#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025625.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_4025625
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_formula_sum            'C13 H16 O3 S'
_chemical_formula_weight         252
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.354(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.883(4)
_cell_length_b                   12.951(2)
_cell_length_c                   8.6539(15)
_cell_measurement_reflns_used    2933
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      3.01
_cell_volume                     2669.0(8)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8867
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plateled
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0553
_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+1.7652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                1910
_reflns_number_total             3042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1009454_si_003.cif
_cod_data_source_block           compound3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_formula_sum        'C13 H16 O3 S1'
_cod_database_code               4025625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.16677(3) 0.49770(6) 0.20005(8) 0.0645(3) Uani 1 1 d . . .
O2 O 0.32450(7) 0.44665(13) 0.1490(2) 0.0566(5) Uani 1 1 d . . .
C4 C 0.23030(11) 0.48973(18) 0.1026(3) 0.0457(6) Uani 1 1 d . . .
C2 C 0.26467(11) 0.58880(17) 0.1192(3) 0.0481(6) Uani 1 1 d . . .
H2 H 0.2500 0.6426 0.0475 0.058 Uiso 1 1 calc R . .
C3 C 0.27268(12) 0.41050(18) 0.1619(3) 0.0518(6) Uani 1 1 d . . .
C5 C 0.12038(11) 0.4105(2) 0.0986(3) 0.0548(6) Uani 1 1 d . . .
C6 C 0.13548(12) 0.3286(2) 0.0089(3) 0.0596(7) Uani 1 1 d . . .
H6 H 0.1732 0.3165 -0.0040 0.072 Uiso 1 1 calc R . .
C12 C 0.37278(13) 0.6116(2) 0.1389(3) 0.0672(8) Uani 1 1 d . . .
H12 H 0.3728 0.6170 0.2519 0.081 Uiso 1 1 calc R . .
C7 C 0.09544(14) 0.2648(3) -0.0615(4) 0.0746(9) Uani 1 1 d . . .
H7 H 0.1062 0.2103 -0.1227 0.090 Uiso 1 1 calc R . .
C8 C 0.04015(16) 0.2808(3) -0.0424(5) 0.0992(12) Uani 1 1 d . . .
H8 H 0.0129 0.2372 -0.0891 0.119 Uiso 1 1 calc R . .
C10 C 0.06481(14) 0.4261(3) 0.1178(5) 0.0939(12) Uani 1 1 d . . .
H10 H 0.0539 0.4804 0.1791 0.113 Uiso 1 1 calc R . .
C9 C 0.02514(16) 0.3622(4) 0.0472(6) 0.1258(18) Uani 1 1 d . . .
H9 H -0.0126 0.3741 0.0600 0.151 Uiso 1 1 calc R . .
O3 O 0.26604(9) 0.62138(15) 0.27627(19) 0.0591(5) Uani 1 1 d . . .
O1 O 0.26477(9) 0.32709(14) 0.2165(3) 0.0763(6) Uani 1 1 d . . .
C1 C 0.32185(11) 0.55074(19) 0.0802(3) 0.0494(6) Uani 1 1 d . . .
H1 H 0.3219 0.5442 -0.0326 0.059 Uiso 1 1 calc R . .
C14 C 0.36862(16) 0.7209(3) 0.0710(4) 0.0906(11) Uani 1 1 d . . .
H14A H 0.4008 0.7603 0.1088 0.136 Uiso 1 1 calc R . .
H14B H 0.3351 0.7536 0.1015 0.136 Uiso 1 1 calc R . .
H14C H 0.3673 0.7171 -0.0400 0.136 Uiso 1 1 calc R . .
C13 C 0.42674(14) 0.5587(3) 0.1009(6) 0.1069(14) Uani 1 1 d . . .
H13A H 0.4285 0.4911 0.1465 0.160 Uiso 1 1 calc R . .
H13B H 0.4583 0.5987 0.1415 0.160 Uiso 1 1 calc R . .
H13C H 0.4275 0.5528 -0.0095 0.160 Uiso 1 1 calc R . .
H4 H 0.2229(11) 0.4756(19) 0.002(3) 0.053(7) Uiso 1 1 d . . .
H16 H 0.2582(14) 0.678(3) 0.274(4) 0.078(11) 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
C5 S1 C4 104.49(11) . . ?
C3 O2 C1 110.06(18) . . ?
C3 C4 C2 101.4(2) . . ?
C3 C4 S1 116.74(17) . . ?
C2 C4 S1 112.08(17) . . ?
O3 C2 C1 110.7(2) . . ?
O3 C2 C4 108.25(19) . . ?
C1 C2 C4 101.16(19) . . ?
O1 C3 O2 121.5(2) . . ?
O1 C3 C4 128.8(3) . . ?
O2 C3 C4 109.6(2) . . ?
C10 C5 C6 118.7(3) . . ?
C10 C5 S1 115.1(2) . . ?
C6 C5 S1 126.2(2) . . ?
C7 C6 C5 120.7(3) . . ?
C1 C12 C13 111.6(3) . . ?
C1 C12 C14 109.1(3) . . ?
C13 C12 C14 111.4(3) . . ?
C8 C7 C6 120.4(3) . . ?
C7 C8 C9 118.9(3) . . ?
C5 C10 C9 120.2(3) . . ?
C10 C9 C8 121.1(4) . . ?
O2 C1 C12 109.5(2) . . ?
O2 C1 C2 102.68(18) . . ?
C12 C1 C2 118.3(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 1.768(3) . ?
S1 C4 1.794(3) . ?
O2 C3 1.336(3) . ?
O2 C1 1.473(3) . ?
C4 C3 1.504(4) . ?
C4 C2 1.524(3) . ?
C2 O3 1.421(3) . ?
C2 C1 1.514(4) . ?
C3 O1 1.200(3) . ?
C5 C10 1.365(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.371(4) . ?
C12 C1 1.505(4) . ?
C12 C13 1.518(5) . ?
C12 C14 1.533(4) . ?
C7 C8 1.359(5) . ?
C8 C9 1.373(6) . ?
C10 C9 1.367(5) . ?
