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_4035928
_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_sum            'C25 H16 Br2 Cl2 O2'
_chemical_formula_weight         579.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 107.042(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6805(16)
_cell_length_b                   9.6013(11)
_cell_length_c                   18.120(2)
_cell_measurement_reflns_used    1768
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.046
_cell_measurement_theta_min      5.263
_cell_volume                     2275.6(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.653
_exptl_absorpt_coefficient_mu    3.818
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+1.9615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2524
_reflns_number_total             4234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02475_si_002.cif
_cod_data_source_block           cd15300
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035928
_shelx_estimated_absorpt_t_min   0.487
_shelx_estimated_absorpt_t_max   0.637
_shelxl_version_number           2013-4
_shelx_res_checksum              11027
_shelx_hkl_checksum              71860