# Supplementary Information (SI) for ChemComm.
# 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_2024sot0018_a1_100k
_database_code_depnum_ccdc_archive 'CCDC 2334898'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-02-23 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 N O5'
_chemical_formula_sum            'C25 H19 N O5'
_chemical_formula_weight         413.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H19N1O5
_chemical_oxdiff_usercomment     MEP272
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.51124(5)
_cell_length_b                   15.99027(9)
_cell_length_c                   12.44468(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.8665(5)
_cell_angle_gamma                90
_cell_volume                     1852.230(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26790
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      73.4870
_cell_measurement_theta_min      4.5500
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.772
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -4 -3 0.0305
5 4 3 0.0305
3 -3 -5 0.0457
2 -5 -2 0.0499
-2 5 2 0.0673
-3 5 3 0.0761
-1 -4 5 0.1631
0 -5 2 0.1221
-1 5 -1 0.1297

_exptl_crystal_recrystallization_method 
'The material was recrystallised from diethyl ether by slow evaporation'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
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
-4.9972 -3.9980 -2.9976 -0.6473 0.8264 0.0567
4.9972 3.9980 2.9976 0.6473 -0.8264 -0.0567
2.9979 -2.9971 -4.9970 0.5809 0.4495 0.2463
1.9986 -4.9955 -1.9990 0.4434 0.3880 -0.1534
-1.9986 4.9955 1.9990 -0.4434 -0.3880 0.1534
-2.9980 4.9953 2.9985 -0.6072 -0.4134 0.0683
-0.9991 -3.9967 4.9965 -0.1111 -0.0975 -0.7143
0.0001 -4.9958 1.9984 0.0957 0.1663 -0.5087
-0.9994 4.9956 -0.9990 -0.2596 -0.1917 0.4236

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0061
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33856
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.644
_diffrn_reflns_theta_min         4.564
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00 118.00   0.50    1.00    --   52.07  64.00 139.00  154
  2  ω    -14.00  63.00   0.50    1.00    --   52.07 -64.00   2.00  154
  3  ω     41.00 118.00   0.50    1.00    --   52.07  64.00 139.00  154
  4  ω    -66.00  11.00   0.50    1.00    --  -55.07  64.00 139.00  154
  5  ω    -74.00 -13.00   0.50    1.00    --  -79.34  64.00 139.00  122
  6  ω   -145.00 -68.00   0.50    1.00    --  -79.34 -64.00   2.00  154
  7  ω     18.00  78.00   0.50    1.00    --   83.39 -64.00   2.00  120
  8  ω     72.00 149.00   0.50    1.00    --   83.39  64.00 139.00  154
  9  ω    -38.00 -10.00   0.50    1.00    --    0.00 114.00  94.11   56
 10  ω      1.00  33.00   0.50    1.00    --   28.00  94.00-142.04   64
 11  ω     13.00  42.00   0.50    1.00    --   36.00  87.00-146.57   58
 12  ω     15.00  42.00   0.50    1.00    --   40.00  91.00 -64.89   54
 13  ω   -121.00 -44.00   0.50    1.00    --  -55.07 -64.00   2.00  154
 14  ω   -151.00 -72.00   0.50    1.00    --  -79.34 -37.00-150.00  158
 15  ω   -139.00 -85.00   0.50    1.00    --  -79.34 -99.00 120.00  108
 16  ω     13.00  41.00   0.50    1.00    --   83.39 -37.00  90.00   56
 17  ω     12.00  43.00   0.50    1.00    --   83.39 -37.00  30.00   62
 18  ω     12.00  43.00   0.50    1.00    --   83.39 -37.00-120.00   62
 19  ω     13.00  43.00   0.50    1.00    --   83.39 -37.00  60.00   60
 20  ω     74.00 105.00   0.50    1.00    --   83.39  57.00-120.00   62
 21  ω     12.00  37.00   0.50    1.00    --   83.39 -37.00-150.00   50
 22  ω     12.00  42.00   0.50    1.00    --   83.39 -37.00-180.00   60
 23  ω   -122.00 -78.00   0.50    1.00    --  -88.00 -31.00-100.84   88
 24  ω   -135.00 -90.00   0.50    1.00    --  -88.00-103.00 -62.92   90
 25  ω   -126.00 -78.00   0.50    1.00    --  -88.00 -50.00 -31.88   96
 26  ω   -116.00 -91.00   0.50    1.00    --  -88.00 -65.00-116.86   50
 27  ω   -142.00 -97.00   0.50    1.00    --  -88.00-120.00-175.27   90
 28  ω   -112.00 -86.00   0.50    1.00    --  -88.00-119.00  -1.76   52
 29  ω   -102.00 -76.00   0.50    1.00    --  -88.00 -78.00 -95.22   52
 30  ω   -118.00 -85.00   0.50    1.00    --  -88.00 -67.00-135.97   66
 31  ω   -152.00-127.00   0.50    1.00    --  -88.00 -67.00-135.97   50
 32  ω   -157.00 -80.00   0.50    1.00    --  -88.00 -33.00  20.75  154
 33  ω     36.00  62.00   0.50    1.00    --   92.00   9.00  76.62   52
 34  ω     33.00  70.00   0.50    1.00    --   92.00 -79.00  98.43   74
 35  ω     31.00 109.00   0.50    1.00    --   92.00 -82.00 136.71  156
 36  ω     58.00 104.00   0.50    1.00    --   92.00 -95.00  23.63   92
 37  ω     50.00  81.00   0.50    1.00    --   92.00  -2.00  31.43   62
 38  ω    123.00 149.00   0.50    1.00    --   92.00  -2.00  31.43   52
 39  ω     51.00 159.00   0.50    1.00    --   92.00  14.00 -64.86  216
 40  ω     57.00  83.00   0.50    1.00    --   92.00  15.00 -51.85   52
 41  ω     31.00  68.00   0.50    1.00    --   92.00 -83.00  80.67   74
 42  ω     31.00  72.00   0.50    1.00    --   92.00 -87.00  55.39   82
 43  ω     31.00  64.00   0.50    1.00    --   92.00 -78.00   8.95   66
 44  ω     31.00  72.00   0.50    1.00    --   92.00 -77.00 -59.31   82
 45  ω     42.00  92.00   0.50    1.00    --   92.00  12.00  33.43  100
 46  ω     32.00  88.00   0.50    1.00    --   92.00  -1.00-120.39  112
 47  ω     54.00 112.00   0.50    1.00    --   92.00  -2.00 -72.75  116
 48  ω    112.00 159.00   0.50    1.00    --   92.00   9.00  76.62   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1540264000
_diffrn_orient_matrix_UB_12      -0.0231437000
_diffrn_orient_matrix_UB_13      -0.0099538000
_diffrn_orient_matrix_UB_21      -0.0600793000
_diffrn_orient_matrix_UB_22      -0.0674920000
_diffrn_orient_matrix_UB_23      -0.0855116000
_diffrn_orient_matrix_UB_31      -0.0075660000
_diffrn_orient_matrix_UB_32      0.0647560000
_diffrn_orient_matrix_UB_33      -0.0926726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3636
_reflns_number_total             3678
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.067
_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     281
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0590
_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)+(0.0658P)²+2.9060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1461
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C15(H15A,H15B), C18(H18A,H18B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C11(H11), C21(H21), C24(H24)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.97126(17) 0.47774(10) 0.68366(13) 0.0294(4) Uani 1 1 d . . . . .
O2 O 0.84739(15) 0.57990(9) 0.75812(12) 0.0240(3) Uani 1 1 d . . . . .
O3 O 0.73954(16) 0.55276(9) 0.12144(12) 0.0232(3) Uani 1 1 d . . . . .
O4 O 0.07467(16) 0.80384(10) 0.09314(12) 0.0254(3) Uani 1 1 d . . . . .
O5 O 0.01678(18) 0.70099(12) -0.03645(13) 0.0363(4) Uani 1 1 d . . . . .
N1 N 0.71839(17) 0.66871(11) 0.22445(13) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.9765(2) 0.53145(14) 0.77696(17) 0.0250(5) Uani 1 1 d . . . . .
H1A H 0.983965 0.497635 0.844534 0.030 Uiso 1 1 calc R U . . .
H1B H 1.061252 0.568708 0.786088 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7862(2) 0.56834(13) 0.64894(17) 0.0204(4) Uani 1 1 d . . . . .
C3 C 0.6676(2) 0.60905(13) 0.59016(18) 0.0237(4) Uani 1 1 d . . . . .
H3 H 0.620552 0.651793 0.622400 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6192(2) 0.58468(13) 0.48040(18) 0.0236(4) Uani 1 1 d . . . . .
C5 C 0.6914(2) 0.52124(14) 0.43569(17) 0.0241(5) Uani 1 1 d . . . . .
C6 C 0.8146(2) 0.48274(14) 0.49760(18) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.865423 0.441247 0.466332 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8587(2) 0.50725(13) 0.60470(17) 0.0215(4) Uani 1 1 d . . . . .
C8 C 0.4869(2) 0.62797(13) 0.40941(17) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.399446 0.593247 0.409461 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4644(2) 0.71499(14) 0.45222(17) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.395708 0.723641 0.496819 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5412(2) 0.77916(13) 0.42700(16) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.530519 0.832665 0.457512 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6419(2) 0.76883(12) 0.35317(16) 0.0184(4) Uani 1 1 d . . . . .
H11 H 0.711691 0.810296 0.347855 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6315(2) 0.69872(13) 0.29372(16) 0.0194(4) Uani 1 1 d . . . . .
C13 C 0.5096(2) 0.63652(13) 0.29098(17) 0.0225(4) Uani 1 1 d . . . . .
C14 C 0.5637(2) 0.55565(13) 0.24048(16) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.6279(2) 0.48800(14) 0.32260(17) 0.0261(5) Uani 1 1 d . . . . .
H15A H 0.552016 0.446912 0.328511 0.031 Uiso 1 1 calc R U . . .
H15B H 0.703840 0.458164 0.294090 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8404(2) 0.71199(13) 0.19604(17) 0.0213(4) Uani 1 1 d . . . . .
H16A H 0.816085 0.729415 0.118941 0.032 Uiso 1 1 calc R U . . .
H16B H 0.923437 0.674328 0.207085 0.032 Uiso 1 1 calc R U . . .
H16C H 0.863871 0.761360 0.242961 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6823(2) 0.58978(12) 0.18656(15) 0.0178(4) Uani 1 1 d . . . . .
C18 C 0.4360(2) 0.52396(14) 0.15265(18) 0.0251(5) Uani 1 1 d . . . . .
H18A H 0.468102 0.506951 0.085082 0.030 Uiso 1 1 calc R U . . .
H18B H 0.388738 0.475721 0.180429 0.030 Uiso 1 1 calc R U . . .
C19 C 0.3357(2) 0.59753(14) 0.13079(18) 0.0234(4) Uani 1 1 d . . . . .
C20 C 0.3720(2) 0.65994(14) 0.20784(17) 0.0247(5) Uani 1 1 d . . . . .
C21 C 0.2908(2) 0.73407(14) 0.20300(17) 0.0247(4) Uani 1 1 d . . . . .
H21 H 0.315146 0.777568 0.255536 0.030 Uiso 1 1 calc R U . . .
C22 C 0.1738(2) 0.73932(14) 0.11700(16) 0.0210(4) Uani 1 1 d . . . . .
C23 C 0.1405(2) 0.67745(15) 0.03849(17) 0.0256(5) Uani 1 1 d . . . . .
C24 C 0.2180(2) 0.60520(15) 0.04231(17) 0.0282(5) Uani 1 1 d . . . . .
H24 H 0.193747 0.562676 -0.011632 0.034 Uiso 1 1 calc R U . . .
C25 C 0.0021(3) 0.78792(16) -0.01760(19) 0.0317(5) Uani 1 1 d . . . . .
H25A H -0.100707 0.803190 -0.027835 0.038 Uiso 1 1 calc R U . . .
H25B H 0.045683 0.821113 -0.069436 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.437(3) . ?
O1 C7 1.379(2) . ?
O2 C1 1.430(2) . ?
O2 C2 1.376(2) . ?
O3 C17 1.219(2) . ?
O4 C22 1.388(3) . ?
O4 C25 1.432(3) . ?
O5 C23 1.395(3) . ?
O5 C25 1.421(3) . ?
N1 C12 1.396(2) . ?
N1 C16 1.456(2) . ?
N1 C17 1.366(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.375(3) . ?
C2 C7 1.375(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C4 C5 1.403(3) . ?
C4 C8 1.545(3) . ?
C5 C6 1.405(3) . ?
C5 C15 1.509(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.370(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.521(3) . ?
C8 C13 1.539(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.334(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.466(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.336(3) . ?
C12 C13 1.523(3) . ?
C13 C14 1.570(3) . ?
C13 C20 1.539(3) . ?
C14 C15 1.527(3) . ?
C14 C17 1.527(3) . ?
C14 C18 1.543(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.504(3) . ?
C19 C20 1.378(3) . ?
C19 C24 1.405(3) . ?
C20 C21 1.409(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.366(3) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C1 105.32(16) . . ?
C2 O2 C1 105.30(15) . . ?
C22 O4 C25 104.22(17) . . ?
C23 O5 C25 104.58(17) . . ?
C12 N1 C16 126.09(17) . . ?
C17 N1 C12 113.08(16) . . ?
C17 N1 C16 120.77(16) . . ?
O1 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
O2 C1 O1 107.79(16) . . ?
O2 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.5 . . ?
C3 C2 O2 126.58(19) . . ?
C7 C2 O2 110.20(18) . . ?
C7 C2 C3 123.2(2) . . ?
C2 C3 H3 121.5 . . ?
C2 C3 C4 117.1(2) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 C8 119.84(19) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 C8 120.33(19) . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 C15 119.3(2) . . ?
C6 C5 C15 119.0(2) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 C5 117.5(2) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 O1 109.75(18) . . ?
C6 C7 O1 129.3(2) . . ?
C6 C7 C2 121.0(2) . . ?
C4 C8 H8 109.3 . . ?
C9 C8 C4 111.50(18) . . ?
C9 C8 H8 109.3 . . ?
C9 C8 C13 108.17(17) . . ?
C13 C8 C4 109.20(17) . . ?
C13 C8 H8 109.3 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.85(18) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.39(18) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.27(18) . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C13 107.83(16) . . ?
C11 C12 N1 130.15(18) . . ?
C11 C12 C13 122.00(18) . . ?
C8 C13 C14 115.61(17) . . ?
C12 C13 C8 107.04(17) . . ?
C12 C13 C14 103.68(16) . . ?
C12 C13 C20 113.25(17) . . ?
C20 C13 C8 113.44(17) . . ?
C20 C13 C14 103.58(16) . . ?
C15 C14 C13 115.76(17) . . ?
C15 C14 C17 108.51(17) . . ?
C15 C14 C18 112.94(17) . . ?
C17 C14 C13 102.34(16) . . ?
C17 C14 C18 110.56(16) . . ?
C18 C14 C13 106.20(17) . . ?
C5 C15 C14 113.76(18) . . ?
C5 C15 H15A 108.8 . . ?
C5 C15 H15B 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 N1 124.29(18) . . ?
O3 C17 C14 126.15(18) . . ?
N1 C17 C14 109.54(16) . . ?
C14 C18 H18A 110.9 . . ?
C14 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 C14 104.42(17) . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
C20 C19 C18 112.45(19) . . ?
C20 C19 C24 121.8(2) . . ?
C24 C19 C18 125.7(2) . . ?
C19 C20 C13 110.40(19) . . ?
C19 C20 C21 121.5(2) . . ?
C21 C20 C13 128.05(19) . . ?
C20 C21 H21 122.2 . . ?
C22 C21 C20 115.6(2) . . ?
C22 C21 H21 122.2 . . ?
C21 C22 O4 128.0(2) . . ?
C21 C22 C23 122.5(2) . . ?
C23 C22 O4 109.53(18) . . ?
C22 C23 O5 108.6(2) . . ?
C24 C23 O5 128.8(2) . . ?
C24 C23 C22 122.5(2) . . ?
C19 C24 H24 122.0 . . ?
C23 C24 C19 116.0(2) . . ?
C23 C24 H24 122.0 . . ?
O4 C25 H25A 110.4 . . ?
O4 C25 H25B 110.4 . . ?
O5 C25 O4 106.77(18) . . ?
O5 C25 H25A 110.4 . . ?
O5 C25 H25B 110.4 . . ?
H25A C25 H25B 108.6 . . ?

