Diethyl 1-acetyl-4′-(4-chloro­phen­yl)-5′-(4-nitro­phen­yl)-2-oxospiro­[indoline-3,3′-pyrrolidine]-2′,2′-dicarboxyl­ate

He, L.

doi:10.1107/S160053680903551X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2388

doi:10.1107/S160053680903551X

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Diethyl 1-acetyl-4′-(4-chlorophenyl)-5′-(4-nitrophenyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-2′,2′-dicarboxylate

Long He ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: helongcwnu@yahoo.com.cn

(Received 24 August 2009; accepted 2 September 2009; online 9 September 2009)

In the title compound, C₃₁H₂₈ClN₃O₈, the pyrrolidine ring exhibits an envelope conformation, with the spiro C atom located at the flap position. A spiro junction links the oxindole ring system and the pyrrolidine ring. The planar oxindole ring system is twisted with respect to the nitrobenzene and chlorobenzene rings, with dihedral angles of 62.34 (11) and 75.93 (9)°, respectively. In the crystal, a weak C—H⋯O interaction links the molecules into chains and two intramolecular C—H⋯O close contacts are seen.

Related literature

For general background to the spirooxindole–pyrrolidine ring system, see: Garnick & Lequesne (1978 ); Jossang et al. (1991 ). For the biological activity of pyrrolidine-containing compounds and their use in catalysis, see: Grigg (1995 ); Kravchenko et al. (2005 ); Witherup et al. (1995 ). For the biological activity of oxindole derivatives, see: Glover et al. (1998 ); Bhattacharya et al. (1982 ).

Experimental

Crystal data

C₃₁H₂₈ClN₃O₈
M_r = 606.01
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.780 (2) Å
b = 14.859 (3) Å
c = 20.466 (5) Å
V = 2974.1 (11) Å³
Z = 4
Cu Kα radiation
μ = 1.61 mm⁻¹
T = 293 K
0.40 × 0.38 × 0.32 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.565, T_max = 0.626
27366 measured reflections
4732 independent reflections
4456 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.066
S = 1.00
4732 reflections
403 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ), with 2017 Friedel pairs
Flack parameter: 0.020 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O8ⁱ	0.96	2.51	3.387 (4)	152
C11—H11⋯O3	0.98	2.54	3.200 (3)	125
C21—H21⋯O3	0.93	2.44	3.181 (3)	136
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro ; 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903551X/xu2602sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903551X/xu2602Isup2.hkl

checkCIF report

Comment top

The spirooxindole-pyrrolidine unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties such as alstonia muelleriana and horsfiline (Garnick & Lequesne, 1978; Jossang et al., 1991). Pyrrolidine-containing compounds are of significant importance because of their biological activities and widespread employment in catalysis (Grigg et al., 1995; Witherup et al., 1995; Kravchenko et al., 2005). Oxindole derivatives are of importance in the total synthesis of indole and oxindole alkaloids such as potent inhibitors of monoamine oxidase (MAO) in human urine and rat tissues (Glover et al., 1998) and atrial natriuretic peptide-stimulated guanylate cyclase and a potent antagonist of in vitro receptor binding by atrial natriuretic peptide besides possessing a wide range of central nervous system activities (Bhattacharya et al., 1982). We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. In the molecule, the pyrrolidine ring exhibits an envelope conformation. The oxyindole ring forms dihedral angles of 62.34 (11)°, 75.93 (9)° with nitrophenyl and chlorophenyl rings, respectively. The crystal packing is stabilized by C—H···O hydrogen bonding (Table 1).

Related literature top

For general background to the spirooxindole–pyrrolidine ring system, see: Garnick & Lequesne (1978); Jossang et al. (1991). For the biological activity of pyrrolidine-containing compounds and their use in catalysis, see: Grigg et al. (1995); Kravchenko et al. (2005); Witherup et al. (1995). For the biological activity of oxindole derivatives, see: Glover et al. (1998); Bhattacharya et al. (1982).

Experimental top

1-acetyl-3-(4-chlorobenzylidene)indolin-2-one (0.09 g, 0.3 mmol), diethyl 2-aminomalonate (0.035 g, 0.2 mmol) and 4-nitrobenzaldehyde (0.036 g, 0.24 mmol) were dissolved in dichloromethane (2 ml). To the stirred mixture, acetic acid (0.006 g, 0.1 mmol) was added. After the mixture had been stirred at 273 K for 24 h, the reaction was quenched with a saturated solution of sodium bicarbonate (5 ml). The mixture was extracted with diethyl ether, removal of solvent under reduced pressure, the residue was purified through column chromatography on silica gel to give target compound. Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). The minor disordered component is omitted for clarity.

