#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157700.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_7157700
loop_
_publ_author_name
'Wang, Xiaonan'
'Gao, Yuan'
'Wei, Zhonglin'
'Cao, Jungang'
'Liang, Dapeng'
'Lin, Yingjie'
'Duan, Haifeng'
_publ_section_title
;
 Enantioselective addition of thiols to trifluoromethyl ketimines:
 synthesis of N,S-ketals.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7431
_journal_page_last               7436
_journal_paper_doi               10.1039/d0ob01725f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 Cl F3 N O2 S'
_chemical_formula_sum            'C19 H19 Cl F3 N O2 S'
_chemical_formula_weight         417.9
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-11-09 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                106.067(2)
_cell_angle_beta                 98.907(2)
_cell_angle_gamma                110.261(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6920(10)
_cell_length_b                   10.4626(12)
_cell_length_c                   12.9164(15)
_cell_measurement_reflns_used    2075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.886
_cell_measurement_theta_min      2.268
_cell_volume                     1017.1(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'XS n/a (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5748
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0870P)²+0.2458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                2927
_reflns_number_total             4007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01725f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
          Adding full bibliography for 7157700.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         41.79
_cod_original_formula_moiety         'C1.9 H1.9 Cl0.1 F0.3 N0.1 O0.2 S0.1'
_cod_original_formula_units_Z            20
_cod_original_formula_sum        'C1.90 H1.90 Cl0.10 F0.30 N0.10 O0.20 S0.10'
_cod_database_code               7157700
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44732(10) 0.29876(8) 0.73703(6) 0.0777(3) Uani 1 1 d . . .
Cl2 Cl -0.07676(11) 0.02263(9) 0.26126(7) 0.0931(3) Uani 1 1 d . . .
N1 N 0.6030(2) 0.50045(18) 0.64480(15) 0.0446(4) Uani 1 1 d . . .
H1 H 0.6234 0.4762 0.5808 0.054 Uiso 1 1 calc R . .
O2 O 0.4849(2) 0.64165(18) 0.59318(13) 0.0615(5) Uani 1 1 d . . .
O3 O 0.5328(2) 0.64734(18) 0.77106(13) 0.0576(4) Uani 1 1 d . . .
F4 F 0.6518(2) 0.24586(17) 0.56430(13) 0.0752(5) Uani 1 1 d . . .
C5 C 0.5354(3) 0.6010(2) 0.66510(18) 0.0462(5) Uani 1 1 d . . .
C6 C 0.6438(3) 0.4306(2) 0.71992(19) 0.0522(5) Uani 1 1 d . . .
F7 F 0.8843(2) 0.4328(2) 0.65272(18) 0.0989(6) Uani 1 1 d . . .
C8 C 0.1638(4) 0.0288(3) 0.4222(2) 0.0678(7) Uani 1 1 d . . .
H8 H 0.1491 -0.0606 0.3724 0.081 Uiso 1 1 calc R . .
C9 C 0.7607(3) 0.5368(3) 0.8359(2) 0.0577(6) Uani 1 1 d . . .
C10 C 0.3025(3) 0.2226(3) 0.6010(2) 0.0636(7) Uani 1 1 d . . .
F11 F 0.7853(3) 0.2755(2) 0.72858(17) 0.1178(8) Uani 1 1 d . . .
C12 C 0.2795(4) 0.0899(3) 0.5264(3) 0.0689(7) Uani 1 1 d . . .
H12 H 0.3433 0.0410 0.5470 0.083 Uiso 1 1 calc R . .
C13 C 0.7406(4) 0.3454(3) 0.6663(2) 0.0695(7) Uani 1 1 d . . .
C14 C 0.8855(3) 0.6689(3) 0.8465(2) 0.0608(6) Uani 1 1 d . . .
H14 H 0.8962 0.6931 0.7831 0.073 Uiso 1 1 calc R . .
C15 C 0.0704(3) 0.1018(3) 0.3930(2) 0.0654(7) Uani 1 1 d . . .
C16 C 0.4830(4) 0.7679(3) 0.8153(2) 0.0660(7) Uani 1 1 d . . .
C17 C 0.2045(3) 0.2922(3) 0.5703(3) 0.0700(7) Uani 1 1 d . . .
H17 H 0.2162 0.3803 0.6205 0.084 Uiso 1 1 calc R . .
C18 C 0.0887(4) 0.2318(3) 0.4651(3) 0.0752(8) Uani 1 1 d . . .
H18 H 0.0241 0.2798 0.4440 0.090 Uiso 1 1 calc R . .
C19 C 0.9943(4) 0.7650(3) 0.9501(3) 0.0775(8) Uani 1 1 d . . .
