4)
C7—S1—N1—C1	79.0 (4)	C1—C2—C3—C4	−0.1 (5)
S1—N1—C1—C2	−161.2 (3)	N2—C2—C3—C4	−179.5 (3)
S1—N1—C1—C6	21.0 (5)	C2—C3—C4—C5	−1.7 (5)
C6—C1—C2—C3	1.3 (5)	C2—C3—C4—Cl1	178.3 (3)
N1—C1—C2—C3	−176.7 (3)	C3—C4—C5—C6	2.2 (6)
C6—C1—C2—N2	−179.3 (3)	Cl1—C4—C5—C6	−177.8 (3)
N1—C1—C2—N2	2.7 (5)	C4—C5—C6—C1	−1.0 (6)
O4—N2—C2—C3	−16.6 (4)	C2—C1—C6—C5	−0.7 (5)
O3—N2—C2—C3	162.5 (3)	N1—C1—C6—C5	177.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.80 (4)	2.03 (4)	2.631 (4)	131 (3)
C3—H3···O3ⁱ	0.93	2.59	3.417 (4)	148
C5—H5···O2ⁱⁱ	0.93	2.47	3.325 (5)	152
C6—H6···O2	0.93	2.27	2.951 (5)	130
C7—H8···O3ⁱⁱⁱ	0.96	2.53	3.394 (5)	150

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

Experimental details

Crystal data
Chemical formula	C₇H₇ClN₂O₄S
M_r	250.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.728 (3), 4.9798 (13), 17.988 (5)
β (°)	107.334 (8)
V (Å³)	1002.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.22 × 0.14 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10700, 2590, 1199
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.148, 0.97
No. of reflections	2556
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.80 (4)	2.03 (4)	2.631 (4)	131 (3)
C3—H3···O3ⁱ	0.93	2.59	3.417 (4)	148
C5—H5···O2ⁱⁱ	0.93	2.47	3.325 (5)	152
C6—H6···O2	0.93	2.27	2.951 (5)	130
C7—H8···O3ⁱⁱⁱ	0.96	2.53	3.394 (5)	150

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

Acknowledgements

The authors are grateful to the PCSIR Laboratories Complex, Lahore, Pakistan, for provision of the necessary chemicals, and to the Higher Education Commission of Pakistan for the grant to purchase the diffractometer.

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