N-(2-Iodophenyl)benzenesulfonamide, C12H10INO2, and N-(4,5-difluoro-2-iodophenyl)benzenesulfonamide, C12H8F2INO2S differ only in the replacement of two H atoms by F atoms, which changes the symmetry from P21/c to P1 and is accompanied by different molecular conformations and packing features.
Keywords: crystal structure; 2-iodophenyl; 4,5-difluoro; benzenesulfonamide; π–π interactions; hydrogen bonding; Hirshfeld surface analysis
Abstract
Two new benzenesulfonyl derivatives, N-(2-iodophenyl)benzenesulfonamide, C12H10INO2, (I), and N-(4,5-difluoro-2-iodophenyl)benzenesulfonamide, C12H8F2INO2S, (II) were synthesized and structurally characterized. In both molecular structures, the conformation of the N—C bond in the –SO2—NH—C segment is gauche relative to the S=O bond. For (I), the crystal packing is dominated by N—H⋯O hydrogen-bonding interactions that link the molecules into chains extending parallel to [010]. In the case of (II), the molecules are linked by N—H⋯O(S) hydrogen bonds into dimers that are located on centers of inversion. These findings are consistent with the results of Hirshfeld surface analyses.
1. Chemical context
Sulfonamide-containing compounds, often referred to as sulfa drugs, form a significant class of pharmacologically active agents. These molecules, which may incorporate one or more pharmacological scaffolds, demonstrate a broad spectrum of biological activities including antiviral, anticancer, antibacterial, anti-carbonic anhydrase (CA), diuretic, COX-2 inhibitory, and protease inhibitory effects (Madhan et al., 2024a ▸,b ▸,c ▸). The sulfonamide moiety is recognized as an important structural unit in medicinal chemistry and is present in many widely marketed drugs (Supuran, 2003 ▸; Elgemeie et al., 2019 ▸). Since their discovery, sulfonamides have been extensively used as antibiotics (Zhao et al., 2016 ▸), particularly for treating infections like malaria, tuberculosis, or HIV, by targeting the dihydropteroate synthase (DHPS) pathway (Dennis et al., 2018 ▸). Even after the advent of penicillin, sulfa drugs have retained their relevance in clinical settings due to their diverse therapeutic actions, including antitumor, anticancer, and antithyroid activities (Scozzafava et al., 2003 ▸). Various sulfonamide derivatives serve as chemotherapeutic agents, exhibiting antibacterial, antifungal, antitumor, and hypoglycemic properties (Chohan et al., 2010 ▸; El-Sayed et al., 2011 ▸ Seri et al., 2000 ▸). Benzenesulfonamide derivatives are particularly known for their antitumor and antifungal activities. Crystallographic studies of these compounds reveal structural parameters consistent with other sulfonamide-based molecules (Chakkaravarthi et al., 2007 ▸; Li & Yang, 2006 ▸). Continued interest in sulfonamides stems from their enduring role in treating bacterial infections, their chemical versatility, and their effectiveness despite the rise of newer antibiotic classes. Modern synthetic approaches aim to produce sulfonamide-functionalized heterocycles with enhanced antiviral and antimicrobial profiles (Madhan et al., 2024a ▸). Research into N-sulfonylated I and F atom-substituted compounds is motivated by the observed enhancement of biological activity. Hence, the introduction of fluorine atoms into drugs is increasingly common due to the strong electron-withdrawing character and small atomic radius of the fluorine atom, which significantly influences the physiological, pharmacological and metabolic properties of a compound (Mueller et al., 2007 ▸; Purser et al., 2008 ▸). The availability of multiple aromatic groups in N-sulfonylated 2-iodophenyl imposes also the possibility for versatile stacking patterns, which may be competitive to the conventional hydrogen-bonding interactions in the crystal packing.
In the context given above, we report herein the crystal structure determinations and Hirshfeld surface analyses of two new 2-iodophenyl benzenesulfonamides: N-(2-iodophenyl)benzenesulfonamide, C12H10INO2, (I), and N-(4,5-difluoro-2-iodophenyl)benzenesulfonamide, C12H8F2INO2S, (II), which feature a complex interplay of weak hydrogen bonding and π–π interactions.
2. Structural commentary
The molecular structures of (I) and (II) are shown in Figs. 1 ▸ and 2 ▸, respectively. In both cases, the conformation of the N—C bond in the –SO2—NH—C segment is gauche relative to the S=O bond. The molecule is twisted at the S—N bond with a torsion angle of C7—N1—S1—C6 = −69.0 (2)° for (I) and −61.1 (6)° for (II) compared to the values of −72.83 (15) and 61.9 (3)° in N-(phenyl)-2-nitrobenzenesulfonamide (Chaithanya et al., 2012a ▸) and 4-nitro-N-phenylbenzenesulfonamide (Chaithanya et al., 2012b ▸), respectively. The two benzene rings are tilted relative to each other by 44.1 (1)° for (I) and 73.1 (1)° for (II). The molecular configuration of (II) is stabilized by a weak intramolecular hydrogen bond C12—H12⋯O1 (Table 1 ▸) with one of the sulfone O-atoms as acceptor, which generates an S(6) ring motif. Other structural parameters (bond lengths and angles) in the molecules of (I) and (II) agree well with those reported for related compounds (Madhan et al., 2022 ▸, 2023a ▸,b ▸, 2024a ▸,b ▸,c ▸).
