Methyl 3′-(2,5-di­methyl­benz­yl)-1′-methyl-2-oxo-4′-phenyl­spiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate chloro­form monosolvate

Karthikeyan, S.; Narayanan, P.; Sethusankar, K.; Devaraj, A.; Bakthadoss, M.

doi:10.1107/S1600536814004073

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o377-o378

doi:10.1107/S1600536814004073

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Methyl 3′-(2,5-dimethylbenzyl)-1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine]-3′-carboxylate chloroform monosolvate

S. Karthikeyan,^a P. Narayanan,^a K. Sethusankar,^a ^* Anthonisamy Devaraj ^b and Manickam Bakthadoss ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 19 February 2014; accepted 21 February 2014; online 28 February 2014)

In the title solvate, C₂₉H₃₀N₂O₃·CHCl₃, the dihedral angle between the indole ring system (r.m.s. deviation = 0.050 Å) and the 4-methylpyrrolidine ring is 88.88 (8)°. The latter ring adopts an envelope conformation with the N atom as the flap. Its mean plane makes dihedral angles of 86.94 (11) and 42.08 (9)° with the phenyl and dimethylbenzene rings, respectively. The molecular conformation is stabilized by intramolecular C—H⋯O hydrogen bonds, which generate S(6) and S(9) ring motifs. The chloroform solvent molecule is linked to the organic molecule by a C—H⋯O hydrogen bond involving the carbonyl O atom of the carboxylate group. In the crystal, molecules are linked via bifurcated N—H⋯(N,O) and C—H⋯O hydrogen bonds, forming chains propagating along [001].

CCDC reference: 988124

Related literature

For the biological activity of spiro compounds and oxindole derivatives, see: Bhattacharya et al. (1982 ); Chande et al. (2005 ); Glover et al. (1998 ). For a related crystal structure, see: Karthikeyan et al. (2014 ). For puckering parameters, see: Cremer & Pople (1975 ). For graph-set motif notation, see: Bernstein et al. (1995 ). For bond-length distortions in small rings, see: Allen (1981 ).

Experimental

Crystal data

C₂₉H₃₀N₂O₃·CHCl₃
M_r = 573.92
Monoclinic, P 2₁ /c
a = 12.9164 (4) Å
b = 17.6167 (5) Å
c = 12.4548 (5) Å
β = 98.135 (2)°
V = 2805.50 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
32563 measured reflections
8093 independent reflections
4986 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.161
S = 1.01
8093 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.45	3.292 (2)	151
C18—H18B⋯O1	0.97	2.52	3.127 (2)	120
C30—H30⋯O2	0.98	2.47	3.319 (3)	144
N2—H2A⋯O2ⁱ	0.86	2.65	3.252 (2)	128
N2—H2A⋯N1ⁱ	0.86	2.20	2.936 (2)	143
C7—H7⋯O1ⁱⁱ	0.98	2.57	3.359 (2)	138
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

CCDC reference: 988124

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814004073/su2703sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004073/su2703Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004073/su2703Isup3.cml

checkCIF report

Comment top

Synthesis of spiro compounds has drawn considerable attention from chemists, in view of their very good antimycobacterial activity (Chande et al., 2005). Oxindole derivatives are known to be potent inhibitors of monoamine oxidase (MAO) in human urine and rat tissues (Glover et al., 1998) and potent antagonists of in vitro receptor binding by atrial natriuretic peptide besides possessing a wide range of central nervous system activities (Bhattacharya et al., 1982).

The molecular structure of the title compound is illustrated in Fig 1. In the molecule, there is C—H···O hydrogen bond, forming an S(6) and S(9) ring motif (Bernstein et al., 1995). The indole ring system is essentially planar with a maximum deviation of 0.0782 (17) Å for the atom C10. The mean plane of the indole ring system forms dihedral angle of 88.88 (8)° with central mean plane of pyrrolidine five membered ring. The latter forms a dihedral angle of 42.08 (10)° with the benzyl ring. Atom O1 significantly deviates from the mean plane of the indole ring system by 0.1965 (12) Å. The molecular dimensions in the title compound are in excellent agreement with the those reported for a related compound (Karthikeyan et al., 2014).

