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_7249273
_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_formula_moiety         'C7 H8 N2 O3 S'
_chemical_formula_sum            'C7 H8 N2 O3 S'
_chemical_formula_weight         200.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-11
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-02-02 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.162(3)
_cell_length_b                   7.1809(10)
_cell_length_c                   10.8505(15)
_cell_measurement_reflns_used    4299
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.0770
_cell_measurement_theta_min      2.9950
_cell_volume                     1726.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00 -32.00   0.50    2.00    --  -10.30  36.00 -54.00   60
  2  \w    -38.00  79.00   0.50    2.00    --  -10.30  57.00  90.00  234
  3  \w     29.00  59.00   0.50    2.00    --  -10.30  36.00 -54.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0152226000
_diffrn_orient_matrix_UB_12      -0.0810768000
_diffrn_orient_matrix_UB_13      0.0205016000
_diffrn_orient_matrix_UB_21      0.0277604000
_diffrn_orient_matrix_UB_22      -0.0370411000
_diffrn_orient_matrix_UB_23      0.0215680000
_diffrn_orient_matrix_UB_31      -0.0049634000
_diffrn_orient_matrix_UB_32      0.0420942000
_diffrn_orient_matrix_UB_33      0.0581652000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7410
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.208
_diffrn_reflns_theta_min         2.982
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.9349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1838
_reflns_number_total             2080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra04959d2.cif
_cod_data_source_block           avs04_106_auto
_cod_database_code               7249273
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CH8N2O3S
_chemical_oxdiff_usercomment     AVS04_106
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.927
_diffrn_oxdiff_digest_frames
;
0166b5f0fe4c86f724e6c3b266d2e968c300029499f
;
_diffrn_oxdiff_digest_hkl
;
01bfc94518f7a7509aef32726d1fcc47ddfe5b
;
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              43409
_shelx_hkl_checksum              51567
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.801