(E)-2-Bromo-1-[2-(2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]ethanone

Kanchanadevi, J.; Anbalagan, G.; Saravanan, V.; Mohanakrishnan, A.K.; Gunasekaran, B.; Manivannan, V.

doi:10.1107/S1600536814000488

organic compounds

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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Page o149

doi:10.1107/S1600536814000488

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(E)-2-Bromo-1-[2-(2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]ethanone

J. Kanchanadevi,^a G. Anbalagan,^b V. Saravanan,^c A. K. Mohanakrishnan,^c B. Gunasekaran ^d ^* and V. Manivannan ^e ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 5 January 2014; accepted 8 January 2014; online 15 January 2014)

In the title compound C₂₄H₁₇BrN₂O₅S, the phenyl ring makes dihedral angles of 85.4 (2) and 8.8 (2)° with the indole ring system and the nitrobenzene ring, respectively, while the indole ring system and nitrobenzene ring make a dihedral angle of 80.1 (2)°. In the crystal, weak C—H⋯O interactions link the molecules, forming a two-dimensional network parallel to the bc plane.

CCDC reference: 980676

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ); Singh et al. (2000 ); Pomarnacka & Kozlarska-Kedra (2003 ); Srivastava & Pandeya (2011 ). For a related structure, see: Umadevi et al. (2013 ); Kanchanadevi et al. (2013 ).

Experimental

Crystal data

C₂₄H₁₇BrN₂O₅S
M_r = 525.37
Monoclinic, P n
a = 10.1823 (7) Å
b = 8.0932 (6) Å
c = 13.8111 (12) Å
β = 102.749 (2)°
V = 1110.08 (15) Å³
Z = 2
Mo Kα radiation
μ = 1.99 mm⁻¹
T = 295 K
0.35 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.543, T_max = 0.609
17011 measured reflections
4323 independent reflections
3368 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.01
4323 reflections
298 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 2093 Friedel pairs
Absolute structure parameter: 0.022 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5ⁱ	0.93	2.38	3.147 (5)	139
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 980676

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814000488/hg5374sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000488/hg5374Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000488/hg5374Isup3.cml

checkCIF report

Comment top

Indole derivatives exhibits antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). These derivatives also exhibits antimicrobial, antibiotic, analgesic, anticancer and anti-HIV (Pomarnacka & Kozlarska-Kedra, 2003; Srivastava & Pandeya, 2011) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Umadevi et al., 2013). The phenyl ring makes a dihedral angles of 85.4 (2)° and 8.8 (2)° with the indole ring system and the nitro benzene ring, respectively. The sum of bond angles around the atom N1 [355.7°] indicates sp² hybridization. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is controlled by weak intermolecular C—H···O interaction.

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Singh et al. (2000); Pomarnacka & Kozlarska-Kedra (2003); Srivastava & Pandeya (2011). For related structures, see: Umadevi et al. (2013); Kanchanadevi et al. (2014).

Experimental top

A solution of 2-nitrophenylvinyl-3-acetylindole (1.0 g, 2.29 mmol) and PTT (Phenyl trimethyl ammonium tribromide) (0.92 g, 2.46 mmol) in dry THF (10 ml) was stirred at 10 ° C for 1 h. After completion of the reaction (monitored by TLC), it was poured into crushed ice (100 g). The solid obtained was filtered and washed with MeOH (5 ml) to afford (E)-2-bromo-1-(2-(2-nitrostyryl)-1-(phenylsulfonyl)-1H- indol-3-yl)ethanone as a yellow solid (0.92 g, 78%) with melting point 184–186 ° C.

Structure description top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Singh et al. (2000); Pomarnacka & Kozlarska-Kedra (2003); Srivastava & Pandeya (2011). For related structures, see: Umadevi et al. (2013); Kanchanadevi et al. (2014).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines.

