# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_GDP41
_database_code_depnum_ccdc_archive 'CCDC 2431744'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-03-17 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_audit_creation_date             2025-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT410_GDP41               
;
PROBLEM: Short Intra H...H Contact  H14      ..H19      .       1.87 Ang.  
RESPONSE: This is expected due to the unique structure of the molecule.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 O3 S'
_chemical_formula_sum            'C26 H16 O3 S'
_chemical_formula_weight         408.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H16ClO3
_chemical_oxdiff_usercomment     GPD41
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.74314(5)
_cell_length_b                   7.47998(5)
_cell_length_c                   31.73273(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.3152(5)
_cell_angle_gamma                90
_cell_volume                     1832.703(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17329
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      79.4740
_cell_measurement_theta_min      5.5900
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.606
_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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            'light yellow'
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0325
0 0 1 0.0382
0 -1 0 0.1028
0 1 0 0.0548
-1 0 1 0.1423
1 0 -1 0.1560

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
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
0.0002 -0.0000 -0.9991 -0.0317 -0.0365 -0.0053
-0.0002 0.0000 0.9991 0.0317 0.0365 0.0053
0.0003 -0.9990 0.0014 0.1188 -0.1203 0.1172
-0.0003 0.9990 -0.0014 -0.1188 0.1203 -0.1172
-0.9994 -0.0007 0.9973 -0.0757 0.0865 0.1657
0.9994 0.0007 -0.9973 0.0757 -0.0865 -0.1657

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            25432
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.671
_diffrn_reflns_theta_min         2.793
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  96.00   0.50    0.17    --   42.08-125.00 -90.00  124
  2  ω     45.00 111.00   0.50    0.68    --  117.50-125.00  60.00  132
  3  ω     46.00 111.00   0.50    0.68    --  117.50-125.00 -60.00  130
  4  ω     69.00  95.00   0.50    0.68    --  117.50-105.00-120.32   52
  5  ω     51.00 105.00   0.50    0.68    --  117.50 -95.00-150.00  108
  6  ω     52.00 102.00   0.50    0.68    --  117.50 -95.00-180.00  100
  7  ω     76.00 101.00   0.50    0.68    --  117.50 -95.00  30.00   50
  8  ω     43.00 154.00   0.50    0.68    --  117.50 -88.00 -68.70  222
  9  ω     43.00 154.00   0.50    0.68    --  117.50 -88.00 -68.70  222
 10  ω     44.00 110.00   0.50    0.68    --  117.50 -78.00 -72.43  132
 11  ω     44.00  85.00   0.50    0.68    --  117.50 -77.00 -30.00   82
 12  ω     46.00 109.00   0.50    0.68    --  117.50 -78.00  40.95  126
 13  ω     44.00  98.00   0.50    0.68    --  117.50 -75.00  70.00  108
 14  ω     50.00  80.00   0.50    0.68    --  117.50 -77.00 120.00   60
 15  ω     44.00 105.00   0.50    0.68    --  117.50 -77.00 150.00  122
 16  ω     44.00  71.00   0.50    0.68    --  117.50 -61.00  90.00   54
 17  ω     44.00  70.00   0.50    0.68    --  117.50 -61.00  30.00   52
 18  ω    -31.00  72.00   0.50    0.17    --   42.08 -75.00  70.00  206
 19  ω    -39.00  27.00   0.50    0.17    --   42.08 -19.00 -60.00  132
 20  ω     45.00  71.00   0.50    0.68    --  117.50 -61.00-180.00   52
 21  ω    149.00 178.00   0.50    0.68    --  117.50   0.00 -60.00   58
 22  ω     88.00 178.00   0.50    0.68    --  117.50  75.00-161.00  180
 23  ω     87.00 146.00   0.50    0.68    --  117.50  77.00 -60.00  118
 24  ω     96.00 122.00   0.50    0.68    --  117.50  61.00 -60.00   52
 25  ω    103.00 128.00   0.50    0.68    --  117.50  45.00-120.00   50
 26  ω     98.00 177.00   0.50    0.68    --  117.50  30.00-180.00  158
