#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/86/2108633.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108633
loop_
_publ_author_name
'Singla, Labhini'
'Yadav, Hare Ram'
'Roy Choudhury, Angshuman'
_publ_section_title
;
 Evaluation of fluorine-mediated intermolecular interactions in
 tetrafluorinated tetrahydroisoquinoline derivatives: synthesis and
 computational studies
;
_journal_coeditor_code           BM5125SUP1
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620006873
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 F4 N O'
_chemical_formula_sum            'C22 H17 F4 N O'
_chemical_formula_weight         387.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2020-03-09T09:07:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.96(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.445(6)
_cell_length_b                   21.293(11)
_cell_length_c                   9.590(6)
_cell_measurement_reflns_used    4135
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     1775.9(18)
_computing_cell_refinement
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
        CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9543
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.024
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.36
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1384P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2162
_reflns_number_gt                2419
_reflns_number_total             3113
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bm5125sup1.cif
_cod_data_source_block           6-9
_cod_database_code               2108633
_cod_database_fobs_code          2108633
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C19 0.2389(3) 0.72638(11) 0.3398(3) 0.0299(6) Uani d 1 . . C
H19 0.2806 0.7533 0.2864 0.036 Uiso calc 1 . . H
C18 0.3151(3) 0.67234(12) 0.4077(3) 0.0273(6) Uani d 1 . . C
C1 0.3425(3) 0.56909(11) 0.5492(3) 0.0270(6) Uani d 1 . . C
H1 0.4531 0.5732 0.5647 0.032 Uiso calc 1 . . H
C22 0.1219(3) 0.64534(11) 0.4955(3) 0.0291(6) Uani d 1 . . C
H22 0.0794 0.6182 0.5477 0.035 Uiso calc 1 . . H
C5 0.1580(3) 0.41691(12) 0.2322(3) 0.0306(6) Uani d 1 . . C
C20 0.1007(3) 0.74069(12) 0.3508(3) 0.0326(6) Uani d 1 . . C
H20 0.045 0.7775 0.3054 0.039 Uiso calc 1 . . H
C7 0.2454(3) 0.52290(12) 0.2881(3) 0.0294(6) Uani d 1 . . C
H7 0.2672 0.5624 0.2549 0.035 Uiso calc 1 . . H
C21 0.0466(3) 0.69961(12) 0.4298(3) 0.0328(6) Uani d 1 . . C
C9 0.2384(3) 0.45655(12) 0.4871(3) 0.0293(6) Uani d 1 . . C
C16 0.5197(3) 0.64586(12) 0.8027(3) 0.0309(6) Uani d 1 . . C
H16 0.5483 0.6444 0.7182 0.037 Uiso calc 1 . . H
C6 0.1882(3) 0.47471(12) 0.1832(3) 0.0312(6) Uani d 1 . . C
H6 0.17 0.4813 0.0796 0.037 Uiso calc 1 . . H
C2 0.3783(3) 0.49289(12) 0.7516(3) 0.0314(6) Uani d 1 . . C
H2A 0.3847 0.4888 0.8567 0.038 Uiso calc 1 . . H
H2B 0.4807 0.4832 0.7513 0.038 Uiso calc 1 . . H
C4 0.1858(3) 0.40822(12) 0.3837(3) 0.0318(6) Uani d 1 . . C
H4 0.1682 0.3681 0.4173 0.038 Uiso calc 1 . . H
C3 0.2608(3) 0.44734(12) 0.6501(3) 0.0345(6) Uani d 1 . . C
H3A 0.2954 0.4038 0.6815 0.041 Uiso calc 1 . . H
H3B 0.1617 0.4537 0.6607 0.041 Uiso calc 1 . . H
C15 0.5895(3) 0.68986(13) 0.9158(3) 0.0356(7) Uani d 1 . . C
H15 0.6631 0.7188 0.9087 0.043 Uiso calc 1 . . H
C12 0.3715(3) 0.60883(13) 0.9355(3) 0.0360(7) Uani d 1 . . C
C13 0.4400(4) 0.65073(14) 1.0511(3) 0.0411(7) Uani d 1 . . C
H13 0.4132 0.6523 1.1367 0.049 Uiso calc 1 . . H
C14 0.5482(3) 0.68998(14) 1.0382(3) 0.0396(7) Uani d 1 . . C
C10 0.0588(4) 0.37515(14) -0.0185(3) 0.0444(8) Uani d 1 . . C
H10A 0.0229 0.3353 -0.0718 0.067 Uiso calc 1 . . H
H10B 0.1465 0.3906 -0.0389 0.067 Uiso calc 1 . . H
H10C -0.0246 0.4061 -0.0539 0.067 Uiso calc 1 . . H
C17 0.2605(3) 0.63054(11) 0.4850(3) 0.0263(6) Uani d 1 . . C
C11 0.4096(3) 0.60381(12) 0.8088(3) 0.0285(6) Uani d 1 . . C
C8 0.2717(3) 0.51507(12) 0.4398(3) 0.0283(6) Uani d 1 . . C
N1 0.3335(2) 0.55777(9) 0.6968(2) 0.0272(5) Uani d 1 . . N
O1 0.1045(2) 0.36568(9) 0.1400(2) 0.0363(5) Uani d 1 . . O
F3 0.45171(17) 0.65968(7) 0.39668(17) 0.0336(4) Uani d 1 . . F
F4 -0.08722(18) 0.71384(7) 0.4449(2) 0.0442(5) Uani d 1 . . F
F1 0.26065(19) 0.57040(8) 0.94415(18) 0.0446(5) Uani d 1 . . F
F2 0.6162(2) 0.73273(9) 1.15037(19) 0.0563(6) Uani d 1 . . F
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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.8(2) . . ?
