Convenient syntheses of 2-acylamino-4-halothiazoles and acylated derivatives using a versatile Boc-intermediate
Pate, Sophie; Taujanskas, Joshua; Wells, Robyn; Robertson, Craig M.; O'Neill, Paul M.; Stachulski, Andrew V.; RSC Advances 14 (2024) 27894–27903; doi:10.1039/D4RA04959D

data_7249275
_publ_section_title
;
 Convenient syntheses of 2-acylamino-4-halothiazoles and acylated
 derivatives using a versatile Boc-intermediate
;
_journal_issue                   38
_journal_name_full               'RSC Advances'
_journal_page_first              27894
_journal_page_last               27903
_journal_paper_doi               10.1039/D4RA04959D
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         '2(C21 H15 Cl N2 O6 S)'
_chemical_formula_sum            'C42 H30 Cl2 N4 O12 S2'
_chemical_formula_weight         917.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-13 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.4035(6)
_cell_length_b                   8.6054(3)
_cell_length_c                   23.5849(6)
_cell_measurement_reflns_used    6735
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.64
_cell_volume                     4141.0(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18121
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.57
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1192 before and 0.0480 after correction. The Ratio of minimum to maximum transmission is 0.9214. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         7989
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0584
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+1.9730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                6797
_reflns_number_total             7989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ra04959d2.cif
_cod_data_source_block           centric
_cod_database_code               7249275
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.54(7)
 0.46(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C32 \\sim O9: within 2A with sigma of 0.00005 and sigma for terminal atoms of
0.00005
4.a Aromatic/amide H refined with riding coordinates:
 C37(H37), C10(H10), C38(H38), C24(H24), C30(H30), C3(H3), C39(H39), C31(H31),
 C40(H40), C16(H16), C17(H17), C8(H8), C9(H9), C28(H28), C19(H19), C18(H18),
 C29(H29), C7(H7)
4.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C33(H33A,H33B,H33C), C21(H21A,H21B,H21C), C42(H42A,H42B,
 H42C)
;
_olex2_submission_special_instructions 'No special instructions were received'