Synthesis of spiro­[indoline-3,3′-pyrrolizines] by 1,3-dipolar reactions between isatins, l-proline and electron-deficient alkenes

Quiroga, J.; Romo, P.; Cobo, J.; Glidewell, C.

doi:10.1107/S2053229617016072

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Synthesis of spiro[indoline-3,3′-pyrrolizines] by 1,3-dipolar reactions between isatins, L-proline and electron-deficient alkenes

J. Quiroga, P. Romo, J. Cobo and C. Glidewell

Two spiro[indoline-3,3′-pyrrolizine] derivatives have been synthesized in good yield with high regio- and stereospecificity using one-pot reactions between readily available starting materials, namely L-proline, substituted 1H-indole-2,3-diones and electron-deficient alkenes. The products have been fully characterized by elemental analysis, IR and NMR spectroscopy, mass spectrometry and crystal structure analysis. In (1′RS,2′RS,3SR,7a′SR)-2′-benzoyl-1-hexyl-2-oxo-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,3′-pyrrolizine]-1′-carboxylic acid, C₂₈H₃₂N₂O₄, (I), the unsubstituted pyrrole ring and the reduced spiro-fused pyrrole ring adopt half-chair and envelope conformations, respectively, while in (1′RS,2′RS,3SR,7a′SR)-1′,2′-bis(4-chlorobenzoyl)-5,7-dichloro-2-oxo-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,3′-pyrrolizine], which crystallizes as a partial dichloromethane solvate, C₂₈H₂₀Cl₄N₂O₃·0.981CH₂Cl₂, (II), where the solvent component is disordered over three sets of atomic sites, these two rings adopt envelope and half-chair conformations, respectively. Molecules of (I) are linked by an O—H

·O hydrogen bond to form cyclic R₆⁶(48) hexamers of $\overline{3}$ (S₆) symmetry, which are further linked by two C—H

O hydrogen bonds to form a three-dimensional framework structure. In compound (II), inversion-related pairs of N—H

O hydrogen bonds link the spiro[indoline-3,3′-pyrrolizine] molecules into simple R₂²(8) dimers.

Keywords: synthesis; heterocycles; molecular conformation; spiro[indoline-3,3′-pyrrolizine]; NMR spectroscopy; reaction mechanism; disorder; hydrogen bonding; supramolecular assembly; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617016072/sk3676sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016072/sk3676Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016072/sk3676IIsup3.hkl Contains datablock II

CCDC references: 1584355; 1584354

Computing details top

Data collection: APEX3 Bruker, 2016) for (I); APEX3 (Bruker, 2016) for (II). For both structures, cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(1'RS,2'RS,3SR,7a'SR)-2'-Benzoyl-1-hexyl-2-oxo-\ 1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-1'-carboxylic acid (I) top

Crystal data top

C₂₈H₃₂N₂O₄	D_x = 1.312 Mg m⁻³
M_r = 460.56	Mo Kα radiation, λ = 0.71073 Å
Rhombohedral, R3:R	Cell parameters from 5197 reflections
a = 19.9182 (9) Å	θ = 2.4–27.2°
α = 116.980 (2)°	µ = 0.09 mm⁻¹
V = 3496.4 (11) Å³	T = 100 K
Z = 6	Plate, colourless
F(000) = 1476	0.27 × 0.21 × 0.13 mm

Data collection top

Bruker D8 Venture diffractometer	5194 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3672 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.067
φ and ω scans	θ_max = 27.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −25→24
T_min = 0.959, T_max = 0.989	k = −21→25
35458 measured reflections	l = −25→25

