4′-(4-Methoxy­phen­yl)-1,1′,1′′-trimethyl­dispiro­[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione

Nirmala, S.; Karthikeyan, K.; Kamala, E.T.S.; Sudha, L.; Perumal, P.T.

doi:10.1107/S1600536809021114

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1655-o1656

doi:10.1107/S1600536809021114

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4′-(4-Methoxyphenyl)-1,1′,1′′-trimethyldispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione

S. Nirmala,^a K. Karthikeyan,^b E. Theboral Sugi Kamala,^a L. Sudha ^c ^* and P. T. Perumal ^b

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 22 May 2009; accepted 3 June 2009; online 20 June 2009)

In the title compound, C₂₄H₂₅N₃O₄, the pyrrolidine ring adopts an envelope conformation while the pyrrolidine-2′′,5′′-dione ring adopts a twist conformation. The indoline unit is planar [maximum deviation of −0.050 (9) Å] and forms a dihedral angle of 40.36 (4)° with the methoxyphenyl ring. Intramolecular C—H⋯O hydrogen bonds are observed. In the crystal, molecules are linked into a two-dimensional network parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of spiro-pyrrolidine-containing compounds, see: Araki et al. (2002 ); Gore et al. (1991 ); James et al. (1991 ); Kobayashi et al. (1991 ); Tietze et al. (1988 ). For the biological activity of indole derivatives, see: Harris & Uhle (1960 ); Ho et al. (1986 ); Stevenson et al. (2000 ). For a related structure, see: Govind et al. (2003 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₅N₃O₄
M_r = 419.47
Orthorhombic, P b c a
a = 11.2074 (3) Å
b = 11.2406 (3) Å
c = 33.6082 (9) Å
V = 4233.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.17 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.978, T_max = 0.987
17736 measured reflections
5023 independent reflections
3269 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.152
S = 1.07
5023 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.93	2.52	3.122 (2)	123
C12—H12A⋯O1	0.97	2.58	3.222 (2)	124
C20—H20⋯O1	0.93	2.56	3.400 (2)	150
C12—H12B⋯O1ⁱ	0.97	2.56	3.264 (2)	129
C16—H16⋯O4ⁱⁱ	0.93	2.50	3.394 (2)	161
C19—H19⋯O2ⁱⁱⁱ	0.93	2.54	3.440 (2)	162
C21—H21C⋯Cg1^iv	0.96	2.93	3.592 (2)	127
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) -x+1, -y+1, -z. Cg1 is the centroid of the C15–C20 ring.

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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021114/ci2815sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021114/ci2815Isup2.hkl

checkCIF report

Comment top

Spiro compounds are a particular class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). The spiro-pyrrolidine ring system is also found in phermones, antibiotics (Gore et al., 1991) and antitumour agents (Tietze et al., 1988; Araki et al., 2002).

Indole compounds can be used as bioactive drugs (Stevenson et al., 2000). Indole derivatives exhibit antiallergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). In view of this biological importance, the crystal structure of the title compound was determined and the results are presented here.

An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig.1. The indole unit is planar, with a maximum deviation of -0.050 (9) Å for atom C1. The dihedral angle between the indole unit and the methoxyphenyl ring is 40.36 (4)°. The sum of angles at atoms N1 (360.0°) and N3 (359.9°) is in accordance with sp² hybridization, whereas the sum of angles at N2 (335.5°) is in accordance with sp³ hybridization. The N1—C5 and C5—O1 bond lengths show electron delocalization over atoms N1, C5 and O1. In the oxindole ring system, the variation in endocyclic angles are due to the fusion of the five- and six-membered rings (Govind et al., 2003). The methoxy group is almost coplanar with the C15-C20 benzene ring [C21—O4—C18—C17 = 174.7 (2)°]. The N2/C1-C4 pyrrolidine ring adopts an envelope conformation with puckering parameters q₂ and ϕ of 0.404 (2) Å and -38.8 (2)° respectively (Cremer & Pople, 1975). Atom N2 deviates by 0.590 Å from the least-squares plane through the remaining four atoms. The N3/C2/C12-C14 pyrrolidine ring adopts a twist conformation, with puckering parameters q₂ and ϕ of 0.233 (2) Å and -13.2 (4)° respectively (Cremer & Pople, 1975).

