Ethyl 2-bromo-3-(1-phenyl­sulfonyl-1H-indol-3-yl)acrylate

In the title compound, C₁₉H₁₆BrNO₄S, the mean plane of the indole ring system (A) and the phenyl ring make a dihedral angle of 77.41 (5)°. An intra­molecular C—H...Br hydrogen bond provides an essential coplanarity of the mean plane of bromo­acrylic acid ethyl ester substituent and plane A, with a dihedral angle of 4.96 (8)°. Weak inter­molecular C—H...O hydrogen bonds and π–π inter­actions stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.089
• Data-to-parameter ratio = 26.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.441     0.631
            Tmin and Tmax expected:      0.353     0.596
            RR =      1.179
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.18
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.945
            Tmax scaled      0.596 Tmin scaled      0.417

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Ethyl 2-bromo-3-(1-phenylsulfonyl-1H-indol-3-yl)acrylate

Crystal data

C19H16BrNO4S	Z = 2
Mr = 434.30	F(000) = 440
Triclinic, P1	Dx = 1.627 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4062 (2) Å	Cell parameters from 9386 reflections
b = 10.3698 (3) Å	θ = 2.9–36.8°
c = 11.2651 (2) Å	µ = 2.46 mm^−1
α = 114.231 (1)°	T = 100 K
β = 114.060 (1)°	Block, colourless
γ = 92.189 (1)°	0.44 × 0.43 × 0.21 mm
V = 886.63 (4) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	6376 independent reflections
Radiation source: fine-focus sealed tube	5312 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.33 pixels mm^-1	θmax = 32.5°, θmin = 2.2°
ω scans	h = −13→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.441, Tmax = 0.631	l = −17→17
22469 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0331P)^2 + 0.8827P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
6376 reflections	Δρmax = 2.09 e Å^−3
237 parameters	Δρmin = −1.67 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.69015 (3)	0.20197 (2)	0.61990 (2)	0.03033 (7)
S1	0.99469 (5)	0.00324 (4)	0.27263 (5)	0.01571 (8)
O1	1.07586 (15)	0.04061 (14)	0.42505 (14)	0.0207 (2)
O2	1.07625 (15)	0.04583 (14)	0.20689 (15)	0.0204 (2)
O3	0.42454 (19)	0.33790 (18)	0.65018 (17)	0.0315 (3)
O4	0.32040 (15)	0.36142 (14)	0.44360 (15)	0.0203 (2)
N1	0.84078 (17)	0.08265 (15)	0.25395 (16)	0.0157 (2)
C1	0.7791 (2)	0.12783 (17)	0.35379 (18)	0.0163 (3)
H1	0.8181	0.1191	0.4416	0.020*
C2	0.65277 (19)	0.18708 (17)	0.30505 (18)	0.0156 (3)
C3	0.63423 (19)	0.17744 (17)	0.16656 (18)	0.0157 (3)
C4	0.5294 (2)	0.22066 (19)	0.0673 (2)	0.0196 (3)
H4	0.4519	0.2695	0.0865	0.023*
C5	0.5416 (2)	0.1905 (2)	−0.0595 (2)	0.0216 (3)
H5	0.4721	0.2200	−0.1272	0.026*
C6	0.6545 (2)	0.1172 (2)	−0.0899 (2)	0.0209 (3)
H6	0.6575	0.0954	−0.1793	0.025*
C7	0.7618 (2)	0.07586 (18)	0.00729 (19)	0.0182 (3)
H7	0.8395	0.0276	−0.0124	0.022*
