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#$Date: 2023-10-16 10:28:05 +0300 (Mon, 16 Oct 2023) $
#$Revision: 286981 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107628.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8107628
loop_
_publ_author_name
'Li, Wen-Xuan'
'Meng, Qing-Guo'
'Hou, Gui-Ge'
'Liu, Yong-Jun'
'Zhang, Meng'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium
 chloride, C20H18ClF4N3O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1021
_journal_page_last               1023
_journal_paper_doi               10.1515/ncrs-2023-0334
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C20 H18 Cl F4 N3 O'
_chemical_formula_sum            'C20 H18 Cl F4 N3 O'
_chemical_formula_weight         427.82
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 104.798(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6123(7)
_cell_length_b                   11.8692(7)
_cell_length_c                   16.9510(12)
_cell_measurement_reflns_used    3255
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2320
_cell_measurement_theta_min      2.8020
_cell_volume                     1869.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8360
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0444
_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/[σ²(Fo²)+(0.0404P)²+0.4949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2830
_reflns_number_total             3489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0334_suppl_001.cif
_cod_data_source_block           bz4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107628
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6647(2) 0.59481(18) 0.05328(12) 0.0137(5) Uani 1 1 d . . . . .
C2 C 0.6391(2) 0.69956(18) 0.02450(12) 0.0138(5) Uani 1 1 d . . . . .
C3 C 0.6648(2) 0.73180(19) -0.05680(13) 0.0182(5) Uani 1 1 d . . . . .
H3A H 0.685627 0.811749 -0.057009 0.022 Uiso 1 1 calc R U . . .
H3B H 0.578550 0.717169 -0.099836 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7900(2) 0.66525(19) -0.07322(14) 0.0202(5) Uani 1 1 d . . . . .
H4A H 0.790303 0.674163 -0.130057 0.024 Uiso 1 1 calc R U . . .
H4B H 0.879661 0.695684 -0.040107 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8370(2) 0.4603(2) -0.09707(13) 0.0202(5) Uani 1 1 d . . . . .
H5 H 0.875510 0.482712 -0.139638 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8366(2) 0.34673(19) -0.07826(13) 0.0184(5) Uani 1 1 d . . . . .
H6 H 0.873070 0.293799 -0.108171 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7811(2) 0.31328(18) -0.01406(13) 0.0158(5) Uani 1 1 d . . . . .
C8 C 0.7247(2) 0.39275(18) 0.02974(13) 0.0148(5) Uani 1 1 d . . . . .
H8 H 0.687412 0.369583 0.072590 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7239(2) 0.50671(17) 0.00986(12) 0.0137(5) Uani 1 1 d . . . . .
C10 C 0.7818(2) 0.54202(18) -0.05467(13) 0.0161(5) Uani 1 1 d . . . . .
C11 C 0.5803(2) 0.78887(18) 0.07019(13) 0.0151(5) Uani 1 1 d . . . . .
H11 H 0.499470 0.825895 0.031899 0.018 Uiso 1 1 calc R U . . .
C12 C 0.5603(2) 0.63519(18) 0.16456(13) 0.0145(5) Uani 1 1 d . . . . .
C13 C 0.6931(2) 0.87868(18) 0.10639(12) 0.0138(5) Uani 1 1 d . . . . .
C14 C 0.6536(2) 0.98680(18) 0.12123(13) 0.0151(5) Uani 1 1 d . . . . .
C15 C 0.7499(2) 1.07043(18) 0.15486(12) 0.0160(5) Uani 1 1 d . . . . .
H15 H 0.718947 1.142611 0.163358 0.019 Uiso 1 1 calc R U . . .
C16 C 0.8947(2) 1.04267(18) 0.17551(12) 0.0150(5) Uani 1 1 d . . . . .
C17 C 0.9403(2) 0.93474(19) 0.16420(13) 0.0179(5) Uani 1 1 d . . . . .
H17 H 1.037603 0.916662 0.179880 0.022 Uiso 1 1 calc R U . . .
C18 C 0.8387(2) 0.85331(18) 0.12904(13) 0.0170(5) Uani 1 1 d . . . . .
H18 H 0.869147 0.780933 0.120644 0.020 Uiso 1 1 calc R U . . .
C19 C 0.8341(3) 0.11889(19) -0.03067(14) 0.0206(5) Uani 1 1 d . . . . .
H19A H 0.787801 0.119732 -0.087997 0.031 Uiso 1 1 calc R U . . .
H19B H 0.821734 0.046227 -0.008531 0.031 Uiso 1 1 calc R U . . .
H19C H 0.934908 0.134011 -0.022551 0.031 Uiso 1 1 calc R U . . .
C20 C 1.0058(3) 1.12925(19) 0.21086(14) 0.0213(5) Uani 1 1 d . . . . .
Cl1 Cl 0.64277(6) 0.34411(4) 0.24215(3) 0.01817(16) Uani 1 1 d . . . . .
F1 F 0.51039(13) 1.01316(10) 0.10092(8) 0.0220(3) Uani 1 1 d . . . . .
