Six-fold C‒H borylation of hexa-peri-hexabenzocoronene
Nagase, Mai; Kato, Kenta; Yagi, Akiko; Segawa, Yasutomo; Itami, Kenichiro; Beilstein Journal of Organic Chemistry 16 (2020) 391–397; doi:10.3762/bjoc.16.37

data_4038065
_publ_section_title
;
 Six-fold C--H borylation of hexa-peri-hexabenzocoronene
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              391
_journal_page_last               397
_journal_paper_doi               10.3762/bjoc.16.37
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C78 H84 B6 O12, 2(C5 H12)'
_chemical_formula_sum            'C88 H108 B6 O12'
_chemical_formula_weight         1422.60
_space_group_crystal_system      cubic
_space_group_IT_number           205
_space_group_name_Hall           '-P 2ac 2ab 3'
_space_group_name_H-M_alt        'P a -3'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9143(8)
_cell_length_b                   19.9143(8)
_cell_length_c                   19.9143(8)
_cell_measurement_reflns_used    2031
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.7200
_cell_measurement_theta_min      2.0380
_cell_volume                     7897.6(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.817
_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      2.00  56.00   0.50   32.81    --   11.29  36.00 128.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0013720000
_diffrn_orient_matrix_UB_12      -0.0105919000
_diffrn_orient_matrix_UB_13      -0.0339679000
_diffrn_orient_matrix_UB_21      -0.0330037000
_diffrn_orient_matrix_UB_22      -0.0123589000
_diffrn_orient_matrix_UB_23      0.0051782000
_diffrn_orient_matrix_UB_31      -0.0133419000
_diffrn_orient_matrix_UB_32      0.0316911000
_diffrn_orient_matrix_UB_33      -0.0093205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8158
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.931
_diffrn_reflns_theta_min         2.045
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             3048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0733
_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^)+(0.1366P)^2^+0.3202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1570
_reflns_number_total             2594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-37-S2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4038065.cif.'
_cod_original_cell_volume        7897.6(10)
_cod_database_code               4038065
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H B O Cl'
_diffrn_oxdiff_digest_frames
;
0146fe26d4e4d62c60e640b82889a34190000255bce
;
_diffrn_oxdiff_digest_hkl
;
01e82df7ace1101f60aeb6995c9a2510afcec7
;
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_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
2. Restrained distances
 C14-C15 = C15-C16 = C16-C17 = C17-C18
 1.54 with sigma of 0.02
 C14-C16 = C16-C18 = C15-C17
 2.54 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.0007 and sigma for 1-3 distances of 0.0007
4. Others
 Fixed Sof: C14(0.33333) H14A(0.33333) H14B(0.33333) H14C(0.33333)
 C15(0.33333) H15A(0.33333) H15B(0.33333) C16(0.33333) H16A(0.33333)
 H16B(0.33333) C17(0.33333) H17A(0.33333) H17B(0.33333) C18(0.33333)
 H18A(0.33333) H18B(0.33333) H18C(0.33333)
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
5.b Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
;
_shelx_res_checksum              35935
_shelx_hkl_checksum              75067
_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 1.069
_oxdiff_exptl_absorpt_empirical_full_min 0.905