Short syntheses of 1-substituted dibenzothiophene derivatives.
Welsh, Erin N.; Robertson, Katherine N.; Speed, Alexander W. H.; Organic & biomolecular chemistry 19 (2021) 2000–2007; doi:10.1039/d0ob01839b

data_7157880
_publ_section_title
;
 Short syntheses of 1-substituted dibenzothiophene derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2000
_journal_page_last               2007
_journal_paper_doi               10.1039/d0ob01839b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H23 N O S2'
_chemical_formula_sum            'C19 H23 N O S2'
_chemical_formula_weight         345.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-01-31 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6260(5)
_cell_length_b                   9.2018(5)
_cell_length_c                   22.6467(11)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.57
_cell_measurement_theta_min      2.53
_cell_volume                     1797.58(17)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_collection
;
Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)
;
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            75947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_min         2.389
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.7478
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2398 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6840
_refine_ls_number_restraints     663
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0345P)^2^+0.5513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6112
_reflns_number_total             6840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01839b2.cif
_cod_data_source_block           compound11c_AS025B
_cod_depositor_comments
'Adding full bibliography for 7157879--7157883.cif.'
_cod_database_code               7157880
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.980
_diffrn_source_source            'microfocus sealed tube'
_shelx_res_checksum              47604