#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/11/1561173.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_1561173
loop_
_publ_author_name
'Shankar, Majji'
'Saha, Arijit'
'Sau, Somratan'
'Ghosh, Arghadip'
'Gandon, Vincent'
'Sahoo, Akhila Kumar'
_publ_section_title
;
 Harnessing Sulfur and Nitrogen in the Cobalt (III)-Catalyzed
 Unsymmetrical Double Annulation of Thioamides: Probing the Origin of
 Chemo- and Regioselectivity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC00765C
_journal_year                    2021
_chemical_formula_sum            'C36 H25 N O S'
_chemical_formula_weight         519.63
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_update_record
;
2020-11-23 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5770(4)
_cell_length_b                   9.7186(3)
_cell_length_c                   21.3735(8)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.60
_cell_volume                     2748.41(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full ACTA50
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18167
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1009P)²+0.9145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2153
_reflns_number_gt                3931
_reflns_number_total             6620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1sc00765c3.cif
_cod_data_source_block           aks
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1561173
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.55798(5) 1.09457(7) 0.86919(5) 0.0695(3) Uani 1 1 d . . .
N1 N 0.40767(13) 1.0117(2) 0.90942(11) 0.0482(5) Uani 1 1 d . . .
C2 C 0.50637(16) 0.8201(2) 0.87914(11) 0.0424(5) Uani 1 1 d . . .
C3 C 0.35242(16) 0.7739(2) 0.91905(12) 0.0461(5) Uani 1 1 d . . .
C4 C 0.59073(16) 0.7767(2) 0.85397(12) 0.0464(5) Uani 1 1 d . . .
C5 C 0.65729(17) 0.8752(2) 0.83127(12) 0.0468(6) Uani 1 1 d . . .
C6 C 0.48439(17) 0.9613(2) 0.88657(12) 0.0473(6) Uani 1 1 d . . .
O1 O 0.41458(15) 0.49807(19) 0.92939(12) 0.0776(7) Uani 1 1 d . . .
C7 C 0.44055(16) 0.7246(2) 0.89908(12) 0.0451(5) Uani 1 1 d . . .
C8 C 0.33872(16) 0.9140(2) 0.92256(12) 0.0457(5) Uani 1 1 d . . .
C9 C 0.73528(18) 0.8184(2) 0.79813(13) 0.0492(6) Uani 1 1 d . . .
C10 C 0.24967(17) 0.9810(2) 0.93999(13) 0.0483(6) Uani 1 1 d . . .
C11 C 0.27270(18) 0.6795(3) 0.93354(15) 0.0562(7) Uani 1 1 d . . .
C12 C 0.46850(19) 0.5833(2) 0.90002(14) 0.0536(6) Uani 1 1 d . . .
C13 C 0.71302(19) 1.1210(3) 0.81639(14) 0.0541(6) Uani 1 1 d . . .
C14 C 0.64821(17) 1.0126(3) 0.83607(13) 0.0505(6) Uani 1 1 d . . .
C15 C 0.5485(2) 0.5415(3) 0.87557(15) 0.0598(7) Uani 1 1 d . . .
H15 H 0.5639 0.4483 0.8749 0.072 Uiso 1 1 calc R . .
C16 C 0.2667(2) 1.0892(3) 0.98342(14) 0.0571(7) Uani 1 1 d . . .
H16 H 0.3326 1.1137 1.0030 0.069 Uiso 1 1 calc R . .
C17 C 0.60680(19) 0.6366(3) 0.85173(14) 0.0578(7) Uani 1 1 d . . .
H17 H 0.6587 0.6049 0.8335 0.069 Uiso 1 1 calc R . .
C18 C 0.15183(19) 0.9484(3) 0.91096(16) 0.0676(8) Uani 1 1 d . . .
H18 H 0.1388 0.8784 0.8806 0.081 Uiso 1 1 calc R . .
C19 C 0.2135(2) 0.6013(3) 0.8845(2) 0.0774(9) Uani 1 1 d . . .
H19 H 0.2259 0.6032 0.8435 0.093 Uiso 1 1 calc R . .
C20 C 0.8318(2) 0.7890(4) 0.83059(16) 0.0757(9) Uani 1 1 d . . .
H20 H 0.8507 0.8051 0.8745 0.091 Uiso 1 1 calc R . .
C21 C 0.8742(3) 0.7100(4) 0.7347(2) 0.0893(11) Uani 1 1 d . . .
