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

In the title compound, C(22)H(27)NO(6), the indole ring system is planar and the ethoxy-carbonyl chains adopt extended conformations. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds occur, resulting in R(2) (2)(16) dimers, which are inter-linked into a chain propagating along the a axis by π-π stacking inter-actions [centroid-centroid distance 3.5916 (9) Å].

Related literature

For general background, see: Hood et al. (1992 ▶); Cram et al. (2001 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H27NO6

M = 401.45

Monoclinic,

a = 9.1933 (3) Å

b = 21.8495 (6) Å

c = 10.7676 (3) Å

β = 96.510 (2)°

V = 2148.93 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.978, T max = 0.982

24241 measured reflections

4766 independent reflections

3534 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.134

S = 1.04

4766 reflections

286 parameters

28 restraints

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.28 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/S1600536809009635/ci2766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009635/ci2766Isup2.hkl

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

C22H27NO6	F(000) = 856
Mr = 401.45	Dx = 1.241 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4766 reflections
a = 9.1933 (3) Å	θ = 2.1–27.2°
b = 21.8495 (6) Å	µ = 0.09 mm−1
c = 10.7676 (3) Å	T = 293 K
β = 96.510 (2)°	Block, brown
V = 2148.93 (11) Å3	0.25 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	4766 independent reflections
Radiation source: fine-focus sealed tube	3534 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω and φ scans	θmax = 27.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.978, Tmax = 0.982	k = −27→28
24241 measured reflections	l = −13→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.6467P] where P = (Fo2 + 2Fc2)/3
4766 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.25 e Å−3
28 restraints	Δρmin = −0.28 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	Occ. (<1)
O1	0.11345 (14)	0.63504 (5)	0.68637 (11)	0.0507 (3)
O2	0.00198 (17)	0.68868 (6)	0.52523 (12)	0.0639 (4)
O3	0.39872 (13)	0.51263 (5)	0.24128 (12)	0.0508 (3)
O4	0.34111 (19)	0.43222 (8)	0.11765 (15)	0.0797 (5)
O5	0.3720 (2)	0.33528 (7)	0.4564 (2)	0.0942 (6)
O6	0.49107 (19)	0.34337 (7)	0.2910 (2)	0.0947 (6)
N1	0.09171 (14)	0.59345 (5)	0.49600 (12)	0.0370 (3)