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
O2 C2 C3 C4 -177.10(19) . . . . ?
O2 C2 C7 O1 -0.8(2) . . . . ?
O2 C2 C7 C6 177.86(19) . . . . ?
O4 C22 C23 O5 -1.1(2) . . . . ?
O4 C22 C23 C24 -178.49(19) . . . . ?
O5 C23 C24 C19 -177.5(2) . . . . ?
N1 C12 C13 C8 139.16(17) . . . . ?
N1 C12 C13 C14 16.5(2) . . . . ?
N1 C12 C13 C20 -95.1(2) . . . . ?
C1 O1 C7 C2 -7.1(2) . . . . ?
C1 O1 C7 C6 174.3(2) . . . . ?
C1 O2 C2 C3 -173.1(2) . . . . ?
C1 O2 C2 C7 8.4(2) . . . . ?
C2 O2 C1 O1 -12.7(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C8 -179.81(18) . . . . ?
C3 C2 C7 O1 -179.36(19) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 C15 172.33(19) . . . . ?
C3 C4 C8 C9 24.3(3) . . . . ?
C3 C4 C8 C13 143.8(2) . . . . ?
C4 C5 C6 C7 2.4(3) . . . . ?
C4 C5 C15 C14 40.6(3) . . . . ?
C4 C8 C9 C10 81.1(2) . . . . ?
C4 C8 C13 C12 -67.6(2) . . . . ?
C4 C8 C13 C14 47.3(2) . . . . ?
C4 C8 C13 C20 166.72(17) . . . . ?
C5 C4 C8 C9 -155.60(19) . . . . ?
C5 C4 C8 C13 -36.1(3) . . . . ?
C5 C6 C7 O1 177.3(2) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
C6 C5 C15 C14 -145.02(19) . . . . ?
C7 O1 C1 O2 12.2(2) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C8 C4 C5 C6 178.02(19) . . . . ?
C8 C4 C5 C15 -7.8(3) . . . . ?
C8 C9 C10 C11 3.6(3) . . . . ?
C8 C13 C14 C15 -17.1(3) . . . . ?
C8 C13 C14 C17 -134.94(17) . . . . ?
C8 C13 C14 C18 109.1(2) . . . . ?
C8 C13 C20 C19 -117.6(2) . . . . ?
C8 C13 C20 C21 64.3(3) . . . . ?
C9 C8 C13 C12 53.9(2) . . . . ?
C9 C8 C13 C14 168.79(17) . . . . ?
C9 C8 C13 C20 -71.8(2) . . . . ?
C9 C10 C11 C12 14.2(3) . . . . ?
C10 C11 C12 N1 -174.13(19) . . . . ?
C10 C11 C12 C13 7.4(3) . . . . ?
C11 C12 C13 C8 -42.0(3) . . . . ?
C11 C12 C13 C14 -164.71(19) . . . . ?
C11 C12 C13 C20 83.7(2) . . . . ?
C12 N1 C17 O3 176.71(19) . . . . ?
C12 N1 C17 C14 -4.7(2) . . . . ?
C12 C13 C14 C15 99.68(19) . . . . ?
C12 C13 C14 C17 -18.1(2) . . . . ?
C12 C13 C14 C18 -134.10(17) . . . . ?
C12 C13 C20 C19 120.1(2) . . . . ?
C12 C13 C20 C21 -58.0(3) . . . . ?
C13 C8 C9 C10 -39.0(3) . . . . ?
C13 C14 C15 C5 -26.6(3) . . . . ?
C13 C14 C17 O3 -166.87(19) . . . . ?
C13 C14 C17 N1 14.6(2) . . . . ?
C13 C14 C18 C19 17.0(2) . . . . ?
C13 C20 C21 C22 178.1(2) . . . . ?
C14 C13 C20 C19 8.5(2) . . . . ?
C14 C13 C20 C21 -169.6(2) . . . . ?
C14 C18 C19 C20 -12.5(2) . . . . ?
C14 C18 C19 C24 166.8(2) . . . . ?
C15 C5 C6 C7 -171.85(19) . . . . ?
C15 C14 C17 O3 70.3(2) . . . . ?
C15 C14 C17 N1 -108.24(18) . . . . ?
C15 C14 C18 C19 144.93(18) . . . . ?
C16 N1 C12 C11 -3.9(3) . . . . ?
C16 N1 C12 C13 174.75(18) . . . . ?
C16 N1 C17 O3 -5.8(3) . . . . ?
C16 N1 C17 C14 172.75(17) . . . . ?
C17 N1 C12 C11 173.4(2) . . . . ?
C17 N1 C12 C13 -7.9(2) . . . . ?
C17 C14 C15 C5 87.8(2) . . . . ?
C17 C14 C18 C19 -93.27(19) . . . . ?
C18 C14 C15 C5 -149.30(18) . . . . ?
C18 C14 C17 O3 -54.1(3) . . . . ?
C18 C14 C17 N1 127.38(18) . . . . ?
C18 C19 C20 C13 2.4(3) . . . . ?
C18 C19 C20 C21 -179.4(2) . . . . ?
C18 C19 C24 C23 179.7(2) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
C20 C13 C14 C15 -141.86(18) . . . . ?
C20 C13 C14 C17 100.34(17) . . . . ?
C20 C13 C14 C18 -15.6(2) . . . . ?
C20 C19 C24 C23 -1.1(3) . . . . ?
C20 C21 C22 O4 178.96(19) . . . . ?
C20 C21 C22 C23 -2.0(3) . . . . ?
C21 C22 C23 O5 179.76(19) . . . . ?
C21 C22 C23 C24 2.4(3) . . . . ?
C22 O4 C25 O5 24.0(2) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C23 O5 C25 O4 -24.7(2) . . . . ?
C24 C19 C20 C13 -176.86(19) . . . . ?
C24 C19 C20 C21 1.4(3) . . . . ?
C25 O4 C22 C21 164.9(2) . . . . ?
C25 O4 C22 C23 -14.2(2) . . . . ?
C25 O5 C23 C22 16.0(2) . . . . ?
C25 O5 C23 C24 -166.8(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP272
_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 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_2024sot0033_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2339972'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-03-13
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 O5'
_chemical_formula_sum            'C20 H16 O5'
_chemical_formula_weight         336.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H16O5
_chemical_oxdiff_usercomment     MEP89
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'

_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'

_cell_length_a                   10.2969(2)
_cell_length_b                   9.8246(2)
_cell_length_c                   14.8656(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.018(2)
_cell_angle_gamma                90.00
_cell_volume                     1501.76(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12137
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.9340
_cell_measurement_theta_min      4.3060
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (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_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 0 0.0371
-5 1 0 0.0371
2 5 3 0.0687
4 -5 -2 0.0515
0 0 -1 0.0489
-1 -4 5 0.0605
1 4 -5 0.0605
5 -3 3 0.0334
-5 1 -4 0.0375
-3 5 -1 0.0432

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_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
4.9953 -0.9948 -0.0118 0.7342 -0.1840 -0.1067
-4.9953 0.9948 0.0118 -0.7342 0.1840 0.1067
1.9921 5.0010 2.9852 0.0153 -0.0344 -0.8992
4.0009 -4.9948 -2.0019 0.8114 -0.1468 0.5672
0.0002 -0.0008 -0.9991 -0.0227 -0.0926 0.0408
-0.9958 -3.9946 5.0035 0.2363 0.6852 0.3882
0.9958 3.9946 -5.0035 -0.2363 -0.6852 -0.3882
4.9968 -2.9913 2.9881 0.9307 0.1821 0.0427
-4.9945 0.9918 -3.9845 -0.8251 -0.1864 0.2700
-3.0014 4.9934 -0.9980 -0.7456 -0.1766 -0.4933

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18915
_diffrn_reflns_theta_full        69.14
_diffrn_reflns_theta_max         69.14
_diffrn_reflns_theta_min         4.30
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.991
_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     47.00 121.00   0.50    1.00    --   48.17  39.00 -68.00  148
  2  ω    -21.00  12.00   0.50    1.00    --   48.17 -39.00 137.00   66
  3  ω   -110.00 -85.00   0.50    1.00    --  -49.92 -39.00 137.00   50
  4  ω    -21.00  18.00   0.50    1.00    --  -49.92  39.00 -68.00   78
  5  ω   -136.00-105.00   0.50    1.00    --  -75.43 -39.00 137.00   62
  6  ω     93.00 119.00   0.50    1.00    --   91.36  39.00 -68.00   52
  7  ω    -17.00   8.00   0.50    1.00    --   48.17 -38.00   0.00   50
  8  ω    -73.00 -48.00   0.50    1.00    --  -49.92 -48.00  21.93   50
  9  ω    -72.00 -47.00   0.50    1.00    --  -49.92 -35.00   5.09   50
 10  ω    -89.00 -48.00   0.50    1.00    --  -49.92 -38.00  60.00   82
 11  ω    -22.00  16.00   0.50    1.00    --  -49.92  38.00  60.00   76
 12  ω    -77.00 -48.00   0.50    1.00    --  -50.00 -50.00 -24.38   58
 13  ω    -77.00 -51.00   0.50    1.00    --  -54.00 -53.00  16.78   52
 14  ω   -119.00 -92.00   0.50    1.00    --  -54.00 -54.00   1.87   54
 15  ω    -75.00 -50.00   0.50    1.00    --  -54.00 -54.00   1.87   50
 16  ω    -85.00 -60.00   0.50    1.00    --  -62.00 -52.00  44.68   50
 17  ω    -91.00 -65.00   0.50    1.00    --  -66.00 -51.00 -34.34   52
 18  ω    -87.00 -62.00   0.50    1.00    --  -66.00 -53.00   5.31   50
 19  ω    -91.00 -66.00   0.50    1.00    --  -70.00 -53.00  16.36   50
 20  ω    -93.00 -68.00   0.50    1.00    --  -70.00 -47.00 -21.12   50
 21  ω    -92.00 -66.00   0.50    1.00    --  -70.00 -53.00  27.07   52
 22  ω    -96.00 -71.00   0.50    1.00    --  -74.00 -52.00  64.13   50
 23  ω   -120.00 -74.00   0.50    1.00    --  -75.43 -45.00 -30.00   92
 24  ω    -30.00  -4.00   0.50    1.00    --  -75.43  45.00 120.00   52
 25  ω    -53.00 -28.00   0.50    1.00    --  -75.43  61.00  60.00   50
 26  ω    -51.00 -24.00   0.50    1.00    --  -75.43  61.00  30.00   54
 27  ω    -33.00  -5.00   0.50    1.00    --  -75.43  45.00 -90.00   56
 28  ω   -139.00 -97.00   0.50    1.00    --  -75.43-125.00  60.00   84
 29  ω    -30.00  -4.00   0.50    1.00    --  -75.43  45.00  90.00   52
 30  ω   -100.00 -75.00   0.50    1.00    --  -78.00 -52.00   4.14   50
 31  ω   -101.00 -75.00   0.50    1.00    --  -78.00 -54.00  46.93   52
 32  ω   -104.00 -79.00   0.50    1.00    --  -82.00 -52.00  -0.95   50
 33  ω   -108.00 -81.00   0.50    1.00    --  -82.00 -54.00 -14.93   54
 34  ω   -150.00-122.00   0.50    1.00    --  -82.00 -55.00  59.86   56
 35  ω     94.00 120.00   0.50    1.00    --   91.36  61.00  60.00   52
 36  ω     97.00 122.00   0.50    1.00    --   91.36  61.00 -30.00   50
 37  ω     49.00  76.00   0.50    1.00    --   91.36 -95.00   0.00   54
 38  ω     34.00  70.00   0.50    1.00    --   91.36 -77.00  60.00   72
 39  ω     40.00  69.00   0.50    1.00    --   91.36 -77.00 150.00   58
 40  ω    100.00 126.00   0.50    1.00    --   91.36  45.00  90.00   52
 41  ω     32.00  58.00   0.50    1.00    --   91.36 -95.00-150.00   52
 42  ω    122.00 158.00   0.50    1.00    --   91.36  61.00   0.00   72
 43  ω    133.00 162.00   0.50    1.00    --   91.36  45.00-150.00   58
 44  ω     86.00 160.00   0.50    1.00    --   91.36  61.00  90.00  148
 45  ω     86.00 111.00   0.50    1.00    --   91.36  61.00   0.00   50
 46  ω     91.00 157.00   0.50    1.00    --   91.36 125.00 150.00  132
 47  ω     35.00  66.00   0.50    1.00    --   91.36 -77.00-120.00   62
 48  ω    116.00 147.00   0.50    1.00    --   91.36  77.00 -60.00   62
 49  ω     94.00 120.00   0.50    1.00    --   91.36  45.00   0.00   52
 50  ω     29.00  70.00   0.50    1.00    --   91.36 -77.00 120.00   82
 51  ω     98.00 124.00   0.50    1.00    --   91.36  45.00  60.00   52
 52  ω    129.00 160.00   0.50    1.00    --   91.36  45.00  60.00   62
 53  ω     29.00  55.00   0.50    1.00    --   91.36 -77.00  90.00   52
 54  ω    127.00 152.00   0.50    1.00    --   91.36  45.00  30.00   50
 55  ω     92.00 118.00   0.50    1.00    --   91.36  45.00  30.00   52
 56  ω     95.00 124.00   0.50    1.00    --   91.36  15.00-180.00   58
 57  ω    134.00 159.00   0.50    1.00    --   91.36  61.00  30.00   50
 58  ω     39.00  76.00   0.50    1.00    --   91.36 -95.00  60.00   74
 59  ω     32.00  57.00   0.50    1.00    --   91.36 -77.00 -60.00   50
 60  ω     86.00 112.00   0.50    1.00    --   91.36  61.00  30.00   52
 61  ω     83.00 108.00   0.50    1.00    --   91.36  15.00-150.00   50
 62  ω    131.00 159.00   0.50    1.00    --   91.36  61.00 -30.00   56
 63  ω     45.00  71.00   0.50    1.00    --   91.36 -77.00 -90.00   52
 64  ω     32.00  62.00   0.50    1.00    --   91.36 -77.00-150.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1342722000
_diffrn_orient_matrix_UB_12      -0.0640483000
_diffrn_orient_matrix_UB_13      0.0228152000
_diffrn_orient_matrix_UB_21      -0.0453914000
_diffrn_orient_matrix_UB_22      -0.0441170000
_diffrn_orient_matrix_UB_23      0.0926907000
_diffrn_orient_matrix_UB_31      -0.0485702000
_diffrn_orient_matrix_UB_32      -0.1361329000
_diffrn_orient_matrix_UB_33      -0.0407585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2493
_reflns_number_total             2781
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.109a 64-bit (release 21-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-1997 97-2 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.4804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B), C15(H15A,H15B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.03947(13) 0.24939(14) 0.26957(9) 0.0259(3) Uani 1 1 d . . .
H1A H 1.0303 0.1559 0.2452 0.031 Uiso 1 1 calc R . .
H1B H 1.1236 0.2869 0.2519 0.031 Uiso 1 1 calc R . .
C2 C 0.73851(11) 0.51962(12) 0.39471(8) 0.0180(3) Uani 1 1 d . . .
C3 C 0.77728(12) 0.47769(12) 0.30969(8) 0.0194(3) Uani 1 1 d . . .
H3 H 0.7359 0.5116 0.2556 0.023 Uiso 1 1 calc R . .
C4 C 0.87749(12) 0.38574(12) 0.30819(8) 0.0196(3) Uani 1 1 d . . .
C5 C 0.93817(12) 0.33543(12) 0.38666(8) 0.0198(3) Uani 1 1 d . . .
C6 C 0.90141(12) 0.37286(12) 0.47026(8) 0.0193(3) Uani 1 1 d . . .
H6 H 0.9439 0.3374 0.5235 0.023 Uiso 1 1 calc R . .
C7 C 0.79742(12) 0.46654(12) 0.47410(8) 0.0180(3) Uani 1 1 d . . .
C8 C 0.74509(11) 0.50599(12) 0.56126(8) 0.0185(3) Uani 1 1 d . . .
C9 C 0.76918(12) 0.42550(13) 0.63822(8) 0.0211(3) Uani 1 1 d . . .
H9 H 0.8217 0.3464 0.6347 0.025 Uiso 1 1 calc R . .
C10 C 0.71729(12) 0.45994(13) 0.71948(8) 0.0229(3) Uani 1 1 d . . .
H10 H 0.7356 0.4052 0.7713 0.028 Uiso 1 1 calc R . .
C11 C 0.63881(12) 0.57391(13) 0.72519(8) 0.0215(3) Uani 1 1 d . . .
H11 H 0.6019 0.5958 0.7806 0.026 Uiso 1 1 calc R . .
C12 C 0.61372(12) 0.65678(13) 0.64986(8) 0.0193(3) Uani 1 1 d . . .
C13 C 0.66647(11) 0.62241(12) 0.56803(8) 0.0178(3) Uani 1 1 d . . .
C14 C 0.52852(12) 0.78085(13) 0.65611(8) 0.0213(3) Uani 1 1 d . . .
H14A H 0.5839 0.8624 0.6662 0.026 Uiso 1 1 calc R . .
H14B H 0.4733 0.7712 0.7083 0.026 Uiso 1 1 calc R . .
C15 C 0.44182(12) 0.80048(13) 0.57042(8) 0.0206(3) Uani 1 1 d . . .
H15A H 0.3750 0.7280 0.5672 0.025 Uiso 1 1 calc R . .
H15B H 0.3963 0.8889 0.5740 0.025 Uiso 1 1 calc R . .
C16 C 0.51510(12) 0.79725(12) 0.48575(8) 0.0187(3) Uani 1 1 d . . .
C17 C 0.64072(11) 0.71050(12) 0.48405(8) 0.0176(3) Uani 1 1 d . . .
C18 C 0.75234(12) 0.81355(12) 0.47702(8) 0.0181(3) Uani 1 1 d . . .
C19 C 0.83394(12) 1.02142(13) 0.53919(9) 0.0245(3) Uani 1 1 d . . .
H19A H 0.8482 1.0499 0.4773 0.037 Uiso 1 1 calc R . .
H19B H 0.9161 0.9892 0.5680 0.037 Uiso 1 1 calc R . .
H19C H 0.8018 1.0988 0.5731 0.037 Uiso 1 1 calc R . .
C20 C 0.62852(12) 0.61987(12) 0.39992(8) 0.0188(3) Uani 1 1 d . . .
H20A H 0.5453 0.5693 0.3999 0.023 Uiso 1 1 calc R . .
H20B H 0.6260 0.6784 0.3456 0.023 Uiso 1 1 calc R . .
O1 O 0.47793(9) 0.85736(9) 0.41810(6) 0.0251(2) Uani 1 1 d . . .
O2 O 0.73900(8) 0.91255(8) 0.53795(6) 0.0214(2) Uani 1 1 d . . .
O3 O 0.83684(9) 0.80907(9) 0.42442(6) 0.0247(2) Uani 1 1 d . . .
O4 O 1.03557(9) 0.24691(9) 0.36557(6) 0.0266(2) Uani 1 1 d . . .
O5 O 0.93438(9) 0.33321(9) 0.23430(6) 0.0256(2) 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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 O4 1.4299(16) . ?
C1 O5 1.4368(15) . ?
C2 C3 1.4070(17) . ?
C2 C7 1.3991(17) . ?
C2 C20 1.5060(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3725(17) . ?
C4 C5 1.3851(18) . ?
C4 O5 1.3724(15) . ?
C5 C6 1.3685(17) . ?
C5 O4 1.3761(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.4154(17) . ?
C7 C8 1.4810(17) . ?
C8 C9 1.4021(17) . ?
C8 C13 1.4079(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3882(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3861(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3976(18) . ?
C12 C13 1.3995(17) . ?
C12 C14 1.5075(17) . ?
C13 C17 1.5306(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5289(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5015(17) . ?
C16 C17 1.5504(16) . ?
C16 O1 1.2109(15) . ?
C17 C18 1.5393(16) . ?
C17 C20 1.5350(16) . ?
C18 O2 1.3410(15) . ?
C18 O3 1.2009(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 O2 1.4485(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.4 . . ?
O4 C1 H1A 110.0 . . ?
O4 C1 H1B 110.0 . . ?
O4 C1 O5 108.29(10) . . ?
O5 C1 H1A 110.0 . . ?
O5 C1 H1B 110.0 . . ?
C3 C2 C20 119.17(10) . . ?
C7 C2 C3 121.18(11) . . ?
C7 C2 C20 119.62(11) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.16(11) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 C5 121.83(11) . . ?
O5 C4 C3 127.84(11) . . ?
O5 C4 C5 110.32(11) . . ?
C6 C5 C4 122.34(11) . . ?
C6 C5 O4 128.06(11) . . ?
O4 C5 C4 109.61(11) . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.22(11) . . ?
C7 C6 H6 121.4 . . ?
C2 C7 C6 120.25(11) . . ?
C2 C7 C8 118.61(11) . . ?
C6 C7 C8 121.09(11) . . ?
C9 C8 C7 120.62(11) . . ?
C9 C8 C13 118.53(11) . . ?
C13 C8 C7 120.81(11) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.86(12) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.17(11) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.35(12) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.48(11) . . ?
C11 C12 C14 120.35(11) . . ?
C13 C12 C14 120.16(11) . . ?
C8 C13 C17 118.47(10) . . ?
C12 C13 C8 120.60(11) . . ?
C12 C13 C17 120.93(11) . . ?
C12 C14 H14A 109.3 . . ?
C12 C14 H14B 109.3 . . ?
C12 C14 C15 111.52(10) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.49(10) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 C17 118.80(10) . . ?
O1 C16 C15 122.35(11) . . ?
O1 C16 C17 118.83(10) . . ?
C13 C17 C16 113.98(9) . . ?
C13 C17 C18 109.23(9) . . ?
C13 C17 C20 109.86(10) . . ?
C18 C17 C16 105.43(9) . . ?
C20 C17 C16 107.43(9) . . ?
C20 C17 C18 110.83(9) . . ?
O2 C18 C17 109.14(10) . . ?
O3 C18 C17 126.11(11) . . ?
O3 C18 O2 124.74(11) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
C2 C20 C17 113.06(10) . . ?
C2 C20 H20A 109.0 . . ?
C2 C20 H20B 109.0 . . ?
C17 C20 H20A 109.0 . . ?
C17 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C18 O2 C19 116.82(9) . . ?
C5 O4 C1 106.00(9) . . ?
C4 O5 C1 105.57(9) . . ?

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
C2 C3 C4 C5 0.21(18) . . . . ?
C2 C3 C4 O5 -177.98(11) . . . . ?
C2 C7 C8 C9 158.91(11) . . . . ?
C2 C7 C8 C13 -18.91(17) . . . . ?
C3 C2 C7 C6 2.48(18) . . . . ?
C3 C2 C7 C8 -174.99(10) . . . . ?
C3 C2 C20 C17 -150.01(11) . . . . ?
C3 C4 C5 C6 0.71(19) . . . . ?
C3 C4 C5 O4 -179.29(11) . . . . ?
C3 C4 O5 C1 176.19(12) . . . . ?
C4 C5 C6 C7 -0.05(18) . . . . ?
C4 C5 O4 C1 3.44(13) . . . . ?
C5 C4 O5 C1 -2.17(13) . . . . ?
C5 C6 C7 C2 -1.51(17) . . . . ?
C5 C6 C7 C8 175.90(11) . . . . ?
C6 C5 O4 C1 -176.55(13) . . . . ?
C6 C7 C8 C9 -18.55(17) . . . . ?
C6 C7 C8 C13 163.64(11) . . . . ?
C7 C2 C3 C4 -1.79(17) . . . . ?
C7 C2 C20 C17 32.05(15) . . . . ?
C7 C8 C9 C10 -178.15(11) . . . . ?
C7 C8 C13 C12 177.88(11) . . . . ?
C7 C8 C13 C17 -2.39(16) . . . . ?
C8 C9 C10 C11 1.02(19) . . . . ?
C8 C13 C17 C16 156.64(10) . . . . ?
C8 C13 C17 C18 -85.74(13) . . . . ?
C8 C13 C17 C20 36.03(14) . . . . ?
C9 C8 C13 C12 0.02(17) . . . . ?
C9 C8 C13 C17 179.75(10) . . . . ?
C9 C10 C11 C12 -1.48(19) . . . . ?
C10 C11 C12 C13 1.21(18) . . . . ?
C10 C11 C12 C14 -179.91(11) . . . . ?
C11 C12 C13 C8 -0.48(17) . . . . ?
C11 C12 C13 C17 179.80(11) . . . . ?
C11 C12 C14 C15 -141.81(11) . . . . ?
C12 C13 C17 C16 -23.63(15) . . . . ?
C12 C13 C17 C18 93.99(13) . . . . ?
C12 C13 C17 C20 -144.25(11) . . . . ?
C12 C14 C15 C16 -51.18(14) . . . . ?
C13 C8 C9 C10 -0.29(18) . . . . ?
C13 C12 C14 C15 37.06(15) . . . . ?
C13 C17 C18 O2 -75.11(12) . . . . ?
C13 C17 C18 O3 106.44(13) . . . . ?
C13 C17 C20 C2 -49.73(13) . . . . ?
C14 C12 C13 C8 -179.36(11) . . . . ?
C14 C12 C13 C17 0.92(17) . . . . ?
C14 C15 C16 C17 29.57(15) . . . . ?
C14 C15 C16 O1 -152.23(12) . . . . ?
C15 C16 C17 C13 7.17(15) . . . . ?
C15 C16 C17 C18 -112.61(11) . . . . ?
C15 C16 C17 C20 129.14(11) . . . . ?
C16 C17 C18 O2 47.76(12) . . . . ?
C16 C17 C18 O3 -130.68(12) . . . . ?
C16 C17 C20 C2 -174.22(9) . . . . ?
C17 C18 O2 C19 -178.20(9) . . . . ?
C18 C17 C20 C2 71.08(12) . . . . ?
C20 C2 C3 C4 -179.70(10) . . . . ?
C20 C2 C7 C6 -179.62(10) . . . . ?
C20 C2 C7 C8 2.90(17) . . . . ?
C20 C17 C18 O2 163.71(9) . . . . ?
C20 C17 C18 O3 -14.74(16) . . . . ?
O1 C16 C17 C13 -171.09(11) . . . . ?
O1 C16 C17 C18 69.12(13) . . . . ?
O1 C16 C17 C20 -49.13(14) . . . . ?
O3 C18 O2 C19 0.27(17) . . . . ?
O4 C1 O5 C4 4.27(13) . . . . ?
O4 C5 C6 C7 179.95(11) . . . . ?
O5 C1 O4 C5 -4.76(13) . . . . ?
O5 C4 C5 C6 179.19(11) . . . . ?
O5 C4 C5 O4 -0.81(14) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP89
_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 1.685
_oxdiff_exptl_absorpt_empirical_full_min 0.652
####################################################################### 
# 
# 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_2024sot0017_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2334954'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-02-23 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O6, C0.5 H0.98 Cl'
_chemical_formula_sum            'C20.50 H16.98 Cl O6'
_chemical_formula_weight         394.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H18O6
_chemical_oxdiff_usercomment     MEP283
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.9727(3)
_cell_length_b                   8.12080(10)
_cell_length_c                   20.9626(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.6850(10)
_cell_angle_gamma                90
_cell_volume                     3508.34(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21711
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.8320
_cell_measurement_theta_min      4.2480
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0176
5 -5 -2 0.0506
-5 2 -1 0.0319
0 0 1 0.0407
3 1 -5 0.0616
-5 -1 1 0.0805
-2 0 -5 0.1020

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0034 0.9989 0.9986 0.0230 -0.1905 -0.0685
4.9773 -4.9946 -1.9904 -0.0593 1.0100 -0.1203
-4.9873 1.9980 -1.0055 -0.0096 -0.4386 0.3259
-0.0006 0.0004 0.9999 -0.0481 -0.0154 -0.0551
3.0045 0.9957 -4.9986 0.4319 -0.0359 0.0837
-5.0004 -0.9967 0.9979 -0.3193 0.0559 0.2559
-1.9954 -0.0014 -5.0006 0.1607 0.0354 0.3947

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31217
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.664
_diffrn_reflns_theta_min         4.291
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00  91.00   0.50    1.00    --   50.60-126.00-106.00  160
  2  ω    -93.00 -17.00   0.50    1.00    --  -52.60 126.00 -29.00  152
  3  ω   -100.00 -17.00   0.50    1.00    --  -74.99 126.00 -29.00  166
  4  ω   -140.00 -93.00   0.50    1.00    --  -74.99-126.00-106.00   94
  5  ω     26.00 100.00   0.50    1.00    --   90.92-126.00-106.00  148
  6  ω     88.00 156.00   0.50    1.00    --   90.92 126.00 -29.00  136
  7  ω     19.00  45.00   0.50    1.00    --   22.00  65.00 157.08   52
  8  ω    -17.00  41.00   0.50    1.00    --   50.60 -57.00 -90.00  116
  9  ω    -20.00  15.00   0.50    1.00    --   50.60 -38.00 -30.00   70
 10  ω    -17.00  41.00   0.50    1.00    --   50.60 -57.00  60.00  116
 11  ω    -23.00  19.00   0.50    1.00    --  -52.60  38.00 150.00   84
 12  ω    -61.00   9.00   0.50    1.00    --  -52.60  77.00 -90.00  140
 13  ω    -23.00  19.00   0.50    1.00    --  -52.60  38.00-150.00   84
 14  ω    -23.00  19.00   0.50    1.00    --  -52.60  38.00  90.00   84
 15  ω    -33.00  -5.00   0.50    1.00    --  -74.99  45.00-150.00   56
 16  ω   -146.00 -75.00   0.50    1.00    --  -74.99 -30.00  60.00  142
 17  ω    -33.00  -5.00   0.50    1.00    --  -74.99  45.00 -30.00   56
 18  ω    -93.00 -22.00   0.50    1.00    --  -82.00  98.00 108.73  142
 19  ω    -92.00 -21.00   0.50    1.00    --  -82.00 100.00-109.29  142
 20  ω    -93.00 -20.00   0.50    1.00    --  -82.00  91.00  33.91  146
 21  ω    -97.00 -20.00   0.50    1.00    --  -82.00 114.00 -46.58  154
 22  ω    -92.00 -20.00   0.50    1.00    --  -82.00  93.00 -34.48  144
 23  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00 -60.00  124
 24  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00 150.00  124
 25  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00 150.00  124
 26  ω     84.00 132.00   0.50    1.00    --   90.92  15.00  30.00   96
 27  ω     38.00  92.00   0.50    1.00    --   90.92 -95.00  60.00  108
 28  ω    105.00 160.00   0.50    1.00    --   90.92  45.00 -60.00  110
 29  ω     64.00  92.00   0.50    1.00    --   90.92 -95.00-120.00   56
 30  ω     30.00  59.00   0.50    1.00    --   90.92 -95.00-120.00   58
 31  ω     66.00  92.00   0.50    1.00    --   90.92 -95.00 -90.00   52
 32  ω     30.00  88.00   0.50    1.00    --   90.92 -95.00  30.00  116
 33  ω     99.00 124.00   0.50    1.00    --   90.92  77.00  90.00   50
 34  ω     31.00  92.00   0.50    1.00    --   90.92 -95.00-180.00  122
 35  ω     32.00  61.00   0.50    1.00    --   90.92 -95.00 -90.00   58
 36  ω     31.00  63.00   0.50    1.00    --   90.92 -77.00 -30.00   64
 37  ω     58.00  84.00   0.50    1.00    --   90.92 -95.00 -30.00   52
 38  ω     96.00 142.00   0.50    1.00    --   90.92  45.00-120.00   92
 39  ω     30.00  56.00   0.50    1.00    --   90.92 -95.00 -30.00   52
 40  ω    108.00 150.00   0.50    1.00    --   90.92  77.00  30.00   84
 41  ω     37.00  89.00   0.50    1.00    --   90.92 -95.00 120.00  104
 42  ω     85.00 129.00   0.50    1.00    --   90.92  15.00  90.00   88
 43  ω     44.00  91.00   0.50    1.00    --   90.92 -95.00  90.00   94
 44  ω     30.00  55.00   0.50    1.00    --   90.92 -77.00 -90.00   50
 45  ω     30.00  55.00   0.50    1.00    --   90.92 -77.00  30.00   50
 46  ω     89.00 115.00   0.50    1.00    --   90.92  15.00   0.00   52
 47  ω     99.00 124.00   0.50    1.00    --   90.92  77.00 120.00   50
 48  ω     99.00 151.00   0.50    1.00    --   90.92  77.00  60.00  104
 49  ω     41.00  92.00   0.50    1.00    --   98.00 -99.00   7.54  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0400859000
_diffrn_orient_matrix_UB_12      0.0710056000
_diffrn_orient_matrix_UB_13      -0.0481564000
_diffrn_orient_matrix_UB_21      0.0207329000
_diffrn_orient_matrix_UB_22      -0.1754606000
_diffrn_orient_matrix_UB_23      -0.0153050000
_diffrn_orient_matrix_UB_31      -0.0595403000
_diffrn_orient_matrix_UB_32      -0.0132646000
_diffrn_orient_matrix_UB_33      -0.0551699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3137
_reflns_number_total             3327
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     240
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0332
_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)+(0.0391P)²+3.9881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0849
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1A-C21 = Cl1B-C21
 1.7 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H21A)=Sof(H21B)=Sof(Cl1B)=1-FVAR(1)
 Sof(Cl1A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C18(H18A,H18B), C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C12(H12), C15(H15)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64032(4) 0.43387(12) 0.29224(4) 0.0222(2) Uani 1 1 d . . . . .
O2 O 0.55637(4) 0.27360(12) 0.31647(4) 0.0223(2) Uani 1 1 d . . . . .
O3 O 0.47602(4) 0.07021(11) 0.58007(5) 0.0210(2) Uani 1 1 d . . . . .
O4 O 0.68370(4) 0.76790(11) 0.61016(5) 0.0217(2) Uani 1 1 d . . . . .
O5 O 0.70171(4) 0.36648(12) 0.69012(4) 0.0207(2) Uani 1 1 d . . . . .
O6 O 0.79503(4) 0.43570(12) 0.65872(5) 0.0240(2) Uani 1 1 d . . . . .
C1 C 0.64541(6) 0.42295(16) 0.35846(6) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.58890(7) 0.3248(2) 0.26510(7) 0.0326(4) Uani 1 1 d . . . . .
H2A H 0.606614 0.227771 0.245689 0.039 Uiso 1 1 calc R U . . .
H2B H 0.558044 0.381684 0.230666 0.039 Uiso 1 1 calc R U . . .
C3 C 0.59538(6) 0.32656(16) 0.37313(6) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.58788(6) 0.29590(15) 0.43572(6) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.553502 0.230139 0.445552 0.019 Uiso 1 1 calc R U . . .
C5 C 0.63459(6) 0.36858(15) 0.48417(6) 0.0151(3) Uani 1 1 d . . . . .
C6 C 0.68574(6) 0.46084(15) 0.46980(6) 0.0157(3) Uani 1 1 d . . . . .
C7 C 0.69190(6) 0.49383(16) 0.40520(6) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.725785 0.560320 0.394727 0.021 Uiso 1 1 calc R U . . .
C8 C 0.63676(6) 0.35510(15) 0.55770(6) 0.0149(3) Uani 1 1 d . . . . .
C9 C 0.64088(6) 0.17581(15) 0.57599(6) 0.0163(3) Uani 1 1 d . . . . .
H9 H 0.681678 0.121376 0.583277 0.020 Uiso 1 1 calc R U . . .
C10 C 0.58728(6) 0.09292(16) 0.58203(6) 0.0177(3) Uani 1 1 d . . . . .
H10 H 0.589852 -0.022355 0.589784 0.021 Uiso 1 1 calc R U . . .
C11 C 0.52480(6) 0.17625(16) 0.57692(6) 0.0168(3) Uani 1 1 d . . . . .
C12 C 0.51917(6) 0.34302(15) 0.57343(6) 0.0167(3) Uani 1 1 d . . . . .
H12 H 0.478130 0.395400 0.569551 0.020 Uiso 1 1 calc R U . . .
C13 C 0.57717(6) 0.43629(15) 0.57581(6) 0.0154(3) Uani 1 1 d . . . . .
C14 C 0.41184(6) 0.13846(17) 0.57554(7) 0.0241(3) Uani 1 1 d . . . . .
H14A H 0.398697 0.192208 0.533293 0.036 Uiso 1 1 calc R U . . .
H14B H 0.412049 0.219471 0.610230 0.036 Uiso 1 1 calc R U . . .
H14C H 0.381168 0.050055 0.580027 0.036 Uiso 1 1 calc R U . . .
C15 C 0.58894(6) 0.59575(16) 0.59330(6) 0.0172(3) Uani 1 1 d . . . . .
H15 H 0.556821 0.671553 0.601287 0.021 Uiso 1 1 calc R U . . .
C16 C 0.65664(6) 0.63476(15) 0.59813(6) 0.0163(3) Uani 1 1 d . . . . .
C17 C 0.69371(6) 0.47550(15) 0.58461(6) 0.0156(3) Uani 1 1 d . . . . .
C18 C 0.73273(6) 0.50760(16) 0.53059(6) 0.0176(3) Uani 1 1 d . . . . .
H18A H 0.745441 0.624845 0.529593 0.021 Uiso 1 1 calc R U . . .
H18B H 0.772206 0.438266 0.536361 0.021 Uiso 1 1 calc R U . . .
C19 C 0.73680(6) 0.42331(15) 0.64783(6) 0.0167(3) Uani 1 1 d . . . . .
C20 C 0.73873(7) 0.31321(18) 0.75217(6) 0.0230(3) Uani 1 1 d . . . . .
H20A H 0.768341 0.224472 0.745166 0.035 Uiso 1 1 calc R U . . .
H20B H 0.709001 0.273041 0.779663 0.035 Uiso 1 1 calc R U . . .
H20C H 0.763824 0.406143 0.773575 0.035 Uiso 1 1 calc R U . . .
C21 C 0.500000 0.0888(3) 0.750000 0.0386(6) Uani 1 2 d DS T P . .
H21A H 0.508065 0.019994 0.789660 0.046 Uiso 0.490(6) 1 calc R U P A 1
H21B H 0.491935 0.019988 0.710342 0.046 Uiso 0.490(6) 1 calc R U P A 1
Cl1B Cl 0.56060(11) 0.2528(4) 0.74886(6) 0.0428(7) Uani 0.490(6) 1 d D . P A 1
Cl1A Cl 0.57149(5) 0.1614(6) 0.74335(5) 0.0499(7) Uani 0.510(6) 1 d D . 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
O1 C1 1.3752(15) . ?
O1 C2 1.4297(17) . ?
O2 C2 1.4389(17) . ?
O2 C3 1.3801(15) . ?
O3 C11 1.3482(15) . ?
O3 C14 1.4425(15) . ?
O4 C16 1.2255(16) . ?
O5 C19 1.3349(16) . ?
O5 C20 1.4517(15) . ?
O6 C19 1.2043(16) . ?
C1 C3 1.3886(18) . ?
C1 C7 1.3739(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3729(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.4037(17) . ?
C5 C6 1.3866(18) . ?
C5 C8 1.5375(16) . ?
C6 C7 1.4097(17) . ?
C6 C18 1.5078(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.5040(17) . ?
C8 C13 1.5220(17) . ?
C8 C17 1.5655(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3361(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.4609(18) . ?
C11 C12 1.3603(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.4260(17) . ?
C13 C15 1.3559(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.4399(18) . ?
C16 C17 1.5618(17) . ?
C17 C18 1.5374(17) . ?
C17 C19 1.5195(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 Cl1B 1.844(2) . ?
C21 Cl1B 1.844(2) 2_656 ?
C21 Cl1A 1.6408(18) . ?
C21 Cl1A 1.6408(18) 2_656 ?