H19 H 1.0768 0.8537 0.9559 0.093 Uiso 1 1 calc R . .
C20 C 0.7509(5) 0.5041(4) 0.9317(2) 0.0968(12) Uani 1 1 d . . .
H20 H 0.6695 0.4155 0.9270 0.116 Uiso 1 1 calc R . .
C21 C 0.9822(5) 0.7318(4) 1.0439(3) 0.0920(10) Uani 1 1 d . . .
H21 H 1.0562 0.7971 1.1134 0.110 Uiso 1 1 calc R . .
C22 C 0.8619(6) 0.6028(5) 1.0354(3) 0.1172(15) Uani 1 1 d . . .
H22 H 0.8532 0.5800 1.0995 0.141 Uiso 1 1 calc R . .
C1 C 0.5975(6) 0.9023(3) 0.7996(3) 0.1032(12) Uani 1 1 d . . .
H1A H 0.7146 0.9194 0.8272 0.155 Uiso 1 1 calc R . .
H1B H 0.5783 0.9847 0.8402 0.155 Uiso 1 1 calc R . .
H1C H 0.5728 0.8888 0.7213 0.155 Uiso 1 1 calc R . .
C2 C 0.5161(7) 0.7879(5) 0.9384(3) 0.1189(15) Uani 1 1 d . . .
H2A H 0.4503 0.6981 0.9465 0.178 Uiso 1 1 calc R . .
H2B H 0.4837 0.8630 0.9767 0.178 Uiso 1 1 calc R . .
H2C H 0.6353 0.8153 0.9702 0.178 Uiso 1 1 calc R . .
C3 C 0.2971(5) 0.7197(5) 0.7604(4) 0.1218(15) Uani 1 1 d . . .
H3A H 0.2813 0.7115 0.6832 0.183 Uiso 1 1 calc R . .
H3B H 0.2581 0.7901 0.7982 0.183 Uiso 1 1 calc R . .
H3C H 0.2330 0.6268 0.7645 0.183 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
C10 S1 C6 102.91(11) . . ?
C5 N1 H1 116.8 . . ?
C5 N1 C6 126.33(18) . . ?
C6 N1 H1 116.8 . . ?
C5 O3 C16 121.74(19) . . ?
O2 C5 N1 122.5(2) . . ?
O2 C5 O3 125.3(2) . . ?
O3 C5 N1 112.21(19) . . ?
N1 C6 S1 112.07(16) . . ?
N1 C6 C9 113.95(19) . . ?
N1 C6 C13 106.1(2) . . ?
C9 C6 S1 108.89(16) . . ?
C9 C6 C13 107.1(2) . . ?
C13 C6 S1 108.43(18) . . ?
C12 C8 H8 120.5 . . ?
C15 C8 H8 120.5 . . ?
C15 C8 C12 119.0(3) . . ?
C14 C9 C6 119.8(2) . . ?
C20 C9 C6 122.3(2) . . ?
C20 C9 C14 117.8(2) . . ?
C12 C10 S1 121.0(2) . . ?
C17 C10 S1 120.2(2) . . ?
C17 C10 C12 118.8(3) . . ?
C8 C12 C10 121.0(3) . . ?
C8 C12 H12 119.5 . . ?
C10 C12 H12 119.5 . . ?
F4 C13 C6 113.7(2) . . ?
F4 C13 F7 105.3(2) . . ?
F7 C13 C6 111.9(2) . . ?
F11 C13 F4 106.8(2) . . ?
F11 C13 C6 111.7(2) . . ?
F11 C13 F7 106.9(2) . . ?
C9 C14 H14 119.7 . . ?
C19 C14 C9 120.7(3) . . ?
C19 C14 H14 119.7 . . ?
C8 C15 Cl2 118.5(2) . . ?
C18 C15 Cl2 120.1(2) . . ?
C18 C15 C8 121.4(3) . . ?
O3 C16 C1 109.8(2) . . ?
O3 C16 C2 101.6(2) . . ?
O3 C16 C3 108.8(2) . . ?
C1 C16 C2 110.6(3) . . ?
C3 C16 C1 113.6(3) . . ?
C3 C16 C2 111.7(3) . . ?
C10 C17 H17 119.8 . . ?
C10 C17 C18 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C15 C18 C17 119.4(3) . . ?
C15 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C14 C19 H19 119.6 . . ?
C21 C19 C14 120.8(3) . . ?
C21 C19 H19 119.6 . . ?
C9 C20 H20 119.8 . . ?
C9 C20 C22 120.5(3) . . ?
C22 C20 H20 119.8 . . ?
C19 C21 H21 120.2 . . ?
