# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_jmhwlb
_database_code_depnum_ccdc_archive 'CCDC 2341582'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   JMHWLB
_nottingham_internal_coll_number 19421
_nottingham_internal_coll_client JM/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '16.00, 4.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczkj1
_nottingham_internal_coll_date   05/04/2023
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 06/04/2023
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 06/04/2023
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 23/04/2023
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date 23/04/2023
_nottingham_internal_self_validation_user pczkj1
_nottingham_internal_validation_date pczspa
_nottingham_internal_validation_user 26/04/2023
_nottingham_internal_archive_date ?
_refine_special_details          
'All hydrogen atoms were observed in the electron density map. Hydroxy hydrogen atoms H1A and H1B were refined with the O-H distance restrained to a target value of 0.84 %A (DFIX esd 0.02 %A). All other hydrogen atoms in the structure were geometrically placed and refined with a riding model.'
_audit_creation_date             2023-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H28 F3 N O8 S'
_chemical_formula_sum            'C23 H28 F3 N O8 S'
_chemical_formula_weight         535.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H28 F3 N O8 S'
_chemical_oxdiff_usercomment     
'JMHWLB #19421 GVA-2051 KJ/HWL fomblin oil on micromount'
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.4612(2)
_cell_length_b                   10.51960(10)
_cell_length_c                   20.4828(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.749(2)
_cell_angle_gamma                90
_cell_volume                     2557.22(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    42076
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.7860
_cell_measurement_theta_min      4.5060
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.650
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
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    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 10 0.0513
-3 0 -10 0.0513
-1 7 0 0.1240
1 -7 0 0.1240
2 -3 10 0.0987
-2 3 -10 0.0987
-7 0 10 0.0623
7 0 -10 0.0173

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc and pentane'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
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
3.0035 0.0024 9.9970 0.0618 0.4042 -0.8919
-3.0035 -0.0024 -9.9970 -0.0618 -0.4042 0.8919
-1.0016 6.9993 -0.0032 0.0193 0.9027 0.5023
1.0016 -6.9993 0.0032 -0.0193 -0.9027 -0.5023
2.0039 -2.9973 9.9990 0.1876 -0.0260 -0.9865
-2.0039 2.9973 -9.9990 -0.1876 0.0260 0.9865
-6.9993 0.0018 9.5017 0.9829 0.0856 -0.0156
6.9993 -0.0018 -9.5017 -0.9829 -0.0856 0.0156

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47567
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.720
_diffrn_reflns_theta_min         3.723
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  20.00   1.00    4.00    --   30.00  92.00  10.38   25
  2  ω     -7.00  18.00   1.00    4.00    --   30.00  95.00-129.62   25
  3  ω     -7.00  18.00   1.00    4.00    --   30.00  94.00  81.51   25
  4  ω    -43.00  26.00   1.00    4.00    --  -43.06  57.00-150.00   69
  5  ω    -21.00  26.00   1.00    4.00    --  -43.06  38.00 150.00   47
  6  ω     24.00  53.00   1.00    4.00    --   43.06  38.00   0.00   29
  7  ω     27.00  96.00   1.00    4.00    --   43.06-125.00  60.00   69
  8  ω     21.00 114.00   1.00    4.00    --   43.06  38.00-180.00   93
  9  ω     14.00  39.00   1.00    4.00    --   46.00  82.00-147.15   25
 10  ω     14.00  42.00   1.00    4.00    --   46.00  81.00 -76.08   28
 11  ω     15.00  40.00   1.00    4.00    --   46.00  80.00 169.89   25
 12  ω     15.00  42.00   1.00    4.00    --   46.00  78.00  29.04   27
 13  ω     14.00  39.00   1.00    4.00    --   46.00  81.00 107.00   25
 14  ω     27.00  77.00   1.00    4.00    --   54.00  70.00  39.95   50
 15  ω     78.00 123.00   1.00    4.00    --   54.00  70.00  39.95   45
 16  ω     32.00  69.00   1.00    4.00    --   58.00  71.00-162.24   37
 17  ω     31.00  56.00   1.00    4.00    --   58.00  69.00 131.30   25
 18  ω     78.00 128.00   1.00    4.00    --   58.00  71.00-162.24   50
 19  ω     35.00  66.00   1.00    4.00    --   62.00  70.00 171.73   31
 20  ω     34.00  60.00   1.00    4.00    --   62.00  71.00 -29.91   26
 21  ω     40.00  67.00   1.00    4.00    --   66.00  64.00 113.40   27
 22  ω     39.00  87.00   1.00    4.00    --   66.00  69.00 -13.02   48
 23  ω     38.00  64.00   1.00    4.00    --   66.00  71.00  16.03   26
 24  ω     38.00  64.00   1.00    4.00    --   66.00  69.00 -65.39   26
 25  ω     44.00  71.00   1.00    4.00    --   70.00  63.00  86.40   27
 26  ω    101.00 127.00   1.00    4.00    --   70.00  69.00-118.12   26
 27  ω     42.00  77.00   1.00    4.00    --   70.00  69.00-118.12   35
 28  ω     42.00  69.00   1.00    4.00    --   70.00  70.00-145.64   27
 29  ω     47.00  73.00   1.00   16.00    --   74.00  66.00 139.87   26
 30  ω     47.00  77.00   1.00   16.00    --   74.00  69.00 -70.99   30
 31  ω    118.00 144.00   1.00   16.00    --   74.00  71.00  43.29   26
 32  ω     46.00  76.00   1.00   16.00    --   74.00  71.00  43.29   30
 33  ω    110.00 136.00   1.00   16.00    --   74.00  66.00 139.87   26
 34  ω     50.00  81.00   1.00   16.00    --   78.00  70.00 158.80   31
 35  ω     60.00  85.00   1.00   16.00    --   86.00  68.00 -58.27   25
 36  ω    100.00 160.00   1.00   16.00    --   94.00  70.00  37.03   60
 37  ω     66.00  93.00   1.00   16.00    --   94.00  70.00  37.03   27
 38  ω     44.00 113.00   1.00   16.00    --  100.81-125.00-120.00   69
 39  ω     77.00 104.00   1.00   16.00    --  100.81  56.00 172.56   27
 40  ω    110.00 162.00   1.00   16.00    --  100.81  61.00 -60.00   52
 41  ω     77.00 104.00   1.00   16.00    --  100.81  61.00 -60.00   27
 42  ω     31.00  92.00   1.00   16.00    --  100.81 -61.00-150.00   61
 43  ω     31.00  80.00   1.00   16.00    --  100.81 -61.00 120.00   49
 44  ω     31.00  56.00   1.00   16.00    --  100.81 -30.00-120.00   25
 45  ω     29.00 113.00   1.00   16.00    --  100.81-125.00   0.00   84
 46  ω     76.00 164.00   1.00   16.00    --  100.81  61.00 -90.00   88
 47  ω     76.00 135.00   1.00   16.00    --  100.81  61.00 120.00   59
 48  ω    119.00 163.00   1.00   16.00    --  100.81  61.00   0.00   44
 49  ω     77.00 166.00   1.00   16.00    --  100.81  59.00 140.97   89
 50  ω     32.00  91.00   1.00   16.00    --  100.81 -61.00 -30.00   59
 51  ω     76.00 103.00   1.00   16.00    --  100.81  61.00   0.00   27
 52  ω    145.00 170.00   1.00   16.00    --  100.81  55.00  24.57   25
 53  ω    118.00 159.00   1.00   16.00    --  100.81  61.00 -30.00   41
 54  ω     77.00 104.00   1.00   16.00    --  100.81  61.00 -30.00   27
 55  ω     77.00 108.00   1.00   16.00    --  100.81  55.00  24.57   31
 56  ω     77.00 117.00   1.00   16.00    --  100.81  61.00-150.00   40
 57  ω     30.00 106.00   1.00   16.00    --  100.81-125.00 150.00   76
 58  ω     76.00 156.00   1.00   16.00    --  100.81  59.00  68.68   80
 59  ω    126.00 170.00   1.00   16.00    --  100.81  63.00-165.42   44
 60  ω     75.00 102.00   1.00   16.00    --  100.81  63.00-165.42   27
 61  ω     76.00 133.00   1.00   16.00    --  100.81  61.00-120.00   57
 62  ω     29.00 113.00   1.00   16.00    --  100.81-125.00 120.00   84
 63  ω     76.00 102.00   1.00   16.00    --  100.81  61.00  90.00   26
 64  ω    121.00 166.00   1.00   16.00    --  100.81  56.00 172.56   45
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0937789000
_diffrn_orient_matrix_UB_12      -0.0106454000
_diffrn_orient_matrix_UB_13      0.0343632000
_diffrn_orient_matrix_UB_21      0.0302912000
_diffrn_orient_matrix_UB_22      0.1333233000
_diffrn_orient_matrix_UB_23      0.0312964000
_diffrn_orient_matrix_UB_31      -0.0844458000
_diffrn_orient_matrix_UB_32      0.0596577000
_diffrn_orient_matrix_UB_33      -0.0638566000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                9719
_reflns_number_total             9978
_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 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 4434 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     663
_refine_ls_number_reflns         9978
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.5226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0649
_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, All O(H) groups
2. Restrained distances
 O1B-H1B = O1A-H1A
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1A(H1AA), C1B(H1BA)
3.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C15A(H15A,
 H15B), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C15B(H15C,H15D)
3.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C18A(H18A), C20A(H20A), C21A(H21A), C5B(H5B), C18B(H18B),
 C20B(H20B), C21B(H21B)
3.d Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C22A(H22A,
 H22B,H22C), C12B(H12D,H12E,H12F), C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F),
 C22B(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S1A S 0.21956(4) 0.60560(5) 0.22711(3) 0.02821(11) Uani 1 1 d . . . . .
F1A F 0.04301(18) 0.4823(2) 0.23016(9) 0.0803(7) Uani 1 1 d . . . . .
F2A F 0.01655(13) 0.6008(2) 0.14202(8) 0.0639(5) Uani 1 1 d . . . . .
F3A F 0.1077(2) 0.42563(18) 0.14838(10) 0.0733(6) Uani 1 1 d . . . . .
O1A O 0.47641(12) 0.35472(14) 0.07627(7) 0.0249(3) Uani 1 1 d D . . . .
H1A H 0.521(2) 0.301(2) 0.0703(14) 0.037 Uiso 1 1 d D U . . .
O2A O 0.81200(13) 0.28599(18) 0.27893(8) 0.0384(4) Uani 1 1 d . . . . .
O3A O 0.38761(12) 0.67000(17) -0.05440(7) 0.0332(3) Uani 1 1 d . . . . .
O4A O 0.28109(11) 0.58701(15) 0.00727(7) 0.0273(3) Uani 1 1 d . . . . .
O5A O 0.24549(12) 0.64356(13) 0.15930(8) 0.0265(3) Uani 1 1 d . . . . .
O6A O 0.29675(17) 0.5137(2) 0.26330(10) 0.0533(5) Uani 1 1 d . . . . .
O7A O 0.19272(16) 0.71241(17) 0.26031(9) 0.0438(4) Uani 1 1 d . . . . .
O8A O 0.18918(13) 1.07730(15) 0.09836(10) 0.0416(4) Uani 1 1 d . . . . .
N1A N 0.46451(13) 0.61738(16) 0.05806(8) 0.0209(3) Uani 1 1 d . . . . .
C1A C 0.45459(15) 0.55554(18) 0.12028(9) 0.0187(4) Uani 1 1 d . . . . .
H1AA H 0.374318 0.528624 0.110799 0.022 Uiso 1 1 calc R U . . .
C2A C 0.57851(16) 0.6576(2) 0.06059(11) 0.0264(4) Uani 1 1 d . . . . .
H2AA H 0.605632 0.723470 0.096332 0.032 Uiso 1 1 calc R U . . .
H2AB H 0.577056 0.694808 0.015947 0.032 Uiso 1 1 calc R U . . .
C3A C 0.65850(16) 0.5437(2) 0.07667(11) 0.0270(4) Uani 1 1 d . . . . .
H3AA H 0.642931 0.489129 0.035447 0.032 Uiso 1 1 calc R U . . .
H3AB H 0.736998 0.574664 0.087501 0.032 Uiso 1 1 calc R U . . .
C4A C 0.64773(16) 0.4653(2) 0.13562(10) 0.0217(4) Uani 1 1 d . . . . .
C5A C 0.73723(16) 0.4196(2) 0.18423(10) 0.0254(4) Uani 1 1 d . . . . .
H5A H 0.809640 0.451765 0.186797 0.030 Uiso 1 1 calc R U . . .
C6A C 0.72903(17) 0.3224(2) 0.23369(10) 0.0261(4) Uani 1 1 d . . . . .
C7A C 0.61424(18) 0.2654(2) 0.22299(11) 0.0269(4) Uani 1 1 d . . . . .
H7AA H 0.610466 0.226556 0.266267 0.032 Uiso 1 1 calc R U . . .
H7AB H 0.600635 0.197781 0.187773 0.032 Uiso 1 1 calc R U . . .
C8A C 0.52377(16) 0.36821(19) 0.19993(10) 0.0223(4) Uani 1 1 d . . . . .
H8AA H 0.448572 0.329300 0.192179 0.027 Uiso 1 1 calc R U . . .
H8AB H 0.534708 0.432372 0.236739 0.027 Uiso 1 1 calc R U . . .
C9A C 0.52785(15) 0.43382(18) 0.13415(9) 0.0188(4) Uani 1 1 d . . . . .
C10A C 0.37866(16) 0.62752(19) -0.00042(10) 0.0227(4) Uani 1 1 d . . . . .
C11A C 0.17477(17) 0.5950(2) -0.04881(11) 0.0312(5) Uani 1 1 d . . . . .
C12A C 0.09192(19) 0.5380(3) -0.01587(14) 0.0449(6) Uani 1 1 d . . . . .
H12A H 0.113073 0.449691 -0.002784 0.067 Uiso 1 1 calc R U . . .
H12B H 0.015877 0.540207 -0.048589 0.067 Uiso 1 1 calc R U . . .
H12C H 0.093338 0.587155 0.025011 0.067 Uiso 1 1 calc R U . . .
C13A C 0.1461(2) 0.7334(3) -0.06631(17) 0.0540(8) Uani 1 1 d . . . . .
H13A H 0.147794 0.779989 -0.024576 0.081 Uiso 1 1 calc R U . . .