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.046P)² + 2.8884P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5194 reflections	Δρ_max = 0.59 e Å⁻³
311 parameters	Δρ_min = −0.35 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N11	0.28565 (15)	0.30066 (15)	0.64134 (15)	0.0136 (3)
C12	0.18369 (18)	0.17781 (18)	0.50967 (18)	0.0127 (4)
O12	0.06331 (12)	0.08598 (13)	0.42607 (12)	0.0160 (3)
C13	0.24343 (18)	0.17338 (18)	0.48159 (18)	0.0123 (4)
C13A	0.39408 (18)	0.30705 (18)	0.62340 (18)	0.0128 (4)
C14	0.50565 (19)	0.36345 (19)	0.67287 (19)	0.0161 (4)
H14	0.4948	0.3144	0.6144	0.019*
C15	0.63468 (19)	0.49387 (19)	0.81038 (19)	0.0188 (4)
H15	0.7121	0.5329	0.8462	0.023*
C16	0.65064 (19)	0.56663 (19)	0.89490 (19)	0.0177 (4)
H16	0.7392	0.6564	0.9874	0.021*
C17	0.53910 (19)	0.51055 (19)	0.84676 (19)	0.0164 (4)
H17	0.5497	0.5601	0.9045	0.020*
C17A	0.41287 (18)	0.38007 (18)	0.71179 (18)	0.0126 (4)
C21	0.17448 (18)	0.00668 (18)	0.31007 (18)	0.0133 (4)
H21	0.2652	0.0647	0.3616	0.016*
C22	0.18358 (18)	0.04304 (18)	0.40260 (18)	0.0124 (4)
H22	0.0898	−0.0305	0.3451	0.015*
N24	0.19334 (16)	0.15696 (16)	0.38496 (15)	0.0150 (3)
C25	0.2857 (2)	0.2729 (2)	0.4332 (2)	0.0210 (5)
H25A	0.3693	0.3579	0.5333	0.025*
H25B	0.2418	0.2818	0.3983	0.025*
C26	0.3174 (2)	0.2422 (2)	0.3787 (2)	0.0235 (5)
H26A	0.3897	0.2670	0.4367	0.028*
H26B	0.3445	0.2900	0.3704	0.028*
C27	0.1820 (2)	0.0895 (2)	0.2404 (2)	0.0225 (5)
H27B	0.1941	0.0489	0.2074	0.027*
H27C	0.1191	0.0668	0.1732	0.027*
C27A	0.1301 (2)	0.04066 (19)	0.26696 (19)	0.0160 (4)
H27A	0.0294	−0.0382	0.1864	0.019*
C111	0.26698 (19)	0.3384 (2)	0.70535 (19)	0.0174 (4)
H11A	0.1691	0.2668	0.6345	0.021*
H11B	0.3108	0.4231	0.7519	0.021*
C112	0.3266 (2)	0.3588 (2)	0.8082 (2)	0.0227 (5)
H11C	0.3484	0.3228	0.7966	0.027*
H11D	0.4124	0.4570	0.9005	0.027*
C113	0.2346 (2)	0.2917 (2)	0.7967 (2)	0.0296 (5)
H11E	0.1536	0.1926	0.7080	0.035*
H11F	0.2827	0.3117	0.8674	0.035*
C114	0.1875 (2)	0.3315 (2)	0.8094 (2)	0.0308 (5)
H11G	0.1278	0.2996	0.7312	0.037*
H11H	0.1329	0.2847	0.8051	0.037*
C115	0.2999 (2)	0.4808 (2)	0.9372 (2)	0.0336 (6)
H11I	0.3443	0.5268	0.9345	0.040*
H11J	0.3683	0.5165	1.0156	0.040*
C116	0.2467 (3)	0.5124 (3)	0.9559 (3)	0.0396 (6)
H11K	0.1756	0.4730	0.8763	0.059*
H11L	0.3211	0.6105	1.0366	0.059*
H11M	0.2097	0.4735	0.9665	0.059*
C211	0.07168 (19)	−0.14083 (19)	0.18908 (18)	0.0151 (4)
O211	−0.03088 (14)	−0.22926 (13)	0.13510 (14)	0.0254 (4)
O212	0.10475 (14)	−0.16276 (14)	0.14691 (14)	0.0220 (3)
H212	0.041 (2)	−0.249 (2)	0.076 (2)	0.026*
C227	0.26501 (18)	0.06015 (17)	0.49367 (18)	0.0131 (4)
O227	0.33092 (13)	0.06284 (13)	0.50208 (13)	0.0186 (3)
C221	0.26486 (19)	0.07644 (18)	0.57438 (19)	0.0153 (4)
C222	0.1553 (2)	0.01930 (19)	0.5305 (2)	0.0187 (4)
H222	0.0791	−0.0285	0.4486	0.022*
C223	0.1567 (2)	0.0318 (2)	0.6057 (2)	0.0240 (5)
H223	0.0807	−0.0093	0.5743	0.029*
C224	0.2691 (2)	0.1044 (2)	0.7267 (2)	0.0279 (5)
H224	0.2708	0.1143	0.7790	0.033*
C225	0.3787 (2)	0.1625 (2)	0.7715 (2)	0.0279 (5)
H225	0.4560	0.2132	0.8552	0.033*
C226	0.3765 (2)	0.1474 (2)	0.6954 (2)	0.0217 (5)
H226	0.4512	0.1855	0.7255	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0124 (8)	0.0151 (8)	0.0121 (8)	0.0113 (7)	0.0104 (7)	0.0109 (7)
C12	0.0154 (9)	0.0153 (9)	0.0126 (9)	0.0132 (9)	0.0116 (9)	0.0127 (9)
O12	0.0112 (6)	0.0163 (7)	0.0120 (6)	0.0107 (6)	0.0090 (6)	0.0108 (6)
C13	0.0136 (9)	0.0141 (9)	0.0126 (9)	0.0118 (8)	0.0111 (8)	0.0115 (8)
C13A	0.0153 (9)	0.0123 (9)	0.0138 (9)	0.0115 (8)	0.0122 (8)	0.0114 (8)
C14	0.0174 (10)	0.0150 (9)	0.0184 (10)	0.0138 (9)	0.0155 (9)	0.0136 (9)
C15	0.0143 (9)	0.0167 (10)	0.0200 (10)	0.0123 (9)	0.0140 (9)	0.0147 (9)
C16	0.0127 (9)	0.0116 (9)	0.0144 (9)	0.0087 (9)	0.0098 (9)	0.0097 (9)
C17	0.0177 (10)	0.0143 (9)	0.0149 (9)	0.0132 (9)	0.0134 (9)	0.0117 (9)
C17A	0.0128 (9)	0.0144 (9)	0.0148 (9)	0.0116 (8)	0.0114 (8)	0.0129 (8)
C21	0.0120 (9)	0.0124 (9)	0.0110 (9)	0.0096 (8)	0.0096 (8)	0.0090 (8)
C22	0.0102 (9)	0.0090 (8)	0.0099 (9)	0.0071 (8)	0.0078 (8)	0.0070 (8)
N24	0.0203 (8)	0.0173 (8)	0.0146 (8)	0.0162 (8)	0.0151 (8)	0.0141 (7)
C25	0.0319 (11)	0.0234 (10)	0.0246 (11)	0.0244 (10)	0.0248 (10)	0.0217 (10)
C26	0.0353 (12)	0.0276 (11)	0.0328 (12)	0.0276 (11)	0.0309 (11)	0.0278 (11)
C27	0.0357 (12)	0.0288 (11)	0.0243 (11)	0.0286 (11)	0.0271 (11)	0.0239 (10)
C27A	0.0178 (9)	0.0170 (9)	0.0130 (9)	0.0146 (9)	0.0126 (9)	0.0125 (9)
C111	0.0164 (9)	0.0185 (10)	0.0152 (9)	0.0149 (9)	0.0134 (9)	0.0128 (9)
C112	0.0263 (11)	0.0272 (11)	0.0237 (11)	0.0228 (10)	0.0221 (10)	0.0217 (10)
C113	0.0258 (12)	0.0280 (12)	0.0225 (11)	0.0203 (11)	0.0202 (11)	0.0197 (11)
C114	0.0310 (12)	0.0347 (13)	0.0313 (12)	0.0267 (12)	0.0272 (11)	0.0279 (12)
C115	0.0288 (12)	0.0330 (13)	0.0324 (13)	0.0243 (12)	0.0244 (12)	0.0278 (12)
C116	0.0353 (14)	0.0413 (14)	0.0438 (15)	0.0325 (13)	0.0336 (13)	0.0343 (14)
C211	0.0154 (9)	0.0147 (9)	0.0125 (9)	0.0122 (9)	0.0113 (8)	0.0110 (8)
O211	0.0171 (7)	0.0137 (7)	0.0214 (7)	0.0102 (7)	0.0157 (7)	0.0109 (7)
O212	0.0192 (7)	0.0111 (7)	0.0173 (7)	0.0104 (6)	0.0156 (7)	0.0086 (6)
C227	0.0108 (9)	0.0073 (8)	0.0100 (9)	0.0064 (8)	0.0075 (8)	0.0063 (8)
O227	0.0200 (7)	0.0210 (7)	0.0205 (7)	0.0178 (7)	0.0173 (7)	0.0174 (7)
C221	0.0171 (9)	0.0124 (9)	0.0155 (9)	0.0119 (9)	0.0133 (9)	0.0119 (9)
C222	0.0181 (10)	0.0168 (10)	0.0191 (10)	0.0138 (9)	0.0153 (9)	0.0151 (9)
C223	0.0269 (11)	0.0244 (11)	0.0303 (11)	0.0211 (10)	0.0256 (11)	0.0236 (10)
C224	0.0358 (12)	0.0290 (12)	0.0269 (11)	0.0257 (11)	0.0278 (11)	0.0247 (11)
C225	0.0272 (12)	0.0308 (12)	0.0203 (11)	0.0228 (11)	0.0190 (10)	0.0217 (11)
C226	0.0208 (10)	0.0241 (11)	0.0190 (10)	0.0185 (10)	0.0164 (10)	0.0179 (10)

