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#$Date: 2022-10-16 03:30:54 +0300 (Sun, 16 Oct 2022) $
#$Revision: 278606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158933.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_7158933
loop_
_publ_author_name
'Yao, Yunfei'
'Lin, Bo'
'Wu, Minze'
'Zhang, Yafang'
'Huang, Yangjie'
'Han, Xiaoyan'
'Weng, Zhiqiang'
_publ_section_title
;
 Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of
 pyridinium 1,4-zwitterionic thiolates with CF3CN
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01749K
_journal_year                    2022
_chemical_formula_moiety         'C8 H6 F3 N O4 S'
_chemical_formula_sum            'C8 H6 F3 N O4 S'
_chemical_formula_weight         269.20
_chemical_name_systematic        P-1
_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     dual
_audit_creation_date             2021-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-17 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                74.601(3)
_cell_angle_beta                 77.073(3)
_cell_angle_gamma                82.099(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7049(7)
_cell_length_b                   8.0698(6)
_cell_length_c                   9.0862(8)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.049
_cell_measurement_theta_min      2.371
_cell_volume                     529.03(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.371
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0312P)²+0.2814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1807
_reflns_number_total             1877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01749k2.cif
_cod_data_source_block           cf3sz
_cod_database_code               7158933
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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 0.16615(5) 0.72814(4) 0.51791(4) 0.02247(14) Uani 1 1 d . . . . .
F3 F 0.24776(14) 0.93432(13) 0.09688(11) 0.0422(3) Uani 1 1 d . . . . .
F1 F 0.05388(15) 1.01752(12) 0.27578(11) 0.0423(3) Uani 1 1 d . . . . .
O2 O 0.47523(15) 0.29070(13) 0.28044(12) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.39611(14) 0.28953(14) 0.71145(12) 0.0305(3) Uani 1 1 d . . . . .
O4 O 0.20767(15) 0.48817(14) 0.81440(12) 0.0296(3) Uani 1 1 d . . . . .
F2 F -0.01747(16) 0.85485(13) 0.15147(14) 0.0527(3) Uani 1 1 d . . . . .
O1 O 0.26449(15) 0.15445(13) 0.47092(14) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.22275(15) 0.58320(15) 0.28916(13) 0.0214(3) Uani 1 1 d . . . . .
C6 C 0.29287(19) 0.41567(18) 0.69910(16) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.26753(18) 0.46086(18) 0.41458(16) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.33307(19) 0.28257(18) 0.39501(16) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.16789(18) 0.72766(18) 0.32963(16) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.24533(18) 0.51514(17) 0.54872(16) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.1121(2) 0.88420(19) 0.21310(17) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.5540(3) 0.1272(2) 0.2465(2) 0.0386(4) Uani 1 1 d . . . . .
H5A H 0.661308 0.145829 0.168778 0.058 Uiso 1 1 calc GR . . . .
H5B H 0.470702 0.078705 0.208787 0.058 Uiso 1 1 calc GR . . . .
H5C H 0.582062 0.049043 0.339710 0.058 Uiso 1 1 calc GR . . . .
C7 C 0.2576(3) 0.4096(2) 0.96421(19) 0.0439(5) Uani 1 1 d . . . . .
H7A H 0.384555 0.408100 0.953338 0.066 Uiso 1 1 calc GR . . . .
H7B H 0.222826 0.293609 1.000374 0.066 Uiso 1 1 calc GR . . . .
H7C H 0.198228 0.475112 1.037908 0.066 Uiso 1 1 calc GR . . . .
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'
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
C1 S1 C3 88.43(7) . . ?
C4 O2 C5 116.06(12) . . ?
C6 O4 C7 114.87(13) . . ?
C1 N1 C2 109.24(12) . . ?
O3 C6 O4 125.95(13) . . ?
O3 C6 C3 123.45(13) . . ?
O4 C6 C3 110.59(12) . . ?
N1 C2 C4 118.51(12) . . ?
C3 C2 N1 115.40(12) . . ?
C3 C2 C4 126.09(13) . . ?
O2 C4 C2 109.51(12) . . ?
O1 C4 O2 126.07(13) . . ?
O1 C4 C2 124.41(13) . . ?
N1 C1 S1 116.82(11) . . ?
N1 C1 C8 120.25(12) . . ?
C8 C1 S1 122.92(10) . . ?
C6 C3 S1 122.24(10) . . ?
C2 C3 S1 110.10(10) . . ?
C2 C3 C6 127.51(13) . . ?
F3 C8 C1 111.31(12) . . ?
F1 C8 F3 106.71(12) . . ?
F1 C8 C1 112.08(12) . . ?
F2 C8 F3 107.40(13) . . ?
F2 C8 F1 107.40(13) . . ?
F2 C8 C1 111.67(12) . . ?
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 C1 1.7088(14) . ?
S1 C3 1.7139(14) . ?
F3 C8 1.3291(18) . ?
F1 C8 1.3272(17) . ?
O2 C4 1.3271(18) . ?
O2 C5 1.4550(18) . ?
O3 C6 1.1992(18) . ?
O4 C6 1.3353(18) . ?
O4 C7 1.4531(19) . ?
F2 C8 1.3238(18) . ?
O1 C4 1.1967(18) . ?
N1 C2 1.3701(18) . ?
N1 C1 1.3021(18) . ?
C6 C3 1.4853(19) . ?
C2 C4 1.5009(19) . ?
C2 C3 1.370(2) . ?
C1 C8 1.498(2) . ?
