#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/25/1512576.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_1512576
loop_
_publ_author_name
'Yugandar, Somaraju'
'Misra, Nimesh C.'
'Parameshwarappa, Gangajji'
'Panda, Kausik'
'Ila, Hiriyakkanavar'
_publ_section_title
;
 Reaction of Cyclic α-Oxoketene Dithioacetals with Methylene Isocyanides:
 A Novel Pyrrole Annulation--Ring-Expansion Domino Process
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              5250
_journal_paper_doi               10.1021/ol402469v
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C20 H15 N O4 S2'
_chemical_formula_weight         397.45
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.357(2)
_cell_angle_beta                 84.196(2)
_cell_angle_gamma                63.703(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7124(11)
_cell_length_b                   8.5857(12)
_cell_length_c                   14.714(2)
_cell_measurement_temperature    293(2)
_cell_volume                     868.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5775
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9547
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.042
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0564
_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)+(0.0503P)²+3.4305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1909
_reflns_number_gt                3399
_reflns_number_total             4125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402469v_si_002.cif
_cod_data_source_block           25mayem
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        868.8(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1512576
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.40868(14) 0.58380(12) 0.27634(6) 0.0220(2) Uani 1 1 d .
S2 S 0.65333(14) 0.12454(12) 0.28597(6) 0.0202(2) Uani 1 1 d .
O1 O 0.4973(4) 0.7856(4) 0.09431(19) 0.0282(6) Uani 1 1 d .
O2 O 0.9767(4) 0.1598(4) -0.06486(19) 0.0278(6) Uani 1 1 d .
O3 O 0.4601(4) 0.1847(4) 0.32980(19) 0.0276(6) Uani 1 1 d .
O4 O 0.7562(4) -0.0487(4) 0.24932(18) 0.0260(6) Uani 1 1 d .
N1 N 0.7723(4) 0.1912(4) 0.1153(2) 0.0179(6) Uani 1 1 d .
H1 H 0.8385 0.0821 0.1027 0.021 Uiso 1 1 calc R
C1 C 0.6545(5) 0.2617(5) 0.1949(2) 0.0203(7) Uani 1 1 d .
C2 C 0.5702(5) 0.4406(5) 0.1906(2) 0.0181(7) Uani 1 1 d .
C3 C 0.6421(5) 0.4795(5) 0.1038(2) 0.0179(7) Uani 1 1 d .
C4 C 0.6085(5) 0.6441(5) 0.0599(2) 0.0197(7) Uani 1 1 d .
C5 C 0.7197(5) 0.6298(5) -0.0325(2) 0.0195(7) Uani 1 1 d .
C6 C 0.6985(5) 0.7802(5) -0.0765(3) 0.0220(7) Uani 1 1 d .
H6 H 0.6186 0.8873 -0.0483 0.026 Uiso 1 1 calc R
C7 C 0.7943(6) 0.7743(5) -0.1621(3) 0.0245(8) Uani 1 1 d .
H7 H 0.7772 0.8768 -0.1915 0.029 Uiso 1 1 calc R
C8 C 0.9162(6) 0.6144(5) -0.2040(3) 0.0232(8) Uani 1 1 d .
H8 H 0.9819 0.6099 -0.2612 0.028 Uiso 1 1 calc R
C9 C 0.9401(5) 0.4616(5) -0.1606(3) 0.0203(7) Uani 1 1 d .
H9 H 1.0211 0.3551 -0.1891 0.024 Uiso 1 1 calc R
C10 C 0.8435(5) 0.4669(5) -0.0745(2) 0.0180(7) Uani 1 1 d .
C11 C 0.8717(5) 0.3017(5) -0.0295(2) 0.0200(7) Uani 1 1 d .
C12 C 0.7665(5) 0.3213(4) 0.0607(2) 0.0172(7) Uani 1 1 d .
C13 C 0.5457(7) 0.6951(6) 0.3055(3) 0.0312(9) Uani 1 1 d .
