# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_NM21005
_database_code_depnum_ccdc_archive 'CCDC 2286804'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_NM21005             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.48 Note
RESPONSE: NoSpherA2.
;
# Added during the CSD deposition process: Friday 04 August 2023 01:18 PM
# end Validation Reply Form

_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.02 svn.rb8f36f48 for OlexSys, GUI svn.r6436)
;
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_publ_section_exptl              
;
Any special experimental details
;
_chemical_formula_moiety         'C32 H26 O4'
_chemical_formula_sum            'C32 H26 O4'
_chemical_formula_weight         474.561
_chemical_absolute_configuration ad
_chemical_oxdiff_formula         C32H26O4
_chemical_oxdiff_usercomment     '@ 120 K K53B9'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           ' F 2 -2d'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z
3 -x+1/4,y+1/4,z+1/4
4 x+1/4,-y+1/4,z+1/4
5 x,y+1/2,z+1/2
6 -x,-y+1/2,z+1/2
7 -x+1/4,y+3/4,z+3/4
8 x+1/4,-y+3/4,z+3/4
9 x+1/2,y,z+1/2
10 -x+1/2,-y,z+1/2
11 -x+3/4,y+1/4,z+3/4
12 x+3/4,-y+1/4,z+3/4
13 x+1/2,y+1/2,z
14 -x+1/2,-y+1/2,z
15 -x+3/4,y+3/4,z+1/4
16 x+3/4,-y+3/4,z+1/4

_symmetry_Int_Tables_number      43
_cell_length_a                   30.9566(5)
_cell_length_b                   17.6585(2)
_cell_length_c                   8.2176(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4492.13(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10706
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.5570
_cell_measurement_theta_min      5.6990
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       blade
_exptl_crystal_F_000             2006.594
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0161
-1 0 0 0.0161
1 -2 0 0.0377
-1 2 0 0.0181
2 0 1 0.1545
-2 0 -1 0.1511

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow cooling'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0003 0.0004 0.0000 0.0410 0.0196 0.0204
-1.0003 -0.0004 -0.0000 -0.0410 -0.0196 -0.0204
1.0001 -2.0000 -0.0002 0.1215 -0.1346 0.0067
-1.0001 2.0000 0.0002 -0.1215 0.1346 -0.0067
2.0003 0.0004 1.0004 0.0199 -0.0083 0.2113
-2.0003 -0.0004 -1.0004 -0.0199 0.0083 -0.2113

_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            28858
_diffrn_reflns_point_group_measured_fraction_full 0.9926
_diffrn_reflns_point_group_measured_fraction_max 0.9880
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.74
_diffrn_reflns_theta_min         5.72
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  27.00   1.00    2.50    --  -41.67  89.00 -96.00   94
  2  ω     -9.00  71.00   1.00    2.50    --   41.67 -89.00 148.00   80
  3  ω     38.00  64.00   1.00    5.00    --  111.00 -89.00 148.00   26
  4  ω    116.00 141.00   1.00    5.00    --  111.00  89.00 -96.00   25
  5  ω   -112.00 -15.00   1.00    2.50    --  -41.67 -57.00-180.00   97
  6  ω    -94.00  -8.00   1.00    2.50    --  -41.67 -19.00 -30.00   86
  7  ω   -113.00 -19.00   1.00    2.50    --  -41.67 -38.00 -90.00   94
  8  ω     61.00 127.00   1.00    2.50    --   41.67 178.00 150.00   66
  9  ω      9.00  34.00   1.00    2.50    --   41.67  82.00 -88.34   25
 10  ω     16.00  42.00   1.00    2.50    --   41.67  57.00  30.00   26
 11  ω     59.00  92.00   1.00    2.50    --   41.67  57.00  30.00   33
 12  ω     14.00  39.00   1.00    2.50    --   46.00  81.00  39.32   25
 13  ω     13.00  41.00   1.00    2.50    --   46.00  82.00 144.14   28
 14  ω     15.00  40.00   1.00    2.50    --   46.00  81.00 -20.07   25
 15  ω     14.00  39.00   1.00    2.50    --   46.00  79.00 117.19   25
 16  ω     14.00  39.00   1.00    2.50    --   46.00  81.00-145.21   25
 17  ω     26.00  53.00   1.00    2.50    --   54.00  70.00 -87.26   27
 18  ω     33.00  58.00   1.00    2.50    --   62.00  70.00 -59.04   25
 19  ω     33.00  58.00   1.00    2.50    --   62.00  71.00   5.95   25
 20  ω     32.00  58.00   1.00    2.50    --   62.00  71.00-133.79   26
 21  ω     33.00  65.00   1.00    2.50    --   62.00  69.00 145.54   32
 22  ω     36.00  63.00   1.00    2.50    --   66.00  71.00  64.01   27
 23  ω     36.00  62.00   1.00    2.50    --   66.00  71.00-163.66   26
 24  ω    109.00 135.00   1.00    2.50    --   66.00  59.00 121.39   26
 25  ω     40.00  65.00   1.00    2.50    --   66.00  59.00 121.39   25
 26  ω    110.00 136.00   1.00    2.50    --   66.00  71.00-163.66   26
 27  ω     36.00  62.00   1.00    2.50    --   66.00  70.00 -28.87   26
 28  ω     40.00  66.00   1.00    2.50    --   70.00  71.00  17.26   26
 29  ω     40.00  66.00   1.00    2.50    --   70.00  71.00 115.39   26
 30  ω    117.00 142.00   1.00    2.50    --   70.00  71.00 115.39   25
 31  ω     46.00  73.00   1.00    2.50    --   74.00  62.00   8.32   27
 32  ω     45.00  72.00   1.00    2.50    --   74.00  70.00-118.86   27
 33  ω     89.00 115.00   1.00    2.50    --   74.00  70.00-118.86   26
 34  ω     44.00  71.00   1.00    2.50    --   74.00  71.00 -37.67   27
 35  ω     44.00  71.00   1.00    2.50    --   74.00  70.00 -88.95   27
 36  ω     48.00  75.00   1.00    5.00    --   78.00  71.00  26.29   27
 37  ω     49.00  76.00   1.00    5.00    --   78.00  69.00-144.42   27
 38  ω     54.00  86.00   1.00    5.00    --   82.00  68.00 127.21   32
 39  ω     54.00  81.00   1.00    5.00    --   82.00  69.00  63.39   27
 40  ω     55.00  82.00   1.00    5.00    --   82.00  63.00 170.50   27
 41  ω     55.00  82.00   1.00    5.00    --   82.00  58.00 -75.98   27
 42  ω     56.00  89.00   1.00    5.00    --   86.00  71.00-171.23   33
 43  ω    125.00 157.00   1.00    5.00    --   86.00  71.00 169.10   32
 44  ω     56.00  82.00   1.00    5.00    --   86.00  71.00 169.10   26
 45  ω     58.00  85.00   1.00    5.00    --   86.00  62.00 -62.59   27
 46  ω     61.00  87.00   1.00    5.00    --   90.00  67.00  36.29   26
 47  ω     65.00  92.00   1.00    5.00    --   90.00  65.00 130.60   27
 48  ω     62.00  88.00   1.00    5.00    --   90.00  65.00  92.31   26
 49  ω     68.00  95.00   1.00    5.00    --   94.00  57.00 -34.69   27
 50  ω     65.00  91.00   1.00    5.00    --   94.00  67.00 -18.80   26
 51  ω    101.00 163.00   1.00    5.00    --   94.00  60.00 151.26   62
 52  ω     67.00  93.00   1.00    5.00    --   94.00  60.00 151.26   26
 53  ω     70.00  96.00   1.00    5.00    --   98.00  61.00   5.68   26
 54  ω     72.00  99.00   1.00    5.00    --  102.00  70.00 172.37   27
 55  ω     73.00 100.00   1.00    5.00    --  102.00  69.00  48.62   27
 56  ω     78.00 104.00   1.00    5.00    --  106.00  64.00 102.76   26
 57  ω    128.00 155.00   1.00    5.00    --  106.00  64.00 102.76   27
 58  ω     81.00 150.00   1.00    5.00    --  110.00  68.00-115.37   69
 59  ω     85.00 114.00   1.00    5.00    --  111.00  61.00-180.00   29
 60  ω     85.00 169.00   1.00    5.00    --  111.00  56.00-128.32   84
 61  ω    124.00 176.00   1.00    5.00    --  111.00  69.00   6.26   52
 62  ω     92.00 133.00   1.00    5.00    --  111.00 -45.00-180.00   41
 63  ω     54.00  79.00   1.00    5.00    --  111.00 -45.00-180.00   25
 64  ω     83.00 147.00   1.00    5.00    --  111.00  61.00 -90.00   64
 65  ω    138.00 168.00   1.00    5.00    --  111.00  61.00-120.00   30
 66  ω     76.00 111.00   1.00    5.00    --  111.00-125.00  90.00   35
 67  ω    122.00 178.00   1.00    5.00    --  111.00  61.00  90.00   56
 68  ω     83.00 119.00   1.00    5.00    --  111.00  69.00   6.26   36
 69  ω     83.00 118.00   1.00    5.00    --  111.00  61.00 150.00   35
 70  ω     83.00 114.00   1.00    5.00    --  111.00  61.00-120.00   31
 71  ω     83.00 120.00   1.00    5.00    --  111.00  61.00  90.00   37
 72  ω     59.00 123.00   1.00    5.00    --  111.00-138.00  57.72   64
 73  ω    120.00 174.00   1.00    5.00    --  111.00  61.00  37.33   54
 74  ω     91.00 176.00   1.00    5.00    --  111.00  45.00-150.00   85
 75  ω     69.00 108.00   1.00    5.00    --  111.00-105.00  75.73   39
 76  ω     83.00 113.00   1.00    5.00    --  111.00  61.00  37.33   30
 77  ω     38.00 105.00   1.00    5.00    --  111.00 -94.00 -60.00   67
 78  ω     85.00 134.00   1.00    5.00    --  111.00 -30.00   0.00   49
 79  ω     56.00  82.00   1.00    5.00    --  111.00 -30.00   0.00   26
 80  ω     84.00 168.00   1.00    5.00    --  111.00  61.00  60.00   84
 81  ω     49.00  99.00   1.00    5.00    --  111.00 -94.00   0.00   50
 82  ω    123.00 149.00   1.00    5.00    --  111.00  61.00-150.00   26
 83  ω     83.00 109.00   1.00    5.00    --  111.00  61.00-150.00   26
 84  ω     72.00 112.00   1.00    5.00    --  111.00-125.00 150.00   40
 85  ω     38.00  98.00   1.00    5.00    --  111.00 -77.00-150.00   60
 86  ω    120.00 169.00   1.00    5.00    --  111.00  63.00  -5.42   49
 87  ω     44.00  70.00   1.00    5.00    --  111.00-125.00 150.00   26
 88  ω     83.00 128.00   1.00    5.00    --  111.00  61.00 -60.75   45
 89  ω     87.00 142.00   1.00    5.00    --  111.00  44.00 -21.04   55
 90  ω     83.00 117.00   1.00    5.00    --  111.00  63.00  -5.42   34
 91  ω    153.00 178.00   1.00    5.00    --  111.00  44.00 -21.04   25
 92  ω    100.00 176.00   1.00    5.00    --  111.00 125.00 -90.00   76
 93  ω    134.00 178.00   1.00    5.00    --  111.00  61.00 120.00   44
 94  ω    129.00 154.00   1.00    5.00    --  111.00  45.00 -60.00   25
 95  ω     92.00 119.00   1.00    5.00    --  111.00  45.00 -60.00   27
 96  ω     40.00  65.00   1.00    5.00    --  111.00 -77.00  30.00   25
 97  ω     97.00 142.00   1.00    5.00    --  111.00 -77.00  30.00   45
 98  ω    141.00 167.00   1.00    5.00    --  111.00  30.00 150.00   26
 99  ω    103.00 131.00   1.00    5.00    --  111.00  30.00 150.00   28
100  ω    113.00 138.00   1.00    5.00    --  111.00 -61.00 -90.00   25
101  ω     83.00 114.00   1.00    5.00    --  111.00  61.00 120.00   31
102  ω     77.00 106.00   1.00    5.00    --  111.00 -94.00-120.00   29
103  ω     93.00 156.00   1.00    5.00    --  111.00  45.00  90.00   63
104  ω     63.00  89.00   1.00    5.00    --  111.00 -61.00 -90.00   26
105  ω     83.00 112.00   1.00    5.00    --  111.00-125.00-150.00   29
106  ω     33.00  75.00   1.00    5.00    --  111.00 -94.00 -90.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0409671000
_diffrn_orient_matrix_UB_12      -0.0402491000
_diffrn_orient_matrix_UB_13      -0.0620085000
_diffrn_orient_matrix_UB_21      0.0195798000
_diffrn_orient_matrix_UB_22      0.0770939000
_diffrn_orient_matrix_UB_23      -0.0474913000
_diffrn_orient_matrix_UB_31      0.0203491000
_diffrn_orient_matrix_UB_32      0.0068074000
_diffrn_orient_matrix_UB_33      0.1704811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.974
_reflns_limit_h_max              38
_reflns_limit_h_min              -38
_reflns_limit_k_max              22
_reflns_limit_k_min              -21
_reflns_limit_l_max              10
_reflns_limit_l_min              -9
_reflns_number_gt                2268
_reflns_number_total             2312
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1538
_refine_diff_density_min         -0.1192
_refine_diff_density_rms         0.0323
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_d_res_high            0.7954
_refine_ls_d_res_low             7.7391
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.0496
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0725
_refine_special_details          
;
The final model was refined using the NoSpherA2 function of Olex2.  Specific details are given elsewhere in the CIF.  H atoms were identified from a difference map and freely refined.


Alert level B
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax < 18) ........       4.48 Note  

NoSpherA2 used

Alert level C
PLAT351_ALERT_3_C Long   C-H (X0.96,N1.08A)  C13      - H13      .       1.11 Ang.  

