# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cry0045_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2nnxx5
_database_code_depnum_ccdc_archive 'CCDC 2462978'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-fx6km 2025
loop_
_audit_author_name
_audit_author_address
'Charlotte Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2025-06-09 deposited with the CCDC.	2026-02-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H15 N O3 S'
_chemical_formula_sum            'C12 H15 N O3 S'
_chemical_formula_weight         253.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H15NO3S
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.69645(13)
_cell_length_b                   5.25071(5)
_cell_length_c                   18.54221(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.5151(9)
_cell_angle_gamma                90
_cell_volume                     1232.29(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12943
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.4530
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.654
_exptl_absorpt_coefficient_mu    2.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0100
0 0 -1 0.0100
-1 0 0 0.0039
1 0 0 0.0069
0 1 0 0.1012
0 -1 0 0.1012

_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.011
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
-0.0001 -0.0001 0.9997 0.0130 0.0208 0.0796
0.0001 0.0001 -0.9997 -0.0130 -0.0208 -0.0796
-0.9986 -0.0003 0.0002 -0.0996 0.0687 -0.0116
0.9986 0.0003 -0.0002 0.0996 -0.0687 0.0116
-0.0012 0.9997 -0.0024 0.1660 0.2259 -0.0864
0.0012 -0.9997 0.0024 -0.1660 -0.2259 0.0864

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.555
_diffrn_reflns_theta_min         4.075
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 -33.00   0.50    0.43    -- -106.00  61.00 120.00   84
  2  ω    -75.00 -33.00   0.50    0.43    -- -106.00  61.00  90.00   84
  3  ω    -75.00 -33.00   0.50    0.43    -- -106.00  61.00  60.00   84
  4  ω    -75.00 -33.00   0.50    0.43    -- -106.00  61.00   0.00   84
  5  ω    -75.00 -33.00   0.50    0.43    -- -106.00  61.00 -30.00   84
  6  ω    -75.00 -33.00   0.50    0.43    -- -106.00  61.00 -90.00   84
  7  ω    -42.00  26.00   0.50    0.11    --  -47.49  37.00-120.00  136
  8  ω   -119.00 -77.00   0.50    0.11    --  -47.49   0.00 -90.00   84
  9  ω   -119.00 -25.00   0.50    0.11    --  -47.49 -77.00 -90.00  188
 10  ω   -119.00 -25.00   0.50    0.11    --  -47.49 -77.00   0.00  188
 11  ω   -119.00 -77.00   0.50    0.11    --  -47.49   0.00  30.00   84
 12  ω   -119.00 -51.00   0.50    0.11    --  -47.49 -77.00 150.00  136
 13  ω     42.00 106.00   0.50    0.43    --  113.25 -94.00 -90.00  128
 14  ω     42.00 106.00   0.50    0.43    --  113.25 -94.00-180.00  128
 15  ω     44.00 111.00   0.50    0.43    --  113.25-125.00-180.00  134
 16  ω     42.00 106.00   0.50    0.43    --  113.25 -94.00 -60.00  128
 17  ω     43.00 106.00   0.50    0.43    --  113.25-101.00   1.00  126
 18  ω     42.00 106.00   0.50    0.43    --  113.25 -94.00  30.00  128
 19  ω    -18.00  81.00   0.50    0.11    --   47.49-101.00   1.00  198
 20  ω    -27.00  17.00   0.50    0.11    --   47.49 -19.00   0.00   88
 21  ω     42.00  71.00   0.50    0.43    --  113.25 -61.00 150.00   58
 22  ω     42.00  71.00   0.50    0.43    --  113.25 -61.00 -30.00   58
 23  ω     42.00  71.00   0.50    0.43    --  113.25 -61.00-180.00   58
 24  ω     33.00 119.00   0.50    0.11    --   47.49  57.00-150.00  172
