N-(2-Bromo­phen­yl)-4-methyl-N-(4-methyl­phen­ylsulfon­yl)benzene­sulfonamide

Arshad, M.N.; Khan, I.U.; Holman, K.T.; Asiri, A.M.; Rafique, H.M.

doi:10.1107/S1600536811032533

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2356

doi:10.1107/S1600536811032533

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N-(2-Bromophenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide

Muhammad Nadeem Arshad,^a,^b ^* Islam Ullah Khan,^b K. Travis Holman,^c Abdullah M. Asiri ^d and H. M. Rafique ^a

^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, and ^dThe 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; online 17 August 2011)

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
M_r = 480.38
Monoclinic, P 2₁ /c
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
Mo Kα radiation
μ = 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 ) T_min = 0.472, T_max = 0.605
23193 measured reflections
4792 independent reflections
4320 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.085
S = 1.24
4792 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.95	2.45	3.199 (3)	135
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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, 2008); molecular graphics: PLATON (Spek, 2009 ) and X-SEED (Barbour, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811032533/pv2443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032533/pv2443Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032533/pv2443Isup3.cml

checkCIF report

Comment top

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).

Related literature top

For general background, see: Ames & Opalko (1984); Arshad et al. (2011). For related crystal structures, see: Zhao et al. (2007); Song (2008); Hanson & Hitchcock (2004).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	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.
	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 top

Crystal data top

C₂₀H₁₈BrNO₄S₂	F(000) = 976
M_r = 480.38	D_x = 1.679 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9904 reflections
a = 10.5819 (15) Å	θ = 2.3–28.1°
b = 13.1465 (19) Å	µ = 2.32 mm⁻¹
c = 14.235 (2) Å	T = 100 K
β = 95.478 (2)°	Blocks, colorless
V = 1971.2 (5) Å³	0.38 × 0.33 × 0.24 mm
Z = 4

Data collection top

Bruker KAPPA APEXII CCD diffractometer	4792 independent reflections
Radiation source: fine-focus sealed tube	4320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→13
T_min = 0.472, T_max = 0.605	k = −17→17
23193 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.24	w = 1/[σ²(F_o²) + (0.0125P)² + 3.1006P] where P = (F_o² + 2F_c²)/3
4792 reflections	(Δ/σ)_max = 0.001
301 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₂₀H₁₈BrNO₄S₂	V = 1971.2 (5) Å³
M_r = 480.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5819 (15) Å	µ = 2.32 mm⁻¹
b = 13.1465 (19) Å	T = 100 K
c = 14.235 (2) Å	0.38 × 0.33 × 0.24 mm
β = 95.478 (2)°

Data collection top

Bruker KAPPA APEXII CCD diffractometer	4792 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4320 reflections with I > 2σ(I)
T_min = 0.472, T_max = 0.605	R_int = 0.031
23193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.24	Δρ_max = 0.52 e Å⁻³
4792 reflections	Δρ_min = −0.53 e Å⁻³
301 parameters

