Consecutive reduction, radical-cyclization, and oxidative-dehydrogenation reaction of ortho-substituted diboryl compound
Yu, Lirong; Li, Yanglizhi; Wang, Xi; Wang, Xingyong; Zhou, Panpan; Jiang, ShangDa; pan, xiaobo; Chem. Commun.  (2017) –; doi:10.1039/C7CC05689C

data_7120529
_publ_section_title
;
 Consecutive reduction, radical-cyclization, and oxidative-dehydrogenation
 reaction of ortho-substituted diboryl compound
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC05689C
_journal_year                    2017
_chemical_formula_moiety         'C54 H56 B2, 2(C H Cl3)'
_chemical_formula_sum            'C56 H58 B2 Cl6'
_chemical_formula_weight         965.34
_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     direct
_audit_creation_date             2017-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-06 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.736(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.3919(7)
_cell_length_b                   8.1281(4)
_cell_length_c                   20.3055(13)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    290.56(10)
_cell_measurement_theta_max      27.1150
_cell_measurement_theta_min      3.7450
_cell_volume                     2537.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.56(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details
;
  1 omega  -28.00   -2.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -38.0000 -120.0000 26

  2 omega  -46.00   65.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000   60.0000 111

  3 omega  -48.00   35.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000    0.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0242653000
_diffrn_orient_matrix_UB_12      0.0289219000
_diffrn_orient_matrix_UB_13      0.0264800000
_diffrn_orient_matrix_UB_21      0.0241440000
_diffrn_orient_matrix_UB_22      -0.0524288000
_diffrn_orient_matrix_UB_23      0.0219582000
_diffrn_orient_matrix_UB_31      0.0309875000
_diffrn_orient_matrix_UB_32      0.0635115000
_diffrn_orient_matrix_UB_33      0.0060810000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10772
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.731
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0502P)^2^+1.5526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1554
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3832
_reflns_number_total             5767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05689c2.cif
_cod_data_source_block           panxb_0518
_cod_original_cell_volume        2537.4(2)
_cod_database_code               7120529
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), C14(H14), C21(H21),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_olex2_date_sample_data_collection 2016-05-18
_olex2_submission_special_instructions 'No special instructions were received'