#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/88/7128828.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_7128828
loop_
_publ_author_name
'Ye, Zhi-Peng'
'Gao, Jie'
'Duan, Xin-Yu'
'Guan, Jian-Ping'
'Liu, Fang'
'Chen, Kai'
'Xiao, Jun-An'
'Xiang, Hao-Yue'
'Yang, Hua'
_publ_section_title
;
 Electrochemical heterodifunctionalization of α-CF₃ alkenes to
 access α-trifluoromethyl-β-sulfonyl tertiary alcohols.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8969
_journal_page_last               8972
_journal_paper_doi               10.1039/d1cc03288g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H17 F3 O3 S'
_chemical_formula_sum            'C21 H17 F3 O3 S'
_chemical_formula_weight         406.40
_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             2021-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-17 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                100.6367(19)
_cell_angle_beta                 95.0698(19)
_cell_angle_gamma                103.2609(19)
_cell_formula_units_Z            2
_cell_length_a                   5.9954(2)
_cell_length_b                   10.0675(4)
_cell_length_c                   16.2734(7)
_cell_measurement_reflns_used    11736
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      1.29
_cell_volume                     930.81(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11736
_diffrn_reflns_theta_full        27.68
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         1.29
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.223
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0431
_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)+(0.0549P)²+0.4761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                3689
_reflns_number_total             4236
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc03288g2.cif
_cod_data_source_block           hyang401_0m
_cod_depositor_comments
;
          Adding full bibliography for 7128828.cif.

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H34 F6 O6 S2'
_cod_original_formula_weight         812.81
_cod_original_formula_moiety         '2(C21 H17 F3 O3 S)'
_cod_original_formula_units_Z            1
_cod_database_code               7128828
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C4(H4), C2(H2), C15(H15), C7(H7), C9(H9), C17(H17), C11(H11),
 C12(H12), C10(H10), C14(H14), C13(H13), C18(H18)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.19503(8) 0.65176(5) 0.44869(3) 0.04279(14) Uani 1 d . . .
F2 F 0.41951(18) 0.28245(12) 0.29550(8) 0.0518(3) Uani 1 d . . .
F1 F 0.1423(2) 0.20021(12) 0.36099(8) 0.0554(3) Uani 1 d . . .
O3 O -0.10880(19) 0.37817(16) 0.31552(8) 0.0459(3) Uani 1 d . . .
H3 H -0.1408 0.3652 0.3618 0.069 Uiso 1 calc . . GR
F3 F 0.0821(2) 0.18835(13) 0.22785(8) 0.0587(3) Uani 1 d . . .
C6 C 0.1933(3) 0.48662(17) 0.24601(10) 0.0313(3) Uani 1 d . . .
C19 C 0.1329(3) 0.41148(18) 0.31726(10) 0.0325(3) Uani 1 d . . .
C5 C 0.0182(3) 0.49320(19) 0.18659(11) 0.0362(4) Uani 1 d . . .
H5 H -0.1346 0.4500 0.1898 0.043 Uiso 1 calc . . R
C21 C 0.1961(3) 0.26999(19) 0.30011(11) 0.0393(4) Uani 1 d . . .
O2 O -0.0491(3) 0.63717(17) 0.43232(11) 0.0624(4) Uani 1 d . . .
C20 C 0.2621(3) 0.49234(18) 0.40405(10) 0.0342(3) Uani 1 d . . .
H20A H 0.4264 0.5129 0.4000 0.041 Uiso 1 calc . . R
H20B H 0.2341 0.4308 0.4435 0.041 Uiso 1 calc . . R
C8 C 0.3440(3) 0.70569(19) 0.04652(11) 0.0400(4) Uani 1 d . . .
C3 C 0.2950(3) 0.62981(18) 0.11556(10) 0.0358(3) Uani 1 d . . .
C1 C 0.4212(3) 0.54981(19) 0.23869(11) 0.0361(4) Uani 1 d . . .
H1 H 0.5412 0.5446 0.2773 0.043 Uiso 1 calc . . R
C4 C 0.0691(3) 0.56343(19) 0.12261(11) 0.0390(4) Uani 1 d . . .
H4 H -0.0508 0.5664 0.0832 0.047 Uiso 1 calc . . R
C2 C 0.4702(3) 0.62015(19) 0.17457(11) 0.0378(4) Uani 1 d . . .
H2 H 0.6232 0.6619 0.1707 0.045 Uiso 1 calc . . R
O1 O 0.2993(3) 0.68234(16) 0.53517(9) 0.0616(4) Uani 1 d . . .
