A concise, efficient and versatile synthesis of amino-substituted benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepines: synthesis and spectroscopic characterization, together with the molecular and supramolecular structures of three products and one intermediate
Acosta Quintero, Lina M.; Burgos, Isidro; Palma, Alirio; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618002176

data_2021026
_publ_section_title
;
 A concise, efficient and versatile synthesis of amino-substituted
 benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepines: synthesis and
 spectroscopic characterization, together with the molecular and
 supramolecular structures of three products and one intermediate
;
_journal_coeditor_code           SK3682
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618002176
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C24 H25 N5'
_chemical_formula_moiety         'C24 H25 N5'
_chemical_formula_sum            'C24 H25 N5'
_chemical_formula_weight         383.49
_chemical_name_systematic
6,7,9,11-Tetramethyl-4-(5-methyl-1<i>H</i>-benzo[<i>d</i>]imidazol-1-yl)-6,11-dihydro-5<i>H</i>-benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                97.816(9)
_cell_angle_beta                 112.433(8)
_cell_angle_gamma                94.149(8)
_cell_formula_units_Z            2
_cell_length_a                   9.7866(13)
_cell_length_b                   10.2122(15)
_cell_length_c                   10.9551(14)
_cell_measurement_reflns_used    3263
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.837
_cell_measurement_theta_min      4.411
_cell_volume                     993.4(2)
_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 0.905
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19629
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         63.837
_diffrn_reflns_theta_min         4.411
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2015; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.254
_refine_ls_extinction_coef       0.0099(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0528P)^2^+0.9104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                2474
_reflns_number_total             3263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3682sup1.cif
_cod_data_source_block           VIIIc
_cod_database_code               2021026
_cod_database_fobs_code          2021026
_shelx_estimated_absorpt_t_min   0.788
_shelx_estimated_absorpt_t_max   0.903
_shelx_hkl_checksum              81506
_shelx_res_checksum              16218
_shelxl_version_number           2.014