Water-Soluble Pd-Imidate Complexes: Broadly Applicable Catalysts for the Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed Cross-Coupling.
Gayakhe, Vijay; Ardhapure, Ajaykumar; Kapdi, Anant R.; Sanghvi, Yogesh S.; Serrano, Jose Luis; García, Luis; Pérez, Jose; García, Joaquím; Sánchez, Gregorio; Fischer, Christian; Schulzke, Carola; The Journal of organic chemistry 81 (2016) 2713–2729; doi:10.1021/acs.joc.5b02475

data_4031966
_publ_section_title
;
 Water-Soluble Pd-Imidate Complexes: Broadly Applicable Catalysts for the
 Synthesis of Chemically Modified Nucleosides via Pd-Catalyzed
 Cross-Coupling.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2713
_journal_page_last               2729
_journal_paper_doi               10.1021/acs.joc.5b02475
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rd
_chemical_formula_sum            'C16 H16 N2 O7'
_chemical_formula_weight         348.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3928(13)
_cell_length_b                   14.653(3)
_cell_length_c                   16.301(3)
_cell_measurement_reflns_used    15820
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      58.7
_cell_measurement_theta_min      3.7
_cell_volume                     1527.0(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15534
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.334
_diffrn_reflns_theta_min         3.423
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       platelet
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0534P)^2^+0.4896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1340
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3471
_reflns_number_total             4110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02475_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4031966
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2013-3
_shelx_res_checksum              7959
_shelx_hkl_checksum              58199