Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures.
Ando, Shin; Miyata, Ryota; Matsunaga, Hirofumi; Ishizuka, Tadao; The Journal of organic chemistry 84 (2019) 128–139; doi:10.1021/acs.joc.8b02480

data_4035899
_publ_section_title
;
 Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              128
_journal_page_last               139
_journal_paper_doi               10.1021/acs.joc.8b02480
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H19 Cl N2'
_chemical_formula_sum            'C19 H19 Cl N2'
_chemical_formula_weight         310.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                71.2729(9)
_cell_angle_beta                 77.0254(10)
_cell_angle_gamma                69.4681(9)
_cell_formula_units_Z            4
_cell_length_a                   11.2159(3)
_cell_length_b                   12.4494(4)
_cell_length_c                   12.6863(5)
_cell_measurement_reflns_used    22548
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.04
_cell_volume                     1558.50(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.041
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656.00
_exptl_crystal_size_max          0.665
_exptl_crystal_size_mid          0.564
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0559P)^2^+1.1414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6505
_reflns_number_total             7142
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b02480_si_002.cif
_cod_data_source_block           RM006-2
_cod_database_code               4035899
_shelx_res_checksum              83047
_shelx_hkl_checksum              89927