Different supra­molecular architectures mediated by different weak inter­actions in the crystals of three N-aryl-2,5-di­meth­oxy­benzene­sulfonamides

Shakuntala, K.; Naveen, S.; Lokanath, N.K.; Suchetan, P. A.; Abdoh, M.

doi:10.1107/S2053229617013195

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

K. Shakuntala, S. Naveen, N. K. Lokanath, P. A. Suchetan and M. Abdoh

The synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety have attracted interest as these compounds are important pharmacophores. The crystal structures of three closely related N-aryl-2,5-dimethoxybenzenesulfonamides, namely N-(2,3-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C₁₄H₁₃Cl₂NO₄S, (I), N-(2,4-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C₁₄H₁₃Cl₂NO₄S, (II), and N-(2,4-dimethylphenyl)-2,5-dimethoxybenzenesulfonamide, C₁₆H₁₉NO₄S, (III), are described. The asymmetric unit of (I) consists of two symmetry-independent molecules, while those of (II) and (III) contain one molecule each. The molecular conformations are stabilized by different intramolecular interactions, viz. C—H

O interactions in (I), N—H

Cl and C—H

O interactions in (II), and C—H

O interactions in (III). The crystals of the three compounds display different supramolecular architectures built by various weak intermolecular interactions of the types C—H

O, C—H

Cl, C—H

π(aryl), π(aryl)–π(aryl) and Cl

Cl. A detailed Hirshfeld surface analysis of these compounds has also been conducted in order to understand the relationship between the crystal structures. The d_norm and shape-index surfaces of (I)–(III) support the presence of various intermolecular interactions in the three structures. Analysis of the fingerprint plots reveals that the greatest contribution to the Hirshfeld surfaces is from H

H contacts, followed by H

O/O

H contacts. In addition, comparisons are made with the structures of some related compounds. Putative N—H

O hydrogen bonds are observed in 29 of the 30 reported structures, wherein the N—H

O hydrogen bonds form either C(4) chain motifs or R₂²(8) rings. Further comparison reveals that the characteristics of the N—H

O hydrogen-bond motifs, the presence of other interactions and the resultant supramolecular architecture is largely decided by the position of the substituents on the benzenesulfonyl ring, with the nature and position of the substituents on the aniline ring exerting little effect. On the other hand, the crystal structures of (I)–(III) display several weak interactions other than the common N—H

O hydrogen bonds, resulting in supramolecular architectures varying from one- to three-dimensional depending on the nature and position of the substituents on the aniline ring.

Keywords: benzenesulfonamides; crystal structure; N—H

O hydrogen bonds; weak interactions; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013195/yp3146sup1.cif Contains datablocks I, II, III, shelx
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013195/yp3146Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013195/yp3146IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013195/yp3146IIIsup4.hkl Contains datablock III

CCDC references: 1574729; 1574728; 1574727

Computing details top

Data collection: APEX2 (Bruker, 2009) for (I), (III); APEX2 (Bruker, 2009 for (II). For all structures, cell refinement: APEX2 and SAINT-Plus (Bruker, 2009). Data reduction: SAINT-Plus and XPREP (Bruker, 2009) for (I), (II); SAINTPlus and XPREP (Bruker, 2009) for (III). For all structures, program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

N-(2,3-Dichlorophenyl)-2,5-dimethoxybenzenesulfonamide (I) top

Crystal data top

C₁₄H₁₃Cl₂NO₄S	F(000) = 744
M_r = 362.21	Prism
Triclinic, P1	D_x = 1.575 Mg m⁻³
a = 9.7575 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.0792 (3) Å	Cell parameters from 143 reflections
c = 15.5286 (4) Å	θ = 5.1–64.6°
α = 88.733 (1)°	µ = 5.26 mm⁻¹
β = 83.753 (1)°	T = 296 K
γ = 66.337 (1)°	Prism, colourless
V = 1528.02 (7) Å³	0.28 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD area diffractometer	5044 independent reflections
Radiation source: fine-focus sealed tube	4940 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
phi and φ scans	θ_max = 64.6°, θ_min = 5.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.286, T_max = 0.314	k = −12→12
17943 measured reflections	l = −17→18

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0576P)² + 0.8603P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5044 reflections	Δρ_max = 0.35 e Å⁻³
409 parameters	Δρ_min = −0.47 e Å⁻³

