#------------------------------------------------------------------------------
#$Date: 2026-04-05 13:52:41 +0200 (Sun, 05 Apr 2026) $
#$Revision: 305334 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/57/64/1576449.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_1576449
loop_
_publ_author_name
'Hwang, Meemie U.'
'Gogoi, Achyut'
'Scurria, Matthew'
'Gutierrez, Osvaldo'
'Scheidt, Karl A.'
_publ_section_title
;
 Photochemical cyclization of α-amino esters to access
 3-azetidinones.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              6766
_journal_page_last               6772
_journal_paper_doi               10.1039/d5sc09994c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C21 H24 N3 O3 S, C F3 O3 S, 0.5(Cl2 H2 C1)'
_chemical_formula_sum            'C22.5 H25 Cl F3 N3 O6 S2'
_chemical_formula_weight         590.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2np1v8
_audit_creation_date             2024-01-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-06-09 deposited with the CCDC.	2026-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.585(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.0211(6)
_cell_length_b                   8.3937(3)
_cell_length_c                   25.1936(6)
_cell_measurement_reflns_used    27664
_cell_measurement_temperature    100.3(6)
_cell_measurement_theta_max      75.2150
_cell_measurement_theta_min      3.4840
_cell_volume                     5244.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.101a 64-bit (release 13-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.3(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -69.00   0.50    0.10    --  -48.85 -10.00-114.00   60
  2  ω    -27.00   0.00   0.50    0.10    --  -48.85  10.00  58.00   54
  3  ω    -11.00  14.00   0.50    0.10    --   48.85 -10.00-114.00   50
  4  ω     57.00  82.00   0.50    0.10    --   48.85  10.00  58.00   50
  5  ω    126.00 151.00   0.50    0.70    --  101.75  10.00  58.00   50
  6  ω   -148.00-107.00   0.50    0.70    -- -103.00 -10.00-114.00   82
  7  ω   -107.00 -42.00   0.50    0.10    --  -48.85 -37.00-180.00  130
  8  ω    -29.00  25.00   0.50    0.10    --  -48.85  19.00-180.00  108
  9  ω     36.00  63.00   0.50    0.10    --   48.85  57.00 120.00   54
 10  ω     92.00 120.00   0.50    0.10    --   48.85  77.00-180.00   56
 11  ω     29.00  59.00   0.50    0.10    --   48.85  77.00  90.00   60
 12  ω     28.00  54.00   0.50    0.10    --   48.85  77.00 150.00   52
 13  ω     36.00  65.00   0.50    0.10    --   48.85  57.00 150.00   58
 14  ω     40.00  65.00   0.50    0.10    --   48.85  57.00-180.00   50
 15  ω     42.00  80.00   0.50    0.10    --   48.85  37.00 120.00   76
 16  ω     79.00 120.00   0.50    0.10    --   48.85  19.00-180.00   82
 17  ω     39.00  76.00   0.50    0.10    --   48.85  57.00-120.00   74
 18  ω     29.00  74.00   0.50    0.10    --   48.85  77.00-150.00   90
 19  ω     45.00  74.00   0.50    0.10    --   48.85  19.00-180.00   58
 20  ω     28.00  63.00   0.50    0.10    --   48.85  77.00-180.00   70
 21  ω     32.00  59.00   0.50    0.10    --   48.85  77.00-120.00   54
 22  ω     41.00  83.00   0.50    0.10    --   48.85  37.00-180.00   84
 23  ω     20.00  91.00   0.50    0.10    --   48.85-125.00  60.00  142
 24  ω     28.00  54.00   0.50    0.10    --   48.85  77.00 120.00   52
 25  ω     90.00 173.00   0.50    0.70    --  101.75  61.00 150.00  166
 26  ω    138.00 163.00   0.50    0.70    --  101.75  77.00-180.00   50
 27  ω     88.00 118.00   0.50    0.70    --  101.75  61.00 120.00   60
 28  ω     33.00  65.00   0.50    0.70    --  101.75 -77.00  60.00   64
 29  ω    135.00 173.00   0.50    0.70    --  101.75  77.00  60.00   76
 30  ω     81.00 107.00   0.50    0.70    --  101.75  77.00-180.00   52
 31  ω     88.00 114.00   0.50    0.70    --  101.75  61.00  90.00   52
 32  ω     89.00 116.00   0.50    0.70    --  101.75  61.00-150.00   54
 33  ω     89.00 118.00   0.50    0.70    --  101.75  61.00-180.00   58
 34  ω     31.00 104.00   0.50    0.70    --  101.75 -94.00   0.00  146
 35  ω     74.00 102.00   0.50    0.70    --  101.75 -77.00  60.00   56
 36  ω     32.00  73.00   0.50    0.70    --  101.75 -61.00  60.00   82
 37  ω     35.00  67.00   0.50    0.70    --  101.75 -77.00-180.00   64
 38  ω     79.00 106.00   0.50    0.70    --  101.75 -94.00-150.00   54
 39  ω     93.00 173.00   0.50    0.70    --  101.75  45.00-150.00  160
 40  ω    135.00 160.00   0.50    0.70    --  101.75  77.00 120.00   50
 41  ω     93.00 173.00   0.50    0.70    --  101.75  45.00 120.00  160
 42  ω    146.00 171.00   0.50    0.70    --  101.75  77.00 150.00   50
 43  ω    143.00 171.00   0.50    0.70    --  101.75  77.00  90.00   56
 44  ω     94.00 173.00   0.50    0.70    --  101.75  45.00  90.00  158
 45  ω     81.00 107.00   0.50    0.70    --  101.75  77.00 120.00   52
 46  ω     81.00 107.00   0.50    0.70    --  101.75  77.00  60.00   52
 47  ω     81.00 107.00   0.50    0.70    --  101.75  77.00 150.00   52
 48  ω     74.00 100.00   0.50    0.70    --  101.75 -77.00-180.00   52
 49  ω     31.00  75.00   0.50    0.70    --  101.75 -61.00  30.00   88
 50  ω    137.00 164.00   0.50    0.70    --  101.75  61.00  60.00   54
 51  ω     81.00 107.00   0.50    0.70    --  101.75  77.00-150.00   52
 52  ω     88.00 114.00   0.50    0.70    --  101.75  61.00  60.00   52
 53  ω     81.00 107.00   0.50    0.70    --  101.75  77.00  90.00   52
 54  ω     34.00 107.00   0.50    0.70    --  101.75-125.00-180.00  146
 55  ω     30.00  75.00   0.50    0.70    --  101.75 -61.00  90.00   90
 56  ω   -110.00 -83.00   0.50    0.70    -- -103.00 -76.00 162.47   54
 57  ω   -109.00 -83.00   0.50    0.70    -- -103.00 -76.00 159.20   52
 58  ω   -109.00 -83.00   0.50    0.70    -- -103.00 -76.00-170.61   52
 59  ω   -112.00 -86.00   0.50    0.70    -- -103.00 -68.00 118.57   52
 60  ω   -136.00 -86.00   0.50    0.70    -- -103.00 -68.00  91.70  100
 61  ω   -121.00 -91.00   0.50    0.70    -- -103.00 -56.00 119.64   60
 62  ω   -108.00 -82.00   0.50    0.70    -- -103.00 -77.00 120.00   52
 63  ω   -110.00 -83.00   0.50    0.70    -- -103.00 -76.00-175.23   54
 64  ω   -109.00 -83.00   0.50    0.70    -- -103.00 -74.00-133.09   52
 65  ω   -173.00-147.00   0.50    0.70    -- -103.00 -76.00-175.23   52
 66  ω   -109.00 -84.00   0.50    0.70    -- -103.00 -72.00-129.67   50
 67  ω   -169.00-119.00   0.50    0.70    -- -103.00 -72.00-129.67  100
 68  ω   -111.00 -84.00   0.50    0.70    -- -103.00 -72.00-141.69   54
 69  ω    -62.00 -34.00   0.50    0.70    -- -103.00  61.00-180.00   56
 70  ω   -106.00 -80.00   0.50    0.70    -- -103.00 -83.00 107.29   52
 71  ω   -105.00 -80.00   0.50    0.70    -- -103.00 -81.00  96.34   50
 72  ω   -174.00-110.00   0.50    0.70    -- -103.00 -81.00  96.34  128
 73  ω   -108.00 -82.00   0.50    0.70    -- -103.00 -77.00-180.00   52
 74  ω   -107.00 -81.00   0.50    0.70    -- -103.00 -80.00-142.36   52
