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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 dnorm 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013195/yp3146sup1.cif
Contains datablocks I, II, III, shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013195/yp3146Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013195/yp3146IIsup3.hkl
Contains datablock II

hkl

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
C14H13Cl2NO4SF(000) = 744
Mr = 362.21Prism
Triclinic, P1Dx = 1.575 Mg m3
a = 9.7575 (3) ÅCu Kα radiation, λ = 1.54178 Å
b = 11.0792 (3) ÅCell parameters from 143 reflections
c = 15.5286 (4) Åθ = 5.1–64.6°
α = 88.733 (1)°µ = 5.26 mm1
β = 83.753 (1)°T = 296 K
γ = 66.337 (1)°Prism, colourless
V = 1528.02 (7) Å30.28 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker APEXII CCD area
diffractometer
5044 independent reflections
Radiation source: fine-focus sealed tube4940 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
phi and φ scansθmax = 64.6°, θmin = 5.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.286, Tmax = 0.314k = 1212
17943 measured reflectionsl = 1718
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0576P)2 + 0.8603P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5044 reflectionsΔρmax = 0.35 e Å3
409 parametersΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
C10.79129 (18)0.32961 (17)0.49002 (11)0.0140 (4)
C20.72234 (19)0.27920 (17)0.43435 (11)0.0138 (3)
C30.61624 (19)0.36781 (18)0.38476 (11)0.0166 (4)
H30.5670700.3372040.3482410.020*
C40.5845 (2)0.50066 (18)0.38998 (11)0.0177 (4)
H40.5148850.5586420.3559940.021*
C50.6540 (2)0.54947 (17)0.44477 (12)0.0167 (4)
C60.75744 (19)0.46390 (17)0.49623 (11)0.0153 (4)
H60.8032610.4957840.5341620.018*
C70.73623 (19)0.18199 (17)0.67699 (11)0.0144 (3)
C80.6264 (2)0.12930 (16)0.68777 (11)0.0149 (4)
C90.5165 (2)0.16888 (18)0.75880 (12)0.0176 (4)
C100.5106 (2)0.26307 (19)0.81767 (12)0.0209 (4)
H100.4364710.2897700.8646090.025*
C110.6167 (2)0.31698 (19)0.80561 (12)0.0214 (4)
H110.6121300.3817350.8442970.026*
C120.7295 (2)0.27653 (18)0.73723 (12)0.0179 (4)
H120.8012490.3124360.7312950.022*
C130.6971 (2)0.09176 (19)0.37678 (13)0.0215 (4)
H13A0.5905980.1253420.3934700.032*
H13B0.7397000.0025050.3807570.032*
H13C0.7157420.1155930.3182130.032*
C140.6932 (2)0.73400 (19)0.49390 (13)0.0251 (4)
H14A0.6736350.7187120.5541850.038*
H14B0.6608020.8269750.4850830.038*
H14C0.7991580.6905230.4760060.038*
C150.2516 (2)0.42712 (17)0.11786 (11)0.0161 (4)
C160.1008 (2)0.50730 (18)0.14647 (12)0.0183 (4)
C170.0218 (2)0.60916 (19)0.09407 (13)0.0216 (4)
H170.0778530.6637270.1119560.026*
C180.0898 (2)0.63065 (18)0.01516 (12)0.0200 (4)
H180.0354280.6996650.0189910.024*
C190.2383 (2)0.54975 (18)0.01301 (12)0.0177 (4)
C200.3196 (2)0.44736 (18)0.03926 (12)0.0166 (4)
H200.4192840.3929660.0212310.020*
C210.2352 (2)0.13263 (17)0.15186 (11)0.0165 (4)
C220.12122 (19)0.09010 (17)0.18136 (11)0.0163 (4)
C230.0896 (2)0.00504 (18)0.13021 (12)0.0187 (4)
C240.1673 (2)0.0356 (2)0.04850 (13)0.0230 (4)
H240.1469870.0933400.0146230.028*
C250.2752 (2)0.0110 (2)0.01808 (12)0.0234 (4)
H250.3248880.0134380.0374110.028*
C260.3103 (2)0.09332 (19)0.06894 (12)0.0203 (4)
H260.3842790.1225680.0477880.024*
C270.1029 (2)0.5665 (2)0.26000 (14)0.0293 (5)
H27A0.1030040.6524920.2664390.044*
H27B0.1275120.5364580.3156590.044*
H27C0.1761270.5706480.2221660.044*
C280.2364 (2)0.6599 (2)0.14688 (13)0.0258 (4)
H28A0.1470910.6492400.1582100.039*
H28B0.2993670.6518180.2002990.039*
H28C0.2091310.7453640.1208920.039*
N10.85352 (17)0.13286 (15)0.60840 (9)0.0141 (3)
N20.27083 (18)0.20936 (16)0.20939 (10)0.0190 (3)
O11.04786 (13)0.12823 (12)0.49395 (8)0.0179 (3)
O20.96577 (14)0.29929 (12)0.60929 (8)0.0181 (3)
O30.76485 (14)0.14672 (12)0.43328 (8)0.0179 (3)
O40.61333 (15)0.68333 (12)0.44419 (9)0.0223 (3)
O50.36419 (16)0.36091 (14)0.26542 (9)0.0268 (3)