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional 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 calculating 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) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.25875 (4)	0.31399 (3)	0.20992 (2)	0.02691 (9)	0.74
Br2	−0.06672 (10)	0.62953 (9)	0.15927 (9)	0.0346 (3)	0.26
S1	0.30298 (5)	0.58728 (4)	0.18802 (4)	0.01811 (12)
S2	0.19193 (5)	0.55064 (5)	0.36828 (4)	0.01938 (12)
O2	0.06261 (16)	0.55206 (14)	0.38987 (12)	0.0240 (4)
O3	0.42299 (16)	0.56000 (13)	0.23665 (13)	0.0239 (4)
O4	0.27382 (16)	0.63481 (13)	0.39241 (12)	0.0236 (4)
O7	0.26821 (17)	0.55219 (13)	0.09413 (12)	0.0237 (4)
N1	0.18608 (18)	0.54032 (15)	0.24974 (13)	0.0180 (4)
C1	0.2899 (2)	0.72024 (17)	0.19019 (17)	0.0185 (4)
C2	0.1987 (2)	0.76797 (19)	0.12845 (17)	0.0214 (5)
H2	0.1401	0.7290	0.0885	0.026*
C3	0.1949 (2)	0.87387 (19)	0.12623 (18)	0.0225 (5)
H3	0.1324	0.9074	0.0850	0.027*
C4	0.2817 (2)	0.93112 (18)	0.18389 (17)	0.0206 (5)
C5	0.3712 (2)	0.88108 (18)	0.24575 (18)	0.0219 (5)
H5	0.4299	0.9197	0.2858	0.026*
C6	0.3756 (2)	0.77596 (19)	0.24962 (17)	0.0216 (5)
H6	0.4363	0.7424	0.2923	0.026*
C7	0.2787 (2)	1.04533 (19)	0.1779 (2)	0.0261 (5)
H7A	0.3330	1.0680	0.1298	0.039*
H7B	0.3100	1.0743	0.2392	0.039*
H7C	0.1914	1.0681	0.1607	0.039*
C8	0.2633 (2)	0.43825 (19)	0.41368 (17)	0.0220 (5)
C9	0.3953 (2)	0.4307 (2)	0.42161 (17)	0.0236 (5)
H9	0.4458	0.4872	0.4069	0.028*
C10	0.4515 (2)	0.3396 (2)	0.45122 (18)	0.0264 (5)
H10	0.5415	0.3342	0.4573	0.032*
C11	0.3788 (3)	0.2558 (2)	0.47224 (19)	0.0291 (6)
C12	0.2467 (3)	0.2666 (2)	0.4662 (2)	0.0335 (6)
H12	0.1960	0.2107	0.4823	0.040*
C13	0.1884 (3)	0.3570 (2)	0.4371 (2)	0.0295 (6)
H13	0.0986	0.3634	0.4333	0.035*
C14	0.4414 (3)	0.1552 (2)	0.4977 (2)	0.0378 (7)
H14A	0.3871	0.1155	0.5361	0.057*
H14B	0.5238	0.1670	0.5335	0.057*
H14C	0.4538	0.1175	0.4399	0.057*
C15	0.0847 (5)	0.4829 (4)	0.2018 (3)	0.0202 (11)	0.74
C16	0.1015 (5)	0.3805 (4)	0.1793 (4)	0.0237 (10)	0.74
C17	0.0016 (5)	0.3249 (3)	0.1337 (3)	0.0275 (9)	0.74
H17	0.0112	0.2545	0.1213	0.033*	0.74
C18	−0.1120 (5)	0.3739 (5)	0.1067 (3)	0.0291 (10)	0.74
H18	−0.1805	0.3365	0.0755	0.035*	0.74
C19	−0.1272 (4)	0.4763 (4)	0.1243 (3)	0.0275 (9)	0.74
H19	−0.2045	0.5095	0.1033	0.033*	0.74
C20	−0.0293 (5)	0.5305 (4)	0.1728 (3)	0.0213 (9)	0.74
H20	−0.0404	0.6005	0.1862	0.026*	0.74
C21	0.1025 (10)	0.4648 (7)	0.1985 (9)	0.012 (4)*	0.26
C22	0.1370 (9)	0.3627 (8)	0.1979 (8)	0.025 (4)	0.26
H22	0.2186	0.3422	0.2249	0.030*	0.26
C23	0.0520 (12)	0.2907 (6)	0.1578 (7)	0.038 (3)	0.26
H23	0.0756	0.2210	0.1574	0.046*	0.26
C24	−0.0673 (11)	0.3207 (8)	0.1183 (6)	0.043 (4)	0.26
H24	−0.1254	0.2715	0.0909	0.052*	0.26
C25	−0.1018 (8)	0.4227 (9)	0.1189 (7)	0.028 (3)	0.26
H25	−0.1834	0.4432	0.0919	0.034*	0.26
C26	−0.0169 (10)	0.4947 (6)	0.1590 (8)	0.024 (3)	0.26

