Ethyl 2-(bromo­meth­yl)-5-meth­oxy-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

Chakkaravarthi, G.; Sureshbabu, R.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536808007319

organic compounds

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Volume 64| Part 4| April 2008| Page o732

doi:10.1107/S1600536808007319

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Ethyl 2-(bromomethyl)-5-methoxy-1-phenylsulfonyl-1H-indole-3-carboxylate

G. Chakkaravarthi,^a ^* Radhakrishnan Sureshbabu,^b A. K. Mohanakrishnan ^b and V. Manivannan ^c

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 11 March 2008; accepted 17 March 2008; online 20 March 2008)

In the title compound, C₁₉H₁₈BrNO₅S, the plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The Br atom is disordered over two positions, with site-occupancy factors of 0.833 (14) and 0.167 (14). The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal packing is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For biological activity, see: Nieto et al. (2005 ); Yang et al. (2002 ). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₉H₁₈BrNO₅S
M_r = 452.31
Triclinic, $[P \overline 1]$
a = 8.9988 (3) Å
b = 9.2343 (2) Å
c = 11.6068 (3) Å
α = 82.524 (1)°
β = 87.666 (2)°
γ = 84.942 (3)°
V = 952.16 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 295 (2) K
0.20 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.593, T_max = 0.692
25160 measured reflections
6169 independent reflections
4163 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.127
S = 1.03
6169 reflections
254 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.56	3.472 (3)	165
C2—H2⋯O5ⁱⁱ	0.93	2.60	3.235 (3)	126
C6—H6⋯O2	0.93	2.54	2.908 (4)	104
C10—H10⋯O4	0.93	2.37	2.892 (3)	116
C13—H13⋯O1	0.93	2.28	2.863 (3)	120
C15—H15A⋯O5	0.97	2.31	2.911 (4)	119
C15—H15D⋯O2	0.97	2.16	2.895 (4)	131
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007319/rk2082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007319/rk2082Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of benzenesulfonamide derivatives, which are known to exhibit anti–bacterial (Nieto et al., 2005) anti–tumour (Yang et al., 2002) activities, we report the crystal structure of the title compound (I). The geometric parameters of the molecule of I (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008).

The plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The N1—S1—C1 plane is orthogonal to indole ring (dihedral angle 88.70 (7)°) and makes 75.97 (9)° with the phenyl ring. The plane of indole ring is almost coplanar (dihedral angle 2.66 (7)°) with the ester group and makes 6.33 (18)° with the methoxy group.

The torsion angles O2–S1–N1–C7 and O1–S1–N1–C14 [-30.0 (2)° and 27.3 (2)°, respectively] indicate syn–conformation of the sulfonyl moiety. The Br1 atom is disordered over two positions with the site occupancy factors of 0.833 (14) and 0.167 (14). The molecular packing is stabilized by weak intramolecular C—H···O interactions and the crystal packing of I (Fig. 2) is stabilized by weak intermolecular C—H···O interactions (see Table).

Related literature top

For biological activity, see: Nieto et al. (2005); Yang et al. (2002). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

Ethyl 2-(methyl)-5-methoxy-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1g, 2.2 mmol), N–bromo succinimide (0.4 g, 2.3 mmol), azo–bis–isobutyronitrile (50 mg) were dissolved in 50 ml of carbon tetrachloride. Refluxed on a waterbath for 2hr. Cooled to room temperature. Succinimide was filtered off over sodium sulfate. Filtrate was evaporated under reduced pressure. Product was recrystallized from methanol. Yield: 78%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of I, with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Only major fragment for disordered Br1 and C15 are drawn. Intramolecular H–bonds are shown as dashed lines.
	Fig. 2. The packing of I, viewed down the a axis. Intermolecular H–bonds are shown as dashed lines H atoms not involving hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z].

