N-(2-Bromo-phen-yl)-4-methyl-N-(4-methyl-phen-ylsulfon-yl)benzene-sulfonamide.

Abstract

In the title compound, C(20)H(18)BrNO(4)S(2), the mean planes formed by the toluene substituents are inclined at a dihedral angle of 45.34 (8)°. The bromo-benzene group is disordered over two positions with an occupancy ratio of 0.74:0.26, resulting in two conformations of the ring; the two rings are oriented at a dihedral angle of 6.6 (6)° with each other. In the crystal structure, weak C-H⋯O inter-actions connect the mol-ecules in a zigzag manner along the a axis.

Full text

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N-(2-Bromophenyl)-4-methyl-N-(4-
methylphenylsulfonyl)benzene-
sulfonamide
Muhammad Nadeem Arshad,a,b* Islam Ullah Khan,b
K. Travis Holman,cAbdullah M. Asiridand H. M. Rafiquea
aX-ray Diffraction and Crystallography Laboratory, Department of Physics, School of
Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore-54590,
Pakistan,bMaterials Chemistry Laboratory, Department of Chemistry, GC University,
Lahore-54000, Pakistan,cDepartment of Chemistry, Goergetown University, 37th
and Oth Street NW, Washington, DC 20057, USA, anddThe Center of Excellence for
Advanced Materials Research, King Abdul Aziz University, Jeddah, PO Box 80203,
Saudi Arabia
Correspondence e-mail: mnachemist@hotmail.com
Received 8 August 2011; accepted 11 August 2011
Key indicators: single-crystal X-ray study; T = 100 K; mean ?(C–C) = 0.004 A ˚;
disorder in main residue; R factor = 0.038; wR factor = 0.085; data-to-parameter
ratio = 15.9.
In the title compound, C20H18BrNO4S2, the mean planes
formed by the toluene substituents are inclined at a dihedral
angle of 45.34 (8)?. The bromobenzene group is disordered
over two positions with an occupancy ratio of 0.74:0.26,
resulting in two conformations of the ring; the two rings are
oriented at a dihedral angle of 6.6 (6)?with each other. In the
crystal structure, weak C—H???O interactions connect the
molecules in a zigzag manner along the a axis.
Related literature
For general background, see: Ames & Opalko (1984); Arshad
et al. (2011). For related structures, see: Zhao et al. (2007);
Song (2008); Hanson & Hitchcock (2004).
Experimental
Crystal data
C20H18BrNO4S2
Mr= 480.38
Monoclinic, P21=c
a = 10.5819 (15) A˚
b = 13.1465 (19) A˚
c = 14.235 (2) A˚
? = 95.478 (2)?
V = 1971.2 (5) A˚3
Z = 4
Mo K? radiation
? = 2.32 mm?1
T = 100 K
0.38 ? 0.33 ? 0.24 mm
Data collection
Bruker KAPPA APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
Tmin= 0.472, Tmax= 0.605
23193 measured reflections
4792 independent reflections
4320 reflections with I > 2?(I)
Rint= 0.031
Refinement
R[F2> 2?(F2)] = 0.038
wR(F2) = 0.085
S = 1.24
4792 reflections
301 parameters
H-atom parameters constrained
??max= 0.52 e A˚?3
??min= ?0.53 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
C5—H5???O3i
Symmetry code: (i) ?x þ 1;y þ1
D—HH???AD???AD—H???A
0.952.453.199 (3)135
2;?z þ1
2.
Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT
(Bruker, 2001); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure:SHELXL97(Sheldrick,
PLATON (Spek, 2009) and X-SEED (Barbour, 2001); software used
to prepare material for publication: WinGX (Farrugia, 1999).
2008);molecular graphics:
MNA acknowledges the Higher Education Commission of
Pakistan for granting a scholarship under its indigenous and
IRSIP schemes.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: PV2443).