NoSpherA2 used
;
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 C11, H11a, H11b, H11c
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, H12a, H12b, H12c
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.49183(3) 0.71365(4) 0.29427(10) 0.02491(18) Uani 1.000000 . .
O2 O 0.59631(3) 0.35318(4) 0.43196(10) 0.02471(19) Uani 1.000000 . .
C1 C 0.51977(3) 0.58835(5) 0.32718(12) 0.0185(2) Uani 1.000000 . .
C2 C 0.52108(3) 0.65843(6) 0.24993(13) 0.0204(2) Uani 1.000000 . .
C3 C 0.55255(4) 0.67788(6) 0.13191(14) 0.0233(2) Uani 1.000000 . .
H3 H 0.5515(6) 0.7284(11) 0.071(3) 0.049(5) Uani 1.000000 . .
C4 C 0.58499(4) 0.62767(6) 0.09926(15) 0.0246(2) Uani 1.000000 . .
H4 H 0.6096(6) 0.6396(11) 0.013(2) 0.042(4) Uani 1.000000 . .
C5 C 0.62226(4) 0.50821(6) 0.15250(14) 0.0245(2) Uani 1.000000 . .
H5 H 0.6458(5) 0.5245(9) 0.065(3) 0.044(5) Uani 1.000000 . .
C6 C 0.62636(4) 0.44106(6) 0.23461(14) 0.0241(2) Uani 1.000000 . .
H6 H 0.6549(5) 0.4072(11) 0.213(3) 0.039(5) Uani 1.000000 . .
C7 C 0.59309(3) 0.41803(5) 0.34170(13) 0.0207(2) Uani 1.000000 . .
C8 C 0.55539(3) 0.46038(5) 0.35939(13) 0.0188(2) Uani 1.000000 . .
C9 C 0.55309(3) 0.53441(5) 0.28906(13) 0.0189(2) Uani 1.000000 . .
C10 C 0.58681(3) 0.55681(6) 0.17948(14) 0.0216(2) Uani 1.000000 . .
C11 C 0.46254(4) 0.73644(7) 0.17023(16) 0.0305(3) Uani 1.000000 . U
H11a H 0.4440(6) 0.7805(10) 0.229(3) 0.047(5) Uani 1.000000 . U
H11b H 0.4799(6) 0.7582(11) 0.075(3) 0.046(4) Uani 1.000000 . U
H11c H 0.4414(6) 0.6893(10) 0.133(3) 0.053(5) Uani 1.000000 . U
C12 C 0.63496(4) 0.30981(7) 0.42083(17) 0.0304(3) Uani 1.000000 . U
H12a H 0.6378(8) 0.2885(11) 0.304(3) 0.054(4) Uani 1.000000 . U
H12b H 0.6626(6) 0.3408(9) 0.448(3) 0.042(4) Uani 1.000000 . U
H12c H 0.6322(6) 0.2657(11) 0.512(3) 0.050(4) Uani 1.000000 . U
C13 C 0.51748(3) 0.42386(6) 0.44743(13) 0.0181(2) Uani 1.000000 . .
H13 H 0.5282(6) 0.3658(8) 0.479(3) 0.037(5) Uani 1.000000 . .
C14 C 0.50736(3) 0.46265(5) 0.60608(14) 0.0190(2) Uani 1.000000 . .
C15 C 0.51520(4) 0.42582(7) 0.75375(14) 0.0236(2) Uani 1.000000 . .
H15 H 0.5268(8) 0.3684(11) 0.750(3) 0.053(6) Uani 1.000000 . .
C16 C 0.50774(4) 0.46294(7) 0.90098(15) 0.0284(2) Uani 1.000000 . .
H16 H 0.5136(9) 0.4365(10) 1.014(3) 0.064(7) Uani 1.000000 . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3796(14) . ?
O1 C11 1.4224(14) . ?
O2 C7 1.3680(13) . ?
O2 C12 1.4235(13) . ?
C1 C2 1.3914(14) . ?
C1 C9 1.4386(13) . ?
C1 C13 1.5338(14) 2_665 ?
C2 C3 1.4170(15) . ?
C3 H3 1.023(18) . ?
C3 C4 1.3663(16) . ?
C4 H4 1.06(2) . ?
C4 C10 1.4154(15) . ?
C5 H5 1.06(2) . ?
C5 C6 1.3702(16) . ?
C5 C10 1.4107(15) . ?
C6 H6 1.082(19) . ?
C6 C7 1.4144(15) . ?
C7 C8 1.3937(14) . ?
C8 C9 1.4311(13) . ?
C8 C13 1.5220(13) . ?
C9 C10 1.4343(14) . ?
C11 H11a 1.081(19) . ?
C11 H11b 1.024(19) . ?
C11 H11c 1.101(19) . ?
C12 H12a 1.03(2) . ?
C12 H12b 1.040(18) . ?
C12 H12c 1.08(2) . ?
C13 H13 1.107(15) . ?
C13 C14 1.5057(14) . ?
C14 C14 1.3955(19) 2_665 ?
C14 C15 1.3981(15) . ?
C15 H15 1.076(19) . ?
C15 C16 1.3953(17) . ?
C16 C16 1.394(2) 2_665 ?
C16 H16 1.06(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C2 115.42(9) . . ?
C12 O2 C7 118.47(9) . . ?
C9 C1 C2 117.94(9) . . ?
C13 C1 C2 116.17(8) 2_665 . ?
C13 C1 C9 125.89(9) 2_665 . ?
C1 C2 O1 119.26(9) . . ?
C3 C2 O1 117.43(9) . . ?
C3 C2 C1 123.23(10) . . ?
H3 C3 C2 121.5(10) . . ?
C4 C3 C2 118.84(10) . . ?
C4 C3 H3 119.6(10) . . ?
H4 C4 C3 121.9(10) . . ?
C10 C4 C3 120.77(11) . . ?
C10 C4 H4 117.3(10) . . ?
C6 C5 H5 120.2(9) . . ?
C10 C5 H5 118.4(9) . . ?
C10 C5 C6 121.41(10) . . ?
H6 C6 C5 118.2(9) . . ?
C7 C6 C5 119.20(10) . . ?
C7 C6 H6 122.6(9) . . ?
C6 C7 O2 121.67(9) . . ?
C8 C7 O2 116.98(9) . . ?
C8 C7 C6 121.35(10) . . ?
C9 C8 C7 119.33(9) . . ?
C13 C8 C7 117.90(9) . . ?
C13 C8 C9 122.72(9) . . ?
C8 C9 C1 123.55(9) . . ?
C10 C9 C1 118.42(9) . . ?
C10 C9 C8 117.98(9) . . ?
C5 C10 C4 119.71(10) . . ?
C9 C10 C4 120.48(10) . . ?
C9 C10 C5 119.81(10) . . ?
H11a C11 O1 102.8(12) . . ?
H11b C11 O1 108.7(10) . . ?
H11b C11 H11a 110.4(15) . . ?
H11c C11 O1 111.2(12) . . ?
H11c C11 H11a 110.6(14) . . ?
H11c C11 H11b 112.6(17) . . ?
H12a C12 O2 109.1(14) . . ?
H12b C12 O2 113.2(9) . . ?
H12b C12 H12a 108.8(17) . . ?
H12c C12 O2 106.1(11) . . ?
H12c C12 H12a 112.5(16) . . ?
H12c C12 H12b 107.1(16) . . ?
C8 C13 C1 109.45(8) . 2_665 ?
H13 C13 C1 104.1(10) . 2_665 ?
H13 C13 C8 105.8(10) . . ?
C14 C13 C1 117.73(8) . 2_665 ?
C14 C13 C8 112.29(8) . . ?
C14 C13 H13 106.4(11) . . ?
C14 C14 C13 119.87(6) 2_665 . ?
C15 C14 C13 120.25(9) . . ?
H15 C15 C14 118.0(11) . . ?
C16 C15 C14 120.36(10) . . ?
C16 C15 H15 121.7(11) . . ?
C16 C16 C15 119.87(7) 2_665 . ?
H16 C16 C15 121.8(11) . . ?

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 C2 C1 C9 -174.43(9) . . . . ?
O1 C2 C1 C13 5.17(11) . . . 2_665 ?
O1 C2 C3 C4 172.45(10) . . . . ?
O2 C7 C6 C5 -177.17(10) . . . . ?
O2 C7 C8 C9 169.95(9) . . . . ?
O2 C7 C8 C13 -12.67(11) . . . . ?
C1 C2 C3 C4 -4.46(13) . . . . ?
C1 C9 C8 C7 -166.93(10) . . . . ?
C1 C9 C8 C13 15.82(12) . . . . ?
C1 C9 C10 C4 -5.88(11) . . . . ?
C1 C9 C10 C5 173.54(9) . . . . ?
C1 C13 C8 C7 -113.40(9) 2_665 . . . ?
C1 C13 C8 C9 63.88(10) 2_665 . . . ?
C1 C13 C14 C14 -63.35(11) . 2_665 2_665 . ?
C1 C13 C14 C15 120.66(9) 2_665 . . . ?
C2 C3 C4 C10 1.15(12) . . . . ?
C3 C4 C10 C5 -175.46(11) . . . . ?
C3 C4 C10 C9 3.96(14) . . . . ?
C4 C10 C5 C6 176.37(10) . . . . ?
C4 C10 C9 C8 176.47(10) . . . . ?
C5 C6 C7 C8 3.11(13) . . . . ?
C5 C10 C9 C8 -4.12(12) . . . . ?
C6 C7 C8 C9 -10.32(12) . . . . ?
C6 C7 C8 C13 167.07(10) . . . . ?
C7 C8 C9 C10 10.60(12) . . . . ?
C7 C8 C13 C14 113.90(10) . . . . ?
C8 C13 C14 C14 65.12(11) . . . 2_665 ?
C8 C13 C14 C15 -110.87(9) . . . . ?
C13 C14 C14 C13 6.37(9) . . 2_665 2_665 ?
C13 C14 C14 C15 -177.62(11) . . 2_665 2_665 ?
C13 C14 C15 C16 177.00(10) . . . . ?
C14 C14 C15 C16 1.01(15) 2_665 . . . ?
C14 C15 C16 C16 0.20(12) . . . 2_665 ?
C15 C16 C16 C15 -0.81(12) . . 2_665 2_665 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K53B9
_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 4.011
_oxdiff_exptl_absorpt_empirical_full_min 0.507
loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
C11 H11a 0.004000 -0.001840 0.001393 -0.003804
C11 H11b 0.004000 0.002091 -0.001750 -0.005507
C11 H11c 0.004000 0.004597 0.002508 -0.007193
H11a H11b 0.004000 -0.010206 -0.009734 -0.002043
H11a H11c 0.004000 -0.015463 0.002093 0.000567
H11b H11c 0.004000 0.008478 -0.017187 -0.000935
C12 H12a 0.004000 -0.004157 0.000512 -0.005479
C12 H12b 0.004000 0.000545 0.003109 -0.005566
C12 H12c 0.004000 -0.002571 0.001176 -0.005823
H12a H12b 0.004000 0.011598 0.008362 0.003046
H12a H12c 0.004000 0.012791 -0.007995 -0.003834
H12b H12c 0.004000 0.009377 0.012169 -0.002964

####################################################################### 
# 
# 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_nm22008
_database_code_depnum_ccdc_archive 'CCDC 2286808'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT414_nm22008             
;
PROBLEM: Short Intra D-H..H-X       H3       ..H31      .       1.80 Ang.
RESPONSE: H atoms freely refined
;
_vrf_PLAT420_nm22008             
;
PROBLEM: D-H Bond Without Acceptor  O2       --H2       .     Please Check
RESPONSE: Consequence of solvent masking
;
_vrf_PLAT910_nm22008             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note
RESPONSE: not significant
;
# Added during the CSD deposition process: Friday 04 August 2023 01:21 PM
# end Validation Reply Form

_audit_creation_date             2022-05-05
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H20 O4, 1.5[CH4O]'
_chemical_formula_sum            'C33.50 H26 O5.50'
_chemical_formula_weight         516.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         C32H20O4
_chemical_oxdiff_usercomment     '@ 120 K K71B49c'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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                   10.4986(5)
_cell_length_b                   11.6083(6)
_cell_length_c                   12.2425(6)
_cell_angle_alpha                97.683(4)
_cell_angle_beta                 106.716(4)
_cell_angle_gamma                100.894(4)
_cell_volume                     1374.87(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9071
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      29.1750
_cell_measurement_theta_min      3.8280
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             542
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0329
0 -1 0 0.0230
0 0 -1 0.0684
1 0 -1 0.0911
-1 0 1 0.0793
-2 1 0 0.0917
2 -1 0 0.0917
1 -1 2 0.0917
-1 1 -2 0.0646
-1 0 2 0.0951

_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow cooling'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_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
0.0009 0.9993 -0.0005 0.0630 0.0048 0.0059
-0.0009 -0.9993 0.0005 -0.0630 -0.0048 -0.0059
-0.0002 -0.0002 -0.9992 -0.0179 -0.0007 0.0590
0.9994 -0.0008 -0.9994 -0.0037 0.0678 0.0398
-0.9994 0.0008 0.9994 0.0037 -0.0678 -0.0398
-1.9983 1.0005 -0.0000 0.0347 -0.1324 0.0444
1.9983 -1.0005 0.0000 -0.0347 0.1324 -0.0444
0.9991 -0.9996 1.9986 -0.0130 0.0653 -0.1432
-0.9991 0.9996 -1.9986 0.0130 -0.0653 0.1432
-0.9992 0.0010 1.9986 0.0216 -0.0671 -0.0988

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36195
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.328
_diffrn_reflns_theta_min         3.648
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  12.00   1.00   30.00    --  -15.66 -22.00 -80.00   99
  2  ω    -43.00  56.00   1.00   30.00    --  -15.66  22.00  85.00   99
  3  ω    -54.00  45.00   1.00   30.00    --   17.38 -22.00 -80.00   99
  4  ω    -10.00  89.00   1.00   30.00    --   17.38  22.00  85.00   99
  5  ω    -39.00  11.00   1.00   30.00    --  -15.66 -77.00 120.00   50
  6  ω    -35.00  53.00   1.00   30.00    --  -15.66  38.00 150.00   88
  7  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00  60.00   48
  8  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00 -60.00   48
  9  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00 -30.00   48
 10  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00-120.00   48
 11  ω    -42.00  39.00   1.00   30.00    --  -15.66  77.00 -90.00   81
 12  ω    -20.00  56.00   1.00   30.00    --   17.38 -99.00  60.00   76
 13  ω    -20.00  56.00   1.00   30.00    --   17.38 -99.00-180.00   76
 14  ω     -9.00  39.00   1.00   30.00    --   17.38  77.00 150.00   48
 15  ω    -20.00  56.00   1.00   30.00    --   17.38 -99.00 -30.00   76
 16  ω    -20.00  56.00   1.00   30.00    --   17.38 -99.00 -90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction XCalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142266000
_diffrn_orient_matrix_UB_12      0.0630581000
_diffrn_orient_matrix_UB_13      0.0178976000
_diffrn_orient_matrix_UB_21      0.0686015000
_diffrn_orient_matrix_UB_22      0.0046945000
_diffrn_orient_matrix_UB_23      0.0007288000
_diffrn_orient_matrix_UB_31      -0.0192555000
_diffrn_orient_matrix_UB_32      0.0058906000
_diffrn_orient_matrix_UB_33      -0.0590850000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5291
_reflns_number_total             6729
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.034
_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)+(0.0626P)²+0.8917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1457
_refine_special_details          
;
H atoms were identified from a difference map and freely refined.  The solvent masking routine of Olex2 was used to handle methanol which could not be modelled using discrete atoms.  Details are given elsewhere in the CIF.

