1-Ethyl-4′-(1H-indol-3-ylcarbon­yl)-1′-methyl-2,2′′-dioxodi­spiro­[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carbo­nitrile dimethyl sulfoxide monosolvate

Inglebert, S.A.; Arun, Y.; Sethusankar, K.; Perumal, P.T.

doi:10.1107/S1600536813020485

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1328-o1329

doi:10.1107/S1600536813020485

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1-Ethyl-4′-(1H-indol-3-ylcarbonyl)-1′-methyl-2,2′′-dioxodispiro[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carbonitrile dimethyl sulfoxide monosolvate

S. Antony Inglebert,^a Yuvaraj Arun,^b K. Sethusankar ^c ^* and Paramasivam T. Perumal ^b

^aSri Ram Engineering College, Chennai 602 024, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 3 July 2013; accepted 23 July 2013; online 27 July 2013)

In the title compound, C₃₁H₂₅N₅O₃·C₂H₆OS, the three indole/indoline units are all essentially planar with maximum deviations of 0.0172 (3), 0.053 (2) and 0.07 (2) Å. The pyrrolidine ring adopts an envelope conformation with the C atoms bearing the 1-ethyl-2-oxoindole substituent (in which the five-membered ring adopts a twisted conformation) as the flap. The dimethyl sulfoxide solvent molecule is disordered over two positions, with an occupancy factor ratio of 0.871 (4):0.129 (4). The solvent components are linked to the heterocyclic molecule via C—H⋯O and C—H⋯S hydrogen bonds. In the crystal, the solvent components are linked to the heterocyclic molecule via C—H⋯O and C—H⋯S interactions, forming R₂²(10) ring motifs. The molecules are further connected into a chain along the a-axis direction via N—H⋯O hydrogen bonds.

Related literature

For applications of indole derivatives, see: Barden (2011 ). For puckering parameters, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₁H₂₅N₅O₃·C₂H₆OS
M_r = 593.70
Orthorhombic, P b c a
a = 14.078 (5) Å
b = 20.416 (5) Å
c = 20.789 (5) Å
V = 5975 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.955, T_max = 0.970
26724 measured reflections
5139 independent reflections
3447 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.03
5139 reflections
431 parameters
48 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O4	0.84 (3)	1.89 (3)	2.714 (3)	166 (2)
N1—H1A⋯O2ⁱ	0.84 (3)	2.10 (3)	2.887 (3)	155 (2)
C22—H22⋯S1ⁱⁱ	0.93	2.85	3.717 (3)	157
C32—H32A⋯O3ⁱⁱⁱ	0.96	2.60	3.219 (4)	123
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

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 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813020485/rk2408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020485/rk2408Isup2.hkl

checkCIF report

Comment top

Indole containing compounds are best known for their medicinal properties in the pharmaceutical industry. In modern times, analogs based on indole are significant players in a diverse array of markets such as dyes, plastics, agriculture, vitamin supplements, over-the-counterdrugs, flavour enhancers and perfumery (Barden, 2011).

In the crystal structure of title compound, C₃₁H₂₅N₅O₃^.C₂H₆OS, (Fig. 1), there is a dispiro centers system, which consists of two oxindole rings, an indole ring and a pyrrolidine ring. In crystals organic heterocycles moiety and solvent molecules connected by two intermolecular C–H···S and C–H···O hydrogen bonds (Table 1). The dimethyl sulfoxide solvent molecule is disordered over two positions with site occupancy factors 0.871 (4) and 0.129 (4).

The pyrrolidine ring (N3/C12/C13/C14/C10) adopts an envelope conformation with puckering parameters, q₂ = 0.402 (2)Å, ϕ(2) = 331.4 (3)°, and with atom C13 deviating by 0.256 (2)Å from the mean plane passing through the rest of the ring atoms (Cremer & Pople, 1975). The carbonitrile group is nearly perpendicular to pyrrolidine ring, as indicated by the torsion angle C12-C10-C11-N2 = 87.4 (2)°. The indole system A makes dihedral angles of 53.13 (15)° and 86.11 (6)° with the oxindole ring systems B & C, respectively. It clearly shows that ring systems A and C are almost perpendicular to each other. Also the dihedral angle between oxindole B and C is 54.40 (5)°. The twisted conformation of the five membered pyrrole ring in oxindole ring system C is observed through the puckering analysis [q₂ = 0.074 (2) Å and ϕ(2) = 277.1 (18)°].

The indole and oxindole ring systems A, B and C are planar with maximum deviations of 0.0172 (3)Å, 0.053 (2)Å and 0.07 (2)Å for the atoms C4, C14 and C26 from the LS planes. The bond lengths of O2-C16, C16-N4 in oxindole unit B and O3-C23, C23-N5 in oxindole unit C show electron delocalization over atoms O2, C16, N4, O3, C23 and N5.