Figure 1.
The molecular structure of compound (I), with atom labeling and displacement ellipsoids drawn at the 50% probability level.
Figure 2.
The molecular structure of compound (II), with atom labeling and displacement ellipsoids drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °) for (I).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1A⋯O2i | 0.86 | 2.37 | 3.144 (3) | 149 |
| C3—H3⋯O1ii | 0.93 | 2.57 | 3.352 (4) | 142 |
Symmetry codes: (i) 
; (ii) 
.
3. Supramolecular features
In the crystal structure of (I), intermolecular N—H⋯O hydrogen-bonding interactions (Table 1 ▸) link the molecules into C(4) chains (Etter et al., 1990 ▸) running parallel to [010] while C—H⋯O interactions interlink these chains (Fig. 3 ▸). In addition, π–π interactions are present with a centroid-to-centroid distance Cg2⋯Cg2 (2 − x, 1 − y, 1 − z) = 3.747 (2) Å and a slippage of 1.035 Å (Cg2 is the centroid of phenyl ring C7–C1).
Figure 3.
Crystal packing of compound (I), showing the N—H⋯O and C—H⋯O interaction that link the molecules into chains.
In the crystal structure of (II), molecules are linked by N—H⋯O(S) hydrogen-bonding interactions (Table 2 ▸, Fig. 4 ▸) into inversion-related dimers with an 
(8) graph-set motif (Etter et al., 1990 ▸). Like for (I), π–π interactions are present that consolidate the crystal packing, here with centroid-to-centroid distances Cg1⋯Cg1(1 − x, 2 − y, −z) = 3.621 (2) and a slippage of 0.998 Å and Cg2⋯Cg2(2 − x, 1 − y, 1 − z) = 3.797 (2) Å and a slippage of 1.617 Å (Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively).
Table 2. Hydrogen-bond geometry (Å, °) for (II).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1A⋯O2i | 0.86 | 2.58 | 3.169 (8) | 126 |
| C12—H12⋯O1 | 0.93 | 2.27 | 2.916 (11) | 126 |
Symmetry code: (i) 
.
Figure 4.
Crystal packing of compound (II), showing the N—H⋯O(S) hydrogen-bonding interactions that lead to inversion-related dimers.
4. Hirshfeld surface analysis
In order to quantify the intermolecular interactions in the crystals of (I) and (II), Hirshfeld surfaces and two-dimensional fingerprint plots were generated using CrystalExplorer (Spackman et al., 2021 ▸).
Plots of dnorm use the normalized functions di and de (Fig. 5 ▸), with white surfaces indicating contacts with distances equal to the sum of van der Waals (vdW) radii, while red and blue colors reflect contacts at the distances below and above sum of the corresponding vdW radii, respectively. Two-dimensional fingerprint plots showing the occurrence of all intermolecular contacts (McKinnon et al., 2007 ▸) and are presented in Fig. 6 ▸. H⋯H in (I) and O⋯H/H⋯O contacts in (II) represent the largest contributions to the Hirshfeld surfaces (37.4 and 44.7%, respectively). Beyond these largest fractions, short contacts are O⋯H/H⋯O (21.7%) for (I) and O⋯C/C⋯O (17.2%) for (II) (Fig. 6 ▸c), C⋯H/H⋯C (16.5%) for (I) and O⋯O (11%) for (II) (Fig. 6 ▸d). The significant increase in the O⋯H/H⋯O contributions when moving from (I) to (II) reflects growing significance of C—H⋯O binding. This is in line with a larger number of the available intermolecular O-atom acceptors in the latter case. Accordingly, a pair of spikes identifying O⋯H/H⋯O contacts on the plots in the case of (I) is more diffuse.
Figure 5.
The Hirshfeld surfaces of compounds (I) and (II) mapped over dnorm.
Figure 6.
Two-dimensional fingerprint plots for (I) and delineated into the principal contributions of H⋯H, O⋯H/H⋯O, C⋯H/H⋯C, I⋯H/H⋯I, I⋯C/C⋯I, C⋯C and I⋯O/O⋯I contacts and for (II) O⋯H/H⋯O, O⋯C/C⋯O, O⋯O, N⋯O/O⋯N, H⋯H, H⋯C/C⋯H, C⋯C, N⋯C/C⋯N and N⋯H/H⋯N. Other contributors account for less than 1.0% contacts to the surface areas.
In brief, the Hirshfeld surface analyses complement the main merit of the structure analyses, and together they suggest possibilities for controlling the supramolecular behavior of benzenesulfonamide as possible biomedical materials.
5. Database survey
A search of the Cambridge Structural Database (CSD, version 5.37; Groom et al., 2016 ▸) indicated 123 compounds incorporating the phenylsulfonamide moiety. The bond lengths and angles in (I) and (II) are very close to those observed in 2,4-dimethyl-N-(phenyl)benzenesulfonamide (Gowda et al., 2009a ▸), 4-chloro-2-methyl-N-(phenyl)benzenesulfonamide (Gowda et al., 2009b ▸), 4-methyl-N-(3,4-dimethylphenyl)benzenesulfonamide (Gowda et al., 2009c ▸) and other aryl sulfonamides Perlovich et al., 2006 ▸; Tatsuta et al., 2009 ▸; Arora & Sundaralingam, 1971 ▸; Gelbrich et al., 2007 ▸). Of these, the most closely related examples are provided by structures of bromosubstituted 3-methyl-1-(phenylsulfonyl)-1H-indole derivatives (Madhan et al., 2024b ▸).
