N-(4-Chloro-2-nitro-phen-yl)methane-sulfonamide.

The title compound, C(7)H(7)ClN(2)O(4)S, is of inter-est as a precursor to biologically active substituted quinolines. Its structure resembles those of the previously reported N-phenyl-methane sulfonamide and its 4-nitro, 4-fluoro and 4-bromo derivatives, with slightly different geometric parameters. An intra-molecular N-H⋯O hydrogen bond gives rise to a six-membered ring. Inter-molecular 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 = 250.67

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.147

S = 0.97

2556 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.39 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H7ClN2O4S	F(000) = 512
Mr = 250.67	Dx = 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

Bruker APEXII CCD area-detector diffractometer	1199 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
graphite	θmax = 28.7°, θmin = 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 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(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3
2556 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .