Synthesis of 7'-Arylidenespiro[indoline-3,1'-pyrrolizines] and 7'-Arylidenespiro[indene-2,1'-pyrrolizines] via [3 + 2] Cycloaddition and β-C-H Functionalized Pyrrolidine.
Huang, Ying; Fang, Hui-Lin; Huang, Yi-Xin; Sun, Jing; Yan, Chao-Guo; The Journal of organic chemistry 84 (2019) 12437–12451; doi:10.1021/acs.joc.9b01920

data_4033978
_publ_section_title
;
 Synthesis of 7'-Arylidenespiro[indoline-3,1'-pyrrolizines] and
 7'-Arylidenespiro[indene-2,1'-pyrrolizines] via [3 + 2] Cycloaddition and
 \b-C-H Functionalized Pyrrolidine.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12437
_journal_page_last               12451
_journal_paper_doi               10.1021/acs.joc.9b01920
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C34 H28 Br2 N2 O'
_chemical_formula_sum            'C34 H28 Br2 N2 O'
_chemical_formula_weight         640.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                94.0352(15)
_cell_angle_beta                 91.0074(15)
_cell_angle_gamma                112.6476(14)
_cell_formula_units_Z            4
_cell_length_a                   12.8692(7)
_cell_length_b                   14.8165(8)
_cell_length_c                   18.1907(9)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      2.59
_cell_volume                     3189.4(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45451
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.089
_exptl_absorpt_coefficient_mu    2.569
_exptl_absorpt_correction_T_max  0.598
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.590
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         12457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0754P)^2^+2.2441P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6504
_reflns_number_total             12457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01920_si_002.cif
_cod_data_source_block           2p
_cod_database_code               4033978
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.602
_shelx_estimated_absorpt_t_max   0.628
_shelx_res_checksum              69212
_shelx_hkl_checksum              40201
_shelx_fab_checksum              16169