6. Synthesis and crystallization
(I): To a solution of 2-iodoaniline (2 g, 9.17 mmol) in dry dichloromethane (DCM; 10 ml), benzenesulfonyl chloride (1.42 ml, 11.01 mmol) and pyridine (1.11 ml, 13.76 mmol) were slowly added and stirred at room temperature for 8 h under nitrogen atmosphere. After completion of the reaction (monitored by TLC), it was poured into ice water containing conc. HCl (1 ml), extracted with DCM (3 × 10 ml) then washed with water (2 × 20 ml) and dried (Na2SO4). Removal of the solvent in vacuo followed by trituration of the crude product with diethyl ether (5 ml) afforded (I) (2.43 g, 84%) as a colorless solid. M.p: 363–365 K. 1H-NMR (300 MHZ, CDCl3): δ 7.70 (d, J = 7.5 Hz, 2H), 7.61 (t, J = 7.5 Hz, 2H), 7.55–7.49 (m, 1 H), 7.41–7.36 (m, 2H), 7.28 (t, J = 7.5 Hz, 1H), 6.82–6.77 (m, 2H) ppm; 13C{1H}-NMR (75 MHz, CDCl3): δ 139.1, 138.8, 137.4, 133.3, 129.6, 127.4, 122.9, 92.5 ppm.
(II): To a solution of 4,5-difluoro2-iodoaniline (2 g, 7.84 mmol) in dry DCM (10 ml), benzenesulfonyl chloride (1.21 ml, 9.41 mmol) and pyridine (0.95 ml, 11.76 mmol) were slowly added and stirred at room temperature for 8 h under nitrogen atmosphere. After completion of the reaction (monitored by TLC), it was poured into ice water containing conc. HCl (1 ml), extracted with DCM (3 × 10 ml) then washed with water (2 × 20 ml) and dried (Na2SO4). Removal of solvent in vacuo followed by trituration of the crude product with diethyl ether (5 mL) afforded benzenesulfonamide (II) (2.56 g, 83%) as a colorless solid. M.p: 393–395 K. 1H-NMR (300 MHZ, CDCl3): δ 7.58 (d, J = 7.5 Hz, 2H), 7.45–7.39 (m, 2 H), 7.30–7.26 (m, 3 H)ppm; 13C{1H}-NMR (75 MHz, CDCl3): δ 150.7 (dd, 1JC–F = 249.4 Hz, 2JC–F = 12.7 Hz), 147.8 (dd, 1JC–F = 252 Hz, 2JC–F = 12.7 Hz), 138.4, 134.3 (dd, 1JC–F = 82 Hz, 2JC–F = 3 Hz), 133.7, 129.3, 127.4, 126.8 (d, JC–F = 19.5 Hz), 112.3 (d, JC–F = 21.7 Hz) ppm.
7. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. All hydrogen atoms were positioned geometrically and refined as riding with N—H = 0.86 and C—H = 0.93 Å (aromatic CH) with Uiso(H) = 1.5Ueq(C) for methyl groups and 1.2Ueq(C) for other H atoms.
Table 3. Experimental details.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C12H10INO2S | C12H8F2INO2S |
| M r | 359.17 | 395.15 |
| Crystal system, space group | Monoclinic, P21/c | Triclinic, P
|
| Temperature (K) | 298 | 298 |
| a, b, c (Å) | 8.3648 (4), 9.8537 (4), 15.3923 (8) | 8.2688 (5), 8.5178 (5), 10.4329 (7) |
| α, β, γ (°) | 90, 90.955 (2), 90 | 81.291 (2), 80.503 (2), 68.383 (2) |
| V (Å3) | 1268.52 (10) | 670.47 (7) |
| Z | 4 | 2 |
| Radiation type | Mo Kα | Cu Kα |
| μ (mm−1) | 2.68 | 20.44 |
| Crystal size (mm) | 0.35 × 0.25 × 0.08 | 0.22 × 0.10 × 0.05 |
| Data collection | ||
| Diffractometer | Bruker D8 Venture Diffractometer | Bruker D8 Venture Diffractometer |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.672, 0.971 | 0.240, 0.521 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 29284, 2591, 2386 | 14553, 2476, 2367 |
| R int | 0.049 | 0.062 |
| (sin θ/λ)max (Å−1) | 0.625 | 0.605 |
| Refinement | ||
| R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.069, 1.09 | 0.072, 0.203, 1.14 |
| No. of reflections | 2591 | 2476 |
| No. of parameters | 155 | 173 |
| H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.54, −0.56 | 1.66, −0.95 |
Supplementary Material
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989025006656/wm5762sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025006656/wm5762Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989025006656/wm5762IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989025006656/wm5762Isup4.cml
Supporting information file. DOI: 10.1107/S2056989025006656/wm5762IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the SAIF, IIT, Madras, India, for the data collection.
