organic papers
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Perlovichet al. C12H10ClNO2S doi:10.1107/S1600536806002303 Acta Cryst.(2006). E62, o780–o782
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
N
-(2-Chlorophenyl)benzenesulfonamide
German L. Perlovich,a,b*
Valery V. Tkachev,cKlaus-Ju¨rgen Schaperd and Oleg A. Raevskya
aLaboratory of Computer-Aided Molecular
Design, Institute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Russian Federation,
bInstitute of Solution Chemistry, Russian
Academy of Sciences, 153045 Ivanovo, Russian Federation,cLaboratory of Structural Chemistry, Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Russian Federation, and
dResearch Center Borstel, Leibniz Center for
Medicine and Biosciences, D-23845 Borstel, Germany
Correspondence e-mail: glp@isc-ras.ru
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C–C) = 0.003 A˚
Rfactor = 0.035
wRfactor = 0.100
Data-to-parameter ratio = 10.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 10 January 2006 Accepted 18 January 2006
#2006 International Union of Crystallography
All rights reserved
In the crystal structure of the title compound, C12H10ClNO2S,
molecules form chains via hydrogen bonds, which create infinite helices along thecaxis. The hydrogen-bond network can be described by graph setC(4) (an infinite chain with four atoms in the repeat pattern).
Comment
Sulfanyls and sulfonamides are drugs used for the treatment of infections, some fungi and certain protozoa. Other therapeutic applications of the compounds are as diuretic and hypogly-caemic agents. On the other hand, the compounds are very interesting from a fundamental point of view,e.g.for studying the relationship between van der Waals interactions and hydrogen-bond topology in the formation of a crystal struc-ture. This communication is a continuation of our work devoted to studying the crystal structures of sulfanyls and sulfonamides (Perlovichet al., 2006).
A view of the title compound, (I), with the atomic numbering is presented in Fig. 1. The conformational state of the molecule in the crystal structure can be characterized and compared with the analogous parameters of N -(4-chloro-phenyl)benzenesulfonamide, (II) (Perlovich et al., 2006) (in square brackets), in the following way. The torsion angle O1— S—C1—C2, which describes the arrangement between the SO2 group and the benzene ring Ph1 (C1–C6), is 5.83 (19)
[30.7 (4)]. The benzene fragments are rotated relative to each other by 49.14 (9) [54.39 (15)]. The torsion angle N1—S—
[image:1.610.207.459.608.726.2]C1—C2, which describes the position of the NH group relative
Figure 1
to Ph1, is 108.50 (17) [83.5 (3)]; the torsion angle S—
N1—C7—C12, which characterizes the location of the SO2
group with respect to benzene fragment Ph2 (C7–C12), is
68.3 (2) [71.1 (4)]. One molecule of the title crystal
structure has two equivalent hydrogen bonds: N1—H1 O2i and O2 (H1—N1)i; the values of the hydrogen-bond geometric parameters for (I) and (II) are summarized in Table 1.
The molecular packing architecture is shown in Figs. 2 and 3. The molecules of (I) form chains with adjacent molecules by means of the hydrogen bonds described above. The hydrogen bonds create infinite helices along the caxis. The hydrogen-bond network can be described by the graph set assignment introduced by Etter (1990) asC(4) (an infinite chain with four
involved atoms). In turn, the chains of molecules interact with adjacent chains by van der Waals forces between parallel chlorophenyl fragments. It should be mentioned that the Ph1 benzene rings are arranged parallel to each other.
Experimental
The chemical synthesis of the title compound has been performed with reference to procedures described previously (Crosley et al., 1940; Andersonet al., 1942; Gutsche et al., 1974) by reaction of a substituted aromatic amine (chloroaniline) with benzenesulfonyl chloride in dry pyridine, followed by precipitation of the end product by pouring the reaction mixture into water and by acidification to pH 5. Generally, the compounds have been recrystallized from ethanol/ water. Single crystals of (I) were grown by vapour diffusion between water and an ethanol solution.
Crystal data
C12H10ClNO2S
Mr= 267.72
Monoclinic,P21=a
a= 14.821 (3) A˚ b= 9.656 (2) A˚ c= 8.365 (2) A˚ = 92.46 (3) V= 1196.0 (4) A˚3
Z= 4
Dx= 1.487 Mg m
3
MoKradiation Cell parameters from 26
reflections = 5–10 = 0.48 mm1
T= 293 (2) K Prism, colourless 0.40.30.2 mm
Data collection
Enraf–Nonius CAD-4 diffractometer !–2scans
Absorption correction: none 2262 measured reflections 2108 independent reflections 1727 reflections withI> 2(I) Rint= 0.027
max= 25.1
h=17!17 k= 0!11 l= 0!9
3 standard reflections frequency: 120 min intensity decay: 2%
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.035
wR(F2) = 0.100
S= 1.05 2108 reflections 194 parameters
All H-atom parameters refined
w= 1/[2(F
o2) + (0.0669P)2
+ 0.0406P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001 max= 0.33 e A˚
3
[image:2.610.46.296.71.286.2]min=0.26 e A˚ 3
Table 1
Hydrogen-bond geometry (A˚ ,) in (I) and (II).
