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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/76/7227631.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_7227631
loop_
_publ_author_name
'Sharma, N.'
'Kumari, N.'
'Chundawat, T. S.'
'Kumar, S.'
'Bhagat, S.'
_publ_section_title
;
 Efficient trifluoromethylation of C(sp2)--H functionalized α-oxoketene
 dithioacetals: a route to the regioselective synthesis of functionalized
 trifluoromethylated pyrazoles
;
_journal_issue                   17
_journal_name_full               'RSC Adv.'
_journal_page_first              10150
_journal_paper_doi               10.1039/C7RA01130J
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C14 H11 F3 O2 S2'
_chemical_formula_sum            'C14 H11 F3 O2 S2'
_chemical_formula_weight         332.35
_chemical_name_systematic        SB-NS-357
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1494zk
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-27 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   13.456(5)
_cell_length_b                   10.034(5)
_cell_length_c                   22.429(5)
_cell_measurement_temperature    293(2)
_cell_volume                     3028(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9837
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_correction_T_min  0.9204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0526P)²+1.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2233
_reflns_number_total             2653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra01130j2.cif
_cod_data_source_block           shelxl
_cod_database_code               7227631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
C1 C 0.39220(17) 0.0429(2) 0.06894(10) 0.0436(6) Uani 1 1 d .
C2 C 0.31711(19) -0.0398(3) 0.04880(11) 0.0553(7) Uani 1 1 d .
H2 H 0.2535 -0.0080 0.0409 0.066 Uiso 1 1 calc R
C3 C 0.3416(2) -0.1712(3) 0.04110(12) 0.0636(8) Uani 1 1 d .
H3 H 0.2934 -0.2302 0.0275 0.076 Uiso 1 1 calc R
C4 C 0.4370(2) -0.2190(3) 0.05304(13) 0.0666(8) Uani 1 1 d .
H4 H 0.4508 -0.3089 0.0471 0.080 Uiso 1 1 calc R
C5 C 0.5110(2) -0.1359(3) 0.07341(13) 0.0596(7) Uani 1 1 d .
H5 H 0.5744 -0.1684 0.0814 0.071 Uiso 1 1 calc R
C6 C 0.48819(17) -0.0012(2) 0.08180(11) 0.0446(6) Uani 1 1 d .
C7 C 0.54013(17) 0.1142(2) 0.10262(11) 0.0445(6) Uani 1 1 d .
H7 H 0.6061 0.1179 0.1149 0.053 Uiso 1 1 calc R
C8 C 0.47527(16) 0.2166(2) 0.10107(10) 0.0411(5) Uani 1 1 d .
C9 C 0.48714(17) 0.3582(2) 0.11484(11) 0.0427(6) Uani 1 1 d .
C10 C 0.58674(16) 0.3965(2) 0.14073(10) 0.0395(5) Uani 1 1 d .
C11 C 0.6556(2) 0.4685(3) 0.09893(13) 0.0576(7) Uani 1 1 d .
C12 C 0.60928(17) 0.3688(2) 0.19752(11) 0.0437(6) Uani 1 1 d .
C13 C 0.7119(3) 0.4556(5) 0.29822(16) 0.1155(15) Uani 1 1 d .
H13A H 0.7749 0.4677 0.3176 0.173 Uiso 1 1 calc R
H13B H 0.6712 0.3971 0.3217 0.173 Uiso 1 1 calc R
H13C H 0.6794 0.5403 0.2941 0.173 Uiso 1 1 calc R
C14 C 0.5584(3) 0.1737(3) 0.28122(17) 0.1013(13) Uani 1 1 d .
H14A H 0.5090 0.1389 0.3079 0.152 Uiso 1 1 calc R
H14B H 0.6168 0.1972 0.3035 0.152 Uiso 1 1 calc R
H14C H 0.5750 0.1073 0.2521 0.152 Uiso 1 1 calc R
O1 O 0.38314(11) 0.17708(16) 0.08027(7) 0.0474(4) Uani 1 1 d .
O2 O 0.42335(14) 0.44120(18) 0.10489(9) 0.0655(5) Uani 1 1 d .
F1 F 0.61353(13) 0.4879(2) 0.04588(8) 0.0875(6) Uani 1 1 d .
F2 F 0.68242(17) 0.58812(18) 0.11837(9) 0.0982(7) Uani 1 1 d .
F3 F 0.73940(13) 0.4028(2) 0.08879(9) 0.0936(7) Uani 1 1 d .
S1 S 0.51059(5) 0.31920(7) 0.24436(3) 0.0580(2) Uani 1 1 d .
