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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/44/1504476.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_1504476
loop_
_publ_author_name
'Yamashita, Fumikazu'
'Kuniyasu, Hitoshi'
'Terao, Jun'
'Kambe, Nobuaki'
_publ_section_title
;
 Platinum-catalyzed regio- and stereoselective arylthiolation of internal
 alkynes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              101
_journal_page_last               104
_journal_paper_doi               10.1021/ol7025069
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C22 H20 O S '
_chemical_formula_sum            'C22 H20 O S'
_chemical_formula_weight         332.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 99.389(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.072(1)
_cell_length_b                   5.6379(3)
_cell_length_c                   18.960(1)
_cell_measurement_reflns_used    12330
_cell_measurement_temperature    273.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     1800.46(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28885
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1490
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.0080
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                1490
_reflns_number_total             4121
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol7025069-file003.cif
_cod_data_source_block           yama27
_cod_original_cell_volume        1800.4(2)
_cod_original_formula_sum        'C22 H20 O S '
_cod_database_code               1504476
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-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_calc_flag
S(1) S 0.83679(5) -0.2559(2) 0.27937(4) 0.0567(3) Uani 1.00 d
O(1) O 0.7013(1) 0.1288(5) 0.0569(1) 0.0776(9) Uani 1.00 d
C(1) C 0.6600(2) -0.0888(8) 0.0481(2) 0.083(1) Uani 1.00 d
C(2) C 0.7175(2) 0.2053(6) 0.1291(2) 0.058(1) Uani 1.00 d
C(3) C 0.7795(2) 0.0553(5) 0.1741(2) 0.0451(9) Uani 1.00 d
C(4) C 0.7649(2) -0.0595(5) 0.2319(2) 0.0436(9) Uani 1.00 d
C(5) C 0.6881(2) -0.0480(5) 0.2607(1) 0.0414(9) Uani 1.00 d
C(6) C 0.6339(2) -0.2319(5) 0.2484(2) 0.0546(10) Uani 1.00 d
C(7) C 0.5639(2) -0.2264(6) 0.2762(2) 0.060(1) Uani 1.00 d
C(8) C 0.5487(2) -0.0377(7) 0.3179(2) 0.057(1) Uani 1.00 d
C(9) C 0.6012(2) 0.1456(6) 0.3301(2) 0.060(1) Uani 1.00 d
C(10) C 0.6712(2) 0.1413(5) 0.3014(2) 0.0544(10) Uani 1.00 d
C(11) C 0.8490(2) -0.1307(6) 0.3660(2) 0.0509(10) Uani 1.00 d
C(12) C 0.8160(2) -0.2321(7) 0.4198(2) 0.081(1) Uani 1.00 d
C(13) C 0.8274(3) -0.1332(10) 0.4869(2) 0.108(2) Uani 1.00 d
C(14) C 0.8721(3) 0.0634(9) 0.5013(2) 0.097(2) Uani 1.00 d
C(15) C 0.9050(3) 0.1688(8) 0.4478(3) 0.103(2) Uani 1.00 d
C(16) C 0.8933(2) 0.0702(7) 0.3805(2) 0.082(1) Uani 1.00 d
C(17) C 0.8586(2) 0.0466(5) 0.1492(2) 0.0429(9) Uani 1.00 d
C(18) C 0.8778(2) -0.1309(6) 0.1052(2) 0.057(1) Uani 1.00 d
C(19) C 0.9500(2) -0.1281(6) 0.0810(2) 0.060(1) Uani 1.00 d
C(20) C 1.0032(2) 0.0520(6) 0.0998(2) 0.053(1) Uani 1.00 d
C(21) C 0.9843(2) 0.2295(6) 0.1433(2) 0.0559(10) Uani 1.00 d
C(22) C 0.9124(2) 0.2275(5) 0.1677(2) 0.0527(9) Uani 1.00 d
H(1) H 0.6097 -0.0819 0.0640 0.0985 Uiso 1.00 calc
H(2) H 0.6514 -0.1410 -0.0007 0.0985 Uiso 1.00 calc
H(3) H 0.6902 -0.2156 0.0759 0.0985 Uiso 1.00 calc
H(4) H 0.7356 0.3681 0.1304 0.0711 Uiso 1.00 calc
H(5) H 0.6696 0.2034 0.1499 0.0711 Uiso 1.00 calc
H(6) H 0.6450 -0.3618 0.2186 0.0675 Uiso 1.00 calc
H(7) H 0.5258 -0.3569 0.2668 0.0726 Uiso 1.00 calc
H(8) H 0.5012 -0.0379 0.3396 0.0680 Uiso 1.00 calc
H(9) H 0.5891 0.2793 0.3577 0.0734 Uiso 1.00 calc
H(10) H 0.7080 0.2739 0.3108 0.0636 Uiso 1.00 calc
H(11) H 0.7837 -0.3789 0.4095 0.0982 Uiso 1.00 calc
H(12) H 0.8029 -0.2042 0.5245 0.1269 Uiso 1.00 calc
H(13) H 0.8835 0.1262 0.5501 0.1168 Uiso 1.00 calc
H(14) H 0.9359 0.3176 0.4574 0.1223 Uiso 1.00 calc
H(15) H 0.9181 0.1430 0.3424 0.1026 Uiso 1.00 calc
H(16) H 0.8402 -0.2607 0.0922 0.0748 Uiso 1.00 calc
H(17) H 0.9641 -0.2539 0.0507 0.0723 Uiso 1.00 calc
H(18) H 1.0533 0.0562 0.0810 0.0634 Uiso 1.00 calc
H(19) H 1.0224 0.3561 0.1583 0.0723 Uiso 1.00 calc
H(20) H 0.8981 0.3543 0.1982 0.0647 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(4) S(1) C(11) 100.8(1) yes
C(1) O(1) C(2) 113.2(3) yes
O(1) C(2) C(3) 112.5(3) yes
C(2) C(3) C(4) 122.0(2) yes
C(2) C(3) C(17) 115.2(2) yes
C(4) C(3) C(17) 122.8(3) yes
S(1) C(4) C(3) 120.7(2) yes
S(1) C(4) C(5) 114.4(2) yes
C(3) C(4) C(5) 124.8(3) yes
C(4) C(5) C(6) 120.4(2) yes
C(4) C(5) C(10) 120.9(3) yes
C(6) C(5) C(10) 118.7(2) yes
C(5) C(6) C(7) 121.0(3) yes
C(6) C(7) C(8) 119.4(3) yes
C(7) C(8) C(9) 120.3(3) yes
C(8) C(9) C(10) 120.2(3) yes
C(5) C(10) C(9) 120.3(3) yes
S(1) C(11) C(12) 121.7(3) yes
S(1) C(11) C(16) 119.6(3) yes
C(12) C(11) C(16) 118.7(3) yes
C(11) C(12) C(13) 120.5(4) yes
C(12) C(13) C(14) 120.8(4) yes
C(13) C(14) C(15) 119.5(4) yes
C(14) C(15) C(16) 119.8(4) yes
C(11) C(16) C(15) 120.8(3) yes
C(3) C(17) C(18) 121.9(3) yes
C(3) C(17) C(22) 119.4(2) yes
C(18) C(17) C(22) 118.6(2) yes