C22 C21 C19 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C22 H22 119.7 . . ?
C21 C22 C20 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C16 C1 H1A 109.5 . . ?
C16 C1 H1B 109.5 . . ?
C16 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 C2 H2A 109.5 . . ?
C16 C2 H2B 109.5 . . ?
C16 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 C3 H3A 109.5 . . ?
C16 C3 H3B 109.5 . . ?
C16 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
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
S1 C6 1.877(2) . ?
S1 C10 1.775(3) . ?
Cl2 C15 1.741(3) . ?
N1 H1 0.8600 . ?
N1 C5 1.358(3) . ?
N1 C6 1.438(3) . ?
O2 C5 1.208(3) . ?
O3 C5 1.326(3) . ?
O3 C16 1.470(3) . ?
F4 C13 1.336(3) . ?
C6 C9 1.528(3) . ?
C6 C13 1.530(4) . ?
F7 C13 1.339(4) . ?
C8 H8 0.9300 . ?
C8 C12 1.375(4) . ?
C8 C15 1.370(4) . ?
C9 C14 1.385(4) . ?
C9 C20 1.379(4) . ?
C10 C12 1.380(4) . ?
C10 C17 1.378(4) . ?
F11 C13 1.326(3) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C19 1.379(4) . ?
C15 C18 1.359(4) . ?
C16 C1 1.504(4) . ?
C16 C2 1.512(4) . ?
C16 C3 1.501(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C21 1.358(4) . ?
C20 H20 0.9300 . ?
C20 C22 1.391(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.353(5) . ?
C22 H22 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
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
S1 C6 C9 C14 -160.3(2) . . . . ?
S1 C6 C9 C20 22.0(3) . . . . ?
S1 C6 C13 F4 61.6(3) . . . . ?
S1 C6 C13 F7 -179.16(18) . . . . ?
S1 C6 C13 F11 -59.3(3) . . . . ?
S1 C10 C12 C8 178.1(2) . . . . ?
S1 C10 C17 C18 -178.6(2) . . . . ?
Cl2 C15 C18 C17 179.0(2) . . . . ?
N1 C6 C9 C14 -34.4(3) . . . . ?
N1 C6 C9 C20 147.9(3) . . . . ?
N1 C6 C13 F4 -59.0(3) . . . . ?
N1 C6 C13 F7 60.3(3) . . . . ?
N1 C6 C13 F11 -179.9(2) . . . . ?
C5 N1 C6 S1 70.2(2) . . . . ?
C5 N1 C6 C9 -54.0(3) . . . . ?
C5 N1 C6 C13 -171.6(2) . . . . ?
C5 O3 C16 C1 -57.9(3) . . . . ?
C5 O3 C16 C2 -174.9(3) . . . . ?
C5 O3 C16 C3 67.1(3) . . . . ?
C6 S1 C10 C12 97.9(2) . . . . ?
C6 S1 C10 C17 -85.4(2) . . . . ?
C6 N1 C5 O2 -170.6(2) . . . . ?
C6 N1 C5 O3 9.6(3) . . . . ?
C6 C9 C14 C19 -178.8(2) . . . . ?
C6 C9 C20 C22 178.8(3) . . . . ?
C8 C15 C18 C17 0.2(4) . . . . ?
C9 C6 C13 F4 179.0(2) . . . . ?
C9 C6 C13 F7 -61.8(3) . . . . ?
C9 C6 C13 F11 58.0(3) . . . . ?
C9 C14 C19 C21 0.5(4) . . . . ?
C9 C20 C22 C21 -0.6(7) . . . . ?
C10 S1 C6 N1 36.2(2) . . . . ?
C10 S1 C6 C9 163.24(17) . . . . ?
C10 S1 C6 C13 -80.58(18) . . . . ?
C10 C17 C18 C15 1.1(4) . . . . ?
C12 C8 C15 Cl2 -179.5(2) . . . . ?
C12 C8 C15 C18 -0.7(4) . . . . ?
C12 C10 C17 C18 -1.9(4) . . . . ?
C13 C6 C9 C14 82.7(3) . . . . ?
C13 C6 C9 C20 -95.1(3) . . . . ?
C14 C9 C20 C22 1.0(5) . . . . ?
C14 C19 C21 C22 -0.1(6) . . . . ?
C15 C8 C12 C10 -0.1(4) . . . . ?
C16 O3 C5 N1 173.09(19) . . . . ?
C16 O3 C5 O2 -6.8(4) . . . . ?
C17 C10 C12 C8 1.4(4) . . . . ?
C19 C21 C22 C20 0.2(7) . . . . ?
C20 C9 C14 C19 -1.0(4) . . . . ?
