Copper(i)-catalysed stereoselective debromoborylation of aliphatic 1,1-dibromo-1-alkenes with bis(pinacolato)diboron.
Pang, Yadong; Kojima, Ryoto; Ito, Hajime; Organic & biomolecular chemistry 16 (2018) 6187–6190; doi:10.1039/c8ob01778f

data_7156371
_publ_section_title
;
 Copper(i)-catalysed stereoselective debromoborylation of aliphatic
 1,1-dibromo-1-alkenes with bis(pinacolato)diboron.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6187
_journal_page_last               6190
_journal_paper_doi               10.1039/c8ob01778f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C18 H21 B Br N O4'
_chemical_formula_sum            'C18 H21 B Br N O4'
_chemical_formula_weight         406.08
_chemical_name_systematic        PYD-138
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-06 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.529(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9737(3)
_cell_length_b                   23.8115(9)
_cell_length_c                   11.0278(5)
_cell_measurement_reflns_used    6219
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.6250
_cell_measurement_theta_min      3.0410
_cell_volume                     1810.96(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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      123
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -19.00   6.00   0.50   17.15    --    5.00  38.00   9.00   50
  2  \w    -34.00  64.00   0.50   17.15    --   -7.20  38.00   9.00  196
  3  \w    -97.00  82.00   0.50   17.15    --   -7.20  29.00  90.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1022868000
_diffrn_orient_matrix_UB_12      -0.0029466000
_diffrn_orient_matrix_UB_13      0.0081846000
_diffrn_orient_matrix_UB_21      0.0043874000
_diffrn_orient_matrix_UB_22      0.0180846000
_diffrn_orient_matrix_UB_23      -0.0506762000
_diffrn_orient_matrix_UB_31      0.0095392000
_diffrn_orient_matrix_UB_32      0.0234740000
_diffrn_orient_matrix_UB_33      0.0400055000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15590
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.935
_diffrn_reflns_theta_min         3.075
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    2.292
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0277P)^2^+0.9678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3390
_reflns_number_total             4117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01778f2.cif
_cod_data_source_block           pyd-138
_cod_depositor_comments          'Adding full bibliography for 7156371.cif.'
_cod_database_code               7156371
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.657
_reflns_odcompleteness_completeness 98.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00G(H00G), C00I(H00I), C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00J(H00E,H00F,H00H), C00M(H00J,H00M,H00N), C00N(H00O,H00P,H00Q), C00P(H00R,
 H00S,H00T)
;
_shelx_res_checksum              25774
_shelx_hkl_checksum              78178
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.702