#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:38:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178435 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025629.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_4025629
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            'C17 H16 O4 S'
_chemical_formula_weight         316.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 106.202(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.101(2)
_cell_length_b                   10.5638(13)
_cell_length_c                   8.9610(11)
_cell_measurement_reflns_used    3050
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.81
_cell_measurement_theta_min      2.29
_cell_volume                     1554.5(3)
_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 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6129
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fiber
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0479
_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)+(0.0878P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                2546
_reflns_number_total             2983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1009454_si_007.cif
_cod_data_source_block           compound7
_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_database_code               4025629
#BEGIN Tags that were not found in dictionaries:
_ratio_of_minimum_to_maximum_apparent_transmision 0.929986
#END Tags that were not found in dictionaries
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'
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 0.03024(5) 0.75656(5) 0.10269(8) 0.04065(17) Uani 1 1 d . . .
O1 O 0.08169(12) 1.11639(17) 0.1200(2) 0.0452(5) Uani 1 1 d . . .
O2 O 0.16344(16) 0.9681(2) 0.2548(4) 0.0691(8) Uani 1 1 d . . .
O3 O -0.06887(12) 0.97657(18) 0.1025(2) 0.0397(4) Uani 1 1 d . . .
H3 H -0.1153 0.9509 0.0634 0.060 Uiso 1 1 calc R . .
O4 O 0.27305(15) 0.4028(2) -0.0223(4) 0.0679(7) Uani 1 1 d . . .
C1 C 0.00839(17) 1.1225(2) -0.0102(3) 0.0382(5) Uani 1 1 d . . .
H1 H 0.0238 1.1363 -0.1064 0.046 Uiso 1 1 calc R . .
C2 C 0.10658(17) 0.9951(3) 0.1488(4) 0.0413(6) Uani 1 1 d . . .
C3 C 0.04874(16) 0.9096(2) 0.0313(3) 0.0342(5) Uani 1 1 d . . .
H3A H 0.0693 0.8987 -0.0597 0.041 Uiso 1 1 calc R . .
C4 C -0.02861(15) 0.9898(2) -0.0137(3) 0.0334(5) Uani 1 1 d . . .
H4 H -0.0638 0.9678 -0.1169 0.040 Uiso 1 1 calc R . .
C5 C 0.10314(16) 0.6567(2) 0.0560(3) 0.0364(5) Uani 1 1 d . . .
C6 C 0.1762(2) 0.6967(3) 0.0367(6) 0.0652(10) Uani 1 1 d . . .
H6 H 0.1889 0.7825 0.0425 0.078 Uiso 1 1 calc R . .
C7 C 0.2311(2) 0.6097(3) 0.0088(6) 0.0736(13) Uani 1 1 d . . .
H7 H 0.2802 0.6374 -0.0053 0.088 Uiso 1 1 calc R . .
C8 C 0.21305(18) 0.4820(2) 0.0017(4) 0.0476(7) Uani 1 1 d . . .
C9 C 0.1403(2) 0.4418(3) 0.0199(5) 0.0637(10) Uani 1 1 d . . .
H9 H 0.1278 0.3560 0.0149 0.076 Uiso 1 1 calc R . .
C10 C 0.0856(2) 0.5294(3) 0.0459(5) 0.0583(9) Uani 1 1 d . . .
H10 H 0.0358 0.5017 0.0568 0.070 Uiso 1 1 calc R . .
C11 C 0.2556(3) 0.2718(3) -0.0405(6) 0.0709(12) Uani 1 1 d . . .
H11A H 0.3018 0.2279 -0.0562 0.106 Uiso 1 1 calc R . .
H11B H 0.2093 0.2588 -0.1288 0.106 Uiso 1 1 calc R . .
H11C H 0.2438 0.2397 0.0511 0.106 Uiso 1 1 calc R . .
C12 C -0.04526(17) 1.2291(2) 0.0120(3) 0.0377(5) Uani 1 1 d . . .
C13 C -0.1028(2) 1.2764(3) -0.1168(4) 0.0481(7) Uani 1 1 d . . .
H13 H -0.1051 1.2456 -0.2152 0.058 Uiso 1 1 calc R . .
C14 C -0.1568(2) 1.3692(3) -0.1003(4) 0.0561(8) Uani 1 1 d . . .
H14 H -0.1957 1.3994 -0.1875 0.067 Uiso 1 1 calc R . .
C15 C -0.1536(2) 1.4172(3) 0.0438(5) 0.0577(8) Uani 1 1 d . . .
H15 H -0.1904 1.4789 0.0547 0.069 Uiso 1 1 calc R . .
C16 C -0.0951(3) 1.3729(3) 0.1716(5) 0.0647(10) Uani 1 1 d . . .
H16 H -0.0915 1.4065 0.2692 0.078 Uiso 1 1 calc R . .
C17 C -0.0414(2) 1.2781(3) 0.1564(4) 0.0515(7) Uani 1 1 d . . .
H17 H -0.0028 1.2478 0.2440 0.062 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 C3 104.24(12) . . ?
C2 O1 C1 110.5(2) . . ?
C8 O4 C11 117.8(3) . . ?
O1 C1 C12 110.4(2) . . ?
O1 C1 C4 103.51(19) . . ?
C12 C1 C4 115.1(2) . . ?
O2 C2 O1 121.6(3) . . ?
O2 C2 C3 129.6(3) . . ?
O1 C2 C3 108.7(2) . . ?
C2 C3 C4 101.60(19) . . ?
C2 C3 S1 115.60(18) . . ?
C4 C3 S1 111.54(17) . . ?
O3 C4 C3 108.4(2) . . ?
O3 C4 C1 111.1(2) . . ?
C3 C4 C1 100.3(2) . . ?
C6 C5 C10 118.8(3) . . ?
C6 C5 S1 124.9(2) . . ?
C10 C5 S1 116.3(2) . . ?
C5 C6 C7 120.3(3) . . ?
C8 C7 C6 120.1(3) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 O4 124.7(3) . . ?
C7 C8 O4 115.5(3) . . ?
C8 C9 C10 119.7(3) . . ?
C5 C10 C9 121.3(3) . . ?
C17 C12 C13 119.0(3) . . ?
C17 C12 C1 122.4(2) . . ?
C13 C12 C1 118.6(3) . . ?
C14 C13 C12 120.4(3) . . ?
C15 C14 C13 120.7(3) . . ?
C14 C15 C16 119.1(3) . . ?
C15 C16 C17 120.7(3) . . ?
C12 C17 C16 120.2(3) . . ?
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 1.770(3) . ?
S1 C3 1.799(2) . ?
O1 C2 1.352(3) . ?
O1 C1 1.456(3) . ?
O2 C2 1.189(4) . ?
O3 C4 1.406(3) . ?
O4 C8 1.386(4) . ?
O4 C11 1.416(4) . ?
C1 C12 1.501(4) . ?
C1 C4 1.535(4) . ?
C2 C3 1.524(4) . ?
C3 C4 1.527(3) . ?
C5 C6 1.375(4) . ?
C5 C10 1.376(4) . ?
C6 C7 1.385(5) . ?
C7 C8 1.382(4) . ?
C8 C9 1.366(5) . ?
C9 C10 1.382(5) . ?
C12 C17 1.379(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.374(5) . ?
C15 C16 1.376(6) . ?
C16 C17 1.390(5) . ?
