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#$Date: 2022-08-13 00:50:46 +0300 (Sat, 13 Aug 2022) $
#$Revision: 277213 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/05/7130514.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_7130514
loop_
_publ_author_name
'Tan, Qingfa'
'Chen, Qianping'
'Zhu, Zitong'
'Liu, Xiaohua'
_publ_section_title
;
 Asymmetric organocatalytic sulfenylation for the construction of a
 diheteroatom-bearing tetrasubstituted carbon centre
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03443C
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 F N O2 S'
_chemical_formula_sum            'C23 H20 F N O2 S'
_chemical_formula_weight         393.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7902(2)
_cell_length_b                   8.5037(2)
_cell_length_c                   11.6291(3)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.81
_cell_volume                     966.65(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12024
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.272
_diffrn_reflns_theta_min         3.807
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       flake
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.040(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0298
_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)+(0.0400P)²+0.0913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0728
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3370
_reflns_number_total             3461
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03443c2.cif
_cod_data_source_block           tqf012
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130514
_shelx_shelxl_version_number     2018/3
_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_min   0.603
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
S1 S 0.99773(4) 0.79271(7) 0.47247(4) 0.02796(15) Uani 1 1 d . . . . .
F1 F 0.82937(14) 0.94408(15) 0.60285(12) 0.0291(3) Uani 1 1 d . . . . .
O1 O 1.03990(16) 0.7573(2) 0.76765(14) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.60008(18) 0.7244(3) 0.07281(15) 0.0443(5) Uani 1 1 d . . . . .
N1 N 0.85143(16) 0.6066(2) 0.69524(14) 0.0224(4) Uani 1 1 d . . . . .
C1 C 0.9462(2) 0.7235(3) 0.70036(18) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.88349(18) 0.7964(3) 0.58735(16) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.7743(2) 0.6614(2) 0.58968(17) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.781671 0.586278 0.524144 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6284(2) 0.7094(3) 0.60576(18) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.5260(2) 0.6693(3) 0.5234(2) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.548281 0.613228 0.456316 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3910(2) 0.7110(3) 0.5391(2) 0.0349(5) Uani 1 1 d . . . . .
H6 H 0.321645 0.682970 0.482412 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3567(2) 0.7924(3) 0.6355(2) 0.0377(5) Uani 1 1 d . . . . .
H7 H 0.264108 0.820005 0.645703 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4584(3) 0.8336(3) 0.7175(2) 0.0397(6) Uani 1 1 d . . . . .
H8 H 0.435555 0.890150 0.784250 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5935(2) 0.7928(3) 0.70283(18) 0.0310(4) Uani 1 1 d . . . . .
H9 H 0.662701 0.821993 0.759350 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8782(2) 0.7720(3) 0.35220(17) 0.0252(4) Uani 1 1 d . . . . .
C12 C 0.7758(3) 0.8816(3) 0.3290(2) 0.0349(5) Uani 1 1 d . . . . .
H12 H 0.768828 0.971105 0.377176 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6840(3) 0.8608(3) 0.2361(2) 0.0385(6) Uani 1 1 d . . . . .
H13 H 0.611942 0.934243 0.222024 0.046 Uiso 1 1 calc R U . . .
C14 C 0.6961(2) 0.7331(3) 0.16267(19) 0.0317(5) Uani 1 1 d . . . . .
C15 C 0.7995(2) 0.6247(3) 0.1840(2) 0.0323(5) Uani 1 1 d . . . . .
H15 H 0.808841 0.537719 0.133777 0.039 Uiso 1 1 calc R U . . .
C16 C 0.8900(2) 0.6437(3) 0.2798(2) 0.0300(5) Uani 1 1 d . . . . .
H16 H 0.960143 0.568338 0.295611 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6168(3) 0.6052(5) -0.0111(2) 0.0541(8) Uani 1 1 d . . . . .
H17A H 0.544059 0.614458 -0.072174 0.081 Uiso 1 1 calc R U . . .
H17B H 0.611713 0.501622 0.025319 0.081 Uiso 1 1 calc R U . . .
H17C H 0.705972 0.617458 -0.044321 0.081 Uiso 1 1 calc R U . . .
C21 C 0.8308(2) 0.4716(2) 0.76226(17) 0.0216(4) Uani 1 1 d . . . . .
C22 C 0.9166(2) 0.4389(3) 0.8590(2) 0.0283(5) Uani 1 1 d . . . . .
H22 H 0.990546 0.507245 0.880316 0.034 Uiso 1 1 calc R U . . .
C23 C 0.8931(2) 0.3061(3) 0.92345(19) 0.0324(5) Uani 1 1 d . . . . .
H23 H 0.951414 0.284433 0.989624 0.039 Uiso 1 1 calc R U . . .
C24 C 0.7861(2) 0.2029(3) 0.8939(2) 0.0320(5) Uani 1 1 d . . . . .
C25 C 0.7020(2) 0.2381(3) 0.7969(2) 0.0318(5) Uani 1 1 d . . . . .
H25 H 0.628842 0.169179 0.774940 0.038 Uiso 1 1 calc R U . . .
C26 C 0.7226(2) 0.3711(3) 0.73182(18) 0.0274(4) Uani 1 1 d . . . . .
H26 H 0.663090 0.393855 0.666592 0.033 Uiso 1 1 calc R U . . .
C27 C 0.7640(3) 0.0568(4) 0.9633(3) 0.0494(7) Uani 1 1 d . . . . .
H27A H 0.774046 0.082100 1.045600 0.074 Uiso 1 1 calc R U . . .
H27B H 0.831702 -0.022826 0.944856 0.074 Uiso 1 1 calc R U . . .
