#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/56/7155647.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_7155647
loop_
_publ_author_name
'Parisi, Giovanna'
'Degennaro, Leonardo'
'Carlucci, Claudia'
'de Candia, Modesto'
'Mastrorilli, Pietro'
'Roller, Alexander'
'Holzer, Wolfgang'
'Altomare, Cosimo Damiano'
'Pace, Vittorio'
'Luisi, Renzo'
_publ_section_title
;
 A Greener and Efficient Access to Substituted Four- and Six-membered
 Sulfur-bearing Heterocycles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00846E
_journal_year                    2017
_chemical_formula_moiety         'C9 H9 F O4 S2'
_chemical_formula_sum            'C9 H9 F O4 S2'
_chemical_formula_weight         264.28
_chemical_name_systematic
'2-fluoro-2-(phenylsulfonyl)thietane 1,1-dioxide'
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-31 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.2020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7355(6)
_cell_length_b                   9.6324(4)
_cell_length_c                   9.0837(4)
_cell_measurement_reflns_used    8490
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      30.112
_cell_measurement_theta_min      2.673
_cell_volume                     1089.15(8)
_computing_cell_refinement       'APEX2 v2011.2-0'
_computing_data_collection       'APEX2 v2011.2-0'
_computing_data_reduction        'APEX2 v2011.2-0'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      130.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12579
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.154
_diffrn_reflns_theta_min         2.674
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0700 before and 0.0291 after correction. 
The Ratio of minimum to maximum transmission is 0.7969. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0318
_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)+(0.0475P)²+0.5910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2997
_reflns_number_total             3203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob00846e2.cif
_cod_data_source_block           smba2bis_p21c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7155647
_shelxl_version_number           2013-3
_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   0.865
_shelx_estimated_absorpt_t_min   0.789
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
S1 S 0.30372(2) 0.38109(3) 0.86091(3) 0.01688(9) Uani 1 1 d .
S2 S 0.30223(2) 0.54428(3) 0.56171(3) 0.01683(9) Uani 1 1 d .
F1 F 0.40427(7) 0.62227(8) 0.82562(9) 0.02253(17) Uani 1 1 d .
O1 O 0.19304(8) 0.35299(12) 0.80097(13) 0.0276(2) Uani 1 1 d .
O2 O 0.33763(9) 0.42287(11) 1.01607(11) 0.0244(2) Uani 1 1 d .
O3 O 0.38020(8) 0.61767(11) 0.49771(12) 0.0240(2) Uani 1 1 d .
O4 O 0.25767(8) 0.41657(11) 0.49512(11) 0.0231(2) Uani 1 1 d .
C1 C 0.37199(9) 0.50093(13) 0.75202(13) 0.0161(2) Uani 1 1 d .
C2 C 0.46009(10) 0.39078(14) 0.75829(15) 0.0198(2) Uani 1 1 d .
H2A H 0.5259 0.4135 0.8340 0.024 Uiso 1 1 calc R
H2B H 0.4783 0.3757 0.6588 0.024 Uiso 1 1 calc R
C3 C 0.39842(11) 0.26601(14) 0.80709(15) 0.0201(2) Uani 1 1 d .
H3A H 0.4410 0.2126 0.8923 0.024 Uiso 1 1 calc R
H3B H 0.3666 0.2036 0.7229 0.024 Uiso 1 1 calc R
C4 C 0.20103(10) 0.65927(13) 0.58739(14) 0.0183(2) Uani 1 1 d .
C5 C 0.22383(11) 0.80079(15) 0.59570(18) 0.0263(3) Uani 1 1 d .
H5 H 0.2920 0.8339 0.5848 0.032 Uiso 1 1 calc R
C6 C 0.14547(12) 0.89247(15) 0.6202(2) 0.0316(3) Uani 1 1 d .
H6 H 0.1596 0.9894 0.6259 0.038 Uiso 1 1 calc R
C7 C 0.04643(12) 0.84251(16) 0.6362(2) 0.0300(3) Uani 1 1 d .
