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

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

data_syhwlj
_database_code_depnum_ccdc_archive 'CCDC 2522306'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SYHWLJ
_nottingham_internal_coll_number 20298
_nottingham_internal_coll_client SY/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 3.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   06/10/2025
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 07/10/2025
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 07/10/2025
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 03/11/2025
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 03/11/2025
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 03/11/2025
_refine_special_details          ?
_audit_creation_date             2025-11-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br Cl O3'
_chemical_formula_sum            'C22 H16 Br Cl O3'
_chemical_formula_weight         443.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H16 O3 Cl1 Br1 '
_chemical_oxdiff_usercomment     
'SYHWLJ #20298 GVA-2379 SY/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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6789(2)
_cell_length_b                   11.1715(5)
_cell_length_c                   12.6773(5)
_cell_angle_alpha                84.693(3)
_cell_angle_beta                 75.054(3)
_cell_angle_gamma                79.844(3)
_cell_volume                     898.48(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10154
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.2120
_cell_measurement_theta_min      5.2590
_shelx_estimated_absorpt_T_max   0.800
_shelx_estimated_absorpt_T_min   0.561
_exptl_absorpt_coefficient_mu    4.661
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.648
_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    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             448
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 -1 0.0246
2 -3 -6 0.0487
2 2 -6 0.0543
0 7 1 0.0233
0 -4 6 0.0530
-4 -5 0 0.0630
-4 -2 -4 0.0572
0 4 -6 0.0572
3 5 -3 0.0487
4 4 0 0.0510
4 1 6 0.0675
1 5 7 0.0526
0 0 8 0.0638
2 6 -3 0.0386
0 -2 -8 0.0638
0 6 4 0.0290
-4 1 0 0.0572
-4 3 -2 0.0566
4 -1 1 0.0598
3 -4 3 0.0612
-3 -4 -6 0.0534

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-heptane, dichloromethane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1495 -7.0725 -0.8682 0.1482 -0.7917 0.5926
1.5409 -3.0111 -5.7790 0.1712 -0.9229 -0.3450
1.7108 2.0390 -6.1720 0.0856 -0.4673 -0.8800
-0.0755 7.1112 0.5992 -0.1436 0.7664 -0.6261
0.2050 -4.2830 6.1515 0.3572 0.0652 0.9317
-3.5293 -4.6720 0.2973 -0.6208 -0.1165 0.7753
-4.1568 -2.2726 -4.0248 -0.9589 -0.1787 0.2204
-0.3380 4.1870 -6.2487 -0.3863 -0.0706 -0.9197
2.6089 5.1584 -2.5288 0.3386 0.0643 -0.9387
3.7546 4.3922 0.4668 0.7011 0.1314 -0.7008
3.7997 0.6441 5.6205 0.9776 0.1818 0.1059
0.8827 4.6055 6.7604 0.3324 0.9404 0.0714
-0.1665 0.2688 7.8632 0.2470 0.6960 0.6742
1.5038 6.0313 -3.0583 0.0723 0.2091 -0.9752
-0.2898 -2.2094 -7.8214 -0.2990 -0.8441 -0.4450
-0.3473 6.3450 3.5323 -0.0766 0.9589 -0.2734
-4.0889 0.7570 -0.4115 -0.8768 0.4178 0.2381
-3.6146 2.8196 -2.2894 -0.8907 0.4238 -0.1646
4.0563 -1.1099 0.7297 0.8891 -0.4236 -0.1736
3.2055 -3.6096 3.0235 0.8495 -0.4039 0.3394
-3.3469 -4.0611 -5.5202 -0.8083 -0.5561 0.1935

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.362
_diffrn_reflns_theta_min         3.613
_diffrn_ambient_environment      'N2 gas'
_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 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  27.00   1.00    1.00    --  -42.12  38.00 -90.00   48
  2  ω     13.00 114.00   1.00    1.00    --   42.12  74.00-106.81  101
  3  ω     13.00  67.00   1.00    1.00    --   42.12  73.00-176.04   54
  4  ω    -28.00  68.00   1.00    1.00    --   42.12 -57.00 120.00   96
  5  ω    -28.00  68.00   1.00    1.00    --   42.12 -57.00 -30.00   96
  6  ω     13.00 103.00   1.00    1.00    --   42.12  70.00  -1.58   90
  7  ω     20.00  59.00   1.00    1.00    --   42.12  57.00 150.00   39
  8  ω     54.00  81.00   1.00    1.00    --   42.12-125.00-120.00   27
  9  ω     69.00  96.00   1.00    1.00    --   42.12  38.00 150.00   27
 10  ω     90.00 115.00   1.00    1.00    --   42.12  74.00  78.91   25
 11  ω     20.00  50.00   1.00    1.00    --   42.12  38.00 150.00   30
 12  ω     11.00  73.00   1.00    1.00    --   42.12  74.00  78.91   62
 13  ω     17.00  44.00   1.00    1.00    --   42.12  57.00 -30.00   27
 14  ω     78.00 146.00   1.00    3.00    --  101.13  54.00  82.37   68
 15  ω     74.00 101.00   1.00    3.00    --  101.13  62.00 -10.16   27
 16  ω     75.00 102.00   1.00    3.00    --  101.13  58.00 139.43   27
 17  ω    128.00 156.00   1.00    3.00    --  101.13  62.00-108.07   28
 18  ω     74.00 100.00   1.00    3.00    --  101.13  61.00-180.00   26
 19  ω     74.00 121.00   1.00    3.00    --  101.13  62.00-108.07   47
 20  ω     77.00 113.00   1.00    3.00    --  101.13  47.00  68.52   36
 21  ω     75.00 123.00   1.00    3.00    --  101.13  61.00 -44.00   48
 22  ω     31.00  93.00   1.00    3.00    --  101.13 -61.00 177.00   62
 23  ω     81.00 123.00   1.00    3.00    --  101.13  51.00-154.41   42
 24  ω    120.00 168.00   1.00    3.00    --  101.13  61.00 120.00   48
 25  ω     29.00 112.00   1.00    3.00    --  101.13-125.00  90.00   83
 26  ω     74.00 100.00   1.00    3.00    --  101.13  61.00  60.00   26
 27  ω     27.00 127.00   1.00    3.00    --  101.13 -77.00 -90.00  100
 28  ω     84.00 113.00   1.00    3.00    --  101.13-125.00 -60.00   29
 29  ω     74.00 100.00   1.00    3.00    --  101.13  61.00-120.00   26
 30  ω     81.00 108.00   1.00    3.00    --  101.13  61.00 150.00   27
 31  ω     75.00 108.00   1.00    3.00    --  101.13  59.00 -70.35   33
 32  ω     28.00 113.00   1.00    3.00    --  101.13-125.00-150.00   85
 33  ω    108.00 133.00   1.00    3.00    --  101.13  61.00 -30.00   25
 34  ω     77.00 170.00   1.00    3.00    --  101.13  48.00  30.60   93
 35  ω     74.00 101.00   1.00    3.00    --  101.13  61.00 -30.00   27
 36  ω    143.00 168.00   1.00    3.00    --  101.13  61.00  30.00   25
 37  ω     74.00 104.00   1.00    3.00    --  101.13  61.00 -60.00   30
 38  ω     73.00 169.00   1.00    3.00    --  101.13  65.00-151.97   96
 39  ω     74.00 101.00   1.00    3.00    --  101.13  61.00  30.00   27
 40  ω     76.00 102.00   1.00    3.00    --  101.13  61.00 120.00   26
 41  ω    144.00 170.00   1.00    3.00    --  101.13  61.00 150.00   26
 42  ω     35.00  92.00   1.00    3.00    --  101.13 -61.00  60.00   57
 43  ω     71.00 172.00   1.00    3.00    --  101.13  74.00  86.92  101
 44  ω     80.00 165.00   1.00    3.00    --  101.13  45.00   0.00   85
 45  ω     74.00 166.00   1.00    3.00    --  101.13  61.00 -90.00   92
 46  ω    136.00 170.00   1.00    3.00    --  101.13  58.00 139.43   34
;
_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      0.2068513000
_diffrn_orient_matrix_UB_12      -0.0210695000
_diffrn_orient_matrix_UB_13      0.0365106000
_diffrn_orient_matrix_UB_21      -0.0920721000
_diffrn_orient_matrix_UB_22      0.0997890000
_diffrn_orient_matrix_UB_23      0.0831505000
_diffrn_orient_matrix_UB_31      -0.0848462000
_diffrn_orient_matrix_UB_32      -0.0962985000
_diffrn_orient_matrix_UB_33      0.0872430000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3332
_reflns_number_total             3487
_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 40.53 (release 29-04-2019))'
_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         0.375
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0190
_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)+(0.0173P)²+0.5282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0461
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_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
C1 C 0.5000(2) 0.69122(13) 0.82066(11) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.392808 0.709146 0.890949 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4956(2) 0.56715(13) 0.78437(11) 0.0165(3) Uani 1 1 d . . . . .
H2 H 0.357023 0.553323 0.775602 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6312(2) 0.45551(12) 0.82344(11) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.7693(2) 0.48177(12) 0.89228(11) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.8527(2) 0.59836(13) 0.86725(11) 0.0158(3) Uani 1 1 d . . . . .
H5 H 0.945326 0.615245 0.912921 0.019 Uiso 1 1 calc R U . . .
C6 C 0.7131(2) 0.70784(13) 0.82918(11) 0.0168(3) Uani 1 1 d . . . . .
H6 H 0.724187 0.788836 0.852900 0.020 Uiso 1 1 calc R U . . .
C7 C 0.9019(2) 0.64697(12) 0.74859(11) 0.0157(3) Uani 1 1 d . . . . .
H7 H 1.023916 0.692182 0.725002 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8707(2) 0.57038(13) 0.66540(11) 0.0156(3) Uani 1 1 d . . . . .
H8 H 0.856085 0.622728 0.598586 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6851(2) 0.50629(13) 0.70414(11) 0.0159(3) Uani 1 1 d . . . . .
H9 H 0.656163 0.457393 0.649083 0.019 Uiso 1 1 calc R U . . .
O10 O 0.80994(16) 0.41163(9) 0.96582(8) 0.0192(2) Uani 1 1 d . . . . .
Br11 Br 1.12784(2) 0.44554(2) 0.62726(2) 0.01936(5) Uani 1 1 d . . . . .
O12 O 0.45493(16) 0.77832(9) 0.73232(8) 0.0200(2) Uani 1 1 d . . . . .
C13 C 0.2657(2) 0.84744(12) 0.74665(12) 0.0166(3) Uani 1 1 d . . . . .
O14 O 0.13159(17) 0.85250(11) 0.83074(9) 0.0264(2) Uani 1 1 d . . . . .
C15 C 0.2460(2) 0.92198(13) 0.64454(12) 0.0164(3) Uani 1 1 d . . . . .
C16 C 0.3030(2) 0.87657(13) 0.54037(12) 0.0177(3) Uani 1 1 d . . . . .
C17 C 0.2903(2) 0.95258(14) 0.44877(13) 0.0216(3) Uani 1 1 d . . . . .
H17 H 0.331020 0.920507 0.378184 0.026 Uiso 1 1 calc R U . . .
C18 C 0.2177(2) 1.07580(15) 0.46107(14) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.211072 1.128672 0.398484 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1548(2) 1.12226(14) 0.56402(15) 0.0252(3) Uani 1 1 d . . . . .
H19 H 0.102030 1.206489 0.572168 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1689(2) 1.04602(13) 0.65493(13) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.125591 1.078400 0.725412 0.025 Uiso 1 1 calc R U . . .
Cl21 Cl 0.37903(6) 0.72102(3) 0.52131(3) 0.02417(9) Uani 1 1 d . . . . .
C22 C 0.5557(2) 0.33480(13) 0.84569(11) 0.0159(3) Uani 1 1 d . . . . .
C23 C 0.3445(2) 0.32507(13) 0.87948(11) 0.0179(3) Uani 1 1 d . . . . .
H23 H 0.242223 0.396626 0.887878 0.021 Uiso 1 1 calc R U . . .
C24 C 0.2807(2) 0.21083(15) 0.90131(12) 0.0224(3) Uani 1 1 d . . . . .
H24 H 0.135517 0.205064 0.924676 0.027 Uiso 1 1 calc R U . . .
C25 C 0.4288(3) 0.10581(14) 0.88894(13) 0.0246(3) Uani 1 1 d . . . . .
H25 H 0.385516 0.028125 0.903754 0.030 Uiso 1 1 calc R U . . .
C26 C 0.6413(3) 0.11491(14) 0.85470(13) 0.0256(3) Uani 1 1 d . . . . .
H26 H 0.743432 0.043315 0.846320 0.031 Uiso 1 1 calc R U . . .
C27 C 0.7038(2) 0.22844(14) 0.83283(13) 0.0216(3) Uani 1 1 d . . . . .
H27 H 0.848979 0.234045 0.808810 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 1.0000 . ?
C1 C2 1.508(2) . ?
C1 C6 1.499(2) . ?
C1 O12 1.4700(17) . ?
C2 H2 1.0000 . ?
C2 C3 1.5295(18) . ?
C2 C9 1.5027(19) . ?
C3 C4 1.5020(18) . ?
C3 C9 1.5398(19) . ?
C3 C22 1.500(2) . ?
C4 C5 1.482(2) . ?
C4 O10 1.2155(17) . ?
C5 H5 1.0000 . ?
C5 C6 1.5226(19) . ?
C5 C7 1.5240(19) . ?
C6 H6 1.0000 . ?
C6 C7 1.5025(19) . ?
C7 H7 1.0000 . ?
C7 C8 1.4936(19) . ?
C8 H8 1.0000 . ?
C8 C9 1.492(2) . ?
C8 Br11 1.9950(13) . ?
C9 H9 1.0000 . ?
O12 C13 1.3376(17) . ?
C13 O14 1.2013(18) . ?
C13 C15 1.496(2) . ?
C15 C16 1.394(2) . ?
C15 C20 1.396(2) . ?
C16 C17 1.386(2) . ?
C16 Cl21 1.7434(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9500 . ?
C22 C23 1.385(2) . ?
C22 C27 1.398(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.392(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(2) . ?
C27 H27 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
C2 C1 H1 110.9 . . ?
C6 C1 H1 110.9 . . ?
C6 C1 C2 113.15(12) . . ?
O12 C1 H1 110.9 . . ?
O12 C1 C2 105.97(11) . . ?
O12 C1 C6 104.81(11) . . ?
C1 C2 H2 115.6 . . ?
C1 C2 C3 119.57(11) . . ?
C3 C2 H2 115.6 . . ?
C9 C2 C1 118.61(12) . . ?
C9 C2 H2 115.6 . . ?
C9 C2 C3 61.03(9) . . ?
C2 C3 C9 58.63(9) . . ?
C4 C3 C2 115.24(11) . . ?
C4 C3 C9 115.20(12) . . ?
C22 C3 C2 120.60(12) . . ?
C22 C3 C4 116.57(12) . . ?
C22 C3 C9 117.96(11) . . ?
C5 C4 C3 116.87(12) . . ?
O10 C4 C3 121.93(13) . . ?
O10 C4 C5 121.20(12) . . ?
C4 C5 H5 116.6 . . ?
C4 C5 C6 117.63(12) . . ?
C4 C5 C7 117.90(11) . . ?
C6 C5 H5 116.6 . . ?
C6 C5 C7 59.10(9) . . ?
C7 C5 H5 116.6 . . ?
C1 C6 C5 118.07(12) . . ?
C1 C6 H6 116.2 . . ?
C1 C6 C7 118.20(12) . . ?
C5 C6 H6 116.2 . . ?
C7 C6 C5 60.50(9) . . ?
C7 C6 H6 116.2 . . ?
C5 C7 H7 116.2 . . ?
C6 C7 C5 60.40(9) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C5 117.22(12) . . ?
C8 C7 C6 119.07(12) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 109.1 . . ?
C7 C8 Br11 106.99(9) . . ?
C9 C8 C7 114.06(12) . . ?
C9 C8 H8 109.1 . . ?
C9 C8 Br11 108.40(9) . . ?
Br11 C8 H8 109.1 . . ?
C2 C9 C3 60.35(9) . . ?
C2 C9 H9 115.9 . . ?
C3 C9 H9 115.9 . . ?
C8 C9 C2 118.53(12) . . ?
C8 C9 C3 118.87(11) . . ?
C8 C9 H9 115.9 . . ?
C13 O12 C1 119.14(11) . . ?
O12 C13 C15 110.74(12) . . ?
O14 C13 O12 125.05(13) . . ?
O14 C13 C15 124.17(13) . . ?
C16 C15 C13 124.52(12) . . ?
C16 C15 C20 118.24(14) . . ?
C20 C15 C13 117.23(13) . . ?
C15 C16 Cl21 121.20(11) . . ?
C17 C16 C15 121.21(13) . . ?
C17 C16 Cl21 117.49(12) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.39(15) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.35(14) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.92(14) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.85(15) . . ?
C19 C20 H20 119.6 . . ?
C23 C22 C3 122.28(13) . . ?
C23 C22 C27 118.91(14) . . ?
C27 C22 C3 118.80(13) . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.51(14) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.17(14) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.62(14) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.01(14) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.77(15) . . ?
C26 C27 H27 119.6 . . ?