D—H A D—H H A D A D—H A
(I) N1—H1 O2Ai
0.75 (2) 2.26 (2) 2.994 (2) 167 (2) (II) N1—H1 O2Aii
0.78 (3) 2.21 (3) 2.993 (4) 175 (4)
Symmetry codes: (i)3 2x;y
1 2;1z; (ii)
1 2x;y
1 2;z.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CELDIM in CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics: XPWin SHELXTL (Sheldrick, 2000); software used to prepare material for publication:CIFTAB (Shel-drick, 1997).
This work was supported by ISTC (project No. 0888).
organic papers
Acta Cryst.(2006). E62, o780–o782 Perlovichet al. C
12H10ClNO2S
o781
Figure 2 [image:2.610.45.295.324.539.2]Projection of the crystal packing of (I) along thebaxis.
Figure 3
[image:2.610.314.565.578.619.2]References
Anderson, G. W., Faith, H. E., Marson, H. W., Winnek, P. S. & Roblin, R. O. (1942).J. Am. Chem. Soc.64, 2902–2905.
Crosley, M. L., Northey, E. H. & Hultquist, M. E. (1940).J. Am. Chem. Soc.62, 372–374.
Enraf–Nonius (1989).CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands.
Etter, M. C. (1990).Acc. Chem. Res.23, 120–126.
Gutsche, K., Schro¨der, E., Rufer, C. & Loge, O. (1974).Arzneim.-Forsch./Drug Res.24, 1028–1039.
Perlovich, G. L., Tkachev, V. V., Schaper, K. J. & Raevsky, O. A. (2006).Acta Cryst.E62, o376–o378.
Sheldrick, G. M. (1997).CIFTAB,SHELXL97andSHELXS97. University of Go¨ttingen, Germany.
Sheldrick, G. M. (2000).SHELXTL. Version 6.14. Bruker AXS Inc., madison, Wisconsin, USA.
organic papers
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Perlovichet al. Csupporting information
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Acta Cryst. (2006). E62, o780–o782
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Acta Cryst. (2006). E62, o780–o782 [https://doi.org/10.1107/S1600536806002303]
N
-(2-Chlorophenyl)benzenesulfonamide
German L. Perlovich, Valery V. Tkachev, Klaus-J
ü
rgen Schaper and Oleg A. Raevsky
N-(2-Chlorophenyl)benzenesulfonamide
Crystal data
C12H10ClNO2S
Mr = 267.72 Monoclinic, P21/a
a = 14.821 (3) Å
b = 9.656 (2) Å
c = 8.365 (2) Å
β = 92.46 (3)°
V = 1196.0 (4) Å3
Z = 4
F(000) = 552
Dx = 1.487 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 26 reflections
θ = 5–10°
µ = 0.48 mm−1
T = 293 K Prism, colourless 0.4 × 0.3 × 0.2 mm
Data collection
Enraf–Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω–2θ scans
2262 measured reflections 2108 independent reflections 1727 reflections with I > 2σ(I)
Rint = 0.027
θmax = 25.1°, θmin = 2.4°
h = −17→17
k = 0→11
l = 0→9
3 standard reflections every 120 min intensity decay: 2%
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.035
wR(F2) = 0.100
S = 1.05 2108 reflections 194 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
All H-atom parameters refined
w = 1/[σ2(F
o2) + (0.0669P)2 + 0.0406P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.33 e Å−3
Δρmin = −0.26 e Å−3
Special details
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Acta Cryst. (2006). E62, o780–o782
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)
x y z Uiso*/Ueq
