#------------------------------------------------------------------------------
#$Date: 2024-09-03 04:18:18 +0300 (Tue, 03 Sep 2024) $
#$Revision: 294336 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/92/7249273.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_7249273
loop_
_publ_author_name
'Pate, Sophie'
'Taujanskas, Joshua'
'Wells, Robyn'
'Robertson, Craig M.'
'O'Neill, Paul M.'
'Stachulski, Andrew V.'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -32.00   0.50    2.00    --  -10.30  36.00 -54.00   60
  2  ω    -38.00  79.00   0.50    2.00    --  -10.30  57.00  90.00  234
  3  ω     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       'ω 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/[σ²(Fo²)+(0.0428P)²+0.9349P] where P=(Fo²+2Fc²)/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 > 2σ(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_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.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, 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 0.48887(2) 0.24759(4) 0.59691(3) 0.01520(12) Uani 1 1 d . . . . .
O1 O 0.37699(4) 0.11863(14) 0.53145(8) 0.0199(2) Uani 1 1 d . . . . .
O2 O 0.63268(4) 0.38637(14) 0.41480(8) 0.0181(2) Uani 1 1 d . . . . .
O3 O 0.68082(5) 0.45906(17) 0.59102(9) 0.0275(3) Uani 1 1 d . . . . .
N2 N 0.43836(5) 0.18026(16) 0.37082(9) 0.0145(2) Uani 1 1 d . . . . .
H2 H 0.441491 0.183755 0.290005 0.017 Uiso 1 1 calc R . . . .
N1 N 0.53848(5) 0.27406(15) 0.38394(10) 0.0141(2) Uani 1 1 d . . . . .
C6 C 0.67898(6) 0.46049(18) 0.48112(12) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.38467(6) 0.12463(18) 0.42024(12) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.57987(5) 0.32779(18) 0.46970(11) 0.0145(3) Uani 1 1 d . . . . .
C7 C 0.72440(6) 0.5435(2) 0.39636(13) 0.0208(3) Uani 1 1 d . . . . .
H7A H 0.723056 0.478860 0.316881 0.031 Uiso 1 1 calc GR . . . .
H7B H 0.764750 0.530663 0.432317 0.031 Uiso 1 1 calc GR . . . .
H7C H 0.715304 0.675801 0.384074 0.031 Uiso 1 1 calc GR . . . .
C5 C 0.33724(6) 0.0725(2) 0.32817(12) 0.0205(3) Uani 1 1 d . . . . .
H5A H 0.322194 -0.052837 0.346469 0.031 Uiso 1 1 calc GR . . . .
H5B H 0.354643 0.074443 0.245154 0.031 Uiso 1 1 calc GR . . . .
H5C H 0.303853 0.161702 0.332656 0.031 Uiso 1 1 calc GR . . . .
C1 C 0.48774(5) 0.23104(17) 0.43919(13) 0.0132(3) Uani 1 1 d . . . . .
C3 C 0.56286(6) 0.32295(19) 0.58913(11) 0.0161(3) Uani 1 1 d . . . . .
H3 H 0.587458 0.355520 0.657521 0.019 Uiso 1 1 calc R . . . .
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
C1 S1 C3 89.24(6) . . ?
C6 O2 C2 122.05(10) . . ?
C4 N2 C1 124.12(11) . . ?
C1 N1 C2 109.38(11) . . ?
O2 C6 C7 109.86(11) . . ?
O3 C6 O2 123.40(12) . . ?
O3 C6 C7 126.73(12) . . ?
O1 C4 N2 121.39(12) . . ?
O1 C4 C5 123.59(11) . . ?
N2 C4 C5 115.02(11) . . ?
N1 C2 O2 111.27(10) . . ?
C3 C2 O2 131.26(11) . . ?
C3 C2 N1 117.41(11) . . ?
N2 C1 S1 124.72(10) . . ?
N1 C1 S1 115.30(10) . . ?
N1 C1 N2 119.98(12) . . ?
C2 C3 S1 108.64(9) . . ?
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 C1 1.7156(14) . ?
S1 C3 1.7289(13) . ?
O1 C4 1.2193(16) . ?
O2 C6 1.3618(15) . ?
O2 C2 1.3790(15) . ?
O3 C6 1.1932(16) . ?
N2 C4 1.3649(16) . ?
N2 C1 1.3714(16) . ?
N1 C2 1.3625(16) . ?
N1 C1 1.3111(17) . ?
C6 C7 1.4881(18) . ?
C4 C5 1.4977(17) . ?
C2 C3 1.3500(17) . ?