S2 S 0.73093(5) 0.38398(9) 0.22588(4) 0.0722(3) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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'
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
O1 C1 C2 125.6(2)
O1 C1 C6 110.7(2)
C2 C1 C6 123.6(2)
C3 C2 C1 116.3(2)
C3 C2 H2 121.9
C1 C2 H2 121.9
C2 C3 C4 121.9(2)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 121.3(3)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 118.1(3)
C4 C5 H5 120.9
C6 C5 H5 120.9
C1 C6 C5 118.8(2)
C1 C6 C7 105.3(2)
C5 C6 C7 135.9(2)
C8 C7 C6 107.0(2)
C8 C7 H7 126.5
C6 C7 H7 126.5
C7 C8 O1 111.8(2)
C7 C8 C9 131.6(2)
O1 C8 C9 116.60(19)
O2 C9 C8 123.3(2)
O2 C9 C10 121.5(2)
C8 C9 C10 115.2(2)
C12 C10 C11 123.6(2)
C12 C10 C9 121.0(2)
C11 C10 C9 115.4(2)
F2 C11 F3 106.0(2)
F2 C11 F1 106.1(2)
F3 C11 F1 106.3(2)
F2 C11 C10 113.4(2)
F3 C11 C10 113.1(2)
F1 C11 C10 111.4(2)
C10 C12 S2 122.42(18)
C10 C12 S1 117.03(18)
S2 C12 S1 120.55(15)
S2 C13 H13A 109.5
S2 C13 H13B 109.5
H13A C13 H13B 109.5
S2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
S1 C14 H14A 109.5
S1 C14 H14B 109.5
H14A C14 H14B 109.5
S1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C1 O1 C8 105.28(17)
C12 S1 C14 103.50(16)
C12 S2 C13 103.21(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.376(3)
C1 C2 1.383(3)
C1 C6 1.395(3)
C2 C3 1.369(4)
C2 H2 0.9300
C3 C4 1.396(4)
C3 H3 0.9300
C4 C5 1.377(4)
C4 H4 0.9300
C5 C6 1.399(4)
C5 H5 0.9300
C6 C7 1.431(3)
C7 C8 1.348(3)
C7 H7 0.9300
C8 O1 1.383(3)
C8 C9 1.463(3)
C9 O2 1.217(3)
C9 C10 1.510(3)
C10 C12 1.338(3)
C10 C11 1.503(3)
C11 F2 1.327(3)
C11 F3 1.326(3)
C11 F1 1.332(3)
C12 S2 1.763(2)
C12 S1 1.765(2)
C13 S2 1.793(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 S1 1.797(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
O1 C1 C2 C3 -179.2(2)
C6 C1 C2 C3 -0.6(4)
C1 C2 C3 C4 0.1(4)
C2 C3 C4 C5 0.2(5)
C3 C4 C5 C6 -0.1(4)
O1 C1 C6 C5 179.5(2)
C2 C1 C6 C5 0.7(4)
O1 C1 C6 C7 0.4(3)
C2 C1 C6 C7 -178.3(2)
C4 C5 C6 C1 -0.3(4)
C4 C5 C6 C7 178.4(3)
C1 C6 C7 C8 -0.1(3)
C5 C6 C7 C8 -178.9(3)
C6 C7 C8 O1 -0.2(3)
C6 C7 C8 C9 -177.3(2)
C7 C8 C9 O2 171.6(3)
O1 C8 C9 O2 -5.4(4)
C7 C8 C9 C10 -6.3(4)
O1 C8 C9 C10 176.66(19)
O2 C9 C10 C12 106.5(3)
C8 C9 C10 C12 -75.5(3)
O2 C9 C10 C11 -72.4(3)
C8 C9 C10 C11 105.6(2)
C12 C10 C11 F2 -57.8(3)
C9 C10 C11 F2 121.0(3)
C12 C10 C11 F3 62.9(3)
C9 C10 C11 F3 -118.3(3)
C12 C10 C11 F1 -177.5(2)
C9 C10 C11 F1 1.4(3)
C11 C10 C12 S2 -12.9(3)
C9 C10 C12 S2 168.35(17)
C11 C10 C12 S1 165.76(19)
C9 C10 C12 S1 -13.0(3)
C2 C1 O1 C8 178.2(2)
C6 C1 O1 C8 -0.5(2)
C7 C8 O1 C1 0.5(3)
C9 C8 O1 C1 178.0(2)
C10 C12 S1 C14 132.2(2)
S2 C12 S1 C14 -49.2(2)
C10 C12 S2 C13 139.3(2)
S1 C12 S2 C13 -39.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203241
