N-(3-Chloro-benzo-yl)-2-nitro-benzene-sulfonamide.

Abstract

In the title compound, C(13)H(9)ClN(2)O(5)S, the N-C bond in the C-SO(2)-NH-C segment has a gauche torsion with respect to the S=O bonds. The conformation between the N-H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, and that between the C=O and the meta-Cl atom in the benzoyl ring is anti. The mol-ecule is twisted at the S-N bond, with a torsion angle of 65.41 (38)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 75.0 (1)°, and that between the sulfonyl and the benzoyl benzene ring is 89.1 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Full text

Page 1

N-(3-Chlorobenzoyl)-2-nitrobenzene-
sulfonamide
P. A. Suchetan,aSabine Foro,bB. Thimme Gowdaa* and
M. Shet Prakashc
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199,
Mangalore, India,bInstitute of Materials Science, Darmstadt University of Tech-
nology, Petersenstrasse 23, D-64287 Darmstadt, Germany, andcDepartment of
Chemistry, University College of Science, Tumkur University, Tumkur 572 102, India
Correspondence e-mail: gowdabt@yahoo.com
Received 8 February 2012; accepted 13 February 2012
Key indicators: single-crystal X-ray study; T = 293 K; mean ?(C–C) = 0.006 A ˚;
R factor = 0.074; wR factor = 0.147; data-to-parameter ratio = 14.3.
In the title compound, C13H9ClN2O5S, the N—C bond in the
C—SO2—NH—C segment has a gauche torsion with respect
to the S O bonds. The conformation between the N—H
bond and the ortho-nitro group in the sulfonyl benzene ring is
syn, and that between the C
O and the meta-Cl atom in the
benzoyl ring is anti. The molecule is twisted at the S—N bond,
with a torsion angle of 65.41 (38)?. The dihedral angle between
the sulfonyl benzene ring and the –SO2—NH—C—O segment
is 75.0 (1)?, and that between the sulfonyl and the benzoyl
benzene ring is 89.1 (1)?. The crystal structure features
inversion-related dimers linked by pairs of N—H???O(S)
hydrogen bonds.
Related literature
For our studies of the effects of substituents on the structures
and other aspects of N-(aryl)-amides, see: Gowda et al. (1999,
2006); N-(aryl)-methanesulfonamides, see: Gowda et al.
(2007);N-(substitutedbenzoyl)-arylsulfonamides,
Suchetan et al. (2012); N-chloroarylamides, see: Jyothi &
Gowda (2004) and N-bromoarylsulfonamides, see: Usha &
Gowda (2006)..
see:
Experimental
Crystal data
C13H9ClN2O5S
Mr= 340.73
Orthorhombic, Pbca
a = 12.2046 (8) A˚
b = 12.6121 (9) A˚
c = 18.433 (1) A˚
V = 2837.3 (3) A˚3
Z = 8
Mo K? radiation
? = 0.44 mm?1
T = 293 K
0.28 ? 0.28 ? 0.08 mm
Data collection
Oxford Xcalibur diffractometer
with Sapphire CCD detector
Absorption correction: multi-scan
(CrysAlis RED; Oxford
Diffraction, 2009)
Tmin= 0.886, Tmax= 0.966
11298 measured reflections
2889 independent reflections
1911 reflections with I > 2?(I)
Rint= 0.051
Refinement
R[F2> 2?(F2)] = 0.074
wR(F2) = 0.147
S = 1.20
2889 reflections
202 parameters
1 restraint
H atoms treated by a mixture of
independent and constrained
refinement
??max= 0.34 e A˚?3
??min= ?0.29 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N1—H1N???O1i
Symmetry code: (i) ?x;?y þ 2;?z.
D—HH???AD???AD—H???A
0.86 (2)2.41 (3)3.193 (4)153 (4)
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
refinement: CrysAlis CCD; 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); soft-
ware used to prepare material for publication: SHELXL97.
BTG thanks the University Grants Commission, Govern-
ment of India, New Delhi, for a special grant under a UGC-
BSR one-time grant to faculty.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: NC2268).
References
Gowda, B. T., Bhat, D. K., Fuess, H. & Weiss, A. (1999). Z. Naturforsch. Teil A,
54, 261–267.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.
Gowda, B. T., Kozisek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588–
594.
Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64–68.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford
Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o274.
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359.
organic compounds
o786
Suchetan et al.
doi:10.1107/S160053681200640X
Acta Cryst. (2012). E68, o786
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials
Acta Cryst. (2012). E68, o786 [doi:10.1107/S160053681200640X]
N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide
P. A. Suchetan, Sabine Foro, B. Thimme Gowda and M. Shet Prakash
Comment
As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al.,
1999, 2006), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et
al., 2012), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in
the present work, the crystal structure of N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide has been determined (Fig.1).
The conformation between the N—H and C═O bonds in the C—SO2—NH—C(O) segment is anti and the N—C bond
in the segment has gauche torsion with respect to the S═O bonds (Fig. 1), similar to that observed in N-(2-chloro-
benzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). In the title compound, the conformation between the N—
H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (I). Further, the
conformation of the C═O is anti to the meta-Cl atom in the benzoyl ring, similar to that observed between the C═O and
the ortho-Cl atom in (I).
The molecule is twisted at the S—N bond with the torsional angle of 65.41 (38)°, compared to the value of -59.68 (17)°
in (I).
The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 75.0 (1)°, compared to
the value of 77.5 (1)° in (I). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is
89.1 (1)°, compared to the value of 71.2 (1)° in (I).
In the crystal structure two molecules each are linked by pairs of intermolecular N—H···O (S) hydrogen bonds into
dimers that are located around centers of inversion (Fig. 2 and Table 1).
Experimental
The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 2-nitrobenzenesulfonamide
(0.02 mole) and excess phosphorous oxychloride for 3 h on a water bath. The resultant mixture was cooled and poured
into crushed ice. The solid, N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide, 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. It was filtered, dried and recrystallized.
Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow
evaporation of the solvent from its toluene solution at room temperature.
Refinement
The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (2) %A. The other H
atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with
isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