The cyano bond distance C11≡N2 agrees well with the reported value of 1.138 (7)Å (Allen et al., 1987). The sum of the angles around atom N5 (359.86°) is in accordance with sp² hybridization, whereas the sum of the angles around atom N3 (337.75°) is in accordance with sp³ one. The oxygen atoms attached to C16 and C23 are coplanar with the oxindole ring system B & C as indicated by the torsion angles O2-C16-N4-C18 = -177.3 (2)° and O3-C23-N5-C24 = -176.3 (2)°, respectively.

In the crystal structure, pairs of molecules are linked by intermolecular C–H···O and C–H···S hydrogen bonds to generate R²₂(10) ring motifs (Bernstein et al., 1995). The molecules are further connected into a chain along the a axis via N–H···O intermolecular hydrogen bonds. The packing view of the title compound is shown in Fig. 2. (Macrae et al., 2008).

Related literature top

For applications of indole derivatives, see: Barden (2011). For puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of 1-ethyl-isatin (1 mmol), sarcosine (1 mmol) and 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindoline-3-ylidene)propane nitrile (1 mmol) were refluxed in ethanol (10 ml). After completion of the reaction as evidenced by TLC analysis, the reaction mixture was poured into ice-water, the resulting solid was filtered off and purified by column chromatography using ethyl acetate : petroleum ether (6 : 4) as an eluent to afford pure spirooxiindoles in 82% yield.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The part of molecular structure of the title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are present as a small spheres of arbitary radius. Only major moiety of solvent is shown.
	Fig. 2. The packing structure of the title compound viewed along the c axis. H atoms not included in H-bonding have omited for clarity.

1-Ethyl-4'-(1H-indol-3-ylcarbonyl)-1'-methyl-2,2''-dioxodispiro[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carbonitrile dimethyl sulfoxide monosolvate top

Crystal data top

C₃₁H₂₅N₅O₃·C₂H₆OS	F(000) = 2496
M_r = 593.70	D_x = 1.320 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5139 reflections
a = 14.078 (5) Å	θ = 2.2–25.0°
b = 20.416 (5) Å	µ = 0.16 mm⁻¹
c = 20.789 (5) Å	T = 295 K
V = 5975 (3) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5139 independent reflections
Radiation source: fine-focus sealed tube	3447 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→15
T_min = 0.955, T_max = 0.970	k = −16→24
26724 measured reflections	l = −24→24

Refinement top

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0509P)² + 2.1171P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5139 reflections	Δρ_max = 0.25 e Å⁻³
431 parameters	Δρ_min = −0.27 e Å⁻³
48 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: 0.0015 (2)