F2 F 1.05961(16) 1.11397(13) 0.29168(8) 0.0367(4) Uani 1 1 d . . . . .
F3 F 0.95714(15) 1.23421(11) 0.20083(9) 0.0372(4) Uani 1 1 d . . . . .
F4 F 1.11989(15) 1.12391(12) 0.17917(10) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.63012(18) 0.56452(15) 0.12681(10) 0.0153(4) Uani 1 1 d . . . . .
H1A H 0.647102 0.503188 0.148457 0.024(7) Uiso 1 1 d R . . . .
N2 N 0.52671(18) 0.73798(15) 0.13564(11) 0.0157(4) Uani 1 1 d . . . . .
H2A H 0.477013 0.777579 0.160731 0.022(7) Uiso 1 1 d R . . . .
N3 N 0.52353(19) 0.60210(16) 0.23133(11) 0.0194(4) Uani 1 1 d . . . . .
H3C H 0.481628 0.646477 0.252868 0.021(7) Uiso 1 1 d R . . . .
H3D H 0.541558 0.537061 0.249716 0.035(8) Uiso 1 1 d R . . . .
O1 O 0.77133(16) 0.20348(12) 0.00972(9) 0.0196(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 N1 119.7(2) . .
C2 C1 C9 122.5(2) . .
N1 C1 C9 117.82(19) . .
C1 C2 C11 121.73(19) . .
C1 C2 C3 120.8(2) . .
C11 C2 C3 117.48(18) . .
C2 C3 C4 110.88(18) . .
C2 C3 H3A 109.5 . .
C4 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
C4 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C10 C4 C3 112.37(18) . .
C10 C4 H4A 109.1 . .
C3 C4 H4A 109.1 . .
C10 C4 H4B 109.1 . .
C3 C4 H4B 109.1 . .
H4A C4 H4B 107.9 . .
C6 C5 C10 122.4(2) . .
C6 C5 H5 118.8 . .
C10 C5 H5 118.8 . .
C5 C6 C7 118.9(2) . .
C5 C6 H6 120.6 . .
C7 C6 H6 120.6 . .
O1 C7 C6 124.8(2) . .
O1 C7 C8 114.89(19) . .
C6 C7 C8 120.3(2) . .
C7 C8 C9 120.5(2) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C10 119.8(2) . .
C8 C9 C1 123.16(19) . .
C10 C9 C1 117.08(19) . .
C5 C10 C9 118.1(2) . .
C5 C10 C4 121.6(2) . .
C9 C10 C4 120.21(19) . .
N2 C11 C2 110.46(17) . .
N2 C11 C13 109.43(17) . .
C2 C11 C13 112.07(17) . .
N2 C11 H11 108.3 . .
C2 C11 H11 108.3 . .
C13 C11 H11 108.3 . .
N2 C12 N3 119.7(2) . .
N2 C12 N1 120.4(2) . .
N3 C12 N1 119.9(2) . .
C14 C13 C18 117.19(19) . .
C14 C13 C11 121.37(19) . .
C18 C13 C11 121.38(19) . .
F1 C14 C15 117.79(19) . .
F1 C14 C13 118.25(18) . .
C15 C14 C13 124.0(2) . .
C14 C15 C16 117.3(2) . .
C14 C15 H15 121.3 . .
C16 C15 H15 121.3 . .
C17 C16 C15 121.2(2) . .
C17 C16 C20 118.3(2) . .
C15 C16 C20 120.5(2) . .
C16 C17 C18 119.3(2) . .
C16 C17 H17 120.4 . .
C18 C17 H17 120.4 . .
C13 C18 C17 121.0(2) . .
C13 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
O1 C19 H19A 109.5 . .
O1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
F3 C20 F4 106.89(18) . .
F3 C20 F2 106.75(19) . .
F4 C20 F2 105.06(19) . .
F3 C20 C16 113.75(19) . .
F4 C20 C16 112.41(19) . .
F2 C20 C16 111.42(18) . .
C12 N1 C1 121.47(18) . .
C12 N1 H1A 114.4 . .
C1 N1 H1A 124.0 . .
C12 N2 C11 124.07(18) . .
C12 N2 H2A 115.8 . .
C11 N2 H2A 119.8 . .
C12 N3 H3C 117.7 . .
C12 N3 H3D 121.1 . .
H3C N3 H3D 121.1 . .
C7 O1 C19 117.12(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.335(3) .
C1 N1 1.416(3) .
C1 C9 1.474(3) .
C2 C11 1.505(3) .
C2 C3 1.510(3) .
C3 C4 1.523(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C10 1.502(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.386(3) .
C5 C10 1.390(3) .
C5 H5 0.9300 .
C6 C7 1.387(3) .
C6 H6 0.9300 .
C7 O1 1.374(3) .
C7 C8 1.393(3) .
C8 C9 1.393(3) .
C8 H8 0.9300 .
C9 C10 1.412(3) .
C11 N2 1.467(3) .
C11 C13 1.532(3) .