O60.50078 (14)0.22685 (13)0.13344 (9)0.0238 (3)
O70.04338 (15)0.47663 (14)0.22377 (9)0.0250 (3)
O80.31633 (15)0.56055 (13)0.08919 (9)0.0248 (3)
S10.92927 (4)0.22078 (4)0.55147 (3)0.01297 (12)
S20.36214 (5)0.30307 (4)0.18441 (3)0.01833 (13)
CL10.62931 (5)0.01467 (4)0.61365 (3)0.01777 (12)
CL20.38522 (5)0.09954 (5)0.77489 (3)0.02456 (13)
CL30.02237 (5)0.14335 (4)0.28231 (3)0.01903 (12)
CL40.04782 (5)0.05037 (5)0.16772 (3)0.02518 (13)
H10.859 (3)0.071 (2)0.5807 (14)0.021 (6)*
H20.210 (3)0.238 (2)0.2535 (15)0.029 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0105 (8)0.0169 (9)0.0137 (8)0.0052 (7)0.0008 (6)0.0020 (7)
C20.0131 (8)0.0151 (9)0.0130 (8)0.0062 (7)0.0020 (6)0.0001 (6)
C30.0139 (9)0.0245 (10)0.0127 (8)0.0093 (7)0.0010 (7)0.0010 (7)
C40.0129 (9)0.0214 (9)0.0160 (9)0.0045 (7)0.0004 (7)0.0058 (7)
C50.0141 (9)0.0154 (9)0.0180 (9)0.0048 (7)0.0042 (7)0.0028 (7)
C60.0142 (8)0.0169 (9)0.0148 (8)0.0071 (7)0.0013 (7)0.0003 (7)
C70.0135 (8)0.0141 (8)0.0142 (8)0.0039 (7)0.0029 (7)0.0044 (7)
C80.0159 (9)0.0129 (8)0.0146 (8)0.0037 (7)0.0043 (7)0.0010 (7)
C90.0137 (9)0.0188 (9)0.0198 (9)0.0062 (7)0.0019 (7)0.0030 (7)
C100.0201 (9)0.0230 (10)0.0174 (9)0.0071 (8)0.0022 (7)0.0017 (7)
C110.0244 (10)0.0228 (9)0.0172 (9)0.0098 (8)0.0013 (7)0.0043 (7)
C120.0185 (9)0.0218 (9)0.0163 (9)0.0107 (7)0.0035 (7)0.0014 (7)
C130.0223 (10)0.0237 (10)0.0235 (10)0.0139 (8)0.0041 (8)0.0038 (8)
C140.0268 (10)0.0190 (9)0.0299 (11)0.0106 (8)0.0006 (8)0.0004 (8)
C150.0171 (9)0.0167 (9)0.0171 (9)0.0092 (7)0.0037 (7)0.0009 (7)
C160.0190 (9)0.0209 (9)0.0167 (9)0.0102 (8)0.0011 (7)0.0024 (7)
C170.0162 (9)0.0203 (9)0.0247 (10)0.0038 (7)0.0005 (7)0.0025 (7)
C180.0200 (9)0.0161 (9)0.0222 (9)0.0048 (7)0.0055 (7)0.0025 (7)
C190.0195 (9)0.0188 (9)0.0156 (9)0.0087 (7)0.0009 (7)0.0001 (7)
C200.0142 (9)0.0168 (9)0.0184 (9)0.0060 (7)0.0003 (7)0.0019 (7)
C210.0147 (9)0.0173 (9)0.0173 (9)0.0058 (7)0.0047 (7)0.0062 (7)
C220.0136 (8)0.0177 (9)0.0141 (9)0.0030 (7)0.0012 (7)0.0034 (7)
C230.0141 (9)0.0200 (9)0.0212 (9)0.0062 (7)0.0022 (7)0.0034 (7)
C240.0188 (10)0.0252 (10)0.0237 (10)0.0072 (8)0.0029 (8)0.0038 (8)
C250.0189 (10)0.0306 (11)0.0166 (9)0.0066 (8)0.0019 (7)0.0030 (8)
C260.0152 (9)0.0259 (10)0.0194 (9)0.0085 (8)0.0006 (7)0.0036 (7)
C270.0203 (10)0.0394 (12)0.0240 (10)0.0096 (9)0.0069 (8)0.0059 (9)
C280.0318 (11)0.0274 (10)0.0181 (9)0.0113 (9)0.0058 (8)0.0071 (8)
N10.0178 (8)0.0123 (7)0.0131 (7)0.0073 (6)0.0009 (6)0.0002 (6)
N20.0209 (8)0.0229 (8)0.0159 (8)0.0120 (7)0.0008 (7)0.0027 (6)
O10.0123 (6)0.0178 (6)0.0206 (6)0.0040 (5)0.0020 (5)0.0006 (5)
O20.0184 (6)0.0205 (6)0.0183 (6)0.0102 (5)0.0045 (5)0.0001 (5)
O30.0209 (7)0.0158 (6)0.0193 (6)0.0093 (5)0.0043 (5)0.0018 (5)
O40.0233 (7)0.0130 (6)0.0298 (7)0.0061 (5)0.0050 (6)0.0048 (5)
O50.0321 (8)0.0355 (8)0.0219 (7)0.0210 (7)0.0118 (6)0.0037 (6)
O60.0146 (6)0.0244 (7)0.0309 (7)0.0064 (5)0.0036 (5)0.0070 (6)
O70.0213 (7)0.0302 (7)0.0194 (7)0.0081 (6)0.0054 (5)0.0013 (6)
O80.0244 (7)0.0251 (7)0.0184 (7)0.0046 (6)0.0019 (5)0.0066 (5)
S10.0106 (2)0.0143 (2)0.0140 (2)0.00506 (17)0.00134 (16)0.00094 (16)
S20.0169 (2)0.0220 (2)0.0192 (2)0.01024 (19)0.00585 (17)0.00503 (18)
CL10.0179 (2)0.0176 (2)0.0191 (2)0.00882 (17)0.00016 (16)0.00352 (16)
CL20.0197 (2)0.0278 (3)0.0284 (3)0.01360 (19)0.00535 (18)0.00312 (19)
CL30.0185 (2)0.0241 (2)0.0140 (2)0.00884 (18)0.00097 (16)0.00255 (16)
CL40.0229 (2)0.0294 (3)0.0289 (3)0.0167 (2)0.00114 (19)0.00075 (19)
Geometric parameters (Å, º) top
C1—C61.392 (3)C16—C171.388 (3)
C1—C21.400 (2)C17—C181.391 (3)
C1—S11.7615 (17)C17—H170.9300
C2—O31.356 (2)C18—C191.390 (3)
C2—C31.397 (2)C18—H180.9300
C3—C41.379 (3)C19—O81.366 (2)
C3—H30.9300C19—C201.397 (3)
C4—C51.385 (3)C20—H200.9300
C4—H40.9300C21—C261.396 (3)
C5—O41.373 (2)C21—C221.403 (3)
C5—C61.389 (3)C21—N21.407 (2)
C6—H60.9300C22—C231.391 (3)
C7—C121.397 (3)C22—CL31.7294 (18)
C7—C81.406 (3)C23—C241.389 (3)