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	0.79129 (18)	0.32961 (17)	0.49002 (11)	0.0140 (4)
C2	0.72234 (19)	0.27920 (17)	0.43435 (11)	0.0138 (3)
C3	0.61624 (19)	0.36781 (18)	0.38476 (11)	0.0166 (4)
H3	0.567070	0.337204	0.348241	0.020*
C4	0.5845 (2)	0.50066 (18)	0.38998 (11)	0.0177 (4)
H4	0.514885	0.558642	0.355994	0.021*
C5	0.6540 (2)	0.54947 (17)	0.44477 (12)	0.0167 (4)
C6	0.75744 (19)	0.46390 (17)	0.49623 (11)	0.0153 (4)
H6	0.803261	0.495784	0.534162	0.018*
C7	0.73623 (19)	0.18199 (17)	0.67699 (11)	0.0144 (3)
C8	0.6264 (2)	0.12930 (16)	0.68777 (11)	0.0149 (4)
C9	0.5165 (2)	0.16888 (18)	0.75880 (12)	0.0176 (4)
C10	0.5106 (2)	0.26307 (19)	0.81767 (12)	0.0209 (4)
H10	0.436471	0.289770	0.864609	0.025*
C11	0.6167 (2)	0.31698 (19)	0.80561 (12)	0.0214 (4)
H11	0.612130	0.381735	0.844297	0.026*
C12	0.7295 (2)	0.27653 (18)	0.73723 (12)	0.0179 (4)
H12	0.801249	0.312436	0.731295	0.022*
C13	0.6971 (2)	0.09176 (19)	0.37678 (13)	0.0215 (4)
H13A	0.590598	0.125342	0.393470	0.032*
H13B	0.739700	−0.002505	0.380757	0.032*
H13C	0.715742	0.115593	0.318213	0.032*
C14	0.6932 (2)	0.73400 (19)	0.49390 (13)	0.0251 (4)
H14A	0.673635	0.718712	0.554185	0.038*
H14B	0.660802	0.826975	0.485083	0.038*
H14C	0.799158	0.690523	0.476006	0.038*
C15	0.2516 (2)	0.42712 (17)	0.11786 (11)	0.0161 (4)
C16	0.1008 (2)	0.50730 (18)	0.14647 (12)	0.0183 (4)
C17	0.0218 (2)	0.60916 (19)	0.09407 (13)	0.0216 (4)
H17	−0.077853	0.663727	0.111956	0.026*
C18	0.0898 (2)	0.63065 (18)	0.01516 (12)	0.0200 (4)
H18	0.035428	0.699665	−0.018991	0.024*
C19	0.2383 (2)	0.54975 (18)	−0.01301 (12)	0.0177 (4)
C20	0.3196 (2)	0.44736 (18)	0.03926 (12)	0.0166 (4)
H20	0.419284	0.392966	0.021231	0.020*
C21	0.2352 (2)	0.13263 (17)	0.15186 (11)	0.0165 (4)
C22	0.12122 (19)	0.09010 (17)	0.18136 (11)	0.0163 (4)
C23	0.0896 (2)	0.00504 (18)	0.13021 (12)	0.0187 (4)
C24	0.1673 (2)	−0.0356 (2)	0.04850 (13)	0.0230 (4)
H24	0.146987	−0.093340	0.014623	0.028*
C25	0.2752 (2)	0.0110 (2)	0.01808 (12)	0.0234 (4)
H25	0.324888	−0.013438	−0.037411	0.028*
C26	0.3103 (2)	0.09332 (19)	0.06894 (12)	0.0203 (4)
H26	0.384279	0.122568	0.047788	0.024*
C27	−0.1029 (2)	0.5665 (2)	0.26000 (14)	0.0293 (5)
H27A	−0.103004	0.652492	0.266439	0.044*
H27B	−0.127512	0.536458	0.315659	0.044*
H27C	−0.176127	0.570648	0.222166	0.044*
C28	0.2364 (2)	0.6599 (2)	−0.14688 (13)	0.0258 (4)
H28A	0.147091	0.649240	−0.158210	0.039*
H28B	0.299367	0.651818	−0.200299	0.039*
H28C	0.209131	0.745364	−0.120892	0.039*
N1	0.85352 (17)	0.13286 (15)	0.60840 (9)	0.0141 (3)
N2	0.27083 (18)	0.20936 (16)	0.20939 (10)	0.0190 (3)
O1	1.04786 (13)	0.12823 (12)	0.49395 (8)	0.0179 (3)
O2	0.96577 (14)	0.29929 (12)	0.60929 (8)	0.0181 (3)
O3	0.76485 (14)	0.14672 (12)	0.43328 (8)	0.0179 (3)
O4	0.61333 (15)	0.68333 (12)	0.44419 (9)	0.0223 (3)
O5	0.36419 (16)	0.36091 (14)	0.26542 (9)	0.0268 (3)
O6	0.50078 (14)	0.22685 (13)	0.13344 (9)	0.0238 (3)
O7	0.04338 (15)	0.47663 (14)	0.22377 (9)	0.0250 (3)
O8	0.31633 (15)	0.56055 (13)	−0.08919 (9)	0.0248 (3)
S1	0.92927 (4)	0.22078 (4)	0.55147 (3)	0.01297 (12)
S2	0.36214 (5)	0.30307 (4)	0.18441 (3)	0.01833 (13)
CL1	0.62931 (5)	0.01467 (4)	0.61365 (3)	0.01777 (12)
CL2	0.38522 (5)	0.09954 (5)	0.77489 (3)	0.02456 (13)
CL3	0.02237 (5)	0.14335 (4)	0.28231 (3)	0.01903 (12)
CL4	−0.04782 (5)	−0.05037 (5)	0.16772 (3)	0.02518 (13)
H1	0.859 (3)	0.071 (2)	0.5807 (14)	0.021 (6)*
H2	0.210 (3)	0.238 (2)	0.2535 (15)	0.029 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0105 (8)	0.0169 (9)	0.0137 (8)	−0.0052 (7)	0.0008 (6)	0.0020 (7)
C2	0.0131 (8)	0.0151 (9)	0.0130 (8)	−0.0062 (7)	0.0020 (6)	−0.0001 (6)
C3	0.0139 (9)	0.0245 (10)	0.0127 (8)	−0.0093 (7)	−0.0010 (7)	0.0010 (7)
C4	0.0129 (9)	0.0214 (9)	0.0160 (9)	−0.0045 (7)	−0.0004 (7)	0.0058 (7)
C5	0.0141 (9)	0.0154 (9)	0.0180 (9)	−0.0048 (7)	0.0042 (7)	0.0028 (7)
C6	0.0142 (8)	0.0169 (9)	0.0148 (8)	−0.0071 (7)	0.0013 (7)	−0.0003 (7)
C7	0.0135 (8)	0.0141 (8)	0.0142 (8)	−0.0039 (7)	−0.0029 (7)	0.0044 (7)
C8	0.0159 (9)	0.0129 (8)	0.0146 (8)	−0.0037 (7)	−0.0043 (7)	0.0010 (7)
C9	0.0137 (9)	0.0188 (9)	0.0198 (9)	−0.0062 (7)	−0.0019 (7)	0.0030 (7)
C10	0.0201 (9)	0.0230 (10)	0.0174 (9)	−0.0071 (8)	0.0022 (7)	−0.0017 (7)
C11	0.0244 (10)	0.0228 (9)	0.0172 (9)	−0.0098 (8)	−0.0013 (7)	−0.0043 (7)
C12	0.0185 (9)	0.0218 (9)	0.0163 (9)	−0.0107 (7)	−0.0035 (7)	0.0014 (7)
C13	0.0223 (10)	0.0237 (10)	0.0235 (10)	−0.0139 (8)	−0.0041 (8)	−0.0038 (8)
C14	0.0268 (10)	0.0190 (9)	0.0299 (11)	−0.0106 (8)	0.0006 (8)	0.0004 (8)
C15	0.0171 (9)	0.0167 (9)	0.0171 (9)	−0.0092 (7)	−0.0037 (7)	0.0009 (7)
C16	0.0190 (9)	0.0209 (9)	0.0167 (9)	−0.0102 (8)	0.0011 (7)	−0.0024 (7)
C17	0.0162 (9)	0.0203 (9)	0.0247 (10)	−0.0038 (7)	−0.0005 (7)	−0.0025 (7)
C18	0.0200 (9)	0.0161 (9)	0.0222 (9)	−0.0048 (7)	−0.0055 (7)	0.0025 (7)
C19	0.0195 (9)	0.0188 (9)	0.0156 (9)	−0.0087 (7)	−0.0009 (7)	−0.0001 (7)
C20	0.0142 (9)	0.0168 (9)	0.0184 (9)	−0.0060 (7)	−0.0003 (7)	−0.0019 (7)
C21	0.0147 (9)	0.0173 (9)	0.0173 (9)	−0.0058 (7)	−0.0047 (7)	0.0062 (7)
C22	0.0136 (8)	0.0177 (9)	0.0141 (9)	−0.0030 (7)	−0.0012 (7)	0.0034 (7)
C23	0.0141 (9)	0.0200 (9)	0.0212 (9)	−0.0062 (7)	−0.0022 (7)	0.0034 (7)
C24	0.0188 (10)	0.0252 (10)	0.0237 (10)	−0.0072 (8)	−0.0029 (8)	−0.0038 (8)
C25	0.0189 (10)	0.0306 (11)	0.0166 (9)	−0.0066 (8)	0.0019 (7)	−0.0030 (8)
C26	0.0152 (9)	0.0259 (10)	0.0194 (9)	−0.0085 (8)	−0.0006 (7)	0.0036 (7)
C27	0.0203 (10)	0.0394 (12)	0.0240 (10)	−0.0096 (9)	0.0069 (8)	−0.0059 (9)
C28	0.0318 (11)	0.0274 (10)	0.0181 (9)	−0.0113 (9)	−0.0058 (8)	0.0071 (8)
N1	0.0178 (8)	0.0123 (7)	0.0131 (7)	−0.0073 (6)	−0.0009 (6)	−0.0002 (6)
N2	0.0209 (8)	0.0229 (8)	0.0159 (8)	−0.0120 (7)	−0.0008 (7)	0.0027 (6)
O1	0.0123 (6)	0.0178 (6)	0.0206 (6)	−0.0040 (5)	0.0020 (5)	−0.0006 (5)
O2	0.0184 (6)	0.0205 (6)	0.0183 (6)	−0.0102 (5)	−0.0045 (5)	0.0001 (5)
O3	0.0209 (7)	0.0158 (6)	0.0193 (6)	−0.0093 (5)	−0.0043 (5)	−0.0018 (5)
O4	0.0233 (7)	0.0130 (6)	0.0298 (7)	−0.0061 (5)	−0.0050 (6)	0.0048 (5)
O5	0.0321 (8)	0.0355 (8)	0.0219 (7)	−0.0210 (7)	−0.0118 (6)	0.0037 (6)
O6	0.0146 (6)	0.0244 (7)	0.0309 (7)	−0.0064 (5)	−0.0036 (5)	0.0070 (6)
O7	0.0213 (7)	0.0302 (7)	0.0194 (7)	−0.0081 (6)	0.0054 (5)	0.0013 (6)
O8	0.0244 (7)	0.0251 (7)	0.0184 (7)	−0.0046 (6)	0.0019 (5)	0.0066 (5)
S1	0.0106 (2)	0.0143 (2)	0.0140 (2)	−0.00506 (17)	−0.00134 (16)	0.00094 (16)
S2	0.0169 (2)	0.0220 (2)	0.0192 (2)	−0.01024 (19)	−0.00585 (17)	0.00503 (18)
CL1	0.0179 (2)	0.0176 (2)	0.0191 (2)	−0.00882 (17)	0.00016 (16)	−0.00352 (16)
CL2	0.0197 (2)	0.0278 (3)	0.0284 (3)	−0.01360 (19)	0.00535 (18)	−0.00312 (19)
CL3	0.0185 (2)	0.0241 (2)	0.0140 (2)	−0.00884 (18)	0.00097 (16)	0.00255 (16)
CL4	0.0229 (2)	0.0294 (3)	0.0289 (3)	−0.0167 (2)	−0.00114 (19)	0.00075 (19)

