#------------------------------------------------------------------------------
#$Date: 2020-09-06 12:18:34 +0200 (Sun 06 de Sep de 2020) $
#$Revision: 256165 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/76/7157668.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_7157668
loop_
_publ_author_name
'Scheutz, Georg M.'
'Rowell, Jonathan L.'
'Wang, Fu-Sheng'
'Abboud, Khalil A.'
'Peng, Chi-How'
'Sumerlin, Brent S.'
_publ_section_title
;
 Synthesis of functional 1,2-dithiolanes from 1,3-bis-tert-butyl
 thioethers.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6509
_journal_page_last               6513
_journal_paper_doi               10.1039/d0ob01577f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C5 H9 O S2'
_chemical_formula_weight         149.24
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-22 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.7501(18)
_cell_length_b                   19.7501(18)
_cell_length_c                   7.4965(6)
_cell_measurement_reflns_used    5435
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     2924.1(4)
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19828
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         2.906
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3--8.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   0.4920
_exptl_transmission_factor_min   0.4221
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0403
_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)+(0.0445P)²+3.0365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1382
_reflns_number_total             1815
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01577f2.cif
_cod_data_source_block           georg8
_cod_depositor_comments
'Adding full bibliography for 7157667--7157668.cif.'
_cod_original_cell_volume        2924.1(6)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7157668
_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_min   0.878
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_file
; 
TITL hkl_a.res in I4(1)/a 
    georg8.res 
    created by SHELXL-2018/3 at 16:09:39 on 20-Aug-2019 
CELL 0.71073 19.7501 19.7501 7.4965 90.000 90.000 90.000 
ZERR 16.00 0.0018 0.0018 0.0006 0.000 0.000 0.000 
LATT 2 
SYMM -y+1/4, x+3/4, z+3/4 
SYMM y+1/4, -x+1/4, z+1/4 
SYMM -x, -y+1/2, z 
SFAC C H O S 
UNIT 80 144 16 32 
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! 
TEMP -100.150 
SIZE 0.035 0.060 0.210 
  
ACTA 50 
L.S. 4 
LIST 4 
FMAP 2 
PLAN -2 0 0.00 
HTAB 
BOND $H 
EQIV $1 y+1/4, -x+5/4, z+1/4 
HTAB O1 O1_$1 
CONF 
  
WGHT    0.044500    3.036500 
FVAR       0.20825 
S1    4    0.549291    0.571754    0.043508    11.00000    0.03493    0.05166 = 
         0.03378    0.00067   -0.00514   -0.00481 
S2    4    0.541669    0.532419    0.297890    11.00000    0.03728    0.04430 = 
         0.03394   -0.00280    0.00403   -0.01405 
O1    3    0.697833    0.547071    0.263032    11.00000    0.03755    0.04207 = 
         0.04391   -0.00988   -0.00978    0.00014 
H1    2    0.723413    0.549147    0.335911    11.00000    0.07428 
C1    1    0.629291    0.616362    0.077455    11.00000    0.03941    0.04312 = 
         0.03409    0.00204    0.00194   -0.00985 
AFIX  23 
H1A   2    0.663192    0.599763   -0.009441    11.00000   -1.20000 
H1B   2    0.622568    0.665392    0.056472    11.00000   -1.20000 
AFIX   0 
C2    1    0.655534    0.605314    0.266071    11.00000    0.03209    0.03333 = 
         0.03132   -0.00428    0.00105   -0.00603 
AFIX  13 
H2A   2    0.683308    0.645410    0.301872    11.00000   -1.20000 
AFIX   0 
C3    1    0.596254    0.597646    0.397936    11.00000    0.03956    0.04648 = 
         0.03053   -0.00942    0.00595   -0.01425 
C4    1    0.558091    0.665139    0.413280    11.00000    0.05917    0.05730 = 
         0.07018   -0.03085    0.02366   -0.00889 
AFIX  33 
H4A   2    0.543982    0.680113    0.294319    11.00000   -1.50000 
H4B   2    0.518053    0.659080    0.488833    11.00000   -1.50000 
H4C   2    0.587884    0.699297    0.466482    11.00000   -1.50000 
AFIX   0 
C5    1    0.619305    0.572126    0.579069    11.00000    0.06868    0.09275 = 
         0.02772    0.00190    0.00142   -0.03608 
AFIX  33 
H5A   2    0.643405    0.529109    0.564437    11.00000   -1.50000 
H5B   2    0.649610    0.605507    0.633668    11.00000   -1.50000 
H5C   2    0.579779    0.565290    0.656020    11.00000   -1.50000 
  
AFIX   0 
HKLF 4 1 1 0 0 0 1 0 0 0 1 
  
  
  
  
REM  hkl_a.res in I4(1)/a 
REM wR2 = 0.112600, GooF = S = 1.13445, Restrained GooF = 1.13445 for all data 
REM R1 = 0.040333 for 1382 Fo > 4sig(Fo) and 0.060856 for all 1815 data 
REM 77 parameters refined using 0 restraints 
  
END 
  
WGHT      0.0438      3.0847 
  
REM Instructions for potential hydrogen bonds 
HTAB O1 O1_$1 
HTAB C2 S1_$1 
HTAB C2 S2_$1 
HTAB C4 S1 
EQIV $2 x, y, z+1 
HTAB C5 S1_$2 
  