The spiro-pyrrolidine ring adopts an envelope conformation with atom N1 at the flap position. The distance to the flap position from the mean plane of the spiro carbon is 0.2628 (15) Å. The puckering parameters (Cremer & Pople, 1975) of the ring are Q₂ = 0.4155 (17) Å and φ₂ = 0.5 (2)°. The central spiro-pyrrolidine ring is perpendicular to the phenyl ring (C1—C6) with a dihedral angle of 86.94 (11)°. The carbonyl group and the benzyl ring have an (+)anti-periplanar conformation with the torsion angle (C18—C17—C25—O2) of 152.45 (17)°.

In the benzene ring (C11—C16) of the indole ring system, the expansion of the ipso angles at C11, C13 and C14 [122.20 (17), 120.82 (19) and 120.86 (19)°, respectively] and contraction of the apical angles at C12, C15 and C16 [117.80 (19), 118.99 (18) and 119.24 (16)°, respectively] are caused by the fusion of the smaller pyrrole ring to the six-membered benzene ring and the strain is taken up by the angular distortion rather than by bond-length distortions (Allen, 1981). The carboxyl group and oxindole ring system are (-)syn-clinal to each other with the torsion angle (C9—C17—C25—O2) of -87.22 (9)°.

In the crystal, (Fig. 2 and Table 1), molecules are linked by N2—H2A···N1⁽ⁱ⁾ [x,-y + 1/2,z + 1/2] and N2—H2A···O2⁽ⁱ⁾ [x,-y + 1/2,z + 1/2] bifurcated hydrogen bonds which together generate C₂¹[R₂¹(6)] chains (Bernstein et al., 1995), running parallel to [001]. The intermolecular C7—H7···O1⁽ⁱⁱ⁾ [x,-y + 1/2,z - 1/2] interaction forms C(6) chains running parallel to the same [001] axis. The CHCl₃ solvent molecule is involved in an intramolecular hydrogen bond with the C═ O atom, O2, of the carboxylate group.

Related literature top

For the biological activity of spiro compounds and oxindole derivatives, see: Bhattacharya et al. (1982); Chande et al. (2005); Glover et al. (1998). For a related crystal structure, see: Karthikeyan et al. (2014). For puckering parameters, see: Cremer & Pople (1975). For graph-set motif notation, see: Bernstein et al. (1995). For bond-length distortions in small rings, see: Allen (1981).

Experimental top

A mixture of (E)-methyl 2-(2,5-dimethylbenzyl)-3-phenylacrylate (2 mmol), isatin (2 mmol) and sarcosine (2 mmol) in acetonitrile (8 ml) was refluxed for 12 h. After completion of the reaction, as indicated by TLC, the mixture was concentrated. The resulting crude mass was diluted with water (10 ml) and extracted with ethyl acetate (3 × 10 ml). The combined organic layers were washed with brine (2 × 10 ml) and dried over anhydrous Na₂SO₄. The organic layer was concentrated and the residue purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate:hexanes (2:8) to afford the title compound as a colourless crystals in 67% 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 molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial view along the a axis of the crystal packing of the title compound. The N—H···N, N-H···O and C—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).

Methyl 3'-(2,5-dimethylbenzyl)-1'-methyl-2-oxo-4'-phenylspiro[indoline-3,2'-pyrrolidine]-3'-carboxylate chloroform monosolvate top

