Aromaticity-Dependent Regioselectivity in Pd(II)-Catalyzed C-H Direct Arylation of Aryl Ureas.
Jiang, Pingping; Li, Feng; Xu, Yongbao; Liu, Qingwen; Wang, Jing; Ding, Hong; Yu, Renfu; Wang, Qifeng; Organic letters 17 (2015) 5918–5921; doi:10.1021/acs.orglett.5b03153

data_1555464
_publ_section_title
;
 Aromaticity-Dependent Regioselectivity in Pd(II)-Catalyzed C-H Direct
 Arylation of Aryl Ureas.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5918
_journal_page_last               5921
_journal_paper_doi               10.1021/acs.orglett.5b03153
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C19 H17 Cl N2 O1.425'
_chemical_formula_weight         663.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-11-10T20:18:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.512(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0804(14)
_cell_length_b                   18.104(2)
_cell_length_c                   15.8995(17)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     3675.7(7)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1998
_diffrn_reflns_av_unetI/netI     0.2199
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23472
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.595
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1387
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.01
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6485
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.2165
_refine_ls_R_factor_gt           0.091
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1397P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2799
_refine_ls_wR_factor_ref         0.329
_reflns_Friedel_coverage         0
_reflns_number_gt                2033
_reflns_number_total             6485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03153_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H34 Cl2 N4 O2.85'
_cod_original_formula_weight         663.24
_cod_original_formula_moiety         'C1  H1  N1  O1  Cl1'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555464
_shelx_estimated_absorpt_t_min   0.9
_shelx_estimated_absorpt_t_max   0.996