Geometric parameters (Å, º) top

C1—C6	1.392 (3)	C16—C17	1.388 (3)
C1—C2	1.400 (2)	C17—C18	1.391 (3)
C1—S1	1.7615 (17)	C17—H17	0.9300
C2—O3	1.356 (2)	C18—C19	1.390 (3)
C2—C3	1.397 (2)	C18—H18	0.9300
C3—C4	1.379 (3)	C19—O8	1.366 (2)
C3—H3	0.9300	C19—C20	1.397 (3)
C4—C5	1.385 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—C26	1.396 (3)
C5—O4	1.373 (2)	C21—C22	1.403 (3)
C5—C6	1.389 (3)	C21—N2	1.407 (2)
C6—H6	0.9300	C22—C23	1.391 (3)
C7—C12	1.397 (3)	C22—CL3	1.7294 (18)
C7—C8	1.406 (3)	C23—C24	1.389 (3)
C7—N1	1.414 (2)	C23—CL4	1.7287 (18)
C8—C9	1.395 (3)	C24—C25	1.384 (3)
C8—CL1	1.7225 (17)	C24—H24	0.9300
C9—C10	1.382 (3)	C25—C26	1.384 (3)
C9—CL2	1.7335 (18)	C25—H25	0.9300
C10—C11	1.384 (3)	C26—H26	0.9300
C10—H10	0.9300	C27—O7	1.433 (2)
C11—C12	1.382 (3)	C27—H27A	0.9600
C11—H11	0.9300	C27—H27B	0.9600
C12—H12	0.9300	C27—H27C	0.9600
C13—O3	1.432 (2)	C28—O8	1.429 (2)
C13—H13A	0.9600	C28—H28A	0.9600
C13—H13B	0.9600	C28—H28B	0.9600
C13—H13C	0.9600	C28—H28C	0.9600
C14—O4	1.421 (2)	N1—S1	1.6354 (15)
C14—H14A	0.9600	N1—H1	0.79 (2)
C14—H14B	0.9600	N2—S2	1.6346 (16)
C14—H14C	0.9600	N2—H2	0.83 (2)
C15—C20	1.383 (3)	O1—S1	1.4323 (13)
C15—C16	1.406 (3)	O2—S1	1.4290 (13)
C15—S2	1.7637 (18)	O5—S2	1.4299 (15)
C16—O7	1.363 (2)	O6—S2	1.4315 (14)

