Enantioselective Palladium-Catalyzed Diboration of 1,1-Disubstituted Allenes
Tang, Wenjun; Liu, Jiawang; Nie, Ming; Zhou, Qing-Hai; Gao, Shen; Jiang, Wenhao; Chung, Lung Wa; Ding, Kuiling; Chem. Sci.  (2017) –; doi:10.1039/C7SC01254C

data_1546042
_publ_section_title
;
 Enantioselective Palladium-Catalyzed Diboration of 1,1-Disubstituted
 Allenes
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01254C
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H31 B2 Br O4'
_chemical_formula_sum            'C22 H31 B2 Br O4'
_chemical_formula_weight         461.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-15 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.930(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1006(17)
_cell_length_b                   6.9951(10)
_cell_length_c                   30.827(5)
_cell_measurement_reflns_used    4389
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.820
_cell_measurement_theta_min      2.36
_cell_volume                     2384.9(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            24139
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.591
_diffrn_reflns_theta_min         1.841
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0786 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8224.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 3064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         14501
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                9343
_reflns_number_total             14501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01254c2.cif
_cod_data_source_block           mo_dm16225_0m
_cod_original_cell_volume        2384.8(6)
_cod_database_code               1546042
_shelx_estimated_absorpt_t_max   0.744
_shelx_estimated_absorpt_t_min   0.622
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C28(H28), C29(H29), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C41(H41A,H41B,
 H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              77193
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'