(E)-2-Bromo-1-[2-(2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]ethanone top

Crystal data top

C₂₄H₁₇BrN₂O₅S	F(000) = 532
M_r = 525.37	D_x = 1.572 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 4350 reflections
a = 10.1823 (7) Å	θ = 2.3–26.3°
b = 8.0932 (6) Å	µ = 1.99 mm⁻¹
c = 13.8111 (12) Å	T = 295 K
β = 102.749 (2)°	Block, yellow
V = 1110.08 (15) Å³	0.35 × 0.25 × 0.25 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	4323 independent reflections
Radiation source: fine-focus sealed tube	3368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0 pixels mm^-1	θ_max = 26.3°, θ_min = 2.3°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
T_min = 0.543, T_max = 0.609	l = −17→17
17011 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0621P)² + 0.3412P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4323 reflections	Δρ_max = 0.85 e Å⁻³
298 parameters	Δρ_min = −0.43 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2093 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.022 (9)

Crystal data top

C₂₄H₁₇BrN₂O₅S	V = 1110.08 (15) Å³
M_r = 525.37	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 10.1823 (7) Å	µ = 1.99 mm⁻¹
b = 8.0932 (6) Å	T = 295 K
c = 13.8111 (12) Å	0.35 × 0.25 × 0.25 mm
β = 102.749 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4323 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3368 reflections with I > 2σ(I)
T_min = 0.543, T_max = 0.609	R_int = 0.027
17011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 0.85 e Å⁻³
S = 1.01	Δρ_min = −0.43 e Å⁻³
4323 reflections	Absolute structure: Flack (1983), 2093 Friedel pairs
298 parameters	Absolute structure parameter: 0.022 (9)
2 restraints