C2	0.03282 (17)	0.58731 (7)	0.37025 (14)	0.0378 (3)
C3	−0.06844 (19)	0.62313 (8)	0.29745 (16)	0.0482 (4)
H3	−0.1061	0.6587	0.3287	0.058*
C4	−0.1107 (2)	0.60389 (9)	0.17750 (17)	0.0572 (5)
H4	−0.1775	0.6273	0.1263	0.069*
C5	−0.0566 (2)	0.55057 (10)	0.13070 (16)	0.0571 (5)
H5	−0.0877	0.5387	0.0490	0.069*
C6	0.0423 (2)	0.51497 (9)	0.20315 (16)	0.0491 (4)
H6	0.0776	0.4790	0.1715	0.059*
C7	0.08915 (17)	0.53353 (7)	0.32463 (14)	0.0386 (3)
C8	0.18327 (17)	0.50633 (7)	0.42574 (15)	0.0381 (3)
C9	0.18175 (16)	0.54260 (7)	0.52819 (14)	0.0368 (3)
C10	0.06355 (18)	0.64434 (7)	0.56895 (15)	0.0425 (4)
C11	0.1044 (2)	0.68359 (8)	0.78201 (17)	0.0514 (4)
C12	0.1872 (3)	0.65426 (12)	0.89548 (19)	0.0792 (7)
H12A	0.1399	0.6167	0.9140	0.119*
H12B	0.1885	0.6815	0.9655	0.119*
H12C	0.2857	0.6459	0.8792	0.119*
C13	0.1810 (2)	0.74056 (9)	0.7464 (2)	0.0657 (5)
H13A	0.2768	0.7302	0.7256	0.099*
H13B	0.1897	0.7687	0.8153	0.099*
H13C	0.1256	0.7592	0.6754	0.099*
C14	−0.0535 (2)	0.69411 (10)	0.7993 (2)	0.0672 (6)
H14A	−0.1032	0.7120	0.7248	0.101*
H14B	−0.0595	0.7213	0.8686	0.101*
H14C	−0.0986	0.6558	0.8157	0.101*
C15	0.26345 (17)	0.44895 (7)	0.42693 (16)	0.0431 (4)
H15	0.2655	0.4263	0.5002	0.052*
C16	0.33461 (18)	0.42406 (7)	0.33802 (17)	0.0465 (4)
C17	0.35749 (19)	0.45525 (8)	0.21940 (18)	0.0513 (4)
C18	0.4202 (3)	0.55038 (11)	0.1348 (2)	0.0752 (6)
H18A	0.3363	0.5474	0.0718	0.090*
H18B	0.5067	0.5373	0.0981	0.090*
C19	0.4382 (4)	0.61385 (13)	0.1811 (3)	0.1133 (11)
H19A	0.3498	0.6270	0.2128	0.170*
H19B	0.4585	0.6402	0.1139	0.170*
H19C	0.5179	0.6156	0.2468	0.170*
C20	0.4073 (2)	0.36390 (8)	0.3563 (2)	0.0626 (5)
C21A	0.4535 (8)	0.2800 (2)	0.5168 (11)	0.093 (2)	0.580 (10)
H21A	0.5473	0.2741	0.4853	0.111*	0.580 (10)
H21B	0.4684	0.2836	0.6071	0.111*	0.580 (10)
C22A	0.3500 (8)	0.2300 (3)	0.4765 (13)	0.089 (3)	0.420 (10)
H22A	0.3897	0.1917	0.5081	0.134*	0.420 (10)
H22B	0.3350	0.2286	0.3869	0.134*	0.420 (10)
H22C	0.2582	0.2374	0.5084	0.134*	0.420 (10)
C21B	0.4319 (10)	0.2723 (3)	0.4519 (9)	0.0645 (19)	0.420 (10)
H21C	0.3936	0.2511	0.3760	0.077*	0.420 (10)
H21D	0.5380	0.2724	0.4591	0.077*	0.420 (10)
C22B	0.3768 (8)	0.2453 (3)	0.5638 (9)	0.096 (2)	0.580 (10)
H22D	0.4068	0.2033	0.5719	0.144*	0.580 (10)
H22E	0.2718	0.2475	0.5552	0.144*	0.580 (10)
H22F	0.4160	0.2675	0.6369	0.144*	0.580 (10)
C23	0.26713 (19)	0.53322 (8)	0.65178 (16)	0.0478 (4)
H23A	0.3283	0.4978	0.6487	0.072*
H23B	0.2014	0.5273	0.7139	0.072*
H23C	0.3271	0.5685	0.6729	0.072*