H13B H 0.070563 0.739381 -0.099455 0.081 Uiso 1 1 calc R U . . .
H13C H 0.201233 0.770227 -0.086223 0.081 Uiso 1 1 calc R U . . .
C14A C 0.1813(3) 0.5181(4) -0.10957(16) 0.0600(9) Uani 1 1 d . . . . .
H14A H 0.230446 0.561321 -0.131814 0.090 Uiso 1 1 calc R U . . .
H14B H 0.105661 0.509212 -0.142285 0.090 Uiso 1 1 calc R U . . .
H14C H 0.211906 0.433687 -0.094116 0.090 Uiso 1 1 calc R U . . .
C15A C 0.48118(16) 0.65189(18) 0.17986(10) 0.0219(4) Uani 1 1 d . . . . .
H15A H 0.468314 0.611442 0.220476 0.026 Uiso 1 1 calc R U . . .
H15B H 0.561524 0.676683 0.192198 0.026 Uiso 1 1 calc R U . . .
C16A C 0.40847(16) 0.76900(19) 0.16068(10) 0.0226(4) Uani 1 1 d . . . . .
C17A C 0.29288(17) 0.76483(19) 0.15170(11) 0.0247(4) Uani 1 1 d . . . . .
C18A C 0.22156(18) 0.8660(2) 0.13185(12) 0.0299(5) Uani 1 1 d . . . . .
H18A H 0.143559 0.857551 0.126850 0.036 Uiso 1 1 calc R U . . .
C19A C 0.26556(18) 0.9816(2) 0.11910(12) 0.0308(5) Uani 1 1 d . . . . .
C20A C 0.38064(18) 0.9922(2) 0.12762(12) 0.0303(5) Uani 1 1 d . . . . .
H20A H 0.411708 1.070833 0.119397 0.036 Uiso 1 1 calc R U . . .
C21A C 0.44936(17) 0.8861(2) 0.14829(11) 0.0275(4) Uani 1 1 d . . . . .
H21A H 0.527663 0.894376 0.154160 0.033 Uiso 1 1 calc R U . . .
C22A C 0.2287(2) 1.1969(2) 0.08314(16) 0.0455(6) Uani 1 1 d . . . . .
H22A H 0.282031 1.232164 0.124747 0.068 Uiso 1 1 calc R U . . .
H22B H 0.164864 1.255116 0.066185 0.068 Uiso 1 1 calc R U . . .
H22C H 0.266490 1.185875 0.047985 0.068 Uiso 1 1 calc R U . . .
C23A C 0.0888(2) 0.5218(3) 0.18398(14) 0.0471(7) Uani 1 1 d . . . . .
S1B S 0.61569(4) 0.68285(5) 0.66614(3) 0.02758(11) Uani 1 1 d . . . . .
F1B F 0.51624(15) 0.48637(16) 0.69398(8) 0.0524(4) Uani 1 1 d . . . . .
F2B F 0.52425(15) 0.48796(17) 0.59057(8) 0.0536(4) Uani 1 1 d . . . . .
F3B F 0.67130(15) 0.44379(15) 0.67341(10) 0.0573(4) Uani 1 1 d . . . . .
O1B O 0.95718(12) 0.37915(14) 0.57865(8) 0.0273(3) Uani 1 1 d D . . . .
H1B H 1.005(2) 0.325(2) 0.5799(15) 0.041 Uiso 1 1 d D U . . .
O2B O 1.25682(13) 0.30421(17) 0.79018(8) 0.0366(4) Uani 1 1 d . . . . .
O3B O 0.91012(12) 0.68534(16) 0.43628(7) 0.0286(3) Uani 1 1 d . . . . .
O4B O 0.77667(11) 0.60965(14) 0.48039(6) 0.0241(3) Uani 1 1 d . . . . .
O5B O 0.67969(11) 0.68589(13) 0.61093(7) 0.0226(3) Uani 1 1 d . . . . .
O6B O 0.69002(17) 0.6989(2) 0.73292(9) 0.0461(4) Uani 1 1 d . . . . .
O7B O 0.51349(16) 0.75142(18) 0.64400(12) 0.0508(5) Uani 1 1 d . . . . .
O8B O 0.65590(13) 1.11275(15) 0.53592(9) 0.0342(3) Uani 1 1 d . . . . .
N1B N 0.95062(12) 0.64232(15) 0.54983(8) 0.0184(3) Uani 1 1 d . . . . .
C1B C 0.92040(14) 0.58544(17) 0.60733(9) 0.0172(3) Uani 1 1 d . . . . .
H1BA H 0.841227 0.553852 0.588683 0.021 Uiso 1 1 calc R U . . .
C2B C 1.06779(15) 0.6845(2) 0.56546(10) 0.0223(4) Uani 1 1 d . . . . .
H2BA H 1.083765 0.750675 0.601535 0.027 Uiso 1 1 calc R U . . .
H2BB H 1.079923 0.722113 0.523958 0.027 Uiso 1 1 calc R U . . .
C3B C 1.14730(16) 0.5726(2) 0.58984(10) 0.0252(4) Uani 1 1 d . . . . .
H3BA H 1.142933 0.516341 0.550365 0.030 Uiso 1 1 calc R U . . .
H3BB H 1.225523 0.604667 0.607556 0.030 Uiso 1 1 calc R U . . .
C4B C 1.12040(15) 0.49650(18) 0.64500(10) 0.0205(4) Uani 1 1 d . . . . .
C5B C 1.20123(16) 0.4476(2) 0.69813(10) 0.0231(4) Uani 1 1 d . . . . .
H5B H 1.276243 0.477013 0.706262 0.028 Uiso 1 1 calc R U . . .
C6B C 1.18021(17) 0.3512(2) 0.74430(10) 0.0261(4) Uani 1 1 d . . . . .
C7B C 1.05998(18) 0.3070(2) 0.72922(12) 0.0299(4) Uani 1 1 d . . . . .
H7BA H 1.047502 0.276129 0.771993 0.036 Uiso 1 1 calc R U . . .
H7BB H 1.045754 0.235472 0.696268 0.036 Uiso 1 1 calc R U . . .
C8B C 0.97802(16) 0.4154(2) 0.69924(10) 0.0251(4) Uani 1 1 d . . . . .
H8BA H 0.988889 0.484404 0.733517 0.030 Uiso 1 1 calc R U . . .
H8BB H 0.899696 0.384058 0.688884 0.030 Uiso 1 1 calc R U . . .
C9B C 0.99609(15) 0.46800(18) 0.63377(9) 0.0190(4) Uani 1 1 d . . . . .
C10B C 0.88149(15) 0.64801(17) 0.48538(9) 0.0186(4) Uani 1 1 d . . . . .
C11B C 0.68868(16) 0.6078(2) 0.41374(10) 0.0247(4) Uani 1 1 d . . . . .
C12B C 0.58773(19) 0.5558(3) 0.43184(14) 0.0472(7) Uani 1 1 d . . . . .
H12D H 0.603853 0.468944 0.449415 0.071 Uiso 1 1 calc R U . . .
H12E H 0.521806 0.555184 0.390808 0.071 Uiso 1 1 calc R U . . .
H12F H 0.572363 0.609663 0.466993 0.071 Uiso 1 1 calc R U . . .
C13B C 0.6640(2) 0.7419(3) 0.38750(16) 0.0494(7) Uani 1 1 d . . . . .
H13D H 0.646692 0.794406 0.422515 0.074 Uiso 1 1 calc R U . . .
H13E H 0.599283 0.741695 0.345774 0.074 Uiso 1 1 calc R U . . .
H13F H 0.729927 0.776695 0.377159 0.074 Uiso 1 1 calc R U . . .
C14B C 0.7229(3) 0.5222(4) 0.36466(19) 0.0781(13) Uani 1 1 d . . . . .
H14D H 0.785594 0.560875 0.352369 0.117 Uiso 1 1 calc R U . . .
H14E H 0.658796 0.510293 0.323210 0.117 Uiso 1 1 calc R U . . .
H14F H 0.746437 0.439562 0.386433 0.117 Uiso 1 1 calc R U . . .
C15B C 0.92098(15) 0.68740(19) 0.66176(9) 0.0206(4) Uani 1 1 d . . . . .
H15C H 0.888690 0.650927 0.696212 0.025 Uiso 1 1 calc R U . . .
H15D H 0.999629 0.712981 0.685671 0.025 Uiso 1 1 calc R U . . .
C16B C 0.85379(16) 0.80274(19) 0.62955(10) 0.0202(4) Uani 1 1 d . . . . .
C17B C 0.73687(16) 0.80214(18) 0.60462(10) 0.0205(4) Uani 1 1 d . . . . .
C18B C 0.67203(16) 0.90301(19) 0.57289(10) 0.0231(4) Uani 1 1 d . . . . .
H18B H 0.592350 0.895674 0.555799 0.028 Uiso 1 1 calc R U . . .
C19B C 0.72539(17) 1.01634(19) 0.56626(11) 0.0238(4) Uani 1 1 d . . . . .
C20B C 0.84274(17) 1.02356(19) 0.59055(11) 0.0248(4) Uani 1 1 d . . . . .
H20B H 0.880270 1.100349 0.586416 0.030 Uiso 1 1 calc R U . . .
C21B C 0.90420(17) 0.9171(2) 0.62088(10) 0.0236(4) Uani 1 1 d . . . . .
H21B H 0.984084 0.922641 0.636368 0.028 Uiso 1 1 calc R U . . .
C22B C 0.7036(2) 1.2358(2) 0.53837(15) 0.0382(5) Uani 1 1 d . . . . .
H22D H 0.753449 1.237747 0.509452 0.057 Uiso 1 1 calc R U . . .
H22E H 0.747101 1.256183 0.585742 0.057 Uiso 1 1 calc R U . . .
H22F H 0.643345 1.298534 0.521587 0.057 Uiso 1 1 calc R U . . .
C23B C 0.5803(2) 0.5136(2) 0.65455(12) 0.0326(5) Uani 1 1 d . . . . .


_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
S1A O5A 1.5706(15) . ?
S1A O6A 1.405(2) . ?
S1A O7A 1.4054(17) . ?
S1A C23A 1.826(3) . ?
F1A C23A 1.313(3) . ?
F2A C23A 1.329(4) . ?
F3A C23A 1.310(4) . ?
O1A H1A 0.83(2) . ?
O1A C9A 1.430(2) . ?
O2A C6A 1.221(3) . ?
O3A C10A 1.229(2) . ?
O4A C10A 1.342(2) . ?
O4A C11A 1.468(2) . ?
O5A C17A 1.434(2) . ?
O8A C19A 1.361(3) . ?
O8A C22A 1.420(3) . ?
N1A C1A 1.469(2) . ?
N1A C2A 1.468(2) . ?
N1A C10A 1.345(2) . ?
C1A H1AA 1.0000 . ?
C1A C9A 1.548(3) . ?
C1A C15A 1.543(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.529(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.502(3) . ?
C4A C5A 1.337(3) . ?
C4A C9A 1.521(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.465(3) . ?
C6A C7A 1.504(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.530(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.528(3) . ?
C11A C12A 1.518(3) . ?
C11A C13A 1.516(4) . ?
C11A C14A 1.507(4) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C15A C16A 1.509(3) . ?
C16A C17A 1.396(3) . ?
C16A C21A 1.386(3) . ?
C17A C18A 1.367(3) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.391(3) . ?
C19A C20A 1.395(3) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.391(3) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
S1B O5B 1.5703(13) . ?
S1B O6B 1.4090(19) . ?
S1B O7B 1.4127(18) . ?
S1B C23B 1.832(2) . ?
F1B C23B 1.328(3) . ?
F2B C23B 1.312(3) . ?
F3B C23B 1.307(3) . ?
O1B H1B 0.83(2) . ?
O1B C9B 1.432(2) . ?
O2B C6B 1.221(3) . ?
O3B C10B 1.229(2) . ?
O4B C10B 1.341(2) . ?
O4B C11B 1.468(2) . ?
O5B C17B 1.441(2) . ?
O8B C19B 1.355(2) . ?
O8B C22B 1.419(3) . ?
N1B C1B 1.469(2) . ?
N1B C2B 1.465(2) . ?
N1B C10B 1.340(2) . ?
C1B H1BA 1.0000 . ?
C1B C9B 1.548(3) . ?
C1B C15B 1.545(3) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.522(3) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.503(3) . ?
C4B C5B 1.340(3) . ?
C4B C9B 1.525(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.464(3) . ?
C6B C7B 1.508(3) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.529(3) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.529(3) . ?
C11B C12B 1.518(3) . ?
C11B C13B 1.508(3) . ?
C11B C14B 1.505(4) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C15B C16B 1.507(3) . ?
C16B C17B 1.389(3) . ?
C16B C21B 1.393(3) . ?
C17B C18B 1.371(3) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.392(3) . ?
C19B C20B 1.396(3) . ?
C20B H20B 0.9500 . ?
C20B C21B 1.392(3) . ?
C21B H21B 0.9500 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 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
O5A S1A C23A 95.09(10) . . ?
O6A S1A O5A 110.43(10) . . ?
O6A S1A O7A 121.36(13) . . ?
O6A S1A C23A 106.84(15) . . ?
O7A S1A O5A 111.60(10) . . ?
O7A S1A C23A 108.12(13) . . ?
C9A O1A H1A 111(2) . . ?
C10A O4A C11A 121.60(15) . . ?
C17A O5A S1A 121.65(13) . . ?
C19A O8A C22A 117.86(18) . . ?
C2A N1A C1A 115.68(15) . . ?
C10A N1A C1A 123.59(15) . . ?
C10A N1A C2A 120.47(16) . . ?
N1A C1A H1AA 107.5 . . ?
N1A C1A C9A 108.95(15) . . ?
N1A C1A C15A 109.92(15) . . ?
C9A C1A H1AA 107.5 . . ?
C15A C1A H1AA 107.5 . . ?
C15A C1A C9A 115.21(15) . . ?
N1A C2A H2AA 109.7 . . ?
N1A C2A H2AB 109.7 . . ?
N1A C2A C3A 110.03(17) . . ?
H2AA C2A H2AB 108.2 . . ?
C3A C2A H2AA 109.7 . . ?
C3A C2A H2AB 109.7 . . ?
C2A C3A H3AA 109.0 . . ?
C2A C3A H3AB 109.0 . . ?
H3AA C3A H3AB 107.8 . . ?
