Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.
O'Duill, Miriam L; Matsuura, Rei; Wang, Yanyan; Turnbull, Joshua L.; Gurak, Jr, John A; Gao, De-Wei; Lu, Gang; Liu, Peng; Engle, Keary M.; Journal of the American Chemical Society 139 (2017) 15576–15579; doi:10.1021/jacs.7b08383

data_4131669
_publ_section_title
;
 Tridentate Directing Groups Stabilize 6-Membered Palladacycles in
 Catalytic Alkene Hydrofunctionalization.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15576
_journal_page_last               15579
_journal_paper_doi               10.1021/jacs.7b08383
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C28 H23 N3 O4, C2 H6 O S'
_chemical_formula_sum            'C30 H29 N3 O5 S'
_chemical_formula_weight         543.62
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_cell_angle_alpha                76.394(3)
_cell_angle_beta                 79.665(4)
_cell_angle_gamma                71.200(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1556(11)
_cell_length_b                   10.4321(13)
_cell_length_c                   16.817(2)
_cell_measurement_reflns_used    6313
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.225
_cell_measurement_theta_min      2.508
_cell_volume                     1308.1(3)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         2.101
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.0909
_exptl_absorpt_correction_T_min  0.0644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1112 before and 0.0771 after correction. The Ratio of minimum to maximum transmission is 0.7085. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       Block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5313
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0360P)^2^+0.4802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4297
_reflns_number_total             5313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08383_si_003.cif
_cod_data_source_block           Engle30
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4131669
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.954
_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,H,H,H) groups
2. Restrained distances
 O2-H2 = N1-H1
 0.95 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(S1S) = Uanis(S1SB)
4. Others
 Sof(S1SB)=Sof(H1SD)=Sof(H1SE)=Sof(H1SF)=Sof(H2SD)=Sof(H2SE)=Sof(H2SF)=1-FVAR(1)
 Sof(S1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
5.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C1S(H1SD,H1SE,H1SF), C2S(H2SA,H2SB,H2SC), C2S(H2SD,H2SE,
 H2SF)
;
_shelx_res_checksum              81101
_shelx_hkl_checksum              2585
_olex2_submission_special_instructions 'No special instructions were received'