Cu-catalyzed cascade difluoroalkylation/5-<i>endo</i> cyclization/β-fluorine cleavage of ynones.
Su, Jingwen; Guo, Wenbin; Liu, Yi; Kong, Lichun; Zheng, Hanliang; Zhu, Gangguo; Chemical communications (Cambridge, England) 59 (2023) 1821–1824; doi:10.1039/d2cc06068j

data_7131161
_publ_section_title
;
 Cu-catalyzed cascade difluoroalkylation/5-<i>endo</i>
 cyclization/&#x3b2;-fluorine cleavage of ynones.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1821
_journal_page_last               1824
_journal_paper_doi               10.1039/d2cc06068j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C12 H8 N2 O S'
_chemical_formula_sum            'C12 H8 N2 O S'
_chemical_formula_weight         228.26
_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     dual
_audit_creation_date             2022-06-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-27 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                75.783(2)
_cell_angle_beta                 85.525(2)
_cell_angle_gamma                77.897(2)
_cell_formula_units_Z            4
_cell_length_a                   7.0055(4)
_cell_length_b                   12.2304(8)
_cell_length_c                   12.5433(8)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    125.00
_cell_measurement_theta_max      36.28
_cell_measurement_theta_min      3.353
_cell_volume                     1018.24(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_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      125.00
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            107429
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.393
_diffrn_reflns_theta_min         1.752
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0917 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.9532.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         9900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.4748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8415
_reflns_number_total             9900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06068j2.cif
_cod_data_source_block           mo_2022_02_08_jdm_se_rd2_101_0_a
_cod_depositor_comments
'Adding full bibliography for 7131160--7131161.cif.'
_cod_database_code               7131161
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.922
_diffrn_source_source            'microfocus sealed tube'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              28439
_shelx_hkl_checksum              46020
_olex2_submission_special_instructions 'No special instructions were received'