#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/86/2108632.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_2108632
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_absolute_configuration unk
_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           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-03-09T09:06:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.559(2)
_cell_length_b                   17.595(2)
_cell_length_c                   6.1048(9)
_cell_measurement_reflns_used    4920
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     1778.7(4)
_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 0.997
_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  0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15664
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.379
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1425 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0438
_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)+(0.0509P)²+0.4424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                3654
_reflns_number_total             4061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bm5125sup1.cif
_cod_data_source_block           6-8
_cod_database_code               2108632
_cod_database_fobs_code          2108632
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.61840(17) 0.17114(16) 0.3861(5) 0.0246(6) Uani d 1 . . C
H19 0.6409 0.1328 0.295 0.03 Uiso calc 1 . . H
C11 0.37187(16) 0.15200(16) 0.5475(5) 0.0214(5) Uani d 1 . . C
C18 0.54189(16) 0.19998(15) 0.3514(5) 0.0221(5) Uani d 1 . . C
C9 0.35821(15) 0.38841(15) 0.6540(5) 0.0213(5) Uani d 1 . . C
C5 0.37694(18) 0.51749(16) 0.5279(5) 0.0250(6) Uani d 1 . . C
C20 0.66008(17) 0.20134(18) 0.5611(5) 0.0281(6) Uani d 1 . . C
C7 0.43560(17) 0.41391(15) 0.3281(5) 0.0238(6) Uani d 1 . . C
H7 0.4668 0.3959 0.2083 0.029 Uiso calc 1 . . H
C17 0.50621(15) 0.25574(15) 0.4780(4) 0.0212(5) Uani d 1 . . C
C4 0.34524(16) 0.46666(15) 0.6772(5) 0.0241(6) Uani d 1 . . C
H4 0.3143 0.485 0.7972 0.029 Uiso calc 1 . . H
C6 0.42307(18) 0.49102(16) 0.3519(5) 0.0262(6) Uani d 1 . . C
H6 0.4456 0.5258 0.2497 0.031 Uiso calc 1 . . H
C14 0.38270(18) -0.00207(16) 0.4610(5) 0.0288(6) Uani d 1 . . C
C22 0.55278(16) 0.28447(15) 0.6496(5) 0.0238(6) Uani d 1 . . C
H22 0.5311 0.3236 0.7391 0.029 Uiso calc 1 . . H
C13 0.34142(17) 0.04346(17) 0.3155(5) 0.0265(6) Uani d 1 . . C
H13 0.317 0.0231 0.1875 0.032 Uiso calc 1 . . H
C15 0.41810(19) 0.02594(17) 0.6464(5) 0.0311(7) Uani d 1 . . C
H15 0.4456 -0.0069 0.7448 0.037 Uiso calc 1 . . H
C21 0.62983(16) 0.25752(16) 0.6932(5) 0.0265(6) Uani d 1 . . C
H21 0.6607 0.2774 0.8112 0.032 Uiso calc 1 . . H
C16 0.41317(17) 0.10340(16) 0.6881(5) 0.0282(6) Uani d 1 . . C
H16 0.4385 0.1236 0.8151 0.034 Uiso calc 1 . . H
C3 0.32257(17) 0.33448(16) 0.8189(5) 0.0241(6) Uani d 1 . . C
H3A 0.264 0.329 0.7907 0.029 Uiso calc 1 . . H
H3B 0.3294 0.3559 0.9677 0.029 Uiso calc 1 . . H
C2 0.36228(17) 0.25690(16) 0.8089(4) 0.0233(6) Uani d 1 . . C
H2A 0.418 0.2599 0.8668 0.028 Uiso calc 1 . . H
H2B 0.3315 0.2202 0.899 0.028 Uiso calc 1 . . H
C10 0.3247(2) 0.62382(18) 0.7232(6) 0.0354(7) Uani d 1 . . C
H10A 0.3233 0.6794 0.7161 0.053 Uiso calc 1 . . H
H10B 0.3517 0.6079 0.8584 0.053 Uiso calc 1 . . H
H10C 0.2694 0.604 0.7217 0.053 Uiso calc 1 . . H
C12 0.33721(16) 0.11964(15) 0.3635(5) 0.0225(6) Uani d 1 . . C
C8 0.40322(16) 0.36187(15) 0.4769(4) 0.0214(5) Uani d 1 . . C
C1 0.41812(16) 0.27787(14) 0.4411(4) 0.0203(5) Uani d 1 . . C
H1 0.4047 0.2663 0.2849 0.024 Uiso calc 1 . . H
N1 0.36361(14) 0.23198(13) 0.5800(4) 0.0215(5) Uani d 1 . . N
O1 0.36772(13) 0.59494(11) 0.5392(4) 0.0307(5) Uani d 1 . . O
F3 0.49966(9) 0.17086(9) 0.1801(3) 0.0289(4) Uani d 1 . . F
F1 0.29748(10) 0.16511(9) 0.2233(3) 0.0290(4) Uani d 1 . . F
F2 0.38839(12) -0.07713(10) 0.4147(3) 0.0393(5) Uani d 1 . . F
F4 0.73537(10) 0.17432(11) 0.5994(3) 0.0394(5) 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 122.1 . . ?