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

	x	y	z	U_iso*/U_eq
C1	0.0805 (4)	0.3950 (5)	0.3857 (3)	0.0358 (8)
C2	0.0594 (5)	0.5284 (5)	0.3192 (3)	0.0516 (11)
H2	−0.0157	0.5329	0.2669	0.062*
C3	0.1535 (5)	0.6512 (5)	0.3345 (4)	0.0556 (11)
H3	0.1419	0.7411	0.2915	0.067*
C4	0.2643 (5)	0.6461 (5)	0.4112 (3)	0.0516 (11)
H4	0.3264	0.7319	0.4184	0.062*
C5	0.2867 (5)	0.5171 (5)	0.4783 (3)	0.0437 (10)
H5	0.3617	0.5156	0.5309	0.052*
C6	0.1926 (4)	0.3890 (4)	0.4643 (3)	0.0327 (8)
C7	0.1862 (4)	0.2356 (4)	0.5157 (3)	0.0307 (7)
C8	0.0699 (4)	0.1549 (4)	0.4711 (3)	0.0332 (8)
C9	0.0184 (4)	0.0034 (4)	0.5039 (3)	0.0353 (8)
H9	−0.0185	−0.0765	0.4574	0.042*
C10	0.0230 (4)	−0.0236 (4)	0.5997 (3)	0.0340 (8)
H10	0.0499	0.0638	0.6432	0.041*
C11	−0.0110 (3)	−0.1803 (5)	0.6424 (3)	0.0330 (8)
C12	0.0184 (4)	−0.3288 (4)	0.6024 (3)	0.0366 (9)
H12	0.0557	−0.3276	0.5467	0.044*
C13	−0.0058 (4)	−0.4776 (5)	0.6424 (3)	0.0445 (10)
H13	0.0152	−0.5753	0.6138	0.053*
C14	−0.0612 (5)	−0.4832 (5)	0.7250 (4)	0.0483 (11)
H14	−0.0772	−0.5844	0.7522	0.058*
C15	−0.0924 (4)	−0.3399 (5)	0.7662 (3)	0.0462 (10)
H15	−0.1307	−0.3427	0.8214	0.055*
C16	−0.0671 (4)	−0.1910 (5)	0.7261 (3)	0.0391 (9)
C17	−0.2379 (4)	0.3680 (6)	0.4081 (3)	0.0478 (11)
C18	−0.2824 (5)	0.3030 (7)	0.4874 (4)	0.0632 (13)
H18	−0.2719	0.1908	0.5016	0.076*
C19	−0.3424 (6)	0.4035 (10)	0.5456 (5)	0.0866 (19)
H19	−0.3735	0.3600	0.5987	0.104*
C20	−0.3552 (5)	0.5662 (10)	0.5243 (6)	0.088 (2)
H20	−0.3955	0.6344	0.5636	0.106*
C21	−0.3106 (6)	0.6341 (8)	0.4465 (6)	0.086 (2)
H21	−0.3205	0.7468	0.4339	0.103*
C22	−0.2511 (5)	0.5356 (6)	0.3871 (5)	0.0660 (14)
H22	−0.2204	0.5803	0.3341	0.079*
C23	0.2995 (4)	0.1765 (5)	0.5939 (3)	0.0380 (8)
C24	0.3438 (5)	−0.0005 (5)	0.5889 (4)	0.0540 (12)
H24A	0.3226	−0.0366	0.5203	0.065*
H24B	0.2936	−0.0696	0.6254	0.065*
N1	0.0045 (3)	0.2503 (4)	0.3896 (2)	0.0356 (7)
N2	−0.1036 (5)	−0.0428 (5)	0.7741 (3)	0.0598 (11)
O1	−0.1734 (3)	0.3120 (5)	0.2399 (2)	0.0654 (9)
O2	−0.2013 (3)	0.0745 (4)	0.3449 (2)	0.0602 (9)
O3	−0.1280 (5)	0.0831 (5)	0.7280 (4)	0.1015 (17)
O4	−0.1194 (10)	−0.0537 (6)	0.8566 (4)	0.171 (4)
O5	0.3599 (4)	0.2701 (4)	0.6549 (3)	0.0840 (13)
S1	−0.16138 (10)	0.24019 (13)	0.33528 (8)	0.0465 (3)
Br1	0.53169 (7)	−0.02967 (7)	0.64210 (6)	0.0930 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.041 (2)	0.0338 (19)	0.0347 (19)	0.0033 (16)	0.0131 (16)	0.0055 (16)
C2	0.068 (3)	0.046 (2)	0.041 (2)	0.009 (2)	0.012 (2)	0.0114 (19)
C3	0.078 (3)	0.035 (2)	0.063 (3)	0.005 (2)	0.035 (3)	0.015 (2)
C4	0.072 (3)	0.031 (2)	0.064 (3)	−0.0046 (19)	0.040 (3)	−0.0004 (19)
C5	0.048 (2)	0.039 (2)	0.050 (2)	0.0000 (17)	0.0229 (19)	−0.0033 (18)
C6	0.0388 (19)	0.0250 (18)	0.037 (2)	0.0017 (15)	0.0154 (16)	−0.0031 (16)
C7	0.0379 (19)	0.0241 (18)	0.0314 (18)	0.0009 (15)	0.0103 (15)	−0.0018 (14)
C8	0.0386 (19)	0.0281 (19)	0.0337 (18)	0.0002 (15)	0.0094 (15)	−0.0067 (15)
C9	0.038 (2)	0.028 (2)	0.039 (2)	−0.0018 (15)	0.0053 (16)	−0.0013 (15)
C10	0.0364 (19)	0.0233 (17)	0.043 (2)	0.0005 (15)	0.0108 (17)	−0.0048 (15)
C11	0.0287 (17)	0.033 (2)	0.038 (2)	−0.0034 (14)	0.0090 (16)	0.0015 (16)
C12	0.0358 (19)	0.033 (2)	0.044 (2)	0.0006 (16)	0.0136 (17)	−0.0053 (16)
C13	0.050 (3)	0.029 (2)	0.057 (3)	0.0020 (16)	0.017 (2)	−0.0053 (19)
C14	0.057 (3)	0.031 (2)	0.059 (3)	−0.0047 (18)	0.016 (2)	0.0098 (19)
C15	0.052 (2)	0.043 (2)	0.049 (2)	0.000 (2)	0.0239 (19)	0.008 (2)
C16	0.045 (2)	0.0307 (19)	0.044 (2)	0.0013 (17)	0.0143 (18)	−0.0052 (17)
C17	0.032 (2)	0.050 (3)	0.057 (3)	−0.0010 (17)	0.0001 (19)	−0.008 (2)
C18	0.052 (3)	0.069 (3)	0.069 (3)	0.001 (2)	0.015 (2)	−0.012 (3)
C19	0.059 (3)	0.102 (5)	0.105 (5)	−0.008 (3)	0.032 (3)	−0.036 (4)
C20	0.042 (3)	0.101 (6)	0.123 (6)	0.002 (3)	0.021 (3)	−0.049 (4)
C21	0.056 (3)	0.064 (4)	0.128 (6)	0.010 (3)	0.001 (4)	−0.033 (4)
C22	0.045 (3)	0.055 (3)	0.092 (4)	0.008 (2)	0.004 (3)	−0.009 (3)
C23	0.045 (2)	0.030 (2)	0.035 (2)	−0.0002 (17)	0.0018 (17)	−0.0032 (16)
C24	0.057 (3)	0.039 (2)	0.056 (3)	0.0065 (19)	−0.009 (2)	0.001 (2)
N1	0.0380 (16)	0.0322 (16)	0.0351 (16)	0.0039 (13)	0.0050 (13)	0.0071 (13)
N2	0.090 (3)	0.039 (2)	0.060 (3)	0.0112 (19)	0.038 (2)	−0.0005 (19)
O1	0.072 (2)	0.073 (2)	0.0417 (17)	0.0108 (18)	−0.0076 (15)	0.0061 (15)
O2	0.0532 (18)	0.0504 (19)	0.068 (2)	−0.0068 (14)	−0.0050 (16)	−0.0124 (15)
O3	0.160 (5)	0.047 (2)	0.127 (4)	0.025 (2)	0.097 (4)	0.008 (2)
O4	0.381 (12)	0.081 (3)	0.095 (4)	0.049 (5)	0.149 (6)	0.003 (3)
O5	0.090 (3)	0.051 (2)	0.084 (3)	0.0122 (18)	−0.037 (2)	−0.0277 (19)
S1	0.0421 (5)	0.0469 (6)	0.0439 (5)	0.0024 (5)	−0.0046 (4)	−0.0057 (5)
Br1	0.0538 (3)	0.0647 (3)	0.1580 (7)	0.0143 (3)	0.0183 (3)	−0.0032 (4)