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
C1 C2 C3 C4 -3.06(18) . . . . ?
C1 C2 C3 C9 -108.37(14) . . . . ?
C1 C2 C3 C22 145.52(13) . . . . ?
C1 C2 C9 C3 109.91(13) . . . . ?
C1 C2 C9 C8 1.06(18) . . . . ?
C1 C6 C7 C5 -108.06(14) . . . . ?
C1 C6 C7 C8 -1.44(19) . . . . ?
C1 O12 C13 O14 6.9(2) . . . . ?
C1 O12 C13 C15 -175.37(11) . . . . ?
C2 C1 C6 C5 -35.03(17) . . . . ?
C2 C1 C6 C7 34.65(17) . . . . ?
C2 C1 O12 C13 105.40(13) . . . . ?
C2 C3 C4 C5 -32.90(17) . . . . ?
C2 C3 C4 O10 146.47(13) . . . . ?
C2 C3 C9 C8 108.28(14) . . . . ?
C2 C3 C22 C23 -29.09(19) . . . . ?
C2 C3 C22 C27 151.51(13) . . . . ?
C3 C2 C9 C8 -108.84(13) . . . . ?
C3 C4 C5 C6 34.51(17) . . . . ?
C3 C4 C5 C7 -33.23(17) . . . . ?
C3 C22 C23 C24 -178.82(13) . . . . ?
C3 C22 C27 C26 178.64(14) . . . . ?
C4 C3 C9 C2 -105.37(13) . . . . ?
C4 C3 C9 C8 2.90(17) . . . . ?
C4 C3 C22 C23 119.10(14) . . . . ?
C4 C3 C22 C27 -60.30(17) . . . . ?
C4 C5 C6 C1 0.69(18) . . . . ?
C4 C5 C6 C7 -107.59(13) . . . . ?
C4 C5 C7 C6 107.14(13) . . . . ?
C4 C5 C7 C8 -2.51(18) . . . . ?
C5 C6 C7 C8 106.62(14) . . . . ?
C5 C7 C8 C9 37.09(17) . . . . ?
C5 C7 C8 Br11 -82.77(13) . . . . ?
C6 C1 C2 C3 36.45(18) . . . . ?
C6 C1 C2 C9 -34.59(17) . . . . ?
C6 C1 O12 C13 -134.69(12) . . . . ?
C6 C5 C7 C8 -109.65(14) . . . . ?
C6 C7 C8 C9 -32.45(18) . . . . ?
C6 C7 C8 Br11 -152.31(10) . . . . ?
C7 C5 C6 C1 108.27(14) . . . . ?
C7 C8 C9 C2 32.47(17) . . . . ?
C7 C8 C9 C3 -37.45(17) . . . . ?
C9 C2 C3 C4 105.30(13) . . . . ?
C9 C2 C3 C22 -106.11(14) . . . . ?
C9 C3 C4 C5 32.63(16) . . . . ?
C9 C3 C4 O10 -148.00(13) . . . . ?
C9 C3 C22 C23 -97.32(16) . . . . ?
C9 C3 C22 C27 83.27(16) . . . . ?
O10 C4 C5 C6 -144.87(13) . . . . ?
O10 C4 C5 C7 147.39(13) . . . . ?
Br11 C8 C9 C2 151.54(10) . . . . ?
Br11 C8 C9 C3 81.62(13) . . . . ?
O12 C1 C2 C3 150.74(12) . . . . ?
O12 C1 C2 C9 79.71(14) . . . . ?
O12 C1 C6 C5 -150.02(11) . . . . ?
O12 C1 C6 C7 -80.34(14) . . . . ?
O12 C13 C15 C16 47.16(18) . . . . ?
O12 C13 C15 C20 -131.46(13) . . . . ?
C13 C15 C16 C17 -176.58(13) . . . . ?
C13 C15 C16 Cl21 7.0(2) . . . . ?
C13 C15 C20 C19 177.02(13) . . . . ?
O14 C13 C15 C16 -135.05(16) . . . . ?
O14 C13 C15 C20 46.3(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C15 C20 C19 -1.7(2) . . . . ?
C16 C17 C18 C19 -1.2(2) . . . . ?
C17 C18 C19 C20 1.5(2) . . . . ?
C18 C19 C20 C15 0.0(2) . . . . ?
C20 C15 C16 C17 2.0(2) . . . . ?
C20 C15 C16 Cl21 -174.40(11) . . . . ?
Cl21 C16 C17 C18 175.93(11) . . . . ?
C22 C3 C4 C5 177.21(11) . . . . ?
C22 C3 C4 O10 -3.42(19) . . . . ?
C22 C3 C9 C2 110.57(14) . . . . ?
C22 C3 C9 C8 -141.16(13) . . . . ?
C22 C23 C24 C25 -0.2(2) . . . . ?
C23 C22 C27 C26 -0.8(2) . . . . ?
C23 C24 C25 C26 0.0(2) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C25 C26 C27 C22 0.6(2) . . . . ?
C27 C22 C23 C24 0.6(2) . . . . ?

_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_syhwla
_database_code_depnum_ccdc_archive 'CCDC 2522308'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SYHWLA
_nottingham_internal_coll_number 19747
_nottingham_internal_coll_client SY/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   12/04/2024
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 15/04/2024
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 15/04/2024
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 15/04/2024
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 16/04/2024
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 16/04/2024
_refine_special_details          
'All hydrogen atoms were observed in the electron denisty map, geometrically placed, and refined using a riding model.'
_audit_creation_date             2024-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O3'
_chemical_formula_sum            'C15 H10 O3'
_chemical_formula_weight         238.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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                   6.42140(10)
_cell_length_b                   10.2233(2)
_cell_length_c                   8.6908(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.113(2)
_cell_angle_gamma                90
_cell_volume                     555.656(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4997
_cell_measurement_temperature    120.0(3)
_cell_measurement_theta_max      72.5340
_cell_measurement_theta_min      5.2160
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -2 0.0353
1 0 2 0.0353
1 -5 2 0.0550
2 4 3 0.0576
-1 5 -2 0.0798
-2 -2 -3 0.0525
-3 -1 4 0.0214
3 1 -4 0.0010