C7—N11.414 (2)C23—CL41.7287 (18)
C8—C91.395 (3)C24—C251.384 (3)
C8—CL11.7225 (17)C24—H240.9300
C9—C101.382 (3)C25—C261.384 (3)
C9—CL21.7335 (18)C25—H250.9300
C10—C111.384 (3)C26—H260.9300
C10—H100.9300C27—O71.433 (2)
C11—C121.382 (3)C27—H27A0.9600
C11—H110.9300C27—H27B0.9600
C12—H120.9300C27—H27C0.9600
C13—O31.432 (2)C28—O81.429 (2)
C13—H13A0.9600C28—H28A0.9600
C13—H13B0.9600C28—H28B0.9600
C13—H13C0.9600C28—H28C0.9600
C14—O41.421 (2)N1—S11.6354 (15)
C14—H14A0.9600N1—H10.79 (2)
C14—H14B0.9600N2—S21.6346 (16)
C14—H14C0.9600N2—H20.83 (2)
C15—C201.383 (3)O1—S11.4323 (13)
C15—C161.406 (3)O2—S11.4290 (13)
C15—S21.7637 (18)O5—S21.4299 (15)
C16—O71.363 (2)O6—S21.4315 (14)
C6—C1—C2121.75 (16)C17—C18—H18119.8
C6—C1—S1118.61 (13)O8—C19—C18125.77 (17)
C2—C1—S1119.61 (13)O8—C19—C20114.88 (16)
O3—C2—C3125.21 (16)C18—C19—C20119.35 (17)
O3—C2—C1116.56 (15)C15—C20—C19119.82 (17)
C3—C2—C1118.22 (16)C15—C20—H20120.1
C4—C3—C2119.98 (17)C19—C20—H20120.1
C4—C3—H3120.0C26—C21—C22118.78 (17)
C2—C3—H3120.0C26—C21—N2123.58 (16)
C3—C4—C5121.36 (16)C22—C21—N2117.60 (16)
C3—C4—H4119.3C23—C22—C21120.22 (16)
C5—C4—H4119.3C23—C22—CL3120.58 (14)
O4—C5—C4116.00 (16)C21—C22—CL3119.20 (14)
O4—C5—C6124.16 (17)C24—C23—C22120.42 (17)
C4—C5—C6119.84 (17)C24—C23—CL4119.42 (15)
C5—C6—C1118.82 (16)C22—C23—CL4120.16 (14)
C5—C6—H6120.6C25—C24—C23119.22 (18)
C1—C6—H6120.6C25—C24—H24120.4
C12—C7—C8118.53 (16)C23—C24—H24120.4
C12—C7—N1122.38 (16)C24—C25—C26121.03 (18)
C8—C7—N1119.01 (16)C24—C25—H25119.5
C9—C8—C7119.98 (16)C26—C25—H25119.5
C9—C8—CL1120.23 (14)C25—C26—C21120.24 (17)
C7—C8—CL1119.79 (14)C25—C26—H26119.9
C10—C9—C8120.87 (17)C21—C26—H26119.9
C10—C9—CL2118.87 (14)O7—C27—H27A109.5
C8—C9—CL2120.26 (14)O7—C27—H27B109.5
C9—C10—C11118.90 (17)H27A—C27—H27B109.5
C9—C10—H10120.5O7—C27—H27C109.5
C11—C10—H10120.5H27A—C27—H27C109.5
C12—C11—C10121.32 (17)H27B—C27—H27C109.5
C12—C11—H11119.3O8—C28—H28A109.5
C10—C11—H11119.3O8—C28—H28B109.5
C11—C12—C7120.34 (17)H28A—C28—H28B109.5
C11—C12—H12119.8O8—C28—H28C109.5
C7—C12—H12119.8H28A—C28—H28C109.5
O3—C13—H13A109.5H28B—C28—H28C109.5
O3—C13—H13B109.5C7—N1—S1125.25 (13)
H13A—C13—H13B109.5C7—N1—H1118.2 (17)
O3—C13—H13C109.5S1—N1—H1110.6 (16)
H13A—C13—H13C109.5C21—N2—S2126.87 (13)
H13B—C13—H13C109.5C21—N2—H2115.7 (17)
O4—C14—H14A109.5S2—N2—H2111.1 (17)
O4—C14—H14B109.5C2—O3—C13118.04 (14)
H14A—C14—H14B109.5C5—O4—C14116.87 (14)
O4—C14—H14C109.5C16—O7—C27117.73 (15)
H14A—C14—H14C109.5C19—O8—C28117.19 (15)
H14B—C14—H14C109.5O2—S1—O1118.72 (7)
C20—C15—C16121.30 (16)O2—S1—N1108.83 (8)
C20—C15—S2118.10 (14)O1—S1—N1105.14 (8)
C16—C15—S2120.52 (14)O2—S1—C1107.29 (8)
O7—C16—C17125.23 (17)O1—S1—C1108.95 (8)
O7—C16—C15116.58 (16)N1—S1—C1107.44 (8)
C17—C16—C15118.19 (17)O5—S2—O6119.88 (8)
C16—C17—C18120.85 (17)O5—S2—N2104.30 (8)
C16—C17—H17119.6O6—S2—N2108.76 (8)
C18—C17—H17119.6O5—S2—C15109.31 (8)
C19—C18—C17120.49 (17)O6—S2—C15107.38 (8)
C19—C18—H18119.8N2—S2—C15106.49 (8)
C6—C1—C2—O3179.57 (15)C26—C21—C22—CL3177.51 (13)
S1—C1—C2—O31.7 (2)N2—C21—C22—CL34.7 (2)
C6—C1—C2—C30.5 (2)C21—C22—C23—C241.9 (3)
S1—C1—C2—C3178.32 (12)CL3—C22—C23—C24178.79 (14)
O3—C2—C3—C4178.60 (16)C21—C22—C23—CL4178.47 (13)
C1—C2—C3—C41.5 (2)CL3—C22—C23—CL40.8 (2)
C2—C3—C4—C51.1 (3)C22—C23—C24—C250.8 (3)
C3—C4—C5—O4179.90 (16)CL4—C23—C24—C25178.80 (15)
C3—C4—C5—C60.4 (3)C23—C24—C25—C262.3 (3)
O4—C5—C6—C1178.96 (15)C24—C25—C26—C211.0 (3)
C4—C5—C6—C11.4 (2)C22—C21—C26—C251.7 (3)
C2—C1—C6—C50.9 (2)N2—C21—C26—C25175.94 (17)
S1—C1—C6—C5176.94 (13)C12—C7—N1—S139.4 (2)
C12—C7—C8—C91.8 (2)C8—C7—N1—S1143.86 (14)
N1—C7—C8—C9175.04 (15)C26—C21—N2—S220.3 (3)
C12—C7—C8—CL1178.86 (13)C22—C21—N2—S2161.97 (14)
N1—C7—C8—CL14.3 (2)C3—C2—O3—C130.4 (2)
C7—C8—C9—C102.2 (3)C1—C2—O3—C13179.69 (15)
CL1—C8—C9—C10178.45 (14)C4—C5—O4—C14174.43 (16)
C7—C8—C9—CL2177.43 (13)C6—C5—O4—C145.9 (2)
CL1—C8—C9—CL21.9 (2)C17—C16—O7—C279.1 (3)
C8—C9—C10—C110.6 (3)C15—C16—O7—C27171.97 (17)