The molecular structure is stabilized by intramolecular C— H···O hydrogen bonds and the crystal packing is determined by intermolecular C—H···O hydrogen bonds and C—H···π interactions involving C15—C20 benzene rings (Table 1). In addition the packing is stabilized by van der Waals forces.

Related literature top

For the biological activity of spiro-pyrrolidine-containing compounds, see: Araki et al. (2002); Gore et al. (1991); James et al. (1991); Kobayashi et al. (1991); Tietze et al. (1988). For the biological activity of indole derivatives, see: Harris & Uhle (1960); Ho et al. (1986); Stevenson et al. (2000). For a related structure, see: Govind et al. (2003). For ring-puckering parameters, see: Cremer & Pople (1975). Cg1 is the centroid of the C15–C20 ring.

Experimental top

A mixture of sarcosine (1 mmol), 1-methylisatin (1 mmol) and 3-(4-methoxybenzylidine)-1-methyl-pyrrolidine-2,5-dione (1 mmol) was refluxed in methanol. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed in vacuo and the crude product subjected to column chromatography (100–200 mesh) using petroleum ether–ethyl acetate as eluent. Single crystals were obtained by crystallization from petroleum ether and ethyl acetate mixture.

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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involed in hydrogen bonds have been omitted.

4'-(4-Methoxyphenyl)-1,1',1''-trimethyldispiro[indoline-3,2'-pyrrolidine- 3',3''-pyrrolidine]-2,2'',5''-trione top

Crystal data top

C₂₄H₂₅N₃O₄	F(000) = 1776
M_r = 419.47	D_x = 1.316 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5049 reflections
a = 11.2074 (3) Å	θ = 2.4–25.7°
b = 11.2406 (3) Å	µ = 0.09 mm⁻¹
c = 33.6082 (9) Å	T = 293 K
V = 4233.9 (2) Å³	Prism, colourless
Z = 8	0.25 × 0.17 × 0.15 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	5023 independent reflections
Radiation source: fine-focus sealed tube	3269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→11
T_min = 0.978, T_max = 0.987	k = −15→11
17736 measured reflections	l = −43→43