supplementary crystallographic information
N-(2-Iodophenyl)benzenesulfonamide (I) . Crystal data
| C12H10INO2S | F(000) = 696 |
| Mr = 359.17 | Dx = 1.881 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.3648 (4) Å | Cell parameters from 29284 reflections |
| b = 9.8537 (4) Å | θ = 1.4–25.0° |
| c = 15.3923 (8) Å | µ = 2.68 mm−1 |
| β = 90.955 (2)° | T = 298 K |
| V = 1268.52 (10) Å3 | Prism, colourless |
| Z = 4 | 0.35 × 0.25 × 0.08 mm |
N-(2-Iodophenyl)benzenesulfonamide (I) . Data collection
| Bruker D8 Venture Diffractometer | 2386 reflections with I > 2σ(I) |
| Radiation source: micro focus sealed tube | Rint = 0.049 |
| ω and φ scans | θmax = 26.4°, θmin = 3.4° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −10→10 |
| Tmin = 0.672, Tmax = 0.971 | k = −12→12 |
| 29284 measured reflections | l = −19→19 |
| 2591 independent reflections |
N-(2-Iodophenyl)benzenesulfonamide (I) . Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0319P)2 + 1.2298P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.069 | (Δ/σ)max = 0.002 |
| S = 1.09 | Δρmax = 0.54 e Å−3 |
| 2591 reflections | Δρmin = −0.56 e Å−3 |
| 155 parameters | Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0085 (7) |
N-(2-Iodophenyl)benzenesulfonamide (I) . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
N-(2-Iodophenyl)benzenesulfonamide (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.5786 (3) | 0.4285 (3) | 0.74857 (19) | 0.0393 (6) | |
| H1 | 0.601455 | 0.365298 | 0.705621 | 0.047* | |
| C2 | 0.4228 (4) | 0.4717 (4) | 0.7611 (2) | 0.0488 (8) | |
| H2 | 0.340905 | 0.439224 | 0.725207 | 0.059* | |
| C3 | 0.3886 (4) | 0.5624 (4) | 0.8263 (3) | 0.0539 (9) | |
| H3 | 0.283767 | 0.590431 | 0.834558 | 0.065* | |
| C4 | 0.5092 (4) | 0.6113 (4) | 0.8791 (3) | 0.0576 (9) | |
| H4 | 0.485310 | 0.671374 | 0.923622 | 0.069* | |
| C5 | 0.6662 (4) | 0.5720 (3) | 0.8666 (2) | 0.0451 (7) | |
| H5 | 0.747984 | 0.606424 | 0.901827 | 0.054* | |
| C6 | 0.6996 (3) | 0.4810 (3) | 0.80115 (17) | 0.0310 (5) | |
| C7 | 0.8849 (3) | 0.4506 (3) | 0.61007 (17) | 0.0311 (5) | |
| C8 | 0.7791 (3) | 0.5277 (3) | 0.55998 (18) | 0.0342 (6) | |
| C9 | 0.7163 (4) | 0.4759 (4) | 0.4824 (2) | 0.0481 (8) | |
| H9 | 0.646575 | 0.528401 | 0.448826 | 0.058* | |
| C10 | 0.7567 (4) | 0.3479 (4) | 0.4552 (2) | 0.0547 (9) | |
| H10 | 0.713859 | 0.313449 | 0.403539 | 0.066* | |
| C11 | 0.8612 (5) | 0.2705 (4) | 0.5049 (2) | 0.0537 (9) | |
| H11 | 0.888068 | 0.183527 | 0.486772 | 0.064* | |
| C12 | 0.9263 (4) | 0.3215 (3) | 0.5814 (2) | 0.0420 (7) | |
| H12 | 0.998086 | 0.269303 | 0.613894 | 0.050* | |
| N1 | 0.9533 (3) | 0.4996 (2) | 0.69018 (14) | 0.0316 (5) | |
| H1A | 1.022622 | 0.564040 | 0.689506 | 0.038* | |
| O1 | 0.9978 (2) | 0.4978 (2) | 0.84793 (13) | 0.0405 (5) | |
| O2 | 0.9031 (3) | 0.28915 (19) | 0.77277 (14) | 0.0408 (5) | |
| S1 | 0.90001 (7) | 0.43340 (6) | 0.78303 (4) | 0.02932 (16) | |
| I1 | 0.71045 (2) | 0.72190 (2) | 0.59939 (2) | 0.04598 (11) |
N-(2-Iodophenyl)benzenesulfonamide (I) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0361 (15) | 0.0437 (16) | 0.0381 (15) | −0.0119 (12) | 0.0004 (12) | 0.0013 (13) |
