#------------------------------------------------------------------------------
#$Date: 2024-11-09 04:04:48 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249561.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_7249561
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         '1.333(C17 H14 N2 O S)'
_chemical_formula_sum            'C22.67 H18.67 N2.67 O1.33 S1.33'
_chemical_formula_weight         392.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 98.509(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   19.262(3)
_cell_length_b                   4.9631(9)
_cell_length_c                   30.819(5)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.0921
_cell_measurement_theta_min      2.3478
_cell_volume                     2913.8(8)
_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-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_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  0.0849
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13672
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.944
_diffrn_reflns_theta_min         1.336
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.576010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0507 before and 0.0352 after correction. The Ratio of minimum to maximum transmission is 0.5760. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0580
_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)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1877
_reflns_number_total             3533
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05436a2.cif
_cod_data_source_block           shp-9
_cod_original_cell_volume        2913.8(9)
_cod_database_code               7249561
_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, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C15A(H15A),
 C16(H16), C16A(H16A), C17(H17), C17(H17A), C18(H18), C18A(H18A), C19(H19),
 C19A(H19A)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_original_sample_id 'shp 9'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.22151(4) 0.10275(16) 0.12386(2) 0.0399(2) Uani 1 1 d . . . . .
O1 O 0.07266(13) 0.6480(6) 0.10463(7) 0.0812(9) Uani 1 1 d . . . . .
N3 N 0.20159(11) 0.1932(5) 0.20335(7) 0.0331(5) Uani 1 1 d . . . . .
N6 N 0.28790(11) -0.1315(5) 0.19897(7) 0.0373(6) Uani 1 1 d . . . . .
H6 H 0.2836 -0.1765 0.2254 0.045 Uiso 1 1 calc R U . . .
C2 C 0.24017(13) 0.0511(5) 0.17979(8) 0.0295(6) Uani 1 1 d . . . . .
C4 C 0.15408(13) 0.3494(5) 0.17705(8) 0.0334(6) Uani 1 1 d . . . . .
C5 C 0.15697(14) 0.3301(6) 0.13277(8) 0.0342(7) Uani 1 1 d . . . . .
C7 C 0.34347(13) -0.2571(6) 0.18156(8) 0.0316(6) Uani 1 1 d . . . . .
C8 C 0.36839(16) -0.1748(7) 0.14423(10) 0.0573(10) Uani 1 1 d . . . . .
H8 H 0.3469 -0.0315 0.1280 0.116(16) Uiso 1 1 calc R . . . .
C9 C 0.42514(17) -0.3024(8) 0.13039(11) 0.0598(10) Uani 1 1 d . . . . .
H9 H 0.4403 -0.2480 0.1045 0.082(12) Uiso 1 1 calc R . . . .
C10 C 0.45860(17) -0.5039(7) 0.15397(11) 0.0580(10) Uani 1 1 d . . . . .
H10 H 0.4982 -0.5830 0.1455 0.134(18) Uiso 1 1 calc R . . . .
C11 C 0.43306(19) -0.5909(8) 0.19098(12) 0.0699(11) Uani 1 1 d . . . . .
H11 H 0.4545 -0.7355 0.2069 0.067(10) Uiso 1 1 calc R . . . .
C12 C 0.37673(16) -0.4678(6) 0.20473(10) 0.0500(8) Uani 1 1 d . . . . .
H12 H 0.3608 -0.5277 0.2301 0.055(9) Uiso 1 1 calc R . . . .
C13 C 0.11429(15) 0.4783(6) 0.09715(9) 0.0397(7) Uani 1 1 d . . . . .
C14 C 0.12157(14) 0.4092(6) 0.05066(9) 0.0369(7) Uani 1 1 d . . . . .
C15 C 0.1007(3) 0.1615(13) 0.03580(19) 0.0442(17) Uani 0.505(4) 1 d . . P A 1
H15 H 0.0859 0.0351 0.0548 0.053 Uiso 0.505(4) 1 calc R U P A 1
C15A C 0.1883(3) 0.4191(13) 0.03483(18) 0.0431(17) Uani 0.495(4) 1 d . . P A 2
H15A H 0.2284 0.4626 0.0542 0.052 Uiso 0.495(4) 1 calc R U P A 2
C16 C 0.1015(3) 0.0975(15) -0.0079(2) 0.0538(19) Uani 0.505(4) 1 d . . P A 1
H16 H 0.0850 -0.0687 -0.0189 0.065 Uiso 0.505(4) 1 calc R U P A 1
C16A C 0.1939(4) 0.3664(14) -0.0077(2) 0.057(2) Uani 0.495(4) 1 d . . P A 2
H16A H 0.2367 0.3754 -0.0181 0.068 Uiso 0.495(4) 1 calc R U P A 2
C17 C 0.1285(2) 0.2942(8) -0.03633(11) 0.0655(11) Uani 1 1 d . . . . .
