Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis
Romine, Andrew M.; Yang, Kin S.; Karunananda, Malkanthi K.; Chen, Jason S.; Engle, Keary M.; ACS Catalysis 9 (2019) 7626–; doi:10.1021/acscatal.9b01471

data_4514845
_publ_section_title
;
 Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether
 Directing Group for Pd(II) Catalysis
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              7626
_journal_paper_doi               10.1021/acscatal.9b01471
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C32 H22 F6 N2 O4 Pd S4, C2 H4 Cl2'
_chemical_formula_sum            'C34 H26 Cl2 F6 N2 O4 Pd S4'
_chemical_formula_weight         946.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                68.768(3)
_cell_angle_beta                 89.673(5)
_cell_angle_gamma                88.327(3)
_cell_formula_units_Z            1
_cell_length_a                   9.0381(9)
_cell_length_b                   10.3207(12)
_cell_length_c                   10.3832(11)
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.38
_cell_volume                     902.40(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10713
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.104
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0657 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.9110.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4397
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0248P)^2^+1.3308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3984
_reflns_number_total             4397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01471_si_014.cif
_cod_data_source_block           engle114_0m_a
_cod_database_code               4514845
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.773
_shelx_estimated_absorpt_t_min   0.760
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F3'-C15 \\sim F1'-C15 \\sim F2'-C15
 with sigma of 0.01
 F3'-C15 \\sim F1-C15 \\sim F1'-C15 \\sim F2-C15 \\sim F2'-C15 \\sim F3-C15
 with sigma of 0.01
3. Others
 Sof(F3)=Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(F2')=Sof(F3')=Sof(F1')=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C9(H9), C13(H13), C11(H11), C10(H10), C3(H3), C12(H12), C4(H4)
;
_shelx_res_checksum              7832
_shelx_hkl_checksum              58378
_olex2_submission_special_instructions 'No special instructions were received'