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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151794.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_7151794
loop_
_publ_author_name
'Vicente, José'
'Chicote, María Teresa'
'Martínez-Martínez, Antonio Jesús'
'Bautista, Delia'
'Jones, Peter G.'
_publ_section_title
;
 Synthesis of a family of 3-alkyl- or 3-aryl-substituted
 1,2-dihydroquinazolinium salts and their isomerization to
 4-iminium-1,2,3,4-tetrahydroquinolines.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2279
_journal_page_last               2285
_journal_paper_doi               10.1039/c0ob00982b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C17 H23 F3 N2 O3 S'
_chemical_formula_weight         392.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.094(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9025(11)
_cell_length_b                   13.0141(13)
_cell_length_c                   13.1294(14)
_cell_measurement_reflns_used    5469
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.21
_cell_volume                     1852.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21913
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.8676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0594P)²+0.9260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                3698
_reflns_number_total             4547
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00982b.txt
_cod_data_source_block           j30s
_cod_original_sg_symbol_H-M      'P 2(1)/n'
_cod_database_code               7151794
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22462(15) 0.49314(12) 0.09481(12) 0.0188(3) Uani 1 1 d . . .
N1 N 0.24468(13) 0.39814(11) 0.12731(10) 0.0190(3) Uani 1 1 d . . .
C2 C 0.12398(15) 0.55022(13) 0.13016(13) 0.0200(3) Uani 1 1 d . . .
C3 C 0.03245(16) 0.49385(13) 0.17539(13) 0.0220(3) Uani 1 1 d . . .
N2 N 0.05914(14) 0.39608(12) 0.20451(12) 0.0249(3) Uani 1 1 d . . .
H02 H 0.005(2) 0.3561(17) 0.2203(18) 0.035(6) Uiso 1 1 d . . .
C4 C -0.08242(16) 0.53984(15) 0.18609(14) 0.0259(4) Uani 1 1 d . . .
H4 H -0.1463 0.5009 0.2115 0.031 Uiso 1 1 calc R . .
C5 C -0.10168(17) 0.64085(15) 0.15981(14) 0.0281(4) Uani 1 1 d . . .
H5 H -0.1789 0.6718 0.1681 0.034 Uiso 1 1 calc R . .
C6 C -0.00900(17) 0.69947(14) 0.12078(14) 0.0265(4) Uani 1 1 d . . .
H6 H -0.0226 0.7702 0.1054 0.032 Uiso 1 1 calc R . .
C7 C 0.10101(16) 0.65439(13) 0.10495(13) 0.0229(4) Uani 1 1 d . . .
H7 H 0.1625 0.6937 0.0767 0.028 Uiso 1 1 calc R . .
C8 C 0.18587(16) 0.36602(13) 0.22002(13) 0.0223(4) Uani 1 1 d . . .
H8 H 0.1901 0.2894 0.2257 0.027 Uiso 1 1 calc R . .
C9 C 0.29960(16) 0.53886(13) 0.01781(13) 0.0217(3) Uani 1 1 d . . .
H9A H 0.3842 0.5126 0.0291 0.033 Uiso 1 1 calc R . .
H9B H 0.3005 0.6138 0.0249 0.033 Uiso 1 1 calc R . .
H9C H 0.2634 0.5202 -0.0513 0.033 Uiso 1 1 calc R . .
C10 C 0.25511(17) 0.41254(14) 0.31584(13) 0.0260(4) Uani 1 1 d . . .
H10A H 0.2530 0.4877 0.3107 0.039 Uiso 1 1 calc R . .
H10B H 0.3410 0.3890 0.3224 0.039 Uiso 1 1 calc R . .
H10C H 0.2160 0.3909 0.3762 0.039 Uiso 1 1 calc R . .
C11 C 0.32265(15) 0.32383(12) 0.07600(13) 0.0195(3) Uani 1 1 d . . .
H11 H 0.3255 0.3482 0.0041 0.023 Uiso 1 1 calc R . .
C12 C 0.26642(16) 0.21627(13) 0.07019(14) 0.0226(4) Uani 1 1 d . . .
H12A H 0.1796 0.2197 0.0395 0.027 Uiso 1 1 calc R . .
H12B H 0.2679 0.1869 0.1399 0.027 Uiso 1 1 calc R . .
