supplementary materials
2-Chloro-5-(2-iodobenzenesulfonamido)benzoic acid
The title compound was synthesized according to a literature method (Deng &
Mani, 2006). 5-Amino-2-chlorobenzoic acid (0.28 g, 1.66 mmol) was
suspended
in distilled water (10 ml) in a round bottom flask. The pH of the solution
was adjusted to 8-9 using Na2CO3 (1 M). Then, 2-iodobenzene sulfonyl
chloride (0.5 g, 1.66 mmol) was added, and stirred at room temperature. The
reaction pH was maintained at 8-9. Completion of reaction was indicated by
the dissolvation of the suspended 2-iodobenzene sulfonyl chloride. Then, pH
was adjusted to 2-3 using HCl (2 N). The precipitate formed was filtered,
washed with distilled water, and then recrystalyzed in methanol.
The iodine atom was disordered over two positions. During the refinement process
the disordered atoms I1A and I1B were refined with occupancies of 0.75 and
0.25,
respectively. H3O (for OH) atom was located in difference syntheses and refined
[O-H = 0.76 (4) Å, Uiso(H) = 1.2Ueq(O)]. The remaining H atoms were
positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 Å for
aromatic H, respectively, and constrained to ride on their parent atoms with
Uiso(H) = 1.2Ueq(C,N).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2003).
2-Chloro-5-(2-iodobenzenesulfonamido)benzoic acid
top
Crystal data top
| C13H9ClINO4S | F(000) = 1696 |
| Mr = 437.62 | Dx = 1.928 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 3738 reflections |
| a = 26.6375 (9) Å | θ = 2.5–28.3° |
| b = 8.5532 (2) Å | µ = 2.45 mm−1 |
| c = 14.2696 (5) Å | T = 296 K |
| β = 111.923 (2)° | Needle, light brown |
| V = 3016.03 (17) Å3 | 0.25 × 0.12 × 0.08 mm |
| Z = 8 | |
Data collection top
Bruker Kappa APEXII CCD
diffractometer | 3738 independent reflections |
| Radiation source: fine-focus sealed tube | 2909 reflections with I > 2σ(I) |
| graphite | Rint = 0.023 |
| Detector resolution: 7.40 pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
| ω scans | h = −34→35 |
Absorption correction: multi-scan
(SADABS; Bruker, 2005) | k = −11→11 |
| Tmin = 0.708, Tmax = 0.819 | l = −18→18 |
| 16794 measured reflections | |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0301P)2 + 3.5121P]
where P = (Fo2 + 2Fc2)/3 |
| 3738 reflections | (Δ/σ)max = 0.002 |
| 203 parameters | Δρmax = 0.54 e Å−3 |
| 0 restraints | Δρmin = −0.31 e Å−3 |
Crystal data top
| C13H9ClINO4S | V = 3016.03 (17) Å3 |
| Mr = 437.62 | Z = 8 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 26.6375 (9) Å | µ = 2.45 mm−1 |