#===============================================================================
#>>> The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

414_ALERT_2_B Short Intra D-H..H-X       H3       ..H31              1.80 Ang.
                                                      x,y,z  =      1_555 Check

H atoms freely refined

420_ALERT_2_B D-H Bond Without Acceptor  O2       --H2       .     Please Check

Consequence of solvent masking

910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         14 Note

Not significant

#===============================================================================
222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        7.0 Ratio
414_ALERT_2_C Short Intra D-H..H-X       H4       ..H32              1.94 Ang.
                                                      x,y,z  =      1_555 Check
906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.600 Check
911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report

Nothing here is significant

#===============================================================================
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 -0.02343(13) 0.42936(12) 0.70554(11) 0.0194(3) Uani 1 1 d . . . . .
H1 H -0.097(3) 0.417(2) 0.722(2) 0.046(8) Uiso 1 1 d . . . . .
O2 O 0.64921(13) 0.30633(13) 0.90867(11) 0.0236(3) Uani 1 1 d . . . . .
H2 H 0.705(3) 0.280(3) 0.967(3) 0.063(9) Uiso 1 1 d . . . . .
O3 O 0.09061(13) 0.59673(13) 0.59577(13) 0.0262(3) Uani 1 1 d . . . . .
H3 H 0.045(3) 0.531(3) 0.618(3) 0.061(9) Uiso 1 1 d . . . . .
O4 O 0.73394(12) 0.39715(12) 0.74473(12) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.709(3) 0.372(3) 0.796(3) 0.056(9) Uiso 1 1 d . . . . .
C1 C 0.08015(17) 0.40436(15) 0.79035(15) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.19389(17) 0.38490(14) 0.76253(14) 0.0133(3) Uani 1 1 d . . . . .
C3 C 0.30430(17) 0.36095(14) 0.85073(14) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.42611(17) 0.33681(15) 0.83183(14) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.52993(17) 0.32452(15) 0.92651(15) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.51836(19) 0.32953(17) 1.03813(16) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.590(2) 0.324(2) 1.097(2) 0.035(6) Uiso 1 1 d . . . . .
C7 C 0.40017(19) 0.34503(16) 1.05556(15) 0.0203(4) Uani 1 1 d . . . . .
H7 H 0.392(2) 0.353(2) 1.132(2) 0.036(6) Uiso 1 1 d . . . . .
C8 C 0.29192(18) 0.36210(15) 0.96445(15) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.17166(19) 0.38060(17) 0.98607(15) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.167(2) 0.3786(19) 1.0597(19) 0.022(5) Uiso 1 1 d . . . . .
C10 C 0.06688(18) 0.40107(16) 0.90141(15) 0.0188(4) Uani 1 1 d . . . . .
H10 H -0.018(2) 0.4130(18) 0.9131(17) 0.020(5) Uiso 1 1 d . . . . .
C11 C 0.22381(18) 0.59787(16) 0.60389(15) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.28507(17) 0.50462(15) 0.62980(14) 0.0141(3) Uani 1 1 d . . . . .
C13 C 0.42892(16) 0.52191(14) 0.64453(13) 0.0126(3) Uani 1 1 d . . . . .
C14 C 0.50880(16) 0.43882(14) 0.68415(13) 0.0126(3) Uani 1 1 d . . . . .
C15 C 0.64822(17) 0.46882(15) 0.70014(14) 0.0152(3) Uani 1 1 d . . . . .
C16 C 0.71300(18) 0.57272(16) 0.67257(15) 0.0171(4) Uani 1 1 d . . . . .
H16 H 0.802(2) 0.5852(18) 0.6762(17) 0.017(5) Uiso 1 1 d . . . . .
C17 C 0.63934(18) 0.65225(16) 0.63457(14) 0.0166(3) Uani 1 1 d . . . . .
H17 H 0.681(2) 0.7260(18) 0.6152(16) 0.018(5) Uiso 1 1 d . . . . .
C18 C 0.49840(17) 0.63073(15) 0.62239(14) 0.0154(3) Uani 1 1 d . . . . .
C19 C 0.42645(19) 0.71876(16) 0.58903(16) 0.0205(4) Uani 1 1 d . . . . .
H19 H 0.479(2) 0.788(2) 0.5735(19) 0.029(6) Uiso 1 1 d . . . . .
C20 C 0.29300(19) 0.70391(17) 0.58122(17) 0.0226(4) Uani 1 1 d . . . . .
H20 H 0.239(2) 0.765(2) 0.5560(19) 0.030(6) Uiso 1 1 d . . . . .
C21 C 0.20880(16) 0.27460(15) 0.57641(14) 0.0132(3) Uani 1 1 d . . . . .
C22 C 0.10210(17) 0.20236(15) 0.48525(14) 0.0150(3) Uani 1 1 d . . . . .
H22 H 0.018(2) 0.2306(17) 0.4565(16) 0.013(5) Uiso 1 1 d . . . . .
C23 C 0.11314(17) 0.09201(15) 0.42840(14) 0.0159(3) Uani 1 1 d . . . . .
C24 C 0.00459(19) 0.01574(16) 0.33334(16) 0.0214(4) Uani 1 1 d . . . . .
H24 H -0.080(2) 0.0383(18) 0.3079(17) 0.021(5) Uiso 1 1 d . . . . .
C25 C 0.0191(2) -0.08925(17) 0.27918(17) 0.0257(4) Uani 1 1 d . . . . .
H25 H -0.058(2) -0.143(2) 0.2137(19) 0.028(6) Uiso 1 1 d . . . . .
C26 C 0.1441(2) -0.12401(17) 0.31762(18) 0.0267(4) Uani 1 1 d . . . . .
H26 H 0.156(2) -0.196(2) 0.282(2) 0.039(7) Uiso 1 1 d . . . . .
C27 C 0.2501(2) -0.05374(16) 0.40964(16) 0.0228(4) Uani 1 1 d . . . . .
H27 H 0.340(2) -0.0765(19) 0.4382(18) 0.026(5) Uiso 1 1 d . . . . .
C28 C 0.23800(18) 0.05618(15) 0.46793(14) 0.0163(3) Uani 1 1 d . . . . .
C29 C 0.34616(17) 0.13235(15) 0.56284(15) 0.0157(3) Uani 1 1 d . . . . .
H29 H 0.433(2) 0.1054(17) 0.5905(16) 0.016(5) Uiso 1 1 d . . . . .
C30 C 0.33286(16) 0.23943(14) 0.61584(14) 0.0130(3) Uani 1 1 d . . . . .
C31 C 0.19323(16) 0.38958(14) 0.63872(14) 0.0122(3) Uani 1 1 d . . . . .
H31 H 0.0994(19) 0.3944(16) 0.5948(15) 0.009(4) Uiso 1 1 d . . . . .
C32 C 0.45074(16) 0.32119(15) 0.71443(14) 0.0131(3) Uani 1 1 d . . . . .
H32 H 0.521(2) 0.2816(17) 0.7236(16) 0.015(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.84(3) . ?
O1 C1 1.377(2) . ?
O2 H2 0.91(3) . ?
O2 C5 1.380(2) . ?
O3 H3 0.94(3) . ?
O3 C11 1.371(2) . ?
O4 H4 0.82(3) . ?
O4 C15 1.3863(19) . ?
C1 C2 1.381(2) . ?
C1 C10 1.411(2) . ?
C2 C3 1.438(2) . ?
C2 C31 1.522(2) . ?
C3 C4 1.434(2) . ?
C3 C8 1.434(2) . ?
C4 C5 1.389(2) . ?
C4 C32 1.526(2) . ?
C5 C6 1.401(3) . ?
C6 H6 0.90(2) . ?
C6 C7 1.358(3) . ?
C7 H7 0.96(2) . ?
C7 C8 1.411(2) . ?
C8 C9 1.411(3) . ?
C9 H9 0.92(2) . ?
C9 C10 1.360(3) . ?
C10 H10 0.97(2) . ?
C11 C12 1.387(2) . ?
C11 C20 1.410(3) . ?
C12 C13 1.440(2) . ?
C12 C31 1.529(2) . ?
C13 C14 1.437(2) . ?
C13 C18 1.435(2) . ?
C14 C15 1.388(2) . ?
C14 C32 1.525(2) . ?
C15 C16 1.401(2) . ?
C16 H16 0.91(2) . ?
C16 C17 1.358(2) . ?
C17 H17 0.98(2) . ?
C17 C18 1.413(2) . ?
C18 C19 1.417(2) . ?
C19 H19 0.96(2) . ?
C19 C20 1.352(3) . ?
C20 H20 1.01(2) . ?
C21 C22 1.371(2) . ?
C21 C30 1.410(2) . ?
C21 C31 1.507(2) . ?
C22 H22 0.987(19) . ?
C22 C23 1.415(2) . ?
C23 C24 1.420(2) . ?
C23 C28 1.421(2) . ?
C24 H24 0.96(2) . ?
C24 C25 1.364(3) . ?
C25 H25 0.99(2) . ?
C25 C26 1.414(3) . ?
C26 H26 0.94(3) . ?
C26 C27 1.365(3) . ?
C27 H27 1.01(2) . ?
C27 C28 1.423(2) . ?
C28 C29 1.417(2) . ?
C29 H29 1.00(2) . ?
C29 C30 1.374(2) . ?
C30 C32 1.510(2) . ?
C31 H31 0.993(18) . ?
C32 H32 0.93(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
C1 O1 H1 110.4(18) . . ?
C5 O2 H2 114.4(19) . . ?
C11 O3 H3 114.7(18) . . ?
C15 O4 H4 107(2) . . ?
O1 C1 C2 117.92(15) . . ?
O1 C1 C10 119.15(15) . . ?
C2 C1 C10 122.93(16) . . ?
C1 C2 C3 118.69(15) . . ?
C1 C2 C31 117.16(14) . . ?
C3 C2 C31 124.14(14) . . ?
C4 C3 C2 123.92(15) . . ?
C8 C3 C2 117.91(15) . . ?
C8 C3 C4 118.17(15) . . ?
C3 C4 C32 125.11(14) . . ?
C5 C4 C3 118.27(15) . . ?
C5 C4 C32 116.61(15) . . ?
O2 C5 C4 117.96(15) . . ?
O2 C5 C6 119.12(15) . . ?
C4 C5 C6 122.92(16) . . ?
C5 C6 H6 119.0(15) . . ?
C7 C6 C5 119.31(16) . . ?
C7 C6 H6 121.7(15) . . ?
C6 C7 H7 120.8(14) . . ?
C6 C7 C8 120.97(17) . . ?
C8 C7 H7 118.0(14) . . ?
C7 C8 C3 120.17(16) . . ?
C9 C8 C3 120.25(16) . . ?
C9 C8 C7 119.57(16) . . ?
C8 C9 H9 117.6(13) . . ?
C10 C9 C8 121.27(16) . . ?
C10 C9 H9 121.1(13) . . ?
C1 C10 H10 117.8(12) . . ?
C9 C10 C1 118.87(16) . . ?
C9 C10 H10 123.3(12) . . ?
O3 C11 C12 124.22(16) . . ?
O3 C11 C20 112.90(15) . . ?
C12 C11 C20 122.87(16) . . ?
C11 C12 C13 118.16(15) . . ?
C11 C12 C31 117.08(15) . . ?
C13 C12 C31 124.75(14) . . ?
C14 C13 C12 124.10(15) . . ?
C18 C13 C12 118.16(14) . . ?
C18 C13 C14 117.70(15) . . ?
C13 C14 C32 123.93(14) . . ?
C15 C14 C13 118.43(15) . . ?
C15 C14 C32 117.60(14) . . ?
O4 C15 C14 122.06(15) . . ?
O4 C15 C16 114.94(15) . . ?
C14 C15 C16 123.00(15) . . ?
C15 C16 H16 120.5(13) . . ?
C17 C16 C15 119.43(16) . . ?
C17 C16 H16 120.0(13) . . ?
C16 C17 H17 121.8(12) . . ?
C16 C17 C18 120.57(16) . . ?
C18 C17 H17 117.6(12) . . ?
C17 C18 C13 120.69(15) . . ?
C17 C18 C19 119.10(16) . . ?
C19 C18 C13 120.21(16) . . ?
C18 C19 H19 115.2(13) . . ?
C20 C19 C18 120.95(17) . . ?
C20 C19 H19 123.8(13) . . ?
C11 C20 H20 118.1(13) . . ?
C19 C20 C11 119.40(16) . . ?
C19 C20 H20 122.4(13) . . ?
C22 C21 C30 120.07(15) . . ?
C22 C21 C31 120.63(14) . . ?
C30 C21 C31 119.25(14) . . ?
C21 C22 H22 118.7(11) . . ?
C21 C22 C23 121.44(15) . . ?
C23 C22 H22 119.8(11) . . ?
C22 C23 C24 122.65(16) . . ?
C22 C23 C28 118.66(15) . . ?
C24 C23 C28 118.68(16) . . ?
C23 C24 H24 119.0(12) . . ?
C25 C24 C23 121.26(17) . . ?
C25 C24 H24 119.8(12) . . ?
C24 C25 H25 120.4(13) . . ?
C24 C25 C26 119.99(18) . . ?
C26 C25 H25 119.6(13) . . ?
C25 C26 H26 121.4(15) . . ?
C27 C26 C25 120.42(18) . . ?
C27 C26 H26 118.2(15) . . ?
C26 C27 H27 121.8(12) . . ?
C26 C27 C28 120.89(18) . . ?
C28 C27 H27 117.3(12) . . ?
C23 C28 C27 118.75(16) . . ?
C29 C28 C23 118.61(15) . . ?
C29 C28 C27 122.64(16) . . ?
C28 C29 H29 117.7(11) . . ?
C30 C29 C28 121.45(15) . . ?
C30 C29 H29 120.9(11) . . ?
C21 C30 C32 119.54(14) . . ?
C29 C30 C21 119.75(15) . . ?
C29 C30 C32 120.69(14) . . ?
C2 C31 C12 113.15(13) . . ?
C2 C31 H31 106.1(10) . . ?
C12 C31 H31 103.8(10) . . ?
C21 C31 C2 112.66(13) . . ?
C21 C31 C12 115.88(13) . . ?
C21 C31 H31 103.8(10) . . ?
C4 C32 H32 105.2(12) . . ?
C14 C32 C4 113.56(13) . . ?
C14 C32 H32 103.9(12) . . ?
C30 C32 C4 114.55(14) . . ?
C30 C32 C14 113.59(13) . . ?
C30 C32 H32 104.6(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.84(3) 1.85(3) 2.6925(18) 174(3) 1_455 yes
O3 H3 O1 0.94(3) 1.87(3) 2.7854(19) 163(3) . yes
O4 H4 O2 0.82(3) 1.86(3) 2.6776(19) 177(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.81(14) . . . . ?
O1 C1 C2 C31 -1.6(2) . . . . ?
O1 C1 C10 C9 -177.66(16) . . . . ?
O2 C5 C6 C7 -178.70(16) . . . . ?
O3 C11 C12 C13 -175.18(16) . . . . ?
O3 C11 C12 C31 5.8(3) . . . . ?
O3 C11 C20 C19 178.34(17) . . . . ?
O4 C15 C16 C17 -176.27(15) . . . . ?
C1 C2 C3 C4 178.59(15) . . . . ?
C1 C2 C3 C8 -1.8(2) . . . . ?
C1 C2 C31 C12 104.65(17) . . . . ?
C1 C2 C31 C21 -121.48(16) . . . . ?
C2 C1 C10 C9 1.6(3) . . . . ?
C2 C3 C4 C5 174.94(16) . . . . ?
C2 C3 C4 C32 -6.1(3) . . . . ?
C2 C3 C8 C7 -176.87(16) . . . . ?
C2 C3 C8 C9 3.0(2) . . . . ?
C3 C2 C31 C12 -75.7(2) . . . . ?
C3 C2 C31 C21 58.1(2) . . . . ?
C3 C4 C5 O2 -177.31(14) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C32 C14 86.06(19) . . . . ?
C3 C4 C32 C30 -46.7(2) . . . . ?
C3 C8 C9 C10 -1.9(3) . . . . ?
C4 C3 C8 C7 2.7(2) . . . . ?
C4 C3 C8 C9 -177.42(16) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C4 C32 C14 -95.01(17) . . . . ?
C5 C4 C32 C30 132.20(16) . . . . ?
C5 C6 C7 C8 -3.2(3) . . . . ?
C6 C7 C8 C3 1.2(3) . . . . ?
C6 C7 C8 C9 -178.60(17) . . . . ?
C7 C8 C9 C10 177.93(17) . . . . ?
C8 C3 C4 C5 -4.6(2) . . . . ?
C8 C3 C4 C32 174.27(15) . . . . ?
C8 C9 C10 C1 -0.4(3) . . . . ?
C10 C1 C2 C3 -0.4(3) . . . . ?
C10 C1 C2 C31 179.21(15) . . . . ?
C11 C12 C13 C14 172.71(16) . . . . ?
C11 C12 C13 C18 -4.9(2) . . . . ?
C11 C12 C31 C2 -93.82(17) . . . . ?
C11 C12 C31 C21 133.87(16) . . . . ?
C12 C11 C20 C19 -2.6(3) . . . . ?
C12 C13 C14 C15 -176.88(15) . . . . ?
C12 C13 C14 C32 0.6(2) . . . . ?
C12 C13 C18 C17 -179.53(15) . . . . ?
C12 C13 C18 C19 1.1(2) . . . . ?
C13 C12 C31 C2 87.19(19) . . . . ?
C13 C12 C31 C21 -45.1(2) . . . . ?
C13 C14 C15 O4 176.05(14) . . . . ?
C13 C14 C15 C16 -4.1(2) . . . . ?
C13 C14 C32 C4 -76.23(19) . . . . ?
C13 C14 C32 C30 57.0(2) . . . . ?
C13 C18 C19 C20 2.2(3) . . . . ?
C14 C13 C18 C17 2.7(2) . . . . ?
C14 C13 C18 C19 -176.71(15) . . . . ?
C14 C15 C16 C17 3.9(3) . . . . ?
C15 C14 C32 C4 101.31(17) . . . . ?
C15 C14 C32 C30 -125.44(16) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C13 -3.0(3) . . . . ?
C16 C17 C18 C19 176.37(16) . . . . ?
C17 C18 C19 C20 -177.15(17) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
C18 C13 C14 C32 178.31(14) . . . . ?
C18 C19 C20 C11 -1.6(3) . . . . ?
C20 C11 C12 C13 5.8(3) . . . . ?
C20 C11 C12 C31 -173.21(16) . . . . ?
C21 C22 C23 C24 -179.62(16) . . . . ?
C21 C22 C23 C28 0.3(2) . . . . ?
C21 C30 C32 C4 67.25(19) . . . . ?
C21 C30 C32 C14 -65.5(2) . . . . ?
C22 C21 C30 C29 -0.2(2) . . . . ?
C22 C21 C30 C32 178.53(15) . . . . ?
C22 C21 C31 C2 111.32(17) . . . . ?
C22 C21 C31 C12 -116.15(17) . . . . ?
C22 C23 C24 C25 178.97(17) . . . . ?
C22 C23 C28 C27 -178.95(16) . . . . ?
C22 C23 C28 C29 0.2(2) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C23 C28 C29 C30 -0.6(2) . . . . ?
C24 C23 C28 C27 0.9(2) . . . . ?
C24 C23 C28 C29 -179.96(16) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C26 C27 C28 C23 -0.2(3) . . . . ?
C26 C27 C28 C29 -179.22(17) . . . . ?
C27 C28 C29 C30 178.44(16) . . . . ?
C28 C23 C24 C25 -0.9(3) . . . . ?
C28 C29 C30 C21 0.7(2) . . . . ?
C28 C29 C30 C32 -178.09(15) . . . . ?
C29 C30 C32 C4 -113.99(17) . . . . ?
C29 C30 C32 C14 113.23(17) . . . . ?
C30 C21 C22 C23 -0.2(2) . . . . ?
C30 C21 C31 C2 -66.16(19) . . . . ?
C30 C21 C31 C12 66.37(19) . . . . ?
C31 C2 C3 C4 -1.0(3) . . . . ?
C31 C2 C3 C8 178.59(14) . . . . ?
C31 C12 C13 C14 -8.3(3) . . . . ?
C31 C12 C13 C18 174.03(15) . . . . ?
C31 C21 C22 C23 -177.69(15) . . . . ?
C31 C21 C30 C29 177.26(15) . . . . ?
C31 C21 C30 C32 -4.0(2) . . . . ?
C32 C4 C5 O2 3.7(2) . . . . ?
C32 C4 C5 C6 -176.17(16) . . . . ?
C32 C14 C15 O4 -1.6(2) . . . . ?
C32 C14 C15 C16 178.22(15) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 51 electrons were 
found in a volume of 404Å³ in 1 void per unit cell. 
This is consistent with the presence of 
1.5[CH4O] per Formula Unit 
which account for 54 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.018 0.000 0.000 404.4 51.1 '3 MeOH'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K71B49c
_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 1.038
_oxdiff_exptl_absorpt_empirical_full_min 0.915
####################################################################### 
# 
# 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_nm22007
_database_code_depnum_ccdc_archive 'CCDC 2286806'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_nm22007             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         15 Note
RESPONSE: not significant
;
# Added during the CSD deposition process: Friday 04 August 2023 01:13 PM
# end Validation Reply Form