H7 H -0.0069 0.9057 0.6538 0.036 Uiso 1 1 calc R
C8 C 0.02413(11) 0.70095(16) 0.62702(19) 0.0286(3) Uani 1 1 d .
H8 H -0.0444 0.6682 0.6371 0.034 Uiso 1 1 calc R
C9 C 0.10186(11) 0.60740(14) 0.60308(17) 0.0231(3) Uani 1 1 d .
H9 H 0.0877 0.5105 0.5975 0.028 Uiso 1 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
O1 S1 O2 119.61(7)
O1 S1 C1 116.89(6)
O1 S1 C3 116.70(7)
O2 S1 C1 105.71(6)
O2 S1 C3 111.22(6)
C3 S1 C1 79.62(6)
O3 S2 C1 104.89(6)
O3 S2 C4 109.47(6)
O4 S2 O3 119.79(6)
O4 S2 C1 105.93(6)
O4 S2 C4 111.22(6)
C4 S2 C1 104.13(6)
S2 C1 S1 117.45(6)
F1 C1 S1 113.49(8)
F1 C1 S2 107.76(8)
F1 C1 C2 115.52(10)
C2 C1 S1 88.36(8)
C2 C1 S2 113.59(8)
C1 C2 C3 97.80(9)
C2 C3 S1 90.54(8)
C5 C4 S2 118.38(10)
C5 C4 C9 121.91(12)
C9 C4 S2 119.68(10)
C6 C5 C4 118.93(13)
C5 C6 C7 119.87(14)
C6 C7 C8 120.82(13)
C9 C8 C7 120.12(13)
C8 C9 C4 118.34(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4256(10)
S1 O2 1.4414(10)
S1 C1 1.8521(12)
S1 C3 1.7809(13)
S2 O3 1.4380(10)
S2 O4 1.4339(11)
S2 C1 1.8174(12)
S2 C4 1.7519(13)
F1 C1 1.3660(14)
C1 C2 1.5366(17)
C2 C3 1.5508(19)
C4 C5 1.3925(19)
C4 C9 1.3933(17)
C5 C6 1.385(2)
C6 C7 1.386(2)
C7 C8 1.392(2)
C8 C9 1.3893(19)
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
S1 C1 C2 C3 15.34(9)
S2 C1 C2 C3 -104.04(10)
S2 C4 C5 C6 -178.23(13)
S2 C4 C9 C8 178.43(12)
F1 C1 C2 C3 130.69(11)
O1 S1 C1 S2 -12.33(10)
O1 S1 C1 F1 114.57(9)
O1 S1 C1 C2 -128.20(8)
O1 S1 C3 C2 128.28(8)
O2 S1 C1 S2 -148.24(7)
O2 S1 C1 F1 -21.33(10)
O2 S1 C1 C2 95.89(8)
O2 S1 C3 C2 -89.67(9)
O3 S2 C1 S1 -170.58(7)
O3 S2 C1 F1 59.78(9)
O3 S2 C1 C2 -69.53(10)
O3 S2 C4 C5 -21.52(14)
O3 S2 C4 C9 160.26(11)
O4 S2 C1 S1 -42.96(8)
O4 S2 C1 F1 -172.60(8)
O4 S2 C1 C2 58.09(10)
O4 S2 C4 C5 -156.15(11)
O4 S2 C4 C9 25.64(13)
C1 S1 C3 C2 13.29(7)
C1 S2 C4 C5 90.20(12)
C1 S2 C4 C9 -88.02(12)
C1 C2 C3 S1 -15.96(9)
C3 S1 C1 S2 102.45(8)
C3 S1 C1 F1 -130.64(10)
C3 S1 C1 C2 -13.42(8)
C4 S2 C1 S1 74.42(8)
C4 S2 C1 F1 -55.22(9)
C4 S2 C1 C2 175.47(9)
C4 C5 C6 C7 0.1(3)
C5 C4 C9 C8 0.3(2)
C5 C6 C7 C8 -0.5(3)
C6 C7 C8 C9 0.7(3)
C7 C8 C9 C4 -0.6(2)
C9 C4 C5 C6 -0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139192980
