Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction.
Vasquez, Alena M.; Gurak, John A.; Joe, Candice; Cherney, Emily C.; Engle, Keary M.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c03040

data_4135034
_publ_section_title
;
 Catalytic \a-Hydroarylation of Acrylates and Acrylamides via an
 Interrupted Hydrodehalogenation Reaction.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c03040
_journal_year                    2020
_chemical_formula_moiety         'C42 H29 F6 I P2 Pd, C H2 Cl2'
_chemical_formula_sum            'C43 H31 Cl2 F6 I P2 Pd'
_chemical_formula_weight         1027.82
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.3650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9867(6)
_cell_length_b                   11.4710(5)
_cell_length_c                   24.2026(10)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.393
_cell_measurement_theta_min      2.263
_cell_volume                     4030.6(3)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_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                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32138
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         1.737
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0878 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.8922. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       block
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         7932
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0209P)^2^+1.9847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7007
_reflns_number_total             7932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c03040_si_002.cif
_cod_data_source_block           engle213
_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/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4135034
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.785
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Restrained distances
 Cl1-C43 \\sim Cl1A-C43
 with sigma of 0.02
 Cl2-C43 \\sim Cl2A-C43
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1A) = Uanis(Cl1)
Uanis(Cl2) = Uanis(Cl2A)
4. Others
 Sof(H43C)=Sof(H43D)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(H43A)=Sof(H43B)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C43(H43C,H43D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
  C27(H27), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
;
_shelx_res_checksum              84109
_shelx_hkl_checksum              56656
_olex2_submission_special_instructions 'No special instructions were received'