4-Hydr­oxy-3-(1′-methyl-2-oxo-4′-phenyl­spiro­[indoline-3,2′-pyrrolidine]-3′-yl­carbon­yl)quinolin-2(1H)-one

Revathi, K.; Sankaran, M.; Ramesh, P.; Mohan, P.S.; Ponnuswamy, M.N.

doi:10.1107/S1600536810010500

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o952

doi:10.1107/S1600536810010500

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4-Hydroxy-3-(1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine]-3′-ylcarbonyl)quinolin-2(1H)-one

K. Revathi,^a ‡ M. Sankaran,^b P. Ramesh,^a P. S. Mohan ^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 Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 15 March 2010; accepted 20 March 2010; online 27 March 2010)

In the title compound, C₂₈H₂₃N₃O₄, the dihedral angle between the quinoline and indole ring systems is 29.30 (5)°. The pyrrolidine ring adopts a twist conformation. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. A weak intramolecular C3—H3⋯O3 interaction is also observed. In the crystal, molecules are linked by two sets of N—H⋯O hydrogen bonds, forming centrosymmetric dimers containing two R₂²(8) ring motifs. The dimers are linked via C—H⋯π interactions.

Related literature

For general background to indole, quinoline and pyrrolidine derivatives, see: Amalraj et al. (2003 ); Cordell (1981 ); Suzuki et al. (1994 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₂₃N₃O₄
M_r = 465.49
Triclinic, $[P \overline 1]$
a = 9.6918 (3) Å
b = 11.0258 (3) Å
c = 12.9663 (4) Å
α = 69.111 (1)°
β = 72.044 (2)°
γ = 66.410 (1)°
V = 1163.93 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.982, T_max = 0.982
21655 measured reflections
5795 independent reflections
4635 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.119
S = 1.03
5795 reflections
329 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2	0.99 (2)	1.56 (2)	2.4840 (14)	155 (2)
N8—H8⋯O3ⁱ	0.89 (2)	1.92 (2)	2.7837 (13)	165 (2)
N18—H18⋯O1ⁱ	0.90 (2)	1.95 (2)	2.8497 (14)	177 (2)
C3—H3⋯O3	0.98	2.21	2.7944 (13)	117
C21—H21⋯Cg6ⁱⁱ	0.93	2.72	3.5360 (18)	147
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+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 (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/S1600536810010500/ci5061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010500/ci5061Isup2.hkl

checkCIF report

Comment top

Substituted pyrrolidine compounds possess antimicrobial and antifungal activities against various pathogens (Amalraj et al., 2003). Several optically active pyrrolidine compounds are used as intermediates in controlled asymmetric synthesis (Suzuki et al., 1994). The spiro- indole-pyrrolidine ring system is a frequently encountered structural motif in many biologically important and pharmacologically relevant alkaloids, e.g. vincrinstine, vinblastine and spirotypostatins (Cordell, 1981). Against this background and to ascertain the detailed information on its molecular conformation, the X-ray structure determination of the title compound has been carried out.

The pyrrolidine ring (N1/C2-C5) in the molecule adopts a twist conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) for this ring are q₂ = 0.426 (1) Å, ϕ = 335.5 (2)° and Δ₂(C3) = 6.8 (2)°. The sum of the bond angles around atom N1 (337.3°) of the pyrrolidine ring indicates sp³ hybridization. The indole and quinoline ring systems are planar and keto atoms O1 and O3 deviate from the attached ring system by 0.011 (1) and -0.122 (1) Å, respectively. The dihedral angle between the indole and quinoline ring systems is 29.30 (5)°. An intramolecular O4—H4···O2 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). A weak intramolecular C3—H3···O3 interaction is also observed.

The molecules at (x, y, z) and (-x, 2-y, -z) are linked by two sets of N8—H8···O3 and N18—H18···O1 hydrogen bonds to form a centrosymmetric dimer containing two R₂²(8) ring motifs (Fig. 2).

Related literature top

For general background to indole, quinoline and pyrrolidine derivatives, see: Amalraj et al. (2003); Cordell (1981); Suzuki et al. (1994). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 3-cinnamoyl-4-hydroxyquinolin-2(1H)-one (0.5 mmol), isatin (0.5 mmol) and sarcosine (0.55 mmol) was refluxed in methanol until the disappearance of the starting materials as evidenced by the TLC. After completion of the reaction, the solvent was removed in vacuo and the residue was chromatographed on silica gel using hexane-ethyl acetate mixture (7:3) as eluent to give the title compound. The compound was recrystallized in DMF-methanol (3:7 v/v).

