Fully-fused boron-doped olympicenes: modular synthesis, tunable optoelectronic properties, and one-electron reduction.
Guo, Jing; Zhang, Kaihua; Wang, Yanpei; Wei, Haipeng; Xiao, Wang; Yang, Kun; Zeng, Zebing; Chemical science 14 (2023) 4158–4165; doi:10.1039/d3sc00342f

data_1568620
_publ_section_title
;
 Fully-fused boron-doped olympicenes: modular synthesis, tunable
 optoelectronic properties, and one-electron reduction.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              4158
_journal_page_last               4165
_journal_paper_doi               10.1039/d3sc00342f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C30 H17 B Br2'
_chemical_formula_sum            'C30 H17 B Br2'
_chemical_formula_weight         548.07
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-06 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                74.925(2)
_cell_angle_beta                 89.781(2)
_cell_angle_gamma                89.984(2)
_cell_formula_units_Z            3
_cell_length_a                   10.2031(2)
_cell_length_b                   11.8054(3)
_cell_length_c                   16.1220(4)
_cell_measurement_reflns_used    11538
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6080
_cell_measurement_theta_min      3.8870
_cell_volume                     1875.08(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -106.00 -23.00   1.00    6.00    --  -34.48 -19.00 -30.00   83
  2  \w     18.00 102.00   1.00    6.00    --   34.48  57.00 -60.00   84
  3  \w     46.00  88.00   1.00    6.00    --   34.48-125.00-120.00   42
  4  \w    -32.00  41.00   1.00    6.00    --   34.48 -57.00-180.00   73
  5  \w     22.00  64.00   1.00    6.00    --   34.48  38.00 150.00   42
  6  \w     27.00  78.00   1.00    6.00    --   34.48-129.00  28.00   51
  7  \w     23.00 102.00   1.00    6.00    --   34.48  38.00  90.00   79
  8  \w     29.00  73.00   1.00    6.00    --   34.48 -99.00  90.00   44
  9  \w     42.00 100.00   1.00    6.00    --   34.48  57.00 150.00   58
 10  \w     57.00 120.00   1.00   24.00    --  105.88 -61.00 -30.00   63
 11  \w    100.00 165.00   1.00   24.00    --  105.88  61.00 -90.00   65
 12  \w     37.00 102.00   1.00   24.00    --  105.88 -94.00 120.00   65
 13  \w     64.00 116.00   1.00   24.00    --  105.88-111.00 -30.00   52
 14  \w     55.00 109.00   1.00   24.00    --  105.88 -94.00-150.00   54
 15  \w    100.00 127.00   1.00   24.00    --  105.88 111.00 120.00   27
 16  \w     36.00 116.00   1.00   24.00    --  105.88 -30.00  90.00   80
 17  \w    120.00 162.00   1.00   24.00    --  105.88  45.00 120.00   42
 18  \w    119.00 148.00   1.00   24.00    --  105.88 178.00-180.00   29
 19  \w     84.00 120.00   1.00   24.00    --  105.88  30.00 -90.00   36
 20  \w     80.00 106.00   1.00   24.00    --  105.88 178.00-180.00   26
 21  \w     60.00 122.00   1.00   24.00    --  105.88 -45.00-120.00   62
 22  \w    141.00 174.00   1.00   24.00    --  105.88 111.00 120.00   33
 23  \w     37.00 112.00   1.00   24.00    --  105.88 -45.00-180.00   75
 24  \w     65.00 111.00   1.00   24.00    --  105.88 -61.00  90.00   46
 25  \w     37.00 139.00   1.00   24.00    --  105.88 -15.00 -60.00  102
 26  \w   -100.00 -56.00   1.00    7.50    --  -34.98 -57.00 -90.00   44
 27  \w    -49.00 -18.00   1.00    7.50    --  -34.98 -57.00 -90.00   31
 28  \w    -14.00  36.00   1.00    7.50    --  -34.98  19.00 -30.00   50
 29  \w    -38.00  36.00   1.00    7.50    --  -34.98  19.00  60.00   74
 30  \w     -1.00  24.00   1.00    7.50    --   34.98  94.00 -20.43   25
 31  \w      3.00  53.00   1.00    7.50    --   34.98 -99.00 -90.00   50
 32  \w     23.00  63.00   1.00    7.50    --   34.98-125.00  60.00   40
 33  \w     -1.00  49.00   1.00    7.50    --   34.98 -57.00  90.00   50
 34  \w      6.00  31.00   1.00    7.50    --   40.00  90.00 -39.46   25
 35  \w      7.00  32.00   1.00    7.50    --   40.00  88.00 145.33   25
 36  \w     14.00  43.00   1.00    7.50    --   44.00  82.00-103.77   29
 37  \w     16.00  41.00   1.00    7.50    --   44.00  80.00  91.71   25
 38  \w     20.00  45.00   1.00    7.50    --   48.00  80.00 169.27   25
 39  \w     18.00  43.00   1.00    7.50    --   48.00  82.00 -60.19   25
 40  \w     18.00  44.00   1.00    7.50    --   48.00  82.00  52.92   26
 41  \w     92.00 119.00   1.00    7.50    --   52.00  76.00 144.24   27
 42  \w     27.00  67.00   1.00    7.50    --   52.00  76.00 144.24   40
 43  \w     29.00  54.00   1.00    7.50    --   56.00  77.00   2.09   25
 44  \w     98.00 123.00   1.00    7.50    --   56.00  75.00  30.53   25
 45  \w     32.00  77.00   1.00    7.50    --   56.00  75.00  30.53   45
 46  \w     29.00  55.00   1.00    7.50    --   56.00  77.00 101.34   26
 47  \w     32.00  83.00   1.00    7.50    --   56.00  76.00-110.56   51