C13 C 0.34099(17) 0.14823(13) 0.00459(14) 0.0251(4) Uani 1 1 d . . .
H13A H 0.3050 0.0783 0.0002 0.030 Uiso 1 1 calc R . .
H13B H 0.3369 0.1766 -0.0656 0.030 Uiso 1 1 calc R . .
C14 C 0.47509(17) 0.14236(13) 0.05057(15) 0.0272(4) Uani 1 1 d . . .
H14A H 0.5230 0.1015 0.0050 0.033 Uiso 1 1 calc R . .
H14B H 0.4798 0.1072 0.1177 0.033 Uiso 1 1 calc R . .
C15 C 0.53141(17) 0.24945(14) 0.06465(16) 0.0291(4) Uani 1 1 d . . .
H15A H 0.5379 0.2804 -0.0035 0.035 Uiso 1 1 calc R . .
H15B H 0.6158 0.2436 0.1003 0.035 Uiso 1 1 calc R . .
C16 C 0.45478(16) 0.32014(13) 0.12631(15) 0.0251(4) Uani 1 1 d . . .
H16A H 0.4561 0.2942 0.1973 0.030 Uiso 1 1 calc R . .
H16B H 0.4905 0.3901 0.1291 0.030 Uiso 1 1 calc R . .
C99 C 0.60162(17) 0.57976(14) 0.36626(14) 0.0275(4) Uani 1 1 d . . .
F1 F 0.72414(10) 0.57689(9) 0.38293(10) 0.0390(3) Uani 1 1 d . . .
F2 F 0.56094(14) 0.63335(13) 0.44222(9) 0.0550(4) Uani 1 1 d . . .
F3 F 0.56092(12) 0.48439(10) 0.37163(11) 0.0513(4) Uani 1 1 d . . .
S1 S 0.55170(4) 0.63829(3) 0.24254(3) 0.01906(12) Uani 1 1 d . . .
O1 O 0.60079(12) 0.57037(10) 0.17072(10) 0.0310(3) Uani 1 1 d . . .
O2 O 0.61015(12) 0.73791(9) 0.25094(11) 0.0289(3) Uani 1 1 d . . .
O3 O 0.41936(11) 0.63996(10) 0.23915(10) 0.0265(3) 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
N1 C1 C2 118.99(14) . . ?
N1 C1 C9 120.66(15) . . ?
C2 C1 C9 120.25(14) . . ?
C1 N1 C11 122.93(13) . . ?
C1 N1 C8 117.07(13) . . ?
C11 N1 C8 119.99(13) . . ?
C7 C2 C3 118.66(15) . . ?
C7 C2 C1 122.78(15) . . ?
C3 C2 C1 117.48(15) . . ?
N2 C3 C4 122.61(16) . . ?
N2 C3 C2 117.74(16) . . ?
C4 C3 C2 119.64(16) . . ?
C3 N2 C8 118.28(14) . . ?
C5 C4 C3 119.80(17) . . ?
C4 C5 C6 121.05(17) . . ?
C7 C6 C5 119.84(17) . . ?
C6 C7 C2 120.78(16) . . ?
N2 C8 N1 107.40(14) . . ?
N2 C8 C10 113.32(14) . . ?
N1 C8 C10 110.11(14) . . ?
N1 C11 C16 112.50(13) . . ?
N1 C11 C12 111.79(13) . . ?
C16 C11 C12 110.46(14) . . ?
C11 C12 C13 108.94(14) . . ?
C14 C13 C12 110.57(14) . . ?
C13 C14 C15 111.04(14) . . ?
C14 C15 C16 112.19(15) . . ?
C11 C16 C15 109.53(14) . . ?
F3 C99 F2 108.15(16) . . ?
F3 C99 F1 107.54(15) . . ?
F2 C99 F1 107.45(16) . . ?
F3 C99 S1 111.67(13) . . ?
F2 C99 S1 110.91(13) . . ?
F1 C99 S1 110.94(12) . . ?
O1 S1 O3 115.54(8) . . ?
O1 S1 O2 114.23(8) . . ?
O3 S1 O2 114.95(8) . . ?
O1 S1 C99 103.36(9) . . ?
O3 S1 C99 103.72(8) . . ?
O2 S1 C99 102.68(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.319(2) . ?
C1 C2 1.442(2) . ?