C8	0.74994 (19)	0.10871 (17)	0.13535 (18)	0.0153 (3)
C9	0.9057 (2)	−0.18478 (18)	0.16769 (19)	0.0169 (3)
C10	0.8401 (2)	−0.25447 (19)	0.2231 (2)	0.0200 (3)
H10	0.8448	−0.2015	0.3169	0.024*
C11	0.7676 (2)	−0.4032 (2)	0.1384 (2)	0.0244 (4)
H11	0.7219	−0.4527	0.1740	0.029*
C12	0.7622 (3)	−0.4794 (2)	0.0017 (2)	0.0310 (4)
H12	0.7122	−0.5809	−0.0560	0.037*
C13	0.8292 (3)	−0.4081 (2)	−0.0511 (2)	0.0336 (5)
H13	0.8256	−0.4614	−0.1443	0.040*
C14	0.9013 (2)	−0.2599 (2)	0.0310 (2)	0.0250 (4)
H14	0.9466	−0.2106	−0.0050	0.030*
C15	0.5478 (2)	0.24609 (18)	0.36745 (19)	0.0173 (3)
H15	0.4679	0.2805	0.3121	0.021*
C16	0.5443 (2)	0.26046 (18)	0.4904 (2)	0.0188 (3)
C17	0.4257 (2)	0.32334 (19)	0.5387 (2)	0.0201 (3)
C18	0.1930 (2)	0.41039 (19)	0.4781 (2)	0.0203 (3)
H18A	0.2383	0.5013	0.5727	0.024*
H18B	0.1356	0.3350	0.4864	0.024*
C19	0.0796 (2)	0.4372 (2)	0.3552 (2)	0.0255 (4)
H19A	−0.0150	0.4586	0.3686	0.038*
H19B	0.0459	0.3501	0.2609	0.038*
H19C	0.1340	0.5203	0.3560	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.04006 (13)	0.04491 (13)	0.03028 (11)	0.02889 (10)	0.02648 (10)	0.02703 (10)
S1	0.01449 (17)	0.01793 (17)	0.01536 (18)	0.00596 (13)	0.00854 (15)	0.00658 (15)
O1	0.0190 (6)	0.0242 (6)	0.0155 (6)	0.0079 (5)	0.0070 (5)	0.0072 (5)
O2	0.0188 (6)	0.0215 (6)	0.0234 (6)	0.0051 (5)	0.0141 (5)	0.0085 (5)
O3	0.0327 (8)	0.0477 (9)	0.0259 (7)	0.0200 (7)	0.0216 (6)	0.0184 (7)
O4	0.0206 (6)	0.0233 (6)	0.0227 (6)	0.0100 (5)	0.0156 (5)	0.0097 (5)
N1	0.0164 (6)	0.0189 (6)	0.0153 (6)	0.0078 (5)	0.0097 (5)	0.0082 (5)
C1	0.0178 (7)	0.0181 (7)	0.0146 (7)	0.0060 (6)	0.0101 (6)	0.0064 (6)
C2	0.0154 (7)	0.0161 (7)	0.0155 (7)	0.0048 (5)	0.0088 (6)	0.0059 (6)
C3	0.0150 (7)	0.0163 (7)	0.0166 (7)	0.0034 (5)	0.0081 (6)	0.0077 (6)
C4	0.0169 (7)	0.0218 (7)	0.0225 (8)	0.0058 (6)	0.0091 (7)	0.0125 (7)
C5	0.0201 (8)	0.0253 (8)	0.0217 (8)	0.0038 (6)	0.0078 (7)	0.0151 (7)
C6	0.0231 (8)	0.0240 (8)	0.0183 (8)	0.0026 (6)	0.0104 (7)	0.0120 (7)
C7	0.0198 (7)	0.0202 (7)	0.0178 (8)	0.0040 (6)	0.0115 (6)	0.0090 (6)
C8	0.0156 (7)	0.0161 (6)	0.0156 (7)	0.0034 (5)	0.0085 (6)	0.0075 (6)
C9	0.0174 (7)	0.0171 (7)	0.0166 (7)	0.0064 (6)	0.0093 (6)	0.0066 (6)
C10	0.0226 (8)	0.0223 (8)	0.0180 (8)	0.0072 (6)	0.0111 (7)	0.0101 (7)
C11	0.0304 (9)	0.0221 (8)	0.0262 (9)	0.0063 (7)	0.0163 (8)	0.0130 (7)
C12	0.0441 (12)	0.0185 (8)	0.0317 (11)	0.0035 (8)	0.0240 (10)	0.0068 (8)
C13	0.0520 (14)	0.0218 (8)	0.0295 (10)	0.0030 (8)	0.0297 (10)	0.0040 (8)
C14	0.0335 (10)	0.0215 (8)	0.0239 (9)	0.0048 (7)	0.0208 (8)	0.0069 (7)
C15	0.0165 (7)	0.0183 (7)	0.0176 (7)	0.0062 (6)	0.0096 (6)	0.0071 (6)
C16	0.0204 (7)	0.0199 (7)	0.0206 (8)	0.0088 (6)	0.0133 (7)	0.0093 (6)
C17	0.0198 (8)	0.0208 (7)	0.0210 (8)	0.0070 (6)	0.0131 (7)	0.0069 (7)
C18	0.0198 (8)	0.0211 (7)	0.0243 (9)	0.0076 (6)	0.0157 (7)	0.0086 (7)
C19	0.0228 (8)	0.0316 (9)	0.0274 (9)	0.0112 (7)	0.0159 (8)	0.0139 (8)