C20 C19 H19 120.6 . . ?
C19 C18 C17 123.8(2) . . ?
F3 C18 C19 117.6(2) . . ?
F3 C18 C17 118.5(2) . . ?
C17 C1 H1 108.7 . . ?
C17 C1 C8 110.7(2) . . ?
C8 C1 H1 108.7 . . ?
N1 C1 H1 108.7 . . ?
N1 C1 C17 108.59(19) . . ?
N1 C1 C8 111.4(2) . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C17 119.4(2) . . ?
C17 C22 H22 120.3 . . ?
C4 C5 C6 119.7(2) . . ?
O1 C5 C6 124.1(2) . . ?
O1 C5 C4 116.2(2) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.7(2) . . ?
C21 C20 H20 121.1 . . ?
C6 C7 H7 119 . . ?
C8 C7 H7 119 . . ?
C8 C7 C6 122.0(2) . . ?
C22 C21 C20 123.3(3) . . ?
F4 C21 C22 118.3(2) . . ?
F4 C21 C20 118.4(2) . . ?
C4 C9 C3 120.9(2) . . ?
C4 C9 C8 119.6(2) . . ?
C8 C9 C3 119.5(2) . . ?
C15 C16 H16 118.8 . . ?
C15 C16 C11 122.4(2) . . ?
C11 C16 H16 118.8 . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.6(2) . . ?
C5 C4 H4 119.3 . . ?
C9 C4 C5 121.5(2) . . ?
C9 C4 H4 119.3 . . ?
C9 C3 C2 110.8(2) . . ?
C9 C3 H3A 109.5 . . ?
C9 C3 H3B 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C16 C15 H15 121.3 . . ?
C14 C15 C16 117.5(3) . . ?
C14 C15 H15 121.3 . . ?
C13 C12 C11 123.4(3) . . ?
F1 C12 C13 118.3(2) . . ?
F1 C12 C11 118.3(2) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 C15 123.3(3) . . ?
C13 C14 F2 118.5(3) . . ?
F2 C14 C15 118.2(3) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
C18 C17 C1 122.3(2) . . ?
C18 C17 C22 116.9(2) . . ?
C22 C17 C1 120.7(2) . . ?
C16 C11 C12 115.9(2) . . ?
C16 C11 N1 125.2(2) . . ?
C12 C11 N1 118.8(2) . . ?
C7 C8 C1 118.8(2) . . ?
C7 C8 C9 118.3(2) . . ?
C9 C8 C1 122.7(2) . . ?
C1 N1 C2 112.24(19) . . ?
C11 N1 C1 114.3(2) . . ?
C11 N1 C2 112.6(2) . . ?
C5 O1 C10 117.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C19 H19 . 0.95 ?
C19 C18 . 1.378(4) ?
C19 C20 . 1.384(4) ?
C18 C17 . 1.380(4) ?
C18 F3 . 1.362(3) ?
C1 H1 . 1 ?
C1 C17 . 1.523(3) ?
C1 C8 . 1.524(3) ?
C1 N1 . 1.471(3) ?
C22 H22 . 0.95 ?
C22 C21 . 1.374(4) ?
C22 C17 . 1.388(4) ?
C5 C6 . 1.386(4) ?
C5 C4 . 1.385(4) ?
C5 O1 . 1.371(3) ?