Ethyl 2-(bromomethyl)-5-methoxy-1-phenylsulfonyl-1H-indole-3-carboxylate top

Crystal data top

C₁₉H₁₈BrNO₅S	Z = 2
M_r = 452.31	F(000) = 460
Triclinic, P1	D_x = 1.578 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9988 (3) Å	Cell parameters from 8207 reflections
b = 9.2343 (2) Å	θ = 2.2–27.5°
c = 11.6068 (3) Å	µ = 2.30 mm⁻¹
α = 82.524 (1)°	T = 295 K
β = 87.666 (2)°	Block, colourless
γ = 84.942 (3)°	0.20 × 0.20 × 0.16 mm
V = 952.16 (5) Å³

Data collection top

Bruker Kappa APEXII diffractometer	6169 independent reflections
Radiation source: Fine–focus sealed tube	4163 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 31.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.593, T_max = 0.692	k = −13→13
25160 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: Geom
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.054P)² + 0.4811P] where P = (F_o² + 2F_c²)/3
6169 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.68 e Å⁻³
3 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

C₁₉H₁₈BrNO₅S	γ = 84.942 (3)°
M_r = 452.31	V = 952.16 (5) Å³
Triclinic, P1	Z = 2
a = 8.9988 (3) Å	Mo Kα radiation
b = 9.2343 (2) Å	µ = 2.30 mm⁻¹
c = 11.6068 (3) Å	T = 295 K
α = 82.524 (1)°	0.20 × 0.20 × 0.16 mm
β = 87.666 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	6169 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4163 reflections with I > 2σ(I)
T_min = 0.593, T_max = 0.692	R_int = 0.027
25160 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	Δρ_max = 0.68 e Å⁻³
6169 reflections	Δρ_min = −0.89 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.2859 (3)	−0.0105 (2)	0.5880 (3)	0.0695 (4)	0.833 (14)
Br1A	0.2613 (8)	0.0063 (7)	0.6105 (7)	0.0695 (4)	0.167 (14)
S1	0.53695 (6)	0.26331 (6)	0.73409 (5)	0.04656 (14)
O1	0.6066 (2)	0.3534 (2)	0.80232 (18)	0.0623 (5)
O2	0.6249 (2)	0.1714 (2)	0.66452 (19)	0.0688 (6)
O3	0.1927 (3)	0.2237 (2)	1.26357 (17)	0.0714 (6)
O4	0.1493 (2)	−0.18350 (18)	1.02343 (16)	0.0551 (4)