| C2 | 0.0328 (15) | 0.059 (2) | 0.0542 (19) | −0.0143 (14) | −0.0079 (13) | 0.0148 (16) |
| C3 | 0.0307 (15) | 0.055 (2) | 0.076 (2) | 0.0046 (14) | 0.0086 (15) | 0.0110 (18) |
| C4 | 0.0435 (18) | 0.057 (2) | 0.072 (2) | 0.0047 (16) | 0.0105 (17) | −0.0175 (19) |
| C5 | 0.0360 (15) | 0.0491 (18) | 0.0500 (17) | −0.0010 (13) | 0.0013 (13) | −0.0111 (15) |
| C6 | 0.0283 (12) | 0.0328 (13) | 0.0320 (13) | −0.0013 (10) | 0.0003 (10) | 0.0059 (11) |
| C7 | 0.0291 (12) | 0.0344 (14) | 0.0300 (13) | −0.0044 (10) | 0.0080 (10) | −0.0005 (11) |
| C8 | 0.0319 (13) | 0.0387 (15) | 0.0320 (13) | −0.0018 (11) | 0.0063 (11) | 0.0002 (11) |
| C9 | 0.0418 (16) | 0.068 (2) | 0.0343 (15) | −0.0020 (15) | −0.0015 (12) | −0.0053 (15) |
| C10 | 0.053 (2) | 0.069 (2) | 0.0419 (17) | −0.0123 (18) | 0.0080 (15) | −0.0218 (17) |
| C11 | 0.060 (2) | 0.0462 (19) | 0.056 (2) | −0.0063 (15) | 0.0219 (17) | −0.0208 (16) |
| C12 | 0.0412 (16) | 0.0392 (15) | 0.0461 (16) | 0.0024 (13) | 0.0133 (13) | −0.0029 (13) |
| N1 | 0.0285 (11) | 0.0322 (11) | 0.0340 (11) | −0.0050 (9) | 0.0015 (9) | 0.0027 (9) |
| O1 | 0.0329 (10) | 0.0483 (12) | 0.0399 (11) | −0.0002 (9) | −0.0090 (8) | 0.0000 (9) |
| O2 | 0.0485 (12) | 0.0293 (10) | 0.0445 (11) | 0.0047 (8) | −0.0005 (9) | 0.0073 (8) |
| S1 | 0.0274 (3) | 0.0295 (3) | 0.0309 (3) | 0.0011 (2) | −0.0029 (2) | 0.0029 (3) |
| I1 | 0.04805 (15) | 0.03807 (15) | 0.05150 (16) | 0.00919 (8) | −0.00858 (9) | 0.00039 (8) |
N-(2-Iodophenyl)benzenesulfonamide (I) . Geometric parameters (Å, º)
| C1—C6 | 1.385 (4) | C7—N1 | 1.434 (3) |
| C1—C2 | 1.388 (5) | C8—C9 | 1.393 (4) |
| C1—H1 | 0.9300 | C8—I1 | 2.091 (3) |
| C2—C3 | 1.377 (5) | C9—C10 | 1.373 (5) |
| C2—H2 | 0.9300 | C9—H9 | 0.9300 |
| C3—C4 | 1.372 (5) | C10—C11 | 1.382 (6) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.386 (5) | C11—C12 | 1.384 (5) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.380 (4) | C12—H12 | 0.9300 |
| C5—H5 | 0.9300 | N1—S1 | 1.640 (2) |
| C6—S1 | 1.768 (3) | N1—H1A | 0.8600 |
| C7—C8 | 1.390 (4) | O1—S1 | 1.429 (2) |
| C7—C12 | 1.392 (4) | O2—S1 | 1.430 (2) |
| C6—C1—C2 | 118.8 (3) | C9—C8—I1 | 118.9 (2) |
| C6—C1—H1 | 120.6 | C10—C9—C8 | 120.5 (3) |
| C2—C1—H1 | 120.6 | C10—C9—H9 | 119.8 |
| C3—C2—C1 | 120.5 (3) | C8—C9—H9 | 119.8 |
| C3—C2—H2 | 119.7 | C9—C10—C11 | 119.6 (3) |
| C1—C2—H2 | 119.7 | C9—C10—H10 | 120.2 |
| C4—C3—C2 | 120.0 (3) | C11—C10—H10 | 120.2 |
| C4—C3—H3 | 120.0 | C10—C11—C12 | 120.5 (3) |
| C2—C3—H3 | 120.0 | C10—C11—H11 | 119.8 |
| C3—C4—C5 | 120.6 (3) | C12—C11—H11 | 119.8 |
| C3—C4—H4 | 119.7 | C11—C12—C7 | 120.3 (3) |
| C5—C4—H4 | 119.7 | C11—C12—H12 | 119.8 |
| C6—C5—C4 | 119.1 (3) | C7—C12—H12 | 119.8 |
| C6—C5—H5 | 120.5 | C7—N1—S1 | 120.34 (18) |
| C4—C5—H5 | 120.5 | C7—N1—H1A | 119.8 |
| C5—C6—C1 | 121.0 (3) | S1—N1—H1A | 119.8 |
| C5—C6—S1 | 119.4 (2) | O1—S1—O2 | 120.50 (13) |
| C1—C6—S1 | 119.6 (2) | O1—S1—N1 | 105.77 (12) |
| C8—C7—C12 | 118.9 (3) | O2—S1—N1 | 107.07 (13) |
| C8—C7—N1 | 122.3 (2) | O1—S1—C6 | 107.76 (13) |
| C12—C7—N1 | 118.8 (3) | O2—S1—C6 | 107.45 (13) |
| C7—C8—C9 | 120.2 (3) | N1—S1—C6 | 107.72 (12) |
| C7—C8—I1 | 121.0 (2) | ||
| C6—C1—C2—C3 | −1.8 (5) | C9—C10—C11—C12 | −0.5 (5) |
