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_4123401
_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_formula_moiety         'C50 H40 I N O P2 Pd, C5 H12'
_chemical_formula_sum            'C55 H52 I N O P2 Pd'
_chemical_formula_weight         1038.21
_chemical_name_systematic
;
 ?
;
_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     direct
_audit_creation_date             2014-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.11 svn.r2872 for OlexSys, GUI svn.r4767)
;
_cell_angle_alpha                63.724(3)
_cell_angle_beta                 70.613(3)
_cell_angle_gamma                66.142(3)
_cell_formula_units_Z            2
_cell_length_a                   12.0643(4)
_cell_length_b                   14.4213(5)
_cell_length_c                   16.2330(5)
_cell_measurement_reflns_used    5504
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.4250
_cell_measurement_theta_min      1.9200
_cell_volume                     2275.44(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0239134000
_diffrn_orient_matrix_UB_12      0.0137972000
_diffrn_orient_matrix_UB_13      0.0407172000
_diffrn_orient_matrix_UB_21      -0.0452583000
_diffrn_orient_matrix_UB_22      -0.0263509000
_diffrn_orient_matrix_UB_23      0.0140200000
_diffrn_orient_matrix_UB_31      0.0407604000
_diffrn_orient_matrix_UB_32      -0.0493090000
_diffrn_orient_matrix_UB_33      0.0246105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13465
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.473
_diffrn_reflns_theta_min         1.754
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.515
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.2275
_exptl_crystal_size_mid          0.1837
_exptl_crystal_size_min          0.1325
_refine_diff_density_max         3.822
_refine_diff_density_min         -4.533
_refine_diff_density_rms         0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         9968
_refine_ls_number_restraints     523
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0867
_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^)+(0.1239P)^2^+44.2877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2516
_refine_ls_wR_factor_ref         0.2753
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7932
_reflns_number_total             9968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511441u_si_005.cif
_cod_data_source_block           2014_02_11
_cod_depositor_comments
'Adding full bibliography for 4123400--4123403.cif.'
_cod_original_cell_volume        2275.44(16)
_cod_database_code               4123401
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C47 H38 I Pd P2 N'
_reflns_odcompleteness_completeness 98.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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) groups
2. Restrained distances
 C55-C18 = C9-C18 = C9-C1B = C1B-C1
 1.54 with sigma of 0.005
 C55-C18 \\sim C9-C18 \\sim C9-C1B \\sim C1B-C1
 with sigma of 0.02
3. 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
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B), C1B(H1BA,H1BB)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C17(H17), C21(H21), C22(H22), C24(H24), C25(H25), C28(H28),
 C30(H30), C32(H32), C33(H33), C34(H34), C36(H36), C38(H38), C40(H40), C41(H41),
  C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C59(H59), C60(H60), C2(H2),
 C4(H4), C19(H19), C1A(H1A)
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C39(H39A,H39B,H39C), C55(H55A,H55B,H55C), C1(H1B,H1C,H1D)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'