Crystal data top

C₂₉H₃₀N₂O₃·CHCl₃	F(000) = 1200
M_r = 573.92	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8093 reflections
a = 12.9164 (4) Å	θ = 2.0–30.0°
b = 17.6167 (5) Å	µ = 0.36 mm⁻¹
c = 12.4548 (5) Å	T = 293 K
β = 98.135 (2)°	Block, colourless
V = 2805.50 (16) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 30.0°, θ_min = 2.0°
ω scans	h = −18→15
32563 measured reflections	k = −24→17
8093 independent reflections	l = −16→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0743P)² + 0.8771P] where P = (F_o² + 2F_c²)/3
8093 reflections	(Δ/σ)_max = 0.029
347 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₉H₃₀N₂O₃·CHCl₃	V = 2805.50 (16) Å³
M_r = 573.92	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9164 (4) Å	µ = 0.36 mm⁻¹
b = 17.6167 (5) Å	T = 293 K
c = 12.4548 (5) Å	0.35 × 0.30 × 0.25 mm
β = 98.135 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4986 reflections with I > 2σ(I)
32563 measured reflections	R_int = 0.032
8093 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.01	Δρ_max = 0.38 e Å⁻³
8093 reflections	Δρ_min = −0.46 e Å⁻³
347 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
C1	0.52972 (18)	0.16392 (14)	0.1611 (2)	0.0606 (6)
H1	0.5616	0.1446	0.1045	0.073*
C2	0.4214 (2)	0.16690 (18)	0.1514 (3)	0.0870 (10)
H2	0.3813	0.1492	0.0884	0.104*
C3	0.3732 (2)	0.19554 (17)	0.2334 (3)	0.0844 (10)
H3	0.3006	0.1969	0.2265	0.101*
C4	0.43157 (18)	0.22214 (14)	0.3255 (3)	0.0670 (7)
H4	0.3987	0.2417	0.3813	0.080*
C5	0.54030 (15)	0.22008 (11)	0.33620 (19)	0.0473 (5)
H5	0.5796	0.2393	0.3986	0.057*
C6	0.59068 (14)	0.18961 (10)	0.25467 (16)	0.0391 (4)
C7	0.70826 (13)	0.19113 (9)	0.25662 (13)	0.0300 (3)
H7	0.7220	0.1678	0.1886	0.036*
C8	0.74566 (13)	0.27309 (9)	0.25403 (14)	0.0319 (3)
H8A	0.7355	0.2928	0.1805	0.038*
H8B	0.7086	0.3053	0.2991	0.038*
C9	0.86380 (12)	0.21922 (9)	0.39155 (12)	0.0269 (3)
C10	0.82724 (13)	0.25825 (9)	0.49252 (13)	0.0309 (3)
C11	0.99571 (13)	0.21963 (10)	0.54390 (14)	0.0347 (4)
C12	1.09263 (16)	0.20958 (12)	0.60490 (17)	0.0482 (5)
H12	1.1043	0.2224	0.6780	0.058*