Geometric parameters (Å, º) top

C1—C6	1.392 (5)	C14—H14	0.9300
C1—C2	1.403 (6)	C15—C16	1.374 (6)
C1—N1	1.412 (5)	C15—H15	0.9300
C2—C3	1.364 (7)	C16—N2	1.457 (5)
C2—H2	0.9300	C17—C18	1.379 (7)
C3—C4	1.368 (7)	C17—C22	1.387 (7)
C3—H3	0.9300	C17—S1	1.742 (4)
C4—C5	1.381 (6)	C18—C19	1.378 (8)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.396 (6)	C19—C20	1.349 (11)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.439 (5)	C20—C21	1.370 (10)
C7—C8	1.373 (5)	C20—H20	0.9300
C7—C23	1.475 (5)	C21—C22	1.378 (8)
C8—N1	1.406 (5)	C21—H21	0.9300
C8—C9	1.445 (5)	C22—H22	0.9300
C9—C10	1.332 (5)	C23—O5	1.197 (5)
C9—H9	0.9300	C23—C24	1.508 (5)
C10—C11	1.472 (5)	C24—Br1	1.907 (5)
C10—H10	0.9300	C24—H24A	0.9700
C11—C12	1.383 (5)	C24—H24B	0.9700
C11—C16	1.400 (5)	N1—S1	1.692 (3)
C12—C13	1.370 (5)	N2—O4	1.188 (6)
C12—H12	0.9300	N2—O3	1.198 (5)
C13—C14	1.380 (6)	O1—S1	1.420 (3)
C13—H13	0.9300	O2—S1	1.416 (3)
C14—C15	1.361 (6)