| b = 8.5532 (2) Å | T = 296 K |
| c = 14.2696 (5) Å | 0.25 × 0.12 × 0.08 mm |
| β = 111.923 (2)° | |
Data collection top
Bruker Kappa APEXII CCD
diffractometer | 3738 independent reflections |
Absorption correction: multi-scan
(SADABS; Bruker, 2005) | 2909 reflections with I > 2σ(I) |
| Tmin = 0.708, Tmax = 0.819 | Rint = 0.023 |
| 16794 measured reflections | θmax = 28.3° |
Refinement top
| R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.069 | Δρmax = 0.54 e Å−3 |
| S = 1.05 | Δρmin = −0.31 e Å−3 |
| 3738 reflections | Absolute structure: ? |
| 203 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | Occ. (<1) |
| I1A | 0.12215 (4) | 0.55411 (16) | 0.41289 (12) | 0.0562 (2) | 0.750 |
| I1B | 0.12364 (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) | |
| S1 | 0.16694 (2) | 0.68574 (6) | 0.21704 (5) | 0.0391 (2) | |
| O1 | 0.18866 (8) | 0.7712 (2) | 0.15530 (16) | 0.0565 (7) | |
| O2 | 0.18272 (7) | 0.52454 (19) | 0.23828 (15) | 0.0482 (6) | |
| O3 | 0.13053 (10) | 1.2455 (2) | 0.1957 (2) | 0.0776 (9) | |
| O4 | 0.05294 (9) | 1.3743 (2) | 0.13943 (18) | 0.0690 (8) | |
| N1 | 0.10171 (8) | 0.6828 (2) | 0.16552 (17) | 0.0441 (7) | |
| C1 | 0.18390 (9) | 0.7924 (3) | 0.33142 (18) | 0.0361 (7) | |
| C2 | 0.16797 (10) | 0.7500 (3) | 0.4100 (2) | 0.0418 (8) | |
| C3 | 0.18262 (12) | 0.8446 (4) | 0.4949 (2) | 0.0556 (10) | |
| C4 | 0.21208 (13) | 0.9786 (4) | 0.5010 (3) | 0.0624 (11) | |
| C5 | 0.22800 (12) | 1.0202 (3) | 0.4236 (3) | 0.0578 (10) | |
| C6 | 0.21433 (10) | 0.9275 (3) | 0.3391 (2) | 0.0453 (8) | |
| C7 | 0.06742 (10) | 0.8137 (2) | 0.15009 (18) | 0.0371 (7) | |
| C8 | 0.08656 (10) | 0.9658 (2) | 0.15617 (19) | 0.0402 (7) | |
| C9 | 0.05220 (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) | |
| C12 | 0.01314 (10) | 0.7883 (3) | 0.1292 (2) | 0.0451 (8) | |
| C13 | 0.07726 (12) | 1.2528 (3) | 0.1587 (2) | 0.0456 (8) | |
| H1 | 0.08656 | 0.59352 | 0.14579 | 0.0529* | |
| H3 | 0.17239 | 0.81700 | 0.54829 | 0.0667* | |
| H3O | 0.1464 (16) | 1.322 (5) | 0.207 (3) | 0.0931* | |
| H4 | 0.22130 | 1.04151 | 0.55811 | 0.0749* | |
| H5 | 0.24800 | 1.11102 | 0.42821 | 0.0695* | |
| H6 | 0.22545 | 0.95503 | 0.28681 | 0.0544* | |
| H8 | 0.12289 | 0.98281 | 0.16784 | 0.0482* | |
| H11 | −0.05802 | 0.89606 | 0.10069 | 0.0588* | |
| H12 | −0.00012 | 0.68681 | 0.12427 | 0.0541* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| I1A | 0.0535 (3) | 0.0462 (3) | 0.0796 (5) | −0.0084 (2) | 0.0373 (3) | 0.0109 (4) |
| I1B | 0.106 (2) | 0.0709 (18) | 0.0809 (13) | −0.0395 (13) | 0.0591 (12) | −0.0108 (9) |
