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_1568621
_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         'C36 H21 B Br2, C H Cl3'
_chemical_formula_sum            'C37 H22 B Br2 Cl3'
_chemical_formula_weight         743.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-09 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                97.089(3)
_cell_angle_beta                 94.219(3)
_cell_angle_gamma                117.910(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6748(3)
_cell_length_b                   10.1293(4)
_cell_length_c                   17.5132(6)
_cell_measurement_reflns_used    4813
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      71.7670
_cell_measurement_theta_min      2.5810
_cell_volume                     1488.08(10)
_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      99.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    -26.00  53.00   1.00    1.00    --   34.23 -38.00  60.00   79
  2  \w     35.00  73.00   1.00    1.00    --   34.23 -99.00 150.00   38
  3  \w     29.00  59.00   1.00    1.00    --   34.23 -99.00  60.00   30
  4  \w     51.00  87.00   1.00    1.00    --   34.23-125.00 -30.00   36
  5  \w     42.00 132.00   1.00    3.00    --  105.88 -77.00   0.00   90
  6  \w     80.00 112.00   1.00    3.00    --  105.88-111.00  30.00   32
  7  \w     68.00 109.00   1.00    3.00    --  105.88 -94.00 -90.00   41
  8  \w     79.00 124.00   1.00    3.00    --  105.88 -61.00-120.00   45
  9  \w     98.00 126.00   1.00    3.00    --  105.88 -15.00-150.00   28
 10  \w     73.00 161.00   1.00    3.00    --  105.88  15.00 -90.00   88
 11  \w    127.00 165.00   1.00    3.00    --  105.88  77.00  90.00   38
 12  \w    115.00 165.00   1.00    3.00    --  105.88 138.00   1.00   50
 13  \w     81.00 110.00   1.00    3.00    --  105.88  77.00  90.00   29
 14  \w     40.00 108.00   1.00    3.00    --  105.88 -30.00 -30.00   68
 15  \w     38.00 114.00   1.00    3.00    --  105.88 -45.00  90.00   76
 16  \w     36.00  62.00   1.00    3.00    --  105.88-111.00  30.00   26
 17  \w     38.00  65.00   1.00    3.00    --  105.88 -15.00-150.00   27
 18  \w     67.00 169.00   1.00    3.00    --  105.88  15.00-180.00  102
 19  \w     55.00 116.00   1.00    3.00    --  105.88-111.00-180.00   61
 20  \w     50.00 124.00   1.00    3.00    --  105.88 -61.00-180.00   74
 21  \w     22.00  50.00   1.00    1.00    --   34.23 -57.00-180.00   28
 22  \w     15.00 103.00   1.00    1.00    --   34.23  38.00 -30.00   88
 23  \w     16.00  98.00   1.00    1.00    --   34.23  38.00  60.00   82
 24  \w      6.00  33.00   1.00    1.00    --  -34.23  57.00-120.00   27
 25  \w    -34.00  37.00   1.00    1.00    --   34.23 -38.00 150.00   71
;
_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      -0.0010964000
_diffrn_orient_matrix_UB_12      -0.0902498000
_diffrn_orient_matrix_UB_13      -0.0777920000
_diffrn_orient_matrix_UB_21      0.0449535000
_diffrn_orient_matrix_UB_22      -0.0997273000
_diffrn_orient_matrix_UB_23      0.0445211000
_diffrn_orient_matrix_UB_31      -0.1766162000
_diffrn_orient_matrix_UB_32      -0.1118594000
_diffrn_orient_matrix_UB_33      -0.0020405000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9009
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         2.571
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65218
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.738
_refine_diff_density_min         -1.286
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0621
_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^)+(0.1314P)^2^+1.6040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4526
_reflns_number_total             5221
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00342f2.cif
_cod_data_source_block           exp_1589
_cod_depositor_comments
'Adding full bibliography for 1568620--1568621.cif.'
_cod_original_cell_volume        1488.07(10)
_cod_database_code               1568621
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C30 H30 B Br2'
_shelx_estimated_absorpt_t_max   0.749
_shelx_estimated_absorpt_t_min   0.260
_reflns_odcompleteness_completeness 99.28
_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.a Ternary CH refined with riding coordinates:
 C37(H37)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C12(H12), C22(H22), C16(H16), C36(H36), C32(H32), C11(H11),
 C35(H35), C6(H6), C17(H17), C24(H24), C23(H23), C1(H1), C10(H10), C4(H4),
 C19(H19), C34(H34), C3(H3), C5(H5), C18(H18), C20(H20)
;
_shelx_res_checksum              36819
_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 2.368
_oxdiff_exptl_absorpt_empirical_full_min 0.705