N-(3-Nitro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536812016765

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1507

doi:10.1107/S1600536812016765

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N-(3-Nitrobenzoyl)benzenesulfonamide

P. A. Suchetan,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 13 April 2012; accepted 17 April 2012; online 21 April 2012)

In the title compound, C₁₃H₁₀N₂O₅S, the C=O bond in the —SO₂—NH—CO— segment is anti to the meta-nitro group in the benzoyl ring, while the N—C bond has gauche torsions with respect to the S=O bonds. The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the —SO₂—NH—CO— segment. Furthermore, the dihedral angle between the benzeneline rings is 86.9 (2)°. In the structure, the molecules are linked into helical chains along the b axis via N—H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000 , 2007 ), of N-(substitutedbenzoyl)-arylsulfonamides, see: Gowda et al. (2009 ), of N-chloroarylamides, see: Jyothi & Gowda (2004 ) and of N-bromoarylsulfonamides, see: Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₃H₁₀N₂O₅S
M_r = 306.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.1053 (5) Å
b = 13.078 (1) Å
c = 20.163 (2) Å
V = 1346.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.48 × 0.12 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with 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 = 0.884, T_max = 0.969
4590 measured reflections
2282 independent reflections
1869 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.137
S = 1.38
2282 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 871 Friedel pairs
Flack parameter: −0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86 (2)	2.05 (2)	2.909 (6)	175 (6)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

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/S1600536812016765/bt5879sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016765/bt5879Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016765/bt5879Isup3.cml

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2007), N-(substitutedbenzoyl)-arylsulfonamides (Gowda et al., 2009), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-nitrobenzoyl)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 (Fig.1), similar to that observed in N-(3-chlorobenzoyl)benzenesulfonamide (I)(Gowda et al., 2009).

Further, the C=O bond in the segment is anti to the meta-nitro group in the benzoyl ring, while the conformation of the N—C bond in the C—SO₂—NH—C(O) segment of the structure has "gauche" torsions with respect to the S═O bonds. The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the C—SO₂—NH—C—O segment, compared to the value of 79.6 (1)° in (I).

The dihedral angles between the sulfonyl and the benzoyl benzene rings is 86.9 (2)°, compared to the value of 89.3 (1)° in (I).

The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) 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 et al. (2000, 2007), on N-(substitutedbenzoyl)-arylsulfonamides, see: Gowda et al. (2009), on N-chloroarylamides, see: Jyothi & Gowda (2004) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental top

The title compound was prepared by refluxing a mixture of 3-nitrobenzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 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 sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point.

Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of the solvent from 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.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-(3-Nitrobenzoyl)benzenesulfonamide top

Crystal data top

C₁₃H₁₀N₂O₅S	F(000) = 632
M_r = 306.29	D_x = 1.511 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1855 reflections
a = 5.1053 (5) Å	θ = 3.0–27.8°
b = 13.078 (1) Å	µ = 0.26 mm⁻¹
c = 20.163 (2) Å	T = 293 K
V = 1346.2 (2) Å³	Rod, colourless
Z = 4	0.48 × 0.12 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2282 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Rotation method data acquisition using ω and phi scans.	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	h = −3→6
T_min = 0.884, T_max = 0.969	k = −15→11
4590 measured reflections	l = −20→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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.P)² + 2.6443P] where P = (F_o² + 2F_c²)/3
S = 1.38	(Δ/σ)_max < 0.001
2282 reflections	Δρ_max = 0.28 e Å⁻³
193 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 871 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (2)

Crystal data top

C₁₃H₁₀N₂O₅S	V = 1346.2 (2) Å³
M_r = 306.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.1053 (5) Å	µ = 0.26 mm⁻¹
b = 13.078 (1) Å	T = 293 K
c = 20.163 (2) Å	0.48 × 0.12 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2282 independent reflections
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	1869 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.969	R_int = 0.028
4590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	Δρ_max = 0.28 e Å⁻³
S = 1.38	Δρ_min = −0.32 e Å⁻³
2282 reflections	Absolute structure: Flack (1983), 871 Friedel pairs
193 parameters	Absolute structure parameter: −0.1 (2)
1 restraint