Geometric parameters (Å, º) top

N11—C12	1.351 (2)	C27A—H27A	1.0000
N11—C17A	1.419 (2)	C111—C112	1.540 (3)
N11—C111	1.464 (2)	C111—H11A	0.9900
C12—O12	1.225 (2)	C111—H11B	0.9900
C12—C13	1.546 (3)	C112—C113	1.521 (3)
C13—N24	1.482 (2)	C112—H11C	0.9900
C13—C13A	1.519 (3)	C112—H11D	0.9900
C13—C22	1.556 (3)	C113—C114	1.511 (3)
C13A—C14	1.384 (3)	C113—H11E	0.9900
C13A—C17A	1.393 (3)	C113—H11F	0.9900
C14—C15	1.398 (3)	C114—C115	1.502 (3)
C14—H14	0.9500	C114—H11G	0.9900
C15—C16	1.385 (3)	C114—H11H	0.9900
C15—H15	0.9500	C115—C116	1.551 (3)
C16—C17	1.395 (3)	C115—H11I	0.9900
C16—H16	0.9500	C115—H11J	0.9900
C17—C17A	1.379 (3)	C116—H11K	0.9800
C17—H17	0.9500	C116—H11L	0.9800
C21—C211	1.507 (3)	C116—H11M	0.9800
C21—C22	1.524 (3)	C211—O211	1.206 (2)
C21—C27A	1.536 (3)	C211—O212	1.327 (2)
C21—H21	1.0000	O212—H212	0.87 (2)
C22—C227	1.518 (3)	C227—O227	1.218 (2)
C22—H22	1.0000	C227—C221	1.490 (3)
N24—C25	1.472 (3)	C221—C222	1.392 (3)
N24—C27A	1.484 (2)	C221—C226	1.395 (3)
C25—C26	1.525 (3)	C222—C223	1.387 (3)
C25—H25A	0.9900	C222—H222	0.9500
C25—H25B	0.9900	C223—C224	1.385 (3)
C26—C27	1.526 (3)	C223—H223	0.9500
C26—H26A	0.9900	C224—C225	1.378 (3)
C26—H26B	0.9900	C224—H224	0.9500
C27—C27A	1.532 (3)	C225—C226	1.382 (3)
C27—H27B	0.9900	C225—H225	0.9500
C27—H27C	0.9900	C226—H226	0.9500

C12—N11—C17A	110.72 (15)	C27—C27A—C21	115.22 (16)
C12—N11—C111	124.01 (16)	N24—C27A—H27A	110.2
C17A—N11—C111	124.73 (15)	C27—C27A—H27A	110.2
O12—C12—N11	125.14 (18)	C21—C27A—H27A	110.2
O12—C12—C13	125.83 (17)	N11—C111—C112	112.56 (16)
N11—C12—C13	109.01 (15)	N11—C111—H11A	109.1
N24—C13—C13A	116.59 (15)	C112—C111—H11A	109.1
N24—C13—C12	107.28 (14)	N11—C111—H11B	109.1
C13A—C13—C12	101.39 (14)	C112—C111—H11B	109.1
N24—C13—C22	103.51 (14)	H11A—C111—H11B	107.8
C13A—C13—C22	116.71 (15)	C113—C112—C111	114.72 (18)
C12—C13—C22	111.19 (15)	C113—C112—H11C	108.6
C14—C13A—C17A	119.41 (17)	C111—C112—H11C	108.6
C14—C13A—C13	132.13 (17)	C113—C112—H11D	108.6
C17A—C13A—C13	108.44 (16)	C111—C112—H11D	108.6
C13A—C14—C15	118.81 (18)	H11C—C112—H11D	107.6
C13A—C14—H14	120.6	C114—C113—C112	117.0 (2)
C15—C14—H14	120.6	C114—C113—H11E	108.1
C16—C15—C14	120.59 (18)	C112—C113—H11E	108.1
C16—C15—H15	119.7	C114—C113—H11F	108.1
C14—C15—H15	119.7	C112—C113—H11F	108.1
C15—C16—C17	121.21 (18)	H11E—C113—H11F	107.3
C15—C16—H16	119.4	C115—C114—C113	114.2 (2)
C17—C16—H16	119.4	C115—C114—H11G	108.7
C17A—C17—C16	117.12 (18)	C113—C114—H11G	108.7
C17A—C17—H17	121.4	C115—C114—H11H	108.7
C16—C17—H17	121.4	C113—C114—H11H	108.7
C17—C17A—C13A	122.75 (17)	H11G—C114—H11H	107.6
C17—C17A—N11	127.36 (17)	C114—C115—C116	111.5 (2)
C13A—C17A—N11	109.89 (16)	C114—C115—H11I	109.3
C211—C21—C22	112.18 (15)	C116—C115—H11I	109.3
C211—C21—C27A	110.95 (15)	C114—C115—H11J	109.3
C22—C21—C27A	102.12 (15)	C116—C115—H11J	109.3
C211—C21—H21	110.4	H11I—C115—H11J	108.0
C22—C21—H21	110.4	C115—C116—H11K	109.5
C27A—C21—H21	110.4	C115—C116—H11L	109.5
C227—C22—C21	113.89 (15)	H11K—C116—H11L	109.5
C227—C22—C13	113.48 (15)	C115—C116—H11M	109.5
C21—C22—C13	104.09 (14)	H11K—C116—H11M	109.5
C227—C22—H22	108.4	H11L—C116—H11M	109.5
C21—C22—H22	108.4	O211—C211—O212	123.90 (18)
C13—C22—H22	108.4	O211—C211—C21	123.33 (17)
C25—N24—C13	119.60 (15)	O212—C211—C21	112.75 (16)
C25—N24—C27A	108.43 (15)	C211—O212—H212	109.3 (15)
C13—N24—C27A	110.41 (14)	O227—C227—C221	120.88 (17)
N24—C25—C26	105.22 (15)	O227—C227—C22	120.39 (17)
N24—C25—H25A	110.7	C221—C227—C22	118.72 (16)
C26—C25—H25A	110.7	C222—C221—C226	119.25 (18)
N24—C25—H25B	110.7	C222—C221—C227	122.06 (17)
C26—C25—H25B	110.7	C226—C221—C227	118.65 (18)
H25A—C25—H25B	108.8	C223—C222—C221	120.28 (19)
C25—C26—C27	101.68 (17)	C223—C222—H222	119.9
C25—C26—H26A	111.4	C221—C222—H222	119.9
C27—C26—H26A	111.4	C224—C223—C222	119.8 (2)
C25—C26—H26B	111.4	C224—C223—H223	120.1
C27—C26—H26B	111.4	C222—C223—H223	120.1
H26A—C26—H26B	109.3	C225—C224—C223	120.2 (2)
C26—C27—C27A	103.40 (16)	C225—C224—H224	119.9
C26—C27—H27B	111.1	C223—C224—H224	119.9
C27A—C27—H27B	111.1	C224—C225—C226	120.3 (2)
C26—C27—H27C	111.1	C224—C225—H225	119.8
C27A—C27—H27C	111.1	C226—C225—H225	119.8
H27B—C27—H27C	109.0	C225—C226—C221	120.1 (2)
N24—C27A—C27	105.61 (15)	C225—C226—H226	120.0
N24—C27A—C21	105.07 (14)	C221—C226—H226	120.0

