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_7129541
_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            'C28 H20 Cl2 N2 O2'
_chemical_formula_weight         487.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4644(7)
_cell_length_b                   11.8934(6)
_cell_length_c                   15.4819(7)
_cell_measurement_reflns_used    4410
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.75
_cell_measurement_theta_min      2.63
_cell_volume                     2295.1(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15384
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.712
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       BLock
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0470P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3284
_reflns_number_total             4038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06544k2.cif
_cod_data_source_block           1756
_cod_database_code               7129541
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              59474