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) = 0.152	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0744P)² + 0.5831P] where P = (F_o² + 2F_c²)/3
5023 reflections	(Δ/σ)_max = 0.001
284 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₄H₂₅N₃O₄	V = 4233.9 (2) Å³
M_r = 419.47	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.2074 (3) Å	µ = 0.09 mm⁻¹
b = 11.2406 (3) Å	T = 293 K
c = 33.6082 (9) Å	0.25 × 0.17 × 0.15 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	5023 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3269 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.987	R_int = 0.028
17736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.07	Δρ_max = 0.24 e Å⁻³
5023 reflections	Δρ_min = −0.18 e Å⁻³
284 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	0.01846 (15)	0.47299 (15)	0.12817 (5)	0.0327 (4)
C2	−0.06510 (14)	0.36884 (14)	0.11357 (5)	0.0316 (4)
C3	−0.09503 (15)	0.40199 (16)	0.06949 (5)	0.0365 (4)
H3	−0.0535	0.3440	0.0527	0.044*
C4	−0.03321 (17)	0.52114 (18)	0.06291 (5)	0.0433 (5)
H4A	−0.0046	0.5282	0.0358	0.052*
H4B	−0.0868	0.5868	0.0685	0.052*
C5	−0.05564 (15)	0.56643 (16)	0.15170 (5)	0.0357 (4)
C6	0.08728 (16)	0.49862 (17)	0.19406 (6)	0.0408 (4)
C7	0.1549 (2)	0.4819 (2)	0.22787 (7)	0.0582 (6)
H7	0.1375	0.5215	0.2515	0.070*
C8	0.2500 (2)	0.4037 (2)	0.22515 (7)	0.0665 (7)
H8	0.2959	0.3885	0.2476	0.080*
C9	0.2780 (2)	0.3480 (2)	0.18998 (7)	0.0608 (6)
H9	0.3434	0.2972	0.1888	0.073*
C10	0.20970 (17)	0.36673 (17)	0.15631 (6)	0.0456 (5)
H10	0.2295	0.3301	0.1324	0.055*
C11	0.11189 (15)	0.44049 (15)	0.15873 (5)	0.0353 (4)
C12	−0.16608 (15)	0.33962 (16)	0.14310 (5)	0.0371 (4)
H12A	−0.1860	0.4087	0.1591	0.045*
H12B	−0.2371	0.3133	0.1291	0.045*
C13	−0.11700 (16)	0.24208 (18)	0.16851 (6)	0.0425 (4)
C14	0.00594 (15)	0.25280 (16)	0.11418 (5)	0.0350 (4)
C15	−0.22493 (16)	0.39732 (16)	0.05782 (5)	0.0364 (4)
C16	−0.26396 (17)	0.30838 (16)	0.03233 (5)	0.0402 (4)
H16	−0.2092	0.2538	0.0224	0.048*
C17	−0.38205 (17)	0.29936 (17)	0.02148 (6)	0.0443 (5)
H17	−0.4061	0.2395	0.0041	0.053*
C18	−0.46497 (16)	0.37864 (17)	0.03623 (5)	0.0385 (4)
C19	−0.42807 (17)	0.46898 (18)	0.06074 (6)	0.0455 (5)
H19	−0.4829	0.5242	0.0702	0.055*
C20	−0.30887 (17)	0.47782 (18)	0.07131 (6)	0.0467 (5)
H20	−0.2848	0.5395	0.0879	0.056*
C21	−0.67018 (18)	0.4326 (2)	0.04175 (7)	0.0595 (6)
H21A	−0.6672	0.4262	0.0702	0.089*
H21B	−0.7469	0.4068	0.0324	0.089*
H21C	−0.6575	0.5139	0.0341	0.089*
C22	−0.0594 (2)	0.6521 (2)	0.21968 (7)	0.0586 (6)
H22A	−0.1135	0.7077	0.2077	0.088*
H22B	0.0048	0.6945	0.2322	0.088*
H22C	−0.1011	0.6058	0.2393	0.088*
C23	0.0372 (2)	0.0838 (2)	0.16109 (7)	0.0633 (6)
H23A	0.0928	0.1050	0.1816	0.095*
H23B	0.0795	0.0491	0.1391	0.095*
H23C	−0.0193	0.0274	0.1713	0.095*
C24	0.12923 (19)	0.63178 (18)	0.09418 (7)	0.0540 (5)