 25  ω     85.00 178.00   0.50    0.43    --  113.25 101.00 105.00  186
 26  ω     25.00 119.00   0.50    0.11    --   47.49  77.00  90.00  188
 27  ω   -177.00 -85.00   0.50    0.43    -- -106.00-101.00   1.00  184
 28  ω   -177.00 -81.00   0.50    0.43    -- -106.00 -81.00  70.67  192
 29  ω   -177.00 -93.00   0.50    0.43    -- -106.00 -30.00 120.00  168
 30  ω   -177.00 -86.00   0.50    0.43    -- -106.00 -69.00  37.75  182
 31  ω   -177.00 -86.00   0.50    0.43    -- -106.00 -69.00  46.14  182
 32  ω   -177.00 -86.00   0.50    0.43    -- -106.00 -69.00  46.14  182
 33  ω   -177.00 -84.00   0.50    0.43    -- -106.00 -74.00-107.65  186
 34  ω   -177.00 -93.00   0.50    0.43    -- -106.00 -45.00 -90.00  168
 35  ω   -177.00 -92.00   0.50    0.43    -- -106.00 -50.00 -67.70  170
 36  ω   -177.00 -93.00   0.50    0.43    -- -106.00 -30.00 120.00  168
 37  ω   -106.00 -35.00   0.50    0.43    -- -106.00 101.00 105.00  142
 38  ω   -107.00 -36.00   0.50    0.43    -- -106.00 107.00 143.66  142
 39  ω   -108.00 -37.00   0.50    0.43    -- -106.00 112.00   4.89  142
 40  ω    -81.00  18.00   0.50    0.11    --  -47.49 101.00 105.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0996724000
_diffrn_orient_matrix_UB_12      0.1662167000
_diffrn_orient_matrix_UB_13      0.0130542000
_diffrn_orient_matrix_UB_21      -0.0689130000
_diffrn_orient_matrix_UB_22      0.2259474000
_diffrn_orient_matrix_UB_23      0.0208208000
_diffrn_orient_matrix_UB_31      0.0117119000
_diffrn_orient_matrix_UB_32      -0.0861893000
_diffrn_orient_matrix_UB_33      0.0796070000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             2617
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.6175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          ?
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C16(H16)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S S 0.41386(2) -0.00364(6) 0.13750(2) 0.01721(11) Uani 1 1 d . . . . .
O1 O 0.67204(8) 0.6575(2) 0.14979(6) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.43082(8) -0.18078(18) 0.08064(5) 0.0223(2) Uani 1 1 d . . . . .
O3 O 0.38825(8) -0.09385(19) 0.20707(5) 0.0222(2) Uani 1 1 d . . . . .
C4 C 0.25292(11) 0.3276(3) 0.15528(7) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.262356 0.285408 0.205187 0.025 Uiso 1 1 calc R U . . .
N5 N 0.52421(9) 0.1520(2) 0.15189(6) 0.0190(2) Uani 1 1 d . . . . .
C6 C 0.57612(12) 0.2820(3) 0.09292(8) 0.0240(3) Uani 1 1 d . . . . .
H6A H 0.526568 0.342371 0.052639 0.029 Uiso 1 1 calc R U . . .
H6B H 0.635651 0.185708 0.074780 0.029 Uiso 1 1 calc R U . . .
C7 C 0.31449(10) 0.2119(3) 0.10581(7) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.16205(11) 0.5679(3) 0.05776(8) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.53882(11) 0.3726(3) 0.20356(7) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.472169 0.472044 0.206683 0.024 Uiso 1 1 calc R U . . .
C10 C 0.30015(11) 0.2697(3) 0.03235(7) 0.0196(3) Uani 1 1 d . . . . .
H10 H 0.342267 0.189627 -0.001211 0.023 Uiso 1 1 calc R U . . .
C11 C 0.22338(11) 0.4461(3) 0.00889(7) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.212466 0.484466 -0.041213 0.025 Uiso 1 1 calc R U . . .
C12 C 0.59098(12) 0.3075(3) 0.27767(8) 0.0243(3) Uani 1 1 d . . . . .
H12A H 0.659317 0.221721 0.272124 0.029 Uiso 1 1 calc R U . . .
H12B H 0.545369 0.188054 0.302364 0.029 Uiso 1 1 calc R U . . .
C13 C 0.08144(12) 0.7664(3) 0.03274(8) 0.0272(3) Uani 1 1 d . . . . .
H13A H 0.110650 0.936559 0.042918 0.041 Uiso 1 1 calc R U . . .
