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#$Date: 2024-11-09 04:04:48 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/95/7249563.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_7249563
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 H16 N2 O S'
_chemical_formula_sum            'C18 H16 N2 O S'
_chemical_formula_weight         308.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1281(15)
_cell_length_b                   6.9154(5)
_cell_length_c                   11.3450(9)
_cell_measurement_reflns_used    3343
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.6638
_cell_measurement_theta_min      2.9456
_cell_volume                     1579.2(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.952
_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  0.0629
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.988
_diffrn_reflns_theta_min         2.024
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.652477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0418 before and 0.0337 after correction. The Ratio of minimum to maximum transmission is 0.6525. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0441
_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)+(0.0737P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1232
_reflns_number_total             2163
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05436a2.cif
_cod_data_source_block           shp-61-pnma
_cod_database_code               7249563
_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. Others
 Fixed Sof: H20A(0.5) H20B(0.5) H20C(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_original_sample_id 'sph 61'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_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 0.31990(3) 0.2500 0.61031(6) 0.0582(3) Uani 1 2 d S T P . .
O1 O 0.26187(9) 0.2500 0.81966(17) 0.0643(6) Uani 1 2 d S T P . .
N3 N 0.22090(9) 0.2500 0.47106(17) 0.0457(5) Uani 1 2 d S T P . .
N6 N 0.18589(9) 0.2500 0.66684(17) 0.0476(5) Uani 1 2 d S T P . .
C2 C 0.23452(11) 0.2500 0.5887(2) 0.0456(6) Uani 1 2 d S T P . .
C4 C 0.27651(12) 0.2500 0.3970(2) 0.0485(6) Uani 1 2 d S T P . .
C5 C 0.33264(13) 0.2500 0.4597(2) 0.0604(8) Uani 1 2 d S T P . .
H5 H 0.3746 0.2500 0.4255 0.073 Uiso 1 2 calc R U P . .
C7 C 0.20373(12) 0.2500 0.7825(2) 0.0474(6) Uani 1 2 d S T P . .
C8 C 0.14639(13) 0.2500 0.8667(2) 0.0460(6) Uani 1 2 d S T P . .
C9 C 0.15804(15) 0.2500 0.9869(2) 0.0617(8) Uani 1 2 d S T P . .
H9 H 0.2016 0.2500 1.0144 0.074 Uiso 1 2 calc R U P . .
C10 C 0.10674(18) 0.2500 1.0659(3) 0.0790(10) Uani 1 2 d S T P . .
H10 H 0.1154 0.2500 1.1464 0.095 Uiso 1 2 calc R U P . .
C11 C 0.04309(19) 0.2500 1.0260(3) 0.1023(14) Uani 1 2 d S T P . .
H11 H 0.0080 0.2500 1.0794 0.123 Uiso 1 2 calc R U P . .
C12 C 0.03032(18) 0.2500 0.9067(3) 0.1147(17) Uani 1 2 d S T P . .
H12 H -0.0134 0.2500 0.8801 0.138 Uiso 1 2 calc R U P . .
C13 C 0.08159(13) 0.2500 0.8269(3) 0.0689(9) Uani 1 2 d S T P . .
H13 H 0.0727 0.2500 0.7464 0.083 Uiso 1 2 calc R U P . .
C14 C 0.15257(11) 0.2500 0.43044(19) 0.0429(6) Uani 1 2 d S T P . .
C15 C 0.12056(9) 0.0771(3) 0.41219(17) 0.0571(5) Uani 1 1 d . . . . .
H15 H 0.1429 -0.0395 0.4217 0.069 Uiso 1 1 calc R U . . .
C16 C 0.05417(9) 0.0799(3) 0.37927(17) 0.0648(6) Uani 1 1 d . . . . .
H16 H 0.0322 -0.0368 0.3670 0.078 Uiso 1 1 calc R U . . .
C17 C 0.01988(13) 0.2500 0.3643(2) 0.0552(7) Uani 1 2 d S T P . .
C20 C 0.26628(13) 0.2500 0.2661(2) 0.0598(7) Uani 1 2 d S T P . .
H20A H 0.2352 0.1504 0.2452 0.090 Uiso 0.5 1 calc R U P A -1
H20B H 0.3079 0.2263 0.2274 0.090 Uiso 0.5 1 calc R U P A -1
H20C H 0.2492 0.3733 0.2418 0.090 Uiso 0.5 1 calc R U P A -1
C21 C -0.05291(13) 0.2500 0.3313(3) 0.0781(10) Uani 1 2 d S T P . .
