Biphenyl- and phenylnaphthalenyl-substituted 1<i>H</i>-imidazole-4,5-dicarbonitrile catalysts for the coupling reaction of nucleoside methyl phosphonamidites
Bats, Jan W.; Schell, Peter; Engels, Joachim W.; Acta Crystallographica Section C 69 (2013) 529–533; doi:10.1107/S0108270113009293

data_2018947
_publ_section_title
;
 Biphenyl- and phenylnaphthalenyl-substituted
 1<i>H</i>-imidazole-4,5-dicarbonitrile catalysts for the coupling
 reaction of nucleoside methyl phosphonamidites
;
_journal_coeditor_code           EG3118
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              529
_journal_page_last               533
_journal_paper_doi               10.1107/S0108270113009293
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C20 H16 N4'
_chemical_formula_moiety         'C20 H16 N4'
_chemical_formula_sum            'C20 H16 N4'
_chemical_formula_weight         312.37
_chemical_melting_point          486.0(10)
_chemical_name_systematic
;
2-(2',4',6'-Trimethylbiphenyl-2-yl)-1<i>H</i>-imidazole-4,5-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.578(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3730(10)
_cell_length_b                   10.303(2)
_cell_length_c                   13.279(2)
_cell_measurement_reflns_used    247
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     1691.1(4)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25406
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  600
_diffrn_standards_number         172
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.201
_refine_ls_extinction_coef       0.0160(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.045P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                3014
_reflns_number_total             4381
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            eg3118.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018947
_cod_database_fobs_code          2018947