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 (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 the atomic numbering and displacement ellipsoids drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

4-Hydroxy-3-(1'-methyl-2-oxo-4'-phenylspiro[indoline-3,2'-pyrrolidine]-3- ylcarbonyl)quinolin-2(1H)-one top

Crystal data top

C₂₈H₂₃N₃O₄	Z = 2
M_r = 465.49	F(000) = 488
Triclinic, P1	D_x = 1.328 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6918 (3) Å	Cell parameters from 1865 reflections
b = 11.0258 (3) Å	θ = 1.7–28.4°
c = 12.9663 (4) Å	µ = 0.09 mm⁻¹
α = 69.111 (1)°	T = 293 K
β = 72.044 (2)°	Block, colourless
γ = 66.410 (1)°	0.20 × 0.20 × 0.20 mm
V = 1163.93 (6) Å³

Data collection top

Bruker SMART APEXII area-detector diffractometer	5795 independent reflections
Radiation source: fine-focus sealed tube	4635 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
T_min = 0.982, T_max = 0.982	k = −14→14
21655 measured reflections	l = −17→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0596P)² + 0.2023P] where P = (F_o² + 2F_c²)/3
5795 reflections	(Δ/σ)_max = 0.008
329 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₈H₂₃N₃O₄	γ = 66.410 (1)°
M_r = 465.49	V = 1163.93 (6) Å³
Triclinic, P1	Z = 2
a = 9.6918 (3) Å	Mo Kα radiation
b = 11.0258 (3) Å	µ = 0.09 mm⁻¹
c = 12.9663 (4) Å	T = 293 K
α = 69.111 (1)°	0.20 × 0.20 × 0.20 mm
β = 72.044 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	5795 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4635 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.982	R_int = 0.023
21655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.22 e Å⁻³
5795 reflections	Δρ_min = −0.19 e Å⁻³
329 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	−0.12393 (11)	0.84110 (9)	0.20477 (8)	0.0513 (2)
O2	0.31591 (12)	0.88012 (10)	0.35337 (8)	0.0540 (2)
O3	0.17428 (11)	0.93755 (10)	0.06203 (7)	0.0489 (2)
O4	0.43677 (12)	1.06028 (12)	0.24273 (9)	0.0577 (3)
N1	−0.11028 (12)	0.89412 (11)	0.41897 (8)	0.0438 (2)
C2	−0.03598 (13)	0.94481 (12)	0.30309 (9)	0.0377 (2)
C3	0.13212 (13)	0.83758 (11)	0.29618 (9)	0.0362 (2)
H3	0.1534	0.7989	0.2334	0.043*
C4	0.12577 (14)	0.72173 (12)	0.40670 (9)	0.0398 (3)
H4	0.1635	0.7380	0.4609	0.048*
C5	−0.04598 (15)	0.74471 (13)	0.44758 (10)	0.0451 (3)
H5A	−0.0828	0.7067	0.4086	0.054*
H5B	−0.0702	0.7047	0.5280	0.054*