 75  ω   -109.00 -82.00   0.50    0.70    -- -103.00 -77.00 150.00   54
 76  ω   -123.00 -87.00   0.50    0.70    -- -103.00 -65.00 109.70   72
 77  ω   -130.00 -89.00   0.50    0.70    -- -103.00 -59.00-154.40   82
 78  ω   -170.00-145.00   0.50    0.70    -- -103.00 -77.00 150.00   50
 79  ω   -137.00 -90.00   0.50    0.70    -- -103.00 -56.00-148.83   94
 80  ω   -107.00 -81.00   0.50    0.70    -- -103.00 -79.00-152.59   52
 81  ω   -160.00-135.00   0.50    0.70    -- -103.00 -79.00-152.59   50
 82  ω   -108.00 -83.00   0.50    0.70    -- -103.00 -76.00 155.88   50
 83  ω   -172.00-146.00   0.50    0.70    -- -103.00 -76.00 155.88   52
 84  ω   -110.00 -81.00   0.50    0.70    -- -103.00 -83.00 119.79   58
 85  ω   -105.00 -80.00   0.50    0.70    -- -103.00 -81.00 121.51   50
 86  ω   -107.00 -80.00   0.50    0.70    -- -103.00 -83.00-132.34   54
 87  ω   -108.00 -81.00   0.50    0.70    -- -103.00 -79.00 176.50   54
 88  ω   -160.00-134.00   0.50    0.70    -- -103.00 -81.00 121.51   52
 89  ω   -108.00 -82.00   0.50    0.70    -- -103.00 -77.00-120.00   52
 90  ω   -114.00 -83.00   0.50    0.70    -- -103.00 -76.00 166.34   62
 91  ω    -59.00 -34.00   0.50    0.70    -- -103.00 125.00 150.00   50
 92  ω   -133.00 -91.00   0.50    0.70    -- -103.00 -57.00 118.00   84
 93  ω   -109.00 -83.00   0.50    0.70    -- -103.00 -74.00 148.63   52
 94  ω   -113.00 -86.00   0.50    0.70    -- -103.00 -68.00 135.58   54
 95  ω   -112.00 -85.00   0.50    0.70    -- -103.00 -71.00 128.66   54
 96  ω   -111.00 -85.00   0.50    0.70    -- -103.00 -71.00-174.97   52
 97  ω   -111.00 -80.00   0.50    0.70    -- -103.00 125.00 150.00   62
 98  ω   -113.00 -86.00   0.50    0.70    -- -103.00 -67.00-122.67   54
 99  ω   -108.00 -82.00   0.50    0.70    -- -103.00 -78.00 128.54   52
100  ω   -108.00 -81.00   0.50    0.70    -- -103.00 -80.00-158.83   54
101  ω   -174.00 -91.00   0.50    0.70    -- -103.00 -61.00-180.00  166
102  ω   -107.00 -80.00   0.50    0.70    -- -103.00 -82.00-143.42   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0455100000
_diffrn_orient_matrix_UB_12      -0.0224081000
_diffrn_orient_matrix_UB_13      0.0350250000
_diffrn_orient_matrix_UB_21      0.0415654000
_diffrn_orient_matrix_UB_22      0.0114509000
_diffrn_orient_matrix_UB_23      0.0508230000
_diffrn_orient_matrix_UB_31      -0.0082918000
_diffrn_orient_matrix_UB_32      0.1814702000
_diffrn_orient_matrix_UB_33      0.0010802000
_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  0.1107
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            60284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.664
_diffrn_reflns_theta_min         3.540
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.364
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.101a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.494
_exptl_crystal_description       needle
_exptl_crystal_F_000             2440
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5429
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0700
_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)+(0.1025P)²+11.8840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1841
_refine_ls_wR_factor_ref         0.1875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5069
_reflns_number_total             5429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc09994c1.cif
_cod_data_source_block           cx3273
_cod_depositor_comments
'Adding full bibliography for 1576448--1576450.cif.'
