N-(4-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812049070

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o7

https://doi.org/10.1107/S1600536812049070

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N-(4-Chlorophenyl)-4-nitrobenzenesulfonamide

U. Chaithanya,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 27 November 2012; accepted 29 November 2012; online 5 December 2012)

In the title compound, C₁₂H₉ClN₂O₄S, the dihedral angle between the benzene rings is 31.4 (2)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains running along the a-axis direction.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994 ), of N-arylsulfonamides, see: Chaithanya et al. (2012 ); Gowda et al. (2003 ) and of N-chloroarylsulfonamides, see: Gowda et al. (2005 ); Shetty & Gowda (2004 ).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M_r = 312.72
Monoclinic, C c
a = 5.0881 (4) Å
b = 13.0313 (9) Å
c = 19.886 (2) Å
β = 94.194 (7)°
V = 1315.00 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.46 × 0.24 × 0.12 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 = 0.815, T_max = 0.947
2432 measured reflections
1557 independent reflections
1432 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.092
S = 1.13
1557 reflections
184 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 203 Friedel pairs
Flack parameter: −0.02 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (2)	2.16 (2)	3.007 (4)	173 (5)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536812049070/bt6873sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049070/bt6873Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812049070/bt6873Isup3.cml

checkCIF report

Comment top

As a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda & Weiss, 1994); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2003) and N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(4-chlorophenyl)-4-nitrobenzenesulfonamide (I) has been determined (Fig. 1).

The conformation of the N—C bond in the —SO₂—NH—C segment has gauche torsions with respect to the S═O bonds (Fig. 1), similar to that observed in N-(phenyl)-4-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of 63.74 (35)°, compared to the value of 61.89 (32)° in (II).

The dihedral angle between the sulfonyl and the anilino rings is 31.40 (23)°, compared to the value of 36.19 (18)° in (II).

In the crystal, intermolecular N—H···O hydrogen bond interactions link the molecules into C(4) chains. Part of the crystal structure is shown in Fig. 2.

Related literature top

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2003) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

Experimental top

The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with 4-chloroaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(4-chlorophenyl)-4-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in an ethanolic solution by slow evaporation of the solvent at room temperature.

Structure description top

The dihedral angle between the sulfonyl and the anilino rings is 31.40 (23)°, compared to the value of 36.19 (18)° in (II).

In the crystal, intermolecular N—H···O hydrogen bond interactions link the molecules into C(4) chains. Part of the crystal structure is shown in Fig. 2.

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2003) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (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 and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N-(4-Chlorophenyl)-4-nitrobenzenesulfonamide top

Crystal data top

C₁₂H₉ClN₂O₄S	F(000) = 640
M_r = 312.72	D_x = 1.580 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1307 reflections
a = 5.0881 (4) Å	θ = 2.6–27.8°
b = 13.0313 (9) Å	µ = 0.46 mm⁻¹
c = 19.886 (2) Å	T = 293 K
β = 94.194 (7)°	Prism, colourless
V = 1315.00 (19) Å³	0.46 × 0.24 × 0.12 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1557 independent reflections
Radiation source: fine-focus sealed tube	1432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→3
T_min = 0.815, T_max = 0.947	k = −8→16
2432 measured reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0318P)² + 1.8686P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
1557 reflections	Δρ_max = 0.29 e Å⁻³
184 parameters	Δρ_min = −0.29 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 203 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (11)

Crystal data top

C₁₂H₉ClN₂O₄S	V = 1315.00 (19) Å³
M_r = 312.72	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.0881 (4) Å	µ = 0.46 mm⁻¹
b = 13.0313 (9) Å	T = 293 K
c = 19.886 (2) Å	0.46 × 0.24 × 0.12 mm
β = 94.194 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1557 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1432 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.947	R_int = 0.014
2432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	Δρ_max = 0.29 e Å⁻³
S = 1.13	Δρ_min = −0.29 e Å⁻³
1557 reflections	Absolute structure: Flack (1983), 203 Friedel pairs
184 parameters	Absolute structure parameter: −0.02 (11)
3 restraints

