#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:36:15 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296680 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160001.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_7160001
loop_
_publ_author_name
'Logvinenko, Ivan G.'
'Sadkova, Iryna V.'
'Tolmachova, Nataliya A.'
'Shishkina, Svitlana V.'
'Daniliuc, Constantin G.'
'Haufe, Günter'
'Kondratov, Ivan S.'
_publ_section_title
;
 4-Trifluoromethoxy proline: synthesis of stereoisomers and lipophilicity
 study.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7982
_journal_page_last               7988
_journal_paper_doi               10.1039/d4ob00688g
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C6 H9 Cl F3 N O3'
_chemical_formula_weight         235.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2024-04-09 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4353(2)
_cell_length_b                   7.0050(3)
_cell_length_c                   23.8253(10)
_cell_measurement_reflns_used    2122
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6339
_cell_measurement_theta_min      6.5870
_cell_volume                     907.13(6)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7754
_diffrn_reflns_theta_full        66.69
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_min         6.59
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.129
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.188
_refine_ls_abs_structure_details
;

Flack x determined using 551 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                1461
_reflns_number_total             1612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00688g2.cif
_cod_data_source_block           dan9182
_cod_depositor_comments
'Adding full bibliography for 7160001--7160004.cif.'
_cod_database_code               7160001
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.30935(14) 0.17038(11) 0.44169(3) 0.01851(19) Uani d . . . 1 . .
F F1 0.6070(4) 0.7632(3) 0.26757(8) 0.0294(5) Uani d . . . 1 . .
F F2 0.2595(4) 0.8877(3) 0.29082(8) 0.0308(5) Uani d . . . 1 . .
F F3 0.2694(4) 0.6658(3) 0.22928(7) 0.0293(5) Uani d . . . 1 . .
N N1 0.1828(6) 0.3868(4) 0.42441(10) 0.0156(6) Uani d . . . 1 . .
H H1A 0.337(8) 0.372(5) 0.4424(16) 0.022(9) Uiso d . . . 1 . .
H H1B 0.087(7) 0.309(6) 0.4449(14) 0.013(8) Uiso d . . . 1 . .
O O1 0.5165(4) 0.6529(3) 0.45445(8) 0.0185(5) Uani d . . . 1 . .
O O2 0.2823(5) 0.8959(4) 0.42417(9) 0.0211(5) Uani d . . . 1 . .
H H2A 0.397(9) 0.969(7) 0.4290(18) 0.031(12) Uiso d . . . 1 . .
O O3 0.3626(4) 0.5921(3) 0.31820(8) 0.0165(5) Uani d . . . 1 . .
C C2 0.0985(6) 0.5908(5) 0.42677(12) 0.0150(7) Uani d . . . 1 . .
H H2 -0.0224 0.6081 0.458 0.018 Uiso calc U . R 1 . .
C C3 -0.0270(6) 0.6219(5) 0.37046(12) 0.0163(7) Uani d . . . 1 . .
H H3A -0.1999 0.5777 0.3715 0.02 Uiso calc U . R 1 . .
H H3B -0.0236 0.7584 0.3597 0.02 Uiso calc U . R 1 . .
C C4 0.1252(6) 0.5021(5) 0.33013(13) 0.0171(7) Uani d . . . 1 . .
H H4 0.0325 0.4713 0.295 0.021 Uiso calc U . R 1 . .
C C5 0.1857(6) 0.3241(5) 0.36382(11) 0.0168(6) Uani d . . . 1 . .
H H5A 0.0613 0.2233 0.3572 0.02 Uiso calc U . R 1 . .
H H5B 0.3497 0.274 0.3534 0.02 Uiso calc U . R 1 . .
C C6 0.3255(6) 0.7159(4) 0.43673(12) 0.0151(6) Uani d . . . 1 . .
C C7 0.3712(6) 0.7237(5) 0.27766(13) 0.0201(8) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 108.4(2) ?
C2 N1 H1A . . 111.(2) ?