C13	1.17168 (16)	0.17983 (13)	0.5537 (2)	0.0540 (5)
H13	1.2374	0.1715	0.5932	0.065*
C14	1.15450 (15)	0.16239 (12)	0.44510 (19)	0.0497 (5)
H14	1.2091	0.1434	0.4117	0.060*
C15	1.05653 (14)	0.17275 (10)	0.38447 (16)	0.0391 (4)
H15	1.0456	0.1616	0.3108	0.047*
C16	0.97590 (13)	0.19984 (9)	0.43528 (13)	0.0301 (3)
C17	0.78538 (12)	0.15185 (9)	0.35030 (12)	0.0272 (3)
C18	0.73755 (13)	0.11476 (9)	0.44370 (14)	0.0324 (4)
H18A	0.7936	0.1058	0.5028	0.039*
H18B	0.6903	0.1511	0.4693	0.039*
C19	0.67848 (13)	0.04089 (9)	0.42034 (15)	0.0356 (4)
C20	0.64281 (14)	0.01636 (10)	0.31604 (17)	0.0418 (4)
H20	0.6602	0.0446	0.2581	0.050*
C21	0.58202 (15)	−0.04865 (11)	0.2939 (2)	0.0506 (5)
C22	0.56029 (16)	−0.09077 (12)	0.3815 (2)	0.0592 (6)
H22	0.5208	−0.1349	0.3698	0.071*
C23	0.59634 (16)	−0.06826 (12)	0.4854 (2)	0.0573 (6)
H23	0.5806	−0.0978	0.5429	0.069*
C24	0.65561 (14)	−0.00280 (11)	0.50774 (18)	0.0443 (5)
C25	0.85308 (13)	0.09330 (9)	0.30117 (14)	0.0314 (3)
C26	0.96441 (19)	−0.01230 (12)	0.3421 (2)	0.0563 (6)
H26A	0.9259	−0.0453	0.2896	0.084*
H26B	0.9945	−0.0414	0.4039	0.084*
H26C	1.0191	0.0123	0.3103	0.084*
C27	0.90549 (16)	0.34317 (11)	0.31638 (17)	0.0454 (5)
H27A	0.8690	0.3715	0.3651	0.068*
H27B	0.9024	0.3701	0.2490	0.068*
H27C	0.9772	0.3368	0.3479	0.068*
C28	0.5391 (2)	−0.06896 (15)	0.1793 (2)	0.0740 (8)
H28A	0.4752	−0.0969	0.1785	0.111*
H28B	0.5891	−0.0995	0.1487	0.111*
H28C	0.5256	−0.0234	0.1373	0.111*
C29	0.69211 (19)	0.01897 (14)	0.6230 (2)	0.0604 (6)
H29A	0.6638	−0.0158	0.6706	0.091*
H29B	0.6689	0.0695	0.6358	0.091*
H29C	0.7671	0.0172	0.6366	0.091*
C30	0.8351 (2)	−0.03717 (16)	0.0148 (2)	0.0727 (7)
H30	0.8775	−0.0035	0.0660	0.087*
N1	0.85668 (11)	0.26899 (7)	0.29684 (11)	0.0297 (3)
N2	0.90658 (11)	0.25256 (9)	0.57607 (12)	0.0391 (4)
H2A	0.9025	0.2674	0.6411	0.047*
O1	0.74367 (10)	0.28839 (7)	0.49619 (10)	0.0406 (3)
O2	0.87103 (11)	0.09300 (8)	0.20917 (10)	0.0470 (3)
O3	0.89518 (10)	0.04398 (7)	0.37572 (10)	0.0376 (3)
Cl1	0.80296 (6)	−0.11741 (5)	0.08605 (8)	0.0992 (3)
Cl2	0.72435 (8)	0.01165 (5)	−0.03976 (10)	0.1107 (3)