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03615 (19)	0.01695 (15)	0.02757 (18)	0.00531 (14)	0.00269 (14)	−0.00062 (13)
Br2	0.0257 (5)	0.0338 (6)	0.0445 (6)	0.0085 (4)	0.0044 (4)	0.0156 (5)
S1	0.0176 (3)	0.0155 (3)	0.0215 (3)	0.0006 (2)	0.0035 (2)	0.0015 (2)
S2	0.0177 (3)	0.0218 (3)	0.0185 (3)	−0.0002 (2)	0.0010 (2)	0.0017 (2)
O2	0.0198 (8)	0.0302 (9)	0.0221 (9)	0.0010 (7)	0.0028 (7)	0.0013 (7)
O3	0.0193 (8)	0.0196 (8)	0.0327 (10)	0.0025 (7)	0.0020 (7)	0.0044 (7)
O4	0.0249 (9)	0.0241 (9)	0.0215 (9)	−0.0024 (7)	0.0003 (7)	−0.0010 (7)
O7	0.0282 (9)	0.0207 (8)	0.0232 (9)	−0.0016 (7)	0.0069 (7)	−0.0007 (7)
N1	0.0181 (9)	0.0184 (9)	0.0175 (9)	−0.0026 (8)	0.0016 (7)	−0.0001 (7)
C1	0.0197 (11)	0.0141 (10)	0.0220 (11)	0.0007 (8)	0.0037 (9)	0.0023 (9)
C2	0.0208 (11)	0.0214 (12)	0.0216 (12)	−0.0004 (9)	−0.0008 (9)	0.0015 (9)
C3	0.0208 (11)	0.0221 (12)	0.0247 (12)	0.0034 (9)	0.0026 (9)	0.0065 (9)
C4	0.0199 (11)	0.0166 (11)	0.0267 (12)	0.0008 (9)	0.0094 (9)	0.0033 (9)
C5	0.0201 (11)	0.0199 (11)	0.0256 (12)	−0.0042 (9)	0.0022 (9)	0.0005 (9)
C6	0.0199 (11)	0.0213 (12)	0.0233 (12)	0.0000 (9)	−0.0001 (9)	0.0046 (9)
C7	0.0249 (12)	0.0175 (11)	0.0367 (14)	0.0030 (9)	0.0072 (11)	0.0042 (10)
C8	0.0204 (11)	0.0246 (12)	0.0207 (11)	0.0016 (9)	0.0002 (9)	0.0067 (9)
C9	0.0211 (12)	0.0281 (13)	0.0212 (12)	−0.0026 (10)	−0.0007 (9)	0.0044 (10)
C10	0.0217 (12)	0.0341 (14)	0.0231 (12)	0.0026 (10)	0.0009 (10)	0.0049 (10)
C11	0.0308 (14)	0.0323 (14)	0.0249 (13)	0.0049 (11)	0.0058 (11)	0.0100 (11)
C12	0.0281 (14)	0.0325 (15)	0.0412 (16)	0.0007 (11)	0.0094 (12)	0.0171 (12)
C13	0.0215 (12)	0.0332 (14)	0.0340 (14)	−0.0008 (11)	0.0047 (11)	0.0121 (12)
C14	0.0371 (16)	0.0335 (15)	0.0436 (17)	0.0088 (13)	0.0087 (13)	0.0165 (13)
C15	0.024 (2)	0.0188 (18)	0.019 (2)	−0.0033 (19)	0.0044 (16)	−0.0018 (15)
C16	0.029 (2)	0.023 (2)	0.020 (2)	−0.0013 (18)	0.0029 (18)	0.0049 (17)
C17	0.040 (3)	0.018 (2)	0.025 (2)	−0.011 (2)	0.006 (2)	−0.0035 (16)
C18	0.032 (3)	0.033 (3)	0.022 (2)	−0.017 (2)	0.0014 (17)	−0.004 (2)
C19	0.024 (2)	0.035 (2)	0.0238 (19)	−0.0046 (18)	0.0000 (14)	0.0022 (19)
C20	0.0201 (19)	0.026 (3)	0.018 (2)	−0.0012 (17)	0.0031 (14)	−0.0011 (18)
C22	0.050 (10)	0.012 (6)	0.013 (6)	−0.003 (6)	0.004 (6)	−0.002 (5)
C23	0.066 (10)	0.021 (6)	0.029 (7)	−0.010 (6)	0.017 (6)	0.001 (5)
C24	0.065 (13)	0.042 (10)	0.023 (7)	−0.033 (10)	0.010 (8)	0.002 (6)
C25	0.030 (7)	0.029 (9)	0.025 (6)	−0.021 (7)	−0.003 (5)	0.006 (7)
C26	0.027 (6)	0.028 (8)	0.017 (6)	0.006 (6)	0.005 (5)	0.002 (5)

Geometric parameters (Å, º) top

Br1—C16	1.893 (5)	C10—C11	1.393 (4)
Br2—C26	1.849 (8)	C10—H10	0.9500
S1—O7	1.4284 (18)	C11—C12	1.399 (4)
S1—O3	1.4328 (18)	C11—C14	1.509 (4)
S1—N1	1.700 (2)	C12—C13	1.384 (4)
S1—C1	1.754 (2)	C12—H12	0.9500
S2—O4	1.4271 (18)	C13—H13	0.9500
S2—O2	1.4310 (18)	C14—H14A	0.9800
S2—N1	1.688 (2)	C14—H14B	0.9800
S2—C8	1.755 (2)	C14—H14C	0.9800
N1—C15	1.431 (4)	C15—C20	1.386 (7)
N1—C21	1.475 (8)	C15—C16	1.399 (8)
C1—C6	1.389 (3)	C16—C17	1.394 (7)
C1—C2	1.391 (3)	C17—C18	1.385 (7)
C2—C3	1.393 (3)	C17—H17	0.9500
C2—H2	0.9500	C18—C19	1.382 (7)
C3—C4	1.393 (4)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.385 (6)
C4—C5	1.395 (3)	C19—H19	0.9500
C4—C7	1.504 (3)	C20—H20	0.9500
C5—C6	1.384 (3)	C21—C22	1.3900
C5—H5	0.9500	C21—C26	1.3900
C6—H6	0.9500	C22—C23	1.3900
C7—H7A	0.9800	C22—H22	0.9500
C7—H7B	0.9800	C23—C24	1.3900
C7—H7C	0.9800	C23—H23	0.9500
C8—C13	1.390 (4)	C24—C25	1.3900
C8—C9	1.393 (3)	C24—H24	0.9500
C9—C10	1.385 (4)	C25—C26	1.3900
C9—H9	0.9500	C25—H25	0.9500

