#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025631.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_4025631
loop_
_publ_author_name
'Florenci V. González'
'Amit Jain'
'Santiago Rodríguez'
'José A. Sáez'
'Cristian Vicent'
'Gabriel Peris'
_publ_section_title
;
 Stereoisomerization of β-Hydroxy-α-sulfenyl-γ-butyrolactones
 Controlled by Two Concomitant 1,4-Type Nonbonded Sulfur-Oxygen
 Interactions As Analyzed by X-ray Crystallography
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5888
_journal_page_last               5894
_journal_paper_doi               10.1021/jo1009454
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_sum            'C14 H18 O4 S'
_chemical_formula_weight         282.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.571(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7000(13)
_cell_length_b                   12.9740(12)
_cell_length_c                   8.7134(8)
_cell_measurement_reflns_used    2316
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.25
_cell_volume                     1434.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0859
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11838
_diffrn_reflns_theta_full        30.62
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATELED
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0794P)²+0.0689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1761
_reflns_number_gt                1931
_reflns_number_total             4302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1009454_si_009.cif
_cod_data_source_block           compound9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4025631
#BEGIN Tags that were not found in dictionaries:
_ratio_of_minimum_to_maximum_apparent_transmision 0.929854
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83283(6) 0.23792(6) 0.21053(8) 0.0644(3) Uani 1 1 d . . .
O1 O 1.01676(18) 0.06946(14) 0.2061(3) 0.0832(7) Uani 1 1 d . . .
O2 O 1.12877(14) 0.18838(11) 0.13368(19) 0.0520(5) Uani 1 1 d . . .
O3 O 1.02379(14) 0.36272(11) 0.27699(17) 0.0506(5) Uani 1 1 d . . .
H3 H 1.0116 0.4246 0.2832 0.076 Uiso 1 1 calc R . .
O4 O 0.52071(16) 0.05554(16) -0.2324(3) 0.0844(7) Uani 1 1 d . . .
C1 C 0.95231(18) 0.23468(17) 0.1061(3) 0.0438(6) Uani 1 1 d . . .
H1 H 0.9328 0.2240 -0.0029 0.053 Uiso 1 1 calc R . .
C2 C 1.0312(2) 0.15386(18) 0.1544(3) 0.0529(7) Uani 1 1 d . . .
C3 C 1.12388(18) 0.29381(16) 0.0712(3) 0.0417(5) Uani 1 1 d . . .
H3A H 1.1218 0.2895 -0.0412 0.050 Uiso 1 1 calc R . .
C4 C 1.01794(18) 0.33237(16) 0.1201(2) 0.0412(5) Uani 1 1 d . . .
H4 H 0.9899 0.3873 0.0529 0.049 Uiso 1 1 calc R . .
C5 C 0.74282(19) 0.17772(19) 0.0792(3) 0.0490(6) Uani 1 1 d . . .
C6 C 0.6558(2) 0.2335(2) 0.0228(3) 0.0592(7) Uani 1 1 d . . .
H6 H 0.6468 0.3013 0.0543 0.071 Uiso 1 1 calc R . .
C7 C 0.5836(2) 0.1901(2) -0.0777(3) 0.0628(7) Uani 1 1 d . . .
H7 H 0.5253 0.2281 -0.1130 0.075 Uiso 1 1 calc R . .
C8 C 0.5963(2) 0.09008(19) -0.1276(3) 0.0550(7) Uani 1 1 d . . .
C9 C 0.6814(2) 0.03388(19) -0.0740(3) 0.0589(7) Uani 1 1 d . . .
H9 H 0.6905 -0.0336 -0.1070 0.071 Uiso 1 1 calc R . .
C10 C 0.7539(2) 0.0781(2) 0.0296(3) 0.0594(7) Uani 1 1 d . . .
H10 H 0.8113 0.0394 0.0663 0.071 Uiso 1 1 calc R . .
C11 C 0.5205(3) -0.0488(2) -0.2740(4) 0.0816(10) Uani 1 1 d . . .
H11A H 0.4635 -0.0616 -0.3477 0.122 Uiso 1 1 calc R . .
H11B H 0.5116 -0.0905 -0.1845 0.122 Uiso 1 1 calc R . .
H11C H 0.5861 -0.0658 -0.3183 0.122 Uiso 1 1 calc R . .
C12 C 1.22115(19) 0.35256(18) 0.1233(3) 0.0513(6) Uani 1 1 d . . .
H12 H 1.2230 0.3571 0.2356 0.062 Uiso 1 1 calc R . .
C13 C 1.3197(2) 0.2972(2) 0.0764(4) 0.0792(10) Uani 1 1 d . . .
H13A H 1.3808 0.3359 0.1107 0.119 Uiso 1 1 calc R . .
H13B H 1.3185 0.2907 -0.0334 0.119 Uiso 1 1 calc R . .
H13C H 1.3224 0.2299 0.1222 0.119 Uiso 1 1 calc R . .
C14 C 1.2146(2) 0.46116(19) 0.0582(4) 0.0687(8) Uani 1 1 d . . .
H14A H 1.2765 0.4991 0.0911 0.103 Uiso 1 1 calc R . .
H14B H 1.1533 0.4950 0.0944 0.103 Uiso 1 1 calc R . .
H14C H 1.2100 0.4580 -0.0519 0.103 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'
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
C5 S1 C1 101.40(11) . . ?
C2 O2 C3 109.70(17) . . ?
C8 O4 C11 118.8(2) . . ?
C2 C1 C4 101.76(19) . . ?
C2 C1 S1 116.23(17) . . ?
C4 C1 S1 114.25(16) . . ?
O1 C2 O2 120.9(2) . . ?
O1 C2 C1 129.2(3) . . ?
O2 C2 C1 109.87(19) . . ?
O2 C3 C12 109.79(17) . . ?
O2 C3 C4 103.05(18) . . ?
C12 C3 C4 118.38(19) . . ?
O3 C4 C3 110.71(17) . . ?
O3 C4 C1 108.28(18) . . ?
C3 C4 C1 101.12(18) . . ?
C10 C5 C6 118.0(2) . . ?
C10 C5 S1 123.3(2) . . ?
C6 C5 S1 118.69(19) . . ?
C7 C6 C5 120.9(2) . . ?
C6 C7 C8 120.5(2) . . ?
C9 C8 O4 124.9(2) . . ?
C9 C8 C7 119.7(2) . . ?
O4 C8 C7 115.4(2) . . ?
C8 C9 C10 119.6(2) . . ?
C5 C10 C9 121.4(2) . . ?
C3 C12 C13 110.8(2) . . ?
C3 C12 C14 109.1(2) . . ?
C13 C12 C14 111.8(2) . . ?
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 C5 1.763(3) . ?
S1 C1 1.805(2) . ?
O1 C2 1.201(3) . ?
O2 C2 1.337(3) . ?
O2 C3 1.473(3) . ?
O3 C4 1.421(3) . ?
O4 C8 1.370(3) . ?
O4 C11 1.402(4) . ?
C1 C2 1.498(3) . ?
C1 C4 1.519(3) . ?
C3 C12 1.504(3) . ?
C3 C4 1.515(3) . ?
C5 C10 1.372(3) . ?
C5 C6 1.392(3) . ?
C6 C7 1.361(4) . ?
C7 C8 1.381(4) . ?
C8 C9 1.369(3) . ?
C9 C10 1.384(3) . ?
C12 C13 1.516(4) . ?
C12 C14 1.520(3) . ?
