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_4036578
_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 H4 O'
_chemical_formula_sum            'C30 H28 O3'
_chemical_formula_weight         436.52
_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             2013-07-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.720(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9484(5)
_cell_length_b                   8.6969(2)
_cell_length_c                   16.5941(5)
_cell_measurement_reflns_used    5753
_cell_measurement_temperature    298.5(10)
_cell_measurement_theta_max      70.7770
_cell_measurement_theta_min      5.9530
_cell_volume                     2438.35(12)
_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      298.5(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9232
_diffrn_measured_fraction_theta_max 0.9789
_diffrn_measurement_details
;
  1 omega  -19.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  -30.0000 50

  2 omega  -72.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  -30.0000 45

  3 omega   -5.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   84.0000 -143.6740 26

  4 omega   -5.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -180.0000 26

  5 omega -115.00  -86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   30.0000 29

  6 omega   25.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -60.0000 98

  7 omega   27.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 53

  8 omega   92.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   30.0000 26

  9 omega   29.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000  -90.0000 81

 10 omega   29.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -120.0000 87

 11 omega  119.00  162.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  150.0000 43

 12 omega   68.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  150.0000 37

 13 omega   95.00  124.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000  120.0000 29

 14 omega  124.00  150.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 26

 15 omega   64.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   90.0000 26

 16 omega   41.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -150.0000 26

 17 omega   40.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 40

 18 omega  119.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -150.0000 59

 19 omega   65.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 26

 20 omega   45.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  153.0000 41

 21 omega  107.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   90.0000 26

 22 omega  146.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   90.0000 32

 23 omega   85.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -150.0000 25

 24 omega  144.00  174.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 30

 25 omega  132.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -180.0000 36

 26 omega   37.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000  120.0000 31

 27 omega   60.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   30.0000 44

 28 omega  144.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000  120.0000 26

 29 omega  143.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000 -120.0000 34

 30 omega  120.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   90.0000 38

 31 omega   40.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -60.0000 46

 32 omega   65.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 51

 33 omega   66.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -90.0000 26

 34 omega   90.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 25

 35 omega   61.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 27

 36 omega   61.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0071065000
_diffrn_orient_matrix_UB_12      -0.0279435000
_diffrn_orient_matrix_UB_13      0.0939707000
_diffrn_orient_matrix_UB_21      -0.0887523000
_diffrn_orient_matrix_UB_22      -0.0398542000
_diffrn_orient_matrix_UB_23      -0.0285494000
_diffrn_orient_matrix_UB_31      0.0195698000
_diffrn_orient_matrix_UB_32      -0.1703882000
_diffrn_orient_matrix_UB_33      -0.0087183000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12499
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.067
_diffrn_reflns_theta_min         5.980
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66061
_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 yellow'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0618
_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^)+(0.1023P)^2^+0.7455P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.1930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3924
_reflns_number_total             4562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02806_si_004.cif
_cod_data_source_block           0631
_cod_original_cell_volume        2438.35(13)
_cod_database_code               4036578
_reflns_odcompleteness_completeness 92.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C19(H19), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_hkl_checksum              51187
_shelx_res_checksum              53769
_shelxl_version_number           2013-2