A concise synthesis of a highly substituted 6-(1<i>H</i>-benzimidazol-1-yl)-5-nitrosopyrimidin-2-amine: synthetic sequence and the molecular and supramolecular structures of one product and two intermediates
Cobo, Justo; Vicentes, Daniel E.; Rodríguez, Ricaurte; Marchal, Antonio; Glidewell, Christopher; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618007015

data_2021129
_publ_section_title
;
 A concise synthesis of a highly substituted
 6-(1<i>H</i>-benzimidazol-1-yl)-5-nitrosopyrimidin-2-amine: synthetic
 sequence and the molecular and supramolecular structures of one product
 and two intermediates
;
_journal_coeditor_code           KY3144
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618007015
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C14 H16 N6 O3, C2 H6 O S'
_chemical_formula_moiety         'C14 H16 N6 O3, C2 H6 O S'
_chemical_formula_sum            'C16 H22 N6 O4 S'
_chemical_formula_weight         394.46
_chemical_name_systematic
'<i>N</i>^4^-{2-[(Ethoxymethylidene)amino]phenyl}-6-methoxy-5-nitrosopyrimidine-2,4-diamine dimethyl sulfoxide monosolvate'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 115.351(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8498(11)
_cell_length_b                   17.2238(15)
_cell_length_c                   11.3806(11)
_cell_measurement_reflns_used    4608
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.936
_cell_measurement_theta_min      2.306
_cell_volume                     1921.9(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0657
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            51879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.936
_diffrn_reflns_theta_min         2.306
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0343P)^2^+1.3229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                3808
_reflns_number_total             4606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ky3144sup1.cif
_cod_data_source_block           III
_cod_database_code               2021129
_cod_database_fobs_code          2021129
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.974
_shelx_hkl_checksum              46562
_shelx_res_checksum              771
_shelxl_version_number           2.014