Ruthenium(II)-Catalyzed ortho-C-H Chalcogenation of Benzoic Acids via Weak O-Coordination: Synthesis of Chalcogenoxanthones.
Mandal, Anup; Dana, Suman; Sahoo, Harekrishna; Grandhi, Gowri Sankar; Baidya, Mahiuddin; Organic letters 19 (2017) 2430–2433; doi:10.1021/acs.orglett.7b00996

data_1545779
_publ_section_title
;
 Ruthenium(II)-Catalyzed ortho-C-H Chalcogenation of Benzoic Acids via
 Weak O-Coordination: Synthesis of Chalcogenoxanthones.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2430
_journal_page_last               2433
_journal_paper_doi               10.1021/acs.orglett.7b00996
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H14 O2 Se2'
_chemical_formula_sum            'C19 H14 O2 Se2'
_chemical_formula_weight         432.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.9530(10)
_cell_angle_beta                 80.0760(10)
_cell_angle_gamma                82.4580(10)
_cell_formula_units_Z            4
_cell_length_a                   10.1260(3)
_cell_length_b                   12.9083(3)
_cell_length_c                   13.2893(4)
_cell_measurement_reflns_used    8609
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.40
_cell_volume                     1665.16(8)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21799
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.585
_exptl_absorpt_coefficient_mu    4.447
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00130(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+0.7069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4563
_reflns_number_total             5855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00996_si_002.cif
_cod_data_source_block           993
_cod_depositor_comments
;
Adding full bibliography for 1545778--1545779.cif.

2019-03-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C38 H28 O4 Se4'
_cod_original_formula_sum        'C38 H28 O4 Se4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     864.44
_cod_database_code               1545779
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.403
_shelx_estimated_absorpt_t_max   0.665
_shelx_res_checksum              64643
_shelx_hkl_checksum              74226