#------------------------------------------------------------------------------
#$Date: 2024-11-09 04:04:48 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249562.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_7249562
loop_
_publ_author_name
'Aggarwal, Ranjana'
'Sharma, Shilpa'
'Jain, Naman'
'Sanz, Dionisia'
'Claramunt, Rosa M.'
'Delgado, Patricia'
'Torralba, M. Carmen'
_publ_section_title
;
 Reaction of unsymmetrical α-bromo-1,3-diketones with N-substituted
 thioureas: regioselective access to
 2-(N-arylamino)-5-acyl-4-methylthiazoles and/or rearranged
 2-(N-acylimino)-3-N-aryl-4-methylthiazoles
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              35585
_journal_page_last               35600
_journal_paper_doi               10.1039/D4RA05436A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C18 H15 Cl N2 O2 S'
_chemical_formula_sum            'C18 H15 Cl N2 O2 S'
_chemical_formula_weight         358.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-12-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                107.810(2)
_cell_angle_beta                 110.578(2)
_cell_angle_gamma                96.950(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4627(10)
_cell_length_b                   9.6608(10)
_cell_length_c                   11.0027(11)
_cell_measurement_reflns_used    2344
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.9914
_cell_measurement_theta_min      2.2908
_cell_volume                     866.57(16)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9152
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_min         2.133
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0442 before and 0.0203 after correction. The Ratio of minimum to maximum transmission is 0.8449. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2063
_reflns_number_total             4133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05436a2.cif
_cod_data_source_block           data1t
_cod_database_code               7249562
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_original_sample_id 'sph 53b'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
Cl1 Cl -0.04027(8) 0.99298(8) 0.29934(8) 0.0912(3) Uani 1 1 d . . . . .
S1 S 0.34999(8) 0.29215(7) 0.43359(7) 0.0704(2) Uani 1 1 d . . . . .
O1 O 0.4530(2) 0.43501(19) 0.70206(17) 0.0744(5) Uani 1 1 d . . . . .
O2 O 0.43855(19) 0.97092(19) 1.20358(16) 0.0741(5) Uani 1 1 d . . . . .
N3 N 0.1966(2) 0.4615(2) 0.33596(19) 0.0586(5) Uani 1 1 d . . . . .
N6 N 0.2944(2) 0.5533(2) 0.57975(18) 0.0551(5) Uani 1 1 d . . . . .
C2 C 0.2787(2) 0.4506(2) 0.4618(2) 0.0547(6) Uani 1 1 d . . . . .
C4 C 0.1877(3) 0.3433(3) 0.2180(3) 0.0706(7) Uani 1 1 d . . . . .
C5 C 0.2639(3) 0.2456(3) 0.2556(3) 0.0771(7) Uani 1 1 d . . . . .
H5 H 0.2699 0.1602 0.1915 0.093 Uiso 1 1 calc R U . . .
C7 C 0.3859(3) 0.5379(3) 0.6995(2) 0.0563(6) Uani 1 1 d . . . . .
C8 C 0.4010(3) 0.6531(2) 0.8317(2) 0.0533(5) Uani 1 1 d . . . . .
C9 C 0.5065(3) 0.6596(3) 0.9586(3) 0.0687(7) Uani 1 1 d . . . . .
H9 H 0.5684 0.5919 0.9594 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5233(3) 0.7631(3) 1.0846(3) 0.0700(7) Uani 1 1 d . . . . .
H10 H 0.5960 0.7652 1.1685 0.084 Uiso 1 1 calc R U . . .
C11 C 0.4315(3) 0.8632(3) 1.0849(2) 0.0591(6) Uani 1 1 d . . . . .
C12 C 0.3246(3) 0.8594(3) 0.9591(3) 0.0668(7) Uani 1 1 d . . . . .
H12 H 0.2624 0.9269 0.9590 0.080 Uiso 1 1 calc R U . . .
C13 C 0.3098(3) 0.7567(3) 0.8345(2) 0.0618(6) Uani 1 1 d . . . . .
H13 H 0.2380 0.7560 0.7508 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1392(2) 0.5913(3) 0.3285(2) 0.0529(5) Uani 1 1 d . . . . .
C15 C 0.0095(3) 0.6103(3) 0.3548(2) 0.0662(7) Uani 1 1 d . . . . .
H15 H -0.0402 0.5402 0.3786 0.079 Uiso 1 1 calc R U . . .
C16 C -0.0465(3) 0.7337(3) 0.3458(3) 0.0699(7) Uani 1 1 d . . . . .
H16 H -0.1347 0.7469 0.3623 0.084 Uiso 1 1 calc R U . . .
C17 C 0.0296(3) 0.8371(3) 0.3120(2) 0.0600(6) Uani 1 1 d . . . . .
C18 C 0.1607(3) 0.8198(3) 0.2878(2) 0.0633(6) Uani 1 1 d . . . . .
H18 H 0.2115 0.8908 0.2657 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2160(3) 0.6958(3) 0.2967(2) 0.0612(6) Uani 1 1 d . . . . .
H19 H 0.3049 0.6830 0.2812 0.073 Uiso 1 1 calc R U . . .