_cod_original_cell_volume        5244.8(2)
_cod_original_formula_sum        'C22.50 H25 Cl F3 N3 O6 S2'
_cod_database_code               1576449
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         C22H24F3N3O6S2
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C23 \\sim Cl1A-C23A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim C23 \\sim Cl1A \\sim C23A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 Cl1, C23, Cl1A, C23A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl1A)=1-FVAR(1)
 Sof(C23A)=Sof(H23C)=Sof(H23D)=0.5*(1-FVAR(2))
 Sof(C23)=Sof(H23A)=Sof(H23B)=0.5*FVAR(2)
 Sof(Cl1)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1A)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C23(H23A,H23B), C23A(H23C,H23D)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16),
 C17(H17), C19(H19), C20(H20)
6.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_olex2_date_sample_data_collection 2024-01-23
_olex2_date_sample_submission    2024-01-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_original_sample_id cx3273
_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 1.881
_oxdiff_exptl_absorpt_empirical_full_min 0.380
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.29213(3) 0.20563(10) 0.80613(3) 0.0405(2) Uani 1 1 d . . . . .
O1 O 0.39186(8) 0.3301(3) 0.67827(8) 0.0348(4) Uani 1 1 d . . . . .
H1 H 0.3879(16) 0.256(5) 0.6544(18) 0.048(11) Uiso 1 1 d . . . . .
O2 O 0.28876(10) 0.0352(3) 0.80385(8) 0.0502(6) Uani 1 1 d . . . . .
O3 O 0.24224(9) 0.2917(4) 0.80020(9) 0.0538(7) Uani 1 1 d . . . . .
N1 N 0.33006(10) 0.2546(3) 0.76021(9) 0.0356(5) Uani 1 1 d . . . . .
N2 N 0.33350(9) 0.6130(3) 0.62966(9) 0.0336(5) Uani 1 1 d . . . . .
N3 N 0.27206(9) 0.4400(3) 0.60335(9) 0.0327(5) Uani 1 1 d . . . . .
C1 C 0.33785(11) 0.4275(4) 0.74567(10) 0.0318(6) Uani 1 1 d . . . . .
H1A H 0.303929 0.488543 0.748089 0.038 Uiso 1 1 calc R U . . .
C2 C 0.33852(11) 0.3667(3) 0.68668(11) 0.0313(6) Uani 1 1 d . . . . .
C3 C 0.30761(12) 0.2192(4) 0.70342(11) 0.0363(6) Uani 1 1 d . . . . .
H3A H 0.267899 0.228902 0.695917 0.044 Uiso 1 1 calc R U . . .
H3B H 0.320149 0.116940 0.689827 0.044 Uiso 1 1 calc R U . . .
C4 C 0.31373(11) 0.4709(3) 0.64138(10) 0.0309(6) Uani 1 1 d . . . . .
C5 C 0.30398(12) 0.6736(4) 0.58428(11) 0.0384(6) Uani 1 1 d . . . . .
H5 H 0.309593 0.772667 0.567636 0.046 Uiso 1 1 calc R U . . .
C6 C 0.26559(12) 0.5656(4) 0.56797(11) 0.0374(6) Uani 1 1 d . . . . .
H6 H 0.238902 0.574363 0.537584 0.045 Uiso 1 1 calc R U . . .
C7 C 0.38440(11) 0.5076(4) 0.77905(11) 0.0333(6) Uani 1 1 d . . . . .
C8 C 0.37639(13) 0.6532(4) 0.80217(13) 0.0428(7) Uani 1 1 d . . . . .
H8 H 0.342740 0.706261 0.794219 0.051 Uiso 1 1 calc R U . . .
C9 C 0.41761(16) 0.7224(5) 0.83716(16) 0.0545(9) Uani 1 1 d . . . . .