O5	0.2440 (3)	−0.2589 (2)	0.8592 (2)	0.0783 (6)
N1	0.4384 (2)	0.15286 (19)	0.82973 (15)	0.0410 (4)
C1	0.4041 (2)	0.3722 (2)	0.64784 (18)	0.0407 (4)
C2	0.3253 (3)	0.4881 (3)	0.6931 (2)	0.0499 (5)
H2	0.3405	0.5062	0.7686	0.060*
C3	0.2243 (3)	0.5759 (3)	0.6245 (3)	0.0627 (7)
H3	0.1703	0.6545	0.6537	0.075*
C4	0.2020 (4)	0.5490 (3)	0.5135 (3)	0.0690 (7)
H4	0.1321	0.6085	0.4682	0.083*
C5	0.2818 (4)	0.4352 (3)	0.4690 (2)	0.0693 (7)
H5	0.2663	0.4178	0.3935	0.083*
C6	0.3860 (3)	0.3453 (3)	0.5360 (2)	0.0561 (6)
H6	0.4422	0.2688	0.5058	0.067*
C7	0.3878 (2)	0.0171 (2)	0.81460 (18)	0.0412 (4)
C8	0.3026 (2)	−0.0297 (2)	0.90984 (18)	0.0393 (4)
C9	0.2973 (2)	0.0781 (2)	0.98934 (17)	0.0380 (4)
C10	0.2300 (3)	0.0839 (3)	1.10015 (19)	0.0452 (5)
H10	0.1742	0.0093	1.1353	0.054*
C11	0.2498 (3)	0.2044 (3)	1.1549 (2)	0.0510 (5)
C12	0.3333 (3)	0.3160 (3)	1.1024 (2)	0.0555 (6)
H12	0.3444	0.3958	1.1417	0.067*
C13	0.3993 (3)	0.3117 (3)	0.9951 (2)	0.0516 (5)
H13	0.4547	0.3871	0.9607	0.062*
C14	0.3808 (2)	0.1902 (2)	0.93842 (18)	0.0399 (4)
C15	0.4242 (3)	−0.0591 (3)	0.7108 (2)	0.0560 (5)
H15A	0.4287	−0.1640	0.7346	0.067*	0.833 (14)
H15B	0.5226	−0.0356	0.6808	0.067*	0.833 (14)
H15C	0.4302	−0.1646	0.7312	0.067*	0.167 (14)
H15D	0.5176	−0.0306	0.6736	0.067*	0.167 (14)
C16	0.0958 (4)	0.1221 (4)	1.3175 (3)	0.0719 (8)
H16A	0.0109	0.1221	1.2700	0.108*
H16B	0.0630	0.1487	1.3922	0.108*
H16C	0.1474	0.0259	1.3271	0.108*
C17	0.2311 (3)	−0.1686 (2)	0.9262 (2)	0.0470 (5)
C18	0.0781 (3)	−0.3188 (3)	1.0520 (3)	0.0738 (9)
H18A	0.1507	−0.4023	1.0488	0.089*
H18B	0.0008	−0.3243	0.9972	0.089*
C19	0.0120 (4)	−0.3191 (5)	1.1716 (4)	0.1037 (15)
H19A	0.0896	−0.3150	1.2252	0.156*
H19B	−0.0375	−0.4070	1.1930	0.156*
H19C	−0.0589	−0.2354	1.1739	0.156*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0960 (5)	0.0791 (4)	0.0381 (5)	−0.0300 (4)	−0.0142 (5)	−0.0064 (4)
Br1A	0.0960 (5)	0.0791 (4)	0.0381 (5)	−0.0300 (4)	−0.0142 (5)	−0.0064 (4)
