A concise and efficient synthesis of amino-substituted (1<i>H</i>-benzo[<i>d</i>]imidazol-1-yl)pyrimidine hybrids: synthetic sequence and the molecular and supramolecular structures of six examples
Vicentes, Daniel E.; Rodríguez, Ricaurte; Ochoa, Patricia; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619012087

data_2021779
_publ_section_title
;
 A concise and efficient synthesis of amino-substituted
 (1<i>H</i>-benzo[<i>d</i>]imidazol-1-yl)pyrimidine hybrids: synthetic
 sequence and the molecular and supramolecular structures of six examples
;
_journal_coeditor_code           OV3133
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619012087
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C21 H17 F3 N6 O2, C H4 O'
_chemical_formula_moiety         'C21 H17 F3 N6 O2, C H4 O'
_chemical_formula_sum            'C22 H21 F3 N6 O3'
_chemical_formula_weight         474.45
_chemical_name_systematic
;
<i>N</i>-{2-Amino-6-methoxy-4-[2-(4-methylphenyl)-1<i>H</i>-\
benzo[<i>d</i>]imidazol-1-yl]pyrimidin-5-yl}-2,2,2-trifluoroacetamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL2014
_cell_angle_alpha                90
_cell_angle_beta                 104.180(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6296(8)
_cell_length_b                   11.2206(7)
_cell_length_c                   15.6480(10)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.520
_cell_measurement_theta_min      2.258
_cell_volume                     2149.9(2)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35768
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.258
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+1.4265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                4034
_reflns_number_total             4939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ov3133sup1.cif
_cod_data_source_block           VIIa
_cod_database_code               2021779
_cod_database_fobs_code          2021779
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              12247
_shelx_res_checksum              85881
_shelxl_version_number           2.014