References
Ames, D. E. & Opalko, A. (1984). Tetrahedron, 40, 1919–1925.
Arshad, M. N., Khan, I. U., Zia-ur-Rehman, M. & Shafiq, M. (2011). Asian J.
Chem. 23, 2801–2805.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2001). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison,
Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Hanson, J. R. & Hitchcock, P. B. (2004). J. Chem. Res. pp. 614–616.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Song, Z.-W. (2008). Acta Cryst. E64, o744.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Zhao, K.-J., Wu, X.-X., Wang, G. & Hu, M.-L. (2007). Acta Cryst. E63, o4472.
organic compounds
o2356
Arshad et al.
doi:10.1107/S1600536811032533
Acta Cryst. (2011). E67, o2356
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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sup-1
Acta Cryst. (2011). E67, o2356 [ doi:10.1107/S1600536811032533 ]
N-(2-Bromophenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide
M. N. Arshad, I. U. Khan, K. T. Holman, A. M. Asiri and H. M. Rafique
Comment
O-Bromoaryl sulfonamides have been used for intramolecular arylation via palladium catalysis (Ames & Opalko, 1984).
Herein, we report the crystal structure of the title compound which was synthesised as a precursor of cyclic sultams (Arshad
et al., 2011).
The N-atom of O-bromoaniline is directly attached to two p-toluene sulfonyl moieties. The interesting feature in the
crystal structure is that bromobenzene group is disordered over two positions (C15—C20/Br1) and (C21—C26/Br2) with
the occupancy of 0.74 and 0.26, respectively. The dihedral angle between the two disordered parts of the ring is 6.6 (6)°.
The two toluene rings (C1—C7) & (C8—C14) are oriented at dihedral angle of 45.34 (89)°. The part (C15—C20/Br1)
of bromobenzene ring formed dihedral angles of 24.0 (2)° and 38.77 (11)° with both of the toluene rings (C1—C7) &
(C8—C14,) respectively, while the other part is oriented at dihedral angles of 19.6 (6)° and 34.8 (2)° with respect to the
toluene rings. No classical hydrogen bonding has been observed in the molecule, only C—H···O type interactions connect
the molecules in a zig-zag mode (Fig. 2 and Tab. 1).
Experimental
A mixture of 2-bromoaniline (300 mg, 1.7 mmol) and triethylamine (529 mg, 5.2 mmol) was prepared in dichloromethane
(20ml). Toluene sulfonylchloride (650 mg, 3.4 mmol) was added to the mixture and stirred for about two hours. The mixture
was poured on ice and pH was adjusted about 2-3. The precipitate obtained was filtered, washed and dried. Suitable crystals
were produced in methanol by slow evaporation.
Refinement
The H-atoms were positioned at idealized geometry with C—H = 0.95 and 0.98 Å for aryl and methyl groups, respectively,
and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) for aromatic & Uiso(H) = 1.5 Ueq(C) for methyl groups.
The bromobenzene ring was disordered over two positions with occupancy ratio 0.74: 0.26. The occupancy factors were
established in earlier stages of refinement and were fixed in the final refinement cycles. The benzene ring of the smaller
fraction of the bromobenzene fragment was constrained as a regular hexagon
Figures
Fig. 1. An ORTEP diagram of the title compound with thermal ellipsoids drawn at the 50%
probability level; smaller fraction of the disordered bromobenzene ring has been plotted with
dashed lines.