 48  \w     29.00  61.00   1.00    7.50    --   56.00  77.00 -46.38   32
 49  \w     30.00  62.00   1.00    7.50    --   56.00  75.00-154.74   32
 50  \w     30.00  80.00   1.00    7.50    --   56.00  75.00 122.16   50
 51  \w     67.00 103.00   1.00    7.50    --   56.00  77.00 -46.38   36
 52  \w     54.00  82.00   1.00   30.00    --   76.00  69.00-141.36   28
 53  \w     93.00 143.00   1.00   30.00    --   76.00  69.00-141.36   50
 54  \w     79.00 112.00   1.00   30.00    --  105.25  77.00 150.00   33
 55  \w     79.00 108.00   1.00   30.00    --  105.25  77.00-150.00   29
 56  \w     79.00 105.00   1.00   30.00    --  105.25  77.00-120.00   26
 57  \w     79.00 104.00   1.00   30.00    --  105.25  77.00 -30.00   25
 58  \w     79.00 105.00   1.00   30.00    --  105.25  77.00  30.00   26
 59  \w     79.00 105.00   1.00   30.00    --  105.25  77.00 120.00   26
 60  \w     79.00 105.00   1.00   30.00    --  105.25  77.00  60.00   26
 61  \w     79.00 110.00   1.00   30.00    --  105.25  77.00 -90.00   31
 62  \w     87.00 154.00   1.00   30.00    --  105.25  61.00  30.00   67
 63  \w     79.00 124.00   1.00   30.00    --  105.25  77.00-180.00   45
 64  \w     87.00 145.00   1.00   30.00    --  105.25  61.00 -30.00   58
 65  \w     79.00 105.00   1.00   30.00    --  105.25  77.00   0.00   26
 66  \w     87.00 159.00   1.00   30.00    --  105.25  61.00  60.00   72
 67  \w     87.00 154.00   1.00   30.00    --  105.25  61.00   0.00   67
 68  \w     87.00 153.00   1.00   30.00    --  105.25  61.00  90.00   66
 69  \w     88.00 114.00   1.00   30.00    --  105.25  61.00 150.00   26
 70  \w     79.00 131.00   1.00   30.00    --  105.25  77.00 -60.00   52
 71  \w     79.00 104.00   1.00   30.00    --  105.25  77.00  90.00   25
 72  \w     88.00 114.00   1.00   30.00    --  105.25  61.00 -90.00   26
 73  \w     87.00 114.00   1.00   30.00    --  105.25  61.00 120.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0390555000
_diffrn_orient_matrix_UB_12      -0.1280773000
_diffrn_orient_matrix_UB_13      0.0420753000
_diffrn_orient_matrix_UB_21      -0.0258180000
_diffrn_orient_matrix_UB_22      0.0195294000
_diffrn_orient_matrix_UB_23      0.0894723000
_diffrn_orient_matrix_UB_31      -0.1435494000
_diffrn_orient_matrix_UB_32      -0.0384648000
_diffrn_orient_matrix_UB_33      -0.0042398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25099
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        65.085
_diffrn_reflns_theta_max         65.085
_diffrn_reflns_theta_min         3.878
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 3873 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     892
_refine_ls_number_reflns         11583
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+3.4636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.811
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                10120
_reflns_number_total             11583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00342f2.cif
_cod_data_source_block           exp_592_sq
_cod_depositor_comments
;
Adding full bibliography for 1568620--1568621.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C90 H51 B3 Br6'
_cod_original_formula_weight         1644.20
_cod_original_formula_moiety         '3(C30 H17 B Br2)'
_cod_original_formula_units_Z            1
_cod_database_code               1568620
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H20 Br2 B'
_shelx_estimated_absorpt_t_max   0.817
_shelx_estimated_absorpt_t_min   0.486
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C20" \\sim C21" \\sim C22" \\sim C23" \\sim C24" \\sim C19": within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C11") \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C30') \\sim Ueq, Uanis(C6")
\\sim Ueq, Uanis(C5") \\sim Ueq, Uanis(C11') \\sim Ueq, Uanis(B1) \\sim Ueq,
Uanis(B1') \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C12') \\sim Ueq, Uanis(C5') \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C11'(H11'), C11(H11), C17"(H17"), C14'(H14'), C20(H20), C10'(H10'),
 C12'(H12'), C11"(H11"), C12(H12), C24(H24), C12"(H12"), C27'(H27'), C23(H23),
 C18(H18), C10(H10), C14"(H14"), C10"(H10"), C16(H16), C14(H14), C18"(H18"),
 C18'(H18'), C16"(H16"), C17'(H17'), C26'(H26'), C17(H17), C16'(H16'), C22(H22),
  C28'(H28'), C21(H21), C24'(H24'), C27"(H27"), C21"(H21"), C26(H26), C29(H29),
 C28(H28), C26"(H26"), C20"(H20"), C21'(H21'), C30(H30), C28"(H28"), C29'(H29'),
  C29"(H29"), C20'(H20'), C27(H27), C22"(H22"), C30'(H30'), C23'(H23'),
 C30"(H30"), C22'(H22'), C23"(H23"), C24"(H24")
;
_shelx_res_checksum              11716
_shelx_fab_checksum              44337
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.899
_oxdiff_exptl_absorpt_empirical_full_min 0.649