| Cl1 | 0.0705 (5) | 0.0508 (4) | 0.0822 (5) | 0.0268 (3) | 0.0318 (4) | 0.0054 (4) |
| S1 | 0.0453 (3) | 0.0250 (3) | 0.0528 (4) | 0.0010 (2) | 0.0250 (3) | −0.0009 (2) |
| O1 | 0.0748 (13) | 0.0452 (10) | 0.0659 (13) | −0.0060 (9) | 0.0452 (11) | −0.0017 (9) |
| O2 | 0.0482 (10) | 0.0272 (8) | 0.0719 (13) | 0.0059 (7) | 0.0255 (9) | −0.0022 (8) |
| O3 | 0.0640 (15) | 0.0245 (9) | 0.140 (2) | −0.0043 (9) | 0.0331 (15) | −0.0062 (11) |
| O4 | 0.0735 (14) | 0.0240 (9) | 0.0982 (17) | 0.0068 (9) | 0.0190 (12) | 0.0050 (9) |
| N1 | 0.0451 (11) | 0.0202 (8) | 0.0602 (14) | 0.0000 (8) | 0.0119 (10) | −0.0022 (8) |
| C1 | 0.0333 (11) | 0.0271 (10) | 0.0489 (14) | 0.0007 (8) | 0.0166 (10) | 0.0000 (9) |
| C2 | 0.0379 (13) | 0.0389 (12) | 0.0531 (15) | 0.0018 (10) | 0.0221 (11) | 0.0042 (11) |
| C3 | 0.0577 (17) | 0.0623 (18) | 0.0538 (17) | 0.0023 (14) | 0.0290 (14) | −0.0012 (13) |
| C4 | 0.0660 (19) | 0.0542 (17) | 0.0633 (19) | −0.0021 (14) | 0.0198 (16) | −0.0204 (14) |
| C5 | 0.0598 (18) | 0.0364 (14) | 0.073 (2) | −0.0110 (12) | 0.0200 (16) | −0.0077 (13) |
| C6 | 0.0444 (14) | 0.0344 (12) | 0.0583 (16) | −0.0061 (10) | 0.0205 (12) | 0.0012 (11) |
| C7 | 0.0459 (13) | 0.0241 (10) | 0.0378 (12) | 0.0028 (9) | 0.0115 (10) | 0.0001 (9) |
| C8 | 0.0458 (13) | 0.0255 (10) | 0.0476 (14) | 0.0015 (9) | 0.0155 (11) | 0.0015 (9) |
| C9 | 0.0551 (15) | 0.0246 (10) | 0.0376 (13) | 0.0035 (9) | 0.0163 (11) | 0.0014 (9) |
| C10 | 0.0545 (15) | 0.0362 (12) | 0.0398 (13) | 0.0129 (10) | 0.0172 (11) | 0.0012 (10) |
| C11 | 0.0456 (14) | 0.0440 (14) | 0.0541 (16) | 0.0017 (11) | 0.0147 (12) | −0.0001 (12) |
| C12 | 0.0465 (14) | 0.0310 (11) | 0.0539 (15) | −0.0024 (10) | 0.0143 (12) | 0.0006 (10) |
| C13 | 0.0632 (17) | 0.0253 (11) | 0.0490 (15) | 0.0040 (10) | 0.0218 (13) | 0.0007 (10) |
Geometric parameters (Å, °) top
| I1A—C2 | 2.082 (3) | C4—C5 | 1.370 (5) |
| I1B—C2 | 2.150 (5) | C5—C6 | 1.374 (4) |
| Cl1—C10 | 1.731 (3) | C7—C12 | 1.380 (4) |
| S1—O1 | 1.423 (2) | C7—C8 | 1.388 (3) |
| S1—O2 | 1.4403 (17) | C8—C9 | 1.399 (3) |
| S1—N1 | 1.614 (2) | C9—C10 | 1.388 (4) |
| S1—C1 | 1.775 (3) | C9—C13 | 1.494 (4) |
| O3—C13 | 1.318 (4) | C10—C11 | 1.384 (4) |
| O4—C13 | 1.201 (3) | C11—C12 | 1.379 (4) |
| O3—H3O | 0.76 (4) | C3—H3 | 0.9300 |
| N1—C7 | 1.409 (3) | C4—H4 | 0.9300 |
| N1—H1 | 0.8600 | C5—H5 | 0.9300 |
| C1—C6 | 1.392 (4) | C6—H6 | 0.9300 |
| C1—C2 | 1.387 (4) | C8—H8 | 0.9300 |
| C2—C3 | 1.386 (4) | C11—H11 | 0.9300 |
| C3—C4 | 1.373 (5) | C12—H12 | 0.9300 |