C6	−0.27726 (17)	0.95032 (17)	0.44161 (13)	0.0608 (4)
H6A	−0.3175	0.9223	0.3981	0.091*
H6B	−0.3085	1.0488	0.4214	0.091*
H6C	−0.3159	0.9170	0.5202	0.091*
C7	−0.10803 (14)	0.94192 (12)	0.21255 (9)	0.0405 (3)
N8	−0.15228 (13)	1.07050 (11)	0.14433 (9)	0.0465 (3)
C9	−0.11390 (14)	1.16162 (12)	0.17404 (10)	0.0437 (3)
C10	−0.13151 (19)	1.29824 (14)	0.12047 (13)	0.0604 (4)
H10	−0.1705	1.3416	0.0546	0.072*
C11	−0.0888 (2)	1.36838 (15)	0.16859 (15)	0.0669 (4)
H11	−0.0970	1.4600	0.1332	0.080*
C12	−0.03449 (19)	1.30537 (14)	0.26777 (14)	0.0594 (4)
H12	−0.0103	1.3559	0.2997	0.071*
C13	−0.01539 (15)	1.16707 (13)	0.32065 (11)	0.0480 (3)
H13	0.0216	1.1243	0.3874	0.058*
C14	−0.05276 (14)	1.09499 (12)	0.27148 (9)	0.0395 (2)
C15	0.25320 (13)	0.90191 (11)	0.27531 (9)	0.0378 (2)
C16	0.29296 (13)	0.99495 (11)	0.16590 (9)	0.0363 (2)
C17	0.24039 (13)	1.01026 (11)	0.06679 (9)	0.0377 (2)
N18	0.26902 (12)	1.11132 (10)	−0.02685 (8)	0.0419 (2)
C19	0.34942 (13)	1.19400 (12)	−0.03571 (10)	0.0408 (3)
C20	0.37500 (16)	1.29242 (13)	−0.13735 (12)	0.0515 (3)
H20	0.3361	1.3035	−0.1986	0.062*
C21	0.45814 (18)	1.37192 (15)	−0.14509 (13)	0.0597 (4)
H21	0.4756	1.4372	−0.2122	0.072*
C22	0.51668 (19)	1.35655 (16)	−0.05436 (14)	0.0624 (4)
H22	0.5725	1.4117	−0.0613	0.075*
C23	0.49284 (16)	1.26065 (15)	0.04533 (13)	0.0533 (3)
H23	0.5326	1.2506	0.1058	0.064*
C24	0.40805 (13)	1.17747 (12)	0.05590 (10)	0.0412 (3)
C25	0.37906 (13)	1.07426 (12)	0.15761 (10)	0.0403 (3)
C26	0.22252 (15)	0.58092 (12)	0.38987 (10)	0.0435 (3)
C27	0.33649 (18)	0.49550 (14)	0.45126 (13)	0.0590 (4)
H27	0.3503	0.5229	0.5064	0.071*
C28	0.4310 (2)	0.36850 (16)	0.43128 (17)	0.0739 (5)
H28	0.5078	0.3124	0.4726	0.089*
C29	0.4112 (2)	0.32639 (15)	0.35130 (16)	0.0695 (4)
H29	0.4755	0.2426	0.3373	0.083*
C30	0.29633 (18)	0.40778 (15)	0.29184 (14)	0.0594 (4)
H30	0.2814	0.3783	0.2385	0.071*
C31	0.20241 (16)	0.53399 (13)	0.31095 (11)	0.0492 (3)
H31	0.1245	0.5883	0.2703	0.059*
H4A	0.405 (3)	0.985 (2)	0.301 (2)	0.106 (7)*
H8	−0.1719 (19)	1.0831 (17)	0.0782 (15)	0.065 (5)*
H18	0.2265 (18)	1.1249 (15)	−0.0844 (14)	0.054 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0677 (6)	0.0516 (5)	0.0457 (5)	−0.0282 (4)	−0.0212 (4)	−0.0070 (4)
O2	0.0656 (6)	0.0651 (6)	0.0408 (5)	−0.0325 (5)	−0.0224 (4)	−0.0019 (4)
O3	0.0688 (6)	0.0569 (5)	0.0340 (4)	−0.0363 (5)	−0.0133 (4)	−0.0061 (4)