O7—S1—O3	120.57 (11)	C10—C11—C12	118.4 (2)
O7—S1—N1	103.36 (10)	C10—C11—C14	120.4 (2)
O3—S1—N1	108.33 (10)	C12—C11—C14	121.1 (3)
O7—S1—C1	108.94 (11)	C13—C12—C11	121.3 (3)
O3—S1—C1	107.99 (11)	C13—C12—H12	119.4
N1—S1—C1	106.86 (10)	C11—C12—H12	119.4
O4—S2—O2	120.62 (11)	C12—C13—C8	118.9 (2)
O4—S2—N1	105.45 (10)	C12—C13—H13	120.5
O2—S2—N1	105.73 (10)	C8—C13—H13	120.5
O4—S2—C8	109.51 (11)	C11—C14—H14A	109.5
O2—S2—C8	108.59 (11)	C11—C14—H14B	109.5
N1—S2—C8	105.90 (11)	H14A—C14—H14B	109.5
C15—N1—C21	12.1 (5)	C11—C14—H14C	109.5
C15—N1—S2	118.3 (2)	H14A—C14—H14C	109.5
C21—N1—S2	120.7 (6)	H14B—C14—H14C	109.5
C15—N1—S1	119.6 (2)	C20—C15—C16	119.5 (4)
C21—N1—S1	114.9 (6)	C20—C15—N1	119.7 (5)
S2—N1—S1	121.89 (12)	C16—C15—N1	120.7 (5)
C6—C1—C2	121.3 (2)	C17—C16—C15	120.2 (5)
C6—C1—S1	119.23 (18)	C17—C16—Br1	118.4 (4)
C2—C1—S1	119.32 (18)	C15—C16—Br1	121.4 (4)
C1—C2—C3	118.8 (2)	C18—C17—C16	119.0 (4)
C1—C2—H2	120.6	C18—C17—H17	120.5
C3—C2—H2	120.6	C16—C17—H17	120.5
C4—C3—C2	120.7 (2)	C19—C18—C17	121.0 (4)
C4—C3—H3	119.7	C19—C18—H18	119.5
C2—C3—H3	119.7	C17—C18—H18	119.5
C3—C4—C5	119.1 (2)	C18—C19—C20	119.8 (4)
C3—C4—C7	119.8 (2)	C18—C19—H19	120.1
C5—C4—C7	121.0 (2)	C20—C19—H19	120.1
C6—C5—C4	121.0 (2)	C19—C20—C15	120.3 (4)
C6—C5—H5	119.5	C19—C20—H20	119.9
C4—C5—H5	119.5	C15—C20—H20	119.9
C5—C6—C1	119.0 (2)	C22—C21—C26	120.0
C5—C6—H6	120.5	C22—C21—N1	120.5 (7)
C1—C6—H6	120.5	C26—C21—N1	119.2 (7)
C4—C7—H7A	109.5	C23—C22—C21	120.0
C4—C7—H7B	109.5	C23—C22—H22	120.0
H7A—C7—H7B	109.5	C21—C22—H22	120.0
C4—C7—H7C	109.5	C22—C23—C24	120.0
H7A—C7—H7C	109.5	C22—C23—H23	120.0
H7B—C7—H7C	109.5	C24—C23—H23	120.0
C13—C8—C9	121.0 (2)	C23—C24—C25	120.0
C13—C8—S2	120.03 (19)	C23—C24—H24	120.0
C9—C8—S2	118.86 (19)	C25—C24—H24	120.0
C10—C9—C8	119.0 (2)	C26—C25—C24	120.0
C10—C9—H9	120.5	C26—C25—H25	120.0
C8—C9—H9	120.5	C24—C25—H25	120.0
C9—C10—C11	121.2 (2)	C25—C26—C21	120.0
C9—C10—H10	119.4	C25—C26—Br2	118.7 (6)
C11—C10—H10	119.4	C21—C26—Br2	121.3 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.45	3.199 (3)	135

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈BrNO₄S₂
M_r	480.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.5819 (15), 13.1465 (19), 14.235 (2)
β (°)	95.478 (2)
V (Å³)	1971.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.32
Crystal size (mm)	0.38 × 0.33 × 0.24

Data collection
Diffractometer	Bruker KAPPA APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.472, 0.605
No. of measured, independent and observed [I > 2σ(I)] reflections	23193, 4792, 4320
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.085, 1.24
No. of reflections	4792
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.53

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and X-SEED (Barbour, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.45	3.199 (3)	135.3

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

MNA acknowledges the Higher Education Commission of Pakistan for granting a scholarship under its indigenous and IRSIP schemes.

References

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