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_7060240
_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 Br F6 N O4 S'
_chemical_formula_sum            'C20 H14 Br F6 N O4 S'
_chemical_formula_weight         558.28
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-10-21 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.291(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.111(3)
_cell_length_b                   5.1760(10)
_cell_length_c                   14.827(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      1.5
_cell_volume                     993.0(4)
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_data_reduction        iMosflm
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.79313
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7742
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        28.417
_diffrn_reflns_theta_max         30.981
_diffrn_reflns_theta_min         1.553
_exptl_absorpt_coefficient_mu    2.965
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_description       prism
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.829
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
;
 Flack x determined using 1752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.041(5)
_refine_ls_extinction_coef       0.041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0557
_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^)+6P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4256
_reflns_number_total             4498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj04328a2.cif
_cod_data_source_block           9b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7060240
_shelx_estimated_absorpt_t_min   0.661
_shelx_estimated_absorpt_t_max   0.795
_shelxl_version_number           2013-4
_shelx_res_checksum              21511