Diethyl 1-acetyl-4'-(4-chlorophenyl)-5'-(4-nitrophenyl)- 2-oxospiro[indoline-3,3'-pyrrolidine]-2',2'-dicarboxylate top

Crystal data top

C₃₁H₂₈ClN₃O₈	F(000) = 1264
M_r = 606.01	D_x = 1.353 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 19085 reflections
a = 9.780 (2) Å	θ = 2.2–62.6°
b = 14.859 (3) Å	µ = 1.61 mm⁻¹
c = 20.466 (5) Å	T = 293 K
V = 2974.1 (11) Å³	Block, colourless
Z = 4	0.40 × 0.38 × 0.32 mm

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	4732 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	4456 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.034
ω scans	θ_max = 62.7°, θ_min = 3.7°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −11→10
T_min = 0.565, T_max = 0.626	k = −16→16
27366 measured reflections	l = −23→23

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.01P)² + 1.12P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4732 reflections	Δρ_max = 0.12 e Å⁻³
403 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 2017 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.020 (15)

Crystal data top

C₃₁H₂₈ClN₃O₈	V = 2974.1 (11) Å³
M_r = 606.01	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 9.780 (2) Å	µ = 1.61 mm⁻¹
b = 14.859 (3) Å	T = 293 K
c = 20.466 (5) Å	0.40 × 0.38 × 0.32 mm

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	4732 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	4456 reflections with I > 2σ(I)
T_min = 0.565, T_max = 0.626	R_int = 0.034
27366 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	Δρ_max = 0.12 e Å⁻³
S = 1.00	Δρ_min = −0.15 e Å⁻³
4732 reflections	Absolute structure: Flack (1983), with 2017 Friedel pairs
403 parameters	Absolute structure parameter: 0.020 (15)
0 restraints