C6—C1—C2	121.75 (16)	C17—C18—H18	119.8
C6—C1—S1	118.61 (13)	O8—C19—C18	125.77 (17)
C2—C1—S1	119.61 (13)	O8—C19—C20	114.88 (16)
O3—C2—C3	125.21 (16)	C18—C19—C20	119.35 (17)
O3—C2—C1	116.56 (15)	C15—C20—C19	119.82 (17)
C3—C2—C1	118.22 (16)	C15—C20—H20	120.1
C4—C3—C2	119.98 (17)	C19—C20—H20	120.1
C4—C3—H3	120.0	C26—C21—C22	118.78 (17)
C2—C3—H3	120.0	C26—C21—N2	123.58 (16)
C3—C4—C5	121.36 (16)	C22—C21—N2	117.60 (16)
C3—C4—H4	119.3	C23—C22—C21	120.22 (16)
C5—C4—H4	119.3	C23—C22—CL3	120.58 (14)
O4—C5—C4	116.00 (16)	C21—C22—CL3	119.20 (14)
O4—C5—C6	124.16 (17)	C24—C23—C22	120.42 (17)
C4—C5—C6	119.84 (17)	C24—C23—CL4	119.42 (15)
C5—C6—C1	118.82 (16)	C22—C23—CL4	120.16 (14)
C5—C6—H6	120.6	C25—C24—C23	119.22 (18)
C1—C6—H6	120.6	C25—C24—H24	120.4
C12—C7—C8	118.53 (16)	C23—C24—H24	120.4
C12—C7—N1	122.38 (16)	C24—C25—C26	121.03 (18)
C8—C7—N1	119.01 (16)	C24—C25—H25	119.5
C9—C8—C7	119.98 (16)	C26—C25—H25	119.5
C9—C8—CL1	120.23 (14)	C25—C26—C21	120.24 (17)
C7—C8—CL1	119.79 (14)	C25—C26—H26	119.9
C10—C9—C8	120.87 (17)	C21—C26—H26	119.9
C10—C9—CL2	118.87 (14)	O7—C27—H27A	109.5
C8—C9—CL2	120.26 (14)	O7—C27—H27B	109.5
C9—C10—C11	118.90 (17)	H27A—C27—H27B	109.5
C9—C10—H10	120.5	O7—C27—H27C	109.5
C11—C10—H10	120.5	H27A—C27—H27C	109.5
C12—C11—C10	121.32 (17)	H27B—C27—H27C	109.5
C12—C11—H11	119.3	O8—C28—H28A	109.5
C10—C11—H11	119.3	O8—C28—H28B	109.5
C11—C12—C7	120.34 (17)	H28A—C28—H28B	109.5
C11—C12—H12	119.8	O8—C28—H28C	109.5
C7—C12—H12	119.8	H28A—C28—H28C	109.5
O3—C13—H13A	109.5	H28B—C28—H28C	109.5
O3—C13—H13B	109.5	C7—N1—S1	125.25 (13)
H13A—C13—H13B	109.5	C7—N1—H1	118.2 (17)
O3—C13—H13C	109.5	S1—N1—H1	110.6 (16)
H13A—C13—H13C	109.5	C21—N2—S2	126.87 (13)
H13B—C13—H13C	109.5	C21—N2—H2	115.7 (17)
O4—C14—H14A	109.5	S2—N2—H2	111.1 (17)
O4—C14—H14B	109.5	C2—O3—C13	118.04 (14)
H14A—C14—H14B	109.5	C5—O4—C14	116.87 (14)
O4—C14—H14C	109.5	C16—O7—C27	117.73 (15)
H14A—C14—H14C	109.5	C19—O8—C28	117.19 (15)
H14B—C14—H14C	109.5	O2—S1—O1	118.72 (7)
C20—C15—C16	121.30 (16)	O2—S1—N1	108.83 (8)
C20—C15—S2	118.10 (14)	O1—S1—N1	105.14 (8)
C16—C15—S2	120.52 (14)	O2—S1—C1	107.29 (8)
O7—C16—C17	125.23 (17)	O1—S1—C1	108.95 (8)
O7—C16—C15	116.58 (16)	N1—S1—C1	107.44 (8)
C17—C16—C15	118.19 (17)	O5—S2—O6	119.88 (8)
C16—C17—C18	120.85 (17)	O5—S2—N2	104.30 (8)
C16—C17—H17	119.6	O6—S2—N2	108.76 (8)
C18—C17—H17	119.6	O5—S2—C15	109.31 (8)
C19—C18—C17	120.49 (17)	O6—S2—C15	107.38 (8)
C19—C18—H18	119.8	N2—S2—C15	106.49 (8)

C6—C1—C2—O3	179.57 (15)	C26—C21—C22—CL3	−177.51 (13)
S1—C1—C2—O3	1.7 (2)	N2—C21—C22—CL3	4.7 (2)
C6—C1—C2—C3	−0.5 (2)	C21—C22—C23—C24	−1.9 (3)
S1—C1—C2—C3	−178.32 (12)	CL3—C22—C23—C24	178.79 (14)
O3—C2—C3—C4	−178.60 (16)	C21—C22—C23—CL4	178.47 (13)
C1—C2—C3—C4	1.5 (2)	CL3—C22—C23—CL4	−0.8 (2)
C2—C3—C4—C5	−1.1 (3)	C22—C23—C24—C25	−0.8 (3)
C3—C4—C5—O4	179.90 (16)	CL4—C23—C24—C25	178.80 (15)
C3—C4—C5—C6	−0.4 (3)	C23—C24—C25—C26	2.3 (3)
O4—C5—C6—C1	−178.96 (15)	C24—C25—C26—C21	−1.0 (3)
C4—C5—C6—C1	1.4 (2)	C22—C21—C26—C25	−1.7 (3)
C2—C1—C6—C5	−0.9 (2)	N2—C21—C26—C25	175.94 (17)
S1—C1—C6—C5	176.94 (13)	C12—C7—N1—S1	−39.4 (2)
C12—C7—C8—C9	−1.8 (2)	C8—C7—N1—S1	143.86 (14)
N1—C7—C8—C9	175.04 (15)	C26—C21—N2—S2	20.3 (3)
C12—C7—C8—CL1	178.86 (13)	C22—C21—N2—S2	−161.97 (14)
N1—C7—C8—CL1	−4.3 (2)	C3—C2—O3—C13	0.4 (2)
C7—C8—C9—C10	2.2 (3)	C1—C2—O3—C13	−179.69 (15)
CL1—C8—C9—C10	−178.45 (14)	C4—C5—O4—C14	−174.43 (16)
C7—C8—C9—CL2	−177.43 (13)	C6—C5—O4—C14	5.9 (2)
CL1—C8—C9—CL2	1.9 (2)	C17—C16—O7—C27	−9.1 (3)
C8—C9—C10—C11	−0.6 (3)	C15—C16—O7—C27	171.97 (17)
CL2—C9—C10—C11	179.01 (14)	C18—C19—O8—C28	−3.1 (3)
C9—C10—C11—C12	−1.3 (3)	C20—C19—O8—C28	177.26 (16)
C10—C11—C12—C7	1.7 (3)	C7—N1—S1—O2	48.38 (16)
C8—C7—C12—C11	−0.1 (3)	C7—N1—S1—O1	176.57 (14)
N1—C7—C12—C11	−176.87 (16)	C7—N1—S1—C1	−67.49 (16)
C20—C15—C16—O7	178.22 (16)	C6—C1—S1—O2	9.03 (15)
S2—C15—C16—O7	−5.2 (2)	C2—C1—S1—O2	−173.06 (13)
C20—C15—C16—C17	−0.8 (3)	C6—C1—S1—O1	−120.68 (13)
S2—C15—C16—C17	175.75 (14)	C2—C1—S1—O1	57.23 (15)
O7—C16—C17—C18	−178.53 (18)	C6—C1—S1—N1	125.91 (14)
C15—C16—C17—C18	0.4 (3)	C2—C1—S1—N1	−56.18 (15)
C16—C17—C18—C19	0.4 (3)	C21—N2—S2—O5	178.51 (15)
C17—C18—C19—O8	179.51 (18)	C21—N2—S2—O6	−52.47 (17)
C17—C18—C19—C20	−0.8 (3)	C21—N2—S2—C15	62.96 (17)
C16—C15—C20—C19	0.4 (3)	C20—C15—S2—O5	119.90 (15)
S2—C15—C20—C19	−176.25 (13)	C16—C15—S2—O5	−56.78 (17)
O8—C19—C20—C15	−179.87 (16)	C20—C15—S2—O6	−11.61 (17)
C18—C19—C20—C15	0.4 (3)	C16—C15—S2—O6	171.71 (14)
C26—C21—C22—C23	3.2 (3)	C20—C15—S2—N2	−127.97 (15)
N2—C21—C22—C23	−174.65 (15)	C16—C15—S2—N2	55.35 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2	0.93	2.31	2.9620	126
C26—H26···O6	0.93	2.42	3.0533	125
N1—H1···O1ⁱ	0.79	2.31	3.0750	163
C3—H3···O5	0.93	2.40	3.2616	154
C14—H14B···Cl1ⁱⁱ	0.96	2.82	3.459 (2)	125
C14—H14C···O2ⁱⁱⁱ	0.96	2.56	3.414 (3)	148
C4—H4···Cg^iv	0.93	2.82	3.7011	159

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y+1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1.

N-(2,4-Dichlorophenyl)-2,5-dimethoxybenzenesulfonamide (II) top

Crystal data top

C₁₄H₁₃Cl₂NO₄S	F(000) = 372
M_r = 362.21	Prism
Triclinic, P1	D_x = 1.604 Mg m⁻³
a = 7.4855 (5) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.1175 (6) Å	Cell parameters from 133 reflections
c = 13.9643 (10) Å	θ = 7.5–64.5°
α = 98.151 (2)°	µ = 5.36 mm⁻¹
β = 95.566 (2)°	T = 296 K
γ = 114.952 (2)°	Prism, colourless
V = 749.84 (9) Å³	0.27 × 0.24 × 0.19 mm
Z = 2

Data collection top

Bruker APEXII CCD area detector diffractometer	2452 independent reflections
Radiation source: fine-focus sealed tube	2393 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and φ scans	θ_max = 64.5°, θ_min = 7.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.294, T_max = 0.361	k = −9→9
9208 measured reflections	l = −16→16

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0635P)² + 0.7485P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
2452 reflections	Δρ_max = 0.31 e Å⁻³
205 parameters	Δρ_min = −0.39 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.6325 (3)	0.7183 (3)	0.64637 (15)	0.0139 (4)
C2	0.7057 (3)	0.5880 (3)	0.62229 (16)	0.0163 (4)
C3	0.7846 (3)	0.5856 (3)	0.53654 (16)	0.0186 (5)
H3	0.835731	0.501147	0.519660	0.022*
C4	0.7883 (3)	0.7081 (3)	0.47535 (16)	0.0183 (5)
H4	0.841093	0.704355	0.417915	0.022*
C5	0.7135 (3)	0.8358 (3)	0.49982 (15)	0.0159 (4)
C6	0.6362 (3)	0.8412 (3)	0.58618 (15)	0.0155 (4)
H6	0.587035	0.927038	0.603518	0.019*
C7	0.8945 (3)	0.8829 (3)	0.86429 (14)	0.0146 (4)
C8	1.0494 (3)	0.8367 (3)	0.89214 (14)	0.0148 (4)
C9	1.2472 (3)	0.9667 (3)	0.91241 (15)	0.0161 (4)
H9	1.347917	0.933638	0.931681	0.019*
C10	1.2931 (3)	1.1472 (3)	0.90359 (15)	0.0174 (5)
C11	1.1447 (3)	1.1994 (3)	0.87695 (16)	0.0183 (5)
H11	1.177565	1.321279	0.871557	0.022*
C12	0.9459 (3)	1.0674 (3)	0.85837 (15)	0.0169 (5)
H12	0.845496	1.102357	0.841716	0.020*
C13	0.7778 (4)	0.3454 (3)	0.66569 (18)	0.0258 (5)
H13A	0.722237	0.271548	0.600547	0.039*
H13B	0.750793	0.265805	0.712533	0.039*
H13C	0.919816	0.415643	0.671122	0.039*
C14	0.7720 (4)	0.9450 (4)	0.35043 (17)	0.0243 (5)
H14A	0.910104	0.968704	0.360573	0.036*
H14B	0.756342	1.033933	0.316222	0.036*
H14C	0.691959	0.822195	0.312121	0.036*
N1	0.6935 (3)	0.7456 (3)	0.84630 (13)	0.0158 (4)
O1	0.3573 (2)	0.5553 (2)	0.75085 (11)	0.0208 (4)
O2	0.5055 (2)	0.8960 (2)	0.76766 (11)	0.0202 (4)
O3	0.6894 (2)	0.4692 (2)	0.68484 (11)	0.0200 (3)
O4	0.7085 (2)	0.9602 (2)	0.44395 (11)	0.0219 (4)
S1	0.52743 (7)	0.72789 (7)	0.75407 (3)	0.01471 (17)
CL1	1.54329 (8)	1.30818 (7)	0.92628 (4)	0.02443 (18)
CL2	0.99583 (7)	0.61177 (7)	0.90466 (4)	0.02040 (18)
H1	0.684 (4)	0.643 (4)	0.854 (2)	0.023 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0113 (9)	0.0165 (10)	0.0120 (10)	0.0051 (8)	0.0017 (8)	0.0005 (8)
C2	0.0132 (10)	0.0156 (11)	0.0198 (11)	0.0062 (8)	0.0004 (8)	0.0044 (9)
C3	0.0162 (10)	0.0199 (11)	0.0219 (11)	0.0111 (9)	0.0027 (9)	0.0016 (9)
C4	0.0170 (11)	0.0217 (12)	0.0155 (10)	0.0083 (9)	0.0045 (8)	0.0012 (9)
C5	0.0141 (10)	0.0185 (11)	0.0150 (10)	0.0070 (9)	0.0004 (8)	0.0051 (9)
C6	0.0138 (10)	0.0151 (11)	0.0171 (10)	0.0068 (9)	0.0010 (8)	0.0016 (8)
C7	0.0147 (10)	0.0182 (11)	0.0104 (9)	0.0061 (9)	0.0044 (8)	0.0038 (8)
C8	0.0187 (11)	0.0157 (11)	0.0116 (10)	0.0082 (9)	0.0044 (8)	0.0045 (8)
C9	0.0162 (10)	0.0194 (11)	0.0145 (10)	0.0090 (9)	0.0043 (8)	0.0044 (9)
C10	0.0167 (11)	0.0179 (11)	0.0150 (10)	0.0043 (9)	0.0058 (8)	0.0041 (9)
C11	0.0233 (11)	0.0146 (11)	0.0181 (11)	0.0081 (9)	0.0070 (9)	0.0053 (9)
C12	0.0190 (11)	0.0189 (11)	0.0164 (10)	0.0105 (9)	0.0044 (8)	0.0066 (9)
C13	0.0349 (13)	0.0222 (12)	0.0295 (13)	0.0214 (11)	0.0042 (10)	0.0054 (10)
C14	0.0233 (12)	0.0364 (14)	0.0176 (11)	0.0143 (11)	0.0077 (9)	0.0126 (10)
N1	0.0160 (9)	0.0161 (10)	0.0167 (9)	0.0069 (8)	0.0034 (7)	0.0077 (7)
O1	0.0125 (7)	0.0259 (9)	0.0206 (8)	0.0046 (7)	0.0042 (6)	0.0059 (7)
O2	0.0235 (8)	0.0260 (9)	0.0191 (8)	0.0178 (7)	0.0062 (6)	0.0048 (6)
O3	0.0257 (8)	0.0199 (8)	0.0215 (8)	0.0150 (7)	0.0065 (6)	0.0081 (6)
O4	0.0263 (8)	0.0276 (9)	0.0196 (8)	0.0158 (7)	0.0094 (7)	0.0129 (7)
S1	0.0127 (3)	0.0189 (3)	0.0142 (3)	0.0080 (2)	0.0038 (2)	0.0040 (2)
CL1	0.0163 (3)	0.0199 (3)	0.0323 (3)	0.0026 (2)	0.0048 (2)	0.0074 (2)
CL2	0.0183 (3)	0.0155 (3)	0.0278 (3)	0.0072 (2)	0.0019 (2)	0.0082 (2)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C9—H9	0.9300
C1—C2	1.398 (3)	C10—C11	1.383 (3)
C1—S1	1.771 (2)	C10—CL1	1.737 (2)
C2—O3	1.367 (3)	C11—C12	1.389 (3)
C2—C3	1.387 (3)	C11—H11	0.9300
C3—C4	1.393 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—O3	1.428 (3)
C4—C5	1.390 (3)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—O4	1.371 (3)	C13—H13C	0.9600
C5—C6	1.390 (3)	C14—O4	1.439 (3)
C6—H6	0.9300	C14—H14A	0.9600
C7—C12	1.398 (3)	C14—H14B	0.9600
C7—C8	1.399 (3)	C14—H14C	0.9600
C7—N1	1.415 (3)	N1—S1	1.6464 (18)
C8—C9	1.379 (3)	N1—H1	0.83 (3)
C8—CL2	1.735 (2)	O1—S1	1.4325 (16)
C9—C10	1.383 (3)	O2—S1	1.4310 (16)

