(1'S,12'R,13'S,17'S)-15',15'-Dimethyl-1,2-dihydro-11',14',16',18'-tetra-oxa-7'-aza-spiro-[indole-3,8'-penta-cyclo-[10.6.0.0(2,9).0(3,7).0(13,17)]octa-deca-ne]-2,10'-dione.

In the title compound, C22H24N2O6, the indole ring has a twist conformation and the tetra-hydro-2H-pyran-2-one ring a half-chair conformation. One of the pyrrolidine rings adopts an envelope conformation on the N atom, while the other has a twist conformation; the 'butterfly' angle between their mean planes is 62.98 (11)°. The dioxolane ring adopts a twist conformation and the tetra-hydro-furan ring has an envelope conformation on the C atom in the fused tetra-hydro-2H-pyran-2-one ring adjacent to the O atom of the tetra-hydro-furan ring. The 'butterfly' angle between the mean planes of these two five-membered rings is 69.14 (10)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of indole derivatives, see: Stevenson et al. (2000 ▶); Rajeswaran et al. (1999 ▶); Amal Raj et al. (2003 ▶). For a related structure, see: Jagadeesan et al. (2012 ▶).

Experimental

Crystal data

C22H24N2O6

M = 412.43

Orthorhombic,

a = 9.2737 (5) Å

b = 11.6543 (8) Å

c = 18.8489 (14) Å

V = 2037.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2008 ▶) T min = 0.922, T max = 0.947

21465 measured reflections

4717 independent reflections

3800 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.04

4717 reflections

324 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005436/su2563sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005436/su2563Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005436/su2563Isup3.cml

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

C22H24N2O6	F(000) = 872
Mr = 412.43	Dx = 1.345 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8834 reflections
a = 9.2737 (5) Å	θ = 2.1–31.2°
b = 11.6543 (8) Å	µ = 0.10 mm−1
c = 18.8489 (14) Å	T = 293 K
V = 2037.2 (2) Å3	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	4717 independent reflections
Radiation source: fine-focus sealed tube	3800 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and φ scan	θmax = 27.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker 2008)	h = −6→12
Tmin = 0.922, Tmax = 0.947	k = −15→14
21465 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.1058P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
4717 reflections	Δρmax = 0.16 e Å−3
324 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (7)

