Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration.
Faizi, Darius J.; Issaian, Adena; Davis, Ashlee J.; Blum, Suzanne A.; Journal of the American Chemical Society 138 (2016) 2126–2129; doi:10.1021/jacs.5b12989

data_4130031
_publ_section_title
;
 Catalyst-Free Synthesis of Borylated Lactones from Esters via
 Electrophilic Oxyboration.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2126
_journal_page_last               2129
_journal_paper_doi               10.1021/jacs.5b12989
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C21 H22 B O4.5'
_chemical_formula_weight         357.19
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 114.3955(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7607(18)
_cell_length_b                   10.0627(9)
_cell_length_c                   20.2687(18)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.21
_cell_volume                     3670.5(6)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0437
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36236
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.386
_diffrn_reflns_theta_max         25.386
_diffrn_reflns_theta_min         1.211
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       needle
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.606
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         6737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0844P)^2^+2.9056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1611
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5266
_reflns_number_total             6737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12989_si_002.cif
_cod_data_source_block           sab15
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C21 H22 B O4.50'
_cod_database_code               4130031
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              11898
_shelx_hkl_checksum              15776