CL2—C9—C10—C11179.01 (14)C18—C19—O8—C283.1 (3)
C9—C10—C11—C121.3 (3)C20—C19—O8—C28177.26 (16)
C10—C11—C12—C71.7 (3)C7—N1—S1—O248.38 (16)
C8—C7—C12—C110.1 (3)C7—N1—S1—O1176.57 (14)
N1—C7—C12—C11176.87 (16)C7—N1—S1—C167.49 (16)
C20—C15—C16—O7178.22 (16)C6—C1—S1—O29.03 (15)
S2—C15—C16—O75.2 (2)C2—C1—S1—O2173.06 (13)
C20—C15—C16—C170.8 (3)C6—C1—S1—O1120.68 (13)
S2—C15—C16—C17175.75 (14)C2—C1—S1—O157.23 (15)
O7—C16—C17—C18178.53 (18)C6—C1—S1—N1125.91 (14)
C15—C16—C17—C180.4 (3)C2—C1—S1—N156.18 (15)
C16—C17—C18—C190.4 (3)C21—N2—S2—O5178.51 (15)
C17—C18—C19—O8179.51 (18)C21—N2—S2—O652.47 (17)
C17—C18—C19—C200.8 (3)C21—N2—S2—C1562.96 (17)
C16—C15—C20—C190.4 (3)C20—C15—S2—O5119.90 (15)
S2—C15—C20—C19176.25 (13)C16—C15—S2—O556.78 (17)
O8—C19—C20—C15179.87 (16)C20—C15—S2—O611.61 (17)
C18—C19—C20—C150.4 (3)C16—C15—S2—O6171.71 (14)
C26—C21—C22—C233.2 (3)C20—C15—S2—N2127.97 (15)
N2—C21—C22—C23174.65 (15)C16—C15—S2—N255.35 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O20.932.312.9620126
C26—H26···O60.932.423.0533125
N1—H1···O1i0.792.313.0750163
C3—H3···O50.932.403.2616154
C14—H14B···Cl1ii0.962.823.459 (2)125
C14—H14C···O2iii0.962.563.414 (3)148
C4—H4···Cgiv0.932.823.7011159
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
C14H13Cl2NO4SF(000) = 372
Mr = 362.21Prism
Triclinic, P1Dx = 1.604 Mg m3
a = 7.4855 (5) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.1175 (6) ÅCell parameters from 133 reflections
c = 13.9643 (10) Åθ = 7.5–64.5°
α = 98.151 (2)°µ = 5.36 mm1
β = 95.566 (2)°T = 296 K
γ = 114.952 (2)°Prism, colourless
V = 749.84 (9) Å30.27 × 0.24 × 0.19 mm
Z = 2
Data collection top
Bruker APEXII CCD area detector
diffractometer
2452 independent reflections
Radiation source: fine-focus sealed tube2393 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
phi and φ scansθmax = 64.5°, θmin = 7.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 88
Tmin = 0.294, Tmax = 0.361k = 99
9208 measured reflectionsl = 1616
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0635P)2 + 0.7485P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2452 reflectionsΔρmax = 0.31 e Å3
205 parametersΔρmin = 0.39 e Å3
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
xyzUiso*/Ueq
C10.6325 (3)0.7183 (3)0.64637 (15)0.0139 (4)
C20.7057 (3)0.5880 (3)0.62229 (16)0.0163 (4)
C30.7846 (3)0.5856 (3)0.53654 (16)0.0186 (5)
H30.8357310.5011470.5196600.022*
C40.7883 (3)0.7081 (3)0.47535 (16)0.0183 (5)
H40.8410930.7043550.4179150.022*
C50.7135 (3)0.8358 (3)0.49982 (15)0.0159 (4)
C60.6362 (3)0.8412 (3)0.58618 (15)0.0155 (4)
H60.5870350.9270380.6035180.019*
C70.8945 (3)0.8829 (3)0.86429 (14)0.0146 (4)
C81.0494 (3)0.8367 (3)0.89214 (14)0.0148 (4)
C91.2472 (3)0.9667 (3)0.91241 (15)0.0161 (4)
H91.3479170.9336380.9316810.019*
C101.2931 (3)1.1472 (3)0.90359 (15)0.0174 (5)
C111.1447 (3)1.1994 (3)0.87695 (16)0.0183 (5)
H111.1775651.3212790.8715570.022*
C120.9459 (3)1.0674 (3)0.85837 (15)0.0169 (5)
H120.8454961.1023570.8417160.020*
C130.7778 (4)0.3454 (3)0.66569 (18)0.0258 (5)
H13A0.7222370.2715480.6005470.039*
H13B0.7507930.2658050.7125330.039*
H13C0.9198160.4156430.6711220.039*
C140.7720 (4)0.9450 (4)0.35043 (17)0.0243 (5)
H14A0.9101040.9687040.3605730.036*
H14B0.7563421.0339330.3162220.036*
H14C0.6919590.8221950.3121210.036*
N10.6935 (3)0.7456 (3)0.84630 (13)0.0158 (4)
O10.3573 (2)0.5553 (2)0.75085 (11)0.0208 (4)
O20.5055 (2)0.8960 (2)0.76766 (11)0.0202 (4)
O30.6894 (2)0.4692 (2)0.68484 (11)0.0200 (3)
O40.7085 (2)0.9602 (2)0.44395 (11)0.0219 (4)
S10.52743 (7)0.72789 (7)0.75407 (3)0.01471 (17)
CL11.54329 (8)1.30818 (7)0.92628 (4)0.02443 (18)
CL20.99583 (7)0.61177 (7)0.90466 (4)0.02040 (18)
H10.684 (4)0.643 (4)0.854 (2)0.023 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0113 (9)0.0165 (10)0.0120 (10)0.0051 (8)0.0017 (8)0.0005 (8)
C20.0132 (10)0.0156 (11)0.0198 (11)0.0062 (8)0.0004 (8)0.0044 (9)
