#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/20/7122083.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_7122083
loop_
_publ_author_name
'Tolmachova, Nataliya A.'
'Kondratov, Ivan S.'
'Dolovanyuk, Violetta G.'
'Pridma, Stanislav O.'
'Chernykh, Anton V.'
'Daniliuc, Constantin G.'
'Haufe, Günter'
_publ_section_title
;
 Synthesis of new fluorinated proline analogues from polyfluoroalkyl
 β-ketoacetals and ethyl isocyanoacetate.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9683
_journal_page_last               9686
_journal_paper_doi               10.1039/c8cc05912h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C7 H11 Cl F5 N O3'
_chemical_formula_weight         287.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2018-07-12 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.426(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5790(5)
_cell_length_b                   10.2974(4)
_cell_length_c                   9.8109(4)
_cell_measurement_reflns_used    5379
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.8042
_cell_measurement_theta_min      4.0484
_cell_volume                     1103.19(8)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14163
_diffrn_reflns_theta_full        66.80
_diffrn_reflns_theta_max         66.80
_diffrn_reflns_theta_min         4.05
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.790
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.68
_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    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0305
_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)+(0.0345P)²+0.4753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                1700
_reflns_number_total             1940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc05912h2.cif
_cod_data_source_block           dan8956
_cod_depositor_comments
'Adding full bibliography for 7122082--7122083.cif.'
_cod_database_code               7122083
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_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_posn
_atom_site_occupancy
Cl Cl1 0.12017(4) 0.32393(4) 0.51492(5) 0.01672(14) Uani d . . 1
N N1 0.12732(15) 0.95513(16) 0.23026(18) 0.0156(3) Uani d . . 1
H H1A 0.103(2) 1.017(2) 0.163(3) 0.023(6) Uiso d . . 1
H H1B 0.064(2) 0.923(2) 0.248(2) 0.021(6) Uiso d . . 1
O O1 0.10205(12) 0.70731(13) 0.31089(14) 0.0191(3) Uani d . . 1
O O2 0.17230(13) 0.62229(14) 0.14308(16) 0.0218(3) Uani d . . 1
H H2A 0.151(3) 0.549(3) 0.171(3) 0.042(8) Uiso d . . 1
O O3 0.09952(13) 0.40489(14) 0.20912(18) 0.0193(3) Uani d . . 1
H H3A 0.101(2) 0.349(3) 0.158(3) 0.033(8) Uiso d . . 1
H H3B 0.127(2) 0.379(2) 0.296(3) 0.029(7) Uiso d . . 1
F F1 0.35710(11) 0.93612(12) 0.02848(12) 0.0258(3) Uani d . . 1
F F2 0.38150(10) 0.73156(11) 0.08580(12) 0.0230(3) Uani d . . 1
F F3 0.56315(11) 0.99738(13) 0.24042(17) 0.0400(4) Uani d . . 1
F F4 0.57914(11) 0.80435(14) 0.33063(14) 0.0368(3) Uani d . . 1
F F5 0.59352(11) 0.83432(12) 0.11990(14) 0.0300(3) Uani d . . 1
C C2 0.18598(17) 0.84783(18) 0.1729(2) 0.0146(4) Uani d . . 1
H H2 0.1626 0.8539 0.0654 0.018 Uiso calc U R 1