H17 H 0.1358 0.2496 -0.0646 0.079 Uiso 0.505(4) 1 calc R U P A 1
H17A H 0.1308 0.2535 -0.0655 0.079 Uiso 0.495(4) 1 calc R U P A 2
C18 C 0.1423(4) 0.5410(15) -0.0200(2) 0.059(2) Uani 0.505(4) 1 d . . P A 1
H18 H 0.1540 0.6753 -0.0387 0.071 Uiso 0.505(4) 1 calc R U P A 1
C18A C 0.0706(4) 0.2848(15) -0.0235(2) 0.0539(19) Uani 0.495(4) 1 d . . P A 2
H18A H 0.0310 0.2383 -0.0432 0.065 Uiso 0.495(4) 1 calc R U P A 2
C19 C 0.1400(3) 0.6067(13) 0.0238(2) 0.0473(17) Uani 0.505(4) 1 d . . P A 1
H19 H 0.1506 0.7797 0.0343 0.057 Uiso 0.505(4) 1 calc R U P A 1
C19A C 0.0640(3) 0.3427(13) 0.01980(19) 0.0450(17) Uani 0.495(4) 1 d . . P A 2
H19A H 0.0198 0.3368 0.0284 0.054 Uiso 0.495(4) 1 calc R U P A 2
C20 C 0.10491(16) 0.5209(7) 0.19824(10) 0.0506(9) Uani 1 1 d . . . . .
H20A H 0.1124 0.4898 0.2293 0.076 Uiso 1 1 calc R U . . .
H20B H 0.0574 0.4759 0.1865 0.076 Uiso 1 1 calc R U . . .
H20C H 0.1134 0.7073 0.1925 0.076 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'
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
C2 S1 C5 89.24(12) . . ?
C2 N3 C4 111.0(2) . . ?
C2 N6 H6 115.5 . . ?
C2 N6 C7 129.1(2) . . ?
C7 N6 H6 115.5 . . ?
N3 C2 S1 114.80(19) . . ?
N3 C2 N6 121.1(2) . . ?
N6 C2 S1 124.00(19) . . ?
N3 C4 C5 115.2(2) . . ?
N3 C4 C20 118.4(2) . . ?
C5 C4 C20 126.4(2) . . ?
C4 C5 S1 109.75(19) . . ?
C4 C5 C13 127.3(2) . . ?
C13 C5 S1 123.0(2) . . ?
C8 C7 N6 124.5(3) . . ?
C12 C7 N6 117.5(2) . . ?
C12 C7 C8 118.0(3) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7(3) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
O1 C13 C5 121.4(3) . . ?
O1 C13 C14 120.0(2) . . ?
C5 C13 C14 118.6(2) . . ?
C15 C14 C13 117.8(3) . . ?
C15 C14 C19 122.6(4) . . ?
C15A C14 C13 122.0(3) . . ?
C19 C14 C13 119.0(4) . . ?
C19A C14 C13 122.1(3) . . ?
C19A C14 C15A 115.9(4) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.5(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15A H15A 119.2 . . ?
C16A C15A C14 121.6(5) . . ?
C16A C15A H15A 119.2 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C15A C16A H16A 121.9 . . ?
C15A C16A C17 116.3(5) . . ?
C17 C16A H16A 121.9 . . ?
C16 C17 H17 121.4 . . ?
C16A C17 H17A 118.3 . . ?
C18 C17 C16 117.1(5) . . ?
C18 C17 H17 121.4 . . ?
C18A C17 C16A 123.3(5) . . ?
C18A C17 H17A 118.3 . . ?
C17 C18 H18 118.5 . . ?
C17 C18 C19 123.0(6) . . ?
C19 C18 H18 118.5 . . ?
C17 C18A H18A 119.6 . . ?
C17 C18A C19A 120.9(6) . . ?
C19A C18A H18A 119.6 . . ?
C14 C19 C18 117.9(6) . . ?
C14 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C14 C19A C18A 122.0(6) . . ?
C14 C19A H19A 119.0 . . ?