Special details top

Experimental. 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	0.3551 (11)	0.4936 (4)	0.9411 (3)	0.0341 (12)
C2	0.3105 (16)	0.5680 (5)	0.8942 (3)	0.0559 (18)
H2	0.1925	0.5564	0.8599	0.067*
C3	0.4420 (17)	0.6597 (5)	0.8985 (4)	0.067 (2)
H3	0.4091	0.7108	0.8675	0.080*
C4	0.6203 (16)	0.6760 (5)	0.9478 (4)	0.064 (2)
H4	0.7113	0.7375	0.9498	0.077*
C5	0.6647 (16)	0.6020 (5)	0.9941 (4)	0.067 (2)
H5	0.7854	0.6137	1.0278	0.081*
C6	0.5320 (14)	0.5097 (5)	0.9915 (3)	0.0539 (18)
H6	0.5620	0.4595	1.0233	0.065*
C7	0.4855 (12)	0.3009 (4)	0.8392 (3)	0.0362 (14)
C8	0.6560 (12)	0.2129 (4)	0.8190 (3)	0.0351 (13)
C9	0.6177 (11)	0.1146 (4)	0.8425 (3)	0.0389 (14)
H9	0.4848	0.1004	0.8727	0.047*
C10	0.7814 (13)	0.0385 (4)	0.8202 (3)	0.0398 (15)
C11	0.9833 (13)	0.0555 (5)	0.7769 (3)	0.0456 (16)
H11	1.0941	0.0026	0.7642	0.055*
C12	1.0182 (13)	0.1533 (4)	0.7527 (3)	0.0450 (16)
H12	1.1517	0.1669	0.7226	0.054*
C13	0.8550 (13)	0.2305 (5)	0.7732 (3)	0.0450 (16)
H13	0.8779	0.2960	0.7562	0.054*
N1	0.3859 (10)	0.2927 (3)	0.9027 (2)	0.0383 (12)
H1N	0.458 (11)	0.256 (4)	0.933 (2)	0.046*
N2	0.7308 (14)	−0.0663 (4)	0.8455 (3)	0.0612 (18)
O1	−0.0348 (8)	0.3898 (3)	0.8930 (2)	0.0584 (13)
O2	0.1461 (10)	0.3402 (3)	1.0022 (2)	0.0561 (13)
O3	0.4341 (9)	0.3708 (3)	0.8029 (2)	0.0504 (11)
O4	0.9051 (11)	−0.1293 (4)	0.8380 (3)	0.0777 (16)
O5	0.5233 (14)	−0.0835 (4)	0.8715 (4)	0.109 (3)
S1	0.1833 (3)	0.37784 (11)	0.93608 (8)	0.0406 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (3)	0.026 (3)	0.040 (3)	−0.003 (2)	0.001 (3)	−0.003 (3)
C2	0.077 (5)	0.043 (4)	0.048 (4)	−0.011 (4)	−0.011 (4)	0.002 (3)
C3	0.101 (6)	0.031 (4)	0.069 (5)	−0.013 (4)	−0.007 (5)	0.012 (3)
C4	0.076 (5)	0.040 (4)	0.077 (5)	−0.016 (4)	0.000 (5)	−0.007 (4)
C5	0.064 (5)	0.060 (5)	0.077 (5)	−0.019 (4)	−0.024 (4)	−0.011 (4)
C6	0.057 (4)	0.044 (4)	0.060 (4)	0.003 (4)	−0.020 (4)	0.005 (3)
C7	0.045 (4)	0.025 (3)	0.039 (3)	−0.007 (3)	−0.008 (3)	0.001 (3)
C8	0.043 (3)	0.029 (3)	0.033 (3)	−0.004 (3)	−0.003 (3)	−0.004 (2)
C9	0.047 (4)	0.035 (3)	0.034 (3)	−0.007 (3)	0.007 (3)	−0.003 (3)
C10	0.052 (4)	0.023 (3)	0.044 (3)	−0.006 (3)	0.005 (3)	0.000 (3)
C11	0.047 (4)	0.042 (4)	0.048 (4)	0.001 (3)	0.010 (3)	−0.013 (3)
C12	0.046 (4)	0.043 (4)	0.046 (3)	−0.008 (3)	0.018 (3)	−0.003 (3)
C13	0.049 (4)	0.046 (4)	0.041 (3)	−0.016 (3)	−0.001 (3)	0.001 (3)
N1	0.047 (3)	0.027 (2)	0.041 (3)	0.007 (2)	0.000 (2)	0.005 (2)
N2	0.089 (6)	0.038 (3)	0.057 (4)	0.012 (3)	0.019 (4)	−0.002 (3)
O1	0.040 (2)	0.048 (3)	0.087 (3)	0.000 (2)	−0.012 (2)	−0.016 (3)
O2	0.074 (3)	0.038 (2)	0.056 (3)	−0.007 (2)	0.022 (3)	0.002 (2)
O3	0.065 (3)	0.040 (2)	0.046 (2)	0.005 (2)	−0.005 (2)	0.012 (2)
O4	0.111 (4)	0.047 (3)	0.074 (3)	0.029 (4)	0.020 (3)	0.007 (3)
O5	0.123 (6)	0.045 (3)	0.160 (6)	0.004 (3)	0.088 (5)	0.019 (3)
S1	0.0403 (8)	0.0314 (7)	0.0502 (8)	−0.0042 (7)	0.0052 (8)	−0.0019 (7)

Geometric parameters (Å, º) top

C1—C2	1.376 (8)	C8—C13	1.391 (8)
C1—C6	1.376 (8)	C9—C10	1.376 (8)
C1—S1	1.753 (5)	C9—H9	0.9300
C2—C3	1.377 (9)	C10—C11	1.368 (8)
C2—H2	0.9300	C10—N2	1.485 (8)
C3—C4	1.365 (10)	C11—C12	1.381 (8)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.363 (9)	C12—C13	1.372 (8)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.386 (9)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.662 (5)
C6—H6	0.9300	N1—H1N	0.86 (2)
C7—O3	1.200 (7)	N2—O5	1.203 (8)
C7—N1	1.382 (7)	N2—O4	1.222 (7)
C7—C8	1.499 (8)	O1—S1	1.421 (4)
C8—C9	1.385 (8)	O2—S1	1.433 (4)

