#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/31/4023157.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_4023157
loop_
_publ_author_name
'Takahiro Tsuchiya'
'Yosuke Okada'
'Toshio Shimizu'
'Kazunori Hirabayashi'
'Nobumasa Kamigata'
_publ_section_title
;
 Molecular Transformations of Unsaturated Thiacrown Ethers
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              76
_journal_page_last               80
_journal_paper_doi               10.1021/jo701757s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H18 O2 S6'
_chemical_formula_weight         410.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.196(12)
_cell_angle_beta                 94.448(13)
_cell_angle_gamma                118.116(8)
_cell_formula_units_Z            4
_cell_length_a                   11.025(3)
_cell_length_b                   11.127(2)
_cell_length_c                   18.890(4)
_cell_measurement_temperature    296(2)
_cell_volume                     2002.8(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9769
_diffrn_reflns_theta_full        21.00
_diffrn_reflns_theta_max         21.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.9347
_exptl_absorpt_correction_T_min  0.7713
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0619
_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)+(0.0822P)²+2.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1661
_reflns_number_gt                3197
_reflns_number_total             4256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701757s-File006.cif
_cod_data_source_block           Compound_12
_cod_database_code               4023157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.95833(18) 0.69438(19) 0.05299(9) 0.0649(5) Uani 1 1 d . A 1
S2 S 0.7720(2) 0.6466(2) 0.18569(11) 0.0835(6) Uani 1 1 d . A 1
S3 S 0.5310(2) 0.7426(2) 0.18156(10) 0.0820(6) Uani 1 1 d . A 1
S4 S 0.3784(2) 0.87527(19) 0.08595(11) 0.0756(6) Uani 1 1 d . A 1
S5 S 0.53222(19) 0.76132(17) -0.02845(11) 0.0698(6) Uani 1 1 d . A 1
S6 S 0.84777(18) 0.82425(17) -0.05011(10) 0.0635(5) Uani 1 1 d . A 1
C1 C 0.9855(9) 0.8239(8) 0.1264(4) 0.098(3) Uani 1 1 d . A 1
H1 H 1.0563 0.9134 0.1270 0.118 Uiso 1 1 calc R A 1
C2 C 0.9143(8) 0.8038(8) 0.1798(4) 0.079(2) Uani 1 1 d . A 1
H2 H 0.9413 0.8785 0.2172 0.095 Uiso 1 1 calc R A 1
C3 C 0.7110(9) 0.6915(10) 0.2624(4) 0.097(3) Uani 1 1 d . A 1
H3 H 0.7500 0.6881 0.3070 0.116 Uiso 1 1 calc R A 1
C4 C 0.6124(9) 0.7305(8) 0.2618(4) 0.085(2) Uani 1 1 d . A 1
H4 H 0.5866 0.7517 0.3054 0.102 Uiso 1 1 calc R A 1
C5 C 0.4206(8) 0.8021(8) 0.2157(4) 0.079(2) Uani 1 1 d . A 1
H5 H 0.4057 0.7966 0.2632 0.095 Uiso 1 1 calc R A 1
C6 C 0.3587(8) 0.8536(8) 0.1775(4) 0.087(2) Uani 1 1 d . A 1
H6 H 0.3005 0.8807 0.1994 0.104 Uiso 1 1 calc R A 1
C7 C 0.3084(7) 0.7005(6) 0.0432(3) 0.0575(17) Uani 1 1 d . A 1
H7 H 0.2247 0.6352 0.0547 0.069 Uiso 1 1 calc R A 1
C8 C 0.3688(6) 0.6566(7) -0.0047(3) 0.0579(17) Uani 1 1 d . A 1
H8 H 0.3207 0.5638 -0.0271 0.069 Uiso 1 1 calc R A 1
C9 C 0.5743(7) 0.6326(6) -0.0598(3) 0.0504(16) Uani 1 1 d . A 1
H9 H 0.5027 0.5414 -0.0722 0.060 Uiso 1 1 calc R A 1
C10 C 0.7020(7) 0.6582(6) -0.0669(3) 0.0541(16) Uani 1 1 d . A 1
H10 H 0.7156 0.5831 -0.0818 0.065 Uiso 1 1 calc R A 1
