#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/80/4028032.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_4028032
loop_
_publ_author_name
'Debjit Das'
'Sanjay Pratihar'
'Sujit Roy'
_publ_section_title
;
 Heterobimetallic Pd-Sn Catalysis: Michael Addition Reaction with C-, N-,
 O-, and S-Nucleophiles and in Situ Diagnostics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2430
_journal_page_last               2442
_journal_paper_doi               10.1021/jo302643v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H14 O S'
_chemical_formula_weight         242.32
_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                 93.565(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6935(7)
_cell_length_b                   7.4544(9)
_cell_length_c                   29.487(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1249.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13761
_diffrn_reflns_theta_full        24.85
_diffrn_reflns_theta_max         24.85
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.4804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                1602
_reflns_number_total             2135
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo302643v_si_003.cif
_cod_data_source_block           rn140out
_cod_original_cell_volume        1249.0(3)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4028032
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
S1 S 0.43871(10) 0.79392(9) 0.182459(19) 0.0527(2) Uani 1 1 d .
C10 C 0.4909(3) 0.7782(3) 0.12435(7) 0.0383(5) Uani 1 1 d .
C1 C 0.9454(3) 0.7436(3) 0.33817(7) 0.0389(5) Uani 1 1 d .
C8 C 0.7033(4) 0.7658(3) 0.26122(7) 0.0432(5) Uani 1 1 d .
H8A H 0.6745 0.8929 0.2652 0.052 Uiso 1 1 calc R
H8B H 0.5731 0.7006 0.2731 0.052 Uiso 1 1 calc R
C4 C 1.1402(3) 0.6757(3) 0.36312(7) 0.0458(5) Uani 1 1 d .
H4 H 1.2577 0.6176 0.3482 0.055 Uiso 1 1 calc R
C2 C 0.7732(4) 0.8311(3) 0.36121(7) 0.0450(5) Uani 1 1 d .
H2 H 0.6410 0.8770 0.3451 0.054 Uiso 1 1 calc R
C11 C 0.6847(4) 0.6971(3) 0.10665(7) 0.0460(5) Uani 1 1 d .
H11 H 0.8018 0.6466 0.1260 0.055 Uiso 1 1 calc R
C3 C 0.9284(4) 0.7146(3) 0.28779(7) 0.0463(5) Uani 1 1 d .
C5 C 1.1619(4) 0.6930(3) 0.40953(8) 0.0526(6) Uani 1 1 d .
H5 H 1.2923 0.6455 0.4259 0.063 Uiso 1 1 calc R
C6 C 0.9900(4) 0.7811(3) 0.43185(7) 0.0518(6) Uani 1 1 d .
H6 H 1.0050 0.7937 0.4633 0.062 Uiso 1 1 calc R
C9 C 0.7132(4) 0.7253(3) 0.21106(7) 0.0489(6) Uani 1 1 d .
H9A H 0.7377 0.5979 0.2066 0.059 Uiso 1 1 calc R
H9B H 0.8429 0.7898 0.1988 0.059 Uiso 1 1 calc R
C12 C 0.7028(4) 0.6917(3) 0.06026(8) 0.0532(6) Uani 1 1 d .
H12 H 0.8336 0.6380 0.0486 0.064 Uiso 1 1 calc R
C7 C 0.7966(4) 0.8505(3) 0.40772(7) 0.0510(6) Uani 1 1 d .
H7 H 0.6814 0.9105 0.4228 0.061 Uiso 1 1 calc R
O1 O 1.0869(3) 0.6504(3) 0.26930(6) 0.0800(6) Uani 1 1 d .
C14 C 0.3395(4) 0.8445(3) 0.04843(8) 0.0538(6) Uani 1 1 d .
H14 H 0.2226 0.8943 0.0289 0.065 Uiso 1 1 calc R
C15 C 0.3190(3) 0.8519(3) 0.09451(7) 0.0460(5) Uani 1 1 d .
H15 H 0.1884 0.9069 0.1059 0.055 Uiso 1 1 calc R
C13 C 0.5311(4) 0.7643(3) 0.03090(7) 0.0544(6) Uani 1 1 d .
H13 H 0.5446 0.7590 -0.0003 0.065 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
C10 S1 C9 104.04(10)
C11 C10 C15 118.65(19)
C11 C10 S1 125.51(16)
C15 C10 S1 115.83(16)
C4 C1 C2 118.49(19)
C4 C1 C3 118.24(18)
C2 C1 C3 123.25(18)
C3 C8 C9 112.01(17)
C5 C4 C1 120.9(2)
C7 C2 C1 120.5(2)
C12 C11 C10 119.8(2)
O1 C3 C1 120.71(19)
O1 C3 C8 120.7(2)
C1 C3 C8 118.60(18)
C4 C5 C6 119.9(2)
C7 C6 C5 120.1(2)
C8 C9 S1 108.45(15)
C13 C12 C11 121.2(2)
C6 C7 C2 120.1(2)
C15 C14 C13 120.6(2)
C14 C15 C10 120.8(2)
C14 C13 C12 119.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.761(2)
S1 C9 1.803(2)
C10 C11 1.388(3)
C10 C15 1.388(3)
C1 C4 1.388(3)
C1 C2 1.390(3)
C1 C3 1.498(3)
C8 C3 1.509(3)
C8 C9 1.514(3)
C4 C5 1.373(3)
C2 C7 1.377(3)
C11 C12 1.379(3)
C3 O1 1.184(2)
C5 C6 1.379(3)
C6 C7 1.374(3)
C12 C13 1.376(3)
C14 C15 1.372(3)
C14 C13 1.373(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12373749
