Synthesis, X-ray characterization and theoretical study of all-cis 1,4:2,3:5,8:6,7-tetraepoxynaphthalenes: on the importance of through-space α-effect
Le , Anh T.; Tran, Thanh Van Thi; Le, Duan T.; Gomila, Rosa Maria; Frontera, Antonio; Zubkov, Fedor Ivanovich; CrystEngComm  (2021) –; doi:10.1039/D1CE01040A

data_7243628
_publ_section_title
;
 Synthesis, X-ray characterization and theoretical study of all-cis
 1,4:2,3:5,8:6,7-tetraepoxynaphthalenes: on the importance of
 through-space \a-effect
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01040A
_journal_year                    2021
_chemical_formula_moiety         'C18 H19 N O9, 1.5(H2 O)'
_chemical_formula_sum            'C18 H22 N O10.5'
_chemical_formula_weight         420.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2021-07-09 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                74.88(3)
_cell_angle_beta                 86.45(3)
_cell_angle_gamma                66.47(3)
_cell_formula_units_Z            4
_cell_length_a                   11.287(2)
_cell_length_b                   11.583(2)
_cell_length_c                   15.893(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      3.3
_cell_volume                     1837.0(8)
_computing_cell_refinement       iMosflm
_computing_data_collection       Automar
_computing_data_reduction        iMosflm
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.1566
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21043
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.519
_diffrn_reflns_theta_min         3.315
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       prism
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0016(3)
_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   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         7318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0618
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3945
_reflns_number_total             7318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01040a2.cif
_cod_data_source_block           XB3
_cod_original_formula_sum        'C18 H22 N O10.50'
_cod_database_code               7243628
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2014/6
_shelx_res_checksum              71697
_shelx_hkl_checksum              18687