S1	0.0417 (3)	0.0457 (3)	0.0503 (3)	−0.0032 (2)	0.0003 (2)	0.0003 (2)
O1	0.0509 (10)	0.0655 (11)	0.0719 (12)	−0.0198 (8)	−0.0153 (8)	0.0002 (9)
O2	0.0616 (11)	0.0617 (11)	0.0763 (13)	0.0099 (9)	0.0226 (10)	−0.0013 (10)
O3	0.0890 (15)	0.0806 (14)	0.0485 (10)	−0.0023 (11)	0.0037 (10)	−0.0285 (10)
O4	0.0634 (10)	0.0476 (9)	0.0544 (10)	−0.0169 (8)	−0.0054 (8)	0.0019 (7)
O5	0.1144 (18)	0.0565 (11)	0.0729 (13)	−0.0309 (11)	0.0018 (12)	−0.0271 (10)
N1	0.0493 (10)	0.0366 (8)	0.0368 (9)	−0.0027 (7)	−0.0047 (7)	−0.0028 (7)
C1	0.0475 (11)	0.0364 (10)	0.0378 (10)	−0.0087 (8)	−0.0007 (8)	0.0004 (8)
C2	0.0592 (14)	0.0448 (12)	0.0446 (12)	−0.0003 (10)	−0.0010 (10)	−0.0046 (9)
C3	0.0667 (17)	0.0526 (14)	0.0643 (17)	0.0067 (12)	−0.0043 (13)	0.0026 (12)
C4	0.0731 (18)	0.0632 (15)	0.0666 (17)	−0.0116 (12)	−0.0220 (14)	0.0176 (12)
C5	0.100 (2)	0.0681 (16)	0.0423 (13)	−0.0282 (13)	−0.0172 (13)	0.0013 (11)
C6	0.0832 (18)	0.0457 (12)	0.0405 (12)	−0.0136 (12)	0.0018 (12)	−0.0054 (9)
C7	0.0482 (11)	0.0377 (10)	0.0378 (10)	0.0006 (8)	−0.0085 (9)	−0.0055 (8)
C8	0.0470 (11)	0.0349 (9)	0.0367 (10)	−0.0014 (8)	−0.0108 (8)	−0.0048 (7)
C9	0.0435 (10)	0.0352 (9)	0.0349 (9)	0.0020 (8)	−0.0096 (8)	−0.0046 (7)
C10	0.0501 (12)	0.0476 (12)	0.0379 (10)	−0.0016 (9)	−0.0074 (9)	−0.0051 (9)
C11	0.0588 (14)	0.0557 (13)	0.0393 (11)	0.0059 (11)	−0.0081 (10)	−0.0143 (10)
C12	0.0738 (17)	0.0448 (12)	0.0515 (13)	−0.0005 (11)	−0.0141 (12)	−0.0183 (10)
C13	0.0666 (15)	0.0386 (11)	0.0517 (13)	−0.0078 (10)	−0.0130 (11)	−0.0074 (9)
C14	0.0467 (11)	0.0357 (10)	0.0373 (10)	0.0005 (8)	−0.0099 (8)	−0.0045 (8)
C15	0.0730 (15)	0.0533 (14)	0.0440 (12)	−0.0058 (11)	0.0002 (9)	−0.0152 (10)
C16	0.0666 (18)	0.097 (2)	0.0486 (15)	0.0153 (16)	0.0053 (13)	−0.0143 (15)
C17	0.0561 (13)	0.0395 (11)	0.0464 (12)	−0.0060 (9)	−0.0160 (10)	−0.0033 (9)
C18	0.0631 (16)	0.0593 (16)	0.096 (2)	−0.0238 (13)	−0.0233 (16)	0.0205 (15)
C19	0.065 (2)	0.128 (3)	0.105 (3)	−0.030 (2)	−0.0010 (19)	0.048 (3)