H27C H 0.671752 0.015982 0.944847 0.074 Uiso 1 1 calc R U . . .
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'
S S 0.3331 0.5567 '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
C11 S1 C2 100.23(9) . . ?
C14 O2 C17 117.5(2) . . ?
C1 N1 C21 133.70(17) . . ?
C1 N1 C3 96.96(17) . . ?
C21 N1 C3 129.30(16) . . ?
O1 C1 N1 134.0(2) . . ?
O1 C1 C2 134.9(2) . . ?
N1 C1 C2 91.04(16) . . ?
F1 C2 C1 112.99(17) . . ?
F1 C2 C3 113.39(15) . . ?
C1 C2 C3 86.03(16) . . ?
F1 C2 S1 111.96(14) . . ?
C1 C2 S1 113.08(14) . . ?
C3 C2 S1 117.04(15) . . ?
N1 C3 C4 115.18(16) . . ?
N1 C3 C2 85.90(14) . . ?
C4 C3 C2 117.07(18) . . ?
N1 C3 H3 112.1 . . ?
C4 C3 H3 112.1 . . ?
C2 C3 H3 112.1 . . ?
C5 C4 C9 119.0(2) . . ?
C5 C4 C3 120.0(2) . . ?
C9 C4 C3 121.01(18) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 S1 121.54(18) . . ?
C16 C11 S1 118.79(16) . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O2 C14 C15 124.6(2) . . ?
O2 C14 C13 115.6(2) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.4(2) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C21 C22 119.9(2) . . ?
C26 C21 N1 119.38(18) . . ?
C22 C21 N1 120.68(18) . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.7(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 117.8(2) . . ?
C25 C24 C27 121.1(2) . . ?
C23 C24 C27 121.0(2) . . ?
C26 C25 C24 121.5(2) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 119.69(19) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C11 1.781(2) . ?
S1 C2 1.7898(19) . ?
F1 C2 1.379(3) . ?
O1 C1 1.207(3) . ?
O2 C14 1.368(3) . ?
O2 C17 1.423(4) . ?
N1 C1 1.359(3) . ?
N1 C21 1.408(3) . ?
N1 C3 1.480(3) . ?
C1 C2 1.549(3) . ?
C2 C3 1.569(3) . ?
C3 C4 1.508(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.390(3) . ?
C4 C9 1.392(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.384(3) . ?
C11 C16 1.386(3) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C26 1.391(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(3) . ?
C24 C27 1.505(3) . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
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
C21 N1 C1 O1 -5.4(4) . . . . ?
C3 N1 C1 O1 176.9(3) . . . . ?
C21 N1 C1 C2 175.7(2) . . . . ?
C3 N1 C1 C2 -2.04(16) . . . . ?
O1 C1 C2 F1 -63.2(3) . . . . ?
N1 C1 C2 F1 115.67(17) . . . . ?
O1 C1 C2 C3 -177.0(3) . . . . ?
N1 C1 C2 C3 1.92(15) . . . . ?
O1 C1 C2 S1 65.3(3) . . . . ?
N1 C1 C2 S1 -115.84(15) . . . . ?
C11 S1 C2 F1 -82.83(15) . . . . ?
C11 S1 C2 C1 148.15(16) . . . . ?
C11 S1 C2 C3 50.51(17) . . . . ?
C1 N1 C3 C4 -116.04(19) . . . . ?
C21 N1 C3 C4 66.1(3) . . . . ?
C1 N1 C3 C2 2.02(16) . . . . ?
C21 N1 C3 C2 -175.9(2) . . . . ?
F1 C2 C3 N1 -115.13(17) . . . . ?
C1 C2 C3 N1 -1.76(14) . . . . ?
S1 C2 C3 N1 112.17(15) . . . . ?
F1 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 114.49(18) . . . . ?
S1 C2 C3 C4 -131.58(16) . . . . ?
N1 C3 C4 C5 -139.5(2) . . . . ?
C2 C3 C4 C5 121.7(2) . . . . ?
N1 C3 C4 C9 39.9(3) . . . . ?
C2 C3 C4 C9 -58.8(3) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 C4 -0.3(4) . . . . ?
C5 C4 C9 C8 0.7(4) . . . . ?
C3 C4 C9 C8 -178.8(2) . . . . ?
C2 S1 C11 C12 58.8(2) . . . . ?
C2 S1 C11 C16 -122.05(17) . . . . ?
C16 C11 C12 C13 1.7(3) . . . . ?
S1 C11 C12 C13 -179.16(19) . . . . ?
C11 C12 C13 C14 -2.2(4) . . . . ?
C17 O2 C14 C15 -7.1(4) . . . . ?
C17 O2 C14 C13 173.6(3) . . . . ?
C12 C13 C14 O2 -179.6(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
O2 C14 C15 C16 -178.6(2) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C12 C11 C16 C15 0.1(3) . . . . ?
S1 C11 C16 C15 -179.16(17) . . . . ?
C14 C15 C16 C11 -1.2(3) . . . . ?
C1 N1 C21 C26 -178.6(2) . . . . ?
C3 N1 C21 C26 -1.5(3) . . . . ?
C1 N1 C21 C22 2.0(3) . . . . ?
C3 N1 C21 C22 179.06(19) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
N1 C21 C22 C23 179.6(2) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C22 C23 C24 C27 178.5(3) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C27 C24 C25 C26 -179.3(3) . . . . ?
C24 C25 C26 C21 1.0(4) . . . . ?
C22 C21 C26 C25 -0.9(3) . . . . ?
N1 C21 C26 C25 179.7(2) . . . . ?
