#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023887.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_4023887
loop_
_publ_author_name
'Ines Vujasinović'
'Jelena Veljković'
'Krešimir Molčanov'
'Biserka Kojić-Prodić'
'Kata Mlinarić-Majerski'
_publ_contact_author_address
;
 Rudjer Bošković Institute
 P.O. Box 180
 HR-10002 Zagreb
 Croatia
;
_publ_contact_author_email       kmolcano@irb.hr
_publ_contact_author_fax         '++ 385 1 4680245'
_publ_contact_author_name        'Krešimir Molćanov'
_publ_contact_author_phone       '++ 385 1 4571203'
_publ_section_title
;
 Thiamacrocyclic Lactones: New Ag(I)-Ionophores
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9221
_journal_page_last               9227
_journal_paper_doi               10.1021/jo801143s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C32 H44 O4 S6'
_chemical_formula_sum            'C32 H44 O4 S6'
_chemical_formula_weight         685.1
_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'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-04-11T15:51:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.307(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8823(4)
_cell_length_b                   6.7130(3)
_cell_length_c                   22.1603(8)
_cell_measurement_reflns_used    4542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2315
_cell_measurement_theta_min      3.9804
_cell_volume                     1618.45(11)
_computing_cell_refinement
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET)
        (compiled Oct 31 2007,17:16:07)
;
_computing_data_collection
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET)
        (compiled Oct 31 2007,17:16:07)
;
_computing_data_reduction
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET)
        (compiled Oct 31 2007,17:16:07)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Oxford Xcalibur Nova'
_diffrn_measurement_method
;
CCD detector
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18041
_diffrn_reflns_theta_full        76.69
_diffrn_reflns_theta_max         76.69
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    4.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0912P)²+0.4016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1829
_reflns_number_gt                2567
_reflns_number_total             3366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801143s_si_002.cif
_cod_data_source_block           ines27
_cod_database_code               4023887
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
S3 S 0.36228(10) 0.1739(2) 0.00807(5) 0.0847(4) Uani 1 d . . .
S2 S 0.53862(9) 0.31262(18) -0.16298(4) 0.0738(3) Uani 1 d . . .
O2 O 0.1411(2) 0.2238(4) -0.04015(11) 0.0691(7) Uani 1 d . . .
C5A C -0.0516(3) 0.2518(5) 0.12576(14) 0.0515(7) Uani 1 d . . .
C9A C 0.0047(3) 0.2318(5) 0.06330(13) 0.0516(7) Uani 1 d . . .
H9A1 H -0.0238 0.1095 0.0443 0.062 Uiso 1 calc R . .
H9A2 H -0.0217 0.3426 0.0381 0.062 Uiso 1 calc R . .
C6 C 0.1999(3) 0.2124(5) 0.00626(15) 0.0562(8) Uani 1 d . . .
C4 C 0.5041(4) 0.3003(6) -0.08367(16) 0.0663(9) Uani 1 d . . .
H4A H 0.575 0.248 -0.0616 0.08 Uiso 1 calc R . .
H4B H 0.4887 0.4338 -0.0689 0.08 Uiso 1 calc R . .
C6A C -0.0075(3) 0.4502(5) 0.15469(15) 0.0580(8) Uani 1 d . . .
H6A1 H -0.0344 0.5615 0.1298 0.07 Uiso 1 calc R . .
H6A2 H -0.0426 0.4654 0.1943 0.07 Uiso 1 calc R . .
C7A C 0.1330(3) 0.4488(5) 0.16037(15) 0.0611(8) Uani 1 d . . .
H7A H 0.1612 0.574 0.1787 0.073 Uiso 1 calc R . .
C1A C 0.1445(3) 0.2295(5) 0.06880(13) 0.0515(7) Uani 1 d . . .
C8A C 0.1882(3) 0.4273(5) 0.09801(15) 0.0582(8) Uani 1 d . . .
H8A1 H 0.2772 0.4284 0.1016 0.07 Uiso 1 calc R . .
H8A2 H 0.1628 0.5385 0.0727 0.07 Uiso 1 calc R . .
C4A C -0.0089(3) 0.0776(5) 0.16598(15) 0.0603(8) Uani 1 d . . .
H4A1 H -0.0443 0.09 0.2056 0.072 Uiso 1 calc R . .
H4A2 H -0.0364 -0.0474 0.1484 0.072 Uiso 1 calc R . .
C10A C 0.1748(4) 0.2747(6) 0.20005(16) 0.0670(9) Uani 1 d . . .
H10A H 0.2637 0.2746 0.2041 0.08 Uiso 1 calc R . .
H10B H 0.1411 0.2887 0.24 0.08 Uiso 1 calc R . .
C5 C 0.3953(4) 0.1725(7) -0.07164(18) 0.0764(11) Uani 1 d . . .
H5A H 0.4115 0.0372 -0.0846 0.092 Uiso 1 calc R . .
H5B H 0.3245 0.2216 -0.0945 0.092 Uiso 1 calc R . .
C2A C 0.1869(3) 0.0545(5) 0.10940(15) 0.0609(8) Uani 1 d . . .