C18A C19A H19A 119.0 . . ?
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 . . ?
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 C2 1.727(3) . ?
S1 C5 1.731(3) . ?
O1 C13 1.209(3) . ?
N3 C2 1.318(3) . ?
N3 C4 1.370(3) . ?
N6 H6 0.8600 . ?
N6 C2 1.362(3) . ?
N6 C7 1.412(3) . ?
C4 C5 1.377(3) . ?
C4 C20 1.494(4) . ?
C5 C13 1.468(4) . ?
C7 C8 1.373(4) . ?
C7 C12 1.371(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.344(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.500(4) . ?
C14 C15 1.352(7) . ?
C14 C15A 1.441(6) . ?
C14 C19 1.364(7) . ?
C14 C19A 1.389(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(8) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.356(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.459(8) . ?
C16A H16A 0.9300 . ?
C16A C17 1.472(8) . ?
C17 H17 0.9300 . ?
C17 H17A 0.9300 . ?
C17 C18 1.336(8) . ?
C17 C18A 1.237(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(8) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.390(8) . ?
C19 H19 0.9300 . ?
C19A H19A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
S1 C5 C13 O1 -175.3(3) . . . . ?
S1 C5 C13 C14 6.5(4) . . . . ?
O1 C13 C14 C15 -112.4(4) . . . . ?
O1 C13 C14 C15A 125.4(4) . . . . ?
O1 C13 C14 C19 59.1(5) . . . . ?
O1 C13 C14 C19A -51.8(5) . . . . ?
N3 C4 C5 S1 0.7(3) . . . . ?
N3 C4 C5 C13 -178.1(3) . . . . ?
N6 C7 C8 C9 177.2(3) . . . . ?
N6 C7 C12 C11 -176.9(3) . . . . ?
C2 S1 C5 C4 -0.2(2) . . . . ?
C2 S1 C5 C13 178.7(3) . . . . ?
C2 N3 C4 C5 -1.0(3) . . . . ?
C2 N3 C4 C20 178.9(2) . . . . ?
C2 N6 C7 C8 14.0(5) . . . . ?
C2 N6 C7 C12 -169.1(3) . . . . ?
C4 N3 C2 S1 0.8(3) . . . . ?
C4 N3 C2 N6 -175.8(2) . . . . ?
C4 C5 C13 O1 3.4(5) . . . . ?
C4 C5 C13 C14 -174.7(3) . . . . ?
C5 S1 C2 N3 -0.3(2) . . . . ?
C5 S1 C2 N6 176.1(2) . . . . ?
C5 C13 C14 C15 65.7(5) . . . . ?
C5 C13 C14 C15A -56.4(5) . . . . ?
C5 C13 C14 C19 -122.7(4) . . . . ?
C5 C13 C14 C19A 126.3(4) . . . . ?
C7 N6 C2 S1 19.0(4) . . . . ?
C7 N6 C2 N3 -164.8(3) . . . . ?
C7 C8 C9 C10 -2.2(6) . . . . ?
C8 C7 C12 C11 0.2(5) . . . . ?
C8 C9 C10 C11 3.4(6) . . . . ?
C9 C10 C11 C12 -2.9(6) . . . . ?
C10 C11 C12 C7 1.1(6) . . . . ?
C12 C7 C8 C9 0.4(5) . . . . ?
C13 C14 C15 C16 175.1(5) . . . . ?
C13 C14 C15A C16A -177.4(5) . . . . ?
C13 C14 C19 C18 -176.2(5) . . . . ?
C13 C14 C19A C18A 178.5(5) . . . . ?
C14 C15 C16 C17 3.3(9) . . . . ?
C14 C15A C16A C17 -1.1(9) . . . . ?
C15 C14 C19 C18 -5.1(8) . . . . ?
C15 C16 C17 C18 -8.9(9) . . . . ?
C15A C14 C19A C18A 1.1(8) . . . . ?
C15A C16A C17 C18A 1.2(9) . . . . ?
C16 C17 C18 C19 7.8(10) . . . . ?
C16A C17 C18A C19A -0.2(11) . . . . ?
C17 C18 C19 C14 -1.1(10) . . . . ?
C17 C18A C19A C14 -1.0(11) . . . . ?
C19 C14 C15 C16 3.8(8) . . . . ?
C19A C14 C15A C16A 0.0(8) . . . . ?
C20 C4 C5 S1 -179.2(2) . . . . ?
C20 C4 C5 C13 2.0(5) . . . . ?