C C3 0.32646(16) 0.86959(18) 0.2462(2) 0.0147(4) Uani d . . 1
H H3 0.3579 0.8045 0.3256 0.018 Uiso calc U R 1
C C4 0.33682(17) 1.00573(19) 0.3142(2) 0.0187(4) Uani d . . 1
H H4A 0.4122 1.0139 0.3991 0.022 Uiso calc U R 1
H H4B 0.3365 1.0742 0.2432 0.022 Uiso calc U R 1
C C5 0.22327(18) 1.01358(19) 0.3581(2) 0.0194(4) Uani d . . 1
H H5A 0.2334 0.9629 0.4471 0.023 Uiso calc U R 1
H H5B 0.2033 1.1047 0.3736 0.023 Uiso calc U R 1
C C6 0.14677(16) 0.71789(18) 0.2167(2) 0.0141(4) Uani d . . 1
C C7 0.39661(17) 0.85372(18) 0.1421(2) 0.0159(4) Uani d . . 1
C C8 0.53617(18) 0.8733(2) 0.2091(2) 0.0230(5) 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
C5 N1 C2 107.92(15)
C5 N1 H1A 107.4(15)
C2 N1 H1A 108.8(15)
C5 N1 H1B 114.8(15)
C2 N1 H1B 108.3(15)
H1A N1 H1B 110.(2)
C6 O2 H2A 110.1(19)
H3A O3 H3B 110.(3)
N1 C2 C6 109.08(15)
N1 C2 C3 104.71(14)
C6 C2 C3 111.08(15)
N1 C2 H2 110.6
C6 C2 H2 110.6
C3 C2 H2 110.6
C7 C3 C4 114.17(15)
C7 C3 C2 112.70(15)
C4 C3 C2 104.43(15)
C7 C3 H3 108.4
C4 C3 H3 108.4
C2 C3 H3 108.4
C5 C4 C3 102.82(15)
C5 C4 H4A 111.2
C3 C4 H4A 111.2
C5 C4 H4B 111.2
C3 C4 H4B 111.2
H4A C4 H4B 109.1
N1 C5 C4 102.26(15)
N1 C5 H5A 111.3
C4 C5 H5A 111.3
N1 C5 H5B 111.3
C4 C5 H5B 111.3
H5A C5 H5B 109.2
O1 C6 O2 125.98(17)
O1 C6 C2 122.77(17)
O2 C6 C2 111.20(16)
F1 C7 F2 106.38(15)
F1 C7 C3 112.24(15)
F2 C7 C3 110.43(15)
F1 C7 C8 106.75(15)
F2 C7 C8 105.59(15)
C3 C7 C8 114.89(16)
F5 C8 F3 108.26(17)
F5 C8 F4 108.02(17)
F3 C8 F4 108.47(18)
F5 C8 C7 111.31(17)
F3 C8 C7 110.93(16)
F4 C8 C7 109.76(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.498(3)
N1 C2 1.501(2)
N1 H1A 0.89(3)
N1 H1B 0.87(3)
O1 C6 1.205(2)
O2 C6 1.312(2)
O2 H2A 0.87(3)
O3 H3A 0.77(3)
O3 H3B 0.85(3)
F1 C7 1.354(2)
F2 C7 1.362(2)
F3 C8 1.327(2)
F4 C8 1.333(3)
F5 C8 1.325(2)
C2 C6 1.520(3)
C2 C3 1.560(2)
C2 H2 1.0
C3 C7 1.510(3)
C3 C4 1.540(3)
C3 H3 1.0
C4 C5 1.516(3)
C4 H4A 0.99
C4 H4B 0.99
C5 H5A 0.99
C5 H5B 0.99
C7 C8 1.542(3)
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
N1 H1A Cl1 4_575 0.89(3) 2.24(3) 3.0871(18) 157.(2)
N1 H1B O3 2 0.87(3) 2.08(3) 2.926(2) 163.(2)
O2 H2A O3 . 0.87(3) 1.68(3) 2.5505(19) 174.(3)
O3 H3A Cl1 4_565 0.77(3) 2.32(3) 3.0891(17) 176.(3)
O3 H3B Cl1 . 0.85(3) 2.24(3) 3.0456(17) 157.(2)
C2 H2 O1 4_575 1.0 2.44 3.404(2) 161.4
C3 H3 F2 4_576 1.0 2.5 3.344(2) 141.5
C5 H5A O2 4_576 0.99 2.42 3.350(2) 155.6
C5 H5B Cl1 1_565 0.99 2.97 3.902(2) 156.9
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
C5 N1 C2 C6 104.46(17)
C5 N1 C2 C3 -14.51(19)
N1 C2 C3 C7 -136.51(16)
C6 C2 C3 C7 105.88(18)
N1 C2 C3 C4 -12.04(19)
C6 C2 C3 C4 -129.65(16)
C7 C3 C4 C5 157.13(16)
C2 C3 C4 C5 33.61(18)
C2 N1 C5 C4 35.74(19)
C3 C4 C5 N1 -42.28(18)
N1 C2 C6 O1 -16.6(2)
C3 C2 C6 O1 98.3(2)
N1 C2 C6 O2 165.68(15)
C3 C2 C6 O2 -79.40(19)
C4 C3 C7 F1 -60.8(2)
C2 C3 C7 F1 58.2(2)
C4 C3 C7 F2 -179.28(14)
C2 C3 C7 F2 -60.34(19)
C4 C3 C7 C8 61.4(2)
C2 C3 C7 C8 -179.62(16)
F1 C7 C8 F5 -66.7(2)
F2 C7 C8 F5 46.2(2)
C3 C7 C8 F5 168.17(16)
F1 C7 C8 F3 53.9(2)
F2 C7 C8 F3 166.85(16)
C3 C7 C8 F3 -71.2(2)
F1 C7 C8 F4 173.76(15)
F2 C7 C8 F4 -73.30(19)
C3 C7 C8 F4 48.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188970