O4	0.0679 (6)	0.0729 (7)	0.0496 (5)	−0.0398 (5)	−0.0200 (5)	−0.0094 (5)
N1	0.0470 (6)	0.0469 (6)	0.0327 (5)	−0.0145 (4)	−0.0058 (4)	−0.0078 (4)
C2	0.0430 (6)	0.0406 (6)	0.0306 (5)	−0.0140 (5)	−0.0105 (4)	−0.0075 (4)
C3	0.0437 (6)	0.0344 (5)	0.0303 (5)	−0.0128 (4)	−0.0101 (4)	−0.0060 (4)
C4	0.0495 (6)	0.0391 (6)	0.0311 (5)	−0.0170 (5)	−0.0125 (4)	−0.0029 (4)
C5	0.0527 (7)	0.0478 (6)	0.0328 (5)	−0.0211 (5)	−0.0077 (5)	−0.0036 (5)
C6	0.0495 (8)	0.0672 (9)	0.0528 (8)	−0.0153 (7)	−0.0008 (6)	−0.0134 (7)
C7	0.0427 (6)	0.0456 (6)	0.0346 (5)	−0.0155 (5)	−0.0099 (4)	−0.0088 (5)
N8	0.0553 (6)	0.0470 (6)	0.0392 (5)	−0.0141 (5)	−0.0214 (5)	−0.0065 (4)
C9	0.0465 (6)	0.0416 (6)	0.0411 (6)	−0.0093 (5)	−0.0138 (5)	−0.0102 (5)
C10	0.0755 (10)	0.0439 (7)	0.0574 (8)	−0.0109 (7)	−0.0311 (7)	−0.0028 (6)
C11	0.0842 (11)	0.0372 (7)	0.0783 (11)	−0.0144 (7)	−0.0298 (9)	−0.0087 (7)
C12	0.0701 (9)	0.0455 (7)	0.0703 (9)	−0.0146 (6)	−0.0219 (7)	−0.0222 (7)
C13	0.0535 (7)	0.0459 (7)	0.0469 (7)	−0.0106 (5)	−0.0150 (5)	−0.0169 (5)
C14	0.0420 (6)	0.0387 (6)	0.0355 (5)	−0.0098 (4)	−0.0089 (4)	−0.0100 (4)
C15	0.0423 (6)	0.0371 (5)	0.0345 (5)	−0.0112 (4)	−0.0100 (4)	−0.0097 (4)
C16	0.0380 (6)	0.0364 (5)	0.0350 (5)	−0.0115 (4)	−0.0076 (4)	−0.0102 (4)
C17	0.0409 (6)	0.0386 (6)	0.0331 (5)	−0.0138 (4)	−0.0059 (4)	−0.0093 (4)
N18	0.0495 (6)	0.0438 (5)	0.0344 (5)	−0.0199 (4)	−0.0101 (4)	−0.0058 (4)
C19	0.0386 (6)	0.0362 (5)	0.0431 (6)	−0.0114 (4)	−0.0028 (5)	−0.0110 (5)
C20	0.0535 (8)	0.0456 (7)	0.0473 (7)	−0.0178 (6)	−0.0058 (6)	−0.0046 (5)
C21	0.0603 (8)	0.0479 (7)	0.0601 (8)	−0.0249 (6)	0.0001 (7)	−0.0038 (6)
C22	0.0618 (9)	0.0573 (8)	0.0727 (10)	−0.0348 (7)	−0.0006 (7)	−0.0157 (7)
C23	0.0503 (7)	0.0564 (8)	0.0598 (8)	−0.0265 (6)	−0.0044 (6)	−0.0179 (6)
C24	0.0374 (6)	0.0399 (6)	0.0462 (6)	−0.0137 (5)	−0.0034 (5)	−0.0142 (5)
C25	0.0389 (6)	0.0436 (6)	0.0408 (6)	−0.0134 (5)	−0.0077 (5)	−0.0142 (5)
C26	0.0488 (7)	0.0377 (6)	0.0413 (6)	−0.0192 (5)	−0.0094 (5)	−0.0012 (5)
C27	0.0668 (9)	0.0463 (7)	0.0622 (9)	−0.0177 (6)	−0.0276 (7)	−0.0006 (6)
C28	0.0695 (10)	0.0471 (8)	0.0905 (12)	−0.0093 (7)	−0.0319 (9)	0.0010 (8)
C29	0.0670 (10)	0.0402 (7)	0.0916 (12)	−0.0172 (7)	−0.0074 (9)	−0.0137 (7)
C30	0.0652 (9)	0.0512 (8)	0.0671 (9)	−0.0294 (7)	−0.0005 (7)	−0.0204 (7)
C31	0.0530 (7)	0.0451 (7)	0.0511 (7)	−0.0209 (6)	−0.0090 (6)	−0.0102 (5)