REM Highest difference peak  0.600,  deepest hole -0.334,  1-sigma level  0.117 
Q1    1   0.5415  0.6124  0.0567  11.00000  0.05    0.60 
Q2    1   0.5575  0.5750  0.3687  11.00000  0.05    0.37 
;
_shelx_res_checksum              67173
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -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
S1 S 0.54929(3) 0.57175(3) 0.04351(8) 0.04012(19) Uani 1 1 d . . . . .
S2 S 0.54167(3) 0.53242(3) 0.29789(8) 0.03851(19) Uani 1 1 d . . . . .
O1 O 0.69783(9) 0.54707(9) 0.2630(2) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.7234(18) 0.5491(18) 0.336(5) 0.074(12) Uiso 1 1 d . . . . .
C1 C 0.62929(12) 0.61636(12) 0.0775(3) 0.0389(5) Uani 1 1 d . . . . .
H1A H 0.663192 0.599763 -0.009441 0.047 Uiso 1 1 calc R U . . .
H1B H 0.622568 0.665392 0.056472 0.047 Uiso 1 1 calc R U . . .
C2 C 0.65553(11) 0.60531(11) 0.2661(3) 0.0322(4) Uani 1 1 d . . . . .
H2A H 0.683308 0.645410 0.301872 0.039 Uiso 1 1 calc R U . . .
C3 C 0.59625(11) 0.59765(12) 0.3979(3) 0.0389(5) Uani 1 1 d . . . . .
C4 C 0.55809(15) 0.66514(15) 0.4133(5) 0.0622(8) Uani 1 1 d . . . . .
H4A H 0.543982 0.680113 0.294319 0.093 Uiso 1 1 calc R U . . .
H4B H 0.518053 0.659080 0.488833 0.093 Uiso 1 1 calc R U . . .
H4C H 0.587884 0.699297 0.466482 0.093 Uiso 1 1 calc R U . . .
C5 C 0.61931(16) 0.57213(18) 0.5791(3) 0.0630(9) Uani 1 1 d . . . . .
H5A H 0.643405 0.529109 0.564437 0.095 Uiso 1 1 calc R U . . .
H5B H 0.649610 0.605507 0.633668 0.095 Uiso 1 1 calc R U . . .
H5C H 0.579779 0.565290 0.656020 0.095 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0349(3) 0.0517(4) 0.0338(3) 0.0007(2) -0.0051(2) -0.0048(2)
S2 0.0373(3) 0.0443(3) 0.0339(3) -0.0028(2) 0.0040(2) -0.0140(2)
O1 0.0375(9) 0.0421(9) 0.0439(10) -0.0099(7) -0.0098(8) 0.0001(7)
C1 0.0394(12) 0.0431(12) 0.0341(11) 0.0020(9) 0.0019(9) -0.0098(9)
C2 0.0321(10) 0.0333(11) 0.0313(11) -0.0043(8) 0.0011(8) -0.0060(8)
C3 0.0396(12) 0.0465(13) 0.0305(11) -0.0094(9) 0.0060(9) -0.0143(10)
C4 0.0592(17) 0.0573(17) 0.070(2) -0.0308(15) 0.0237(15) -0.0089(13)
C5 0.0687(18) 0.093(2) 0.0277(13) 0.0019(13) 0.0014(12) -0.0361(16)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 S2 96.65(8) . . ?
C3 S2 S1 94.03(8) . . ?
C2 O1 H1 110(3) . . ?
C2 C1 S1 110.79(15) . . ?
C2 C1 H1A 109.5 . . ?
S1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C1 107.53(18) . . ?
O1 C2 C3 112.18(18) . . ?
C1 C2 C3 110.59(18) . . ?
O1 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C5 C3 C4 111.6(2) . . ?
C5 C3 C2 112.3(2) . . ?
C4 C3 C2 109.6(2) . . ?
C5 C3 S2 107.93(18) . . ?
C4 C3 S2 110.53(17) . . ?
C2 C3 S2 104.64(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 1.827(2) . ?
S1 S2 2.0646(8) . ?
S2 C3 1.840(2) . ?
O1 C2 1.422(3) . ?
O1 H1 0.75(4) . ?
C1 C2 1.522(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.540(3) . ?
C2 H2A 1.0000 . ?
C3 C5 1.518(4) . ?
C3 C4 1.536(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O1 0.75(4) 1.97(4) 2.7137(18) 175(4) 3_565 yes
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
S2 S1 C1 C2 0.98(17) . . . . ?
S1 C1 C2 O1 90.57(19) . . . . ?
S1 C1 C2 C3 -32.2(2) . . . . ?
O1 C2 C3 C5 48.0(3) . . . . ?
C1 C2 C3 C5 168.0(2) . . . . ?
O1 C2 C3 C4 172.7(2) . . . . ?
C1 C2 C3 C4 -67.3(2) . . . . ?
O1 C2 C3 S2 -68.8(2) . . . . ?
C1 C2 C3 S2 51.3(2) . . . . ?
S1 S2 C3 C5 -162.97(18) . . . . ?
S1 S2 C3 C4 74.71(18) . . . . ?
S1 S2 C3 C2 -43.23(15) . . . . ?