C11 C 0.9916(6) 0.7950(7) -0.0196(3) 0.0585(17) Uani 1 1 d . A 1
H11 H 1.0707 0.8867 0.0008 0.070 Uiso 1 1 calc R A 1
C12 C 1.0408(7) 0.7307(8) -0.0803(4) 0.0659(19) Uani 1 1 d . A 1
H12 H 1.1209 0.7232 -0.0597 0.079 Uiso 1 1 calc R A 1
C13 C 1.2226(9) 0.9105(11) -0.1256(5) 0.134(4) Uani 1 1 d . A 1
H13 H 1.2502 0.9731 -0.0803 0.201 Uiso 1 1 calc R A 1
H14 H 1.2398 0.9619 -0.1643 0.201 Uiso 1 1 calc R A 1
H15 H 1.2753 0.8621 -0.1266 0.201 Uiso 1 1 calc R A 1
C14 C 0.9703(10) 0.5268(8) -0.1671(5) 0.108(3) Uani 1 1 d . A 1
H16 H 0.9659 0.5597 -0.2113 0.161 Uiso 1 1 calc R A 1
H17 H 0.9066 0.4291 -0.1743 0.161 Uiso 1 1 calc R A 1
H18 H 1.0632 0.5437 -0.1526 0.161 Uiso 1 1 calc R A 1
S7 S 0.76264(18) 0.29793(17) 0.45816(9) 0.0597(5) Uani 1 1 d . B 2
S8 S 0.5808(2) 0.3364(2) 0.32641(11) 0.0879(7) Uani 1 1 d . B 2
S9 S 0.2582(2) 0.26749(19) 0.32694(9) 0.0714(6) Uani 1 1 d . B 2
S10 S -0.00056(19) 0.12594(19) 0.42143(11) 0.0744(6) Uani 1 1 d . B 2
S11 S 0.29761(18) 0.24288(17) 0.52846(10) 0.0624(5) Uani 1 1 d . B 2
S12 S 0.54771(17) 0.17361(17) 0.55851(10) 0.0631(5) Uani 1 1 d . B 2
C15 C 0.6662(8) 0.1707(7) 0.3812(4) 0.076(2) Uani 1 1 d . B 2
H19 H 0.6648 0.0859 0.3779 0.092 Uiso 1 1 calc R B 2
C16 C 0.5954(8) 0.1886(7) 0.3278(4) 0.073(2) Uani 1 1 d . B 2
H20 H 0.5504 0.1168 0.2881 0.087 Uiso 1 1 calc R B 2
C17 C 0.4575(10) 0.2877(10) 0.2475(4) 0.105(3) Uani 1 1 d . B 2
H21 H 0.4855 0.2784 0.2029 0.126 Uiso 1 1 calc R B 2
C18 C 0.3293(9) 0.2639(8) 0.2484(4) 0.087(2) Uani 1 1 d . B 2
H22 H 0.2734 0.2441 0.2044 0.104 Uiso 1 1 calc R B 2
C19 C 0.0812(9) 0.1940(8) 0.2906(4) 0.084(2) Uani 1 1 d . B 2
H23 H 0.0582 0.1934 0.2421 0.100 Uiso 1 1 calc R B 2
C20 C -0.0221(9) 0.1389(8) 0.3297(5) 0.086(2) Uani 1 1 d . B 2
H24 H -0.1126 0.1047 0.3064 0.104 Uiso 1 1 calc R B 2
C21 C 0.1075(7) 0.3000(6) 0.4619(3) 0.0585(17) Uani 1 1 d . B 2
H25 H 0.0804 0.3640 0.4512 0.070 Uiso 1 1 calc R B 2
C22 C 0.2262(7) 0.3472(7) 0.5072(3) 0.0586(17) Uani 1 1 d . B 2
H26 H 0.2734 0.4406 0.5285 0.070 Uiso 1 1 calc R B 2
C23 C 0.4705(6) 0.3724(6) 0.5645(3) 0.0544(16) Uani 1 1 d . B 2
H27 H 0.4898 0.4640 0.5765 0.065 Uiso 1 1 calc R B 2
C24 C 0.5732(7) 0.3434(7) 0.5749(3) 0.0577(17) Uani 1 1 d . B 2
H28 H 0.6628 0.4161 0.5916 0.069 Uiso 1 1 calc R B 2
C25 C 0.7107(6) 0.1977(6) 0.5302(3) 0.0555(17) Uani 1 1 d . B 2
H29 H 0.6932 0.1046 0.5095 0.067 Uiso 1 1 calc R B 2
C26 C 0.8365(7) 0.2554(6) 0.5903(3) 0.0575(17) Uani 1 1 d . B 2
H30 H 0.9104 0.2412 0.5720 0.069 Uiso 1 1 calc R B 2
C27 C 0.7919(10) 0.0610(8) 0.6458(4) 0.099(3) Uani 1 1 d . B 2
H31 H 0.7073 -0.0065 0.6147 0.149 Uiso 1 1 calc R B 2
H32 H 0.7919 0.0365 0.6927 0.149 Uiso 1 1 calc R B 2
H33 H 0.8702 0.0635 0.6257 0.149 Uiso 1 1 calc R B 2
C28 C 1.0237(7) 0.4693(8) 0.6525(4) 0.077(2) Uani 1 1 d . B 2
H34 H 1.0239 0.4312 0.6953 0.116 Uiso 1 1 calc R B 2
H35 H 1.0534 0.5664 0.6657 0.116 Uiso 1 1 calc R B 2
H36 H 1.0861 0.4573 0.6234 0.116 Uiso 1 1 calc R B 2
O1 O 1.0803(5) 0.8146(5) -0.1338(2) 0.0719(14) Uani 1 1 d . A 1
O2 O 0.9329(5) 0.5986(5) -0.1116(3) 0.0777(14) Uani 1 1 d . A 1
O3 O 0.8010(5) 0.1934(5) 0.6519(2) 0.0677(13) Uani 1 1 d . B 2
O4 O 0.8847(4) 0.3989(4) 0.6119(2) 0.0650(12) Uani 1 1 d . B 2
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
C1 S1 C11 99.6(3) . . ?
