#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/73/7157386.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_7157386
loop_
_publ_author_name
'Teng, Qiaoqiao'
'Singh, Chandan'
'Han, Yuan'
'Huynh, Han Vinh'
_publ_section_title
;
 Fused azole-thiazolines via one-pot cyclization of functionalized
 N-heterocyclic carbene precursors.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2487
_journal_page_last               2491
_journal_paper_doi               10.1039/c9ob02548k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C15 H17 N3 S2'
_chemical_formula_weight         303.44
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_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
_audit_update_record
;
2017-03-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5462(6)
_cell_length_b                   11.8138(6)
_cell_length_c                   24.1532(13)
_cell_measurement_reflns_used    5839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.56
_cell_volume                     3009.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20165
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.8188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0467
_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)+(0.0590P)²+2.1451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                3130
_reflns_number_total             3455
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob02548k2.cif
_cod_data_source_block           9490
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157386--7157390.cif.
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7157386
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C4A C 0.4329(3) 0.3417(6) 0.5796(4) 0.0267(14) Uani 0.565(19) 1 d PD A 1
H4AA H 0.3758 0.3065 0.6072 0.032 Uiso 0.565(19) 1 calc PR A 1
H4AB H 0.3807 0.3872 0.5538 0.032 Uiso 0.565(19) 1 calc PR A 1
C4B C 0.4522(8) 0.3665(5) 0.5605(4) 0.0235(18) Uani 0.435(19) 1 d PD A 2
H4BA H 0.3629 0.3608 0.5728 0.028 Uiso 0.435(19) 1 calc PR A 2
H4BB H 0.4547 0.4135 0.5266 0.028 Uiso 0.435(19) 1 calc PR A 2
S1 S 0.54726(4) 0.43318(4) 0.61464(2) 0.02048(14) Uani 1 1 d D . .
S2 S 0.32558(5) 0.64905(5) 0.61294(2) 0.02707(15) Uani 1 1 d . . .
N1 N 0.62796(13) 0.24218(12) 0.57351(6) 0.0162(3) Uani 1 1 d . . .
N2 N 0.77862(14) 0.31393(12) 0.62339(6) 0.0149(3) Uani 1 1 d . . .
N3 N 0.26593(17) 0.57066(15) 0.50641(7) 0.0294(4) Uani 1 1 d . . .
C1 C 0.82344(17) 0.21322(14) 0.60023(8) 0.0177(4) Uani 1 1 d . A .
H1 H 0.9054 0.1817 0.6055 0.021 Uiso 1 1 calc R . .
C2 C 0.72971(17) 0.16857(15) 0.56895(7) 0.0188(4) Uani 1 1 d . A .
H2 H 0.7329 0.1005 0.5481 0.023 Uiso 1 1 calc R . .
C3 C 0.50249(17) 0.25096(18) 0.54803(9) 0.0281(4) Uani 1 1 d D A .
H3A H 0.4569 0.1779 0.5507 0.034 Uiso 0.565(19) 1 calc PR A 1
H3B H 0.5101 0.2719 0.5085 0.034 Uiso 0.565(19) 1 calc PR A 1
H3C H 0.4452 0.1926 0.5635 0.034 Uiso 0.435(19) 1 d PR A 2
H3D H 0.5087 0.2394 0.5075 0.034 Uiso 0.435(19) 1 d PR A 2
C5 C 0.65990(16) 0.32861(15) 0.60580(7) 0.0154(3) Uani 1 1 d . A .
C6 C 0.84695(15) 0.39166(14) 0.65889(7) 0.0142(3) Uani 1 1 d . A .
C7 C 0.80564(16) 0.40574(14) 0.71331(7) 0.0155(3) Uani 1 1 d . . .
C8 C 0.86838(16) 0.48648(14) 0.74560(7) 0.0165(3) Uani 1 1 d . A .
H8 H 0.8409 0.4993 0.7825 0.020 Uiso 1 1 calc R . .
C9 C 0.97015(16) 0.54858(14) 0.72493(7) 0.0168(3) Uani 1 1 d . . .
C10 C 1.01035(16) 0.52862(14) 0.67096(7) 0.0175(4) Uani 1 1 d . A .