	U11	U22	U33	U12	U13	U23
O1	0.0686 (8)	0.0437 (6)	0.0384 (6)	0.0115 (6)	−0.0001 (6)	−0.0066 (5)
O2	0.0922 (10)	0.0455 (7)	0.0517 (8)	0.0258 (7)	−0.0018 (7)	−0.0023 (6)
O3	0.0479 (7)	0.0487 (7)	0.0557 (8)	0.0009 (5)	0.0059 (6)	0.0031 (5)
O4	0.0929 (12)	0.0852 (11)	0.0638 (9)	−0.0061 (9)	0.0205 (8)	−0.0259 (8)
O5	0.0943 (12)	0.0479 (8)	0.1461 (17)	0.0286 (8)	0.0386 (12)	0.0268 (10)
O6	0.0797 (11)	0.0628 (10)	0.1485 (17)	0.0245 (8)	0.0437 (11)	−0.0134 (10)
N1	0.0403 (7)	0.0349 (6)	0.0353 (7)	0.0041 (5)	0.0019 (5)	−0.0001 (5)
C2	0.0400 (8)	0.0386 (8)	0.0349 (8)	0.0015 (6)	0.0047 (6)	0.0018 (6)
C3	0.0525 (10)	0.0458 (9)	0.0454 (10)	0.0110 (7)	0.0022 (8)	0.0056 (7)
C4	0.0592 (11)	0.0679 (12)	0.0421 (10)	0.0134 (9)	−0.0045 (8)	0.0110 (8)
C5	0.0597 (11)	0.0756 (13)	0.0348 (9)	0.0058 (10)	−0.0003 (8)	−0.0023 (8)
C6	0.0504 (10)	0.0566 (10)	0.0406 (9)	0.0053 (8)	0.0058 (7)	−0.0074 (7)
C7	0.0378 (8)	0.0409 (8)	0.0375 (8)	0.0012 (6)	0.0058 (6)	0.0008 (6)
C8	0.0361 (8)	0.0367 (8)	0.0416 (9)	0.0019 (6)	0.0050 (6)	0.0006 (6)
C9	0.0337 (7)	0.0344 (7)	0.0419 (8)	0.0017 (6)	0.0027 (6)	0.0028 (6)
C10	0.0488 (9)	0.0369 (8)	0.0417 (9)	0.0052 (7)	0.0043 (7)	−0.0016 (7)
C11	0.0596 (11)	0.0500 (10)	0.0446 (10)	0.0031 (8)	0.0055 (8)	−0.0149 (7)
C12	0.1044 (18)	0.0845 (16)	0.0454 (11)	0.0108 (14)	−0.0056 (11)	−0.0163 (11)
C13	0.0655 (13)	0.0569 (11)	0.0758 (14)	−0.0066 (9)	0.0130 (11)	−0.0185 (10)
C14	0.0648 (13)	0.0679 (13)	0.0716 (14)	−0.0075 (10)	0.0198 (11)	−0.0251 (10)
C15	0.0403 (8)	0.0369 (8)	0.0517 (10)	0.0015 (6)	0.0037 (7)	0.0014 (7)
C16	0.0400 (9)	0.0372 (8)	0.0625 (11)	0.0010 (7)	0.0070 (8)	−0.0074 (7)
C17	0.0416 (9)	0.0527 (10)	0.0606 (11)	0.0030 (8)	0.0098 (8)	−0.0116 (9)
C18	0.0777 (15)	0.0826 (16)	0.0658 (14)	−0.0049 (12)	0.0107 (11)	0.0210 (12)
C19	0.147 (3)	0.0703 (17)	0.117 (2)	−0.0217 (17)	−0.009 (2)	0.0326 (16)
C20	0.0486 (10)	0.0378 (9)	0.1030 (17)	0.0015 (8)	0.0151 (11)	−0.0059 (10)
C21A	0.107 (4)	0.057 (3)	0.112 (5)	0.024 (3)	0.001 (4)	0.002 (4)
C22A	0.094 (4)	0.072 (4)	0.101 (6)	0.004 (3)	0.008 (4)	0.009 (4)
C21B	0.090 (4)	0.038 (3)	0.067 (4)	0.022 (3)	0.014 (3)	0.011 (3)
C22B	0.117 (4)	0.073 (3)	0.102 (5)	0.028 (3)	0.031 (4)	0.037 (3)
C23	0.0466 (9)	0.0463 (9)	0.0477 (10)	0.0074 (7)	−0.0065 (7)	0.0002 (7)