Geometric parameters (Å, º) top

Br1—C15	1.914 (3)	C7—C15	1.484 (3)
Br1A—C15	1.9152 (10)	C8—C9	1.439 (3)
S1—O2	1.417 (2)	C8—C17	1.472 (3)
S1—O1	1.419 (2)	C9—C14	1.389 (3)
S1—N1	1.6862 (19)	C9—C10	1.405 (3)
S1—C1	1.751 (2)	C10—C11	1.379 (3)
O3—C11	1.370 (3)	C10—H10	0.9300
O3—C16	1.407 (4)	C11—C12	1.390 (4)
O4—C17	1.320 (3)	C12—C13	1.362 (4)
O4—C18	1.448 (3)	C12—H12	0.9300
O5—C17	1.208 (3)	C13—C14	1.398 (3)
N1—C7	1.405 (3)	C13—H13	0.9300
N1—C14	1.417 (3)	C15—H15A	0.9700
C1—C6	1.372 (3)	C15—H15B	0.9700
C1—C2	1.381 (3)	C15—H15C	0.9700
C2—C3	1.371 (4)	C15—H15D	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.369 (4)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.365 (5)	C18—C19	1.487 (5)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.388 (4)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.364 (3)	C19—H19C	0.9600

O2—S1—O1	120.09 (13)	C11—C12—H12	119.1
O2—S1—N1	106.72 (11)	C12—C13—C14	117.7 (2)
O1—S1—N1	105.29 (11)	C12—C13—H13	121.1
O2—S1—C1	109.30 (12)	C14—C13—H13	121.1
O1—S1—C1	108.93 (11)	C9—C14—C13	121.2 (2)
N1—S1—C1	105.49 (10)	C9—C14—N1	107.98 (17)
C11—O3—C16	117.9 (2)	C13—C14—N1	130.8 (2)
C17—O4—C18	117.3 (2)	C7—C15—Br1	114.7 (2)
C7—N1—C14	107.77 (17)	C7—C15—Br1A	103.7 (4)
C7—N1—S1	127.88 (15)	C7—C15—H15A	108.6
C14—N1—S1	124.15 (15)	Br1—C15—H15A	108.6
C6—C1—C2	121.7 (2)	Br1A—C15—H15A	111.8
C6—C1—S1	119.67 (19)	C7—C15—H15B	108.6
C2—C1—S1	118.53 (18)	Br1—C15—H15B	108.6
C3—C2—C1	118.6 (2)	Br1A—C15—H15B	116.3
C3—C2—H2	120.7	H15A—C15—H15B	107.6
C1—C2—H2	120.7	C7—C15—H15C	111.1
C4—C3—C2	120.6 (3)	Br1—C15—H15C	107.3
C4—C3—H3	119.7	Br1A—C15—H15C	111.0
C2—C3—H3	119.7	H15B—C15—H15C	106.2
C5—C4—C3	120.4 (3)	C7—C15—H15D	111.1
C5—C4—H4	119.8	Br1—C15—H15D	102.7
C3—C4—H4	119.8	Br1A—C15—H15D	110.4
C4—C5—C6	120.3 (3)	H15A—C15—H15D	111.1
C4—C5—H5	119.8	H15C—C15—H15D	109.5
C6—C5—H5	119.8	O3—C16—H16A	109.5
C1—C6—C5	118.4 (3)	O3—C16—H16B	109.5
C1—C6—H6	120.8	H16A—C16—H16B	109.5
C5—C6—H6	120.8	O3—C16—H16C	109.5
C8—C7—N1	108.66 (18)	H16A—C16—H16C	109.5
C8—C7—C15	127.3 (2)	H16B—C16—H16C	109.5
N1—C7—C15	124.1 (2)	O5—C17—O4	123.3 (2)
C7—C8—C9	108.47 (18)	O5—C17—C8	124.7 (2)
C7—C8—C17	124.5 (2)	O4—C17—C8	112.02 (19)
C9—C8—C17	127.0 (2)	O4—C18—C19	107.3 (3)
C14—C9—C10	120.41 (19)	O4—C18—H18A	110.3
C14—C9—C8	107.12 (18)	C19—C18—H18A	110.3
C10—C9—C8	132.5 (2)	O4—C18—H18B	110.3
C11—C10—C9	117.5 (2)	C19—C18—H18B	110.3
C11—C10—H10	121.2	H18A—C18—H18B	108.5
C9—C10—H10	121.2	C18—C19—H19A	109.5
O3—C11—C10	123.9 (2)	C18—C19—H19B	109.5
O3—C11—C12	114.8 (2)	H19A—C19—H19B	109.5
C10—C11—C12	121.3 (2)	C18—C19—H19C	109.5
C13—C12—C11	121.8 (2)	H19A—C19—H19C	109.5
C13—C12—H12	119.1	H19B—C19—H19C	109.5

