Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities.
Li, Wanfang; Boon, Jie Kang; Zhao, Yu; Chemical science 9 (2018) 600–607; doi:10.1039/c7sc03149a

data_1547805
_publ_section_title
;
 Nickel-catalyzed difunctionalization of allyl moieties using
 organoboronic acids and halides with divergent regioselectivities.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              600
_journal_page_last               607
_journal_paper_doi               10.1039/c7sc03149a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C21H19.50N3O0.50 '
_chemical_formula_sum            'C21 H19.5 N3 O0.5'
_chemical_formula_weight         321.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-19 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.0890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.5176(9)
_cell_length_b                   4.65940(10)
_cell_length_c                   23.3989(6)
_cell_measurement_reflns_used    1688
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.383
_cell_measurement_theta_min      2.770
_cell_volume                     3477.76(15)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.6.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.6.0'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13510
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.383
_diffrn_reflns_theta_min         2.770
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       rod
_exptl_crystal_F_000             1364
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0637P)^2^+2.0991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2819
_reflns_number_total             3419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03149a2.cif
_cod_data_source_block           6a
_cod_depositor_comments          'Adding full bibliography for 1547805.cif.'
_cod_original_formula_sum        'C21 H19.50 N3 O0.50'
_cod_database_code               1547805
_shelx_estimated_absorpt_t_min   0.785
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              80