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 C2 105.87(10) . . ?
C3 O2 C2 105.45(10) . . ?
C11 O3 C14 117.30(10) . . ?
C19 O5 C20 115.40(10) . . ?
O1 C1 C3 109.84(11) . . ?
C7 C1 O1 127.21(12) . . ?
C7 C1 C3 122.95(12) . . ?
O1 C2 O2 107.96(11) . . ?
O1 C2 H2A 110.1 . . ?
O1 C2 H2B 110.1 . . ?
O2 C2 H2A 110.1 . . ?
O2 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O2 C3 C1 109.68(11) . . ?
C4 C3 O2 127.69(12) . . ?
C4 C3 C1 122.62(12) . . ?
C3 C4 H4 122.4 . . ?
C3 C4 C5 115.27(11) . . ?
C5 C4 H4 122.4 . . ?
C4 C5 C8 125.62(11) . . ?
C6 C5 C4 122.30(11) . . ?
C6 C5 C8 112.08(10) . . ?
C5 C6 C7 121.59(11) . . ?
C5 C6 C18 111.30(11) . . ?
C7 C6 C18 127.01(11) . . ?
C1 C7 C6 115.21(11) . . ?
C1 C7 H7 122.4 . . ?
C6 C7 H7 122.4 . . ?
C5 C8 C17 101.28(10) . . ?
C9 C8 C5 108.31(10) . . ?
C9 C8 C13 111.51(10) . . ?
C9 C8 C17 120.59(10) . . ?
C13 C8 C5 110.25(10) . . ?
C13 C8 C17 104.26(10) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.15(11) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.24(12) . . ?
C11 C10 H10 119.4 . . ?
O3 C11 C10 112.27(11) . . ?
O3 C11 C12 125.41(12) . . ?
C12 C11 C10 122.20(12) . . ?
C11 C12 H12 121.2 . . ?
C11 C12 C13 117.51(12) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 C8 119.72(11) . . ?
C15 C13 C8 111.38(11) . . ?
C15 C13 C12 128.90(12) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15 124.5 . . ?
C13 C15 C16 110.90(11) . . ?
C16 C15 H15 124.5 . . ?
O4 C16 C15 128.45(12) . . ?
O4 C16 C17 122.73(11) . . ?
C15 C16 C17 108.82(10) . . ?
C16 C17 C8 102.15(10) . . ?
C18 C17 C8 108.37(10) . . ?
C18 C17 C16 110.13(10) . . ?
C19 C17 C8 115.51(10) . . ?
C19 C17 C16 107.95(10) . . ?
C19 C17 C18 112.21(10) . . ?
C6 C18 C17 103.06(10) . . ?
C6 C18 H18A 111.2 . . ?
C6 C18 H18B 111.2 . . ?
C17 C18 H18A 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
O5 C19 C17 111.33(10) . . ?
O6 C19 O5 124.58(12) . . ?
O6 C19 C17 124.07(12) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H21A C21 H21B 111.2 . . ?
Cl1B C21 H21A 114.1 2_656 . ?
Cl1B C21 H21A 114.1 . . ?
Cl1B C21 H21B 114.1 2_656 . ?
Cl1B C21 H21B 114.1 . . ?
Cl1B C21 Cl1B 87.5(3) . 2_656 ?
Cl1A C21 Cl1A 137.9(3) 2_656 . ?

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
O1 C1 C3 O2 -0.39(15) . . . . ?
O1 C1 C3 C4 -179.26(11) . . . . ?
O1 C1 C7 C6 -179.42(12) . . . . ?
O2 C3 C4 C5 -178.83(12) . . . . ?
O3 C11 C12 C13 174.95(11) . . . . ?
O4 C16 C17 C8 -168.12(11) . . . . ?
O4 C16 C17 C18 -53.14(15) . . . . ?
O4 C16 C17 C19 69.68(15) . . . . ?
C1 O1 C2 O2 10.53(16) . . . . ?
C1 C3 C4 C5 -0.18(18) . . . . ?
C2 O1 C1 C3 -6.34(15) . . . . ?
C2 O1 C1 C7 173.59(14) . . . . ?
C2 O2 C3 C1 6.89(15) . . . . ?
C2 O2 C3 C4 -174.32(14) . . . . ?
C3 O2 C2 O1 -10.73(16) . . . . ?
C3 C1 C7 C6 0.50(19) . . . . ?
C3 C4 C5 C6 -1.79(18) . . . . ?
C3 C4 C5 C8 179.28(11) . . . . ?
C4 C5 C6 C7 3.22(19) . . . . ?
C4 C5 C6 C18 -173.39(11) . . . . ?
C4 C5 C8 C9 58.25(15) . . . . ?
C4 C5 C8 C13 -64.02(15) . . . . ?
C4 C5 C8 C17 -173.98(12) . . . . ?
C5 C6 C7 C1 -2.44(18) . . . . ?
C5 C6 C18 C17 -15.95(14) . . . . ?
C5 C8 C9 C10 -97.27(13) . . . . ?
C5 C8 C13 C12 87.51(13) . . . . ?
C5 C8 C13 C15 -93.08(12) . . . . ?
C5 C8 C17 C16 99.52(10) . . . . ?
C5 C8 C17 C18 -16.73(12) . . . . ?
C5 C8 C17 C19 -143.60(10) . . . . ?
C6 C5 C8 C9 -120.78(11) . . . . ?
C6 C5 C8 C13 116.95(12) . . . . ?
C6 C5 C8 C17 6.99(13) . . . . ?
C7 C1 C3 O2 179.68(11) . . . . ?
C7 C1 C3 C4 0.8(2) . . . . ?
C7 C6 C18 C17 167.66(12) . . . . ?
C8 C5 C6 C7 -177.71(11) . . . . ?
C8 C5 C6 C18 5.67(14) . . . . ?
C8 C9 C10 C11 -5.58(18) . . . . ?
C8 C13 C15 C16 -7.88(14) . . . . ?
C8 C17 C18 C6 20.04(13) . . . . ?
C8 C17 C19 O5 -43.38(14) . . . . ?
C8 C17 C19 O6 138.31(13) . . . . ?
C9 C8 C13 C12 -32.85(15) . . . . ?
C9 C8 C13 C15 146.56(11) . . . . ?
C9 C8 C17 C16 -141.13(11) . . . . ?
C9 C8 C17 C18 102.61(13) . . . . ?
C9 C8 C17 C19 -24.25(16) . . . . ?
C9 C10 C11 O3 175.90(11) . . . . ?
C9 C10 C11 C12 -7.81(19) . . . . ?
C10 C11 C12 C13 -0.83(18) . . . . ?
C11 C12 C13 C8 22.03(17) . . . . ?
C11 C12 C13 C15 -157.26(13) . . . . ?
C12 C13 C15 C16 171.46(12) . . . . ?
C13 C8 C9 C10 24.22(16) . . . . ?
C13 C8 C17 C16 -14.99(12) . . . . ?
C13 C8 C17 C18 -131.25(10) . . . . ?
C13 C8 C17 C19 101.89(11) . . . . ?
C13 C15 C16 O4 176.76(12) . . . . ?
C13 C15 C16 C17 -2.72(14) . . . . ?
C14 O3 C11 C10 -179.99(11) . . . . ?
C14 O3 C11 C12 3.86(18) . . . . ?
C15 C16 C17 C8 11.39(12) . . . . ?
C15 C16 C17 C18 126.37(11) . . . . ?
C15 C16 C17 C19 -110.81(11) . . . . ?
C16 C17 C18 C6 -90.93(11) . . . . ?
C16 C17 C19 O5 70.17(13) . . . . ?
C16 C17 C19 O6 -108.13(14) . . . . ?
C17 C8 C9 C10 146.95(12) . . . . ?
C17 C8 C13 C12 -164.49(10) . . . . ?
C17 C8 C13 C15 14.91(13) . . . . ?
C18 C6 C7 C1 173.60(12) . . . . ?
C18 C17 C19 O5 -168.29(10) . . . . ?
C18 C17 C19 O6 13.41(18) . . . . ?
C19 C17 C18 C6 148.79(10) . . . . ?
C20 O5 C19 O6 -1.78(18) . . . . ?
C20 O5 C19 C17 179.92(10) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP283
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.811
####################################################################### 
# 
# 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_2024sot0014_r1_100k
_database_code_depnum_ccdc_archive 'CCDC 2339968'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-03-13
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H14 O5'
_chemical_formula_sum            'C19 H14 O5'
_chemical_formula_weight         322.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H14O5
_chemical_oxdiff_usercomment     MEP87
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'

_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'

_cell_length_a                   8.36270(10)
_cell_length_b                   10.98390(10)
_cell_length_c                   16.0035(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5250(10)
_cell_angle_gamma                90.00
_cell_volume                     1457.34(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20406
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.0040
_cell_measurement_theta_min      4.0550
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (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_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 -1 0.0315
-5 1 1 0.0315
0 2 5 0.0946
0 -2 -5 0.0946
0 1 -1 0.0447
0 -3 5 0.0675
-1 -5 -4 0.0755

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
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
4.9963 -1.0001 -0.9986 -0.4561 -0.8108 -0.0354
-4.9963 1.0001 0.9986 0.4561 0.8108 0.0354
0.0007 1.9985 4.9949 0.0310 0.0403 -0.5582
-0.0007 -1.9985 -4.9949 -0.0310 -0.0403 0.5582
0.0002 0.9990 -0.9992 -0.1354 0.1025 0.0139
-0.0004 -2.9968 4.9958 0.4924 -0.3546 -0.2091
-1.0007 -4.9954 -3.9954 0.3899 -0.1496 0.7218