C6—C1—C2	121.35 (19)	C10—C11—C12	119.2 (2)
C6—C1—S1	117.92 (16)	C10—C11—H11	120.4
C2—C1—S1	120.71 (16)	C12—C11—H11	120.4
O3—C2—C3	124.94 (19)	C11—C12—C7	121.1 (2)
O3—C2—C1	116.80 (19)	C11—C12—H12	119.5
C3—C2—C1	118.24 (19)	C7—C12—H12	119.5
C2—C3—C4	120.9 (2)	O3—C13—H13A	109.5
C2—C3—H3	119.6	O3—C13—H13B	109.5
C4—C3—H3	119.6	H13A—C13—H13B	109.5
C5—C4—C3	120.3 (2)	O3—C13—H13C	109.5
C5—C4—H4	119.9	H13A—C13—H13C	109.5
C3—C4—H4	119.9	H13B—C13—H13C	109.5
O4—C5—C6	115.97 (19)	O4—C14—H14A	109.5
O4—C5—C4	124.56 (19)	O4—C14—H14B	109.5
C6—C5—C4	119.5 (2)	H14A—C14—H14B	109.5
C1—C6—C5	119.81 (19)	O4—C14—H14C	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
C5—C6—H6	120.1	H14B—C14—H14C	109.5
C12—C7—C8	117.8 (2)	C7—N1—S1	122.50 (14)
C12—C7—N1	122.36 (19)	C7—N1—H1	112 (2)
C8—C7—N1	119.83 (19)	S1—N1—H1	112 (2)
C9—C8—C7	121.8 (2)	C2—O3—C13	117.48 (17)
C9—C8—CL2	117.90 (16)	C5—O4—C14	116.37 (18)
C7—C8—CL2	120.23 (17)	O2—S1—O1	119.39 (10)
C8—C9—C10	118.8 (2)	O2—S1—N1	107.92 (9)
C8—C9—H9	120.6	O1—S1—N1	104.97 (9)
C10—C9—H9	120.6	O2—S1—C1	106.61 (10)
C9—C10—C11	121.3 (2)	O1—S1—C1	110.39 (10)
C9—C10—CL1	118.36 (17)	N1—S1—C1	106.94 (9)
C11—C10—CL1	120.37 (17)

C6—C1—C2—O3	−177.93 (18)	C9—C10—C11—C12	−0.3 (3)
S1—C1—C2—O3	0.8 (3)	CL1—C10—C11—C12	179.42 (16)
C6—C1—C2—C3	0.6 (3)	C10—C11—C12—C7	−1.3 (3)
S1—C1—C2—C3	179.37 (16)	C8—C7—C12—C11	1.7 (3)
O3—C2—C3—C4	177.6 (2)	N1—C7—C12—C11	179.65 (18)
C1—C2—C3—C4	−0.9 (3)	C12—C7—N1—S1	43.3 (3)
C2—C3—C4—C5	0.3 (3)	C8—C7—N1—S1	−138.80 (17)
C3—C4—C5—O4	−179.2 (2)	C3—C2—O3—C13	6.5 (3)
C3—C4—C5—C6	0.4 (3)	C1—C2—O3—C13	−175.07 (19)
C2—C1—C6—C5	0.1 (3)	C6—C5—O4—C14	−174.79 (19)
S1—C1—C6—C5	−178.64 (16)	C4—C5—O4—C14	4.9 (3)
O4—C5—C6—C1	179.03 (19)	C7—N1—S1—O2	−61.92 (19)
C4—C5—C6—C1	−0.7 (3)	C7—N1—S1—O1	169.74 (16)
C12—C7—C8—C9	−0.6 (3)	C7—N1—S1—C1	52.45 (19)
N1—C7—C8—C9	−178.62 (18)	C6—C1—S1—O2	−12.68 (19)
C12—C7—C8—CL2	178.02 (15)	C2—C1—S1—O2	168.52 (17)
N1—C7—C8—CL2	0.0 (3)	C6—C1—S1—O1	118.41 (17)
C7—C8—C9—C10	−0.9 (3)	C2—C1—S1—O1	−60.38 (19)
CL2—C8—C9—C10	−179.54 (15)	C6—C1—S1—N1	−127.93 (17)
C8—C9—C10—C11	1.3 (3)	C2—C1—S1—N1	53.3 (2)
C8—C9—C10—CL1	−178.37 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.83 (3)	2.50 (3)	2.989 (2)	119 (3)
C12—H12···O2	0.93	2.40	3.038 (3)	126
C14—H14B···O2ⁱ	0.96	2.49	3.302 (3)	142
C14—H14A···Cgⁱⁱ	0.96	2.89	3.645 (3)	136

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y, −z+1.

N-(2,4-Dimethylphenyl)-2,5-dimethoxybenzenesulfonamide (III) top

Crystal data top

C₁₆H₁₉NO₄S	F(000) = 340
M_r = 321.38	Prism
Triclinic, P1	D_x = 1.314 Mg m⁻³
a = 8.2859 (14) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.7197 (15) Å	Cell parameters from 136 reflections
c = 12.232 (2) Å	θ = 3.9–64.5°
α = 70.522 (5)°	µ = 1.92 mm⁻¹
β = 80.171 (5)°	T = 296 K
γ = 78.856 (5)°	Prism, colourless
V = 812.1 (2) Å³	0.25 × 0.22 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD area diffractometer	2648 independent reflections
Radiation source: fine-focus sealed tube	2563 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
phi and φ scans	θ_max = 64.5°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.649, T_max = 0.681	k = −10→10
7355 measured reflections	l = −13→14