C11 H11 0.9800 .
C12 N2 1.324(3) .
C12 N3 1.328(3) .
C12 N1 1.335(3) .
C13 C14 1.380(3) .
C13 C18 1.387(3) .
C14 F1 1.367(2) .
C14 C15 1.378(3) .
C15 C16 1.385(3) .
C15 H15 0.9300 .
C16 C17 1.383(3) .
C16 C20 1.493(3) .
C17 C18 1.395(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 O1 1.433(3) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 F3 1.326(3) .
C20 F4 1.341(3) .
C20 F2 1.347(3) .
N1 H1A 0.8127 .
N2 H2A 0.8567 .
N3 H3C 0.8051 .
N3 H3D 0.8339 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3D Cl1 0.83 2.50 3.258(2) 150.9 . yes
N3 H3C Cl1 0.81 2.64 3.373(2) 151.4 2_655 yes
N2 H2A Cl1 0.86 2.37 3.2026(19) 163.4 2_655 yes
N1 H1A Cl1 0.81 2.47 3.2495(19) 159.8 . yes
C19 H19A Cl1 0.96 2.89 3.845(2) 171.9 4_565 yes
C15 H15 Cl1 0.93 2.92 3.818(2) 162.2 1_565 yes
C11 H11 O1 0.98 2.54 3.306(3) 134.8 3_665 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 C11 2.8(3) . . . .
C9 C1 C2 C11 -179.23(18) . . . .
N1 C1 C2 C3 -175.53(18) . . . .
C9 C1 C2 C3 2.4(3) . . . .
C1 C2 C3 C4 -32.3(3) . . . .
C11 C2 C3 C4 149.26(19) . . . .
C2 C3 C4 C10 45.8(3) . . . .
C10 C5 C6 C7 -0.9(3) . . . .
C5 C6 C7 O1 178.46(19) . . . .
C5 C6 C7 C8 0.9(3) . . . .
O1 C7 C8 C9 -177.94(18) . . . .
C6 C7 C8 C9 -0.2(3) . . . .
C7 C8 C9 C10 -0.6(3) . . . .
C7 C8 C9 C1 179.41(19) . . . .
C2 C1 C9 C8 -166.8(2) . . . .
N1 C1 C9 C8 11.1(3) . . . .
C2 C1 C9 C10 13.2(3) . . . .
N1 C1 C9 C10 -168.82(17) . . . .
C6 C5 C10 C9 0.1(3) . . . .
C6 C5 C10 C4 176.8(2) . . . .
C8 C9 C10 C5 0.7(3) . . . .
C1 C9 C10 C5 -179.35(19) . . . .
C8 C9 C10 C4 -176.12(19) . . . .
C1 C9 C10 C4 3.8(3) . . . .
C3 C4 C10 C5 149.7(2) . . . .
C3 C4 C10 C9 -33.6(3) . . . .
C1 C2 C11 N2 -13.2(3) . . . .
C3 C2 C11 N2 165.27(17) . . . .
C1 C2 C11 C13 109.1(2) . . . .
C3 C2 C11 C13 -72.4(2) . . . .
N2 C11 C13 C14 -83.3(2) . . . .
C2 C11 C13 C14 153.8(2) . . . .
N2 C11 C13 C18 93.8(2) . . . .
C2 C11 C13 C18 -29.1(3) . . . .
C18 C13 C14 F1 -178.73(17) . . . .
C11 C13 C14 F1 -1.6(3) . . . .
C18 C13 C14 C15 1.7(3) . . . .
C11 C13 C14 C15 178.9(2) . . . .
F1 C14 C15 C16 179.75(17) . . . .
C13 C14 C15 C16 -0.7(3) . . . .
C14 C15 C16 C17 -1.2(3) . . . .
C14 C15 C16 C20 178.9(2) . . . .
C15 C16 C17 C18 2.0(3) . . . .
C20 C16 C17 C18 -178.11(19) . . . .
C14 C13 C18 C17 -0.9(3) . . . .
C11 C13 C18 C17 -178.1(2) . . . .
C16 C17 C18 C13 -0.9(3) . . . .
C17 C16 C20 F3 164.1(2) . . . .
C15 C16 C20 F3 -16.0(3) . . . .
C17 C16 C20 F4 42.5(3) . . . .
C15 C16 C20 F4 -137.6(2) . . . .
C17 C16 C20 F2 -75.2(3) . . . .
C15 C16 C20 F2 104.7(2) . . . .
N2 C12 N1 C1 -2.9(3) . . . .
N3 C12 N1 C1 176.80(18) . . . .
C2 C1 N1 C12 6.2(3) . . . .
C9 C1 N1 C12 -171.81(18) . . . .
N3 C12 N2 C11 170.45(19) . . . .
N1 C12 N2 C11 -9.9(3) . . . .
C2 C11 N2 C12 17.0(3) . . . .
C13 C11 N2 C12 -106.8(2) . . . .
C6 C7 O1 C19 5.4(3) . . . .
C8 C7 O1 C19 -176.98(18) . . . .