H10 H 1.0809 0.5697 0.6570 0.021 Uiso 1 1 calc R . .
C11 C 0.95045(16) 0.45031(14) 0.63684(7) 0.0154(3) Uani 1 1 d . . .
C12 C 0.69908(17) 0.33645(15) 0.73760(8) 0.0195(4) Uani 1 1 d . A .
H12A H 0.6176 0.3707 0.7276 0.029 Uiso 1 1 calc R . .
H12B H 0.7074 0.3345 0.7780 0.029 Uiso 1 1 calc R . .
H12C H 0.7030 0.2592 0.7230 0.029 Uiso 1 1 calc R . .
C13 C 1.03941(18) 0.63331(16) 0.76055(8) 0.0217(4) Uani 1 1 d . A .
H13A H 1.1168 0.5987 0.7753 0.032 Uiso 1 1 calc R . .
H13B H 0.9846 0.6567 0.7913 0.032 Uiso 1 1 calc R . .
H13C H 1.0618 0.6996 0.7382 0.032 Uiso 1 1 calc R . .
C14 C 0.99772(18) 0.42948(15) 0.57890(7) 0.0200(4) Uani 1 1 d . A .
H14A H 1.0561 0.4902 0.5682 0.030 Uiso 1 1 calc R . .
H14B H 0.9257 0.4280 0.5533 0.030 Uiso 1 1 calc R . .
H14C H 1.0421 0.3567 0.5775 0.030 Uiso 1 1 calc R . .
C15 C 0.29094(16) 0.60431(15) 0.55024(8) 0.0190(4) Uani 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'
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
C3 C4A S1 109.5(2) . . ?
C3 C4B S1 110.1(2) . . ?
C5 S1 C4B 88.88(17) . . ?
C5 S1 C4A 88.50(15) . . ?
C4B S1 C4A 18.38(19) . . ?
C5 N1 C2 109.43(14) . . ?
C5 N1 C3 114.96(15) . . ?
C2 N1 C3 135.35(15) . . ?
C5 N2 C1 107.51(14) . . ?
C5 N2 C6 124.98(14) . . ?
C1 N2 C6 127.49(14) . . ?
C2 C1 N2 107.98(15) . . ?
C1 C2 N1 106.08(15) . . ?
N1 C3 C4B 107.5(2) . . ?
N1 C3 C4A 106.1(2) . . ?
C4B C3 C4A 22.4(2) . . ?
N1 C5 N2 108.98(15) . . ?
N1 C5 S1 116.61(13) . . ?
N2 C5 S1 134.38(14) . . ?
C7 C6 C11 122.94(15) . . ?
C7 C6 N2 118.57(15) . . ?
C11 C6 N2 118.49(15) . . ?
C6 C7 C8 117.33(16) . . ?
C6 C7 C12 122.30(15) . . ?
C8 C7 C12 120.36(16) . . ?
C9 C8 C7 121.59(16) . . ?
C10 C9 C8 118.79(16) . . ?
C10 C9 C13 119.97(16) . . ?
C8 C9 C13 121.21(16) . . ?
C11 C10 C9 121.98(16) . . ?
C10 C11 C6 117.29(16) . . ?
C10 C11 C14 120.60(16) . . ?
C6 C11 C14 122.10(15) . . ?
N3 C15 S2 178.66(18) . . ?
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
C4A C3 1.507(4) . ?
C4A S1 1.827(3) . ?
C4B C3 1.495(4) . ?
C4B S1 1.826(4) . ?
S1 C5 1.7271(18) . ?
S2 C15 1.645(2) . ?
N1 C5 1.328(2) . ?
N1 C2 1.386(2) . ?
N1 C3 1.463(2) . ?
N2 C5 1.333(2) . ?
N2 C1 1.397(2) . ?
N2 C6 1.448(2) . ?
N3 C15 1.161(3) . ?
C1 C2 1.351(3) . ?
C6 C7 1.395(2) . ?
C6 C11 1.398(2) . ?
C7 C8 1.399(2) . ?
C7 C12 1.509(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.391(3) . ?
C9 C13 1.508(2) . ?
C10 C11 1.391(2) . ?
C11 C14 1.506(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353305