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	Occ. (<1)
Cl1	1.09946 (7)	0.04005 (5)	−0.15933 (4)	0.0854 (2)
O1	0.64684 (17)	−0.06223 (10)	0.10179 (8)	0.0676 (4)
O2	0.6735 (2)	0.19830 (13)	0.17061 (9)	0.0952 (6)
O3	0.4061 (2)	−0.20875 (10)	0.04919 (9)	0.0884 (6)
O4	0.36139 (19)	−0.12113 (11)	0.13466 (8)	0.0711 (5)
O5	0.13360 (19)	0.01337 (13)	0.03482 (10)	0.0905 (6)
O6	0.28979 (16)	0.05350 (10)	0.10874 (8)	0.0645 (4)
O7	0.5892 (3)	−0.37919 (15)	−0.29155 (11)	0.1140 (8)
O8	0.4917 (3)	−0.45986 (14)	−0.22027 (12)	0.1298 (10)
N1	0.5298 (3)	−0.38745 (15)	−0.24018 (12)	0.0773 (6)
N2	0.3198 (2)	−0.07998 (13)	−0.03716 (9)	0.0550 (5)
H4	0.252 (2)	−0.0467 (15)	−0.0536 (11)	0.057 (7)*
N3	0.60487 (19)	0.09166 (11)	0.09909 (8)	0.0524 (4)
C1	0.4012 (3)	0.23572 (15)	−0.04607 (12)	0.0635 (6)
H1	0.3536	0.2652	−0.0791	0.076*
C2	0.4675 (3)	0.28445 (15)	0.00113 (13)	0.0653 (6)
H2	0.4643	0.3470	−0.0006	0.078*
C3	0.5388 (3)	0.24359 (14)	0.05103 (12)	0.0618 (6)
H3	0.5826	0.2774	0.0831	0.074*
C4	0.5428 (2)	0.15029 (13)	0.05182 (10)	0.0500 (5)
C5	0.4780 (2)	0.09924 (13)	0.00393 (10)	0.0465 (5)
C6	0.4053 (2)	0.14167 (14)	−0.04455 (11)	0.0554 (5)
H6	0.3593	0.1082	−0.0760	0.067*
C7	0.4978 (2)	−0.00011 (13)	0.01833 (10)	0.0463 (5)
C8	0.5901 (2)	0.00172 (14)	0.07806 (10)	0.0517 (5)
C9	0.6535 (3)	0.11918 (18)	0.16049 (12)	0.0661 (6)
C10	0.6741 (4)	0.0499 (2)	0.21150 (12)	0.0956 (9)
H10A	0.5943	0.0125	0.2142	0.143*
H10B	0.6893	0.0787	0.2529	0.143*
H10C	0.7520	0.0137	0.2005	0.143*
C11	0.5600 (2)	−0.05979 (13)	−0.03652 (10)	0.0475 (5)
H11	0.5788	−0.1183	−0.0163	0.057*
C12	0.4372 (2)	−0.07482 (13)	−0.08216 (10)	0.0505 (5)
H12	0.4265	−0.0221	−0.1105	0.061*
C13	0.3575 (2)	−0.05148 (13)	0.02874 (10)	0.0501 (5)
C14	0.3776 (2)	−0.13656 (15)	0.07181 (12)	0.0601 (6)
C15	0.3784 (3)	−0.19894 (19)	0.17846 (14)	0.0859 (8)
H15A	0.3345	−0.2511	0.1591	0.103*
H15B	0.3334	−0.1864	0.2197	0.103*
C16	0.5243 (4)	−0.2199 (2)	0.19082 (17)	0.1080 (11)
H16A	0.5308	−0.2698	0.2205	0.162*
H16B	0.5684	−0.1683	0.2097	0.162*
H16C	0.5683	−0.2351	0.1504	0.162*
C17	0.2462 (3)	0.00796 (15)	0.05735 (12)	0.0580 (6)
C18	0.1908 (18)	0.1190 (11)	0.1331 (5)	0.078 (3)	0.663 (5)
H18A	0.1077	0.0897	0.1479	0.093*	0.663 (5)
H18B	0.1679	0.1630	0.0998	0.093*	0.663 (5)
C19	0.2687 (5)	0.1632 (4)	0.1910 (3)	0.1042 (18)	0.663 (5)
H19A	0.2114	0.2078	0.2112	0.156*	0.663 (5)
H19B	0.3506	0.1912	0.1751	0.156*	0.663 (5)
H19C	0.2920	0.1180	0.2226	0.156*	0.663 (5)
C18B	0.201 (4)	0.109 (2)	0.1530 (12)	0.078 (3)	0.337 (5)
H18C	0.1051	0.0958	0.1446	0.093*	0.337 (5)
H18D	0.2201	0.0945	0.1983	0.093*	0.337 (5)
C19B	0.2277 (11)	0.2020 (8)	0.1410 (6)	0.1042 (18)	0.337 (5)
H19D	0.1689	0.2383	0.1677	0.156*	0.337 (5)
H19E	0.2111	0.2152	0.0957	0.156*	0.337 (5)
H19F	0.3214	0.2150	0.1513	0.156*	0.337 (5)
C20	0.4548 (2)	−0.15803 (14)	−0.12431 (10)	0.0520 (5)
C21	0.4107 (3)	−0.24182 (15)	−0.10433 (13)	0.0880 (10)
H21	0.3640	−0.2477	−0.0650	0.106*
C22	0.4351 (4)	−0.31696 (17)	−0.14218 (13)	0.0920 (10)
H22	0.4056	−0.3734	−0.1285	0.110*
C23	0.5028 (2)	−0.30745 (15)	−0.19981 (11)	0.0591 (6)
C24	0.5454 (3)	−0.22572 (15)	−0.22211 (11)	0.0637 (6)
H24	0.5899	−0.2204	−0.2621	0.076*
C25	0.5206 (3)	−0.15126 (15)	−0.18380 (11)	0.0612 (6)
H25	0.5489	−0.0950	−0.1984	0.073*
C26	0.6926 (2)	−0.02983 (13)	−0.06711 (10)	0.0482 (5)
C27	0.8076 (2)	−0.08192 (15)	−0.05669 (12)	0.0619 (6)
H27	0.8008	−0.1323	−0.0300	0.074*
C28	0.9330 (2)	−0.06145 (17)	−0.08482 (12)	0.0688 (7)
H28	1.0089	−0.0978	−0.0775	0.083*
C29	0.9422 (2)	0.01330 (16)	−0.12345 (11)	0.0611 (6)
C30	0.8322 (2)	0.06705 (15)	−0.13547 (11)	0.0622 (6)
