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_1570235
_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         'C22 H22 F2 O2 S'
_chemical_formula_sum            'C22 H22 F2 O2 S'
_chemical_formula_weight         388.45
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-08 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                68.135(2)
_cell_angle_beta                 83.265(2)
_cell_angle_gamma                86.091(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1488(5)
_cell_length_b                   13.7389(7)
_cell_length_c                   15.2173(8)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.37
_cell_volume                     1954.89(17)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            96899
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.137
_diffrn_reflns_theta_min         1.449
_diffrn_source                   'rotating anode x-ray tube'
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.132
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     663
_refine_ls_number_reflns         11514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.5748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9278
_reflns_number_total             11514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04749k2.cif
_cod_data_source_block           dkr117_0m
_cod_depositor_comments
'Adding full bibliography for 1570235--1570236.cif.'
_cod_database_code               1570235
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              16379
_shelx_hkl_checksum              61018