tert-Butyl 3-[2,2-bis­(ethoxy­carbon­yl)­vinyl]-2-methyl-1H-indole-1-carboxyl­ate

Thenmozhi, M.; Kavitha, T.; Dhayalan, V.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536809009635

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o825

doi:10.1107/S1600536809009635

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tert-Butyl 3-[2,2-bis(ethoxycarbonyl)vinyl]-2-methyl-1H-indole-1-carboxylate

M. Thenmozhi,^a T. Kavitha,^a V. Dhayalan,^b A. K. Mohanakrishnan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 28 January 2009; accepted 16 March 2009; online 25 March 2009)

In the title compound, C₂₂H₂₇NO₆, the indole ring system is planar and the ethoxycarbonyl chains adopt extended conformations. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur, resulting in R₂²(16) dimers, which are interlinked into a chain propagating along the a axis by π–π stacking interactions [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_r = 401.45
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.134
S = 1.04
4766 reflections
286 parameters
28 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009635/ci2766sup1.cif

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

checkCIF report

Comment top

Indole-carboxylate derivatives are known to be sensitive to N-methyl-D-aspartate (NMDA) antagonists and capable of reducing the damage associated with an ischemic insult in Mongolian gerbil hippocampal neurons (Hood et al., 1992). Also the naturally occurring indole compounds can induce cell cycle to arrest the human breast cancer cells (Cram et al., 2001).

The indole ring system is planar and both ethoxycarbonyl groups adopt extended conformation as can be seen from the torsion angles C17—O3—C18—C19 [169.7 (2)°], C18—O3—C17—C16 [-177.6 (2)°], C21A/C21B—O5—C20—C16 [-165.5 (4)° /170.9 (5)°] and C20—O5—C21A/C21B—C22A/C22B [-105.2 (6)° / -176.8 (5)°]. The sum of bond angles around N1 [359.96°] indicates that atom N1 exhibits sp² hybridization (Beddoes et al., 1986). In the tert-butoxycarbonyl group, the three C—C bond lengths lie between 1.501 (3) Å and 1.507 (3) Å, while the three tert-butyl C—C—C angles are in the range 110.6 (2)°–113.1 (2)°, indicating a slight opening up from the ideal tetrahedral value.

In the crystal structure, the molecules form R₂²(16) dimers through paired C23—H23C···O6 hydrogen bonds (Bernstein et al., 1995). A π-π stacking interaction is observed between pyrrole rings of moloecules at (x, y, z) and (2 - x, -y, -z), with a centroid to centroid distance of 3.5916 (9) Å.

Related literature top

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 top

To a solution of tert-butyl 3-formyl-2-methyl-1H-indole-1-carboxylate (4 g, 15.44 mmol) in dry benzene (120 ml), diethylmalonate (2.8 ml, 18.53 mmol), piperidine (6 drops) and acetic acid (3 drops) were added and refluxed in Dean-Stark apparatus for 48 h. Removal of solvent followed by recrystallization from methanol afforded the product as brown crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity. Both disorder components are shown.
	Fig. 2. The packing of the molecules viewed down c axis, showing C—H···O interactions (dashed lines).

tert-Butyl 3-[2,2-bis(ethoxycarbonyl)vinyl]-2-methyl- 1H-indole-1-carboxylate top

Crystal data top

C₂₂H₂₇NO₆	F(000) = 856
M_r = 401.45	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0561P)² + 0.6467P] where P = (F_o² + 2F_c²)/3
4766 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.25 e Å⁻³
28 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₂H₂₇NO₆	V = 2148.93 (11) Å³
M_r = 401.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1933 (3) Å	µ = 0.09 mm⁻¹
b = 21.8495 (6) Å	T = 293 K
c = 10.7676 (3) Å	0.25 × 0.20 × 0.20 mm
β = 96.510 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4766 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3534 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.982	R_int = 0.030
24241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	28 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
4766 reflections	Δρ_min = −0.28 e Å⁻³
286 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₇NO₆
M_r	401.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.1933 (3), 21.8495 (6), 10.7676 (3)
β (°)	96.510 (2)
V (Å³)	2148.93 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.978, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	24241, 4766, 3534
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.134, 1.04
No. of reflections	4766
No. of parameters	286
No. of restraints	28
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

MT thanks Dr Babu Varghese, SAIF, IIT–Madras, India, for his help with the data collection.

References

Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cram, E. J., Liu, B. D., Bjeldanes, L. F. & Firestone, G. L. (2001). J. Biol. Chem. 276, 22332–22340. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hood, W. F., Gray, N. M., Dappen, M. S., Watson, G. B., Compton, R. P., Cordia, A., Lanthorn, T. H. & Mohanan, J. B. (1992). J. Pharmacol. Exp. Ther. 262, 654–660. PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 4| April 2009| Page o825

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

tert-Butyl 3-[2,2-bis­­(eth­oxy­carbon­yl)­vinyl]-2-methyl-1H-indole-1-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

tert-Butyl 3-[2,2-bis(ethoxycarbonyl)vinyl]-2-methyl-1H-indole-1-carboxylate