C20 C19 H19 122.1 . . ?
C20 C19 C18 115.9(3) . . ?
C16 C11 N1 124.5(3) . . ?
C12 C11 C16 116.9(3) . . ?
C12 C11 N1 118.6(2) . . ?
C19 C18 C17 124.6(3) . . ?
F3 C18 C19 116.9(2) . . ?
F3 C18 C17 118.6(2) . . ?
C4 C9 C3 119.5(2) . . ?
C8 C9 C4 119.3(3) . . ?
C8 C9 C3 121.2(2) . . ?
C4 C5 C6 120.0(3) . . ?
O1 C5 C4 124.5(3) . . ?
O1 C5 C6 115.5(3) . . ?
C21 C20 C19 123.4(3) . . ?
F4 C20 C19 117.3(3) . . ?
F4 C20 C21 119.2(3) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C18 C17 C22 116.1(2) . . ?
C18 C17 C1 120.5(2) . . ?
C22 C17 C1 123.1(2) . . ?
C9 C4 H4 119.6 . . ?
C5 C4 C9 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C15 C14 C13 122.5(3) . . ?
F2 C14 C13 117.8(3) . . ?
F2 C14 C15 119.7(3) . . ?
C17 C22 H22 119 . . ?
C21 C22 C17 121.9(3) . . ?
C21 C22 H22 119 . . ?
C14 C13 H13 121.5 . . ?
C12 C13 C14 117.0(3) . . ?
C12 C13 H13 121.5 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.7(3) . . ?
C16 C15 H15 120.6 . . ?
C20 C21 C22 118.0(3) . . ?
C20 C21 H21 121 . . ?
C22 C21 H21 121 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C9 C3 H3A 109.3 . . ?
C9 C3 H3B 109.3 . . ?
C9 C3 C2 111.8(2) . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C3 C2 H2A 110 . . ?
C3 C2 H2B 110 . . ?
H2A C2 H2B 108.4 . . ?
N1 C2 C3 108.3(2) . . ?
N1 C2 H2A 110 . . ?
N1 C2 H2B 110 . . ?
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 . . ?
C13 C12 C11 123.6(3) . . ?
F1 C12 C11 118.4(2) . . ?
F1 C12 C13 118.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 C1 121.8(2) . . ?
C7 C8 C1 118.9(2) . . ?
C17 C1 H1 107.5 . . ?
C8 C1 C17 112.5(2) . . ?
C8 C1 H1 107.5 . . ?
N1 C1 C17 111.1(2) . . ?
N1 C1 C8 110.5(2) . . ?
N1 C1 H1 107.5 . . ?
C11 N1 C2 115.4(2) . . ?
C11 N1 C1 113.6(2) . . ?
C2 N1 C1 113.1(2) . . ?
C5 O1 C10 116.7(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 . 1.381(4) ?
C19 C20 . 1.378(4) ?
C11 C16 . 1.391(4) ?
C11 C12 . 1.384(4) ?
C11 N1 . 1.428(3) ?
C18 C17 . 1.382(4) ?
C18 F3 . 1.358(3) ?
C9 C4 . 1.401(4) ?
C9 C3 . 1.504(4) ?
C9 C8 . 1.393(4) ?
C5 C4 . 1.381(4) ?
C5 C6 . 1.398(4) ?
C5 O1 . 1.373(3) ?
C20 C21 . 1.371(4) ?
C20 F4 . 1.355(3) ?
C7 H7 . 0.95 ?
