Synthesis of fluorine-containing bicyclo[4.1.1]octenes <i>via</i> photocatalyzed defluorinative (4 + 3) annulation of bicyclo[1.1.0]butanes with <i>gem</i>-difluoroalkenes.
Zhang, Kuan; Gao, Zhengyang; Xia, Yan; Li, Pengfei; Gao, Pin; Duan, Xin-Hua; Guo, Li-Na; Chemical science 16 (2025) 1411–1416; doi:10.1039/d4sc07243j

data_1573464
_publ_section_title
;
 Synthesis of fluorine-containing bicyclo[4.1.1]octenes <i>via</i>
 photocatalyzed defluorinative (4 + 3) annulation of bicyclo[1.1.0]butanes
 with <i>gem</i>-difluoroalkenes.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1411
_journal_page_last               1416
_journal_paper_doi               10.1039/d4sc07243j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C26 H25 F O6'
_chemical_formula_sum            'C26 H25 F O6'
_chemical_formula_weight         452.46
_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             2024-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-05 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                88.0640(10)
_cell_angle_beta                 84.5890(10)
_cell_angle_gamma                80.1740(10)
_cell_formula_units_Z            2
_cell_length_a                   7.28910(10)
_cell_length_b                   9.7884(2)
_cell_length_c                   15.6447(3)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      66.624
_cell_measurement_theta_min      2.837
_cell_volume                     1094.77(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19597
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.624
_diffrn_reflns_theta_max         66.624
_diffrn_reflns_theta_min         2.838
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.7569.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0165(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0714P)^2^+0.3697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3612
_reflns_number_total             3861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07243j2.cif
_cod_data_source_block           cu_240523_zk40mm_0m
_cod_depositor_comments
'Adding full bibliography for 1573464--1573465.cif.'
_cod_database_code               1573464
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.848
_shelx_estimated_absorpt_t_min   0.848
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C13(H13a,H13b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C24(H24a,H24b,H24c), C26(H26a,H26b,H26c)
;
_shelx_res_checksum              58076
_shelx_hkl_checksum              90873
_olex2_submission_special_instructions 'No special instructions were received'