#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/86/2108630.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_2108630
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           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-03-09T09:04:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.459(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.323(8)
_cell_length_b                   13.499(5)
_cell_length_c                   11.828(5)
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3
_cell_volume                     3525(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10335
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         3.018
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.46
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.094
_refine_ls_R_factor_gt           0.0567
_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)+(0.0481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                2301
_reflns_number_total             4010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bm5125sup1.cif
_cod_data_source_block           6-6
_cod_original_cell_volume        3526(2)
_cod_database_code               2108630
_cod_database_fobs_code          2108630
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
F1 0.57206(6) 0.27905(11) 0.35110(10) 0.0487(4) Uani d 1 . . F
F2 0.56593(6) 0.08251(11) 0.33378(12) 0.0597(4) Uani d 1 . . F
F3 0.78495(6) 0.16624(12) 0.67940(10) 0.0537(4) Uani d 1 . . F
F4 0.80789(5) 0.49115(11) 0.82131(11) 0.0547(4) Uani d 1 . . F
O1 0.62123(6) 0.83390(12) 0.46662(13) 0.0411(4) Uani d 1 . . O
N1 0.57938(7) 0.37686(15) 0.55817(13) 0.0336(4) Uani d 1 . . N
C1 0.63623(8) 0.41640(17) 0.52456(16) 0.0322(5) Uani d 1 . . C
H1 0.6401 0.3872 0.4483 0.039 Uiso calc 1 . . H
C2 0.56389(9) 0.42765(18) 0.66019(16) 0.0378(6) Uani d 1 . . C
H2A 0.5985 0.4235 0.7228 0.045 Uiso calc 1 . . H
H2B 0.5287 0.3946 0.686 0.045 Uiso calc 1 . . H
C3 0.54879(9) 0.53591(18) 0.63334(17) 0.0357(6) Uani d 1 . . C
H3A 0.5067 0.5404 0.5935 0.043 Uiso calc 1 . . H
H3B 0.551 0.573 0.706 0.043 Uiso calc 1 . . H
C4 0.58813(8) 0.68581(18) 0.54228(16) 0.0354(6) Uani d 1 . . C
H4 0.5597 0.7243 0.5756 0.042 Uiso calc 1 . . H
C5 0.62674(9) 0.73243(19) 0.47644(17) 0.0356(5) Uani d 1 . . C
C6 0.66779(9) 0.67609(19) 0.42611(16) 0.0358(6) Uani d 1 . . C
H6 0.6943 0.7068 0.3809 0.043 Uiso calc 1 . . H
C7 0.66939(9) 0.57458(19) 0.44291(16) 0.0361(6) Uani d 1 . . C
H7 0.6976 0.5362 0.4087 0.043 Uiso calc 1 . . H
C8 0.63099(8) 0.52670(18) 0.50841(16) 0.0313(5) Uani d 1 . . C
C9 0.59056(8) 0.58428(18) 0.56003(16) 0.0319(5) Uani d 1 . . C
C10 0.66642(10) 0.8848(2) 0.41514(19) 0.0454(6) Uani d 1 . . C
H10A 0.6633 0.8655 0.3346 0.068 Uiso calc 1 . . H
H10B 0.7067 0.8673 0.4551 0.068 Uiso calc 1 . . H
H10C 0.6603 0.9564 0.4204 0.068 Uiso calc 1 . . H
C11 0.57253(8) 0.27336(18) 0.55267(18) 0.0349(5) Uani d 1 . . C
C12 0.57032(9) 0.22502(19) 0.44788(18) 0.0391(6) Uani d 1 . . C
C13 0.56650(10) 0.1236(2) 0.4390(2) 0.0455(6) Uani d 1 . . C
C14 0.56326(9) 0.0645(2) 0.5321(2) 0.0506(7) Uani d 1 . . C
H14 0.5618 -0.0056 0.5255 0.061 Uiso calc 1 . . H
C15 0.56222(10) 0.1112(2) 0.6368(2) 0.0497(7) Uani d 1 . . C
H15 0.5579 0.0724 0.7021 0.06 Uiso calc 1 . . H
C16 0.56729(9) 0.2126(2) 0.64755(19) 0.0417(6) Uani d 1 . . C
H16 0.5673 0.2422 0.7204 0.05 Uiso calc 1 . . H
C17 0.69308(8) 0.38555(19) 0.60696(16) 0.0349(6) Uani d 1 . . C
C18 0.72549(8) 0.4542(2) 0.68005(17) 0.0375(6) Uani d 1 . . C
H18 0.7124 0.5211 0.6813 0.045 Uiso calc 1 . . H
C19 0.77678(9) 0.4232(2) 0.75037(17) 0.0420(6) Uani d 1 . . C
C20 0.79861(10) 0.3276(2) 0.75261(18) 0.0463(7) Uani d 1 . . C
H20 0.8345 0.3085 0.8011 0.056 Uiso calc 1 . . H
C21 0.76531(9) 0.2618(2) 0.68036(18) 0.0421(6) Uani d 1 . . C
C22 0.71334(9) 0.28752(19) 0.60739(17) 0.0380(6) Uani d 1 . . C
H22 0.6919 0.2395 0.5585 0.046 Uiso calc 1 . . H
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
C5 O1 C10 116.99(17) . . ?