H21 H 0.9209 0.6743 0.7131 0.107 Uiso 1 1 calc R . .
C22 C 0.1873(3) 1.1604(3) 0.99771(16) 0.0736(9) Uani 1 1 d . . .
H22 H 0.1995 1.2331 1.0267 0.088 Uiso 1 1 calc R . .
C1 C 0.4385(3) 0.3583(3) 0.93578(17) 0.0731(9) Uani 1 1 d . . .
H1A H 0.4269 0.3166 0.8940 0.110 Uiso 1 1 calc R . .
H1B H 0.3967 0.3144 0.9607 0.110 Uiso 1 1 calc R . .
H1C H 0.5083 0.3477 0.9570 0.110 Uiso 1 1 calc R . .
C23 C 0.0725(2) 1.0193(4) 0.9266(2) 0.0846(11) Uani 1 1 d . . .
H23 H 0.0063 0.9944 0.9077 0.102 Uiso 1 1 calc R . .
C24 C 0.0898(3) 1.1243(4) 0.9692(2) 0.0871(11) Uani 1 1 d . . .
H24 H 0.0359 1.1719 0.9791 0.105 Uiso 1 1 calc R . .
C25 C 0.2525(2) 0.6760(3) 0.99386(18) 0.0752(9) Uani 1 1 d . . .
H25 H 0.2911 0.7281 1.0270 0.090 Uiso 1 1 calc R . .
C26 C 0.6702(3) 1.2175(4) 0.77038(16) 0.0782(9) Uani 1 1 d . . .
H26 H 0.6023 1.2102 0.7498 0.094 Uiso 1 1 calc R . .
C27 C 0.7278(3) 1.3249(4) 0.75485(18) 0.0921(11) Uani 1 1 d . . .
H27 H 0.6986 1.3892 0.7240 0.111 Uiso 1 1 calc R . .
C28 C 0.7096(3) 0.7907(4) 0.73401(16) 0.0882(11) Uani 1 1 d . . .
H28 H 0.6442 0.8088 0.7111 0.106 Uiso 1 1 calc R . .
C29 C 0.1362(3) 0.5210(4) 0.8973(3) 0.1066(15) Uani 1 1 d . . .
H29 H 0.0970 0.4686 0.8645 0.128 Uiso 1 1 calc R . .
C30 C 0.8275(3) 1.3361(4) 0.7850(2) 0.0893(11) Uani 1 1 d . . .
H30 H 0.8666 1.4064 0.7737 0.107 Uiso 1 1 calc R . .
C31 C 0.9022(2) 0.7355(4) 0.7987(2) 0.0917(11) Uani 1 1 d . . .
H31 H 0.9679 0.7173 0.8211 0.110 Uiso 1 1 calc R . .
C32 C 0.8692(2) 1.2452(4) 0.8311(2) 0.0985(13) Uani 1 1 d . . .
H32 H 0.9368 1.2541 0.8520 0.118 Uiso 1 1 calc R . .
C33 C 0.1743(3) 0.5941(4) 1.0051(3) 0.1069(15) Uani 1 1 d . . .
H33 H 0.1607 0.5911 1.0458 0.128 Uiso 1 1 calc R . .
C34 C 0.1168(3) 0.5174(4) 0.9559(4) 0.1208(19) Uani 1 1 d . . .
H34 H 0.0644 0.4630 0.9636 0.145 Uiso 1 1 calc R . .
C35 C 0.8119(2) 1.1387(4) 0.8476(2) 0.0868(11) Uani 1 1 d . . .
H35 H 0.8410 1.0785 0.8803 0.104 Uiso 1 1 calc R . .
C36 C 0.7788(4) 0.7364(5) 0.7023(2) 0.1030(13) Uani 1 1 d . . .
H36 H 0.7596 0.7180 0.6586 0.124 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C14 103.78(12) . . ?
C6 N1 C8 115.70(19) . . ?
C7 C2 C6 115.9(2) . . ?
C7 C2 C4 122.0(2) . . ?
C6 C2 C4 122.1(2) . . ?
C8 C3 C7 118.5(2) . . ?
C8 C3 C11 118.6(2) . . ?
C7 C3 C11 122.8(2) . . ?
C17 C4 C2 116.7(2) . . ?
C17 C4 C5 121.1(2) . . ?
C2 C4 C5 122.3(2) . . ?
C14 C5 C4 123.1(2) . . ?