C17A—N11—C12—O12	176.43 (17)	C13A—C13—N24—C27A	119.76 (17)
C111—N11—C12—O12	4.5 (3)	C12—C13—N24—C27A	−127.47 (16)
C17A—N11—C12—C13	−4.7 (2)	C22—C13—N24—C27A	−9.83 (18)
C111—N11—C12—C13	−176.63 (16)	C13—N24—C25—C26	106.85 (19)
O12—C12—C13—N24	63.1 (2)	C27A—N24—C25—C26	−20.9 (2)
N11—C12—C13—N24	−115.74 (16)	N24—C25—C26—C27	36.7 (2)
O12—C12—C13—C13A	−174.14 (18)	C25—C26—C27—C27A	−38.3 (2)
N11—C12—C13—C13A	7.00 (19)	C25—N24—C27A—C27	−3.6 (2)
O12—C12—C13—C22	−49.4 (2)	C13—N24—C27A—C27	−136.37 (16)
N11—C12—C13—C22	131.74 (16)	C25—N24—C27A—C21	118.67 (16)
N24—C13—C13A—C14	−69.0 (3)	C13—N24—C27A—C21	−14.13 (19)
C12—C13—C13A—C14	174.9 (2)	C26—C27—C27A—N24	26.4 (2)
C22—C13—C13A—C14	53.9 (3)	C26—C27—C27A—C21	−89.02 (19)
N24—C13—C13A—C17A	109.22 (18)	C211—C21—C27A—N24	152.19 (15)
C12—C13—C13A—C17A	−6.86 (19)	C22—C21—C27A—N24	32.47 (18)
C22—C13—C13A—C17A	−127.80 (17)	C211—C21—C27A—C27	−92.03 (19)
C17A—C13A—C14—C15	−1.3 (3)	C22—C21—C27A—C27	148.25 (16)
C13—C13A—C14—C15	176.82 (19)	C12—N11—C111—C112	111.4 (2)
C13A—C14—C15—C16	−1.6 (3)	C17A—N11—C111—C112	−59.4 (2)
C14—C15—C16—C17	2.3 (3)	N11—C111—C112—C113	−134.04 (19)
C15—C16—C17—C17A	−0.1 (3)	C111—C112—C113—C114	−57.4 (3)
C16—C17—C17A—C13A	−2.9 (3)	C112—C113—C114—C115	−55.4 (3)
C16—C17—C17A—N11	177.67 (18)	C113—C114—C115—C116	−170.0 (2)
C14—C13A—C17A—C17	3.7 (3)	C22—C21—C211—O211	33.0 (3)
C13—C13A—C17A—C17	−174.86 (17)	C27A—C21—C211—O211	−80.5 (2)
C14—C13A—C17A—N11	−176.84 (16)	C22—C21—C211—O212	−148.45 (16)
C13—C13A—C17A—N11	4.6 (2)	C27A—C21—C211—O212	98.03 (19)
C12—N11—C17A—C17	179.56 (18)	C21—C22—C227—O227	9.8 (2)
C111—N11—C17A—C17	−8.6 (3)	C13—C22—C227—O227	−109.04 (19)
C12—N11—C17A—C13A	0.1 (2)	C21—C22—C227—C221	−171.46 (15)
C111—N11—C17A—C13A	171.94 (17)	C13—C22—C227—C221	69.7 (2)
C211—C21—C22—C227	78.58 (19)	O227—C227—C221—C222	−151.83 (18)
C27A—C21—C22—C227	−162.57 (15)	C22—C227—C221—C222	29.5 (3)
C211—C21—C22—C13	−157.34 (15)	O227—C227—C221—C226	26.0 (3)
C27A—C21—C22—C13	−38.49 (17)	C22—C227—C221—C226	−152.74 (17)
N24—C13—C22—C227	154.56 (15)	C226—C221—C222—C223	−0.6 (3)
C13A—C13—C22—C227	25.0 (2)	C227—C221—C222—C223	177.16 (18)
C12—C13—C22—C227	−90.56 (18)	C221—C222—C223—C224	1.7 (3)
N24—C13—C22—C21	30.21 (17)	C222—C223—C224—C225	−1.0 (3)
C13A—C13—C22—C21	−99.30 (17)	C223—C224—C225—C226	−0.8 (3)
C12—C13—C22—C21	145.09 (15)	C224—C225—C226—C221	1.8 (3)
C13A—C13—N24—C25	−7.1 (2)	C222—C221—C226—C225	−1.1 (3)
C12—C13—N24—C25	105.71 (18)	C227—C221—C226—C225	−178.98 (19)
C22—C13—N24—C25	−136.64 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O212—H212···O12ⁱ	0.87 (3)	1.79 (3)	2.652 (3)	176 (4)
C111—H11B···O227ⁱⁱ	0.99	2.46	3.392 (4)	157
C223—H223···O12ⁱⁱⁱ	0.95	2.56	3.452 (6)	156

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

(1'RS,2'RS,3SR,7a'SR)-1',2'-Bis(4-chlorobenzoyl)-5,7-dichloro-2-oxo-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine] dichloromethane 0.981-solvate (II) top

Crystal data top

C₂₈H₂₀Cl₄N₂O₃·0.981CH₂Cl₂	F(000) = 1340.8
M_r = 657.57	D_x = 1.483 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.800 (4) Å	Cell parameters from 6780 reflections
b = 12.511 (5) Å	θ = 2.2–27.5°
c = 18.638 (5) Å	µ = 0.62 mm⁻¹
β = 99.325 (12)°	T = 100 K
V = 2945.3 (17) Å³	Plate, colourless
Z = 4	0.38 × 0.35 × 0.16 mm

Data collection top

Bruker D8 Venture diffractometer	6778 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	6162 reflections with I > 2σ(I)
Multilayer mirror monochromator	R_int = 0.031
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −16→16
T_min = 0.889, T_max = 0.910	k = −16→16
92566 measured reflections	l = −24→24