H24A	0.0752	0.6924	0.1031	0.081*
H24B	0.1609	0.6532	0.0686	0.081*
H24C	0.1934	0.6240	0.1129	0.081*
N1	−0.01162 (14)	0.57366 (14)	0.18924 (4)	0.0424 (4)
N2	0.06588 (13)	0.51895 (13)	0.09103 (4)	0.0381 (4)
N3	−0.02527 (14)	0.18934 (13)	0.14773 (5)	0.0416 (4)
O1	−0.13847 (12)	0.62471 (12)	0.13906 (4)	0.0506 (4)
O2	0.07934 (11)	0.21993 (11)	0.09054 (4)	0.0455 (3)
O3	−0.14963 (13)	0.21122 (15)	0.20112 (4)	0.0626 (4)
O4	−0.58015 (12)	0.36018 (13)	0.02477 (4)	0.0529 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0316 (9)	0.0305 (9)	0.0360 (9)	0.0035 (7)	−0.0024 (7)	−0.0031 (7)
C2	0.0300 (8)	0.0310 (8)	0.0337 (9)	0.0008 (7)	0.0001 (7)	−0.0048 (7)
C3	0.0377 (9)	0.0411 (10)	0.0308 (9)	0.0030 (8)	−0.0017 (7)	−0.0047 (8)
C4	0.0462 (11)	0.0472 (11)	0.0365 (10)	−0.0004 (9)	−0.0011 (8)	0.0048 (9)
C5	0.0345 (9)	0.0329 (9)	0.0397 (10)	0.0020 (8)	−0.0012 (8)	−0.0045 (8)
C6	0.0390 (10)	0.0426 (10)	0.0409 (11)	−0.0025 (8)	−0.0057 (8)	−0.0017 (8)
C7	0.0603 (13)	0.0691 (15)	0.0453 (12)	−0.0024 (12)	−0.0145 (10)	−0.0015 (11)
C8	0.0634 (14)	0.0700 (16)	0.0662 (16)	0.0002 (13)	−0.0310 (13)	0.0131 (13)
C9	0.0487 (12)	0.0501 (12)	0.0835 (17)	0.0085 (10)	−0.0224 (12)	0.0048 (12)
C10	0.0367 (10)	0.0390 (10)	0.0611 (12)	0.0032 (8)	−0.0081 (9)	−0.0028 (9)
C11	0.0318 (9)	0.0318 (9)	0.0423 (10)	−0.0023 (7)	−0.0050 (8)	−0.0006 (8)
C12	0.0317 (9)	0.0398 (10)	0.0400 (10)	−0.0002 (8)	0.0002 (8)	−0.0027 (8)
C13	0.0392 (10)	0.0468 (11)	0.0416 (11)	−0.0076 (9)	−0.0038 (9)	0.0011 (9)
C14	0.0350 (9)	0.0315 (9)	0.0385 (10)	−0.0002 (7)	−0.0022 (8)	−0.0044 (8)
C15	0.0407 (10)	0.0363 (9)	0.0323 (9)	0.0044 (8)	−0.0059 (8)	−0.0029 (8)
C16	0.0436 (10)	0.0376 (10)	0.0394 (10)	0.0054 (8)	−0.0029 (8)	−0.0079 (8)
C17	0.0499 (11)	0.0392 (10)	0.0438 (11)	−0.0027 (9)	−0.0081 (9)	−0.0104 (9)
C18	0.0379 (10)	0.0417 (10)	0.0360 (10)	−0.0021 (8)	−0.0071 (8)	0.0024 (8)
C19	0.0438 (11)	0.0444 (11)	0.0482 (11)	0.0102 (9)	−0.0038 (9)	−0.0114 (9)
C20	0.0457 (11)	0.0451 (11)	0.0492 (11)	0.0061 (9)	−0.0118 (9)	−0.0176 (9)
C21	0.0392 (11)	0.0701 (15)	0.0692 (15)	0.0060 (11)	−0.0010 (10)	−0.0035 (12)
C22	0.0547 (13)	0.0710 (15)	0.0501 (13)	0.0037 (11)	0.0039 (10)	−0.0247 (11)
C23	0.0818 (16)	0.0473 (13)	0.0608 (14)	0.0158 (12)	−0.0029 (12)	0.0122 (11)
C24	0.0500 (12)	0.0444 (12)	0.0675 (14)	−0.0118 (9)	0.0000 (11)	0.0069 (10)
N1	0.0433 (9)	0.0453 (9)	0.0387 (9)	0.0044 (7)	−0.0038 (7)	−0.0107 (7)
N2	0.0369 (8)	0.0362 (8)	0.0411 (9)	−0.0048 (7)	0.0012 (7)	0.0017 (7)
N3	0.0475 (9)	0.0348 (8)	0.0427 (9)	0.0038 (7)	−0.0018 (7)	0.0043 (7)
O1	0.0501 (8)	0.0470 (8)	0.0548 (8)	0.0192 (6)	−0.0080 (7)	−0.0098 (7)
O2	0.0473 (7)	0.0394 (7)	0.0498 (8)	0.0078 (6)	0.0059 (6)	−0.0087 (6)
O3	0.0606 (9)	0.0849 (12)	0.0423 (8)	−0.0018 (8)	0.0053 (7)	0.0165 (8)
O4	0.0391 (8)	0.0582 (9)	0.0615 (9)	0.0001 (6)	−0.0094 (7)	−0.0099 (7)

