#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024434.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_4024434
loop_
_publ_author_name
'Chao Zhou'
'Zhao Fang'
'Chunling Fu'
'Shengming Ma'
_publ_section_title
;
Highly Regio- and Stereoselective Oxidative Hydroacetoxylation of
1,2-Allenylic Sulfoxides via a Different Mechanism
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2887
_journal_page_last               2890
_journal_paper_doi               10.1021/jo802755k
_journal_volume                  74
_journal_year                    2009
_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                 111.071(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3591(13)
_cell_length_b                   23.949(4)
_cell_length_c                   8.0712(13)
_cell_measurement_reflns_used    1566
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.148
_cell_measurement_theta_min      5.222
_cell_volume                     1507.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.1402
_diffrn_reflns_av_sigmaI/netI    0.1152
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8774
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75917
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.404
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.094
_refine_ls_shift/su_mean         0.033
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0826P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                1695
_reflns_number_total             3276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802755k_si_004.cif
_cod_data_source_block           cd26150
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024434
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 0.17244(10) 0.66397(3) 0.66124(11) 0.0654(3) Uani 1 1 d . . .
O1 O 0.2714(3) 0.71272(9) 0.6620(4) 0.0913(8) Uani 1 1 d . . .
O2 O 0.1283(4) 0.62769(10) 0.5099(3) 0.0961(8) Uani 1 1 d . . .
O3 O 0.2270(3) 0.47649(8) 0.7937(3) 0.0761(7) Uani 1 1 d . . .
O4 O -0.0376(3) 0.50135(12) 0.7669(4) 0.1012(9) Uani 1 1 d . . .
C1 C 0.2829(4) 0.62664(12) 0.8583(4) 0.0615(8) Uani 1 1 d . . .
C2 C 0.3033(4) 0.57147(14) 0.8575(5) 0.0693(9) Uani 1 1 d . . .
C3 C 0.2491(5) 0.52918(13) 0.7133(5) 0.0708(9) Uani 1 1 d . . .
C4 C 0.3837(5) 0.51835(15) 0.6342(6) 0.0952(12) Uani 1 1 d . . .
H4A H 0.4907 0.5099 0.7272 0.123 Uiso 1 1 calc R . .
H4B H 0.3969 0.5509 0.5709 0.123 Uiso 1 1 calc R . .
H4C H 0.3494 0.4873 0.5539 0.123 Uiso 1 1 calc R . .
C5 C 0.0771(5) 0.46865(15) 0.8140(5) 0.0779(10) Uani 1 1 d . . .
C6 C 0.0750(6) 0.41424(16) 0.9049(5) 0.1038(13) Uani 1 1 d . . .
H6A H 0.0757 0.4213 1.0223 0.136 Uiso 1 1 calc R . .
H6B H 0.1744 0.3928 0.9124 0.136 Uiso 1 1 calc R . .
H6C H -0.0266 0.3938 0.8382 0.136 Uiso 1 1 calc R . .
C7 C -0.0172(3) 0.68520(12) 0.6884(4) 0.0573(7) Uani 1 1 d . . .
C8 C -0.0346(4) 0.73980(14) 0.7354(4) 0.0701(9) Uani 1 1 d . . .
H8 H 0.0552 0.7649 0.7555 0.084 Uiso 1 1 calc R . .
C9 C -0.1838(5) 0.75671(17) 0.7521(5) 0.0864(11) Uani 1 1 d . . .
H9 H -0.1954 0.7934 0.7839 0.104 Uiso 1 1 calc R . .
C10 C -0.3157(5) 0.7202(2) 0.7226(6) 0.0973(13) Uani 1 1 d . . .
H10 H -0.4174 0.7322 0.7333 0.117 Uiso 1 1 calc R . .
C11 C -0.3004(5) 0.6662(2) 0.6774(6) 0.1041(15) Uani 1 1 d . . .
H11 H -0.3904 0.6413 0.6599 0.125 Uiso 1 1 calc R . .
C12 C -0.1505(4) 0.64827(15) 0.6574(5) 0.0817(10) Uani 1 1 d . . .
H12 H -0.1404 0.6117 0.6235 0.098 Uiso 1 1 calc R . .
C13 C 0.3501(5) 0.66344(15) 1.0184(5) 0.0874(11) Uani 1 1 d . . .
H13A H 0.4352 0.6882 1.0021 0.105 Uiso 1 1 calc R . .
