#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/35/7213518.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213518
loop_
_publ_author_name
'Derek R. Boyd'
'Narain D. Sharma'
'Simon A. Haughey'
'John F. Malone'
'Alistair W. T. King'
'Brian T. McMurray'
'André Alves-Areias'
'Christopher C. R. Allen'
'Robert Holt'
'Howard Dalton'
_publ_section_title
;
 Dioxygenase-catalysed mono-, di- and tri-oxygenation of dialkyl sulfides
 and thioacetals: chemoenzymatic synthesis of enantiopure cis-diol
 sulfoxides
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3288
_journal_page_last               3296
_journal_paper_doi               10.1039/b108620k
_journal_year                    2001
_chemical_formula_sum            'C10 H12 O S2'
_chemical_formula_weight         212.32
_chemical_melting_point          156.0(10)
_chemical_name_systematic        (1S,2S)-2-phenyl-1,3-dithiane-1-oxide
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6341(17)
_cell_length_b                   10.142(4)
_cell_length_c                   18.013(7)
_cell_measurement_temperature    300(2)
_cell_volume                     1029.3(6)
_computing_cell_refinement       'Siemens P3/V2000'
_computing_data_collection       'Siemens P3/V2000'
_computing_data_reduction        'Siemens P3/V2000'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P3 diffractometer'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2775
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.26
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refined
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.1052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                2117
_reflns_number_total             2362
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b108620ksup1.cif
_cod_data_source_block           20
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '155-157' was changed to '156.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

data name '_atom_site_symmetry_multiplicit' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7213518
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
S1 S 0.94261(8) 0.64334(5) 0.07942(3) 0.04081(13) Uani 1 1 d
O1 O 0.9280(3) 0.63018(16) -0.00327(8) 0.0585(4) Uani 1 1 d
C2 C 0.6544(4) 0.58919(17) 0.11468(10) 0.0359(4) Uani 1 1 d
H2 H 0.532(4) 0.641(2) 0.0883(11) 0.045(6) Uiso 1 1 d
S3 S 0.62750(12) 0.62603(5) 0.21263(3) 0.05496(17) Uani 1 1 d
C4 C 0.6585(5) 0.8034(2) 0.21217(14) 0.0568(6) Uani 1 1 d
H4A H 0.539(5) 0.846(2) 0.1811(13) 0.062(7) Uiso 1 1 d
H4B H 0.640(4) 0.828(2) 0.2635(14) 0.058(7) Uiso 1 1 d
C5 C 0.8907(5) 0.8483(2) 0.18039(12) 0.0525(5) Uani 1 1 d
H5A H 0.899(5) 0.936(3) 0.1864(14) 0.065(8) Uiso 1 1 d
H5B H 1.016(5) 0.810(2) 0.2057(13) 0.055(7) Uiso 1 1 d
C6 C 0.9151(4) 0.8173(2) 0.09816(11) 0.0451(5) Uani 1 1 d
H6A H 0.770(4) 0.851(3) 0.0694(13) 0.053(6) Uiso 1 1 d
