#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/88/1508885.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_1508885
loop_
_publ_author_name
'Xu, Xiao-Bo'
'Liu, Jian'
'Zhang, Jian-Jian'
'Wang, Ya-Wen'
'Peng, Yu'
_publ_section_title
;
 Nickel-mediated inter- and intramolecular C-s coupling of thiols and
 thioacetates with aryl iodides at room temperature.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              550
_journal_page_last               553
_journal_paper_doi               10.1021/ol303366u
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C13 H13 N O2 S'
_chemical_formula_weight         247.30
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.132(5)
_cell_length_b                   12.907(7)
_cell_length_c                   23.129(13)
_cell_measurement_reflns_used    1961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      3.06
_cell_volume                     2428(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9625
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9555
_exptl_absorpt_correction_T_min  0.9390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0467
_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)+(0.0572P)²+0.9716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                1609
_reflns_number_total             2251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303366u_si_004.cif
_cod_data_source_block           pbca
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1508885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C -0.1140(4) 0.6908(2) 0.19907(11) 0.0505(7) Uani 1 1 d .
C2 C -0.1678(4) 0.7926(3) 0.20121(13) 0.0661(9) Uani 1 1 d .
H2 H -0.2128 0.8204 0.2348 0.079 Uiso 1 1 calc R
C3 C -0.1523(4) 0.8504(2) 0.15208(14) 0.0669(9) Uani 1 1 d .
H3 H -0.1884 0.9187 0.1528 0.080 Uiso 1 1 calc R
C4 C -0.0851(4) 0.8122(2) 0.10108(13) 0.0561(8) Uani 1 1 d .
H4 H -0.0750 0.8546 0.0688 0.067 Uiso 1 1 calc R
C5 C -0.0336(3) 0.7103(2) 0.09906(10) 0.0417(6) Uani 1 1 d .
C6 C -0.0493(3) 0.64917(19) 0.14785(10) 0.0401(6) Uani 1 1 d .
C7 C -0.0079(3) 0.5441(2) 0.15751(10) 0.0413(6) Uani 1 1 d .
C8 C -0.0446(4) 0.5248(2) 0.21391(11) 0.0555(8) Uani 1 1 d .
H8 H -0.0282 0.4620 0.2327 0.067 Uiso 1 1 calc R
C9 C 0.0567(3) 0.4768(2) 0.10991(11) 0.0461(6) Uani 1 1 d .
H9 H -0.0394 0.4505 0.0890 0.055 Uiso 1 1 calc R
C10 C 0.1558(3) 0.5416(2) 0.06659(10) 0.0432(6) Uani 1 1 d .
H10 H 0.1816 0.4956 0.0341 0.052 Uiso 1 1 calc R
C11 C 0.3183(3) 0.57935(19) 0.08984(10) 0.0414(6) Uani 1 1 d .
C12 C 0.5917(4) 0.6195(3) 0.06613(16) 0.0707(9) Uani 1 1 d .
H12A H 0.5795 0.6874 0.0825 0.106 Uiso 1 1 calc R
H12B H 0.6620 0.6232 0.0329 0.106 Uiso 1 1 calc R
H12C H 0.6395 0.5739 0.0943 0.106 Uiso 1 1 calc R
C13 C 0.1516(4) 0.3825(2) 0.13087(15) 0.0700(9) Uani 1 1 d .
H13A H 0.2426 0.4045 0.1543 0.105 Uiso 1 1 calc R
H13B H 0.1918 0.3442 0.0982 0.105 Uiso 1 1 calc R
H13C H 0.0802 0.3391 0.1534 0.105 Uiso 1 1 calc R
N1 N -0.1093(4) 0.6124(2) 0.23873(11) 0.0644(8) Uani 1 1 d .
O1 O 0.3430(3) 0.60694(17) 0.13828(8) 0.0668(6) Uani 1 1 d .
O2 O 0.4320(2) 0.58039(16) 0.04912(8) 0.0581(5) Uani 1 1 d .
S1 S 0.04686(9) 0.65255(6) 0.03600(3) 0.0496(2) Uani 1 1 d .
