#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/58/1505828.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_1505828
loop_
_publ_author_name
'Liu, Haibo'
'Siegel, Dionicio R.'
'Danishefsky, Samuel J.'
_publ_section_title
;
 Studies directed toward the synthesis of terreulactone A: rapid
 construction of the A, B, C rings.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              423
_journal_page_last               425
_journal_paper_doi               10.1021/ol052618p
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C22 H30 O5 S'
_chemical_formula_weight         406.52
_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                 102.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.055(2)
_cell_length_b                   14.345(3)
_cell_length_c                   15.008(3)
_cell_measurement_temperature    106(2)
_cell_volume                     2111.0(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      106(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'ω 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  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8903
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.8704
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0551
_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)+(0.0425P)²+0.9974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                3046
_reflns_number_total             4816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol052618psi20051028_112736.cif
_cod_data_source_block           x1518l
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2111.0(7)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1505828
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
S S 0.44108(6) 0.44031(4) 0.27909(4) 0.02321(16) Uani 1 1 d .
O2 O 0.22167(16) 0.52274(11) 0.12887(11) 0.0261(4) Uani 1 1 d .
O4 O 0.28587(16) 0.33336(11) -0.00817(10) 0.0251(4) Uani 1 1 d .
O8 O 0.62568(14) 0.24745(11) 0.17476(10) 0.0239(4) Uani 1 1 d .
O10 O 0.30471(18) 0.48322(13) -0.04709(11) 0.0358(5) Uani 1 1 d .
O20 O 0.79476(16) 0.20475(12) 0.09767(11) 0.0300(4) Uani 1 1 d .
C1 C 0.4053(2) 0.39675(15) 0.16254(14) 0.0184(5) Uani 1 1 d .
H1A H 0.4802 0.4186 0.1336 0.022 Uiso 1 1 calc R
C2 C 0.2661(2) 0.43698(16) 0.10405(15) 0.0222(5) Uani 1 1 d .
C3 C 0.1599(2) 0.35792(16) 0.10247(16) 0.0236(5) Uani 1 1 d .
C4 C 0.2553(2) 0.28506(17) 0.07337(16) 0.0233(5) Uani 1 1 d .
C5 C 0.2114(2) 0.18833(17) 0.04121(17) 0.0293(6) Uani 1 1 d .
H5A H 0.1270 0.1914 -0.0074 0.035 Uiso 1 1 calc R
H5B H 0.1920 0.1514 0.0926 0.035 Uiso 1 1 calc R
C6 C 0.3249(3) 0.14142(18) 0.00415(17) 0.0321(6) Uani 1 1 d .
H6A H 0.3291 0.1705 -0.0550 0.039 Uiso 1 1 calc R
H6B H 0.3019 0.0748 -0.0074 0.039 Uiso 1 1 calc R
C7 C 0.4660(2) 0.14869(17) 0.06921(16) 0.0268(6) Uani 1 1 d .
H7A H 0.4683 0.1070 0.1221 0.032 Uiso 1 1 calc R
H7B H 0.5359 0.1265 0.0370 0.032 Uiso 1 1 calc R
C8 C 0.5030(2) 0.24744(17) 0.10441(15) 0.0216(5) Uani 1 1 d .
H8A H 0.5157 0.2879 0.0527 0.026 Uiso 1 1 calc R
C9 C 0.3902(2) 0.28860(16) 0.14717(15) 0.0188(5) Uani 1 1 d .
C10 C 0.2876(2) 0.42627(17) 0.00806(16) 0.0247(6) Uani 1 1 d .
C11 C 0.6223(2) 0.43343(16) 0.30694(15) 0.0204(5) Uani 1 1 d .
C12 C 0.6878(2) 0.37969(17) 0.37996(15) 0.0263(6) Uani 1 1 d .
H12A H 0.6359 0.3438 0.4132 0.032 Uiso 1 1 calc R
C13 C 0.8291(3) 0.37795(18) 0.40497(17) 0.0315(6) Uani 1 1 d .
H13A H 0.8734 0.3415 0.4558 0.038 Uiso 1 1 calc R
C14 C 0.9051(2) 0.42867(18) 0.35663(17) 0.0301(6) Uani 1 1 d .
H14A H 1.0019 0.4273 0.3740 0.036 Uiso 1 1 calc R
C15 C 0.8408(2) 0.48169(17) 0.28263(16) 0.0266(6) Uani 1 1 d .
H15A H 0.8933 0.5161 0.2486 0.032 Uiso 1 1 calc R
C16 C 0.6999(2) 0.48461(16) 0.25826(15) 0.0216(5) Uani 1 1 d .
H16A H 0.6558 0.5218 0.2080 0.026 Uiso 1 1 calc R
C17 C 0.3068(3) 0.60171(17) 0.12068(18) 0.0316(6) Uani 1 1 d .