_audit_creation_date             2022-05-04
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
g.s.nichol@ed.ac.uk
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H2 Cl2), C44 H22 N4 O4'
_chemical_formula_sum            'C46 H26 Cl4 N4 O4'
_chemical_formula_weight         840.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C46 H26 Cl4 N4 O4'
_chemical_oxdiff_usercomment     '@ 120 K K76B71b'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   10.0081(3)
_cell_length_b                   14.3562(5)
_cell_length_c                   14.6779(4)
_cell_angle_alpha                63.466(3)
_cell_angle_beta                 75.953(2)
_cell_angle_gamma                81.918(2)
_cell_volume                     1829.09(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    20930
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      32.7690
_cell_measurement_theta_min      3.7430
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.91915
_exptl_absorpt_correction_T_min  0.91915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             860
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1064
0 1 0 0.0800
0 1 2 0.2027
0 0 -1 0.1707
1 0 0 0.1022
-2 -1 -2 0.0825
-1 0 1 0.1971
-1 1 -1 0.0874
1 -1 0 0.1152
1 1 0 0.1068
-2 2 1 0.1589
1 2 2 0.1951

_exptl_crystal_recrystallization_method 
'The material was recrystallised from dichloromethane by slow cooling'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_size_rad          0.145
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
0.0000 -1.0000 -0.0000 -0.0542 0.0038 -0.0099
-0.0000 1.0000 0.0000 0.0542 -0.0038 0.0099
0.0000 1.0000 2.0000 0.0257 0.0016 -0.0966
-0.0000 -0.0000 -1.0000 0.0143 -0.0027 0.0532
1.0000 -0.0000 0.0000 -0.0013 0.0705 0.0193
-2.0000 -1.0000 -2.0000 -0.0230 -0.1426 0.0579
-1.0000 0.0000 1.0000 -0.0129 -0.0678 -0.0725
-1.0000 1.0000 -1.0000 0.0699 -0.0770 0.0437
1.0000 -1.0000 0.0000 -0.0556 0.0743 0.0095
1.0000 1.0000 0.0000 0.0529 0.0667 0.0292
-2.0000 2.0000 1.0000 0.0969 -0.1459 -0.0721
1.0000 2.0000 2.0000 0.0786 0.0683 -0.0674

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            58989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.998
_diffrn_reflns_theta_min         3.174
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  61.00   1.00   10.00    --  -17.52  20.00-107.00  113
  2  ω    -59.00  54.00   1.00   10.00    --   19.09 -20.00  85.00  113
  3  ω    -16.00  97.00   1.00   10.00    --   19.09  20.00-107.00  113
  4  ω   -103.00 -58.00   1.00   10.00    --  -17.52 178.00 -90.00   45
  5  ω    -42.00  14.00   1.00   10.00    --  -17.52 -77.00-150.00   56
  6  ω    -42.00  14.00   1.00   10.00    --  -17.52 -77.00  30.00   56
  7  ω   -103.00 -58.00   1.00   10.00    --  -17.52 178.00-120.00   45
  8  ω    -15.00  59.00   1.00   10.00    --   19.09 -99.00-120.00   74
  9  ω     39.00 106.00   1.00   10.00    --   19.09 178.00 -30.00   67
 10  ω     39.00 106.00   1.00   10.00    --   19.09 178.00-120.00   67
 11  ω     37.00 105.00   1.00   10.00    --   19.09-178.00  90.00   68
 12  ω    -42.00  14.00   1.00   10.00    --  -17.52 -77.00 -60.00   56
 13  ω    -49.00 -24.00   1.00   10.00    --  -17.52  77.00  90.00   25
 14  ω     -3.00  92.00   1.00   10.00    --   19.09  38.00 150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0013400000
_diffrn_orient_matrix_UB_12      0.0542435000
_diffrn_orient_matrix_UB_13      -0.0142862000
_diffrn_orient_matrix_UB_21      0.0704950000
_diffrn_orient_matrix_UB_22      -0.0037941000
_diffrn_orient_matrix_UB_23      0.0026942000
_diffrn_orient_matrix_UB_31      0.0193223000
_diffrn_orient_matrix_UB_32      0.0098550000
_diffrn_orient_matrix_UB_33      -0.0532132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10470
_reflns_number_total             12741
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         12741
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.036
_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)+(0.0488P)²+1.0706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          
;
H atoms were identified from a difference map and freely refined. One chlorine atom was modelled as disordered.  Geometric restraints were used.


#===============================================================================
#>>> The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         15 Note

Not significant

#===============================================================================
222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        6.3 Ratio
244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C46 Check
906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.654 Check

