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#$Date: 2023-11-28 10:42:56 +0200 (Tue, 28 Nov 2023) $
#$Revision: 287828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107690.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_8107690
loop_
_publ_author_name
'Yu, Lu'
'Meng, Qing-Guo'
'Hou, Gui-Ge'
'Liu, Yong-Jun'
'Geng, Zi-Kai'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium
 chloride, C20H18ClF4N3O
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1161
_journal_page_last               1163
_journal_paper_doi               10.1515/ncrs-2023-0374
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5254(4)
_cell_length_b                   12.6845(5)
_cell_length_c                   24.1490(11)
_cell_measurement_reflns_used    7131
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7390
_cell_measurement_theta_min      3.5530
_cell_volume                     3836.8(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15274
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.894
_diffrn_reflns_theta_min         3.661
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0485
_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)+(0.0696P)²+3.3077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3361
_reflns_number_total             3805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0374_suppl_001.cif
_cod_data_source_block           xf-2-2-1
_cod_database_code               8107690
_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   0.727
_shelx_estimated_absorpt_t_max   0.773
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.30840(16) 0.12858(17) 0.96703(8) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.23258(17) -0.03005(17) 0.92281(9) 0.0254(4) Uani 1 1 d . . . . .
H2 H 0.196956 -0.087685 0.942537 0.031 Uiso 1 1 calc R U . . .
C3 C 0.42679(17) 0.00620(16) 0.92360(8) 0.0242(4) Uani 1 1 d . . . . .
C4 C 0.34727(17) -0.06157(17) 0.91374(8) 0.0255(4) Uani 1 1 d . . . . .
C5 C 0.37032(17) -0.17070(18) 0.89178(9) 0.0288(5) Uani 1 1 d . . . . .
H5A H 0.307908 -0.197654 0.872669 0.035 Uiso 1 1 calc R U . . .
H5B H 0.386304 -0.217742 0.922342 0.035 Uiso 1 1 calc R U . . .
C6 C 0.46457(17) -0.16732(19) 0.85214(10) 0.0300(5) Uani 1 1 d . . . . .
H6A H 0.486494 -0.238748 0.843386 0.036 Uiso 1 1 calc R U . . .
H6B H 0.442855 -0.133391 0.817949 0.036 Uiso 1 1 calc R U . . .
C7 C 0.66270(18) -0.13206(18) 0.86310(10) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.676359 -0.191188 0.841456 0.036 Uiso 1 1 calc R U . . .
C8 C 0.74780(17) -0.07028(18) 0.88084(9) 0.0295(5) Uani 1 1 d . . . . .
H8 H 0.817419 -0.088135 0.871275 0.035 Uiso 1 1 calc R U . . .
C9 C 0.72789(17) 0.01795(18) 0.91283(9) 0.0272(5) Uani 1 1 d . . . . .
C10 C 0.62408(17) 0.04198(17) 0.92874(9) 0.0267(4) Uani 1 1 d . . . . .
H10 H 0.611432 0.099480 0.951717 0.032 Uiso 1 1 calc R U . . .
C11 C 0.53901(16) -0.01928(17) 0.91057(8) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.55823(17) -0.10792(18) 0.87679(9) 0.0270(4) Uani 1 1 d . . . . .
C13 C 0.17654(16) -0.01599(18) 0.86689(9) 0.0262(4) Uani 1 1 d . . . . .
C14 C 0.20727(17) 0.06165(17) 0.82983(9) 0.0269(5) Uani 1 1 d . . . . .
C15 C 0.16062(19) 0.07353(19) 0.77779(9) 0.0330(5) Uani 1 1 d . . . . .
C16 C 0.0802(2) 0.0040(2) 0.76248(10) 0.0407(6) Uani 1 1 d . . . . .
H16 H 0.047463 0.010721 0.728103 0.049 Uiso 1 1 calc R U . . .
C17 C 0.0488(2) -0.0752(2) 0.79826(11) 0.0405(6) Uani 1 1 d . . . . .
H17 H -0.004475 -0.122119 0.787646 0.049 Uiso 1 1 calc R U . . .
C18 C 0.09643(18) -0.0851(2) 0.85013(9) 0.0326(5) Uani 1 1 d . . . . .
H18 H 0.074436 -0.138563 0.873875 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2015(2) 0.1571(2) 0.73930(10) 0.0400(6) Uani 1 1 d . . . . .
C20 C 0.90917(17) 0.07421(19) 0.90861(10) 0.0318(5) Uani 1 1 d . . . . .
H20A H 0.939270 0.008785 0.921084 0.048 Uiso 1 1 calc R U . . .
H20B H 0.953645 0.131551 0.920490 0.048 Uiso 1 1 calc R U . . .
H20C H 0.904789 0.074016 0.868927 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.53974(4) 0.31046(4) 0.97499(2) 0.02830(16) Uani 1 1 d . . . . .
F1 F 0.28703(10) 0.12832(10) 0.84377(5) 0.0310(3) Uani 1 1 d . . . . .
F2 F 0.30268(14) 0.13926(13) 0.72382(7) 0.0561(5) Uani 1 1 d . . . . .
