Boron Recycling in the Metal-Free Transfer C‒H Borylation of Terminal Alkynes and Heteroarenes
Desrosiers, Vincent; Garcia, Cecilia Zavaleta; Fontaine, Frédéric-Georges; ACS Catalysis  (2020) 11046–; doi:10.1021/acscatal.0c02682

data_4518041
_publ_section_title
;
 Boron Recycling in the Metal-Free Transfer C--H Borylation of Terminal
 Alkynes and Heteroarenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11046
_journal_paper_doi               10.1021/acscatal.0c02682
_journal_year                    2020
_chemical_formula_moiety         'C15 H19 B N2 O2 S Si, C3 H3 O'
_chemical_formula_sum            'C18 H22 B N2 O3 S Si'
_chemical_formula_weight         385.33
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                104.461(2)
_cell_angle_beta                 99.599(2)
_cell_angle_gamma                96.061(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5976(4)
_cell_length_b                   9.2734(5)
_cell_length_c                   12.5694(6)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.876
_cell_measurement_theta_min      4.985
_cell_volume                     945.36(8)
_computing_cell_refinement
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25688
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.115
_diffrn_reflns_theta_min         4.985
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.7340.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       prism
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0481
_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^)+(0.1004P)^2^+0.3033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3534
_reflns_number_total             3602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02682_si_002.cif
_cod_data_source_block           fred75
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4518041
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.632
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H21A-O21 = H22A-O22
 0.87 with sigma of 0.02
3. Others
 Fixed Sof: H21(0.5) H22(0.5) O21(0.5) H21A(0.5) O22(0.5) H22A(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C21(H21),
 C22(H22), C23(H23)
4.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              39272
_shelx_hkl_checksum              30241
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'