Refinement top

Refinement on F²	9 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0299P)² + 2.0129P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
6778 reflections	Δρ_max = 0.48 e Å⁻³
397 parameters	Δρ_min = −0.55 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N11	0.43284 (8)	0.61892 (8)	0.46172 (5)	0.0123 (2)
H11	0.4751 (12)	0.6057 (13)	0.5009 (9)	0.015*
C12	0.39675 (9)	0.54291 (9)	0.41183 (6)	0.0114 (2)
O12	0.41299 (7)	0.44655 (7)	0.41841 (5)	0.01519 (18)
C13	0.33169 (9)	0.59797 (9)	0.34400 (6)	0.0107 (2)
C13A	0.34080 (9)	0.71562 (9)	0.36652 (6)	0.0113 (2)
C14	0.30039 (10)	0.80815 (10)	0.33166 (6)	0.0136 (2)
H14	0.2593	0.8056	0.2844	0.016*
C15	0.32191 (10)	0.90520 (10)	0.36805 (7)	0.0144 (2)
Cl15	0.27105 (3)	1.02188 (2)	0.32509 (2)	0.02081 (8)
C16	0.38010 (10)	0.91148 (10)	0.43773 (7)	0.0150 (2)
H16	0.3928	0.9786	0.4614	0.018*
C17	0.41944 (10)	0.81773 (10)	0.47228 (6)	0.0139 (2)
Cl17	0.48725 (3)	0.81961 (3)	0.56084 (2)	0.02249 (8)
C17A	0.40057 (9)	0.72119 (9)	0.43617 (6)	0.0114 (2)
C21	0.28396 (9)	0.59190 (9)	0.21334 (6)	0.0118 (2)
H21	0.2772	0.6702	0.2030	0.014*
C22	0.37775 (9)	0.57028 (9)	0.27360 (6)	0.0113 (2)
H22	0.3944	0.4922	0.2740	0.014*
N24	0.22596 (8)	0.55076 (8)	0.32714 (5)	0.0118 (2)
C25	0.14005 (10)	0.59019 (11)	0.36463 (7)	0.0164 (2)
H25A	0.1539	0.6645	0.3819	0.020*
H25B	0.1321	0.5441	0.4066	0.020*
C26	0.04113 (10)	0.58455 (11)	0.30572 (7)	0.0180 (3)
H26A	−0.0137	0.6358	0.3157	0.022*
H26B	0.0107	0.5116	0.3018	0.022*
C27	0.08530 (10)	0.61535 (11)	0.23659 (7)	0.0166 (2)
H27B	0.0371	0.5931	0.1921	0.020*
H27C	0.0986	0.6932	0.2345	0.020*
C27A	0.18843 (9)	0.55161 (10)	0.24688 (6)	0.0123 (2)
H27A	0.1722	0.4765	0.2303	0.015*
C217	0.29062 (10)	0.53006 (10)	0.14365 (6)	0.0136 (2)
O217	0.35076 (8)	0.45461 (8)	0.14349 (5)	0.0233 (2)
C211	0.21473 (9)	0.55919 (10)	0.07655 (6)	0.0125 (2)
C212	0.17137 (10)	0.66137 (10)	0.06474 (7)	0.0162 (2)
H212	0.1874	0.7146	0.1012	0.019*
C213	0.10482 (11)	0.68601 (10)	0.00000 (7)	0.0179 (3)
H213	0.0770	0.7561	−0.0085	0.021*
C214	0.08003 (10)	0.60648 (11)	−0.05172 (7)	0.0158 (2)
Cl14	−0.00203 (3)	0.63716 (3)	−0.13326 (2)	0.02432 (8)
C215	0.11886 (10)	0.50323 (11)	−0.04051 (7)	0.0167 (2)
H215	0.0989	0.4491	−0.0759	0.020*
C216	0.18744 (10)	0.48039 (10)	0.02338 (7)	0.0154 (2)
H216	0.2162	0.4105	0.0311	0.018*
C227	0.47804 (10)	0.63247 (10)	0.26712 (6)	0.0132 (2)
O227	0.47487 (7)	0.71308 (7)	0.23002 (5)	0.01870 (19)
C221	0.57943 (10)	0.59336 (10)	0.31058 (7)	0.0149 (2)
C222	0.59639 (11)	0.48510 (11)	0.32730 (8)	0.0197 (3)
H222	0.5419	0.4346	0.3121	0.024*
C223	0.69288 (11)	0.45120 (12)	0.36608 (8)	0.0240 (3)
H223	0.7048	0.3777	0.3773	0.029*
C224	0.77115 (11)	0.52611 (13)	0.38809 (7)	0.0237 (3)
Cl24	0.89258 (3)	0.48244 (4)	0.43545 (2)	0.03470 (10)
C225	0.75602 (11)	0.63409 (13)	0.37267 (8)	0.0243 (3)
H225	0.8106	0.6843	0.3886	0.029*
C226	0.65967 (10)	0.66774 (11)	0.33350 (7)	0.0196 (3)
H226	0.6483	0.7413	0.3223	0.023*
C31	0.2138 (3)	0.2919 (10)	0.37798 (18)	0.0210 (5)	0.615 (7)
H31A	0.2449	0.3646	0.3816	0.025*	0.615 (7)
H31B	0.2700	0.2406	0.3977	0.025*	0.615 (7)
Cl31	0.1104 (2)	0.28576 (13)	0.42976 (12)	0.0433 (5)	0.615 (7)
Cl32	0.1673 (2)	0.2616 (2)	0.28628 (10)	0.0365 (5)	0.615 (7)
C41	0.2280 (10)	0.293 (3)	0.3719 (6)	0.0210 (5)	0.187 (5)
H41A	0.2652	0.3617	0.3687	0.025*	0.187 (5)
H41B	0.2822	0.2360	0.3818	0.025*	0.187 (5)
Cl41	0.1552 (11)	0.2985 (3)	0.4443 (2)	0.0498 (9)	0.187 (5)
Cl42	0.1467 (14)	0.2669 (17)	0.2883 (4)	0.042 (2)	0.187 (5)
C51	0.2471 (8)	0.2952 (10)	0.3618 (3)	0.0210 (5)	0.179 (2)
H51A	0.2676	0.3687	0.3501	0.025*	0.179 (2)
H51B	0.3061	0.2469	0.3553	0.025*	0.179 (2)
Cl51	0.2272 (4)	0.2903 (2)	0.45308 (15)	0.0498 (9)	0.179 (2)
Cl52	0.1333 (12)	0.2577 (16)	0.3010 (4)	0.042 (2)	0.179 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0166 (5)	0.0099 (5)	0.0081 (4)	0.0017 (4)	−0.0045 (4)	0.0000 (4)
C12	0.0133 (5)	0.0118 (5)	0.0083 (5)	0.0001 (4)	−0.0011 (4)	0.0004 (4)
O12	0.0208 (4)	0.0095 (4)	0.0128 (4)	0.0015 (3)	−0.0048 (3)	0.0008 (3)
C13	0.0136 (5)	0.0090 (5)	0.0082 (5)	0.0010 (4)	−0.0021 (4)	0.0008 (4)
C13A	0.0143 (5)	0.0101 (5)	0.0092 (5)	0.0007 (4)	0.0014 (4)	−0.0007 (4)
C14	0.0185 (6)	0.0120 (6)	0.0099 (5)	0.0018 (4)	0.0010 (4)	0.0010 (4)
C15	0.0198 (6)	0.0094 (5)	0.0149 (6)	0.0027 (4)	0.0058 (5)	0.0029 (4)
Cl15	0.03592 (18)	0.00971 (13)	0.01741 (15)	0.00627 (12)	0.00616 (13)	0.00424 (11)
C16	0.0188 (6)	0.0100 (5)	0.0166 (6)	−0.0008 (4)	0.0038 (5)	−0.0026 (4)
C17	0.0157 (6)	0.0137 (6)	0.0114 (5)	−0.0006 (4)	−0.0008 (4)	−0.0024 (4)
Cl17	0.03090 (17)	0.01686 (15)	0.01538 (15)	0.00224 (12)	−0.00924 (12)	−0.00640 (11)
C17A	0.0135 (5)	0.0100 (5)	0.0104 (5)	0.0008 (4)	0.0013 (4)	0.0004 (4)
C21	0.0152 (5)	0.0108 (5)	0.0080 (5)	0.0015 (4)	−0.0017 (4)	−0.0004 (4)
C22	0.0147 (5)	0.0106 (5)	0.0075 (5)	0.0016 (4)	−0.0016 (4)	−0.0009 (4)
N24	0.0133 (5)	0.0133 (5)	0.0077 (4)	−0.0004 (4)	−0.0015 (4)	0.0000 (4)
C25	0.0167 (6)	0.0202 (6)	0.0125 (5)	0.0001 (5)	0.0030 (5)	0.0003 (5)
C26	0.0152 (6)	0.0213 (6)	0.0171 (6)	0.0007 (5)	0.0010 (5)	0.0014 (5)
C27	0.0150 (6)	0.0207 (6)	0.0126 (5)	0.0027 (5)	−0.0020 (4)	0.0018 (5)
C27A	0.0150 (5)	0.0122 (5)	0.0080 (5)	0.0003 (4)	−0.0030 (4)	−0.0006 (4)
C217	0.0170 (6)	0.0136 (6)	0.0094 (5)	−0.0002 (4)	−0.0001 (4)	−0.0008 (4)
O217	0.0293 (5)	0.0226 (5)	0.0159 (4)	0.0116 (4)	−0.0029 (4)	−0.0053 (4)
C211	0.0143 (5)	0.0152 (6)	0.0077 (5)	−0.0018 (4)	0.0011 (4)	0.0001 (4)
C212	0.0212 (6)	0.0158 (6)	0.0105 (5)	−0.0012 (5)	−0.0012 (5)	−0.0012 (4)
C213	0.0222 (6)	0.0162 (6)	0.0138 (6)	0.0004 (5)	−0.0017 (5)	0.0028 (5)
C214	0.0149 (6)	0.0215 (6)	0.0096 (5)	−0.0053 (5)	−0.0023 (4)	0.0037 (5)
Cl14	0.02718 (17)	0.02621 (17)	0.01487 (14)	−0.00592 (13)	−0.01070 (12)	0.00483 (12)
C215	0.0192 (6)	0.0194 (6)	0.0105 (5)	−0.0054 (5)	−0.0001 (5)	−0.0025 (5)
C216	0.0191 (6)	0.0157 (6)	0.0110 (5)	−0.0008 (5)	0.0011 (5)	−0.0007 (4)
C227	0.0161 (6)	0.0137 (6)	0.0093 (5)	0.0020 (4)	0.0007 (4)	−0.0026 (4)
O227	0.0211 (5)	0.0178 (4)	0.0163 (4)	−0.0004 (4)	0.0004 (4)	0.0044 (4)
C221	0.0143 (6)	0.0186 (6)	0.0119 (5)	0.0027 (5)	0.0022 (4)	0.0004 (5)
C222	0.0166 (6)	0.0197 (6)	0.0233 (6)	0.0039 (5)	0.0044 (5)	0.0027 (5)
C223	0.0188 (6)	0.0264 (7)	0.0280 (7)	0.0088 (5)	0.0072 (6)	0.0108 (6)
C224	0.0133 (6)	0.0401 (8)	0.0179 (6)	0.0075 (6)	0.0029 (5)	0.0109 (6)
Cl24	0.01454 (15)	0.0578 (3)	0.03092 (19)	0.00889 (16)	0.00122 (13)	0.02106 (18)
C225	0.0160 (6)	0.0341 (8)	0.0217 (7)	−0.0030 (6)	−0.0003 (5)	0.0035 (6)
C226	0.0180 (6)	0.0218 (7)	0.0184 (6)	−0.0004 (5)	0.0013 (5)	0.0015 (5)
C31	0.0174 (14)	0.0201 (8)	0.0238 (11)	−0.004 (2)	−0.0020 (8)	−0.0029 (14)
Cl31	0.0493 (9)	0.0322 (5)	0.0562 (6)	0.0023 (5)	0.0317 (6)	0.0035 (5)
Cl32	0.0686 (15)	0.0170 (5)	0.0189 (5)	0.0106 (8)	−0.0073 (6)	0.0005 (3)
C41	0.0174 (14)	0.0201 (8)	0.0238 (11)	−0.004 (2)	−0.0020 (8)	−0.0029 (14)
Cl41	0.078 (3)	0.0434 (11)	0.0296 (10)	−0.0187 (17)	0.0146 (16)	0.0091 (7)
Cl42	0.041 (3)	0.022 (3)	0.048 (3)	−0.014 (2)	−0.032 (3)	0.008 (3)
C51	0.0174 (14)	0.0201 (8)	0.0238 (11)	−0.004 (2)	−0.0020 (8)	−0.0029 (14)
Cl51	0.078 (3)	0.0434 (11)	0.0296 (10)	−0.0187 (17)	0.0146 (16)	0.0091 (7)
Cl52	0.041 (3)	0.022 (3)	0.048 (3)	−0.014 (2)	−0.032 (3)	0.008 (3)

