Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Diverse C-H Nucleophiles.
Yang, Kin S.; Gurak, Jr, John A; Liu, Zhen; Engle, Keary M.; Journal of the American Chemical Society 138 (2016) 14705–14712; doi:10.1021/jacs.6b08850

data_4131040
_publ_section_title
;
 Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated
 Alkenes with Diverse C-H Nucleophiles.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14705
_journal_page_last               14712
_journal_paper_doi               10.1021/jacs.6b08850
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C22 H16 N2 O4 Pd, C3 H7 N O'
_chemical_formula_sum            'C25 H23 N3 O5 Pd'
_chemical_formula_weight         551.86
_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
_audit_creation_date             2016-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.080(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1532(7)
_cell_length_b                   22.9508(13)
_cell_length_c                   7.4256(4)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.38
_cell_volume                     2192.0(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0281
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            26864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         1.775
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.4903
_exptl_absorpt_correction_T_min  0.4548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1302 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.9276.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.419
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.413
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0439
_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^)+9.6022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3878
_reflns_number_total             3999
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08850_si_005.cif
_cod_data_source_block           engle17
_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               4131040
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.028) H2(0.032) H3(0.034) H5(0.031) H6(0.033) H7(0.033)
 H11A(0.034) H11B(0.034) H11C(0.034) H11D(0.034) H17(0.032) H18(0.038)
 H19(0.037) H20(0.029) H12(0.028) H13A(0.03) H13B(0.03) H12B(0.028) H13C(0.03)
 H13D(0.03) H23(0.035) H24A(0.057) H24B(0.057) H24C(0.057) H25A(0.051)
 H25B(0.051) H25C(0.051) H1(0.051)
 Fixed X: H1A(1.1285) H2(1.0665) H3(0.9035) H5(0.7373) H6(0.6461) H7(0.7154)
 H11A(0.9037) H11B(0.9284) H11C(0.9576) H11D(0.8883) H17(1.3369) H18(1.505)
 H19(1.6124) H20(1.5517) H12(1.0874) H13A(1.0965) H13B(1.0578) H12B(0.9966)
 H13C(1.1016) H13D(1.1375) H23(0.5833) H24A(0.455) H24B(0.4983) H24C(0.4649)
 H25A(0.7416) H25B(0.6468) H25C(0.6723)
 Fixed Y: H1A(0.2849) H2(0.3797) H3(0.3938) H5(0.3502) H6(0.268) H7(0.1749)
 H11A(0.0315) H11B(0.0143) H11C(0.0254) H11D(0.0188) H17(0.2141) H18(0.2325)
 H19(0.1547) H20(0.059) H12(0.0584) H13A(-0.0061) H13B(0.0442) H12B(0.0614)
 H13C(-0.0101) H13D(0.0357) H23(-0.0089) H24A(-0.0712) H24B(-0.1254) H24C(-
 0.1339) H25A(-0.1267) H25B(-0.1626) H25C(-0.1678)
 Fixed Z: H1A(0.7307) H2(0.7477) H3(0.813) H5(0.8766) H6(0.9215) H7(0.9074)
 H11A(0.6567) H11B(0.8704) H11C(0.8988) H11D(0.6956) H17(0.6715) H18(0.6304)
 H19(0.5867) H20(0.5769) H12(0.9274) H13A(0.6851) H13B(0.5378) H12B(0.57)
 H13C(0.7437) H13D(0.9073) H23(0.8674) H24A(0.8791) H24B(1.0081) H24C(0.7897)
 H25A(0.8635) H25B(0.744) H25C(0.9638)
;
_shelx_res_checksum              88036
_shelx_hkl_checksum              80773
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'