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Acta Cryst. (2012). E68, o786
Computing details
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).
Figure 1
Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the
50% probability level.

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Acta Cryst. (2012). E68, o786
Figure 2
View of the inversion-related dimers linked by pairs of N—H···O(S) hydrogen bonds (Hydrogen bonding is shown as
dashed lines)..
N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide
Crystal data
C13H9ClN2O5S
Mr = 340.73
Orthorhombic, Pbca
Hall symbol: -P 2ac 2ab
a = 12.2046 (8) Å
b = 12.6121 (9) Å
c = 18.433 (1) Å
V = 2837.3 (3) Å3
Z = 8
F(000) = 1392
Dx = 1.595 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 1818 reflections
θ = 2.6–27.9°
µ = 0.44 mm−1
T = 293 K
Rod, colourless
0.28 × 0.28 × 0.08 mm
Data collection
Oxford Xcalibur
diffractometer with Sapphire CCD detector
Radiation source: fine-focus sealed tube
Graphite monochromator
Rotation method data acquisition using ω and φ
scans

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Acta Cryst. (2012). E68, o786
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin = 0.886, Tmax = 0.966
11298 measured reflections
2889 independent reflections
1911 reflections with I > 2σ(I)
Rint = 0.051
θmax = 26.4°, θmin = 2.6°
h = −13→15
k = −15→11
l = −22→23
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.074
wR(F2) = 0.147
S = 1.20
2889 reflections
202 parameters
1 restraint
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0362P)2 + 4.7309P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.34 e Å−3
Δρmin = −0.29 e Å−3
Special details
Experimental. 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)
xyzUiso*/Ueq
C1
C2
C3
H3
C4
H4
C5
H5
C6
H6
C7
C8
C9
H9
C10
C11
H11
−0.0112 (3)
−0.0862 (3)
−0.1369 (4)
−0.1854
−0.1152 (4)
−0.1498
−0.0427 (4)
−0.0286
0.0092 (4)
0.0582
−0.0490 (3)
−0.1239 (3)
−0.1284 (3)
−0.0812
−0.2036 (4)
−0.2730 (4)
−0.3240
0.7252 (3)
0.7030 (3)
0.6063 (4)
0.5924
0.5307 (4)
0.4652
0.5506 (4)
0.4986
0.6469 (3)
0.6598
0.9234 (3)
1.0094 (3)
1.1061 (3)
1.1205
1.1812 (3)
1.1613 (4)
1.2119
0.0676 (2)
0.0131 (2)
0.0079 (3)
−0.0298
0.0590 (3)
0.0563
0.1143 (3)
0.1488
0.1188 (2)
0.1564
0.1845 (2)
0.2089 (2)
0.1738 (2)
0.1354
0.1960 (2)
0.2528 (2)
0.2672
0.0347 (9)
0.0402 (10)
0.0503 (12)
0.060*
0.0552 (13)
0.066*
0.0537 (13)
0.064*
0.0450 (11)
0.054*
0.0389 (10)
0.0354 (9)
0.0390 (10)
0.047*
0.0400 (10)
0.0456 (11)
0.055*