C6—C1—C2	121.2 (4)	C16—C15—H15	120.1
C6—C1—N1	107.7 (3)	C15—C16—C11	122.3 (3)
C2—C1—N1	131.1 (4)	C15—C16—N2	116.7 (4)
C3—C2—C1	117.3 (4)	C11—C16—N2	121.1 (3)
C3—C2—H2	121.3	C18—C17—C22	120.4 (5)
C1—C2—H2	121.3	C18—C17—S1	119.9 (4)
C2—C3—C4	121.9 (4)	C22—C17—S1	119.6 (4)
C2—C3—H3	119.0	C19—C18—C17	120.3 (6)
C4—C3—H3	119.0	C19—C18—H18	119.9
C3—C4—C5	121.9 (4)	C17—C18—H18	119.9
C3—C4—H4	119.0	C20—C19—C18	118.8 (7)
C5—C4—H4	119.0	C20—C19—H19	120.6
C4—C5—C6	117.5 (4)	C18—C19—H19	120.6
C4—C5—H5	121.3	C19—C20—C21	122.0 (6)
C6—C5—H5	121.3	C19—C20—H20	119.0
C1—C6—C5	120.1 (4)	C21—C20—H20	119.0
C1—C6—C7	107.2 (3)	C20—C21—C22	120.0 (6)
C5—C6—C7	132.6 (4)	C20—C21—H21	120.0
C8—C7—C6	108.5 (3)	C22—C21—H21	120.0
C8—C7—C23	129.2 (3)	C21—C22—C17	118.4 (6)
C6—C7—C23	121.8 (3)	C21—C22—H22	120.8
C7—C8—N1	107.9 (3)	C17—C22—H22	120.8
C7—C8—C9	126.8 (3)	O5—C23—C7	120.4 (4)
N1—C8—C9	125.2 (3)	O5—C23—C24	121.4 (4)
C10—C9—C8	121.0 (3)	C7—C23—C24	117.9 (3)
C10—C9—H9	119.5	C23—C24—Br1	112.6 (3)
C8—C9—H9	119.5	C23—C24—H24A	109.1
C9—C10—C11	125.5 (3)	Br1—C24—H24A	109.1
C9—C10—H10	117.3	C23—C24—H24B	109.1
C11—C10—H10	117.3	Br1—C24—H24B	109.1
C12—C11—C16	116.1 (3)	H24A—C24—H24B	107.8
C12—C11—C10	119.8 (3)	C8—N1—C1	108.6 (3)
C16—C11—C10	124.0 (3)	C8—N1—S1	125.4 (2)
C13—C12—C11	121.9 (4)	C1—N1—S1	121.7 (2)
C13—C12—H12	119.0	O4—N2—O3	121.1 (4)
C11—C12—H12	119.0	O4—N2—C16	118.5 (4)
C12—C13—C14	120.3 (4)	O3—N2—C16	120.1 (4)
C12—C13—H13	119.8	O2—S1—O1	120.4 (2)
C14—C13—H13	119.8	O2—S1—N1	106.46 (17)
C15—C14—C13	119.6 (4)	O1—S1—N1	105.34 (19)
C15—C14—H14	120.2	O2—S1—C17	109.5 (2)
C13—C14—H14	120.2	O1—S1—C17	109.5 (2)
C14—C15—C16	119.8 (4)	N1—S1—C17	104.24 (17)
C14—C15—H15	120.1