H17A H 0.4027 0.5825 0.1354 0.047 Uiso 1 1 calc R
H17B H 0.2926 0.6507 0.1631 0.047 Uiso 1 1 calc R
H17C H 0.2831 0.6256 0.0580 0.047 Uiso 1 1 calc R
C18 C 0.1185(2) 0.34573(18) 0.19395(17) 0.0314(6) Uani 1 1 d .
H18A H 0.0473 0.3910 0.1984 0.047 Uiso 1 1 calc R
H18B H 0.1981 0.3559 0.2441 0.047 Uiso 1 1 calc R
H18C H 0.0836 0.2824 0.1980 0.047 Uiso 1 1 calc R
C19 C 0.0281(2) 0.37220(19) 0.02955(18) 0.0329(6) Uani 1 1 d .
H19A H -0.0334 0.3194 0.0306 0.049 Uiso 1 1 calc R
H19B H 0.0498 0.3764 -0.0308 0.049 Uiso 1 1 calc R
H19C H -0.0164 0.4299 0.0423 0.049 Uiso 1 1 calc R
C20 C 0.7454(2) 0.27380(17) 0.14828(17) 0.0263(6) Uani 1 1 d .
H20A H 0.8165 0.2882 0.2036 0.032 Uiso 1 1 calc R
H20B H 0.7276 0.3313 0.1111 0.032 Uiso 1 1 calc R
C21 C 0.8370(3) 0.12307(19) 0.1505(2) 0.0412(7) Uani 1 1 d .
H21A H 0.9036 0.1401 0.2063 0.062 Uiso 1 1 calc R
H21B H 0.8789 0.0793 0.1147 0.062 Uiso 1 1 calc R
H21C H 0.7577 0.0937 0.1668 0.062 Uiso 1 1 calc R
C22 C 0.3862(2) 0.23148(17) 0.23281(15) 0.0250(6) Uani 1 1 d .
H22A H 0.3654 0.1663 0.2156 0.038 Uiso 1 1 calc R
H22B H 0.3156 0.2565 0.2619 0.038 Uiso 1 1 calc R
H22C H 0.4751 0.2351 0.2757 0.038 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
C11 S C1 100.45(11)
C2 O2 C17 116.19(19)
C10 O4 C4 107.78(17)
C20 O8 C8 116.38(18)
C20 O20 C21 112.11(19)
C9 C1 C2 103.50(17)
C9 C1 S 118.25(15)
C2 C1 S 111.72(15)
O2 C2 C10 117.95(19)
O2 C2 C3 112.98(19)
C10 C2 C3 98.87(18)
O2 C2 C1 118.08(18)
C10 C2 C1 101.27(18)
C3 C2 C1 105.16(18)
C18 C3 C19 106.9(2)
C18 C3 C4 119.0(2)
C19 C3 C4 112.4(2)
C18 C3 C2 113.1(2)
C19 C3 C2 113.3(2)
C4 C3 C2 91.77(17)
O4 C4 C5 105.29(18)
O4 C4 C3 99.83(18)
C5 C4 C3 124.0(2)
O4 C4 C9 105.26(17)
C5 C4 C9 114.07(19)
C3 C4 C9 105.99(18)
C4 C5 C6 109.4(2)
C5 C6 C7 113.4(2)
C8 C7 C6 113.69(19)
O8 C8 C7 110.97(18)
O8 C8 C9 106.62(17)
C7 C8 C9 110.76(19)
C22 C9 C8 107.65(18)
C22 C9 C4 113.59(18)
C8 C9 C4 107.36(18)
C22 C9 C1 115.12(18)
C8 C9 C1 112.60(18)
C4 C9 C1 100.25(17)
O10 C10 O4 122.9(2)
O10 C10 C2 131.3(2)
O4 C10 C2 105.82(19)
C12 C11 C16 119.2(2)
C12 C11 S 120.04(19)
C16 C11 S 120.76(17)
C11 C12 C13 120.3(2)
C14 C13 C12 120.3(2)
C13 C14 C15 120.0(2)
C14 C15 C16 119.9(2)
C15 C16 C11 120.4(2)
O8 C20 O20 113.07(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C11 1.780(2)
S C1 1.817(2)
O2 C2 1.387(3)
O2 C17 1.442(3)
O4 C10 1.354(3)
O4 C4 1.496(3)
O8 C20 1.401(3)
O8 C8 1.435(3)
O10 C10 1.202(3)
O20 C20 1.404(3)
O20 C21 1.426(3)
C1 C9 1.571(3)
C1 C2 1.587(3)
C2 C10 1.511(3)
C2 C3 1.554(3)
C3 C18 1.530(3)
C3 C19 1.535(3)
C3 C4 1.545(3)
C4 C5 1.503(3)
C4 C9 1.551(3)
C5 C6 1.531(4)
C6 C7 1.538(3)
C7 C8 1.529(3)
C8 C9 1.539(3)
C9 C22 1.532(3)
C11 C12 1.382(3)
C11 C16 1.390(3)
C12 C13 1.386(3)
C13 C14 1.374(4)
C14 C15 1.383(3)
C15 C16 1.383(3)
