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_4036576
_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 H24 O2, C4 H8 O2'
_chemical_formula_sum            'C30 H32 O4'
_chemical_formula_weight         456.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-06-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.553(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8861(5)
_cell_length_b                   23.7464(14)
_cell_length_c                   10.5247(15)
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    295.6(2)
_cell_measurement_theta_max      21.2550
_cell_measurement_theta_min      3.7100
_cell_volume                     2454.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295.6(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.8950
_diffrn_measurement_details
;
  1 omega   -7.00   26.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000  -30.0000 22

  2 omega   15.00   93.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000    0.0000 52

  3 omega   -3.00   45.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -77.0000 -180.0000 32

  4 omega  -10.00   93.50   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000  120.0000 69
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0718202000
_diffrn_orient_matrix_UB_12      0.0032563000
_diffrn_orient_matrix_UB_13      -0.0048461000
_diffrn_orient_matrix_UB_21      -0.0041028000
_diffrn_orient_matrix_UB_22      -0.0039997000
_diffrn_orient_matrix_UB_23      -0.0672276000
_diffrn_orient_matrix_UB_31      -0.0073296000
_diffrn_orient_matrix_UB_32      -0.0294559000
_diffrn_orient_matrix_UB_33      0.0085714000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.489
_diffrn_reflns_theta_min         3.123
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74127
_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 light colourless'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0769
_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^)+(0.0779P)^2^+0.8532P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.2243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2818
_reflns_number_total             5570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02806_si_003.cif
_cod_data_source_block           zhangyfei0613
_cod_database_code               4036576
_reflns_odcompleteness_completeness 99.63
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_hkl_checksum              88004
_shelx_res_checksum              10697
_shelxl_version_number           2013-2