Cl3	0.91063 (9)	−0.06436 (6)	−0.08484 (8)	0.1116 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0494 (12)	0.0582 (13)	0.0670 (15)	−0.0072 (10)	−0.0171 (11)	0.0041 (11)
C2	0.0539 (16)	0.086 (2)	0.108 (3)	−0.0188 (15)	−0.0341 (16)	0.0200 (18)
C3	0.0336 (12)	0.0785 (19)	0.137 (3)	−0.0047 (12)	−0.0028 (16)	0.0423 (19)
C4	0.0418 (12)	0.0548 (13)	0.108 (2)	0.0071 (10)	0.0222 (13)	0.0316 (14)
C5	0.0376 (10)	0.0399 (10)	0.0651 (14)	0.0012 (8)	0.0102 (9)	0.0142 (9)
C6	0.0340 (9)	0.0296 (8)	0.0517 (11)	−0.0008 (7)	−0.0013 (8)	0.0098 (8)
C7	0.0339 (8)	0.0287 (8)	0.0267 (8)	−0.0002 (6)	0.0018 (6)	0.0003 (6)
C8	0.0367 (9)	0.0299 (8)	0.0287 (8)	0.0003 (7)	0.0039 (7)	0.0051 (6)
C9	0.0298 (8)	0.0286 (7)	0.0228 (7)	−0.0004 (6)	0.0055 (6)	−0.0013 (6)
C10	0.0341 (9)	0.0312 (8)	0.0283 (8)	−0.0014 (7)	0.0072 (7)	−0.0031 (6)
C11	0.0317 (8)	0.0382 (9)	0.0341 (9)	−0.0009 (7)	0.0044 (7)	−0.0018 (7)
C12	0.0415 (11)	0.0599 (13)	0.0399 (11)	0.0017 (9)	−0.0056 (8)	−0.0038 (9)
C13	0.0344 (10)	0.0611 (13)	0.0632 (14)	0.0037 (9)	−0.0046 (9)	−0.0019 (11)
C14	0.0335 (10)	0.0517 (12)	0.0653 (14)	0.0056 (8)	0.0119 (9)	−0.0041 (10)
C15	0.0374 (9)	0.0410 (10)	0.0402 (10)	0.0003 (8)	0.0100 (8)	−0.0042 (8)
C16	0.0306 (8)	0.0298 (8)	0.0301 (8)	−0.0030 (6)	0.0055 (6)	−0.0002 (6)
C17	0.0314 (8)	0.0250 (7)	0.0253 (8)	−0.0013 (6)	0.0046 (6)	0.0003 (6)
C18	0.0356 (9)	0.0304 (8)	0.0324 (9)	−0.0007 (7)	0.0090 (7)	0.0043 (6)
C19	0.0292 (8)	0.0284 (8)	0.0502 (11)	0.0026 (6)	0.0093 (7)	0.0089 (7)
C20	0.0380 (10)	0.0307 (9)	0.0562 (12)	−0.0020 (7)	0.0049 (8)	0.0039 (8)
C21	0.0340 (10)	0.0314 (9)	0.0848 (16)	0.0004 (8)	0.0029 (10)	−0.0025 (10)
C22	0.0367 (10)	0.0332 (10)	0.107 (2)	−0.0054 (8)	0.0098 (12)	0.0091 (12)
C23	0.0420 (11)	0.0420 (11)	0.0911 (19)	0.0000 (9)	0.0208 (12)	0.0279 (11)
C24	0.0349 (9)	0.0375 (9)	0.0637 (13)	0.0059 (8)	0.0178 (9)	0.0191 (9)
C25	0.0345 (8)	0.0276 (8)	0.0318 (9)	−0.0022 (7)	0.0036 (7)	−0.0021 (6)
C26	0.0637 (14)	0.0415 (11)	0.0639 (14)	0.0206 (10)	0.0101 (11)	−0.0004 (10)
C27	0.0527 (11)	0.0331 (9)	0.0501 (12)	−0.0124 (8)	0.0055 (9)	0.0033 (8)