H30	0.8408	0.1175	−0.1621	0.075*
C31	0.7064 (2)	0.04538 (15)	−0.10724 (11)	0.0583 (5)
H31	0.6307	0.0816	−0.1153	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0629 (4)	0.1033 (5)	0.0900 (5)	−0.0142 (4)	0.0124 (3)	0.0004 (4)
O1	0.0756 (11)	0.0570 (9)	0.0701 (10)	0.0076 (8)	−0.0155 (8)	0.0078 (8)
O2	0.1405 (18)	0.0780 (13)	0.0672 (11)	−0.0327 (13)	−0.0184 (12)	−0.0167 (10)
O3	0.1411 (18)	0.0437 (9)	0.0805 (12)	0.0019 (10)	0.0153 (13)	0.0014 (9)
O4	0.0926 (13)	0.0613 (10)	0.0595 (10)	0.0072 (9)	0.0060 (9)	0.0083 (8)
O5	0.0607 (11)	0.0989 (14)	0.1119 (15)	0.0141 (10)	−0.0127 (11)	−0.0356 (12)
O6	0.0650 (9)	0.0594 (9)	0.0692 (10)	0.0006 (8)	0.0083 (8)	−0.0157 (8)
O7	0.154 (2)	0.0987 (15)	0.0888 (15)	−0.0116 (15)	0.0374 (16)	−0.0396 (12)
O8	0.195 (3)	0.0629 (13)	0.1315 (19)	−0.0220 (16)	0.0478 (19)	−0.0379 (13)
N1	0.0878 (16)	0.0643 (14)	0.0798 (16)	−0.0093 (12)	0.0046 (13)	−0.0251 (12)
N2	0.0546 (11)	0.0537 (11)	0.0566 (11)	−0.0051 (9)	−0.0018 (9)	−0.0087 (9)
N3	0.0583 (11)	0.0502 (10)	0.0487 (10)	−0.0053 (8)	−0.0071 (9)	−0.0043 (8)
C1	0.0697 (15)	0.0501 (13)	0.0708 (15)	0.0102 (12)	0.0029 (13)	0.0104 (11)
C2	0.0719 (16)	0.0399 (12)	0.0840 (17)	−0.0005 (11)	0.0056 (14)	0.0018 (12)
C3	0.0664 (14)	0.0449 (12)	0.0739 (15)	−0.0098 (11)	0.0039 (13)	−0.0123 (11)
C4	0.0516 (11)	0.0450 (11)	0.0533 (12)	−0.0037 (9)	0.0016 (10)	−0.0026 (10)
C5	0.0514 (12)	0.0369 (10)	0.0510 (12)	0.0004 (9)	0.0002 (9)	−0.0026 (9)
C6	0.0590 (13)	0.0463 (12)	0.0610 (13)	0.0031 (10)	−0.0055 (11)	−0.0019 (10)
C7	0.0525 (12)	0.0377 (10)	0.0487 (11)	0.0001 (9)	−0.0032 (9)	−0.0006 (9)
C8	0.0529 (12)	0.0497 (12)	0.0523 (12)	−0.0009 (10)	0.0001 (10)	0.0019 (10)
C9	0.0693 (15)	0.0755 (17)	0.0534 (13)	−0.0155 (13)	−0.0037 (12)	−0.0043 (13)
C10	0.132 (3)	0.098 (2)	0.0573 (15)	−0.014 (2)	−0.0244 (17)	0.0039 (15)
C11	0.0546 (12)	0.0357 (10)	0.0521 (11)	−0.0015 (9)	−0.0004 (10)	−0.0010 (9)
C12	0.0595 (13)	0.0397 (11)	0.0523 (12)	−0.0044 (9)	0.0005 (10)	−0.0022 (9)
C13	0.0540 (12)	0.0412 (11)	0.0552 (12)	−0.0020 (9)	0.0000 (10)	−0.0038 (9)
C14	0.0651 (14)	0.0495 (13)	0.0658 (15)	−0.0077 (11)	0.0064 (12)	0.0007 (11)
C15	0.105 (2)	0.0771 (18)	0.0751 (17)	0.0016 (17)	0.0107 (17)	0.0251 (15)
C16	0.112 (3)	0.100 (2)	0.112 (3)	0.006 (2)	−0.011 (2)	0.048 (2)
C17	0.0604 (14)	0.0491 (12)	0.0645 (14)	−0.0033 (10)	0.0052 (12)	−0.0050 (11)
C18	0.078 (3)	0.076 (4)	0.080 (7)	0.010 (3)	0.007 (6)	−0.031 (5)
C19	0.092 (3)	0.116 (4)	0.105 (4)	−0.007 (3)	0.015 (3)	−0.060 (3)
C18B	0.078 (3)	0.076 (4)	0.080 (7)	0.010 (3)	0.007 (6)	−0.031 (5)
C19B	0.092 (3)	0.116 (4)	0.105 (4)	−0.007 (3)	0.015 (3)	−0.060 (3)
C20	0.0603 (13)	0.0450 (11)	0.0507 (12)	−0.0084 (10)	−0.0007 (10)	−0.0051 (9)
C21	0.138 (3)	0.0526 (14)	0.0734 (16)	−0.0306 (16)	0.0429 (18)	−0.0163 (13)
C22	0.141 (3)	0.0499 (14)	0.0848 (19)	−0.0320 (16)	0.0378 (19)	−0.0142 (13)
C23	0.0673 (15)	0.0525 (13)	0.0576 (13)	−0.0043 (11)	0.0008 (11)	−0.0163 (11)
C24	0.0789 (16)	0.0616 (14)	0.0506 (12)	−0.0091 (13)	0.0038 (12)	−0.0063 (11)
C25	0.0818 (17)	0.0478 (12)	0.0540 (13)	−0.0077 (12)	0.0038 (12)	0.0027 (10)
C26	0.0533 (11)	0.0392 (11)	0.0522 (12)	−0.0026 (9)	−0.0021 (10)	−0.0053 (9)
C27	0.0607 (14)	0.0519 (13)	0.0731 (15)	0.0013 (11)	0.0011 (12)	0.0100 (11)
C28	0.0524 (14)	0.0690 (16)	0.0849 (18)	0.0069 (12)	0.0008 (12)	0.0059 (14)
C29	0.0580 (14)	0.0645 (14)	0.0608 (13)	−0.0121 (11)	0.0028 (11)	−0.0111 (11)
C30	0.0674 (15)	0.0516 (13)	0.0674 (15)	−0.0039 (11)	0.0043 (12)	0.0038 (11)
C31	0.0620 (13)	0.0495 (12)	0.0635 (13)	0.0034 (11)	0.0037 (11)	0.0053 (11)