Geometric parameters (Å, º) top

N11—C12	1.3577 (15)	C217—C211	1.4988 (16)
N11—C17A	1.4039 (16)	C211—C212	1.3969 (18)
N11—H11	0.852 (17)	C211—C216	1.4015 (17)
C12—O12	1.2261 (15)	C212—C213	1.3941 (17)
C12—C13	1.5572 (16)	C212—H212	0.9500
C13—N24	1.4633 (15)	C213—C214	1.3859 (18)
C13—C13A	1.5298 (17)	C213—H213	0.9500
C13—C22	1.5622 (16)	C214—C215	1.3877 (19)
C13A—C14	1.3858 (17)	C214—Cl14	1.7445 (13)
C13A—C17A	1.3977 (16)	C215—C216	1.3896 (17)
C14—C15	1.3963 (17)	C215—H215	0.9500
C14—H14	0.9500	C216—H216	0.9500
C15—C16	1.3907 (18)	C227—O227	1.2197 (16)
C15—Cl15	1.7398 (13)	C227—C221	1.4964 (17)
C16—C17	1.3923 (18)	C221—C222	1.3989 (19)
C16—H16	0.9500	C221—C226	1.4003 (19)
C17—C17A	1.3847 (17)	C222—C223	1.3922 (19)
C17—Cl17	1.7361 (13)	C222—H222	0.9500
C21—C217	1.5260 (16)	C223—C224	1.385 (2)
C21—C22	1.5293 (16)	C223—H223	0.9500
C21—C27A	1.5453 (17)	C224—C225	1.388 (2)
C21—H21	1.0000	C224—Cl24	1.7462 (14)
C22—C227	1.5225 (17)	C225—C226	1.3926 (19)
C22—H22	1.0000	C225—H225	0.9500
N24—C25	1.4797 (16)	C226—H226	0.9500
N24—C27A	1.4951 (15)	C31—Cl32	1.758 (2)
C25—C26	1.5372 (17)	C31—Cl31	1.761 (3)
C25—H25A	0.9900	C31—H31A	0.9900
C25—H25B	0.9900	C31—H31B	0.9900
C26—C27	1.5377 (18)	C41—Cl42	1.758 (4)
C26—H26A	0.9900	C41—Cl41	1.761 (5)
C26—H26B	0.9900	C41—H41B	0.9900
C27—C27A	1.5276 (17)	C41—H41A	0.9900
C27—H27B	0.9900	C51—Cl52	1.758 (4)
C27—H27C	0.9900	C51—Cl51	1.763 (5)
C27A—H27A	1.0000	C51—H51B	0.9900
C217—O217	1.2185 (16)	C51—H51A	0.9900