 27  ω    152.00 177.00   0.50    0.68    --  117.50  61.00 -90.00   50
 28  ω     98.00 177.00   0.50    0.68    --  117.50  30.00-180.00  158
 29  ω    133.00 176.00   0.50    0.68    --  117.50  77.00 -30.00   86
 30  ω     36.00 178.00   0.50    0.68    --  117.50   0.00 -60.00  284
 31  ω    133.00 159.00   0.50    0.68    --  117.50  30.00   0.00   52
 32  ω    116.00 142.00   0.50    0.68    --  117.50  45.00 120.00   52
 33  ω    128.00 178.00   0.50    0.68    --  117.50  77.00 120.00  100
 34  ω     96.00 163.00   0.50    0.68    --  117.50 125.00 150.00  134
 35  ω    130.00 167.00   0.50    0.68    --  117.50 125.00 120.00   74
 36  ω    102.00 144.00   0.50    0.68    --  117.50 125.00-180.00   84
 37  ω   -116.00 -12.00   0.50    0.17    --  -42.08 -75.00  70.00  208
 38  ω   -171.00 -66.00   0.50    0.68    --  -96.00 -75.00  70.00  210
 39  ω    -51.00 -19.00   0.50    0.68    --  -96.00  45.00 -30.00   64
 40  ω    -71.00 -21.00   0.50    0.68    --  -96.00  61.00  30.00  100
 41  ω    -72.00  33.00   0.50    0.17    --  -42.08  75.00-161.00  210
 42  ω    -98.00 -21.00   0.50    0.68    --  -96.00  75.00-161.00  154
 43  ω    -98.00 -21.00   0.50    0.68    --  -96.00  75.00-161.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1074809000
_diffrn_orient_matrix_UB_12      -0.1188934000
_diffrn_orient_matrix_UB_13      0.0317602000
_diffrn_orient_matrix_UB_21      -0.0501982000
_diffrn_orient_matrix_UB_22      0.1204518000
_diffrn_orient_matrix_UB_23      0.0365128000
_diffrn_orient_matrix_UB_31      -0.1604540000
_diffrn_orient_matrix_UB_32      -0.1173563000
_diffrn_orient_matrix_UB_33      0.0052987000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3855
_reflns_number_total             3976
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.9609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0905
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19),
 C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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
S1 S 0.89436(4) 0.81039(4) 0.61299(2) 0.01685(10) Uani 1 1 d . . . . .
O6 O 0.22697(11) 0.62390(12) 0.52919(3) 0.01588(18) Uani 1 1 d . . . . .
O21 O 0.74240(12) 0.64008(14) 0.67742(3) 0.0222(2) Uani 1 1 d . . . . .
O28 O 0.09095(11) 0.61664(12) 0.78261(3) 0.01877(19) Uani 1 1 d . . . . .
C2 C 0.68653(15) 0.75487(16) 0.59264(4) 0.0146(2) Uani 1 1 d . . . . .
C3 C 0.55421(16) 0.68849(15) 0.61696(4) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.39525(15) 0.64571(16) 0.59596(4) 0.0154(2) Uani 1 1 d . . . . .
H4 H 0.302212 0.601774 0.610878 0.018 Uiso 1 1 calc R U . . .
C5 C 0.37741(15) 0.66937(16) 0.55262(4) 0.0143(2) Uani 1 1 d . . . . .
C7 C 0.25619(16) 0.66291(16) 0.48812(4) 0.0149(2) Uani 1 1 d . . . . .
C8 C 0.12821(15) 0.63584(17) 0.45502(4) 0.0170(2) Uani 1 1 d . . . . .
H8 H 0.017295 0.589377 0.459910 0.020 Uiso 1 1 calc R U . . .
C9 C 0.17156(16) 0.67981(17) 0.41546(4) 0.0174(2) Uani 1 1 d . . . . .
H9 H 0.087092 0.668566 0.392302 0.021 Uiso 1 1 calc R U . . .
C10 C 0.34083(16) 0.74233(16) 0.40800(4) 0.0156(2) Uani 1 1 d . . . . .
C11 C 0.38310(17) 0.77571(17) 0.36601(4) 0.0185(2) Uani 1 1 d . . . . .
H11 H 0.295152 0.767581 0.343547 0.022 Uiso 1 1 calc R U . . .
C12 C 0.54869(18) 0.81953(17) 0.35722(4) 0.0200(3) Uani 1 1 d . . . . .
H12 H 0.574913 0.842132 0.328942 0.024 Uiso 1 1 calc R U . . .
C13 C 0.67941(17) 0.83075(18) 0.39044(4) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.794939 0.857205 0.384367 0.023 Uiso 1 1 calc R U . . .
C14 C 0.64129(16) 0.80371(17) 0.43165(4) 0.0174(2) Uani 1 1 d . . . . .
H14 H 0.731250 0.812943 0.453612 0.021 Uiso 1 1 calc R U . . .
C15 C 0.47146(15) 0.76253(15) 0.44205(4) 0.0142(2) Uani 1 1 d . . . . .
C16 C 0.42226(15) 0.72856(15) 0.48409(4) 0.0139(2) Uani 1 1 d . . . . .
C17 C 0.50297(15) 0.73627(15) 0.52722(4) 0.0136(2) Uani 1 1 d . . . . .
C18 C 0.66372(15) 0.78778(16) 0.54861(4) 0.0142(2) Uani 1 1 d . . . . .
C19 C 0.81601(16) 0.86872(17) 0.53362(4) 0.0171(2) Uani 1 1 d . . . . .
