Catalyst- and solvent-free Csp2‒H functionalization of 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling under ball-milling
Brahmachari, Goutam; Karmakar, Indrajit; Karmakar, Pintu; Green Chemistry 23 (2021) 4762–4770; doi:10.1039/D1GC01341F

data_7242945
_publ_section_title
;
 Catalyst- and solvent-free Csp2--H functionalization of
 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling under
 ball-milling
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              4762
_journal_page_last               4770
_journal_paper_doi               10.1039/D1GC01341F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C17 H8 F6 N2 O3'
_chemical_formula_sum            'C17 H8 F6 N2 O3'
_chemical_formula_weight         402.25
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-12 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.130(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.1491(11)
_cell_length_b                   7.2268(4)
_cell_length_c                   13.9772(7)
_cell_measurement_reflns_used    1450
_cell_measurement_temperature    150.01(11)
_cell_measurement_theta_max      27.5610
_cell_measurement_theta_min      2.6160
_cell_volume                     3144.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.01(11)
_diffrn_detector_area_resol_mean 15.9974
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4195
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.617
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crys Alis Red'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.1088
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2891
_refine_ls_wR_factor_ref         0.3394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1788
_reflns_number_total             2733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc01341f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7242945.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7242945
_shelx_shelxl_version_number     2018/3
_exptl_absorpt_special_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_shelx_res_checksum              71673