Efficient (11)C-Carbonylation of Isolated Aryl Palladium Complexes for PET: Application to Challenging Radiopharmaceutical Synthesis.
Andersen, Thomas L.; Friis, Stig D.; Audrain, Hélène; Nordeman, Patrik; Antoni, Gunnar; Skrydstrup, Troels; Journal of the American Chemical Society 137 (2015) 1548–1555; doi:10.1021/ja511441u

data_4123403
_publ_section_title
;
 Efficient (11)C-Carbonylation of Isolated Aryl Palladium Complexes for
 PET: Application to Challenging Radiopharmaceutical Synthesis.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1548
_journal_page_last               1555
_journal_paper_doi               10.1021/ja511441u
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C46 H37 Cl2 I O3 P2 Pd'
_chemical_formula_sum            'C46 H37 Cl2 I O3 P2 Pd'
_chemical_formula_weight         1003.90
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.173(8)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   81.353(8)
_cell_length_b                   11.6324(10)
_cell_length_c                   17.8269(18)
_cell_measurement_reflns_used    9680
_cell_measurement_temperature    100
_cell_measurement_theta_max      19.90
_cell_volume                     16605(3)
_computing_cell_refinement       'SAINT v8.34A (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  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       97
_diffrn_reflns_limit_h_min       -101
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            167121
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        18.000
_diffrn_reflns_theta_max         21.410
_diffrn_reflns_theta_min         1.396
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms Ag'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.8368
_exptl_absorpt_correction_T_min  0.7729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.9236.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_description       block
_exptl_crystal_F_000             8000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.578(18)
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1999
_refine_ls_number_reflns         29043
_refine_ls_number_restraints     2018
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+23.1546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                26225
_reflns_number_total             29043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511441u_si_002.cif
_cod_data_source_block           test
_cod_depositor_comments
'Adding full bibliography for 4123400--4123403.cif.'
_cod_database_code               4123403
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C(H), C1F(H1F), C1G(H1G), C1I(H1I), C1J(H1J), C1O(H1O), C1R(H1R), C1X(H1X),
 C2(H2), C2G(H2G), C29(H29), C33(H33), C54(H54), C57(H57), C75(H75), C97(H97),
 C98(H98), C125(H125), C160(H160), C221(H221), C225(H225), C230(H230),
 C244(H244), C249(H249), C262(H262), C292(H292), C293(H293), C1E(H1E), C1N(H1N),
  C1V(H1V), C2I(H2I), C35(H35), C56(H56), C74(H74), C76(H76), C79(H79),
 C82(H82), C85(H85), C86(H86), C89(H89), C91(H91), C93(H93), C104(H104),
 C108(H108), C114(H114), C117(H117), C121(H121), C124(H124), C145(H145),
 C146(H146), C150(H150), C207(H207), C220(H220), C231(H231), C1B(H1BA),
 C1D(H1D), C1H(H1H), C1S(H1S), C2C(H2C), C2F(H2F), C2J(H2J), C16(H16), C17(H17),
  C26(H26), C46(H46), C67(H67), C73(H73), C101(H101), C107(H107), C115(H115),
 C118(H118), C130(H130), C132(H132), C141(H141), C165(H165), C173(H173),
 C197(H197), C198(H198), C236(H236), C250(H250), C277(H277), C1K(H1K), C1Q(H1Q),
  C1U(H1U), C1Y(H1Y), C1Z(H1Z), C2A(H2A), C2B(H2B), C2D(H2D), C2E(H2E),
 C2M(H2M), C2N(H2N), C3(H3), C6(H6), C7(H7), C24(H24), C65(H65), C92(H92),
 C96(H96), C110(H110), C140(H140), C155(H155), C175(H175), C189(H189),
 C210(H210), C229(H229), C239(H239), C264(H264)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C50(H50A,H50B,H50C), C72(H72A,H72B,H72C), C5(H5A,H5B,H5C),
 C32(H32A,H32B,H32C), C99(H99A,H99B,H99C), C1(H1A,H1B,H1C), C113(H11A,H11B,
 H11C), C176(H17A,H17B,H17C), C68(H68A,H68B,H68C), C200(H20A,H20B,H20C),
 C286(H28A,H28B,H28C)
3.c Idealised tetrahedral OH refined as rotating group:
 O18(H18), O27(H27), O37(H37), O23(H23)
;
_olex2_submission_original_sample_id 2014_10_23
_olex2_submission_special_instructions 'No special instructions were received'