O2—S1—N1—C7	−30.0 (2)	C17—C8—C9—C10	1.3 (4)
O1—S1—N1—C7	−158.62 (19)	C14—C9—C10—C11	0.3 (3)
C1—S1—N1—C7	86.2 (2)	C8—C9—C10—C11	178.5 (2)
O2—S1—N1—C14	155.94 (18)	C16—O3—C11—C10	−6.6 (4)
O1—S1—N1—C14	27.3 (2)	C16—O3—C11—C12	174.3 (2)
C1—S1—N1—C14	−87.87 (18)	C9—C10—C11—O3	−179.0 (2)
O2—S1—C1—C6	8.6 (2)	C9—C10—C11—C12	0.0 (3)
O1—S1—C1—C6	141.6 (2)	O3—C11—C12—C13	179.0 (2)
N1—S1—C1—C6	−105.8 (2)	C10—C11—C12—C13	−0.1 (4)
O2—S1—C1—C2	−168.24 (19)	C11—C12—C13—C14	−0.1 (4)
O1—S1—C1—C2	−35.3 (2)	C10—C9—C14—C13	−0.5 (3)
N1—S1—C1—C2	77.3 (2)	C8—C9—C14—C13	−179.1 (2)
C6—C1—C2—C3	1.4 (4)	C10—C9—C14—N1	178.12 (19)
S1—C1—C2—C3	178.2 (2)	C8—C9—C14—N1	−0.5 (2)
C1—C2—C3—C4	0.1 (4)	C12—C13—C14—C9	0.4 (3)
C2—C3—C4—C5	−0.9 (5)	C12—C13—C14—N1	−177.8 (2)
C3—C4—C5—C6	0.2 (5)	C7—N1—C14—C9	0.6 (2)
C2—C1—C6—C5	−2.1 (4)	S1—N1—C14—C9	175.69 (14)
S1—C1—C6—C5	−178.8 (2)	C7—N1—C14—C13	179.0 (2)
C4—C5—C6—C1	1.2 (4)	S1—N1—C14—C13	−5.9 (3)
C14—N1—C7—C8	−0.4 (2)	C8—C7—C15—Br1	90.2 (3)
S1—N1—C7—C8	−175.24 (15)	N1—C7—C15—Br1	−90.1 (2)
C14—N1—C7—C15	179.9 (2)	C8—C7—C15—Br1A	87.5 (3)
S1—N1—C7—C15	5.0 (3)	N1—C7—C15—Br1A	−92.8 (3)
N1—C7—C8—C9	0.0 (2)	C18—O4—C17—O5	2.9 (4)
C15—C7—C8—C9	179.8 (2)	C18—O4—C17—C8	−177.4 (2)
N1—C7—C8—C17	−179.39 (19)	C7—C8—C17—O5	2.7 (4)
C15—C7—C8—C17	0.4 (4)	C9—C8—C17—O5	−176.6 (2)
C7—C8—C9—C14	0.3 (2)	C7—C8—C17—O4	−176.9 (2)
C17—C8—C9—C14	179.7 (2)	C9—C8—C17—O4	3.8 (3)
C7—C8—C9—C10	−178.1 (2)	C17—O4—C18—C19	171.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.56	3.472 (3)	165
C2—H2···O5ⁱⁱ	0.93	2.60	3.235 (3)	126
C6—H6···O2	0.93	2.54	2.908 (4)	104
C10—H10···O4	0.93	2.37	2.892 (3)	116
C13—H13···O1	0.93	2.28	2.863 (3)	120
C15—H15A···O5	0.97	2.31	2.911 (4)	119
C15—H15D···O2	0.97	2.16	2.895 (4)	131

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈BrNO₅S
M_r	452.31
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.9988 (3), 9.2343 (2), 11.6068 (3)
α, β, γ (°)	82.524 (1), 87.666 (2), 84.942 (3)
V (Å³)	952.16 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.20 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.593, 0.692
No. of measured, independent and observed [I > 2σ(I)] reflections	25160, 6169, 4163
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.730

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.04
No. of reflections	6169
No. of parameters	254
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.89

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.56	3.472 (3)	165
C2—H2···O5ⁱⁱ	0.93	2.60	3.235 (3)	126
C6—H6···O2	0.93	2.54	2.908 (4)	104
C10—H10···O4	0.93	2.37	2.892 (3)	116
C13—H13···O1	0.93	2.28	2.863 (3)	120
C15—H15A···O5	0.97	2.31	2.911 (4)	119
C15—H15D···O2	0.97	2.16	2.895 (4)	131

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

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

References

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