H9 H 0.411893 0.821893 0.853504 0.065 Uiso 1 1 calc R U . . .
C10 C 0.46699(15) 0.6463(5) 0.84816(15) 0.0532(9) Uani 1 1 d . . . . .
H10 H 0.494987 0.693591 0.872182 0.064 Uiso 1 1 calc R U . . .
C11 C 0.47567(13) 0.5023(4) 0.82440(13) 0.0457(8) Uani 1 1 d . . . . .
H11 H 0.509780 0.451476 0.831600 0.055 Uiso 1 1 calc R U . . .
C12 C 0.43431(12) 0.4311(4) 0.78975(12) 0.0381(6) Uani 1 1 d . . . . .
H12 H 0.440051 0.331467 0.773556 0.046 Uiso 1 1 calc R U . . .
C13 C 0.37738(12) 0.7003(4) 0.66156(13) 0.0400(7) Uani 1 1 d . . . . .
H13A H 0.363233 0.756334 0.690856 0.060 Uiso 1 1 calc R U . . .
H13B H 0.392798 0.777709 0.638721 0.060 Uiso 1 1 calc R U . . .
H13C H 0.405414 0.625135 0.676386 0.060 Uiso 1 1 calc R U . . .
C14 C 0.23764(12) 0.2989(4) 0.59688(11) 0.0382(6) Uani 1 1 d . . . . .
H14A H 0.259961 0.202945 0.602798 0.057 Uiso 1 1 calc R U . . .
H14B H 0.218019 0.296890 0.560552 0.057 Uiso 1 1 calc R U . . .
H14C H 0.211851 0.302118 0.622950 0.057 Uiso 1 1 calc R U . . .
C15 C 0.33139(12) 0.2660(4) 0.86539(11) 0.0354(6) Uani 1 1 d . . . . .
C16 C 0.31394(14) 0.3877(4) 0.89571(13) 0.0429(7) Uani 1 1 d . . . . .
H16 H 0.281418 0.442872 0.883790 0.051 Uiso 1 1 calc R U . . .
C17 C 0.34432(15) 0.4281(4) 0.94352(13) 0.0449(7) Uani 1 1 d . . . . .
H17 H 0.332455 0.511749 0.964508 0.054 Uiso 1 1 calc R U . . .
C18 C 0.39175(13) 0.3490(4) 0.96143(12) 0.0394(6) Uani 1 1 d . . . . .
C19 C 0.40863(12) 0.2269(4) 0.93042(13) 0.0418(7) Uani 1 1 d . . . . .
H19 H 0.441046 0.171339 0.942441 0.050 Uiso 1 1 calc R U . . .
C20 C 0.37879(13) 0.1850(4) 0.88212(12) 0.0403(7) Uani 1 1 d . . . . .
H20 H 0.390698 0.102091 0.860850 0.048 Uiso 1 1 calc R U . . .
C21 C 0.42414(17) 0.3905(5) 1.01444(15) 0.0560(9) Uani 1 1 d . . . . .
H21A H 0.407511 0.481641 1.030263 0.084 Uiso 1 1 calc R U . . .
H21B H 0.461043 0.418075 1.008836 0.084 Uiso 1 1 calc R U . . .
H21C H 0.424899 0.298951 1.038647 0.084 Uiso 1 1 calc R U . . .
S2 S 0.36096(3) 0.11240(8) 0.54786(3) 0.0327(2) Uani 1 1 d . . . . .
F1 F 0.45835(8) -0.0043(3) 0.54730(11) 0.0611(6) Uani 1 1 d . . . . .
F2 F 0.45586(9) 0.2461(3) 0.56591(11) 0.0641(6) Uani 1 1 d . . . . .
F3 F 0.43447(10) 0.1646(3) 0.48461(10) 0.0693(7) Uani 1 1 d . . . . .
O4 O 0.36614(10) 0.0864(3) 0.60538(8) 0.0443(5) Uani 1 1 d . . . . .
O5 O 0.34092(9) -0.0232(3) 0.51673(9) 0.0428(5) Uani 1 1 d . . . . .