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Fig. 2. Unit cell packing for the title compound showing weak C—H···O interactions as
dashed lines.
N-(2-Bromophenyl)-4-methyl-N- (4-methylphenylsulfonyl)benzenesulfonamide
Crystal data
C20H18BrNO4S2
F(000) = 976
Dx = 1.679 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9904 reflections
θ = 2.3–28.1°
µ = 2.32 mm−1
T = 100 K
Blocks, colorless
Mr = 480.38
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 10.5819 (15) Å
b = 13.1465 (19) Å
c = 14.235 (2) Å
β = 95.478 (2)°
V = 1971.2 (5) Å3
Z = 4
0.38 × 0.33 × 0.24 mm
Data collection
Bruker KAPPA APEXII CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
Tmin = 0.472, Tmax = 0.605
23193 measured reflections
4792 independent reflections
4320 reflections with I > 2σ(I)
Rint = 0.031
θmax = 28.3°, θmin = 1.9°
h = −14→13
k = −17→17
l = −18→18
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.038
wR(F2) = 0.085
H-atom parameters constrained
S = 1.24
w = 1/[σ2(Fo2) + (0.0125P)2 + 3.1006P]
where P = (Fo2 + 2Fc2)/3

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4792 reflections
(Δ/σ)max = 0.001
Δρmax = 0.52 e Å−3
Δρmin = −0.53 e Å−3
301 parameters
0 restraints
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The
cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds
in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used
for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, convention-
al R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculat-
ing R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice
as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.25875 (4)
−0.06672 (10)
0.30298 (5)
0.19193 (5)
0.06261 (16)
0.42299 (16)
0.27382 (16)
0.26821 (17)
0.18608 (18)
0.2899 (2)
0.1987 (2)
0.1401
0.1949 (2)
0.1324
0.2817 (2)
0.3712 (2)
0.4299
0.3756 (2)
0.4363
0.2787 (2)
0.3330
0.3100
0.1914
0.2633 (2)
0.3953 (2)
0.4458
0.4515 (2)
0.5415
0.3788 (3)
y
0.31399 (3)
0.62953 (9)
0.58728 (4)
0.55064 (5)
0.55206 (14)
0.56000 (13)
0.63481 (13)
0.55219 (13)
0.54032 (15)
0.72024 (17)
0.76797 (19)
0.7290
0.87387 (19)
0.9074
0.93112 (18)
0.88108 (18)
0.9197
0.77596 (19)
0.7424
1.04533 (19)
1.0680
1.0743
1.0681
0.43825 (19)
0.4307 (2)
0.4872
0.3396 (2)
0.3342
0.2558 (2)
z
0.20992 (2)
0.15927 (9)
0.18802 (4)
0.36828 (4)
0.38987 (12)
0.23665 (13)
0.39241 (12)
0.09413 (12)
0.24974 (13)
0.19019 (17)
0.12845 (17)
0.0885
0.12623 (18)
0.0850
0.18389 (17)
0.24575 (18)
0.2858
0.24962 (17)
0.2923
0.1779 (2)
0.1298
0.2392
0.1607
0.41368 (17)
0.42161 (17)
0.4069
0.45122 (18)
0.4573
0.47224 (19)
Uiso*/Ueq
0.02691 (9)
0.0346 (3)
0.01811 (12)
0.01938 (12)
0.0240 (4)
0.0239 (4)
0.0236 (4)
0.0237 (4)
0.0180 (4)
0.0185 (4)
0.0214 (5)
0.026*
0.0225 (5)
0.027*
0.0206 (5)
0.0219 (5)
0.026*
0.0216 (5)
0.026*
0.0261 (5)
0.039*
0.039*
0.039*
0.0220 (5)
0.0236 (5)
0.028*
0.0264 (5)
0.032*
0.0291 (6)
Occ. (<1)
0.74
0.26
Br1
Br2
S1
S2
O2
O3
O4
O7
N1
C1
C2
H2
C3
H3
C4
C5
H5
C6
H6
C7
H7A
H7B
H7C
C8
C9
H9
C10
H10
C11