Not significant

#===============================================================================
;
_olex2_refinement_description    
;
1. Restrained distances
 Cl4-C46 \\sim Cl4A-C46
 with sigma of 0.02
2. Others
 Sof(Cl4A)=1-FVAR(1)
 Sof(Cl4)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_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
Cl1 Cl 0.45882(5) -0.00550(5) 0.62530(5) 0.05004(14) Uani 1 1 d . . . A 1
Cl2 Cl 0.18853(4) -0.01966(3) 0.76142(3) 0.03031(9) Uani 1 1 d . . . . .
C45 C 0.34823(18) 0.04126(14) 0.71021(14) 0.0287(3) Uani 1 1 d . . . . .
Cl3 Cl 0.07927(5) 0.53040(5) 0.34464(5) 0.04560(13) Uani 1 1 d . . . . .
Cl4 Cl 0.0222(5) 0.75230(18) 0.2302(2) 0.0519(8) Uani 0.578(10) 1 d D . P B 1
C46 C 0.0732(2) 0.65519(17) 0.34091(16) 0.0380(4) Uani 1 1 d D . . . .
O1 O 0.37574(10) 0.26515(7) 0.46023(7) 0.01588(18) Uani 1 1 d . . . . .
O2 O 0.38155(10) 0.26394(7) 0.27267(7) 0.01514(17) Uani 1 1 d . . . . .
O3 O 0.52407(10) 0.82212(7) 0.19856(7) 0.01504(17) Uani 1 1 d . . . . .
O4 O 0.49734(10) 0.82315(7) 0.01780(7) 0.01545(17) Uani 1 1 d . . . . .
N1 N 0.15721(12) 0.20018(9) 0.52481(8) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.16360(12) 0.19955(9) 0.33165(8) 0.0157(2) Uani 1 1 d . . . . .
N3 N 0.36173(12) 0.95712(9) 0.17917(8) 0.0161(2) Uani 1 1 d . . . . .
N4 N 0.31895(12) 0.94662(9) 0.00067(8) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.26148(13) 0.23282(10) 0.44719(10) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.26520(13) 0.23157(10) 0.34931(10) 0.0143(2) Uani 1 1 d . . . . .
C3 C 0.04881(13) 0.16374(10) 0.50918(10) 0.0150(2) Uani 1 1 d . . . . .
C4 C -0.06529(14) 0.12233(11) 0.59154(10) 0.0180(2) Uani 1 1 d . . . . .
C5 C -0.17147(14) 0.08375(10) 0.57590(11) 0.0184(2) Uani 1 1 d . . . . .
C6 C -0.16981(14) 0.08655(11) 0.47846(11) 0.0192(3) Uani 1 1 d . . . . .
C7 C -0.06009(14) 0.12632(11) 0.39730(11) 0.0181(2) Uani 1 1 d . . . . .
C8 C 0.05173(13) 0.16446(10) 0.41193(10) 0.0148(2) Uani 1 1 d . . . . .
C9 C 0.42806(13) 0.89038(10) 0.14590(9) 0.0143(2) Uani 1 1 d . . . . .
C10 C 0.40973(13) 0.88750(10) 0.05317(9) 0.0144(2) Uani 1 1 d . . . . .
C11 C 0.26632(14) 1.02212(10) 0.12428(10) 0.0155(2) Uani 1 1 d . . . . .
C12 C 0.24131(14) 1.01442(10) 0.03701(10) 0.0157(2) Uani 1 1 d . . . . .
C13 C 0.13698(15) 1.07786(11) -0.01433(11) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.06175(15) 1.14788(11) 0.01994(11) 0.0209(3) Uani 1 1 d . . . . .
C15 C 0.09143(16) 1.15914(11) 0.10396(11) 0.0209(3) Uani 1 1 d . . . . .
C16 C 0.19157(15) 1.09770(10) 0.15534(10) 0.0191(3) Uani 1 1 d . . . . .
C17 C 0.36557(13) 0.36609(10) 0.45561(10) 0.0144(2) Uani 1 1 d . . . . .
C18 C 0.43177(12) 0.44596(10) 0.36643(9) 0.0124(2) Uani 1 1 d . . . . .
C19 C 0.42401(12) 0.54711(10) 0.36505(9) 0.0122(2) Uani 1 1 d . . . . .
C20 C 0.48265(12) 0.63798(10) 0.27615(9) 0.0123(2) Uani 1 1 d . . . . .
C21 C 0.46700(13) 0.73139(10) 0.28421(9) 0.0138(2) Uani 1 1 d . . . . .
C22 C 0.40135(14) 0.74186(10) 0.37547(10) 0.0158(2) Uani 1 1 d . . . . .
C23 C 0.34476(14) 0.65644(11) 0.46043(10) 0.0158(2) Uani 1 1 d . . . . .
C24 C 0.35300(13) 0.55876(10) 0.45709(9) 0.0139(2) Uani 1 1 d . . . . .
C25 C 0.29052(13) 0.47244(11) 0.54628(10) 0.0165(2) Uani 1 1 d . . . . .
C26 C 0.29609(14) 0.37720(11) 0.54580(10) 0.0166(2) Uani 1 1 d . . . . .
C27 C 0.36744(13) 0.36522(10) 0.19426(9) 0.0135(2) Uani 1 1 d . . . . .
C28 C 0.42905(12) 0.44559(9) 0.19370(9) 0.0120(2) Uani 1 1 d . . . . .
C29 C 0.41182(12) 0.54853(10) 0.11416(9) 0.0122(2) Uani 1 1 d . . . . .
C30 C 0.46956(12) 0.63891(9) 0.10524(9) 0.0122(2) Uani 1 1 d . . . . .
C31 C 0.43915(13) 0.73415(10) 0.02846(9) 0.0140(2) Uani 1 1 d . . . . .
C32 C 0.35858(15) 0.74793(11) -0.04292(10) 0.0184(2) Uani 1 1 d . . . . .
C33 C 0.30603(15) 0.66252(11) -0.03667(10) 0.0178(2) Uani 1 1 d . . . . .
C34 C 0.33076(13) 0.56192(10) 0.04091(9) 0.0138(2) Uani 1 1 d . . . . .
C35 C 0.27445(13) 0.47495(11) 0.04444(10) 0.0157(2) Uani 1 1 d . . . . .
C36 C 0.29280(13) 0.37729(10) 0.11944(10) 0.0152(2) Uani 1 1 d . . . . .
C37 C 0.65649(13) 0.45364(10) 0.23740(9) 0.0130(2) Uani 1 1 d . . . . .
C38 C 0.76686(13) 0.38101(11) 0.24992(10) 0.0161(2) Uani 1 1 d . . . . .
C39 C 0.90214(14) 0.41370(12) 0.21101(11) 0.0203(3) Uani 1 1 d . . . . .
C40 C 0.92712(14) 0.51949(12) 0.16016(11) 0.0205(3) Uani 1 1 d . . . . .
C41 C 0.81700(13) 0.59204(11) 0.14854(10) 0.0168(2) Uani 1 1 d . . . . .
C42 C 0.68163(12) 0.55922(10) 0.18646(9) 0.0132(2) Uani 1 1 d . . . . .
C43 C 0.51026(12) 0.41783(10) 0.27856(9) 0.0125(2) Uani 1 1 d . . . . .
C44 C 0.56339(13) 0.63869(10) 0.17331(9) 0.0125(2) Uani 1 1 d . . . . .
Cl4A Cl 0.0907(8) 0.7557(3) 0.21123(19) 0.0671(10) Uani 0.422(10) 1 d D . P B 2
H44 H 0.6060(15) 0.7030(12) 0.1352(11) 0.004(3) Uiso 1 1 d . . . . .
H43 H 0.5200(17) 0.3426(13) 0.3090(13) 0.012(4) Uiso 1 1 d . . . . .
H26 H 0.2587(18) 0.3145(14) 0.6055(14) 0.019(4) Uiso 1 1 d . . . . .
H41 H 0.8334(19) 0.6666(15) 0.1124(14) 0.021(4) Uiso 1 1 d . . . . .
H23 H 0.2990(19) 0.6607(14) 0.5238(14) 0.020(4) Uiso 1 1 d . . . . .
H4 H -0.0660(18) 0.1209(14) 0.6577(14) 0.018(4) Uiso 1 1 d . . . . .
H36 H 0.255(2) 0.3170(15) 0.1233(15) 0.024(5) Uiso 1 1 d . . . . .
H35 H 0.224(2) 0.4862(15) -0.0058(15) 0.024(5) Uiso 1 1 d . . . . .
H33 H 0.2542(19) 0.6678(14) -0.0836(14) 0.022(4) Uiso 1 1 d . . . . .
H32 H 0.3420(19) 0.8161(15) -0.0945(15) 0.024(5) Uiso 1 1 d . . . . .
H6 H -0.245(2) 0.0594(15) 0.4696(14) 0.023(5) Uiso 1 1 d . . . . .
H7 H -0.0570(19) 0.1265(14) 0.3308(14) 0.020(4) Uiso 1 1 d . . . . .
H13 H 0.1203(19) 1.0707(15) -0.0740(15) 0.024(5) Uiso 1 1 d . . . . .
H38 H 0.7487(18) 0.3083(14) 0.2851(13) 0.016(4) Uiso 1 1 d . . . . .
H40 H 1.021(2) 0.5403(15) 0.1361(15) 0.023(5) Uiso 1 1 d . . . . .
H15 H 0.0418(19) 1.2115(14) 0.1222(14) 0.019(4) Uiso 1 1 d . . . . .
H22 H 0.3957(19) 0.8103(15) 0.3766(14) 0.022(5) Uiso 1 1 d . . . . .
H5 H -0.247(2) 0.0520(15) 0.6317(15) 0.025(5) Uiso 1 1 d . . . . .
H25 H 0.2458(19) 0.4821(15) 0.6057(15) 0.023(5) Uiso 1 1 d . . . . .
H14 H -0.013(2) 1.1874(15) -0.0123(15) 0.024(5) Uiso 1 1 d . . . . .
H39 H 0.976(2) 0.3619(15) 0.2192(15) 0.024(5) Uiso 1 1 d . . . . .
H16 H 0.2127(19) 1.1057(15) 0.2110(15) 0.023(5) Uiso 1 1 d . . . . .
H45A H 0.335(2) 0.1173(17) 0.6688(17) 0.035(5) Uiso 1 1 d . . . . .
H45B H 0.388(2) 0.0237(17) 0.7681(17) 0.038(6) Uiso 1 1 d . . . . .
H46A H 0.160(3) 0.667(2) 0.348(2) 0.063(8) Uiso 1 1 d . . . . .
H46B H -0.009(3) 0.660(2) 0.393(2) 0.057(7) Uiso 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
Cl1 C45 1.7600(19) . ?
Cl2 C45 1.7627(17) . ?
C45 H45A 0.99(2) . ?
C45 H45B 0.94(2) . ?
Cl3 C46 1.760(2) . ?
Cl4 C46 1.738(2) . ?
C46 Cl4A 1.786(3) . ?
C46 H46A 0.95(3) . ?
C46 H46B 0.99(3) . ?
O1 C1 1.3765(15) . ?
O1 C17 1.4104(15) . ?
O2 C2 1.3735(15) . ?
O2 C27 1.4088(15) . ?
O3 C9 1.3784(16) . ?
O3 C21 1.4145(15) . ?
O4 C10 1.3680(15) . ?
O4 C31 1.4080(15) . ?
N1 C1 1.2999(17) . ?
N1 C3 1.3751(17) . ?
N2 C2 1.2955(17) . ?
N2 C8 1.3724(16) . ?
N3 C9 1.2957(17) . ?
N3 C11 1.3721(17) . ?
N4 C10 1.2955(17) . ?
N4 C12 1.3731(17) . ?
C1 C2 1.4362(17) . ?
C3 C4 1.4133(18) . ?
C3 C8 1.4161(17) . ?
C4 C5 1.373(2) . ?
C4 H4 0.961(18) . ?
C5 C6 1.409(2) . ?
C5 H5 0.955(19) . ?
C6 C7 1.3728(19) . ?
C6 H6 0.957(19) . ?
C7 C8 1.4115(18) . ?
C7 H7 0.968(18) . ?
C9 C10 1.4359(17) . ?
C11 C12 1.4163(18) . ?
C11 C16 1.4118(18) . ?
C12 C13 1.4102(19) . ?
C13 C14 1.373(2) . ?
C13 H13 0.981(19) . ?
C14 C15 1.416(2) . ?
C14 H14 0.954(19) . ?
C15 C16 1.369(2) . ?
C15 H15 0.945(18) . ?
C16 H16 0.948(19) . ?
C17 C18 1.3852(17) . ?
C17 C26 1.4043(18) . ?
C18 C19 1.4344(17) . ?
C18 C43 1.5258(17) . ?
C19 C20 1.4393(17) . ?
C19 C24 1.4355(17) . ?
C20 C21 1.3822(17) . ?
C20 C44 1.5258(17) . ?
C21 C22 1.4049(17) . ?
C22 C23 1.3660(19) . ?
C22 H22 0.984(19) . ?
C23 C24 1.4152(18) . ?
C23 H23 0.956(18) . ?
C24 C25 1.4183(18) . ?
C25 C26 1.3636(19) . ?
C25 H25 0.939(19) . ?
C26 H26 0.974(18) . ?
C27 C28 1.3787(17) . ?
C27 C36 1.4091(18) . ?
C28 C29 1.4358(17) . ?
C28 C43 1.5257(17) . ?
C29 C30 1.4342(17) . ?
C29 C34 1.4303(17) . ?
C30 C31 1.3802(17) . ?
C30 C44 1.5270(17) . ?
C31 C32 1.4026(18) . ?
C32 C33 1.3586(19) . ?
C32 H32 0.954(19) . ?
C33 C34 1.4180(18) . ?
C33 H33 0.930(19) . ?
C34 C35 1.4160(18) . ?
C35 C36 1.3631(19) . ?
C35 H35 0.933(19) . ?
C36 H36 0.966(19) . ?
C37 C38 1.3944(18) . ?
C37 C42 1.3868(17) . ?
C37 C43 1.5086(17) . ?
C38 C39 1.3941(19) . ?
C38 H38 0.957(18) . ?
C39 C40 1.389(2) . ?
C39 H39 0.96(2) . ?
C40 C41 1.392(2) . ?
C40 H40 0.958(19) . ?
C41 C42 1.3952(17) . ?
C41 H41 0.977(19) . ?
C42 C44 1.5079(18) . ?
C43 H43 0.968(17) . ?
C44 H44 0.938(15) . ?

