Enantioselective Desymmetrization of Prochiral Cyclopentene-1,3-diones Triggered by Remote C(sp2)-N Bond Formation.
Donthoju, Ashok; Magham, Lakshmi Revati; Singh, Neetu; Manjula, Nemali; Chegondi, Rambabu; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02411

data_4036073
_publ_section_title
;
 Enantioselective Desymmetrization of Prochiral Cyclopentene-1,3-diones
 Triggered by Remote C(sp2)-N Bond Formation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02411
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H16 I N O3'
_chemical_formula_sum            'C20 H16 I N O3'
_chemical_formula_weight         445.23
_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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.742(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8379(5)
_cell_length_b                   14.0015(6)
_cell_length_c                   12.0981(6)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.027
_cell_measurement_theta_min      2.311
_cell_volume                     1920.24(15)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33109
_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         2.121
_exptl_absorpt_coefficient_mu    1.685
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6751
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0449
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5421
_reflns_number_total             6751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02411_si_002.cif
_cod_data_source_block           KA850_0m
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_moiety     '2(C20 H16 I1 N1 O3)'
_cod_original_formula_sum        'C40 H32 I2 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     890.47
_cod_database_code               4036073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.719
_shelx_estimated_absorpt_t_max   0.786
_shelx_res_checksum              65993
_shelx_hkl_checksum              21904