C2 N1 C1 111.42(17) . . ?
C11 N1 C1 115.89(16) . . ?
C11 N1 C2 117.62(17) . . ?
N1 C1 H1 106.9 . . ?
N1 C1 C8 109.67(16) . . ?
N1 C1 C17 113.01(16) . . ?
C8 C1 H1 106.9 . . ?
C8 C1 C17 112.95(18) . . ?
C17 C1 H1 106.9 . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C3 110.33(17) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C9 C3 C2 113.45(17) . . ?
C9 C3 H3A 108.9 . . ?
C9 C3 H3B 108.9 . . ?
C5 C4 H4 119.4 . . ?
C9 C4 H4 119.4 . . ?
C9 C4 C5 121.16(19) . . ?
O1 C5 C4 116.16(19) . . ?
O1 C5 C6 124.3(2) . . ?
C6 C5 C4 119.5(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C1 119.10(18) . . ?
C7 C8 C9 118.3(2) . . ?
C9 C8 C1 122.58(19) . . ?
C4 C9 C3 120.01(18) . . ?
C4 C9 C8 119.8(2) . . ?
C8 C9 C3 120.2(2) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C16 124.2(2) . . ?
C12 C11 N1 119.7(2) . . ?
C12 C11 C16 116.1(2) . . ?
F1 C12 C11 119.6(2) . . ?
F1 C12 C13 118.5(2) . . ?
C13 C12 C11 121.8(2) . . ?
F2 C13 C12 117.9(2) . . ?
F2 C13 C14 120.2(3) . . ?
C14 C13 C12 121.9(2) . . ?
C13 C14 H14 121.3 . . ?
C13 C14 C15 117.4(3) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C1 121.1(2) . . ?
C18 C17 C22 119.25(19) . . ?
C22 C17 C1 119.6(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
F4 C19 C18 118.0(2) . . ?
F4 C19 C20 118.15(19) . . ?
C20 C19 C18 123.8(2) . . ?
C19 C20 H20 122.1 . . ?
C21 C20 C19 115.9(2) . . ?
C21 C20 H20 122.1 . . ?
F3 C21 C20 118.2(2) . . ?
F3 C21 C22 118.2(2) . . ?
C20 C21 C22 123.5(2) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 C17 118.7(2) . . ?
C21 C22 H22 120.6 . . ?
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
F1 C12 . 1.363(3) ?
F2 C13 . 1.361(3) ?
F3 C21 . 1.363(3) ?
F4 C19 . 1.363(3) ?
O1 C5 . 1.379(3) ?
O1 C10 . 1.429(2) ?
N1 C1 . 1.484(2) ?
N1 C2 . 1.473(2) ?
N1 C11 . 1.406(3) ?
C1 H1 . 1 ?
C1 C8 . 1.504(3) ?
C1 C17 . 1.540(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 C3 . 1.523(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C9 . 1.512(3) ?