C6—C1—C2—C3	0.4 (6)	C17—C18—C19—C20	−0.8 (8)
N1—C1—C2—C3	−179.1 (4)	C18—C19—C20—C21	0.1 (9)
C1—C2—C3—C4	0.0 (7)	C19—C20—C21—C22	0.3 (9)
C2—C3—C4—C5	−0.7 (7)	C20—C21—C22—C17	0.0 (8)
C3—C4—C5—C6	1.0 (6)	C18—C17—C22—C21	−0.7 (7)
C2—C1—C6—C5	0.0 (6)	S1—C17—C22—C21	−179.3 (4)
N1—C1—C6—C5	179.6 (3)	C8—C7—C23—O5	−146.1 (4)
C2—C1—C6—C7	−178.3 (4)	C6—C7—C23—O5	42.6 (6)
N1—C1—C6—C7	1.3 (4)	C8—C7—C23—C24	39.2 (6)
C4—C5—C6—C1	−0.7 (5)	C6—C7—C23—C24	−132.1 (4)
C4—C5—C6—C7	177.1 (4)	O5—C23—C24—Br1	−25.8 (6)
C1—C6—C7—C8	−2.4 (4)	C7—C23—C24—Br1	148.9 (3)
C5—C6—C7—C8	179.6 (4)	C7—C8—N1—C1	−1.6 (4)
C1—C6—C7—C23	170.6 (3)	C9—C8—N1—C1	175.4 (3)
C5—C6—C7—C23	−7.4 (6)	C7—C8—N1—S1	−158.3 (3)
C6—C7—C8—N1	2.4 (4)	C9—C8—N1—S1	18.7 (5)
C23—C7—C8—N1	−169.8 (4)	C6—C1—N1—C8	0.2 (4)
C6—C7—C8—C9	−174.6 (3)	C2—C1—N1—C8	179.7 (4)
C23—C7—C8—C9	13.2 (6)	C6—C1—N1—S1	157.9 (2)
C7—C8—C9—C10	41.5 (6)	C2—C1—N1—S1	−22.6 (6)
N1—C8—C9—C10	−135.1 (4)	C15—C16—N2—O4	19.0 (8)
C8—C9—C10—C11	−172.1 (4)	C11—C16—N2—O4	−162.0 (7)
C9—C10—C11—C12	34.8 (6)	C15—C16—N2—O3	−154.8 (5)
C9—C10—C11—C16	−148.3 (4)	C11—C16—N2—O3	24.3 (7)
C16—C11—C12—C13	−0.1 (5)	C8—N1—S1—O2	−32.0 (3)
C10—C11—C12—C13	177.0 (4)	C1—N1—S1—O2	174.2 (3)
C11—C12—C13—C14	0.1 (6)	C8—N1—S1—O1	−160.9 (3)
C12—C13—C14—C15	0.3 (7)	C1—N1—S1—O1	45.2 (3)
C13—C14—C15—C16	−0.7 (7)	C8—N1—S1—C17	83.8 (3)
C14—C15—C16—C11	0.8 (6)	C1—N1—S1—C17	−70.1 (3)
C14—C15—C16—N2	179.8 (4)	C18—C17—S1—O2	22.6 (4)
C12—C11—C16—C15	−0.3 (6)	C22—C17—S1—O2	−158.8 (3)
C10—C11—C16—C15	−177.3 (4)	C18—C17—S1—O1	156.7 (4)
C12—C11—C16—N2	−179.4 (4)	C22—C17—S1—O1	−24.7 (4)
C10—C11—C16—N2	3.7 (6)	C18—C17—S1—N1	−91.0 (4)
C22—C17—C18—C19	1.1 (7)	C22—C17—S1—N1	87.6 (4)
S1—C17—C18—C19	179.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱ	0.93	2.38	3.147 (5)	139
C2—H2···O1	0.93	2.38	2.957 (6)	120
C9—H9···O2	0.93	2.47	2.827 (5)	103
C10—H10···O3	0.93	2.37	2.730 (5)	103

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱ	0.93	2.38	3.147 (5)	139.4

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

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Volume 70| Part 2| February 2014| Page o149

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