H2A1 H 0.1603 -0.0708 0.0916 0.073 Uiso 1 calc R . .
H2A2 H 0.2759 0.0532 0.1131 0.073 Uiso 1 calc R . .
C3A C 0.1313(4) 0.0793(6) 0.17178(14) 0.0635(9) Uani 1 d . . .
H3C H 0.1581 -0.0315 0.1977 0.076 Uiso 1 calc R . .
C3 C 0.4096(4) 0.4626(7) -0.19027(17) 0.0737(11) Uani 1 d . . .
H3A H 0.4068 0.4583 -0.234 0.088 Uiso 1 calc R . .
H3B H 0.334 0.4041 -0.1761 0.088 Uiso 1 calc R . .
S1 S 0.27103(9) 0.79975(18) -0.18745(4) 0.0729(3) Uani 1 d . . .
C2 C 0.4154(3) 0.6758(7) -0.17040(18) 0.0696(10) Uani 1 d . . .
H2A H 0.4813 0.7433 -0.1909 0.084 Uiso 1 calc R . .
H2B H 0.4328 0.6819 -0.1273 0.084 Uiso 1 calc R . .
O1 O 0.2449(2) 0.6729(5) -0.07595(12) 0.0789(8) Uani 1 d . . .
C1 C 0.1903(3) 0.7341(5) -0.12004(14) 0.0591(8) Uani 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 0.018 0.009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.333 0.557 '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
C6 S3 C5 101.36(18) . . ?
C4 S2 C3 99.93(18) . . ?
C1 C5A C9A 110.3(3) 3_565 . ?
C1 C5A C4A 112.5(3) 3_565 . ?
C9A C5A C4A 109.6(3) . . ?
C1 C5A C6A 106.2(3) 3_565 . ?
C9A C5A C6A 108.8(3) . . ?
C4A C5A C6A 109.1(3) . . ?
C1A C9A C5A 110.3(3) . . ?
C1A C9A H9A1 109.6 . . ?
C5A C9A H9A1 109.6 . . ?
C1A C9A H9A2 109.6 . . ?
C5A C9A H9A2 109.6 . . ?
H9A1 C9A H9A2 108.1 . . ?
O2 C6 C1A 123.9(3) . . ?
O2 C6 S3 122.4(3) . . ?
C1A C6 S3 113.7(2) . . ?
C5 C4 S2 112.6(3) . . ?
C5 C4 H4A 109.1 . . ?
S2 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
S2 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C7A C6A C5A 109.1(3) . . ?
C7A C6A H6A1 109.9 . . ?
C5A C6A H6A1 109.9 . . ?
C7A C6A H6A2 109.9 . . ?
C5A C6A H6A2 109.9 . . ?
H6A1 C6A H6A2 108.3 . . ?
C10A C7A C8A 109.3(3) . . ?
C10A C7A C6A 109.6(3) . . ?
C8A C7A C6A 109.8(3) . . ?
C10A C7A H7A 109.4 . . ?
C8A C7A H7A 109.4 . . ?
C6A C7A H7A 109.4 . . ?
C9A C1A C6 110.0(3) . . ?
C9A C1A C2A 109.8(3) . . ?
C6 C1A C2A 110.6(3) . . ?
C9A C1A C8A 108.8(3) . . ?
C6 C1A C8A 108.7(3) . . ?
C2A C1A C8A 108.9(3) . . ?
C7A C8A C1A 109.7(3) . . ?
C7A C8A H8A1 109.7 . . ?
C1A C8A H8A1 109.7 . . ?
C7A C8A H8A2 109.7 . . ?
C1A C8A H8A2 109.7 . . ?
H8A1 C8A H8A2 108.2 . . ?
C3A C4A C5A 109.3(3) . . ?
C3A C4A H4A1 109.8 . . ?
C5A C4A H4A1 109.8 . . ?
C3A C4A H4A2 109.8 . . ?
C5A C4A H4A2 109.8 . . ?
H4A1 C4A H4A2 108.3 . . ?
C3A C10A C7A 109.7(3) . . ?
C3A C10A H10A 109.7 . . ?
C7A C10A H10A 109.7 . . ?
C3A C10A H10B 109.7 . . ?
C7A C10A H10B 109.7 . . ?
H10A C10A H10B 108.2 . . ?
C4 C5 S3 110.3(3) . . ?
C4 C5 H5A 109.6 . . ?
S3 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
S3 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C3A C2A C1A 108.9(3) . . ?
C3A C2A H2A1 109.9 . . ?
C1A C2A H2A1 109.9 . . ?
C3A C2A H2A2 109.9 . . ?
C1A C2A H2A2 109.9 . . ?
H2A1 C2A H2A2 108.3 . . ?
C10A C3A C4A 110.0(3) . . ?
C10A C3A C2A 109.8(3) . . ?
C4A C3A C2A 109.8(3) . . ?
C10A C3A H3C 109.1 . . ?
C4A C3A H3C 109.1 . . ?
C2A C3A H3C 109.1 . . ?