C2—C1—C6	120.6 (6)	C8—C9—H9	120.9
C2—C1—S1	119.2 (5)	C11—C10—C9	123.3 (5)
C6—C1—S1	120.2 (5)	C11—C10—N2	120.0 (6)
C1—C2—C3	119.5 (6)	C9—C10—N2	116.7 (5)
C1—C2—H2	120.3	C10—C11—C12	118.2 (6)
C3—C2—H2	120.3	C10—C11—H11	120.9
C4—C3—C2	120.4 (7)	C12—C11—H11	120.9
C4—C3—H3	119.8	C13—C12—C11	119.7 (6)
C2—C3—H3	119.8	C13—C12—H12	120.1
C5—C4—C3	120.0 (7)	C11—C12—H12	120.1
C5—C4—H4	120.0	C12—C13—C8	121.5 (6)
C3—C4—H4	120.0	C12—C13—H13	119.3
C4—C5—C6	120.7 (7)	C8—C13—H13	119.3
C4—C5—H5	119.6	C7—N1—S1	123.5 (4)
C6—C5—H5	119.6	C7—N1—H1N	123 (4)
C1—C6—C5	118.8 (6)	S1—N1—H1N	111 (4)
C1—C6—H6	120.6	O5—N2—O4	124.7 (6)
C5—C6—H6	120.6	O5—N2—C10	118.4 (6)
O3—C7—N1	122.9 (6)	O4—N2—C10	116.9 (6)
O3—C7—C8	123.1 (5)	O1—S1—O2	120.2 (3)
N1—C7—C8	114.0 (5)	O1—S1—N1	108.3 (3)
C9—C8—C13	118.9 (6)	O2—S1—N1	103.2 (3)
C9—C8—C7	122.5 (5)	O1—S1—C1	109.4 (3)
C13—C8—C7	118.6 (5)	O2—S1—C1	108.0 (3)
C10—C9—C8	118.3 (5)	N1—S1—C1	106.9 (3)
C10—C9—H9	120.9

C6—C1—C2—C3	−0.9 (10)	C11—C12—C13—C8	1.0 (10)
S1—C1—C2—C3	179.0 (6)	C9—C8—C13—C12	−2.0 (9)
C1—C2—C3—C4	1.7 (12)	C7—C8—C13—C12	179.9 (5)
C2—C3—C4—C5	−1.5 (12)	O3—C7—N1—S1	0.4 (8)
C3—C4—C5—C6	0.5 (13)	C8—C7—N1—S1	−177.7 (4)
C2—C1—C6—C5	−0.1 (10)	C11—C10—N2—O5	−164.3 (7)
S1—C1—C6—C5	180.0 (6)	C9—C10—N2—O5	15.9 (10)
C4—C5—C6—C1	0.3 (12)	C11—C10—N2—O4	15.4 (9)
O3—C7—C8—C9	−147.0 (6)	C9—C10—N2—O4	−164.4 (6)
N1—C7—C8—C9	31.1 (8)	C7—N1—S1—O1	54.4 (5)
O3—C7—C8—C13	31.0 (9)	C7—N1—S1—O2	−177.2 (5)
N1—C7—C8—C13	−150.9 (5)	C7—N1—S1—C1	−63.4 (5)
C13—C8—C9—C10	0.9 (8)	C2—C1—S1—O1	−16.3 (6)
C7—C8—C9—C10	178.8 (5)	C6—C1—S1—O1	163.6 (5)
C8—C9—C10—C11	1.4 (9)	C2—C1—S1—O2	−148.7 (5)
C8—C9—C10—N2	−178.8 (5)	C6—C1—S1—O2	31.2 (6)
C9—C10—C11—C12	−2.4 (9)	C2—C1—S1—N1	100.8 (5)
N2—C10—C11—C12	177.8 (6)	C6—C1—S1—N1	−79.3 (5)
C10—C11—C12—C13	1.2 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86 (2)	2.05 (2)	2.909 (6)	175 (6)

Symmetry code: (i) x+1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂O₅S
M_r	306.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.1053 (5), 13.078 (1), 20.163 (2)
V (Å³)	1346.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.48 × 0.12 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector
Absorption correction	Multi-scan CrysAlis RED (Oxford Diffraction, 2009)
T_min, T_max	0.884, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	4590, 2282, 1869
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.137, 1.38
No. of reflections	2282
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.32
Absolute structure	Flack (1983), 871 Friedel pairs
Absolute structure parameter	−0.1 (2)

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	0.86 (2)	2.05 (2)	2.909 (6)	175 (6)

Symmetry code: (i) x+1/2, −y+1/2, −z+2.

Acknowledgements

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

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