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_7249274
_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         'C5 H5 Cl N2 O S'
_chemical_formula_sum            'C5 H5 Cl N2 O S'
_chemical_formula_weight         176.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                90.462(3)
_cell_angle_beta                 91.106(3)
_cell_angle_gamma                108.081(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0499(2)
_cell_length_b                   7.4591(3)
_cell_length_c                   9.4964(3)
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.1260
_cell_measurement_theta_min      2.1620
_cell_volume                     339.94(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.834
_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   -100.00  29.00   0.50    5.00    --  -10.20 -72.00  90.00  258
  2  \w   -100.00  26.00   0.50    5.00    --  -10.20 -57.00 -30.00  252
  3  \w   -100.00  79.00   0.50    5.00    --  -10.20  19.00-180.00  358
  4  \w   -100.00  39.00   0.50    5.00    --  -10.20 -38.00-150.00  278
  5  \w    -50.00  53.00   0.50    5.00    --  -10.20  72.00-120.00  206
  6  \w    -50.00  79.00   0.50    5.00    --  -10.20  72.00 -60.00  258
;
_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      -0.0060843000
_diffrn_orient_matrix_UB_12      -0.0484248000
_diffrn_orient_matrix_UB_13      -0.0651621000
_diffrn_orient_matrix_UB_21      0.0467842000
_diffrn_orient_matrix_UB_22      -0.0690890000
_diffrn_orient_matrix_UB_23      0.0343493000
_diffrn_orient_matrix_UB_31      -0.1400599000
_diffrn_orient_matrix_UB_32      -0.0537614000
_diffrn_orient_matrix_UB_33      0.0124959000
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7149
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.213
_diffrn_reflns_theta_min         2.145
_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    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76389
_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    1.725
_exptl_crystal_description       needle
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.1190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1578
_reflns_number_total             1682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra04959d2.cif
_cod_data_source_block           avs_30_11_23_dry_auto
_cod_database_code               7249274
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     'AVS_30_11_23 dry sample'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.925
_diffrn_oxdiff_digest_frames
;
01cb9a27efd4f1e71af5e66352a1c5f623000260564
;
_diffrn_oxdiff_digest_hkl
;
01e777fa1d499bcd35d46013f7b7097d2593d1
;
_reflns_odcompleteness_completeness 99.79
_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), C2(H2A)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              8124
_shelx_hkl_checksum              47267
_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 1.859
_oxdiff_exptl_absorpt_empirical_full_min 0.375