Geometric parameters (Å, º) top

Cl1—C29	1.750 (2)	C12—H12	0.9800
O1—C8	1.203 (2)	C13—C17	1.519 (3)
O2—C9	1.210 (3)	C13—C14	1.554 (3)
O3—C14	1.201 (3)	C15—C16	1.482 (4)
O4—C14	1.316 (3)	C15—H15A	0.9700
O4—C15	1.472 (3)	C15—H15B	0.9700
O5—C17	1.197 (3)	C16—H16A	0.9600
O6—C17	1.321 (3)	C16—H16B	0.9600
O6—C18	1.460 (16)	C16—H16C	0.9600
O6—C18B	1.50 (3)	C18—C19	1.555 (15)
O7—N1	1.208 (3)	C18—H18A	0.9700
O8—N1	1.209 (3)	C18—H18B	0.9700
N1—C23	1.471 (3)	C19—H19A	0.9600
N2—C13	1.461 (3)	C19—H19B	0.9600
N2—C12	1.474 (3)	C19—H19C	0.9600
N2—H4	0.90 (2)	C18B—C19B	1.43 (4)
N3—C9	1.404 (3)	C18B—H18C	0.9700
N3—C8	1.411 (3)	C18B—H18D	0.9700
N3—C4	1.437 (3)	C19B—H19D	0.9600
C1—C2	1.370 (3)	C19B—H19E	0.9600
C1—C6	1.398 (3)	C19B—H19F	0.9600
C1—H1	0.9300	C20—C21	1.380 (3)
C2—C3	1.377 (3)	C20—C25	1.381 (3)
C2—H2	0.9300	C21—C22	1.380 (3)
C3—C4	1.387 (3)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.360 (3)
C4—C5	1.392 (3)	C22—H22	0.9300
C5—C6	1.374 (3)	C23—C24	1.363 (3)
C5—C7	1.518 (3)	C24—C25	1.378 (3)
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.520 (3)	C25—H25	0.9300
C7—C11	1.554 (3)	C26—C27	1.382 (3)
C7—C13	1.585 (3)	C26—C31	1.393 (3)
C9—C10	1.479 (4)	C27—C28	1.388 (3)
C10—H10A	0.9600	C27—H27	0.9300
C10—H10B	0.9600	C28—C29	1.366 (3)
C10—H10C	0.9600	C28—H28	0.9300
C11—C26	1.508 (3)	C29—C30	1.362 (3)
C11—C12	1.537 (3)	C30—C31	1.398 (3)
C11—H11	0.9800	C30—H30	0.9300
C12—C20	1.517 (3)	C31—H31	0.9300

