#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151644.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_7151644
loop_
_publ_author_name
'Čížková, Martina'
'Kolivoška, Viliam'
'Císařová, Ivana'
'Šaman, David'
'Pospíšil, Lubomír'
'Teplý, Filip'
_publ_section_title
;
 Nitrogen heteroaromatic cations by [2+2+2] cycloaddition.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              450
_journal_page_last               462
_journal_paper_doi               10.1039/C0OB00507J
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C18 H16 N, C F3 O3 S'
_chemical_formula_sum            'C19 H16 F3 N O3 S'
_chemical_formula_weight         395.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.0166(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4866(2)
_cell_length_b                   14.3369(2)
_cell_length_c                   17.3851(3)
_cell_measurement_reflns_used    4377
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1837.58(6)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.040
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37823
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²+0.7320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                3558
_reflns_number_total             4219
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            C0OB00507J.TXT
_cod_data_source_block           zel-roz-ccl2-et2o-uochb
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151644
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22156(18) 0.34479(10) -0.01900(8) 0.0280(3) Uani 1 1 d . . .
N2 N 0.17185(15) 0.28814(8) 0.03682(7) 0.0297(3) Uani 1 1 d . . .
C3 C 0.1517(2) 0.19528(11) 0.02466(10) 0.0392(4) Uani 1 1 d . . .
H3 H 0.1185 0.1569 0.0644 0.047 Uiso 1 1 calc R . .
C4 C 0.1786(2) 0.15570(11) -0.04425(11) 0.0442(4) Uani 1 1 d . . .
H4 H 0.1639 0.0904 -0.0522 0.053 Uiso 1 1 calc R . .
C5 C 0.2271(2) 0.21138(12) -0.10179(10) 0.0412(4) Uani 1 1 d . . .
H5 H 0.2452 0.1848 -0.1499 0.049 Uiso 1 1 calc R . .
C6 C 0.2492(2) 0.30616(11) -0.08922(9) 0.0342(3) Uani 1 1 d . . .
H6 H 0.2833 0.3449 -0.1286 0.041 Uiso 1 1 calc R . .
C7 C 0.24145(19) 0.44172(10) -0.00310(8) 0.0299(3) Uani 1 1 d . . .
C8 C 0.25937(19) 0.52407(10) 0.00824(8) 0.0297(3) Uani 1 1 d . . .
C9 C 0.27815(18) 0.62216(10) 0.02154(8) 0.0281(3) Uani 1 1 d . . .
C10 C 0.2582(2) 0.65992(11) 0.09384(8) 0.0333(3) Uani 1 1 d . . .
H10 H 0.2317 0.6203 0.1342 0.040 Uiso 1 1 calc R . .
C11 C 0.2771(2) 0.75490(11) 0.10637(9) 0.0364(3) Uani 1 1 d . . .
H11 H 0.2637 0.7799 0.1556 0.044 Uiso 1 1 calc R . .
C12 C 0.3156(2) 0.81490(10) 0.04793(9) 0.0341(3) Uani 1 1 d . . .
C13 C 0.33315(19) 0.77663(10) -0.02405(9) 0.0323(3) Uani 1 1 d . . .
H13 H 0.3580 0.8164 -0.0646 0.039 Uiso 1 1 calc R . .
C14 C 0.31510(19) 0.68174(10) -0.03749(8) 0.0295(3) Uani 1 1 d . . .
H14 H 0.3278 0.6569 -0.0869 0.035 Uiso 1 1 calc R . .
C15 C 0.1392(2) 0.32825(12) 0.11183(9) 0.0360(3) Uani 1 1 d . . .
H15A H 0.0651 0.2842 0.1369 0.043 Uiso 1 1 calc R . .
H15B H 0.0697 0.3870 0.1013 0.043 Uiso 1 1 calc R . .
C16 C 0.3166(2) 0.34803(12) 0.16776(9) 0.0373(3) Uani 1 1 d . . .
H16A H 0.3918 0.3911 0.1423 0.045 Uiso 1 1 calc R . .
H16B H 0.2892 0.3791 0.2152 0.045 Uiso 1 1 calc R . .