H6B H 1.071(5) 0.853(2) 0.0761(13) 0.055(6) Uiso 1 1 d
C1' C 0.6312(3) 0.44175(17) 0.10596(9) 0.0351(4) Uani 1 1 d
C2' C 0.4364(4) 0.38691(19) 0.07063(11) 0.0422(4) Uani 1 1 d
H2' H 0.319(5) 0.445(2) 0.0473(13) 0.052(7) Uiso 1 1 d
C3' C 0.4113(4) 0.2507(2) 0.06699(12) 0.0488(5) Uani 1 1 d
H3' H 0.280(5) 0.215(2) 0.0423(14) 0.057(7) Uiso 1 1 d
C4' C 0.5805(5) 0.1693(2) 0.09784(12) 0.0504(5) Uani 1 1 d
H4' H 0.561(5) 0.081(2) 0.0933(12) 0.052(6) Uiso 1 1 d
C5' C 0.7768(4) 0.2239(2) 0.13202(13) 0.0511(5) Uani 1 1 d
H5' H 0.893(5) 0.164(2) 0.1555(13) 0.057(7) Uiso 1 1 d
C6' C 0.8018(4) 0.3588(2) 0.13608(11) 0.0437(4) Uani 1 1 d
H6' H 0.934(5) 0.3933(19) 0.1578(11) 0.044(6) Uiso 1 1 d
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 0.0386(2) 0.0418(2) 0.0421(2) -0.0042(2) 0.00389(19) 0.0020(2)
O1 0.0664(10) 0.0679(9) 0.0413(7) -0.0127(7) 0.0167(7) -0.0126(10)
C2 0.0380(9) 0.0364(9) 0.0334(8) -0.0025(7) 0.0025(8) 0.0032(8)
S3 0.0852(4) 0.0436(3) 0.0361(2) -0.0059(2) 0.0164(2) -0.0046(3)
C4 0.0795(16) 0.0407(11) 0.0501(12) -0.0106(10) 0.0111(13) 0.0027(11)
C5 0.0754(16) 0.0364(10) 0.0456(11) -0.0064(9) -0.0085(10) -0.0039(11)
C6 0.0536(13) 0.0386(9) 0.0432(10) 0.0026(8) -0.0007(9) -0.0030(9)
C1' 0.0391(9) 0.0363(9) 0.0298(8) -0.0018(7) 0.0044(7) 0.0022(8)
C2' 0.0389(9) 0.0458(10) 0.0420(9) -0.0042(8) -0.0009(8) 0.0050(9)
C3' 0.0502(12) 0.0505(11) 0.0457(10) -0.0096(9) 0.0018(10) -0.0084(10)
C4' 0.0666(14) 0.0360(9) 0.0487(11) -0.0028(8) 0.0082(10) -0.0040(10)
C5' 0.0603(13) 0.0396(11) 0.0534(12) 0.0080(9) -0.0014(11) 0.0057(10)
C6' 0.0463(10) 0.0437(10) 0.0411(9) 0.0020(8) -0.0071(8) -0.0027(10)
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
O1 S1 C6 105.59(9)
O1 S1 C2 105.66(9)
C6 S1 C2 98.78(10)
C1' C2 S3 107.38(12)
C1' C2 S1 109.77(13)
S3 C2 S1 110.54(10)
C4 S3 C2 101.13(10)
C5 C4 S3 112.87(17)
C4 C5 C6 112.9(2)
C5 C6 S1 113.12(15)
C2' C1' C6' 119.02(18)
C2' C1' C2 120.93(17)
C6' C1' C2 120.01(18)
C1' C2' C3' 120.1(2)
C4' C3' C2' 120.4(2)
C3' C4' C5' 119.6(2)
C6' C5' C4' 120.2(2)
C5' C6' C1' 120.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4978(15)
S1 C6 1.803(2)
S1 C2 1.828(2)
C2 C1' 1.509(2)
C2 S3 1.8099(19)
S3 C4 1.807(2)
C4 C5 1.499(4)
C5 C6 1.520(3)
C1' C2' 1.386(3)
C1' C6' 1.388(3)
C2' C3' 1.390(3)
C3' C4' 1.378(3)
C4' C5' 1.382(3)
C5' C6' 1.377(3)
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
O1 S1 C2 C1' 71.48(15)
C6 S1 C2 C1' -179.51(14)
O1 S1 C2 S3 -170.25(10)
C6 S1 C2 S3 -61.24(12)
C1' C2 S3 C4 -179.90(16)
S1 C2 S3 C4 60.38(14)
C2 S3 C4 C5 -59.6(2)
S3 C4 C5 C6 66.1(3)
C4 C5 C6 S1 -69.0(2)
O1 S1 C6 C5 171.78(17)
C2 S1 C6 C5 62.71(19)
S3 C2 C1' C2' 112.32(17)
S1 C2 C1' C2' -127.47(17)
S3 C2 C1' C6' -65.1(2)
S1 C2 C1' C6' 55.1(2)
C6' C1' C2' C3' 1.3(3)
C2 C1' C2' C3' -176.21(18)
C1' C2' C3' C4' -0.5(3)
C2' C3' C4' C5' -0.5(3)
C3' C4' C5' C6' 0.8(3)
C4' C5' C6' C1' -0.1(3)
C2' C1' C6' C5' -1.0(3)
C2 C1' C6' C5' 176.55(19)