C14—O4—C15	116.40 (19)	O4—C15—C16	112.2 (2)
C17—O6—C18	113.5 (6)	O4—C15—H15A	109.2
C17—O6—C18B	125.0 (13)	C16—C15—H15A	109.2
C18—O6—C18B	17.2 (12)	O4—C15—H15B	109.2
O7—N1—O8	122.1 (2)	C16—C15—H15B	109.2
O7—N1—C23	119.5 (2)	H15A—C15—H15B	107.9
O8—N1—C23	118.3 (2)	C15—C16—H16A	109.5
C13—N2—C12	111.43 (17)	C15—C16—H16B	109.5
C13—N2—H4	112.0 (15)	H16A—C16—H16B	109.5
C12—N2—H4	108.5 (15)	C15—C16—H16C	109.5
C9—N3—C8	125.68 (18)	H16A—C16—H16C	109.5
C9—N3—C4	124.68 (18)	H16B—C16—H16C	109.5
C8—N3—C4	109.00 (16)	O5—C17—O6	124.7 (2)
C2—C1—C6	119.9 (2)	O5—C17—C13	123.4 (2)
C2—C1—H1	120.0	O6—C17—C13	112.0 (2)
C6—C1—H1	120.0	O6—C18—C19	102.5 (9)
C1—C2—C3	121.9 (2)	O6—C18—H18A	111.3
C1—C2—H2	119.0	C19—C18—H18A	111.3
C3—C2—H2	119.0	O6—C18—H18B	111.3
C2—C3—C4	117.6 (2)	C19—C18—H18B	111.3
C2—C3—H3	121.2	H18A—C18—H18B	109.2
C4—C3—H3	121.2	C19B—C18B—O6	109 (2)
C3—C4—C5	121.6 (2)	C19B—C18B—H18C	110.0
C3—C4—N3	128.8 (2)	O6—C18B—H18C	110.0
C5—C4—N3	109.64 (16)	C19B—C18B—H18D	110.0
C6—C5—C4	119.60 (18)	O6—C18B—H18D	110.0
C6—C5—C7	130.76 (18)	H18C—C18B—H18D	108.4
C4—C5—C7	109.57 (18)	C18B—C19B—H19D	109.5
C5—C6—C1	119.3 (2)	C18B—C19B—H19E	109.5
C5—C6—H6	120.3	H19D—C19B—H19E	109.5
C1—C6—H6	120.3	C18B—C19B—H19F	109.5
C5—C7—C8	102.40 (16)	H19D—C19B—H19F	109.5
C5—C7—C11	117.69 (17)	H19E—C19B—H19F	109.5
C8—C7—C11	111.05 (16)	C21—C20—C25	118.2 (2)
C5—C7—C13	112.56 (17)	C21—C20—C12	122.09 (19)
C8—C7—C13	114.50 (17)	C25—C20—C12	119.66 (19)
C11—C7—C13	99.26 (15)	C22—C21—C20	120.7 (2)
O1—C8—N3	125.27 (19)	C22—C21—H21	119.7
O1—C8—C7	125.77 (19)	C20—C21—H21	119.7
N3—C8—C7	108.86 (17)	C23—C22—C21	119.1 (2)
O2—C9—N3	119.4 (2)	C23—C22—H22	120.4
O2—C9—C10	122.2 (2)	C21—C22—H22	120.4
N3—C9—C10	118.4 (2)	C22—C23—C24	122.1 (2)
C9—C10—H10A	109.5	C22—C23—N1	119.4 (2)
C9—C10—H10B	109.5	C24—C23—N1	118.5 (2)
H10A—C10—H10B	109.5	C23—C24—C25	118.1 (2)
C9—C10—H10C	109.5	C23—C24—H24	120.9
H10A—C10—H10C	109.5	C25—C24—H24	120.9
H10B—C10—H10C	109.5	C24—C25—C20	121.7 (2)
C26—C11—C12	117.55 (17)	C24—C25—H25	119.2
C26—C11—C7	117.90 (16)	C20—C25—H25	119.2
C12—C11—C7	102.50 (16)	C27—C26—C31	117.5 (2)
C26—C11—H11	106.0	C27—C26—C11	118.09 (18)
C12—C11—H11	106.0	C31—C26—C11	124.4 (2)
C7—C11—H11	106.0	C26—C27—C28	122.1 (2)
N2—C12—C20	113.65 (17)	C26—C27—H27	118.9
N2—C12—C11	103.66 (16)	C28—C27—H27	118.9
C20—C12—C11	112.04 (18)	C29—C28—C27	118.5 (2)
N2—C12—H12	109.1	C29—C28—H28	120.8
C20—C12—H12	109.1	C27—C28—H28	120.8
C11—C12—H12	109.1	C30—C29—C28	121.9 (2)
N2—C13—C17	110.12 (18)	C30—C29—Cl1	119.01 (18)
N2—C13—C14	108.65 (17)	C28—C29—Cl1	119.05 (19)
C17—C13—C14	110.18 (18)	C29—C30—C31	119.1 (2)
N2—C13—C7	103.52 (16)	C29—C30—H30	120.5
C17—C13—C7	113.09 (16)	C31—C30—H30	120.5
C14—C13—C7	111.02 (17)	C26—C31—C30	120.9 (2)
O3—C14—O4	124.1 (2)	C26—C31—H31	119.6
O3—C14—C13	122.5 (2)	C30—C31—H31	119.6
O4—C14—C13	113.43 (19)