Geometric parameters (Å, º)

Br1—C16	1.8807 (17)	C7—C8	1.393 (2)
S1—O2	1.4276 (13)	C7—H7	0.95
S1—O1	1.4295 (13)	C9—C14	1.393 (2)
S1—N1	1.6742 (14)	C9—C10	1.394 (2)
S1—C9	1.7540 (17)	C10—C11	1.391 (3)
O3—C17	1.206 (2)	C10—H10	0.95
O4—C17	1.341 (2)	C11—C12	1.390 (3)
O4—C18	1.452 (2)	C11—H11	0.95
N1—C1	1.394 (2)	C12—C13	1.388 (3)
N1—C8	1.404 (2)	C12—H12	0.95
C1—C2	1.375 (2)	C13—C14	1.386 (3)
C1—H1	0.95	C13—H13	0.95
C2—C15	1.450 (2)	C14—H14	0.95
C2—C3	1.457 (2)	C15—C16	1.345 (2)
C3—C4	1.404 (2)	C15—H15	0.95
C3—C8	1.408 (2)	C16—C17	1.492 (2)
C4—C5	1.386 (3)	C18—C19	1.506 (3)
C4—H4	0.95	C18—H18A	0.99
C5—C6	1.403 (3)	C18—H18B	0.99
C5—H5	0.95	C19—H19A	0.98
C6—C7	1.385 (2)	C19—H19B	0.98
C6—H6	0.95	C19—H19C	0.98
O2—S1—O1	120.60 (8)	C11—C10—C9	118.62 (16)
O2—S1—N1	106.37 (7)	C11—C10—H10	120.7
O1—S1—N1	104.97 (7)	C9—C10—H10	120.7
O2—S1—C9	109.07 (8)	C12—C11—C10	120.05 (17)
O1—S1—C9	109.55 (8)	C12—C11—H11	120.0
N1—S1—C9	105.10 (7)	C10—C11—H11	120.0
C17—O4—C18	114.31 (14)	C13—C12—C11	120.43 (18)
C1—N1—C8	109.43 (13)	C13—C12—H12	119.8
C1—N1—S1	124.10 (12)	C11—C12—H12	119.8
C8—N1—S1	126.42 (11)	C14—C13—C12	120.57 (19)
C2—C1—N1	109.24 (14)	C14—C13—H13	119.7
C2—C1—H1	125.4	C12—C13—H13	119.7
N1—C1—H1	125.4	C13—C14—C9	118.41 (17)
C1—C2—C15	130.46 (16)	C13—C14—H14	120.8
C1—C2—C3	106.77 (14)	C9—C14—H14	120.8
C15—C2—C3	122.75 (14)	C16—C15—C2	131.03 (16)
C4—C3—C8	118.80 (15)	C16—C15—H15	114.5
C4—C3—C2	133.43 (15)	C2—C15—H15	114.5
C8—C3—C2	107.77 (14)	C15—C16—C17	124.25 (16)
C5—C4—C3	118.50 (16)	C15—C16—Br1	122.96 (12)
C5—C4—H4	120.7	C17—C16—Br1	112.79 (13)
C3—C4—H4	120.7	O3—C17—O4	124.01 (16)
C4—C5—C6	121.28 (16)	O3—C17—C16	123.94 (17)
C4—C5—H5	119.4	O4—C17—C16	112.05 (15)
C6—C5—H5	119.4	O4—C18—C19	107.33 (14)
C7—C6—C5	121.58 (16)	O4—C18—H18A	110.2
C7—C6—H6	119.2	C19—C18—H18A	110.2
C5—C6—H6	119.2	O4—C18—H18B	110.2
