Synthesis of Allenyl-Bdan via the Cu(I)-Catalyzed Borylation of Propargylic Alcohols with the Unsymmetric Diboron Reagent (Bpin-Bdan).
Mao, Lujia; Li, Chunlei; Xiang, Libo; Fu, Dejun; Ma, Wangyang; Ye, Qing; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03319

data_4037845
_publ_section_title
;
 Synthesis of Allenyl-Bdan via the Cu(I)-Catalyzed Borylation of
 Propargylic Alcohols with the Unsymmetric Diboron Reagent (Bpin-Bdan).
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03319
_journal_year                    2020
_chemical_formula_moiety         'C22 H21 B N2 O'
_chemical_formula_sum            'C22 H21 B N2 O'
_chemical_formula_weight         340.22
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9494(7)
_cell_length_b                   9.2406(6)
_cell_length_c                   21.1428(13)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.01
_cell_volume                     1943.8(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0984
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            49766
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         3.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1673 before and 0.0965 after correction. The Ratio of minimum to maximum transmission is 0.7928. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1260 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0456P)^2^+0.1177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2907
_reflns_number_total             3392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03319_si_001.cif
_cod_data_source_block           2k
_cod_database_code               4037845
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C16(H16), C22(H22), C21(H21), C20(H20), C15(H15), C14(H14),
 C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C4(H4a,H4b,H4c), C5(H5a,H5b,H5c)
;
_shelx_res_checksum              18814
_shelx_hkl_checksum              59623
_olex2_submission_special_instructions 'No special instructions were received'