| C1—C2—C3—C4 | 0.4 (5) | C10—C11—C12—C7 | 1.2 (5) |
| C2—C3—C4—C5 | 1.0 (6) | C8—C7—C12—C11 | −0.8 (4) |
| C3—C4—C5—C6 | −1.1 (6) | N1—C7—C12—C11 | 179.3 (3) |
| C4—C5—C6—C1 | −0.4 (5) | C8—C7—N1—S1 | 110.1 (3) |
| C4—C5—C6—S1 | 178.5 (3) | C12—C7—N1—S1 | −70.0 (3) |
| C2—C1—C6—C5 | 1.8 (4) | C7—N1—S1—O1 | 176.0 (2) |
| C2—C1—C6—S1 | −177.1 (2) | C7—N1—S1—O2 | 46.3 (2) |
| C12—C7—C8—C9 | −0.1 (4) | C7—N1—S1—C6 | −69.0 (2) |
| N1—C7—C8—C9 | 179.7 (3) | C5—C6—S1—O1 | 3.3 (3) |
| C12—C7—C8—I1 | 179.6 (2) | C1—C6—S1—O1 | −177.9 (2) |
| N1—C7—C8—I1 | −0.6 (3) | C5—C6—S1—O2 | 134.5 (2) |
| C7—C8—C9—C10 | 0.8 (5) | C1—C6—S1—O2 | −46.6 (3) |
| I1—C8—C9—C10 | −178.9 (3) | C5—C6—S1—N1 | −110.4 (2) |
| C8—C9—C10—C11 | −0.5 (5) | C1—C6—S1—N1 | 68.4 (2) |
N-(2-Iodophenyl)benzenesulfonamide (I) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.86 | 2.37 | 3.144 (3) | 149 |
| C3—H3···O1ii | 0.93 | 2.57 | 3.352 (4) | 142 |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x−1, y, z.
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Crystal data
| C12H8F2INO2S | Z = 2 |
| Mr = 395.15 | F(000) = 380 |
| Triclinic, P1 | Dx = 1.957 Mg m−3 |
| a = 8.2688 (5) Å | Cu Kα radiation, λ = 1.54178 Å |
| b = 8.5178 (5) Å | Cell parameters from 14553 reflections |
| c = 10.4329 (7) Å | θ = 1.4–25.0° |
| α = 81.291 (2)° | µ = 20.44 mm−1 |
| β = 80.503 (2)° | T = 298 K |
| γ = 68.383 (2)° | Prism, colourless |
| V = 670.47 (7) Å3 | 0.22 × 0.10 × 0.05 mm |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Data collection
| Bruker D8 Venture Diffractometer | 2367 reflections with I > 2σ(I) |
| Radiation source: micro focus sealed tube | Rint = 0.062 |
| ω and φ scans | θmax = 69.0°, θmin = 4.3° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −9→10 |
| Tmin = 0.240, Tmax = 0.521 | k = −10→10 |
| 14553 measured reflections | l = −12→12 |
| 2476 independent reflections |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.072 | w = 1/[σ2(Fo2) + (0.1461P)2 + 0.5316P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.203 | (Δ/σ)max < 0.001 |
| S = 1.14 | Δρmax = 1.66 e Å−3 |
| 2476 reflections | Δρmin = −0.94 e Å−3 |
| 173 parameters | Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.017 (2) |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.6043 (11) | 0.6893 (10) | 0.0209 (8) | 0.0690 (17) | |
| H1 | 0.692052 | 0.606880 | −0.025462 | 0.083* | |
| C2 | 0.4337 (12) | 0.7289 (12) | 0.0029 (10) | 0.079 (2) | |
| H2 | 0.405262 | 0.675110 | −0.056593 | 0.095* | |
| C3 | 0.3033 (11) | 0.8488 (11) | 0.0732 (10) | 0.081 (2) | |
| H3 | 0.186655 | 0.875898 | 0.061633 | 0.097* | |
| C4 | 0.3467 (10) | 0.9284 (11) | 0.1607 (10) | 0.080 (2) | |
| H4 | 0.257809 | 1.008690 | 0.208075 | 0.096* | |
| C5 | 0.5138 (10) | 0.8932 (9) | 0.1794 (8) | 0.0674 (16) | |
| H5 | 0.540488 | 0.948502 | 0.238810 | 0.081* | |
| C6 | 0.6479 (9) | 0.7712 (8) | 0.1076 (6) | 0.0582 (14) | |
| C7 | 0.8376 (8) | 0.5366 (8) | 0.3596 (6) | 0.0571 (14) | |
| C8 | 0.7924 (10) | 0.3964 (9) | 0.4144 (7) | 0.0614 (15) | |
| C9 | 0.7196 (12) | 0.3840 (12) | 0.5445 (8) | 0.078 (2) | |
| H9 | 0.692000 | 0.289102 | 0.581056 | 0.093* | |
| C10 | 0.6899 (13) | 0.5163 (13) | 0.6173 (8) | 0.081 (2) | |