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Acta Cryst. (2012). E68, o786
C12
H12
C13
H13
N1
H1N
N2
O1
O2
O3
O4
O5
Cl1
S1
−0.2663 (4)
−0.3127
−0.1921 (4)
−0.1879
−0.0153 (3)
−0.050 (3)
−0.1148 (3)
0.0765 (2)
0.1576 (2)
−0.0201 (3)
−0.1559 (3)
−0.0955 (3)
−0.20968 (12)
0.06425 (8)
1.0654 (4)
1.0518
0.9897 (3)
0.9254
0.9315 (3)
0.966 (3)
0.7825 (3)
0.8844 (2)
0.8265 (2)
0.8509 (2)
0.8640 (3)
0.7592 (3)
1.29932 (10)
0.84464 (8)
0.2884 (2)
0.3273
0.2670 (2)
0.2915
0.11212 (18)
0.0794 (18)
−0.0428 (2)
−0.00038 (15)
0.11536 (16)
0.22210 (16)
−0.0218 (2)
−0.10577 (18)
0.14917 (7)
0.07160 (6)
0.0499 (12)
0.060*
0.0452 (11)
0.054*
0.0400 (9)
0.048*
0.0528 (10)
0.0478 (8)
0.0514 (8)
0.0538 (8)
0.0730 (11)
0.0747 (11)
0.0697 (4)
0.0381 (3)
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
N1
N2
O1
O2
O3
O4
O5
Cl1
S1
0.036 (2)
0.037 (2)
0.042 (3)
0.063 (3)
0.068 (3)
0.052 (3)
0.044 (3)
0.039 (2)
0.043 (3)
0.049 (3)
0.047 (3)
0.060 (3)
0.061 (3)
0.048 (2)
0.049 (2)
0.0518 (19)
0.0366 (17)
0.068 (2)
0.090 (3)
0.087 (3)
0.0894 (11)
0.0379 (6)
0.030 (2)
0.044 (3)
0.054 (3)
0.037 (3)
0.041 (3)
0.043 (3)
0.037 (2)
0.036 (2)
0.041 (2)
0.033 (2)
0.048 (3)
0.050 (3)
0.037 (2)
0.040 (2)
0.057 (3)
0.0507 (18)
0.060 (2)
0.0485 (19)
0.052 (2)
0.098 (3)
0.0479 (7)
0.0399 (6)
0.038 (2)
0.040 (2)
0.055 (3)
0.066 (3)
0.052 (3)
0.040 (2)
0.035 (2)
0.031 (2)
0.033 (2)
0.037 (2)
0.042 (2)
0.040 (2)
0.037 (2)
0.0329 (19)
0.053 (3)
0.0411 (16)
0.0577 (19)
0.0450 (17)
0.077 (3)
0.0394 (19)
0.0718 (9)
0.0365 (5)
0.0025 (18)
0.007 (2)
−0.004 (2)
−0.011 (2)
0.005 (2)
0.007 (2)
−0.004 (2)
−0.003 (2)
−0.004 (2)
−0.004 (2)
0.002 (2)
−0.008 (3)
−0.006 (2)
0.0065 (18)
−0.004 (2)
−0.0011 (15)
0.0028 (16)
0.0083 (18)
0.018 (2)
−0.011 (2)
0.0188 (7)
0.0018 (5)
0.0033 (19)
0.0002 (19)
−0.008 (2)
−0.001 (3)
−0.005 (3)
−0.010 (2)
0.0004 (19)
0.0033 (18)
0.0097 (19)
0.001 (2)
0.009 (2)
0.018 (2)
0.009 (2)
0.0043 (16)
−0.012 (2)
0.0137 (14)
−0.0076 (15)
0.0041 (16)
−0.007 (2)
−0.0108 (19)
0.0221 (7)
0.0035 (5)
0.0001 (18)
0.011 (2)
0.004 (2)
0.007 (2)
0.013 (2)
0.003 (2)
0.0011 (19)
−0.0040 (17)
−0.0018 (18)
−0.0022 (18)
−0.013 (2)
−0.005 (2)
−0.0048 (19)
0.0036 (16)
0.016 (2)
0.0022 (14)
−0.0045 (16)
0.0094 (16)
0.0162 (19)
0.0131 (19)
0.0146 (6)
−0.0007 (5)
Geometric parameters (Å, º)
C1—C6
C1—C2
C1—S1
C2—C3
C2—N2
C3—C4
C3—H3
1.388 (5)
1.389 (6)
1.767 (4)
1.371 (6)
1.479 (5)
1.366 (6)
0.9300
C8—C9
C9—C10
C9—H9
C10—C11
C10—Cl1
C11—C12
C11—H11
1.382 (5)
1.381 (6)
0.9300
1.369 (6)
1.723 (4)
1.378 (6)
0.9300