C2 S2 C3 102.3(4) . . ?
C4 S3 C5 100.8(4) . . ?
C7 S4 C6 100.2(3) . . ?
C9 S5 C8 99.3(3) . . ?
C10 S6 C11 103.8(3) . . ?
C2 C1 S1 125.1(6) . . ?
C1 C2 S2 124.3(6) . . ?
C4 C3 S2 125.3(6) . . ?
C3 C4 S3 122.1(6) . . ?
C6 C5 S3 123.4(7) . . ?
C5 C6 S4 124.3(6) . . ?
C8 C7 S4 123.8(5) . . ?
C7 C8 S5 124.8(5) . . ?
C10 C9 S5 123.6(5) . . ?
C9 C10 S6 124.3(5) . . ?
C12 C11 S6 114.6(4) . . ?
C12 C11 S1 109.3(5) . . ?
S6 C11 S1 113.6(3) . . ?
O2 C12 O1 109.4(5) . . ?
O2 C12 C11 109.4(5) . . ?
O1 C12 C11 110.3(6) . . ?
C15 S7 C25 101.6(3) . . ?
C16 S8 C17 102.4(4) . . ?
C18 S9 C19 100.4(4) . . ?
C21 S10 C20 101.4(4) . . ?
C22 S11 C23 99.9(3) . . ?
C24 S12 C25 102.7(3) . . ?
C16 C15 S7 123.6(6) . . ?
C15 C16 S8 124.5(6) . . ?
C18 C17 S8 124.0(7) . . ?
C17 C18 S9 123.7(6) . . ?
C20 C19 S9 123.1(6) . . ?
C19 C20 S10 125.4(6) . . ?
C22 C21 S10 124.5(5) . . ?
C21 C22 S11 123.5(5) . . ?
C24 C23 S11 122.2(5) . . ?
C23 C24 S12 122.9(5) . . ?
C26 C25 S12 116.3(4) . . ?
C26 C25 S7 108.5(4) . . ?
S12 C25 S7 114.4(3) . . ?
O4 C26 O3 107.5(5) . . ?
O4 C26 C25 108.0(5) . . ?
O3 C26 C25 112.1(5) . . ?
C13 O1 C12 115.2(6) . . ?
C12 O2 C14 113.8(6) . . ?
C26 O3 C27 114.3(5) . . ?
C26 O4 C28 111.7(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 C1 1.765(8) . ?
S1 C11 1.829(6) . ?
S2 C2 1.738(8) . ?
S2 C3 1.757(8) . ?
S3 C4 1.754(8) . ?
S3 C5 1.763(8) . ?
S4 C7 1.768(6) . ?
S4 C6 1.792(9) . ?
S5 C9 1.753(6) . ?
S5 C8 1.756(7) . ?
S6 C10 1.753(6) . ?
S6 C11 1.828(7) . ?
C1 C2 1.303(10) . ?
C3 C4 1.347(10) . ?
C5 C6 1.307(10) . ?
C7 C8 1.339(8) . ?
C9 C10 1.321(8) . ?
C11 C12 1.542(9) . ?
C12 O2 1.397(8) . ?
C12 O1 1.417(7) . ?
C13 O1 1.403(9) . ?
C14 O2 1.439(8) . ?
S7 C15 1.753(7) . ?
S7 C25 1.823(6) . ?
S8 C16 1.730(8) . ?
S8 C17 1.775(8) . ?
S9 C18 1.736(8) . ?
S9 C19 1.759(8) . ?
S10 C21 1.752(7) . ?
S10 C20 1.764(9) . ?
S11 C22 1.749(6) . ?
S11 C23 1.771(6) . ?
S12 C24 1.756(6) . ?
S12 C25 1.822(6) . ?
C15 C16 1.321(9) . ?
C17 C18 1.311(11) . ?
C19 C20 1.343(11) . ?
C21 C22 1.336(8) . ?
C23 C24 1.323(8) . ?
C25 C26 1.537(8) . ?
C26 O4 1.415(7) . ?
C26 O3 1.414(7) . ?
C27 O3 1.417(8) . ?
C28 O4 1.444(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658629