C30.0162 (10)0.0199 (11)0.0219 (11)0.0111 (9)0.0027 (9)0.0016 (9)
C40.0170 (11)0.0217 (12)0.0155 (10)0.0083 (9)0.0045 (8)0.0012 (9)
C50.0141 (10)0.0185 (11)0.0150 (10)0.0070 (9)0.0004 (8)0.0051 (9)
C60.0138 (10)0.0151 (11)0.0171 (10)0.0068 (9)0.0010 (8)0.0016 (8)
C70.0147 (10)0.0182 (11)0.0104 (9)0.0061 (9)0.0044 (8)0.0038 (8)
C80.0187 (11)0.0157 (11)0.0116 (10)0.0082 (9)0.0044 (8)0.0045 (8)
C90.0162 (10)0.0194 (11)0.0145 (10)0.0090 (9)0.0043 (8)0.0044 (9)
C100.0167 (11)0.0179 (11)0.0150 (10)0.0043 (9)0.0058 (8)0.0041 (9)
C110.0233 (11)0.0146 (11)0.0181 (11)0.0081 (9)0.0070 (9)0.0053 (9)
C120.0190 (11)0.0189 (11)0.0164 (10)0.0105 (9)0.0044 (8)0.0066 (9)
C130.0349 (13)0.0222 (12)0.0295 (13)0.0214 (11)0.0042 (10)0.0054 (10)
C140.0233 (12)0.0364 (14)0.0176 (11)0.0143 (11)0.0077 (9)0.0126 (10)
N10.0160 (9)0.0161 (10)0.0167 (9)0.0069 (8)0.0034 (7)0.0077 (7)
O10.0125 (7)0.0259 (9)0.0206 (8)0.0046 (7)0.0042 (6)0.0059 (7)
O20.0235 (8)0.0260 (9)0.0191 (8)0.0178 (7)0.0062 (6)0.0048 (6)
O30.0257 (8)0.0199 (8)0.0215 (8)0.0150 (7)0.0065 (6)0.0081 (6)
O40.0263 (8)0.0276 (9)0.0196 (8)0.0158 (7)0.0094 (7)0.0129 (7)
S10.0127 (3)0.0189 (3)0.0142 (3)0.0080 (2)0.0038 (2)0.0040 (2)
CL10.0163 (3)0.0199 (3)0.0323 (3)0.0026 (2)0.0048 (2)0.0074 (2)
CL20.0183 (3)0.0155 (3)0.0278 (3)0.0072 (2)0.0019 (2)0.0082 (2)
Geometric parameters (Å, º) top
C1—C61.386 (3)C9—H90.9300
C1—C21.398 (3)C10—C111.383 (3)
C1—S11.771 (2)C10—CL11.737 (2)
C2—O31.367 (3)C11—C121.389 (3)
C2—C31.387 (3)C11—H110.9300
C3—C41.393 (3)C12—H120.9300
C3—H30.9300C13—O31.428 (3)
C4—C51.390 (3)C13—H13A0.9600
C4—H40.9300C13—H13B0.9600
C5—O41.371 (3)C13—H13C0.9600
C5—C61.390 (3)C14—O41.439 (3)
C6—H60.9300C14—H14A0.9600
C7—C121.398 (3)C14—H14B0.9600
C7—C81.399 (3)C14—H14C0.9600
C7—N11.415 (3)N1—S11.6464 (18)
C8—C91.379 (3)N1—H10.83 (3)
C8—CL21.735 (2)O1—S11.4325 (16)
C9—C101.383 (3)O2—S11.4310 (16)
C6—C1—C2121.35 (19)C10—C11—C12119.2 (2)
C6—C1—S1117.92 (16)C10—C11—H11120.4
C2—C1—S1120.71 (16)C12—C11—H11120.4
O3—C2—C3124.94 (19)C11—C12—C7121.1 (2)
O3—C2—C1116.80 (19)C11—C12—H12119.5
C3—C2—C1118.24 (19)C7—C12—H12119.5
C2—C3—C4120.9 (2)O3—C13—H13A109.5
C2—C3—H3119.6O3—C13—H13B109.5
C4—C3—H3119.6H13A—C13—H13B109.5
C5—C4—C3120.3 (2)O3—C13—H13C109.5
C5—C4—H4119.9H13A—C13—H13C109.5
C3—C4—H4119.9H13B—C13—H13C109.5
O4—C5—C6115.97 (19)O4—C14—H14A109.5
O4—C5—C4124.56 (19)O4—C14—H14B109.5
C6—C5—C4119.5 (2)H14A—C14—H14B109.5
C1—C6—C5119.81 (19)O4—C14—H14C109.5
C1—C6—H6120.1H14A—C14—H14C109.5
C5—C6—H6120.1H14B—C14—H14C109.5
C12—C7—C8117.8 (2)C7—N1—S1122.50 (14)
C12—C7—N1122.36 (19)C7—N1—H1112 (2)
C8—C7—N1119.83 (19)S1—N1—H1112 (2)
C9—C8—C7121.8 (2)C2—O3—C13117.48 (17)
C9—C8—CL2117.90 (16)C5—O4—C14116.37 (18)
C7—C8—CL2120.23 (17)O2—S1—O1119.39 (10)
C8—C9—C10118.8 (2)O2—S1—N1107.92 (9)
C8—C9—H9120.6O1—S1—N1104.97 (9)
C10—C9—H9120.6O2—S1—C1106.61 (10)
C9—C10—C11121.3 (2)O1—S1—C1110.39 (10)
C9—C10—CL1118.36 (17)N1—S1—C1106.94 (9)
C11—C10—CL1120.37 (17)
C6—C1—C2—O3177.93 (18)C9—C10—C11—C120.3 (3)
S1—C1—C2—O30.8 (3)CL1—C10—C11—C12179.42 (16)
C6—C1—C2—C30.6 (3)C10—C11—C12—C71.3 (3)
S1—C1—C2—C3179.37 (16)C8—C7—C12—C111.7 (3)
O3—C2—C3—C4177.6 (2)N1—C7—C12—C11179.65 (18)
C1—C2—C3—C40.9 (3)C12—C7—N1—S143.3 (3)
C2—C3—C4—C50.3 (3)C8—C7—N1—S1138.80 (17)
C3—C4—C5—O4179.2 (2)C3—C2—O3—C136.5 (3)
C3—C4—C5—C60.4 (3)C1—C2—O3—C13175.07 (19)
C2—C1—C6—C50.1 (3)C6—C5—O4—C14174.79 (19)
S1—C1—C6—C5178.64 (16)C4—C5—O4—C144.9 (3)
O4—C5—C6—C1179.03 (19)C7—N1—S1—O261.92 (19)
C4—C5—C6—C10.7 (3)C7—N1—S1—O1169.74 (16)
C12—C7—C8—C90.6 (3)C7—N1—S1—C152.45 (19)
N1—C7—C8—C9178.62 (18)C6—C1—S1—O212.68 (19)
C12—C7—C8—CL2178.02 (15)C2—C1—S1—O2168.52 (17)
N1—C7—C8—CL20.0 (3)C6—C1—S1—O1118.41 (17)
C7—C8—C9—C100.9 (3)C2—C1—S1—O160.38 (19)
CL2—C8—C9—C10179.54 (15)C6—C1—S1—N1127.93 (17)
C8—C9—C10—C111.3 (3)C2—C1—S1—N153.3 (2)
C8—C9—C10—CL1178.37 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.83 (3)2.50 (3)2.989 (2)119 (3)