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supplementary materials
sup-4
C12
H12
C13
H13
C14
H14A
H14B
H14C
C15
C16
C17
H17
C18
H18
C19
H19
C20
H20
C21
C22
H22
C23
H23
C24
H24
C25
H25
C26
0.2467 (3)
0.1960
0.1884 (3)
0.0986
0.4414 (3)
0.3871
0.5238
0.4538
0.0847 (5)
0.1015 (5)
0.0016 (5)
0.0112
−0.1120 (5)
−0.1805
−0.1272 (4)
−0.2045
−0.0293 (5)
−0.0404
0.1025 (10)
0.1370 (9)
0.2186
0.0520 (12)
0.0756
−0.0673 (11)
−0.1254
−0.1018 (8)
−0.1834
−0.0169 (10)
0.2666 (2)
0.2107
0.3570 (2)
0.3634
0.1552 (2)
0.1155
0.1670
0.1175
0.4829 (4)
0.3805 (4)
0.3249 (3)
0.2545
0.3739 (5)
0.3365
0.4763 (4)
0.5095
0.5305 (4)
0.6005
0.4648 (7)
0.3627 (8)
0.3422
0.2907 (6)
0.2210
0.3207 (8)
0.2715
0.4227 (9)
0.4432
0.4947 (6)
0.4662 (2)
0.4823
0.4371 (2)
0.4333
0.4977 (2)
0.5361
0.5335
0.4399
0.2018 (3)
0.1793 (4)
0.1337 (3)
0.1213
0.1067 (3)
0.0755
0.1243 (3)
0.1033
0.1728 (3)
0.1862
0.1985 (9)
0.1979 (8)
0.2249
0.1578 (7)
0.1574
0.1183 (6)
0.0909
0.1189 (7)
0.0919
0.1590 (8)
0.0335 (6)
0.040*
0.0295 (6)
0.035*
0.0378 (7)
0.057*
0.057*
0.057*
0.0202 (11)
0.0237 (10)
0.0275 (9)
0.033*
0.0291 (10)
0.035*
0.0275 (9)
0.033*
0.0213 (9)
0.026*
0.012 (4)*
0.025 (4)
0.030*
0.038 (3)
0.046*
0.043 (4)
0.052*
0.028 (3)
0.034*
0.024 (3)
0.74
0.74
0.74
0.74
0.74
0.74
0.74
0.74
0.74
0.74
0.26
0.26
0.26
0.26
0.26
0.26
0.26
0.26
0.26
0.26
Atomic displacement parameters (Å2)
U11
0.03615 (19)
0.0257 (5)
0.0176 (3)
0.0177 (3)
0.0198 (8)
0.0193 (8)
0.0249 (9)
0.0282 (9)
0.0181 (9)
0.0197 (11)
0.0208 (11)
0.0208 (11)
0.0199 (11)
0.0201 (11)
0.0199 (11)
0.0249 (12)
U22
0.01695 (15)
0.0338 (6)
0.0155 (3)
0.0218 (3)
0.0302 (9)
0.0196 (8)
0.0241 (9)
0.0207 (8)
0.0184 (9)
0.0141 (10)
0.0214 (12)
0.0221 (12)
0.0166 (11)
0.0199 (11)
0.0213 (12)
0.0175 (11)
U33
0.02757 (18)
0.0445 (6)
0.0215 (3)
0.0185 (3)
0.0221 (9)
0.0327 (10)
0.0215 (9)
0.0232 (9)
0.0175 (9)
0.0220 (11)
0.0216 (12)
0.0247 (12)
0.0267 (12)
0.0256 (12)
0.0233 (12)
0.0367 (14)
U12
0.00531 (14)
0.0085 (4)
0.0006 (2)
−0.0002 (2)
0.0010 (7)
0.0025 (7)
−0.0024 (7)
−0.0016 (7)
−0.0026 (8)
0.0007 (8)
−0.0004 (9)
0.0034 (9)
0.0008 (9)
−0.0042 (9)
0.0000 (9)
0.0030 (9)
U13
0.00269 (14)
0.0044 (4)
0.0035 (2)
0.0010 (2)
0.0028 (7)
0.0020 (7)
0.0003 (7)
0.0069 (7)
0.0016 (7)
0.0037 (9)
−0.0008 (9)
0.0026 (9)
0.0094 (9)
0.0022 (9)
−0.0001 (9)
0.0072 (11)
U23
−0.00062 (13)
0.0156 (5)
0.0015 (2)
0.0017 (2)
0.0013 (7)
0.0044 (7)
−0.0010 (7)
−0.0007 (7)
−0.0001 (7)
0.0023 (9)
0.0015 (9)
0.0065 (9)
0.0033 (9)
0.0005 (9)
0.0046 (9)
0.0042 (10)
Br1
Br2
S1
S2
O2
O3
O4
O7
N1
C1
C2
C3
C4
C5
C6
C7

