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_4034387
_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            'C14 H6 Br4'
_chemical_formula_weight         493.83
_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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.7707(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3875(5)
_cell_length_b                   15.8910(13)
_cell_length_c                   6.5698(5)
_cell_measurement_reflns_used    3326
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.56
_cell_volume                     655.11(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         2.563
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    12.262
_exptl_absorpt_correction_T_max  0.3357
_exptl_absorpt_correction_T_min  0.2521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.503
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0193
_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^)+(0.0206P)^2^+0.5395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0462
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1664
_reflns_number_total             1833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01567_si_001.cif
_cod_data_source_block           heh18
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034387
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.131
_shelx_estimated_absorpt_t_max   0.321
_shelx_res_checksum              3513
_shelx_hkl_checksum              3624