C14 C5 C9 119.1(2) . . ?
C4 C5 C9 117.7(2) . . ?
N1 C6 C2 126.5(2) . . ?
N1 C6 S1 109.82(17) . . ?
C2 C6 S1 123.67(18) . . ?
C12 O1 C1 120.3(2) . . ?
C2 C7 C12 116.8(2) . . ?
C2 C7 C3 119.5(2) . . ?
C12 C7 C3 123.6(2) . . ?
C3 C8 N1 123.5(2) . . ?
C3 C8 C10 124.8(2) . . ?
N1 C8 C10 111.64(19) . . ?
C28 C9 C20 117.9(3) . . ?
C28 C9 C5 119.8(2) . . ?
C20 C9 C5 122.2(2) . . ?
C18 C10 C16 118.5(2) . . ?
C18 C10 C8 122.9(2) . . ?
C16 C10 C8 118.4(2) . . ?
C25 C11 C19 119.2(3) . . ?
C25 C11 C3 120.8(3) . . ?
C19 C11 C3 119.9(3) . . ?
O1 C12 C15 123.7(2) . . ?
O1 C12 C7 115.3(2) . . ?
C15 C12 C7 120.8(2) . . ?
C35 C13 C26 118.0(3) . . ?
C35 C13 C14 121.8(3) . . ?
C26 C13 C14 119.8(2) . . ?
C5 C14 C13 127.5(2) . . ?
C5 C14 S1 124.7(2) . . ?
C13 C14 S1 107.75(17) . . ?
C12 C15 C17 120.7(2) . . ?
C22 C16 C10 120.6(3) . . ?
C4 C17 C15 122.5(2) . . ?
C10 C18 C23 120.3(3) . . ?
C29 C19 C11 119.7(4) . . ?
C9 C20 C31 120.9(3) . . ?
C36 C21 C31 120.0(3) . . ?
C16 C22 C24 120.0(3) . . ?
C24 C23 C18 120.8(3) . . ?
C23 C24 C22 119.8(3) . . ?
C11 C25 C33 119.7(4) . . ?
C13 C26 C27 120.5(3) . . ?
C30 C27 C26 119.9(3) . . ?
C9 C28 C36 121.4(3) . . ?
C34 C29 C19 121.1(4) . . ?
C32 C30 C27 120.1(3) . . ?
C21 C31 C20 119.6(3) . . ?
C30 C32 C35 120.4(3) . . ?
C34 C33 C25 120.2(4) . . ?
C29 C34 C33 120.2(4) . . ?
C13 C35 C32 121.0(3) . . ?
C21 C36 C28 120.1(4) . . ?
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 C6 1.727(2) . ?
S1 C14 1.739(2) . ?
N1 C6 1.338(3) . ?
N1 C8 1.405(3) . ?
C2 C7 1.418(3) . ?
C2 C6 1.421(3) . ?
C2 C4 1.434(3) . ?
C3 C8 1.378(3) . ?
C3 C7 1.440(3) . ?
C3 C11 1.503(3) . ?
C4 C17 1.382(3) . ?
C4 C5 1.472(3) . ?
C5 C14 1.347(3) . ?
C5 C9 1.505(3) . ?
O1 C12 1.350(3) . ?
O1 C1 1.396(3) . ?
C7 C12 1.424(3) . ?
C8 C10 1.492(3) . ?
C9 C28 1.363(4) . ?
C9 C20 1.369(4) . ?
C10 C18 1.371(4) . ?
C10 C16 1.387(4) . ?
C11 C25 1.377(4) . ?
C11 C19 1.394(4) . ?
C12 C15 1.369(4) . ?
C13 C35 1.369(4) . ?
C13 C26 1.389(4) . ?
C13 C14 1.493(3) . ?
C15 C17 1.386(4) . ?
C16 C22 1.372(4) . ?
C18 C23 1.382(4) . ?
C19 C29 1.384(5) . ?
C20 C31 1.392(4) . ?
C21 C36 1.349(6) . ?
C21 C31 1.360(5) . ?
C22 C24 1.373(5) . ?
C23 C24 1.352(5) . ?
C25 C33 1.390(5) . ?
C26 C27 1.389(5) . ?
C27 C30 1.366(5) . ?
C28 C36 1.380(5) . ?
C29 C34 1.338(7) . ?
C30 C32 1.351(5) . ?
C32 C35 1.387(4) . ?
C33 C34 1.379(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307344