O6 O 0.33782(9) 0.2630(3) 0.53024(9) 0.0415(5) Uani 1 1 d . . . . .
C22 C 0.43099(14) 0.1301(4) 0.53587(15) 0.0497(8) Uani 1 1 d . . . . .
Cl1 Cl 0.4725(10) 0.0203(10) 0.7028(8) 0.075(4) Uani 0.34(3) 1 d D U P A 1
C23 C 0.500000 -0.115(3) 0.750000 0.114(11) Uani 0.34(3) 2 d DS TU P A 1
H23A H 0.527772 -0.183053 0.736690 0.136 Uiso 0.170(17) 1 calc R U P A 1
H23B H 0.472229 -0.183060 0.763309 0.136 Uiso 0.170(17) 1 calc R U P A 1
Cl1A Cl 0.4894(3) 0.0379(8) 0.6872(4) 0.0724(14) Uani 0.66(3) 1 d D U P A 2
C23A C 0.500000 -0.053(3) 0.750000 0.145(7) Uani 0.66(3) 2 d DS TU P A 2
H23C H 0.531418 -0.123668 0.748863 0.174 Uiso 0.330(17) 1 calc R U P A 2
H23D H 0.468585 -0.123678 0.751137 0.174 Uiso 0.330(17) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-fx6km 2025
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0312
0 0 -1 0.0312
1 0 0 0.0180
-1 0 0 0.0030
0 1 0 0.1970
0 -1 0 0.1560
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
O2 S1 N1 104.94(14) . . ?
O2 S1 C15 110.27(15) . . ?
O3 S1 O2 116.95(16) . . ?
O3 S1 N1 112.13(14) . . ?
O3 S1 C15 109.03(16) . . ?
N1 S1 C15 102.54(13) . . ?
C2 O1 H1 104(3) . . ?
C1 N1 S1 120.95(19) . . ?
C3 N1 S1 116.42(18) . . ?
C3 N1 C1 90.2(2) . . ?
C4 N2 C5 109.8(2) . . ?
C4 N2 C13 126.5(2) . . ?
C5 N2 C13 123.5(3) . . ?
C4 N3 C6 109.1(2) . . ?
C4 N3 C14 128.8(3) . . ?
C6 N3 C14 122.1(2) . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 C2 86.3(2) . . ?
C2 C1 H1A 109.8 . . ?
C7 C1 N1 114.1(2) . . ?
C7 C1 H1A 109.8 . . ?
C7 C1 C2 124.7(2) . . ?
O1 C2 C1 109.9(2) . . ?
O1 C2 C3 112.5(2) . . ?
O1 C2 C4 108.4(2) . . ?
C3 C2 C1 86.2(2) . . ?
C4 C2 C1 118.2(2) . . ?
C4 C2 C3 120.1(2) . . ?
N1 C3 C2 87.9(2) . . ?
N1 C3 H3A 114.0 . . ?
N1 C3 H3B 114.0 . . ?
C2 C3 H3A 114.0 . . ?
C2 C3 H3B 114.0 . . ?
H3A C3 H3B 111.2 . . ?
N2 C4 N3 106.8(2) . . ?
N2 C4 C2 123.9(2) . . ?
N3 C4 C2 129.1(3) . . ?
N2 C5 H5 126.6 . . ?
C6 C5 N2 106.8(3) . . ?
C6 C5 H5 126.6 . . ?
N3 C6 H6 126.3 . . ?
C5 C6 N3 107.5(3) . . ?
C5 C6 H6 126.3 . . ?
C8 C7 C1 119.2(3) . . ?
C8 C7 C12 120.1(3) . . ?
C12 C7 C1 120.6(3) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S1 120.2(2) . . ?
C16 C15 C20 121.1(3) . . ?
C20 C15 S1 118.7(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 C21 121.0(3) . . ?
C19 C18 C21 120.1(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 118.9(3) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 S2 C22 102.48(16) . . ?
O5 S2 O4 113.84(14) . . ?
O5 S2 O6 115.58(14) . . ?