Crystal data top

C₃₁H₂₅N₅O₃·C₂H₆OS	V = 5975 (3) Å³
M_r = 593.70	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.078 (5) Å	µ = 0.16 mm⁻¹
b = 20.416 (5) Å	T = 295 K
c = 20.789 (5) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5139 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3447 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.970	R_int = 0.035
26724 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	48 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
5139 reflections	Δρ_min = −0.27 e Å⁻³
431 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)
C1	0.65192 (17)	0.06281 (11)	0.33748 (10)	0.0472 (6)
C2	0.5854 (2)	0.02329 (12)	0.36920 (13)	0.0661 (7)
H2	0.5206	0.0308	0.3648	0.079*
C3	0.6188 (3)	−0.02699 (14)	0.40713 (16)	0.0868 (10)
H3	0.5754	−0.0536	0.4285	0.104*
C4	0.7148 (3)	−0.03925 (14)	0.41453 (15)	0.0853 (10)
H4	0.7341	−0.0740	0.4403	0.102*
C5	0.7820 (2)	−0.00148 (13)	0.38480 (13)	0.0683 (8)
H5	0.8466	−0.0095	0.3898	0.082*
C6	0.74840 (18)	0.04948 (11)	0.34678 (10)	0.0501 (6)
C7	0.73904 (17)	0.13393 (11)	0.27982 (10)	0.0482 (6)
H7	0.7573	0.1679	0.2527	0.058*
C8	0.64624 (16)	0.11757 (10)	0.29381 (10)	0.0434 (5)
C9	0.55927 (17)	0.14783 (11)	0.27187 (10)	0.0470 (6)
C10	0.56313 (15)	0.20484 (10)	0.22079 (10)	0.0407 (5)
C11	0.62745 (17)	0.25514 (11)	0.24702 (11)	0.0468 (6)
C12	0.46423 (16)	0.23568 (11)	0.20902 (11)	0.0503 (6)
H12A	0.4175	0.2166	0.2378	0.060*
H12B	0.4663	0.2826	0.2163	0.060*
C13	0.52858 (15)	0.21989 (10)	0.10596 (10)	0.0399 (5)
C14	0.59516 (14)	0.18003 (9)	0.15212 (10)	0.0374 (5)
C15	0.36806 (17)	0.26636 (12)	0.11622 (13)	0.0619 (7)
H15A	0.3895	0.3107	0.1210	0.093*
H15B	0.3096	0.2606	0.1393	0.093*
H15C	0.3580	0.2571	0.0715	0.093*
C16	0.57207 (16)	0.10561 (10)	0.14492 (10)	0.0413 (5)
C17	0.69758 (15)	0.18221 (10)	0.13168 (9)	0.0382 (5)
C18	0.72407 (15)	0.12012 (11)	0.11078 (10)	0.0433 (5)
C19	0.81171 (18)	0.10731 (13)	0.08455 (12)	0.0598 (7)
H19	0.8281	0.0655	0.0707	0.072*
C20	0.87455 (19)	0.15900 (15)	0.07958 (13)	0.0695 (8)
H20	0.9344	0.1519	0.0619	0.083*
C21	0.85034 (17)	0.22058 (14)	0.10016 (13)	0.0617 (7)
H21	0.8940	0.2545	0.0964	0.074*
C22	0.76217 (16)	0.23289 (12)	0.12629 (10)	0.0482 (6)
H22	0.7463	0.2748	0.1401	0.058*
C23	0.57066 (16)	0.28945 (11)	0.09338 (11)	0.0461 (5)
C24	0.57243 (16)	0.23597 (11)	−0.00259 (11)	0.0480 (6)
C25	0.52630 (15)	0.19253 (11)	0.03842 (10)	0.0426 (5)
C26	0.49175 (17)	0.13434 (12)	0.01454 (12)	0.0536 (6)
H26	0.4580	0.1057	0.0408	0.064*
C27	0.5084 (2)	0.11921 (15)	−0.05004 (13)	0.0680 (8)
H27	0.4859	0.0801	−0.0671	0.082*
C28	0.5577 (2)	0.16173 (16)	−0.08827 (13)	0.0713 (8)
H28	0.5699	0.1502	−0.1308	0.086*