H13A H 0.4723 0.7798 0.3529 0.047 Uiso 1 1 calc R
H13B H 0.5720 0.7522 0.2526 0.047 Uiso 1 1 calc R
H13C H 0.6662 0.6128 0.3265 0.047 Uiso 1 1 calc R
C14 C 0.7962(5) 0.1589(5) 0.3628(2) 0.0195(7) Uani 1 1 d .
C15 C 0.7055(6) 0.2797(5) 0.4333(3) 0.0228(8) Uani 1 1 d .
H15 H 0.5707 0.3387 0.4424 0.027 Uiso 1 1 calc R
C16 C 0.8195(6) 0.3110(5) 0.4901(3) 0.0233(8) Uani 1 1 d .
H16 H 0.7602 0.3918 0.5378 0.028 Uiso 1 1 calc R
C17 C 1.0219(6) 0.2233(5) 0.4769(3) 0.0260(8) Uani 1 1 d .
C18 C 1.1080(6) 0.1014(5) 0.4063(3) 0.0271(8) Uani 1 1 d .
H18 H 1.2428 0.0423 0.3972 0.033 Uiso 1 1 calc R
C19 C 0.9980(6) 0.0656(5) 0.3490(3) 0.0230(8) Uani 1 1 d .
H19 H 1.0569 -0.0182 0.3026 0.028 Uiso 1 1 calc R
C20 C 1.1448(7) 0.2616(6) 0.5377(3) 0.0362(10) Uani 1 1 d .
H20A H 1.0620 0.3483 0.5827 0.054 Uiso 1 1 calc R
H20B H 1.2254 0.3036 0.5015 0.054 Uiso 1 1 calc R
H20C H 1.2252 0.1573 0.5677 0.054 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
C2 S1 C13 100.58(18)
O3 S2 O4 120.44(18)
O3 S2 C1 109.51(18)
O4 S2 C1 105.73(17)
O3 S2 C14 107.93(17)
O4 S2 C14 108.86(18)
C1 S2 C14 103.02(17)
C12 N1 C1 108.7(3)
N1 C1 C2 109.5(3)
N1 C1 S2 119.5(3)
C2 C1 S2 130.6(3)
C1 C2 C3 105.8(3)
C1 C2 S1 125.3(3)
C3 C2 S1 128.9(3)
C12 C3 C2 106.9(3)
C12 C3 C4 121.0(3)
C2 C3 C4 132.1(3)
O1 C4 C3 123.1(3)
O1 C4 C5 121.1(3)
C3 C4 C5 115.8(3)
C6 C5 C10 119.6(3)
C6 C5 C4 118.7(3)
C10 C5 C4 121.7(3)
C5 C6 C7 121.0(4)
C6 C7 C8 119.7(3)
C9 C8 C7 120.2(4)
C8 C9 C10 120.3(3)
C9 C10 C5 119.2(3)
C9 C10 C11 119.3(3)
C5 C10 C11 121.5(3)
O2 C11 C12 122.4(3)
O2 C11 C10 122.5(3)
C12 C11 C10 115.0(3)
N1 C12 C3 109.1(3)
N1 C12 C11 125.9(3)
C3 C12 C11 125.0(3)
C15 C14 C19 121.9(4)
C15 C14 S2 119.4(3)
C19 C14 S2 118.7(3)
C16 C15 C14 118.7(4)
C15 C16 C17 121.1(4)
C18 C17 C16 118.8(4)
C18 C17 C20 120.6(4)
C16 C17 C20 120.6(4)
C19 C18 C17 121.6(4)
C18 C19 C14 118.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.752(4)
S1 C13 1.796(4)
S2 O3 1.430(3)
S2 O4 1.431(3)
S2 C1 1.761(4)
S2 C14 1.771(4)
