Synthesis, crystal structures and anti-inflammatory activity of fluorine-substituted 1,4,5,6-tetrahydrobenzo[<i>h</i>]quinazolin-2-amine derivatives
Sun, Yue; Gao, Zhongfei; Wang, Chunhua; Hou, Guige; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619010118

data_2021733
_publ_section_title
;
 Synthesis, crystal structures and anti-inflammatory activity of
 fluorine-substituted 1,4,5,6-tetrahydrobenzo[<i>h</i>]quinazolin-2-amine
 derivatives
;
_journal_coeditor_code           SK3735
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619010118
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C19 H19 F N3 O +, Cl -'
_chemical_formula_moiety         'C19 H19 F N3 O +, Cl -'
_chemical_formula_sum            'C19 H19 Cl F N3 O'
_chemical_formula_weight         359.82
_chemical_name_systematic
'2-Amino-4-(4-fluorophenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[<i>h</i>]quinazolin-3-ium chloride'
_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-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 102.626(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7725(9)
_cell_length_b                   11.9161(10)
_cell_length_c                   17.1473(15)
_cell_measurement_reflns_used    3293
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2340
_cell_measurement_theta_min      2.9030
_cell_volume                     1749.1(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2017 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7647
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.098
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0568P)^2^+0.5265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                2698
_reflns_number_total             3252
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3735sup1.cif
_cod_data_source_block           4HF
_cod_database_code               2021733
_cod_database_fobs_code          2021733
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.972
_shelx_hkl_checksum              28440
_shelx_res_checksum              47820