C12—H12···O20.932.403.038 (3)126
C14—H14B···O2i0.962.493.302 (3)142
C14—H14A···Cgii0.962.893.645 (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
C16H19NO4SF(000) = 340
Mr = 321.38Prism
Triclinic, P1Dx = 1.314 Mg m3
a = 8.2859 (14) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.7197 (15) ÅCell parameters from 136 reflections
c = 12.232 (2) Åθ = 3.9–64.5°
α = 70.522 (5)°µ = 1.92 mm1
β = 80.171 (5)°T = 296 K
γ = 78.856 (5)°Prism, colourless
V = 812.1 (2) Å30.25 × 0.22 × 0.20 mm
Z = 2
Data collection top
Bruker APEXII CCD area
diffractometer
2648 independent reflections
Radiation source: fine-focus sealed tube2563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
phi and φ scansθmax = 64.5°, θmin = 3.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 99
Tmin = 0.649, Tmax = 0.681k = 1010
7355 measured reflectionsl = 1314
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.108P)2 + 0.118P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
2648 reflectionsΔρmax = 0.19 e Å3
207 parametersΔρmin = 0.39 e Å3
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
xyzUiso*/Ueq
S10.34336 (5)0.38129 (4)0.18309 (3)0.0470 (2)
O10.44860 (18)0.32376 (16)0.09529 (11)0.0618 (4)
O20.19850 (16)0.30652 (16)0.23631 (12)0.0610 (4)
O30.64057 (17)0.5301 (2)0.16088 (12)0.0698 (4)
O40.4391 (2)0.1532 (2)0.60613 (12)0.0763 (5)
N10.28789 (19)0.57568 (18)0.12078 (13)0.0497 (4)
C60.4092 (2)0.2693 (2)0.40838 (15)0.0489 (4)
H60.3148320.2194380.4228570.059*
C10.45925 (19)0.36296 (19)0.29687 (14)0.0445 (4)
C70.19017 (19)0.6872 (2)0.17771 (15)0.0485 (4)
C120.1028 (2)0.6344 (2)0.28766 (18)0.0577 (5)
H120.1078730.5223770.3271150.069*
C20.6007 (2)0.4398 (2)0.27360 (15)0.0507 (4)
C110.0082 (2)0.7466 (3)0.3391 (2)0.0685 (6)
H110.0504150.7085760.4123850.082*
C50.4996 (2)0.2490 (2)0.49952 (16)0.0538 (4)
C40.6377 (2)0.3252 (2)0.47736 (17)0.0581 (5)
H40.6979650.3127550.5380970.070*
C30.6877 (2)0.4200 (2)0.36550 (18)0.0595 (5)
H30.7810620.4711960.3518900.071*
C100.0009 (3)0.9127 (3)0.2844 (3)0.0783 (7)
C80.1819 (3)0.8543 (3)0.1200 (2)0.0697 (6)
C130.7981 (3)0.5837 (3)0.1296 (2)0.0859 (7)
H13A0.8038160.6597990.1697340.129*
H13B0.8140020.6368310.0468490.129*
H13C0.8829410.4906750.1509910.129*
C90.0867 (3)0.9620 (3)0.1756 (3)0.0878 (8)
H90.0819351.0741930.1371320.105*
C140.5346 (4)0.1151 (3)0.69984 (19)0.0855 (7)
H14A0.6444070.0655130.6789830.128*
H14B0.4839970.0398510.7678400.128*
H14C0.5402750.2140740.7162380.128*
C150.2757 (4)0.9172 (3)0.0005 (3)0.1157 (13)
H15A0.2457551.0342490.0297530.174*
H15B0.2483740.8660650.0509420.174*
H15C0.3925170.8913320.0063910.174*
C160.1017 (4)1.0371 (4)0.3400 (4)0.1162 (13)
H16A0.0403911.1257900.3265710.174*
H16B0.1246540.9852120.4224220.174*
H16C0.2039641.0793190.3062400.174*
H10.359 (3)0.617 (3)0.068 (2)0.073 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0493 (3)0.0462 (3)0.0487 (3)0.01127 (19)0.00489 (19)0.0169 (2)
O10.0766 (9)0.0560 (7)0.0551 (7)0.0082 (6)0.0005 (6)0.0250 (6)
O20.0596 (8)0.0612 (8)0.0671 (8)0.0266 (6)0.0089 (6)0.0156 (6)
O30.0569 (8)0.0875 (10)0.0565 (8)0.0334 (7)0.0084 (6)0.0026 (7)
O40.0836 (10)0.0914 (11)0.0479 (7)0.0308 (8)0.0070 (7)0.0040 (7)
N10.0487 (8)0.0497 (8)0.0484 (8)0.0082 (6)0.0039 (6)0.0126 (6)
C60.0474 (9)0.0471 (9)0.0517 (9)0.0108 (7)0.0015 (7)0.0147 (7)
C10.0417 (8)0.0427 (8)0.0495 (9)0.0055 (6)0.0037 (7)0.0157 (7)
C70.0367 (8)0.0530 (9)0.0585 (10)0.0072 (7)0.0082 (7)0.0191 (8)
C120.0484 (9)0.0602 (11)0.0655 (11)0.0090 (8)0.0024 (8)0.0220 (9)
C20.0459 (9)0.0504 (9)0.0523 (10)0.0109 (7)0.0040 (7)0.0102 (7)
C110.0495 (10)0.0844 (14)0.0796 (14)0.0177 (9)0.0084 (9)0.0394 (12)
C50.0586 (10)0.0522 (9)0.0468 (9)0.0065 (8)0.0039 (8)0.0125 (7)
C40.0580 (10)0.0624 (11)0.0564 (10)0.0082 (8)0.0159 (8)0.0175 (8)
C30.0498 (10)0.0639 (11)0.0647 (11)0.0170 (8)0.0115 (8)0.0127 (9)
C100.0485 (11)0.0750 (14)0.122 (2)0.0167 (9)0.0137 (12)0.0524 (14)
