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#$Date: 2025-03-04 20:44:30 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298063 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134070.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_7134070
loop_
_publ_author_name
'Kraemer, Yannick'
'Stephens, Alexander M.'
'Buldt, Jón Atiba'
'Young, Aurelius'
'McLoughlin, Connor P.'
'Fettinger, James C.'
'Holder, Lauren M.'
'Pitts, Cody Ross'
_publ_section_title
;
 Strain-release trifluoromethoxylation and pentafluorosulfanoxylation of
 [1.1.0]bicyclobutanes: expanded access to fluorinated cyclobutane hybrid
 bioisosteres.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3159
_journal_page_last               3162
_journal_paper_doi               10.1039/d4cc06616b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C10 H9 F6 I O3 S2'
_chemical_formula_sum            'C10 H9 F6 I O3 S2'
_chemical_formula_weight         482.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-05-14 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.756(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4528(12)
_cell_length_b                   9.0531(9)
_cell_length_c                   14.0965(14)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.67
_cell_volume                     1459.9(3)
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12715
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.675
_exptl_absorpt_coefficient_mu    2.554
_exptl_absorpt_correction_T_max  0.7899
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.031
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0254
_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)+(0.0211P)²+5.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3175
_reflns_number_total             3344
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc06616b2.cif
_cod_data_source_block           A1CMI
_cod_depositor_comments          'Adding full bibliography for 7134070.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7134070
_shelx_shelxl_version_number     2016/6
_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   0.578
_shelx_estimated_absorpt_t_max   0.925
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_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
I1 I 0.33694(2) 0.45356(2) 0.34490(2) 0.01965(7) Uani 1 1 d . . . . .
S1 S 0.40149(6) 0.79977(7) 0.34807(5) 0.01256(13) Uani 1 1 d . . . . .
S2 S 0.04349(6) 0.75275(10) 0.63113(5) 0.02095(16) Uani 1 1 d . . . . .
F1 F 0.90180(15) 0.6783(2) 0.37746(13) 0.0246(4) Uani 1 1 d . . . . .
F2 F -0.07437(17) 0.8190(3) 0.66642(15) 0.0374(5) Uani 1 1 d . . . . .
F3 F 0.02648(16) 0.8540(2) 0.53987(14) 0.0251(4) Uani 1 1 d . . . . .
F4 F 0.10953(18) 0.8816(3) 0.68518(16) 0.0383(5) Uani 1 1 d . . . . .
F5 F 0.05279(18) 0.6547(3) 0.72249(13) 0.0356(5) Uani 1 1 d . . . . .
F6 F -0.03181(16) 0.6295(2) 0.57925(14) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.36531(18) 0.7899(2) 0.24957(14) 0.0170(4) Uani 1 1 d . . . . .
O2 O 0.38344(19) 0.9377(2) 0.39747(15) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.16155(18) 0.6807(2) 0.59838(14) 0.0181(4) Uani 1 1 d . . . . .
C1 C 0.7859(2) 0.7031(3) 0.3724(2) 0.0177(6) Uani 1 1 d . . . . .
C2 C 0.7398(3) 0.7976(3) 0.4384(2) 0.0188(6) Uani 1 1 d . . . . .
H2 H 0.788615 0.842935 0.486350 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6201(3) 0.8239(3) 0.4323(2) 0.0167(6) Uani 1 1 d . . . . .
H3 H 0.585676 0.887923 0.476498 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5512(2) 0.7558(3) 0.36105(19) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.5997(2) 0.6604(3) 0.29531(19) 0.0136(5) Uani 1 1 d . . . . .
H5 H 0.551466 0.614899 0.246981 0.016 Uiso 1 1 calc R U . . .
C6 C 0.7191(2) 0.6332(3) 0.3017(2) 0.0160(5) Uani 1 1 d . . . . .
H6 H 0.753963 0.568013 0.258491 0.019 Uiso 1 1 calc R U . . .
C7 C 0.3227(2) 0.6635(3) 0.4122(2) 0.0135(5) Uani 1 1 d . . . . .
C8 C 0.3473(2) 0.6684(3) 0.5226(2) 0.0155(5) Uani 1 1 d . . . . .
H8A H 0.347716 0.570057 0.553335 0.019 Uiso 1 1 calc R U . . .
H8B H 0.417542 0.726086 0.542853 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2319(2) 0.7533(3) 0.5299(2) 0.0158(5) Uani 1 1 d . . . . .
H9 H 0.243298 0.861061 0.542793 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1958(2) 0.7194(3) 0.4256(2) 0.0161(5) Uani 1 1 d . . . . .
H10A H 0.174420 0.808071 0.387487 0.019 Uiso 1 1 calc R U . . .
H10B H 0.135390 0.641672 0.417539 0.019 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 0.0033 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'
I I -0.4742 1.8119 '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
O1 S1 O2 118.57(13) . . ?
O1 S1 C4 108.75(13) . . ?
O2 S1 C4 107.77(13) . . ?
O1 S1 C7 108.41(13) . . ?