C7 C6 . 1.380(4) ?
C7 C8 . 1.397(4) ?
C17 C22 . 1.396(4) ?
C17 C1 . 1.526(4) ?
C4 H4 . 0.95 ?
C6 H6 . 0.95 ?
C14 C13 . 1.378(4) ?
C14 C15 . 1.366(4) ?
C14 F2 . 1.354(3) ?
C22 H22 . 0.95 ?
C22 C21 . 1.387(4) ?
C13 H13 . 0.95 ?
C13 C12 . 1.374(4) ?
C15 H15 . 0.95 ?
C15 C16 . 1.389(4) ?
C21 H21 . 0.95 ?
C16 H16 . 0.95 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C3 C2 . 1.516(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C2 N1 . 1.465(3) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 O1 . 1.424(4) ?
C12 F1 . 1.344(3) ?
C8 C1 . 1.514(4) ?
C1 H1 . 1 ?
C1 N1 . 1.478(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 C22 1.0(4) . . . . ?
C19 C18 C17 C1 -173.5(3) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C18 C19 C20 C21 -1.2(4) . . . . ?
C18 C19 C20 F4 -179.9(3) . . . . ?
C18 C17 C22 C21 -1.3(4) . . . . ?
C18 C17 C1 C8 -144.6(3) . . . . ?
C18 C17 C1 N1 90.8(3) . . . . ?
C9 C3 C2 N1 -49.5(3) . . . . ?
C9 C8 C1 C17 -110.9(3) . . . . ?
C9 C8 C1 N1 13.9(4) . . . . ?
C20 C19 C18 C17 0.2(4) . . . . ?
C20 C19 C18 F3 -179.8(2) . . . . ?
C7 C8 C1 C17 69.1(3) . . . . ?
C7 C8 C1 N1 -166.1(2) . . . . ?
C17 C22 C21 C20 0.4(4) . . . . ?
C17 C1 N1 C11 -57.0(3) . . . . ?
C17 C1 N1 C2 77.1(3) . . . . ?
C4 C9 C3 C2 -162.9(2) . . . . ?
C4 C9 C8 C7 1.0(4) . . . . ?
C4 C9 C8 C1 -179.0(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C4 C5 O1 C10 2.3(4) . . . . ?
C6 C5 C4 C9 -0.5(4) . . . . ?
C6 C5 O1 C10 -176.7(3) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 C1 179.3(3) . . . . ?
C14 C13 C12 C11 0.1(4) . . . . ?
C14 C13 C12 F1 179.8(2) . . . . ?
C14 C15 C16 C11 1.2(4) . . . . ?
C22 C17 C1 C8 41.3(3) . . . . ?
C22 C17 C1 N1 -83.3(3) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C15 C14 C13 C12 0.2(4) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C16 C11 C12 F1 -179.4(2) . . . . ?
C16 C11 N1 C2 -30.5(4) . . . . ?
C16 C11 N1 C1 102.4(3) . . . . ?
C3 C9 C4 C5 -179.7(3) . . . . ?
C3 C9 C8 C7 -179.7(2) . . . . ?
C3 C9 C8 C1 0.3(4) . . . . ?
C3 C2 N1 C11 -158.8(2) . . . . ?
C3 C2 N1 C1 68.0(3) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C12 C11 N1 C2 149.8(2) . . . . ?
C12 C11 N1 C1 -77.2(3) . . . . ?
C8 C9 C4 C5 -0.4(4) . . . . ?
C8 C9 C3 C2 17.8(4) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?
C8 C1 N1 C11 177.4(2) . . . . ?
C8 C1 N1 C2 -48.5(3) . . . . ?
C1 C17 C22 C21 173.1(3) . . . . ?
N1 C11 C16 C15 179.5(3) . . . . ?
N1 C11 C12 C13 179.9(3) . . . . ?
N1 C11 C12 F1 0.2(4) . . . . ?
O1 C5 C4 C9 -179.5(3) . . . . ?
O1 C5 C6 C7 179.8(3) . . . . ?
F3 C18 C17 C22 -179.0(2) . . . . ?
F3 C18 C17 C1 6.5(4) . . . . ?
F2 C14 C13 C12 -179.1(2) . . . . ?
F2 C14 C15 C16 178.5(3) . . . . ?
F4 C20 C21 C22 179.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168308514
