Ethyl 2-(bromo-meth-yl)-5-meth-oxy-1-phenyl-sulfonyl-1H-indole-3-carboxyl-ate.

In the title compound, C(19)H(18)BrNO(5)S, 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 mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions and the crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions.

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 = 452.31

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.03

6169 reflections

254 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.89 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H18BrNO5S	Z = 2
Mr = 452.31	F000 = 460
Triclinic, P1	Dx = 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 = 2.2–27.5º
c = 11.6068 (3) Å	µ = 2.30 mm−1
α = 82.524 (1)º	T = 295 (2) K
β = 87.666 (2)º	Block, colourless
γ = 84.942 (3)º	0.20 × 0.20 × 0.16 mm
V = 952.16 (5) Å3

Bruker Kappa APEXII diffractometer	6169 independent reflections
Radiation source: Fine–focus sealed tube	4163 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.027
T = 295(2) K	θmax = 31.2º
ω and φ scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.593, Tmax = 0.692	k = −13→13
25160 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.054P)2 + 0.4811P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
6169 reflections	Δρmax = 0.68 e Å−3
254 parameters	Δρmin = −0.89 e Å−3
3 restraints	Extinction correction: None
Primary atom site location: Direct

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) .