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26744
_diffrn_reflns_theta_full        70.17
_diffrn_reflns_theta_max         70.17
_diffrn_reflns_theta_min         4.90
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  63.00   0.50    1.00    --   50.60 -82.00  78.00  146
  2  ω    -64.00   9.00   0.50    1.00    --  -52.60  82.00-159.00  146
  3  ω    -87.00 -13.00   0.50    1.00    --  -74.99  82.00-159.00  148
  4  ω     30.00  80.00   0.50    1.00    --   90.92 -82.00  78.00  100
  5  ω    100.00 152.00   0.50    1.00    --   90.92  82.00-159.00  104
  6  ω     12.00  51.00   0.50    1.00    --   14.00  62.00   5.19   78
  7  ω     28.00  56.00   0.50    1.00    --   30.00  61.00  36.20   56
  8  ω    -20.00  15.00   0.50    1.00    --   50.60 -38.00 150.00   70
  9  ω     53.00 121.00   0.50    1.00    --   50.60  38.00 150.00  136
 10  ω    -20.00  15.00   0.50    1.00    --   50.60 -38.00-180.00   70
 11  ω    -23.00  19.00   0.50    1.00    --  -52.60  38.00   0.00   84
 12  ω   -124.00 -55.00   0.50    1.00    --  -52.60 -38.00 -30.00  138
 13  ω    -33.00  -5.00   0.50    1.00    --  -74.99  45.00 -60.00   56
 14  ω   -142.00 -86.00   0.50    1.00    --  -74.99 -61.00 150.00  112
 15  ω   -140.00 -68.00   0.50    1.00    --  -74.99 -15.00 -90.00  144
 16  ω    -33.00  -5.00   0.50    1.00    --  -74.99  45.00 -90.00   56
 17  ω    -33.00  -5.00   0.50    1.00    --  -74.99  45.00 150.00   56
 18  ω   -140.00 -68.00   0.50    1.00    --  -74.99 -15.00 -90.00  144
 19  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00   0.00  124
 20  ω     30.00  71.00   0.50    1.00    --   90.92 -77.00 -90.00   82
 21  ω     27.00 100.00   0.50    1.00    --   90.92-125.00 150.00  146
 22  ω     99.00 152.00   0.50    1.00    --   90.92  77.00 -90.00  106
 23  ω     88.00 155.00   0.50    1.00    --   90.92 125.00 -30.00  134
 24  ω     88.00 158.00   0.50    1.00    --   90.92  61.00 120.00  140
 25  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00 150.00  124
 26  ω     99.00 152.00   0.50    1.00    --   90.92  77.00 -30.00  106
 27  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00  60.00  124
 28  ω     88.00 158.00   0.50    1.00    --   90.92  61.00 150.00  140
 29  ω     30.00  71.00   0.50    1.00    --   90.92 -77.00 150.00   82
 30  ω     30.00  71.00   0.50    1.00    --   90.92 -77.00  30.00   82
 31  ω     99.00 152.00   0.50    1.00    --   90.92  77.00-180.00  106
 32  ω     93.00 161.00   0.50    1.00    --   90.92  45.00 -30.00  136
 33  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00-150.00  124
 34  ω     88.00 155.00   0.50    1.00    --   90.92 125.00-150.00  134
 35  ω     84.00 132.00   0.50    1.00    --   90.92  15.00 -60.00   96
 36  ω     30.00  71.00   0.50    1.00    --   90.92 -77.00   0.00   82
 37  ω     30.00  71.00   0.50    1.00    --   90.92 -77.00 -60.00   82
 38  ω     88.00 155.00   0.50    1.00    --   90.92 125.00 -90.00  134
 39  ω     84.00 132.00   0.50    1.00    --   90.92  15.00 150.00   96
 40  ω     30.00  92.00   0.50    1.00    --   90.92 -95.00 120.00  124
 41  ω     93.00 161.00   0.50    1.00    --   90.92  45.00-180.00  136
 42  ω     93.00 161.00   0.50    1.00    --   90.92  45.00 150.00  136
 43  ω     84.00 132.00   0.50    1.00    --   90.92  15.00  30.00   96
 44  ω     24.00  51.00   0.50    1.00    --   26.00  62.00-110.52   54
 45  ω     28.00  56.00   0.50    1.00    --   30.00  60.00 102.62   56
 46  ω     51.00 117.00   0.50    1.00    --   50.60  50.00  65.71  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1011306000
_diffrn_orient_matrix_UB_12      -0.0923237000
_diffrn_orient_matrix_UB_13      0.0431683000
_diffrn_orient_matrix_UB_21      -0.1511672000
_diffrn_orient_matrix_UB_22      0.0790675000
_diffrn_orient_matrix_UB_23      -0.0235542000
_diffrn_orient_matrix_UB_31      -0.0378272000
_diffrn_orient_matrix_UB_32      -0.0698985000
_diffrn_orient_matrix_UB_33      -0.0837893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2650
_reflns_number_total             2766
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.109a 64-bit (release 21-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-1997 97-2 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.6606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0801
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62859(15) 0.80648(11) 0.61432(8) 0.0259(3) Uani 1 1 d . . .
H1A H 0.6722 0.8519 0.6657 0.031 Uiso 1 1 calc R . .
H1B H 0.5240 0.8432 0.5912 0.031 Uiso 1 1 calc R . .
C2 C 0.81843(12) 0.52893(10) 0.44076(6) 0.0146(2) Uani 1 1 d . . .
C3 C 0.82353(13) 0.65451(10) 0.45740(7) 0.0168(2) Uani 1 1 d . . .
H3 H 0.8762 0.7093 0.4240 0.020 Uiso 1 1 calc R . .
C4 C 0.74932(13) 0.69505(10) 0.52390(7) 0.0175(2) Uani 1 1 d . . .
C5 C 0.67145(12) 0.61661(10) 0.57294(6) 0.0165(2) Uani 1 1 d . . .
C6 C 0.66768(12) 0.49346(10) 0.56003(6) 0.0155(2) Uani 1 1 d . . .
H6 H 0.6159 0.4403 0.5949 0.019 Uiso 1 1 calc R . .
C7 C 0.74416(12) 0.44880(10) 0.49264(6) 0.0143(2) Uani 1 1 d . . .
C8 C 0.75609(12) 0.31677(10) 0.47781(7) 0.0150(2) Uani 1 1 d . . .
C9 C 0.74779(14) 0.22688(10) 0.53885(7) 0.0190(2) Uani 1 1 d . . .
H9 H 0.7211 0.2487 0.5928 0.023 Uiso 1 1 calc R . .
C10 C 0.77831(15) 0.10540(11) 0.52126(7) 0.0234(3) Uani 1 1 d . . .
H10 H 0.7684 0.0453 0.5630 0.028 Uiso 1 1 calc R . .
C11 C 0.82299(14) 0.07005(11) 0.44390(8) 0.0233(3) Uani 1 1 d . . .
H11 H 0.8464 -0.0127 0.4331 0.028 Uiso 1 1 calc R . .
C12 C 0.83241(13) 0.15908(11) 0.38283(7) 0.0198(2) Uani 1 1 d . . .
C13 C 0.79348(12) 0.27846(10) 0.39971(7) 0.0158(2) Uani 1 1 d . . .
C14 C 0.89647(15) 0.15099(11) 0.29929(7) 0.0248(3) Uani 1 1 d . . .
H14A H 0.8178 0.1110 0.2563 0.030 Uiso 1 1 calc R . .
H14B H 0.9996 0.1056 0.3045 0.030 Uiso 1 1 calc R . .
C15 C 0.92085(14) 0.28474(11) 0.27711(7) 0.0212(3) Uani 1 1 d . . .
C16 C 0.81882(13) 0.36589(10) 0.33003(6) 0.0164(2) Uani 1 1 d . . .
C17 C 0.66117(13) 0.39781(10) 0.27392(6) 0.0182(2) Uani 1 1 d . . .
C18 C 0.44658(15) 0.31664(13) 0.17922(8) 0.0300(3) Uani 1 1 d . . .
H18A H 0.4645 0.3697 0.1321 0.045 Uiso 1 1 calc R . .
H18B H 0.3679 0.3545 0.2114 0.045 Uiso 1 1 calc R . .
H18C H 0.4053 0.2378 0.1574 0.045 Uiso 1 1 calc R . .
C19 C 0.90066(13) 0.48129(10) 0.36796(7) 0.0167(2) Uani 1 1 d . . .
H19A H 1.0152 0.4635 0.3883 0.020 Uiso 1 1 calc R . .
H19B H 0.8973 0.5447 0.3238 0.020 Uiso 1 1 calc R . .
O1 O 1.00798(11) 0.32316(9) 0.22890(5) 0.0305(2) Uani 1 1 d . . .
O2 O 0.59767(9) 0.29880(8) 0.23363(5) 0.0228(2) Uani 1 1 d . . .
O3 O 0.60452(10) 0.49836(8) 0.26524(5) 0.0276(2) Uani 1 1 d . . .
O4 O 0.60705(10) 0.68101(7) 0.63412(5) 0.02253(19) Uani 1 1 d . . .
O5 O 0.73941(11) 0.81245(7) 0.55303(5) 0.0255(2) 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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 O4 1.4307(14) . ?
C1 O5 1.4365(15) . ?
C2 C3 1.4045(15) . ?
C2 C7 1.4089(15) . ?
C2 C19 1.5211(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3745(16) . ?
C4 C5 1.3842(16) . ?
C4 O5 1.3773(13) . ?
C5 C6 1.3681(16) . ?
C5 O4 1.3738(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.4119(15) . ?
C7 C8 1.4749(14) . ?
C8 C9 1.3971(15) . ?
C8 C13 1.3926(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3942(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3944(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3920(17) . ?
C12 C13 1.3862(16) . ?
C12 C14 1.5066(16) . ?
C13 C16 1.5075(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5313(17) . ?
C15 C16 1.5584(15) . ?
C15 O1 1.2048(15) . ?
C16 C17 1.5354(15) . ?
C16 C19 1.5280(15) . ?
C17 O2 1.3382(14) . ?
C17 O3 1.2025(15) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 O2 1.4508(14) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.5 . . ?
O4 C1 H1A 110.1 . . ?
O4 C1 H1B 110.1 . . ?
O4 C1 O5 107.84(9) . . ?
O5 C1 H1A 110.1 . . ?
O5 C1 H1B 110.1 . . ?
C3 C2 C7 120.44(10) . . ?
C3 C2 C19 118.52(9) . . ?
C7 C2 C19 120.99(10) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 C2 117.35(10) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C5 122.07(10) . . ?
C3 C4 O5 128.22(10) . . ?
O5 C4 C5 109.71(10) . . ?
C6 C5 C4 122.22(10) . . ?
C6 C5 O4 127.83(10) . . ?
O4 C5 C4 109.93(10) . . ?
C5 C6 H6 121.5 . . ?
C5 C6 C7 117.07(10) . . ?
C7 C6 H6 121.5 . . ?
C2 C7 C6 120.79(10) . . ?
C2 C7 C8 118.36(9) . . ?
C6 C7 C8 120.76(10) . . ?
C9 C8 C7 124.87(10) . . ?
C13 C8 C7 118.00(9) . . ?
C13 C8 C9 116.84(10) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.53(10) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.55(11) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.31(11) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C14 129.86(11) . . ?
C13 C12 C11 119.43(10) . . ?
C13 C12 C14 110.41(10) . . ?
C8 C13 C16 122.77(10) . . ?
C12 C13 C8 123.15(10) . . ?
C12 C13 C16 113.52(9) . . ?
C12 C14 H14A 111.2 . . ?
C12 C14 H14B 111.2 . . ?
C12 C14 C15 102.87(9) . . ?
H14A C14 H14B 109.1 . . ?
C15 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C14 C15 C16 108.89(9) . . ?
O1 C15 C14 126.48(11) . . ?
O1 C15 C16 124.59(11) . . ?
C13 C16 C15 100.23(9) . . ?
C13 C16 C17 112.64(9) . . ?
C13 C16 C19 109.49(8) . . ?
C17 C16 C15 107.58(8) . . ?
C19 C16 C15 116.21(9) . . ?
C19 C16 C17 110.40(9) . . ?
O2 C17 C16 110.63(9) . . ?
O3 C17 C16 124.92(10) . . ?
O3 C17 O2 124.42(10) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
C2 C19 C16 111.46(8) . . ?
C2 C19 H19A 109.3 . . ?
C2 C19 H19B 109.3 . . ?
C16 C19 H19A 109.3 . . ?
C16 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C17 O2 C18 116.03(10) . . ?
C5 O4 C1 105.41(8) . . ?
C4 O5 C1 105.14(9) . . ?

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
C2 C3 C4 C5 -0.30(16) . . . . ?
C2 C3 C4 O5 179.25(10) . . . . ?
C2 C7 C8 C9 153.86(10) . . . . ?
C2 C7 C8 C13 -19.75(14) . . . . ?
C3 C2 C7 C6 2.68(15) . . . . ?
C3 C2 C7 C8 -173.98(9) . . . . ?
C3 C2 C19 C16 -151.16(9) . . . . ?
C3 C4 C5 C6 2.08(17) . . . . ?
C3 C4 C5 O4 -179.44(9) . . . . ?
C3 C4 O5 C1 171.22(11) . . . . ?
C4 C5 C6 C7 -1.40(16) . . . . ?
C4 C5 O4 C1 7.79(12) . . . . ?
C5 C4 O5 C1 -9.18(12) . . . . ?
C5 C6 C7 C2 -0.94(15) . . . . ?
C5 C6 C7 C8 175.64(10) . . . . ?
C6 C5 O4 C1 -173.84(11) . . . . ?
C6 C7 C8 C9 -22.80(16) . . . . ?
C6 C7 C8 C13 163.59(9) . . . . ?
C7 C2 C3 C4 -2.01(15) . . . . ?
C7 C2 C19 C16 31.33(13) . . . . ?
C7 C8 C9 C10 -172.78(10) . . . . ?
C7 C8 C13 C12 169.68(10) . . . . ?
C7 C8 C13 C16 -1.18(15) . . . . ?
C8 C9 C10 C11 2.14(18) . . . . ?
C8 C13 C16 C15 158.07(10) . . . . ?
C8 C13 C16 C17 -87.85(12) . . . . ?
C8 C13 C16 C19 35.39(14) . . . . ?
C9 C8 C13 C12 -4.44(16) . . . . ?
C9 C8 C13 C16 -175.30(10) . . . . ?
C9 C10 C11 C12 -1.75(18) . . . . ?
C10 C11 C12 C13 -1.65(17) . . . . ?
C10 C11 C12 C14 171.38(11) . . . . ?
C11 C12 C13 C8 4.89(17) . . . . ?
C11 C12 C13 C16 176.52(10) . . . . ?
C11 C12 C14 C15 -162.96(12) . . . . ?
C12 C13 C16 C15 -13.59(12) . . . . ?
C12 C13 C16 C17 100.49(11) . . . . ?
C12 C13 C16 C19 -136.27(10) . . . . ?
C12 C14 C15 C16 -19.09(12) . . . . ?
C12 C14 C15 O1 158.71(11) . . . . ?
C13 C8 C9 C10 0.89(16) . . . . ?
C13 C12 C14 C15 10.56(12) . . . . ?
C13 C16 C17 O2 -63.73(11) . . . . ?
C13 C16 C17 O3 118.29(12) . . . . ?
C13 C16 C19 C2 -47.66(12) . . . . ?
C14 C12 C13 C8 -169.40(10) . . . . ?
C14 C12 C13 C16 2.22(13) . . . . ?
C14 C15 C16 C13 19.80(11) . . . . ?
C14 C15 C16 C17 -98.08(10) . . . . ?
C14 C15 C16 C19 137.62(10) . . . . ?
C15 C16 C17 O2 45.79(11) . . . . ?
C15 C16 C17 O3 -132.19(12) . . . . ?
C15 C16 C19 C2 -160.26(9) . . . . ?
C16 C17 O2 C18 179.19(9) . . . . ?
C17 C16 C19 C2 76.90(11) . . . . ?
C19 C2 C3 C4 -179.53(9) . . . . ?
C19 C2 C7 C6 -179.86(9) . . . . ?
C19 C2 C7 C8 3.48(14) . . . . ?
C19 C16 C17 O2 173.54(8) . . . . ?
C19 C16 C17 O3 -4.44(15) . . . . ?
O1 C15 C16 C13 -158.05(11) . . . . ?
O1 C15 C16 C17 84.07(13) . . . . ?
O1 C15 C16 C19 -40.23(15) . . . . ?
O3 C17 O2 C18 -2.82(16) . . . . ?
O4 C1 O5 C4 13.90(12) . . . . ?
O4 C5 C6 C7 -179.58(10) . . . . ?
O5 C1 O4 C5 -13.38(12) . . . . ?
O5 C4 C5 C6 -177.54(10) . . . . ?
O5 C4 C5 O4 0.93(12) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP87
_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 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.795
####################################################################### 
# 
# 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_2024sot0015_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2339960'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-03-13
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21h20O4
_chemical_oxdiff_usercomment     MEP257
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.84460(10)
_cell_length_b                   8.68530(10)
_cell_length_c                   11.0599(3)
_cell_angle_alpha                77.008(2)
_cell_angle_beta                 83.439(2)
_cell_angle_gamma                81.3120(10)
_cell_volume                     723.30(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    20856
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.9790
_cell_measurement_theta_min      4.1140
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (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_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 -1 0.0223
1 5 1 0.0223
-2 0 5 0.0594
2 0 -5 0.0594
1 0 0 0.0564
-1 0 -1 0.0467
0 0 1 0.0499
0 0 -1 0.0499

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_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
-0.9996 -4.9964 -0.9998 -0.3715 -0.8099 -0.0045
0.9996 4.9964 0.9998 0.3715 0.8099 0.0045
-1.9989 0.0003 4.9967 -0.0022 -0.0873 -0.8441
1.9989 -0.0003 -4.9967 0.0022 0.0873 0.8441
0.9994 -0.0001 0.0001 -0.1500 0.0851 0.0997
-0.9993 0.0001 -0.9995 0.2105 -0.1017 0.0292
-0.0000 0.0000 0.9994 -0.0604 0.0166 -0.1289
0.0000 -0.0000 -0.9994 0.0604 -0.0166 0.1289

