Synthesis of spiro[indoline-3,3'-pyrrolizines] by 1,3-dipolar reactions between isatins, L-proline and electron-deficient alkenes.
Quiroga, Jairo; Romo, Pablo; Cobo, Justo; Glidewell, Christopher; Acta crystallographica. Section C, Structural chemistry 73 (2017) 1109–1115; doi:10.1107/S2053229617016072

data_2311966
_publ_section_title
;
 Synthesis of spiro[indoline-3,3'-pyrrolizines] by 1,3-dipolar reactions
 between isatins, L-proline and electron-deficient alkenes.
;
_journal_coeditor_code           SK3676
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              1109
_journal_page_last               1115
_journal_paper_doi               10.1107/S2053229617016072
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C28 H20 Cl4 N2 O3, 0.981C H2 Cl2'
_chemical_formula_moiety         'C28 H20 Cl4 N2 O3, 0.981(C H2 Cl2)'
_chemical_formula_sum            'C28.981 H21.962 Cl5.962 N2 O3'
_chemical_formula_weight         657.57
_chemical_name_systematic
;(1'<i>RS</i>,2'<i>RS</i>,3<i>SR</i>,7a'<i>SR</i>)-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
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 99.325(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.800(4)
_cell_length_b                   12.511(5)
_cell_length_c                   18.638(5)
_cell_measurement_reflns_used    6780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.532
_cell_measurement_theta_min      2.215
_cell_volume                     2945.3(17)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS86 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            92566
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         2.215
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             1340.8
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.553
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6778
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+2.0129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                6162
_reflns_number_total             6778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3676sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311966
_shelx_estimated_absorpt_t_min   0.800
_shelx_estimated_absorpt_t_max   0.910
_shelx_hkl_checksum              53338
_shelx_res_checksum              3724
_shelxl_version_number           2.014