C28	0.0675 (16)	0.0518 (14)	0.097 (2)	−0.0107 (12)	−0.0083 (14)	−0.0168 (13)
C29	0.0594 (14)	0.0661 (14)	0.0595 (14)	0.0025 (11)	0.0219 (11)	0.0265 (11)
C30	0.0636 (16)	0.0764 (17)	0.0758 (18)	−0.0125 (13)	0.0022 (13)	−0.0162 (14)
N1	0.0347 (7)	0.0274 (7)	0.0272 (7)	−0.0048 (5)	0.0050 (5)	0.0023 (5)
N2	0.0374 (8)	0.0554 (9)	0.0243 (7)	0.0019 (7)	0.0037 (6)	−0.0096 (6)
O1	0.0380 (7)	0.0472 (7)	0.0373 (7)	0.0077 (6)	0.0084 (5)	−0.0086 (5)
O2	0.0607 (9)	0.0490 (8)	0.0330 (7)	0.0132 (7)	0.0124 (6)	−0.0031 (6)
O3	0.0426 (7)	0.0309 (6)	0.0394 (7)	0.0085 (5)	0.0064 (5)	0.0036 (5)
Cl1	0.0716 (5)	0.1114 (6)	0.1077 (7)	−0.0031 (4)	−0.0107 (4)	0.0367 (5)
Cl2	0.0970 (6)	0.0791 (5)	0.1532 (9)	0.0107 (4)	0.0078 (6)	0.0290 (5)
Cl3	0.1246 (8)	0.1139 (7)	0.1039 (7)	−0.0108 (6)	0.0420 (6)	−0.0332 (5)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C17—C18	1.538 (2)
C1—C2	1.388 (4)	C18—C19	1.516 (2)
C1—H1	0.9300	C18—H18A	0.9700
C2—C3	1.366 (5)	C18—H18B	0.9700
C2—H2	0.9300	C19—C20	1.385 (3)
C3—C4	1.363 (5)	C19—C24	1.398 (3)
C3—H3	0.9300	C20—C21	1.394 (3)
C4—C5	1.392 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.380 (3)
C5—C6	1.389 (3)	C21—C28	1.500 (4)
C5—H5	0.9300	C22—C23	1.371 (4)
C6—C7	1.516 (2)	C22—H22	0.9300
C7—C8	1.524 (2)	C23—C24	1.390 (3)
C7—C17	1.582 (2)	C23—H23	0.9300
C7—H7	0.9800	C24—C29	1.497 (3)
C8—N1	1.459 (2)	C25—O2	1.201 (2)
C8—H8A	0.9700	C25—O3	1.330 (2)
C8—H8B	0.9700	C26—O3	1.437 (2)
C9—N1	1.462 (2)	C26—H26A	0.9600
C9—C16	1.512 (2)	C26—H26B	0.9600
C9—C10	1.564 (2)	C26—H26C	0.9600
C9—C17	1.597 (2)	C27—N1	1.456 (2)
C10—O1	1.210 (2)	C27—H27A	0.9600
C10—N2	1.357 (2)	C27—H27B	0.9600
C11—C12	1.381 (3)	C27—H27C	0.9600
C11—C16	1.385 (2)	C28—H28A	0.9600
C11—N2	1.397 (2)	C28—H28B	0.9600
C12—C13	1.382 (3)	C28—H28C	0.9600
C12—H12	0.9300	C29—H29A	0.9600
C13—C14	1.374 (3)	C29—H29B	0.9600
C13—H13	0.9300	C29—H29C	0.9600
C14—C15	1.391 (3)	C30—Cl2	1.724 (3)
C14—H14	0.9300	C30—Cl1	1.750 (3)
C15—C16	1.378 (2)	C30—Cl3	1.751 (3)
C15—H15	0.9300	C30—H30	0.9800
C17—C25	1.534 (2)	N2—H2A	0.8600