C4A C3A C2A 113.05(16) . . ?
C4A C3A H3AA 109.0 . . ?
C4A C3A H3AB 109.0 . . ?
C3A C4A C9A 115.56(16) . . ?
C5A C4A C3A 122.49(18) . . ?
C5A C4A C9A 121.84(18) . . ?
C4A C5A H5A 118.4 . . ?
C4A C5A C6A 123.19(19) . . ?
C6A C5A H5A 118.4 . . ?
O2A C6A C5A 121.5(2) . . ?
O2A C6A C7A 122.2(2) . . ?
C5A C6A C7A 116.19(17) . . ?
C6A C7A H7AA 109.7 . . ?
C6A C7A H7AB 109.7 . . ?
C6A C7A C8A 109.97(17) . . ?
H7AA C7A H7AB 108.2 . . ?
C8A C7A H7AA 109.7 . . ?
C8A C7A H7AB 109.7 . . ?
C7A C8A H8AA 109.2 . . ?
C7A C8A H8AB 109.2 . . ?
H8AA C8A H8AB 107.9 . . ?
C9A C8A C7A 111.85(16) . . ?
C9A C8A H8AA 109.2 . . ?
C9A C8A H8AB 109.2 . . ?
O1A C9A C1A 103.82(14) . . ?
O1A C9A C4A 109.39(15) . . ?
O1A C9A C8A 109.95(16) . . ?
C4A C9A C1A 110.15(15) . . ?
C4A C9A C8A 112.15(15) . . ?
C8A C9A C1A 111.05(15) . . ?
O3A C10A O4A 123.70(17) . . ?
O3A C10A N1A 124.37(18) . . ?
O4A C10A N1A 111.92(16) . . ?
O4A C11A C12A 101.74(17) . . ?
O4A C11A C13A 109.4(2) . . ?
O4A C11A C14A 110.6(2) . . ?
C13A C11A C12A 109.9(2) . . ?
C14A C11A C12A 111.7(2) . . ?
C14A C11A C13A 112.9(3) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C1A C15A H15A 109.4 . . ?
C1A C15A H15B 109.4 . . ?
H15A C15A H15B 108.0 . . ?
C16A C15A C1A 111.31(15) . . ?
C16A C15A H15A 109.4 . . ?
C16A C15A H15B 109.4 . . ?
C17A C16A C15A 121.48(18) . . ?
C21A C16A C15A 123.27(18) . . ?
C21A C16A C17A 115.21(18) . . ?
C16A C17A O5A 117.13(17) . . ?
C18A C17A O5A 118.24(18) . . ?
C18A C17A C16A 124.47(19) . . ?
C17A C18A H18A 120.7 . . ?
C17A C18A C19A 118.62(19) . . ?
C19A C18A H18A 120.7 . . ?
O8A C19A C18A 115.27(19) . . ?
O8A C19A C20A 125.1(2) . . ?
C18A C19A C20A 119.7(2) . . ?
C19A C20A H20A 120.4 . . ?
C21A C20A C19A 119.2(2) . . ?
C21A C20A H20A 120.4 . . ?
C16A C21A C20A 122.82(19) . . ?
C16A C21A H21A 118.6 . . ?
C20A C21A H21A 118.6 . . ?
O8A C22A H22A 109.5 . . ?
O8A C22A H22B 109.5 . . ?
O8A C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
F1A C23A S1A 108.92(18) . . ?
F1A C23A F2A 107.9(3) . . ?
F2A C23A S1A 109.9(2) . . ?
F3A C23A S1A 110.9(2) . . ?
F3A C23A F1A 110.3(3) . . ?
F3A C23A F2A 108.9(2) . . ?
O5B S1B C23B 94.69(9) . . ?
O6B S1B O5B 111.65(9) . . ?
O6B S1B O7B 120.78(13) . . ?
O6B S1B C23B 107.67(12) . . ?
O7B S1B O5B 111.38(10) . . ?
O7B S1B C23B 107.25(12) . . ?
C9B O1B H1B 111(2) . . ?
C10B O4B C11B 120.61(14) . . ?
C17B O5B S1B 117.09(12) . . ?
C19B O8B C22B 117.66(17) . . ?
C2B N1B C1B 115.48(14) . . ?
C10B N1B C1B 124.29(15) . . ?
C10B N1B C2B 120.02(15) . . ?
N1B C1B H1BA 107.1 . . ?
N1B C1B C9B 109.13(14) . . ?
N1B C1B C15B 110.48(15) . . ?
C9B C1B H1BA 107.1 . . ?
C15B C1B H1BA 107.1 . . ?
C15B C1B C9B 115.66(14) . . ?
N1B C2B H2BA 109.6 . . ?
N1B C2B H2BB 109.6 . . ?
N1B C2B C3B 110.05(16) . . ?
H2BA C2B H2BB 108.2 . . ?
C3B C2B H2BA 109.6 . . ?
C3B C2B H2BB 109.6 . . ?
C2B C3B H3BA 109.0 . . ?
C2B C3B H3BB 109.0 . . ?
H3BA C3B H3BB 107.8 . . ?
C4B C3B C2B 112.74(15) . . ?
C4B C3B H3BA 109.0 . . ?
C4B C3B H3BB 109.0 . . ?
C3B C4B C9B 116.12(16) . . ?
C5B C4B C3B 122.02(18) . . ?
C5B C4B C9B 121.63(18) . . ?
C4B C5B H5B 118.2 . . ?
C4B C5B C6B 123.55(18) . . ?
C6B C5B H5B 118.2 . . ?
O2B C6B C5B 121.70(19) . . ?
O2B C6B C7B 121.9(2) . . ?
C5B C6B C7B 116.32(17) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B C8B 110.66(17) . . ?
H7BA C7B H7BB 108.1 . . ?
C8B C7B H7BA 109.5 . . ?
C8B C7B H7BB 109.5 . . ?
C7B C8B H8BA 109.4 . . ?
C7B C8B H8BB 109.4 . . ?
C7B C8B C9B 111.29(16) . . ?
H8BA C8B H8BB 108.0 . . ?
C9B C8B H8BA 109.4 . . ?
C9B C8B H8BB 109.4 . . ?
O1B C9B C1B 102.79(14) . . ?
O1B C9B C4B 109.36(14) . . ?
O1B C9B C8B 110.51(16) . . ?
C4B C9B C1B 112.23(15) . . ?
C4B C9B C8B 110.69(15) . . ?
C8B C9B C1B 111.00(15) . . ?
O3B C10B O4B 123.54(16) . . ?
O3B C10B N1B 124.09(17) . . ?
N1B C10B O4B 112.36(15) . . ?
O4B C11B C12B 102.55(16) . . ?
O4B C11B C13B 109.42(18) . . ?
O4B C11B C14B 110.25(19) . . ?
C13B C11B C12B 109.3(2) . . ?
C14B C11B C12B 111.8(3) . . ?
C14B C11B C13B 113.0(3) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11B C14B H14D 109.5 . . ?
C11B C14B H14E 109.5 . . ?
C11B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C1B C15B H15C 109.4 . . ?
C1B C15B H15D 109.4 . . ?
H15C C15B H15D 108.0 . . ?
C16B C15B C1B 111.29(15) . . ?
C16B C15B H15C 109.4 . . ?
C16B C15B H15D 109.4 . . ?
C17B C16B C15B 122.52(17) . . ?
C17B C16B C21B 114.84(18) . . ?
C21B C16B C15B 122.62(17) . . ?
C16B C17B O5B 117.57(17) . . ?
C18B C17B O5B 117.59(16) . . ?
C18B C17B C16B 124.82(18) . . ?
C17B C18B H18B 120.7 . . ?
C17B C18B C19B 118.63(18) . . ?
C19B C18B H18B 120.7 . . ?
O8B C19B C18B 115.37(18) . . ?
O8B C19B C20B 125.19(18) . . ?
C18B C19B C20B 119.45(18) . . ?
C19B C20B H20B 120.3 . . ?
C21B C20B C19B 119.31(18) . . ?
C21B C20B H20B 120.3 . . ?
C16B C21B H21B 118.5 . . ?
C20B C21B C16B 122.93(18) . . ?
C20B C21B H21B 118.5 . . ?
O8B C22B H22D 109.5 . . ?
O8B C22B H22E 109.5 . . ?
O8B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
F1B C23B S1B 107.25(17) . . ?
F2B C23B S1B 111.29(16) . . ?
F2B C23B F1B 109.14(19) . . ?
F3B C23B S1B 110.77(16) . . ?
F3B C23B F1B 109.1(2) . . ?
F3B C23B F2B 109.2(2) . . ?

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
O1A H1A O3A 0.83(2) 1.87(2) 2.704(2) 175(3) 2_645 yes
O1B H1B O3B 0.83(2) 1.89(2) 2.700(2) 166(3) 2_746 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
S1A O5A C17A C16A 100.22(19) . . . . ?
S1A O5A C17A C18A -84.1(2) . . . . ?
O2A C6A C7A C8A 144.6(2) . . . . ?
O5A S1A C23A F1A -177.2(2) . . . . ?
O5A S1A C23A F2A -59.23(19) . . . . ?
O5A S1A C23A F3A 61.2(2) . . . . ?
O5A C17A C18A C19A -174.99(19) . . . . ?
O6A S1A O5A C17A -108.10(17) . . . . ?
O6A S1A C23A F1A 69.7(3) . . . . ?
O6A S1A C23A F2A -172.37(17) . . . . ?
O6A S1A C23A F3A -51.9(2) . . . . ?
O7A S1A O5A C17A 30.03(18) . . . . ?
O7A S1A C23A F1A -62.5(3) . . . . ?
O7A S1A C23A F2A 55.5(2) . . . . ?
O7A S1A C23A F3A 175.94(19) . . . . ?
O8A C19A C20A C21A -179.2(2) . . . . ?
N1A C1A C9A O1A -63.89(17) . . . . ?
N1A C1A C9A C4A 53.14(19) . . . . ?
N1A C1A C9A C8A 178.00(15) . . . . ?
N1A C1A C15A C16A 54.5(2) . . . . ?
N1A C2A C3A C4A -47.3(2) . . . . ?
C1A N1A C2A C3A 57.1(2) . . . . ?
C1A N1A C10A O3A -174.1(2) . . . . ?
C1A N1A C10A O4A 6.7(3) . . . . ?
C1A C15A C16A C17A 69.5(2) . . . . ?
C1A C15A C16A C21A -108.1(2) . . . . ?
C2A N1A C1A C9A -60.5(2) . . . . ?
C2A N1A C1A C15A 66.6(2) . . . . ?
C2A N1A C10A O3A -0.4(3) . . . . ?
C2A N1A C10A O4A -179.60(17) . . . . ?
C2A C3A C4A C5A -137.5(2) . . . . ?
C2A C3A C4A C9A 46.2(2) . . . . ?
C3A C4A C5A C6A -166.98(19) . . . . ?
C3A C4A C9A O1A 64.8(2) . . . . ?
C3A C4A C9A C1A -48.8(2) . . . . ?
C3A C4A C9A C8A -172.98(17) . . . . ?
C4A C5A C6A O2A -177.4(2) . . . . ?
C4A C5A C6A C7A 5.9(3) . . . . ?
C5A C4A C9A O1A -111.5(2) . . . . ?
C5A C4A C9A C1A 134.9(2) . . . . ?
C5A C4A C9A C8A 10.7(3) . . . . ?
C5A C6A C7A C8A -38.7(2) . . . . ?
C6A C7A C8A C9A 57.8(2) . . . . ?
C7A C8A C9A O1A 78.06(19) . . . . ?
C7A C8A C9A C1A -167.61(16) . . . . ?
C7A C8A C9A C4A -43.9(2) . . . . ?
C9A C1A C15A C16A 178.02(16) . . . . ?
C9A C4A C5A C6A 9.1(3) . . . . ?
C10A O4A C11A C12A 179.5(2) . . . . ?
C10A O4A C11A C13A -64.2(3) . . . . ?
C10A O4A C11A C14A 60.7(3) . . . . ?
C10A N1A C1A C9A 113.48(19) . . . . ?
C10A N1A C1A C15A -119.41(19) . . . . ?
C10A N1A C2A C3A -117.2(2) . . . . ?
C11A O4A C10A O3A -2.3(3) . . . . ?
C11A O4A C10A N1A 176.92(18) . . . . ?
C15A C1A C9A O1A 172.07(15) . . . . ?
C15A C1A C9A C4A -70.90(19) . . . . ?
C15A C1A C9A C8A 54.0(2) . . . . ?
C15A C16A C17A O5A -2.0(3) . . . . ?
C15A C16A C17A C18A -177.4(2) . . . . ?
C15A C16A C21A C20A 177.0(2) . . . . ?
C16A C17A C18A C19A 0.4(3) . . . . ?
C17A C16A C21A C20A -0.7(3) . . . . ?
C17A C18A C19A O8A 178.9(2) . . . . ?
C17A C18A C19A C20A -0.8(3) . . . . ?
C18A C19A C20A C21A 0.5(3) . . . . ?
C19A C20A C21A C16A 0.3(4) . . . . ?
C21A C16A C17A O5A 175.78(18) . . . . ?
C21A C16A C17A C18A 0.4(3) . . . . ?
C22A O8A C19A C18A -178.7(2) . . . . ?
C22A O8A C19A C20A 1.0(4) . . . . ?
C23A S1A O5A C17A 141.81(17) . . . . ?
S1B O5B C17B C16B 106.99(17) . . . . ?
S1B O5B C17B C18B -74.6(2) . . . . ?
O2B C6B C7B C8B 150.9(2) . . . . ?
O5B S1B C23B F1B -175.79(16) . . . . ?
O5B S1B C23B F2B -56.49(17) . . . . ?
O5B S1B C23B F3B 65.24(17) . . . . ?
O5B C17B C18B C19B 179.95(16) . . . . ?
O6B S1B O5B C17B -62.70(16) . . . . ?
O6B S1B C23B F1B 69.71(19) . . . . ?
O6B S1B C23B F2B -170.98(17) . . . . ?
O6B S1B C23B F3B -49.25(19) . . . . ?
O7B S1B O5B C17B 75.60(16) . . . . ?
O7B S1B C23B F1B -61.7(2) . . . . ?
O7B S1B C23B F2B 57.62(19) . . . . ?
O7B S1B C23B F3B 179.35(17) . . . . ?
O8B C19B C20B C21B 179.87(19) . . . . ?
N1B C1B C9B O1B -68.94(17) . . . . ?
N1B C1B C9B C4B 48.45(19) . . . . ?
N1B C1B C9B C8B 172.90(15) . . . . ?
N1B C1B C15B C16B 49.92(19) . . . . ?
N1B C2B C3B C4B -49.3(2) . . . . ?
C1B N1B C2B C3B 59.9(2) . . . . ?
C1B N1B C10B O3B -173.26(18) . . . . ?
C1B N1B C10B O4B 7.5(2) . . . . ?
C1B C15B C16B C17B 72.4(2) . . . . ?
C1B C15B C16B C21B -105.9(2) . . . . ?
C2B N1B C1B C9B -59.3(2) . . . . ?
C2B N1B C1B C15B 68.96(19) . . . . ?
C2B N1B C10B O3B 1.3(3) . . . . ?
C2B N1B C10B O4B -178.03(16) . . . . ?
C2B C3B C4B C5B -141.49(19) . . . . ?
C2B C3B C4B C9B 43.8(2) . . . . ?
C3B C4B C5B C6B -166.19(18) . . . . ?
C3B C4B C9B O1B 69.9(2) . . . . ?
C3B C4B C9B C1B -43.5(2) . . . . ?
C3B C4B C9B C8B -168.15(17) . . . . ?
C4B C5B C6B O2B 176.4(2) . . . . ?
C4B C5B C6B C7B 0.2(3) . . . . ?
C5B C4B C9B O1B -104.8(2) . . . . ?
C5B C4B C9B C1B 141.77(18) . . . . ?
C5B C4B C9B C8B 17.1(3) . . . . ?
C5B C6B C7B C8B -33.0(3) . . . . ?
C6B C7B C8B C9B 58.0(2) . . . . ?
C7B C8B C9B O1B 71.8(2) . . . . ?
C7B C8B C9B C1B -174.87(16) . . . . ?
C7B C8B C9B C4B -49.5(2) . . . . ?
C9B C1B C15B C16B 174.50(15) . . . . ?
C9B C4B C5B C6B 8.2(3) . . . . ?
C10B O4B C11B C12B 178.50(19) . . . . ?
C10B O4B C11B C13B -65.6(2) . . . . ?
C10B O4B C11B C14B 59.3(3) . . . . ?
C10B N1B C1B C9B 115.47(18) . . . . ?
C10B N1B C1B C15B -116.30(18) . . . . ?
C10B N1B C2B C3B -115.10(18) . . . . ?
C11B O4B C10B O3B 1.3(3) . . . . ?
C11B O4B C10B N1B -179.41(16) . . . . ?
C15B C1B C9B O1B 165.79(15) . . . . ?
C15B C1B C9B C4B -76.82(19) . . . . ?
C15B C1B C9B C8B 47.6(2) . . . . ?
C15B C16B C17B O5B 0.5(3) . . . . ?
C15B C16B C17B C18B -177.75(18) . . . . ?
C15B C16B C21B C20B 179.31(18) . . . . ?
C16B C17B C18B C19B -1.8(3) . . . . ?
C17B C16B C21B C20B 0.9(3) . . . . ?
C17B C18B C19B O8B -178.44(18) . . . . ?
C17B C18B C19B C20B 1.4(3) . . . . ?
C18B C19B C20B C21B 0.1(3) . . . . ?
C19B C20B C21B C16B -1.3(3) . . . . ?
C21B C16B C17B O5B 178.92(16) . . . . ?
C21B C16B C17B C18B 0.7(3) . . . . ?
C22B O8B C19B C18B 169.4(2) . . . . ?
C22B O8B C19B C20B -10.4(3) . . . . ?
C23B S1B O5B C17B -173.81(14) . . . . ?

_olex2_submission_original_sample_id JMHWLB
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.812
####################################################################### 
# 
# 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_jmhwlc
_database_code_depnum_ccdc_archive 'CCDC 2341583'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   JMHWLC
_nottingham_internal_coll_number 19434
_nottingham_internal_coll_client JM/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '12.00, 3.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczkj1
_nottingham_internal_coll_date   25/04/2023
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 26/04/2023
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 26/04/2023
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 26/04/2023
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_self_archive_date 26/04/2023
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date pczspa
_nottingham_internal_validation_user 26/04/2023
_nottingham_internal_archive_date ?
_refine_special_details          
'All hydrogen atoms were observed in the electron density map. Hydroxy hydrogen atoms H1A were refined with the O-H distance restrained to a target value of 0.84 %A (DFIX esd 0.02%A). All other hydrogen atoms in the structure were geometrically placed and refined with a riding model.'
_audit_creation_date             2023-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H28 F3 N O8 S'
_chemical_formula_sum            'C23 H28 F3 N O8 S'
_chemical_formula_weight         535.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H28F3NO8S
_chemical_oxdiff_usercomment     
'JMHWLC #19434 GVA-2056 KDJ/HWL fomblin oil on micromount'
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'
F F 0.0727 0.0534 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.0308(2)
_cell_length_b                   11.67240(10)
_cell_length_c                   11.0847(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.773(3)
_cell_angle_gamma                90
_cell_volume                     1274.22(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17249
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.6210
_cell_measurement_theta_min      4.4660
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.721
_exptl_absorpt_coefficient_mu    1.751
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
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_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -5 0.0516
1 0 5 0.0586
0 1 0 0.0980
0 -1 0 0.0980
-1 0 1 0.0140
1 0 -1 0.0254
-3 3 -4 0.0783
3 -3 4 0.0783
1 6 3 0.0879

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc and pentane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
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
-1.0001 -0.0003 -4.9955 0.2743 0.0647 -0.8120
1.0001 0.0003 4.9955 -0.2743 -0.0647 0.8120
0.0004 0.9993 -0.0003 -0.1244 -0.0093 -0.0426
-0.0004 -0.9993 0.0003 0.1244 0.0093 0.0426
-0.9992 0.0002 0.9995 -0.0057 -0.1554 0.0507
0.9992 -0.0002 -0.9995 0.0057 0.1554 -0.0507
-2.9975 2.9981 -3.9965 -0.0639 -0.2373 -0.9824
2.9975 -2.9981 3.9965 0.0639 0.2373 0.9824
1.0022 5.9962 2.9956 -0.9276 -0.0473 0.2686

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.736
_diffrn_reflns_theta_min         4.468
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  27.00   1.00    3.00    --  -43.06  38.00-180.00   47
  2  ω    -69.00  26.00   1.00    3.00    --  -43.06  77.00  60.00   95
  3  ω     16.00  43.00   1.00    3.00    --   43.06  66.00 -15.22   27
  4  ω     68.00  97.00   1.00    3.00    --   43.06  57.00 -60.00   29
  5  ω     13.00  39.00   1.00    3.00    --   43.06  77.00-159.07   26
  6  ω     27.00  78.00   1.00    3.00    --   43.06  57.00-120.00   51
  7  ω     63.00  94.00   1.00    3.00    --   43.06  38.00  60.00   31
  8  ω    -26.00  67.00   1.00    3.00    --   43.06 -57.00-120.00   93
  9  ω     19.00  96.00   1.00    3.00    --   43.06  57.00  90.00   77
 10  ω     21.00  71.00   1.00    3.00    --   43.06  67.00  20.17   50
 11  ω     55.00  98.00   1.00    3.00    --   43.06  57.00-180.00   43
 12  ω     21.00  66.00   1.00    3.00    --   43.06  57.00 -60.00   45
 13  ω     19.00  46.00   1.00    3.00    --   43.06  57.00-180.00   27
 14  ω     23.00  61.00   1.00    3.00    --   43.06  38.00  60.00   38
 15  ω     13.00  39.00   1.00    3.00    --   43.06  76.00 128.52   26
 16  ω     72.00 170.00   1.00   12.00    --  100.81  71.00 158.77   98
 17  ω     75.00 105.00   1.00   12.00    --  100.81  63.00 -72.76   30
 18  ω     77.00 102.00   1.00   12.00    --  100.81  59.00 142.45   25
 19  ω     78.00 169.00   1.00   12.00    --  100.81  57.00 129.15   91
 20  ω     33.00  93.00   1.00   12.00    --  100.81 -61.00  60.00   60
 21  ω    130.00 170.00   1.00   12.00    --  100.81  64.00-160.47   40
 22  ω    133.00 169.00   1.00   12.00    --  100.81  59.00  52.59   36
 23  ω     76.00 103.00   1.00   12.00    --  100.81  61.00 150.00   27
 24  ω     76.00 102.00   1.00   12.00    --  100.81  61.00 -30.00   26
 25  ω     76.00 170.00   1.00   12.00    --  100.81  61.00 -90.00   94
 26  ω     29.00  71.00   1.00   12.00    --  100.81 -77.00 150.00   42
 27  ω     97.00 124.00   1.00   12.00    --  100.81 -77.00 150.00   27
 28  ω     81.00 110.00   1.00   12.00    --  100.81  45.00   0.00   29
 29  ω    137.00 170.00   1.00   12.00    --  100.81  61.00-180.00   33
 30  ω     72.00 107.00   1.00   12.00    --  100.81-125.00 120.00   35
 31  ω     75.00 101.00   1.00   12.00    --  100.81  64.00-160.47   26
 32  ω     29.00 127.00   1.00   12.00    --  100.81 -77.00 -60.00   98
 33  ω     30.00 113.00   1.00   12.00    --  100.81-125.00-120.00   83
 34  ω    128.00 158.00   1.00   12.00    --  100.81  54.00 120.82   30
 35  ω     76.00 103.00   1.00   12.00    --  100.81  59.00  52.59   27
 36  ω     76.00 103.00   1.00   12.00    --  100.81  61.00  30.00   27
 37  ω     76.00 125.00   1.00   12.00    --  100.81  61.00  90.00   49
 38  ω     78.00 109.00   1.00   12.00    --  100.81  61.00  68.58   31
 39  ω    127.00 166.00   1.00   12.00    --  100.81  61.00  30.00   39
 40  ω     77.00 123.00   1.00   12.00    --  100.81  54.00 120.82   46
 41  ω     76.00 108.00   1.00   12.00    --  100.81  61.00   0.00   32
 42  ω     76.00 102.00   1.00   12.00    --  100.81  61.00-180.00   26
 43  ω     29.00 106.00   1.00   12.00    --  100.81-125.00 -30.00   77
 44  ω     77.00 102.00   1.00   12.00    --  100.81  61.00-120.00   25
 45  ω     78.00 105.00   1.00   12.00    --  100.81  48.00-148.68   27
 46  ω     76.00 102.00   1.00   12.00    --  100.81  61.00 -60.00   26
 47  ω     81.00 158.00   1.00   12.00    --  100.81  45.00 -30.00   77
 48  ω     79.00 111.00   1.00   12.00    --  100.81  45.00-120.00   32
 49  ω     54.00  80.00   1.00   12.00    --  100.81-125.00  30.00   26
 50  ω     88.00 113.00   1.00   12.00    --  100.81-125.00  30.00   25
 51  ω     73.00 150.00   1.00   12.00    --  100.81  68.00-110.87   77
 52  ω     73.00 170.00   1.00   12.00    --  100.81  70.00   5.06   97
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0409812000
_diffrn_orient_matrix_UB_12      -0.1245226000
_diffrn_orient_matrix_UB_13      -0.0466926000
_diffrn_orient_matrix_UB_21      0.1187548000
_diffrn_orient_matrix_UB_22      -0.0093905000
_diffrn_orient_matrix_UB_23      -0.0367308000
_diffrn_orient_matrix_UB_31      0.0932206000
_diffrn_orient_matrix_UB_32      -0.0426647000
_diffrn_orient_matrix_UB_33      0.1438859000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4947
_reflns_number_total             4978
_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 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 2289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.030
_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)+(0.0346P)²+0.2029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0565
_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, All O(H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C18(H18), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.87573(4) 0.49127(3) 0.41338(4) 0.01996(10) Uani 1 1 d . . . . .
F1 F 0.97673(15) 0.38431(11) 0.27539(15) 0.0422(3) Uani 1 1 d . . . . .
F2 F 0.87111(13) 0.27534(10) 0.35084(14) 0.0379(3) Uani 1 1 d . . . . .
F3 F 1.06834(13) 0.33847(13) 0.48601(14) 0.0441(3) Uani 1 1 d . . . . .
O1 O 0.59259(12) 0.81189(10) 0.51117(13) 0.0193(2) Uani 1 1 d D . . . .
H1 H 0.541(2) 0.852(2) 0.445(2) 0.029 Uiso 1 1 d D U . . .
O2 O 0.15088(14) 0.55797(16) 0.26057(15) 0.0372(3) Uani 1 1 d . . . . .
O3 O 0.57535(12) 0.43385(10) 0.71919(12) 0.0195(2) Uani 1 1 d . . . . .
O4 O 0.53561(12) 0.55183(10) 0.86052(12) 0.0202(2) Uani 1 1 d . . . . .
O5 O 0.82404(11) 0.44118(11) 0.51350(12) 0.0183(2) Uani 1 1 d . . . . .
O6 O 0.97987(15) 0.57309(12) 0.47643(15) 0.0320(3) Uani 1 1 d . . . . .
O7 O 0.75789(15) 0.51412(12) 0.29150(14) 0.0311(3) Uani 1 1 d . . . . .
O8 O 1.13284(14) 0.28865(12) 0.94973(14) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.62407(13) 0.62498(12) 0.73153(13) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.63888(16) 0.62095(14) 0.60581(16) 0.0145(3) Uani 1 1 d . . . . .
H1A H 0.619045 0.540807 0.570334 0.017 Uiso 1 1 calc R U . . .
C2 C 0.59220(16) 0.73968(14) 0.76396(17) 0.0161(3) Uani 1 1 d . . . . .
H2A H 0.656258 0.796549 0.758743 0.019 Uiso 1 1 calc R U . . .
H2B H 0.601218 0.740529 0.856949 0.019 Uiso 1 1 calc R U . . .
C3 C 0.44542(17) 0.77065(15) 0.66192(17) 0.0178(3) Uani 1 1 d . . . . .
H3A H 0.381445 0.746371 0.697219 0.021 Uiso 1 1 calc R U . . .
H3B H 0.436884 0.854537 0.647330 0.021 Uiso 1 1 calc R U . . .
C4 C 0.41250(17) 0.71001(14) 0.53059(16) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.29260(18) 0.66038(15) 0.45646(17) 0.0202(3) Uani 1 1 d . . . . .
H5 H 0.222230 0.670225 0.482617 0.024 Uiso 1 1 calc R U . . .
C6 C 0.26476(18) 0.59090(16) 0.33570(18) 0.0224(4) Uani 1 1 d . . . . .
C7 C 0.38632(17) 0.55851(15) 0.31550(17) 0.0202(3) Uani 1 1 d . . . . .
H7A H 0.356179 0.537961 0.219583 0.024 Uiso 1 1 calc R U . . .
H7B H 0.430472 0.490376 0.371211 0.024 Uiso 1 1 calc R U . . .
C8 C 0.48907(18) 0.65611(15) 0.35416(17) 0.0189(3) Uani 1 1 d . . . . .
H8A H 0.449097 0.719768 0.289100 0.023 Uiso 1 1 calc R U . . .
H8B H 0.570628 0.628927 0.347050 0.023 Uiso 1 1 calc R U . . .
C9 C 0.53203(16) 0.70129(14) 0.49735(17) 0.0157(3) Uani 1 1 d . . . . .
C10 C 0.57670(15) 0.52874(14) 0.76607(16) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.4621(2) 0.46452(16) 0.8985(2) 0.0303(4) Uani 1 1 d . . . . .
C12 C 0.5554(3) 0.3663(2) 0.9710(3) 0.0477(6) Uani 1 1 d . . . . .
H12A H 0.581071 0.325939 0.908441 0.072 Uiso 1 1 calc R U . . .
H12B H 0.508533 0.313169 1.004413 0.072 Uiso 1 1 calc R U . . .
H12C H 0.637064 0.395885 1.047312 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3351(3) 0.4280(3) 0.7731(3) 0.0473(6) Uani 1 1 d . . . . .
H13A H 0.290543 0.495728 0.719079 0.071 Uiso 1 1 calc R U . . .
H13B H 0.272575 0.389182 0.800473 0.071 Uiso 1 1 calc R U . . .
H13C H 0.360382 0.375526 0.719207 0.071 Uiso 1 1 calc R U . . .
C14 C 0.4231(3) 0.5311(2) 0.9940(3) 0.0437(6) Uani 1 1 d . . . . .
H14A H 0.505523 0.557523 1.071949 0.065 Uiso 1 1 calc R U . . .
H14B H 0.371290 0.481286 1.025043 0.065 Uiso 1 1 calc R U . . .
H14C H 0.367460 0.597313 0.946485 0.065 Uiso 1 1 calc R U . . .
C15 C 0.78553(17) 0.64897(14) 0.63438(18) 0.0183(3) Uani 1 1 d . . . . .
H15A H 0.789971 0.659018 0.547774 0.022 Uiso 1 1 calc R U . . .
H15B H 0.813803 0.721847 0.685208 0.022 Uiso 1 1 calc R U . . .
C16 C 0.88157(16) 0.55456(15) 0.71507(17) 0.0183(3) Uani 1 1 d . . . . .
C17 C 0.90071(16) 0.45526(14) 0.65745(16) 0.0172(3) Uani 1 1 d . . . . .
C18 C 0.98066(17) 0.36349(15) 0.72793(18) 0.0197(3) Uani 1 1 d . . . . .
H18 H 0.988523 0.297173 0.682255 0.024 Uiso 1 1 calc R U . . .
C19 C 1.04898(17) 0.37178(16) 0.86778(18) 0.0221(4) Uani 1 1 d . . . . .
C20 C 1.03485(18) 0.47034(17) 0.93169(18) 0.0260(4) Uani 1 1 d . . . . .
H20 H 1.081634 0.476368 1.027343 0.031 Uiso 1 1 calc R U . . .
C21 C 0.95286(18) 0.55927(17) 0.85607(18) 0.0230(4) Uani 1 1 d . . . . .
H21 H 0.944724 0.625705 0.901398 0.028 Uiso 1 1 calc R U . . .
C22 C 1.1497(2) 0.18727(17) 0.8863(2) 0.0279(4) Uani 1 1 d . . . . .
H22A H 1.188547 0.207629 0.825194 0.042 Uiso 1 1 calc R U . . .
H22B H 1.061328 0.150447 0.834817 0.042 Uiso 1 1 calc R U . . .
H22C H 1.210948 0.134304 0.955592 0.042 Uiso 1 1 calc R U . . .
C23 C 0.95372(19) 0.36359(16) 0.3797(2) 0.0247(4) Uani 1 1 d . . . . .


_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 O5 1.5713(12) . ?
S1 O6 1.4130(14) . ?
S1 O7 1.4156(15) . ?
S1 C23 1.8413(19) . ?
F1 C23 1.313(2) . ?
F2 C23 1.316(2) . ?
F3 C23 1.316(2) . ?
O1 H1 0.84(2) . ?
O1 C9 1.430(2) . ?
O2 C6 1.215(2) . ?
O3 C10 1.221(2) . ?
O4 C10 1.3422(19) . ?
O4 C11 1.477(2) . ?
O5 C17 1.440(2) . ?
O8 C19 1.366(2) . ?
O8 C22 1.431(2) . ?
N1 C1 1.475(2) . ?
N1 C2 1.469(2) . ?
N1 C10 1.364(2) . ?
C1 H1A 1.0000 . ?
C1 C9 1.561(2) . ?
C1 C15 1.537(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.543(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.509(2) . ?
C4 C5 1.335(3) . ?
C4 C9 1.524(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.474(2) . ?
C6 C7 1.504(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.531(2) . ?
C11 C12 1.508(3) . ?
C11 C13 1.524(3) . ?
C11 C14 1.523(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
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 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.511(2) . ?
C16 C17 1.385(2) . ?
C16 C21 1.399(3) . ?
C17 C18 1.384(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 C20 1.396(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O5 S1 C23 101.15(8) . . ?
O6 S1 O5 112.02(8) . . ?
O6 S1 O7 122.49(9) . . ?
O6 S1 C23 107.30(9) . . ?
O7 S1 O5 105.95(7) . . ?
O7 S1 C23 105.72(9) . . ?
C9 O1 H1 107.9(18) . . ?
C10 O4 C11 120.35(13) . . ?
C17 O5 S1 121.43(10) . . ?
C19 O8 C22 117.39(14) . . ?
C2 N1 C1 113.62(13) . . ?
C10 N1 C1 117.27(13) . . ?
C10 N1 C2 121.16(13) . . ?
N1 C1 H1A 107.7 . . ?
N1 C1 C9 109.99(12) . . ?
N1 C1 C15 110.65(13) . . ?
C9 C1 H1A 107.7 . . ?
C15 C1 H1A 107.7 . . ?
C15 C1 C9 112.97(13) . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
N1 C2 C3 108.77(13) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 108.32(13) . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 C9 113.97(14) . . ?
C5 C4 C3 122.60(15) . . ?
C5 C4 C9 123.20(15) . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.76(16) . . ?
C6 C5 H5 118.6 . . ?
O2 C6 C5 121.63(17) . . ?
O2 C6 C7 122.29(17) . . ?
C5 C6 C7 116.00(15) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.70(14) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 113.09(13) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O1 C9 C1 107.79(13) . . ?
O1 C9 C4 109.10(13) . . ?
O1 C9 C8 109.49(13) . . ?
C4 C9 C1 106.81(13) . . ?
C4 C9 C8 112.10(14) . . ?
C8 C9 C1 111.41(13) . . ?
O3 C10 O4 124.79(14) . . ?
O3 C10 N1 124.08(14) . . ?
O4 C10 N1 111.11(13) . . ?
O4 C11 C12 110.26(18) . . ?
O4 C11 C13 109.33(17) . . ?
O4 C11 C14 102.07(15) . . ?
C12 C11 C13 113.6(2) . . ?
C12 C11 C14 110.83(19) . . ?
C14 C11 C13 110.2(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 H15A 109.4 . . ?
C1 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C1 111.04(13) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C17 C16 C15 123.32(15) . . ?
C17 C16 C21 114.99(16) . . ?
C21 C16 C15 121.60(16) . . ?
C16 C17 O5 118.12(14) . . ?
C18 C17 O5 116.37(14) . . ?
C18 C17 C16 125.34(16) . . ?
C17 C18 H18 121.2 . . ?
C17 C18 C19 117.62(16) . . ?
C19 C18 H18 121.2 . . ?
O8 C19 C18 123.87(17) . . ?
O8 C19 C20 116.42(16) . . ?
C18 C19 C20 119.70(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.17(16) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 118.9 . . ?
C20 C21 C16 122.16(17) . . ?
C20 C21 H21 118.9 . . ?
O8 C22 H22A 109.5 . . ?
O8 C22 H22B 109.5 . . ?
O8 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 S1 108.83(13) . . ?
F1 C23 F2 108.52(16) . . ?
F1 C23 F3 109.93(16) . . ?
F2 C23 S1 110.32(12) . . ?
F2 C23 F3 108.91(17) . . ?
F3 C23 S1 110.30(13) . . ?

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 O3 0.84(2) 1.94(2) 2.7780(17) 174(2) 2_656 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 O5 C17 C16 86.01(16) . . . . ?
S1 O5 C17 C18 -98.53(16) . . . . ?
O2 C6 C7 C8 144.42(19) . . . . ?
O5 S1 C23 F1 166.69(13) . . . . ?
O5 S1 C23 F2 47.73(15) . . . . ?
O5 S1 C23 F3 -72.63(14) . . . . ?
O5 C17 C18 C19 -175.99(15) . . . . ?
O6 S1 O5 C17 -15.65(15) . . . . ?
O6 S1 C23 F1 -75.81(15) . . . . ?
O6 S1 C23 F2 165.23(13) . . . . ?
O6 S1 C23 F3 44.87(16) . . . . ?
O7 S1 O5 C17 -151.56(13) . . . . ?
O7 S1 C23 F1 56.42(15) . . . . ?
O7 S1 C23 F2 -62.54(16) . . . . ?
O7 S1 C23 F3 177.10(13) . . . . ?
O8 C19 C20 C21 179.35(17) . . . . ?
N1 C1 C9 O1 90.68(15) . . . . ?
N1 C1 C9 C4 -26.44(17) . . . . ?
N1 C1 C9 C8 -149.17(13) . . . . ?
N1 C1 C15 C16 68.78(17) . . . . ?
N1 C2 C3 C4 -29.20(18) . . . . ?
C1 N1 C2 C3 70.62(16) . . . . ?
C1 N1 C10 O3 17.4(2) . . . . ?
C1 N1 C10 O4 -164.29(13) . . . . ?
C1 C15 C16 C17 82.23(19) . . . . ?
C1 C15 C16 C21 -94.34(19) . . . . ?
C2 N1 C1 C9 -38.19(17) . . . . ?
C2 N1 C1 C15 87.33(16) . . . . ?
C2 N1 C10 O3 164.37(16) . . . . ?
C2 N1 C10 O4 -17.3(2) . . . . ?
C2 C3 C4 C5 138.80(16) . . . . ?
C2 C3 C4 C9 -35.91(18) . . . . ?
C3 C4 C5 C6 -173.48(16) . . . . ?
C3 C4 C9 O1 -49.77(18) . . . . ?
C3 C4 C9 C1 66.50(17) . . . . ?
C3 C4 C9 C8 -171.20(14) . . . . ?
C4 C5 C6 O2 -171.04(19) . . . . ?
C4 C5 C6 C7 12.0(3) . . . . ?
C5 C4 C9 O1 135.55(17) . . . . ?
C5 C4 C9 C1 -108.18(18) . . . . ?
C5 C4 C9 C8 14.1(2) . . . . ?
C5 C6 C7 C8 -38.6(2) . . . . ?
C6 C7 C8 C9 53.73(19) . . . . ?
C7 C8 C9 O1 -162.16(13) . . . . ?
C7 C8 C9 C1 78.70(17) . . . . ?
C7 C8 C9 C4 -40.94(19) . . . . ?
C9 C1 C15 C16 -167.40(13) . . . . ?
C9 C4 C5 C6 0.8(3) . . . . ?
C10 O4 C11 C12 68.2(2) . . . . ?
C10 O4 C11 C13 -57.3(2) . . . . ?
C10 O4 C11 C14 -174.00(17) . . . . ?
C10 N1 C1 C9 111.21(15) . . . . ?
C10 N1 C1 C15 -123.27(15) . . . . ?
C10 N1 C2 C3 -77.46(17) . . . . ?
C11 O4 C10 O3 -10.7(3) . . . . ?
C11 O4 C10 N1 170.95(15) . . . . ?
C15 C1 C9 O1 -33.49(17) . . . . ?
C15 C1 C9 C4 -150.62(14) . . . . ?
C15 C1 C9 C8 86.65(16) . . . . ?
C15 C16 C17 O5 -0.6(2) . . . . ?
C15 C16 C17 C18 -175.60(16) . . . . ?
C15 C16 C21 C20 176.07(16) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 O8 -178.94(16) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C21 C16 C17 O5 176.18(14) . . . . ?
C21 C16 C17 C18 1.2(2) . . . . ?
C22 O8 C19 C18 -0.3(3) . . . . ?
C22 O8 C19 C20 -179.49(17) . . . . ?
C23 S1 O5 C17 98.35(13) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id JMHWLC
_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_jmhwld
_database_code_depnum_ccdc_archive 'CCDC 2341584'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-03-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   JMHWLD
_nottingham_internal_coll_number 19555
_nottingham_internal_coll_client JM/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '12.00, 3.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   11/10/2023
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 17/10/2023
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 17/10/2023
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 12/03/2024
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 12/03/2024
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 12/03/2024
_refine_special_details          
;
A residual electron density peak with height 0.67 e %A⁻³ is observed in the electron density map 1.01 and 1.41 %A from oxygen atom O18B and carbon atom C17B respectively. The atom can be modelled as an oxygen atom with a partial occupancy fraction of 0.08, however, no sensible disorder model in agreement with the bulk analysis data for this compound could be developed.
All hydrogen atoms in the structure were observed in the electron denisty map. All hydroxy hydrogen atoms were refined with their O-H distances restrained to target values of 0.84 %A (DFIX, esd 0.02 %A). All other hydrogen atoms were geometrically placed and refined with a riding model.
;
_vrf_PLAT094_jmhwld              
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.01 Report
RESPONSE:
 A residual electron density peak with height 0.67 e %A^-3^ is observed in
 the electron density map 1.01 and 1.41 %A from oxygen atom O18B and carbon
 atom C17B respectively. The atom can be modelled as an oxygen atom with a
 partial occupancy fraction of 0.08, however, no sensible disorder model in
 agreement with the bulk analysis data for this compound could be developed.
;
_audit_creation_date             2024-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 N O3'
_chemical_formula_sum            'C19 H23 N O3'
_chemical_formula_weight         313.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H23NO3
_chemical_oxdiff_usercomment     
'JMHWLD #19555 GVA-2085 JM/HWL fomblin oil on micromount'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.16300(10)
_cell_length_b                   13.6943(2)
_cell_length_c                   11.41840(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.8890(10)
_cell_angle_gamma                90
_cell_volume                     1587.14(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20442
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.3680
_cell_measurement_theta_min      3.8210
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.63a (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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 7 2 0.0748
-2 0 7 0.0796
-4 -7 1 0.0824
0 -3 -7 0.0602
2 1 -7 0.0565
3 2 6 0.0523
1 -9 0 0.0955
-4 1 -6 0.0406
-4 5 -4 0.0518
-1 0 0 0.0327
1 0 0 0.0638

_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.096
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
3.2820 7.2200 2.0678 0.0333 -0.4289 0.9027
-1.9590 -0.3495 7.1741 -0.0678 0.8467 0.5278
-3.9091 -7.1445 0.6264 -0.0573 0.7279 -0.6833
0.0581 -3.1506 -6.9245 0.0402 -0.4966 -0.8671
2.1312 0.7112 -7.1019 0.0697 -0.8717 -0.4850
3.4526 1.6674 5.9581 -0.5097 0.1790 0.8415
1.3040 -8.6991 -0.4789 -0.7228 0.2561 -0.6418
-3.7805 0.5193 -5.8380 0.6914 -0.2434 -0.6802
-3.6398 5.1028 -4.2742 0.9273 -0.3273 -0.1814
-0.9991 0.0001 -0.0002 0.1153 0.0849 -0.0499
0.9991 -0.0001 0.0002 -0.1153 -0.0849 0.0499

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.331
_diffrn_reflns_theta_min         3.876
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  29.00   1.00    3.00    --   30.00  89.00 159.58   33
  2  ω     -7.00  21.00   1.00    3.00    --   30.00  93.00   9.01   28
  3  ω     -6.00  20.00   1.00    3.00    --   30.00  93.00 112.60   26
  4  ω    -43.00  26.00   1.00    3.00    --  -42.25  57.00 -30.00   69
  5  ω    -73.00  25.00   1.00    3.00    --  -42.25  77.00  90.00   98
  6  ω     53.00 112.00   1.00    3.00    --   42.25  38.00   0.00   59
  7  ω     18.00  49.00   1.00    3.00    --   42.25  38.00   0.00   31
  8  ω     28.00  74.00   1.00    3.00    --   42.25-125.00 -90.00   46
  9  ω     13.00  38.00   1.00    3.00    --   46.00  82.00 -15.86   25
 10  ω     13.00  41.00   1.00    3.00    --   46.00  82.00  68.99   28
 11  ω     14.00  42.00   1.00    3.00    --   46.00  78.00 175.18   28
 12  ω     14.00  39.00   1.00    3.00    --   46.00  80.00 -77.14   25
 13  ω     29.00  54.00   1.00    3.00    --   58.00  70.00   4.17   25
 14  ω     73.00  99.00   1.00    3.00    --   58.00  71.00-135.67   26
 15  ω     90.00 126.00   1.00    3.00    --   58.00  70.00   4.17   36
 16  ω     30.00  56.00   1.00    3.00    --   58.00  69.00 117.98   26
 17  ω     28.00  56.00   1.00    3.00    --   58.00  71.00-135.67   28
 18  ω     35.00  72.00   1.00    3.00    --   62.00  71.00 -95.50   37
 19  ω     34.00 102.00   1.00    3.00    --   62.00  70.00 155.58   68
 20  ω     37.00  67.00   1.00    3.00    --   66.00  70.00  22.68   30
 21  ω     40.00  65.00   1.00    3.00    --   66.00  71.00 -51.01   25
 22  ω    112.00 137.00   1.00    3.00    --   66.00  70.00  22.68   25
 23  ω     41.00  84.00   1.00    3.00    --   70.00  70.00 -72.78   43
 24  ω     40.00  66.00   1.00    3.00    --   70.00  71.00  63.25   26
 25  ω     45.00 114.00   1.00   12.00    --   74.00  70.00 165.01   69
 26  ω     49.00  85.00   1.00   12.00    --   78.00  67.00  89.85   36
 27  ω     48.00  87.00   1.00   12.00    --   78.00  71.00-137.29   39
 28  ω     54.00  91.00   1.00   12.00    --   82.00  64.00   6.14   37
 29  ω     60.00  86.00   1.00   12.00    --   86.00  59.00 133.03   26
 30  ω     57.00  92.00   1.00   12.00    --   86.00  70.00 -42.34   35
 31  ω     31.00  77.00   1.00   12.00    --  101.13 -94.00  90.00   46
 32  ω     81.00 111.00   1.00   12.00    --  101.13-125.00   0.00   30
 33  ω     43.00 113.00   1.00   12.00    --  101.13-125.00  90.00   70
 34  ω    132.00 171.00   1.00   12.00    --  101.13 125.00 -60.00   39
 35  ω    125.00 163.00   1.00   12.00    --  101.13  61.00 120.00   38
 36  ω     76.00 119.00   1.00   12.00    --  101.13  61.00 120.00   43
 37  ω     74.00 136.00   1.00   12.00    --  101.13  61.00   0.00   62
 38  ω     76.00 166.00   1.00   12.00    --  101.13  61.00 150.00   90
 39  ω    114.00 164.00   1.00   12.00    --  101.13  61.00 -60.00   50
 40  ω     76.00 103.00   1.00   12.00    --  101.13  61.00 -60.00   27
 41  ω     33.00  91.00   1.00   12.00    --  101.13 -61.00-120.00   58
 42  ω     75.00 104.00   1.00   12.00    --  101.13  61.00  60.00   29
 43  ω     32.00  87.00   1.00   12.00    --  101.13 -61.00  90.00   55
 44  ω    123.00 170.00   1.00   12.00    --  101.13  61.00-180.00   47
 45  ω    118.00 170.00   1.00   12.00    --  101.13  61.00  60.00   52
 46  ω     74.00 124.00   1.00   12.00    --  101.13  61.00-150.00   50
 47  ω     75.00 112.00   1.00   12.00    --  101.13  61.00-180.00   37
 48  ω     31.00  93.00   1.00   12.00    --  101.13 -61.00 -60.00   62
 49  ω    116.00 163.00   1.00   12.00    --  101.13  61.00  30.00   47
 50  ω     75.00 112.00   1.00   12.00    --  101.13  61.00  30.00   37
 51  ω     36.00 113.00   1.00   12.00    --  101.13-125.00 -90.00   77
 52  ω    124.00 160.00   1.00   12.00    --  101.13  61.00  90.00   36
 53  ω     76.00 105.00   1.00   12.00    --  101.13  61.00  90.00   29
 54  ω     74.00 171.00   1.00   12.00    --  101.13  61.00 -90.00   97
 55  ω    112.00 171.00   1.00   12.00    --  101.13  61.00 -30.00   59
 56  ω    105.00 165.00   1.00   12.00    --  101.13  71.00-132.69   60
 57  ω     79.00 104.00   1.00   12.00    --  101.13  61.00 -30.00   25
 58  ω     80.00 106.00   1.00   12.00    --  101.13 -94.00  90.00   26
 59  ω     71.00  97.00   1.00   12.00    --  101.13  71.00-132.69   26
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1154148000
_diffrn_orient_matrix_UB_12      0.0678623000
_diffrn_orient_matrix_UB_13      -0.0376574000
_diffrn_orient_matrix_UB_21      -0.0849756000
_diffrn_orient_matrix_UB_22      -0.0472719000
_diffrn_orient_matrix_UB_23      0.0925094000
_diffrn_orient_matrix_UB_31      0.0499850000
_diffrn_orient_matrix_UB_32      0.0762680000
_diffrn_orient_matrix_UB_33      0.0909338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6103
_reflns_number_total             6170
_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 1.171.43.63a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 41.123a (release 20-01-2022))'
_computing_data_reduction        'CrysAlisPro 1.171.43.63a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6170
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.4191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0863
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H22A of C22A, H7A of C7A, H14A of C14A, H15A of C15A,
  H7B of C7B, H11B of C11B, H11A of C11A, H14B of C14B, H15B of C15B, H22B of
  C22B, H22C of C22C
 At 1.5 times of:
  All O(H) groups, H13B of C23C
2. Restrained distances
 O6B-H6B = O6A-H6A = O13A-H13A
 0.84 with sigma of 0.02
 C5B-H6B
 1.85 with sigma of 0.02
 N1B-C21B \\sim N1B-C21C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O18B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
2A
C17B \\sim O18B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
4. Same fragment restrains
{C21A, C22A, C23A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C21C, C22C, C23C}
{C21A, C22A, C23A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C21B, C22B, C23B}
5. Others
 Sof(C21C)=Sof(H21C)=Sof(H21D)=Sof(C22C)=Sof(H22C)=Sof(C23C)=Sof(H23C)=
 Sof(H23D)=1-FVAR(1)
 Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23A)=
 Sof(H23B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7A(H7A), C7B(H7B)
6.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C8A(H8AA,H8AB), C16A(H16C,H16D), C19A(H19C,
 H19D), C20A(H20C,H20D), C21A(H21E,H21F), C2B(H2BA,H2BB), C3B(H3BA,H3BB),
 C8B(H8BA,H8BB), C16B(H16A,H16B), C19B(H19A,H19B), C20B(H20A,H20B), C21B(H21A,
 H21B), C21C(H21C,H21D)
6.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C14A(H14A), C15A(H15A), C22A(H22A), C11B(H11B), C14B(H14B),
 C15B(H15B), C22B(H22B), C22C(H22C)
6.d X=CH2 refined with riding coordinates:
 C23A(H23E,H23F), C23B(H23A,H23B), C23C(H23C,H23D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
N1A N 0.74262(17) 0.19556(15) 0.54237(15) 0.0259(4) Uani 1 1 d . . . . .
C2A C 0.6563(2) 0.23895(17) 0.44965(19) 0.0269(5) Uani 1 1 d . . . . .
H2AA H 0.682935 0.307344 0.435736 0.032 Uiso 1 1 calc R U . . .
H2AB H 0.564046 0.239002 0.473681 0.032 Uiso 1 1 calc R U . . .
C3A C 0.66689(19) 0.17950(16) 0.33810(18) 0.0233(4) Uani 1 1 d . . . . .
H3AA H 0.616864 0.212679 0.272958 0.028 Uiso 1 1 calc R U . . .
H3AB H 0.626576 0.114535 0.349036 0.028 Uiso 1 1 calc R U . . .
C4A C 0.81114(19) 0.16611(14) 0.30494(17) 0.0191(4) Uani 1 1 d . . . . .
C5A C 0.89357(19) 0.12452(15) 0.41204(17) 0.0202(4) Uani 1 1 d . . . . .
O6A O 0.84312(15) 0.03172(11) 0.44543(13) 0.0245(3) Uani 1 1 d D . . . .
H6A H 0.778(2) 0.048(2) 0.483(2) 0.037 Uiso 1 1 d D U . . .
C7A C 0.88270(19) 0.19667(16) 0.51348(17) 0.0230(4) Uani 1 1 d . . . . .
H7A H 0.935392 0.169923 0.582532 0.028 Uiso 1 1 calc R U . . .
C8A C 0.9411(2) 0.29699(16) 0.48365(18) 0.0258(4) Uani 1 1 d . . . . .
H8AA H 0.901326 0.347001 0.533551 0.031 Uiso 1 1 calc R U . . .
H8AB H 1.036866 0.295710 0.504256 0.031 Uiso 1 1 calc R U . . .
C9A C 0.92080(19) 0.32825(15) 0.35615(18) 0.0212(4) Uani 1 1 d . . . . .
C10A C 0.86380(19) 0.26618(14) 0.27090(18) 0.0189(4) Uani 1 1 d . . . . .
C11A C 0.84516(19) 0.29946(15) 0.15573(18) 0.0210(4) Uani 1 1 d . . . . .
H11A H 0.805957 0.257354 0.097775 0.025 Uiso 1 1 calc R U . . .
C12A C 0.8828(2) 0.39278(16) 0.12426(19) 0.0234(4) Uani 1 1 d . . . . .
O13A O 0.85905(17) 0.41917(12) 0.00948(14) 0.0321(4) Uani 1 1 d D . . . .
H13A H 0.880(3) 0.4781(18) -0.001(3) 0.048 Uiso 1 1 d D U . . .
C14A C 0.9443(2) 0.45362(15) 0.20787(19) 0.0251(4) Uani 1 1 d . . . . .
H14A H 0.973632 0.516800 0.186764 0.030 Uiso 1 1 calc R U . . .
C15A C 0.9623(2) 0.42070(16) 0.32256(19) 0.0246(4) Uani 1 1 d . . . . .
H15A H 1.004054 0.462297 0.379717 0.030 Uiso 1 1 calc R U . . .
C16A C 0.8164(2) 0.09072(15) 0.20470(18) 0.0215(4) Uani 1 1 d . . . . .
H16C H 0.773826 0.029313 0.228483 0.026 Uiso 1 1 calc R U . . .
H16D H 0.766896 0.116078 0.134251 0.026 Uiso 1 1 calc R U . . .
C17A C 0.9566(2) 0.07002(14) 0.17531(19) 0.0230(4) Uani 1 1 d . . . . .
O18A O 0.99551(16) 0.07895(12) 0.07674(14) 0.0313(4) Uani 1 1 d . . . . .
C19A C 1.0452(2) 0.03686(16) 0.27759(19) 0.0252(4) Uani 1 1 d . . . . .
H19C H 1.137329 0.034215 0.253554 0.030 Uiso 1 1 calc R U . . .
H19D H 1.019328 -0.029714 0.301225 0.030 Uiso 1 1 calc R U . . .
C20A C 1.03623(19) 0.10646(16) 0.38230(18) 0.0220(4) Uani 1 1 d . . . . .
H20C H 1.085129 0.078153 0.451393 0.026 Uiso 1 1 calc R U . . .
H20D H 1.078143 0.169454 0.363664 0.026 Uiso 1 1 calc R U . . .
C21A C 0.7193(2) 0.2342(2) 0.6583(2) 0.0348(5) Uani 1 1 d D . . . .
H21E H 0.623274 0.241078 0.666905 0.042 Uiso 1 1 calc R U . . .
H21F H 0.759527 0.299839 0.666579 0.042 Uiso 1 1 calc R U . . .
C22A C 0.7764(2) 0.1685(2) 0.7533(2) 0.0348(5) Uani 1 1 d D . . . .
H22A H 0.769608 0.099960 0.742086 0.042 Uiso 1 1 calc R U . . .
C23A C 0.8347(3) 0.2004(2) 0.8505(2) 0.0415(6) Uani 1 1 d D . . . .
H23E H 0.842914 0.268610 0.864168 0.050 Uiso 1 1 calc R U . . .
H23F H 0.868950 0.155348 0.907511 0.050 Uiso 1 1 calc R U . . .
N1B N 0.7376(2) 0.80212(16) -0.04409(19) 0.0382(5) Uani 1 1 d D . . . .
C2B C 0.7980(2) 0.86570(18) 0.0466(2) 0.0334(5) Uani 1 1 d . . . . .
H2BA H 0.735738 0.918348 0.065366 0.040 Uiso 1 1 calc R U . . .
H2BB H 0.878313 0.896284 0.017358 0.040 Uiso 1 1 calc R U . . .
C3B C 0.8338(2) 0.80659(17) 0.1567(2) 0.0323(5) Uani 1 1 d . . . . .
H3BA H 0.865214 0.851385 0.220141 0.039 Uiso 1 1 calc R U . . .
H3BB H 0.906552 0.761253 0.140604 0.039 Uiso 1 1 calc R U . . .
C4B C 0.7149(2) 0.74729(16) 0.1981(2) 0.0253(4) Uani 1 1 d . . . . .
C5B C 0.6588(2) 0.68506(17) 0.0926(2) 0.0282(5) Uani 1 1 d D . . . .
O6B O 0.75996(18) 0.62160(12) 0.05262(17) 0.0372(4) Uani 1 1 d D . . . .
H6B H 0.800(3) 0.657(2) 0.005(3) 0.056 Uiso 1 1 d D U . . .
C7B C 0.6161(2) 0.75472(18) -0.0065(2) 0.0311(5) Uani 1 1 d . . . . .
H7B H 0.580256 0.714106 -0.073553 0.037 Uiso 1 1 calc R U . . .
C8B C 0.5055(2) 0.82250(18) 0.02947(19) 0.0297(5) Uani 1 1 d . . . . .
H8BA H 0.502590 0.879817 -0.023431 0.036 Uiso 1 1 calc R U . . .
H8BB H 0.420586 0.787550 0.017568 0.036 Uiso 1 1 calc R U . . .
C9B C 0.5177(2) 0.85860(16) 0.15499(18) 0.0245(4) Uani 1 1 d . . . . .
C10B C 0.61207(19) 0.82061(15) 0.23631(19) 0.0220(4) Uani 1 1 d . . . . .
C11B C 0.6197(2) 0.85782(16) 0.35044(19) 0.0233(4) Uani 1 1 d . . . . .
H11B H 0.684063 0.832690 0.405710 0.028 Uiso 1 1 calc R U . . .
C12B C 0.5350(2) 0.93086(16) 0.38441(18) 0.0236(4) Uani 1 1 d . . . . .
O13B O 0.55235(16) 0.96516(13) 0.49666(13) 0.0297(3) Uani 1 1 d . . . . .
C14B C 0.4400(2) 0.96771(17) 0.30429(19) 0.0264(4) Uani 1 1 d . . . . .
H14B H 0.380897 1.017184 0.327037 0.032 Uiso 1 1 calc R U . . .
C15B C 0.4325(2) 0.93135(17) 0.19094(19) 0.0268(4) Uani 1 1 d . . . . .
H15B H 0.367679 0.956629 0.136233 0.032 Uiso 1 1 calc R U . . .
C16B C 0.7637(2) 0.67774(16) 0.2972(2) 0.0286(5) Uani 1 1 d . . . . .
H16A H 0.840675 0.640773 0.271176 0.034 Uiso 1 1 calc R U . . .
H16B H 0.793153 0.716905 0.366538 0.034 Uiso 1 1 calc R U . . .
C17B C 0.6597(2) 0.60673(16) 0.3322(2) 0.0284(5) Uani 1 1 d . U . . .
O18B O 0.63617(18) 0.59390(14) 0.43506(15) 0.0376(4) Uani 1 1 d . U . A 1
C19B C 0.5908(2) 0.55185(18) 0.2332(2) 0.0336(5) Uani 1 1 d . . . . .
H19A H 0.512379 0.518758 0.262558 0.040 Uiso 1 1 calc R U . . .
H19B H 0.650689 0.500955 0.204949 0.040 Uiso 1 1 calc R U . . .
C20B C 0.5475(2) 0.61900(17) 0.1302(2) 0.0290(5) Uani 1 1 d . . . . .
H20A H 0.516274 0.578361 0.062650 0.035 Uiso 1 1 calc R U . . .
H20B H 0.472890 0.659972 0.153317 0.035 Uiso 1 1 calc R U . . .
C21B C 0.7429(8) 0.8404(6) -0.1538(6) 0.0317(16) Uani 0.530(9) 1 d D . P B 1
H21A H 0.828251 0.874098 -0.161102 0.038 Uiso 0.530(9) 1 calc R U P B 1
H21B H 0.671753 0.889240 -0.166438 0.038 Uiso 0.530(9) 1 calc R U P B 1
C22B C 0.7281(5) 0.7636(4) -0.2439(4) 0.0293(15) Uani 0.530(9) 1 d D . P B 1
H22B H 0.768409 0.702334 -0.226552 0.035 Uiso 0.530(9) 1 calc R U P B 1
C23B C 0.6643(4) 0.7726(4) -0.3457(5) 0.0326(15) Uani 0.530(9) 1 d D . P B 1
H23A H 0.622585 0.832574 -0.366615 0.039 Uiso 0.530(9) 1 calc R U P B 1
H23B H 0.659774 0.719057 -0.398685 0.039 Uiso 0.530(9) 1 calc R U P B 1
C21C C 0.7006(8) 0.8653(7) -0.1589(7) 0.0289(17) Uani 0.470(9) 1 d D . P B 2
H21C H 0.623064 0.905944 -0.142506 0.035 Uiso 0.470(9) 1 calc R U P B 2
H21D H 0.774680 0.910384 -0.171398 0.035 Uiso 0.470(9) 1 calc R U P B 2
C22C C 0.6698(5) 0.8112(4) -0.2730(5) 0.0300(16) Uani 0.470(9) 1 d D . P B 2
H22C H 0.636968 0.848432 -0.338333 0.036 Uiso 0.470(9) 1 calc R U P B 2
C23C C 0.6850(5) 0.7181(5) -0.2882(5) 0.0328(17) Uani 0.470(9) 1 d D . P B 2
H23C H 0.717691 0.678443 -0.225003 0.039 Uiso 0.470(9) 1 calc R U P B 2
H23D H 0.663518 0.689632 -0.362590 0.039 Uiso 0.470(9) 1 calc R U P B 2
H13B H 0.482(3) 1.007(3) 0.516(3) 0.049 Uiso 1 1 d . 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
N1A C2A 1.466(3) . ?
N1A C7A 1.477(3) . ?
N1A C21A 1.456(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.520(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.543(3) . ?
C4A C5A 1.555(2) . ?
C4A C10A 1.529(3) . ?
C4A C16A 1.544(3) . ?
C5A O6A 1.429(2) . ?
C5A C7A 1.531(3) . ?
C5A C20A 1.526(3) . ?
O6A H6A 0.83(2) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.541(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.522(3) . ?
C9A C10A 1.396(3) . ?
C9A C15A 1.394(3) . ?
C10A C11A 1.396(3) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.387(3) . ?
C12A O13A 1.369(3) . ?
C12A C14A 1.392(3) . ?
O13A H13A 0.85(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.388(3) . ?
C15A H15A 0.9500 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17A 1.507(3) . ?
C17A O18A 1.218(3) . ?
C17A C19A 1.508(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.535(3) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21E 0.9900 . ?
C21A H21F 0.9900 . ?
C21A C22A 1.503(3) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.307(4) . ?
C23A H23E 0.9500 . ?
C23A H23F 0.9500 . ?
N1B C2B 1.464(3) . ?
N1B C7B 1.478(3) . ?
N1B C21B 1.361(8) . ?
N1B C21C 1.600(9) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.524(4) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.549(3) . ?
C4B C5B 1.559(3) . ?
C4B C10B 1.528(3) . ?
C4B C16B 1.542(3) . ?
C5B O6B 1.438(3) . ?
C5B C7B 1.527(4) . ?
C5B C20B 1.527(3) . ?
O6B H6B 0.85(2) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.530(3) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.515(3) . ?
C9B C10B 1.401(3) . ?
C9B C15B 1.395(3) . ?
C10B C11B 1.398(3) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.388(3) . ?
C12B O13B 1.368(3) . ?
C12B C14B 1.391(3) . ?
O13B H13B 0.96(4) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.385(3) . ?
C15B H15B 0.9500 . ?
C16B H16A 0.9900 . ?
C16B H16B 0.9900 . ?
C16B C17B 1.505(3) . ?
C17B O18B 1.222(3) . ?
C17B C19B 1.501(3) . ?
C19B H19A 0.9900 . ?
C19B H19B 0.9900 . ?
C19B C20B 1.540(3) . ?
C20B H20A 0.9900 . ?
C20B H20B 0.9900 . ?
C21B H21A 0.9900 . ?
C21B H21B 0.9900 . ?
C21B C22B 1.474(9) . ?
C22B H22B 0.9500 . ?
C22B C23B 1.308(8) . ?
C23B H23A 0.9500 . ?
C23B H23B 0.9500 . ?
C21C H21C 0.9900 . ?
C21C H21D 0.9900 . ?
C21C C22C 1.517(9) . ?
C22C H22C 0.9500 . ?
C22C C23C 1.297(9) . ?
C23C H23C 0.9500 . ?
C23C H23D 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
C2A N1A C7A 112.51(16) . . ?
C21A N1A C2A 112.95(17) . . ?
C21A N1A C7A 113.71(18) . . ?
N1A C2A H2AA 109.9 . . ?
N1A C2A H2AB 109.9 . . ?
N1A C2A C3A 108.83(17) . . ?
H2AA C2A H2AB 108.3 . . ?
C3A C2A H2AA 109.9 . . ?
C3A C2A H2AB 109.9 . . ?
C2A C3A H3AA 109.2 . . ?
C2A C3A H3AB 109.2 . . ?
C2A C3A C4A 112.18(16) . . ?
H3AA C3A H3AB 107.9 . . ?
C4A C3A H3AA 109.2 . . ?
C4A C3A H3AB 109.2 . . ?
C3A C4A C5A 109.35(15) . . ?
C3A C4A C16A 109.28(16) . . ?
C10A C4A C3A 107.75(16) . . ?
C10A C4A C5A 110.29(16) . . ?
C10A C4A C16A 112.66(16) . . ?
C16A C4A C5A 107.49(15) . . ?
O6A C5A C4A 110.43(16) . . ?
O6A C5A C7A 109.36(16) . . ?
O6A C5A C20A 105.84(16) . . ?
C7A C5A C4A 107.58(16) . . ?
C20A C5A C4A 111.38(15) . . ?
C20A C5A C7A 112.25(16) . . ?
C5A O6A H6A 102(2) . . ?
N1A C7A C5A 105.62(16) . . ?
N1A C7A H7A 107.7 . . ?
N1A C7A C8A 116.39(18) . . ?
C5A C7A H7A 107.7 . . ?
C5A C7A C8A 111.40(16) . . ?
C8A C7A H7A 107.7 . . ?
C7A C8A H8AA 108.5 . . ?
C7A C8A H8AB 108.5 . . ?
H8AA C8A H8AB 107.5 . . ?
C9A C8A C7A 115.28(17) . . ?
C9A C8A H8AA 108.5 . . ?
C9A C8A H8AB 108.5 . . ?
C10A C9A C8A 121.83(19) . . ?
C15A C9A C8A 119.36(18) . . ?
C15A C9A C10A 118.80(18) . . ?
C9A C10A C4A 120.45(17) . . ?
C11A C10A C4A 119.99(18) . . ?
C11A C10A C9A 119.34(18) . . ?
C10A C11A H11A 119.4 . . ?
C12A C11A C10A 121.27(19) . . ?
C12A C11A H11A 119.4 . . ?
C11A C12A C14A 119.62(19) . . ?
O13A C12A C11A 116.99(19) . . ?
O13A C12A C14A 123.37(19) . . ?
C12A O13A H13A 111(2) . . ?
C12A C14A H14A 120.5 . . ?
C15A C14A C12A 119.1(2) . . ?
C15A C14A H14A 120.5 . . ?
C9A C15A H15A 119.1 . . ?
C14A C15A C9A 121.80(19) . . ?
C14A C15A H15A 119.1 . . ?
C4A C16A H16C 109.4 . . ?
C4A C16A H16D 109.4 . . ?
H16C C16A H16D 108.0 . . ?
C17A C16A C4A 111.05(16) . . ?
C17A C16A H16C 109.4 . . ?
C17A C16A H16D 109.4 . . ?
C16A C17A C19A 114.72(18) . . ?
O18A C17A C16A 122.8(2) . . ?
O18A C17A C19A 122.5(2) . . ?
C17A C19A H19C 109.4 . . ?
C17A C19A H19D 109.4 . . ?
C17A C19A C20A 111.09(17) . . ?
H19C C19A H19D 108.0 . . ?
C20A C19A H19C 109.4 . . ?
C20A C19A H19D 109.4 . . ?
C5A C20A C19A 111.59(16) . . ?
C5A C20A H20C 109.3 . . ?
C5A C20A H20D 109.3 . . ?
C19A C20A H20C 109.3 . . ?
C19A C20A H20D 109.3 . . ?
H20C C20A H20D 108.0 . . ?
N1A C21A H21E 109.4 . . ?
N1A C21A H21F 109.4 . . ?
