Diastereoselective access to [4,4]-carbospirocycles: governance of thermodynamic enolates with organocatalyst in vinylogous cascade annulation
Bhajammanavar, Vinod; Mallik, Sumitava; Choutipalli, Venkata Surya Kumar; Subramanian, Venkatesan; Baidya, Mahiuddin; Chemical Communications  (2022) –; doi:10.1039/D1CC06544K

data_7129539
_publ_section_title
;
 Diastereoselective access to [4,4]-carbospirocycles: governance of
 thermodynamic enolates with organocatalyst in vinylogous cascade
 annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06544K
_journal_year                    2022
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-07-13 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.829(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5635(6)
_cell_length_b                   6.7073(3)
_cell_length_c                   15.8118(8)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.49
_cell_measurement_theta_min      2.47
_cell_volume                     1014.15(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.130
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0388P)^2^+0.0483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2715
_reflns_number_total             3558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06544k2.cif
_cod_data_source_block           1090
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129539
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              24991