Geometric parameters (Å, º) top

O1—C7	1.2232 (15)	C12—H12	0.93
O2—C15	1.2412 (14)	C13—C14	1.3797 (17)
O3—C17	1.2360 (14)	C13—H13	0.93
O4—C25	1.3210 (15)	C15—C16	1.4679 (15)
O4—H4A	0.99 (2)	C16—C25	1.3908 (16)
N1—C6	1.4572 (18)	C16—C17	1.4559 (15)
N1—C5	1.4577 (16)	C17—N18	1.3666 (15)
N1—C2	1.4645 (15)	N18—C19	1.3748 (16)
C2—C14	1.5092 (16)	N18—H18	0.900 (16)
C2—C7	1.5546 (16)	C19—C24	1.3950 (17)
C2—C3	1.5824 (16)	C19—C20	1.4035 (17)
C3—C15	1.5123 (16)	C20—C21	1.371 (2)
C3—C4	1.5466 (15)	C20—H20	0.93
C3—H3	0.98	C21—C22	1.388 (2)
C4—C26	1.5124 (17)	C21—H21	0.93
C4—C5	1.5265 (18)	C22—C23	1.371 (2)
C4—H4	0.98	C22—H22	0.93
C5—H5A	0.97	C23—C24	1.4068 (18)
C5—H5B	0.97	C23—H23	0.93
C6—H6A	0.96	C24—C25	1.4389 (17)
C6—H6B	0.96	C26—C27	1.3840 (18)
C6—H6C	0.96	C26—C31	1.3907 (18)
C7—N8	1.3526 (16)	C27—C28	1.397 (2)
N8—C9	1.3999 (17)	C27—H27	0.93
N8—H8	0.886 (18)	C28—C29	1.366 (3)
C9—C10	1.3791 (18)	C28—H28	0.93
C9—C14	1.3922 (16)	C29—C30	1.369 (2)
C10—C11	1.385 (2)	C29—H29	0.93
C10—H10	0.93	C30—C31	1.385 (2)
C11—C12	1.379 (2)	C30—H30	0.93
C11—H11	0.93	C31—H31	0.93
C12—C13	1.3915 (19)

C25—O4—H4A	102.8 (13)	C14—C13—H13	120.9
C6—N1—C5	115.61 (11)	C12—C13—H13	120.9
C6—N1—C2	115.01 (10)	C13—C14—C9	120.22 (11)
C5—N1—C2	106.72 (9)	C13—C14—C2	131.02 (10)
N1—C2—C14	113.47 (9)	C9—C14—C2	108.75 (10)
N1—C2—C7	113.94 (10)	O2—C15—C16	119.22 (11)
C14—C2—C7	101.31 (9)	O2—C15—C3	119.46 (10)
N1—C2—C3	102.76 (8)	C16—C15—C3	121.25 (9)
C14—C2—C3	117.72 (10)	C25—C16—C17	119.02 (10)
C7—C2—C3	107.99 (9)	C25—C16—C15	118.98 (10)
C15—C3—C4	114.61 (9)	C17—C16—C15	121.97 (10)
C15—C3—C2	112.81 (9)	O3—C17—N18	118.80 (10)
C4—C3—C2	105.06 (9)	O3—C17—C16	124.44 (10)
C15—C3—H3	108.0	N18—C17—C16	116.76 (10)
C4—C3—H3	108.0	N18—C19—C24	119.67 (11)
C2—C3—H3	108.0	N18—C19—C20	119.99 (12)
C26—C4—C5	115.35 (10)	C24—C19—C20	120.32 (12)
C26—C4—C3	112.53 (9)	C21—C20—C19	119.04 (14)
C5—C4—C3	102.87 (9)	C21—C20—H20	120.5
C26—C4—H4	108.6	C19—C20—H20	120.5
C5—C4—H4	108.6	C20—C21—C22	121.10 (13)
C3—C4—H4	108.6	C20—C21—H21	119.4
N1—C5—C4	102.03 (10)	C22—C21—H21	119.4
N1—C5—H5A	111.4	C23—C22—C21	120.47 (14)
C4—C5—H5A	111.4	C23—C22—H22	119.8
N1—C5—H5B	111.4	C21—C22—H22	119.8
C4—C5—H5B	111.4	C22—C23—C24	119.78 (14)
H5A—C5—H5B	109.2	C22—C23—H23	120.1
N1—C6—H6A	109.5	C24—C23—H23	120.1
N1—C6—H6B	109.5	C19—C24—C23	119.28 (12)
H6A—C6—H6B	109.5	C19—C24—C25	117.81 (11)
N1—C6—H6C	109.5	C23—C24—C25	122.91 (12)
H6A—C6—H6C	109.5	O4—C25—C16	121.98 (11)
H6B—C6—H6C	109.5	O4—C25—C24	116.49 (11)
O1—C7—N8	125.56 (11)	C16—C25—C24	121.52 (11)
O1—C7—C2	126.01 (10)	C27—C26—C31	117.78 (13)
N8—C7—C2	108.42 (10)	C27—C26—C4	120.84 (12)
C7—N8—C9	111.31 (10)	C31—C26—C4	121.36 (11)
C7—N8—H8	119.7 (11)	C26—C27—C28	120.68 (15)
C9—N8—H8	125.8 (11)	C26—C27—H27	119.7
C10—C9—C14	121.77 (12)	C28—C27—H27	119.7
C10—C9—N8	128.28 (12)	C29—C28—C27	120.29 (15)
C14—C9—N8	109.94 (10)	C29—C28—H28	119.9
C9—C10—C11	117.42 (13)	C27—C28—H28	119.9
C9—C10—H10	121.3	C28—C29—C30	119.90 (15)
C11—C10—H10	121.3	C28—C29—H29	120.0
C12—C11—C10	121.45 (14)	C30—C29—H29	120.0
C12—C11—H11	119.3	C29—C30—C31	120.13 (15)
C10—C11—H11	119.3	C29—C30—H30	119.9
C11—C12—C13	120.76 (13)	C31—C30—H30	119.9
C11—C12—H12	119.6	C30—C31—C26	121.18 (13)
C13—C12—H12	119.6	C30—C31—H31	119.4
C14—C13—C12	118.27 (12)	C26—C31—H31	119.4