H19 H 0.824814 0.905026 0.505170 0.021 Uiso 1 1 calc R U . . .
C20 C 0.94539(16) 0.88759(17) 0.56439(4) 0.0188(2) Uani 1 1 d . . . . .
H20 H 1.054469 0.938796 0.559599 0.023 Uiso 1 1 calc R U . . .
C21 C 0.59159(16) 0.65605(16) 0.66291(4) 0.0164(2) Uani 1 1 d . . . . .
C22 C 0.44856(16) 0.64487(16) 0.69164(4) 0.0152(2) Uani 1 1 d . . . . .
C23 C 0.47459(15) 0.53702(17) 0.72782(4) 0.0168(2) Uani 1 1 d . . . . .
H23 H 0.577428 0.468035 0.732110 0.020 Uiso 1 1 calc R U . . .
C24 C 0.35220(16) 0.53051(17) 0.75713(4) 0.0171(2) Uani 1 1 d . . . . .
H24 H 0.369749 0.455057 0.781153 0.021 Uiso 1 1 calc R U . . .
C25 C 0.20224(15) 0.63463(16) 0.75162(4) 0.0154(2) Uani 1 1 d . . . . .
C26 C 0.17407(15) 0.74443(16) 0.71622(4) 0.0156(2) Uani 1 1 d . . . . .
H26 H 0.072736 0.816020 0.712485 0.019 Uiso 1 1 calc R U . . .
C27 C 0.29775(16) 0.74702(16) 0.68640(4) 0.0154(2) Uani 1 1 d . . . . .
H27 H 0.278762 0.819990 0.661985 0.019 Uiso 1 1 calc R U . . .
C28 C -0.05582(18) 0.7337(2) 0.78110(4) 0.0243(3) Uani 1 1 d . . . . .
H28A H -0.127172 0.714409 0.754659 0.036 Uiso 1 1 calc R U . . .
H28B H -0.016093 0.858091 0.782501 0.036 Uiso 1 1 calc R U . . .
H28C H -0.124584 0.708640 0.805115 0.036 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
S1 C2 1.7386(12) . ?
S1 C20 1.7204(13) . ?
O6 C5 1.3767(14) . ?
O6 C7 1.3709(14) . ?
O21 C21 1.2284(16) . ?
O28 C25 1.3620(15) . ?
O28 C28 1.4325(16) . ?
C2 C3 1.4181(17) . ?
C2 C18 1.4167(17) . ?
C3 C4 1.3922(17) . ?
C3 C21 1.4850(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3830(17) . ?
C5 C17 1.4012(16) . ?
C7 C8 1.4034(17) . ?
C7 C16 1.3913(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3639(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.4281(17) . ?
C10 C11 1.4178(17) . ?
C10 C15 1.4315(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3723(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.4078(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3771(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.4137(17) . ?
C15 C16 1.4371(16) . ?
C16 C17 1.4624(16) . ?
C17 C18 1.4252(16) . ?
C18 C19 1.4380(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3527(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.4888(17) . ?
C22 C23 1.4054(17) . ?
C22 C27 1.3949(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.3776(17) . ?
C24 H24 0.9500 . ?
C24 C25 1.3982(17) . ?
C25 C26 1.3954(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.3962(17) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 S1 C2 90.91(6) . . ?
C7 O6 C5 105.51(9) . . ?
C25 O28 C28 117.32(10) . . ?
C3 C2 S1 124.61(9) . . ?
C18 C2 S1 111.59(9) . . ?
C18 C2 C3 123.78(11) . . ?
C2 C3 C21 119.75(11) . . ?
C4 C3 C2 117.96(11) . . ?
C4 C3 C21 122.18(11) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.72(11) . . ?
C5 C4 H4 121.1 . . ?
O6 C5 C4 121.51(11) . . ?
O6 C5 C17 111.90(10) . . ?
C4 C5 C17 126.59(11) . . ?
O6 C7 C8 121.53(11) . . ?
O6 C7 C16 112.48(10) . . ?
C16 C7 C8 125.98(11) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 C7 116.44(11) . . ?
C9 C8 H8 121.8 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.61(11) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C15 120.97(11) . . ?
C11 C10 C9 119.55(11) . . ?
C11 C10 C15 119.40(11) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.22(12) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.48(12) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.59(12) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.55(12) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C16 117.41(11) . . ?
C14 C15 C10 117.62(11) . . ?
C14 C15 C16 124.85(11) . . ?
C7 C16 C15 117.33(11) . . ?
C7 C16 C17 105.11(10) . . ?
C15 C16 C17 137.50(11) . . ?
C5 C17 C16 104.97(10) . . ?
C5 C17 C18 116.20(11) . . ?
C18 C17 C16 138.83(11) . . ?
C2 C18 C17 117.54(11) . . ?