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-pentane, dichloromethane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7346
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.778
_diffrn_reflns_theta_min         5.226
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120.0(3)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  29.00   1.00    4.00    --  -41.82  19.00 120.00   27
  2  ω    -44.00  26.00   1.00    4.00    --  -41.82  57.00  30.00   70
  3  ω     -4.00  37.00   1.00    4.00    --  -41.82  19.00 -30.00   41
  4  ω    -98.00 -11.00   1.00    4.00    --  -41.82 125.00 150.00   87
  5  ω      8.00  33.00   1.00    4.00    --   41.82  82.00  70.83   25
  6  ω     15.00  41.00   1.00    4.00    --   41.82  57.00 150.00   26
  7  ω      8.00  41.00   1.00    4.00    --   41.82  81.00 175.75   33
  8  ω     66.00  93.00   1.00    4.00    --   41.82  57.00 150.00   27
  9  ω     15.00  41.00   1.00    4.00    --   41.82  57.00-120.00   26
 10  ω     -4.00  24.00   1.00    4.00    --   41.82 -19.00-150.00   28
 11  ω      9.00  38.00   1.00    4.00    --   41.82  80.00 -98.93   29
 12  ω     26.00 111.00   1.00    4.00    --   41.82  38.00 -30.00   85
 13  ω      7.00  32.00   1.00    4.00    --   41.82  84.00 -31.15   25
 14  ω     55.00 107.00   1.00    4.00    --   41.82  57.00-120.00   52
 15  ω     61.00 105.00   1.00    4.00    --   41.82  57.00  30.00   44
 16  ω     29.00  62.00   1.00    4.00    --   41.82  38.00 120.00   33
 17  ω     20.00  60.00   1.00    4.00    --   41.82  57.00  30.00   40
 18  ω     77.00 145.00   1.00   16.00    --  104.05  61.00-150.00   68
 19  ω     21.00  93.00   1.00   16.00    --  104.05 -94.00  30.00   72
 20  ω    135.00 162.00   1.00   16.00    --  104.05  60.00 -33.99   27
 21  ω     76.00 110.00   1.00   16.00    --  104.05  61.00 -60.00   34
 22  ω    114.00 173.00   1.00   16.00    --  104.05  61.00-180.00   59
 23  ω     76.00 102.00   1.00   16.00    --  104.05  61.00-180.00   26
 24  ω     75.00 101.00   1.00   16.00    --  104.05  60.00 -33.99   26
 25  ω     75.00 175.00   1.00   16.00    --  104.05  61.00-120.00  100
 26  ω    134.00 172.00   1.00   16.00    --  104.05  61.00 -60.00   38
 27  ω     75.00 112.00   1.00   16.00    --  104.05  61.00  90.00   37
 28  ω    132.00 158.00   1.00   16.00    --  104.05  61.00  90.00   26
 29  ω     80.00 105.00   1.00   16.00    --  104.05  45.00   0.00   25
 30  ω     82.00 109.00   1.00   16.00    --  104.05  45.00 120.00   27
 31  ω     38.00  92.00   1.00   16.00    --  104.05 -61.00 120.00   54
 32  ω     77.00 173.00   1.00   16.00    --  104.05  61.00 120.00   96
 33  ω    133.00 174.00   1.00   16.00    --  104.05  61.00  60.00   41
 34  ω     34.00 111.00   1.00   16.00    --  104.05-125.00 -90.00   77
 35  ω     80.00 131.00   1.00   16.00    --  104.05  38.00 169.37   51
 36  ω     75.00 104.00   1.00   16.00    --  104.05  61.00  60.00   29
 37  ω     75.00 106.00   1.00   16.00    --  104.05  61.00   0.00   31
 38  ω     32.00  57.00   1.00   16.00    --  104.05 -30.00 150.00   25
 39  ω     41.00 111.00   1.00   16.00    --  104.05-125.00   0.00   70
 40  ω     24.00 105.00   1.00   16.00    --  104.05 -94.00  90.00   81
 41  ω     79.00 104.00   1.00   16.00    --  104.05  45.00-180.00   25
 42  ω     80.00 107.00   1.00   16.00    --  104.05  45.00-150.00   27
 43  ω    132.00 174.00   1.00   16.00    --  104.05  61.00 -90.00   42
 44  ω     75.00 174.00   1.00   16.00    --  104.05  61.00  30.00   99
 45  ω     42.00  72.00   1.00   16.00    --  104.05 -61.00-120.00   30
 46  ω     75.00 103.00   1.00   16.00    --  104.05  61.00 -90.00   28
 47  ω     77.00 126.00   1.00   16.00    --  104.05  59.00  12.91   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2120
_reflns_number_total             2165
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.043
_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)+(0.0389P)²+0.1102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0714
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.9645(2) 0.48846(16) 1.00565(18) 0.0295(4) Uani 1 1 d . . . . .
O2 O 1.0840(3) 0.43811(16) 0.46920(19) 0.0342(4) Uani 1 1 d . . . . .
O3 O 0.5320(3) 0.16098(17) 0.6539(2) 0.0320(4) Uani 1 1 d . . . . .
C1 C 0.7440(3) 0.48618(18) 0.7466(2) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.6253(3) 0.60554(19) 0.7786(2) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.6869(3) 0.7294(2) 0.7388(2) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.806777 0.738688 0.692631 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5736(4) 0.8394(2) 0.7663(2) 0.0261(4) Uani 1 1 d . . . . .
H4 H 0.616767 0.923685 0.739517 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3979(4) 0.8264(2) 0.8326(3) 0.0301(5) Uani 1 1 d . . . . .
H5 H 0.318064 0.901421 0.848651 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3385(4) 0.7032(2) 0.8756(3) 0.0339(5) Uani 1 1 d . . . . .
H6 H 0.220053 0.694476 0.923422 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4515(4) 0.5933(2) 0.8490(3) 0.0286(5) Uani 1 1 d . . . . .
H7 H 0.410570 0.509365 0.878693 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6193(3) 0.38381(19) 0.6341(2) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.466069 0.404513 0.586274 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6711(3) 0.24376(19) 0.6714(2) 0.0214(4) Uani 1 1 d . . . . .
C10 C 0.8995(3) 0.2126(2) 0.7340(2) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.936379 0.118478 0.756805 0.027 Uiso 1 1 calc R U . . .
C11 C 1.0651(3) 0.2960(2) 0.6797(2) 0.0226(4) Uani 1 1 d . . . . .
H11 H 1.200287 0.251418 0.670296 0.027 Uiso 1 1 calc R U . . .
C12 C 0.9875(3) 0.4041(2) 0.5667(2) 0.0224(4) Uani 1 1 d . . . . .
C13 C 0.7846(3) 0.46786(19) 0.5811(2) 0.0207(4) Uani 1 1 d . . . . .
H13 H 0.728248 0.537849 0.502285 0.025 Uiso 1 1 calc R U . . .
C14 C 1.0291(3) 0.3133(2) 0.8465(2) 0.0221(4) Uani 1 1 d . . . . .
H14 H 1.142708 0.278375 0.935305 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9172(3) 0.43420(19) 0.8788(2) 0.0200(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
O1 C15 1.210(3) . ?
O2 C12 1.209(3) . ?
O3 C9 1.215(3) . ?
C1 C2 1.498(3) . ?
C1 C8 1.529(3) . ?
C1 C13 1.531(2) . ?
C1 C15 1.503(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.489(3) . ?
C8 C13 1.517(3) . ?
C9 C10 1.479(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.519(3) . ?
C10 C14 1.529(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.488(3) . ?
C11 C14 1.529(3) . ?
C12 C13 1.487(3) . ?
C13 H13 1.0000 . ?
C14 H14 1.0000 . ?
C14 C15 1.488(3) . ?

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
C2 C1 C8 117.49(16) . . ?
C2 C1 C13 118.45(16) . . ?
C2 C1 C15 117.77(16) . . ?
C8 C1 C13 59.43(13) . . ?
C15 C1 C8 115.86(16) . . ?
C15 C1 C13 114.86(16) . . ?
C3 C2 C1 120.63(17) . . ?
C3 C2 C7 119.40(19) . . ?
C7 C2 C1 119.96(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.26(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 119.9 . . ?
C1 C8 H8 116.4 . . ?
C9 C8 C1 117.41(16) . . ?
C9 C8 H8 116.4 . . ?
C9 C8 C13 118.26(17) . . ?
C13 C8 C1 60.34(12) . . ?
C13 C8 H8 116.4 . . ?
O3 C9 C8 121.40(18) . . ?
O3 C9 C10 122.39(18) . . ?
C10 C9 C8 116.19(17) . . ?
C9 C10 H10 116.8 . . ?
C9 C10 C11 118.08(17) . . ?
C9 C10 C14 116.14(17) . . ?
C11 C10 H10 116.8 . . ?
C11 C10 C14 60.20(13) . . ?
C14 C10 H10 116.8 . . ?
C10 C11 H11 116.8 . . ?
C10 C11 C14 60.22(13) . . ?
C12 C11 C10 117.95(18) . . ?
C12 C11 H11 116.8 . . ?
C12 C11 C14 116.11(16) . . ?
C14 C11 H11 116.8 . . ?
O2 C12 C11 121.90(19) . . ?
O2 C12 C13 122.08(18) . . ?
C13 C12 C11 116.01(17) . . ?
C1 C13 H13 116.3 . . ?
C8 C13 C1 60.22(12) . . ?
C8 C13 H13 116.3 . . ?
C12 C13 C1 118.18(16) . . ?
C12 C13 C8 117.68(17) . . ?
C12 C13 H13 116.3 . . ?
C10 C14 H14 116.7 . . ?
C11 C14 C10 59.58(13) . . ?
C11 C14 H14 116.7 . . ?
C15 C14 C10 117.64(16) . . ?
C15 C14 C11 117.26(16) . . ?
C15 C14 H14 116.7 . . ?
O1 C15 C1 121.57(18) . . ?
O1 C15 C14 121.37(18) . . ?
C14 C15 C1 117.05(16) . . ?

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
O2 C12 C13 C1 -143.0(2) . . . . ?
O2 C12 C13 C8 147.8(2) . . . . ?
O3 C9 C10 C11 150.2(2) . . . . ?
O3 C9 C10 C14 -141.2(2) . . . . ?
C1 C2 C3 C4 178.86(18) . . . . ?
C1 C2 C7 C6 -178.6(2) . . . . ?
C1 C8 C9 O3 140.0(2) . . . . ?
C1 C8 C9 C10 -38.6(3) . . . . ?
C1 C8 C13 C12 108.31(19) . . . . ?
C2 C1 C8 C9 -142.99(18) . . . . ?
C2 C1 C8 C13 108.44(19) . . . . ?
C2 C1 C13 C8 -106.84(19) . . . . ?
C2 C1 C13 C12 145.67(18) . . . . ?
C2 C1 C15 O1 -2.1(3) . . . . ?
C2 C1 C15 C14 178.22(16) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C8 C1 C2 C3 -118.6(2) . . . . ?
C8 C1 C2 C7 61.5(3) . . . . ?
C8 C1 C13 C12 -107.5(2) . . . . ?
C8 C1 C15 O1 -148.70(18) . . . . ?
C8 C1 C15 C14 31.6(2) . . . . ?
C8 C9 C10 C11 -31.2(3) . . . . ?
C8 C9 C10 C14 37.4(3) . . . . ?
C9 C8 C13 C1 -107.18(19) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C10 C11 C14 105.7(2) . . . . ?
C9 C10 C14 C11 -108.9(2) . . . . ?
C9 C10 C14 C15 -1.9(3) . . . . ?
C10 C11 C12 O2 -148.2(2) . . . . ?
C10 C11 C12 C13 31.9(3) . . . . ?
C10 C11 C14 C15 -107.61(19) . . . . ?
C10 C14 C15 O1 147.44(19) . . . . ?
C10 C14 C15 C1 -32.9(2) . . . . ?
C11 C10 C14 C15 106.98(19) . . . . ?
C11 C12 C13 C1 36.9(3) . . . . ?
C11 C12 C13 C8 -32.3(3) . . . . ?
C11 C14 C15 O1 -144.47(19) . . . . ?
C11 C14 C15 C1 35.2(2) . . . . ?
C12 C11 C14 C10 108.7(2) . . . . ?
C12 C11 C14 C15 1.1(3) . . . . ?
C13 C1 C2 C3 -50.3(3) . . . . ?
C13 C1 C2 C7 129.8(2) . . . . ?
C13 C1 C8 C9 108.6(2) . . . . ?
C13 C1 C15 O1 144.77(18) . . . . ?
C13 C1 C15 C14 -34.9(2) . . . . ?
C13 C8 C9 O3 -150.71(19) . . . . ?
C13 C8 C9 C10 30.7(3) . . . . ?
C14 C10 C11 C12 -105.69(19) . . . . ?
C14 C11 C12 O2 143.3(2) . . . . ?
C14 C11 C12 C13 -36.7(3) . . . . ?
C15 C1 C2 C3 95.4(2) . . . . ?
C15 C1 C2 C7 -84.6(2) . . . . ?
C15 C1 C8 C9 3.7(2) . . . . ?
C15 C1 C8 C13 -104.86(18) . . . . ?
C15 C1 C13 C8 106.53(18) . . . . ?
C15 C1 C13 C12 -1.0(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_syhwlg
_database_code_depnum_ccdc_archive 'CCDC 2522307'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SYHWLG
_nottingham_internal_coll_number 20019
_nottingham_internal_coll_client SY/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '8.00, 2.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   30/01/2025
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 07/02/2025
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 07/02/2025
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 07/02/2025
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 07/02/2025
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 07/02/2025
_refine_special_details          
;
Hydroxy hydrogen atoms H10 and H11 were refined with their O-H distances restrained to target values of 0.84 %A (DFIX, esd 0.02 %A).
Dichloromethane chlorine atom Cl3 is disordered over positions. The occupancies of the sites were refined and constrained to sum to unity, giving a value of 0.53(1) for the major site. The C-Cl distances for the disordered atoms were restrained to be similar (SADI). Rigid bond and similarity restraints were applied to the anisotropic displacemement parameters of the disordered atoms (RIGU, SIMU).
;
_audit_creation_date             2025-02-07
_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         'C15 H14 O3, C H2 Cl2'
_chemical_formula_sum            'C16 H16 Cl2 O3'
_chemical_formula_weight         327.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H14O3
_chemical_oxdiff_usercomment     
'SYHWLG #20019 GVA-2223 SY/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'
Cl Cl 0.3639 0.7018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.15220(10)
_cell_length_b                   19.1069(3)
_cell_length_c                   12.9283(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.1070(10)
_cell_angle_gamma                90
_cell_volume                     1511.09(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12918
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.0690
_cell_measurement_theta_min      4.1100
_shelx_estimated_absorpt_T_max   0.859
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    3.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.720
_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    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0223
0 -1 0 0.0223
2 0 1 0.0411
-4 0 1 0.0297
0 -1 -5 0.1005
0 1 5 0.1133

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-heptane, dichloromethane'
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.045
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 0.9998 0.0002 0.0003 -0.0796 0.0127
0.0001 -0.9998 -0.0002 -0.0003 0.0796 -0.0127
1.9992 0.0009 0.9990 -0.4885 0.0303 0.2026
-3.9986 -0.0013 1.0015 1.0000 -0.0046 -0.0508
0.0003 -1.0006 -4.9996 -0.0388 -0.0138 -0.6033
-0.0003 1.0006 4.9996 0.0388 0.0138 0.6033