Geometric parameters (Å, º) top

C1—N2	1.452 (2)	C13—N3	1.377 (2)
C1—C11	1.511 (2)	C14—O2	1.202 (2)
C1—C5	1.555 (2)	C14—N3	1.379 (2)
C1—C2	1.577 (2)	C15—C20	1.382 (2)
C2—C14	1.528 (2)	C15—C16	1.387 (2)
C2—C12	1.541 (2)	C16—C17	1.377 (3)
C2—C3	1.564 (2)	C16—H16	0.93
C3—C15	1.509 (2)	C17—C18	1.380 (3)
C3—C4	1.524 (3)	C17—H17	0.93
C3—H3	0.98	C18—O4	1.363 (2)
C4—N2	1.458 (2)	C18—C19	1.371 (3)
C4—H4A	0.97	C19—C20	1.386 (3)
C4—H4B	0.97	C19—H19	0.93
C5—O1	1.213 (2)	C20—H20	0.93
C5—N1	1.357 (2)	C21—O4	1.417 (2)
C6—C7	1.379 (3)	C21—H21A	0.96
C6—C11	1.383 (3)	C21—H21B	0.96
C6—N1	1.402 (2)	C21—H21C	0.96
C7—C8	1.384 (3)	C22—N1	1.453 (2)
C7—H7	0.93	C22—H22A	0.96
C8—C9	1.374 (3)	C22—H22B	0.96
C8—H8	0.93	C22—H22C	0.96
C9—C10	1.382 (3)	C23—N3	1.449 (2)
C9—H9	0.93	C23—H23A	0.96
C10—C11	1.377 (2)	C23—H23B	0.96
C10—H10	0.93	C23—H23C	0.96
C12—C13	1.495 (3)	C24—N2	1.457 (2)
C12—H12A	0.97	C24—H24A	0.96
C12—H12B	0.97	C24—H24B	0.96
C13—O3	1.206 (2)	C24—H24C	0.96

N2—C1—C11	114.62 (14)	O2—C14—C2	127.58 (17)
N2—C1—C5	113.10 (14)	N3—C14—C2	108.69 (15)
C11—C1—C5	100.82 (13)	C20—C15—C16	117.38 (16)
N2—C1—C2	102.35 (13)	C20—C15—C3	123.29 (16)
C11—C1—C2	116.31 (14)	C16—C15—C3	119.33 (16)
C5—C1—C2	110.02 (13)	C17—C16—C15	121.32 (17)
C14—C2—C12	101.07 (14)	C17—C16—H16	119.3
C14—C2—C3	109.14 (14)	C15—C16—H16	119.3
C12—C2—C3	120.23 (14)	C16—C17—C18	120.32 (17)
C14—C2—C1	108.66 (13)	C16—C17—H17	119.8
C12—C2—C1	113.20 (13)	C18—C17—H17	119.8
C3—C2—C1	104.19 (13)	O4—C18—C19	124.61 (17)
C15—C3—C4	115.57 (15)	O4—C18—C17	115.98 (16)
C15—C3—C2	116.42 (14)	C19—C18—C17	119.41 (17)
C4—C3—C2	104.44 (13)	C18—C19—C20	119.84 (18)
C15—C3—H3	106.6	C18—C19—H19	120.1
C4—C3—H3	106.6	C20—C19—H19	120.1
C2—C3—H3	106.6	C15—C20—C19	121.69 (17)
N2—C4—C3	103.73 (14)	C15—C20—H20	119.2
N2—C4—H4A	111.0	C19—C20—H20	119.2
C3—C4—H4A	111.0	O4—C21—H21A	109.5
N2—C4—H4B	111.0	O4—C21—H21B	109.5
C3—C4—H4B	111.0	H21A—C21—H21B	109.5
H4A—C4—H4B	109.0	O4—C21—H21C	109.5
O1—C5—N1	124.84 (17)	H21A—C21—H21C	109.5
O1—C5—C1	126.55 (16)	H21B—C21—H21C	109.5
N1—C5—C1	108.61 (15)	N1—C22—H22A	109.5
C7—C6—C11	122.24 (18)	N1—C22—H22B	109.5
C7—C6—N1	127.72 (18)	H22A—C22—H22B	109.5
C11—C6—N1	110.04 (15)	N1—C22—H22C	109.5
C6—C7—C8	117.1 (2)	H22A—C22—H22C	109.5
C6—C7—H7	121.5	H22B—C22—H22C	109.5
C8—C7—H7	121.5	N3—C23—H23A	109.5
C9—C8—C7	121.5 (2)	N3—C23—H23B	109.5
C9—C8—H8	119.3	H23A—C23—H23B	109.5
C7—C8—H8	119.3	N3—C23—H23C	109.5
C8—C9—C10	120.6 (2)	H23A—C23—H23C	109.5
C8—C9—H9	119.7	H23B—C23—H23C	109.5
C10—C9—H9	119.7	N2—C24—H24A	109.5
C11—C10—C9	118.96 (19)	N2—C24—H24B	109.5
C11—C10—H10	120.5	H24A—C24—H24B	109.5
C9—C10—H10	120.5	N2—C24—H24C	109.5
C10—C11—C6	119.59 (17)	H24A—C24—H24C	109.5
C10—C11—C1	131.08 (17)	H24B—C24—H24C	109.5
C6—C11—C1	109.33 (15)	C5—N1—C6	111.01 (15)
C13—C12—C2	104.72 (14)	C5—N1—C22	123.85 (17)
C13—C12—H12A	110.8	C6—N1—C22	125.11 (16)
C2—C12—H12A	110.8	C1—N2—C24	115.17 (15)
C13—C12—H12B	110.8	C1—N2—C4	106.52 (13)
C2—C12—H12B	110.8	C24—N2—C4	113.80 (15)
H12A—C12—H12B	108.9	C13—N3—C14	112.41 (15)
O3—C13—N3	124.28 (19)	C13—N3—C23	123.79 (17)
O3—C13—C12	128.21 (18)	C14—N3—C23	123.66 (16)
N3—C13—C12	107.50 (16)	C18—O4—C21	118.25 (16)
O2—C14—N3	123.71 (17)