C2 C18 C19 110.79(11) . . ?
C17 C18 C19 131.67(11) . . ?
C18 C19 H19 123.6 . . ?
C20 C19 C18 112.73(11) . . ?
C20 C19 H19 123.6 . . ?
S1 C20 H20 123.1 . . ?
C19 C20 S1 113.86(9) . . ?
C19 C20 H20 123.1 . . ?
O21 C21 C3 119.56(11) . . ?
O21 C21 C22 119.67(11) . . ?
C3 C21 C22 120.76(11) . . ?
C23 C22 C21 117.71(11) . . ?
C27 C22 C21 123.42(11) . . ?
C27 C22 C23 118.63(11) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.54(11) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.19(11) . . ?
C25 C24 H24 119.9 . . ?
O28 C25 C24 114.79(11) . . ?
O28 C25 C26 124.77(11) . . ?
C26 C25 C24 120.44(11) . . ?
C25 C26 H26 120.7 . . ?
C25 C26 C27 118.70(11) . . ?
C27 C26 H26 120.7 . . ?
C22 C27 C26 121.48(11) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
O28 C28 H28A 109.5 . . ?
O28 C28 H28B 109.5 . . ?
O28 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 C4 -178.42(9) . . . . ?
S1 C2 C3 C21 -2.24(16) . . . . ?
S1 C2 C18 C17 175.64(9) . . . . ?
S1 C2 C18 C19 -3.66(13) . . . . ?
O6 C5 C17 C16 -0.84(13) . . . . ?
O6 C5 C17 C18 179.82(10) . . . . ?
O6 C7 C8 C9 179.83(11) . . . . ?
O6 C7 C16 C15 175.85(10) . . . . ?
O6 C7 C16 C17 -1.83(13) . . . . ?
O21 C21 C22 C23 -30.02(17) . . . . ?
O21 C21 C22 C27 144.30(13) . . . . ?
O28 C25 C26 C27 -178.62(11) . . . . ?
C2 S1 C20 C19 -1.83(11) . . . . ?
C2 C3 C4 C5 0.56(17) . . . . ?
C2 C3 C21 O21 -19.42(18) . . . . ?
C2 C3 C21 C22 159.84(11) . . . . ?
C2 C18 C19 C20 2.35(15) . . . . ?
C3 C2 C18 C17 -5.63(18) . . . . ?
C3 C2 C18 C19 175.07(11) . . . . ?
C3 C4 C5 O6 177.45(10) . . . . ?
C3 C4 C5 C17 -1.41(19) . . . . ?
C3 C21 C22 C23 150.72(12) . . . . ?
C3 C21 C22 C27 -34.95(18) . . . . ?
C4 C3 C21 O21 156.60(12) . . . . ?
C4 C3 C21 C22 -24.15(18) . . . . ?
C4 C5 C17 C16 178.11(12) . . . . ?
C4 C5 C17 C18 -1.23(18) . . . . ?
C5 O6 C7 C8 -179.04(11) . . . . ?
C5 O6 C7 C16 1.33(13) . . . . ?
C5 C17 C18 C2 4.51(16) . . . . ?
C5 C17 C18 C19 -176.37(12) . . . . ?
C7 O6 C5 C4 -179.25(11) . . . . ?
C7 O6 C5 C17 -0.24(13) . . . . ?
C7 C8 C9 C10 2.75(19) . . . . ?
C7 C16 C17 C5 1.56(13) . . . . ?
C7 C16 C17 C18 -179.35(14) . . . . ?
C8 C7 C16 C15 -3.76(19) . . . . ?
C8 C7 C16 C17 178.55(12) . . . . ?
C8 C9 C10 C11 176.07(12) . . . . ?
C8 C9 C10 C15 -0.50(19) . . . . ?
C9 C10 C11 C12 -173.78(12) . . . . ?
C9 C10 C15 C14 172.37(11) . . . . ?
C9 C10 C15 C16 -3.89(17) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C10 C15 C16 C7 5.75(17) . . . . ?
C10 C15 C16 C17 -177.56(13) . . . . ?
C11 C10 C15 C14 -4.20(17) . . . . ?
C11 C10 C15 C16 179.54(11) . . . . ?
C11 C12 C13 C14 -2.1(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C10 2.57(18) . . . . ?
C13 C14 C15 C16 178.52(12) . . . . ?
C14 C15 C16 C7 -170.21(11) . . . . ?
C14 C15 C16 C17 6.5(2) . . . . ?
C15 C10 C11 C12 2.84(19) . . . . ?
C15 C16 C17 C5 -175.39(14) . . . . ?
C15 C16 C17 C18 3.7(3) . . . . ?
C16 C7 C8 C9 -0.59(19) . . . . ?
C16 C17 C18 C2 -174.52(13) . . . . ?
C16 C17 C18 C19 4.6(2) . . . . ?
