Ruthenium(II)-Catalyzed Regioselective Ortho Amidation of Imidazo Heterocycles with Isocyanates.
Shakoor, S. M. Abdul; Kumari, Santosh; Khullar, Sadhika; Mandal, Sanjay K.; Kumar, Anil; Sakhuja, Rajeev; The Journal of organic chemistry 81 (2016) 12340–12349; doi:10.1021/acs.joc.6b02282

data_4037418
_publ_section_title
;
 Ruthenium(II)-Catalyzed Regioselective Ortho Amidation of Imidazo
 Heterocycles with Isocyanates.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12340
_journal_page_last               12349
_journal_paper_doi               10.1021/acs.joc.6b02282
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H18 Cl N3 O'
_chemical_formula_sum            'C22 H18 Cl N3 O'
_chemical_formula_weight         375.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.4130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8372(5)
_cell_length_b                   10.5719(5)
_cell_length_c                   16.5469(8)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      25.0809
_cell_measurement_theta_min      2.4618
_cell_volume                     1895.73(16)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'APEX2 (Bruker)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            48825
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'sealed tube'
_diffrn_source_type              'micro focus'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.8148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2619
_reflns_number_total             3370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02282_si_002.cif
_cod_data_source_block           3d
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037418