Literature DB >> 21581894

2-Chloro-5-(2-iodo-benzene-sulfonamido)-benzoic acid.

Muhammad Nadeem Arshad, M Nawaz Tahir, Islam Ullah Khan, Waseeq Ahmad Siddiqui, Muhammad Shafiq.   

Abstract

In the mol-ecule of the title compound, C(13)H(9)ClINO(4)S, the coordination around the S atom is distorted tetra-hedral. The aromatic rings are oriented at a dihedral angle of 74.46 (9)°. Intra-molecular C-H⋯O hydrogen bonds result in the formation of two five- and one six-membered rings, which adopt planar, envelope and twisted conformations, respectively. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules to form R(2) (2)(8) ring motifs, which are further linked by C-H⋯O hydrogen bonds. π-π contacts between the benzene rings [centroid-centroid distances = 3.709 (3) and 3.772 (3) Å] may further stabilize the structure. The I atom is disordered over two positions, refined with occupancies of ca 0.75 and 0.25.

Entities:  

Year:  2009        PMID： 21581894      PMCID： PMC2968399          DOI： 10.1107/S1600536808043869

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Arshad, Tahir, Khan, Ahmad & Shafiq (2008 ▶); Arshad, Tahir, Khan, Shafiq & Siddiqui (2008 ▶); Arshad et al. (2009 ▶); Deng & Mani (2006 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9ClINO4S M = 437.62 Monoclinic, a = 26.6375 (9) Å b = 8.5532 (2) Å c = 14.2696 (5) Å β = 111.923 (2)° V = 3016.03 (17) Å3 Z = 8 Mo Kα radiation μ = 2.45 mm−1 T = 296 (2) K 0.25 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.708, T max = 0.819 16794 measured reflections 3738 independent reflections 2909 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026 wR(F 2) = 0.069 S = 1.05 3738 reflections 203 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.54 e Å−3 Δρmin = −0.31 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043869/hk2607sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043869/hk2607Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H9ClINO4SF(000) = 1696
Mr = 437.62Dx = 1.928 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3738 reflections
a = 26.6375 (9) Åθ = 2.5–28.3°
b = 8.5532 (2) ŵ = 2.45 mm−1
c = 14.2696 (5) ÅT = 296 K
β = 111.923 (2)°Needle, light brown
V = 3016.03 (17) Å30.25 × 0.12 × 0.08 mm
Z = 8
Bruker Kappa APEXII CCD diffractometer3738 independent reflections
Radiation source: fine-focus sealed tube2909 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.5°
ω scansh = −34→35
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −11→11
Tmin = 0.708, Tmax = 0.819l = −18→18
16794 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0301P)2 + 3.5121P] where P = (Fo2 + 2Fc2)/3
3738 reflections(Δ/σ)max = 0.002
203 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/UeqOcc. (<1)
I1A0.12215 (4)0.55411 (16)0.41289 (12)0.0562 (2)0.750
I1B0.12364 (17)0.5371 (5)0.4021 (4)0.0789 (10)0.250
Cl1−0.04930 (3)1.21242 (9)0.10878 (7)0.0669 (3)
S10.16694 (2)0.68574 (6)0.21704 (5)0.0391 (2)
O10.18866 (8)0.7712 (2)0.15530 (16)0.0565 (7)
O20.18272 (7)0.52454 (19)0.23828 (15)0.0482 (6)
O30.13053 (10)1.2455 (2)0.1957 (2)0.0776 (9)
O40.05294 (9)1.3743 (2)0.13943 (18)0.0690 (8)
N10.10171 (8)0.6828 (2)0.16552 (17)0.0441 (7)