C17 C18 C19 C20 -176.81(12) . . . . ?
C18 C2 C3 C4 3.01(18) . . . . ?
C18 C2 C3 C21 179.19(11) . . . . ?
C18 C19 C20 S1 0.03(15) . . . . ?
C20 S1 C2 C3 -175.58(11) . . . . ?
C20 S1 C2 C18 3.14(10) . . . . ?
C21 C3 C4 C5 -175.52(11) . . . . ?
C21 C22 C23 C24 175.59(11) . . . . ?
C21 C22 C27 C26 -174.03(11) . . . . ?
C22 C23 C24 C25 -1.47(19) . . . . ?
C23 C22 C27 C26 0.25(18) . . . . ?
C23 C24 C25 O28 179.91(11) . . . . ?
C23 C24 C25 C26 0.73(19) . . . . ?
C24 C25 C26 C27 0.47(18) . . . . ?
C25 C26 C27 C22 -0.96(18) . . . . ?
C27 C22 C23 C24 0.98(18) . . . . ?
C28 O28 C25 C24 173.53(11) . . . . ?
C28 O28 C25 C26 -7.33(18) . . . . ?

_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 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# 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_1265-cl
_database_code_depnum_ccdc_archive 'CCDC 2431756'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-03-17 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_audit_creation_date             2024-09-13
_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         'C28 H19 Cl O3'
_chemical_formula_sum            'C28 H19 Cl O3'
_chemical_formula_weight         438.88
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H23N2O3Cl
_chemical_oxdiff_usercomment     1265-Cl
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.43650(10)
_cell_length_b                   11.7816(2)
_cell_length_c                   40.0556(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2093.67(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7109
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6030
_cell_measurement_theta_min      2.2150
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    1.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.134a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0309
0 1 0 0.0231
2 0 1 0.0637
-2 0 -1 0.1219
0 0 -1 0.0286
0 0 1 0.0209
0 1 -2 0.0272
0 1 1 0.0194
0 -1 -1 0.0309

_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.031
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
-0.0003 -0.9990 -0.0013 -0.1194 -0.0457 0.0268
0.0003 0.9990 0.0013 0.1194 0.0457 -0.0268
1.9986 -0.0084 0.9734 0.1268 0.0683 0.6820
-1.9986 0.0084 -0.9734 -0.1268 -0.0683 -0.6820
-0.0000 0.0006 -0.9979 0.0135 -0.0358 -0.0011
0.0000 -0.0006 0.9979 -0.0135 0.0358 0.0011
0.0002 1.0002 -1.9945 0.1464 -0.0260 -0.0289
0.0003 0.9985 0.9992 0.1058 0.0815 -0.0258
-0.0003 -0.9985 -0.9992 -0.1058 -0.0815 0.0258

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            8900
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.761
_diffrn_reflns_theta_min         2.206
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  35.00   0.50    7.00    --  -44.13  16.00 -82.00  120
  2  ω   -110.00 -17.00   0.50    7.00    --  -44.13 -16.00 108.00  186
  3  ω    -82.00  -1.00   0.50    7.00    --  -44.13 110.00  68.00  162
  4  ω    -97.00 -22.00   0.50   28.00    --  -96.00 139.00 140.00  150
  5  ω     45.00 122.00   0.50   28.00    --  117.50-139.00  80.00  154
  6  ω     89.00 178.00   0.50   28.00    --  117.50  16.00 -82.00  178
  7  ω    103.00 178.00   0.50   28.00    --  117.50 110.00  68.00  150
  8  ω   -110.00 -17.00   0.50    7.00    --  -44.13 -16.00 108.00  186
  9  ω    -25.00  32.00   0.50    7.00    --  -44.13  19.00-150.00  114
 10  ω     99.00 132.00   0.50   28.00    --  117.50  61.00 -30.00   66
 11  ω     59.00  85.00   0.50   28.00    --  117.50 -95.00 -90.00   52
 12  ω     99.00 124.00   0.50   28.00    --  117.50  27.00 -17.10   50
 13  ω    142.00 173.00   0.50   28.00    --  117.50  27.00 -17.10   62
 14  ω    130.00 156.00   0.50   28.00    --  117.50  61.00  60.00   52
 15  ω     99.00 127.00   0.50   28.00    --  117.50  45.00  90.00   56
 16  ω     47.00  75.00   0.50   28.00    --  117.50 -95.00 -60.00   56