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Acta Cryst. (2012). E68, o786
C4—C5
C4—H4
C5—C6
C5—H5
C6—H6
C7—O3
C7—N1
C7—C8
C8—C13
1.373 (6)
0.9300
1.372 (6)
0.9300
0.9300
1.201 (5)
1.399 (5)
1.489 (6)
1.379 (5)
C12—C13
C12—H12
C13—H13
N1—S1
N1—H1N
N2—O4
N2—O5
O1—S1
O2—S1
1.374 (6)
0.9300
0.9300
1.643 (4)
0.857 (19)
1.207 (5)
1.221 (5)
1.426 (3)
1.414 (3)
C6—C1—C2
C6—C1—S1
C2—C1—S1
C3—C2—C1
C3—C2—N2
C1—C2—N2
C4—C3—C2
C4—C3—H3
C2—C3—H3
C3—C4—C5
C3—C4—H4
C5—C4—H4
C6—C5—C4
C6—C5—H5
C4—C5—H5
C5—C6—C1
C5—C6—H6
C1—C6—H6
O3—C7—N1
O3—C7—C8
N1—C7—C8
C13—C8—C9
C13—C8—C7
C9—C8—C7
C10—C9—C8
C10—C9—H9
117.8 (4)
119.0 (3)
123.1 (3)
121.9 (4)
116.7 (4)
121.5 (4)
119.0 (4)
120.5
120.5
120.7 (4)
119.7
119.7
120.2 (4)
119.9
119.9
120.4 (4)
119.8
119.8
121.3 (4)
124.1 (4)
114.5 (4)
119.9 (4)
118.3 (4)
121.7 (4)
119.5 (4)
120.2
C8—C9—H9
C11—C10—C9
C11—C10—Cl1
C9—C10—Cl1
C10—C11—C12
C10—C11—H11
C12—C11—H11
C13—C12—C11
C13—C12—H12
C11—C12—H12
C12—C13—C8
C12—C13—H13
C8—C13—H13
C7—N1—S1
C7—N1—H1N
S1—N1—H1N
O4—N2—O5
O4—N2—C2
O5—N2—C2
O2—S1—O1
O2—S1—N1
O1—S1—N1
O2—S1—C1
O1—S1—C1
N1—S1—C1
120.2
120.8 (4)
121.0 (3)
118.2 (3)
119.2 (4)
120.4
120.4
120.8 (4)
119.6
119.6
119.7 (4)
120.2
120.2
123.9 (3)
124 (3)
108 (3)
126.1 (4)
116.9 (4)
117.0 (4)
120.19 (19)
108.94 (18)
104.51 (18)
107.76 (19)
108.41 (19)
106.23 (18)
C6—C1—C2—C3
S1—C1—C2—C3
C6—C1—C2—N2
S1—C1—C2—N2
C1—C2—C3—C4
N2—C2—C3—C4
C2—C3—C4—C5
C3—C4—C5—C6
C4—C5—C6—C1
C2—C1—C6—C5
S1—C1—C6—C5
O3—C7—C8—C13
−1.8 (6)
174.5 (3)
178.6 (4)
−5.0 (6)
1.8 (7)
−178.7 (4)
−0.7 (7)
−0.2 (7)
0.1 (7)
0.9 (6)
−175.6 (3)
−22.3 (6)
Cl1—C10—C11—C12
C10—C11—C12—C13
C11—C12—C13—C8
C9—C8—C13—C12
C7—C8—C13—C12
O3—C7—N1—S1
C8—C7—N1—S1
C3—C2—N2—O4
C1—C2—N2—O4
C3—C2—N2—O5
C1—C2—N2—O5
C7—N1—S1—O2
179.3 (3)
−0.7 (7)
−0.4 (7)
1.7 (6)
−176.5 (4)
0.6 (6)
−178.1 (3)
119.2 (5)
−61.2 (6)
−60.2 (6)
119.4 (5)
−50.4 (4)

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supplementary materials
sup-7
Acta Cryst. (2012). E68, o786
N1—C7—C8—C13
O3—C7—C8—C9
N1—C7—C8—C9
C13—C8—C9—C10
C7—C8—C9—C10
C8—C9—C10—C11
C8—C9—C10—Cl1
C9—C10—C11—C12
156.3 (4)
159.5 (4)
−21.9 (6)
−1.7 (6)
176.4 (4)
0.5 (6)
−178.1 (3)
0.7 (7)
C7—N1—S1—O1
C7—N1—S1—C1
C6—C1—S1—O2
C2—C1—S1—O2
C6—C1—S1—O1
C2—C1—S1—O1
C6—C1—S1—N1
C2—C1—S1—N1
179.9 (3)
65.4 (4)
17.3 (4)
−159.0 (3)
148.9 (3)
−27.4 (4)
−99.3 (3)
84.4 (4)
Hydrogen-bond geometry (Å, º)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i
0.86 (2) 2.41 (3) 3.193 (4)153 (4)
Symmetry code: (i) −x, −y+2, −z.