tert-Butyl 3-[2,2-bis-(ethoxy-carbon-yl)vin-yl]-2-bromo-methyl-1H-indole-1-carboxyl-ate.

In the title compound, C(22)H(26)BrNO(6), the indole ring system is planar [maximum deviation 0.029 (2) Å]. The tert-butyl bound carboxyl-ate group forms a dihedral angle of 17.54 (8)° with the indole ring system. In the crystal, mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers by paired C-H⋯O hydrogen bonds.

Related literature

For general background to indoles, see: Gribble (1996 ▶); Jing-Ru et al. (2007 ▶); Ximenes et al. (2005 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H26BrNO6

M = 480.35

Triclinic,

a = 10.8682 (3) Å

b = 11.1094 (4) Å

c = 11.5699 (6) Å

α = 111.984 (3)°

β = 105.841 (2)°

γ = 106.926 (2)°

V = 1118.51 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.88 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS, Sheldrick, 2001 ▶) T min = 0.603, T max = 0.706

32165 measured reflections

8669 independent reflections

5490 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.01

8669 reflections

271 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041567/ci2911sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041567/ci2911Isup2.hkl

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

C22H26BrNO6	Z = 2
Mr = 480.35	F(000) = 496
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8682 (3) Å	Cell parameters from 8669 reflections
b = 11.1094 (4) Å	θ = 2.1–33.8°
c = 11.5699 (6) Å	µ = 1.88 mm−1
α = 111.984 (3)°	T = 293 K
β = 105.841 (2)°	Block, colourless
γ = 106.926 (2)°	0.30 × 0.25 × 0.20 mm
V = 1118.51 (9) Å3

Bruker Kappa APEXII area-detector diffractometer	8669 independent reflections
Radiation source: fine-focus sealed tube	5490 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 33.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS, Sheldrick, 2001)	h = −17→16
Tmin = 0.603, Tmax = 0.706	k = −16→17
32165 measured reflections	l = −17→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1525P] where P = (Fo2 + 2Fc2)/3
8669 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.29 e Å−3
1 restraint	Δρmin = −0.60 e Å−3

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.

