Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation and Benzylation at the Benzene Core of 2-Phenylpyrroles.
Wiest, Johannes M.; Pöthig, Alexander; Bach, Thorsten; Organic letters 18 (2016) 852–855; doi:10.1021/acs.orglett.6b00141

data_1555486
_publ_section_title
;
 Pyrrole as a Directing Group: Regioselective Pd(II)-Catalyzed Alkylation
 and Benzylation at the Benzene Core of 2-Phenylpyrroles.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              852
_journal_page_last               855
_journal_paper_doi               10.1021/acs.orglett.6b00141
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C25 H19 N3 O2 Pd, 0.39(H2 O)'
_chemical_formula_sum            'C25 H19.78 N3 O2.39 Pd'
_chemical_formula_weight         506.88
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                80.687(3)
_cell_angle_beta                 83.765(3)
_cell_angle_gamma                78.031(3)
_cell_formula_units_Z            4
_cell_length_a                   8.4976(4)
_cell_length_b                   11.7441(5)
_cell_length_c                   20.5928(10)
_cell_measurement_reflns_used    5512
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.9880
_cell_measurement_theta_min      2.4575
_cell_volume                     1977.91(16)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX II Control Software (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'
_computing_structure_refinement
'SHELXL2014 (Sheldrick, 2014), SHELXLE (Huebschle, 2011)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       ' \k-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34782
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         8107
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0307P)^2^] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                6037
_reflns_number_total             8107
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol6b00141_si_002.cif
_cod_data_source_block           wiejo2_0m
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H39.56 N6 O4.78 Pd2'
_cod_original_formula_weight         1013.76
_cod_original_formula_moiety         'C50 H38 N6 O4 Pd2, 0.78(H2 O)'
_cod_original_formula_units_Z            2
_cod_database_code               1555486