F3 F 0.20003(13) 0.25397(12) 0.76144(6) 0.0452(4) Uani 1 1 d . . . . .
F4 F 0.14390(17) 0.16261(15) 0.69268(6) 0.0643(5) Uani 1 1 d . . . . .
N1 N 0.40529(14) 0.10538(14) 0.94739(7) 0.0251(4) Uani 1 1 d . . . . .
H1A H 0.458166 0.152892 0.953256 0.033(7) Uiso 1 1 d R . . . .
N2 N 0.22689(14) 0.06415(14) 0.95774(7) 0.0261(4) Uani 1 1 d . . . . .
H2A H 0.164557 0.082781 0.970729 0.031(7) Uiso 1 1 d R . . . .
N3 N 0.29398(14) 0.21691(15) 0.99561(8) 0.0279(4) Uani 1 1 d . . . . .
H3A H 0.347756 0.251484 1.003201 0.045(8) Uiso 1 1 d R . . . .
H3B H 0.229409 0.229185 1.008687 0.042(8) Uiso 1 1 d R . . . .
O1 O 0.80455(12) 0.08656(13) 0.93148(7) 0.0316(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
N2 C1 N3 120.19(19) . .
N2 C1 N1 120.22(19) . .
N3 C1 N1 119.60(19) . .
N2 C2 C4 110.28(17) . .
N2 C2 C13 112.98(17) . .
C4 C2 C13 109.84(17) . .
N2 C2 H2 107.9 . .
C4 C2 H2 107.9 . .
C13 C2 H2 107.9 . .
C4 C3 N1 120.28(19) . .
C4 C3 C11 122.04(19) . .
N1 C3 C11 117.67(18) . .
C3 C4 C2 120.90(19) . .
C3 C4 C5 120.62(19) . .
C2 C4 C5 118.45(18) . .
C4 C5 C6 110.10(18) . .
C4 C5 H5A 109.6 . .
C6 C5 H5A 109.6 . .
C4 C5 H5B 109.6 . .
C6 C5 H5B 109.6 . .
H5A C5 H5B 108.2 . .
C12 C6 C5 111.57(18) . .
C12 C6 H6A 109.3 . .
C5 C6 H6A 109.3 . .
C12 C6 H6B 109.3 . .
C5 C6 H6B 109.3 . .
H6A C6 H6B 108.0 . .
C12 C7 C8 121.8(2) . .
C12 C7 H7 119.1 . .
C8 C7 H7 119.1 . .
C9 C8 C7 119.3(2) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
O1 C9 C8 124.80(19) . .
O1 C9 C10 115.15(19) . .
C8 C9 C10 120.1(2) . .
C9 C10 C11 120.5(2) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C10 C11 C12 119.85(19) . .
C10 C11 C3 122.70(19) . .
C12 C11 C3 117.42(18) . .
C7 C12 C11 118.4(2) . .
C7 C12 C6 121.9(2) . .
C11 C12 C6 119.44(19) . .
C14 C13 C18 117.4(2) . .
C14 C13 C2 121.66(19) . .
C18 C13 C2 120.9(2) . .
F1 C14 C13 119.29(19) . .
F1 C14 C15 117.8(2) . .
C13 C14 C15 122.9(2) . .
C16 C15 C14 118.4(2) . .
C16 C15 C19 122.1(2) . .
C14 C15 C19 119.5(2) . .
C17 C16 C15 120.1(2) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C18 120.4(2) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C13 C18 C17 120.9(2) . .
C13 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
F4 C19 F3 106.3(2) . .
F4 C19 F2 106.5(2) . .
F3 C19 F2 106.2(2) . .
F4 C19 C15 112.0(2) . .
F3 C19 C15 113.33(19) . .
F2 C19 C15 112.1(2) . .
O1 C20 H20A 109.5 . .
O1 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O1 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C1 N1 C3 121.01(18) . .
C1 N1 H1A 117.5 . .
C3 N1 H1A 121.2 . .
C1 N2 C2 124.24(18) . .
C1 N2 H2A 117.4 . .
C2 N2 H2A 118.1 . .
C1 N3 H3A 116.9 . .
C1 N3 H3B 117.4 . .
H3A N3 H3B 125.1 . .
C9 O1 C20 116.42(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.327(3) .
C1 N3 1.328(3) .
C1 N1 1.336(3) .
C2 N2 1.464(3) .
C2 C4 1.507(3) .
C2 C13 1.532(3) .
C2 H2 0.9800 .
C3 C4 1.337(3) .
C3 N1 1.409(3) .
C3 C11 1.476(3) .
C4 C5 1.510(3) .
C5 C6 1.521(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C12 1.516(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C12 1.384(3) .
C7 C8 1.391(3) .
C7 H7 0.9300 .
C8 C9 1.383(3) .
C8 H8 0.9300 .
C9 O1 1.372(3) .
C9 C10 1.390(3) .
C10 C11 1.390(3) .
C10 H10 0.9300 .
C11 C12 1.410(3) .