| C11 | 0.7353 (14) | 0.6529 (12) | 0.5661 (9) | 0.082 (2) | |
| C12 | 0.8116 (11) | 0.6642 (10) | 0.4384 (8) | 0.0700 (18) | |
| H12 | 0.845408 | 0.756575 | 0.405198 | 0.084* | |
| N1 | 0.9216 (7) | 0.5461 (7) | 0.2298 (6) | 0.0597 (12) | |
| H1A | 1.004065 | 0.457002 | 0.202938 | 0.072* | |
| O1 | 0.8802 (7) | 0.8532 (7) | 0.1911 (6) | 0.0691 (12) | |
| O2 | 0.9746 (7) | 0.6771 (7) | 0.0082 (5) | 0.0717 (13) | |
| S1 | 0.8673 (2) | 0.7215 (2) | 0.12842 (16) | 0.0582 (5) | |
| I1 | 0.83499 (6) | 0.19041 (6) | 0.30905 (4) | 0.0749 (4) | |
| F1 | 0.6177 (10) | 0.5090 (9) | 0.7433 (5) | 0.116 (2) | |
| F2 | 0.7077 (11) | 0.7780 (9) | 0.6410 (6) | 0.112 (2) |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.085 (5) | 0.061 (4) | 0.068 (4) | −0.032 (3) | −0.006 (3) | −0.014 (3) |
| C2 | 0.089 (5) | 0.080 (5) | 0.083 (5) | −0.043 (4) | −0.024 (4) | −0.005 (4) |
| C3 | 0.064 (4) | 0.076 (5) | 0.102 (6) | −0.028 (4) | −0.017 (4) | 0.007 (4) |
| C4 | 0.061 (4) | 0.074 (5) | 0.091 (6) | −0.016 (3) | 0.008 (4) | −0.010 (4) |
| C5 | 0.074 (4) | 0.057 (3) | 0.068 (4) | −0.020 (3) | 0.004 (3) | −0.014 (3) |
| C6 | 0.067 (3) | 0.054 (3) | 0.054 (3) | −0.023 (3) | −0.001 (3) | −0.007 (3) |
| C7 | 0.056 (3) | 0.059 (3) | 0.053 (3) | −0.012 (2) | −0.007 (2) | −0.015 (3) |
| C8 | 0.070 (4) | 0.061 (4) | 0.053 (3) | −0.022 (3) | −0.004 (3) | −0.010 (3) |
| C9 | 0.092 (5) | 0.084 (5) | 0.059 (4) | −0.038 (4) | 0.002 (4) | −0.006 (4) |
| C10 | 0.095 (5) | 0.092 (6) | 0.048 (4) | −0.026 (4) | 0.001 (3) | −0.014 (4) |
| C11 | 0.100 (6) | 0.078 (5) | 0.060 (4) | −0.015 (4) | −0.011 (4) | −0.023 (4) |
| C12 | 0.085 (5) | 0.062 (4) | 0.063 (4) | −0.024 (3) | −0.008 (3) | −0.014 (3) |
| N1 | 0.065 (3) | 0.056 (3) | 0.055 (3) | −0.018 (2) | 0.000 (2) | −0.014 (2) |
| O1 | 0.079 (3) | 0.064 (3) | 0.073 (3) | −0.033 (2) | −0.002 (2) | −0.020 (2) |
| O2 | 0.078 (3) | 0.076 (3) | 0.059 (3) | −0.030 (3) | 0.014 (2) | −0.018 (2) |
| S1 | 0.0632 (9) | 0.0577 (9) | 0.0560 (9) | −0.0254 (7) | 0.0028 (7) | −0.0127 (7) |
| I1 | 0.0903 (5) | 0.0698 (5) | 0.0695 (5) | −0.0344 (3) | 0.0010 (3) | −0.0166 (3) |
| F1 | 0.154 (6) | 0.122 (5) | 0.052 (3) | −0.036 (4) | 0.022 (3) | −0.018 (3) |
| F2 | 0.156 (6) | 0.104 (4) | 0.077 (3) | −0.038 (4) | −0.001 (3) | −0.045 (3) |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Geometric parameters (Å, º)
| C1—C2 | 1.363 (12) | C7—N1 | 1.422 (9) |
| C1—C6 | 1.386 (10) | C8—C9 | 1.396 (10) |
| C1—H1 | 0.9300 | C8—I1 | 2.100 (7) |
| C2—C3 | 1.377 (14) | C9—C10 | 1.378 (13) |
| C2—H2 | 0.9300 | C9—H9 | 0.9300 |
| C3—C4 | 1.376 (14) | C10—F1 | 1.353 (9) |
| C3—H3 | 0.9300 | C10—C11 | 1.360 (15) |
| C4—C5 | 1.343 (12) | C11—F2 | 1.346 (10) |
| C4—H4 | 0.9300 | C11—C12 | 1.382 (12) |
| C5—C6 | 1.408 (10) | C12—H12 | 0.9300 |
| C5—H5 | 0.9300 | N1—S1 | 1.655 (6) |
| C6—S1 | 1.748 (7) | N1—H1A | 0.8600 |
| C7—C12 | 1.394 (10) | O1—S1 | 1.425 (5) |
| C7—C8 | 1.394 (10) | O2—S1 | 1.425 (5) |
| C2—C1—C6 | 120.4 (8) | C9—C8—I1 | 116.3 (6) |
| C2—C1—H1 | 119.8 | C10—C9—C8 | 118.2 (8) |
| C6—C1—H1 | 119.8 | C10—C9—H9 | 120.9 |
| C1—C2—C3 | 119.9 (8) | C8—C9—H9 | 120.9 |
| C1—C2—H2 | 120.1 | F1—C10—C11 | 118.9 (9) |
