Practical synthesis of polysubstituted unsymmetric 1,10-phenanthrolines by palladium catalyzed intramolecular oxidative cross coupling of C(sp2)–H and C(sp3)–H bonds of carboxamides
Sun, Wen-Wu; Liu, Ji-Kai; Wu, Bin; Organic Chemistry Frontiers 6 (2019) 544–; doi:10.1039/C8QO01290C

data_1554562
_publ_section_title
;
 Practical synthesis of polysubstituted unsymmetric 1,10-phenanthrolines
 by palladium catalyzed intramolecular oxidative cross coupling of
 C(sp2)--H and C(sp3)--H bonds of carboxamides
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              544
_journal_paper_doi               10.1039/C8QO01290C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C25 H24 N4 O Pd, 0.5(C H2 Cl2), 1.5(H2 O)'
_chemical_formula_sum            'C25.5 H28 Cl N4 O2.5 Pd'
_chemical_formula_weight         572.37
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-04-08 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.795(4)
_cell_length_b                   9.1440(15)
_cell_length_c                   21.256(4)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.26
_cell_measurement_theta_min      2.42
_cell_volume                     5013.6(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49980
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  0.9172
_exptl_absorpt_correction_T_min  0.3602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          1.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         4.795
_refine_diff_density_min         -2.050
_refine_diff_density_rms         0.245
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         13756
_refine_ls_number_restraints     409
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1138P)^2^+37.2340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2181
_reflns_number_gt                11994
_reflns_number_total             13756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo01290c2.cif
_cod_data_source_block           mo_bsh50_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/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 

2022-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C51 H56 Cl2 N8 O5 Pd2'
_cod_original_formula_weight         1144.74
_cod_original_formula_moiety         '2(C25 H24 N4 O Pd), C H2 Cl2, 3(H2 O)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        5013.7(15)
_cod_database_code               1554562