C29	0.58995 (18)	0.22098 (14)	−0.06587 (12)	0.0632 (7)
H29	0.6224	0.2499	−0.0926	0.076*
C30	0.6331 (2)	0.35405 (14)	0.00144 (14)	0.0722 (8)
H30A	0.6172	0.3909	0.0288	0.087*
H30B	0.6025	0.3609	−0.0398	0.087*
C31	0.7364 (2)	0.35289 (15)	−0.00822 (14)	0.0824 (9)
H31A	0.7673	0.3436	0.0319	0.124*
H31B	0.7571	0.3947	−0.0239	0.124*
H31C	0.7523	0.3196	−0.0390	0.124*
C32	0.8172 (3)	−0.05035 (18)	0.2089 (2)	0.0967 (14)	0.871 (4)
H32A	0.8741	−0.0559	0.1840	0.145*	0.871 (4)
H32B	0.8265	−0.0684	0.2511	0.145*	0.871 (4)
H32C	0.8028	−0.0045	0.2125	0.145*	0.871 (4)
C33	0.6338 (4)	−0.0748 (3)	0.2305 (3)	0.1150 (16)	0.871 (4)
H33A	0.6239	−0.0284	0.2338	0.173*	0.871 (4)
H33B	0.6547	−0.0916	0.2712	0.173*	0.871 (4)
H33C	0.5753	−0.0957	0.2185	0.173*	0.871 (4)
S1	0.72223 (14)	−0.09108 (5)	0.17075 (6)	0.0784 (5)	0.871 (4)
C32'	0.735 (3)	−0.0416 (12)	0.2131 (13)	0.098 (3)	0.129 (4)
H32D	0.7569	−0.0172	0.1765	0.147*	0.129 (4)
H32E	0.7884	−0.0607	0.2349	0.147*	0.129 (4)
H32F	0.7021	−0.0127	0.2420	0.147*	0.129 (4)
C33'	0.569 (3)	−0.0689 (17)	0.2306 (18)	0.109 (4)	0.129 (4)
H33D	0.5729	−0.0220	0.2331	0.164*	0.129 (4)
H33E	0.5681	−0.0870	0.2732	0.164*	0.129 (4)
H33F	0.5117	−0.0810	0.2084	0.164*	0.129 (4)
S1'	0.6645 (11)	−0.0983 (4)	0.1898 (6)	0.101 (2)	0.129 (4)
N1	0.79922 (17)	0.09409 (9)	0.31071 (10)	0.0512 (5)
N2	0.67536 (17)	0.29310 (10)	0.27061 (10)	0.0656 (6)
N3	0.43995 (12)	0.22165 (8)	0.14198 (9)	0.0441 (5)
N4	0.64895 (14)	0.07659 (10)	0.11969 (9)	0.0475 (5)
N5	0.59495 (13)	0.29407 (9)	0.03049 (9)	0.0506 (5)
O1	0.48161 (12)	0.13018 (9)	0.29122 (9)	0.0708 (5)
O2	0.49819 (11)	0.07829 (7)	0.15947 (8)	0.0540 (4)
O3	0.57737 (12)	0.33293 (7)	0.13313 (8)	0.0601 (5)
O4	0.69303 (17)	−0.05270 (9)	0.11415 (10)	0.0955 (7)
H1A	0.8589 (18)	0.0966 (11)	0.3091 (12)	0.054 (8)*
H4A	0.6529 (17)	0.0356 (13)	0.1161 (12)	0.062 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0615 (16)	0.0409 (12)	0.0393 (12)	−0.0039 (11)	0.0042 (11)	−0.0048 (10)
C2	0.077 (2)	0.0549 (15)	0.0662 (17)	−0.0057 (14)	0.0170 (14)	0.0055 (13)
C3	0.113 (3)	0.0589 (18)	0.088 (2)	−0.0037 (18)	0.029 (2)	0.0228 (16)
C4	0.122 (3)	0.0550 (17)	0.079 (2)	0.0146 (18)	0.009 (2)	0.0199 (15)
C5	0.085 (2)	0.0548 (16)	0.0655 (17)	0.0089 (15)	−0.0058 (15)	0.0032 (13)
C6	0.0648 (17)	0.0405 (13)	0.0448 (13)	−0.0022 (11)	−0.0040 (12)	−0.0036 (10)
C7	0.0530 (15)	0.0473 (13)	0.0444 (13)	−0.0065 (11)	−0.0049 (11)	0.0037 (10)
C8	0.0472 (15)	0.0441 (12)	0.0389 (12)	−0.0044 (11)	0.0013 (10)	−0.0014 (10)
C9	0.0485 (15)	0.0509 (13)	0.0418 (13)	−0.0049 (11)	0.0087 (11)	−0.0026 (10)
C10	0.0398 (13)	0.0415 (12)	0.0408 (12)	0.0001 (10)	0.0053 (9)	−0.0028 (9)
