Palladium-catalyzed carbomonofluoromethylation of unactivated alkenes: rapid access to γ-monofluoromethyl carboxylic acid derivatives.
Liu, Xiao-Li; Ji, Shun-Jun; Cai, Zhong-Jian; Chemical communications (Cambridge, England) 60 (2024) 730–733; doi:10.1039/d3cc05380f

data_7132468
_publ_section_title
;
 Palladium-catalyzed carbomonofluoromethylation of unactivated alkenes:
 rapid access to &#x3b3;-monofluoromethyl carboxylic acid derivatives.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              730
_journal_page_last               733
_journal_paper_doi               10.1039/d3cc05380f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C33 H29 F N2 O5 S2'
_chemical_formula_sum            'C33 H29 F N2 O5 S2'
_chemical_formula_weight         616.70
_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             2023-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-24 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                112.009(2)
_cell_angle_beta                 98.334(2)
_cell_angle_gamma                104.508(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3017(4)
_cell_length_b                   13.9812(7)
_cell_length_c                   14.6108(7)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.63
_cell_volume                     1467.25(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            65792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.765
_diffrn_reflns_theta_min         2.629
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1613 before and 0.0994 after correction.
The Ratio of minimum to maximum transmission is 0.8401.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0634P)^2^+0.7478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4494
_reflns_number_total             6846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05380f2.cif
_cod_data_source_block           b221114b_0m
_cod_depositor_comments          'Adding full bibliography for 7132468.cif.'
_cod_database_code               7132468
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C14(H14), C19(H19), C27(H27), C18(H18), C23(H23), C7(H7),
 C5(H5), C24(H24), C1(H1A), C26(H26), C6(H6), C25(H25), C2(H2), C29(H29),
 C3(H3), C33(H33), C32(H32), C31(H31), C30(H30)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              46647
_shelx_hkl_checksum              515
_olex2_submission_special_instructions 'No special instructions were received'