#------------------------------------------------------------------------------
#$Date: 2025-03-07 17:30:27 +0100 (Fri 07 de Mar de 2025) $
#$Revision: 298328 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/61/7246126.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_7246126
loop_
_publ_author_name
'Zhao, Mingming'
'Guo, Yiming'
'Wang, Qi'
'Liu, Lanqi'
'Zhang, Shujie'
'Guo, Wei'
'Wu, Lin-Ping'
'Qiu, Fayang G.'
_publ_section_title
;
 Synthesis of 2-iminothiazolidin-4-ones via copper-catalyzed [2 + 1 + 2]
 tandem annulation
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2220
_journal_page_last               2224
_journal_paper_doi               10.1039/D2RA07872D
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.935(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5249(3)
_cell_length_b                   5.74470(10)
_cell_length_c                   12.9917(2)
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.1130
_cell_measurement_theta_min      5.0390
_cell_volume                     1307.76(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -31.00   0.50    0.50    --    0.90 -36.00  21.00   50
  2  ω     10.00  35.00   0.50    0.50    --    0.90  36.00 178.00   50
  3  ω     48.00  73.00   0.50    0.50    --  105.10 -36.00  21.00   50
  4  ω    138.00 182.00   0.50    0.50    --  105.10  36.00 178.00   88
  5  ω    -39.00  13.00   0.50    0.50    --   -0.90 -82.00 120.00  104
  6  ω    -37.00  26.00   0.50    0.50    --   -0.90 -82.00  30.00  126
  7  ω    -47.00 -13.00   0.50    0.50    --   -0.90 -77.00-180.00   68
  8  ω     82.00 127.00   0.50    0.50    --  105.10  82.00 120.00   90
  9  ω    150.00 191.00   0.50    0.50    --  105.10  38.00 -60.00   82
 10  ω     82.00 194.00   0.50    0.50    --  105.10  82.00  90.00  224
 11  ω     75.00 119.00   0.50    0.50    --  105.10 -77.00 150.00   88
 12  ω    110.00 136.00   0.50    0.50    --  105.10  38.00 -60.00   52
 13  ω     98.00 123.00   0.50    0.50    --  105.10  38.00  60.00   50
 14  ω    161.00 187.00   0.50    0.50    --  105.10  38.00  60.00   52
 15  ω     73.00 194.00   0.50    0.50    --  105.10  19.00-120.00  242
 16  ω     19.00 106.00   0.50    0.50    --  105.10 -38.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003178000
_diffrn_orient_matrix_UB_12      -0.0250901000
_diffrn_orient_matrix_UB_13      -0.1179187000
_diffrn_orient_matrix_UB_21      0.0779208000
_diffrn_orient_matrix_UB_22      0.1236714000
_diffrn_orient_matrix_UB_23      0.0312654000
_diffrn_orient_matrix_UB_31      0.0407478000
_diffrn_orient_matrix_UB_32      -0.2365693000
_diffrn_orient_matrix_UB_33      0.0288409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6834
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.734
_diffrn_reflns_theta_min         5.048
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    8.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             722
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0622P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2488
_reflns_number_total             2654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra07872d2.cif
_cod_data_source_block           lj-0704
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H N O S'
_cod_original_formula_weight         75.09
_cod_original_formula_moiety         '0.211(C13 H14 N2 O3 S)'
_cod_original_formula_units_Z            19
_cod_database_code               7246126
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C N O H S '
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C9(H9), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.309
_oxdiff_exptl_absorpt_empirical_full_min 0.535
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31132(2) 0.26053(6) 0.64716(3) 0.02649(13) Uani 1 1 d . . . . .
O3 O 0.39120(5) 0.59007(17) 0.40106(7) 0.0281(2) Uani 1 1 d . . . . .
O2 O 0.36898(5) 0.63386(18) 0.56065(7) 0.0305(2) Uani 1 1 d . . . . .
O1 O 0.17342(7) -0.24493(17) 0.52033(9) 0.0351(3) Uani 1 1 d . . . . .