| | | |
| I1A···O2 | 3.446 (2) | C1···C8 | 3.215 (3) |
| I1A···N1 | 3.540 (3) | C2···C4ii | 3.552 (5) |
| I1A···Cl1i | 3.4575 (16) | C4···C2ii | 3.552 (5) |
| I1A···C5ii | 3.851 (4) | C4···O1x | 3.293 (4) |
| I1B···O2 | 3.271 (6) | C5···I1Aii | 3.851 (4) |
| I1B···N1 | 3.438 (6) | C5···I1Bii | 3.835 (6) |
| I1B···C5ii | 3.835 (6) | C6···C8 | 3.445 (4) |
| I1B···Cl1i | 3.381 (5) | C6···O2xi | 3.419 (3) |
| I1A···H12iii | 3.2900 | C7···Cl1v | 3.549 (3) |
| I1A···H11iii | 3.3600 | C8···O1 | 3.193 (3) |
| Cl1···O4 | 2.939 (3) | C8···C6 | 3.445 (4) |
| Cl1···I1Aiv | 3.4575 (16) | C8···C1 | 3.215 (3) |
| Cl1···I1Biv | 3.381 (5) | C9···C11v | 3.499 (4) |
| Cl1···C7v | 3.549 (3) | C10···C10iii | 3.552 (4) |
| S1···H3Ovi | 3.15 (4) | C11···C11iii | 3.568 (4) |
| S1···H8 | 2.7800 | C11···C9v | 3.499 (4) |
| O1···C8 | 3.193 (3) | C1···H8 | 2.8100 |
| O1···C4vii | 3.293 (4) | C6···H8 | 2.7700 |
| O2···O3vi | 2.714 (3) | C13···H1ix | 2.9400 |
| O2···I1B | 3.271 (6) | H1···O4vi | 2.0700 |
| O2···I1A | 3.446 (2) | H1···C13vi | 2.9400 |
| O2···C6viii | 3.419 (3) | H1···H12 | 2.3500 |
| O3···O2ix | 2.714 (3) | H3···O3x | 2.7800 |
| O4···N1ix | 2.903 (3) | H3O···S1ix | 3.15 (4) |
| O4···Cl1 | 2.939 (3) | H3O···O2ix | 1.95 (4) |
| O1···H8 | 2.5700 | H4···O1x | 2.4800 |
| O1···H4vii | 2.4800 | H5···O1xi | 2.7600 |
| O1···H6 | 2.3600 | H6···O1 | 2.3600 |
| O1···H5viii | 2.7600 | H6···O2xi | 2.6700 |
| O2···H6viii | 2.6700 | H8···S1 | 2.7800 |
| O2···H3Ovi | 1.95 (4) | H8···O1 | 2.5700 |
| O3···H3vii | 2.7800 | H8···O3 | 2.2800 |
| O3···H8 | 2.2800 | H8···C1 | 2.8100 |
| O4···H1ix | 2.0700 | H8···C6 | 2.7700 |
| N1···I1A | 3.540 (3) | H11···I1Aiii | 3.3600 |
| N1···I1B | 3.438 (6) | H12···H1 | 2.3500 |
| N1···O4vi | 2.903 (3) | H12···I1Aiii | 3.2900 |
| | | |
| O1—S1—O2 | 117.89 (12) | C8—C9—C10 | 118.2 (2) |
| O1—S1—N1 | 110.08 (12) | C8—C9—C13 | 117.2 (2) |
| O1—S1—C1 | 106.41 (12) | C10—C9—C13 | 124.6 (2) |
| O2—S1—N1 | 105.12 (11) | Cl1—C10—C9 | 123.3 (2) |
| O2—S1—C1 | 110.15 (12) | Cl1—C10—C11 | 116.3 (2) |
| N1—S1—C1 | 106.73 (12) | C9—C10—C11 | 120.4 (3) |
| C13—O3—H3O | 118 (3) | C10—C11—C12 | 120.8 (3) |
| S1—N1—C7 | 125.69 (16) | C7—C12—C11 | 119.9 (2) |
| C7—N1—H1 | 117.00 | O3—C13—O4 | 122.7 (3) |
| S1—N1—H1 | 117.00 | O3—C13—C9 | 111.8 (2) |
| S1—C1—C6 | 116.10 (19) | O4—C13—C9 | 125.5 (3) |
| S1—C1—C2 | 124.0 (2) | C2—C3—H3 | 120.00 |
| C2—C1—C6 | 119.9 (2) | C4—C3—H3 | 120.00 |
| I1A—C2—C1 | 125.8 (2) | C3—C4—H4 | 120.00 |
| I1A—C2—C3 | 115.4 (2) | C5—C4—H4 | 120.00 |