C5 N1 H1A . . 113.(2) ?
C2 N1 H1B . . 112.(2) ?
C5 N1 H1B . . 110.(2) ?
H1A N1 H1B . . 102.(3) ?
C6 O2 H2A . . 116.(3) ?
C7 O3 C4 . . 117.9(2) ?
N1 C2 C3 . . 103.9(3) ?
N1 C2 C6 . . 107.7(3) ?
C3 C2 C6 . . 114.6(3) ?
N1 C2 H2 . . 110.1 ?
C3 C2 H2 . . 110.1 ?
C6 C2 H2 . . 110.1 ?
C4 C3 C2 . . 103.6(3) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
O3 C4 C5 . . 105.4(3) ?
O3 C4 C3 . . 111.4(3) ?
C5 C4 C3 . . 103.7(3) ?
O3 C4 H4 . . 112.0 ?
C5 C4 H4 . . 112.0 ?
C3 C4 H4 . . 112.0 ?
N1 C5 C4 . . 105.3(3) ?
N1 C5 H5A . . 110.7 ?
C4 C5 H5A . . 110.7 ?
N1 C5 H5B . . 110.7 ?
C4 C5 H5B . . 110.7 ?
H5A C5 H5B . . 108.8 ?
O1 C6 O2 . . 125.7(3) ?
O1 C6 C2 . . 122.6(3) ?
O2 C6 C2 . . 111.7(3) ?
F1 C7 F2 . . 107.5(3) ?
F1 C7 O3 . . 107.9(3) ?
F2 C7 O3 . . 114.1(3) ?
F1 C7 F3 . . 107.7(3) ?
F2 C7 F3 . . 105.9(3) ?
O3 C7 F3 . . 113.5(3) ?
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 C7 . 1.333(4) ?
F2 C7 . 1.336(4) ?
F3 C7 . 1.341(4) ?
N1 C2 . 1.502(4) ?
N1 C5 . 1.509(4) ?
N1 H1A . 0.95(4) ?
N1 H1B . 0.90(4) ?
O1 C6 . 1.205(4) ?
O2 C6 . 1.317(4) ?
O2 H2A . 0.82(5) ?
O3 C7 . 1.336(4) ?
O3 C4 . 1.464(4) ?
C2 C3 . 1.521(4) ?
C2 C6 . 1.532(4) ?
C2 H2 . 1.0 ?
C3 C4 . 1.520(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.519(5) ?
C4 H4 . 1.0 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A Cl1 1_655 0.95(4) 2.39(4) 3.176(3) 141.(3) ?
N1 H1B Cl1 . 0.90(4) 2.36(4) 3.102(3) 140.(3) ?
O2 H2A Cl1 1_665 0.82(5) 2.15(5) 2.966(3) 178.(4) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 C3 . . . . 18.5(3) ?
C5 N1 C2 C6 . . . . -103.5(3) ?
N1 C2 C3 C4 . . . . -35.2(3) ?
C6 C2 C3 C4 . . . . 82.1(3) ?
C7 O3 C4 C5 . . . . 163.5(3) ?
C7 O3 C4 C3 . . . . -84.7(3) ?
C2 C3 C4 O3 . . . . -74.1(3) ?
C2 C3 C4 C5 . . . . 38.7(3) ?
C2 N1 C5 C4 . . . . 5.4(3) ?
O3 C4 C5 N1 . . . . 89.9(3) ?
C3 C4 C5 N1 . . . . -27.2(3) ?
N1 C2 C6 O1 . . . . -18.1(4) ?
C3 C2 C6 O1 . . . . -133.2(3) ?
N1 C2 C6 O2 . . . . 162.5(2) ?
C3 C2 C6 O2 . . . . 47.5(4) ?
C4 O3 C7 F1 . . . . -170.0(3) ?
C4 O3 C7 F2 . . . . 70.7(4) ?
C4 O3 C7 F3 . . . . -50.7(4) ?