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23557
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.076
_diffrn_reflns_theta_min         4.145
_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 0.997
_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    -39.00  27.00   1.00    2.00    --  -42.25  57.00-120.00   66
  2  ω    -73.00  30.00   1.00    2.00    --  -42.25  77.00 120.00  103
  3  ω    -95.00 -16.00   1.00    2.00    --  -42.25 -29.00  65.91   79
  4  ω     12.00  40.00   1.00    2.00    --   42.25  77.00-163.40   28
  5  ω     13.00  92.00   1.00    2.00    --   42.25  71.00  89.79   79
  6  ω     17.00  68.00   1.00    2.00    --   42.25  57.00   0.00   51
  7  ω     20.00  45.00   1.00    2.00    --   42.25  57.00-180.00   25
  8  ω     10.00  41.00   1.00    2.00    --   42.25  78.00  -4.19   31
  9  ω     22.00 101.00   1.00    2.00    --   42.25  38.00-120.00   79
 10  ω     17.00  71.00   1.00    2.00    --   42.25  57.00 -60.00   54
 11  ω      6.00  76.00   1.00    2.00    --   42.25 -99.00 -30.00   70
 12  ω     22.00  72.00   1.00    2.00    --   42.25  57.00  30.00   50
 13  ω     52.00  77.00   1.00    2.00    --   42.25  57.00-180.00   25
 14  ω     14.00  39.00   1.00    2.00    --   42.25  78.00-115.35   25
 15  ω     72.00  98.00   1.00    8.00    --  100.82  69.00 -78.74   26
 16  ω     75.00 101.00   1.00    8.00    --  100.82  58.00-109.10   26
 17  ω     75.00 171.00   1.00    8.00    --  100.82  48.00 125.77   96
 18  ω    127.00 172.00   1.00    8.00    --  100.82  69.00-108.69   45
 19  ω     75.00 114.00   1.00    8.00    --  100.82  45.00-180.00   39
 20  ω     72.00  98.00   1.00    8.00    --  100.82  69.00-108.69   26
 21  ω     74.00 167.00   1.00    8.00    --  100.82  61.00  12.55   93
 22  ω     27.00 126.00   1.00    8.00    --  100.82 -77.00  60.00   99
 23  ω     27.00 109.00   1.00    8.00    --  100.82-125.00 -30.00   82
 24  ω    143.00 168.00   1.00    8.00    --  100.82  69.00 119.83   25
 25  ω     31.00  92.00   1.00    8.00    --  100.82 -61.00-180.00   61
 26  ω     77.00 104.00   1.00    8.00    --  100.82  61.00-150.00   27
 27  ω     29.00  57.00   1.00    8.00    --  100.82 -30.00 120.00   28
 28  ω     26.00 110.00   1.00    8.00    --  100.82-116.00  46.00   84
 29  ω     74.00 121.00   1.00    8.00    --  100.82  61.00 -30.00   47
 30  ω     80.00 110.00   1.00    8.00    --  100.82-125.00-120.00   30
 31  ω    138.00 164.00   1.00    8.00    --  100.82  61.00 150.00   26
 32  ω     72.00 159.00   1.00    8.00    --  100.82  67.00 -17.45   87
 33  ω     73.00  99.00   1.00    8.00    --  100.82  69.00 119.83   26
 34  ω    144.00 169.00   1.00    8.00    --  100.82  59.00  82.25   25
 35  ω     74.00 130.00   1.00    8.00    --  100.82  61.00-180.00   56
 36  ω     75.00 102.00   1.00    8.00    --  100.82  59.00  82.25   27
 37  ω     72.00 163.00   1.00    8.00    --  100.82  69.00-133.39   91
 38  ω     74.00 100.00   1.00    8.00    --  100.82  61.00 150.00   26
 39  ω     74.00  99.00   1.00    8.00    --  100.82  61.00  60.00   25
 40  ω     28.00  56.00   1.00    8.00    --  100.82 -30.00-150.00   28
 41  ω     71.00 159.00   1.00    8.00    --  100.82  70.00-171.84   88
 42  ω     75.00 100.00   1.00    8.00    --  100.82  61.00   0.00   25
 43  ω     75.00 113.00   1.00    8.00    --  100.82  52.00 -70.28   38
 44  ω     76.00 107.00   1.00    8.00    --  100.82  45.00 -30.00   31
 45  ω     74.00 101.00   1.00    8.00    --  100.82  61.00  90.00   27
 46  ω     74.00 100.00   1.00    8.00    --  100.82  61.00 120.00   26
 47  ω     57.00  91.00   1.00    8.00    --  100.82 -61.00 -90.00   34
 48  ω     75.00 171.00   1.00    8.00    --  100.82  45.00  60.00   96
 49  ω    124.00 171.00   1.00    8.00    --  100.82  69.00 -78.74   47
 50  ω     71.00  98.00   1.00    8.00    --  100.82  70.00  11.47   27
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku OD SuperNova GV1000 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      -0.2481685000
_diffrn_orient_matrix_UB_12      0.0002515000
_diffrn_orient_matrix_UB_13      0.0076987000
_diffrn_orient_matrix_UB_21      0.0058524000
_diffrn_orient_matrix_UB_22      -0.0796273000
_diffrn_orient_matrix_UB_23      0.0187028000
_diffrn_orient_matrix_UB_31      0.0422999000
_diffrn_orient_matrix_UB_32      0.0126318000
_diffrn_orient_matrix_UB_33      0.1181354000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2747
_reflns_number_total             2948
_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         0.899
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.052
_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)+(0.0394P)²+1.2217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0920
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O11-H11 = O10-H10
 0.84 with sigma of 0.02
 C1S-Cl3S \\sim C1S-Cl3T
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl3T \\sim Cl3S: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
4. Rigid body (RIGU) restrains
 Cl3S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl3T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H1SC)=Sof(H1SD)=Sof(Cl3T)=1-FVAR(1)
 Sof(H1SA)=Sof(H1SB)=Sof(Cl3S)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
6.b Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C1S(H1SC,H1SD)
6.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_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
C1 C 0.6202(2) 0.25853(8) 0.32109(11) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.4716(2) 0.29221(8) 0.38977(12) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.3990(3) 0.36374(8) 0.36264(12) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.302040 0.386651 0.409982 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5545(3) 0.41149(8) 0.31128(12) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.547486 0.462270 0.329369 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7760(2) 0.38469(8) 0.29018(13) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.881835 0.394035 0.352833 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7737(2) 0.30688(8) 0.26880(12) 0.0177(3) Uani 1 1 d . . . . .
H6 H 0.917256 0.285989 0.255614 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5771(2) 0.27736(8) 0.20532(11) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.606813 0.239387 0.155477 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3960(2) 0.32775(8) 0.16780(12) 0.0176(3) Uani 1 1 d . . . . .
H8 H 0.257417 0.301338 0.148143 0.021 Uiso 1 1 calc R U . . .
C9 C 0.3589(2) 0.38281(8) 0.24739(12) 0.0183(3) Uani 1 1 d . . . . .
H9 H 0.237472 0.416626 0.227705 0.022 Uiso 1 1 calc R U . . .
O10 O 0.45737(19) 0.36541(6) 0.07915(9) 0.0218(2) Uani 1 1 d D . . . .
H10 H 0.467(4) 0.3361(10) 0.0327(15) 0.033 Uiso 1 1 d D U . . .
O11 O 0.84705(18) 0.42220(6) 0.20362(10) 0.0254(3) Uani 1 1 d D . . . .
H11 H 0.760(3) 0.4120(12) 0.1516(15) 0.038 Uiso 1 1 d D U . . .
O12 O 0.40891(19) 0.26150(6) 0.46436(9) 0.0243(3) Uani 1 1 d . . . . .
C13 C 0.6901(2) 0.18560(8) 0.35067(11) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.5419(3) 0.13067(8) 0.33182(12) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.399994 0.139688 0.297893 0.024 Uiso 1 1 calc R U . . .
C15 C 0.5999(3) 0.06291(8) 0.36221(13) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.497359 0.025879 0.349924 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8079(3) 0.04941(8) 0.41058(13) 0.0262(4) Uani 1 1 d . . . . .
H16 H 0.848682 0.002968 0.430437 0.031 Uiso 1 1 calc R U . . .
C17 C 0.9566(3) 0.10372(9) 0.42997(14) 0.0274(4) Uani 1 1 d . . . . .
H17 H 1.098971 0.094415 0.463092 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8972(3) 0.17184(8) 0.40089(12) 0.0219(3) Uani 1 1 d . . . . .
H18 H 0.998302 0.209040 0.415388 0.026 Uiso 1 1 calc R U . . .
C1S C -0.0491(3) 0.42077(10) 0.65342(15) 0.0350(4) Uani 1 1 d D . . . .
H1SA H -0.142455 0.401597 0.704466 0.042 Uiso 0.47(2) 1 calc R U P A 1
H1SB H 0.059980 0.452257 0.691106 0.042 Uiso 0.47(2) 1 calc R U P A 1
H1SC H -0.098727 0.405313 0.720128 0.042 Uiso 0.53(2) 1 calc R U P A 2
H1SD H 0.052467 0.460610 0.667907 0.042 Uiso 0.53(2) 1 calc R U P A 2
Cl2S Cl 0.08730(10) 0.35157(3) 0.59785(4) 0.05150(18) Uani 1 1 d . . . . .
Cl3S Cl -0.2109(16) 0.4687(2) 0.5595(3) 0.0575(11) Uani 0.47(2) 1 d D U P A 1
Cl3T Cl -0.2743(11) 0.4475(6) 0.5686(3) 0.0680(17) Uani 0.53(2) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.487(2) . ?
C1 C6 1.529(2) . ?
C1 C7 1.535(2) . ?
C1 C13 1.496(2) . ?
C2 C3 1.469(2) . ?
C2 O12 1.2256(19) . ?
C3 H3 1.0000 . ?
C3 C4 1.524(2) . ?
C3 C9 1.528(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.507(2) . ?
C4 C9 1.490(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.512(2) . ?
C5 O11 1.4357(19) . ?
C6 H6 1.0000 . ?
C6 C7 1.498(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.513(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.506(2) . ?
C8 O10 1.4374(18) . ?
C9 H9 1.0000 . ?
O10 H10 0.828(16) . ?
O11 H11 0.836(16) . ?
C13 C14 1.395(2) . ?
C13 C18 1.392(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(2) . ?
C18 H18 0.9500 . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S H1SC 0.9900 . ?
C1S H1SD 0.9900 . ?
C1S Cl2S 1.7598(19) . ?
C1S Cl3S 1.746(5) . ?
C1S Cl3T 1.749(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.78(12) . . ?
C2 C1 C7 115.33(12) . . ?
C2 C1 C13 115.40(13) . . ?
C6 C1 C7 58.53(9) . . ?
C13 C1 C6 120.08(12) . . ?
C13 C1 C7 118.86(12) . . ?
C3 C2 C1 116.80(13) . . ?
O12 C2 C1 121.85(14) . . ?
O12 C2 C3 121.34(14) . . ?
C2 C3 H3 116.6 . . ?
C2 C3 C4 118.16(13) . . ?
C2 C3 C9 117.92(13) . . ?
C4 C3 H3 116.6 . . ?
C4 C3 C9 58.42(10) . . ?
C9 C3 H3 116.6 . . ?
C3 C4 H4 115.7 . . ?
C5 C4 C3 119.78(13) . . ?
C5 C4 H4 115.7 . . ?
C9 C4 C3 60.92(10) . . ?
C9 C4 H4 115.7 . . ?
C9 C4 C5 117.84(13) . . ?
C4 C5 H5 108.4 . . ?
C4 C5 C6 112.11(12) . . ?
C6 C5 H5 108.4 . . ?
O11 C5 C4 109.12(12) . . ?
O11 C5 H5 108.4 . . ?
O11 C5 C6 110.24(13) . . ?
C1 C6 H6 115.6 . . ?
C5 C6 C1 120.47(13) . . ?
C5 C6 H6 115.6 . . ?
C7 C6 C1 60.92(9) . . ?
C7 C6 C5 117.48(12) . . ?
C7 C6 H6 115.6 . . ?
C1 C7 H7 115.7 . . ?
C6 C7 C1 60.55(10) . . ?
C6 C7 H7 115.7 . . ?
C6 C7 C8 117.41(13) . . ?
C8 C7 C1 120.44(12) . . ?
C8 C7 H7 115.7 . . ?
C7 C8 H8 109.8 . . ?
C9 C8 C7 112.68(12) . . ?
C9 C8 H8 109.8 . . ?
O10 C8 C7 109.10(12) . . ?
O10 C8 H8 109.8 . . ?
O10 C8 C9 105.48(12) . . ?
C3 C9 H9 116.2 . . ?
C4 C9 C3 60.66(10) . . ?
C4 C9 C8 117.63(12) . . ?
C4 C9 H9 116.2 . . ?
C8 C9 C3 118.63(13) . . ?
C8 C9 H9 116.2 . . ?
C8 O10 H10 106.5(16) . . ?
C5 O11 H11 106.8(16) . . ?
C14 C13 C1 119.43(13) . . ?
C18 C13 C1 121.27(14) . . ?
C18 C13 C14 119.24(14) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.56(15) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.86(15) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.05(15) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.06(15) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.21(15) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
H1SA C1S H1SB 107.9 . . ?
H1SC C1S H1SD 108.2 . . ?
Cl2S C1S H1SA 109.3 . . ?
Cl2S C1S H1SB 109.3 . . ?
Cl2S C1S H1SC 109.6 . . ?
Cl2S C1S H1SD 109.6 . . ?
Cl3S C1S H1SA 109.3 . . ?
Cl3S C1S H1SB 109.3 . . ?
Cl3S C1S Cl2S 111.82(18) . . ?
Cl3T C1S H1SC 109.6 . . ?
Cl3T C1S H1SD 109.6 . . ?
Cl3T C1S Cl2S 110.1(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
O10 H10 O12 0.828(16) 2.078(17) 2.8421(16) 153(2) 4_565 yes
O11 H11 O10 0.836(16) 2.184(18) 2.9484(17) 152(2) . 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
C1 C2 C3 C4 -31.9(2) . . . . ?
C1 C2 C3 C9 35.21(19) . . . . ?
C1 C6 C7 C8 111.26(14) . . . . ?
C1 C7 C8 C9 31.95(19) . . . . ?
C1 C7 C8 O10 148.74(13) . . . . ?
C1 C13 C14 C15 -177.46(14) . . . . ?
C1 C13 C18 C17 178.39(15) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C2 C1 C6 C7 -104.65(14) . . . . ?
C2 C1 C7 C6 107.14(14) . . . . ?
C2 C1 C7 C8 0.8(2) . . . . ?
C2 C1 C13 C14 74.32(18) . . . . ?
C2 C1 C13 C18 -102.77(17) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C9 107.12(15) . . . . ?
C2 C3 C9 C4 -107.53(15) . . . . ?
C2 C3 C9 C8 -0.1(2) . . . . ?
C3 C4 C5 C6 30.9(2) . . . . ?
C3 C4 C5 O11 153.35(13) . . . . ?
C3 C4 C9 C8 -109.04(15) . . . . ?
C4 C3 C9 C8 107.42(15) . . . . ?
C4 C5 C6 C1 -31.82(19) . . . . ?
C4 C5 C6 C7 38.93(19) . . . . ?
C5 C4 C9 C3 110.42(15) . . . . ?
C5 C4 C9 C8 1.4(2) . . . . ?
C5 C6 C7 C1 -111.40(15) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C1 C2 C3 30.85(19) . . . . ?
C6 C1 C2 O12 -150.53(14) . . . . ?
C6 C1 C7 C8 -106.34(15) . . . . ?
C6 C1 C13 C14 -137.34(15) . . . . ?
C6 C1 C13 C18 45.6(2) . . . . ?
C6 C7 C8 C9 -38.31(18) . . . . ?
C6 C7 C8 O10 78.48(16) . . . . ?
C7 C1 C2 C3 -35.06(18) . . . . ?
C7 C1 C2 O12 143.55(15) . . . . ?
C7 C1 C6 C5 106.58(15) . . . . ?
C7 C1 C13 C14 -69.03(19) . . . . ?
C7 C1 C13 C18 113.88(16) . . . . ?
C7 C8 C9 C3 -32.11(18) . . . . ?
C7 C8 C9 C4 37.75(18) . . . . ?
C9 C3 C4 C5 -107.30(16) . . . . ?
C9 C4 C5 C6 -39.74(19) . . . . ?
C9 C4 C5 O11 82.68(16) . . . . ?
O10 C8 C9 C3 -151.03(13) . . . . ?
O10 C8 C9 C4 -81.17(15) . . . . ?
O11 C5 C6 C1 -153.60(13) . . . . ?
O11 C5 C6 C7 -82.85(16) . . . . ?
O12 C2 C3 C4 149.45(15) . . . . ?
O12 C2 C3 C9 -143.41(15) . . . . ?
C13 C1 C2 C3 -179.72(13) . . . . ?
C13 C1 C2 O12 -1.1(2) . . . . ?
C13 C1 C6 C5 -145.99(14) . . . . ?
C13 C1 C6 C7 107.42(15) . . . . ?
C13 C1 C7 C6 -109.49(15) . . . . ?
C13 C1 C7 C8 144.17(14) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C13 C18 C17 1.3(2) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?