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sup-5
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C22
C23
C24
C25
C26
0.0204 (11)
0.0211 (12)
0.0217 (12)
0.0308 (14)
0.0281 (14)
0.0215 (12)
0.0371 (16)
0.024 (2)
0.029 (2)
0.040 (3)
0.032 (3)
0.024 (2)
0.0201 (19)
0.050 (10)
0.066 (10)
0.065 (13)
0.030 (7)
0.027 (6)
0.0246 (12)
0.0281 (13)
0.0341 (14)
0.0323 (14)
0.0325 (15)
0.0332 (14)
0.0335 (15)
0.0188 (18)
0.023 (2)
0.018 (2)
0.033 (3)
0.035 (2)
0.026 (3)
0.012 (6)
0.021 (6)
0.042 (10)
0.029 (9)
0.028 (8)
0.0207 (11)
0.0212 (12)
0.0231 (12)
0.0249 (13)
0.0412 (16)
0.0340 (14)
0.0436 (17)
0.019 (2)
0.020 (2)
0.025 (2)
0.022 (2)
0.0238 (19)
0.018 (2)
0.013 (6)
0.029 (7)
0.023 (7)
0.025 (6)
0.017 (6)
0.0016 (9)
−0.0026 (10)
0.0026 (10)
0.0049 (11)
0.0007 (11)
−0.0008 (11)
0.0088 (13)
−0.0033 (19)
−0.0013 (18)
−0.011 (2)
−0.017 (2)
−0.0046 (18)
−0.0012 (17)
−0.003 (6)
−0.010 (6)
−0.033 (10)
−0.021 (7)
0.006 (6)
0.0002 (9)
−0.0007 (9)
0.0009 (10)
0.0058 (11)
0.0094 (12)
0.0047 (11)
0.0087 (13)
0.0044 (16)
0.0029 (18)
0.006 (2)
0.0014 (17)
0.0000 (14)
0.0031 (14)
0.004 (6)
0.017 (6)
0.010 (8)
−0.003 (5)
0.005 (5)
0.0067 (9)
0.0044 (10)
0.0049 (10)
0.0100 (11)
0.0171 (12)
0.0121 (12)
0.0165 (13)
−0.0018 (15)
0.0049 (17)
−0.0035 (16)
−0.004 (2)
0.0022 (19)
−0.0011 (18)
−0.002 (5)
0.001 (5)
0.002 (6)
0.006 (7)
0.002 (5)
Geometric parameters (Å, °)
Br1—C16
Br2—C26
S1—O7
S1—O3
S1—N1
S1—C1
S2—O4
S2—O2
S2—N1
S2—C8
N1—C15
N1—C21
C1—C6
C1—C2
C2—C3
C2—H2
C3—C4
C3—H3
C4—C5
C4—C7
C5—C6
C5—H5
C6—H6
C7—H7A
C7—H7B
C7—H7C
C8—C13
C8—C9
1.893 (5)
1.849 (8)
1.4284 (18)
1.4328 (18)
1.700 (2)
1.754 (2)
1.4271 (18)
1.4310 (18)
1.688 (2)
1.755 (2)
1.431 (4)
1.475 (8)
1.389 (3)
1.391 (3)
1.393 (3)
0.9500
1.393 (4)
0.9500
1.395 (3)
1.504 (3)
1.384 (3)
0.9500
0.9500
0.9800
0.9800
0.9800
1.390 (4)
1.393 (3)
C10—C11
C10—H10
C11—C12
C11—C14
C12—C13
C12—H12
C13—H13
C14—H14A
C14—H14B
C14—H14C
C15—C20
C15—C16
C16—C17
C17—C18
C17—H17
C18—C19
C18—H18
C19—C20
C19—H19
C20—H20
C21—C22
C21—C26
C22—C23
C22—H22
C23—C24
C23—H23
C24—C25
C24—H24
1.393 (4)
0.9500
1.399 (4)
1.509 (4)
1.384 (4)
0.9500
0.9500
0.9800
0.9800
0.9800
1.386 (7)
1.399 (8)
1.394 (7)
1.385 (7)
0.9500
1.382 (7)
0.9500
1.385 (6)
0.9500
0.9500
1.3900
1.3900
1.3900
0.9500
1.3900
0.9500
1.3900
0.9500

