Synthesis of 1,3-diselenyl-dihydroisobenzofurans via electrochemical radical selenylation with substituted o-divinylbenzenes and diselenides
Wang, Ying; Xu, Ning; Li, Weiwei; Li, Jiaojiao; Huo, Yijun; Zhu, Wenrong; Liu, Qiang; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00254J

data_7158593
_publ_section_title
;
 Synthesis of 1,3-diselenyl-dihydroisobenzofurans via electrochemical
 radical selenylation with substituted o-divinylbenzenes and diselenides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00254J
_journal_year                    2022
_chemical_formula_moiety         'C26 H24 O5 Se2'
_chemical_formula_sum            'C26 H24 O5 Se2'
_chemical_formula_weight         574.37
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-22 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                89.185(11)
_cell_angle_beta                 88.372(13)
_cell_angle_gamma                62.580(9)
_cell_formula_units_Z            4
_cell_length_a                   9.754(3)
_cell_length_b                   9.783(3)
_cell_length_c                   27.883(9)
_cell_measurement_reflns_used    4963
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.226
_cell_measurement_theta_min      2.445
_cell_volume                     2360.8(13)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25339
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.791
_diffrn_reflns_theta_min         2.192
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.0145
_exptl_absorpt_correction_T_min  0.0029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0908 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.2000. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.336
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         8928
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0917
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1681P)^2^+7.5904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2493
_refine_ls_wR_factor_ref         0.2987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5621
_reflns_number_total             8928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00254j2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2360.9(14)
_cod_database_code               7158593
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.858
_shelx_estimated_absorpt_t_min   0.648
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8012(15)
 0.1988(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18), C36(H36), C7(H7), C44(H44), C33(H33), C43(H43), C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C40(H40), C13(H13), C26(H26), C24(H24), C29(H29), C39(H39),
 C16(H16), C5(H5), C51(H51), C14(H14), C6(H6), C52(H52), C15(H15), C2(H2),
 C49(H49), C50(H50), C27(H27), C38(H38), C30(H30), C25(H25), C3(H3), C23(H23),
 C28(H28), C31(H31), C48(H48), C4(H4), C22(H22)
4.c Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C20(H20A,H20B,H20C), C35(H35A,H35B,H35C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'