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_2311965
_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 H32 N2 O4'
_chemical_formula_moiety         'C28 H32 N2 O4'
_chemical_formula_sum            'C28 H32 N2 O4'
_chemical_formula_weight         460.56
_chemical_name_systematic
;
(1'<i>RS</i>,2'<i>RS</i>,3<i>SR</i>,7a'<i>SR</i>)-2'-Benzoyl-1-hexyl-2-oxo-\
1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-1'-carboxylic
acid
;
_space_group_crystal_system      rhombohedral
_space_group_IT_number           148
_space_group_name_Hall           '-P 3*'
_space_group_name_H-M_alt        'R -3 :R'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                116.980(2)
_cell_angle_beta                 116.980(2)
_cell_angle_gamma                116.980(2)
_cell_formula_units_Z            6
_cell_length_a                   19.9182(9)
_cell_length_b                   19.9182(9)
_cell_length_c                   19.9182(9)
_cell_measurement_reflns_used    5197
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.185
_cell_measurement_theta_min      2.383
_cell_volume                     3496.4(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0670
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35458
_diffrn_reflns_theta_full        27.185
_diffrn_reflns_theta_max         27.185
_diffrn_reflns_theta_min         2.383
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.352
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+2.8884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3672
_reflns_number_total             5194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3676sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        3496.4(11)
_cod_database_code               2311965
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.989
_shelx_hkl_checksum              4084
_shelx_res_checksum              93310
_shelxl_version_number           2.014