O1—C10	1.311 (2)	C12—H12C	0.96
O1—C11	1.4874 (19)	C13—H13A	0.96
O2—C10	1.1917 (19)	C13—H13B	0.96
O3—C17	1.323 (2)	C13—H13C	0.96
O3—C18	1.444 (2)	C14—H14A	0.96
O4—C17	1.200 (2)	C14—H14B	0.96
O5—C20	1.318 (3)	C14—H14C	0.96
O5—C21B	1.484 (6)	C15—C16	1.335 (2)
O5—C21A	1.528 (6)	C15—H15	0.93
O6—C20	1.188 (2)	C16—C20	1.478 (2)
N1—C10	1.402 (2)	C16—C17	1.484 (3)
N1—C9	1.4053 (19)	C18—C19	1.477 (4)
N1—C2	1.4065 (19)	C18—H18A	0.97
C2—C3	1.389 (2)	C18—H18B	0.97
C2—C7	1.396 (2)	C19—H19A	0.96
C3—C4	1.372 (3)	C19—H19B	0.96
C3—H3	0.93	C19—H19C	0.96
C4—C5	1.384 (3)	C21A—C22A	1.481 (7)
C4—H4	0.93	C21A—H21A	0.97
C5—C6	1.371 (3)	C21A—H21B	0.97
C5—H5	0.93	C22A—H22A	0.96
C6—C7	1.390 (2)	C22A—H22B	0.96
C6—H6	0.93	C22A—H22C	0.96
C7—C8	1.440 (2)	C21B—C22B	1.482 (6)
C8—C9	1.360 (2)	C21B—H21C	0.97
C8—C15	1.454 (2)	C21B—H21D	0.97
C9—C23	1.481 (2)	C22B—H22D	0.96
C11—C13	1.501 (3)	C22B—H22E	0.96
C11—C14	1.502 (3)	C22B—H22F	0.96
C11—C12	1.507 (3)	C23—H23A	0.96
C12—H12A	0.96	C23—H23B	0.96
C12—H12B	0.96	C23—H23C	0.96
C10—O1—C11	121.09 (13)	H14A—C14—H14C	109.5
C17—O3—C18	117.53 (16)	H14B—C14—H14C	109.5
C20—O5—C21B	106.6 (3)	C16—C15—C8	129.37 (16)
C20—O5—C21A	124.6 (4)	C16—C15—H15	115.3
C10—N1—C9	129.03 (13)	C8—C15—H15	115.3
C10—N1—C2	122.65 (12)	C15—C16—C20	121.19 (18)
C9—N1—C2	108.28 (12)	C15—C16—C17	123.98 (15)
C3—C2—C7	121.85 (15)	C20—C16—C17	114.67 (16)
C3—C2—N1	130.54 (15)	O4—C17—O3	124.32 (19)
C7—C2—N1	107.54 (13)	O4—C17—C16	125.33 (18)
C4—C3—C2	117.33 (16)	O3—C17—C16	110.35 (15)
C4—C3—H3	121.3	O3—C18—C19	106.8 (2)
C2—C3—H3	121.3	O3—C18—H18A	110.4
C3—C4—C5	121.69 (17)	C19—C18—H18A	110.4
C3—C4—H4	119.2	O3—C18—H18B	110.4
C5—C4—H4	119.2	C19—C18—H18B	110.4
C6—C5—C4	120.87 (17)	H18A—C18—H18B	108.6
C6—C5—H5	119.6	C18—C19—H19A	109.5
C4—C5—H5	119.6	C18—C19—H19B	109.5
C5—C6—C7	118.98 (17)	H19A—C19—H19B	109.5
C5—C6—H6	120.5	C18—C19—H19C	109.5
C7—C6—H6	120.5	H19A—C19—H19C	109.5
C6—C7—C2	119.28 (15)	H19B—C19—H19C	109.5
C6—C7—C8	133.34 (15)	O6—C20—O5	122.79 (19)
C2—C7—C8	107.25 (13)	O6—C20—C16	124.8 (2)
C9—C8—C7	108.20 (13)	O5—C20—C16	112.41 (17)
C9—C8—C15	123.19 (14)	C22A—C21A—O5	101.0 (5)
C7—C8—C15	128.55 (15)	C22A—C21A—H21A	111.6
C8—C9—N1	108.70 (13)	O5—C21A—H21A	111.6
C8—C9—C23	126.54 (14)	C22A—C21A—H21B	111.6
N1—C9—C23	124.65 (14)	O5—C21A—H21B	111.6
O2—C10—O1	127.26 (15)	H21A—C21A—H21B	109.4
O2—C10—N1	122.20 (15)	C21A—C22A—H22A	109.5
O1—C10—N1	110.53 (13)	C21A—C22A—H22B	109.5
O1—C11—C13	110.46 (15)	H22A—C22A—H22B	109.5
