#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:36:15 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296680 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160004.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_7160004
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_formula_moiety         'Cl, C6 H9 F3 N O3'
_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   geom
_audit_creation_date             2024-05-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-26 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                   8.3231(7)
_cell_length_b                   8.6507(7)
_cell_length_c                   13.3347(11)
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      24.24
_cell_measurement_theta_min      2.88
_cell_volume                     960.11(14)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      172.65
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.807
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 576 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0316
_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)+(0.0361P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1518
_reflns_number_total             1691
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00688g2.cif
_cod_data_source_block           v387
_cod_depositor_comments
'Adding full bibliography for 7160001--7160004.cif.'
_cod_database_code               7160004
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.76281(8) 0.76334(9) 0.37240(6) 0.0281(2) Uani 1 1 d . . . . .
F1 F 0.4231(3) 0.3776(3) 0.47417(19) 0.0605(7) Uani 1 1 d . . . . .
F2 F 0.5432(3) 0.2310(3) 0.57995(18) 0.0608(7) Uani 1 1 d . . . . .
F3 F 0.6678(3) 0.3117(3) 0.45071(17) 0.0566(7) Uani 1 1 d . . . . .
O1 O 0.9285(3) 0.9294(3) 0.7278(2) 0.0473(7) Uani 1 1 d . . . . .
O2 O 0.6661(3) 0.9457(3) 0.7612(2) 0.0496(8) Uani 1 1 d . . . . .
H2 H 0.692237 1.028483 0.789819 0.074 Uiso 1 1 calc R U . . .
O3 O 0.6007(2) 0.4816(2) 0.56898(18) 0.0325(6) Uani 1 1 d . . . . .
N1 N 0.8845(3) 0.7082(3) 0.58448(19) 0.0260(6) Uani 1 1 d . . . . .
H1A H 0.978881 0.743185 0.610410 0.031 Uiso 1 1 calc R U . . .
H1B H 0.869599 0.753005 0.523438 0.031 Uiso 1 1 calc R U . . .
C2 C 0.7480(3) 0.7488(3) 0.6533(2) 0.0251(7) Uani 1 1 d . . . . .
H2A H 0.650414 0.774153 0.612672 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7193(4) 0.5994(4) 0.7119(3) 0.0330(9) Uani 1 1 d . . . . .
H3A H 0.797345 0.588090 0.767381 0.040 Uiso 1 1 calc R U . . .
H3B H 0.608856 0.595478 0.739360 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7443(4) 0.4772(3) 0.6326(2) 0.0292(7) Uani 1 1 d . . . . .
H4 H 0.762840 0.372545 0.662297 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8893(4) 0.5349(3) 0.5739(3) 0.0294(8) Uani 1 1 d . . . . .
H5A H 0.990155 0.492609 0.602159 0.035 Uiso 1 1 calc R U . . .
H5B H 0.881534 0.504291 0.502504 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7920(4) 0.8853(4) 0.7179(3) 0.0295(8) Uani 1 1 d . . . . .
C7 C 0.5610(5) 0.3543(4) 0.5203(3) 0.0383(9) 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'
Cl Cl 0.1484 0.1585 '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 0.0060 '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
C6 O2 H2 109.5 . . ?
C7 O3 C4 117.8(2) . . ?
H1A N1 H1B 108.4 . . ?
C2 N1 H1A 110.1 . . ?
C2 N1 H1B 110.1 . . ?
C2 N1 C5 108.1(2) . . ?
C5 N1 H1A 110.1 . . ?
C5 N1 H1B 110.1 . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 C3 103.5(2) . . ?
N1 C2 C6 110.4(2) . . ?
C3 C2 H2A 109.6 . . ?
C6 C2 H2A 109.6 . . ?
C6 C2 C3 114.1(3) . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 C2 102.3(2) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
O3 C4 C3 105.9(3) . . ?
O3 C4 H4 112.2 . . ?
O3 C4 C5 109.9(3) . . ?
C3 C4 H4 112.2 . . ?
C3 C4 C5 103.9(3) . . ?
C5 C4 H4 112.2 . . ?
N1 C5 C4 104.9(2) . . ?
N1 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.8 . . ?
O1 C6 O2 125.6(3) . . ?
O1 C6 C2 122.6(3) . . ?
O2 C6 C2 111.8(3) . . ?
F1 C7 F2 107.6(3) . . ?
F1 C7 F3 107.3(3) . . ?
F1 C7 O3 108.7(3) . . ?
F3 C7 F2 105.4(3) . . ?
O3 C7 F2 113.6(3) . . ?
O3 C7 F3 113.9(3) . . ?
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
F1 C7 1.318(5) . ?
F2 C7 1.338(4) . ?
F3 C7 1.337(4) . ?
O1 C6 1.206(4) . ?
O2 H2 0.8400 . ?
O2 C6 1.306(4) . ?
O3 C4 1.466(4) . ?
O3 C7 1.320(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.502(4) . ?
N1 C5 1.506(4) . ?
C2 H2A 1.0000 . ?
C2 C3 1.529(4) . ?
C2 C6 1.508(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.509(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.523(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
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
O3 C4 C5 N1 84.9(3) . . . . ?
N1 C2 C3 C4 -38.3(3) . . . . ?
N1 C2 C6 O1 -15.5(5) . . . . ?
N1 C2 C6 O2 165.2(3) . . . . ?
C2 N1 C5 C4 3.9(3) . . . . ?
C2 C3 C4 O3 -74.6(3) . . . . ?
C2 C3 C4 C5 41.1(3) . . . . ?
C3 C2 C6 O1 100.4(4) . . . . ?
C3 C2 C6 O2 -78.8(4) . . . . ?
C3 C4 C5 N1 -28.0(3) . . . . ?
C4 O3 C7 F1 175.1(3) . . . . ?
C4 O3 C7 F2 55.3(4) . . . . ?
C4 O3 C7 F3 -65.4(4) . . . . ?
C5 N1 C2 C3 21.3(3) . . . . ?
C5 N1 C2 C6 143.8(3) . . . . ?
C6 C2 C3 C4 -158.3(3) . . . . ?
C7 O3 C4 C3 -154.2(3) . . . . ?
C7 O3 C4 C5 94.2(3) . . . . ?