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supplementary materials
sup-6
C9—C10
C9—H9
1.385 (4)
0.9500
C25—C26
C25—H25
1.3900
0.9500
O7—S1—O3
O7—S1—N1
O3—S1—N1
O7—S1—C1
O3—S1—C1
N1—S1—C1
O4—S2—O2
O4—S2—N1
O2—S2—N1
O4—S2—C8
O2—S2—C8
N1—S2—C8
C15—N1—C21
C15—N1—S2
C21—N1—S2
C15—N1—S1
C21—N1—S1
S2—N1—S1
C6—C1—C2
C6—C1—S1
C2—C1—S1
C1—C2—C3
C1—C2—H2
C3—C2—H2
C4—C3—C2
C4—C3—H3
C2—C3—H3
C3—C4—C5
C3—C4—C7
C5—C4—C7
C6—C5—C4
C6—C5—H5
C4—C5—H5
C5—C6—C1
C5—C6—H6
C1—C6—H6
C4—C7—H7A
C4—C7—H7B
H7A—C7—H7B
C4—C7—H7C
H7A—C7—H7C
H7B—C7—H7C
C13—C8—C9
C13—C8—S2
C9—C8—S2
C10—C9—C8
C10—C9—H9
120.57 (11)
103.36 (10)
108.33 (10)
108.94 (11)
107.99 (11)
106.86 (10)
120.62 (11)
105.45 (10)
105.73 (10)
109.51 (11)
108.59 (11)
105.90 (11)
12.1 (5)
118.3 (2)
120.7 (6)
119.6 (2)
114.9 (6)
121.89 (12)
121.3 (2)
119.23 (18)
119.32 (18)
118.8 (2)
120.6
120.6
120.7 (2)
119.7
119.7
119.1 (2)
119.8 (2)
121.0 (2)
121.0 (2)
119.5
119.5
119.0 (2)
120.5
120.5
109.5
109.5
109.5
109.5
109.5
109.5
121.0 (2)
120.03 (19)
118.86 (19)
119.0 (2)
120.5
C10—C11—C12
C10—C11—C14
C12—C11—C14
C13—C12—C11
C13—C12—H12
C11—C12—H12
C12—C13—C8
C12—C13—H13
C8—C13—H13
C11—C14—H14A
C11—C14—H14B
H14A—C14—H14B
C11—C14—H14C
H14A—C14—H14C
H14B—C14—H14C
C20—C15—C16
C20—C15—N1
C16—C15—N1
C17—C16—C15
C17—C16—Br1
C15—C16—Br1
C18—C17—C16
C18—C17—H17
C16—C17—H17
C19—C18—C17
C19—C18—H18
C17—C18—H18
C18—C19—C20
C18—C19—H19
C20—C19—H19
C19—C20—C15
C19—C20—H20
C15—C20—H20
C22—C21—C26
C22—C21—N1
C26—C21—N1
C23—C22—C21
C23—C22—H22
C21—C22—H22
C22—C23—C24
C22—C23—H23
C24—C23—H23
C23—C24—C25
C23—C24—H24
C25—C24—H24
C26—C25—C24
C26—C25—H25
118.4 (2)
120.4 (2)
121.1 (3)
121.3 (3)
119.4
119.4
118.9 (2)
120.5
120.5
109.5
109.5
109.5
109.5
109.5
109.5
119.5 (4)
119.7 (5)
120.7 (5)
120.2 (5)
118.4 (4)
121.4 (4)
119.0 (4)
120.5
120.5
121.0 (4)
119.5
119.5
119.8 (4)
120.1
120.1
120.3 (4)
119.9
119.9
120.0
120.5 (7)
119.2 (7)
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0
120.0

