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_7120531
_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         'C70 H88 B2 K2 O4, 2(C4 H8 O)'
_chemical_formula_sum            'C78 H104 B2 K2 O6'
_chemical_formula_weight         1237.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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                72.277(8)
_cell_angle_beta                 70.112(7)
_cell_angle_gamma                67.341(8)
_cell_formula_units_Z            1
_cell_length_a                   12.2166(9)
_cell_length_b                   12.8705(12)
_cell_length_c                   13.0567(12)
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    291.43(10)
_cell_measurement_theta_max      22.6460
_cell_measurement_theta_min      3.7310
_cell_volume                     1745.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      291.43(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -102.00  -72.00   1.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  -30.0000 20

  2 omega   -4.00   26.00   1.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -60.0000 20

  3 omega    3.00   81.00   1.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -180.0000 52

  4 omega   36.00  105.00   1.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000  -60.0000 46

  5 omega    5.00   89.00   1.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -60.0000 56

  6 omega  -38.00   89.50   1.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -30.0000 85
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0135847000
_diffrn_orient_matrix_UB_12      -0.0497917000
_diffrn_orient_matrix_UB_13      -0.0205917000
_diffrn_orient_matrix_UB_21      -0.0017344000
_diffrn_orient_matrix_UB_22      -0.0337301000
_diffrn_orient_matrix_UB_23      0.0544386000
_diffrn_orient_matrix_UB_31      -0.0635847000
_diffrn_orient_matrix_UB_32      0.0098891000
_diffrn_orient_matrix_UB_33      0.0094099000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.245
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.177
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0633P)^2^+0.5256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3901
_reflns_number_total             6847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05689c2.cif
_cod_data_source_block           yulr_1114
_cod_database_code               7120531
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.82
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C14(H14), C21(H21), C23(H23)
2.d 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 2016-11-14
_olex2_submission_special_instructions 'No special instructions were received'