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
H9A	0.090 (2)	0.2846 (19)	0.0396 (11)	0.064 (6)*
H11A	0.384 (2)	0.2235 (18)	0.1817 (11)	0.059 (6)*
H11B	0.251 (2)	0.278 (2)	0.2138 (12)	0.078 (7)*
H10B	0.242 (3)	0.136 (3)	0.1028 (15)	0.109 (10)*
H10A	0.115 (4)	0.178 (4)	0.1375 (19)	0.162 (15)*
H12	0.3470 (19)	0.4460 (16)	0.1690 (10)	0.044 (5)*
H9B	0.251 (2)	0.2576 (16)	0.0170 (10)	0.051 (5)*
H17	0.6125 (17)	0.3803 (14)	0.1785 (9)	0.031 (4)*
H16	0.5679 (19)	0.5796 (16)	0.1708 (10)	0.041 (5)*
H14	0.4660 (17)	0.4184 (14)	−0.0175 (9)	0.034 (4)*
H18	0.929 (2)	0.4543 (16)	0.0878 (10)	0.049 (5)*
H13	0.4947 (16)	0.3027 (15)	0.0749 (8)	0.030 (4)*
H19	0.8300 (18)	0.6200 (17)	0.1434 (9)	0.042 (5)*
O4	0.74044 (11)	0.37954 (10)	0.09447 (6)	0.0428 (3)
O1	0.30443 (14)	0.64064 (10)	0.11353 (7)	0.0494 (3)
C13	0.48045 (16)	0.37792 (13)	0.08903 (9)	0.0321 (3)
O2	0.51578 (14)	0.62812 (10)	−0.03068 (7)	0.0553 (4)
N2	0.22433 (13)	0.39789 (11)	0.08173 (7)	0.0343 (3)
O3	0.62164 (13)	0.59996 (10)	0.07089 (7)	0.0458 (3)
O6	0.79932 (13)	0.52782 (12)	0.23306 (6)	0.0519 (3)
O5	0.91693 (13)	0.38056 (12)	0.18080 (7)	0.0553 (4)
N1	0.14101 (17)	0.64572 (13)	0.02193 (9)	0.0517 (4)
H1	0.0942	0.7067	0.0334	0.062*
C14	0.44834 (16)	0.45548 (13)	0.02581 (9)	0.0321 (3)
C17	0.61096 (16)	0.41353 (14)	0.13092 (9)	0.0346 (3)
C5	0.20045 (16)	0.48417 (13)	−0.03945 (9)	0.0364 (4)
C12	0.33988 (16)	0.37913 (14)	0.13385 (9)	0.0353 (4)
C7	0.24724 (18)	0.59935 (14)	0.06148 (9)	0.0392 (4)
C11	0.3016 (2)	0.26639 (17)	0.17006 (12)	0.0498 (5)
C16	0.63188 (18)	0.54190 (14)	0.13806 (9)	0.0382 (4)
C8	0.11618 (19)	0.58297 (15)	−0.03980 (10)	0.0465 (4)
C4	0.20154 (18)	0.41338 (15)	−0.09800 (9)	0.0435 (4)
H4	0.2601	0.3486	−0.0991	0.052*
C6	0.28163 (15)	0.47975 (12)	0.02961 (8)	0.0329 (3)
C15	0.53006 (18)	0.56665 (14)	0.02019 (9)	0.0386 (4)
C9	0.1869 (2)	0.28246 (15)	0.05469 (11)	0.0471 (4)
C19	0.78866 (19)	0.54907 (17)	0.15952 (10)	0.0439 (4)
C20	0.91327 (19)	0.4474 (2)	0.24389 (11)	0.0555 (5)
C1	0.0264 (2)	0.6093 (2)	−0.09595 (12)	0.0644 (6)
H1A	−0.0322	0.6740	−0.0951	0.077*
C3	0.1137 (2)	0.44023 (19)	−0.15530 (10)	0.0558 (5)
H3	0.1136	0.3933	−0.1952	0.067*
C18	0.85583 (18)	0.44176 (16)	0.12504 (10)	0.0437 (4)
C2	0.0269 (2)	0.5360 (2)	−0.15326 (12)	0.0688 (6)
H2	−0.0330	0.5516	−0.1916	0.083*
C10	0.2036 (3)	0.2056 (2)	0.11837 (16)	0.0706 (7)
C21	1.0539 (2)	0.5104 (3)	0.25265 (17)	0.0961 (10)
H21B	1.1302	0.4561	0.2602	0.144*
H21C	1.0476	0.5610	0.2927	0.144*
H21A	1.0736	0.5542	0.2106	0.144*
C22	0.8736 (3)	0.3709 (3)	0.30471 (13)	0.0978 (10)
H22A	0.9498	0.3167	0.3128	0.147*
H22C	0.7862	0.3306	0.2937	0.147*
H22B	0.8595	0.4165	0.3466	0.147*