C20 H20 . 0.95 ?
C20 C21 . 1.380(4) ?
C7 H7 . 0.95 ?
C7 C6 . 1.391(4) ?
C7 C8 . 1.387(4) ?
C21 F4 . 1.362(3) ?
C9 C4 . 1.380(4) ?
C9 C3 . 1.507(4) ?
C9 C8 . 1.403(4) ?
C16 H16 . 0.95 ?
C16 C15 . 1.389(4) ?
C16 C11 . 1.391(4) ?
C6 H6 . 0.95 ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.509(4) ?
C2 N1 . 1.480(3) ?
C4 H4 . 0.95 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C15 H15 . 0.95 ?
C15 C14 . 1.374(4) ?
C12 C13 . 1.373(4) ?
C12 C11 . 1.399(4) ?
C12 F1 . 1.356(3) ?
C13 H13 . 0.95 ?
C13 C14 . 1.362(5) ?
C14 F2 . 1.364(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.423(4) ?
C11 N1 . 1.424(3) ?
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
C19 C18 C17 C1 175.7(2) . . . . ?
C19 C18 C17 C22 -1.1(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C19 C20 C21 F4 178.4(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C20 C19 C18 C17 1.0(4) . . . . ?
C20 C19 C18 F3 -179.3(2) . . . . ?
C21 C22 C17 C18 0.1(4) . . . . ?
C21 C22 C17 C1 -176.7(2) . . . . ?
C16 C15 C14 C13 -2.0(4) . . . . ?
C16 C15 C14 F2 179.7(2) . . . . ?
C16 C11 N1 C1 -18.0(3) . . . . ?
C16 C11 N1 C2 111.7(3) . . . . ?
C6 C5 C4 C9 2.1(4) . . . . ?
C6 C5 O1 C10 -8.4(4) . . . . ?
C6 C7 C8 C1 176.8(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C4 C5 O1 C10 173.1(2) . . . . ?
C4 C9 C3 C2 155.2(2) . . . . ?
C4 C9 C8 C1 -174.9(2) . . . . ?
C4 C9 C8 C7 2.1(4) . . . . ?
C3 C9 C4 C5 177.0(2) . . . . ?
C3 C9 C8 C1 5.0(4) . . . . ?
C3 C9 C8 C7 -177.9(2) . . . . ?
C3 C2 N1 C1 -67.2(3) . . . . ?
C3 C2 N1 C11 162.1(2) . . . . ?
C15 C16 C11 C12 0.7(4) . . . . ?
C15 C16 C11 N1 179.8(2) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C12 C13 C14 F2 179.0(2) . . . . ?
C12 C11 N1 C1 161.2(2) . . . . ?
C12 C11 N1 C2 -69.2(3) . . . . ?
C13 C12 C11 C16 -2.1(4) . . . . ?
C13 C12 C11 N1 178.7(2) . . . . ?
C17 C1 C8 C7 47.6(3) . . . . ?
C17 C1 C8 C9 -135.4(2) . . . . ?
C17 C1 N1 C2 167.02(19) . . . . ?
C17 C1 N1 C11 -63.1(3) . . . . ?
C17 C22 C21 C20 0.9(4) . . . . ?
C17 C22 C21 F4 -178.4(2) . . . . ?
C11 C16 C15 C14 1.3(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C8 C1 C17 C18 -96.1(3) . . . . ?
C8 C1 C17 C22 80.6(3) . . . . ?
C8 C1 N1 C2 44.9(3) . . . . ?
C8 C1 N1 C11 174.77(19) . . . . ?
C8 C7 C6 C5 -0.7(4) . . . . ?
C8 C9 C4 C5 -3.1(4) . . . . ?
C8 C9 C3 C2 -24.7(3) . . . . ?
N1 C1 C17 C18 141.4(2) . . . . ?
N1 C1 C17 C22 -42.0(3) . . . . ?
N1 C1 C8 C7 168.5(2) . . . . ?
N1 C1 C8 C9 -14.5(3) . . . . ?
N1 C2 C3 C9 54.3(3) . . . . ?
O1 C5 C6 C7 -178.6(2) . . . . ?
O1 C5 C4 C9 -179.4(2) . . . . ?
F3 C18 C17 C1 -4.0(3) . . . . ?
F3 C18 C17 C22 179.2(2) . . . . ?
F1 C12 C13 C14 -178.3(2) . . . . ?
F1 C12 C11 C16 177.7(2) . . . . ?
F1 C12 C11 N1 -1.5(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308515
