A highly diastereoselective strain-release Doyle-Kirmse reaction: access to functionalized difluoro(methylene)cyclopropanes.
Midya, Suparnak; Hari, Durga Prasad; Chemical science 14 (2023) 13560–13567; doi:10.1039/d3sc04749k

data_1570236
_publ_section_title
;
 A highly diastereoselective strain-release Doyle-Kirmse reaction: access
 to functionalized difluoro(methylene)cyclopropanes.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              13560
_journal_page_last               13567
_journal_paper_doi               10.1039/d3sc04749k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C20 H18 F2 O2 Se'
_chemical_formula_sum            'C20 H18 F2 O2 Se'
_chemical_formula_weight         407.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-22 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.134(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8764(10)
_cell_length_b                   12.9635(12)
_cell_length_c                   12.9906(12)
_cell_measurement_reflns_used    9694
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.94
_cell_volume                     1830.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            92660
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.590
_diffrn_reflns_theta_min         3.143
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+1.6095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4759
_reflns_number_total             5120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04749k2.cif
_cod_data_source_block           reduced1
_cod_depositor_comments
'Adding full bibliography for 1570235--1570236.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570236
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.505
_shelx_estimated_absorpt_t_max   0.868
_shelx_res_checksum              24880
_shelx_hkl_checksum              61597