S 0.78658 (3) 0.06254 (4) 0.40936 (5) 0.03269 (17) Cl 0.59519 (4) −0.20847 (6) 0.23017 (8) 0.0639 (2) O1 0.85365 (9) −0.00117 (15) 0.51171 (15) 0.0446 (3) O2 0.77374 (9) 0.20887 (13) 0.41317 (16) 0.0445 (3) N1 0.69062 (10) −0.00742 (17) 0.45428 (18) 0.0357 (4) C1 0.80792 (12) 0.01758 (19) 0.2098 (2) 0.0337 (4) C2 0.87507 (16) −0.0759 (2) 0.1800 (2) 0.0477 (5) C3 0.8922 (2) −0.1097 (3) 0.0239 (3) 0.0621 (6) C4 0.84126 (19) −0.0531 (3) −0.1008 (3) 0.0584 (6) C5 0.77488 (17) 0.0398 (3) −0.0706 (3) 0.0558 (6) C6 0.75731 (15) 0.0777 (2) 0.0849 (2) 0.0452 (5) C7 0.60828 (12) 0.03916 (18) 0.3793 (2) 0.0341 (4) C8 0.55762 (13) −0.0441 (2) 0.2742 (2) 0.0402 (4) C9 0.47735 (15) 0.0028 (3) 0.2046 (3) 0.0519 (5) C10 0.44732 (15) 0.1329 (3) 0.2367 (3) 0.0581 (6) C11 0.49725 (16) 0.2170 (3) 0.3394 (3) 0.0563 (6) C12 0.57632 (14) 0.1699 (2) 0.4119 (3) 0.0455 (5) H1 0.6943 (14) −0.082 (2) 0.476 (2) 0.030 (5)* H2 0.9127 (19) −0.106 (3) 0.275 (3) 0.070 (8)* H3 0.9419 (19) −0.167 (3) 0.008 (3) 0.073 (8)* H4 0.8514 (18) −0.079 (3) −0.200 (3) 0.065 (7)* H5 0.747 (2) 0.077 (3) −0.148 (3) 0.072 (8)* H6 0.7160 (15) 0.140 (2) 0.103 (3) 0.041 (6)* H9 0.446 (2) −0.057 (3) 0.138 (3) 0.081 (9)* H10 0.3944 (19) 0.158 (3) 0.199 (3) 0.068 (8)* H11 0.4815 (18) 0.300 (3) 0.363 (3) 0.063 (7)* H12 0.6093 (16) 0.224 (2) 0.490 (3) 0.051 (6)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
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Acta Cryst. (2006). E62, o780–o782
C5 0.0634 (14) 0.0710 (16) 0.0323 (11) −0.0109 (11) −0.0072 (10) 0.0157 (10) C6 0.0444 (12) 0.0520 (12) 0.0391 (10) 0.0019 (9) 0.0002 (8) 0.0104 (9) C7 0.0350 (9) 0.0347 (9) 0.0333 (9) −0.0012 (7) 0.0082 (7) 0.0034 (7) C8 0.0408 (10) 0.0415 (10) 0.0387 (10) 0.0003 (8) 0.0049 (8) −0.0009 (8) C9 0.0419 (11) 0.0647 (14) 0.0487 (12) 0.0014 (10) −0.0038 (9) −0.0011 (10) C10 0.0411 (12) 0.0742 (16) 0.0591 (14) 0.0148 (11) 0.0047 (10) 0.0140 (12) C11 0.0495 (12) 0.0466 (12) 0.0742 (15) 0.0151 (10) 0.0191 (11) 0.0069 (11) C12 0.0435 (11) 0.0415 (11) 0.0525 (12) 0.0000 (9) 0.0128 (9) −0.0050 (9)
Geometric parameters (Å, º)
S—O1 1.4236 (14) C4—H4 0.89 (3)
S—O2 1.4262 (14) C5—C6 1.387 (3)
S—N1 1.6328 (16) C5—H5 0.83 (3)
S—C1 1.7666 (18) C6—H6 0.88 (2)
Cl—C8 1.727 (2) C7—C12 1.380 (3)
N1—C7 1.421 (2) C7—C8 1.388 (3)
N1—H1 0.75 (2) C8—C9 1.378 (3)
C1—C2 1.374 (3) C9—C10 1.364 (3)
C1—C6 1.387 (3) C9—H9 0.92 (3)
C2—C3 1.380 (3) C10—C11 1.375 (4)
C2—H2 1.00 (3) C10—H10 0.87 (3)
C3—C4 1.374 (4) C11—C12 1.374 (3)
C3—H3 0.94 (3) C11—H11 0.86 (3)
C4—C5 1.363 (4) C12—H12 0.96 (2)
O1—S—O2 120.34 (8) C6—C5—H5 121 (2)
O1—S—N1 105.98 (9) C5—C6—C1 118.6 (2)
O2—S—N1 106.65 (8) C5—C6—H6 120.1 (14)
O1—S—C1 108.26 (9) C1—C6—H6 121.2 (14)
O2—S—C1 107.10 (8) C12—C7—C8 118.29 (18)
N1—S—C1 107.99 (8) C12—C7—N1 119.88 (17)
C7—N1—S 120.50 (13) C8—C7—N1 121.82 (17)
C7—N1—H1 117.8 (16) C9—C8—C7 120.74 (19)
S—N1—H1 113.7 (16) C9—C8—Cl 119.47 (17)
C2—C1—C6 120.73 (18) C7—C8—Cl 119.79 (15)
C2—C1—S 119.54 (14) C10—C9—C8 120.2 (2)
C6—C1—S 119.73 (15) C10—C9—H9 122 (2)
C1—C2—C3 119.4 (2) C8—C9—H9 117.4 (19)
C1—C2—H2 115.6 (16) C9—C10—C11 119.7 (2)
C3—C2—H2 124.6 (16) C9—C10—H10 118.8 (19)
C4—C3—C2 120.5 (2) C11—C10—H10 121.2 (19)
C4—C3—H3 122.4 (17) C12—C11—C10 120.4 (2)
C2—C3—H3 117.0 (17) C12—C11—H11 116.3 (17)
C5—C4—C3 119.9 (2) C10—C11—H11 123.2 (17)
C5—C4—H4 120.7 (18) C11—C12—C7 120.6 (2)
C3—C4—H4 119.4 (18) C11—C12—H12 121.5 (14)
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Acta Cryst. (2006). E62, o780–o782
C4—C5—H5 118 (2)