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0075
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24672
_diffrn_reflns_theta_full        69.13
_diffrn_reflns_theta_max         69.13
_diffrn_reflns_theta_min         4.12
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   9.00   0.50    1.00    --   48.17 -34.00  85.00   66
  2  ω     46.00 122.00   0.50    1.00    --   48.17  34.00-116.00  152
  3  ω    -16.00  24.00   0.50    1.00    --  -49.92  34.00-116.00   80
  4  ω   -123.00 -47.00   0.50    1.00    --  -49.92 -34.00  85.00  152
  5  ω   -149.00 -73.00   0.50    1.00    --  -75.43 -34.00  85.00  152
  6  ω     89.00 164.00   0.50    1.00    --   91.36  34.00-116.00  150
  7  ω    -21.00   5.00   0.50    1.00    --    2.00  93.00-105.51   52
  8  ω      3.00  35.00   0.50    1.00    --   10.00  68.00  75.24   64
  9  ω      7.00  35.00   0.50    1.00    --   14.00  68.00  -7.81   56
 10  ω    -41.00 -15.00   0.50    1.00    --  -22.00 -68.00 -15.18   52
 11  ω    -51.00 -20.00   0.50    1.00    --  -26.00 -65.00  80.13   62
 12  ω    -56.00 -25.00   0.50    1.00    --  -30.00 -62.00 155.50   62
 13  ω    -51.00 -24.00   0.50    1.00    --  -30.00 -64.00  19.56   54
 14  ω    -62.00 -25.00   0.50    1.00    --  -30.00 -60.00-154.32   74
 15  ω    -54.00 -28.00   0.50    1.00    --  -34.00 -63.00  90.93   52
 16  ω    -62.00 -29.00   0.50    1.00    --  -34.00 -60.00 -78.68   66
 17  ω    -62.00 -30.00   0.50    1.00    --  -34.00 -57.00  46.22   64
 18  ω    -54.00 -28.00   0.50    1.00    --  -34.00 -63.00 125.03   52
 19  ω    -62.00 -33.00   0.50    1.00    --  -38.00 -59.00   1.96   58
 20  ω    -62.00 -33.00   0.50    1.00    --  -38.00 -60.00  26.94   58
 21  ω    -62.00 -33.00   0.50    1.00    --  -38.00 -58.00 179.28   58
 22  ω    -62.00 -33.00   0.50    1.00    --  -38.00 -60.00  99.47   58
 23  ω    -62.00 -34.00   0.50    1.00    --  -38.00 -57.00-109.91   56
 24  ω    -62.00 -33.00   0.50    1.00    --  -38.00 -60.00-121.28   58
 25  ω   -112.00 -39.00   0.50    1.00    --  -42.00 -52.00-157.07  146
 26  ω   -112.00 -39.00   0.50    1.00    --  -42.00 -53.00 120.98  146
 27  ω   -117.00 -44.00   0.50    1.00    --  -46.00 -47.00 -94.16  146
 28  ω   -117.00 -44.00   0.50    1.00    --  -46.00 -48.00 178.24  146
 29  ω   -116.00 -42.00   0.50    1.00    --  -46.00 -54.00 -52.41  148
 30  ω    -91.00 -16.00   0.50    1.00    --  -49.92 125.00 -60.00  150
 31  ω   -120.00 -47.00   0.50    1.00    --  -49.92 -53.00-130.74  146
 32  ω   -120.00 -47.00   0.50    1.00    --  -50.00 -52.00 -34.99  146
 33  ω   -128.00 -55.00   0.50    1.00    --  -58.00 -53.00  99.18  146
 34  ω   -128.00 -55.00   0.50    1.00    --  -58.00 -53.00 156.60  146
 35  ω   -128.00 -55.00   0.50    1.00    --  -58.00 -53.00-110.32  146
 36  ω   -129.00 -55.00   0.50    1.00    --  -58.00 -50.00 -63.58  148
 37  ω   -129.00 -55.00   0.50    1.00    --  -58.00 -49.00  66.29  148
 38  ω   -129.00 -56.00   0.50    1.00    --  -58.00 -48.00  -1.94  146
 39  ω   -132.00 -58.00   0.50    1.00    --  -62.00 -54.00  -2.86  148
 40  ω   -133.00 -59.00   0.50    1.00    --  -62.00 -50.00-143.98  148
 41  ω   -133.00 -59.00   0.50    1.00    --  -62.00 -50.00  45.35  148
 42  ω   -132.00 -58.00   0.50    1.00    --  -62.00 -54.00 -84.71  148
 43  ω   -133.00 -59.00   0.50    1.00    --  -62.00 -52.00  28.76  148
 44  ω   -132.00 -59.00   0.50    1.00    --  -62.00 -53.00 119.87  146
 45  ω   -137.00 -63.00   0.50    1.00    --  -66.00 -51.00 168.44  148
 46  ω   -137.00 -63.00   0.50    1.00    --  -66.00 -52.00-174.34  148
 47  ω   -137.00 -64.00   0.50    1.00    --  -66.00 -48.00  -9.01  146
 48  ω   -141.00 -68.00   0.50    1.00    --  -70.00 -48.00-147.56  146
 49  ω   -140.00 -66.00   0.50    1.00    --  -70.00 -53.00-156.98  148
 50  ω   -140.00 -66.00   0.50    1.00    --  -70.00 -54.00  -9.64  148
 51  ω    -91.00 -66.00   0.50    1.00    --  -70.00 -54.00 -86.61   50
 52  ω   -100.00 -71.00   0.50    1.00    --  -74.00 -49.00 133.13   58
 53  ω   -137.00 -96.00   0.50    1.00    --  -75.43-125.00  30.00   82
 54  ω    -32.00  -4.00   0.50    1.00    --  -75.43  45.00  60.00   56
 55  ω    -31.00  -6.00   0.50    1.00    --  -75.43  45.00  90.00   50
 56  ω   -100.00 -75.00   0.50    1.00    --  -78.00 -50.00 -35.75   50
 57  ω   -108.00 -83.00   0.50    1.00    --  -82.00 -52.00  68.14   50
 58  ω    -86.00 -33.00   0.50    1.00    --  -82.00  90.00 111.50  106
 59  ω   -103.00 -78.00   0.50    1.00    --  -82.00 -54.00  43.91   50
 60  ω   -104.00 -79.00   0.50    1.00    --  -82.00 -51.00 -24.29   50
 61  ω   -145.00-119.00   0.50    1.00    --  -82.00 -51.00 -24.29   52
 62  ω   -104.00 -79.00   0.50    1.00    --  -82.00 -51.00 155.79   50
 63  ω   -153.00-124.00   0.50    1.00    --  -82.00 -51.00 155.79   58
 64  ω   -106.00 -79.00   0.50    1.00    --  -82.00 -52.00 101.27   54
 65  ω   -118.00 -82.00   0.50    1.00    --  -82.00 -50.00 173.41   72
 66  ω   -105.00 -79.00   0.50    1.00    --  -82.00 -53.00 -49.37   52
 67  ω   -106.00 -80.00   0.50    1.00    --  -82.00 -52.00-158.71   52
 68  ω    -93.00 -19.00   0.50    1.00    --  -82.00  93.00-111.81  148
 69  ω   -104.00 -79.00   0.50    1.00    --  -82.00 -51.00 123.99   50
 70  ω   -153.00-128.00   0.50    1.00    --  -82.00 -51.00 123.99   50
 71  ω   -114.00 -83.00   0.50    1.00    --  -82.00 -53.00 -57.31   62
 72  ω   -115.00 -78.00   0.50    1.00    --  -82.00 -54.00 -97.63   74
 73  ω   -150.00-124.00   0.50    1.00    --  -82.00 -54.00  43.91   52
 74  ω     92.00 142.00   0.50    1.00    --   91.36  61.00   0.00  100
 75  ω     91.00 124.00   0.50    1.00    --   91.36  45.00 -60.00   66
 76  ω    126.00 157.00   0.50    1.00    --   91.36  61.00 150.00   62
 77  ω     67.00  92.00   0.50    1.00    --   91.36 -95.00  90.00   50
 78  ω     86.00 123.00   0.50    1.00    --   91.36  61.00 150.00   74
 79  ω     30.00  58.00   0.50    1.00    --   91.36 -95.00  90.00   56
 80  ω     89.00 115.00   0.50    1.00    --   91.36  61.00 -90.00   52
 81  ω     50.00 101.00   0.50    1.00    --   91.36-125.00 -30.00  102
 82  ω     68.00  98.00   0.50    1.00    --   91.36-125.00 -90.00   60
 83  ω     66.00  92.00   0.50    1.00    --   91.36 -95.00  30.00   52
 84  ω     33.00  84.00   0.50    1.00    --   91.36 -95.00   0.00  102
 85  ω     34.00  60.00   0.50    1.00    --   91.36 -95.00  30.00   52
 86  ω     34.00  60.00   0.50    1.00    --   91.36-125.00 -90.00   52
 87  ω     90.00 159.00   0.50    1.00    --   91.36  61.00 -60.00  138
 88  ω     88.00 113.00   0.50    1.00    --   91.36  61.00-120.00   50
 89  ω     33.00  68.00   0.50    1.00    --   91.36 -77.00-180.00   70
 90  ω    129.00 160.00   0.50    1.00    --   91.36  61.00 120.00   62
 91  ω     94.00 120.00   0.50    1.00    --   91.36  45.00  30.00   52
 92  ω    124.00 163.00   0.50    1.00    --   91.36  45.00 -30.00   78
 93  ω     89.00 124.00   0.50    1.00    --   91.36  61.00 120.00   70
 94  ω     98.00 123.00   0.50    1.00    --   91.36  45.00 -30.00   50
 95  ω     65.00  91.00   0.50    1.00    --   91.36 -95.00  60.00   52
 96  ω     86.00 126.00   0.50    1.00    --   91.36  61.00  30.00   80
 97  ω     34.00  60.00   0.50    1.00    --   91.36 -95.00  60.00   52
 98  ω     62.00  88.00   0.50    1.00    --   91.36 -95.00-180.00   52
 99  ω    128.00 157.00   0.50    1.00    --   91.36  61.00-150.00   58
100  ω     73.00  98.00   0.50    1.00    --   91.36-125.00   0.00   50
101  ω     34.00  60.00   0.50    1.00    --   91.36 -95.00-180.00   52
102  ω     86.00 122.00   0.50    1.00    --   91.36  61.00-150.00   72
103  ω     38.00  69.00   0.50    1.00    --   91.36-125.00   0.00   62
104  ω     86.00 150.00   0.50    1.00    --   91.36  61.00  60.00  128
105  ω     90.00 116.00   0.50    1.00    --   91.36  45.00  60.00   52
106  ω    125.00 151.00   0.50    1.00    --   91.36  61.00  90.00   52
107  ω     32.00  78.00   0.50    1.00    --   91.36 -95.00 150.00   92
108  ω     86.00 114.00   0.50    1.00    --   91.36  61.00  90.00   56
109  ω    118.00 154.00   0.50    1.00    --   91.36  77.00  30.00   72
110  ω     90.00 160.00   0.50    1.00    --   91.36  45.00 -90.00  140
111  ω     88.00 159.00   0.50    1.00    --   91.36  61.00-180.00  142
112  ω     29.00  55.00   0.50    1.00    --   91.36 -77.00  90.00   52
113  ω     36.00  63.00   0.50    1.00    --   91.36 -77.00-120.00   54
114  ω     29.00  54.00   0.50    1.00    --   91.36 -77.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1500983000
_diffrn_orient_matrix_UB_12      0.1164803000
_diffrn_orient_matrix_UB_13      -0.0604920000
_diffrn_orient_matrix_UB_21      0.0851619000
_diffrn_orient_matrix_UB_22      0.1417349000
_diffrn_orient_matrix_UB_23      0.0165860000
_diffrn_orient_matrix_UB_31      0.0998081000
_diffrn_orient_matrix_UB_32      0.0067482000
_diffrn_orient_matrix_UB_33      -0.1290120000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2575
_reflns_number_total             2653
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.109a 64-bit (release 21-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-1997 97-2 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0411P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31893(14) 1.06307(13) 0.79421(11) 0.0188(2) Uani 1 1 d . . .
H1A H 0.3731 1.0062 0.8701 0.028 Uiso 1 1 calc R . .
H1B H 0.1938 1.0856 0.8134 0.028 Uiso 1 1 calc R . .
H1C H 0.3672 1.1635 0.7618 0.028 Uiso 1 1 calc R . .
C2 C 0.35402(14) 0.96129(12) 0.69760(10) 0.0156(2) Uani 1 1 d . . .
C3 C 0.21930(14) 0.96685(13) 0.62344(11) 0.0175(2) Uani 1 1 d . . .
H3 H 0.1138 1.0332 0.6363 0.021 Uiso 1 1 calc R . .
C4 C 0.23474(14) 0.87898(13) 0.53219(11) 0.0182(2) Uani 1 1 d . . .
H4 H 0.1423 0.8873 0.4816 0.022 Uiso 1 1 calc R . .
C5 C 0.38669(14) 0.77823(13) 0.51497(10) 0.0166(2) Uani 1 1 d . . .
H5 H 0.3978 0.7164 0.4531 0.020 Uiso 1 1 calc R . .
C6 C 0.52210(14) 0.76779(12) 0.58801(10) 0.0145(2) Uani 1 1 d . . .
C7 C 0.51030(14) 0.86161(12) 0.67821(10) 0.0141(2) Uani 1 1 d . . .
C8 C 0.66606(14) 0.84749(13) 0.74762(10) 0.0139(2) Uani 1 1 d . . .
C9 C 0.70496(14) 0.97355(13) 0.79513(10) 0.0159(2) Uani 1 1 d . . .
H9 H 0.6323 1.0727 0.7808 0.019 Uiso 1 1 calc R . .
C10 C 0.84768(14) 0.95600(13) 0.86272(10) 0.0176(2) Uani 1 1 d . . .
H10 H 0.8691 1.0413 0.8972 0.021 Uiso 1 1 calc R . .
C11 C 0.95900(14) 0.81447(14) 0.88005(10) 0.0177(2) Uani 1 1 d . . .
H11 H 1.0548 0.8020 0.9283 0.021 Uiso 1 1 calc R . .
C12 C 0.93105(14) 0.69033(13) 0.82707(10) 0.0154(2) Uani 1 1 d . . .
C13 C 0.78458(13) 0.70620(12) 0.76190(10) 0.0133(2) Uani 1 1 d . . .
C14 C 1.06393(15) 0.54444(14) 0.83119(11) 0.0190(2) Uani 1 1 d . . .
H14A H 1.0259 0.4557 0.8969 0.023 Uiso 1 1 calc R . .
H14B H 1.1759 0.5675 0.8514 0.023 Uiso 1 1 calc R . .
C15 C 1.08631(14) 0.49634(13) 0.70482(11) 0.0176(2) Uani 1 1 d . . .
H15A H 1.1259 0.5846 0.6393 0.021 Uiso 1 1 calc R . .
H15B H 1.1752 0.4020 0.7069 0.021 Uiso 1 1 calc R . .
C16 C 0.91838(14) 0.45830(13) 0.67517(10) 0.0153(2) Uani 1 1 d . . .
C17 C 0.75350(13) 0.57465(12) 0.69883(10) 0.0136(2) Uani 1 1 d . . .
C18 C 0.68393(14) 0.65375(13) 0.57198(10) 0.0146(2) Uani 1 1 d . . .
H18A H 0.7732 0.7120 0.5179 0.018 Uiso 1 1 calc R . .
H18B H 0.6581 0.5707 0.5309 0.018 Uiso 1 1 calc R . .
C19 C 0.62501(14) 0.46763(12) 0.77708(10) 0.0140(2) Uani 1 1 d . . .
C20 C 0.55891(15) 0.31006(13) 0.97540(11) 0.0194(2) Uani 1 1 d . . .
H20A H 0.5675 0.2103 0.9464 0.029 Uiso 1 1 calc R . .
H20B H 0.4391 0.3623 0.9742 0.029 Uiso 1 1 calc R . .
H20C H 0.5940 0.2870 1.0605 0.029 Uiso 1 1 calc R . .
O1 O 0.90513(11) 0.34359(10) 0.63386(8) 0.0251(2) Uani 1 1 d . . .
O2 O 0.67131(10) 0.41428(9) 0.89429(7) 0.01744(19) Uani 1 1 d . . .
O3 O 0.50275(10) 0.43005(9) 0.73996(8) 0.0211(2) 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5109(15) . ?
C2 C3 1.3989(16) . ?
C2 C7 1.4146(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3806(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3895(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3868(15) . ?
C6 C7 1.4104(15) . ?
C6 C18 1.5072(14) . ?
C7 C8 1.4913(15) . ?
C8 C9 1.4016(15) . ?
C8 C13 1.4131(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3870(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3850(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3924(15) . ?
C12 C13 1.3984(15) . ?
C12 C14 1.5100(15) . ?
C13 C17 1.5274(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5307(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.4936(15) . ?
C16 C17 1.5522(14) . ?
C16 O1 1.2079(14) . ?
C17 C18 1.5383(14) . ?
C17 C19 1.5332(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.3468(13) . ?
C19 O3 1.1999(13) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O2 1.4480(13) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 116.42(10) . . ?
C3 C2 C7 118.56(10) . . ?
C7 C2 C1 125.02(10) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.09(10) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.41(10) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.11(10) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.95(10) . . ?
C5 C6 C18 119.78(10) . . ?
C7 C6 C18 119.27(9) . . ?
C2 C7 C8 124.37(10) . . ?
C6 C7 C2 118.81(10) . . ?
C6 C7 C8 116.82(9) . . ?
C9 C8 C7 122.18(10) . . ?
C9 C8 C13 117.82(10) . . ?
C13 C8 C7 119.93(9) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.13(10) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.20(10) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.27(10) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.53(10) . . ?
C11 C12 C14 120.53(10) . . ?
C13 C12 C14 119.78(10) . . ?
C8 C13 C17 118.30(9) . . ?
C12 C13 C8 120.82(10) . . ?
C12 C13 C17 120.81(9) . . ?
C12 C14 H14A 109.7 . . ?
C12 C14 H14B 109.7 . . ?
C12 C14 C15 109.66(9) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 109.89(9) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 C17 117.29(9) . . ?
O1 C16 C15 123.64(10) . . ?
O1 C16 C17 119.08(10) . . ?
C13 C17 C16 114.04(8) . . ?
C13 C17 C18 108.12(8) . . ?
C13 C17 C19 112.39(8) . . ?
C18 C17 C16 107.76(8) . . ?
C19 C17 C16 104.66(8) . . ?
C19 C17 C18 109.73(8) . . ?
C6 C18 C17 110.67(9) . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
O2 C19 C17 110.75(9) . . ?
O3 C19 C17 125.71(10) . . ?
O3 C19 O2 123.48(10) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
C19 O2 C20 114.98(8) . . ?

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 -179.74(10) . . . . ?
C1 C2 C7 C6 177.26(10) . . . . ?
C1 C2 C7 C8 -2.46(16) . . . . ?
C2 C3 C4 C5 1.76(16) . . . . ?
C2 C7 C8 C9 -29.24(16) . . . . ?
C2 C7 C8 C13 153.90(10) . . . . ?
C3 C2 C7 C6 -2.14(15) . . . . ?
C3 C2 C7 C8 178.14(10) . . . . ?
C3 C4 C5 C6 -0.75(16) . . . . ?
C4 C5 C6 C7 -1.71(16) . . . . ?
C4 C5 C6 C18 177.75(10) . . . . ?
C5 C6 C7 C2 3.16(15) . . . . ?
C5 C6 C7 C8 -177.10(9) . . . . ?
C5 C6 C18 C17 -141.24(10) . . . . ?
C6 C7 C8 C9 151.03(10) . . . . ?
C6 C7 C8 C13 -25.82(14) . . . . ?
C7 C2 C3 C4 -0.28(16) . . . . ?
C7 C6 C18 C17 38.24(13) . . . . ?
C7 C8 C9 C10 177.98(10) . . . . ?
C7 C8 C13 C12 -179.75(9) . . . . ?
C7 C8 C13 C17 3.28(15) . . . . ?
C8 C9 C10 C11 2.71(17) . . . . ?
C8 C13 C17 C16 157.36(9) . . . . ?
C8 C13 C17 C18 37.54(12) . . . . ?
C8 C13 C17 C19 -83.72(12) . . . . ?
C9 C8 C13 C12 3.26(16) . . . . ?
C9 C8 C13 C17 -173.71(9) . . . . ?
C9 C10 C11 C12 1.68(17) . . . . ?
C10 C11 C12 C13 -3.47(17) . . . . ?
C10 C11 C12 C14 171.95(10) . . . . ?
C11 C12 C13 C8 0.94(16) . . . . ?
C11 C12 C13 C17 177.84(10) . . . . ?
C11 C12 C14 C15 -137.23(11) . . . . ?
C12 C13 C17 C16 -19.61(14) . . . . ?
C12 C13 C17 C18 -139.44(10) . . . . ?
C12 C13 C17 C19 99.30(11) . . . . ?
C12 C14 C15 C16 -60.50(12) . . . . ?
C13 C8 C9 C10 -5.10(16) . . . . ?
C13 C12 C14 C15 38.18(14) . . . . ?
C13 C17 C18 C6 -56.81(11) . . . . ?
C13 C17 C19 O2 -51.30(11) . . . . ?
C13 C17 C19 O3 131.29(11) . . . . ?
C14 C12 C13 C8 -174.51(10) . . . . ?
C14 C12 C13 C17 2.39(15) . . . . ?
C14 C15 C16 C17 44.86(13) . . . . ?
C14 C15 C16 O1 -135.45(11) . . . . ?
C15 C16 C17 C13 -5.53(13) . . . . ?
C15 C16 C17 C18 114.50(10) . . . . ?
C15 C16 C17 C19 -128.75(10) . . . . ?
C16 C17 C18 C6 179.50(8) . . . . ?
C16 C17 C19 O2 72.97(10) . . . . ?
C16 C17 C19 O3 -104.44(12) . . . . ?
C17 C19 O2 C20 -179.21(8) . . . . ?
C18 C6 C7 C2 -176.31(9) . . . . ?
C18 C6 C7 C8 3.43(14) . . . . ?
C18 C17 C19 O2 -171.64(8) . . . . ?
C18 C17 C19 O3 10.95(14) . . . . ?
C19 C17 C18 C6 66.09(11) . . . . ?
O1 C16 C17 C13 174.77(10) . . . . ?
O1 C16 C17 C18 -65.20(13) . . . . ?
O1 C16 C17 C19 51.56(13) . . . . ?
O3 C19 O2 C20 -1.73(15) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP257
_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 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.907
####################################################################### 
# 
# 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_2024sot0038_d1_100k_
_database_code_depnum_ccdc_archive 'CCDC 2352648'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-05-02
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N O3 S'
_chemical_formula_sum            'C16 H11 N O3 S'
_chemical_formula_weight         297.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H11NO3S
_chemical_oxdiff_usercomment     MEP266
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   10.3033(2)
_cell_length_b                   16.8149(4)
_cell_length_c                   7.34640(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.449(2)
_cell_angle_gamma                90
_cell_volume                     1271.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.9380
_cell_measurement_theta_min      4.2820
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.719
_exptl_absorpt_coefficient_mu    2.359
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (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            'clear pale yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pale
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -5 0 0.0148
-4 5 0 0.0148
1 2 -5 0.0278
-1 -2 5 0.0278
-2 -5 -1 0.0684
2 5 1 0.0684
1 2 -2 0.0249