C6—C1—C2—C3	−0.3 (4)	C8—C7—C13—C14	−38.4 (2)
C1—C2—C3—C4	0.7 (4)	C11—C7—C13—C14	79.90 (19)
C2—C3—C4—C5	0.3 (4)	C15—O4—C14—O3	−0.8 (4)
C2—C3—C4—N3	−177.5 (2)	C15—O4—C14—C13	179.8 (2)
C9—N3—C4—C3	12.0 (4)	N2—C13—C14—O3	24.4 (3)
C8—N3—C4—C3	−176.8 (2)	C17—C13—C14—O3	145.1 (3)
C9—N3—C4—C5	−166.0 (2)	C7—C13—C14—O3	−88.8 (3)
C8—N3—C4—C5	5.3 (2)	N2—C13—C14—O4	−156.19 (19)
C3—C4—C5—C6	−1.6 (3)	C17—C13—C14—O4	−35.5 (3)
N3—C4—C5—C6	176.57 (19)	C7—C13—C14—O4	90.6 (2)
C3—C4—C5—C7	−178.9 (2)	C14—O4—C15—C16	79.3 (3)
N3—C4—C5—C7	−0.8 (2)	C18—O6—C17—O5	−5.4 (7)
C4—C5—C6—C1	1.9 (3)	C18B—O6—C17—O5	9.4 (15)
C7—C5—C6—C1	178.6 (2)	C18—O6—C17—C13	173.4 (7)
C2—C1—C6—C5	−1.0 (4)	C18B—O6—C17—C13	−171.8 (15)
C6—C5—C7—C8	179.5 (2)	N2—C13—C17—O5	15.1 (3)
C4—C5—C7—C8	−3.5 (2)	C14—C13—C17—O5	−104.8 (3)
C6—C5—C7—C11	57.4 (3)	C7—C13—C17—O5	130.3 (2)
C4—C5—C7—C11	−125.59 (19)	N2—C13—C17—O6	−163.76 (18)
C6—C5—C7—C13	−57.1 (3)	C14—C13—C17—O6	76.4 (2)
C4—C5—C7—C13	119.90 (19)	C7—C13—C17—O6	−48.5 (2)
C9—N3—C8—O1	−19.7 (4)	C17—O6—C18—C19	−178.6 (6)
C4—N3—C8—O1	169.1 (2)	C18B—O6—C18—C19	46 (7)
C9—N3—C8—C7	163.62 (19)	C17—O6—C18B—C19B	−108 (2)
C4—N3—C8—C7	−7.5 (2)	C18—O6—C18B—C19B	−55 (6)
C5—C7—C8—O1	−169.9 (2)	N2—C12—C20—C21	−27.4 (3)
C11—C7—C8—O1	−43.5 (3)	C11—C12—C20—C21	89.7 (3)
C13—C7—C8—O1	67.9 (3)	N2—C12—C20—C25	154.6 (2)
C5—C7—C8—N3	6.7 (2)	C11—C12—C20—C25	−88.3 (2)
C11—C7—C8—N3	133.17 (18)	C25—C20—C21—C22	1.7 (4)
C13—C7—C8—N3	−115.43 (19)	C12—C20—C21—C22	−176.3 (3)
C8—N3—C9—O2	173.1 (3)	C20—C21—C22—C23	−0.3 (5)
C4—N3—C9—O2	−17.0 (4)	C21—C22—C23—C24	−1.2 (5)
C8—N3—C9—C10	−8.8 (4)	C21—C22—C23—N1	179.6 (3)
C4—N3—C9—C10	161.0 (2)	O7—N1—C23—C22	179.6 (3)
C5—C7—C11—C26	52.6 (3)	O8—N1—C23—C22	−0.7 (4)
C8—C7—C11—C26	−64.9 (2)	O7—N1—C23—C24	0.4 (4)
C13—C7—C11—C26	174.27 (17)	O8—N1—C23—C24	−179.9 (3)
C5—C7—C11—C12	−78.2 (2)	C22—C23—C24—C25	1.3 (4)
C8—C7—C11—C12	164.33 (16)	N1—C23—C24—C25	−179.5 (2)
C13—C7—C11—C12	43.47 (17)	C23—C24—C25—C20	0.1 (4)
C13—N2—C12—C20	133.41 (19)	C21—C20—C25—C24	−1.6 (4)
C13—N2—C12—C11	11.5 (2)	C12—C20—C25—C24	176.5 (2)
C26—C11—C12—N2	−165.99 (17)	C12—C11—C26—C27	−123.4 (2)
C7—C11—C12—N2	−34.98 (18)	C7—C11—C26—C27	113.1 (2)
C26—C11—C12—C20	71.1 (2)	C12—C11—C26—C31	54.3 (3)
C7—C11—C12—C20	−157.92 (16)	C7—C11—C26—C31	−69.3 (3)
C12—N2—C13—C17	137.36 (18)	C31—C26—C27—C28	−0.2 (3)
C12—N2—C13—C14	−101.9 (2)	C11—C26—C27—C28	177.6 (2)
C12—N2—C13—C7	16.2 (2)	C26—C27—C28—C29	0.7 (4)
C5—C7—C13—N2	88.8 (2)	C27—C28—C29—C30	−0.7 (4)
C8—C7—C13—N2	−154.82 (17)	C27—C28—C29—Cl1	−179.96 (19)
C11—C7—C13—N2	−36.52 (19)	C28—C29—C30—C31	0.3 (4)
C5—C7—C13—C17	−30.4 (2)	Cl1—C29—C30—C31	179.52 (18)
C8—C7—C13—C17	86.0 (2)	C27—C26—C31—C30	−0.3 (3)
C11—C7—C13—C17	−155.66 (17)	C11—C26—C31—C30	−177.9 (2)
C5—C7—C13—C14	−154.82 (17)	C29—C30—C31—C26	0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O8ⁱ	0.96	2.51	3.387 (4)	152
C11—H11···O3	0.98	2.54	3.200 (3)	125
C21—H21···O3	0.93	2.44	3.181 (3)	136