C6—C1—C2	120.4 (3)	C19—C18—H18A	107.9
C6—C1—H1	119.8	C17—C18—H18A	107.9
C2—C1—H1	119.8	C19—C18—H18B	107.9
C3—C2—C1	120.6 (3)	C17—C18—H18B	107.9
C3—C2—H2	119.7	H18A—C18—H18B	107.2
C1—C2—H2	119.7	C20—C19—C24	118.66 (17)
C4—C3—C2	120.0 (2)	C20—C19—C18	122.66 (16)
C4—C3—H3	120.0	C24—C19—C18	118.63 (17)
C2—C3—H3	120.0	C19—C20—C21	123.04 (19)
C3—C4—C5	120.1 (3)	C19—C20—H20	118.5
C3—C4—H4	120.0	C21—C20—H20	118.5
C5—C4—H4	120.0	C22—C21—C20	117.2 (2)
C6—C5—C4	120.7 (2)	C22—C21—C28	122.3 (2)
C6—C5—H5	119.6	C20—C21—C28	120.4 (2)
C4—C5—H5	119.6	C23—C22—C21	120.71 (19)
C1—C6—C5	118.11 (19)	C23—C22—H22	119.6
C1—C6—C7	117.89 (19)	C21—C22—H22	119.6
C5—C6—C7	123.60 (17)	C22—C23—C24	122.2 (2)
C6—C7—C8	109.65 (14)	C22—C23—H23	118.9
C6—C7—C17	121.93 (14)	C24—C23—H23	118.9
C8—C7—C17	105.16 (13)	C23—C24—C19	118.2 (2)
C6—C7—H7	106.4	C23—C24—C29	119.59 (19)
C8—C7—H7	106.4	C19—C24—C29	122.23 (18)
C17—C7—H7	106.4	O2—C25—O3	123.23 (16)
N1—C8—C7	104.09 (13)	O2—C25—C17	125.55 (15)
N1—C8—H8A	110.9	O3—C25—C17	111.12 (14)
C7—C8—H8A	110.9	O3—C26—H26A	109.5
N1—C8—H8B	110.9	O3—C26—H26B	109.5
C7—C8—H8B	110.9	H26A—C26—H26B	109.5
H8A—C8—H8B	109.0	O3—C26—H26C	109.5
N1—C9—C16	111.94 (13)	H26A—C26—H26C	109.5
N1—C9—C10	113.17 (13)	H26B—C26—H26C	109.5
C16—C9—C10	101.09 (12)	N1—C27—H27A	109.5
N1—C9—C17	102.79 (12)	N1—C27—H27B	109.5
C16—C9—C17	118.65 (13)	H27A—C27—H27B	109.5
C10—C9—C17	109.60 (12)	N1—C27—H27C	109.5
O1—C10—N2	125.77 (16)	H27A—C27—H27C	109.5
O1—C10—C9	126.59 (15)	H27B—C27—H27C	109.5
N2—C10—C9	107.64 (14)	C21—C28—H28A	109.5
C12—C11—C16	122.20 (17)	C21—C28—H28B	109.5
C12—C11—N2	127.95 (17)	H28A—C28—H28B	109.5
C16—C11—N2	109.79 (15)	C21—C28—H28C	109.5
C11—C12—C13	117.80 (19)	H28A—C28—H28C	109.5
C11—C12—H12	121.1	H28B—C28—H28C	109.5
C13—C12—H12	121.1	C24—C29—H29A	109.5
C14—C13—C12	120.82 (19)	C24—C29—H29B	109.5
C14—C13—H13	119.6	H29A—C29—H29B	109.5
C12—C13—H13	119.6	C24—C29—H29C	109.5
C13—C14—C15	120.86 (19)	H29A—C29—H29C	109.5
C13—C14—H14	119.6	H29B—C29—H29C	109.5
C15—C14—H14	119.6	Cl2—C30—Cl1	111.11 (15)
C16—C15—C14	118.99 (18)	Cl2—C30—Cl3	111.84 (17)
C16—C15—H15	120.5	Cl1—C30—Cl3	109.54 (16)
C14—C15—H15	120.5	Cl2—C30—H30	108.1
C15—C16—C11	119.24 (16)	Cl1—C30—H30	108.1
C15—C16—C9	131.30 (15)	Cl3—C30—H30	108.1
C11—C16—C9	109.27 (14)	C27—N1—C8	113.35 (14)
C25—C17—C18	109.19 (13)	C27—N1—C9	115.28 (14)
C25—C17—C7	109.56 (13)	C8—N1—C9	105.71 (12)
C18—C17—C7	117.73 (13)	C10—N2—C11	111.97 (14)
C25—C17—C9	104.86 (12)	C10—N2—H2A	124.0
C18—C17—C9	112.13 (13)	C11—N2—H2A	124.0
C7—C17—C9	102.51 (12)	C25—O3—C26	117.19 (15)
C19—C18—C17	117.69 (15)