C6—N1—C2—C14	67.51 (14)	C4—C3—C15—O2	−14.08 (15)
C5—N1—C2—C14	−162.83 (10)	C2—C3—C15—O2	106.11 (12)
C6—N1—C2—C7	−47.74 (15)	C4—C3—C15—C16	168.83 (10)
C5—N1—C2—C7	81.91 (12)	C2—C3—C15—C16	−70.98 (13)
C6—N1—C2—C3	−164.29 (11)	O2—C15—C16—C25	−10.92 (17)
C5—N1—C2—C3	−34.63 (11)	C3—C15—C16—C25	166.18 (10)
N1—C2—C3—C15	−116.48 (10)	O2—C15—C16—C17	171.31 (11)
C14—C2—C3—C15	9.00 (13)	C3—C15—C16—C17	−11.59 (16)
C7—C2—C3—C15	122.80 (10)	C25—C16—C17—O3	173.82 (11)
N1—C2—C3—C4	9.05 (11)	C15—C16—C17—O3	−8.41 (18)
C14—C2—C3—C4	134.53 (10)	C25—C16—C17—N18	−5.28 (16)
C7—C2—C3—C4	−111.68 (10)	C15—C16—C17—N18	172.49 (10)
C15—C3—C4—C26	−93.05 (12)	O3—C17—N18—C19	−175.84 (11)
C2—C3—C4—C26	142.55 (10)	C16—C17—N18—C19	3.31 (17)
C15—C3—C4—C5	142.18 (10)	C17—N18—C19—C24	−0.20 (18)
C2—C3—C4—C5	17.79 (11)	C17—N18—C19—C20	178.42 (11)
C6—N1—C5—C4	176.30 (10)	N18—C19—C20—C21	−178.69 (12)
C2—N1—C5—C4	46.99 (11)	C24—C19—C20—C21	−0.08 (19)
C26—C4—C5—N1	−161.42 (9)	C19—C20—C21—C22	−0.1 (2)
C3—C4—C5—N1	−38.53 (11)	C20—C21—C22—C23	0.2 (2)
N1—C2—C7—O1	−56.11 (16)	C21—C22—C23—C24	−0.2 (2)
C14—C2—C7—O1	−178.34 (12)	N18—C19—C24—C23	178.72 (11)
C3—C2—C7—O1	57.35 (15)	C20—C19—C24—C23	0.10 (18)
N1—C2—C7—N8	123.09 (11)	N18—C19—C24—C25	−0.94 (16)
C14—C2—C7—N8	0.87 (12)	C20—C19—C24—C25	−179.56 (11)
C3—C2—C7—N8	−123.44 (11)	C22—C23—C24—C19	0.0 (2)
O1—C7—N8—C9	−178.42 (12)	C22—C23—C24—C25	179.67 (13)
C2—C7—N8—C9	2.37 (14)	C17—C16—C25—O4	−176.49 (11)
C7—N8—C9—C10	175.61 (14)	C15—C16—C25—O4	5.67 (17)
C7—N8—C9—C14	−5.01 (15)	C17—C16—C25—C24	4.40 (17)
C14—C9—C10—C11	−1.3 (2)	C15—C16—C25—C24	−173.44 (10)
N8—C9—C10—C11	178.02 (15)	C19—C24—C25—O4	179.58 (11)
C9—C10—C11—C12	−1.6 (3)	C23—C24—C25—O4	−0.07 (18)
C10—C11—C12—C13	2.4 (3)	C19—C24—C25—C16	−1.26 (17)
C11—C12—C13—C14	−0.2 (2)	C23—C24—C25—C16	179.10 (12)
C12—C13—C14—C9	−2.6 (2)	C5—C4—C26—C27	−118.66 (13)
C12—C13—C14—C2	175.60 (13)	C3—C4—C26—C27	123.74 (13)
C10—C9—C14—C13	3.5 (2)	C5—C4—C26—C31	62.68 (15)
N8—C9—C14—C13	−175.95 (11)	C3—C4—C26—C31	−54.92 (15)
C10—C9—C14—C2	−175.11 (13)	C31—C26—C27—C28	2.1 (2)
N8—C9—C14—C2	5.46 (14)	C4—C26—C27—C28	−176.58 (14)
N1—C2—C14—C13	55.29 (17)	C26—C27—C28—C29	−0.6 (3)
C7—C2—C14—C13	177.84 (13)	C27—C28—C29—C30	−1.2 (3)
C3—C2—C14—C13	−64.72 (17)	C28—C29—C30—C31	1.4 (2)
N1—C2—C14—C9	−126.32 (11)	C29—C30—C31—C26	0.2 (2)
C7—C2—C14—C9	−3.78 (12)	C27—C26—C31—C30	−2.0 (2)
C3—C2—C14—C9	113.66 (11)	C4—C26—C31—C30	176.74 (12)