| C1—C2—C3 | 118.9 (3) | C4—C5—H5 | 120.00 |
| I1B—C2—C1 | 120.5 (2) | C6—C5—H5 | 120.00 |
| I1B—C2—C3 | 120.7 (3) | C1—C6—H6 | 120.00 |
| C2—C3—C4 | 120.7 (3) | C5—C6—H6 | 120.00 |
| C3—C4—C5 | 120.5 (3) | C7—C8—H8 | 119.00 |
| C4—C5—C6 | 119.8 (3) | C9—C8—H8 | 119.00 |
| C1—C6—C5 | 120.3 (3) | C10—C11—H11 | 120.00 |
| C8—C7—C12 | 119.5 (2) | C12—C11—H11 | 120.00 |
| N1—C7—C8 | 122.2 (2) | C7—C12—H12 | 120.00 |
| N1—C7—C12 | 118.31 (19) | C11—C12—H12 | 120.00 |
| C7—C8—C9 | 121.2 (3) | | |
| | | |
| O1—S1—N1—C7 | −65.6 (2) | C3—C4—C5—C6 | 0.1 (5) |
| O2—S1—N1—C7 | 166.5 (2) | C4—C5—C6—C1 | 0.7 (5) |
| C1—S1—N1—C7 | 49.5 (2) | N1—C7—C8—C9 | −177.1 (2) |
| O1—S1—C1—C2 | 177.4 (2) | C12—C7—C8—C9 | 2.3 (4) |
| O1—S1—C1—C6 | −1.6 (2) | N1—C7—C12—C11 | 178.7 (2) |
| O2—S1—C1—C2 | −53.8 (3) | C8—C7—C12—C11 | −0.7 (4) |
| O2—S1—C1—C6 | 127.3 (2) | C7—C8—C9—C10 | −2.3 (4) |
| N1—S1—C1—C2 | 59.8 (3) | C7—C8—C9—C13 | 176.6 (2) |
| N1—S1—C1—C6 | −119.1 (2) | C8—C9—C10—Cl1 | 179.79 (19) |
| S1—N1—C7—C8 | 15.6 (4) | C8—C9—C10—C11 | 0.8 (4) |
| S1—N1—C7—C12 | −163.8 (2) | C13—C9—C10—Cl1 | 1.0 (4) |
| S1—C1—C2—I1A | 0.7 (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—I1A | 179.6 (2) | C8—C9—C13—O4 | 170.0 (3) |
| C6—C1—C2—C3 | 0.4 (4) | C10—C9—C13—O3 | 168.5 (3) |
| S1—C1—C6—C5 | 178.0 (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—C12 | 0.8 (4) |
| C1—C2—C3—C4 | 0.4 (5) | C10—C11—C12—C7 | −0.8 (4) |
| C2—C3—C4—C5 | −0.7 (5) | | |
| Symmetry codes: (i) −x, y−1, −z+1/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) −x, y, −z+1/2; (iv) −x, y+1, −z+1/2; (v) −x, −y+2, −z; (vi) x, y−1, z; (vii) x, −y+2, z−1/2; (viii) −x+1/2, y−1/2, −z+1/2; (ix) x, y+1, z; (x) x, −y+2, z+1/2; (xi) −x+1/2, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O4vi | 0.86 | 2.07 | 2.903 (3) | 164 |
| O3—H3O···O2ix | 0.76 (4) | 1.95 (4) | 2.714 (3) | 176 (5) |
| C4—H4···O1x | 0.93 | 2.48 | 3.293 (4) | 146 |
| C6—H6···O1 | 0.93 | 2.36 | 2.792 (3) | 108 |
| C8—H8···O1 | 0.93 | 2.57 | 3.193 (3) | 125 |
| C8—H8···O3 | 0.93 | 2.28 | 2.631 (3) | 102 |
| Symmetry codes: (vi) x, y−1, z; (ix) x, y+1, z; (x) x, −y+2, z+1/2. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O4i | 0.86 | 2.07 | 2.903 (3) | 164 |
| O3—H3O···O2ii | 0.76 (4) | 1.95 (4) | 2.714 (3) | 176 (5) |
| C4—H4···O1iii | 0.93 | 2.48 | 3.293 (4) | 146 |
| C6—H6···O1 | 0.93 | 2.36 | 2.792 (3) | 108 |
| C8—H8···O1 | 0.93 | 2.57 | 3.193 (3) | 125 |
| C8—H8···O3 | 0.93 | 2.28 | 2.631 (3) | 102 |
| Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x, −y+2, z+1/2. |