	x	y	z	Uiso*/Ueq
C2	0.09184 (16)	0.74325 (17)	1.16827 (16)	0.0342 (3)
C3	0.07086 (19)	0.8044 (2)	1.28578 (19)	0.0441 (4)
H3	0.1358	0.8307	1.3725	0.053*
C4	−0.0521 (2)	0.8242 (2)	1.2671 (2)	0.0537 (5)
H4	−0.0694	0.8659	1.3435	0.064*
C5	−0.14938 (19)	0.7836 (2)	1.1379 (2)	0.0528 (5)
H5	−0.2299	0.7997	1.1293	0.063*
C6	−0.12946 (17)	0.7201 (2)	1.0217 (2)	0.0427 (4)
H6	−0.1966	0.6909	0.9349	0.051*
C7	−0.00584 (15)	0.70013 (16)	1.03705 (17)	0.0341 (3)
C8	0.04611 (15)	0.63561 (16)	0.94006 (16)	0.0328 (3)
C9	0.17083 (15)	0.63964 (16)	1.01285 (15)	0.0323 (3)
C10	0.31912 (16)	0.73467 (18)	1.26701 (16)	0.0365 (3)
C11	0.51726 (16)	0.67167 (19)	1.32235 (17)	0.0391 (3)
C12	0.5566 (2)	0.5718 (3)	1.2261 (2)	0.0578 (5)
H12A	0.4829	0.4747	1.1791	0.087*
H12B	0.6448	0.5760	1.2782	0.087*
H12C	0.5671	0.6010	1.1598	0.087*
C13	0.4815 (2)	0.6177 (3)	1.4162 (2)	0.0565 (5)
H13A	0.4495	0.6784	1.4716	0.085*
H13B	0.5647	0.6199	1.4752	0.085*
H13C	0.4074	0.5202	1.3616	0.085*
C14	0.6292 (2)	0.8251 (2)	1.3980 (2)	0.0603 (5)
H14A	0.6402	0.8560	1.3328	0.090*
H14B	0.7180	0.8316	1.4517	0.090*
H14C	0.6009	0.8861	1.4582	0.090*
C15	−0.02203 (15)	0.56833 (17)	0.78999 (16)	0.0361 (3)
H15	−0.0246	0.4788	0.7407	0.043*
C16	−0.08096 (15)	0.62017 (18)	0.71535 (16)	0.0367 (3)
C17	−0.06921 (18)	0.76980 (19)	0.77787 (18)	0.0425 (4)
C18	−0.1952 (2)	0.9111 (2)	0.8069 (3)	0.0658 (6)
H18A	−0.1147	0.9770	0.8966	0.079*
H18B	−0.1864	0.9505	0.7460	0.079*
C19	−0.3273 (3)	0.8959 (3)	0.8200 (4)	0.1028 (11)
H19A	−0.4062	0.8172	0.7355	0.154*
H19B	−0.3367	0.9837	0.8387	0.154*
H19C	−0.3262	0.8766	0.8944	0.154*
C20	−0.14814 (17)	0.5379 (2)	0.56162 (18)	0.0428 (4)
C21	−0.2390 (2)	0.3118 (2)	0.36364 (19)	0.0571 (5)
H21A	−0.1787	0.3480	0.3245	0.069*
H21B	−0.3299	0.3122	0.3247	0.069*
C22	−0.2597 (4)	0.1643 (3)	0.3329 (3)	0.0913 (9)
H22A	−0.1688	0.1647	0.3688	0.137*
H22B	−0.3073	0.1009	0.2347	0.137*
H22C	−0.3165	0.1311	0.3750	0.137*
C23	0.26606 (17)	0.59735 (18)	0.95525 (16)	0.0373 (3)
H23A	0.2140	0.5362	0.8558	0.045*
H23B	0.2997	0.5423	0.9929	0.045*
N1	0.20188 (13)	0.70606 (14)	1.15357 (13)	0.0331 (3)
O1	0.38397 (12)	0.65566 (13)	1.22367 (11)	0.0397 (2)
O2	0.34760 (15)	0.81621 (16)	1.38221 (13)	0.0570 (4)
O3	−0.19532 (13)	0.77004 (13)	0.75104 (14)	0.0476 (3)
O4	0.04207 (15)	0.87474 (16)	0.84512 (19)	0.0707 (4)
O5	−0.17187 (14)	0.40133 (14)	0.51266 (12)	0.0483 (3)
O6	−0.17445 (18)	0.59307 (18)	0.49278 (15)	0.0668 (4)
Br1	0.429587 (19)	0.76941 (2)	0.99976 (2)	0.05385 (8)

	U11	U22	U33	U12	U13	U23
C2	0.0370 (7)	0.0337 (8)	0.0387 (8)	0.0197 (6)	0.0174 (6)	0.0204 (7)
C3	0.0481 (9)	0.0488 (10)	0.0408 (9)	0.0256 (8)	0.0221 (8)	0.0219 (8)
C4	0.0559 (10)	0.0622 (12)	0.0581 (12)	0.0346 (10)	0.0359 (10)	0.0291 (10)
C5	0.0445 (9)	0.0635 (12)	0.0712 (13)	0.0335 (9)	0.0335 (9)	0.0392 (11)
C6	0.0344 (7)	0.0478 (10)	0.0531 (10)	0.0204 (7)	0.0174 (7)	0.0311 (8)
C7	0.0342 (7)	0.0320 (7)	0.0414 (8)	0.0164 (6)	0.0152 (6)	0.0224 (7)
C8	0.0346 (7)	0.0316 (7)	0.0334 (7)	0.0160 (6)	0.0114 (6)	0.0184 (6)
C9	0.0361 (7)	0.0323 (7)	0.0299 (7)	0.0182 (6)	0.0112 (6)	0.0163 (6)
C10	0.0384 (7)	0.0385 (8)	0.0335 (8)	0.0202 (7)	0.0123 (6)	0.0185 (7)
C11	0.0334 (7)	0.0500 (10)	0.0342 (8)	0.0223 (7)	0.0086 (6)	0.0221 (7)
C12	0.0541 (10)	0.0722 (14)	0.0528 (11)	0.0435 (10)	0.0189 (9)	0.0271 (10)
C13	0.0495 (10)	0.0813 (15)	0.0576 (12)	0.0335 (10)	0.0208 (9)	0.0497 (11)
C14	0.0430 (9)	0.0559 (12)	0.0664 (14)	0.0151 (9)	0.0151 (9)	0.0268 (11)
C15	0.0340 (7)	0.0369 (8)	0.0340 (8)	0.0155 (6)	0.0096 (6)	0.0181 (7)
C16	0.0311 (7)	0.0401 (8)	0.0356 (8)	0.0142 (6)	0.0084 (6)	0.0209 (7)
C17	0.0402 (8)	0.0410 (9)	0.0419 (9)	0.0148 (7)	0.0079 (7)	0.0256 (8)
C18	0.0744 (14)	0.0448 (11)	0.0804 (16)	0.0348 (11)	0.0287 (12)	0.0297 (11)
C19	0.0846 (18)	0.0762 (19)	0.129 (3)	0.0495 (16)	0.0475 (19)	0.0222 (18)
C20	0.0338 (7)	0.0545 (11)	0.0392 (9)	0.0184 (7)	0.0104 (7)	0.0268 (8)
C21	0.0551 (10)	0.0651 (13)	0.0308 (9)	0.0161 (10)	0.0135 (8)	0.0163 (9)
C22	0.129 (3)	0.0657 (16)	0.0488 (14)	0.0332 (17)	0.0320 (15)	0.0117 (12)
C23	0.0413 (7)	0.0407 (8)	0.0314 (8)	0.0238 (7)	0.0135 (6)	0.0164 (7)
N1	0.0359 (6)	0.0358 (7)	0.0297 (6)	0.0204 (5)	0.0115 (5)	0.0165 (5)
O1	0.0410 (5)	0.0488 (7)	0.0298 (5)	0.0282 (5)	0.0088 (5)	0.0179 (5)
O2	0.0569 (7)	0.0709 (9)	0.0311 (6)	0.0389 (7)	0.0105 (6)	0.0118 (6)
O3	0.0427 (6)	0.0366 (6)	0.0566 (8)	0.0189 (5)	0.0121 (6)	0.0220 (6)
O4	0.0441 (7)	0.0440 (8)	0.0922 (12)	0.0081 (6)	0.0071 (8)	0.0281 (8)
O5	0.0547 (7)	0.0486 (7)	0.0314 (6)	0.0190 (6)	0.0119 (5)	0.0178 (6)
O6	0.0823 (10)	0.0742 (10)	0.0452 (8)	0.0385 (9)	0.0118 (7)	0.0387 (8)
Br1	0.05092 (11)	0.05899 (14)	0.05578 (13)	0.02350 (9)	0.02807 (10)	0.02914 (10)