Special details top

Experimental. Absorption correction: 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
C1	0.3399 (8)	0.8673 (3)	0.3654 (2)	0.0386 (9)
C2	0.5320 (9)	0.8525 (3)	0.3209 (2)	0.0464 (11)
H2	0.6101	0.7885	0.3173	0.056*
C3	0.6079 (10)	0.9336 (3)	0.2819 (2)	0.0479 (12)
H3	0.7365	0.9249	0.2514	0.057*
C4	0.4895 (9)	1.0268 (3)	0.2889 (2)	0.0405 (10)
C5	0.2944 (10)	1.0418 (3)	0.3320 (3)	0.0522 (12)
H5	0.2142	1.1056	0.3350	0.063*
C6	0.2198 (9)	0.9608 (3)	0.3704 (3)	0.0499 (11)
H6	0.0878	0.9694	0.3999	0.060*
C7	0.4286 (8)	0.8807 (4)	0.5281 (2)	0.0417 (10)
C8	0.5769 (10)	0.9675 (4)	0.5181 (3)	0.0549 (12)
H8	0.7061	0.9655	0.4873	0.066*
C9	0.5366 (12)	1.0564 (4)	0.5527 (3)	0.0635 (15)
H9	0.6395	1.1141	0.5464	0.076*
C10	0.3403 (11)	1.0586 (4)	0.5970 (2)	0.0539 (13)
C11	0.1964 (11)	0.9734 (4)	0.6082 (2)	0.0584 (14)
H11	0.0676	0.9757	0.6390	0.070*
C12	0.2400 (10)	0.8829 (4)	0.5740 (2)	0.0535 (12)
H12	0.1425	0.8243	0.5821	0.064*
N1	0.4632 (7)	0.7883 (3)	0.4904 (2)	0.0454 (9)
H1N	0.620 (5)	0.783 (4)	0.479 (2)	0.055*
N2	0.5752 (9)	1.1153 (3)	0.2495 (2)	0.0540 (10)
O1	0.3503 (6)	0.6725 (2)	0.39544 (17)	0.0528 (8)
O2	0.0062 (6)	0.7821 (2)	0.44006 (16)	0.0508 (8)
O3	0.7655 (9)	1.1042 (3)	0.2172 (2)	0.0846 (14)
O4	0.4539 (9)	1.1952 (3)	0.2524 (2)	0.0773 (13)
Cl1	0.2766 (3)	1.17181 (11)	0.63901 (8)	0.0816 (5)
S1	0.27032 (19)	0.76820 (7)	0.42212 (6)	0.0408 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.035 (2)	0.034 (2)	0.047 (2)	−0.0002 (18)	0.0082 (19)	0.0000 (18)
C2	0.049 (3)	0.035 (2)	0.057 (3)	0.004 (2)	0.017 (2)	−0.005 (2)
C3	0.052 (3)	0.048 (3)	0.046 (2)	0.003 (2)	0.019 (2)	−0.002 (2)
C4	0.043 (2)	0.038 (2)	0.042 (2)	−0.002 (2)	0.009 (2)	0.0015 (18)
C5	0.054 (3)	0.032 (2)	0.072 (3)	0.010 (2)	0.016 (3)	0.005 (2)
C6	0.043 (3)	0.043 (2)	0.066 (3)	0.007 (2)	0.023 (2)	0.001 (2)
C7	0.035 (2)	0.046 (3)	0.044 (2)	0.003 (2)	0.0044 (19)	−0.001 (2)
C8	0.049 (3)	0.053 (3)	0.066 (3)	−0.010 (2)	0.021 (2)	−0.005 (2)
C9	0.075 (4)	0.045 (3)	0.073 (4)	−0.011 (3)	0.017 (3)	−0.001 (2)
C10	0.070 (3)	0.042 (3)	0.049 (3)	0.011 (2)	0.000 (3)	−0.002 (2)
C11	0.057 (3)	0.069 (4)	0.051 (3)	0.000 (3)	0.021 (2)	−0.008 (2)
C12	0.060 (3)	0.053 (3)	0.050 (3)	−0.011 (2)	0.020 (2)	0.000 (2)
N1	0.0347 (19)	0.045 (2)	0.058 (2)	0.0038 (17)	0.0116 (17)	−0.0014 (17)
N2	0.061 (3)	0.045 (2)	0.058 (2)	0.000 (2)	0.015 (2)	0.0051 (18)
O1	0.055 (2)	0.0328 (15)	0.072 (2)	0.0009 (14)	0.0165 (17)	−0.0057 (14)
O2	0.0334 (17)	0.0510 (19)	0.070 (2)	−0.0034 (14)	0.0145 (16)	0.0022 (15)
O3	0.087 (3)	0.069 (3)	0.106 (3)	0.008 (2)	0.057 (3)	0.022 (2)
O4	0.091 (3)	0.0454 (19)	0.100 (3)	0.013 (2)	0.038 (3)	0.0190 (19)
Cl1	0.1210 (14)	0.0577 (8)	0.0657 (9)	0.0210 (9)	0.0044 (9)	−0.0131 (7)
S1	0.0349 (5)	0.0353 (5)	0.0534 (6)	−0.0006 (5)	0.0110 (4)	−0.0006 (5)

Geometric parameters (Å, º) top

C1—C6	1.370 (6)	C8—C9	1.370 (7)
C1—C2	1.378 (6)	C8—H8	0.9300
C1—S1	1.768 (4)	C9—C10	1.381 (7)
C2—C3	1.383 (6)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.357 (7)
C3—C4	1.368 (6)	C10—Cl1	1.737 (5)
C3—H3	0.9300	C11—C12	1.387 (7)
C4—C5	1.371 (6)	C11—H11	0.9300
C4—N2	1.479 (6)	C12—H12	0.9300
C5—C6	1.374 (6)	N1—S1	1.637 (4)
C5—H5	0.9300	N1—H1N	0.85 (2)
C6—H6	0.9300	N2—O3	1.209 (5)
C7—C12	1.373 (6)	N2—O4	1.214 (5)
C7—C8	1.382 (7)	O1—S1	1.426 (3)
C7—N1	1.436 (6)	O2—S1	1.427 (3)