	U11	U22	U33	U12	U13	U23
O4	0.0336 (5)	0.0432 (6)	0.0518 (7)	0.0007 (5)	0.0049 (5)	−0.0152 (6)
O1	0.0596 (7)	0.0338 (6)	0.0546 (8)	0.0031 (5)	−0.0002 (6)	−0.0115 (6)
C13	0.0352 (7)	0.0216 (8)	0.0394 (9)	0.0007 (6)	0.0028 (6)	−0.0012 (7)
O2	0.0696 (8)	0.0466 (7)	0.0496 (8)	−0.0215 (6)	−0.0061 (6)	0.0149 (6)
N2	0.0331 (6)	0.0280 (6)	0.0419 (7)	−0.0016 (5)	0.0016 (5)	0.0005 (6)
O3	0.0509 (7)	0.0329 (6)	0.0535 (7)	−0.0120 (6)	−0.0089 (6)	0.0030 (6)
O6	0.0454 (7)	0.0664 (9)	0.0441 (7)	0.0126 (6)	−0.0043 (5)	−0.0161 (6)
O5	0.0511 (7)	0.0602 (9)	0.0545 (8)	0.0143 (6)	−0.0071 (6)	−0.0121 (7)
N1	0.0562 (9)	0.0333 (8)	0.0657 (10)	0.0160 (7)	−0.0051 (8)	−0.0021 (8)
C14	0.0336 (7)	0.0280 (8)	0.0346 (8)	−0.0032 (6)	0.0036 (6)	−0.0044 (7)
C17	0.0335 (8)	0.0327 (8)	0.0375 (9)	0.0038 (6)	0.0040 (7)	−0.0002 (7)
C5	0.0356 (8)	0.0292 (8)	0.0444 (9)	−0.0045 (6)	−0.0007 (7)	0.0028 (7)
C12	0.0367 (8)	0.0330 (8)	0.0362 (9)	0.0007 (7)	0.0041 (6)	0.0002 (7)
C7	0.0423 (8)	0.0278 (8)	0.0474 (10)	0.0007 (7)	0.0057 (8)	−0.0012 (7)
C11	0.0486 (10)	0.0453 (11)	0.0554 (12)	−0.0017 (9)	0.0066 (9)	0.0142 (9)
C16	0.0405 (8)	0.0339 (9)	0.0402 (9)	−0.0007 (7)	−0.0011 (7)	−0.0050 (7)
C8	0.0477 (9)	0.0358 (9)	0.0559 (11)	0.0019 (8)	−0.0069 (9)	0.0064 (9)
C4	0.0430 (9)	0.0398 (9)	0.0478 (10)	−0.0094 (8)	−0.0006 (8)	−0.0002 (8)
C6	0.0336 (7)	0.0245 (7)	0.0404 (9)	−0.0003 (6)	0.0016 (6)	−0.0007 (7)
C15	0.0412 (8)	0.0328 (8)	0.0418 (9)	−0.0052 (7)	0.0030 (7)	0.0011 (8)
C9	0.0533 (11)	0.0297 (9)	0.0584 (12)	−0.0073 (8)	0.0010 (10)	−0.0008 (8)
C19	0.0434 (9)	0.0417 (10)	0.0466 (10)	−0.0042 (8)	−0.0017 (8)	−0.0079 (8)
C20	0.0406 (9)	0.0743 (14)	0.0518 (11)	0.0117 (9)	−0.0063 (8)	−0.0156 (11)
C1	0.0631 (12)	0.0561 (12)	0.0740 (15)	0.0123 (11)	−0.0187 (11)	0.0104 (11)
C3	0.0543 (11)	0.0626 (13)	0.0504 (11)	−0.0167 (10)	−0.0088 (9)	−0.0014 (10)
C18	0.0340 (8)	0.0526 (11)	0.0445 (10)	−0.0053 (7)	0.0061 (8)	−0.0099 (9)
C2	0.0627 (13)	0.0754 (15)	0.0684 (15)	−0.0042 (12)	−0.0246 (11)	0.0161 (13)
C10	0.0868 (17)	0.0419 (12)	0.0830 (17)	−0.0201 (12)	−0.0164 (14)	0.0179 (12)
C21	0.0457 (12)	0.119 (2)	0.123 (2)	0.0087 (14)	−0.0179 (13)	−0.057 (2)
C22	0.108 (2)	0.126 (3)	0.0594 (15)	0.040 (2)	−0.0009 (14)	0.0199 (17)