C2—C3	1.389 (2)	C14—H14A	0.96
C2—C7	1.393 (2)	C14—H14B	0.96
C2—N1	1.4057 (17)	C14—H14C	0.96
C3—C4	1.390 (2)	C15—C16	1.331 (2)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.383 (3)	C16—C20	1.489 (2)
C4—H4	0.93	C16—C17	1.493 (2)
C5—C6	1.374 (3)	C17—O4	1.189 (2)
C5—H5	0.93	C17—O3	1.321 (2)
C6—C7	1.399 (2)	C18—C19	1.452 (3)
C6—H6	0.93	C18—O3	1.454 (2)
C7—C8	1.439 (2)	C18—H18A	0.97
C8—C9	1.365 (2)	C18—H18B	0.97
C8—C15	1.458 (2)	C19—H19A	0.96
C9—N1	1.4017 (19)	C19—H19B	0.96
C9—C23	1.4701 (19)	C19—H19C	0.96
C10—O2	1.183 (2)	C20—O6	1.198 (2)
C10—O1	1.3199 (18)	C20—O5	1.318 (2)
C10—N1	1.409 (2)	C21—O5	1.450 (2)
C11—O1	1.4929 (17)	C21—C22	1.471 (4)
C11—C14	1.498 (3)	C21—H21A	0.97
C11—C12	1.504 (2)	C21—H21B	0.97
C11—C13	1.507 (2)	C22—H22A	0.96
C12—H12A	0.96	C22—H22B	0.96
C12—H12B	0.96	C22—H22C	0.96
C12—H12C	0.96	C23—Br1	1.9654 (17)
C13—H13A	0.96	C23—H23A	0.97
C13—H13B	0.96	C23—H23B	0.97
C13—H13C	0.96
C3—C2—C7	122.51 (14)	H14B—C14—H14C	109.5
C3—C2—N1	129.77 (15)	C16—C15—C8	127.53 (15)
C7—C2—N1	107.63 (12)	C16—C15—H15	116.2
C2—C3—C4	116.62 (17)	C8—C15—H15	116.2
C2—C3—H3	121.7	C15—C16—C20	121.44 (15)
C4—C3—H3	121.7	C15—C16—C17	122.82 (15)
C5—C4—C3	121.64 (17)	C20—C16—C17	115.34 (14)
C5—C4—H4	119.2	O4—C17—O3	125.11 (17)
C3—C4—H4	119.2	O4—C17—C16	122.78 (16)
C6—C5—C4	121.34 (15)	O3—C17—C16	112.10 (14)
C6—C5—H5	119.3	C19—C18—O3	109.1 (2)
C4—C5—H5	119.3	C19—C18—H18A	109.9
C5—C6—C7	118.48 (17)	O3—C18—H18A	109.9
C5—C6—H6	120.8	C19—C18—H18B	109.9
C7—C6—H6	120.8	O3—C18—H18B	109.9
C2—C7—C6	119.38 (14)	H18A—C18—H18B	108.3
C2—C7—C8	107.57 (12)	C18—C19—H19A	109.5
C6—C7—C8	133.01 (15)	C18—C19—H19B	109.5
C9—C8—C7	107.60 (13)	H19A—C19—H19B	109.5
C9—C8—C15	124.17 (13)	C18—C19—H19C	109.5
C7—C8—C15	128.12 (13)	H19A—C19—H19C	109.5
C8—C9—N1	109.10 (12)	H19B—C19—H19C	109.5
C8—C9—C23	125.35 (14)	O6—C20—O5	125.09 (17)
N1—C9—C23	125.16 (13)	O6—C20—C16	122.46 (18)
O2—C10—O1	127.84 (15)	O5—C20—C16	112.44 (14)
O2—C10—N1	122.20 (14)	O5—C21—C22	107.12 (18)
O1—C10—N1	109.93 (13)	O5—C21—H21A	110.3
O1—C11—C14	110.16 (14)	C22—C21—H21A	110.3
O1—C11—C12	101.60 (13)	O5—C21—H21B	110.3
C14—C11—C12	111.45 (16)	C22—C21—H21B	110.3
O1—C11—C13	108.63 (13)	H21A—C21—H21B	108.5
C14—C11—C13	113.56 (17)	C21—C22—H22A	109.5