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.108P)² + 0.118P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
2648 reflections	Δρ_max = 0.19 e Å⁻³
207 parameters	Δρ_min = −0.39 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.34336 (5)	0.38129 (4)	0.18309 (3)	0.0470 (2)
O1	0.44860 (18)	0.32376 (16)	0.09529 (11)	0.0618 (4)
O2	0.19850 (16)	0.30652 (16)	0.23631 (12)	0.0610 (4)
O3	0.64057 (17)	0.5301 (2)	0.16088 (12)	0.0698 (4)
O4	0.4391 (2)	0.1532 (2)	0.60613 (12)	0.0763 (5)
N1	0.28789 (19)	0.57568 (18)	0.12078 (13)	0.0497 (4)
C6	0.4092 (2)	0.2693 (2)	0.40838 (15)	0.0489 (4)
H6	0.314832	0.219438	0.422857	0.059*
C1	0.45925 (19)	0.36296 (19)	0.29687 (14)	0.0445 (4)
C7	0.19017 (19)	0.6872 (2)	0.17771 (15)	0.0485 (4)
C12	0.1028 (2)	0.6344 (2)	0.28766 (18)	0.0577 (5)
H12	0.107873	0.522377	0.327115	0.069*
C2	0.6007 (2)	0.4398 (2)	0.27360 (15)	0.0507 (4)
C11	0.0082 (2)	0.7466 (3)	0.3391 (2)	0.0685 (6)
H11	−0.050415	0.708576	0.412385	0.082*
C5	0.4996 (2)	0.2490 (2)	0.49952 (16)	0.0538 (4)
C4	0.6377 (2)	0.3252 (2)	0.47736 (17)	0.0581 (5)
H4	0.697965	0.312755	0.538097	0.070*
C3	0.6877 (2)	0.4200 (2)	0.36550 (18)	0.0595 (5)
H3	0.781062	0.471196	0.351890	0.071*
C10	−0.0009 (3)	0.9127 (3)	0.2844 (3)	0.0783 (7)
C8	0.1819 (3)	0.8543 (3)	0.1200 (2)	0.0697 (6)
C13	0.7981 (3)	0.5837 (3)	0.1296 (2)	0.0859 (7)
H13A	0.803816	0.659799	0.169734	0.129*
H13B	0.814002	0.636831	0.046849	0.129*
H13C	0.882941	0.490675	0.150991	0.129*
C9	0.0867 (3)	0.9620 (3)	0.1756 (3)	0.0878 (8)
H9	0.081935	1.074193	0.137132	0.105*
C14	0.5346 (4)	0.1151 (3)	0.69984 (19)	0.0855 (7)
H14A	0.644407	0.065513	0.678983	0.128*
H14B	0.483997	0.039851	0.767840	0.128*
H14C	0.540275	0.214074	0.716238	0.128*
C15	0.2757 (4)	0.9172 (3)	0.0005 (3)	0.1157 (13)
H15A	0.245755	1.034249	−0.029753	0.174*
H15B	0.248374	0.866065	−0.050942	0.174*
H15C	0.392517	0.891332	0.006391	0.174*
C16	−0.1017 (4)	1.0371 (4)	0.3400 (4)	0.1162 (13)
H16A	−0.040391	1.125790	0.326571	0.174*
H16B	−0.124654	0.985212	0.422422	0.174*
H16C	−0.203964	1.079319	0.306240	0.174*
H1	0.359 (3)	0.617 (3)	0.068 (2)	0.073 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0493 (3)	0.0462 (3)	0.0487 (3)	−0.01127 (19)	−0.00489 (19)	−0.0169 (2)
O1	0.0766 (9)	0.0560 (7)	0.0551 (7)	−0.0082 (6)	0.0005 (6)	−0.0250 (6)
O2	0.0596 (8)	0.0612 (8)	0.0671 (8)	−0.0266 (6)	−0.0089 (6)	−0.0156 (6)
O3	0.0569 (8)	0.0875 (10)	0.0565 (8)	−0.0334 (7)	−0.0084 (6)	0.0026 (7)
O4	0.0836 (10)	0.0914 (11)	0.0479 (7)	−0.0308 (8)	−0.0070 (7)	−0.0040 (7)
N1	0.0487 (8)	0.0497 (8)	0.0484 (8)	−0.0082 (6)	−0.0039 (6)	−0.0126 (6)
C6	0.0474 (9)	0.0471 (9)	0.0517 (9)	−0.0108 (7)	−0.0015 (7)	−0.0147 (7)
C1	0.0417 (8)	0.0427 (8)	0.0495 (9)	−0.0055 (6)	−0.0037 (7)	−0.0157 (7)
C7	0.0367 (8)	0.0530 (9)	0.0585 (10)	−0.0072 (7)	−0.0082 (7)	−0.0191 (8)
C12	0.0484 (9)	0.0602 (11)	0.0655 (11)	−0.0090 (8)	−0.0024 (8)	−0.0220 (9)
C2	0.0459 (9)	0.0504 (9)	0.0523 (10)	−0.0109 (7)	−0.0040 (7)	−0.0102 (7)
C11	0.0495 (10)	0.0844 (14)	0.0796 (14)	−0.0177 (9)	0.0084 (9)	−0.0394 (12)
C5	0.0586 (10)	0.0522 (9)	0.0468 (9)	−0.0065 (8)	−0.0039 (8)	−0.0125 (7)
C4	0.0580 (10)	0.0624 (11)	0.0564 (10)	−0.0082 (8)	−0.0159 (8)	−0.0175 (8)
C3	0.0498 (10)	0.0639 (11)	0.0647 (11)	−0.0170 (8)	−0.0115 (8)	−0.0127 (9)
C10	0.0485 (11)	0.0750 (14)	0.122 (2)	−0.0167 (9)	0.0137 (12)	−0.0524 (14)
C8	0.0572 (11)	0.0544 (11)	0.0865 (14)	−0.0058 (8)	0.0075 (10)	−0.0164 (10)
C13	0.0685 (13)	0.1039 (18)	0.0752 (14)	−0.0457 (13)	−0.0026 (11)	0.0012 (13)
C9	0.0700 (14)	0.0550 (12)	0.128 (2)	−0.0105 (10)	0.0196 (14)	−0.0296 (13)
C14	0.1138 (19)	0.0856 (15)	0.0505 (11)	−0.0181 (14)	−0.0197 (12)	−0.0054 (11)
C15	0.120 (2)	0.0573 (13)	0.117 (2)	0.0038 (14)	0.0445 (19)	0.0044 (14)
C16	0.0821 (17)	0.099 (2)	0.188 (4)	−0.0286 (15)	0.042 (2)	−0.092 (2)

Geometric parameters (Å, º) top

S1—O1	1.4269 (13)	C5—C4	1.376 (3)
S1—O2	1.4291 (13)	C4—C3	1.383 (3)
S1—N1	1.6193 (15)	C4—H4	0.9300
S1—C1	1.7701 (17)	C3—H3	0.9300
O3—C2	1.361 (2)	C10—C9	1.375 (4)
O3—C13	1.419 (2)	C10—C16	1.512 (3)
O4—C5	1.364 (2)	C8—C9	1.387 (3)
O4—C14	1.416 (3)	C8—C15	1.510 (3)
N1—C7	1.429 (2)	C13—H13A	0.9600
N1—H1	0.83 (2)	C13—H13B	0.9600
C6—C1	1.376 (2)	C13—H13C	0.9600
C6—C5	1.392 (3)	C9—H9	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C1—C2	1.402 (2)	C14—H14B	0.9600
C7—C8	1.385 (3)	C14—H14C	0.9600
C7—C12	1.389 (3)	C15—H15A	0.9600
C12—C11	1.383 (3)	C15—H15B	0.9600
C12—H12	0.9300	C15—H15C	0.9600
C2—C3	1.383 (3)	C16—H16A	0.9600
C11—C10	1.371 (3)	C16—H16B	0.9600
C11—H11	0.9300	C16—H16C	0.9600

