Metal-free regioselective C-H chalcogenylation of coumarins/(hetero)arenes at ambient temperature.
Song, Zengqiang; Ding, Chaochao; Wang, Shaoli; Dai, Qian; Sheng, Yaoguang; Zheng, Zhilong; Liang, Guang; Chemical communications (Cambridge, England) 56 (2020) 1847–1850; doi:10.1039/c9cc09001k

data_7125773
_publ_section_title
;
 Metal-free regioselective C-H chalcogenylation of
 coumarins/(hetero)arenes at ambient temperature.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1847
_journal_page_last               1850
_journal_paper_doi               10.1039/c9cc09001k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C15 H10 O2 Se'
_chemical_formula_sum            'C15 H10 O2 Se'
_chemical_formula_weight         301.19
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-07-31 deposited with the CCDC.	2020-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.104(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7843(10)
_cell_length_b                   6.4537(5)
_cell_length_c                   13.8723(11)
_cell_measurement_reflns_used    1275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6830
_cell_measurement_theta_min      4.2250
_cell_volume                     1258.08(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5395
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         3.474
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0436P)^2^+0.7927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1526
_reflns_number_total             2878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09001k2.cif
_cod_data_source_block           dcc-181-8
_cod_depositor_comments          'Adding full bibliography for 7125773.cif.'
_cod_original_cell_volume        1258.09(17)
_cod_database_code               7125773
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C13(H13), C5(H5), C3(H3), C12(H12), C1(H1), C11(H11),
 C4(H4), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'