N2 N 0.31305(6) 0.3367(2) 0.43782(9) 0.0253(2) Uani 1 1 d . . . . .
N1 N 0.24019(6) 0.03944(19) 0.46851(9) 0.0245(2) Uani 1 1 d . . . . .
C11 C 0.35902(7) 0.5291(2) 0.47596(10) 0.0245(3) Uani 1 1 d . . . . .
C3 C 0.28949(7) 0.2229(2) 0.50645(10) 0.0233(3) Uani 1 1 d . . . . .
C5 C 0.14897(7) 0.1354(2) 0.28497(10) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.12404(7) 0.3313(2) 0.32635(11) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.1445 0.3668 0.4000 0.031 Uiso 1 1 calc R U . . .
C2 C 0.21834(7) -0.0858(2) 0.54465(11) 0.0263(3) Uani 1 1 d . . . . .
C4 C 0.21197(7) -0.0222(2) 0.35331(10) 0.0250(3) Uani 1 1 d . . . . .
H4A H 0.1931 -0.1809 0.3464 0.030 Uiso 1 1 calc R U . . .
H4B H 0.2542 -0.0173 0.3246 0.030 Uiso 1 1 calc R U . . .
C6 C 0.11684(8) 0.0821(2) 0.17481(11) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.1325 -0.0505 0.1469 0.034 Uiso 1 1 calc R U . . .
C12 C 0.44274(8) 0.7875(2) 0.42869(11) 0.0280(3) Uani 1 1 d . . . . .
H12A H 0.4822 0.7618 0.4981 0.034 Uiso 1 1 calc R U . . .
H12B H 0.4151 0.9281 0.4337 0.034 Uiso 1 1 calc R U . . .
C9 C 0.06825(8) 0.4751(2) 0.25751(12) 0.0302(3) Uani 1 1 d . . . . .
H9 H 0.0518 0.6066 0.2854 0.036 Uiso 1 1 calc R U . . .
C8 C 0.06160(9) 0.2257(3) 0.10656(12) 0.0334(3) Uani 1 1 d . . . . .
H8 H 0.0408 0.1900 0.0330 0.040 Uiso 1 1 calc R U . . .
C1 C 0.25876(8) 0.0006(2) 0.65811(11) 0.0284(3) Uani 1 1 d . . . . .
H1A H 0.2934 -0.1175 0.6998 0.034 Uiso 1 1 calc R U . . .
H1B H 0.2220 0.0362 0.6947 0.034 Uiso 1 1 calc R U . . .
C10 C 0.03727(8) 0.4225(3) 0.14782(12) 0.0334(3) Uani 1 1 d . . . . .
H10 H 0.0003 0.5188 0.1020 0.040 Uiso 1 1 calc R U . . .
C13 C 0.47748(8) 0.8096(3) 0.33915(12) 0.0323(3) Uani 1 1 d . . . . .
H13A H 0.4377 0.8318 0.2709 0.048 Uiso 1 1 calc R U . . .
H13B H 0.5054 0.6705 0.3360 0.048 Uiso 1 1 calc R U . . .
H13C H 0.5114 0.9407 0.3535 0.048 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 S1 C1 91.85(6) . . ?
C11 O3 C12 115.86(10) . . ?
C3 N2 C11 117.62(11) . . ?
C3 N1 C2 117.09(11) . . ?
C3 N1 C4 121.87(11) . . ?
C2 N1 C4 121.04(11) . . ?
O3 C11 N2 108.36(11) . . ?
O2 C11 O3 123.70(12) . . ?
O2 C11 N2 127.92(12) . . ?
N2 C3 S1 130.01(10) . . ?
N2 C3 N1 118.31(12) . . ?
N1 C3 S1 111.68(9) . . ?
C7 C5 C4 123.14(12) . . ?
C7 C5 C6 119.37(12) . . ?
C6 C5 C4 117.46(11) . . ?
C5 C7 H7 120.0 . . ?
