Synthesis and Application of Substituted 1,16-Dihydroxytetraphenylenes in Catalytic Asymmetric Allylboration of Ketones.
Chai, Guo-Li; Zhu, Bo; Chang, Junbiao; The Journal of organic chemistry 84 (2019) 120–127; doi:10.1021/acs.joc.8b02475

data_4035929
_publ_section_title
;
 Synthesis and Application of Substituted 1,16-Dihydroxytetraphenylenes in
 Catalytic Asymmetric Allylboration of Ketones.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              120
_journal_page_last               127
_journal_paper_doi               10.1021/acs.joc.8b02475
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H12 Br2 O2'
_chemical_formula_sum            'C24 H12 Br2 O2'
_chemical_formula_weight         492.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.866(7)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   22.832(8)
_cell_length_b                   13.024(5)
_cell_length_c                   20.260(8)
_cell_measurement_reflns_used    1762
_cell_measurement_temperature    293
_cell_measurement_theta_max      18.71
_cell_measurement_theta_min      2.40
_cell_volume                     5823(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_av_unetI/netI     0.1668
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23782
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.043
_diffrn_reflns_theta_min         1.816
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.193
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.5687.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       block
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1995
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2713
_reflns_number_total             6910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02475_si_001.cif
_cod_data_source_block           mo_dm15933_0m
_cod_database_code               4035929
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.420
_shelx_estimated_absorpt_t_min   0.338
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C28(H28), C29(H29), C32(H32), C33(H33),
  C34(H34), C35(H35)
;
_shelx_res_checksum              62025
_shelx_hkl_checksum              27465
_olex2_submission_special_instructions 'No special instructions were received'