C11	0.0543 (16)	0.0471 (13)	0.0389 (12)	0.0006 (12)	0.0039 (11)	−0.0016 (10)
C12	0.0481 (15)	0.0512 (14)	0.0515 (14)	0.0070 (11)	0.0088 (11)	−0.0056 (11)
C13	0.0345 (12)	0.0399 (12)	0.0451 (12)	0.0002 (9)	0.0026 (9)	0.0006 (9)
C14	0.0343 (12)	0.0373 (11)	0.0405 (12)	−0.0001 (9)	0.0042 (9)	−0.0016 (9)
C15	0.0467 (16)	0.0659 (16)	0.0732 (18)	0.0148 (12)	−0.0017 (13)	0.0018 (13)
C16	0.0412 (14)	0.0379 (11)	0.0449 (13)	0.0015 (10)	0.0005 (10)	−0.0003 (10)
C17	0.0364 (13)	0.0438 (12)	0.0344 (11)	0.0027 (10)	−0.0006 (9)	0.0008 (9)
C18	0.0385 (14)	0.0508 (13)	0.0405 (12)	0.0051 (11)	−0.0012 (10)	−0.0010 (10)
C19	0.0507 (17)	0.0676 (17)	0.0611 (16)	0.0177 (13)	0.0089 (12)	−0.0044 (13)
C20	0.0408 (16)	0.095 (2)	0.0724 (18)	0.0072 (15)	0.0150 (13)	0.0071 (16)
C21	0.0399 (15)	0.0752 (18)	0.0701 (17)	−0.0080 (13)	0.0053 (13)	0.0116 (15)
C22	0.0421 (14)	0.0542 (14)	0.0483 (13)	−0.0060 (11)	−0.0020 (11)	0.0037 (11)
C23	0.0412 (14)	0.0433 (13)	0.0539 (14)	0.0019 (10)	−0.0023 (11)	0.0040 (11)
C24	0.0385 (14)	0.0616 (15)	0.0438 (13)	0.0058 (11)	−0.0035 (10)	0.0041 (11)
C25	0.0349 (13)	0.0492 (13)	0.0439 (12)	0.0052 (10)	−0.0032 (10)	−0.0029 (10)
C26	0.0485 (15)	0.0563 (15)	0.0562 (15)	0.0023 (11)	−0.0063 (11)	−0.0068 (12)
C27	0.0685 (19)	0.0746 (19)	0.0609 (18)	0.0085 (15)	−0.0121 (14)	−0.0219 (15)
C28	0.0685 (19)	0.100 (2)	0.0459 (15)	0.0131 (17)	−0.0011 (14)	−0.0111 (16)
C29	0.0514 (16)	0.090 (2)	0.0482 (15)	0.0054 (14)	0.0008 (12)	0.0055 (14)
C30	0.068 (2)	0.0710 (18)	0.0780 (19)	−0.0083 (14)	0.0082 (15)	0.0260 (15)
C31	0.075 (2)	0.090 (2)	0.082 (2)	−0.0139 (17)	0.0022 (16)	0.0151 (17)
C32	0.122 (4)	0.069 (2)	0.099 (3)	0.013 (2)	−0.021 (3)	−0.023 (2)
C33	0.141 (4)	0.100 (3)	0.104 (3)	−0.005 (3)	0.031 (4)	−0.025 (3)
S1	0.1168 (12)	0.0372 (5)	0.0811 (7)	0.0140 (6)	−0.0054 (7)	−0.0141 (4)
C32'	0.130 (6)	0.070 (5)	0.094 (5)	0.000 (5)	0.010 (5)	−0.030 (5)
C33'	0.131 (8)	0.086 (7)	0.111 (7)	0.001 (8)	0.019 (8)	−0.017 (7)
S1'	0.125 (5)	0.072 (4)	0.107 (5)	0.004 (4)	0.006 (5)	−0.020 (4)
N1	0.0474 (14)	0.0503 (12)	0.0558 (13)	−0.0038 (10)	−0.0075 (11)	0.0002 (9)
N2	0.0839 (17)	0.0565 (13)	0.0565 (13)	−0.0127 (12)	−0.0081 (11)	−0.0086 (11)
N3	0.0367 (11)	0.0452 (10)	0.0505 (11)	0.0051 (8)	0.0016 (8)	−0.0018 (8)
N4	0.0482 (13)	0.0377 (11)	0.0565 (12)	0.0047 (10)	0.0022 (9)	−0.0080 (9)
N5	0.0497 (12)	0.0499 (11)	0.0523 (12)	−0.0026 (9)	0.0026 (9)	0.0098 (9)
O1	0.0512 (11)	0.0866 (13)	0.0746 (12)	−0.0016 (9)	0.0207 (9)	0.0231 (10)
O2	0.0473 (10)	0.0415 (9)	0.0732 (11)	−0.0066 (7)	0.0078 (8)	0.0011 (8)
O3	0.0705 (12)	0.0417 (9)	0.0683 (11)	−0.0048 (8)	0.0002 (9)	−0.0053 (8)
O4	0.145 (2)	0.0573 (12)	0.0838 (15)	0.0281 (12)	−0.0163 (13)	−0.0165 (11)