O1 C4 1.222(5)
O2 C11 1.219(4)
N1 C12 1.345(4)
N1 C1 1.378(5)
C1 C2 1.379(5)
C2 C3 1.430(5)
C3 C12 1.392(5)
C3 C4 1.463(5)
C4 C5 1.509(5)
C5 C6 1.379(5)
C5 C10 1.414(5)
C6 C7 1.385(5)
C7 C8 1.391(5)
C8 C9 1.387(5)
C9 C10 1.394(5)
C10 C11 1.483(5)
C11 C12 1.456(5)
C14 C15 1.383(5)
C14 C19 1.395(5)
C15 C16 1.383(5)
C16 C17 1.396(6)
C17 C18 1.387(6)
C17 C20 1.507(6)
C18 C19 1.384(6)
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
C12 N1 C1 C2 0.6(4)
C12 N1 C1 S2 -172.6(3)
O3 S2 C1 N1 -142.4(3)
O4 S2 C1 N1 -11.3(3)
C14 S2 C1 N1 102.9(3)
O3 S2 C1 C2 46.0(4)
O4 S2 C1 C2 177.1(4)
C14 S2 C1 C2 -68.7(4)
N1 C1 C2 C3 -0.3(4)
S2 C1 C2 C3 172.0(3)
N1 C1 C2 S1 179.7(3)
S2 C1 C2 S1 -8.1(5)
C13 S1 C2 C1 117.5(4)
C13 S1 C2 C3 -62.7(4)
C1 C2 C3 C12 -0.2(4)
S1 C2 C3 C12 179.9(3)
C1 C2 C3 C4 -179.3(4)
S1 C2 C3 C4 0.8(6)
C12 C3 C4 O1 178.3(4)
C2 C3 C4 O1 -2.7(6)
C12 C3 C4 C5 -1.3(5)
C2 C3 C4 C5 177.7(4)
O1 C4 C5 C6 2.1(5)
C3 C4 C5 C6 -178.3(3)
O1 C4 C5 C10 -177.7(4)
C3 C4 C5 C10 1.9(5)
C10 C5 C6 C7 1.0(6)
C4 C5 C6 C7 -178.7(3)
C5 C6 C7 C8 -1.0(6)
C6 C7 C8 C9 0.7(6)
C7 C8 C9 C10 -0.5(6)
C8 C9 C10 C5 0.5(5)
C8 C9 C10 C11 -179.9(3)
C6 C5 C10 C9 -0.8(5)
C4 C5 C10 C9 179.0(3)
C6 C5 C10 C11 179.6(3)
C4 C5 C10 C11 -0.6(5)
C9 C10 C11 O2 -0.1(6)
C5 C10 C11 O2 179.5(4)
C9 C10 C11 C12 179.2(3)
C5 C10 C11 C12 -1.2(5)
C1 N1 C12 C3 -0.7(4)
C1 N1 C12 C11 179.7(3)
C2 C3 C12 N1 0.6(4)
C4 C3 C12 N1 179.8(3)
C2 C3 C12 C11 -179.8(3)
C4 C3 C12 C11 -0.6(6)
O2 C11 C12 N1 0.8(6)
C10 C11 C12 N1 -178.5(3)
O2 C11 C12 C3 -178.8(4)
C10 C11 C12 C3 1.9(5)
O3 S2 C14 C15 -20.9(4)
O4 S2 C14 C15 -153.2(3)
C1 S2 C14 C15 94.9(3)
O3 S2 C14 C19 160.5(3)
O4 S2 C14 C19 28.2(3)
C1 S2 C14 C19 -83.7(3)
C19 C14 C15 C16 1.6(6)
S2 C14 C15 C16 -177.0(3)
C14 C15 C16 C17 0.1(6)
C15 C16 C17 C18 -0.9(6)
C15 C16 C17 C20 178.5(4)
C16 C17 C18 C19 0.1(6)
C20 C17 C18 C19 -179.2(4)
C17 C18 C19 C14 1.4(6)
C15 C14 C19 C18 -2.3(6)
S2 C14 C19 C18 176.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139041366
