• No results found

N (2 Chloro­phen­yl)benzene­sulfonamide

N/A
N/A
Protected

Academic year: 2020

Share "N (2 Chloro­phen­yl)benzene­sulfonamide"

Copied!
7
0
0

Loading.... (view fulltext now)

Full text

(1)

organic papers

o780

Perlovichet al. C

12H10ClNO2S 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

(2)

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]
(3)

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

o782

Perlovichet al. C

(4)

supporting information

sup-1

Acta Cryst. (2006). E62, o780–o782

supporting information

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 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

(5)

supporting information

sup-2

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

(6)

supporting information

sup-3

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)

(7)

supporting information

sup-4

Acta Cryst. (2006). E62, o780–o782

C4—C5—H5 118 (2)

Figure

Figure 1A view of (I) with the atomic numbering scheme. Displacement ellipsoidsare drawn at the 20% probability level.
Table 1

References

Related documents

In this study, we identified 9 protein markers for predicting time to recurrence using the protein expression data on 222 TCGA pri- marily high-grade serous ovarian cancers

For the purpose of analyzing the impurities in the water samples coming from different roofs, four building within the KCAET campus viz location 1(library -

To overcome the problems and weakness, this project need to do some research and studying to develop better technology. There are list of the objectives to be conduct

The above block diagram shows the SPV fed to Dc/Dc Converter for different dc applications, To analysis the performance of dc-dc converters(Buck, Boost,

22 subjects showing low or undetectable activities of BAT were randomly divided into 2 groups: one was exposed to cold at 17°C for 2 hours every day for 6 weeks (cold group; n

Foxo deletion on osteoblast differentiation in both bone marrow and calvaria cells suggests that the increases in ALP activity and mineralization observed in the bone

Histologically, the lesion is composed of fibrous connective tissue trabeculae (top quarter of image) and adipose connective tissue (bottom three quarters of image); within

• Data shows credit using and rationing of risk averts, risk neutrals and risk lovers respectively. As to risk averts, the credit is mainly used to pay children’s tuition, medical