H13B H 0.017548 0.743519 0.058442 0.041 Uiso 1 1 calc R U . . .
H13C H 0.063721 0.748115 -0.019405 0.041 Uiso 1 1 calc R U . . .
C14 C 0.60960(11) 0.4870(3) 0.14844(8) 0.0204(3) Uani 1 1 d . . . . .
C15 C 0.60977(14) 0.5460(3) 0.32380(8) 0.0319(4) Uani 1 1 d . . . . .
H15A H 0.652565 0.667256 0.298511 0.048 Uiso 1 1 calc R U . . .
H15B H 0.647061 0.499876 0.370244 0.048 Uiso 1 1 calc R U . . .
H15C H 0.541759 0.624223 0.332282 0.048 Uiso 1 1 calc R U . . .
C16 C 0.17761(11) 0.5053(3) 0.13086(8) 0.0230(3) Uani 1 1 d . . . . .
H16 H 0.135843 0.585760 0.164556 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S O2 1.4347(10) . ?
S O3 1.4354(10) . ?
S N5 1.6257(12) . ?
S C7 1.7611(14) . ?
O1 C14 1.1949(18) . ?
C4 H4 0.9500 . ?
C4 C7 1.3907(19) . ?
C4 C16 1.386(2) . ?
N5 C6 1.4866(18) . ?
N5 C9 1.5053(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C14 1.5264(19) . ?
C7 C10 1.3934(19) . ?
C8 C11 1.396(2) . ?
C8 C13 1.5080(19) . ?
C8 C16 1.394(2) . ?
C9 H9 1.0000 . ?
C9 C12 1.5167(19) . ?
C9 C14 1.536(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C15 1.525(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?

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 S O3 120.27(6) . . ?
O2 S N5 105.62(6) . . ?
O2 S C7 108.45(6) . . ?
O3 S N5 105.76(6) . . ?
O3 S C7 107.75(6) . . ?
N5 S C7 108.50(6) . . ?
C7 C4 H4 120.4 . . ?
C16 C4 H4 120.4 . . ?
C16 C4 C7 119.18(13) . . ?
C6 N5 S 122.43(9) . . ?
C6 N5 C9 94.31(10) . . ?
C9 N5 S 123.55(9) . . ?
N5 C6 H6A 114.2 . . ?
N5 C6 H6B 114.2 . . ?
N5 C6 C14 86.78(10) . . ?
H6A C6 H6B 111.4 . . ?
C14 C6 H6A 114.2 . . ?
C14 C6 H6B 114.2 . . ?
C4 C7 S 119.07(10) . . ?
C4 C7 C10 120.84(13) . . ?
C10 C7 S 120.07(11) . . ?
C11 C8 C13 121.11(13) . . ?
C16 C8 C11 118.67(13) . . ?
C16 C8 C13 120.21(13) . . ?
N5 C9 H9 112.1 . . ?
N5 C9 C12 115.24(11) . . ?
N5 C9 C14 85.80(10) . . ?
C12 C9 H9 112.1 . . ?
C12 C9 C14 117.03(12) . . ?
C14 C9 H9 112.1 . . ?
C7 C10 H10 120.5 . . ?
C11 C10 C7 119.06(13) . . ?
C11 C10 H10 120.5 . . ?
C8 C11 H11 119.5 . . ?
C10 C11 C8 121.04(13) . . ?
C10 C11 H11 119.5 . . ?
C9 C12 H12A 109.4 . . ?
C9 C12 H12B 109.4 . . ?
C9 C12 C15 111.16(12) . . ?
H12A C12 H12B 108.0 . . ?
C15 C12 H12A 109.4 . . ?
C15 C12 H12B 109.4 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 C6 133.76(14) . . ?
O1 C14 C9 134.54(13) . . ?
C6 C14 C9 91.52(10) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 C8 121.20(13) . . ?
C4 C16 H16 119.4 . . ?
C8 C16 H16 119.4 . . ?

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
S N5 C6 C14 144.48(10) . . . . ?
S N5 C9 C12 98.32(13) . . . . ?
S N5 C9 C14 -143.69(10) . . . . ?
S C7 C10 C11 -178.07(10) . . . . ?