C17 C 0.4191(2) 0.26251(12) 0.19027(8) 0.0376(4) Uani 1 1 d . . .
C18 C 0.4983(2) 0.19204(14) 0.20549(10) 0.0456(4) Uani 1 1 d . . .
H18 H 0.5622 0.1352 0.2178 0.055 Uiso 1 1 calc R . .
C19 C 0.3377(3) 0.91821(12) 0.06216(12) 0.0474(4) Uani 1 1 d . . .
H19A H 0.3679 0.9484 0.0155 0.071 Uiso 1 1 calc R . .
H19B H 0.4354 0.9292 0.1066 0.071 Uiso 1 1 calc R . .
H19C H 0.2241 0.9442 0.0736 0.071 Uiso 1 1 calc R . .
C20 C 0.1136(2) -0.01434(11) 0.25365(9) 0.0407(4) Uani 1 1 d . . .
S1 S -0.05822(5) 0.05908(3) 0.19690(2) 0.03561(12) Uani 1 1 d . . .
F1 F 0.1069(2) -0.00820(9) 0.32977(6) 0.0729(4) Uani 1 1 d . . .
F2 F 0.27962(16) 0.00925(10) 0.24498(8) 0.0722(4) Uani 1 1 d . . .
F3 F 0.08940(15) -0.10390(7) 0.23514(6) 0.0509(3) Uani 1 1 d . . .
O1 O -0.22373(19) 0.01811(10) 0.21286(10) 0.0632(4) Uani 1 1 d . . .
O2 O -0.0168(2) 0.15068(8) 0.22719(8) 0.0586(4) Uani 1 1 d . . .
O3 O -0.02906(18) 0.04521(8) 0.11843(7) 0.0462(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'
F F 0.0171 0.0103 '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'
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
N2 C1 C6 119.22(13) . . ?
N2 C1 C7 118.43(13) . . ?
C6 C1 C7 122.34(13) . . ?
C3 N2 C1 120.73(13) . . ?
C3 N2 C15 119.21(13) . . ?
C1 N2 C15 120.06(12) . . ?
N2 C3 C4 120.97(15) . . ?
N2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.47(15) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 119.65(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.95(15) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C1 178.13(16) . . ?
C7 C8 C9 179.24(16) . . ?
C14 C9 C10 119.20(13) . . ?
C14 C9 C8 120.59(13) . . ?
C10 C9 C8 120.21(13) . . ?
C11 C10 C9 119.89(14) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.31(14) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 118.27(14) . . ?
C13 C12 C19 120.67(15) . . ?
C11 C12 C19 121.06(15) . . ?
C14 C13 C12 121.16(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 120.17(13) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N2 C15 C16 111.86(12) . . ?
N2 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 111.82(14) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 177.22(18) . . ?
C17 C18 H18 180.0 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F2 C20 F3 108.14(15) . . ?
F2 C20 F1 107.13(14) . . ?
F3 C20 F1 106.06(13) . . ?
F2 C20 S1 112.41(11) . . ?
F3 C20 S1 112.01(11) . . ?
F1 C20 S1 110.77(13) . . ?
O2 S1 O3 114.79(8) . . ?
O2 S1 O1 116.27(9) . . ?
O3 S1 O1 113.91(9) . . ?
O2 S1 C20 104.17(8) . . ?
O3 S1 C20 103.06(8) . . ?
O1 S1 C20 102.17(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 N2 1.3659(18) . ?
C1 C6 1.388(2) . ?
C1 C7 1.4197(19) . ?
N2 C3 1.352(2) . ?
N2 C15 1.4840(19) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.201(2) . ?
C8 C9 1.428(2) . ?
C9 C14 1.3993(19) . ?
C9 C10 1.400(2) . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(2) . ?
C12 C19 1.506(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.530(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.463(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.178(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 F2 1.321(2) . ?
C20 F3 1.3285(19) . ?
C20 F1 1.3360(19) . ?
C20 S1 1.8154(18) . ?
S1 O2 1.4287(13) . ?
S1 O3 1.4324(12) . ?
S1 O1 1.4412(13) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26993558
2 PubChem 50993565