Symmetry code: (i) x+1/2, −y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₃₁H₂₈ClN₃O₈
M_r	606.01
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.780 (2), 14.859 (3), 20.466 (5)
V (Å³)	2974.1 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.40 × 0.38 × 0.32

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.565, 0.626
No. of measured, independent and observed [I > 2σ(I)] reflections	27366, 4732, 4456
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.066, 1.00
No. of reflections	4732
No. of parameters	403
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.15
Absolute structure	Flack (1983), with 2017 Friedel pairs
Absolute structure parameter	0.020 (15)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O8ⁱ	0.96	2.51	3.387 (4)	152.0
C11—H11···O3	0.98	2.54	3.200 (3)	124.5
C21—H21···O3	0.93	2.44	3.181 (3)	136.4

Symmetry code: (i) x+1/2, −y−1/2, −z.

Acknowledgements

The diffraction data were collected at the Centre for Test and Analysis, Chengdu Branch, Chinese Academy of Sciences. The author acknowledges financial support from China West Normal University.

References

Bhattacharya, S. K., Glover, V., Melntyre, I., Oxenkrug, G. & Sandler, M. (1982). Neurosci. Lett. 92, 218–221. CrossRef Web of Science Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­ethyl 1-acetyl-4′-(4-chloro­phen­yl)-5′-(4-nitro­phen­yl)-2-oxo­spiro­[indoline-3,3′-pyrrolidine]-2′,2′-di­carboxyl­ate

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Experimental

Crystal data

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Supporting information

Acknowledgements

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organic compounds

Diethyl 1-acetyl-4′-(4-chlorophenyl)-5′-(4-nitrophenyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-2′,2′-dicarboxylate