O2 S N5 C6 53.11(12) . . . . ?
O2 S N5 C9 174.99(10) . . . . ?
O2 S C7 C4 152.97(11) . . . . ?
O2 S C7 C10 -28.69(13) . . . . ?
O3 S N5 C6 -178.37(10) . . . . ?
O3 S N5 C9 -56.49(12) . . . . ?
O3 S C7 C4 21.30(13) . . . . ?
O3 S C7 C10 -160.36(11) . . . . ?
C4 C7 C10 C11 0.2(2) . . . . ?
N5 S C7 C4 -92.76(12) . . . . ?
N5 S C7 C10 85.57(12) . . . . ?
N5 C6 C14 O1 165.92(16) . . . . ?
N5 C6 C14 C9 -9.47(10) . . . . ?
N5 C9 C12 C15 175.66(12) . . . . ?
N5 C9 C14 O1 -165.97(17) . . . . ?
N5 C9 C14 C6 9.36(10) . . . . ?
C6 N5 C9 C12 -127.62(13) . . . . ?
C6 N5 C9 C14 -9.64(10) . . . . ?
C7 S N5 C6 -63.00(12) . . . . ?
C7 S N5 C9 58.88(12) . . . . ?
C7 C4 C16 C8 0.6(2) . . . . ?
C7 C10 C11 C8 1.0(2) . . . . ?
C9 N5 C6 C14 9.69(10) . . . . ?
C11 C8 C16 C4 0.6(2) . . . . ?
C12 C9 C14 O1 -49.7(2) . . . . ?
C12 C9 C14 C6 125.63(13) . . . . ?
C13 C8 C11 C10 177.76(13) . . . . ?
C13 C8 C16 C4 -178.53(13) . . . . ?
C14 C9 C12 C15 77.06(16) . . . . ?
C16 C4 C7 S 177.35(11) . . . . ?
C16 C4 C7 C10 -1.0(2) . . . . ?
C16 C8 C11 C10 -1.4(2) . . . . ?

_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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.660
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cx3273
_audit_block_doi                 10.5517/ccdc.csd.cc2np1v8
_database_code_depnum_ccdc_archive 'CCDC 2463100'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-fx6km 2025
loop_
_audit_author_name
_audit_author_address
'Charlotte Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2025-06-09 deposited with the CCDC.	2026-02-03 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 N3 O3 S, C F3 O3 S, 0.5(Cl2 H2 C1)'
_chemical_formula_sum            'C22.50 H25 Cl F3 N3 O6 S2'
_chemical_formula_weight         590.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H24F3N3O6S2
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'

_cell_length_a                   25.0211(6)
_cell_length_b                   8.3937(3)
_cell_length_c                   25.1936(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.585(2)
_cell_angle_gamma                90
_cell_volume                     5244.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    27664
_cell_measurement_temperature    100.3(6)
_cell_measurement_theta_max      75.2150
_cell_measurement_theta_min      3.4840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2440
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

_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
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

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5069
_reflns_number_total             5429
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.087
_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
_refine_special_details          
'Distance restraints were imposed on the disordered dichloromethane. The enhanced rigid-bond restraint (SHELX keyword RIGU) as well as restraints on similar amplitudes separated by less than 1.7 (SIMU) were also applied on the disordered solvent molecule. (Acta Cryst. A68 (2012) 448-451).'
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cry0225
_database_code_depnum_ccdc_archive 'CCDC 2480795'
loop_
_audit_author_name
_audit_author_address
'Charlotte Stern'
;Northwestern University
United States of America
;
_audit_update_record             
;
2025-08-15 deposited with the CCDC.	2026-02-03 downloaded from the CCDC.