O4—C18	1.415 (2)	C7—C6	1.551 (2)
O4—C17	1.4390 (18)	C11—C10	1.509 (3)
O1—C7	1.215 (2)	C11—H11A	0.94 (2)
C13—C17	1.503 (2)	C11—H11B	0.96 (2)
C13—C14	1.525 (2)	C16—C19	1.511 (2)
C13—C12	1.553 (2)	C16—H16	0.962 (19)
C13—H13	0.925 (17)	C8—C1	1.381 (3)
O2—C15	1.204 (2)	C4—C3	1.388 (3)
N2—C6	1.469 (2)	C4—H4	0.9300
N2—C12	1.470 (2)	C9—C10	1.506 (3)
N2—C9	1.480 (2)	C9—H9A	0.95 (2)
O3—C15	1.336 (2)	C9—H9B	0.97 (2)
O3—C16	1.439 (2)	C19—C18	1.541 (2)
O6—C19	1.411 (2)	C19—H19	0.961 (19)
O6—C20	1.427 (2)	C20—C22	1.498 (3)
O5—C18	1.391 (2)	C20—C21	1.505 (3)
O5—C20	1.422 (2)	C1—C2	1.377 (3)
N1—C7	1.348 (2)	C1—H1A	0.9300
N1—C8	1.393 (2)	C3—C2	1.376 (3)
N1—H1	0.8600	C3—H3	0.9300
C14—C15	1.505 (2)	C18—H18	0.985 (19)
C14—C6	1.573 (2)	C2—H2	0.9300
C14—H14	0.938 (17)	C10—H10B	0.93 (3)
C17—C16	1.515 (2)	C10—H10A	0.95 (4)
C17—H17	0.977 (17)	C21—H21B	0.9600
C5—C4	1.378 (2)	C21—H21C	0.9600
C5—C8	1.392 (2)	C21—H21A	0.9600
C5—C6	1.505 (2)	C22—H22A	0.9600
C12—C11	1.523 (2)	C22—H22C	0.9600
C12—H12	1.026 (19)	C22—H22B	0.9600
C18—O4—C17	107.19 (11)	N2—C6—C7	104.49 (12)
C17—C13—C14	113.82 (13)	C5—C6—C7	101.62 (13)
C17—C13—C12	112.80 (14)	N2—C6—C14	105.62 (12)
C14—C13—C12	104.82 (12)	C5—C6—C14	117.28 (13)
C17—C13—H13	107.3 (10)	C7—C6—C14	112.42 (12)
C14—C13—H13	111.4 (10)	O2—C15—O3	117.81 (14)
C12—C13—H13	106.6 (10)	O2—C15—C14	120.85 (15)
C6—N2—C12	106.25 (11)	O3—C15—C14	121.33 (15)
C6—N2—C9	116.41 (13)	N2—C9—C10	104.02 (17)
C12—N2—C9	105.42 (13)	N2—C9—H9A	107.6 (14)
C15—O3—C16	122.32 (12)	C10—C9—H9A	110.7 (13)
C19—O6—C20	107.92 (14)	N2—C9—H9B	112.2 (11)
C18—O5—C20	109.96 (15)	C10—C9—H9B	110.0 (11)
C7—N1—C8	111.83 (14)	H9A—C9—H9B	112.0 (17)
C7—N1—H1	124.1	O6—C19—C16	108.69 (15)
C8—N1—H1	124.1	O6—C19—C18	104.10 (15)
C15—C14—C13	117.84 (13)	C16—C19—C18	103.36 (14)
C15—C14—C6	110.08 (13)	O6—C19—H19	115.7 (10)
C13—C14—C6	105.24 (12)	C16—C19—H19	110.3 (10)
C15—C14—H14	104.3 (10)	C18—C19—H19	113.9 (10)
C13—C14—H14	111.9 (10)	O5—C20—O6	104.94 (14)
C6—C14—H14	107.1 (10)	O5—C20—C22	108.7 (2)
O4—C17—C13	110.19 (13)	O6—C20—C22	108.59 (17)
O4—C17—C16	101.97 (13)	O5—C20—C21	109.76 (17)
C13—C17—C16	114.99 (14)	O6—C20—C21	109.69 (19)
O4—C17—H17	108.4 (9)	C22—C20—C21	114.7 (2)
C13—C17—H17	112.6 (9)	C2—C1—C8	117.46 (19)
C16—C17—H17	108.0 (10)	C2—C1—H1A	121.3
C4—C5—C8	119.72 (15)	C8—C1—H1A	121.3
C4—C5—C6	131.97 (14)	C2—C3—C4	120.3 (2)
C8—C5—C6	108.26 (14)	C2—C3—H3	119.9
N2—C12—C11	104.95 (14)	C4—C3—H3	119.9
N2—C12—C13	104.46 (12)	O5—C18—O4	110.66 (15)
C11—C12—C13	115.57 (14)	O5—C18—C19	105.19 (14)
N2—C12—H12	111.5 (10)	O4—C18—C19	106.37 (13)
C11—C12—H12	112.4 (10)	O5—C18—H18	109.7 (11)
C13—C12—H12	107.7 (10)	O4—C18—H18	107.7 (11)
O1—C7—N1	127.35 (15)	C19—C18—H18	117.2 (11)
O1—C7—C6	125.38 (15)	C3—C2—C1	121.80 (19)
N1—C7—C6	107.24 (14)	C3—C2—H2	119.1
C10—C11—C12	104.84 (17)	C1—C2—H2	119.1
C10—C11—H11A	113.1 (13)	C9—C10—C11	107.29 (16)
C12—C11—H11A	111.9 (13)	C9—C10—H10B	107.9 (18)
C10—C11—H11B	108.9 (14)	C11—C10—H10B	112.7 (19)
C12—C11—H11B	112.5 (15)	C9—C10—H10A	114 (2)
H11A—C11—H11B	105.7 (18)	C11—C10—H10A	116 (2)
O3—C16—C19	105.85 (14)	H10B—C10—H10A	99 (3)
O3—C16—C17	112.20 (14)	C20—C21—H21B	109.5
C19—C16—C17	101.63 (14)	C20—C21—H21C	109.5
O3—C16—H16	108.0 (11)	H21B—C21—H21C	109.5
C19—C16—H16	113.4 (10)	C20—C21—H21A	109.5
C17—C16—H16	115.4 (11)	H21B—C21—H21A	109.5
C1—C8—C5	121.73 (18)	H21C—C21—H21A	109.5
C1—C8—N1	128.53 (18)	C20—C22—H22A	109.5
C5—C8—N1	109.73 (15)	C20—C22—H22C	109.5
C5—C4—C3	118.93 (17)	H22A—C22—H22C	109.5
C5—C4—H4	120.5	C20—C22—H22B	109.5
C3—C4—H4	120.5	H22A—C22—H22B	109.5
N2—C6—C5	114.83 (12)	H22C—C22—H22B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.06	2.8849 (19)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.06	2.8849 (19)	161

Symmetry code: (i) .