The crystal structures and Hirshfeld surface analysis of the 2-iodophenyl- and 4,5-difluoro-2-iodophenyl derivatives of benzenesulfonamide

Madhan, S.; NizamMohideen, M.H.; Pavunkumar, V.; MohanaKrishnan, A.K.

doi:10.1107/S2056989025006656

research communications

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ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 811-815

https://doi.org/10.1107/S2056989025006656

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The crystal structures and Hirshfeld surface analysis of the 2-iodophenyl- and 4,5-difluoro-2-iodophenyl derivatives of benzenesulfonamide

Sundarasamy Madhan,^a MohamedHanifa NizamMohideen,^a ^* Vinayagam Pavunkumar ^b and Arasambattu K. MohanaKrishnan ^b

^aDepartment of Physics, The New College, Chennai 600 014, University of Madras, Tamil Nadu, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-600 025, Tamilnadu, India
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 June 2025; accepted 24 July 2025; online 7 August 2025)

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.

Keywords: crystal structure; 2-iodophenyl; 4,5-difluoro; benzenesulfonamide; π–π interactions; hydrogen bonding; Hirshfeld surface analysis.

CCDC references: 2475707; 2475706

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).

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) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) .

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.

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 R₂²(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 d_norm use the normalized functions d_i and d_e (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. 6c), C⋯H/H⋯C (16.5%) for (I) and O⋯O (11%) for (II) (Fig. 6d). 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 d_norm.

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, ¹J_C–F = 249.4 Hz, ²J_C–F = 12.7 Hz), 147.8 (dd, ¹J_C–F = 252 Hz, ²J_C–F = 12.7 Hz), 138.4, 134.3 (dd, ¹J_C–F = 82 Hz, ²J_C–F = 3 Hz), 133.7, 129.3, 127.4, 126.8 (d, J_C–F = 19.5 Hz), 112.3 (d, J_C–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 U_iso(H) = 1.5U_eq(C) for methyl groups and 1.2U_eq(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 $[\overline{1}]$
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)
T_min, T_max	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
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.56	1.66, −0.95
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ), publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC references: 2475707; 2475706

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989025006656/wm5762sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025006656/wm5762Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989025006656/wm5762IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025006656/wm5762Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989025006656/wm5762IIsup5.cml

checkCIF report

Computing details top

N-(2-Iodophenyl)benzenesulfonamide (I) top

Crystal data top

C₁₂H₁₀INO₂S	F(000) = 696
M_r = 359.17	D_x = 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

Data collection top

Bruker D8 Venture Diffractometer	2386 reflections with I > 2σ(I)
Radiation source: micro focus sealed tube	R_int = 0.049
ω and φ scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.672, T_max = 0.971	k = −12→12
29284 measured reflections	l = −19→19
2591 independent reflections

Refinement top

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(F_o²) + (0.0319P)² + 1.2298P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.069	(Δ/σ)_max = 0.002
S = 1.09	Δρ_max = 0.54 e Å⁻³
2591 reflections	Δρ_min = −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)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) top

Crystal data top

C₁₂H₈F₂INO₂S	Z = 2
M_r = 395.15	F(000) = 380
Triclinic, P1	D_x = 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

Data collection top

Bruker D8 Venture Diffractometer	2367 reflections with I > 2σ(I)
Radiation source: micro focus sealed tube	R_int = 0.062
ω and φ scans	θ_max = 69.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→10
T_min = 0.240, T_max = 0.521	k = −10→10
14553 measured reflections	l = −12→12
2476 independent reflections

Refinement top

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(F_o²) + (0.1461P)² + 0.5316P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.203	(Δ/σ)_max < 0.001
S = 1.14	Δρ_max = 1.66 e Å⁻³
2476 reflections	Δρ_min = −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)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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, °). top

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.]

Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the data collection.

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 811-815

https://doi.org/10.1107/S2056989025006656

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

The crystal structures and Hirshfeld surface analysis of the 2-iodo­phenyl- and 4,5-di­fluoro-2-iodo­phenyl derivatives of benzenesulfonamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

The crystal structures and Hirshfeld surface analysis of the 2-iodophenyl- and 4,5-difluoro-2-iodophenyl derivatives of benzenesulfonamide

3. Supramolecular features