2,3-Dihalo- and 2,3,6,7-Tetrahaloanthracenes by Vollhardt Trimerization.
Hoffmann, Hendrik; Mukanov, Diana; Ganschow, Michael; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F.; The Journal of organic chemistry 84 (2019) 9826–9834; doi:10.1021/acs.joc.9b01567

data_4034388
_publ_section_title
;
 2,3-Dihalo- and 2,3,6,7-Tetrahaloanthracenes by Vollhardt Trimerization.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9826
_journal_page_last               9834
_journal_paper_doi               10.1021/acs.joc.9b01567
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C74 H78 O2 Si4'
_chemical_formula_weight         1111.72
_chemical_name_common            '18 in manuscript'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 103.887(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1699(9)
_cell_length_b                   12.3706(3)
_cell_length_c                   25.2309(11)
_cell_measurement_reflns_used    13750
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.89
_cell_measurement_theta_min      2.15
_cell_volume                     6414.4(4)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.144.0 (STOE, 2018)'
_computing_data_reduction        'X-Area Integrate 1.73.0.0 (STOE, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_unetI/netI     0.1173
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            39325
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         2.150
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  1.577
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       plank
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         11179
_refine_ls_number_restraints     674
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1784
_refine_ls_R_factor_gt           0.0786
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+8.0227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5615
_reflns_number_total             11179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01567_si_001.cif
_cod_data_source_block           heh27
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034388
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.978
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_shelx_res_checksum              98354
_shelx_hkl_checksum              50271