Geometric parameters (Å, º) top

C1—C6	1.399 (3)	C20—H20	0.9300
C1—C2	1.401 (3)	C21—C22	1.378 (3)
C1—C8	1.442 (3)	C21—H21	0.9300
C2—C3	1.377 (4)	C22—H22	0.9300
C2—H2	0.9300	C23—O3	1.216 (3)
C3—C4	1.383 (5)	C23—N5	1.355 (3)
C3—H3	0.9300	C24—C29	1.373 (3)
C4—C5	1.368 (4)	C24—C25	1.391 (3)
C4—H4	0.9300	C24—N5	1.407 (3)
C5—C6	1.389 (3)	C25—C26	1.376 (3)
C5—H5	0.9300	C26—C27	1.397 (3)
C6—N1	1.380 (3)	C26—H26	0.9300
C7—N1	1.339 (3)	C27—C28	1.366 (4)
C7—C8	1.379 (3)	C27—H27	0.9300
C7—H7	0.9300	C28—C29	1.373 (4)
C8—C9	1.445 (3)	C28—H28	0.9300
C9—O1	1.219 (3)	C29—H29	0.9300
C9—C10	1.577 (3)	C30—N5	1.467 (3)
C10—C11	1.474 (3)	C30—C31	1.468 (4)
C10—C12	1.547 (3)	C30—H30A	0.9700
C10—C14	1.580 (3)	C30—H30B	0.9700
C11—N2	1.138 (3)	C31—H31A	0.9600
C12—N3	1.463 (3)	C31—H31B	0.9600
C12—H12A	0.9700	C31—H31C	0.9600
C12—H12B	0.9700	C32—S1	1.764 (4)
C13—N3	1.456 (3)	C32—H32A	0.9600
C13—C25	1.512 (3)	C32—H32B	0.9600
C13—C23	1.561 (3)	C32—H32C	0.9600
C13—C14	1.569 (3)	C33—S1	1.790 (5)
C14—C17	1.504 (3)	C33—H33A	0.9600
C14—C16	1.561 (3)	C33—H33B	0.9600
C15—N3	1.464 (3)	C33—H33C	0.9600
C15—H15A	0.9600	S1—O4	1.472 (2)
C15—H15B	0.9600	C32'—S1'	1.60 (3)
C15—H15C	0.9600	C32'—H32D	0.9600
C16—O2	1.218 (2)	C32'—H32E	0.9600
C16—N4	1.341 (3)	C32'—H32F	0.9600
C17—C22	1.382 (3)	C33'—S1'	1.70 (3)
C17—C18	1.391 (3)	C33'—H33D	0.9600
C18—C19	1.374 (3)	C33'—H33E	0.9600
C18—N4	1.394 (3)	C33'—H33F	0.9600
C19—C20	1.381 (4)	S1'—O4	1.871 (14)
C19—H19	0.9300	N1—H1A	0.84 (2)
C20—C21	1.371 (4)	N4—H4A	0.84 (3)