O2 S1 C7 105.25(13) . . ?
C4 S1 C7 107.60(13) . . ?
F5 S2 F4 90.56(14) . . ?
F5 S2 F6 89.68(13) . . ?
F4 S2 F6 175.52(12) . . ?
F5 S2 F2 88.94(12) . . ?
F4 S2 F2 87.93(12) . . ?
F6 S2 F2 87.60(12) . . ?
F5 S2 F3 176.69(11) . . ?
F4 S2 F3 90.09(13) . . ?
F6 S2 F3 89.42(11) . . ?
F2 S2 F3 87.84(12) . . ?
F5 S2 O3 88.93(11) . . ?
F4 S2 O3 92.82(12) . . ?
F6 S2 O3 91.66(12) . . ?
F2 S2 O3 177.75(13) . . ?
F3 S2 O3 94.29(11) . . ?
C9 O3 S2 121.12(19) . . ?
F1 C1 C6 118.3(3) . . ?
F1 C1 C2 118.3(3) . . ?
C6 C1 C2 123.4(3) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 S1 119.4(2) . . ?
C5 C4 S1 119.0(2) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C10 C7 C8 89.7(2) . . ?
C10 C7 S1 109.34(19) . . ?
C8 C7 S1 114.1(2) . . ?
C10 C7 I1 115.78(19) . . ?
C8 C7 I1 116.90(19) . . ?
S1 C7 I1 109.66(13) . . ?
C9 C8 C7 88.1(2) . . ?
C9 C8 H8A 114.0 . . ?
C7 C8 H8A 114.0 . . ?
C9 C8 H8B 114.0 . . ?
C7 C8 H8B 114.0 . . ?
H8A C8 H8B 111.2 . . ?
O3 C9 C8 109.1(2) . . ?
O3 C9 C10 114.5(2) . . ?
C8 C9 C10 91.6(2) . . ?
O3 C9 H9 113.2 . . ?
C8 C9 H9 113.2 . . ?
C10 C9 H9 113.2 . . ?
C9 C10 C7 88.4(2) . . ?
C9 C10 H10A 113.9 . . ?
C7 C10 H10A 113.9 . . ?
C9 C10 H10B 113.9 . . ?
C7 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?
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
I1 C7 2.134(3) . ?
S1 O1 1.433(2) . ?
S1 O2 1.450(2) . ?
S1 C4 1.761(3) . ?
S1 C7 1.798(3) . ?
S2 F5 1.563(2) . ?
S2 F4 1.568(2) . ?
S2 F6 1.570(2) . ?
S2 F2 1.579(2) . ?
S2 F3 1.584(2) . ?
S2 O3 1.589(2) . ?
F1 C1 1.345(3) . ?
O3 C9 1.444(3) . ?
C1 C6 1.380(4) . ?
C1 C2 1.386(4) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C10 1.559(4) . ?
C7 C8 1.568(4) . ?
C8 C9 1.537(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.538(4) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
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
F5 S2 O3 C9 -159.2(2) . . . . ?
F4 S2 O3 C9 -68.7(2) . . . . ?
F6 S2 O3 C9 111.1(2) . . . . ?
F3 S2 O3 C9 21.6(2) . . . . ?
F1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 S1 -175.4(2) . . . . ?
O1 S1 C4 C3 147.7(2) . . . . ?
O2 S1 C4 C3 18.0(3) . . . . ?
C7 S1 C4 C3 -95.1(2) . . . . ?
O1 S1 C4 C5 -28.1(3) . . . . ?
O2 S1 C4 C5 -157.8(2) . . . . ?
C7 S1 C4 C5 89.1(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
S1 C4 C5 C6 175.8(2) . . . . ?
F1 C1 C6 C5 -179.0(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
O1 S1 C7 C10 -77.4(2) . . . . ?
O2 S1 C7 C10 50.4(2) . . . . ?
C4 S1 C7 C10 165.12(19) . . . . ?
O1 S1 C7 C8 -176.14(19) . . . . ?
O2 S1 C7 C8 -48.3(2) . . . . ?
C4 S1 C7 C8 66.4(2) . . . . ?
O1 S1 C7 I1 50.50(16) . . . . ?
O2 S1 C7 I1 178.32(13) . . . . ?
C4 S1 C7 I1 -66.95(16) . . . . ?
C10 C7 C8 C9 -11.1(2) . . . . ?
S1 C7 C8 C9 100.0(2) . . . . ?
I1 C7 C8 C9 -130.15(19) . . . . ?
S2 O3 C9 C8 172.58(19) . . . . ?
S2 O3 C9 C10 -86.4(3) . . . . ?
C7 C8 C9 O3 128.0(2) . . . . ?
C7 C8 C9 C10 11.3(2) . . . . ?
O3 C9 C10 C7 -123.2(2) . . . . ?
C8 C9 C10 C7 -11.4(2) . . . . ?
C8 C7 C10 C9 11.1(2) . . . . ?
S1 C7 C10 C9 -104.5(2) . . . . ?
I1 C7 C10 C9 131.1(2) . . . . ?