C80.0572 (11)0.0544 (11)0.0865 (14)0.0058 (8)0.0075 (10)0.0164 (10)
C130.0685 (13)0.1039 (18)0.0752 (14)0.0457 (13)0.0026 (11)0.0012 (13)
C90.0700 (14)0.0550 (12)0.128 (2)0.0105 (10)0.0196 (14)0.0296 (13)
C140.1138 (19)0.0856 (15)0.0505 (11)0.0181 (14)0.0197 (12)0.0054 (11)
C150.120 (2)0.0573 (13)0.117 (2)0.0038 (14)0.0445 (19)0.0044 (14)
C160.0821 (17)0.099 (2)0.188 (4)0.0286 (15)0.042 (2)0.092 (2)
Geometric parameters (Å, º) top
S1—O11.4269 (13)C5—C41.376 (3)
S1—O21.4291 (13)C4—C31.383 (3)
S1—N11.6193 (15)C4—H40.9300
S1—C11.7701 (17)C3—H30.9300
O3—C21.361 (2)C10—C91.375 (4)
O3—C131.419 (2)C10—C161.512 (3)
O4—C51.364 (2)C8—C91.387 (3)
O4—C141.416 (3)C8—C151.510 (3)
N1—C71.429 (2)C13—H13A0.9600
N1—H10.83 (2)C13—H13B0.9600
C6—C11.376 (2)C13—H13C0.9600
C6—C51.392 (3)C9—H90.9300
C6—H60.9300C14—H14A0.9600
C1—C21.402 (2)C14—H14B0.9600
C7—C81.385 (3)C14—H14C0.9600
C7—C121.389 (3)C15—H15A0.9600
C12—C111.383 (3)C15—H15B0.9600
C12—H120.9300C15—H15C0.9600
C2—C31.383 (3)C16—H16A0.9600
C11—C101.371 (3)C16—H16B0.9600
C11—H110.9300C16—H16C0.9600
O1—S1—O2118.43 (8)C2—C3—H3119.6
O1—S1—N1105.33 (8)C4—C3—H3119.6
O2—S1—N1108.81 (8)C11—C10—C9116.8 (2)
O1—S1—C1109.46 (8)C11—C10—C16122.1 (2)
O2—S1—C1107.06 (8)C9—C10—C16121.0 (2)
N1—S1—C1107.28 (7)C7—C8—C9118.0 (2)
C2—O3—C13118.15 (15)C7—C8—C15120.9 (2)
C5—O4—C14117.57 (17)C9—C8—C15121.0 (2)
C7—N1—S1125.25 (12)O3—C13—H13A109.5
C7—N1—H1114.3 (17)O3—C13—H13B109.5
S1—N1—H1112.3 (17)H13A—C13—H13B109.5
C1—C6—C5120.16 (16)O3—C13—H13C109.5
C1—C6—H6119.9H13A—C13—H13C109.5
C5—C6—H6119.9H13B—C13—H13C109.5
C6—C1—C2120.68 (15)C10—C9—C8123.9 (2)
C6—C1—S1118.58 (13)C10—C9—H9118.0
C2—C1—S1120.73 (13)C8—C9—H9118.0
C8—C7—C12119.12 (18)O4—C14—H14A109.5
C8—C7—N1118.30 (17)O4—C14—H14B109.5
C12—C7—N1122.57 (16)H14A—C14—H14B109.5
C11—C12—C7120.68 (19)O4—C14—H14C109.5
C11—C12—H12119.7H14A—C14—H14C109.5
C7—C12—H12119.7H14B—C14—H14C109.5
O3—C2—C3125.06 (16)C8—C15—H15A109.5
O3—C2—C1116.57 (15)C8—C15—H15B109.5
C3—C2—C1118.37 (15)H15A—C15—H15B109.5
C10—C11—C12121.4 (2)C8—C15—H15C109.5
C10—C11—H11119.3H15A—C15—H15C109.5
C12—C11—H11119.3H15B—C15—H15C109.5
O4—C5—C4125.46 (17)C10—C16—H16A109.5
O4—C5—C6115.13 (16)C10—C16—H16B109.5
C4—C5—C6119.41 (16)H16A—C16—H16B109.5
C5—C4—C3120.53 (17)C10—C16—H16C109.5
C5—C4—H4119.7H16A—C16—H16C109.5
C3—C4—H4119.7H16B—C16—H16C109.5
C2—C3—C4120.86 (16)
O1—S1—N1—C7175.71 (13)C7—C12—C11—C100.8 (3)
O2—S1—N1—C756.34 (15)C14—O4—C5—C46.7 (3)
C1—S1—N1—C759.16 (15)C14—O4—C5—C6173.99 (19)
C5—C6—C1—C20.4 (3)C1—C6—C5—O4179.72 (16)
C5—C6—C1—S1178.50 (13)C1—C6—C5—C40.9 (3)
O1—S1—C1—C6121.84 (14)O4—C5—C4—C3179.88 (19)
O2—S1—C1—C67.70 (16)C6—C5—C4—C30.6 (3)
N1—S1—C1—C6124.36 (14)O3—C2—C3—C4179.80 (18)
O1—S1—C1—C257.05 (15)C1—C2—C3—C40.8 (3)
O2—S1—C1—C2173.42 (13)C5—C4—C3—C20.3 (3)
N1—S1—C1—C256.76 (15)C12—C11—C10—C90.7 (3)
S1—N1—C7—C8166.60 (15)C12—C11—C10—C16179.1 (2)
S1—N1—C7—C1213.9 (2)C12—C7—C8—C90.4 (3)
C8—C7—C12—C110.2 (3)N1—C7—C8—C9179.95 (19)
N1—C7—C12—C11179.31 (16)C12—C7—C8—C15179.7 (3)
C13—O3—C2—C312.3 (3)N1—C7—C8—C150.8 (3)
C13—O3—C2—C1168.32 (19)C11—C10—C9—C80.1 (4)
C6—C1—C2—O3179.91 (16)C16—C10—C9—C8179.8 (3)
S1—C1—C2—O31.2 (2)C7—C8—C9—C100.5 (4)
C6—C1—C2—C30.5 (3)C15—C8—C9—C10179.8 (3)
S1—C1—C2—C3179.31 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O20.932.433.0572125
N1—H1···O1i0.832.313.1218165
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
Parameters2,3-dc3,4-dc3,5-dc2,4-dm2,5-dm2,6-dm3,4-dm3,5-dm
Crystal SystemMonoclinicTriclinicTriclinicMonoclinicMonoclinicMonoclinicMonoclinicMonoclinic
Z'11113111
DA between the two aromatic rings67.7 (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 InteractionsNilN—H···ON—H···ON—H···ON—H···ON—H···ON—H···ON—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 architecture0D0D0D0D0D1 D chain0D0D
ReferenceVinola 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)
Notes: DA = dihedral angle; dc = dichloro; dm = dimethyl.