C10.18390 (9)0.7924 (3)0.33142 (18)0.0361 (7)
C20.16797 (10)0.7500 (3)0.4100 (2)0.0418 (8)
C30.18262 (12)0.8446 (4)0.4949 (2)0.0556 (10)
C40.21208 (13)0.9786 (4)0.5010 (3)0.0624 (11)
C50.22800 (12)1.0202 (3)0.4236 (3)0.0578 (10)
C60.21433 (10)0.9275 (3)0.3391 (2)0.0453 (8)
C70.06742 (10)0.8137 (2)0.15009 (18)0.0371 (7)
C80.08656 (10)0.9658 (2)0.15617 (19)0.0402 (7)
C90.05220 (10)1.0940 (3)0.14506 (18)0.0394 (7)
C10−0.00221 (11)1.0655 (3)0.12406 (19)0.0436 (8)
C11−0.02139 (11)0.9137 (3)0.1157 (2)0.0490 (8)
C120.01314 (10)0.7883 (3)0.1292 (2)0.0451 (8)
C130.07726 (12)1.2528 (3)0.1587 (2)0.0456 (8)
H10.086560.593520.145790.0529*
H30.172390.817000.548290.0667*
H3O0.1464 (16)1.322 (5)0.207 (3)0.0931*
H40.221301.041510.558110.0749*
H50.248001.111020.428210.0695*
H60.225450.955030.286810.0544*
H80.122890.982810.167840.0482*
H11−0.058020.896060.100690.0588*
H12−0.000120.686810.124270.0541*
U11U22U33U12U13U23
I1A0.0535 (3)0.0462 (3)0.0796 (5)−0.0084 (2)0.0373 (3)0.0109 (4)
I1B0.106 (2)0.0709 (18)0.0809 (13)−0.0395 (13)0.0591 (12)−0.0108 (9)
Cl10.0705 (5)0.0508 (4)0.0822 (5)0.0268 (3)0.0318 (4)0.0054 (4)
S10.0453 (3)0.0250 (3)0.0528 (4)0.0010 (2)0.0250 (3)−0.0009 (2)
O10.0748 (13)0.0452 (10)0.0659 (13)−0.0060 (9)0.0452 (11)−0.0017 (9)
O20.0482 (10)0.0272 (8)0.0719 (13)0.0059 (7)0.0255 (9)−0.0022 (8)
O30.0640 (15)0.0245 (9)0.140 (2)−0.0043 (9)0.0331 (15)−0.0062 (11)
O40.0735 (14)0.0240 (9)0.0982 (17)0.0068 (9)0.0190 (12)0.0050 (9)
N10.0451 (11)0.0202 (8)0.0602 (14)0.0000 (8)0.0119 (10)−0.0022 (8)
C10.0333 (11)0.0271 (10)0.0489 (14)0.0007 (8)0.0166 (10)0.0000 (9)
C20.0379 (13)0.0389 (12)0.0531 (15)0.0018 (10)0.0221 (11)0.0042 (11)
C30.0577 (17)0.0623 (18)0.0538 (17)0.0023 (14)0.0290 (14)−0.0012 (13)
C40.0660 (19)0.0542 (17)0.0633 (19)−0.0021 (14)0.0198 (16)−0.0204 (14)
C50.0598 (18)0.0364 (14)0.073 (2)−0.0110 (12)0.0200 (16)−0.0077 (13)
C60.0444 (14)0.0344 (12)0.0583 (16)−0.0061 (10)0.0205 (12)0.0012 (11)
C70.0459 (13)0.0241 (10)0.0378 (12)0.0028 (9)0.0115 (10)0.0001 (9)
C80.0458 (13)0.0255 (10)0.0476 (14)0.0015 (9)0.0155 (11)0.0015 (9)
C90.0551 (15)0.0246 (10)0.0376 (13)0.0035 (9)0.0163 (11)0.0014 (9)
C100.0545 (15)0.0362 (12)0.0398 (13)0.0129 (10)0.0172 (11)0.0012 (10)
C110.0456 (14)0.0440 (14)0.0541 (16)0.0017 (11)0.0147 (12)−0.0001 (12)
C120.0465 (14)0.0310 (11)0.0539 (15)−0.0024 (10)0.0143 (12)0.0006 (10)
C130.0632 (17)0.0253 (11)0.0490 (15)0.0040 (10)0.0218 (13)0.0007 (10)
I1A—C22.082 (3)C4—C51.370 (5)
I1B—C22.150 (5)C5—C61.374 (4)
Cl1—C101.731 (3)C7—C121.380 (4)
S1—O11.423 (2)C7—C81.388 (3)
S1—O21.4403 (17)C8—C91.399 (3)
S1—N11.614 (2)C9—C101.388 (4)
S1—C11.775 (3)C9—C131.494 (4)
O3—C131.318 (4)C10—C111.384 (4)
O4—C131.201 (3)C11—C121.379 (4)
O3—H3O0.76 (4)C3—H30.9300
N1—C71.409 (3)C4—H40.9300
N1—H10.8600C5—H50.9300
C1—C61.392 (4)C6—H60.9300
C1—C21.387 (4)C8—H80.9300
C2—C31.386 (4)C11—H110.9300
C3—C41.373 (5)C12—H120.9300
I1A···O23.446 (2)C1···C83.215 (3)
I1A···N13.540 (3)C2···C4ii3.552 (5)
I1A···Cl1i3.4575 (16)C4···C2ii3.552 (5)
I1A···C5ii3.851 (4)C4···O1x3.293 (4)
I1B···O23.271 (6)C5···I1Aii3.851 (4)
I1B···N13.438 (6)C5···I1Bii3.835 (6)
I1B···C5ii3.835 (6)C6···C83.445 (4)
I1B···Cl1i3.381 (5)C6···O2xi3.419 (3)
I1A···H12iii3.2900C7···Cl1v3.549 (3)
I1A···H11iii3.3600C8···O13.193 (3)
Cl1···O42.939 (3)C8···C63.445 (4)
Cl1···I1Aiv3.4575 (16)C8···C13.215 (3)
Cl1···I1Biv3.381 (5)C9···C11v3.499 (4)
Cl1···C7v3.549 (3)C10···C10iii3.552 (4)
S1···H3Ovi3.15 (4)C11···C11iii3.568 (4)
S1···H82.7800C11···C9v3.499 (4)
O1···C83.193 (3)C1···H82.8100
O1···C4vii3.293 (4)C6···H82.7700
O2···O3vi2.714 (3)C13···H1ix2.9400
O2···I1B3.271 (6)H1···O4vi2.0700
O2···I1A3.446 (2)H1···C13vi2.9400
O2···C6viii3.419 (3)H1···H122.3500
O3···O2ix2.714 (3)H3···O3x2.7800
O4···N1ix2.903 (3)H3O···S1ix3.15 (4)
O4···Cl12.939 (3)H3O···O2ix1.95 (4)
O1···H82.5700H4···O1x2.4800
O1···H4vii2.4800H5···O1xi2.7600
O1···H62.3600H6···O12.3600
O1···H5viii2.7600H6···O2xi2.6700
O2···H6viii2.6700H8···S12.7800
O2···H3Ovi1.95 (4)H8···O12.5700
O3···H3vii2.7800H8···O32.2800
O3···H82.2800H8···C12.8100
O4···H1ix2.0700H8···C62.7700
N1···I1A3.540 (3)H11···I1Aiii3.3600
N1···I1B3.438 (6)H12···H12.3500
N1···O4vi2.903 (3)H12···I1Aiii3.2900
O1—S1—O2117.89 (12)C8—C9—C10118.2 (2)
O1—S1—N1110.08 (12)C8—C9—C13117.2 (2)
O1—S1—C1106.41 (12)C10—C9—C13124.6 (2)
O2—S1—N1105.12 (11)Cl1—C10—C9123.3 (2)
O2—S1—C1110.15 (12)Cl1—C10—C11116.3 (2)
N1—S1—C1106.73 (12)C9—C10—C11120.4 (3)
C13—O3—H3O118 (3)C10—C11—C12120.8 (3)
S1—N1—C7125.69 (16)C7—C12—C11119.9 (2)
C7—N1—H1117.00O3—C13—O4122.7 (3)
S1—N1—H1117.00O3—C13—C9111.8 (2)
S1—C1—C6116.10 (19)O4—C13—C9125.5 (3)
S1—C1—C2124.0 (2)C2—C3—H3120.00
C2—C1—C6119.9 (2)C4—C3—H3120.00
I1A—C2—C1125.8 (2)C3—C4—H4120.00
I1A—C2—C3115.4 (2)C5—C4—H4120.00
C1—C2—C3118.9 (3)C4—C5—H5120.00
I1B—C2—C1120.5 (2)C6—C5—H5120.00
I1B—C2—C3120.7 (3)C1—C6—H6120.00
C2—C3—C4120.7 (3)C5—C6—H6120.00
C3—C4—C5120.5 (3)C7—C8—H8119.00
C4—C5—C6119.8 (3)C9—C8—H8119.00
C1—C6—C5120.3 (3)C10—C11—H11120.00
C8—C7—C12119.5 (2)C12—C11—H11120.00
N1—C7—C8122.2 (2)C7—C12—H12120.00
N1—C7—C12118.31 (19)C11—C12—H12120.00
C7—C8—C9121.2 (3)
O1—S1—N1—C7−65.6 (2)C3—C4—C5—C60.1 (5)
O2—S1—N1—C7166.5 (2)C4—C5—C6—C10.7 (5)
C1—S1—N1—C749.5 (2)N1—C7—C8—C9−177.1 (2)
O1—S1—C1—C2177.4 (2)C12—C7—C8—C92.3 (4)
O1—S1—C1—C6−1.6 (2)N1—C7—C12—C11178.7 (2)
O2—S1—C1—C2−53.8 (3)C8—C7—C12—C11−0.7 (4)
O2—S1—C1—C6127.3 (2)C7—C8—C9—C10−2.3 (4)
N1—S1—C1—C259.8 (3)C7—C8—C9—C13176.6 (2)
N1—S1—C1—C6−119.1 (2)C8—C9—C10—Cl1179.79 (19)
S1—N1—C7—C815.6 (4)C8—C9—C10—C110.8 (4)
S1—N1—C7—C12−163.8 (2)C13—C9—C10—Cl11.0 (4)
S1—C1—C2—I1A0.7 (4)C13—C9—C10—C11−178.1 (2)
S1—C1—C2—C3−178.5 (2)C8—C9—C13—O3−10.3 (3)
C6—C1—C2—I1A179.6 (2)C8—C9—C13—O4170.0 (3)
C6—C1—C2—C30.4 (4)C10—C9—C13—O3168.5 (3)
S1—C1—C6—C5178.0 (2)C10—C9—C13—O4−11.2 (4)
C2—C1—C6—C5−0.9 (4)Cl1—C10—C11—C12−178.3 (2)
I1A—C2—C3—C4−178.9 (3)C9—C10—C11—C120.8 (4)
C1—C2—C3—C40.4 (5)C10—C11—C12—C7−0.8 (4)
C2—C3—C4—C5−0.7 (5)
D—H···AD—HH···AD···AD—H···A
N1—H1···O4vi0.862.072.903 (3)164
O3—H3O···O2ix0.76 (4)1.95 (4)2.714 (3)176 (5)
C4—H4···O1x0.932.483.293 (4)146
C6—H6···O10.932.362.792 (3)108
C8—H8···O10.932.573.193 (3)125
C8—H8···O30.932.282.631 (3)102
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O4i0.862.072.903 (3)164
O3—H3O⋯O2ii0.76 (4)1.95 (4)2.714 (3)176 (5)
C4—H4⋯O1iii0.932.483.293 (4)146
C6—H6⋯O10.932.362.792 (3)108
C8—H8⋯O10.932.573.193 (3)125
C8—H8⋯O30.932.282.631 (3)102