C6—C1—C2—C3	0.4 (4)	C10—C9—C17—C25	−149.46 (13)
C1—C2—C3—C4	0.6 (4)	N1—C9—C17—C18	−151.71 (13)
C2—C3—C4—C5	−0.1 (4)	C16—C9—C17—C18	84.19 (17)
C3—C4—C5—C6	−1.4 (3)	C10—C9—C17—C18	−31.11 (17)
C2—C1—C6—C5	−1.8 (3)	N1—C9—C17—C7	−24.50 (14)
C2—C1—C6—C7	−174.9 (2)	C16—C9—C17—C7	−148.60 (14)
C4—C5—C6—C1	2.3 (3)	C10—C9—C17—C7	96.10 (14)
C4—C5—C6—C7	174.93 (18)	C25—C17—C18—C19	−52.72 (19)
C1—C6—C7—C8	109.52 (19)	C7—C17—C18—C19	72.97 (19)
C5—C6—C7—C8	−63.2 (2)	C9—C17—C18—C19	−168.48 (14)
C1—C6—C7—C17	−127.14 (19)	C17—C18—C19—C20	−17.2 (2)
C5—C6—C7—C17	60.2 (2)	C17—C18—C19—C24	165.28 (15)
C6—C7—C8—N1	159.17 (14)	C24—C19—C20—C21	2.2 (3)
C17—C7—C8—N1	26.43 (16)	C18—C19—C20—C21	−175.26 (17)
N1—C9—C10—O1	55.2 (2)	C19—C20—C21—C22	−2.1 (3)
C16—C9—C10—O1	175.02 (17)	C19—C20—C21—C28	175.4 (2)
C17—C9—C10—O1	−58.9 (2)	C20—C21—C22—C23	0.9 (3)
N1—C9—C10—N2	−124.66 (15)	C28—C21—C22—C23	−176.5 (2)
C16—C9—C10—N2	−4.79 (17)	C21—C22—C23—C24	0.1 (3)
C17—C9—C10—N2	121.26 (15)	C22—C23—C24—C19	0.0 (3)
C16—C11—C12—C13	1.1 (3)	C22—C23—C24—C29	179.6 (2)
N2—C11—C12—C13	−175.89 (19)	C20—C19—C24—C23	−1.1 (3)
C11—C12—C13—C14	1.3 (3)	C18—C19—C24—C23	176.45 (16)
C12—C13—C14—C15	−1.3 (3)	C20—C19—C24—C29	179.27 (18)
C13—C14—C15—C16	−1.0 (3)	C18—C19—C24—C29	−3.1 (3)
C14—C15—C16—C11	3.2 (3)	C18—C17—C25—O2	152.45 (17)
C14—C15—C16—C9	177.68 (17)	C7—C17—C25—O2	22.2 (2)
C12—C11—C16—C15	−3.3 (3)	C9—C17—C25—O2	−87.22 (19)
N2—C11—C16—C15	174.10 (16)	C18—C17—C25—O3	−30.95 (18)
C12—C11—C16—C9	−178.93 (17)	C7—C17—C25—O3	−161.22 (13)
N2—C11—C16—C9	−1.49 (19)	C9—C17—C25—O3	89.38 (15)
N1—C9—C16—C15	−50.4 (2)	C7—C8—N1—C27	−171.60 (14)
C10—C9—C16—C15	−171.15 (18)	C7—C8—N1—C9	−44.41 (16)
C17—C9—C16—C15	69.1 (2)	C16—C9—N1—C27	−62.53 (18)
N1—C9—C16—C11	124.47 (15)	C10—C9—N1—C27	50.92 (19)
C10—C9—C16—C11	3.73 (16)	C17—C9—N1—C27	169.04 (14)
C17—C9—C16—C11	−116.06 (15)	C16—C9—N1—C8	171.44 (13)
C6—C7—C17—C25	122.61 (16)	C10—C9—N1—C8	−75.11 (15)
C8—C7—C17—C25	−111.99 (14)	C17—C9—N1—C8	43.01 (15)
C6—C7—C17—C18	−2.9 (2)	O1—C10—N2—C11	−175.49 (17)
C8—C7—C17—C18	122.51 (15)	C9—C10—N2—C11	4.3 (2)
C6—C7—C17—C9	−126.44 (15)	C12—C11—N2—C10	175.34 (19)
C8—C7—C17—C9	−1.03 (16)	C16—C11—N2—C10	−1.9 (2)
N1—C9—C17—C25	89.93 (14)	O2—C25—O3—C26	−0.7 (3)
C16—C9—C17—C25	−34.17 (17)	C17—C25—O3—C26	−177.36 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.45	3.292 (2)	151
C18—H18B···O1	0.97	2.52	3.127 (2)	120
C30—H30···O2	0.98	2.47	3.319 (3)	144
N2—H2A···O2ⁱ	0.86	2.65	3.252 (2)	128
N2—H2A···N1ⁱ	0.86	2.20	2.936 (2)	143
C7—H7···O1ⁱⁱ	0.98	2.57	3.359 (2)	138

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.45	3.292 (2)	151
C18—H18B···O1	0.97	2.52	3.127 (2)	120
C30—H30···O2	0.98	2.47	3.319 (3)	144
N2—H2A···O2ⁱ	0.86	2.65	3.252 (2)	128
N2—H2A···N1ⁱ	0.86	2.20	2.936 (2)	143
C7—H7···O1ⁱⁱ	0.98	2.57	3.359 (2)	138

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

Acknowledgements

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

References

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Volume 70| Part 3| March 2014| Pages o377-o378

doi:10.1107/S1600536814004073

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

Methyl 3′-(2,5-di­methyl­benz­yl)-1′-methyl-2-oxo-4′-phenyl­spiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate chloro­form monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 3′-(2,5-dimethylbenzyl)-1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine]-3′-carboxylate chloroform monosolvate