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_2021023
_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          'C22 H24 N4'
_chemical_formula_moiety         'C22 H24 N4'
_chemical_formula_sum            'C22 H24 N4'
_chemical_formula_weight         344.45
_chemical_name_systematic
<i>N</i>,2,6,11-Tetramethyl-<i>N</i>-phenyl-6,11-dihydro-5<i>H</i>-benzo[<i>b</i>]pyrimido[5,4-<i>f</i>]azepin-4-amine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2020(19)
_cell_length_b                   16.609(3)
_cell_length_c                   19.850(6)
_cell_measurement_reflns_used    4234
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.509
_cell_measurement_theta_min      2.742
_cell_volume                     3693.2(14)
_computing_cell_refinement
;
DIRAX/LSQ (Duisenberg, 1992)
;
_computing_data_collection
;
COLLECT (Bruker, 2008)
;
_computing_data_reduction
;
EvalCCD  (Duisenberg <i>et al.</i>,  2003)
;
_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      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34307
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.048
_diffrn_reflns_theta_min         3.638
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2008; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.240
_refine_ls_extinction_coef       0.0053(3)
_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   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0151P)^2^+4.0628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                2278
_reflns_number_total             3635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3682sup1.cif
_cod_data_source_block           III
_cod_database_code               2021023
_cod_database_fobs_code          2021023
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              20336
_shelx_res_checksum              3259
_shelxl_version_number           2.014