O5 S2 C22 104.37(15) . . ?
O6 S2 O4 114.81(13) . . ?
O6 S2 C22 103.55(15) . . ?
F1 C22 S2 111.9(3) . . ?
F1 C22 F2 107.9(3) . . ?
F1 C22 F3 107.2(3) . . ?
F2 C22 S2 110.6(2) . . ?
F2 C22 F3 107.7(3) . . ?
F3 C22 S2 111.4(3) . . ?
C23 Cl1 H23D 20.5(3) . 2_656 ?
Cl1 C23 Cl1 97.2(16) . 2_656 ?
Cl1 C23 H23A 112.3 2_656 . ?
Cl1 C23 H23A 112.3 . . ?
Cl1 C23 H23B 112.3 . . ?
Cl1 C23 H23B 112.3 2_656 . ?
Cl1 C23 H23C 77.1(15) . 2_656 ?
Cl1 C23 H23C 109.9(18) 2_656 2_656 ?
Cl1 C23 H23D 77.1(15) 2_656 2_656 ?
Cl1 C23 H23D 109.9(18) . 2_656 ?
H23A C23 H23B 109.9 . . ?
H23A C23 H23C 134.8 . 2_656 ?
H23A C23 H23D 36.3 . 2_656 ?
H23B C23 H23C 36.3 . 2_656 ?
H23B C23 H23D 134.8 . 2_656 ?
H23C C23 H23D 169.9 2_656 2_656 ?
H23A C23A H23B 73.0 2_656 2_656 ?
Cl1A C23A H23C 105.2 . . ?
Cl1A C23A H23C 105.2 2_656 . ?
Cl1A C23A H23D 105.2 2_656 . ?
Cl1A C23A H23D 105.2 . . ?
H23C C23A H23D 105.9 . . ?
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 O2 1.433(3) . ?
S1 O3 1.433(3) . ?
S1 N1 1.643(2) . ?
S1 C15 1.750(3) . ?
O1 H1 0.86(4) . ?
O1 C2 1.413(3) . ?
N1 C1 1.516(4) . ?
N1 C3 1.496(3) . ?
N2 C4 1.339(4) . ?
N2 C5 1.374(4) . ?
N2 C13 1.468(4) . ?
N3 C4 1.345(4) . ?
N3 C6 1.376(4) . ?
N3 C14 1.461(4) . ?
C1 H1A 1.0000 . ?
C1 C2 1.574(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.548(4) . ?
C2 C4 1.505(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.345(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(5) . ?
C7 C12 1.398(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.380(5) . ?
C15 C20 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(5) . ?
C18 C19 1.388(5) . ?
C18 C21 1.509(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
S2 O4 1.454(2) . ?
S2 O5 1.435(2) . ?
S2 O6 1.436(2) . ?
S2 C22 1.823(4) . ?
F1 C22 1.331(4) . ?
F2 C22 1.336(4) . ?
F3 C22 1.338(4) . ?
Cl1 C23 1.723(17) . ?
Cl1 H23D 2.128(17) 2_656 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 H23C 0.794(3) 2_656 ?
C23 H23D 0.793(3) 2_656 ?
Cl1A C23A 1.743(9) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.86(4) 1.92(4) 2.767(3) 169(4) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -144.48(19) . . . . ?
S1 N1 C1 C7 88.9(3) . . . . ?
S1 N1 C3 C2 148.6(2) . . . . ?
S1 C15 C16 C17 177.0(3) . . . . ?
S1 C15 C20 C19 -176.7(2) . . . . ?
O1 C2 C3 N1 87.4(2) . . . . ?
O1 C2 C4 N2 -59.6(3) . . . . ?
O1 C2 C4 N3 115.0(3) . . . . ?
O2 S1 N1 C1 172.7(2) . . . . ?
O2 S1 N1 C3 65.1(3) . . . . ?
O2 S1 C15 C16 -134.2(3) . . . . ?
O2 S1 C15 C20 43.2(3) . . . . ?
O3 S1 N1 C1 44.8(3) . . . . ?
O3 S1 N1 C3 -62.8(3) . . . . ?