C6—C1—C2	118.1 (2)	C21—C20—H20	119.4
C6—C1—C8	107.0 (2)	C19—C20—H20	119.4
C2—C1—C8	134.9 (2)	C20—C21—C22	120.9 (2)
C3—C2—C1	118.1 (3)	C20—C21—H21	119.5
C3—C2—H2	120.9	C22—C21—H21	119.5
C1—C2—H2	120.9	C21—C22—C17	119.2 (2)
C2—C3—C4	122.1 (3)	C21—C22—H22	120.4
C2—C3—H3	118.9	C17—C22—H22	120.4
C4—C3—H3	118.9	O3—C23—N5	125.8 (2)
C5—C4—C3	121.5 (3)	O3—C23—C13	125.4 (2)
C5—C4—H4	119.2	N5—C23—C13	108.72 (19)
C3—C4—H4	119.2	C29—C24—C25	121.9 (2)
C4—C5—C6	116.4 (3)	C29—C24—N5	128.0 (2)
C4—C5—H5	121.8	C25—C24—N5	110.06 (19)
C6—C5—H5	121.8	C26—C25—C24	119.6 (2)
N1—C6—C5	128.8 (3)	C26—C25—C13	131.4 (2)
N1—C6—C1	107.4 (2)	C24—C25—C13	108.89 (19)
C5—C6—C1	123.7 (2)	C25—C26—C27	118.5 (2)
N1—C7—C8	110.6 (2)	C25—C26—H26	120.7
N1—C7—H7	124.7	C27—C26—H26	120.7
C8—C7—H7	124.7	C28—C27—C26	120.3 (3)
C7—C8—C1	105.5 (2)	C28—C27—H27	119.9
C7—C8—C9	129.2 (2)	C26—C27—H27	119.9
C1—C8—C9	125.2 (2)	C27—C28—C29	122.0 (3)
O1—C9—C8	121.9 (2)	C27—C28—H28	119.0
O1—C9—C10	118.1 (2)	C29—C28—H28	119.0
C8—C9—C10	119.94 (19)	C24—C29—C28	117.5 (3)
C11—C10—C12	109.13 (18)	C24—C29—H29	121.2
C11—C10—C9	106.63 (17)	C28—C29—H29	121.2
C12—C10—C9	112.08 (17)	N5—C30—C31	113.9 (2)
C11—C10—C14	112.47 (17)	N5—C30—H30A	108.8
C12—C10—C14	104.15 (16)	C31—C30—H30A	108.8
C9—C10—C14	112.44 (16)	N5—C30—H30B	108.8
N2—C11—C10	176.2 (2)	C31—C30—H30B	108.8
N3—C12—C10	106.32 (17)	H30A—C30—H30B	107.7
N3—C12—H12A	110.5	C30—C31—H31A	109.5
C10—C12—H12A	110.5	C30—C31—H31B	109.5
N3—C12—H12B	110.5	H31A—C31—H31B	109.5
C10—C12—H12B	110.5	C30—C31—H31C	109.5
H12A—C12—H12B	108.7	H31A—C31—H31C	109.5
N3—C13—C25	117.96 (18)	H31B—C31—H31C	109.5
N3—C13—C23	112.90 (17)	O4—S1—C32	108.70 (19)
C25—C13—C23	100.88 (17)	O4—S1—C33	105.2 (2)
N3—C13—C14	102.13 (16)	C32—S1—C33	97.3 (2)
C25—C13—C14	112.90 (16)	S1'—C32'—H32D	109.5
C23—C13—C14	110.34 (17)	S1'—C32'—H32E	109.5
C17—C14—C16	101.62 (16)	H32D—C32'—H32E	109.5
C17—C14—C13	112.62 (17)	S1'—C32'—H32F	109.5
C16—C14—C13	108.76 (16)	H32D—C32'—H32F	109.5
C17—C14—C10	121.29 (17)	H32E—C32'—H32F	109.5
C16—C14—C10	109.83 (16)	S1'—C33'—H33D	109.5
C13—C14—C10	102.46 (15)	S1'—C33'—H33E	109.5
N3—C15—H15A	109.5	H33D—C33'—H33E	109.5
N3—C15—H15B	109.5	S1'—C33'—H33F	109.5
H15A—C15—H15B	109.5	H33D—C33'—H33F	109.5
N3—C15—H15C	109.5	H33E—C33'—H33F	109.5
H15A—C15—H15C	109.5	C32'—S1'—C33'	94.8 (17)
H15B—C15—H15C	109.5	C32'—S1'—O4	76.2 (12)
O2—C16—N4	125.7 (2)	C33'—S1'—O4	114.4 (14)
O2—C16—C14	126.84 (19)	C7—N1—C6	109.5 (2)
N4—C16—C14	107.43 (19)	C7—N1—H1A	125.1 (17)
C22—C17—C18	118.7 (2)	C6—N1—H1A	125.3 (17)
C22—C17—C14	132.5 (2)	C13—N3—C12	107.13 (17)
C18—C17—C14	108.56 (18)	C13—N3—C15	114.81 (18)
C19—C18—C17	122.6 (2)	C12—N3—C15	112.82 (18)
C19—C18—N4	127.8 (2)	C16—N4—C18	112.51 (19)
C17—C18—N4	109.64 (19)	C16—N4—H4A	121.9 (17)
C18—C19—C20	117.4 (2)	C18—N4—H4A	124.8 (17)
C18—C19—H19	121.3	C23—N5—C24	110.86 (19)
C20—C19—H19	121.3	C23—N5—C30	123.2 (2)
C21—C20—C19	121.2 (2)	C24—N5—C30	125.8 (2)