N2—C1—C2—C14	93.48 (15)	C3—C2—C14—O2	35.9 (2)
C11—C1—C2—C14	−32.26 (19)	C1—C2—C14—O2	−77.1 (2)
C5—C1—C2—C14	−146.03 (14)	C12—C2—C14—N3	−17.91 (17)
N2—C1—C2—C12	−155.10 (13)	C3—C2—C14—N3	−145.57 (14)
C11—C1—C2—C12	79.16 (18)	C1—C2—C14—N3	101.41 (15)
C5—C1—C2—C12	−34.61 (18)	C4—C3—C15—C20	−52.9 (2)
N2—C1—C2—C3	−22.77 (15)	C2—C3—C15—C20	70.3 (2)
C11—C1—C2—C3	−148.51 (14)	C4—C3—C15—C16	127.21 (18)
C5—C1—C2—C3	97.71 (15)	C2—C3—C15—C16	−109.68 (18)
C14—C2—C3—C15	113.00 (16)	C20—C15—C16—C17	−1.2 (3)
C12—C2—C3—C15	−2.9 (2)	C3—C15—C16—C17	178.77 (17)
C1—C2—C3—C15	−131.08 (15)	C15—C16—C17—C18	−0.7 (3)
C14—C2—C3—C4	−118.28 (15)	C16—C17—C18—O4	−178.00 (17)
C12—C2—C3—C4	125.78 (16)	C16—C17—C18—C19	2.2 (3)
C1—C2—C3—C4	−2.36 (17)	O4—C18—C19—C20	178.42 (18)
C15—C3—C4—N2	155.96 (14)	C17—C18—C19—C20	−1.8 (3)
C2—C3—C4—N2	26.73 (18)	C16—C15—C20—C19	1.6 (3)
N2—C1—C5—O1	52.8 (2)	C3—C15—C20—C19	−178.35 (18)
C11—C1—C5—O1	175.67 (18)	C18—C19—C20—C15	−0.1 (3)
C2—C1—C5—O1	−61.0 (2)	O1—C5—N1—C6	−177.45 (18)
N2—C1—C5—N1	−126.61 (16)	C1—C5—N1—C6	2.0 (2)
C11—C1—C5—N1	−3.74 (18)	O1—C5—N1—C22	0.8 (3)
C2—C1—C5—N1	119.62 (15)	C1—C5—N1—C22	−179.82 (17)
C11—C6—C7—C8	0.0 (3)	C7—C6—N1—C5	−179.8 (2)
N1—C6—C7—C8	−179.1 (2)	C11—C6—N1—C5	0.9 (2)
C6—C7—C8—C9	2.0 (4)	C7—C6—N1—C22	2.0 (3)
C7—C8—C9—C10	−1.5 (4)	C11—C6—N1—C22	−177.27 (18)
C8—C9—C10—C11	−1.1 (3)	C11—C1—N2—C24	−64.5 (2)
C9—C10—C11—C6	3.1 (3)	C5—C1—N2—C24	50.3 (2)
C9—C10—C11—C1	−176.66 (19)	C2—C1—N2—C24	168.64 (14)
C7—C6—C11—C10	−2.6 (3)	C11—C1—N2—C4	168.29 (15)
N1—C6—C11—C10	176.70 (16)	C5—C1—N2—C4	−76.88 (17)
C7—C6—C11—C1	177.21 (18)	C2—C1—N2—C4	41.45 (16)
N1—C6—C11—C1	−3.5 (2)	C3—C4—N2—C1	−43.87 (18)
N2—C1—C11—C10	−54.1 (3)	C3—C4—N2—C24	−171.88 (15)
C5—C1—C11—C10	−175.93 (19)	O3—C13—N3—C14	−170.56 (18)
C2—C1—C11—C10	65.2 (2)	C12—C13—N3—C14	10.2 (2)
N2—C1—C11—C6	126.08 (16)	O3—C13—N3—C23	5.3 (3)
C5—C1—C11—C6	4.28 (18)	C12—C13—N3—C23	−174.00 (18)
C2—C1—C11—C6	−114.63 (16)	O2—C14—N3—C13	−175.89 (17)