C1 C9 1.490(2) . ?
N1 C11 1.494(2) . ?
N1 C8 1.494(2) . ?
C2 C7 1.412(2) . ?
C2 C3 1.419(2) . ?
C3 N2 1.351(2) . ?
C3 C4 1.408(2) . ?
N2 C8 1.430(2) . ?
C4 C5 1.370(3) . ?
C5 C6 1.405(3) . ?
C6 C7 1.371(2) . ?
C8 C10 1.522(3) . ?
C11 C16 1.520(2) . ?
C11 C12 1.527(2) . ?
C12 C13 1.528(2) . ?
C13 C14 1.523(3) . ?
C14 C15 1.526(2) . ?
C15 C16 1.531(2) . ?
C99 F3 1.323(2) . ?
C99 F2 1.331(2) . ?
C99 F1 1.331(2) . ?
C99 S1 1.8240(19) . ?
S1 O1 1.4367(13) . ?
S1 O3 1.4390(13) . ?
S1 O2 1.4437(13) . ?
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
N2 H02 O2 0.83(2) 2.05(2) 2.8663(19) 170(2) 2_545
C8 H8 O3 1.00 2.35 3.223(2) 144.9 2_545
C9 H9C O1 0.98 2.56 3.146(2) 118.7 3_665
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
_geom_torsion_publ_flag
C2 C1 N1 C11 163.44(15) . . . . ?
C9 C1 N1 C11 -12.8(2) . . . . ?
C2 C1 N1 C8 -16.8(2) . . . . ?
C9 C1 N1 C8 166.92(14) . . . . ?
N1 C1 C2 C7 175.55(15) . . . . ?
C9 C1 C2 C7 -8.2(2) . . . . ?
N1 C1 C2 C3 -16.5(2) . . . . ?
C9 C1 C2 C3 159.77(15) . . . . ?
C7 C2 C3 N2 -176.15(15) . . . . ?
C1 C2 C3 N2 15.4(2) . . . . ?
C7 C2 C3 C4 5.4(2) . . . . ?
C1 C2 C3 C4 -163.12(15) . . . . ?
C4 C3 N2 C8 -161.36(16) . . . . ?
C2 C3 N2 C8 20.2(2) . . . . ?
N2 C3 C4 C5 176.77(17) . . . . ?
C2 C3 C4 C5 -4.8(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 2.5(3) . . . . ?
C5 C6 C7 C2 -1.8(3) . . . . ?
C3 C2 C7 C6 -2.0(2) . . . . ?
C1 C2 C7 C6 165.78(16) . . . . ?
C3 N2 C8 N1 -50.2(2) . . . . ?
C3 N2 C8 C10 71.6(2) . . . . ?
C1 N1 C8 N2 48.46(19) . . . . ?
C11 N1 C8 N2 -131.79(15) . . . . ?
C1 N1 C8 C10 -75.36(18) . . . . ?
C11 N1 C8 C10 104.39(17) . . . . ?
C1 N1 C11 C16 95.85(18) . . . . ?
C8 N1 C11 C16 -83.87(18) . . . . ?
C1 N1 C11 C12 -139.18(16) . . . . ?
C8 N1 C11 C12 41.1(2) . . . . ?
N1 C11 C12 C13 172.43(14) . . . . ?
C16 C11 C12 C13 -61.48(18) . . . . ?
C11 C12 C13 C14 59.37(19) . . . . ?
C12 C13 C14 C15 -55.7(2) . . . . ?
C13 C14 C15 C16 53.8(2) . . . . ?
N1 C11 C16 C15 -175.37(14) . . . . ?
C12 C11 C16 C15 58.94(19) . . . . ?
C14 C15 C16 C11 -55.0(2) . . . . ?
F3 C99 S1 O1 -58.14(15) . . . . ?
F2 C99 S1 O1 -178.84(13) . . . . ?
F1 C99 S1 O1 61.81(15) . . . . ?
F3 C99 S1 O3 62.80(15) . . . . ?
F2 C99 S1 O3 -57.91(15) . . . . ?
F1 C99 S1 O3 -177.25(13) . . . . ?
F3 C99 S1 O2 -177.21(13) . . . . ?
F2 C99 S1 O2 62.09(15) . . . . ?
F1 C99 S1 O2 -57.25(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190624