Symmetry codes: (i) ; (ii) ; (iii) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Methyl (4-bromo-benzene-sulfonamido)acetate.

Authors:  Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Ejaz Ahmad; Muhammad Shafiq
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-20

3.  Sodium 2-iodo-benzene-sulfonate monohydrate.

Authors:  Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Muhammad Shafiq; Waseeq Ahmad Siddiqui
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-29

4.  4-(2-Iodo-benzene-sulfonamido)benzoic acid monohydrate.

Authors:  Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Waseeq Ahmad Siddiqui; Muhammad Shafiq
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-01-08
  4 in total
  4 in total

1.  5-Benzene-sulfonamido-2-chloro-benzoic acid.

Authors:  Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Muhammad Shafiq; Hafiz Muhammad Adeel Sharif
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-25

2.  2-Chloro-6-(2,3-di-chloro-benzene-sulfonamido)-benzoic acid.

Authors:  Ayesha Munir; Hafiz Mubashar-Ur-Rehman; Abdullah M Asiri; Islam Ullah Khan; Muhammad Nadeem Arshad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-05-04

3.  2-Chloro-4-(2-iodo-benzene-sulfonamido)-benzoic acid.

Authors:  Muhammad Nadeem Arshad; Islam Ullah Khan; H M Rafique; Abdullah M Asiri; Muhammad Shafiq
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-07

4.  N-[Amino-(azido)-meth-ylidene]-4-methyl-benzene-sulfonamide.

Authors:  Ayyaz Mahmood; Islam Ullah Khan; Muhammad Nadeem Arshad; Jamil Ahmed
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-23
  4 in total

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