C14—C2—C12—C13	22.91 (17)	C2—C14—N3—C13	5.5 (2)
C3—C2—C12—C13	142.96 (15)	O2—C14—N3—C23	8.3 (3)
C1—C2—C12—C13	−93.10 (16)	C2—C14—N3—C23	−170.30 (17)
C2—C12—C13—O3	159.54 (19)	C19—C18—O4—C21	−5.5 (3)
C2—C12—C13—N3	−21.23 (19)	C17—C18—O4—C21	174.65 (18)
C12—C2—C14—O2	163.58 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.93	2.52	3.122 (2)	123
C12—H12A···O1	0.97	2.58	3.222 (2)	124
C20—H20···O1	0.93	2.56	3.400 (2)	150
C12—H12B···O1ⁱ	0.97	2.56	3.264 (2)	129
C16—H16···O4ⁱⁱ	0.93	2.50	3.394 (2)	161
C19—H19···O2ⁱⁱⁱ	0.93	2.54	3.440 (2)	162
C21—H21C···Cg1^iv	0.96	2.93	3.592 (2)	127

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₅N₃O₄
M_r	419.47
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	11.2074 (3), 11.2406 (3), 33.6082 (9)
V (Å³)	4233.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.17 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.978, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17736, 5023, 3269
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.152, 1.07
No. of reflections	5023
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.93	2.52	3.122 (2)	123
C12—H12A···O1	0.97	2.58	3.222 (2)	124
C20—H20···O1	0.93	2.56	3.400 (2)	150
C12—H12B···O1ⁱ	0.97	2.56	3.264 (2)	129
C16—H16···O4ⁱⁱ	0.93	2.50	3.394 (2)	161
C19—H19···O2ⁱⁱⁱ	0.93	2.54	3.440 (2)	162
C21—H21C···Cg1^iv	0.96	2.93	3.592 (2)	127

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

Acknowledgements

SN thanks Dr Babu Vargheese, SAIF, IIT Madras, India, for his help with the data collection. SN also thanks SRM management, India, for their support.

References

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Volume 65| Part 7| July 2009| Pages o1655-o1656

doi:10.1107/S1600536809021114

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

4′-(4-Meth­oxy­phen­yl)-1,1′,1′′-tri­methyl­di­spiro­[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4′-(4-Methoxyphenyl)-1,1′,1′′-trimethyldispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione