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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/1/50/46/1504694.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_1504694
loop_
_publ_author_name
'Minami, Yasunori'
'Kuniyasu, Hitoshi'
'Kambe, Nobuaki'
_publ_section_title
;
 One-pot syntheses of 2,3-dihydrothiopyran-4-one derivatives by
 Pd/Cu-catalyzed reactions of alpha,beta-unsaturated thioesters with
 propargyl alcohols.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2469
_journal_page_last               2472
_journal_paper_doi               10.1021/ol800754w
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C15 H17 N O4 S '
_chemical_formula_sum            'C15 H17 N O4 S'
_chemical_formula_weight         307.36
_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                 122.578(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1771(4)
_cell_length_b                   14.9463(5)
_cell_length_c                   11.0961(6)
_cell_measurement_reflns_used    13422
_cell_measurement_temperature    274.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     1562.01(12)
_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 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_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  0.035
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14595
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.843
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2490
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.0805
_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         0.1844
_reflns_number_gt                2490
_reflns_number_total             3581
_reflns_threshold_expression     F²>3.0σ(F²)
_cod_data_source_file            ol800754w-file003.cif
_cod_data_source_block           1620
_cod_original_cell_volume        1562.0(1)
_cod_original_formula_sum        'C15 H17 N O4 S '
_cod_database_code               1504694
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 -0.94978(9) -0.34915(6) 0.4921(1) 0.0634(3) Uani 1.00 d
O(1) O -0.8367(2) -0.2220(2) 0.7219(2) 0.0554(6) Uani 1.00 d
O(5) O -0.7563(4) -0.4501(2) 1.2282(3) 0.0946(10) Uani 1.00 d
O(6) O -0.9841(3) -0.4336(2) 1.1109(3) 0.085(1) Uani 1.00 d
O(7) O -1.4040(2) -0.2926(2) 0.1997(3) 0.0881(9) Uani 1.00 d
N(2) N -0.8683(4) -0.4214(2) 1.1261(3) 0.0662(9) Uani 1.00 d
C(1) C -1.0462(3) -0.2563(2) 0.4863(3) 0.0445(7) Uani 1.00 d
C(2) C -0.9553(3) -0.1830(2) 0.5927(3) 0.0482(8) Uani 1.00 d
C(4) C -0.7292(3) -0.2913(2) 0.9428(4) 0.0574(9) Uani 1.00 d
C(5) C -0.9835(3) -0.3034(2) 0.7872(3) 0.0549(9) Uani 1.00 d
C(6) C -0.8827(4) -0.1314(2) 0.5304(4) 0.0584(9) Uani 1.00 d
C(7) C -0.8632(3) -0.3709(2) 1.0169(4) 0.0541(9) Uani 1.00 d
C(9) C -0.9870(3) -0.3529(2) 0.8903(4) 0.0539(9) Uani 1.00 d
C(10) C -0.7330(3) -0.3413(2) 1.0442(3) 0.0586(9) Uani 1.00 d
C(11) C -1.0368(4) -0.1181(2) 0.6301(4) 0.064(1) Uani 1.00 d
C(12) C -1.2786(4) -0.3082(3) 0.2778(4) 0.067(1) Uani 1.00 d
C(14) C -1.2153(6) -0.3913(5) 0.2637(9) 0.184(3) Uani 1.00 d
C(15) C -1.0813(6) -0.4058(4) 0.3373(6) 0.117(2) Uani 1.00 d
C(16) C -0.8545(3) -0.2716(2) 0.8144(3) 0.0495(8) Uani 1.00 d
C(17) C -1.1858(3) -0.2460(2) 0.3909(3) 0.0496(8) Uani 1.00 d
C(18) C -1.3161(7) -0.4468(5) 0.1341(8) 0.158(3) Uani 1.00 d
H(1) H -0.6390 -0.2699 0.9611 0.0693 Uiso 1.00 calc
H(2) H -1.0693 -0.2911 0.6976 0.0646 Uiso 1.00 calc
H(3) H -1.0761 -0.3749 0.8718 0.0655 Uiso 1.00 calc
H(4) H -0.6477 -0.3558 1.1333 0.0694 Uiso 1.00 calc
H(5) H -0.8264 -0.1709 0.5119 0.0697 Uiso 1.00 calc
H(6) H -0.9502 -0.1024 0.4431 0.0697 Uiso 1.00 calc
H(7) H -0.8197 -0.0864 0.5964 0.0697 Uiso 1.00 calc
H(8) H -0.9750 -0.0712 0.6896 0.0765 Uiso 1.00 calc
H(9) H -1.1139 -0.0922 0.5446 0.0765 Uiso 1.00 calc
H(10) H -1.0726 -0.1486 0.6790 0.0765 Uiso 1.00 calc
H(11) H -1.2277 -0.1911 0.3977 0.0593 Uiso 1.00 calc
H(12) H -1.4159 -0.4359 0.1007 0.1906 Uiso 1.00 calc
H(13) H -1.3030 -0.4273 0.0608 0.1906 Uiso 1.00 calc
H(14) H -1.3024 -0.5102 0.1453 0.1906 Uiso 1.00 calc
H(15) H -1.2319 -0.4307 0.3405 0.2450 Uiso 1.00 calc
H(16) H -1.0615 -0.3883 0.2627 0.1485 Uiso 1.00 calc
H(17) H -1.0583 -0.4678 0.3543 0.1485 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)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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(1) S(1) C(15) 99.9(2) yes
C(2) O(1) C(16) 122.4(2) yes
O(5) N(2) O(6) 123.4(3) yes
O(5) N(2) C(7) 118.2(3) yes
O(6) N(2) C(7) 118.4(3) yes
S(1) C(1) C(2) 113.8(2) yes
S(1) C(1) C(17) 123.7(2) yes
C(2) C(1) C(17) 122.3(3) yes
O(1) C(2) C(1) 110.4(2) yes
O(1) C(2) C(6) 103.0(2) yes
O(1) C(2) C(11) 110.3(3) yes
C(1) C(2) C(6) 107.9(3) yes
C(1) C(2) C(11) 114.7(2) yes
C(6) C(2) C(11) 110.0(3) yes
C(10) C(4) C(16) 119.9(3) yes
C(9) C(5) C(16) 119.5(3) yes
N(2) C(7) C(9) 119.1(3) yes
N(2) C(7) C(10) 119.3(3) yes
C(9) C(7) C(10) 121.6(3) yes
C(5) C(9) C(7) 119.5(3) yes
C(4) C(10) C(7) 119.1(3) yes
O(7) C(12) C(14) 121.5(4) yes
O(7) C(12) C(17) 120.5(4) yes
C(14) C(12) C(17) 117.9(3) yes
C(12) C(14) C(15) 122.5(4) yes
C(12) C(14) C(18) 114.1(5) yes
C(15) C(14) C(18) 122.0(5) yes
S(1) C(15) C(14) 128.0(4) yes
O(1) C(16) C(4) 114.3(3) yes
O(1) C(16) C(5) 125.2(3) yes
C(4) C(16) C(5) 120.4(3) yes
C(1) C(17) C(12) 126.5(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(1) 1.737(3) yes
S(1) C(15) 1.763(5) yes
O(1) C(2) 1.451(4) yes
O(1) C(16) 1.365(4) yes
O(5) N(2) 1.227(4) yes
O(6) N(2) 1.226(4) yes
O(7) C(12) 1.209(4) yes
N(2) C(7) 1.454(4) yes
C(1) C(2) 1.527(4) yes
C(1) C(17) 1.342(4) yes
C(2) C(6) 1.528(4) yes
C(2) C(11) 1.533(5) yes
C(4) C(10) 1.371(5) yes
C(4) C(16) 1.388(4) yes
C(5) C(9) 1.381(4) yes
C(5) C(16) 1.388(4) yes
C(7) C(9) 1.366(4) yes
C(7) C(10) 1.389(4) yes
C(12) C(14) 1.478(7) yes
C(12) C(17) 1.454(5) yes
C(14) C(15) 1.281(7) yes
C(14) C(18) 1.510(7) 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(9) 3.487(4) 4_545
O(5) C(17) 3.306(4) 4_546
O(5) C(6) 3.529(4) 2_347
O(6) O(6) 3.029(6) 3_347
O(6) N(2) 3.108(4) 3_347
O(6) C(9) 3.205(4) 3_347
O(6) C(15) 3.257(7) 1_556
O(6) C(7) 3.294(4) 3_347
O(6) O(7) 3.501(4) 4_546
O(7) C(4) 3.191(4) 1_454
O(7) C(10) 3.193(4) 1_454
O(7) C(7) 3.361(5) 4_444
O(7) N(2) 3.378(4) 4_444
N(2) C(17) 3.549(4) 4_546
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(1) C(2) O(1) -33.3(3) yes
S(1) C(1) C(2) C(6) 78.5(3) yes
S(1) C(1) C(2) C(11) -158.6(2) yes
S(1) C(1) C(17) C(12) -0.5(5) yes
S(1) C(15) C(14) C(12) 15(1) yes
S(1) C(15) C(14) C(18) -178.8(6) yes
O(1) C(2) C(1) C(17) 151.3(3) yes
O(1) C(16) C(4) C(10) -179.5(3) yes
O(1) C(16) C(5) C(9) 180.0(3) yes
O(5) N(2) C(7) C(9) 167.8(3) yes
O(5) N(2) C(7) C(10) -12.9(5) yes
O(6) N(2) C(7) C(9) -11.7(5) yes
O(6) N(2) C(7) C(10) 167.6(3) yes
O(7) C(12) C(14) C(15) 174.1(8) yes
O(7) C(12) C(14) C(18) 7(1) yes
O(7) C(12) C(17) C(1) 178.4(4) yes
N(2) C(7) C(9) C(5) 178.6(3) yes
N(2) C(7) C(10) C(4) -177.9(3) yes
C(1) S(1) C(15) C(14) -13.8(9) yes
C(1) C(2) O(1) C(16) -67.7(3) yes
C(1) C(17) C(12) C(14) -0.5(7) yes
C(2) O(1) C(16) C(4) -170.1(3) yes
C(2) O(1) C(16) C(5) 11.5(5) yes
C(2) C(1) S(1) C(15) -169.4(3) yes
C(2) C(1) C(17) C(12) 174.4(3) yes
C(4) C(10) C(7) C(9) 1.4(5) yes
C(4) C(16) C(5) C(9) 1.7(5) yes
C(5) C(9) C(7) C(10) -0.7(5) yes
C(5) C(16) C(4) C(10) -1.0(5) yes
C(6) C(2) O(1) C(16) 177.4(3) yes
C(6) C(2) C(1) C(17) -96.9(3) yes
C(7) C(9) C(5) C(16) -0.8(5) yes
C(7) C(10) C(4) C(16) -0.5(5) yes
C(11) C(2) O(1) C(16) 60.1(4) yes
C(11) C(2) C(1) C(17) 26.0(4) yes
C(15) S(1) C(1) C(17) 5.9(4) yes
C(15) C(14) C(12) C(17) -7(1) yes
C(17) C(12) C(14) C(18) -173.8(6) yes
C(17) C(12) C(14) C(18) -173.8(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102078947