C6—C1—C2	120.8 (4)	C8—C9—C10	118.7 (5)
C6—C1—S1	119.4 (3)	C8—C9—H9	120.7
C2—C1—S1	119.5 (3)	C10—C9—H9	120.7
C1—C2—C3	119.6 (4)	C11—C10—C9	120.8 (5)
C1—C2—H2	120.2	C11—C10—Cl1	119.6 (4)
C3—C2—H2	120.2	C9—C10—Cl1	119.6 (4)
C4—C3—C2	118.5 (4)	C10—C11—C12	120.5 (4)
C4—C3—H3	120.8	C10—C11—H11	119.7
C2—C3—H3	120.8	C12—C11—H11	119.7
C3—C4—C5	122.4 (4)	C7—C12—C11	119.2 (4)
C3—C4—N2	119.3 (4)	C7—C12—H12	120.4
C5—C4—N2	118.3 (4)	C11—C12—H12	120.4
C4—C5—C6	118.7 (4)	C7—N1—S1	118.6 (3)
C4—C5—H5	120.7	C7—N1—H1N	111 (4)
C6—C5—H5	120.7	S1—N1—H1N	106 (4)
C1—C6—C5	120.0 (4)	O3—N2—O4	123.9 (4)
C1—C6—H6	120.0	O3—N2—C4	117.8 (4)
C5—C6—H6	120.0	O4—N2—C4	118.3 (4)
C12—C7—C8	119.6 (4)	O1—S1—O2	120.2 (2)
C12—C7—N1	118.9 (4)	O1—S1—N1	106.2 (2)
C8—C7—N1	121.5 (4)	O2—S1—N1	106.9 (2)
C9—C8—C7	121.1 (4)	O1—S1—C1	109.0 (2)
C9—C8—H8	119.5	O2—S1—C1	107.7 (2)
C7—C8—H8	119.5	N1—S1—C1	106.1 (2)

C6—C1—C2—C3	1.2 (7)	N1—C7—C12—C11	−176.8 (5)
S1—C1—C2—C3	−172.7 (4)	C10—C11—C12—C7	−0.7 (8)
C1—C2—C3—C4	0.4 (7)	C12—C7—N1—S1	83.9 (5)
C2—C3—C4—C5	−1.7 (8)	C8—C7—N1—S1	−94.8 (5)
C2—C3—C4—N2	177.7 (4)	C3—C4—N2—O3	−7.2 (7)
C3—C4—C5—C6	1.5 (8)	C5—C4—N2—O3	172.3 (5)
N2—C4—C5—C6	−177.9 (5)	C3—C4—N2—O4	174.2 (5)
C2—C1—C6—C5	−1.4 (7)	C5—C4—N2—O4	−6.3 (7)
S1—C1—C6—C5	172.5 (4)	C7—N1—S1—O1	179.6 (3)
C4—C5—C6—C1	0.0 (8)	C7—N1—S1—O2	−50.9 (4)
C12—C7—C8—C9	−0.8 (8)	C7—N1—S1—C1	63.7 (3)
N1—C7—C8—C9	177.8 (5)	C6—C1—S1—O1	162.6 (4)
C7—C8—C9—C10	−1.3 (9)	C2—C1—S1—O1	−23.4 (4)
C8—C9—C10—C11	2.5 (9)	C6—C1—S1—O2	30.7 (4)
C8—C9—C10—Cl1	−177.5 (4)	C2—C1—S1—O2	−155.3 (4)
C9—C10—C11—C12	−1.5 (8)	C6—C1—S1—N1	−83.4 (4)
Cl1—C10—C11—C12	178.5 (4)	C2—C1—S1—N1	90.5 (4)
C8—C7—C12—C11	1.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.85 (2)	2.16 (2)	3.007 (4)	173 (5)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₉ClN₂O₄S
M_r	312.72
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	5.0881 (4), 13.0313 (9), 19.886 (2)
β (°)	94.194 (7)
V (Å³)	1315.00 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.46 × 0.24 × 0.12

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	0.815, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	2432, 1557, 1432
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.092, 1.13
No. of reflections	1557
No. of parameters	184
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29
Absolute structure	Flack (1983), 203 Friedel pairs
Absolute structure parameter	−0.02 (11)

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···O2ⁱ	0.85 (2)	2.16 (2)	3.007 (4)	173 (5)

Symmetry code: (i) x+1, y, z.

Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2872. CSD CrossRef IUCr Journals Google Scholar
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