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supplementary materials
sup-7
C8—C9—H9
C9—C10—C11
C9—C10—H10
C11—C10—H10
120.5
121.2 (2)
119.4
119.4
C24—C25—H25
C25—C26—C21
C25—C26—Br2
C21—C26—Br2
120.0
120.0
118.7 (6)
121.3 (6)
O4—S2—N1—C15
O2—S2—N1—C15
C8—S2—N1—C15
O4—S2—N1—C21
O2—S2—N1—C21
C8—S2—N1—C21
O4—S2—N1—S1
O2—S2—N1—S1
C8—S2—N1—S1
O7—S1—N1—C15
O3—S1—N1—C15
C1—S1—N1—C15
O7—S1—N1—C21
O3—S1—N1—C21
C1—S1—N1—C21
O7—S1—N1—S2
O3—S1—N1—S2
C1—S1—N1—S2
O7—S1—C1—C6
O3—S1—C1—C6
N1—S1—C1—C6
O7—S1—C1—C2
O3—S1—C1—C2
N1—S1—C1—C2
C6—C1—C2—C3
S1—C1—C2—C3
C1—C2—C3—C4
C2—C3—C4—C5
C2—C3—C4—C7
C3—C4—C5—C6
C7—C4—C5—C6
C4—C5—C6—C1
C2—C1—C6—C5
S1—C1—C6—C5
O4—S2—C8—C13
O2—S2—C8—C13
N1—S2—C8—C13
O4—S2—C8—C9
O2—S2—C8—C9
N1—S2—C8—C9
C13—C8—C9—C10
S2—C8—C9—C10
−162.2 (3)
−33.4 (4)
81.8 (3)
−175.9 (5)
−47.0 (5)
68.1 (5)
23.07 (16)
151.89 (13)
−92.98 (15)
−1.2 (4)
−130.2 (3)
113.7 (3)
11.4 (5)
−117.6 (5)
126.2 (5)
173.46 (13)
44.46 (16)
−71.67 (16)
−145.08 (19)
−12.5 (2)
103.9 (2)
31.2 (2)
163.77 (19)
−79.9 (2)
0.5 (4)
−175.65 (19)
0.8 (4)
−1.4 (4)
177.8 (2)
0.8 (4)
−178.5 (2)
0.5 (4)
−1.2 (4)
174.99 (19)
151.7 (2)
18.1 (3)
−95.1 (2)
−31.2 (2)
−164.8 (2)
82.1 (2)
1.6 (4)
−175.6 (2)
C8—C9—C10—C11
C9—C10—C11—C12
C9—C10—C11—C14
C10—C11—C12—C13
C14—C11—C12—C13
C11—C12—C13—C8
C9—C8—C13—C12
S2—C8—C13—C12
C21—N1—C15—C20
S2—N1—C15—C20
S1—N1—C15—C20
C21—N1—C15—C16
S2—N1—C15—C16
S1—N1—C15—C16
C20—C15—C16—C17
N1—C15—C16—C17
C20—C15—C16—Br1
N1—C15—C16—Br1
C15—C16—C17—C18
Br1—C16—C17—C18
C16—C17—C18—C19
C17—C18—C19—C20
C18—C19—C20—C15
C16—C15—C20—C19
N1—C15—C20—C19
C15—N1—C21—C22
S2—N1—C21—C22
S1—N1—C21—C22
C15—N1—C21—C26
S2—N1—C21—C26
S1—N1—C21—C26
C26—C21—C22—C23
N1—C21—C22—C23
C21—C22—C23—C24
C22—C23—C24—C25
C23—C24—C25—C26
C24—C25—C26—C21
C24—C25—C26—Br2
C22—C21—C26—C25
N1—C21—C26—C25
C22—C21—C26—Br2
N1—C21—C26—Br2
0.6 (4)
−2.3 (4)
175.6 (3)
2.1 (4)
−175.9 (3)
0.0 (4)
−1.8 (4)
175.3 (2)
−167 (4)
88.1 (4)
−97.1 (4)
10 (3)
−95.3 (4)
79.5 (4)
−4.2 (6)
179.2 (5)
175.9 (4)
−0.7 (6)
3.3 (7)
−176.8 (4)
−0.1 (7)
−2.3 (8)
1.4 (7)
1.8 (6)
178.5 (4)
−159 (4)
−77.5 (7)
84.8 (7)
14 (3)
95.9 (7)
−101.7 (6)
0.0
173.4 (11)
0.0
0.0
0.0
0.0
−179.5 (8)
0.0
−173.5 (11)
179.5 (8)
6.0 (8)

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supplementary materials
sup-8
Hydrogen-bond geometry (Å, °)
D—H···A
C5—H5···O3i
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
D—HH···AD···AD—H···A
0.952.453.199 (3)135.

Page 11

supplementary materials
sup-9
Fig. 1

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supplementary materials
sup-10
Fig. 2