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
Cl1 C45 Cl2 111.90(9) . . ?
Cl1 C45 H45A 106.2(12) . . ?
Cl1 C45 H45B 108.6(14) . . ?
Cl2 C45 H45A 110.5(13) . . ?
Cl2 C45 H45B 105.6(13) . . ?
H45A C45 H45B 114.1(18) . . ?
Cl3 C46 Cl4A 111.99(16) . . ?
Cl3 C46 H46A 108.8(17) . . ?
Cl3 C46 H46B 107.4(15) . . ?
Cl4 C46 Cl3 112.56(12) . . ?
Cl4 C46 H46A 112.7(17) . . ?
Cl4 C46 H46B 98.1(15) . . ?
Cl4A C46 H46A 93.4(17) . . ?
Cl4A C46 H46B 117.6(16) . . ?
H46A C46 H46B 117(2) . . ?
C1 O1 C17 116.16(10) . . ?
C2 O2 C27 113.72(10) . . ?
C9 O3 C21 113.84(10) . . ?
C10 O4 C31 116.02(10) . . ?
C1 N1 C3 116.73(11) . . ?
C2 N2 C8 116.92(11) . . ?
C9 N3 C11 116.53(11) . . ?
C10 N4 C12 116.69(11) . . ?
O1 C1 C2 118.31(11) . . ?
N1 C1 O1 119.18(11) . . ?
N1 C1 C2 122.44(12) . . ?
O2 C2 C1 118.63(11) . . ?
N2 C2 O2 119.14(11) . . ?
N2 C2 C1 122.23(12) . . ?
N1 C3 C4 119.97(12) . . ?
N1 C3 C8 120.67(11) . . ?
C4 C3 C8 119.33(12) . . ?
C3 C4 H4 119.0(11) . . ?
C5 C4 C3 119.53(12) . . ?
C5 C4 H4 121.5(11) . . ?
C4 C5 C6 121.08(12) . . ?
C4 C5 H5 120.7(12) . . ?
C6 C5 H5 118.2(12) . . ?
C5 C6 H6 119.3(11) . . ?
C7 C6 C5 120.46(13) . . ?
C7 C6 H6 120.2(11) . . ?
C6 C7 C8 119.60(12) . . ?
C6 C7 H7 120.9(11) . . ?
C8 C7 H7 119.5(11) . . ?
N2 C8 C3 121.00(12) . . ?
N2 C8 C7 119.01(11) . . ?
C7 C8 C3 119.97(12) . . ?
O3 C9 C10 118.30(11) . . ?
N3 C9 O3 119.23(11) . . ?
N3 C9 C10 122.42(12) . . ?
O4 C10 C9 117.51(11) . . ?
N4 C10 O4 120.01(11) . . ?
N4 C10 C9 122.39(12) . . ?
N3 C11 C12 121.02(12) . . ?
N3 C11 C16 119.57(12) . . ?
C16 C11 C12 119.41(12) . . ?
N4 C12 C11 120.69(12) . . ?
N4 C12 C13 119.38(12) . . ?
C13 C12 C11 119.93(12) . . ?
C12 C13 H13 118.7(11) . . ?
C14 C13 C12 119.56(13) . . ?
C14 C13 H13 121.7(11) . . ?
C13 C14 C15 120.44(13) . . ?
C13 C14 H14 119.2(11) . . ?
C15 C14 H14 120.4(11) . . ?
C14 C15 H15 118.0(11) . . ?
C16 C15 C14 120.85(13) . . ?
C16 C15 H15 121.2(11) . . ?
C11 C16 H16 119.2(12) . . ?
C15 C16 C11 119.68(13) . . ?
C15 C16 H16 121.1(12) . . ?
C18 C17 O1 118.79(11) . . ?
C18 C17 C26 124.05(12) . . ?
C26 C17 O1 117.00(11) . . ?
C17 C18 C19 117.74(11) . . ?
C17 C18 C43 116.81(11) . . ?
C19 C18 C43 125.44(11) . . ?
C18 C19 C20 123.66(11) . . ?
C18 C19 C24 118.31(11) . . ?
C24 C19 C20 118.03(11) . . ?
C19 C20 C44 124.68(11) . . ?
C21 C20 C19 118.16(11) . . ?
C21 C20 C44 117.15(11) . . ?
C20 C21 O3 119.66(11) . . ?
C20 C21 C22 123.67(12) . . ?
C22 C21 O3 116.62(11) . . ?
C21 C22 H22 119.6(11) . . ?
C23 C22 C21 118.87(12) . . ?
C23 C22 H22 121.5(11) . . ?
C22 C23 C24 120.69(12) . . ?
C22 C23 H23 121.2(11) . . ?
C24 C23 H23 118.1(11) . . ?
C23 C24 C19 120.53(11) . . ?
C23 C24 C25 118.95(11) . . ?
C25 C24 C19 120.52(12) . . ?
C24 C25 H25 118.7(12) . . ?
C26 C25 C24 120.58(12) . . ?
C26 C25 H25 120.7(12) . . ?
C17 C26 H26 116.9(11) . . ?
C25 C26 C17 118.75(12) . . ?
C25 C26 H26 124.3(11) . . ?
O2 C27 C36 117.26(11) . . ?
C28 C27 O2 118.69(11) . . ?
C28 C27 C36 124.04(12) . . ?
C27 C28 C29 117.92(11) . . ?
C27 C28 C43 117.06(11) . . ?
C29 C28 C43 125.02(11) . . ?
C30 C29 C28 123.54(11) . . ?
C34 C29 C28 118.22(11) . . ?
C34 C29 C30 118.23(11) . . ?
C29 C30 C44 125.39(11) . . ?
C31 C30 C29 117.69(11) . . ?
C31 C30 C44 116.92(11) . . ?
C30 C31 O4 118.15(11) . . ?
C30 C31 C32 124.33(12) . . ?
C32 C31 O4 117.47(11) . . ?
C31 C32 H32 120.1(11) . . ?
C33 C32 C31 118.44(12) . . ?
C33 C32 H32 121.5(11) . . ?
C32 C33 C34 120.80(12) . . ?
C32 C33 H33 121.3(12) . . ?
C34 C33 H33 117.8(12) . . ?
C33 C34 C29 120.48(12) . . ?
C35 C34 C29 120.55(12) . . ?
C35 C34 C33 118.97(11) . . ?
C34 C35 H35 118.4(12) . . ?
C36 C35 C34 120.80(12) . . ?
C36 C35 H35 120.8(12) . . ?
C27 C36 H36 119.5(11) . . ?
C35 C36 C27 118.37(12) . . ?
C35 C36 H36 122.1(11) . . ?
C38 C37 C43 120.31(11) . . ?
C42 C37 C38 119.69(12) . . ?
C42 C37 C43 119.99(11) . . ?
C37 C38 H38 119.2(11) . . ?
C39 C38 C37 120.53(13) . . ?
C39 C38 H38 120.2(11) . . ?
C38 C39 H39 118.7(12) . . ?
C40 C39 C38 119.69(13) . . ?
C40 C39 H39 121.6(12) . . ?
C39 C40 C41 119.80(13) . . ?
C39 C40 H40 118.4(11) . . ?
C41 C40 H40 121.8(11) . . ?
C40 C41 C42 120.45(13) . . ?
C40 C41 H41 120.4(11) . . ?
C42 C41 H41 119.1(11) . . ?
C37 C42 C41 119.83(12) . . ?
C37 C42 C44 120.31(11) . . ?
C41 C42 C44 119.85(11) . . ?
C18 C43 H43 106.1(10) . . ?
C28 C43 C18 112.99(10) . . ?
C28 C43 H43 104.6(10) . . ?
C37 C43 C18 113.95(10) . . ?
C37 C43 C28 113.72(10) . . ?
C37 C43 H43 104.3(10) . . ?
C20 C44 C30 112.45(10) . . ?
C20 C44 H44 106.8(9) . . ?
C30 C44 H44 104.1(9) . . ?
C42 C44 C20 113.02(10) . . ?
C42 C44 C30 115.13(10) . . ?
C42 C44 H44 104.2(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
O1 C1 C2 O2 -0.87(17) . . . . ?
O1 C1 C2 N2 178.07(11) . . . . ?
O1 C17 C18 C19 -177.81(10) . . . . ?
O1 C17 C18 C43 0.67(16) . . . . ?
O1 C17 C26 C25 176.51(11) . . . . ?
O2 C27 C28 C29 -179.07(10) . . . . ?
O2 C27 C28 C43 0.71(16) . . . . ?
O2 C27 C36 C35 178.22(11) . . . . ?
O3 C9 C10 O4 -5.51(17) . . . . ?
O3 C9 C10 N4 177.86(11) . . . . ?
O3 C21 C22 C23 -179.89(11) . . . . ?
O4 C31 C32 C33 177.39(12) . . . . ?
N1 C1 C2 O2 -177.64(12) . . . . ?
N1 C1 C2 N2 1.3(2) . . . . ?
N1 C3 C4 C5 -178.38(12) . . . . ?
N1 C3 C8 N2 1.27(19) . . . . ?
N1 C3 C8 C7 179.69(12) . . . . ?
N3 C9 C10 O4 171.79(11) . . . . ?
N3 C9 C10 N4 -4.8(2) . . . . ?
N3 C11 C12 N4 -4.67(19) . . . . ?
N3 C11 C12 C13 176.21(12) . . . . ?
N3 C11 C16 C15 -176.73(13) . . . . ?
N4 C12 C13 C14 -178.14(13) . . . . ?
C1 O1 C17 C18 -103.74(13) . . . . ?
C1 O1 C17 C26 80.65(14) . . . . ?
C1 N1 C3 C4 176.97(12) . . . . ?
C1 N1 C3 C8 -1.23(18) . . . . ?
C2 O2 C27 C28 104.27(13) . . . . ?
C2 O2 C27 C36 -77.06(14) . . . . ?
C2 N2 C8 C3 0.02(18) . . . . ?
C2 N2 C8 C7 -178.42(12) . . . . ?
C3 N1 C1 O1 -176.72(11) . . . . ?
C3 N1 C1 C2 0.03(18) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C3 C8 N2 -176.94(12) . . . . ?
C4 C3 C8 C7 1.49(19) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 N2 177.01(12) . . . . ?
C6 C7 C8 C3 -1.4(2) . . . . ?
C8 N2 C2 O2 177.69(11) . . . . ?
C8 N2 C2 C1 -1.24(18) . . . . ?
C8 C3 C4 C5 -0.2(2) . . . . ?
C9 O3 C21 C20 104.53(13) . . . . ?
C9 O3 C21 C22 -78.02(13) . . . . ?
C9 N3 C11 C12 1.01(18) . . . . ?
C9 N3 C11 C16 -179.15(12) . . . . ?
C10 O4 C31 C30 -105.50(13) . . . . ?
C10 O4 C31 C32 77.16(14) . . . . ?
C10 N4 C12 C11 3.41(18) . . . . ?
C10 N4 C12 C13 -177.46(12) . . . . ?
C11 N3 C9 O3 -179.22(11) . . . . ?
C11 N3 C9 C10 3.50(18) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 N4 C10 O4 -175.50(11) . . . . ?
C12 N4 C10 C9 1.04(18) . . . . ?
C12 C11 C16 C15 3.1(2) . . . . ?
C12 C13 C14 C15 2.1(2) . . . . ?
C13 C14 C15 C16 -2.7(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C16 C11 C12 N4 175.50(12) . . . . ?
C16 C11 C12 C13 -3.62(19) . . . . ?
C17 O1 C1 N1 -78.81(14) . . . . ?
C17 O1 C1 C2 104.31(13) . . . . ?
C17 C18 C19 C20 -177.18(11) . . . . ?
C17 C18 C19 C24 2.34(17) . . . . ?
C17 C18 C43 C28 98.93(13) . . . . ?
C17 C18 C43 C37 -129.27(12) . . . . ?
C18 C17 C26 C25 1.1(2) . . . . ?
C18 C19 C20 C21 179.33(11) . . . . ?
C18 C19 C20 C44 -1.65(18) . . . . ?
C18 C19 C24 C23 178.75(11) . . . . ?
C18 C19 C24 C25 -0.95(17) . . . . ?
C19 C18 C43 C28 -82.71(14) . . . . ?
C19 C18 C43 C37 49.09(16) . . . . ?
C19 C20 C21 O3 179.61(10) . . . . ?
C19 C20 C21 C22 2.36(18) . . . . ?
C19 C20 C44 C30 78.88(14) . . . . ?
C19 C20 C44 C42 -53.56(15) . . . . ?
C19 C24 C25 C26 -0.45(19) . . . . ?
C20 C19 C24 C23 -1.69(17) . . . . ?
C20 C19 C24 C25 178.60(11) . . . . ?
C20 C21 C22 C23 -2.56(19) . . . . ?
C21 O3 C9 N3 84.71(14) . . . . ?
C21 O3 C9 C10 -97.90(13) . . . . ?
C21 C20 C44 C30 -102.09(13) . . . . ?
C21 C20 C44 C42 125.47(12) . . . . ?
C21 C22 C23 C24 0.53(19) . . . . ?
C22 C23 C24 C19 1.54(19) . . . . ?
C22 C23 C24 C25 -178.74(12) . . . . ?
C23 C24 C25 C26 179.84(12) . . . . ?
C24 C19 C20 C21 -0.19(17) . . . . ?
C24 C19 C20 C44 178.83(11) . . . . ?
C24 C25 C26 C17 0.40(19) . . . . ?
C26 C17 C18 C19 -2.53(19) . . . . ?
C26 C17 C18 C43 175.96(12) . . . . ?
C27 O2 C2 N2 78.41(14) . . . . ?
C27 O2 C2 C1 -102.62(13) . . . . ?
C27 C28 C29 C30 179.54(11) . . . . ?
C27 C28 C29 C34 0.64(17) . . . . ?
C27 C28 C43 C18 -102.14(13) . . . . ?
C27 C28 C43 C37 125.94(12) . . . . ?
C28 C27 C36 C35 -3.19(19) . . . . ?
C28 C29 C30 C31 -176.65(11) . . . . ?
C28 C29 C30 C44 3.87(19) . . . . ?
C28 C29 C34 C33 177.52(11) . . . . ?
C28 C29 C34 C35 -2.75(17) . . . . ?
C29 C28 C43 C18 77.63(14) . . . . ?
C29 C28 C43 C37 -54.30(16) . . . . ?
C29 C30 C31 O4 -178.86(10) . . . . ?
C29 C30 C31 C32 -1.72(19) . . . . ?
C29 C30 C44 C20 -83.13(14) . . . . ?
C29 C30 C44 C42 48.26(16) . . . . ?
C29 C34 C35 C36 1.99(19) . . . . ?
C30 C29 C34 C33 -1.44(17) . . . . ?
C30 C29 C34 C35 178.28(11) . . . . ?
C30 C31 C32 C33 0.2(2) . . . . ?
C31 O4 C10 N4 -73.98(15) . . . . ?
C31 O4 C10 C9 109.31(13) . . . . ?
C31 C30 C44 C20 97.39(13) . . . . ?
C31 C30 C44 C42 -131.21(12) . . . . ?
C31 C32 C33 C34 0.7(2) . . . . ?
C32 C33 C34 C29 -0.1(2) . . . . ?
C32 C33 C34 C35 -179.78(13) . . . . ?
C33 C34 C35 C36 -178.28(12) . . . . ?
C34 C29 C30 C31 2.25(17) . . . . ?
C34 C29 C30 C44 -177.22(11) . . . . ?
C34 C35 C36 C27 0.91(19) . . . . ?
C36 C27 C28 C29 2.36(18) . . . . ?
C36 C27 C28 C43 -177.86(11) . . . . ?
C37 C38 C39 C40 0.6(2) . . . . ?
C37 C42 C44 C20 66.39(14) . . . . ?
C37 C42 C44 C30 -64.73(15) . . . . ?
C38 C37 C42 C41 -0.28(18) . . . . ?
C38 C37 C42 C44 -179.35(11) . . . . ?
C38 C37 C43 C18 114.45(13) . . . . ?
C38 C37 C43 C28 -114.10(13) . . . . ?
C38 C39 C40 C41 0.1(2) . . . . ?
C39 C40 C41 C42 -0.8(2) . . . . ?
C40 C41 C42 C37 0.93(19) . . . . ?
C40 C41 C42 C44 180.00(12) . . . . ?
C41 C42 C44 C20 -112.67(13) . . . . ?
C41 C42 C44 C30 116.20(13) . . . . ?
C42 C37 C38 C39 -0.46(19) . . . . ?
C42 C37 C43 C18 -65.81(15) . . . . ?
C42 C37 C43 C28 65.64(15) . . . . ?
C43 C18 C19 C20 4.48(19) . . . . ?
C43 C18 C19 C24 -176.00(11) . . . . ?
C43 C28 C29 C30 -0.22(19) . . . . ?
C43 C28 C29 C34 -179.13(11) . . . . ?
C43 C37 C38 C39 179.28(12) . . . . ?
C43 C37 C42 C41 179.97(11) . . . . ?
C43 C37 C42 C44 0.90(17) . . . . ?
C44 C20 C21 O3 0.51(17) . . . . ?
C44 C20 C21 C22 -176.74(11) . . . . ?
C44 C30 C31 O4 0.65(16) . . . . ?
C44 C30 C31 C32 177.80(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K76B71b
_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 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# 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_nm22004
_database_code_depnum_ccdc_archive 'CCDC 2286809'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT414_nm22004             
;
PROBLEM: Short Intra D-H..H-X       H1       ..H26      .       1.89 Ang.
RESPONSE:  H atoms freely refined.
;
_vrf_PLAT910_nm22004             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: Not significant
;
# Added during the CSD deposition process: Friday 04 August 2023 01:21 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H16 O4 S, 2(C2 D6 O S)'
_chemical_formula_sum            'C30 H16 D12 O6 S3'
_chemical_formula_weight         592.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H16O4S
_chemical_oxdiff_usercomment     '@ 120 K K75B61a'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5199(2)
_cell_length_b                   18.4144(3)
_cell_length_c                   13.8648(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.763(2)
_cell_angle_gamma                90
_cell_volume                     2654.50(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24763
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      31.5970
_cell_measurement_theta_min      3.8630
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1295
0 -1 0 0.1328
-1 1 0 0.1763
1 -1 0 0.1704
-1 -1 0 0.1702
1 1 0 0.1761
0 0 1 0.0489
0 0 -1 0.0203
1 0 0 0.1705
-1 0 0 0.1688

