Metal-free trans-hydroboration without a B-H bond: reactions of propargyl amines with Lewis acidic boranes
Wang, Jingjing; Zhou, Haiyu; Wei, Junhui; Liu, Fei; Wang, Tongdao; Chemical Communications  (2022) –; doi:10.1039/D2CC02687B

data_7130124
_publ_section_title
;
 Metal-free trans-hydroboration without a B-H bond: reactions of propargyl
 amines with Lewis acidic boranes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02687B
_journal_year                    2022
_chemical_formula_moiety         'C33 H21 B F15 N, C3 H7'
_chemical_formula_sum            'C36 H28 B F15 N'
_chemical_formula_weight         770.40
_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
_audit_creation_date             2022-03-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-22 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.900(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.053(5)
_cell_length_b                   16.413(7)
_cell_length_c                   18.289(9)
_cell_measurement_reflns_used    5172
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      21.221
_cell_measurement_theta_min      2.221
_cell_volume                     3317(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1448
_diffrn_reflns_av_unetI/netI     0.1433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_min         2.168
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7284
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0995 after correction.
The Ratio of minimum to maximum transmission is 0.8294.
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    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             1564
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         7575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0728P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3472
_reflns_number_total             7575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02687b2.cif
_cod_data_source_block           mo_21aug29wjj1_0m_pl
_cod_database_code               7130124
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C17(H17A,H17B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C16(H16), C12(H12), C15(H15), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C18(H18A,
 H18B,H18C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              8209
_olex2_exptl_crystal_mounting_method 'The crystal was mounted on a None'
_olex2_submission_special_instructions 'No special instructions were received'