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_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
3.9967 -4.9916 0.0002 -0.3940 -0.6412 -0.0197
-3.9967 4.9916 -0.0002 0.3940 0.6412 0.0197
0.9954 1.9967 -4.9958 -0.4879 0.3054 0.9004
-0.9954 -1.9967 4.9958 0.4879 -0.3054 -0.9004
-1.9970 -4.9979 -1.0003 0.3490 -0.2664 0.3946
1.9970 4.9979 1.0003 -0.3490 0.2664 -0.3946
0.9972 1.9982 -1.9980 -0.3092 0.1887 0.3084

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11803
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.185
_diffrn_reflns_theta_min         4.295
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00 -11.00   0.50    1.00    --  -75.43 104.00 159.00  162
  2  ω    -79.00  -3.00   0.50    1.00    --  -49.92 104.00 159.00  152
  3  ω    -55.00  -7.00   0.50    1.00    --  -75.43  61.00 120.00   96
  4  ω    -33.00  -4.00   0.50    1.00    --  -75.43  45.00-120.00   58
  5  ω    -33.00  -4.00   0.50    1.00    --  -75.43  45.00-180.00   58
  6  ω    -24.00  15.00   0.50    1.00    --   48.17 -38.00  90.00   78
  7  ω    -24.00  15.00   0.50    1.00    --   48.17 -38.00 120.00   78
  8  ω    -24.00  15.00   0.50    1.00    --   48.17 -38.00  60.00   78
  9  ω    -24.00  15.00   0.50    1.00    --   48.17 -38.00 -30.00   78
 10  ω     88.00 157.00   0.50    1.00    --   91.36 125.00-120.00  138
 11  ω    100.00 156.00   0.50    1.00    --   91.36 104.00 159.00  112
 12  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00  90.00   84
 13  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00 120.00   84
 14  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00 150.00   84
 15  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00   0.00   84
 16  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00 -60.00   84
 17  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00-180.00   84
 18  ω     -3.00  78.00   0.50    1.00    --   48.17-104.00  57.00  162
 19  ω     -3.00  78.00   0.50    1.00    --   48.17-104.00  57.00  162
 20  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00  90.00  126
 21  ω     27.00  92.00   0.50    1.00    --   91.36-104.00  57.00  130
 22  ω     78.00 132.00   0.50    1.00    --   91.36  15.00-180.00  108
 23  ω     78.00 132.00   0.50    1.00    --   91.36  15.00-150.00  108
 24  ω     99.00 154.00   0.50    1.00    --   91.36  77.00-150.00  110
 25  ω     78.00 132.00   0.50    1.00    --   91.36  15.00 -60.00  108
 26  ω   -123.00 -75.00   0.50    1.00    --  -49.92 -38.00  60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1338880000
_diffrn_orient_matrix_UB_12      -0.0282696000
_diffrn_orient_matrix_UB_13      0.0596817000
_diffrn_orient_matrix_UB_21      -0.0561204000
_diffrn_orient_matrix_UB_22      0.0835209000
_diffrn_orient_matrix_UB_23      -0.0389276000
_diffrn_orient_matrix_UB_31      -0.0361432000
_diffrn_orient_matrix_UB_32      -0.0250068000
_diffrn_orient_matrix_UB_33      -0.1974206000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2217
_reflns_number_total             2348
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.120a 64-bit (release 16-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.105
_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)+(0.0418P)²+0.4579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.02888(13) 0.08776(8) 0.6348(2) 0.0237(3) Uani 1 1 d . . . . .
H1A H 1.019727 0.070149 0.762221 0.028 Uiso 1 1 calc R U . . .
H1B H 1.089226 0.051087 0.575462 0.028 Uiso 1 1 calc R U . . .
C2 C 0.86561(13) 0.16633(8) 0.53814(17) 0.0170(3) Uani 1 1 d . . . . .
C3 C 0.96954(12) 0.21389(8) 0.59415(17) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.96060(12) 0.29506(8) 0.59975(17) 0.0173(3) Uani 1 1 d . . . . .
H4 H 1.032292 0.327406 0.637966 0.021 Uiso 1 1 calc R U . . .
C5 C 0.83996(12) 0.32783(8) 0.54606(17) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.73451(12) 0.28034(8) 0.48698(17) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.74773(12) 0.19691(8) 0.48195(17) 0.0168(3) Uani 1 1 d . . . . .
H7 H 0.677945 0.163529 0.441398 0.020 Uiso 1 1 calc R U . . .
C8 C 0.81810(12) 0.41580(8) 0.55997(18) 0.0177(3) Uani 1 1 d . . . . .
H8A H 0.777430 0.428092 0.676363 0.021 Uiso 1 1 calc R U . . .
H8B H 0.902531 0.443868 0.559039 0.021 Uiso 1 1 calc R U . . .
C9 C 0.61232(12) 0.32039(8) 0.42714(17) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.49257(13) 0.28130(8) 0.42016(18) 0.0202(3) Uani 1 1 d . . . . .
H10 H 0.487928 0.227695 0.460187 0.024 Uiso 1 1 calc R U . . .
C11 C 0.38026(13) 0.31940(9) 0.35577(19) 0.0228(3) Uani 1 1 d . . . . .
H11 H 0.299261 0.292382 0.354741 0.027 Uiso 1 1 calc R U . . .
C12 C 0.38659(13) 0.39702(9) 0.29293(18) 0.0205(3) Uani 1 1 d . . . . .
H12 H 0.310358 0.422305 0.244031 0.025 Uiso 1 1 calc R U . . .
C13 C 0.50410(13) 0.43814(8) 0.30110(17) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.61610(12) 0.40084(8) 0.37392(16) 0.0159(3) Uani 1 1 d . . . . .
C15 C 0.67551(13) 0.53620(8) 0.16039(18) 0.0190(3) Uani 1 1 d . . . . .
H15A H 0.682016 0.498375 0.057914 0.023 Uiso 1 1 calc R U . . .
H15B H 0.700385 0.589601 0.117086 0.023 Uiso 1 1 calc R U . . .
C16 C 0.76687(13) 0.51104(8) 0.31623(18) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.73338(10) 0.44376(7) 0.40670(15) 0.0163(2) Uani 1 1 d . . . . .
O1 O 0.90423(9) 0.08751(5) 0.53839(13) 0.0209(2) Uani 1 1 d . . . . .
O2 O 1.07785(9) 0.16727(6) 0.63117(14) 0.0221(2) Uani 1 1 d . . . . .
O3 O 0.86568(9) 0.54864(6) 0.35622(14) 0.0240(2) Uani 1 1 d . . . . .
S1 S 0.51085(3) 0.53854(2) 0.23355(4) 0.01892(12) 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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 O1 1.4399(16) . ?
C1 O2 1.4297(16) . ?
C2 C3 1.3848(19) . ?
C2 C7 1.3664(19) . ?
C2 O1 1.3838(16) . ?
C3 C4 1.3687(19) . ?
C3 O2 1.3813(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.4008(18) . ?
C5 C6 1.4021(18) . ?
C5 C8 1.5005(18) . ?
C6 C7 1.4101(19) . ?
C6 C9 1.4780(18) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N1 1.4720(16) . ?
C9 C10 1.3970(18) . ?
C9 C14 1.4091(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3880(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.3933(19) . ?
C13 C14 1.3994(18) . ?
C13 S1 1.7618(14) . ?
C14 N1 1.4192(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5112(18) . ?
C15 S1 1.8018(14) . ?
C16 N1 1.3638(17) . ?
C16 O3 1.2235(17) . ?

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
H1A C1 H1B 108.5 . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
O2 C1 H1A 110.2 . . ?
O2 C1 H1B 110.2 . . ?
O2 C1 O1 107.55(10) . . ?
C7 C2 C3 122.58(12) . . ?
C7 C2 O1 127.78(12) . . ?
O1 C2 C3 109.51(11) . . ?
C4 C3 C2 122.18(12) . . ?
C4 C3 O2 127.94(12) . . ?
O2 C3 C2 109.80(12) . . ?
C3 C4 H4 121.8 . . ?
C3 C4 C5 116.34(12) . . ?
C5 C4 H4 121.8 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 C8 120.17(11) . . ?
C6 C5 C8 117.76(11) . . ?
C5 C6 C7 120.01(12) . . ?
C5 C6 C9 118.14(12) . . ?
C7 C6 C9 121.84(12) . . ?
C2 C7 C6 116.88(12) . . ?
C2 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C5 C8 H8A 109.6 . . ?
C5 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C8 C5 110.40(10) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C10 C9 C6 122.43(12) . . ?
C10 C9 C14 118.45(12) . . ?
C14 C9 C6 119.12(11) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.16(13) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.83(13) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.38(12) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.66(13) . . ?
C12 C13 S1 120.53(10) . . ?
C14 C13 S1 119.69(10) . . ?
C9 C14 N1 118.33(11) . . ?
C13 C14 C9 120.28(12) . . ?
C13 C14 N1 121.27(12) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C16 C15 S1 110.13(9) . . ?
S1 C15 H15A 109.6 . . ?
S1 C15 H15B 109.6 . . ?
N1 C16 C15 116.05(11) . . ?
O3 C16 C15 121.48(12) . . ?
O3 C16 N1 122.47(12) . . ?
C14 N1 C8 116.11(10) . . ?
C16 N1 C8 118.92(11) . . ?
C16 N1 C14 124.78(11) . . ?
C2 O1 C1 104.38(10) . . ?
C3 O2 C1 104.57(10) . . ?
C13 S1 C15 96.44(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
C2 C3 C4 C5 0.18(19) . . . . ?
C2 C3 O2 C1 -12.59(14) . . . . ?
C3 C2 C7 C6 -1.40(19) . . . . ?
C3 C2 O1 C1 12.08(14) . . . . ?
C3 C4 C5 C6 -0.98(18) . . . . ?
C3 C4 C5 C8 175.75(12) . . . . ?
C4 C3 O2 C1 170.60(14) . . . . ?
C4 C5 C6 C7 0.60(19) . . . . ?
C4 C5 C6 C9 -177.98(11) . . . . ?
C4 C5 C8 N1 144.04(12) . . . . ?
C5 C6 C7 C2 0.59(18) . . . . ?
C5 C6 C9 C10 -159.66(12) . . . . ?
C5 C6 C9 C14 20.73(17) . . . . ?
C5 C8 N1 C14 50.34(14) . . . . ?
C5 C8 N1 C16 -134.41(12) . . . . ?
C6 C5 C8 N1 -39.10(15) . . . . ?
C6 C9 C10 C11 -177.12(12) . . . . ?
C6 C9 C14 C13 174.18(11) . . . . ?
C6 C9 C14 N1 -9.71(17) . . . . ?
C7 C2 C3 C4 1.0(2) . . . . ?
C7 C2 C3 O2 -175.98(11) . . . . ?
C7 C2 O1 C1 -171.92(13) . . . . ?
C7 C6 C9 C10 21.79(19) . . . . ?
C7 C6 C9 C14 -157.82(12) . . . . ?
C8 C5 C6 C7 -176.20(12) . . . . ?
C8 C5 C6 C9 5.21(17) . . . . ?
C9 C6 C7 C2 179.12(11) . . . . ?
C9 C10 C11 C12 1.6(2) . . . . ?
C9 C14 N1 C8 -26.85(16) . . . . ?
C9 C14 N1 C16 158.22(12) . . . . ?
C10 C9 C14 C13 -5.45(18) . . . . ?
C10 C9 C14 N1 170.67(11) . . . . ?
C10 C11 C12 C13 -2.7(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 S1 -176.36(10) . . . . ?
C12 C13 C14 C9 4.39(19) . . . . ?
C12 C13 C14 N1 -171.62(11) . . . . ?
C12 C13 S1 C15 -150.77(11) . . . . ?
C13 C14 N1 C8 149.23(12) . . . . ?
C13 C14 N1 C16 -25.71(19) . . . . ?
C14 C9 C10 C11 2.49(19) . . . . ?
C14 C13 S1 C15 33.14(12) . . . . ?
C15 C16 N1 C8 179.96(11) . . . . ?
C15 C16 N1 C14 -5.23(18) . . . . ?
C16 C15 S1 C13 -58.36(10) . . . . ?
O1 C1 O2 C3 19.99(14) . . . . ?
O1 C2 C3 C4 177.29(12) . . . . ?
O1 C2 C3 O2 0.27(14) . . . . ?
O1 C2 C7 C6 -176.92(12) . . . . ?
O2 C1 O1 C2 -19.83(14) . . . . ?
O2 C3 C4 C5 176.63(12) . . . . ?
O3 C16 N1 C8 0.90(19) . . . . ?
O3 C16 N1 C14 175.70(12) . . . . ?
S1 C13 C14 C9 -179.49(9) . . . . ?
S1 C13 C14 N1 4.51(17) . . . . ?
S1 C15 C16 N1 50.25(14) . . . . ?
S1 C15 C16 O3 -130.67(12) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP266
_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 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.641
####################################################################### 
# 
# 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_2024sot0039_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2355891'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_audit_creation_date             2024-05-16
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
mep1m22@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 I O6'
_chemical_formula_sum            'C22 H21 I O6'
_chemical_formula_weight         508.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H21IO6
_chemical_oxdiff_usercomment     MEP261
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'
I I -0.3257 6.8362 '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                   9.0209(2)
_cell_length_b                   9.6030(2)
_cell_length_c                   13.9670(2)
_cell_angle_alpha                73.6950(10)
_cell_angle_beta                 71.4480(10)
_cell_angle_gamma                66.600(2)
_cell_volume                     1036.01(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17660
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      68.9150
_cell_measurement_theta_min      3.3710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 3 0.0519
-5 0 -3 0.0111
5 0 3 0.0111
-5 0 -4 0.0279
5 0 4 0.0279
0 1 5 0.1003
1 -1 -5 0.1444
-2 -5 -1 0.0412
2 5 1 0.0412
0 1 5 0.1058
0 -1 -5 0.1058
-5 0 -3 0.0371
5 0 3 0.0371
-1 5 -1 0.0557
1 -5 1 0.0557
-5 0 -4 0.0353
5 0 4 0.0353
-2 -5 -2 0.0477
2 5 2 0.0477
-1 0 5 0.1247
1 0 -5 0.1247

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_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
4.9940 -0.0001 2.9973 0.7654 -0.5411 0.0432
-4.9940 0.0001 -2.9973 -0.7654 0.5411 -0.0432
4.9940 -0.0001 2.9973 0.7654 -0.5411 0.0432
-4.9937 0.0001 -3.9965 -0.7968 0.5341 0.0705
4.9937 -0.0001 3.9965 0.7968 -0.5341 -0.0705
-0.0010 0.9989 4.9960 0.0046 -0.0551 -0.5832
0.9999 -0.9989 -4.9961 0.1297 -0.0573 0.6601
-1.9990 -4.9948 -0.9987 0.4613 0.6674 0.0339
1.9990 4.9948 0.9987 -0.4613 -0.6674 -0.0339
-0.0010 0.9989 4.9960 0.0046 -0.0551 -0.5832
0.0010 -0.9989 -4.9960 -0.0046 0.0551 0.5832
-4.9940 0.0001 -2.9973 -0.7654 0.5411 -0.0432
4.9940 -0.0001 2.9973 0.7654 -0.5411 0.0432
-0.9973 4.9949 -0.9995 -0.9268 -0.3442 -0.0371
0.9973 -4.9949 0.9995 0.9268 0.3442 0.0371
-4.9937 0.0001 -3.9965 -0.7968 0.5341 0.0705
4.9937 -0.0001 3.9965 0.7968 -0.5341 -0.0705
-1.9987 -4.9948 -1.9979 0.4299 0.6605 0.1476
1.9987 4.9948 1.9979 -0.4299 -0.6605 -0.1476
-1.0002 -0.0000 4.9962 0.0225 0.1472 -0.6453
1.0002 0.0000 -4.9962 -0.0225 -0.1472 0.6453