;
_audit_creation_date             2025-07-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/2
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N3 O3'
_chemical_formula_sum            'C20 H27 N3 O3'
_chemical_formula_weight         357.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H27N3O3
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.6584(6)
_cell_length_b                   10.8794(7)
_cell_length_c                   16.6188(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1927.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.8770
_cell_measurement_theta_min      4.8140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.114a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0037
0 0 1 0.0010
-1 0 0 0.1576
1 0 0 0.1576
0 1 0 0.0201
0 -1 0 0.0051

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.005
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
-0.0008 -0.0013 -0.9988 -0.0575 0.0715 -0.0113
0.0008 0.0013 0.9988 0.0575 -0.0715 0.0113
-1.0003 0.0008 0.0008 -0.1017 -0.0690 0.0764
1.0003 -0.0008 -0.0008 0.1017 0.0690 -0.0764
0.0011 0.9996 -0.0004 0.0500 0.0583 0.1190
-0.0011 -0.9996 0.0004 -0.0500 -0.0583 -0.1190

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16395
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.382
_diffrn_reflns_theta_min         4.858
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  71.00   0.50   15.00    --   47.59 -79.00 -28.00  190
  2  ω   -109.00 -30.00   0.50   35.00    -- -103.00 119.00 170.00  158
  3  ω   -109.00 -30.00   0.50   35.00    -- -103.00 119.00 170.00  158
  4  ω     37.00 107.00   0.50   35.00    --  109.25 -79.00 -28.00  140
  5  ω     96.00 178.00   0.50   35.00    --  109.25  43.00 -54.00  164
  6  ω     37.00 110.00   0.50   35.00    --  109.25-119.00  85.00  146
  7  ω    -30.00  28.00   0.50   15.00    --  -47.59  19.00-180.00  116
  8  ω   -119.00 -73.00   0.50   15.00    --  -47.59-125.00-150.00   92
  9  ω     59.00 119.00   0.50   15.00    --   47.59 155.00 -32.00  120
 10  ω    -27.00  40.00   0.50   15.00    --   47.59 -19.00 -30.00  134
 11  ω   -174.00 -90.00   0.50   35.00    -- -103.00 -30.00-180.00  168
 12  ω    -92.00 -30.00   0.50   35.00    -- -103.00  77.00  30.00  124
 13  ω    -65.00 -30.00   0.50   35.00    -- -103.00  61.00 150.00   70
 14  ω    -65.00 -30.00   0.50   35.00    -- -103.00  61.00  30.00   70
 15  ω     97.00 178.00   0.50   35.00    --  109.25  30.00  30.00  162
 16  ω     37.00  75.00   0.50   35.00    --  109.25 -61.00 120.00   76
 17  ω     37.00 106.00   0.50   35.00    --  109.25 -94.00-120.00  138
 18  ω     37.00 111.00   0.50   35.00    --  109.25-125.00   0.00  148
 19  ω     37.00 102.00   0.50   35.00    --  109.25 -77.00-120.00  130
 20  ω   -119.00 -33.00   0.50   15.00    --  -47.59 -57.00-120.00  172
 21  ω     25.00 111.00   0.50   15.00    --   47.59  77.00 -30.00  172
 22  ω     25.00 119.00   0.50   15.00    --   47.59  77.00  60.00  188
;
_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      0.1017114000
_diffrn_orient_matrix_UB_12      0.0498958000
_diffrn_orient_matrix_UB_13      0.0573956000
_diffrn_orient_matrix_UB_21      0.0689843000
_diffrn_orient_matrix_UB_22      0.0582514000
_diffrn_orient_matrix_UB_23      -0.0717577000
_diffrn_orient_matrix_UB_31      -0.0763107000
_diffrn_orient_matrix_UB_32      0.1191136000
_diffrn_orient_matrix_UB_33      0.0112517000
_diffrn_oxdiff_digest_hkl        
;
43462323637db2fafc9c70f20b6a1109903a36
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name cry0225.par
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                2934
_reflns_number_total             3911
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.44.114a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.114a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.114a (Rigaku OD, 2025)'
_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)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1131P)²+0.3578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.1955
_refine_special_details          ?
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C13(H13), C12(H12), C11(H11), C17(H17), C18(H18)
2.d Fitted hexagon refined as free rotating group:
 C10(C15,C14,C13,C12,C11)
2.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.3279(3) 0.0570(3) 0.7039(2) 0.0390(8) Uani 1 1 d . . . . .
O2 O 0.2083(3) 0.2121(4) 0.7588(2) 0.0441(9) Uani 1 1 d . . . . .
O3 O 0.1460(3) 0.2358(3) 0.4661(2) 0.0371(8) Uani 1 1 d . . . . .