_exptl_crystal_recrystallization_method 
'The material was recrystallised from d6-DMSO by slow cooling'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.9998 0.0000 -0.0034 0.0384 0.0001
0.0000 -0.9998 -0.0000 0.0034 -0.0384 -0.0001
-1.0004 0.9999 0.0010 -0.0077 0.0381 -0.0680
1.0004 -0.9999 -0.0010 0.0077 -0.0381 0.0680
-1.0004 -0.9996 0.0010 -0.0008 -0.0386 -0.0682
1.0004 0.9996 -0.0010 0.0008 0.0386 0.0682
0.0011 0.0004 0.9998 -0.0504 -0.0045 0.0110
-0.0011 -0.0004 -0.9998 0.0504 0.0045 -0.0110
1.0004 -0.0002 -0.0010 0.0043 0.0003 0.0681
-1.0004 0.0002 0.0010 -0.0043 -0.0003 -0.0681

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            90040
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         3.440
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  -6.00   1.00   30.00    --  -24.07 134.00 -51.00   77
  2  ω    -83.00  -6.00   1.00   30.00    --  -24.07 135.00 128.00   77
  3  ω      6.00  85.00   1.00   30.00    --   25.94-134.00-118.00   79
  4  ω      6.00  85.00   1.00   30.00    --   25.94-135.00  61.00   79
  5  ω    -91.00  -7.00   1.00   30.00    --  -24.07 -57.00  30.00   84
  6  ω    -51.00  39.00   1.00   30.00    --  -24.07  77.00-180.00   90
  7  ω    -95.00   5.00   1.00   30.00    --  -24.07 -19.00  30.00  100
  8  ω    -20.00  65.00   1.00   30.00    --   25.94 -99.00 120.00   85
  9  ω    -39.00  53.00   1.00   30.00    --   25.94 -77.00-120.00   92
 10  ω    -20.00  65.00   1.00   30.00    --   25.94 -99.00 -90.00   85
 11  ω    -43.00  45.00   1.00   30.00    --   25.94 -38.00 -60.00   88
 12  ω    -91.00  -7.00   1.00   30.00    --  -24.07 -57.00-120.00   84
 13  ω    -91.00  -7.00   1.00   30.00    --  -24.07 -57.00 -60.00   84
 14  ω    -91.00  -7.00   1.00   30.00    --  -24.07 -57.00 150.00   84
 15  ω    -91.00  -7.00   1.00   30.00    --  -24.07 -57.00  90.00   84
 16  ω    -96.00 -39.00   1.00   30.00    --  -24.07-178.00  30.00   57
 17  ω    -41.00  43.00   1.00   30.00    --   25.94 -57.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction XCalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042007000
_diffrn_orient_matrix_UB_12      -0.0034329000
_diffrn_orient_matrix_UB_13      -0.0503902000
_diffrn_orient_matrix_UB_21      0.0002795000
_diffrn_orient_matrix_UB_22      0.0383633000
_diffrn_orient_matrix_UB_23      -0.0045194000
_diffrn_orient_matrix_UB_31      0.0680789000
_diffrn_orient_matrix_UB_32      0.0000564000
_diffrn_orient_matrix_UB_33      0.0109239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6842
_reflns_number_total             7436
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         7436
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.205
_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)+(0.0453P)²+2.3915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          
;
With the exception of disorder, H/D atoms were identified from a difference map and freely refined.  Atoms S1-C23-C24 were modelled as disordered, with geometric and displacement ellipsoid restraints used.

#===============================================================================
#>>> The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text

414_ALERT_2_B Short Intra D-H..H-X       H1       ..H26              1.89 Ang.

H atoms freely refined.

                                                      x,y,z  =      1_555 Check
910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         12 Note

Not significant

#===============================================================================
213_ALERT_2_C Atom C23A            has ADP max/min Ratio .....        3.5 oblate
213_ALERT_2_C Atom C24             has ADP max/min Ratio .....        3.2 prolat
222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        6.9 Ratio
242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S2 Check
414_ALERT_2_C Short Intra D-H..H-X       H3       ..H21              1.90 Ang.
                                                      x,y,z  =      1_555 Check
906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.525 Check