C6—C1—C2—C3	−0.8 (4)	C22—C17—C18—N4	−179.31 (19)
C8—C1—C2—C3	178.4 (3)	C14—C17—C18—N4	−3.7 (2)
C1—C2—C3—C4	0.0 (4)	C17—C18—C19—C20	0.2 (4)
C2—C3—C4—C5	0.6 (5)	N4—C18—C19—C20	178.8 (2)
C3—C4—C5—C6	−0.2 (4)	C18—C19—C20—C21	0.1 (4)
C4—C5—C6—N1	−178.7 (2)	C19—C20—C21—C22	−0.3 (4)
C4—C5—C6—C1	−0.7 (4)	C20—C21—C22—C17	0.0 (4)
C2—C1—C6—N1	179.6 (2)	C18—C17—C22—C21	0.4 (3)
C8—C1—C6—N1	0.2 (2)	C14—C17—C22—C21	−174.0 (2)
C2—C1—C6—C5	1.2 (3)	N3—C13—C23—O3	45.5 (3)
C8—C1—C6—C5	−178.2 (2)	C25—C13—C23—O3	172.3 (2)
N1—C7—C8—C1	0.2 (2)	C14—C13—C23—O3	−68.1 (3)
N1—C7—C8—C9	179.1 (2)	N3—C13—C23—N5	−132.22 (19)
C6—C1—C8—C7	−0.3 (2)	C25—C13—C23—N5	−5.4 (2)
C2—C1—C8—C7	−179.5 (3)	C14—C13—C23—N5	114.21 (19)
C6—C1—C8—C9	−179.2 (2)	C29—C24—C25—C26	−4.0 (3)
C2—C1—C8—C9	1.5 (4)	N5—C24—C25—C26	175.3 (2)
C7—C8—C9—O1	−175.8 (2)	C29—C24—C25—C13	173.3 (2)
C1—C8—C9—O1	2.8 (3)	N5—C24—C25—C13	−7.4 (2)
C7—C8—C9—C10	5.0 (3)	N3—C13—C25—C26	−52.2 (3)
C1—C8—C9—C10	−176.37 (19)	C23—C13—C25—C26	−175.6 (2)
O1—C9—C10—C11	126.3 (2)	C14—C13—C25—C26	66.7 (3)
C8—C9—C10—C11	−54.5 (2)	N3—C13—C25—C24	130.97 (19)
O1—C9—C10—C12	6.9 (3)	C23—C13—C25—C24	7.6 (2)
C8—C9—C10—C12	−173.86 (18)	C14—C13—C25—C24	−110.2 (2)
O1—C9—C10—C14	−110.0 (2)	C24—C25—C26—C27	3.1 (3)
C8—C9—C10—C14	69.2 (2)	C13—C25—C26—C27	−173.4 (2)
C11—C10—C12—N3	126.58 (19)	C25—C26—C27—C28	−0.2 (4)
C9—C10—C12—N3	−115.54 (19)	C26—C27—C28—C29	−2.0 (4)
C14—C10—C12—N3	6.3 (2)	C25—C24—C29—C28	1.8 (4)
N3—C13—C14—C17	−168.92 (16)	N5—C24—C29—C28	−177.4 (2)
C25—C13—C14—C17	63.4 (2)	C27—C28—C29—C24	1.2 (4)
C23—C13—C14—C17	−48.6 (2)	C8—C7—N1—C6	−0.1 (3)
N3—C13—C14—C16	79.25 (19)	C5—C6—N1—C7	178.3 (2)
C25—C13—C14—C16	−48.4 (2)	C1—C6—N1—C7	−0.1 (2)
C23—C13—C14—C16	−160.48 (17)	C25—C13—N3—C12	167.45 (18)
N3—C13—C14—C10	−36.98 (18)	C23—C13—N3—C12	−75.4 (2)
C25—C13—C14—C10	−164.67 (17)	C14—C13—N3—C12	43.1 (2)
C23—C13—C14—C10	83.29 (19)	C25—C13—N3—C15	−66.4 (2)
C11—C10—C14—C17	27.0 (3)	C23—C13—N3—C15	50.7 (2)
C12—C10—C14—C17	145.03 (19)	C14—C13—N3—C15	169.20 (17)
C9—C10—C14—C17	−93.4 (2)	C10—C12—N3—C13	−31.4 (2)
C11—C10—C14—C16	145.00 (18)	C10—C12—N3—C15	−158.72 (18)
C12—C10—C14—C16	−96.96 (19)	O2—C16—N4—C18	−177.3 (2)
C9—C10—C14—C16	24.6 (2)	C14—C16—N4—C18	2.5 (2)
C11—C10—C14—C13	−99.54 (19)	C19—C18—N4—C16	−178.1 (2)
C12—C10—C14—C13	18.50 (19)	C17—C18—N4—C16	0.7 (3)
C9—C10—C14—C13	140.06 (17)	O3—C23—N5—C24	−176.3 (2)
C17—C14—C16—O2	175.5 (2)	C13—C23—N5—C24	1.4 (2)
C13—C14—C16—O2	−65.6 (3)	O3—C23—N5—C30	−0.3 (4)
C10—C14—C16—O2	45.8 (3)	C13—C23—N5—C30	177.3 (2)
C17—C14—C16—N4	−4.4 (2)	C29—C24—N5—C23	−176.9 (2)
C13—C14—C16—N4	114.59 (19)	C25—C24—N5—C23	3.8 (3)
C10—C14—C16—N4	−134.02 (18)	C29—C24—N5—C30	7.2 (4)
C16—C14—C17—C22	179.6 (2)	C25—C24—N5—C30	−172.1 (2)
C13—C14—C17—C22	63.4 (3)	C31—C30—N5—C23	102.0 (3)
C10—C14—C17—C22	−58.4 (3)	C31—C30—N5—C24	−82.7 (3)
C16—C14—C17—C18	4.8 (2)	C32—S1—O4—S1'	−131.2 (7)
C13—C14—C17—C18	−111.40 (19)	C33—S1—O4—S1'	−27.8 (6)
C10—C14—C17—C18	126.82 (19)	C32'—S1'—O4—S1	59.2 (13)
C22—C17—C18—C19	−0.5 (3)	C33'—S1'—O4—S1	148.3 (16)
C14—C17—C18—C19	175.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O4	0.84 (3)	1.89 (3)	2.714 (3)	166 (2)
N1—H1A···O2ⁱ	0.84 (3)	2.10 (3)	2.887 (3)	155 (2)
C22—H22···S1ⁱⁱ	0.93	2.85	3.717 (3)	157
C32—H32A···O3ⁱⁱⁱ	0.96	2.60	3.219 (4)	123

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+3/2, y+1/2, z; (iii) −x+3/2, y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O4	0.84 (3)	1.89 (3)	2.714 (3)	166 (2)
N1—H1A···O2ⁱ	0.84 (3)	2.10 (3)	2.887 (3)	155 (2)
C22—H22···S1ⁱⁱ	0.93	2.85	3.717 (3)	157
C32—H32A···O3ⁱⁱⁱ	0.96	2.60	3.219 (4)	123

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+3/2, y+1/2, z; (iii) −x+3/2, y−1/2, z.

Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

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Volume 69| Part 8| August 2013| Pages o1328-o1329

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

1-Ethyl-4′-(1H-indol-3-ylcarbon­yl)-1′-methyl-2,2′′-dioxodi­spiro­[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carbo­nitrile di­methyl sulfoxide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Ethyl-4′-(1H-indol-3-ylcarbonyl)-1′-methyl-2,2′′-dioxodispiro[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carbonitrile dimethyl sulfoxide monosolvate