C(17) C(18) C(19) 120.3(3) yes
C(18) C(19) C(20) 120.8(3) yes
C(19) C(20) C(21) 119.1(3) yes
C(20) C(21) C(22) 120.4(3) yes
C(17) C(22) C(21) 120.8(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(4) 1.784(3) yes
S(1) C(11) 1.770(3) yes
O(1) C(1) 1.411(4) yes
O(1) C(2) 1.419(4) yes
C(2) C(3) 1.507(4) yes
C(3) C(4) 1.331(4) yes
C(3) C(17) 1.503(4) yes
C(4) C(5) 1.502(4) yes
C(5) C(6) 1.384(4) yes
C(5) C(10) 1.374(4) yes
C(6) C(7) 1.383(4) yes
C(7) C(8) 1.375(4) yes
C(8) C(9) 1.363(4) yes
C(9) C(10) 1.393(4) yes
C(11) C(12) 1.367(4) yes
C(11) C(16) 1.366(4) yes
C(12) C(13) 1.373(5) yes
C(13) C(14) 1.348(6) yes
C(14) C(15) 1.372(6) yes
C(15) C(16) 1.376(5) yes
C(17) C(18) 1.376(4) yes
C(17) C(22) 1.378(4) yes
C(18) C(19) 1.383(4) yes
C(19) C(20) 1.370(4) yes
C(20) C(21) 1.368(4) yes
C(21) C(22) 1.381(4) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) C(18) 3.428(4) 2_655
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_publ_flag
S(1) C(4) C(3) C(2) 174.5(2) yes
S(1) C(4) C(3) C(17) -5.9(4) yes
S(1) C(4) C(5) C(6) -75.0(3) yes
S(1) C(4) C(5) C(10) 103.1(3) yes
S(1) C(11) C(12) C(13) 179.0(3) yes
S(1) C(11) C(16) C(15) -178.8(3) yes
O(1) C(2) C(3) C(4) -121.6(3) yes
O(1) C(2) C(3) C(17) 58.8(3) yes
C(1) O(1) C(2) C(3) 70.7(3) yes
C(2) C(3) C(4) C(5) -2.4(4) yes
C(2) C(3) C(17) C(18) -94.1(4) yes
C(2) C(3) C(17) C(22) 82.5(3) yes
C(3) C(4) S(1) C(11) 123.4(3) yes
C(3) C(4) C(5) C(6) 102.0(4) yes
C(3) C(4) C(5) C(10) -79.8(4) yes
C(3) C(17) C(18) C(19) 177.4(3) yes
C(3) C(17) C(22) C(21) -177.4(3) yes
C(4) S(1) C(11) C(12) 104.1(3) yes
C(4) S(1) C(11) C(16) -76.9(3) yes
C(4) C(3) C(17) C(18) 86.3(4) yes
C(4) C(3) C(17) C(22) -97.1(4) yes
C(4) C(5) C(6) C(7) 178.4(3) yes
C(4) C(5) C(10) C(9) -177.5(3) yes
C(5) C(4) S(1) C(11) -59.4(2) yes
C(5) C(4) C(3) C(17) 177.2(3) yes
C(5) C(6) C(7) C(8) -1.5(5) yes
C(5) C(10) C(9) C(8) -0.2(5) yes
C(6) C(5) C(10) C(9) 0.6(5) yes
C(6) C(7) C(8) C(9) 2.0(5) yes
C(7) C(6) C(5) C(10) 0.2(5) yes
C(7) C(8) C(9) C(10) -1.1(5) yes
C(11) C(12) C(13) C(14) -0.9(7) yes
C(11) C(16) C(15) C(14) 0.5(7) yes
C(12) C(11) C(16) C(15) 0.2(6) yes
C(12) C(13) C(14) C(15) 1.6(7) yes
C(13) C(12) C(11) C(16) 0.0(6) yes
C(13) C(14) C(15) C(16) -1.4(7) yes
C(17) C(18) C(19) C(20) -0.6(5) yes
C(17) C(22) C(21) C(20) 0.3(5) yes
C(18) C(17) C(22) C(21) -0.6(5) yes
C(18) C(19) C(20) C(21) 0.3(5) yes
C(19) C(18) C(17) C(22) 0.8(5) yes
C(19) C(20) C(21) C(22) -0.2(5) yes
C(19) C(20) C(21) C(22) -0.2(5) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101457722