 17  ω     80.00 105.00   0.50   28.00    --  117.50 -95.00 -60.00   50
 18  ω     87.00 128.00   0.50   28.00    --  117.50  15.00 -90.00   82
 19  ω     45.00  70.00   0.50   28.00    --  117.50 -61.00  30.00   50
 20  ω     45.00  70.00   0.50   28.00    --  117.50 -61.00  60.00   50
 21  ω     45.00  70.00   0.50   28.00    --  117.50 -61.00 150.00   50
 22  ω     47.00  78.00   0.50   28.00    --  117.50 -77.00 -30.00   62
 23  ω    148.00 178.00   0.50   28.00    --  117.50  61.00 -30.00   60
 24  ω    153.00 178.00   0.50   28.00    --  117.50  45.00  90.00   50
 25  ω     97.00 145.00   0.50   28.00    --  117.50  61.00   0.00   96
 26  ω     88.00 114.00   0.50   28.00    --  117.50 -83.00  27.62   52
 27  ω     53.00 104.00   0.50   28.00    --  117.50 -77.00   0.00  102
 28  ω    126.00 162.00   0.50   28.00    --  117.50  30.00 -30.00   72
 29  ω     45.00  71.00   0.50   28.00    --  117.50 -61.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0705163000
_diffrn_orient_matrix_UB_12      0.1194704000
_diffrn_orient_matrix_UB_13      -0.0134910000
_diffrn_orient_matrix_UB_21      0.0168385000
_diffrn_orient_matrix_UB_22      0.0456431000
_diffrn_orient_matrix_UB_23      0.0359476000
_diffrn_orient_matrix_UB_31      0.3406260000
_diffrn_orient_matrix_UB_32      -0.0269298000
_diffrn_orient_matrix_UB_33      0.0010339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                8349
_reflns_number_total             8900
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.134a 64-bit (release 09-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         8900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.086
_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)+(0.0880P)²+0.6317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7288(13)
 0.2712(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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
Cl1 Cl 0.9336(3) 0.94002(7) 0.52968(2) 0.0436(3) Uani 1 1 d . . . . .
O1 O 0.7070(6) 0.4000(2) 0.65445(6) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.0987(6) 0.7396(2) 0.68686(6) 0.0302(5) Uani 1 1 d . . . . .
O3 O -0.5524(7) 0.5554(2) 0.81526(6) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.8952(8) 0.3385(3) 0.63455(8) 0.0262(7) Uani 1 1 d . . . . .
C2 C 0.9769(9) 0.2263(3) 0.64190(8) 0.0289(7) Uani 1 1 d . . . . .
H2 H 0.905594 0.188341 0.661286 0.035 Uiso 1 1 calc R U . . .
C3 C 1.1637(9) 0.1749(3) 0.61970(9) 0.0288(7) Uani 1 1 d . . . . .
H3 H 1.222578 0.098453 0.623537 0.035 Uiso 1 1 calc R U . . .
C4 C 1.2746(8) 0.2322(3) 0.59073(9) 0.0259(7) Uani 1 1 d . . . . .
C5 C 1.4673(9) 0.1742(3) 0.56842(9) 0.0295(7) Uani 1 1 d . . . . .
H5 H 1.517791 0.097141 0.572670 0.035 Uiso 1 1 calc R U . . .
C6 C 1.5827(9) 0.2272(3) 0.54072(8) 0.0299(7) Uani 1 1 d . . . . .
H6 H 1.710624 0.187087 0.525809 0.036 Uiso 1 1 calc R U . . .
C7 C 1.5101(8) 0.3413(3) 0.53463(8) 0.0267(7) Uani 1 1 d . . . . .
H7 H 1.592669 0.378481 0.515669 0.032 Uiso 1 1 calc R U . . .
C8 C 1.3215(8) 0.4001(3) 0.55561(8) 0.0251(7) Uani 1 1 d . . . . .
H8 H 1.275591 0.477275 0.550939 0.030 Uiso 1 1 calc R U . . .
C9 C 1.1944(8) 0.3473(3) 0.58417(8) 0.0237(7) Uani 1 1 d . . . . .
C10 C 0.9922(8) 0.4017(3) 0.60726(8) 0.0244(7) Uani 1 1 d . . . . .
C11 C 0.8550(8) 0.5118(3) 0.61119(8) 0.0233(6) Uani 1 1 d . . . . .
C12 C 0.8797(8) 0.6166(3) 0.59066(8) 0.0234(6) Uani 1 1 d . . . . .
C13 C 0.8375(8) 0.6152(3) 0.55598(8) 0.0248(7) Uani 1 1 d . . . . .
H13 H 0.796060 0.545197 0.545125 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8551(9) 0.7137(3) 0.53722(8) 0.0277(7) Uani 1 1 d . . . . .
H14 H 0.826238 0.711524 0.513724 0.033 Uiso 1 1 calc R U . . .
C15 C 0.9155(10) 0.8154(3) 0.55320(9) 0.0308(8) Uani 1 1 d . . . . .
C16 C 0.9581(10) 0.8204(3) 0.58742(9) 0.0315(8) Uani 1 1 d . . . . .
