Regioselective convergent synthesis of 2-arylidene thiazolo[3,2-a]pyrimidines as potential anti-chikungunya agents
Fares, Mohamed; McCosker, Patrick M.; Alsherbiny, Muhammad A.; Willis, Anthony C.; Clark, Timothy; Neyts, Johan; Jochmans, Dirk; Keller, Paul A.; RSC Advances 10 (2020) 5191–5195; doi:10.1039/D0RA00257G

data_7239858
_publ_section_title
;
 Regioselective convergent synthesis of 2-arylidene
 thiazolo[3,2-a]pyrimidines as potential anti-chikungunya agents
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              5191
_journal_page_last               5195
_journal_paper_doi               10.1039/D0RA00257G
_journal_volume                  10
_journal_year                    2020
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_moiety         'C18 H16 N2 O5 S'
_chemical_formula_sum            'C18 H16 N2 O5 S'
_chemical_formula_weight         372.40
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             16-08-03
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2019-11-26 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                87.176(4)
_cell_angle_beta                 74.562(4)
_cell_angle_gamma                73.335(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8375(3)
_cell_length_b                   8.2458(3)
_cell_length_c                   14.5394(7)
_cell_measurement_reflns_used    12423
_cell_measurement_temperature    150
_cell_measurement_theta_max      74
_cell_measurement_theta_min      6
_cell_volume                     867.31(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16946
_diffrn_reflns_theta_full        72.801
_diffrn_reflns_theta_max         74.003
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.952
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro version 1.171.38.43 (Rigaku Oxford Diffraction, 2016)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.0012428
_refine_ls_shift/su_mean         0.0000359
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.51P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0885
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0885
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3396
_reflns_number_total             3491
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.35
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0349
_oxford_refine_ls_scale          5.45(10)
_oxford_reflns_number_all        3491
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\kel1609SN\Tony_kel1609SN_data At 16:18 on'
_cod_data_source_file            d0ra00257g2.cif
_cod_data_source_block           kel1609SN
_cod_depositor_comments          'Adding full bibliography for 7239858.cif.'
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7239858
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S O(5,OCC) O(6,OCC) 
EQUIV O(5,OCC) O(6,OCC) 
WEIGHT -1 O(6,OCC) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
VIBR 0.0, .001 = O(5) TO O(6) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;