C13 C14 1.385(3) .
C13 C18 1.392(3) .
C14 F1 1.351(2) .
C14 C15 1.394(3) .
C15 C16 1.389(4) .
C15 C19 1.500(4) .
C16 C17 1.382(4) .
C16 H16 0.9300 .
C17 C18 1.393(3) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 F4 1.339(3) .
C19 F3 1.340(3) .
C19 F2 1.340(3) .
C20 O1 1.431(3) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
N1 H1A 0.9066 .
N2 H2A 0.8740 .
N3 H3A 0.8244 .
N3 H3B 0.8821 .
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 H3B Cl1 0.88 2.46 3.2810(19) 155.0 4_457 yes
N3 H3A O1 0.82 2.65 3.055(2) 112.2 4_457 yes
N3 H3A Cl1 0.82 2.61 3.3365(19) 147.9 . yes
N2 H2A Cl1 0.87 2.45 3.2655(18) 155.8 4_457 yes
N1 H1A Cl1 0.91 2.31 3.1698(18) 159.3 . yes
C20 H20B Cl1 0.96 2.84 3.566(2) 133.0 4_557 yes
C20 H20A Cl1 0.96 2.84 3.764(2) 160.8 8_755 yes
C10 H10 Cl1 0.93 2.88 3.736(2) 154.0 . 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 C3 C4 C2 5.7(3) . . . .
C11 C3 C4 C2 -174.64(18) . . . .
N1 C3 C4 C5 -175.94(19) . . . .
C11 C3 C4 C5 3.7(3) . . . .
N2 C2 C4 C3 -17.2(3) . . . .
C13 C2 C4 C3 108.0(2) . . . .
N2 C2 C4 C5 164.42(18) . . . .
C13 C2 C4 C5 -70.4(2) . . . .
C3 C4 C5 C6 -35.3(3) . . . .
C2 C4 C5 C6 143.11(19) . . . .
C4 C5 C6 C12 49.1(3) . . . .
C12 C7 C8 C9 -0.3(4) . . . .
C7 C8 C9 O1 -178.1(2) . . . .
C7 C8 C9 C10 2.4(3) . . . .
O1 C9 C10 C11 177.41(19) . . . .
C8 C9 C10 C11 -3.1(3) . . . .
C9 C10 C11 C12 1.5(3) . . . .
C9 C10 C11 C3 -176.4(2) . . . .
C4 C3 C11 C10 -169.0(2) . . . .
N1 C3 C11 C10 10.7(3) . . . .
C4 C3 C11 C12 13.1(3) . . . .
N1 C3 C11 C12 -167.27(18) . . . .
C8 C7 C12 C11 -1.3(3) . . . .
C8 C7 C12 C6 172.7(2) . . . .
C10 C11 C12 C7 0.7(3) . . . .
C3 C11 C12 C7 178.7(2) . . . .
C10 C11 C12 C6 -173.5(2) . . . .
C3 C11 C12 C6 4.6(3) . . . .
C5 C6 C12 C7 150.0(2) . . . .
C5 C6 C12 C11 -36.0(3) . . . .
N2 C2 C13 C14 59.4(3) . . . .
C4 C2 C13 C14 -64.2(3) . . . .
N2 C2 C13 C18 -124.3(2) . . . .
C4 C2 C13 C18 112.1(2) . . . .
C18 C13 C14 F1 -177.97(19) . . . .
C2 C13 C14 F1 -1.5(3) . . . .
C18 C13 C14 C15 0.9(3) . . . .
C2 C13 C14 C15 177.3(2) . . . .
F1 C14 C15 C16 178.6(2) . . . .
C13 C14 C15 C16 -0.3(3) . . . .
F1 C14 C15 C19 1.2(3) . . . .
C13 C14 C15 C19 -177.7(2) . . . .
C14 C15 C16 C17 -0.6(4) . . . .
C19 C15 C16 C17 176.7(2) . . . .
C15 C16 C17 C18 0.8(4) . . . .
C14 C13 C18 C17 -0.6(3) . . . .
C2 C13 C18 C17 -177.1(2) . . . .
C16 C17 C18 C13 -0.2(4) . . . .
C16 C15 C19 F4 6.8(3) . . . .
C14 C15 C19 F4 -176.0(2) . . . .
C16 C15 C19 F3 127.0(3) . . . .
C14 C15 C19 F3 -55.8(3) . . . .
C16 C15 C19 F2 -112.8(3) . . . .
C14 C15 C19 F2 64.4(3) . . . .
N2 C1 N1 C3 -9.2(3) . . . .
N3 C1 N1 C3 171.25(19) . . . .
C4 C3 N1 C1 8.7(3) . . . .
C11 C3 N1 C1 -171.00(18) . . . .
N3 C1 N2 C2 174.50(19) . . . .
N1 C1 N2 C2 -5.0(3) . . . .
C4 C2 N2 C1 17.3(3) . . . .
C13 C2 N2 C1 -106.0(2) . . . .
C8 C9 O1 C20 10.4(3) . . . .
C10 C9 O1 C20 -170.14(19) . . . .