C12—N11—C17A	110.93 (10)	C27—C27A—C21	120.22 (10)
C12—N11—H11	123.3 (11)	N24—C27A—H27A	108.6
C17A—N11—H11	125.4 (11)	C27—C27A—H27A	108.6
O12—C12—N11	125.93 (11)	C21—C27A—H27A	108.6
O12—C12—C13	125.17 (10)	O217—C217—C211	120.71 (11)
N11—C12—C13	108.90 (10)	O217—C217—C21	121.15 (11)
N24—C13—C13A	118.30 (10)	C211—C217—C21	117.96 (10)
N24—C13—C12	110.49 (9)	C212—C211—C216	119.03 (11)
C13A—C13—C12	101.30 (9)	C212—C211—C217	122.77 (11)
N24—C13—C22	101.06 (9)	C216—C211—C217	118.20 (11)
C13A—C13—C22	114.92 (10)	C213—C212—C211	120.68 (12)
C12—C13—C22	111.02 (9)	C213—C212—H212	119.7
C14—C13A—C17A	120.02 (11)	C211—C212—H212	119.7
C14—C13A—C13	131.99 (11)	C214—C213—C212	118.82 (12)
C17A—C13A—C13	107.98 (10)	C214—C213—H213	120.6
C13A—C14—C15	118.00 (11)	C212—C213—H213	120.6
C13A—C14—H14	121.0	C213—C214—C215	121.84 (11)
C15—C14—H14	121.0	C213—C214—Cl14	119.05 (10)
C16—C15—C14	122.43 (11)	C215—C214—Cl14	119.11 (10)
C16—C15—Cl15	119.10 (10)	C214—C215—C216	118.78 (12)
C14—C15—Cl15	118.46 (10)	C214—C215—H215	120.6
C15—C16—C17	118.89 (11)	C216—C215—H215	120.6
C15—C16—H16	120.6	C215—C216—C211	120.78 (12)
C17—C16—H16	120.6	C215—C216—H216	119.6
C17A—C17—C16	119.24 (11)	C211—C216—H216	119.6
C17A—C17—Cl17	119.66 (9)	O227—C227—C221	121.57 (12)
C16—C17—Cl17	121.06 (9)	O227—C227—C22	121.09 (11)
C17—C17A—C13A	121.40 (11)	C221—C227—C22	117.28 (10)
C17—C17A—N11	127.70 (11)	C222—C221—C226	119.72 (12)
C13A—C17A—N11	110.88 (10)	C222—C221—C227	121.79 (12)
C217—C21—C22	112.96 (10)	C226—C221—C227	118.47 (12)
C217—C21—C27A	109.63 (10)	C223—C222—C221	120.21 (13)
C22—C21—C27A	102.92 (9)	C223—C222—H222	119.9
C217—C21—H21	110.4	C221—C222—H222	119.9
C22—C21—H21	110.4	C224—C223—C222	119.08 (13)
C27A—C21—H21	110.4	C224—C223—H223	120.5
C227—C22—C21	115.02 (10)	C222—C223—H223	120.5
C227—C22—C13	113.03 (9)	C223—C224—C225	121.83 (13)
C21—C22—C13	102.68 (9)	C223—C224—Cl24	118.69 (12)
C227—C22—H22	108.6	C225—C224—Cl24	119.47 (12)
C21—C22—H22	108.6	C224—C225—C226	118.99 (13)
C13—C22—H22	108.6	C224—C225—H225	120.5
C13—N24—C25	119.75 (10)	C226—C225—H225	120.5
C13—N24—C27A	110.37 (9)	C225—C226—C221	120.16 (13)
C25—N24—C27A	109.10 (9)	C225—C226—H226	119.9
N24—C25—C26	103.69 (10)	C221—C226—H226	119.9
N24—C25—H25A	111.0	Cl32—C31—Cl31	110.93 (18)
C26—C25—H25A	111.0	Cl32—C31—H31A	109.5
N24—C25—H25B	111.0	Cl31—C31—H31A	109.5
C26—C25—H25B	111.0	Cl32—C31—H31B	109.5
H25A—C25—H25B	109.0	Cl31—C31—H31B	109.5
C25—C26—C27	102.41 (10)	H31A—C31—H31B	108.0
C25—C26—H26A	111.3	Cl42—C41—Cl41	112.0 (5)
C27—C26—H26A	111.3	Cl42—C41—H41B	109.2
C25—C26—H26B	111.3	Cl41—C41—H41B	109.2
C27—C26—H26B	111.3	Cl42—C41—H41A	109.2
H26A—C26—H26B	109.2	Cl41—C41—H41A	109.2
C27A—C27—C26	101.04 (10)	H41B—C41—H41A	107.9
C27A—C27—H27B	111.6	Cl52—C51—Cl51	112.2 (4)
C26—C27—H27B	111.6	Cl52—C51—H51B	109.2
C27A—C27—H27C	111.6	Cl51—C51—H51B	109.2
C26—C27—H27C	111.6	Cl52—C51—H51A	109.2
H27B—C27—H27C	109.4	Cl51—C51—H51A	109.2
N24—C27A—C27	105.09 (10)	H51B—C51—H51A	107.9
N24—C27A—C21	105.08 (9)