C2 C3 S2 113.8(3) . . ?
C2 C3 H3A 108.8 . . ?
S2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
S2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C1 S1 C2 98.72(18) . . ?
C3 C2 S1 110.3(3) . . ?
C3 C2 H2A 109.6 . . ?
S1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
S1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O1 C1 C5A 124.2(3) . 3_565 ?
O1 C1 S1 120.9(3) . . ?
C5A C1 S1 114.7(2) 3_565 . ?
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
S3 C6 1.785(4) . ?
S3 C5 1.811(4) . ?
S2 C4 1.808(4) . ?
S2 C3 1.820(4) . ?
O2 C6 1.201(4) . ?
C5A C1 1.515(5) 3_565 ?
C5A C9A 1.532(4) . ?
C5A C4A 1.536(5) . ?
C5A C6A 1.550(5) . ?
C9A C1A 1.524(5) . ?
C9A H9A1 0.97 . ?
C9A H9A2 0.97 . ?
C6 C1A 1.528(4) . ?
C4 C5 1.491(6) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C6A C7A 1.531(5) . ?
C6A H6A1 0.97 . ?
C6A H6A2 0.97 . ?
C7A C10A 1.526(5) . ?
C7A C8A 1.526(5) . ?
C7A H7A 0.98 . ?
C1A C2A 1.544(4) . ?
C1A C8A 1.547(4) . ?
C8A H8A1 0.97 . ?
C8A H8A2 0.97 . ?
C4A C3A 1.528(5) . ?
C4A H4A1 0.97 . ?
C4A H4A2 0.97 . ?
C10A C3A 1.524(6) . ?
C10A H10A 0.97 . ?
C10A H10B 0.97 . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C2A C3A 1.531(4) . ?
C2A H2A1 0.97 . ?
C2A H2A2 0.97 . ?
C3A H3C 0.98 . ?
C3 C2 1.498(6) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
S1 C1 1.805(3) . ?
S1 C2 1.810(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
O1 C1 1.205(4) . ?
C1 C5A 1.515(5) 3_565 ?
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
C1 C5A C9A C1A 176.8(3) 3_565 . . . ?
C4A C5A C9A C1A -58.7(3) . . . . ?
C6A C5A C9A C1A 60.6(3) . . . . ?
C5 S3 C6 O2 2.3(4) . . . . ?
C5 S3 C6 C1A -177.5(3) . . . . ?
C3 S2 C4 C5 70.9(4) . . . . ?
C1 C5A C6A C7A -178.5(3) 3_565 . . . ?
C9A C5A C6A C7A -59.7(4) . . . . ?
C4A C5A C6A C7A 59.9(3) . . . . ?
C5A C6A C7A C10A -60.0(3) . . . . ?
C5A C6A C7A C8A 60.1(4) . . . . ?
C5A C9A C1A C6 -179.3(3) . . . . ?
C5A C9A C1A C2A 58.8(3) . . . . ?
C5A C9A C1A C8A -60.3(3) . . . . ?
O2 C6 C1A C9A 8.3(5) . . . . ?
S3 C6 C1A C9A -171.8(2) . . . . ?
O2 C6 C1A C2A 129.8(4) . . . . ?
S3 C6 C1A C2A -50.3(3) . . . . ?
O2 C6 C1A C8A -110.6(4) . . . . ?
S3 C6 C1A C8A 69.2(3) . . . . ?
C10A C7A C8A C1A 60.1(4) . . . . ?
C6A C7A C8A C1A -60.2(4) . . . . ?
C9A C1A C8A C7A 59.7(3) . . . . ?
C6 C1A C8A C7A 179.5(3) . . . . ?
C2A C1A C8A C7A -60.0(4) . . . . ?
C1 C5A C4A C3A -177.4(3) 3_565 . . . ?
C9A C5A C4A C3A 59.3(4) . . . . ?
C6A C5A C4A C3A -59.8(3) . . . . ?
C8A C7A C10A C3A -60.3(4) . . . . ?
C6A C7A C10A C3A 60.1(4) . . . . ?
S2 C4 C5 S3 -177.9(2) . . . . ?
C6 S3 C5 C4 133.6(3) . . . . ?
C9A C1A C2A C3A -59.3(4) . . . . ?
C6 C1A C2A C3A 179.0(3) . . . . ?
C8A C1A C2A C3A 59.7(4) . . . . ?
C7A C10A C3A C4A -60.1(4) . . . . ?
C7A C10A C3A C2A 60.8(4) . . . . ?
C5A C4A C3A C10A 60.1(3) . . . . ?
C5A C4A C3A C2A -60.9(4) . . . . ?
C1A C2A C3A C10A -60.4(4) . . . . ?
C1A C2A C3A C4A 60.6(4) . . . . ?
C4 S2 C3 C2 70.3(3) . . . . ?
S2 C3 C2 S1 -169.25(19) . . . . ?
C1 S1 C2 C3 86.3(3) . . . . ?
C2 S1 C1 O1 16.2(4) . . . . ?
C2 S1 C1 C5A -159.6(3) . . . 3_565 ?