O1—S1—O2	118.43 (8)	C2—C3—H3	119.6
O1—S1—N1	105.33 (8)	C4—C3—H3	119.6
O2—S1—N1	108.81 (8)	C11—C10—C9	116.8 (2)
O1—S1—C1	109.46 (8)	C11—C10—C16	122.1 (2)
O2—S1—C1	107.06 (8)	C9—C10—C16	121.0 (2)
N1—S1—C1	107.28 (7)	C7—C8—C9	118.0 (2)
C2—O3—C13	118.15 (15)	C7—C8—C15	120.9 (2)
C5—O4—C14	117.57 (17)	C9—C8—C15	121.0 (2)
C7—N1—S1	125.25 (12)	O3—C13—H13A	109.5
C7—N1—H1	114.3 (17)	O3—C13—H13B	109.5
S1—N1—H1	112.3 (17)	H13A—C13—H13B	109.5
C1—C6—C5	120.16 (16)	O3—C13—H13C	109.5
C1—C6—H6	119.9	H13A—C13—H13C	109.5
C5—C6—H6	119.9	H13B—C13—H13C	109.5
C6—C1—C2	120.68 (15)	C10—C9—C8	123.9 (2)
C6—C1—S1	118.58 (13)	C10—C9—H9	118.0
C2—C1—S1	120.73 (13)	C8—C9—H9	118.0
C8—C7—C12	119.12 (18)	O4—C14—H14A	109.5
C8—C7—N1	118.30 (17)	O4—C14—H14B	109.5
C12—C7—N1	122.57 (16)	H14A—C14—H14B	109.5
C11—C12—C7	120.68 (19)	O4—C14—H14C	109.5
C11—C12—H12	119.7	H14A—C14—H14C	109.5
C7—C12—H12	119.7	H14B—C14—H14C	109.5
O3—C2—C3	125.06 (16)	C8—C15—H15A	109.5
O3—C2—C1	116.57 (15)	C8—C15—H15B	109.5
C3—C2—C1	118.37 (15)	H15A—C15—H15B	109.5
C10—C11—C12	121.4 (2)	C8—C15—H15C	109.5
C10—C11—H11	119.3	H15A—C15—H15C	109.5
C12—C11—H11	119.3	H15B—C15—H15C	109.5
O4—C5—C4	125.46 (17)	C10—C16—H16A	109.5
O4—C5—C6	115.13 (16)	C10—C16—H16B	109.5
C4—C5—C6	119.41 (16)	H16A—C16—H16B	109.5
C5—C4—C3	120.53 (17)	C10—C16—H16C	109.5
C5—C4—H4	119.7	H16A—C16—H16C	109.5
C3—C4—H4	119.7	H16B—C16—H16C	109.5
C2—C3—C4	120.86 (16)

O1—S1—N1—C7	−175.71 (13)	C7—C12—C11—C10	−0.8 (3)
O2—S1—N1—C7	56.34 (15)	C14—O4—C5—C4	−6.7 (3)
C1—S1—N1—C7	−59.16 (15)	C14—O4—C5—C6	173.99 (19)
C5—C6—C1—C2	−0.4 (3)	C1—C6—C5—O4	−179.72 (16)
C5—C6—C1—S1	178.50 (13)	C1—C6—C5—C4	0.9 (3)
O1—S1—C1—C6	−121.84 (14)	O4—C5—C4—C3	−179.88 (19)
O2—S1—C1—C6	7.70 (16)	C6—C5—C4—C3	−0.6 (3)
N1—S1—C1—C6	124.36 (14)	O3—C2—C3—C4	−179.80 (18)
O1—S1—C1—C2	57.05 (15)	C1—C2—C3—C4	0.8 (3)
O2—S1—C1—C2	−173.42 (13)	C5—C4—C3—C2	−0.3 (3)
N1—S1—C1—C2	−56.76 (15)	C12—C11—C10—C9	0.7 (3)
S1—N1—C7—C8	166.60 (15)	C12—C11—C10—C16	−179.1 (2)
S1—N1—C7—C12	−13.9 (2)	C12—C7—C8—C9	0.4 (3)
C8—C7—C12—C11	0.2 (3)	N1—C7—C8—C9	179.95 (19)
N1—C7—C12—C11	−179.31 (16)	C12—C7—C8—C15	179.7 (3)
C13—O3—C2—C3	12.3 (3)	N1—C7—C8—C15	−0.8 (3)
C13—O3—C2—C1	−168.32 (19)	C11—C10—C9—C8	−0.1 (4)
C6—C1—C2—O3	−179.91 (16)	C16—C10—C9—C8	179.8 (3)
S1—C1—C2—O3	1.2 (2)	C7—C8—C9—C10	−0.5 (4)
C6—C1—C2—C3	−0.5 (3)	C15—C8—C9—C10	−179.8 (3)
S1—C1—C2—C3	−179.31 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2	0.93	2.43	3.0572	125
N1—H1···O1ⁱ	0.83	2.31	3.1218	165

Symmetry code: (i) −x+1, −y+1, −z.

Comparison of various parameters in the crystal structures of 2,4-dichloro-N-(disubstituted phenyl)benzenesulfonamides (Series 1) top

Parameters	2,3-dc	3,4-dc	3,5-dc	2,4-dm	2,5-dm	2,6-dm	3,4-dm	3,5-dm
Crystal System	Monoclinic	Triclinic	Triclinic	Monoclinic	Monoclinic	Monoclinic	Monoclinic	Monoclinic
Z'	1	1	1	1	3	1	1	1
DA between the two aromatic rings	67.7 (1)	68.9 (1)	61.9 (1)	44.6 (1)	68.8 (1), 64.1 (1), 68.5 (1)	69.6 (1)	66.4 (1)	82.8 (1)
Intermolecular Interactions	Nil	N—H···O	N—H···O	N—H···O	N—H···O	N—H···O	N—H···O	N—H···O, C—H···O
Geometry of the N—H···O interactions	-	R₂²(8)	R₂²(8)	R₂²(8)	R₂²(8)	C(4)	R₂²(8)	R₂²(8)
Supramolecular architecture	0D	0D	0D	0D	0D	1 D chain	0D	0D
Reference	Vinola et al. (2011a)	Gowda et al. (2009a)	Vinola et al. (2011b)	Vinola et al. (2011c)	Vinola et al. (2011d)	Vinola et al. (2011e)	Vinola et al. (2011f)	Vinola et al. (2011g)