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_7120528
_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         'C32 H64 K2 O14, 2(C4 H8 O), C54 H54 B2'
_chemical_formula_sum            'C94 H134 B2 K2 O16'
_chemical_formula_weight         1619.82
_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   geom
_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                95.007(8)
_cell_angle_beta                 105.069(8)
_cell_angle_gamma                93.255(7)
_cell_formula_units_Z            1
_cell_length_a                   12.0148(10)
_cell_length_b                   12.4531(11)
_cell_length_c                   15.4631(15)
_cell_measurement_reflns_used    1202
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2310
_cell_measurement_theta_min      3.5190
_cell_volume                     2217.9(4)
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -40.00   14.00   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -77.0000  -90.0000 45

  2 omega  -16.00   10.40   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000 -180.0000 22

  3 omega  -47.00   46.60   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000    0.0000 78

  4 omega   -1.00   92.60   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   57.0000  150.0000 78

  5 omega   35.00   65.00   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  178.0000   30.0000 25

  6 omega    5.00   92.60   1.2000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   57.0000 -120.0000 73
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0419141000
_diffrn_orient_matrix_UB_12      -0.0444272000
_diffrn_orient_matrix_UB_13      -0.0061142000
_diffrn_orient_matrix_UB_21      -0.0056552000
_diffrn_orient_matrix_UB_22      -0.0048439000
_diffrn_orient_matrix_UB_23      -0.0470210000
_diffrn_orient_matrix_UB_31      0.0444382000
_diffrn_orient_matrix_UB_32      -0.0359763000
_diffrn_orient_matrix_UB_33      0.0058176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_unetI/netI     0.2432
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.344
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88947
_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    1.213
_exptl_crystal_description       needle
_exptl_crystal_F_000             874
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.2134
_refine_ls_R_factor_gt           0.0926
_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^)+(0.0331P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.2156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3003
_reflns_number_total             7780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05689c2.cif
_cod_data_source_block           yulr_1104_3
_cod_database_code               7120528
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.10
_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:
 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), C40(H40A,H40B), C41(H41A,H41B),
  C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), 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_submission_special_instructions 'No special instructions were received'