Borylative transition metal-free couplings of vinyl iodides with various nucleophiles, alkenes or alkynes.
Seidler, Gesa; Schwenzer, Max; Clausen, Florian; Daniliuc, Constantin G.; Studer, Armido; Chemical science 15 (2024) 1672–1678; doi:10.1039/d3sc06131k

data_1570601
_publ_section_title
;
 Borylative transition metal-free couplings of vinyl iodides with various
 nucleophiles, alkenes or alkynes.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1672
_journal_page_last               1678
_journal_paper_doi               10.1039/d3sc06131k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C15 H21 B Cl I O2'
_chemical_formula_weight         406.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX3 v2019.11-0'
_audit_update_record
;
2023-09-07 deposited with the CCDC.	2023-12-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7648(5)
_cell_length_b                   11.9997(5)
_cell_length_c                   9.9650(5)
_cell_measurement_reflns_used    5279
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      25.3313
_cell_measurement_theta_min      2.6569
_cell_volume                     1765.53(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Venture Photon III Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11246
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.66
_diffrn_source                   MoK\a
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.963
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.453
_refine_ls_abs_structure_details
;

Flack x determined using 1182 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     578
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0237
_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^)+0.7738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0448
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2875
_reflns_number_total             3208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06131k2.cif
_cod_data_source_block           stu10009_2c
_cod_depositor_comments
'Adding full bibliography for 1570601--1570606.cif.'
_cod_database_code               1570601
_shelx_res_checksum              56900