H16 H 0.999137 0.890749 0.598063 0.038 Uiso 1 1 calc R U . . .
C17 C 0.9398(9) 0.7209(3) 0.60597(8) 0.0276(7) Uani 1 1 d . . . . .
H17 H 0.968708 0.723824 0.629458 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6826(8) 0.5053(3) 0.63981(8) 0.0249(7) Uani 1 1 d . . . . .
C19 C 0.4837(8) 0.5835(3) 0.65603(8) 0.0261(7) Uani 1 1 d . . . . .
H19 H 0.462700 0.657107 0.646640 0.031 Uiso 1 1 calc R U . . .
C20 C 0.3244(8) 0.5593(3) 0.68376(8) 0.0259(6) Uani 1 1 d . . . . .
H20 H 0.342042 0.486291 0.693635 0.031 Uiso 1 1 calc R U . . .
C21 C 0.1234(8) 0.6441(3) 0.69901(8) 0.0256(7) Uani 1 1 d . . . . .
C22 C -0.0496(8) 0.6139(3) 0.72949(8) 0.0249(7) Uani 1 1 d . . . . .
C23 C -0.0717(9) 0.5039(3) 0.74192(8) 0.0275(7) Uani 1 1 d . . . . .
H23 H 0.030026 0.444073 0.730714 0.033 Uiso 1 1 calc R U . . .
C24 C -0.2401(9) 0.4796(3) 0.77049(9) 0.0293(7) Uani 1 1 d . . . . .
H24 H -0.255102 0.403907 0.778528 0.035 Uiso 1 1 calc R U . . .
C25 C -0.3859(8) 0.5681(3) 0.78704(8) 0.0268(7) Uani 1 1 d . . . . .
C26 C -0.3689(9) 0.6787(3) 0.77477(9) 0.0302(7) Uani 1 1 d . . . . .
H26 H -0.470494 0.738628 0.785970 0.036 Uiso 1 1 calc R U . . .
C27 C -0.2042(9) 0.7008(3) 0.74631(9) 0.0275(7) Uani 1 1 d . . . . .
H27 H -0.195067 0.776128 0.737932 0.033 Uiso 1 1 calc R U . . .
C28 C -0.5735(10) 0.4452(3) 0.82974(9) 0.0355(8) Uani 1 1 d . . . . .
H28A H -0.674456 0.393760 0.814096 0.053 Uiso 1 1 calc R U . . .
H28B H -0.689924 0.449448 0.850497 0.053 Uiso 1 1 calc R U . . .
H28C H -0.370760 0.416617 0.834580 0.053 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
Cl1 C15 1.746(4) . ?
O1 C1 1.363(4) . ?
O1 C18 1.377(4) . ?
O2 C21 1.231(4) . ?
O3 C25 1.359(4) . ?
O3 C28 1.425(4) . ?
C1 C2 1.403(5) . ?
C1 C10 1.391(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.358(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.430(5) . ?
C4 C5 1.413(5) . ?
C4 C9 1.427(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.404(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.419(5) . ?
C9 C10 1.439(5) . ?
C10 C11 1.442(5) . ?
C11 C12 1.487(4) . ?
C11 C18 1.380(5) . ?
C12 C13 1.402(4) . ?
C12 C17 1.399(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(5) . ?
C15 C16 1.385(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.431(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.347(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.472(5) . ?
C21 C22 1.486(5) . ?
C22 C23 1.392(5) . ?
C22 C27 1.404(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.395(5) . ?
C25 C26 1.395(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.379(5) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C18 106.1(3) . . ?
C25 O3 C28 118.3(3) . . ?
O1 C1 C2 122.5(3) . . ?
O1 C1 C10 111.4(3) . . ?
C10 C1 C2 126.1(3) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 C1 116.1(3) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.1(3) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 C9 119.6(3) . . ?
C9 C4 C3 120.8(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C10 117.4(3) . . ?
C8 C9 C4 117.8(3) . . ?
C8 C9 C10 124.8(3) . . ?
C1 C10 C9 117.4(3) . . ?
C1 C10 C11 105.3(3) . . ?
C9 C10 C11 137.2(3) . . ?
C10 C11 C12 131.0(3) . . ?
C18 C11 C10 106.0(3) . . ?
C18 C11 C12 123.1(3) . . ?
C13 C12 C11 121.9(3) . . ?
C17 C12 C11 120.1(3) . . ?
C17 C12 C13 118.0(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 Cl1 119.2(3) . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 Cl1 119.5(3) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.1(3) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
O1 C18 C11 111.1(3) . . ?
O1 C18 C19 115.8(3) . . ?
C11 C18 C19 133.1(3) . . ?
C18 C19 H19 117.9 . . ?
C20 C19 C18 124.2(3) . . ?
C20 C19 H19 117.9 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
O2 C21 C20 120.7(3) . . ?