H21A H -0.0589 0.1795 0.2592 0.117 Uiso 0.5 1 calc R U P B -1
H21B H -0.0678 0.3807 0.3208 0.117 Uiso 0.5 1 calc R U P B -1
H21C H -0.0782 0.1897 0.3929 0.117 Uiso 0.5 1 calc R U P B -1
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
C5 S1 C2 90.41(12) . . ?
C2 N3 C4 115.28(19) . . ?
C2 N3 C14 120.13(18) . . ?
C4 N3 C14 124.6(2) . . ?
C2 N6 C7 116.9(2) . . ?
N3 C2 S1 109.73(17) . . ?
N6 C2 S1 129.70(19) . . ?
N6 C2 N3 120.6(2) . . ?
N3 C4 C20 119.0(2) . . ?
C5 C4 N3 110.9(2) . . ?
C5 C4 C20 130.1(2) . . ?
S1 C5 H5 123.2 . . ?
C4 C5 S1 113.64(19) . . ?
C4 C5 H5 123.2 . . ?
O1 C7 N6 125.1(2) . . ?
O1 C7 C8 120.6(2) . . ?
N6 C7 C8 114.3(2) . . ?
C9 C8 C7 119.8(2) . . ?
C13 C8 C7 121.3(2) . . ?
C13 C8 C9 118.9(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C15 C14 N3 119.50(12) . . ?
C15 C14 N3 119.50(12) 8_565 . ?
C15 C14 C15 121.0(2) 8_565 . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.68(19) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C16 117.7(2) 8_565 . ?
C16 C17 C21 121.14(12) 8_565 . ?
C16 C17 C21 121.14(12) . . ?
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 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 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
S1 C2 1.736(2) . ?
S1 C5 1.728(3) . ?
O1 C7 1.244(3) . ?
N3 C2 1.362(3) . ?
N3 C4 1.399(3) . ?
N3 C14 1.451(3) . ?
N6 C2 1.321(3) . ?
N6 C7 1.361(3) . ?
C4 C5 1.335(3) . ?
C4 C20 1.500(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.498(4) . ?
C8 C9 1.383(3) . ?
C8 C13 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.359(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C14 C15 1.374(2) 8_565 ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 C16 1.375(3) 8_565 ?
C17 C21 1.512(3) . ?
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
O1 C7 C8 C9 0.000(1) . . . . ?
O1 C7 C8 C13 180.000(1) . . . . ?
N3 C4 C5 S1 0.000(0) . . . . ?
N3 C14 C15 C16 176.68(18) . . . . ?
N6 C7 C8 C9 180.000(1) . . . . ?
N6 C7 C8 C13 0.000(1) . . . . ?
C2 S1 C5 C4 0.000(0) . . . . ?
C2 N3 C4 C5 0.000(0) . . . . ?
C2 N3 C4 C20 180.000(0) . . . . ?
C2 N3 C14 C15 -89.60(19) . . . . ?
C2 N3 C14 C15 89.60(19) . . . 8_565 ?
C2 N6 C7 O1 0.000(1) . . . . ?
C2 N6 C7 C8 180.000(0) . . . . ?
C4 N3 C2 S1 0.000(0) . . . . ?
C4 N3 C2 N6 180.000(0) . . . . ?
C4 N3 C14 C15 90.40(19) . . . . ?
C4 N3 C14 C15 -90.40(19) . . . 8_565 ?
C5 S1 C2 N3 0.000(0) . . . . ?
C5 S1 C2 N6 180.000(0) . . . . ?
C7 N6 C2 S1 0.000(0) . . . . ?
C7 N6 C2 N3 180.000(0) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C7 C8 C13 C12 180.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C8 C13 C12 0.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C11 C12 C13 C8 0.000(1) . . . . ?
C13 C8 C9 C10 0.000(1) . . . . ?
C14 N3 C2 S1 180.000(0) . . . . ?
C14 N3 C2 N6 0.000(0) . . . . ?
C14 N3 C4 C5 180.000(0) . . . . ?
C14 N3 C4 C20 0.000(0) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C15 C16 -2.5(4) 8_565 . . . ?
C15 C16 C17 C16 2.1(4) . . . 8_565 ?
C15 C16 C17 C21 -178.5(2) . . . . ?
C20 C4 C5 S1 180.000(0) . . . . ?