_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.810
####################################################################### 
# 
# 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_syhwlb
_database_code_depnum_ccdc_archive 'CCDC 2522309'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SYHWLB
_nottingham_internal_coll_number 19766
_nottingham_internal_coll_client SY/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   09/05/2024
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 16/05/2024
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 16/05/2024
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 16/05/2024
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 26/05/2024
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 26/05/2024
_refine_special_details          
'All hydrogen atoms were observed in the electron denisty map, geometrically placed, and refined using the riding model.'
_audit_creation_date             2024-05-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 O3'
_chemical_formula_sum            'C17 H14 O3'
_chemical_formula_weight         266.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H14O3
_chemical_oxdiff_usercomment     
'SYHWLB #19766 GVB-1999 SY/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'
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                   9.70520(10)
_cell_length_b                   6.45340(10)
_cell_length_c                   21.6445(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.9690(10)
_cell_angle_gamma                90
_cell_volume                     1345.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14407
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.6160
_cell_measurement_theta_min      4.1020
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_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
-5 0 -1 0.0842
5 0 1 0.0842
1 -4 -2 0.1090
1 4 3 0.1158
0 0 1 0.0223
0 0 -1 0.0213
-5 2 -2 0.0969

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane, dichloromethane'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_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
-4.9942 -0.0012 -1.0164 -0.0646 -0.0044 -0.8083
4.9942 0.0012 1.0164 0.0646 0.0044 0.8083
1.0016 -3.9970 -2.0156 -0.9386 -0.1689 0.2060
0.9960 3.9974 3.0219 0.9645 0.2127 0.1261
-0.0002 -0.0002 0.9995 0.0001 0.0701 0.0146
0.0002 0.0002 -0.9995 -0.0001 -0.0701 -0.0146
-4.9952 1.9979 -2.0060 0.4110 -0.0668 -0.8613

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20447
_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         72.820
_diffrn_reflns_theta_min         4.115
_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 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  19.00   1.00    4.00    --  -41.70  57.00 150.00   63
  2  ω    -20.00  21.00   1.00    4.00    --  -41.70  38.00  90.00   41
  3  ω    -21.00  33.00   1.00    4.00    --  -41.70  38.00-120.00   54
  4  ω     16.00  42.00   1.00    4.00    --   41.70  57.00  90.00   26
  5  ω     65.00  96.00   1.00    4.00    --   41.70-125.00  30.00   31
  6  ω      8.00  40.00   1.00    4.00    --   41.70  82.00 -85.76   32
  7  ω      7.00  34.00   1.00    4.00    --   41.70  83.00-154.96   27
  8  ω     17.00 116.00   1.00    4.00    --   41.70  38.00   0.00   99
  9  ω     17.00  56.00   1.00    4.00    --   41.70 -99.00 -90.00   39
 10  ω     16.00  56.00   1.00    4.00    --   41.70  57.00-120.00   40
 11  ω     44.00 115.00   1.00    4.00    --   41.70  57.00  90.00   71
 12  ω     14.00  69.00   1.00    4.00    --   41.70  57.00-180.00   55
 13  ω     13.00  40.00   1.00    4.00    --   41.70  81.00  28.82   27
 14  ω      9.00  34.00   1.00    4.00    --   41.70  83.00  95.54   25
 15  ω     75.00 113.00   1.00    4.00    --   41.70  57.00-120.00   38
 16  ω    -32.00  62.00   1.00    4.00    --   41.70 -38.00 -60.00   94
 17  ω      7.00  33.00   1.00    4.00    --   41.70  84.00 -14.66   26
 18  ω     22.00  75.00   1.00   16.00    --  104.05 -94.00  99.12   53
 19  ω     74.00 174.00   1.00   16.00    --  104.05  69.00  60.12  100
 20  ω    125.00 157.00   1.00   16.00    --  104.05  74.00 -56.75   32
 21  ω     72.00  98.00   1.00   16.00    --  104.05  74.00 -32.58   26
 22  ω     75.00 101.00   1.00   16.00    --  104.05  61.00-150.00   26
 23  ω     32.00 112.00   1.00   16.00    --  104.05-125.00  90.00   80
 24  ω     77.00 103.00   1.00   16.00    --  104.05  50.00-168.79   26
 25  ω     75.00 103.00   1.00   16.00    --  104.05  61.00 -90.00   28
 26  ω    122.00 175.00   1.00   16.00    --  104.05  61.00 -90.00   53
 27  ω     72.00 116.00   1.00   16.00    --  104.05  74.00 -56.75   44
 28  ω     74.00 138.00   1.00   16.00    --  104.05  68.00  99.26   64
 29  ω     31.00  78.00   1.00   16.00    --  104.05-125.00  60.00   47
 30  ω     87.00 112.00   1.00   16.00    --  104.05-125.00  60.00   25
 31  ω     78.00 138.00   1.00   16.00    --  104.05  45.00-150.00   60
 32  ω     82.00 107.00   1.00   16.00    --  104.05  45.00-180.00   25
 33  ω    122.00 175.00   1.00   16.00    --  104.05  57.00 134.66   53
 34  ω     33.00 124.00   1.00   16.00    --  104.05 -77.00-120.00   91
 35  ω     79.00 104.00   1.00   16.00    --  104.05  45.00  60.00   25
 36  ω     76.00 102.00   1.00   16.00    --  104.05  57.00 134.66   26
 37  ω     72.00 144.00   1.00   16.00    --  104.05  73.00-148.26   72
 38  ω     75.00 101.00   1.00   16.00    --  104.05  61.00 150.00   26
 39  ω     75.00 111.00   1.00   16.00    --  104.05  61.00  60.00   36
 40  ω     41.00  93.00   1.00   16.00    --  104.05 -61.00  90.00   52
 41  ω     78.00 104.00   1.00   16.00    --  104.05  45.00 -90.00   26
 42  ω     75.00 101.00   1.00   16.00    --  104.05  61.00 -60.00   26
 43  ω    130.00 171.00   1.00   16.00    --  104.05  64.00  24.03   41
 44  ω     75.00 148.00   1.00   16.00    --  104.05  61.00 -30.00   73
 45  ω    145.00 172.00   1.00   16.00    --  104.05  61.00  90.00   27
 46  ω     83.00 110.00   1.00   16.00    --  104.05  45.00 -60.00   27
 47  ω     75.00 101.00   1.00   16.00    --  104.05  61.00  90.00   26
 48  ω     76.00 171.00   1.00   16.00    --  104.05  61.00-120.00   95
 49  ω     75.00 173.00   1.00   16.00    --  104.05  61.00   0.00   98
 50  ω     31.00 109.00   1.00   16.00    --  104.05-111.00-137.00   78
 51  ω     78.00 107.00   1.00   16.00    --  104.05 -94.00  99.12   29
 52  ω     74.00 101.00   1.00   16.00    --  104.05  64.00  24.03   27
 53  ω    152.00 177.00   1.00   16.00    --  104.05  68.00  99.26   25
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas 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      0.0128532000
_diffrn_orient_matrix_UB_12      0.2379732000
_diffrn_orient_matrix_UB_13      0.0001504000
_diffrn_orient_matrix_UB_21      -0.0134049000
_diffrn_orient_matrix_UB_22      0.0035163000
_diffrn_orient_matrix_UB_23      0.0701582000
_diffrn_orient_matrix_UB_31      0.1588724000
_diffrn_orient_matrix_UB_32      -0.0191341000
_diffrn_orient_matrix_UB_33      0.0146775000
_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'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                5122
_reflns_number_total             5250
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 2271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.044
_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)+(0.0322P)²+0.2081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0635
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4B(H4B), C4A(H4A), C9A(H9A), C6A(H6A), C9B(H9B), C7B(H7B), C3B(H3B),
 C3A(H3A), C7A(H7A), C6B(H6B)
2.b Secondary CH2 refined with riding coordinates:
 C10B(H10A,H10B), C10A(H10C,H10D), C11A(H11C,H11D), C11B(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C17B(H17B), C16B(H16B), C13A(H13A), C13B(H13B), C15B(H15B), C17A(H17A),
 C14B(H14B), C14A(H14A), C15A(H15A), C16A(H16A)
;
_atom_sites_solution_hydrogens   geom
_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
O2B O 0.42635(11) 0.58944(18) 0.09141(5) 0.0239(2) Uani 1 1 d . . . . .
O3B O -0.01279(12) 0.98138(18) 0.07008(5) 0.0271(2) Uani 1 1 d . . . . .
O2A O 0.82882(12) -0.13777(18) 0.17570(5) 0.0269(2) Uani 1 1 d . . . . .
O1B O 0.07425(12) 0.3899(2) 0.22577(5) 0.0312(3) Uani 1 1 d . . . . .
O1A O 0.40125(11) 0.24327(19) 0.18438(5) 0.0271(3) Uani 1 1 d . . . . .
O3A O 0.71453(12) 0.44780(19) 0.02384(5) 0.0292(3) Uani 1 1 d . . . . .
C5B C 0.05682(16) 0.8433(2) 0.09636(7) 0.0207(3) Uani 1 1 d . . . . .
C2A C 0.50532(16) 0.2273(2) 0.15867(7) 0.0212(3) Uani 1 1 d . . . . .
C8B C 0.31166(16) 0.6159(2) 0.10759(7) 0.0204(3) Uani 1 1 d . . . . .
C4B C 0.05029(16) 0.6291(3) 0.07187(7) 0.0220(3) Uani 1 1 d . . . . .
H4B H -0.017702 0.602025 0.034210 0.026 Uiso 1 1 calc R U . . .
C1A C 0.63613(16) 0.3407(2) 0.18166(7) 0.0210(3) Uani 1 1 d . . . . .
C2B C 0.10600(16) 0.5062(3) 0.18554(7) 0.0221(3) Uani 1 1 d . . . . .
C5A C 0.68661(16) 0.3395(3) 0.06668(7) 0.0216(3) Uani 1 1 d . . . . .
C4A C 0.60599(16) 0.1455(3) 0.05617(7) 0.0222(3) Uani 1 1 d . . . . .
H4A H 0.574112 0.107725 0.011943 0.027 Uiso 1 1 calc R U . . .
C8A C 0.75468(16) 0.0020(3) 0.15343(7) 0.0213(3) Uani 1 1 d . . . . .
C9A C 0.64310(16) -0.0330(2) 0.10127(7) 0.0224(3) Uani 1 1 d . . . . .
H9A H 0.633268 -0.176505 0.083892 0.027 Uiso 1 1 calc R U . . .
C6A C 0.73109(16) 0.3936(2) 0.13251(7) 0.0208(3) Uani 1 1 d . . . . .
H6A H 0.787063 0.523310 0.139807 0.025 Uiso 1 1 calc R U . . .
C9B C 0.18672(16) 0.5096(3) 0.07682(7) 0.0226(3) Uani 1 1 d . . . . .
H9B H 0.200070 0.412006 0.042156 0.027 Uiso 1 1 calc R U . . .
C7B C 0.29019(15) 0.7586(2) 0.15933(7) 0.0202(3) Uani 1 1 d . . . . .
H7B H 0.374399 0.832753 0.179431 0.024 Uiso 1 1 calc R U . . .
C1B C 0.17965(16) 0.7060(2) 0.20139(7) 0.0204(3) Uani 1 1 d . . . . .
C3B C 0.07649(16) 0.4529(2) 0.11842(7) 0.0223(3) Uani 1 1 d . . . . .
H3B H 0.024035 0.321530 0.108119 0.027 Uiso 1 1 calc R U . . .
C3A C 0.50973(16) 0.0905(3) 0.10389(7) 0.0222(3) Uani 1 1 d . . . . .
H3A H 0.421069 0.019370 0.087767 0.027 Uiso 1 1 calc R U . . .
C7A C 0.76932(16) 0.2168(3) 0.17821(7) 0.0214(3) Uani 1 1 d . . . . .
H7A H 0.847655 0.242719 0.211785 0.026 Uiso 1 1 calc R U . . .
C6B C 0.15396(16) 0.8800(3) 0.15355(7) 0.0210(3) Uani 1 1 d . . . . .
H6B H 0.158812 1.024808 0.170130 0.025 Uiso 1 1 calc R U . . .
C10B C 0.20714(17) 0.7660(3) 0.26924(7) 0.0248(3) Uani 1 1 d . . . . .
H10A H 0.276470 0.879245 0.273908 0.030 Uiso 1 1 calc R U . . .
H10B H 0.247256 0.645766 0.293495 0.030 Uiso 1 1 calc R U . . .
C10A C 0.63005(18) 0.4932(3) 0.23410(7) 0.0252(3) Uani 1 1 d . . . . .
H10C H 0.542509 0.572759 0.225971 0.030 Uiso 1 1 calc R U . . .
H10D H 0.707657 0.592517 0.233650 0.030 Uiso 1 1 calc R U . . .
C12B C 0.10678(18) 0.8926(3) 0.36398(8) 0.0319(4) Uani 1 1 d . . . . .
C12A C 0.61461(19) 0.5656(3) 0.34621(8) 0.0321(4) Uani 1 1 d . . . . .
C17B C 0.08862(19) 0.7491(4) 0.41004(9) 0.0389(4) Uani 1 1 d . . . . .
H17B H 0.052661 0.615553 0.398933 0.047 Uiso 1 1 calc R U . . .
C11A C 0.6377(2) 0.3985(3) 0.29924(8) 0.0320(4) Uani 1 1 d . . . . .
H11C H 0.566045 0.289548 0.299702 0.038 Uiso 1 1 calc R U . . .
H11D H 0.729810 0.333790 0.310522 0.038 Uiso 1 1 calc R U . . .
C11B C 0.07619(19) 0.8371(3) 0.29593(8) 0.0342(4) Uani 1 1 d . . . . .
H11A H 0.036789 0.959210 0.272385 0.041 Uiso 1 1 calc R U . . .
H11B H 0.006128 0.724903 0.290937 0.041 Uiso 1 1 calc R U . . .
C16B C 0.1230(2) 0.8005(4) 0.47267(9) 0.0483(6) Uani 1 1 d . . . . .
H16B H 0.109510 0.702280 0.504062 0.058 Uiso 1 1 calc R U . . .
C13A C 0.7020(2) 0.7365(3) 0.35425(8) 0.0416(5) Uani 1 1 d . . . . .
H13A H 0.780327 0.744299 0.331968 0.050 Uiso 1 1 calc R U . . .
C13B C 0.1585(2) 1.0878(4) 0.38135(9) 0.0419(5) Uani 1 1 d . . . . .
H13B H 0.169747 1.188386 0.350310 0.050 Uiso 1 1 calc R U . . .
C15B C 0.1767(2) 0.9937(5) 0.48910(9) 0.0503(6) Uani 1 1 d . . . . .
H15B H 0.201571 1.027576 0.531708 0.060 Uiso 1 1 calc R U . . .
C17A C 0.5025(2) 0.5569(5) 0.37996(9) 0.0505(6) Uani 1 1 d . . . . .
H17A H 0.442193 0.440403 0.375936 0.061 Uiso 1 1 calc R U . . .
C14B C 0.1939(2) 1.1366(4) 0.44369(10) 0.0513(6) Uani 1 1 d . . . . .
H14B H 0.230223 1.269812 0.455018 0.062 Uiso 1 1 calc R U . . .
C14A C 0.6764(3) 0.8964(4) 0.39448(10) 0.0627(7) Uani 1 1 d . . . . .
H14A H 0.737042 1.012323 0.399409 0.075 Uiso 1 1 calc R U . . .
C15A C 0.5639(4) 0.8867(6) 0.42699(11) 0.0746(10) Uani 1 1 d . . . . .
H15A H 0.546101 0.996222 0.454254 0.090 Uiso 1 1 calc R U . . .
C16A C 0.4775(3) 0.7197(7) 0.42011(10) 0.0709(10) Uani 1 1 d . . . . .
H16A H 0.399661 0.713374 0.442733 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2B C8B 1.2188(19) . ?
O3B C5B 1.217(2) . ?
O2A C8A 1.216(2) . ?
O1B C2B 1.217(2) . ?
O1A C2A 1.2153(19) . ?
O3A C5A 1.218(2) . ?
C5B C4B 1.479(2) . ?
C5B C6B 1.481(2) . ?
C2A C1A 1.497(2) . ?
C2A C3A 1.483(2) . ?
C8B C9B 1.479(2) . ?
C8B C7B 1.484(2) . ?
C4B H4B 1.0000 . ?
C4B C9B 1.525(2) . ?
C4B C3B 1.520(2) . ?
C1A C6A 1.528(2) . ?
C1A C7A 1.530(2) . ?
C1A C10A 1.509(2) . ?
C2B C1B 1.494(2) . ?
C2B C3B 1.487(2) . ?
C5A C4A 1.479(2) . ?
C5A C6A 1.480(2) . ?
C4A H4A 1.0000 . ?
C4A C9A 1.525(2) . ?
C4A C3A 1.516(2) . ?
C8A C9A 1.484(2) . ?
C8A C7A 1.487(2) . ?
C9A H9A 1.0000 . ?
C9A C3A 1.527(2) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.526(2) . ?
C9B H9B 1.0000 . ?
C9B C3B 1.524(2) . ?
C7B H7B 1.0000 . ?
C7B C1B 1.527(2) . ?
C7B C6B 1.529(2) . ?
C1B C6B 1.527(2) . ?
C1B C10B 1.511(2) . ?
C3B H3B 1.0000 . ?
C3A H3A 1.0000 . ?
C7A H7A 1.0000 . ?
C6B H6B 1.0000 . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C10B C11B 1.529(2) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.530(2) . ?
C12B C17B 1.387(3) . ?
C12B C11B 1.510(2) . ?
C12B C13B 1.391(3) . ?
C12A C11A 1.517(3) . ?
C12A C13A 1.389(3) . ?
C12A C17A 1.384(3) . ?
C17B H17B 0.9500 . ?
C17B C16B 1.396(3) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.381(4) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.392(3) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.388(3) . ?
C15B H15B 0.9500 . ?
C15B C14B 1.373(4) . ?
C17A H17A 0.9500 . ?
C17A C16A 1.403(4) . ?
C14B H14B 0.9500 . ?
C14A H14A 0.9500 . ?
C14A C15A 1.371(5) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.362(5) . ?
C16A H16A 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
O3B C5B C4B 121.32(14) . . ?
O3B C5B C6B 122.31(14) . . ?
C4B C5B C6B 116.36(13) . . ?
O1A C2A C1A 121.63(15) . . ?
O1A C2A C3A 121.53(14) . . ?
C3A C2A C1A 116.82(13) . . ?
O2B C8B C9B 122.19(14) . . ?
O2B C8B C7B 121.38(14) . . ?
C9B C8B C7B 116.43(13) . . ?
C5B C4B H4B 116.8 . . ?
C5B C4B C9B 116.64(13) . . ?
C5B C4B C3B 117.73(13) . . ?
C9B C4B H4B 116.8 . . ?
C3B C4B H4B 116.8 . . ?
C3B C4B C9B 60.08(10) . . ?
C2A C1A C6A 115.87(13) . . ?
C2A C1A C7A 114.55(13) . . ?
C2A C1A C10A 117.39(14) . . ?
C6A C1A C7A 59.88(10) . . ?
C10A C1A C6A 117.39(13) . . ?
C10A C1A C7A 119.22(13) . . ?
O1B C2B C1B 121.57(14) . . ?
O1B C2B C3B 121.39(15) . . ?
C3B C2B C1B 117.02(13) . . ?
O3A C5A C4A 122.08(14) . . ?
O3A C5A C6A 122.14(15) . . ?
C4A C5A C6A 115.77(13) . . ?
C5A C4A H4A 116.8 . . ?
C5A C4A C9A 117.49(13) . . ?
C5A C4A C3A 116.85(13) . . ?
C9A C4A H4A 116.8 . . ?
C3A C4A H4A 116.8 . . ?
C3A C4A C9A 60.27(10) . . ?
O2A C8A C9A 122.06(15) . . ?
O2A C8A C7A 121.49(14) . . ?
C9A C8A C7A 116.44(13) . . ?
C4A C9A H9A 117.0 . . ?
C4A C9A C3A 59.60(10) . . ?
C8A C9A C4A 117.79(13) . . ?
C8A C9A H9A 117.0 . . ?
C8A C9A C3A 115.86(13) . . ?
C3A C9A H9A 117.0 . . ?
C1A C6A H6A 116.0 . . ?
C5A C6A C1A 119.18(13) . . ?
C5A C6A H6A 116.0 . . ?
C5A C6A C7A 117.86(13) . . ?
C7A C6A C1A 60.11(10) . . ?
C7A C6A H6A 116.0 . . ?
C8B C9B C4B 117.02(13) . . ?
C8B C9B H9B 117.1 . . ?
C8B C9B C3B 116.18(13) . . ?
C4B C9B H9B 117.1 . . ?
C3B C9B C4B 59.81(10) . . ?
C3B C9B H9B 117.1 . . ?
C8B C7B H7B 116.3 . . ?
C8B C7B C1B 119.03(13) . . ?
C8B C7B C6B 117.09(13) . . ?
C1B C7B H7B 116.3 . . ?
C1B C7B C6B 59.97(10) . . ?
C6B C7B H7B 116.3 . . ?
C2B C1B C7B 113.96(13) . . ?
C2B C1B C6B 116.40(13) . . ?
C2B C1B C10B 117.88(13) . . ?
C7B C1B C6B 60.08(10) . . ?
C10B C1B C7B 117.94(13) . . ?
C10B C1B C6B 117.74(14) . . ?
C4B C3B C9B 60.12(10) . . ?
C4B C3B H3B 116.5 . . ?
C2B C3B C4B 118.13(13) . . ?
C2B C3B C9B 117.13(13) . . ?
C2B C3B H3B 116.5 . . ?
C9B C3B H3B 116.5 . . ?
C2A C3A C4A 119.01(13) . . ?
C2A C3A C9A 116.56(13) . . ?
C2A C3A H3A 116.4 . . ?
C4A C3A C9A 60.13(10) . . ?
C4A C3A H3A 116.4 . . ?
C9A C3A H3A 116.4 . . ?
C1A C7A H7A 116.7 . . ?
C8A C7A C1A 117.44(13) . . ?
C8A C7A C6A 117.27(13) . . ?
C8A C7A H7A 116.7 . . ?
C6A C7A C1A 60.01(10) . . ?
C6A C7A H7A 116.7 . . ?
C5B C6B C7B 116.28(13) . . ?
C5B C6B C1B 118.95(14) . . ?
C5B C6B H6B 116.5 . . ?
C7B C6B H6B 116.5 . . ?
C1B C6B C7B 59.95(10) . . ?
C1B C6B H6B 116.5 . . ?
C1B C10B H10A 109.0 . . ?
C1B C10B H10B 109.0 . . ?
C1B C10B C11B 112.79(13) . . ?
H10A C10B H10B 107.8 . . ?
C11B C10B H10A 109.0 . . ?
C11B C10B H10B 109.0 . . ?
C1A C10A H10C 108.4 . . ?
C1A C10A H10D 108.4 . . ?
C1A C10A C11A 115.52(14) . . ?
H10C C10A H10D 107.5 . . ?
C11A C10A H10C 108.4 . . ?
C11A C10A H10D 108.4 . . ?
C17B C12B C11B 121.04(19) . . ?
C17B C12B C13B 118.90(17) . . ?
C13B C12B C11B 120.03(18) . . ?
C13A C12A C11A 120.71(17) . . ?
C17A C12A C11A 121.0(2) . . ?
C17A C12A C13A 118.3(2) . . ?
C12B C17B H17B 119.9 . . ?
C12B C17B C16B 120.2(2) . . ?
C16B C17B H17B 119.9 . . ?
C10A C11A H11C 109.7 . . ?
C10A C11A H11D 109.7 . . ?
C12A C11A C10A 109.81(15) . . ?
C12A C11A H11C 109.7 . . ?
C12A C11A H11D 109.7 . . ?
H11C C11A H11D 108.2 . . ?
C10B C11B H11A 109.3 . . ?
C10B C11B H11B 109.3 . . ?
C12B C11B C10B 111.45(14) . . ?
C12B C11B H11A 109.3 . . ?
C12B C11B H11B 109.3 . . ?
H11A C11B H11B 108.0 . . ?
C17B C16B H16B 119.9 . . ?
C15B C16B C17B 120.2(2) . . ?
C15B C16B H16B 119.9 . . ?
C12A C13A H13A 119.5 . . ?
C12A C13A C14A 121.0(2) . . ?
C14A C13A H13A 119.5 . . ?
C12B C13B H13B 119.8 . . ?
C14B C13B C12B 120.5(2) . . ?
C14B C13B H13B 119.8 . . ?
C16B C15B H15B 120.1 . . ?
C14B C15B C16B 119.79(18) . . ?
C14B C15B H15B 120.1 . . ?
C12A C17A H17A 119.9 . . ?
C12A C17A C16A 120.2(3) . . ?
C16A C17A H17A 119.9 . . ?
C13B C14B H14B 119.8 . . ?
C15B C14B C13B 120.4(2) . . ?
C15B C14B H14B 119.8 . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A C13A 120.1(3) . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A C14A 119.9(2) . . ?
C16A C15A H15A 120.1 . . ?
C17A C16A H16A 119.7 . . ?
C15A C16A C17A 120.7(2) . . ?
C15A C16A H16A 119.7 . . ?

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
O2B C8B C9B C4B -145.90(15) . . . . ?
O2B C8B C9B C3B 146.33(15) . . . . ?
O2B C8B C7B C1B -146.11(15) . . . . ?
O2B C8B C7B C6B 144.93(15) . . . . ?
O3B C5B C4B C9B 141.58(15) . . . . ?
O3B C5B C4B C3B -149.94(15) . . . . ?
O3B C5B C6B C7B -142.66(15) . . . . ?
O3B C5B C6B C1B 148.75(15) . . . . ?
O2A C8A C9A C4A -149.95(15) . . . . ?
O2A C8A C9A C3A 142.40(15) . . . . ?
O2A C8A C7A C1A -141.30(15) . . . . ?
O2A C8A C7A C6A 150.17(15) . . . . ?
O1B C2B C1B C7B 141.34(16) . . . . ?
O1B C2B C1B C6B -151.54(15) . . . . ?
O1B C2B C1B C10B -3.3(2) . . . . ?
O1B C2B C3B C4B 150.22(15) . . . . ?
O1B C2B C3B C9B -140.94(16) . . . . ?
O1A C2A C1A C6A -151.92(15) . . . . ?
O1A C2A C1A C7A 141.14(15) . . . . ?
O1A C2A C1A C10A -6.1(2) . . . . ?
O1A C2A C3A C4A 151.21(15) . . . . ?
O1A C2A C3A C9A -139.86(15) . . . . ?
O3A C5A C4A C9A 145.44(16) . . . . ?
O3A C5A C4A C3A -145.85(16) . . . . ?
O3A C5A C6A C1A 145.27(16) . . . . ?
O3A C5A C6A C7A -145.24(16) . . . . ?
C5B C4B C9B C8B 2.1(2) . . . . ?
C5B C4B C9B C3B 108.17(15) . . . . ?
C5B C4B C3B C2B 0.4(2) . . . . ?
C5B C4B C3B C9B -106.38(16) . . . . ?
C2A C1A C6A C5A 2.6(2) . . . . ?
C2A C1A C6A C7A -104.62(15) . . . . ?
C2A C1A C7A C8A -0.41(19) . . . . ?
C2A C1A C7A C6A 106.83(14) . . . . ?
C2A C1A C10A C11A 79.75(19) . . . . ?
C8B C9B C3B C4B 107.44(15) . . . . ?
C8B C9B C3B C2B -1.0(2) . . . . ?
C8B C7B C1B C2B 1.5(2) . . . . ?
C8B C7B C1B C6B -106.31(15) . . . . ?
C8B C7B C1B C10B 146.07(15) . . . . ?
C8B C7B C6B C5B -0.2(2) . . . . ?
C8B C7B C6B C1B 109.51(15) . . . . ?
C4B C5B C6B C7B 36.31(19) . . . . ?
C4B C5B C6B C1B -32.3(2) . . . . ?
C4B C9B C3B C2B -108.46(15) . . . . ?
C1A C2A C3A C4A -30.2(2) . . . . ?
C1A C2A C3A C9A 38.73(19) . . . . ?
C1A C6A C7A C8A 107.52(15) . . . . ?
C1A C10A C11A C12A -173.80(14) . . . . ?
C2B C1B C6B C5B 1.6(2) . . . . ?
C2B C1B C6B C7B -103.73(15) . . . . ?
C2B C1B C10B C11B -73.45(19) . . . . ?
C5A C4A C9A C8A 1.6(2) . . . . ?
C5A C4A C9A C3A 106.81(15) . . . . ?
C5A C4A C3A C2A -2.1(2) . . . . ?
C5A C4A C3A C9A -107.86(15) . . . . ?
C5A C6A C7A C1A -109.41(15) . . . . ?
C5A C6A C7A C8A -1.9(2) . . . . ?
C4A C5A C6A C1A -34.7(2) . . . . ?
C4A C5A C6A C7A 34.8(2) . . . . ?
C4A C9A C3A C2A -109.76(15) . . . . ?
C8A C9A C3A C2A -1.3(2) . . . . ?
C8A C9A C3A C4A 108.43(15) . . . . ?
C9A C4A C3A C2A 105.73(15) . . . . ?
C9A C8A C7A C1A 37.37(19) . . . . ?
C9A C8A C7A C6A -31.2(2) . . . . ?
C6A C1A C7A C8A -107.24(15) . . . . ?
C6A C1A C10A C11A -134.98(15) . . . . ?
C6A C5A C4A C9A -34.6(2) . . . . ?
C6A C5A C4A C3A 34.13(19) . . . . ?
C9B C8B C7B C1B 34.2(2) . . . . ?
C9B C8B C7B C6B -34.74(19) . . . . ?
C9B C4B C3B C2B 106.80(15) . . . . ?
C7B C8B C9B C4B 33.8(2) . . . . ?
C7B C8B C9B C3B -34.0(2) . . . . ?
C7B C1B C6B C5B 105.35(15) . . . . ?
C7B C1B C10B C11B 143.37(16) . . . . ?
C1B C2B C3B C4B -31.4(2) . . . . ?
C1B C2B C3B C9B 37.5(2) . . . . ?
C1B C7B C6B C5B -109.75(15) . . . . ?
C1B C10B C11B C12B 179.09(16) . . . . ?
C3B C4B C9B C8B -106.03(15) . . . . ?
C3B C2B C1B C7B -37.06(19) . . . . ?
C3B C2B C1B C6B 30.1(2) . . . . ?
C3B C2B C1B C10B 178.34(14) . . . . ?
C3A C2A C1A C6A 29.49(19) . . . . ?
C3A C2A C1A C7A -37.45(18) . . . . ?
C3A C2A C1A C10A 175.29(13) . . . . ?
C3A C4A C9A C8A -105.22(15) . . . . ?
C7A C1A C6A C5A 107.24(16) . . . . ?
C7A C1A C10A C11A -65.94(19) . . . . ?
C7A C8A C9A C4A 31.4(2) . . . . ?
C7A C8A C9A C3A -36.3(2) . . . . ?
C6B C5B C4B C9B -37.40(19) . . . . ?
C6B C5B C4B C3B 31.1(2) . . . . ?
C6B C7B C1B C2B 107.80(14) . . . . ?
C6B C7B C1B C10B -107.62(16) . . . . ?
C6B C1B C10B C11B 74.41(19) . . . . ?
C10B C1B C6B C5B -146.71(14) . . . . ?
C10B C1B C6B C7B 107.94(15) . . . . ?
C10A C1A C6A C5A -143.18(15) . . . . ?
C10A C1A C6A C7A 109.58(15) . . . . ?
C10A C1A C7A C8A 146.21(14) . . . . ?
C10A C1A C7A C6A -106.55(15) . . . . ?
C12B C17B C16B C15B -0.7(3) . . . . ?
C12B C13B C14B C15B -0.8(3) . . . . ?
C12A C13A C14A C15A 0.1(3) . . . . ?
C12A C17A C16A C15A -0.8(3) . . . . ?
C17B C12B C11B C10B -94.8(2) . . . . ?
C17B C12B C13B C14B 1.2(3) . . . . ?
C17B C16B C15B C14B 1.1(3) . . . . ?
C11A C12A C13A C14A 176.06(19) . . . . ?
C11A C12A C17A C16A -175.74(19) . . . . ?
C11B C12B C17B C16B 177.28(18) . . . . ?
C11B C12B C13B C14B -176.58(19) . . . . ?
C16B C15B C14B C13B -0.4(3) . . . . ?
C13A C12A C11A C10A -59.2(2) . . . . ?
C13A C12A C17A C16A 1.3(3) . . . . ?
C13A C14A C15A C16A 0.4(4) . . . . ?
C13B C12B C17B C16B -0.5(3) . . . . ?
C13B C12B C11B C10B 83.0(2) . . . . ?
C17A C12A C11A C10A 117.70(19) . . . . ?
C17A C12A C13A C14A -0.9(3) . . . . ?
C14A C15A C16A C17A -0.1(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 1.198
_oxdiff_exptl_absorpt_empirical_full_min 0.817
####################################################################### 
# 
# 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_SYHWLF
_database_code_depnum_ccdc_archive 'CCDC 2522310'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2026-01-12 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SYHWLF
_nottingham_internal_coll_number 19970
_nottingham_internal_coll_client SY/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '0.50, 1.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczkj1
_nottingham_internal_coll_date   06/12/2024
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 07/02/2025
_nottingham_internal_process_user pczkj1
_nottingham_internal_solution_date 07/02/2025
_nottingham_internal_solution_user pczkj1
_nottingham_internal_refinement_date 07/02/2025
_nottingham_internal_refinement_user pczkj1
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 09/12/2025
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
'All hydrogen atoms were observed in the electron density map and were geometrically placed and refined with a riding model. A close intermolecular contact was observed between bromine atom Br7 and adjacent oxygen atom O19 (Br...O distance 3.022(4) %A. The geometry of the contact is consistent with a halogen bond interaction with the lone pair of  the ketone oxygen atom directed towards the sigma hole of the bromine atom.'
_vrf_PLAT431_SYHWLF              
;
PROBLEM: Short Inter HL..A Contact  Br7      ..O19      .       3.02 Ang.  
RESPONSE: A close intermolecular contact was observed between bromine atom Br7 
and adjacent oxygen atom O19 (Br...O distance 3.022(4) %A. The geometry of the
 contact is consistent with a halogen bond interaction with the lone pair of
  the ketone oxygen atom directed towards the sigma hole of the bromine atom."
;
_audit_creation_date             2025-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H6 Br2 O3 S'
_chemical_formula_sum            'C13 H6 Br2 O3 S'
_chemical_formula_weight         402.064
_chemical_oxdiff_formula         C13H6Br2O3S
_chemical_oxdiff_usercomment     
'SYHWLF #19970 MM-1132 SY/HWL Fomblin Micromount'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.66955 1.28295 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.33376 0.55840 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.6081(8)
_cell_length_b                   13.0496(6)
_cell_length_c                   6.7220(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.104(5)
_cell_angle_gamma                90
_cell_volume                     1261.54(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6282
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2110
_cell_measurement_theta_min      2.9970
_exptl_absorpt_coefficient_mu    9.726
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.450
_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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_description       block
_exptl_crystal_F_000             773.821
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 0 0.0172
1 5 0 0.0082
5 -1 -3 0.0648
-5 0 3 0.0779
1 0 0 0.0065
-1 0 0 0.0185
1 0 4 0.0726

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-heptane, dichloromethane'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
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
-1.0267 -4.9940 0.0046 0.1248 0.5861 -0.0224
1.0267 4.9940 -0.0046 -0.1248 -0.5861 0.0224
4.9884 -1.0091 -3.0000 -0.0125 0.0135 -0.8104
-4.9934 0.0099 3.0008 0.0189 0.1033 0.7953
1.0013 -0.0019 -0.0006 -0.0930 -0.0021 -0.0533
-1.0013 0.0019 0.0006 0.0930 0.0021 0.0533
1.0185 -0.0017 3.9966 -0.6880 0.1218 0.6515

