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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036470.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_4036470
loop_
_publ_author_name
'Degennaro, Leonardo'
'Carroccia, Laura'
'Parisi, Giovanna'
'Zenzola, Marina'
'Romanazzi, Giuseppe'
'Fanelli, Flavio'
'Pisano, Luisa'
'Luisi, Renzo'
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Sulfur-Bearing Four-Membered
 Heterocycles: Direct Access to 2,4-Disubstituted Thietane 1-Oxides.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12201
_journal_page_last               12211
_journal_paper_doi               10.1021/acs.joc.5b02126
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C16 H16 O2 S'
_chemical_formula_weight         272.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.537(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4710(8)
_cell_length_b                   7.8890(7)
_cell_length_c                   15.2460(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1377.05(18)
_computing_cell_refinement
'DIRAX (Duisenberg,1992; Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'EVAL (Nonius, 2002; Duisenberg et al., 2000)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '\f scans and \w scans'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'Bruker-Nonius KappaCCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15333
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         5.012
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0593
_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)+(0.0707P)²+0.8525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2074
_reflns_number_total             3131
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b02126_si_003.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4036470
_shelx_shelxl_version_number     2014/7
_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   0.894
_shelx_estimated_absorpt_t_max   0.894
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.39926(7) 0.09686(9) 0.66720(5) 0.0514(2) Uani 1 1 d . .
O1 O 0.52861(18) 0.1215(3) 0.67582(14) 0.0589(6) Uani 1 1 d . .
O2 O 0.51404(16) 0.3565(3) 0.80313(15) 0.0544(5) Uani 1 1 d . .
H100 H 0.535(3) 0.281(5) 0.763(2) 0.082 Uiso 1 1 d . U
C2 C 0.4016(2) 0.4019(3) 0.76654(16) 0.0354(5) Uani 1 1 d . .
C3 C 0.3441(2) 0.5090(3) 0.83510(15) 0.0351(5) Uani 1 1 d . .
C4 C 0.3295(3) 0.0984(3) 0.81934(19) 0.0488(7) Uani 1 1 d . .
H4A H 0.3898 0.1127 0.8662 0.059 Uiso 1 1 calc R U
H4B H 0.2536 0.0857 0.8434 0.059 Uiso 1 1 calc R U
C5 C 0.4114(2) 0.5077(3) 0.68220(16) 0.0391(6) Uani 1 1 d . .
C6 C 0.3317(2) 0.2404(3) 0.74659(17) 0.0395(6) Uani 1 1 d . .
H6 H 0.2518 0.2691 0.7252 0.047 Uiso 1 1 calc R U
C7 C 0.4103(2) 0.5780(3) 0.90515(17) 0.0451(6) Uani 1 1 d . .
H7 H 0.4894 0.5524 0.9125 0.054 Uiso 1 1 calc R U
C8 C 0.2261(2) 0.5476(4) 0.82729(19) 0.0523(7) Uani 1 1 d . .
H8 H 0.1793 0.5018 0.7813 0.063 Uiso 1 1 calc R U
C9 C 0.2449(3) 0.7237(4) 0.95547(19) 0.0616(9) Uani 1 1 d . .
H9 H 0.2121 0.7970 0.9949 0.074 Uiso 1 1 calc R U
C10 C 0.5119(3) 0.5989(4) 0.6723(2) 0.0620(8) Uani 1 1 d . .
H10 H 0.5729 0.5931 0.7152 0.074 Uiso 1 1 calc R U
C11 C 0.3604(3) 0.6846(4) 0.96451(19) 0.0612(8) Uani 1 1 d . .
H11 H 0.4064 0.7299 1.0111 0.073 Uiso 1 1 calc R U
C12 C 0.3572(3) -0.0447(4) 0.7539(2) 0.0720(10) Uani 1 1 d . .
H12A H 0.2893 -0.1127 0.7365 0.086 Uiso 1 1 calc R U
H12B H 0.4209 -0.1170 0.7760 0.086 Uiso 1 1 calc R U
C13 C 0.3224(3) 0.5211(4) 0.6181(2) 0.0603(8) Uani 1 1 d . .
H13 H 0.2532 0.4618 0.6239 0.072 Uiso 1 1 calc R U
C14 C 0.1771(3) 0.6536(5) 0.8873(2) 0.0664(9) Uani 1 1 d . .
H14 H 0.0976 0.6777 0.8814 0.080 Uiso 1 1 calc R U
C15 C 0.3347(4) 0.6225(6) 0.5448(2) 0.0843(12) Uani 1 1 d . .
H15 H 0.2740 0.6302 0.5017 0.101 Uiso 1 1 calc R U
C16 C 0.5228(4) 0.7005(5) 0.5982(3) 0.0873(13) Uani 1 1 d . .
H16 H 0.5912 0.7615 0.5920 0.105 Uiso 1 1 calc R U
C17 C 0.4350(5) 0.7106(5) 0.5356(3) 0.0914(15) Uani 1 1 d . .
H17 H 0.4429 0.7778 0.4862 0.110 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'
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 C12 108.80(16)
O1 S1 C6 108.33(12)
C12 S1 C6 76.17(13)
O2 C2 C3 106.95(19)
O2 C2 C6 108.7(2)
C3 C2 C6 110.81(19)
O2 C2 C5 110.6(2)
C3 C2 C5 109.19(19)
C6 C2 C5 110.5(2)
C7 C3 C8 117.8(2)
C7 C3 C2 120.4(2)
C8 C3 C2 121.6(2)
C12 C4 C6 93.0(2)
C13 C5 C10 118.2(3)
C13 C5 C2 123.1(2)
C10 C5 C2 118.7(3)
C2 C6 C4 119.0(2)
C2 C6 S1 113.79(17)
C4 C6 S1 92.90(16)
C3 C7 C11 120.9(3)
C14 C8 C3 120.7(3)
C11 C9 C14 119.2(3)
C5 C10 C16 120.4(4)
C9 C11 C7 120.8(3)
C4 C12 S1 95.45(19)
C5 C13 C15 120.6(3)
C9 C14 C8 120.6(3)
C17 C15 C13 120.5(4)
C17 C16 C10 120.4(4)
C16 C17 C15 119.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.494(2)
S1 C12 1.819(3)
S1 C6 1.861(3)
O2 C2 1.420(3)
C2 C3 1.525(3)
C2 C6 1.526(3)
C2 C5 1.543(3)
C3 C7 1.383(4)
C3 C8 1.385(4)
C4 C12 1.552(4)
C4 C6 1.578(4)
C5 C13 1.373(4)
C5 C10 1.375(4)
C7 C11 1.385(4)
C8 C14 1.384(4)
C9 C11 1.360(5)
C9 C14 1.376(5)
C10 C16 1.397(5)
C13 C15 1.389(5)
C15 C17 1.358(6)
C16 C17 1.347(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139191525