| C3—C2—H2 | 120.1 | F1—C10—C9 | 119.6 (9) |
| C4—C3—C2 | 119.7 (7) | C11—C10—C9 | 121.4 (8) |
| C4—C3—H3 | 120.2 | F2—C11—C10 | 119.7 (8) |
| C2—C3—H3 | 120.2 | F2—C11—C12 | 119.5 (9) |
| C5—C4—C3 | 121.8 (8) | C10—C11—C12 | 120.8 (8) |
| C5—C4—H4 | 119.1 | C11—C12—C7 | 119.7 (8) |
| C3—C4—H4 | 119.1 | C11—C12—H12 | 120.1 |
| C4—C5—C6 | 118.9 (8) | C7—C12—H12 | 120.1 |
| C4—C5—H5 | 120.5 | C7—N1—S1 | 122.7 (4) |
| C6—C5—H5 | 120.5 | C7—N1—H1A | 118.7 |
| C1—C6—C5 | 119.3 (7) | S1—N1—H1A | 118.7 |
| C1—C6—S1 | 120.1 (6) | O1—S1—O2 | 118.7 (4) |
| C5—C6—S1 | 120.6 (5) | O1—S1—N1 | 107.5 (3) |
| C12—C7—C8 | 118.5 (7) | O2—S1—N1 | 105.5 (3) |
| C12—C7—N1 | 119.4 (7) | O1—S1—C6 | 108.4 (3) |
| C8—C7—N1 | 121.8 (6) | O2—S1—C6 | 109.5 (3) |
| C7—C8—C9 | 121.3 (7) | N1—S1—C6 | 106.5 (3) |
| C7—C8—I1 | 122.4 (5) | ||
| C6—C1—C2—C3 | −1.2 (12) | F1—C10—C11—C12 | 179.1 (9) |
| C1—C2—C3—C4 | 0.3 (13) | C9—C10—C11—C12 | 0.7 (15) |
| C2—C3—C4—C5 | 0.4 (14) | F2—C11—C12—C7 | −178.8 (8) |
| C3—C4—C5—C6 | −0.2 (13) | C10—C11—C12—C7 | 2.0 (13) |
| C2—C1—C6—C5 | 1.4 (11) | C8—C7—C12—C11 | −2.8 (11) |
| C2—C1—C6—S1 | −179.2 (6) | N1—C7—C12—C11 | −177.8 (7) |
| C4—C5—C6—C1 | −0.7 (11) | C12—C7—N1—S1 | −47.0 (8) |
| C4—C5—C6—S1 | 179.9 (6) | C8—C7—N1—S1 | 138.2 (6) |
| C12—C7—C8—C9 | 1.2 (11) | C7—N1—S1—O1 | 55.0 (6) |
| N1—C7—C8—C9 | 176.1 (7) | C7—N1—S1—O2 | −177.4 (5) |
| C12—C7—C8—I1 | −177.3 (5) | C7—N1—S1—C6 | −61.1 (6) |
| N1—C7—C8—I1 | −2.4 (9) | C1—C6—S1—O1 | 163.4 (6) |
| C7—C8—C9—C10 | 1.3 (13) | C5—C6—S1—O1 | −17.1 (7) |
| I1—C8—C9—C10 | 179.9 (7) | C1—C6—S1—O2 | 32.5 (7) |
| C8—C9—C10—F1 | 179.3 (8) | C5—C6—S1—O2 | −148.0 (6) |
| C8—C9—C10—C11 | −2.3 (14) | C1—C6—S1—N1 | −81.1 (6) |
| F1—C10—C11—F2 | −0.1 (15) | C5—C6—S1—N1 | 98.4 (6) |
| C9—C10—C11—F2 | −178.6 (9) |
N-(4,5-Difluoro-2-iodophenyl)benzenesulfonamide (II) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.86 | 2.58 | 3.169 (8) | 126 |
| C12—H12···O1 | 0.93 | 2.27 | 2.916 (11) | 126 |
Symmetry code: (i) −x+2, −y+1, −z.
Geometry of stacking interactions for I and II (Å, °).
| Compound | Group A | Group B | Shortest contacts | CgA···CgB | Plane···CgB | ipa | sa |
| I | (C7–C12) | (C7–C12)ii | 3.747 (2) | 3.747 (2) | 3.602 (2) | 0 | 16.0 (1) |
| II | (C1–C6) | (C1–C6)ˆiii | 3.225 (2) | 3.621 (2) | 3.480 (2) | 0 | 16.0 (2) |
| (C7–C12) | (C7–C12)iv | 3.499 (2) | 3.797 (2) | 3.436 (2) | 0 | 25.2 (2) |
a) Cg is a group centroid; Plane···CgB is the distance between mean plane of Group A and centroid of the interacting Group B; ipa is interplanar angle; sa is slippage angle, which is the angle of CgA···CgB axis to the Group A mean plane normal. [Symmetry codes for I: (ii) 2-X,-Y,-Z; for II: (iii) 1-X,2-Y,-Z; (iv) 2-X,1-Y,1-Z.]
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989025006656/wm5762sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025006656/wm5762Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989025006656/wm5762IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989025006656/wm5762Isup4.cml
Supporting information file. DOI: 10.1107/S2056989025006656/wm5762IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report