MNA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan,
for providing a scholarship under the Indigenous PhD Program (PIN
042-120607-PS2-183).
Arshad, M. N., Tahir, M. N., Khan, I. U., Ahmad, E. & Shafiq, M. (2008). Acta Cryst. E64, o2380.
Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, m1628.
Arshad, M. N., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Shafiq, M. (2009). Acta Cryst. E65, o230. Please check; reference not found
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, X. & Mani, N. S. (2006). Green Chem. 8, 835–838.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
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, intermolecular N-H![[pi]](/logos/entities/pi_rmgif.gif)
-![[Figure 1]](./hk2607fig1thm.gif)
![[Figure 2]](./hk2607fig2thm.gif)
In continuation to our researches with sulfonamides (Arshad, Tahir, Khan, Ahmad & Shafiq, 2008; Arshad, Tahir, Khan, Shafiq & Siddiqui, 2008; Arshad et al., 2009), the title compound has been synthesized, and we report herein its crystal structure.
The structure of the title compound, (I), (Fig 1), differs from 4-[(2-iodo- phenyl)sulfonyl]aminobenzoic acid hydrate, (II) (Arshad et al., 2009), due to the attachment of Cl atom and the change of the position of carboxylate group. Also in (I), there is no water molecule. The coordination around the S atom is a distorted tetrahedral. Rings A(C1-C6) and B(C7-C12) are oriented at a dihedral angle of 74.46 (9)°, which is nearly the same with the corresponding value [74.18 (17)°] in (II). The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of two five- and one six-membered rings: C (S1/O1/C1/C6/H6), D (O3/C8/C9/C13/H8) and E (S1/O1/N1/C7/C8/H8). Ring C is planar. Ring D adopts envelope conformation with O3 atom displaced by -0.260 (4) Å from the plane of the other rings atoms, while ring E has twisted conformation. The dihedral angle between rings A and C is 2.18 (3)°.
In the crystal structure, intermolecular N-H···O and O-H···O hydrogen bonds (Table 1) link the molecules to form R22(8) ring motifs (Bernstein et al., 1995), they are further linked by C-H···O hydrogen bonds (Table 1, Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contacts between the phenyl rings and the benzene rings, Cg1—Cg1i and Cg2—Cg2ii [symmetry codes: (i) 1/2 - x, 3/2 - y, 1 - z; (ii) -x, 2 - y, -z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B(C7-C12), respectively] may further stabilize the structure, with centroid-centroid distances of 3.709 (3) Å and 3.772 (3) Å.