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_7120530
_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         '2(C20 H40 K O8), C54 H56 B2, 2(C4 H8 O)'
_chemical_formula_sum            'C102 H152 B2 K2 O18'
_chemical_formula_weight         1766.05
_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                104.712(4)
_cell_angle_beta                 107.141(4)
_cell_angle_gamma                103.546(4)
_cell_formula_units_Z            1
_cell_length_a                   12.8138(5)
_cell_length_b                   13.8501(6)
_cell_length_c                   16.3243(7)
_cell_measurement_reflns_used    3489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.424
_cell_measurement_theta_min      3.780
_cell_volume                     2523.5(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -18.00   25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   60.0000 43

  2 omega -102.00  -77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   90.0000 25

  3 omega  -47.00   54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000    0.0000 101

  4 omega  -45.00   53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -38.0000   90.0000 98

  5 omega    1.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -120.0000 85

  6 omega   16.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -60.0000 61

  7 omega   17.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   30.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0518472000
_diffrn_orient_matrix_UB_12      0.0105950000
_diffrn_orient_matrix_UB_13      0.0372133000
_diffrn_orient_matrix_UB_21      0.0228659000
_diffrn_orient_matrix_UB_22      0.0502374000
_diffrn_orient_matrix_UB_23      -0.0030460000
_diffrn_orient_matrix_UB_31      -0.0238130000
_diffrn_orient_matrix_UB_32      0.0228138000
_diffrn_orient_matrix_UB_33      0.0309466000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18549
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.325
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         9906
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0894
_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^)+(0.1349P)^2^+2.2114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2362
_refine_ls_wR_factor_ref         0.2779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6178
_reflns_number_total             9906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc05689c2.cif
_cod_data_source_block           yulr_1213_2
_cod_database_code               7120530
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.78
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C55) \\sim Ueq, Uanis(C54) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C47) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C48) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(O9) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H44C(0.4) H44D(0.4) H44A(0.6) H44B(0.6) H51C(0.5) H51D(0.5)
 H51A(0.5) H51B(0.5) H53A(0.5) H53B(0.5) H53C(0.5) H53D(0.5) O10(0.5) C48(0.6)
 H48A(0.6) H48B(0.6) C49(0.6) H49A(0.6) H49B(0.6) C50(0.6) H50A(0.6) H50B(0.6)
 C54(0.65) H54A(0.65) H54B(0.65) O9(0.5) C45(0.4) H45A(0.4) H45B(0.4) C46(0.4)
 H46A(0.4) H46B(0.4) C47(0.4) H47A(0.4) H47B(0.4) C55(0.35) H55A(0.35)
 H55B(0.35)
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.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), C44(H44C,H44D), C44(H44A,H44B),
  C51(H51C,H51D), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C53(H53C,
 H53D), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C54(H54A,H54B),
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C55(H55A,H55B), C40(H40A,H40B),
  C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
4.c 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)
4.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 2016-12-13
_olex2_submission_special_instructions 'No special instructions were received'