C17A—N11—C12—O12	179.26 (12)	C27A—N24—C25—C26	15.32 (13)
C17A—N11—C12—C13	−0.25 (14)	N24—C25—C26—C27	−36.26 (12)
O12—C12—C13—N24	54.83 (16)	C25—C26—C27—C27A	42.92 (12)
N11—C12—C13—N24	−125.66 (11)	C13—N24—C27A—C27	−121.73 (11)
O12—C12—C13—C13A	−178.96 (12)	C25—N24—C27A—C27	11.79 (12)
N11—C12—C13—C13A	0.56 (12)	C13—N24—C27A—C21	6.05 (12)
O12—C12—C13—C22	−56.46 (16)	C25—N24—C27A—C21	139.57 (10)
N11—C12—C13—C22	123.05 (11)	C26—C27—C27A—N24	−33.76 (12)
N24—C13—C13A—C14	−58.43 (18)	C26—C27—C27A—C21	−151.72 (10)
C12—C13—C13A—C14	−179.30 (13)	C217—C21—C27A—N24	141.06 (10)
C22—C13—C13A—C14	60.94 (17)	C22—C21—C27A—N24	20.61 (11)
N24—C13—C13A—C17A	120.20 (11)	C217—C21—C27A—C27	−100.97 (12)
C12—C13—C13A—C17A	−0.67 (12)	C22—C21—C27A—C27	138.58 (11)
C22—C13—C13A—C17A	−120.43 (11)	C22—C21—C217—O217	15.85 (17)
C17A—C13A—C14—C15	0.36 (18)	C27A—C21—C217—O217	−98.29 (14)
C13—C13A—C14—C15	178.86 (12)	C22—C21—C217—C211	−168.99 (10)
C13A—C14—C15—C16	−1.24 (19)	C27A—C21—C217—C211	76.86 (13)
C13A—C14—C15—Cl15	−179.66 (9)	O217—C217—C211—C212	−157.38 (13)
C14—C15—C16—C17	0.74 (19)	C21—C217—C211—C212	27.44 (17)
Cl15—C15—C16—C17	179.15 (10)	O217—C217—C211—C216	21.93 (18)
C15—C16—C17—C17A	0.65 (18)	C21—C217—C211—C216	−153.25 (11)
C15—C16—C17—Cl17	−176.92 (10)	C216—C211—C212—C213	−2.22 (19)
C16—C17—C17A—C13A	−1.53 (18)	C217—C211—C212—C213	177.08 (12)
Cl17—C17—C17A—C13A	176.08 (9)	C211—C212—C213—C214	1.8 (2)
C16—C17—C17A—N11	−179.64 (12)	C212—C213—C214—C215	0.5 (2)
Cl17—C17—C17A—N11	−2.02 (18)	C212—C213—C214—Cl14	−179.30 (10)
C14—C13A—C17A—C17	1.01 (18)	C213—C214—C215—C216	−2.29 (19)
C13—C13A—C17A—C17	−177.81 (11)	Cl14—C214—C215—C216	177.56 (10)
C14—C13A—C17A—N11	179.41 (11)	C214—C215—C216—C211	1.78 (19)
C13—C13A—C17A—N11	0.59 (14)	C212—C211—C216—C215	0.43 (19)
C12—N11—C17A—C17	178.06 (12)	C217—C211—C216—C215	−178.90 (11)
C12—N11—C17A—C13A	−0.22 (14)	C21—C22—C227—O227	19.59 (16)
C217—C21—C22—C227	80.51 (13)	C13—C22—C227—O227	−97.90 (13)
C27A—C21—C22—C227	−161.35 (10)	C21—C22—C227—C221	−163.02 (10)
C217—C21—C22—C13	−156.29 (10)	C13—C22—C227—C221	79.49 (13)
C27A—C21—C22—C13	−38.15 (11)	O227—C227—C221—C222	−152.22 (13)
N24—C13—C22—C227	166.02 (9)	C22—C227—C221—C222	30.40 (17)
C13A—C13—C22—C227	37.45 (13)	O227—C227—C221—C226	26.43 (18)
C12—C13—C22—C227	−76.76 (12)	C22—C227—C221—C226	−150.95 (11)
N24—C13—C22—C21	41.50 (11)	C226—C221—C222—C223	−0.5 (2)
C13A—C13—C22—C21	−87.07 (11)	C227—C221—C222—C223	178.15 (12)
C12—C13—C22—C21	158.72 (9)	C221—C222—C223—C224	0.4 (2)
C13A—C13—N24—C25	−30.89 (15)	C222—C223—C224—C225	0.1 (2)
C12—C13—N24—C25	85.14 (13)	C222—C223—C224—Cl24	−179.01 (11)
C22—C13—N24—C25	−157.26 (10)	C223—C224—C225—C226	−0.5 (2)
C13A—C13—N24—C27A	96.99 (12)	Cl24—C224—C225—C226	178.63 (11)
C12—C13—N24—C27A	−146.98 (10)	C224—C225—C226—C221	0.4 (2)
C22—C13—N24—C27A	−29.38 (11)	C222—C221—C226—C225	0.1 (2)
C13—N24—C25—C26	143.79 (10)	C227—C221—C226—C225	−178.57 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12ⁱ	0.852 (16)	2.011 (16)	2.8509 (17)	168.8 (16)
C31—H31A···O12	0.99	2.38	3.192 (8)	139
C31—H31A···N24	0.99	2.54	3.385 (12)	144
C41—H41A···O12	0.99	2.24	3.06 (3)	140
C41—H41A···N24	0.99	2.51	3.33 (4)	140
C51—H51A···O12	0.99	2.29	2.912 (11)	119
C51—H51A···N24	0.99	2.36	3.265 (12)	151

Symmetry code: (i) −x+1, −y+1, −z+1.

Selected geometric parameters (Å, °) top

(a) Ring-puckering parameters
	Q₂	φ₂
(I), ring 2	0.379 (4)	92.8 (6)
(I), ring 3	0.388 (4)	77.8 (6)
(II), ring 2	0.4160 (12)	65.69 (17)
(II), ring 3	0.4257 (14)	267.55 (17)
Ideal envelope		36k
Ideal half-chair		(36k + 18)

(b) Torsion angles
	(I)	(II)
H22—C22—C13—C13A	145	158
H21—C21—C22—H22	-166	-165
H21—C21—C27A—H27A	156	147

In both compounds, ring 1 (atoms N11/C12/C13/C13A/C17A) is planar. The puckering parameters are calculated for the atoms sequences N24–C13–C22–C21–C27A and N24–C25–C26–C27–C27A for rings 2 and 3, respectively. In the ideal values, k represents an integer.

Hydrogen bonds and short intermolecular contacts (Å, °) top

D—H···A	D—H	H···A	D···A	D—H···A
Compound (I)
O212—H212···O12ⁱ	0.87 (3)	1.79 (3)	2.652 (3)	176 (4)
C111—H11B···O227ⁱⁱ	0.99	2.46	3.392 (4)	157
C223—H223···O12ⁱⁱⁱ	0.95	2.56	3.452 (6)	156

Compound (I)
N11—H11···O12ⁱⁱ	0.852 (16)	2.011 (16)	2.8509 (17)	168.8 (16)
C31—H31A···O12	0.99	2.38	3.192 (8)	139
C31—H31A···N24	0.99	2.54	3.385 (12)	144
C41—H41A···O12	0.99	2.24	3.06 (3)	140
C41—H41A···N24	0.99	2.51	3.33 (4)	140
C51—H51A···O12	0.99	2.29	2.912 (11)	119
C51—H51A···N24	0.99	2.36	3.265 (12)	151

Symmetry codes: (i) -y, -z, -x; (ii) -z+1, -x+1, -y+1; (iii) -x, -y, -z+1.

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Synthesis of spiro­[indoline-3,3′-pyrrolizines] by 1,3-dipolar reactions between isatins, L-proline and electron-deficient alkenes

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Synthesis of spiro[indoline-3,3′-pyrrolizines] by 1,3-dipolar reactions between isatins, L-proline and electron-deficient alkenes