Comparison of various parameters in the crystal structures of N-(disubstituted phenyl)-2,4-dimethylbenzenesulfonamides (Series 2) top
Parameters2,3-dc2,4-dc3,4-dc3,5-dc2,3-dm2,4-dm2,6-dm3,4-dm3,5-dm
Crystal SystemMonoclinicTriclinicMonoclinicMonoclinicTriclinicTriclinicMonoclinicMonoclinicMonoclinic
Z'111121111
DA between the two aromatic rings70.4 (1)44.0 (1)82.4 (1)82.3 (2)41.5 (1), 43.8 (1)41.0 (1)41.7 (1)47.2 (2)82.1 (1)
Intermolecular InteractionsNilN—H···ON—H···ON—H···O, C—H···πN—H···ON—H···ON—H···ON—H···ON—H···O
Geometry of the N—H···O interactions-R22(8)C(4)R22(8)D(2)D(2)[R22(8)]R22(8)R22(8)C(4)R22(8)
Supramolecular architecture0D0D1D chain1D ribbon0D0D0D1D chain0D
ReferenceNirmala et al. (2010a)Nirmala et al. (2010b)Gowda et al. (2009b)Nirmala et al. (2010e)Nirmala et al. (2010c)Nirmala et al. (2010d)Nirmala et al. (2011)Gowda et al. (2010)Gowda et al. (2009c)
Notes: DA = dihedral angle; dc = dichloro; dm = dimethyl.
Comparison of various parameters in the crystal structures of 4-chloro-N-(disubstitutedphenyl)-2-methylbenzenesulfonamides (Series 3) top
Parameters2,3-dc3,4-dc3,5-dc2,3-dm2,4-dm2,5-dm2,6-dm3,4-dm
Crystal SystemMonoclinicMonoclinicTriclinicTriclinicMonoclinicTriclinicTriclinicTriclinic
Z'11121311
DA between the two aromatic rings69.6 (1)54.6 (1)84.2 (1)44.1 (1), 39.7 (1)44.5 (1)43.0 (2), 37.0 (2), 46.0 (1)38.8 (1)71.6 (1)
Intermolecular InteractionsN—H···ON—H···ON—H···ON—H···ON—H···ON—H···ON—H···ON—H···O
Geometry of the N—H···O interactionsC(4)C(4)R22(8)D(2)D(2)[R22(8)]R22(8)R22(8)R22(8)R22(8)
Supramolecular architecture1D chain1D chain0D0D0D0D0D0D
ReferenceVinola et al. (2011h)Vinola et al. (2011m)Vinola et al. (2011n)Vinola et al. (2011i)Vinola et al. (2011j)Vinola et al. (2011k)Vinola et al. (2011l)Vinola et al. (2011o)
Notes: DA = dihedral angle; dc = dichloro; dm = dimethyl.
Comparison of various parameters in the crystal structures of 3,5-dichloro-N-(disubstituted phenyl)benzenesulfonamides (Series 4) top
Parameters2,4-dc2,3-dm2,6-dm3,5-dm
Crystal SystemTriclinicMonoclinicTriclinicMonoclinic
Z'1111
DA between the two aromatic rings40.23 (2)41.3 (6)42.1 (2)54.4 (3)
Intermolecular InteractionsN—H···O, C—H···O, Cl···Cl, ππN—H···O, C—H···O, ππN—H···O, ππN—H···O, C—H···π, ππ
Geometry of the N—H···O interactionsR22(8)R22(8)R22(8)C(4)
Supramolecular architecture3D3D1D3D
ReferenceShakuntala et al. (2017b)Shakuntala et al. (2017a)Shakuntala et al. (2017a)Shakuntala et al. (2017a)
Notes: DA = dihedral angle; dc = dichloro; dm = dimethyl.
Comparison of various parameters in the crystal structures of N-aryl-2,5-dimethoxybenzenesulfonamides (Series 5) top
ParametersH2,3-dc (I)2,4-dc (II)2,4-dm (III)
Crystal SystemMonoclinicTriclinicTriclinicTriclinic
Z'1211
DA between the two aromatic rings89.17 (9)86.05 (2), 89.28 (2)71.57 (10)82.85 (1)
Intermolecular InteractionsN—H···ON—H···O, C—H···O, C—H···Cl, C—H···π, ππC—H···O, C—H···π, Cl···Cl, ππN—H···O
Geometry of the N—H···O interactionsR22(8)R22(8)-R22(8)
Supramolecular architecture0D2D2D0D
ReferenceShakuntala et al. (2017c)---
Notes: DA = dihedral angle; dc = dichloro; dm = dimethyl.
 

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