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_7131160
_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         'C19 H24 F N O2'
_chemical_formula_sum            'C19 H24 F N O2'
_chemical_formula_weight         317.39
_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             2022-10-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-26 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                98.240(2)
_cell_angle_beta                 98.468(2)
_cell_angle_gamma                91.823(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2396(2)
_cell_length_b                   9.9099(4)
_cell_length_c                   14.5635(6)
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      68.028
_cell_measurement_theta_min      5.854
_cell_volume                     880.22(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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      298.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10704
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.196
_diffrn_reflns_theta_min         5.854
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.057(7)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0682
_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^)+(0.0974P)^2^+0.2087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.2032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2453
_reflns_number_total             3199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06068j2.cif
_cod_data_source_block           20221019s_0m
_cod_depositor_comments
'Adding full bibliography for 7131160--7131161.cif.'
_cod_database_code               7131160
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.811
_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 Ternary CH refined with riding coordinates:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00C), C00G(H00F,H00G), C00K(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00I(H00K), C00J(H00L)
2.d Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J), C00L(H00O,H00P,H00Q), C00M(H00R,H00S,H00T), C00N(H00U,
 H00V,H00W)
;
_shelx_res_checksum              72443
_shelx_hkl_checksum              28444
_olex2_submission_special_instructions 'No special instructions were received'