H1N H -0.141(4) 0.616(2) 0.2718(14) 0.073(11) Uiso 1 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 0.0033 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'
N N 0.0061 0.0033 '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
N1 C1 C2 133.4(3)
N1 C1 C6 105.8(3)
C2 C1 C6 120.8(3)
C3 C2 C1 117.3(3)
C3 C2 H2 121.3
C1 C2 H2 121.3
C2 C3 C4 123.3(3)
C2 C3 H3 118.4
C4 C3 H3 118.4
C5 C4 C3 119.0(3)
C5 C4 H4 120.5
C3 C4 H4 120.5
C4 C5 C6 119.2(2)
C4 C5 S1 122.9(2)
C6 C5 S1 117.9(2)
C5 C6 C1 120.3(2)
C5 C6 C7 130.8(2)
C1 C6 C7 108.8(2)
C8 C7 C6 105.9(2)
C8 C7 C9 132.5(2)
C6 C7 C9 121.6(2)
C7 C8 N1 109.5(3)
C7 C8 H8 125.2
N1 C8 H8 125.2
C7 C9 C13 114.1(2)
C7 C9 C10 110.4(2)
C13 C9 C10 112.2(2)
C7 C9 H9 106.5
C13 C9 H9 106.5
C10 C9 H9 106.5
C11 C10 C9 113.8(2)
C11 C10 S1 108.06(18)
C9 C10 S1 115.18(18)
C11 C10 H10 106.4
C9 C10 H10 106.4
S1 C10 H10 106.4
O1 C11 O2 123.3(2)
O1 C11 C10 125.4(2)
O2 C11 C10 111.3(2)
O2 C12 H12A 109.5
O2 C12 H12B 109.5
H12A C12 H12B 109.5
O2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C9 C13 H13A 109.5
C9 C13 H13B 109.5
H13A C13 H13B 109.5
C9 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C1 N1 C8 109.9(2)
C1 N1 H1N 125(2)
C8 N1 H1N 125(2)
C11 O2 C12 116.0(2)
C5 S1 C10 101.02(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.366(4)
C1 C2 1.386(4)
C1 C6 1.403(3)
C2 C3 1.365(4)
C2 H2 0.9300
C3 C4 1.390(4)
C3 H3 0.9300
C4 C5 1.380(4)
C4 H4 0.9300
C5 C6 1.383(3)
C5 S1 1.764(3)
C6 C7 1.415(4)
C7 C8 1.361(3)
C7 C9 1.498(3)
C8 N1 1.372(4)
C8 H8 0.9300
C9 C13 1.521(4)
C9 C10 1.534(4)
C9 H9 0.9800
C10 C11 1.507(4)
C10 S1 1.827(3)
C10 H10 0.9800
C11 O1 1.193(3)
C11 O2 1.320(3)
C12 O2 1.448(4)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
N1 H1N 0.81(3)
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
N1 C1 C2 C3 179.6(3)
C6 C1 C2 C3 -1.2(5)
C1 C2 C3 C4 -0.4(5)
C2 C3 C4 C5 1.2(5)
C3 C4 C5 C6 -0.3(4)
C3 C4 C5 S1 177.8(2)
C4 C5 C6 C1 -1.2(4)
S1 C5 C6 C1 -179.4(2)
C4 C5 C6 C7 179.7(3)
S1 C5 C6 C7 1.5(4)
N1 C1 C6 C5 -178.6(2)
C2 C1 C6 C5 2.0(4)
N1 C1 C6 C7 0.7(3)
C2 C1 C6 C7 -178.7(3)
C5 C6 C7 C8 178.0(3)
C1 C6 C7 C8 -1.2(3)
C5 C6 C7 C9 -3.9(4)
C1 C6 C7 C9 177.0(2)
C6 C7 C8 N1 1.2(3)
C9 C7 C8 N1 -176.6(3)
C8 C7 C9 C13 -23.7(4)
C6 C7 C9 C13 158.7(3)
C8 C7 C9 C10 -151.2(3)
C6 C7 C9 C10 31.3(3)
C7 C9 C10 C11 70.7(3)
C13 C9 C10 C11 -57.7(3)
C7 C9 C10 S1 -54.9(3)
C13 C9 C10 S1 176.68(19)
C9 C10 C11 O1 -36.9(4)
S1 C10 C11 O1 92.4(3)
C9 C10 C11 O2 144.4(2)
S1 C10 C11 O2 -86.3(2)
C2 C1 N1 C8 179.3(3)
C6 C1 N1 C8 0.0(3)
C7 C8 N1 C1 -0.8(4)
O1 C11 O2 C12 -1.2(4)
C10 C11 O2 C12 177.5(2)
C4 C5 S1 C10 160.5(2)
C6 C5 S1 C10 -21.4(2)
C11 C10 S1 C5 -79.78(18)
C9 C10 S1 C5 48.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 4425218 ChemSpider
2 11118391 PubChem