H3 H 0.102(9) 0.209(9) 0.498(7) 0.11(4) Uiso 1 1 d . . . . .
N1 N 0.2681(4) 0.4479(4) 0.4062(3) 0.0352(9) Uani 1 1 d . . . . .
N2 N 0.4455(3) 0.3619(4) 0.4458(3) 0.0348(9) Uani 1 1 d . . . . .
N3 N 0.2555(4) 0.2049(4) 0.6258(2) 0.0340(9) Uani 1 1 d . . . . .
C1 C 0.2120(4) 0.3245(5) 0.5977(3) 0.0357(11) Uani 1 1 d . . . . .
H1 H 0.119161 0.334151 0.603752 0.043 Uiso 1 1 calc R U . . .
C2 C 0.2496(4) 0.2808(4) 0.5108(3) 0.0331(10) Uani 1 1 d . . . . .
C3 C 0.3276(4) 0.1766(4) 0.5527(3) 0.0333(10) Uani 1 1 d . . . . .
H3A H 0.417040 0.202453 0.559198 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2605(4) 0.1628(5) 0.7015(3) 0.0361(11) Uani 1 1 d . . . . .
C5 C 0.3289(5) -0.0223(5) 0.7762(3) 0.0403(12) Uani 1 1 d . . . . .
C6 C 0.3885(5) 0.0462(6) 0.8456(3) 0.0441(13) Uani 1 1 d . . . . .
H6A H 0.469729 0.079504 0.828587 0.066 Uiso 1 1 calc R U . . .
H6B H 0.400915 -0.010223 0.890836 0.066 Uiso 1 1 calc R U . . .
H6C H 0.333446 0.113711 0.862232 0.066 Uiso 1 1 calc R U . . .
C7 C 0.1944(5) -0.0645(6) 0.7942(4) 0.0474(13) Uani 1 1 d . . . . .
H7A H 0.143460 0.006528 0.809922 0.071 Uiso 1 1 calc R U . . .
H7B H 0.195569 -0.124456 0.838265 0.071 Uiso 1 1 calc R U . . .
H7C H 0.158310 -0.102632 0.746082 0.071 Uiso 1 1 calc R U . . .
C8 C 0.4061(5) -0.1307(5) 0.7505(4) 0.0472(13) Uani 1 1 d . . . . .
H8A H 0.371012 -0.165488 0.701016 0.071 Uiso 1 1 calc R U . . .
H8B H 0.405045 -0.193042 0.793056 0.071 Uiso 1 1 calc R U . . .
H8C H 0.492676 -0.104263 0.740743 0.071 Uiso 1 1 calc R U . . .
C9 C 0.2837(4) 0.4329(5) 0.6328(3) 0.0382(11) Uani 1 1 d . . . . .
H9A H 0.280561 0.427861 0.692244 0.046 Uiso 1 1 calc R U . . .
H9B H 0.372701 0.426731 0.616335 0.046 Uiso 1 1 calc R U . . .
C10 C 0.2330(3) 0.5567(2) 0.6067(2) 0.0382(11) Uani 1 1 d G . . . .
C15 C 0.2966(2) 0.6268(3) 0.5499(2) 0.0395(12) Uani 1 1 d G . . . .
H15 H 0.375831 0.600396 0.530331 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2442(3) 0.7357(3) 0.5218(2) 0.0448(13) Uani 1 1 d G . . . .
H14 H 0.287659 0.783630 0.483011 0.054 Uiso 1 1 calc R U . . .
C13 C 0.1282(3) 0.7744(3) 0.5505(2) 0.0507(14) Uani 1 1 d G . . . .
H13 H 0.092437 0.848790 0.531280 0.061 Uiso 1 1 calc R U . . .
C12 C 0.0646(2) 0.7043(3) 0.6073(2) 0.0476(14) Uani 1 1 d G . . . .
H12 H -0.014614 0.730716 0.626869 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1170(3) 0.5954(3) 0.6354(2) 0.0421(13) Uani 1 1 d G . . . .
H11 H 0.073557 0.547482 0.674190 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3223(4) 0.3626(4) 0.4550(3) 0.0318(10) Uani 1 1 d . . . . .