O2 C21 C22 119.9(3) . . ?
C20 C21 C22 119.4(3) . . ?
C23 C22 C21 123.6(3) . . ?
C23 C22 C27 118.2(3) . . ?
C27 C22 C21 118.2(3) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.5(3) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 118.9(3) . . ?
C25 C24 H24 120.5 . . ?
O3 C25 C24 124.5(3) . . ?
O3 C25 C26 115.1(3) . . ?
C24 C25 C26 120.4(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.1 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.2(3) . . ?
C26 C27 H27 119.4 . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C15 C16 C17 179.3(3) . . . . ?
O1 C1 C2 C3 179.4(3) . . . . ?
O1 C1 C10 C9 179.6(3) . . . . ?
O1 C1 C10 C11 1.0(4) . . . . ?
O1 C18 C19 C20 -0.4(5) . . . . ?
O2 C21 C22 C23 169.8(4) . . . . ?
O2 C21 C22 C27 -8.9(5) . . . . ?
O3 C25 C26 C27 179.7(3) . . . . ?
C1 O1 C18 C11 -0.7(4) . . . . ?
C1 O1 C18 C19 177.7(3) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C1 C10 C11 C12 178.0(4) . . . . ?
C1 C10 C11 C18 -1.4(4) . . . . ?
C2 C1 C10 C9 0.2(6) . . . . ?
C2 C1 C10 C11 -178.4(4) . . . . ?
C2 C3 C4 C5 -179.7(4) . . . . ?
C2 C3 C4 C9 0.7(6) . . . . ?
C3 C4 C5 C6 -178.7(4) . . . . ?
C3 C4 C9 C8 177.7(3) . . . . ?
C3 C4 C9 C10 -1.7(5) . . . . ?
C4 C5 C6 C7 0.6(6) . . . . ?
C4 C9 C10 C1 1.3(5) . . . . ?
C4 C9 C10 C11 179.3(4) . . . . ?
C5 C4 C9 C8 -1.9(5) . . . . ?
C5 C4 C9 C10 178.6(3) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C4 1.4(5) . . . . ?
C7 C8 C9 C10 -179.2(3) . . . . ?
C8 C9 C10 C1 -178.1(3) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C4 C5 C6 0.9(6) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C9 C10 C11 C18 -179.5(4) . . . . ?
C10 C1 C2 C3 -1.3(6) . . . . ?
C10 C11 C12 C13 50.4(6) . . . . ?
C10 C11 C12 C17 -131.1(4) . . . . ?
C10 C11 C18 O1 1.3(4) . . . . ?
C10 C11 C18 C19 -176.6(4) . . . . ?
C11 C12 C13 C14 178.7(3) . . . . ?
C11 C12 C17 C16 -178.7(4) . . . . ?
C11 C18 C19 C20 177.5(4) . . . . ?
C12 C11 C18 O1 -178.2(3) . . . . ?
C12 C11 C18 C19 3.9(6) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C13 C12 C17 C16 -0.1(6) . . . . ?
C13 C14 C15 Cl1 -179.3(3) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C12 0.0(6) . . . . ?
C17 C12 C13 C14 0.1(5) . . . . ?
C18 O1 C1 C2 179.1(3) . . . . ?
C18 O1 C1 C10 -0.3(4) . . . . ?
C18 C11 C12 C13 -130.3(4) . . . . ?
C18 C11 C12 C17 48.2(5) . . . . ?
C18 C19 C20 C21 -179.9(3) . . . . ?
C19 C20 C21 O2 -0.7(5) . . . . ?
C19 C20 C21 C22 179.7(3) . . . . ?
C20 C21 C22 C23 -10.6(5) . . . . ?
C20 C21 C22 C27 170.7(3) . . . . ?
C21 C22 C23 C24 -179.3(3) . . . . ?
C21 C22 C27 C26 -180.0(3) . . . . ?
C22 C23 C24 C25 -0.8(6) . . . . ?
C23 C22 C27 C26 1.3(6) . . . . ?
C23 C24 C25 O3 -179.0(3) . . . . ?
C23 C24 C25 C26 1.4(6) . . . . ?
C24 C25 C26 C27 -0.7(6) . . . . ?
C25 C26 C27 C22 -0.6(6) . . . . ?
C27 C22 C23 C24 -0.6(6) . . . . ?
C28 O3 C25 C24 2.0(5) . . . . ?
C28 O3 C25 C26 -178.4(3) . . . . ?

_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.721
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7288(13) 13340 1728 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2712(13) 12990 1728 nmt -0.9952 -0.0223 0.0002 0.1632 -0.9983 0.0001 0.0154
0.0022 1.0015

_twin_special_details            
;
Component 2 rotated by 176.4797° 
around [-0.00 0.00 1.00] (reciprocal) or [0.01 0.00 1.00] (direct)
;