C16 C 0.3393(3) 0.78189(19) 0.39970(12) 0.0422(4) Uani 1 d . . .
C15 C 0.2200(4) 0.8196(2) 0.33516(14) 0.0528(5) Uani 1 d . . .
H15 H 0.0640 0.7772 0.3173 0.063 Uiso 1 calc . . R
C7 C 0.5261(4) 0.6910(2) 0.00138(13) 0.0499(5) Uani 1 d . . .
H7 H 0.6228 0.6366 0.0163 0.060 Uiso 1 calc . . R
C9 C 0.2045(4) 0.7887(2) 0.02323(13) 0.0500(5) Uani 1 d . . .
H9 H 0.0823 0.8005 0.0529 0.060 Uiso 1 calc . . R
C17 C 0.5709(4) 0.8440(2) 0.42722(15) 0.0555(5) Uani 1 d . . .
H17 H 0.6494 0.8174 0.4708 0.067 Uiso 1 calc . . R
C11 C 0.4250(5) 0.8372(3) -0.08808(15) 0.0678(7) Uani 1 d . . .
H11 H 0.4511 0.8804 -0.1334 0.081 Uiso 1 calc . . R
C12 C 0.5653(4) 0.7566(3) -0.06554(14) 0.0620(6) Uani 1 d . . .
H12 H 0.6878 0.7458 -0.0953 0.074 Uiso 1 calc . . R
C10 C 0.2451(5) 0.8542(2) -0.04366(15) 0.0636(6) Uani 1 d . . .
H10 H 0.1505 0.9097 -0.0586 0.076 Uiso 1 calc . . R
C14 C 0.3380(5) 0.9223(2) 0.29734(16) 0.0672(7) Uani 1 d . . .
H14 H 0.2612 0.9489 0.2534 0.081 Uiso 1 calc . . R
C13 C 0.5677(5) 0.9845(3) 0.32463(19) 0.0731(7) Uani 1 d . . .
H13 H 0.6456 1.0535 0.2991 0.088 Uiso 1 calc . . R
C18 C 0.6833(5) 0.9465(3) 0.3888(2) 0.0726(7) Uani 1 d . . .
H18 H 0.8389 0.9899 0.4068 0.087 Uiso 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'
F F 0.0171 0.0103 '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
O2 S1 C20 109.85(9) . . ?
O2 S1 O1 117.83(10) . . ?
O2 S1 C16 108.94(9) . . ?
O1 S1 C20 103.89(9) . . ?
O1 S1 C16 108.13(10) . . ?
C16 S1 C20 107.73(8) . . ?
C19 O3 H3 109.5 . . ?
C5 C6 C19 119.55(14) . . ?
C5 C6 C1 118.59(15) . . ?
C1 C6 C19 121.86(14) . . ?
O3 C19 C6 108.55(12) . . ?
O3 C19 C21 105.19(14) . . ?
O3 C19 C20 112.65(13) . . ?
C6 C19 C21 109.49(13) . . ?
C6 C19 C20 113.52(13) . . ?
C20 C19 C21 107.07(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.40(15) . . ?
C4 C5 H5 119.8 . . ?
F2 C21 F1 107.09(14) . . ?
F2 C21 F3 106.73(15) . . ?
F2 C21 C19 113.03(14) . . ?
F1 C21 C19 111.09(14) . . ?
F3 C21 F1 106.79(15) . . ?
F3 C21 C19 111.75(15) . . ?
S1 C20 H20A 107.8 . . ?
S1 C20 H20B 107.8 . . ?
C19 C20 S1 118.00(12) . . ?
C19 C20 H20A 107.8 . . ?
C19 C20 H20B 107.8 . . ?
H20A C20 H20B 107.1 . . ?
C7 C8 C3 120.70(17) . . ?
C9 C8 C3 121.05(17) . . ?
C9 C8 C7 118.21(18) . . ?
C4 C3 C8 120.46(15) . . ?
C4 C3 C2 117.43(15) . . ?
C2 C3 C8 122.10(15) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.54(15) . . ?
C2 C1 H1 119.7 . . ?
C5 C4 C3 121.72(15) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.30(15) . . ?
C1 C2 H2 119.4 . . ?
C15 C16 S1 119.59(16) . . ?
C15 C16 C17 121.59(19) . . ?
C17 C16 S1 118.81(16) . . ?
C16 C15 H15 120.8 . . ?
C16 C15 C14 118.5(2) . . ?