C12—C11—C13	110.76 (17)	C21—C22—H22B	109.5
C11—C12—H12A	109.5	H22A—C22—H22B	109.5
C11—C12—H12B	109.5	C21—C22—H22C	109.5
H12A—C12—H12B	109.5	H22A—C22—H22C	109.5
C11—C12—H12C	109.5	H22B—C22—H22C	109.5
H12A—C12—H12C	109.5	C9—C23—Br1	110.47 (11)
H12B—C12—H12C	109.5	C9—C23—H23A	109.6
C11—C13—H13A	109.5	Br1—C23—H23A	109.6
C11—C13—H13B	109.5	C9—C23—H23B	109.6
H13A—C13—H13B	109.5	Br1—C23—H23B	109.6
C11—C13—H13C	109.5	H23A—C23—H23B	108.1
H13A—C13—H13C	109.5	C9—N1—C2	108.08 (12)
H13B—C13—H13C	109.5	C9—N1—C10	129.37 (12)
C11—C14—H14A	109.5	C2—N1—C10	122.55 (13)
C11—C14—H14B	109.5	C10—O1—C11	120.94 (12)
H14A—C14—H14B	109.5	C17—O3—C18	116.27 (15)
C11—C14—H14C	109.5	C20—O5—C21	116.52 (15)
H14A—C14—H14C	109.5
C7—C2—C3—C4	−1.5 (3)	C17—C16—C20—O6	9.1 (2)
N1—C2—C3—C4	−177.75 (17)	C15—C16—C20—O5	15.1 (2)
C2—C3—C4—C5	0.7 (3)	C17—C16—C20—O5	−171.97 (14)
C3—C4—C5—C6	0.8 (3)	C8—C9—C23—Br1	101.19 (16)
C4—C5—C6—C7	−1.6 (3)	N1—C9—C23—Br1	−70.93 (17)
C3—C2—C7—C6	0.8 (2)	C8—C9—N1—C2	0.55 (17)
N1—C2—C7—C6	177.74 (14)	C23—C9—N1—C2	173.76 (14)
C3—C2—C7—C8	−177.20 (15)	C8—C9—N1—C10	−179.59 (15)
N1—C2—C7—C8	−0.23 (17)	C23—C9—N1—C10	−6.4 (3)
C5—C6—C7—C2	0.8 (2)	C3—C2—N1—C9	176.49 (17)
C5—C6—C7—C8	178.15 (17)	C7—C2—N1—C9	−0.18 (17)
C2—C7—C8—C9	0.57 (17)	C3—C2—N1—C10	−3.4 (3)
C6—C7—C8—C9	−177.01 (17)	C7—C2—N1—C10	179.95 (14)
C2—C7—C8—C15	176.90 (15)	O2—C10—N1—C9	164.58 (17)
C6—C7—C8—C15	−0.7 (3)	O1—C10—N1—C9	−17.1 (2)
C7—C8—C9—N1	−0.68 (17)	O2—C10—N1—C2	−15.6 (3)
C15—C8—C9—N1	−177.20 (14)	O1—C10—N1—C2	162.71 (14)
C7—C8—C9—C23	−173.88 (15)	O2—C10—O1—C11	−5.6 (3)
C15—C8—C9—C23	9.6 (2)	N1—C10—O1—C11	176.24 (13)
C9—C8—C15—C16	−136.69 (17)	C14—C11—O1—C10	−57.2 (2)
C7—C8—C15—C16	47.5 (3)	C12—C11—O1—C10	−175.45 (16)
C8—C15—C16—C20	−179.46 (14)	C13—C11—O1—C10	67.7 (2)
C8—C15—C16—C17	8.1 (3)	O4—C17—O3—C18	1.3 (3)
C15—C16—C17—O4	57.9 (3)	C16—C17—O3—C18	−179.61 (16)
C20—C16—C17—O4	−115.0 (2)	C19—C18—O3—C17	−156.5 (2)
C15—C16—C17—O3	−121.20 (17)	O6—C20—O5—C21	−1.9 (3)
C20—C16—C17—O3	65.95 (19)	C16—C20—O5—C21	179.18 (14)
C15—C16—C20—O6	−163.84 (17)	C22—C21—O5—C20	−177.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O4i	0.97	2.56	3.392 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯O4i	0.97	2.56	3.392 (3)	144

Symmetry code: (i) .