C20 C 0.0988(4) 0.3395(3) 0.0746(3) 0.0998(10) Uani 1 1 d . . . . .
H20A H -0.0047 0.3479 0.0634 0.150 Uiso 1 1 calc R U . . .
H20B H 0.0928 0.2463 0.0063 0.150 Uiso 1 1 calc R U . . .
H20C H 0.1510 0.4219 0.0616 0.150 Uiso 1 1 calc R U . . .
C21 C 0.5628(3) 0.9951(3) 1.3340(3) 0.0869(8) Uani 1 1 d . . . . .
H21A H 0.6610 1.0165 1.3274 0.130 Uiso 1 1 calc R U . . .
H21B H 0.5518 0.9064 1.3557 0.130 Uiso 1 1 calc R U . . .
H21C H 0.5592 1.0786 1.4066 0.130 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C5 S1 C2 90.93(12) . . ?
C11 O2 C21 118.1(2) . . ?
C2 N3 C4 114.4(2) . . ?
C2 N3 C14 121.73(18) . . ?
C4 N3 C14 123.6(2) . . ?
C2 N6 C7 115.99(19) . . ?
N3 C2 S1 109.73(16) . . ?
N6 C2 S1 129.95(18) . . ?
N6 C2 N3 120.3(2) . . ?
N3 C4 C20 119.9(2) . . ?
C5 C4 N3 111.2(2) . . ?
C5 C4 C20 128.9(2) . . ?
S1 C5 H5 123.1 . . ?
C4 C5 S1 113.7(2) . . ?
C4 C5 H5 123.1 . . ?
O1 C7 N6 124.0(2) . . ?
O1 C7 C8 120.5(2) . . ?
N6 C7 C8 115.5(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 C13 117.3(2) . . ?
C13 C8 C7 122.6(2) . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.3(2) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
O2 C11 C10 124.3(2) . . ?
O2 C11 C12 116.1(2) . . ?
C10 C11 C12 119.6(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 N3 119.8(2) . . ?
C19 C14 N3 119.34(19) . . ?
C19 C14 C15 120.8(2) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 Cl1 119.80(19) . . ?
C18 C17 Cl1 118.99(18) . . ?
C18 C17 C16 121.2(2) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 C18 119.8(2) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Cl1 C17 1.741(2) . ?
S1 C2 1.732(2) . ?
S1 C5 1.718(3) . ?
O1 C7 1.245(2) . ?
O2 C11 1.372(3) . ?
O2 C21 1.428(3) . ?
N3 C2 1.373(3) . ?
N3 C4 1.410(3) . ?
N3 C14 1.439(3) . ?
N6 C2 1.316(3) . ?
N6 C7 1.363(3) . ?
C4 C5 1.333(3) . ?
C4 C20 1.491(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.483(3) . ?
C8 C9 1.379(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 C19 1.373(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(3) . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
Cl1 C17 C18 C19 -179.52(17) . . . . ?
O1 C7 C8 C9 9.0(3) . . . . ?
O1 C7 C8 C13 -169.9(2) . . . . ?
O2 C11 C12 C13 179.4(2) . . . . ?
N3 C4 C5 S1 -0.4(3) . . . . ?
N3 C14 C15 C16 -179.1(2) . . . . ?
N3 C14 C19 C18 179.28(19) . . . . ?
N6 C7 C8 C9 -171.57(19) . . . . ?
N6 C7 C8 C13 9.5(3) . . . . ?
C2 S1 C5 C4 0.9(2) . . . . ?
C2 N3 C4 C5 -0.6(3) . . . . ?
C2 N3 C4 C20 178.6(2) . . . . ?
C2 N3 C14 C15 -75.9(3) . . . . ?
C2 N3 C14 C19 103.4(2) . . . . ?
C2 N6 C7 O1 0.1(3) . . . . ?
C2 N6 C7 C8 -179.24(18) . . . . ?
C4 N3 C2 S1 1.2(2) . . . . ?
C4 N3 C2 N6 -179.41(19) . . . . ?
C4 N3 C14 C15 110.5(2) . . . . ?
C4 N3 C14 C19 -70.2(3) . . . . ?
C5 S1 C2 N3 -1.18(16) . . . . ?
C5 S1 C2 N6 179.5(2) . . . . ?
C7 N6 C2 S1 3.2(3) . . . . ?
C7 N6 C2 N3 -176.05(17) . . . . ?
C7 C8 C9 C10 -179.0(2) . . . . ?
C7 C8 C13 C12 178.5(2) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C9 C10 C11 O2 -179.8(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C14 N3 C2 S1 -172.88(15) . . . . ?
C14 N3 C2 N6 6.5(3) . . . . ?
C14 N3 C4 C5 173.4(2) . . . . ?
C14 N3 C4 C20 -7.4(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C14 C19 C18 -1.5(3) . . . . ?
C15 C16 C17 Cl1 179.68(18) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C19 C14 C15 C16 1.6(3) . . . . ?
C20 C4 C5 S1 -179.4(2) . . . . ?
C21 O2 C11 C10 9.0(3) . . . . ?
C21 O2 C11 C12 -170.4(2) . . . . ?
