Synthesis, X-ray characterization and theoretical study of 3a,6:7,9a-diepoxybenzo[de]isoquinoline derivatives: on the importance of F⋯O interactions
Grudova, Mariya V.; Gil, Diego M.; Khrustalev, Victor N.; Nikitina, Eugeniya V.; Sinelshchikova, Anna A.; Grigoriev, Mikhail S.; Kletskov, Alexey V.; Frontera, Antonio; Zubkov, Fedor I.; New Journal of Chemistry 44 (2020) 20167–20180; doi:10.1039/D0NJ04328A

data_7060237
_publ_section_title
;
 Synthesis, X-ray characterization and theoretical study of
 3a,6:7,9a-diepoxybenzo[de]isoquinoline derivatives: on the importance of
 F&#x22EF;O interactions
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20167
_journal_page_last               20180
_journal_paper_doi               10.1039/D0NJ04328A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C20 H14 Cl F6 N O4 S'
_chemical_formula_sum            'C20 H14 Cl F6 N O4 S'
_chemical_formula_weight         513.83
_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     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-18 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.776(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1445(5)
_cell_length_b                   15.3437(6)
_cell_length_c                   10.8727(4)
_cell_measurement_reflns_used    6972
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.81
_cell_measurement_theta_min      2.65
_cell_volume                     1983.39(13)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27385
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         4.337
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
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_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5767
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0441P)^2^+0.7050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4235
_reflns_number_total             5767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj04328a2.cif
_cod_data_source_block           8a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060237
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.831
_shelx_estimated_absorpt_t_max   0.887
_shelx_res_checksum              82854