C4 H4 . 0.95 ?
C4 C5 . 1.394(3) ?
C4 C9 . 1.386(3) ?
C5 C6 . 1.390(3) ?
C6 H6 . 0.95 ?
C6 C7 . 1.384(3) ?
C7 H7 . 0.95 ?
C7 C8 . 1.396(3) ?
C8 C9 . 1.398(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.395(3) ?
C11 C16 . 1.408(3) ?
C12 C13 . 1.375(4) ?
C13 C14 . 1.371(4) ?
C14 H14 . 0.95 ?
C14 C15 . 1.392(3) ?
C15 H15 . 0.95 ?
C15 C16 . 1.378(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.395(3) ?
C17 C22 . 1.398(3) ?
C18 H18 . 0.95 ?
C18 C19 . 1.378(3) ?
C19 C20 . 1.377(3) ?
C20 H20 . 0.95 ?
C20 C21 . 1.373(3) ?
C21 C22 . 1.385(3) ?
C22 H22 . 0.95 ?
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
F1 C12 C13 F2 1.3(3) . . . . ?
F1 C12 C13 C14 -178.59(18) . . . . ?
F2 C13 C14 C15 -178.14(18) . . . . ?
F3 C21 C22 C17 -179.45(16) . . . . ?
F4 C19 C20 C21 179.39(17) . . . . ?
O1 C5 C6 C7 179.50(18) . . . . ?
N1 C1 C8 C7 -159.54(17) . . . . ?
N1 C1 C8 C9 22.9(2) . . . . ?
N1 C1 C17 C18 -109.0(2) . . . . ?
N1 C1 C17 C22 72.1(2) . . . . ?
N1 C2 C3 C9 -41.3(2) . . . . ?
N1 C11 C12 F1 -3.0(3) . . . . ?
N1 C11 C12 C13 176.92(18) . . . . ?
N1 C11 C16 C15 -178.32(18) . . . . ?
C1 N1 C2 C3 65.9(2) . . . . ?
C1 N1 C11 C12 -62.1(2) . . . . ?
C1 N1 C11 C16 118.2(2) . . . . ?
C1 C8 C9 C3 -1.4(3) . . . . ?
C1 C8 C9 C4 179.63(18) . . . . ?
C1 C17 C18 C19 -178.63(17) . . . . ?
C1 C17 C22 C21 178.60(17) . . . . ?
C2 N1 C1 C8 -55.0(2) . . . . ?
C2 N1 C1 C17 72.0(2) . . . . ?
C2 N1 C11 C12 162.53(17) . . . . ?
C2 N1 C11 C16 -17.2(3) . . . . ?
C2 C3 C9 C4 -170.65(17) . . . . ?
C2 C3 C9 C8 10.4(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C4 C9 C3 179.05(18) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C1 -178.86(18) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C3 -179.01(17) . . . . ?
C7 C8 C9 C4 2.1(3) . . . . ?
C8 C1 C17 C18 16.2(2) . . . . ?
C8 C1 C17 C22 -162.66(17) . . . . ?
C9 C4 C5 O1 -178.63(17) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C10 O1 C5 C4 170.38(17) . . . . ?
C10 O1 C5 C6 -9.3(3) . . . . ?
C11 N1 C1 C8 166.97(16) . . . . ?
C11 N1 C1 C17 -66.0(2) . . . . ?
C11 N1 C2 C3 -156.81(16) . . . . ?
C11 C12 C13 F2 -178.55(17) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C11 C16 C15 2.0(3) . . . . ?
C12 C13 C14 C15 1.8(3) . . . . ?
C13 C14 C15 C16 -3.2(3) . . . . ?
C14 C15 C16 C11 1.3(3) . . . . ?
C16 C11 C12 F1 176.77(17) . . . . ?
C16 C11 C12 C13 -3.3(3) . . . . ?
C17 C1 C8 C7 73.4(2) . . . . ?
C17 C1 C8 C9 -104.1(2) . . . . ?
C17 C18 C19 F4 -179.95(17) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 F3 -179.93(17) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C22 C17 C18 C19 0.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308512