C17 C 0.3637(5) 0.5041(5) 0.3632(3) 0.0404(12) Uani 1 1 d . . . . .
H17 H 0.355775 0.567452 0.324225 0.049 Uiso 1 1 calc R U . . .
C18 C 0.4707(4) 0.4495(5) 0.3886(3) 0.0387(12) Uani 1 1 d . . . . .
H18 H 0.552218 0.469124 0.369331 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1360(4) 0.4850(5) 0.4017(4) 0.0437(13) Uani 1 1 d . . . . .
H19A H 0.130287 0.568086 0.379230 0.066 Uiso 1 1 calc R U . . .
H19B H 0.099405 0.484218 0.455822 0.066 Uiso 1 1 calc R U . . .
H19C H 0.090118 0.427556 0.367156 0.066 Uiso 1 1 calc R U . . .
C20 C 0.3202(5) 0.0484(5) 0.5198(3) 0.0401(12) Uani 1 1 d . . . . .
H20A H 0.356158 -0.009252 0.558790 0.060 Uiso 1 1 calc R U . . .
H20B H 0.367419 0.043763 0.469256 0.060 Uiso 1 1 calc R U . . .
H20C H 0.232300 0.026914 0.509775 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C4 1.357(6) . ?
O1 C5 1.478(6) . ?
O2 C4 1.226(6) . ?
O3 H3 0.76(10) . ?
O3 C2 1.419(6) . ?
N1 C16 1.361(6) . ?
N1 C17 1.387(6) . ?
N1 C19 1.466(6) . ?
N2 C16 1.321(6) . ?
N2 C18 1.374(7) . ?
N3 C1 1.458(6) . ?
N3 C3 1.470(6) . ?
N3 C4 1.340(7) . ?
C1 H1 1.0000 . ?
C1 C2 1.573(7) . ?
C1 C9 1.521(7) . ?
C2 C3 1.568(7) . ?
C2 C16 1.500(7) . ?
C3 H3A 1.0000 . ?
C3 C20 1.501(7) . ?
C5 C6 1.513(8) . ?
C5 C7 1.535(7) . ?
C5 C8 1.499(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(6) . ?
C10 C15 1.3900 . ?
C10 C11 1.3900 . ?
C15 H15 0.9500 . ?
C15 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 H13 0.9500 . ?
C13 C12 1.3900 . ?
C12 H12 0.9500 . ?
C12 C11 1.3900 . ?
C11 H11 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.353(7) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C4 O1 C5 121.5(4) . . ?
C2 O3 H3 105(8) . . ?
C16 N1 C17 107.2(4) . . ?
C16 N1 C19 128.7(4) . . ?
C17 N1 C19 123.9(4) . . ?
C16 N2 C18 105.7(4) . . ?
C1 N3 C3 95.0(4) . . ?
C4 N3 C1 128.2(4) . . ?
C4 N3 C3 133.2(4) . . ?
N3 C1 H1 112.1 . . ?
N3 C1 C2 86.8(4) . . ?
N3 C1 C9 114.1(4) . . ?
C2 C1 H1 112.1 . . ?
C9 C1 H1 112.1 . . ?
C9 C1 C2 117.3(4) . . ?
O3 C2 C1 112.7(4) . . ?
O3 C2 C3 113.3(4) . . ?
O3 C2 C16 106.5(4) . . ?
C3 C2 C1 86.9(4) . . ?
C16 C2 C1 121.3(4) . . ?
C16 C2 C3 115.4(4) . . ?
N3 C3 C2 86.5(3) . . ?
N3 C3 H3A 110.5 . . ?
N3 C3 C20 117.9(4) . . ?
C2 C3 H3A 110.5 . . ?
C20 C3 C2 118.8(4) . . ?
C20 C3 H3A 110.5 . . ?
O2 C4 O1 126.0(5) . . ?
O2 C4 N3 124.2(5) . . ?
N3 C4 O1 109.8(4) . . ?
O1 C5 C6 109.5(4) . . ?
O1 C5 C7 109.1(4) . . ?
O1 C5 C8 103.4(4) . . ?
C6 C5 C7 113.0(5) . . ?
C8 C5 C6 111.9(5) . . ?