_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9771
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12011
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9771
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.52
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9771
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  124
  2  ω     89.00 169.00   0.50    1.00    --   97.40  82.00-118.00  160
  3  ω     60.00 130.00   0.50    1.00    --   97.40 -82.00 120.00  140
  4  ω    -29.00  24.00   0.50    0.50    --    0.00 -82.00   0.00  106
  5  ω    -21.00  26.00   0.50    0.50    --    0.00 -82.00 -60.00   94
  6  ω    -31.00  29.00   0.50    0.50    --    0.00 -82.00  60.00  120
  7  ω    -31.00  27.00   0.50    0.50    --    0.00 -82.00-120.00  116
  8  ω    -26.00   2.00   0.50    0.50    --    0.00 -82.00-180.00   56
  9  ω     74.00 171.00   0.50    1.00    --   97.40  30.00-150.00  194
 10  ω     34.00 130.00   0.50    1.00    --   97.40 -82.00 -90.00  192
 11  ω     75.00 165.00   0.50    1.00    --   97.40  45.00  90.00  180
 12  ω     10.00  39.00   0.50    1.00    --   97.40 -61.00 120.00   58
 13  ω     90.00 117.00   0.50    1.00    --   97.40 -82.00  30.00   54
 14  ω     71.00 120.00   0.50    1.00    --   97.40 -61.00 120.00   98
 15  ω     81.00 130.00   0.50    1.00    --   97.40 -82.00 -30.00   98
 16  ω      9.00 119.00   0.50    1.00    --   97.40 -30.00 -90.00  220
 17  ω     14.00  66.00   0.50    1.00    --   97.40 -82.00 -30.00  104
 18  ω    101.00 131.00   0.50    1.00    --   97.40 -82.00   0.00   60
 19  ω     37.00  74.00   0.50    1.00    --   97.40 -82.00   0.00   74
 20  ω     20.00  75.00   0.50    1.00    --   97.40 -45.00 150.00  110
 21  ω     96.00 121.00   0.50    1.00    --   97.40 -82.00 150.00   50
 22  ω      9.00 124.00   0.50    1.00    --   97.40 -61.00  60.00  230
 23  ω     93.00 187.00   0.50    1.00    --   97.40  82.00-180.00  188
 24  ω    137.00 162.00   0.50    1.00    --   97.40  82.00-150.00   50
 25  ω     93.00 138.00   0.50    1.00    --   97.40  82.00 120.00   90
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_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      -0.0929960000
_diffrn_orient_matrix_UB_12      -0.0060154000
_diffrn_orient_matrix_UB_13      -0.1484412000
_diffrn_orient_matrix_UB_21      -0.0022811000
_diffrn_orient_matrix_UB_22      -0.1168645000
_diffrn_orient_matrix_UB_23      0.0310081000
_diffrn_orient_matrix_UB_31      -0.0531308000
_diffrn_orient_matrix_UB_32      0.0155618000
_diffrn_orient_matrix_UB_33      0.1765695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184

_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2265
_reflns_number_total             2563
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.63a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.2363
_refine_diff_density_min         -0.9500
_refine_diff_density_rms         0.1803
_refine_ls_d_res_high            0.7962
_refine_ls_d_res_low             14.3815
_refine_ls_goodness_of_fit_ref   1.0515
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.0515
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+4.8152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1320
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_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_refinement_flags_posn
Br7 Br 0.23063(4) 0.31255(4) 0.40473(7) 0.03323(19) Uani 1.000000 .
Br8 Br 0.50630(4) 0.62442(5) 0.19197(8) 0.0380(2) Uani 1.000000 .
S5 S 0.39017(9) 0.42724(10) 0.24449(17) 0.0307(3) Uani 1.000000 .
O18 O 0.2343(2) 0.7255(2) 1.0295(5) 0.0268(7) Uani 1.000000 .
O19 O 0.1090(3) 0.3744(3) 0.9101(5) 0.0318(8) Uani 1.000000 .
O16 O 0.1174(2) 0.5920(3) 0.3165(5) 0.0283(7) Uani 1.000000 .
C2 C 0.2964(3) 0.5213(4) 0.4786(7) 0.0252(9) Uani 1.000000 .
C15 C 0.1347(3) 0.5849(3) 0.4993(7) 0.0220(9) Uani 1.000000 .
C1 C 0.2257(3) 0.5450(3) 0.6081(6) 0.0217(9) Uani 1.000000 .
C17 C 0.2003(3) 0.6617(3) 0.9072(6) 0.0232(9) Uani 1.000000 .
C9 C 0.2584(3) 0.5857(4) 0.8216(7) 0.0234(9) Uani 1.000000 .
H9 H 0.3271(3) 0.5926(4) 0.8650(7) 0.0281(11) Uiso 1.000000 R
C10 C 0.2215(3) 0.4769(3) 0.7919(6) 0.0232(9) Uani 1.000000 .
H10 H 0.2680(3) 0.4202(3) 0.8190(6) 0.0279(11) Uiso 1.000000 R
C12 C 0.0605(4) 0.5416(4) 0.8088(7) 0.0251(9) Uani 1.000000 .
H12 H -0.0022(4) 0.5284(4) 0.8439(7) 0.0301(11) Uiso 1.000000 R
C13 C 0.0983(3) 0.6511(3) 0.8387(7) 0.0240(9) Uani 1.000000 .
H13 H 0.0579(3) 0.7024(3) 0.8921(7) 0.0288(11) Uiso 1.000000 R
C14 C 0.0643(3) 0.6114(3) 0.6249(7) 0.0237(9) Uani 1.000000 .
H14 H 0.0037(3) 0.6391(3) 0.5525(7) 0.0284(11) Uiso 1.000000 R
C11 C 0.1283(3) 0.4574(4) 0.8439(6) 0.0240(9) Uani 1.000000 .
C3 C 0.3608(3) 0.5942(4) 0.4280(7) 0.0257(9) Uani 1.000000 .
H3 H 0.3651(3) 0.6630(4) 0.4749(7) 0.0309(11) Uiso 1.000000 R
C6 C 0.3033(4) 0.4296(4) 0.3876(7) 0.0305(11) Uani 1.000000 .
C4 C 0.4155(4) 0.5537(4) 0.3046(7) 0.0305(10) Uani 1.000000 .


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
Br7 C6 1.875(5) . ?
Br8 C4 1.881(5) . ?
S5 C6 1.722(5) . ?
S5 C4 1.724(6) . ?
O18 C17 1.213(6) . ?
O19 C11 1.223(6) . ?
O16 C15 1.214(5) . ?
C2 C1 1.495(6) . ?
C2 C3 1.421(7) . ?
C2 C6 1.356(7) . ?
C15 C1 1.495(6) . ?
C15 C14 1.481(7) . ?
C1 C9 1.525(6) . ?
C1 C10 1.533(6) . ?
C17 C9 1.486(6) . ?
C17 C13 1.486(7) . ?
C9 H9 1.0000 . ?
C9 C10 1.519(6) . ?
C10 H10 1.0000 . ?
C10 C11 1.485(7) . ?
C12 H12 1.0000 . ?
C12 C13 1.532(6) . ?
C12 C14 1.544(6) . ?
C12 C11 1.469(7) . ?
C13 H13 1.0000 . ?
C13 C14 1.527(6) . ?
C14 H14 1.0000 . ?
C3 H3 0.9500 . ?
C3 C4 1.356(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S5 C6 90.1(3) . . ?
C3 C2 C1 123.7(4) . . ?
C6 C2 C1 124.0(5) . . ?
C6 C2 C3 112.2(4) . . ?
C1 C15 O16 122.1(4) . . ?
C14 C15 O16 121.2(4) . . ?
C14 C15 C1 116.7(4) . . ?
C15 C1 C2 115.7(4) . . ?
C9 C1 C2 119.1(4) . . ?
C9 C1 C15 116.3(4) . . ?
C10 C1 C2 118.6(4) . . ?
C10 C1 C15 116.0(4) . . ?
C10 C1 C9 59.6(3) . . ?
C9 C17 O18 121.8(4) . . ?
C13 C17 O18 122.9(4) . . ?
C13 C17 C9 115.3(4) . . ?
C17 C9 C1 119.4(4) . . ?
H9 C9 C1 116.0(3) . . ?
H9 C9 C17 116.0(3) . . ?
C10 C9 C1 60.5(3) . . ?
C10 C9 C17 117.5(4) . . ?
C10 C9 H9 116.0(3) . . ?
C9 C10 C1 60.0(3) . . ?
H10 C10 C1 116.9(2) . . ?
H10 C10 C9 116.9(3) . . ?
C11 C10 C1 117.2(4) . . ?
C11 C10 C9 116.6(4) . . ?
C11 C10 H10 116.9(3) . . ?
C13 C12 H12 116.9(3) . . ?
C14 C12 H12 116.9(3) . . ?
C14 C12 C13 59.5(3) . . ?
C11 C12 H12 116.9(3) . . ?
C11 C12 C13 117.3(4) . . ?
C11 C12 C14 116.9(4) . . ?
C12 C13 C17 116.5(4) . . ?
H13 C13 C17 116.7(2) . . ?
H13 C13 C12 116.7(3) . . ?
C14 C13 C17 117.8(4) . . ?
C14 C13 C12 60.6(3) . . ?
C14 C13 H13 116.7(3) . . ?
C12 C14 C15 116.4(4) . . ?
C13 C14 C15 118.2(4) . . ?
C13 C14 C12 59.9(3) . . ?
H14 C14 C15 116.8(2) . . ?
H14 C14 C12 116.8(3) . . ?
H14 C14 C13 116.8(3) . . ?
C10 C11 O19 121.1(4) . . ?
C12 C11 O19 121.9(5) . . ?
C12 C11 C10 117.0(4) . . ?
H3 C3 C2 124.1(3) . . ?
C4 C3 C2 111.8(5) . . ?
C4 C3 H3 124.1(3) . . ?
S5 C6 Br7 120.0(3) . . ?
C2 C6 Br7 127.1(4) . . ?
C2 C6 S5 112.8(4) . . ?
S5 C4 Br8 120.9(3) . . ?
C3 C4 Br8 126.0(4) . . ?
C3 C4 S5 113.0(4) . . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_site_symmetry_2
_geom_contact_distance
_geom_contact_publ_flag
O19 Br7 4_566 3.022(4) yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br7 C6 S5 C4 178.8(3) . . . . ?
Br7 C6 C2 C1 -1.4(5) . . . . ?
Br7 C6 C2 C3 -178.3(4) . . . . ?
Br8 C4 S5 C6 -176.4(3) . . . . ?
Br8 C4 C3 C2 177.2(4) . . . . ?
S5 C6 C2 C1 178.7(3) . . . . ?
S5 C6 C2 C3 1.9(4) . . . . ?
S5 C4 C3 C2 0.5(4) . . . . ?
O18 C17 C9 C1 -149.8(4) . . . . ?
O18 C17 C9 C10 140.3(4) . . . . ?
O18 C17 C13 C12 -140.7(4) . . . . ?
O18 C17 C13 C14 150.2(4) . . . . ?
O19 C11 C10 C1 144.0(4) . . . . ?
O19 C11 C10 C9 -147.8(4) . . . . ?
O19 C11 C12 C13 147.6(4) . . . . ?
O19 C11 C12 C14 -144.7(4) . . . . ?
O16 C15 C1 C2 4.0(5) . . . . ?
O16 C15 C1 C9 151.2(4) . . . . ?
O16 C15 C1 C10 -141.6(4) . . . . ?
O16 C15 C14 C12 140.9(4) . . . . ?
O16 C15 C14 C13 -150.8(4) . . . . ?
C2 C1 C15 C14 -178.6(4) . . . . ?
C2 C1 C9 C17 145.2(4) . . . . ?
C2 C1 C9 C10 -108.0(6) . . . . ?
C2 C1 C10 C9 108.8(6) . . . . ?
C2 C1 C10 C11 -144.7(4) . . . . ?
C2 C6 S5 C4 -1.4(4) . . . . ?
C15 C1 C2 C3 88.4(4) . . . . ?
C15 C1 C2 C6 -88.0(5) . . . . ?
C15 C1 C9 C17 -0.8(5) . . . . ?
C15 C1 C9 C10 106.0(5) . . . . ?
C15 C1 C10 C9 -106.6(5) . . . . ?
C15 C1 C10 C11 -0.1(4) . . . . ?
C15 C14 C12 C13 108.7(6) . . . . ?
C15 C14 C12 C11 1.4(5) . . . . ?
C15 C14 C13 C17 0.6(5) . . . . ?
C15 C14 C13 C12 -105.8(6) . . . . ?
C1 C2 C3 C4 -178.4(5) . . . . ?
C1 C15 C14 C12 -36.5(4) . . . . ?
C1 C15 C14 C13 31.8(4) . . . . ?
C1 C9 C17 C13 32.5(5) . . . . ?
C1 C9 C10 C11 -107.6(3) . . . . ?
C1 C10 C9 C17 110.0(3) . . . . ?
C1 C10 C11 C12 -35.0(4) . . . . ?
C17 C9 C1 C10 -106.8(6) . . . . ?
C17 C9 C10 C11 2.4(4) . . . . ?
C17 C13 C12 C14 -108.5(6) . . . . ?
C17 C13 C12 C11 -1.9(5) . . . . ?
C17 C13 C14 C12 106.4(6) . . . . ?
C9 C1 C2 C3 -57.8(5) . . . . ?
C9 C1 C2 C6 125.8(4) . . . . ?
C9 C1 C15 C14 -31.4(4) . . . . ?
C9 C1 C10 C11 106.5(3) . . . . ?
C9 C17 C13 C12 36.9(4) . . . . ?
C9 C17 C13 C14 -32.2(4) . . . . ?
C9 C10 C11 C12 33.2(4) . . . . ?
C10 C1 C2 C3 -126.9(4) . . . . ?
C10 C1 C2 C6 56.6(5) . . . . ?
C10 C1 C15 C14 35.8(4) . . . . ?
C10 C9 C17 C13 -37.3(4) . . . . ?
C10 C11 C12 C13 -33.5(4) . . . . ?
C10 C11 C12 C14 34.3(4) . . . . ?
C13 C14 C12 C11 -107.3(3) . . . . ?
C14 C13 C12 C11 106.6(3) . . . . ?
C3 C4 S5 C6 0.4(4) . . . . ?
C6 C2 C3 C4 -1.6(5) . . . . ?
_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.701
