Palladium-Catalyzed Oxidative Heck Reaction of Non-activated Alkenes Directed by Fluorinated Alcohol
Zhu, Baiyao; Li, Zhewei; Chen, Fulin; Xiong, Wenfang; Tan, Xiaobin; Lei, Ming; Jiang, Huanfeng; Wu, Wanqing; Chemical Communications  (2022) –; doi:10.1039/D2CC04921J

data_7130883
_publ_section_title
;
 Palladium-Catalyzed Oxidative Heck Reaction of Non-activated Alkenes
 Directed by Fluorinated Alcohol
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04921J
_journal_year                    2022
_chemical_formula_moiety         'C23 H19 F3 O'
_chemical_formula_sum            'C23 H19 F3 O'
_chemical_formula_weight         368.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2022-05-09 deposited with the CCDC.	2022-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.663(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1043(13)
_cell_length_b                   5.8211(4)
_cell_length_c                   16.8027(12)
_cell_measurement_reflns_used    2397
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      28.8270
_cell_measurement_theta_min      2.2680
_cell_volume                     1750.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -86.00   6.00   1.00    6.50    --  -11.59 -77.00-150.00   92
  2  \w    -85.00   9.00   1.00    6.50    --  -11.59 -57.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0379023000
_diffrn_orient_matrix_UB_12      -0.0190050000
_diffrn_orient_matrix_UB_13      -0.0043246000
_diffrn_orient_matrix_UB_21      0.0081295000
_diffrn_orient_matrix_UB_22      -0.0294942000
_diffrn_orient_matrix_UB_23      0.0413413000
_diffrn_orient_matrix_UB_31      -0.0082709000
_diffrn_orient_matrix_UB_32      -0.1166678000
_diffrn_orient_matrix_UB_33      -0.0097413000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.276
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0611P)^2^+0.8693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2366
_reflns_number_total             3066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04921j2.cif
_cod_data_source_block           hg0725
_cod_database_code               7130883
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C9(H9), C11(H11), C2(H2), C8(H8), C19(H19), C13(H13),
 C23(H23), C3(H3), C14(H14), C5(H5), C4(H4), C22(H22), C21(H21), C20(H20)
;
_shelx_res_checksum              70576
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.528