H13B H 0.2564 0.6866 1.0224 0.105 Uiso 1 1 calc R . .
C14 C 0.4285(5) 0.63574(17) 1.1938(5) 0.1049(13) Uani 1 1 d . . .
H14A H 0.3496 0.6089 1.2090 0.137 Uiso 1 1 calc R . .
H14B H 0.4544 0.6633 1.2863 0.137 Uiso 1 1 calc R . .
H14C H 0.5321 0.6172 1.1994 0.137 Uiso 1 1 calc R . .
H3 H 0.141(4) 0.5379(12) 0.620(4) 0.075(10) Uiso 1 1 d . . .
H2 H 0.362(4) 0.5553(14) 0.962(4) 0.082(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
O1 S1 O2 117.99(15) . . ?
O1 S1 C7 108.10(14) . . ?
O2 S1 C7 108.36(15) . . ?
O1 S1 C1 107.16(15) . . ?
O2 S1 C1 110.54(15) . . ?
C7 S1 C1 103.75(13) . . ?
C5 O3 C3 116.8(3) . . ?
C2 C1 C13 125.4(3) . . ?
C2 C1 S1 121.6(3) . . ?
C13 C1 S1 113.1(2) . . ?
C1 C2 C3 132.6(3) . . ?
C1 C2 H2 117(2) . . ?
C3 C2 H2 111(2) . . ?
O3 C3 C2 107.1(3) . . ?
O3 C3 C4 105.9(3) . . ?
C2 C3 C4 112.8(3) . . ?
O3 C3 H3 107.4(18) . . ?
C2 C3 H3 113.4(18) . . ?
C4 C3 H3 109.9(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 O3 123.5(3) . . ?
O4 C5 C6 125.4(4) . . ?
O3 C5 C6 111.1(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 120.0(3) . . ?
C12 C7 S1 120.1(3) . . ?
C8 C7 S1 119.9(2) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 119.1(4) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C1 117.4(3) . . ?
C14 C13 H13A 108.0 . . ?
C1 C13 H13A 108.0 . . ?
C14 C13 H13B 107.9 . . ?
C1 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 O1 1.430(2) . ?
S1 O2 1.435(2) . ?
S1 C7 1.752(3) . ?
S1 C1 1.768(3) . ?
O3 C5 1.335(4) . ?
O3 C3 1.460(4) . ?
O4 C5 1.190(4) . ?
C1 C2 1.333(4) . ?
C1 C13 1.497(4) . ?
C2 C3 1.485(5) . ?
C2 H2 0.89(3) . ?
C3 C4 1.502(4) . ?
C3 H3 0.97(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.498(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.374(4) . ?
C7 C8 1.384(4) . ?
C8 C9 1.363(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.359(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.485(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 C2 -135.5(3) . . . . ?
O2 S1 C1 C2 -5.7(3) . . . . ?
C7 S1 C1 C2 110.3(3) . . . . ?
O1 S1 C1 C13 43.6(3) . . . . ?
O2 S1 C1 C13 173.4(2) . . . . ?
C7 S1 C1 C13 -70.6(3) . . . . ?
C13 C1 C2 C3 -178.8(3) . . . . ?
S1 C1 C2 C3 0.2(5) . . . . ?
C5 O3 C3 C2 83.4(4) . . . . ?
C5 O3 C3 C4 -156.0(3) . . . . ?
C1 C2 C3 O3 -151.6(4) . . . . ?
C1 C2 C3 C4 92.4(5) . . . . ?
C3 O3 C5 O4 1.8(5) . . . . ?
C3 O3 C5 C6 -177.5(3) . . . . ?
O1 S1 C7 C12 167.0(3) . . . . ?
O2 S1 C7 C12 38.1(3) . . . . ?
C1 S1 C7 C12 -79.4(3) . . . . ?
O1 S1 C7 C8 -10.8(3) . . . . ?
O2 S1 C7 C8 -139.8(3) . . . . ?
C1 S1 C7 C8 102.7(3) . . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
S1 C7 C8 C9 178.3(2) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 -1.4(6) . . . . ?
C8 C7 C12 C11 -1.3(5) . . . . ?
S1 C7 C12 C11 -179.1(3) . . . . ?
C10 C11 C12 C7 1.7(6) . . . . ?
C2 C1 C13 C14 -7.4(5) . . . . ?
S1 C1 C13 C14 173.5(3) . . . . ?