C6—C7—C8	116.59 (16)	C19—C18—H18B	110.2
C6—C7—H7	121.7	H18A—C18—H18B	108.5
C8—C7—H7	121.7	C18—C19—H19A	109.5
C7—C8—N1	130.08 (15)	C18—C19—H19B	109.5
C7—C8—C3	123.19 (15)	H19A—C19—H19B	109.5
N1—C8—C3	106.72 (14)	C18—C19—H19C	109.5
C14—C9—C10	121.92 (16)	H19A—C19—H19C	109.5
C14—C9—S1	119.14 (13)	H19B—C19—H19C	109.5
C10—C9—S1	118.93 (13)
O2—S1—N1—C1	−148.63 (14)	C4—C3—C8—N1	177.90 (15)
O1—S1—N1—C1	−19.74 (16)	C2—C3—C8—N1	−2.35 (18)
C9—S1—N1—C1	95.79 (15)	O2—S1—C9—C14	−10.11 (17)
O2—S1—N1—C8	34.24 (16)	O1—S1—C9—C14	−144.09 (15)
O1—S1—N1—C8	163.12 (14)	N1—S1—C9—C14	103.60 (15)
C9—S1—N1—C8	−81.35 (15)	O2—S1—C9—C10	170.45 (13)
C8—N1—C1—C2	−1.85 (19)	O1—S1—C9—C10	36.48 (16)
S1—N1—C1—C2	−179.41 (12)	N1—S1—C9—C10	−75.84 (15)
N1—C1—C2—C15	178.52 (16)	C14—C9—C10—C11	−0.3 (3)
N1—C1—C2—C3	0.35 (18)	S1—C9—C10—C11	179.08 (14)
C1—C2—C3—C4	−179.03 (18)	C9—C10—C11—C12	0.2 (3)
C15—C2—C3—C4	2.6 (3)	C10—C11—C12—C13	0.2 (3)
C1—C2—C3—C8	1.26 (18)	C11—C12—C13—C14	−0.5 (4)
C15—C2—C3—C8	−177.09 (15)	C12—C13—C14—C9	0.4 (3)
C8—C3—C4—C5	1.6 (2)	C10—C9—C14—C13	0.0 (3)
C2—C3—C4—C5	−178.09 (17)	S1—C9—C14—C13	−179.39 (17)
C3—C4—C5—C6	0.6 (3)	C1—C2—C15—C16	0.4 (3)
C4—C5—C6—C7	−2.0 (3)	C3—C2—C15—C16	178.31 (18)
C5—C6—C7—C8	1.0 (3)	C2—C15—C16—C17	−179.45 (17)
C6—C7—C8—N1	−179.36 (16)	C2—C15—C16—Br1	0.4 (3)
C6—C7—C8—C3	1.3 (2)	C18—O4—C17—O3	−5.4 (3)
C1—N1—C8—C7	−176.78 (17)	C18—O4—C17—C16	174.46 (14)
S1—N1—C8—C7	0.7 (3)	C15—C16—C17—O3	−178.88 (19)
C1—N1—C8—C3	2.60 (18)	Br1—C16—C17—O3	1.3 (2)
S1—N1—C8—C3	−179.91 (12)	C15—C16—C17—O4	1.3 (3)
C4—C3—C8—C7	−2.7 (2)	Br1—C16—C17—O4	−178.59 (12)
C2—C3—C8—C7	177.09 (15)	C17—O4—C18—C19	−175.66 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1	0.95	2.62	3.237 (2)	123
C7—H7···O2^i	0.95	2.47	3.222 (2)	136
C10—H10···O1^ii	0.95	2.44	3.369 (2)	166

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