C8 C5 C7 109.4(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C9 H9A 108.8 . . ?
C1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C1 113.6(4) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C15 C10 C9 120.6(3) . . ?
C15 C10 C11 120.0 . . ?
C11 C10 C9 119.2(3) . . ?
C10 C15 H15 120.0 . . ?
C10 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
N1 C16 C2 123.6(4) . . ?
N2 C16 N1 110.9(4) . . ?
N2 C16 C2 125.5(4) . . ?
N1 C17 H17 127.3 . . ?
C18 C17 N1 105.4(4) . . ?
C18 C17 H17 127.3 . . ?
N2 C18 H18 124.6 . . ?
C17 C18 N2 110.8(4) . . ?
C17 C18 H18 124.6 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
O3 C2 C3 N3 -97.7(4) . . . . ?
O3 C2 C3 C20 22.5(6) . . . . ?
O3 C2 C16 N1 45.1(6) . . . . ?
O3 C2 C16 N2 -134.5(5) . . . . ?
N1 C17 C18 N2 -0.2(6) . . . . ?
N3 C1 C2 O3 98.1(4) . . . . ?
N3 C1 C2 C3 -15.9(3) . . . . ?
N3 C1 C2 C16 -134.0(4) . . . . ?
N3 C1 C9 C10 -176.8(4) . . . . ?
C1 N3 C3 C2 -17.1(3) . . . . ?
C1 N3 C3 C20 -138.1(4) . . . . ?
C1 N3 C4 O1 -168.7(4) . . . . ?
C1 N3 C4 O2 13.2(8) . . . . ?
C1 C2 C3 N3 15.8(3) . . . . ?
C1 C2 C3 C20 136.0(4) . . . . ?
C1 C2 C16 N1 -85.6(6) . . . . ?
C1 C2 C16 N2 94.9(6) . . . . ?
C1 C9 C10 C15 -105.2(4) . . . . ?
C1 C9 C10 C11 69.8(5) . . . . ?
C2 C1 C9 C10 83.9(5) . . . . ?
C3 N3 C1 C2 17.1(3) . . . . ?
C3 N3 C1 C9 -101.5(4) . . . . ?
C3 N3 C4 O1 -15.7(7) . . . . ?
C3 N3 C4 O2 166.3(5) . . . . ?
C3 C2 C16 N1 171.8(4) . . . . ?
C3 C2 C16 N2 -7.8(7) . . . . ?
C4 O1 C5 C6 -64.3(6) . . . . ?
C4 O1 C5 C7 59.8(6) . . . . ?
C4 O1 C5 C8 176.2(4) . . . . ?
C4 N3 C1 C2 177.6(5) . . . . ?
C4 N3 C1 C9 59.1(6) . . . . ?
C4 N3 C3 C2 -176.1(5) . . . . ?
C4 N3 C3 C20 62.9(7) . . . . ?
C5 O1 C4 O2 9.9(7) . . . . ?
C5 O1 C4 N3 -168.2(4) . . . . ?
C9 C1 C2 O3 -146.3(4) . . . . ?
C9 C1 C2 C3 99.7(4) . . . . ?
C9 C1 C2 C16 -18.4(6) . . . . ?
C9 C10 C15 C14 174.9(4) . . . . ?
C9 C10 C11 C12 -175.0(4) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C16 N1 C17 C18 -0.1(6) . . . . ?
C16 N2 C18 C17 0.4(6) . . . . ?
C16 C2 C3 N3 139.2(4) . . . . ?
C16 C2 C3 C20 -100.6(5) . . . . ?
C17 N1 C16 N2 0.3(6) . . . . ?
C17 N1 C16 C2 -179.3(5) . . . . ?
C18 N2 C16 N1 -0.5(6) . . . . ?
C18 N2 C16 C2 179.1(5) . . . . ?
C19 N1 C16 N2 -175.0(5) . . . . ?
C19 N1 C16 C2 5.4(8) . . . . ?
C19 N1 C17 C18 175.5(5) . . . . ?

_olex2_date_sample_data_collection 2025-07-28
_olex2_date_sample_submission    2025-07-25
_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 cry0225
_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 2.217
_oxdiff_exptl_absorpt_empirical_full_min 0.404
