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_7060238
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 F7 N O4 S'
_chemical_formula_sum            'C20 H14 F7 N O4 S'
_chemical_formula_weight         497.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 99.951(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1261(11)
_cell_length_b                   5.3231(5)
_cell_length_c                   15.7434(14)
_cell_measurement_reflns_used    2037
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      3.37
_cell_volume                     1000.92(16)
_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 0.990
_diffrn_measured_fraction_theta_max 0.992
_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  0.0547
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10943
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.412
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0919
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1410P)^2^+1.4957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2438
_refine_ls_wR_factor_ref         0.2739
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    0.720
_reflns_Friedel_fraction_max     0.659
_reflns_number_gt                2506
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj04328a2.cif
_cod_data_source_block           7b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7060238
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.905
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              81583