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_4034386
_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            'C38 H24 O2.5 S2'
_chemical_formula_weight         583.68
_chemical_name_common            '10 in manuscript'
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 103.906(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   42.404(6)
_cell_length_b                   7.2286(7)
_cell_length_c                   20.011(4)
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      48.25
_cell_measurement_theta_min      4.56
_cell_volume                     5954.0(16)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_data_reduction        'X-Area Integrate 1.71.0.0 (STOE, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.1368
_diffrn_reflns_av_unetI/netI     0.1196
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7121
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        42.086
_diffrn_reflns_theta_max         42.086
_diffrn_reflns_theta_min         7.531
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  2.611
_exptl_absorpt_correction_T_min  0.427
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       plate
_exptl_crystal_F_000             2424
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     146
_refine_ls_restrained_S_all      3.115
_refine_ls_R_factor_all          0.4247
_refine_ls_R_factor_gt           0.3019
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5621
_refine_ls_wR_factor_ref         0.6120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1029
_reflns_number_total             2043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01567_si_001.cif
_cod_data_source_block           heh14
_cod_original_cell_volume        5954.0(17)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C38 H24 O2.50 S2'
_cod_database_code               4034386
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.963
_exptl_absorpt_special_details   'X-Area LANA 1.70.0.0 (STOE, 2017)'
_shelx_res_checksum              15283
_shelx_hkl_checksum              44920