O3 S1 C15 C16 -4.5(3) . . . . ?
O3 S1 C15 C20 172.8(2) . . . . ?
N1 S1 C15 C16 114.5(3) . . . . ?
N1 S1 C15 C20 -68.2(3) . . . . ?
N1 C1 C2 O1 -90.2(2) . . . . ?
N1 C1 C2 C3 22.3(2) . . . . ?
N1 C1 C2 C4 144.6(2) . . . . ?
N1 C1 C7 C8 -130.4(3) . . . . ?
N1 C1 C7 C12 45.2(3) . . . . ?
N2 C5 C6 N3 -0.2(3) . . . . ?
C1 N1 C3 C2 23.5(2) . . . . ?
C1 C2 C3 N1 -22.6(2) . . . . ?
C1 C2 C4 N2 66.3(3) . . . . ?
C1 C2 C4 N3 -119.2(3) . . . . ?
C1 C7 C8 C9 174.1(3) . . . . ?
C1 C7 C12 C11 -174.8(3) . . . . ?
C2 C1 C7 C8 126.7(3) . . . . ?
C2 C1 C7 C12 -57.7(4) . . . . ?
C3 N1 C1 C2 -23.1(2) . . . . ?
C3 N1 C1 C7 -149.7(2) . . . . ?
C3 C2 C4 N2 169.3(3) . . . . ?
C3 C2 C4 N3 -16.2(4) . . . . ?
C4 N2 C5 C6 -0.3(3) . . . . ?
C4 N3 C6 C5 0.5(3) . . . . ?
C4 C2 C3 N1 -143.3(3) . . . . ?
C5 N2 C4 N3 0.6(3) . . . . ?
C5 N2 C4 C2 176.2(2) . . . . ?
C6 N3 C4 N2 -0.7(3) . . . . ?
C6 N3 C4 C2 -176.0(3) . . . . ?
C7 C1 C2 O1 26.7(4) . . . . ?
C7 C1 C2 C3 139.2(3) . . . . ?
C7 C1 C2 C4 -98.5(3) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C8 C7 C12 C11 0.7(4) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C12 C7 C8 C9 -1.5(5) . . . . ?
C13 N2 C4 N3 176.4(3) . . . . ?
C13 N2 C4 C2 -8.0(4) . . . . ?
C13 N2 C5 C6 -176.2(3) . . . . ?
C14 N3 C4 N2 178.3(3) . . . . ?
C14 N3 C4 C2 3.1(5) . . . . ?
C14 N3 C6 C5 -178.6(3) . . . . ?
C15 S1 N1 C1 -72.0(2) . . . . ?
C15 S1 N1 C3 -179.6(2) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C15 C20 C19 0.6(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C16 C17 C18 C21 -178.4(3) . . . . ?
C17 C18 C19 C20 0.4(5) . . . . ?
C18 C19 C20 C15 -0.6(5) . . . . ?
C20 C15 C16 C17 -0.3(5) . . . . ?
C21 C18 C19 C20 178.7(3) . . . . ?
O4 S2 C22 F1 63.8(3) . . . . ?
O4 S2 C22 F2 -56.5(3) . . . . ?
O4 S2 C22 F3 -176.2(3) . . . . ?
O5 S2 C22 F1 -55.1(3) . . . . ?
O5 S2 C22 F2 -175.4(2) . . . . ?
O5 S2 C22 F3 64.8(3) . . . . ?
O6 S2 C22 F1 -176.5(2) . . . . ?
O6 S2 C22 F2 63.2(3) . . . . ?
O6 S2 C22 F3 -56.5(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0048 0.0028 1.0029 0.0353 0.0508 0.0016
0.0048 -0.0028 -1.0029 -0.0353 -0.0508 -0.0016
0.9977 0.0021 0.0048 -0.0453 0.0417 -0.0079
-0.9977 -0.0021 -0.0048 0.0453 -0.0417 0.0079
-0.0024 0.9930 -0.0121 -0.0226 0.0107 0.1802
0.0024 -0.9930 0.0121 0.0226 -0.0107 -0.1802
