#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:18:34 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256165 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157667.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_7157667
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            'C15 H30 O S2'
_chemical_formula_weight         290.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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            4
_cell_length_a                   5.0392(2)
_cell_length_b                   8.4897(3)
_cell_length_c                   38.3953(13)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     1642.60(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            22184
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.154
_diffrn_reflns_theta_min         2.457
_diffrn_source                   'I\mS microsource 3.0'
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9490
_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    1.175
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   0.5648
_exptl_transmission_factor_min   0.5159
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1758 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.006(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0301P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                4580
_reflns_number_total             4854
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01577f2.cif
_cod_data_source_block           georg7
_cod_depositor_comments
'Adding full bibliography for 7157667--7157668.cif.'
_cod_database_code               7157667
_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   0.941
_shelx_estimated_absorpt_t_max   0.984
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-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 0.86879(9) -0.06353(5) 0.74445(2) 0.03066(10) Uani 1 1 d . . . . .
S2 S 0.65034(9) 0.14051(5) 0.75008(2) 0.03188(10) Uani 1 1 d . . . . .
O1 O 0.3489(2) 0.02864(16) 0.68462(3) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.7634(3) -0.09992(18) 0.69971(4) 0.0238(3) Uani 1 1 d . . . . .
H1A H 0.919444 -0.129478 0.685474 0.029 Uiso 1 1 calc R U . . .
H1B H 0.636881 -0.189100 0.699310 0.029 Uiso 1 1 calc R U . . .
C2 C 0.6301(3) 0.04702(18) 0.68379(3) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.7078(3) 0.19228(18) 0.70508(4) 0.0263(3) Uani 1 1 d . . . . .
H3A H 0.597746 0.283972 0.698354 0.032 Uiso 1 1 calc R U . . .
H3B H 0.896825 0.218916 0.701269 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7111(3) 0.06225(19) 0.64562(4) 0.0233(3) Uani 1 1 d . . . . .
H4A H 0.905729 0.077177 0.644541 0.028 Uiso 1 1 calc R U . . .
H4B H 0.669602 -0.038119 0.633670 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5794(3) 0.19583(19) 0.62562(4) 0.0258(3) Uani 1 1 d . . . . .
H5A H 0.605453 0.295748 0.638467 0.031 Uiso 1 1 calc R U . . .
H5B H 0.386208 0.175677 0.624121 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6922(3) 0.2128(2) 0.58897(4) 0.0270(3) Uani 1 1 d . . . . .
H6A H 0.885981 0.230598 0.590625 0.032 Uiso 1 1 calc R U . . .
H6B H 0.664072 0.112901 0.576191 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5689(3) 0.3467(2) 0.56827(4) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.588894 0.445797 0.581590 0.032 Uiso 1 1 calc R U . . .
H7B H 0.376619 0.326099 0.565535 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6917(3) 0.3683(2) 0.53241(4) 0.0273(3) Uani 1 1 d . . . . .
H8A H 0.884248 0.387920 0.535140 0.033 Uiso 1 1 calc R U . . .
H8B H 0.670354 0.269434 0.519025 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5703(3) 0.5029(2) 0.51177(4) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.588296 0.601411 0.525368 0.032 Uiso 1 1 calc R U . . .
H9B H 0.378526 0.482174 0.508596 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6974(3) 0.52649(19) 0.47620(4) 0.0281(3) Uani 1 1 d . . . . .
H10A H 0.888794 0.548366 0.479425 0.034 Uiso 1 1 calc R U . . .
H10B H 0.681419 0.427471 0.462746 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5748(3) 0.6598(2) 0.45522(4) 0.0272(3) Uani 1 1 d . . . . .
H11A H 0.585506 0.758299 0.468955 0.033 Uiso 1 1 calc R U . . .
H11B H 0.384679 0.636317 0.451279 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7089(3) 0.6859(2) 0.42016(4) 0.0276(3) Uani 1 1 d . . . . .
H12A H 0.700744 0.586883 0.406592 0.033 Uiso 1 1 calc R U . . .
H12B H 0.898309 0.711085 0.424133 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5838(3) 0.8176(2) 0.39883(4) 0.0278(3) Uani 1 1 d . . . . .
H13A H 0.397267 0.789405 0.393669 0.033 Uiso 1 1 calc R U . . .
H13B H 0.582043 0.915160 0.412971 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7269(3) 0.8504(2) 0.36480(4) 0.0303(3) Uani 1 1 d . . . . .
H14A H 0.734289 0.752059 0.350980 0.036 Uiso 1 1 calc R U . . .
H14B H 0.911536 0.882649 0.369965 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5944(4) 0.9781(2) 0.34317(5) 0.0401(4) Uani 1 1 d . . . . .
H15A H 0.699568 0.997593 0.322141 0.060 Uiso 1 1 calc R U . . .
H15B H 0.582502 1.075186 0.356881 0.060 Uiso 1 1 calc R U . . .
H15C H 0.415709 0.943747 0.336548 0.060 Uiso 1 1 calc R U . . .
H1 H 0.311(6) 0.029(3) 0.7036(7) 0.061(8) Uiso 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'
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 94.91(5) . . ?
C3 S2 S1 91.05(5) . . ?
C2 O1 H1 106(2) . . ?
C2 C1 S1 111.28(10) . . ?
C2 C1 H1A 109.4 . . ?
S1 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
S1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C4 107.24(11) . . ?
O1 C2 C3 109.28(13) . . ?
C4 C2 C3 112.10(13) . . ?
O1 C2 C1 109.58(12) . . ?
C4 C2 C1 109.43(12) . . ?
C3 C2 C1 109.18(12) . . ?
C2 C3 S2 105.90(10) . . ?
C2 C3 H3A 110.6 . . ?
S2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
S2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C5 C4 C2 115.53(12) . . ?
C5 C4 H4A 108.4 . . ?
C2 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C2 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 C6 111.93(13) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 113.63(13) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 113.41(13) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 113.52(14) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 113.43(13) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 113.74(13) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.35(13) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.48(14) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.62(14) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.10(15) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 1.8240(16) . ?
S1 S2 2.0638(6) . ?
S2 C3 1.8063(15) . ?
O1 C2 1.4263(18) . ?
O1 H1 0.75(3) . ?
C1 C2 1.543(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.5266(19) . ?
C2 C3 1.530(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.525(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 S1 0.75(3) 2.84(3) 3.4264(13) 137(3) 1_455 yes
O1 H1 S2 0.75(3) 2.65(3) 3.0866(13) 119(3) . yes