N1A C21A C22A 111.4(2) . . ?
H21E C21A H21F 108.0 . . ?
C22A C21A H21E 109.4 . . ?
C22A C21A H21F 109.4 . . ?
C21A C22A H22A 118.1 . . ?
C23A C22A C21A 123.8(3) . . ?
C23A C22A H22A 118.1 . . ?
C22A C23A H23E 120.0 . . ?
C22A C23A H23F 120.0 . . ?
H23E C23A H23F 120.0 . . ?
C2B N1B C7B 112.49(18) . . ?
C2B N1B C21C 109.3(3) . . ?
C7B N1B C21C 108.0(3) . . ?
C21B N1B C2B 112.8(4) . . ?
C21B N1B C7B 120.6(4) . . ?
N1B C2B H2BA 109.7 . . ?
N1B C2B H2BB 109.7 . . ?
N1B C2B C3B 110.0(2) . . ?
H2BA C2B H2BB 108.2 . . ?
C3B C2B H2BA 109.7 . . ?
C3B C2B H2BB 109.7 . . ?
C2B C3B H3BA 109.2 . . ?
C2B C3B H3BB 109.2 . . ?
C2B C3B C4B 111.90(19) . . ?
H3BA C3B H3BB 107.9 . . ?
C4B C3B H3BA 109.2 . . ?
C4B C3B H3BB 109.2 . . ?
C3B C4B C5B 108.12(18) . . ?
C10B C4B C3B 107.32(17) . . ?
C10B C4B C5B 110.56(17) . . ?
C10B C4B C16B 113.30(18) . . ?
C16B C4B C3B 108.71(18) . . ?
C16B C4B C5B 108.70(18) . . ?
O6B C5B C4B 109.67(18) . . ?
O6B C5B C7B 108.87(18) . . ?
O6B C5B C20B 106.43(18) . . ?
C7B C5B C4B 108.07(18) . . ?
C7B C5B C20B 113.02(19) . . ?
C20B C5B C4B 110.74(17) . . ?
C5B O6B H6B 103.4(19) . . ?
N1B C7B C5B 106.2(2) . . ?
N1B C7B H7B 107.4 . . ?
N1B C7B C8B 116.6(2) . . ?
C5B C7B H7B 107.4 . . ?
C5B C7B C8B 111.45(18) . . ?
C8B C7B H7B 107.4 . . ?
C7B C8B H8BA 108.5 . . ?
C7B C8B H8BB 108.5 . . ?
H8BA C8B H8BB 107.5 . . ?
C9B C8B C7B 115.19(19) . . ?
C9B C8B H8BA 108.5 . . ?
C9B C8B H8BB 108.5 . . ?
C10B C9B C8B 121.8(2) . . ?
C15B C9B C8B 119.3(2) . . ?
C15B C9B C10B 118.97(19) . . ?
C9B C10B C4B 120.64(19) . . ?
C11B C10B C4B 119.93(19) . . ?
C11B C10B C9B 119.12(19) . . ?
C10B C11B H11B 119.4 . . ?
C12B C11B C10B 121.14(19) . . ?
C12B C11B H11B 119.4 . . ?
C11B C12B C14B 119.84(19) . . ?
O13B C12B C11B 117.18(19) . . ?
O13B C12B C14B 123.0(2) . . ?
C12B O13B H13B 111.4(19) . . ?
C12B C14B H14B 120.4 . . ?
C15B C14B C12B 119.2(2) . . ?
C15B C14B H14B 120.4 . . ?
C9B C15B H15B 119.1 . . ?
C14B C15B C9B 121.7(2) . . ?
C14B C15B H15B 119.1 . . ?
C4B C16B H16A 109.0 . . ?
C4B C16B H16B 109.0 . . ?
H16A C16B H16B 107.8 . . ?
C17B C16B C4B 112.95(18) . . ?
C17B C16B H16A 109.0 . . ?
C17B C16B H16B 109.0 . . ?
O18B C17B C16B 121.5(2) . . ?
O18B C17B C19B 123.0(2) . . ?
C19B C17B C16B 115.49(19) . . ?
C17B C19B H19A 109.1 . . ?
C17B C19B H19B 109.1 . . ?
C17B C19B C20B 112.40(19) . . ?
H19A C19B H19B 107.9 . . ?
C20B C19B H19A 109.1 . . ?
C20B C19B H19B 109.1 . . ?
C5B C20B C19B 112.39(19) . . ?
C5B C20B H20A 109.1 . . ?
C5B C20B H20B 109.1 . . ?
C19B C20B H20A 109.1 . . ?
C19B C20B H20B 109.1 . . ?
H20A C20B H20B 107.9 . . ?
N1B C21B H21A 109.4 . . ?
N1B C21B H21B 109.4 . . ?
N1B C21B C22B 111.1(6) . . ?
H21A C21B H21B 108.0 . . ?
C22B C21B H21A 109.4 . . ?
C22B C21B H21B 109.4 . . ?
C21B C22B H22B 117.2 . . ?
C23B C22B C21B 125.6(6) . . ?
C23B C22B H22B 117.2 . . ?
C22B C23B H23A 120.0 . . ?
C22B C23B H23B 120.0 . . ?
H23A C23B H23B 120.0 . . ?
N1B C21C H21C 107.8 . . ?
N1B C21C H21D 107.8 . . ?
H21C C21C H21D 107.1 . . ?
C22C C21C N1B 118.0(6) . . ?
C22C C21C H21C 107.8 . . ?
C22C C21C H21D 107.8 . . ?
C21C C22C H22C 117.5 . . ?
C23C C22C C21C 125.0(7) . . ?
C23C C22C H22C 117.5 . . ?
C22C C23C H23C 120.0 . . ?
C22C C23C H23D 120.0 . . ?
H23C C23C H23D 120.0 . . ?

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
O6A H6A N1A 0.83(2) 2.17(3) 2.723(2) 124(3) . yes
O13A H13A O18A 0.85(2) 2.09(3) 2.844(2) 149(3) 2_755 yes
O6B H6B N1B 0.85(2) 2.15(3) 2.712(3) 123(2) . yes
O13B H13B O18B 0.96(4) 1.79(4) 2.745(2) 173(3) 2_656 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
N1A C2A C3A C4A -52.5(2) . . . . ?
N1A C7A C8A C9A -85.8(2) . . . . ?
N1A C21A C22A C23A 141.2(2) . . . . ?
C2A N1A C7A C5A -68.6(2) . . . . ?
C2A N1A C7A C8A 55.6(2) . . . . ?
C2A N1A C21A C22A 162.3(2) . . . . ?
C2A C3A C4A C5A 52.7(2) . . . . ?
C2A C3A C4A C10A -67.2(2) . . . . ?
C2A C3A C4A C16A 170.08(17) . . . . ?
C3A C4A C5A O6A 60.7(2) . . . . ?
C3A C4A C5A C7A -58.6(2) . . . . ?
C3A C4A C5A C20A 177.95(17) . . . . ?
C3A C4A C10A C9A 87.8(2) . . . . ?
C3A C4A C10A C11A -86.8(2) . . . . ?
C3A C4A C16A C17A -175.96(16) . . . . ?
C4A C5A C7A N1A 64.93(19) . . . . ?
C4A C5A C7A C8A -62.3(2) . . . . ?
C4A C5A C20A C19A -57.2(2) . . . . ?
C4A C10A C11A C12A 174.99(18) . . . . ?
C4A C16A C17A O18A -124.9(2) . . . . ?
C4A C16A C17A C19A 55.4(2) . . . . ?
C5A C4A C10A C9A -31.5(2) . . . . ?
C5A C4A C10A C11A 153.87(17) . . . . ?
C5A C4A C16A C17A -57.4(2) . . . . ?
C5A C7A C8A C9A 35.3(2) . . . . ?
O6A C5A C7A N1A -55.0(2) . . . . ?
O6A C5A C7A C8A 177.71(15) . . . . ?
O6A C5A C20A C19A 62.8(2) . . . . ?
C7A N1A C2A C3A 61.7(2) . . . . ?
C7A N1A C21A C22A -67.9(3) . . . . ?
C7A C5A C20A C19A -177.94(17) . . . . ?
C7A C8A C9A C10A -5.5(3) . . . . ?
C7A C8A C9A C15A 175.68(18) . . . . ?
C8A C9A C10A C4A 4.1(3) . . . . ?
C8A C9A C10A C11A 178.71(18) . . . . ?
C8A C9A C15A C14A -178.92(19) . . . . ?
C9A C10A C11A C12A 0.3(3) . . . . ?
C10A C4A C5A O6A 178.96(15) . . . . ?
C10A C4A C5A C7A 59.67(19) . . . . ?
C10A C4A C5A C20A -63.7(2) . . . . ?
C10A C4A C16A C17A 64.3(2) . . . . ?
C10A C9A C15A C14A 2.3(3) . . . . ?
C10A C11A C12A O13A -179.25(18) . . . . ?
C10A C11A C12A C14A 2.2(3) . . . . ?
C11A C12A C14A C15A -2.4(3) . . . . ?
C12A C14A C15A C9A 0.2(3) . . . . ?
O13A C12A C14A C15A 179.10(19) . . . . ?
C15A C9A C10A C4A -177.14(18) . . . . ?
C15A C9A C10A C11A -2.5(3) . . . . ?
C16A C4A C5A O6A -57.87(19) . . . . ?
C16A C4A C5A C7A -177.16(15) . . . . ?
C16A C4A C5A C20A 59.4(2) . . . . ?
C16A C4A C10A C9A -151.63(17) . . . . ?
C16A C4A C10A C11A 33.8(2) . . . . ?
C16A C17A C19A C20A -50.9(2) . . . . ?
C17A C19A C20A C5A 51.0(2) . . . . ?
O18A C17A C19A C20A 129.3(2) . . . . ?
C20A C5A C7A N1A -172.19(16) . . . . ?
C20A C5A C7A C8A 60.6(2) . . . . ?
C21A N1A C2A C3A -167.91(19) . . . . ?
C21A N1A C7A C5A 161.36(18) . . . . ?
C21A N1A C7A C8A -74.5(2) . . . . ?
N1B C2B C3B C4B -52.7(3) . . . . ?
N1B C7B C8B C9B -83.7(3) . . . . ?
N1B C21B C22B C23B 142.7(6) . . . . ?
N1B C21C C22C C23C -7.9(9) . . . . ?
C2B N1B C7B C5B -66.6(2) . . . . ?
C2B N1B C7B C8B 58.3(3) . . . . ?
C2B N1B C21B C22B 159.0(4) . . . . ?
C2B N1B C21C C22C 164.5(5) . . . . ?
C2B C3B C4B C5B 53.4(2) . . . . ?
C2B C3B C4B C10B -65.8(2) . . . . ?
C2B C3B C4B C16B 171.27(18) . . . . ?
C3B C4B C5B O6B 58.6(2) . . . . ?
C3B C4B C5B C7B -59.9(2) . . . . ?
C3B C4B C5B C20B 175.80(19) . . . . ?
C3B C4B C10B C9B 87.9(2) . . . . ?
C3B C4B C10B C11B -85.6(2) . . . . ?
C3B C4B C16B C17B -171.93(18) . . . . ?
C4B C5B C7B N1B 65.4(2) . . . . ?
C4B C5B C7B C8B -62.6(2) . . . . ?
C4B C5B C20B C19B -56.4(2) . . . . ?
C4B C10B C11B C12B 174.17(19) . . . . ?
C4B C16B C17B O18B -131.3(2) . . . . ?
C4B C16B C17B C19B 50.2(3) . . . . ?
C5B C4B C10B C9B -29.8(3) . . . . ?
C5B C4B C10B C11B 156.66(19) . . . . ?
C5B C4B C16B C17B -54.5(2) . . . . ?
C5B C7B C8B C9B 38.4(3) . . . . ?
O6B C5B C7B N1B -53.7(2) . . . . ?
O6B C5B C7B C8B 178.38(17) . . . . ?
O6B C5B C20B C19B 62.7(2) . . . . ?
C7B N1B C2B C3B 59.9(3) . . . . ?
C7B N1B C21B C22B -64.1(6) . . . . ?
C7B N1B C21C C22C -72.7(6) . . . . ?
C7B C5B C20B C19B -177.87(18) . . . . ?
C7B C8B C9B C10B -9.4(3) . . . . ?
C7B C8B C9B C15B 170.9(2) . . . . ?
C8B C9B C10B C4B 5.5(3) . . . . ?
C8B C9B C10B C11B 179.13(19) . . . . ?
C8B C9B C15B C14B -179.4(2) . . . . ?
C9B C10B C11B C12B 0.5(3) . . . . ?
C10B C4B C5B O6B 175.85(17) . . . . ?
C10B C4B C5B C7B 57.3(2) . . . . ?
C10B C4B C5B C20B -67.0(2) . . . . ?
C10B C4B C16B C17B 68.9(2) . . . . ?
C10B C9B C15B C14B 0.8(3) . . . . ?
C10B C11B C12B O13B -177.90(19) . . . . ?
C10B C11B C12B C14B 0.4(3) . . . . ?
C11B C12B C14B C15B -0.7(3) . . . . ?
C12B C14B C15B C9B 0.1(3) . . . . ?
O13B C12B C14B C15B 177.5(2) . . . . ?
C15B C9B C10B C4B -174.71(19) . . . . ?
C15B C9B C10B C11B -1.1(3) . . . . ?
C16B C4B C5B O6B -59.2(2) . . . . ?
C16B C4B C5B C7B -177.75(17) . . . . ?
C16B C4B C5B C20B 58.0(2) . . . . ?
C16B C4B C10B C9B -152.11(19) . . . . ?
C16B C4B C10B C11B 34.4(3) . . . . ?
C16B C17B C19B C20B -46.4(3) . . . . ?
C17B C19B C20B C5B 49.6(3) . . . . ?
O18B C17B C19B C20B 135.2(2) . . . . ?
C20B C5B C7B N1B -171.70(17) . . . . ?
C20B C5B C7B C8B 60.4(2) . . . . ?
C21B N1B C2B C3B -159.7(4) . . . . ?
C21B N1B C7B C5B 156.5(4) . . . . ?
C21B N1B C7B C8B -78.7(5) . . . . ?
C21C N1B C2B C3B 179.9(4) . . . . ?
C21C N1B C7B C5B 172.7(3) . . . . ?
C21C N1B C7B C8B -62.5(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.854
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc and pentane'