C5 C7 C9 120.08(12) . . ?
C9 C7 H7 120.0 . . ?
O1 C2 N1 122.86(12) . . ?
O1 C2 C1 126.02(12) . . ?
N1 C2 C1 111.12(11) . . ?
N1 C4 C5 114.02(10) . . ?
N1 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C6 H6 119.8 . . ?
C8 C6 C5 120.40(13) . . ?
C8 C6 H6 119.8 . . ?
O3 C12 H12A 110.4 . . ?
O3 C12 H12B 110.4 . . ?
O3 C12 C13 106.66(11) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C7 C9 H9 119.9 . . ?
C10 C9 C7 120.20(13) . . ?
C10 C9 H9 119.9 . . ?
C6 C8 H8 119.9 . . ?
C6 C8 C10 120.15(14) . . ?
C10 C8 H8 119.9 . . ?
S1 C1 H1A 110.2 . . ?
S1 C1 H1B 110.2 . . ?
C2 C1 S1 107.71(9) . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C9 C10 C8 119.79(14) . . ?
C9 C10 H10 120.1 . . ?
C8 C10 H10 120.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 C3 1.7529(13) . ?
S1 C1 1.8131(14) . ?
O3 C11 1.3422(15) . ?
O3 C12 1.4505(16) . ?
O2 C11 1.2145(16) . ?
O1 C2 1.2072(17) . ?
N2 C11 1.3850(17) . ?
N2 C3 1.2904(17) . ?
N1 C3 1.3770(17) . ?
N1 C2 1.3857(16) . ?
N1 C4 1.4597(16) . ?
C5 C7 1.3892(19) . ?
C5 C4 1.5158(18) . ?
C5 C6 1.3942(18) . ?
C7 H7 0.9300 . ?
C7 C9 1.3967(19) . ?
C2 C1 1.5045(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C8 1.387(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5064(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(2) . ?
C8 H8 0.9300 . ?
C8 C10 1.388(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C10 H10 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C1 S1 -174.00(12) . . . . ?
N1 C2 C1 S1 7.08(13) . . . . ?
C11 O3 C12 C13 174.67(11) . . . . ?
C11 N2 C3 S1 -4.68(19) . . . . ?
C11 N2 C3 N1 176.30(11) . . . . ?
C3 S1 C1 C2 -6.85(10) . . . . ?
C3 N2 C11 O3 166.13(11) . . . . ?
C3 N2 C11 O2 -15.4(2) . . . . ?
C3 N1 C2 O1 177.43(12) . . . . ?
C3 N1 C2 C1 -3.62(16) . . . . ?
C3 N1 C4 C5 -77.53(14) . . . . ?
C5 C7 C9 C10 0.3(2) . . . . ?
C5 C6 C8 C10 -0.7(2) . . . . ?
C7 C5 C4 N1 4.50(17) . . . . ?
C7 C5 C6 C8 1.3(2) . . . . ?
C7 C9 C10 C8 0.3(2) . . . . ?
C2 N1 C3 S1 -1.85(15) . . . . ?
C2 N1 C3 N2 177.35(11) . . . . ?
C2 N1 C4 C5 102.61(14) . . . . ?
C4 N1 C3 S1 178.28(9) . . . . ?
C4 N1 C3 N2 -2.53(18) . . . . ?
C4 N1 C2 O1 -2.7(2) . . . . ?
C4 N1 C2 C1 176.26(11) . . . . ?
C4 C5 C7 C9 176.91(12) . . . . ?
C4 C5 C6 C8 -176.82(12) . . . . ?
C6 C5 C7 C9 -1.10(19) . . . . ?
C6 C5 C4 N1 -177.45(11) . . . . ?
C6 C8 C10 C9 -0.1(2) . . . . ?
C12 O3 C11 O2 2.61(19) . . . . ?
C12 O3 C11 N2 -178.88(11) . . . . ?
C1 S1 C3 N2 -173.87(13) . . . . ?
C1 S1 C3 N1 5.20(10) . . . . ?
