Conjunctive functionalization of vinyl boronate complexes with electrophiles: a diastereoselective three-component coupling.
Armstrong, Roly J.; Sandford, Christopher; García-Ruiz, Cristina; Aggarwal, Varinder K.; Chemical communications (Cambridge, England) 53 (2017) 4922–4925; doi:10.1039/c7cc01671a

data_7119992
_publ_section_title
;
 Conjunctive functionalization of vinyl boronate complexes with
 electrophiles: a diastereoselective three-component coupling.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4922
_journal_page_last               4925
_journal_paper_doi               10.1039/c7cc01671a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C27 H31 B O2 Se'
_chemical_formula_sum            'C27 H31 B O2 Se'
_chemical_formula_weight         477.29
_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
_audit_creation_date             2016-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-02-22 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.032(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4862(5)
_cell_length_b                   11.7144(5)
_cell_length_c                   20.1408(9)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.42
_cell_volume                     2419.73(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_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  0.0576
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            53076
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.249
_diffrn_reflns_theta_min         2.023
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.572
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8154.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         7168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+1.2188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5701
_reflns_number_total             7168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01671a2.cif
_cod_data_source_block           rja131rc
_cod_depositor_comments          'Adding full bibliography for 7119992.cif.'
_cod_original_cell_volume        2419.74(19)
_cod_database_code               7119992
_shelxl_version_number           2013-4
_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 Ternary CH refined with riding coordinates:
 C7(H7), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              15524
_olex2_submission_special_instructions 'No special instructions were received'