o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions.
Zhang, Yu-Fei; Tian, Wan-Fa; Cao, Xiao-Ping; Kuck, Dietmar; Chow, Hak-Fun; The Journal of organic chemistry 81 (2016) 2308–2319; doi:10.1021/acs.joc.5b02806

data_4036573
_publ_section_title
;
 o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner
 Bay Positions and Use for Single-Wing Extensions.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2308
_journal_page_last               2319
_journal_paper_doi               10.1021/acs.joc.5b02806
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C26 H22 Br2 O2'
_chemical_formula_sum            'C26 H22 Br2 O2'
_chemical_formula_weight         526.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.118(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7101(9)
_cell_length_b                   6.3887(5)
_cell_length_c                   37.130(3)
_cell_measurement_reflns_used    988
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      24.5860
_cell_measurement_theta_min      3.8530
_cell_volume                     4184.3(5)
_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      273.77(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 0.997
_diffrn_measurement_details
;
  1 omega    9.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000   30.0000 80

  2 omega    6.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  -60.0000 83

  3 omega   -5.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  120.0000 26

  4 omega  -48.00  -21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000 -150.0000 27
;
_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      0.0053448000
_diffrn_orient_matrix_UB_12      -0.0202645000
_diffrn_orient_matrix_UB_13      -0.0183831000
_diffrn_orient_matrix_UB_21      0.0395924000
_diffrn_orient_matrix_UB_22      -0.0098384000
_diffrn_orient_matrix_UB_23      0.0045555000
_diffrn_orient_matrix_UB_31      -0.0045677000
_diffrn_orient_matrix_UB_32      -0.1087182000
_diffrn_orient_matrix_UB_33      0.0030167000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.1097
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            7718
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.332
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65791
_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    1.671
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0704
_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^)+(0.0400P)^2^+17.8566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2471
_reflns_number_total             4109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02806_si_005.cif
_cod_data_source_block           zhangyf_1215_2
_cod_database_code               4036573
_reflns_odcompleteness_completeness 99.72
_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, All O(H) groups
2. Restrained distances
 H1-O1
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-17
_olex2_submission_special_instructions 'No special instructions were received'