O1—C11—C14	109.02 (15)	C21A—C22A—H22C	109.5
C13—C11—C14	113.14 (17)	H22A—C22A—H22C	109.5
O1—C11—C12	101.26 (14)	H22B—C22A—H22C	109.5
C13—C11—C12	110.58 (18)	C22B—C21B—O5	100.4 (4)
C14—C11—C12	111.74 (19)	C22B—C21B—H21C	111.7
C11—C12—H12A	109.5	O5—C21B—H21C	111.7
C11—C12—H12B	109.5	C22B—C21B—H21D	111.7
H12A—C12—H12B	109.5	O5—C21B—H21D	111.7
C11—C12—H12C	109.5	H21C—C21B—H21D	109.5
H12A—C12—H12C	109.5	C21B—C22B—H22D	109.5
H12B—C12—H12C	109.5	C21B—C22B—H22E	109.5
C11—C13—H13A	109.5	H22D—C22B—H22E	109.5
C11—C13—H13B	109.5	C21B—C22B—H22F	109.5
H13A—C13—H13B	109.5	H22D—C22B—H22F	109.5
C11—C13—H13C	109.5	H22E—C22B—H22F	109.5
H13A—C13—H13C	109.5	C9—C23—H23A	109.5
H13B—C13—H13C	109.5	C9—C23—H23B	109.5
C11—C14—H14A	109.5	H23A—C23—H23B	109.5
C11—C14—H14B	109.5	C9—C23—H23C	109.5
H14A—C14—H14B	109.5	H23A—C23—H23C	109.5
C11—C14—H14C	109.5	H23B—C23—H23C	109.5
C10—N1—C2—C3	−6.4 (3)	C2—N1—C10—O2	−8.8 (3)
C9—N1—C2—C3	175.54 (17)	C9—N1—C10—O1	−11.4 (2)
C10—N1—C2—C7	176.75 (14)	C2—N1—C10—O1	171.02 (14)
C9—N1—C2—C7	−1.29 (16)	C10—O1—C11—C13	−57.4 (2)
C7—C2—C3—C4	−0.5 (3)	C10—O1—C11—C14	67.5 (2)
N1—C2—C3—C4	−176.98 (17)	C10—O1—C11—C12	−174.57 (17)
C2—C3—C4—C5	0.8 (3)	C9—C8—C15—C16	−143.93 (18)
C3—C4—C5—C6	−0.2 (3)	C7—C8—C15—C16	39.3 (3)
C4—C5—C6—C7	−0.7 (3)	C8—C15—C16—C20	−178.54 (16)
C5—C6—C7—C2	0.9 (3)	C8—C15—C16—C17	6.3 (3)
C5—C6—C7—C8	176.11 (18)	C18—O3—C17—O4	2.3 (3)
C3—C2—C7—C6	−0.3 (2)	C18—O3—C17—C16	−177.62 (16)
N1—C2—C7—C6	176.85 (14)	C15—C16—C17—O4	−135.4 (2)
C3—C2—C7—C8	−176.65 (15)	C20—C16—C17—O4	49.2 (3)
N1—C2—C7—C8	0.51 (17)	C15—C16—C17—O3	44.5 (2)
C6—C7—C8—C9	−175.13 (18)	C20—C16—C17—O3	−130.88 (16)
C2—C7—C8—C9	0.47 (18)	C17—O3—C18—C19	169.7 (2)
C6—C7—C8—C15	2.0 (3)	C21B—O5—C20—O6	−10.6 (5)
C2—C7—C8—C15	177.64 (15)	C21A—O5—C20—O6	13.0 (5)
C7—C8—C9—N1	−1.27 (17)	C21B—O5—C20—C16	170.9 (5)
C15—C8—C9—N1	−178.63 (14)	C21A—O5—C20—C16	−165.5 (4)
C7—C8—C9—C23	−177.64 (15)	C15—C16—C20—O6	−167.6 (2)
C15—C8—C9—C23	5.0 (3)	C17—C16—C20—O6	8.0 (3)
C10—N1—C9—C8	−176.27 (15)	C15—C16—C20—O5	10.9 (3)
C2—N1—C9—C8	1.60 (17)	C17—C16—C20—O5	−173.58 (18)
C10—N1—C9—C23	0.2 (2)	C20—O5—C21A—C22A	−105.2 (6)
C2—N1—C9—C23	178.06 (15)	C21B—O5—C21A—C22A	−49.7 (9)
C11—O1—C10—O2	−3.5 (3)	C20—O5—C21B—C22B	−176.8 (5)
C11—O1—C10—N1	176.67 (14)	C21A—O5—C21B—C22B	48.2 (9)
C9—N1—C10—O2	168.77 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23C···O6i	0.96	2.55	3.503 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23C⋯O6i	0.96	2.55	3.503 (3)	171

Symmetry code: (i) .