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18426
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.130
_diffrn_reflns_theta_min         3.392
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00 121.00   0.50    1.00    --   48.17  21.00  95.00  158
  2  ω   -148.00 -69.00   0.50    1.00    --  -75.43 -21.00 -70.00  158
  3  ω   -148.00 -69.00   0.50    1.00    --  -75.43 -21.00 -70.00  158
  4  ω     86.00 149.00   0.50    1.00    --   91.36  21.00  95.00  126
  5  ω     -2.00  25.00   0.50    1.00    --    6.00  73.00-158.52   54
  6  ω     -3.00  28.00   0.50    1.00    --    6.00  72.00  16.06   62
  7  ω    -24.00  15.00   0.50    1.00    --   48.17 -38.00 150.00   78
  8  ω   -123.00 -44.00   0.50    1.00    --  -49.92 -21.00 -70.00  158
  9  ω    -23.00  24.00   0.50    1.00    --  -49.92  38.00-150.00   94
 10  ω   -123.00 -44.00   0.50    1.00    --  -49.92 -21.00 -70.00  158
 11  ω    -79.00 -13.00   0.50    1.00    --  -75.43  77.00 -90.00  132
 12  ω    -33.00  -4.00   0.50    1.00    --  -75.43  45.00 -90.00   58
 13  ω    -79.00 -13.00   0.50    1.00    --  -75.43  77.00 -90.00  132
 14  ω    -33.00  -4.00   0.50    1.00    --  -75.43  45.00 -30.00   58
 15  ω    -79.00 -13.00   0.50    1.00    --  -75.43  77.00 120.00  132
 16  ω    -92.00 -19.00   0.50    1.00    --  -82.00  95.00-159.16  146
 17  ω    -93.00 -17.00   0.50    1.00    --  -82.00 104.00   0.63  152
 18  ω    -92.00 -19.00   0.50    1.00    --  -82.00  95.00-159.16  146
 19  ω    -93.00 -19.00   0.50    1.00    --  -82.00  90.00  50.82  148
 20  ω    -97.00 -18.00   0.50    1.00    --  -82.00 114.00 151.49  158
 21  ω    -93.00 -17.00   0.50    1.00    --  -82.00 104.00   0.63  152
 22  ω    -93.00 -19.00   0.50    1.00    --  -82.00  90.00  50.82  148
 23  ω     29.00  71.00   0.50    1.00    --   91.36 -77.00-180.00   84
 24  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00 120.00  126
 25  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00 -90.00  126
 26  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00 -90.00  126
 27  ω     99.00 154.00   0.50    1.00    --   91.36  77.00 -90.00  110
 28  ω     78.00 132.00   0.50    1.00    --   91.36  15.00-150.00  108
 29  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00 150.00  126
 30  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00  90.00  126
 31  ω     29.00  92.00   0.50    1.00    --   91.36 -95.00-150.00  126
 32  ω     78.00 132.00   0.50    1.00    --   91.36  15.00 -90.00  108
 33  ω     43.00  89.00   0.50    1.00    --   91.36 -95.00  60.00   92
 34  ω     38.00  90.00   0.50    1.00    --   91.36 -95.00-120.00  104
 35  ω    135.00 160.00   0.50    1.00    --   91.36  61.00 150.00   50
 36  ω     31.00  57.00   0.50    1.00    --   91.36 -77.00  60.00   52
 37  ω     86.00 119.00   0.50    1.00    --   91.36  61.00 150.00   66
 38  ω     58.00  92.00   0.50    1.00    --   91.36 -95.00 -60.00   68
 39  ω    114.00 159.00   0.50    1.00    --   91.36  45.00 150.00   90
 40  ω     31.00  64.00   0.50    1.00    --   91.36 -77.00 -90.00   66
 41  ω     29.00  56.00   0.50    1.00    --   91.36 -95.00   0.00   54
 42  ω     64.00  90.00   0.50    1.00    --   91.36 -95.00   0.00   52
 43  ω     58.00  92.00   0.50    1.00    --   91.36 -95.00 -30.00   68
 44  ω     30.00  92.00   0.50    1.00    --   91.36 -95.00  30.00  124
 45  ω     94.00 130.00   0.50    1.00    --   91.36  15.00 120.00   72
 46  ω     29.00  68.00   0.50    1.00    --   91.36-125.00   0.00   78
 47  ω    113.00 141.00   0.50    1.00    --   91.36  77.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1344107000
_diffrn_orient_matrix_UB_12      -0.1524212000
_diffrn_orient_matrix_UB_13      0.0314162000
_diffrn_orient_matrix_UB_21      -0.1125174000
_diffrn_orient_matrix_UB_22      -0.0899845000
_diffrn_orient_matrix_UB_23      0.0069440000
_diffrn_orient_matrix_UB_31      0.0769232000
_diffrn_orient_matrix_UB_32      -0.0148289000
_diffrn_orient_matrix_UB_33      -0.1137596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3774
_reflns_number_total             3788
_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 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0172
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.9754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0451
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4677(2) 0.6176(2) 0.79779(14) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.3229(2) 0.6070(2) 0.78795(15) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.331255 0.542333 0.744595 0.022 Uiso 1 1 calc R U . . .
C3 C 0.1677(2) 0.6895(2) 0.84063(16) 0.0204(4) Uani 1 1 d . . . . .
H3 H 0.070466 0.683297 0.831819 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1539(2) 0.7813(2) 0.90621(15) 0.0194(4) Uani 1 1 d . . . . .
H4 H 0.047206 0.838306 0.941713 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2955(2) 0.7903(2) 0.92025(14) 0.0161(4) Uani 1 1 d . . . . .
C6 C 0.2819(3) 0.8813(2) 0.99656(16) 0.0209(4) Uani 1 1 d . . . . .
H6A H 0.175102 0.892256 1.048290 0.025 Uiso 1 1 calc R U . . .
H6B H 0.282600 0.985881 0.960665 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4252(3) 0.8024(2) 1.05050(15) 0.0209(4) Uani 1 1 d . . . . .
H7A H 0.416561 0.867807 1.097003 0.025 Uiso 1 1 calc R U . . .
H7B H 0.417179 0.702680 1.092592 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5899(2) 0.7750(2) 0.97468(15) 0.0173(4) Uani 1 1 d . . . . .
C9 C 0.6105(2) 0.7171(2) 0.87682(14) 0.0143(4) Uani 1 1 d . . . . .
C10 C 0.4518(2) 0.7096(2) 0.86562(14) 0.0138(4) Uani 1 1 d . . . . .
C11 C 0.6063(3) 1.0773(3) 0.68745(18) 0.0334(5) Uani 1 1 d . . . . .
H11A H 0.652226 1.036922 0.623122 0.050 Uiso 1 1 calc R U . . .
H11B H 0.690967 1.101505 0.703021 0.050 Uiso 1 1 calc R U . . .
H11C H 0.509727 1.171031 0.680444 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6775(2) 0.8283(2) 0.78706(14) 0.0149(4) Uani 1 1 d . . . . .
C13 C 0.7422(2) 0.5550(2) 0.88173(15) 0.0152(4) Uani 1 1 d . . . . .
H13A H 0.848389 0.561396 0.883128 0.018 Uiso 1 1 calc R U . . .
H13B H 0.706303 0.487990 0.945920 0.018 Uiso 1 1 calc R U . . .
C14 C 0.7695(2) 0.4840(2) 0.79091(14) 0.0142(4) Uani 1 1 d . . . . .
C15 C 0.9227(2) 0.3765(2) 0.75294(14) 0.0158(4) Uani 1 1 d . . . . .
C16 C 0.9467(2) 0.3123(2) 0.66902(15) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.8179(2) 0.3594(2) 0.62017(15) 0.0170(4) Uani 1 1 d . . . . .
C18 C 0.6653(2) 0.4678(2) 0.65620(14) 0.0152(4) Uani 1 1 d . . . . .
C19 C 0.6357(2) 0.5255(2) 0.74517(14) 0.0142(4) Uani 1 1 d . . . . .
C20 C 1.1095(3) 0.0543(3) 0.6513(2) 0.0448(7) Uani 1 1 d . . . . .
H20A H 1.035352 0.043870 0.617582 0.067 Uiso 1 1 calc R U . . .
H20B H 1.075962 0.021206 0.725585 0.067 Uiso 1 1 calc R U . . .
H20C H 1.223972 -0.010082 0.625349 0.067 Uiso 1 1 calc R U . . .
C21 C 0.9132(3) 0.3678(3) 0.44131(17) 0.0314(5) Uani 1 1 d . . . . .
H21A H 0.926939 0.313902 0.387352 0.047 Uiso 1 1 calc R U . . .
H21B H 1.022089 0.364618 0.443419 0.047 Uiso 1 1 calc R U . . .
H21C H 0.841697 0.475379 0.426734 0.047 Uiso 1 1 calc R U . . .
C22 C 0.5093(3) 0.6676(2) 0.54710(16) 0.0227(4) Uani 1 1 d . . . . .
H22A H 0.610079 0.680732 0.497820 0.034 Uiso 1 1 calc R U . . .
H22B H 0.468780 0.738028 0.595963 0.034 Uiso 1 1 calc R U . . .
H22C H 0.423665 0.690738 0.510400 0.034 Uiso 1 1 calc R U . . .
I1 I 1.12065(2) 0.29995(2) 0.82403(2) 0.01938(5) Uani 1 1 d . . . . .
O1 O 0.70690(18) 0.79376(17) 0.98698(11) 0.0249(3) Uani 1 1 d . . . . .
O2 O 0.55566(17) 0.96224(16) 0.77016(11) 0.0245(3) Uani 1 1 d . . . . .
O3 O 0.81898(17) 0.80229(17) 0.74046(12) 0.0253(3) Uani 1 1 d . . . . .
O4 O 1.09971(17) 0.21288(16) 0.62990(11) 0.0242(3) Uani 1 1 d . . . . .
O5 O 0.83824(18) 0.29396(16) 0.53873(11) 0.0217(3) Uani 1 1 d . . . . .
O6 O 0.54646(17) 0.51102(16) 0.60164(11) 0.0196(3) 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
C1 C2 1.401(3) . ?
C1 C10 1.408(3) . ?
C1 C19 1.487(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 C6 1.506(3) . ?
C5 C10 1.397(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.528(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.497(3) . ?
C8 C9 1.548(3) . ?
C8 O1 1.209(2) . ?
C9 C10 1.519(2) . ?
C9 C12 1.535(3) . ?
C9 C13 1.537(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 O2 1.453(2) . ?
C12 O2 1.338(2) . ?
C12 O3 1.193(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.513(3) . ?
C14 C15 1.402(3) . ?
C14 C19 1.411(3) . ?
C15 C16 1.392(3) . ?
C15 I1 2.0957(18) . ?
C16 C17 1.391(3) . ?
C16 O4 1.371(2) . ?
C17 C18 1.395(3) . ?
C17 O5 1.378(2) . ?
C18 C19 1.407(3) . ?
C18 O6 1.375(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O4 1.439(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 O5 1.437(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 O6 1.440(2) . ?

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 C10 118.29(17) . . ?
C2 C1 C19 121.77(17) . . ?
C10 C1 C19 119.77(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.86(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.16(18) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.37(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.58(17) . . ?
C4 C5 C10 119.49(18) . . ?
C10 C5 C6 119.89(17) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.25(16) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.28(16) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 C9 117.79(16) . . ?
O1 C8 C7 123.32(18) . . ?
O1 C8 C9 118.89(18) . . ?
C10 C9 C8 114.20(15) . . ?
C10 C9 C12 111.40(15) . . ?
C10 C9 C13 109.32(15) . . ?
C12 C9 C8 105.29(15) . . ?
C12 C9 C13 109.59(15) . . ?
C13 C9 C8 106.84(15) . . ?
C1 C10 C9 117.50(16) . . ?
C5 C10 C1 120.78(17) . . ?
C5 C10 C9 121.72(16) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
O2 C12 C9 110.44(15) . . ?
O3 C12 C9 125.39(17) . . ?
O3 C12 O2 124.13(18) . . ?
C9 C13 H13A 109.3 . . ?
C9 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C9 111.70(15) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C15 C14 C13 121.64(16) . . ?
C15 C14 C19 119.62(17) . . ?
C19 C14 C13 118.73(16) . . ?
C14 C15 I1 121.17(14) . . ?
C16 C15 C14 121.20(17) . . ?
C16 C15 I1 117.59(14) . . ?
C17 C16 C15 119.29(17) . . ?
O4 C16 C15 120.33(17) . . ?
O4 C16 C17 120.18(17) . . ?
C16 C17 C18 120.20(17) . . ?
O5 C17 C16 119.98(17) . . ?
O5 C17 C18 119.76(17) . . ?
C17 C18 C19 121.00(17) . . ?
O6 C18 C17 116.34(16) . . ?
O6 C18 C19 122.65(17) . . ?
C14 C19 C1 118.40(16) . . ?
C18 C19 C1 123.07(16) . . ?
C18 C19 C14 118.35(17) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
C12 O2 C11 115.02(16) . . ?
C16 O4 C20 114.34(17) . . ?
C17 O5 C21 113.78(15) . . ?
C18 O6 C22 113.79(14) . . ?

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 -1.6(3) . . . . ?
C2 C1 C10 C5 -1.1(3) . . . . ?
C2 C1 C10 C9 178.81(16) . . . . ?
C2 C1 C19 C14 -150.99(18) . . . . ?
C2 C1 C19 C18 24.0(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -175.93(18) . . . . ?
C3 C4 C5 C10 1.8(3) . . . . ?
C4 C5 C6 C7 143.21(18) . . . . ?
C4 C5 C10 C1 -1.0(3) . . . . ?
C4 C5 C10 C9 179.12(17) . . . . ?
C5 C6 C7 C8 55.7(2) . . . . ?
C6 C5 C10 C1 176.77(17) . . . . ?
C6 C5 C10 C9 -3.2(3) . . . . ?
C6 C7 C8 C9 -41.8(2) . . . . ?
C6 C7 C8 O1 139.30(19) . . . . ?
C7 C8 C9 C10 5.5(2) . . . . ?
C7 C8 C9 C12 128.00(17) . . . . ?
C7 C8 C9 C13 -115.51(18) . . . . ?
C8 C9 C10 C1 -161.57(16) . . . . ?
C8 C9 C10 C5 18.4(2) . . . . ?
C8 C9 C12 O2 -76.30(18) . . . . ?
C8 C9 C12 O3 101.4(2) . . . . ?
C8 C9 C13 C14 178.28(15) . . . . ?
C9 C12 O2 C11 179.09(17) . . . . ?
C9 C13 C14 C15 151.34(17) . . . . ?
C9 C13 C14 C19 -30.0(2) . . . . ?
C10 C1 C2 C3 2.4(3) . . . . ?
C10 C1 C19 C14 24.1(3) . . . . ?
C10 C1 C19 C18 -160.84(17) . . . . ?
C10 C5 C6 C7 -34.5(2) . . . . ?
C10 C9 C12 O2 48.0(2) . . . . ?
C10 C9 C12 O3 -134.31(19) . . . . ?
C10 C9 C13 C14 54.2(2) . . . . ?
C12 C9 C10 C1 79.3(2) . . . . ?
C12 C9 C10 C5 -100.8(2) . . . . ?
C12 C9 C13 C14 -68.12(19) . . . . ?
C13 C9 C10 C1 -42.0(2) . . . . ?
C13 C9 C10 C5 137.97(18) . . . . ?
C13 C9 C12 O2 169.11(15) . . . . ?
C13 C9 C12 O3 -13.2(3) . . . . ?
C13 C14 C15 C16 -179.73(17) . . . . ?
C13 C14 C15 I1 2.7(2) . . . . ?
C13 C14 C19 C1 -9.4(2) . . . . ?
C13 C14 C19 C18 175.38(16) . . . . ?
C14 C15 C16 C17 2.0(3) . . . . ?
C14 C15 C16 O4 176.85(16) . . . . ?
C15 C14 C19 C1 169.35(16) . . . . ?
C15 C14 C19 C18 -5.9(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C15 C16 C17 O5 -178.29(16) . . . . ?
C15 C16 O4 C20 107.5(2) . . . . ?
C16 C17 C18 C19 -3.4(3) . . . . ?
C16 C17 C18 O6 178.24(16) . . . . ?
C16 C17 O5 C21 -86.5(2) . . . . ?
C17 C16 O4 C20 -77.6(2) . . . . ?
C17 C18 C19 C1 -168.18(17) . . . . ?
C17 C18 C19 C14 6.8(3) . . . . ?
C17 C18 O6 C22 -111.14(19) . . . . ?
C18 C17 O5 C21 96.4(2) . . . . ?
C19 C1 C2 C3 177.61(18) . . . . ?
C19 C1 C10 C5 -176.40(16) . . . . ?
C19 C1 C10 C9 3.5(3) . . . . ?
C19 C14 C15 C16 1.6(3) . . . . ?
C19 C14 C15 I1 -175.92(13) . . . . ?
C19 C18 O6 C22 70.5(2) . . . . ?
I1 C15 C16 C17 179.60(13) . . . . ?
I1 C15 C16 O4 -5.5(2) . . . . ?
O1 C8 C9 C10 -175.53(17) . . . . ?
O1 C8 C9 C12 -53.0(2) . . . . ?
O1 C8 C9 C13 63.5(2) . . . . ?
O3 C12 O2 C11 1.4(3) . . . . ?
O4 C16 C17 C18 -175.99(16) . . . . ?
O4 C16 C17 O5 6.8(3) . . . . ?
O5 C17 C18 C19 173.81(16) . . . . ?
O5 C17 C18 O6 -4.6(3) . . . . ?
O6 C18 C19 C1 10.1(3) . . . . ?
O6 C18 C19 C14 -174.86(16) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id MEP261
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.627
_oxdiff_exptl_absorpt_empirical_full_min 0.562