Hydrogen-bond geometry (Å, º) top

Cg6 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2	0.99 (2)	1.56 (2)	2.4840 (14)	155 (2)
N8—H8···O3ⁱ	0.89 (2)	1.92 (2)	2.7837 (13)	165 (2)
N18—H18···O1ⁱ	0.90 (2)	1.95 (2)	2.8497 (14)	177 (2)
C3—H3···O3	0.98	2.21	2.7944 (13)	117
C21—H21···Cg6ⁱⁱ	0.93	2.72	3.5360 (18)	147

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₃N₃O₄
M_r	465.49
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6918 (3), 11.0258 (3), 12.9663 (4)
α, β, γ (°)	69.111 (1), 72.044 (2), 66.410 (1)
V (Å³)	1163.93 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.982, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	21655, 5795, 4635
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.119, 1.03
No. of reflections	5795
No. of parameters	329
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

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

Hydrogen-bond geometry (Å, º) top

Cg6 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2	0.99 (2)	1.56 (2)	2.4840 (14)	155 (2)
N8—H8···O3ⁱ	0.89 (2)	1.92 (2)	2.7837 (13)	165 (2)
N18—H18···O1ⁱ	0.90 (2)	1.95 (2)	2.8497 (14)	177 (2)
C3—H3···O3	0.98	2.21	2.7944 (13)	117
C21—H21···Cg6ⁱⁱ	0.93	2.72	3.5360 (18)	147

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

Footnotes

‡Parent department: Department of Chemistry, Thiagarajar College (Autonomous), Madurai 625 009, India.

References

Amalraj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419. Web of Science PubMed 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 (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cordell, G. (1981). Introduction to Alkaloids: A Biogenic Approach. New York: Wiley International. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals 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
Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119–6122. CrossRef CAS Web of Science Google Scholar

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Volume 66| Part 4| April 2010| Page o952

doi:10.1107/S1600536810010500

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

4-Hydr­­oxy-3-(1′-methyl-2-oxo-4′-phenyl­spiro­[indoline-3,2′-pyrrolidine]-3′-yl­carbon­yl)quinolin-2(1H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

References

organic compounds

4-Hydroxy-3-(1′-methyl-2-oxo-4′-phenylspiro[indoline-3,2′-pyrrolidine]-3′-ylcarbonyl)quinolin-2(1H)-one