C14 C15 H15 120.8 . . ?
C8 C7 H7 119.6 . . ?
C12 C7 C8 120.7(2) . . ?
C12 C7 H7 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(2) . . ?
C18 C17 H17 120.7 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C14 C13 H13 119.6 . . ?
C18 C13 C14 120.8(2) . . ?
C18 C13 H13 119.6 . . ?
C17 C18 H18 119.8 . . ?
C13 C18 C17 120.4(2) . . ?
C13 C18 H18 119.8 . . ?
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 O2 1.4327(16) . ?
S1 C20 1.7840(18) . ?
S1 O1 1.4362(16) . ?
S1 C16 1.7572(18) . ?
F2 C21 1.326(2) . ?
F1 C21 1.337(2) . ?
O3 H3 0.8200 . ?
O3 C19 1.4069(18) . ?
F3 C21 1.330(2) . ?
C6 C19 1.523(2) . ?
C6 C5 1.385(2) . ?
C6 C1 1.394(2) . ?
C19 C21 1.539(2) . ?
C19 C20 1.533(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C8 C3 1.485(2) . ?
C8 C7 1.389(3) . ?
C8 C9 1.387(3) . ?
C3 C4 1.391(2) . ?
C3 C2 1.392(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(2) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C16 C15 1.378(3) . ?
C16 C17 1.381(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C12 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(4) . ?
C11 C10 1.375(4) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C18 1.364(4) . ?
C18 H18 0.9300 . ?
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 C16 C15 C14 -179.80(16) . . . . ?
S1 C16 C17 C18 -179.77(18) . . . . ?
O3 C19 C21 F2 176.91(13) . . . . ?
O3 C19 C21 F1 -62.68(17) . . . . ?
O3 C19 C21 F3 56.48(17) . . . . ?
O3 C19 C20 S1 -56.60(17) . . . . ?
C6 C19 C21 F2 60.44(18) . . . . ?
C6 C19 C21 F1 -179.15(13) . . . . ?
C6 C19 C21 F3 -59.99(17) . . . . ?
C6 C19 C20 S1 67.29(16) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C19 C6 C5 C4 178.60(16) . . . . ?
C19 C6 C1 C2 -178.41(16) . . . . ?
C5 C6 C19 O3 -8.9(2) . . . . ?
C5 C6 C19 C21 105.41(17) . . . . ?
C5 C6 C19 C20 -135.01(16) . . . . ?
C5 C6 C1 C2 1.5(3) . . . . ?
C21 C19 C20 S1 -171.76(11) . . . . ?
O2 S1 C20 C19 39.83(15) . . . . ?
O2 S1 C16 C15 -19.74(19) . . . . ?
O2 S1 C16 C17 160.22(16) . . . . ?
C20 S1 C16 C15 99.37(17) . . . . ?
C20 S1 C16 C17 -80.67(18) . . . . ?
C20 C19 C21 F2 -63.03(18) . . . . ?
C20 C19 C21 F1 57.38(17) . . . . ?
C20 C19 C21 F3 176.54(13) . . . . ?
C8 C3 C4 C5 -179.40(16) . . . . ?
C8 C3 C2 C1 179.61(17) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C3 C8 C7 C12 176.99(19) . . . . ?
C3 C8 C9 C10 -177.10(18) . . . . ?
C1 C6 C19 O3 170.96(15) . . . . ?
C1 C6 C19 C21 -74.71(19) . . . . ?
C1 C6 C19 C20 44.9(2) . . . . ?
C1 C6 C5 C4 -1.3(3) . . . . ?
C4 C3 C2 C1 -1.3(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
O1 S1 C20 C19 166.74(13) . . . . ?
O1 S1 C16 C15 -148.92(16) . . . . ?
O1 S1 C16 C17 31.04(19) . . . . ?
C16 S1 C20 C19 -78.70(14) . . . . ?
C16 C15 C14 C13 -0.4(3) . . . . ?
C16 C17 C18 C13 -0.5(4) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C15 C14 C13 C18 0.2(4) . . . . ?
C7 C8 C3 C4 -135.96(19) . . . . ?
C7 C8 C3 C2 43.1(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C9 C8 C3 C4 41.6(3) . . . . ?
C9 C8 C3 C2 -139.38(19) . . . . ?
C9 C8 C7 C12 -0.6(3) . . . . ?
C17 C16 C15 C14 0.2(3) . . . . ?
C12 C11 C10 C9 -0.7(4) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C14 C13 C18 C17 0.3(4) . . . . ?