Not significant


#===============================================================================
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C23A-C24A \\sim C24-C23
 with sigma of 0.02
 S1A-C25 \\sim S1-C22
 with sigma of 0.02
 C24A-C23A \\sim C24-C23
 with sigma of 0.02
 C24A-C22 \\sim C25-C24
 with sigma of 0.02
 S1A-C23A \\sim S1-C23
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 S1A, C22, C23A, C24A, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1, C22, C23, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(S1A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
 Sof(S1)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C23A(H23A), C24(H24), C24A(H24A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0450(5) 0.2087(3) 0.2942(3) 0.0212(7) Uani 0.475(3) 1 d D . P A 1
S1A S -0.1001(4) 0.3235(2) 0.3244(2) 0.0244(5) Uani 0.525(3) 1 d D . P A 2
O1 O 0.06833(15) 0.48960(8) 0.60027(11) 0.0277(3) Uani 1 1 d . . . . .
H1 H 0.002(3) 0.4631(18) 0.595(2) 0.049(9) Uiso 1 1 d . . . . .
O2 O 0.43849(13) 0.17371(7) 0.48435(11) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.514(3) 0.1627(19) 0.485(3) 0.055(10) Uiso 1 1 d . . . . .
O3 O 0.28085(14) 0.08842(8) 0.57480(11) 0.0251(3) Uani 1 1 d . . . . .
H3 H 0.329(3) 0.1146(16) 0.545(2) 0.036(8) Uiso 1 1 d . . . . .
O4 O -0.13541(15) 0.40211(9) 0.62183(13) 0.0317(4) Uani 1 1 d . . . . .
H4 H -0.181(3) 0.4143(19) 0.658(3) 0.053(10) Uiso 1 1 d . . . . .
C1 C 0.17271(19) 0.45400(10) 0.57580(13) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.16996(17) 0.38357(10) 0.53916(12) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.29036(16) 0.34917(9) 0.52958(12) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.30405(16) 0.27398(9) 0.50388(12) 0.0132(3) Uani 1 1 d . . . . .
C5 C 0.42633(17) 0.24621(10) 0.50303(13) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.53849(17) 0.28934(11) 0.52183(14) 0.0202(4) Uani 1 1 d . . . . .
H6 H 0.625(3) 0.2676(15) 0.523(2) 0.034(7) Uiso 1 1 d . . . . .
C7 C 0.52676(18) 0.36032(11) 0.54448(14) 0.0216(4) Uani 1 1 d . . . . .
H7 H 0.602(3) 0.3889(15) 0.560(2) 0.032(7) Uiso 1 1 d . . . . .
C8 C 0.40543(18) 0.39145(10) 0.55053(13) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.3995(2) 0.46505(11) 0.57923(14) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.473(3) 0.4919(15) 0.592(2) 0.032(7) Uiso 1 1 d . . . . .
C10 C 0.2864(2) 0.49584(11) 0.59137(15) 0.0238(4) Uani 1 1 d . . . . .
H10 H 0.284(3) 0.5453(15) 0.611(2) 0.033(7) Uiso 1 1 d . . . . .
C11 C 0.18941(17) 0.12822(10) 0.61189(13) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.14236(16) 0.19433(10) 0.57396(12) 0.0146(3) Uani 1 1 d . . . . .
C13 C 0.04987(16) 0.23240(10) 0.62215(12) 0.0164(3) Uani 1 1 d . . . . .
C14 C -0.00117(17) 0.30318(10) 0.59536(13) 0.0180(3) Uani 1 1 d . . . . .
C15 C -0.08960(18) 0.33419(12) 0.64800(15) 0.0241(4) Uani 1 1 d . . . . .
C16 C -0.1309(2) 0.29903(14) 0.72780(17) 0.0319(5) Uani 1 1 d . . . . .
H16 H -0.191(3) 0.3210(16) 0.758(2) 0.041(8) Uiso 1 1 d . . . . .
C17 C -0.0834(2) 0.23254(14) 0.75429(16) 0.0304(5) Uani 1 1 d . . . . .
H17 H -0.108(2) 0.2079(14) 0.809(2) 0.028(6) Uiso 1 1 d . . . . .
C18 C 0.00610(18) 0.19751(12) 0.70360(14) 0.0225(4) Uani 1 1 d . . . . .
C19 C 0.0535(2) 0.12823(13) 0.73504(15) 0.0262(4) Uani 1 1 d . . . . .
H19 H 0.019(2) 0.1061(14) 0.786(2) 0.030(7) Uiso 1 1 d . . . . .
C20 C 0.1430(2) 0.09448(12) 0.69107(15) 0.0242(4) Uani 1 1 d . . . . .
H20 H 0.176(3) 0.0506(16) 0.711(2) 0.037(7) Uiso 1 1 d . . . . .
C21 C 0.19228(15) 0.22075(9) 0.48229(12) 0.0124(3) Uani 1 1 d . . . . .
H21 H 0.2280(19) 0.1794(12) 0.4585(15) 0.008(5) Uiso 1 1 d . . . . .
C22 C 0.08771(16) 0.24749(10) 0.40498(12) 0.0152(3) Uani 1 1 d D . . . .
C23 C -0.0730(9) 0.2732(4) 0.2643(7) 0.0263(16) Uani 0.475(3) 1 d D . P A 1
H23 H -0.132316 0.271269 0.205362 0.032 Uiso 0.475(3) 1 calc R U P A 1
C23A C -0.0577(8) 0.2507(4) 0.2594(5) 0.0217(12) Uani 0.525(3) 1 d D . P A 2
H23A H -0.098258 0.238488 0.195517 0.026 Uiso 0.525(3) 1 calc R U P A 2
C24 C -0.0753(15) 0.3276(9) 0.3319(10) 0.029(3) Uani 0.475(3) 1 d D . P A 1
H24 H -0.127173 0.370091 0.324417 0.035 Uiso 0.475(3) 1 calc R U P A 1
C24A C 0.0415(16) 0.2124(9) 0.3104(10) 0.019(2) Uani 0.525(3) 1 d D . P A 2
H24A H 0.076086 0.168978 0.288014 0.023 Uiso 0.525(3) 1 calc R U P A 2
C25 C 0.01834(17) 0.30745(10) 0.41860(12) 0.0166(3) Uani 1 1 d D . . . .
C26 C 0.03712(17) 0.34871(10) 0.51274(13) 0.0166(3) Uani 1 1 d . . . . .
H26 H -0.021(2) 0.3882(12) 0.5003(16) 0.012(5) Uiso 1 1 d . . . . .
S2 S -0.24547(5) 0.51929(3) 0.80110(4) 0.02596(12) Uani 1 1 d . . . . .
O5 O -0.28550(16) 0.45419(12) 0.73751(16) 0.0513(6) Uani 1 1 d . . . . .
C27 C -0.1975(5) 0.5844(2) 0.7219(3) 0.0689(12) Uani 1 1 d . . . . .
D27A D -0.123(4) 0.569(2) 0.700(3) 0.092(15) Uiso 1 1 d . . . . .
D27B D -0.163(4) 0.623(2) 0.773(3) 0.081(13) Uiso 1 1 d . . . . .
D27C D -0.270(6) 0.605(3) 0.684(5) 0.14(2) Uiso 1 1 d . . . . .
C30 C -0.0921(3) 0.4970(2) 0.8659(3) 0.0515(8) Uani 1 1 d . . . . .
D30A D -0.037(4) 0.483(2) 0.818(3) 0.068(11) Uiso 1 1 d . . . . .
D30B D -0.062(3) 0.541(2) 0.897(3) 0.063(10) Uiso 1 1 d . . . . .
D30C D -0.104(5) 0.464(3) 0.906(4) 0.099(17) Uiso 1 1 d . . . . .
S3 S 0.77635(5) 0.14539(3) 0.43525(4) 0.02616(12) Uani 1 1 d . . . . .
O6 O 0.67067(15) 0.12651(10) 0.49429(14) 0.0370(4) Uani 1 1 d . . . . .
C28 C 0.7162(3) 0.11747(18) 0.3137(2) 0.0416(6) Uani 1 1 d . . . . .
D28A D 0.686(3) 0.0677(17) 0.319(2) 0.037(7) Uiso 1 1 d . . . . .
D28B D 0.783(3) 0.1170(17) 0.276(2) 0.043(8) Uiso 1 1 d . . . . .
D28C D 0.651(3) 0.1534(19) 0.294(3) 0.058(10) Uiso 1 1 d . . . . .
C29 C 0.89188(19) 0.07540(12) 0.46556(17) 0.0258(4) Uani 1 1 d . . . . .
D29A D 0.931(3) 0.0839(15) 0.536(2) 0.034(7) Uiso 1 1 d . . . . .
D29B D 0.958(3) 0.0776(15) 0.423(2) 0.033(7) Uiso 1 1 d . . . . .
D29C D 0.852(3) 0.0304(15) 0.458(2) 0.031(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C22 1.692(4) . ?
S1 C23 1.722(8) . ?
S1A C23A 1.712(6) . ?
S1A C25 1.688(3) . ?
O1 H1 0.85(3) . ?
O1 C1 1.365(2) . ?
O2 H2 0.81(4) . ?
O2 C5 1.370(2) . ?
O3 H3 0.85(3) . ?
O3 C11 1.370(2) . ?
O4 H4 0.77(4) . ?
O4 C15 1.369(3) . ?
C1 C2 1.392(2) . ?
C1 C10 1.411(3) . ?
C2 C3 1.440(2) . ?
C2 C26 1.531(2) . ?
C3 C4 1.442(2) . ?
C3 C8 1.431(2) . ?
C4 C5 1.386(2) . ?
C4 C21 1.525(2) . ?
C5 C6 1.413(2) . ?
C6 H6 1.00(3) . ?
C6 C7 1.354(3) . ?
C7 H7 0.95(3) . ?
C7 C8 1.413(3) . ?
C8 C9 1.416(3) . ?
C9 H9 0.91(3) . ?
C9 C10 1.352(3) . ?
C10 H10 0.95(3) . ?
C11 C12 1.387(3) . ?
C11 C20 1.412(3) . ?
C12 C13 1.443(2) . ?
C12 C21 1.527(2) . ?
C13 C14 1.437(3) . ?
C13 C18 1.435(3) . ?
C14 C15 1.390(3) . ?
C14 C26 1.522(3) . ?
C15 C16 1.407(3) . ?
C16 H16 0.90(3) . ?
C16 C17 1.352(4) . ?
C17 H17 0.95(3) . ?
C17 C18 1.413(3) . ?
C18 C19 1.414(3) . ?
C19 H19 0.93(3) . ?
C19 C20 1.349(3) . ?
C20 H20 0.91(3) . ?
C21 H21 0.93(2) . ?
C21 C22 1.497(2) . ?
C22 C24A 1.477(12) . ?
C22 C25 1.352(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.375(15) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.364(15) . ?
C24 H24 0.9500 . ?
C24 C25 1.481(12) . ?
C24A H24A 0.9500 . ?
C25 C26 1.497(2) . ?
C26 H26 0.95(2) . ?
S2 O5 1.5095(18) . ?
S2 C27 1.751(3) . ?
S2 C30 1.772(3) . ?
C27 D27A 0.92(5) . ?
C27 D27B 1.03(5) . ?
C27 D27C 0.94(6) . ?
C30 D30A 0.98(4) . ?
C30 D30B 0.96(4) . ?
C30 D30C 0.85(5) . ?
S3 O6 1.5181(17) . ?
S3 C28 1.784(3) . ?
S3 C29 1.777(2) . ?
C28 D28A 0.98(3) . ?
C28 D28B 0.94(3) . ?
C28 D28C 0.96(4) . ?
C29 D29A 1.01(3) . ?
C29 D29B 0.98(3) . ?
C29 D29C 0.93(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 S1 C23 90.6(4) . . ?
C25 S1A C23A 92.8(3) . . ?
C1 O1 H1 113(2) . . ?
C5 O2 H2 111(2) . . ?
C11 O3 H3 112.5(19) . . ?
C15 O4 H4 109(3) . . ?
O1 C1 C2 124.44(18) . . ?
O1 C1 C10 113.24(17) . . ?
C2 C1 C10 122.33(18) . . ?
C1 C2 C3 118.29(16) . . ?
C1 C2 C26 116.46(16) . . ?
C3 C2 C26 125.25(15) . . ?
C2 C3 C4 124.56(15) . . ?
C8 C3 C2 118.07(16) . . ?
C8 C3 C4 117.33(16) . . ?
C3 C4 C21 124.23(15) . . ?
C5 C4 C3 118.95(15) . . ?
C5 C4 C21 116.75(15) . . ?
O2 C5 C4 118.34(16) . . ?
O2 C5 C6 118.90(16) . . ?
C4 C5 C6 122.75(17) . . ?
C5 C6 H6 121.0(16) . . ?
C7 C6 C5 118.83(17) . . ?
C7 C6 H6 120.1(16) . . ?
C6 C7 H7 119.2(16) . . ?
C6 C7 C8 121.35(17) . . ?
C8 C7 H7 119.4(16) . . ?
C7 C8 C3 120.72(17) . . ?
C7 C8 C9 118.90(17) . . ?
C9 C8 C3 120.37(17) . . ?
C8 C9 H9 120.2(17) . . ?
C10 C9 C8 120.88(18) . . ?
C10 C9 H9 118.9(17) . . ?
C1 C10 H10 120.6(16) . . ?
C9 C10 C1 119.58(18) . . ?
C9 C10 H10 119.8(16) . . ?
O3 C11 C12 123.88(17) . . ?
O3 C11 C20 113.70(17) . . ?
C12 C11 C20 122.38(18) . . ?
C11 C12 C13 118.53(16) . . ?
C11 C12 C21 116.56(16) . . ?
C13 C12 C21 124.91(16) . . ?
C14 C13 C12 124.94(16) . . ?
C18 C13 C12 117.82(17) . . ?
C18 C13 C14 117.24(17) . . ?
C13 C14 C26 124.24(16) . . ?
C15 C14 C13 119.38(18) . . ?
C15 C14 C26 116.36(17) . . ?
O4 C15 C14 118.22(19) . . ?
O4 C15 C16 119.37(19) . . ?
C14 C15 C16 122.4(2) . . ?
C15 C16 H16 119(2) . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 H16 122.4(19) . . ?
C16 C17 H17 120.8(16) . . ?
C16 C17 C18 121.7(2) . . ?
C18 C17 H17 117.5(16) . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 C19 119.24(19) . . ?
C19 C18 C13 120.43(18) . . ?
C18 C19 H19 118.0(16) . . ?
C20 C19 C18 120.92(19) . . ?
C20 C19 H19 121.1(16) . . ?
C11 C20 H20 117.9(18) . . ?
C19 C20 C11 119.8(2) . . ?
C19 C20 H20 122.3(18) . . ?
C4 C21 C12 113.21(13) . . ?
C4 C21 H21 104.8(12) . . ?
C12 C21 H21 104.0(13) . . ?
C22 C21 C4 112.92(14) . . ?
C22 C21 C12 113.10(14) . . ?
C22 C21 H21 107.9(13) . . ?
C21 C22 S1 125.2(2) . . ?
C24A C22 C21 126.8(6) . . ?
C25 C22 S1 113.4(2) . . ?
C25 C22 C21 121.45(15) . . ?
C25 C22 C24A 111.7(6) . . ?
S1 C23 H23 122.4 . . ?
C24 C23 S1 115.2(8) . . ?
C24 C23 H23 122.4 . . ?
S1A C23A H23A 124.1 . . ?
C24A C23A S1A 111.9(7) . . ?
C24A C23A H23A 124.1 . . ?
C23 C24 H24 126.5 . . ?
C23 C24 C25 107.0(11) . . ?
C25 C24 H24 126.5 . . ?
C22 C24A H24A 124.6 . . ?
C23A C24A C22 110.9(11) . . ?
C23A C24A H24A 124.6 . . ?
C22 C25 S1A 112.67(19) . . ?
C22 C25 C24 113.4(6) . . ?
C22 C25 C26 122.26(15) . . ?
C24 C25 C26 124.3(6) . . ?
C26 C25 S1A 124.70(19) . . ?
C2 C26 H26 105.4(13) . . ?
C14 C26 C2 112.80(14) . . ?
C14 C26 H26 108.5(13) . . ?
C25 C26 C2 114.57(15) . . ?
C25 C26 C14 111.20(15) . . ?
C25 C26 H26 103.5(13) . . ?
O5 S2 C27 105.0(2) . . ?
O5 S2 C30 105.28(14) . . ?
C27 S2 C30 98.6(2) . . ?
S2 C27 D27A 109(3) . . ?
S2 C27 D27B 99(2) . . ?
S2 C27 D27C 110(4) . . ?
D27A C27 D27B 102(4) . . ?
D27A C27 D27C 127(5) . . ?
D27B C27 D27C 106(4) . . ?
S2 C30 D30A 108(2) . . ?
S2 C30 D30B 104(2) . . ?
S2 C30 D30C 107(3) . . ?
D30A C30 D30B 110(3) . . ?
D30A C30 D30C 114(4) . . ?
D30B C30 D30C 113(4) . . ?
O6 S3 C28 105.09(12) . . ?
O6 S3 C29 103.71(10) . . ?
C29 S3 C28 98.38(13) . . ?
S3 C28 D28A 106.1(17) . . ?
S3 C28 D28B 109.7(19) . . ?
S3 C28 D28C 102(2) . . ?
D28A C28 D28B 108(3) . . ?
D28A C28 D28C 116(3) . . ?
D28B C28 D28C 115(3) . . ?
S3 C29 D29A 106.1(15) . . ?
S3 C29 D29B 110.5(16) . . ?
S3 C29 D29C 109.9(16) . . ?
D29A C29 D29B 111(2) . . ?
D29A C29 D29C 111(2) . . ?
D29B C29 D29C 109(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.85(3) 1.91(3) 2.734(3) 164(3) . yes
O2 H2 O6 0.81(4) 1.77(4) 2.576(2) 172(4) . yes
O3 H3 O2 0.85(3) 1.87(3) 2.725(2) 178(3) . yes
O4 H4 O5 0.77(4) 1.83(4) 2.599(2) 173(4) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C22 C25 C24 -2.6(8) . . . . ?
S1 C22 C25 C26 177.8(3) . . . . ?
S1 C23 C24 C25 -7.3(15) . . . . ?
S1A C23A C24A C22 -3.1(15) . . . . ?
S1A C25 C26 C2 -123.7(2) . . . . ?
S1A C25 C26 C14 107.0(2) . . . . ?
O1 C1 C2 C3 -171.32(17) . . . . ?
O1 C1 C2 C26 8.3(3) . . . . ?
O1 C1 C10 C9 173.65(18) . . . . ?
O2 C5 C6 C7 -177.15(17) . . . . ?
O3 C11 C12 C13 -177.49(16) . . . . ?
O3 C11 C12 C21 3.3(3) . . . . ?
O3 C11 C20 C19 179.36(17) . . . . ?
O4 C15 C16 C17 -178.78(19) . . . . ?
C1 C2 C3 C4 172.34(16) . . . . ?
C1 C2 C3 C8 -5.2(2) . . . . ?
C1 C2 C26 C14 -94.10(19) . . . . ?
C1 C2 C26 C25 137.33(17) . . . . ?
C2 C1 C10 C9 -6.3(3) . . . . ?
C2 C3 C4 C5 -175.97(16) . . . . ?
C2 C3 C4 C21 0.6(3) . . . . ?
C2 C3 C8 C7 178.64(16) . . . . ?
C2 C3 C8 C9 -0.4(3) . . . . ?
C3 C2 C26 C14 85.5(2) . . . . ?
C3 C2 C26 C25 -43.1(2) . . . . ?
C3 C4 C5 O2 176.07(15) . . . . ?
C3 C4 C5 C6 -3.1(3) . . . . ?
C3 C4 C21 C12 -76.2(2) . . . . ?
C3 C4 C21 C22 54.0(2) . . . . ?
C3 C8 C9 C10 2.8(3) . . . . ?
C4 C3 C8 C7 1.0(3) . . . . ?
C4 C3 C8 C9 -178.03(16) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
C4 C21 C22 S1 114.8(3) . . . . ?
C4 C21 C22 C24A 119.4(9) . . . . ?
C4 C21 C22 C25 -64.4(2) . . . . ?
C5 C4 C21 C12 100.50(18) . . . . ?
C5 C4 C21 C22 -129.35(16) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C3 -2.1(3) . . . . ?
C6 C7 C8 C9 176.90(18) . . . . ?
C7 C8 C9 C10 -176.20(19) . . . . ?
C8 C3 C4 C5 1.5(2) . . . . ?
C8 C3 C4 C21 178.15(15) . . . . ?
C8 C9 C10 C1 0.4(3) . . . . ?
C10 C1 C2 C3 8.6(3) . . . . ?
C10 C1 C2 C26 -171.77(17) . . . . ?
C11 C12 C13 C14 175.84(16) . . . . ?
C11 C12 C13 C18 -3.5(2) . . . . ?
C11 C12 C21 C4 -96.54(18) . . . . ?
C11 C12 C21 C22 133.40(16) . . . . ?
C12 C11 C20 C19 -2.8(3) . . . . ?
C12 C13 C14 C15 -179.73(16) . . . . ?
C12 C13 C14 C26 -1.0(3) . . . . ?
C12 C13 C18 C17 179.30(17) . . . . ?
C12 C13 C18 C19 0.3(3) . . . . ?
C12 C21 C22 S1 -115.0(3) . . . . ?
C12 C21 C22 C24A -110.4(9) . . . . ?
C12 C21 C22 C25 65.8(2) . . . . ?
C13 C12 C21 C4 84.32(19) . . . . ?
C13 C12 C21 C22 -45.7(2) . . . . ?
C13 C14 C15 O4 179.11(16) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C13 C14 C26 C2 -75.5(2) . . . . ?
C13 C14 C26 C25 54.8(2) . . . . ?
C13 C18 C19 C20 1.8(3) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
C14 C13 C18 C19 -179.12(17) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C15 C14 C26 C2 103.28(18) . . . . ?
C15 C14 C26 C25 -126.41(17) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C16 C17 C18 C19 179.5(2) . . . . ?
C17 C18 C19 C20 -177.16(19) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?
C18 C13 C14 C26 178.38(16) . . . . ?
C18 C19 C20 C11 -0.7(3) . . . . ?
C20 C11 C12 C13 4.9(3) . . . . ?
C20 C11 C12 C21 -174.31(16) . . . . ?
C21 C4 C5 O2 -0.8(2) . . . . ?
C21 C4 C5 C6 -179.96(16) . . . . ?
C21 C12 C13 C14 -5.0(3) . . . . ?
C21 C12 C13 C18 175.58(15) . . . . ?
C21 C22 C24A C23A 178.1(7) . . . . ?
C21 C22 C25 S1A -176.2(2) . . . . ?
C21 C22 C25 C24 176.7(8) . . . . ?
C21 C22 C25 C26 -2.9(3) . . . . ?
C22 S1 C23 C24 5.4(11) . . . . ?
C22 C25 C26 C2 63.9(2) . . . . ?
C22 C25 C26 C14 -65.5(2) . . . . ?
C23 S1 C22 C21 179.4(4) . . . . ?
C23 S1 C22 C25 -1.4(5) . . . . ?
C23 C24 C25 C22 6.3(14) . . . . ?
C23 C24 C25 C26 -174.2(7) . . . . ?
C23A S1A C25 C22 -1.9(4) . . . . ?
C23A S1A C25 C26 -175.0(3) . . . . ?
C24 C25 C26 C2 -115.6(9) . . . . ?
C24 C25 C26 C14 115.0(9) . . . . ?
C24A C22 C25 S1A 0.5(8) . . . . ?
C24A C22 C25 C26 173.8(8) . . . . ?
C25 S1A C23A C24A 2.9(10) . . . . ?
C25 C22 C24A C23A 1.7(14) . . . . ?
C26 C2 C3 C4 -7.2(3) . . . . ?
C26 C2 C3 C8 175.27(16) . . . . ?
C26 C14 C15 O4 0.3(2) . . . . ?
C26 C14 C15 C16 -178.29(18) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K75B61a
_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 1.157
_oxdiff_exptl_absorpt_empirical_full_min 0.944
####################################################################### 
# 
# 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_NM22011
_database_code_depnum_ccdc_archive 'CCDC 2286807'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;
_audit_creation_date             2022-06-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_chemical_formula_moiety         'C30 H22 O4'
_chemical_formula_sum            'C30 H22 O4'
_chemical_formula_weight         446.507
_chemical_oxdiff_formula         C30H22O4
_chemical_oxdiff_usercomment     '@ 100 K K73B53c'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   17.9101(6)
_cell_length_b                   8.2287(3)
_cell_length_c                   14.3468(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.751(4)
_cell_angle_gamma                90
_cell_volume                     2034.98(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7886
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      32.4080
_cell_measurement_theta_min      3.7910
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       prism
_exptl_crystal_F_000             936.599
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0875
1 0 0 0.0794
1 0 -1 0.0700
-1 0 1 0.0835
0 1 0 0.0280
0 -1 0 0.0275
-2 1 0 0.0617
2 -1 0 0.0558
-1 -1 -2 0.1065
1 1 2 0.1111
2 1 0 0.0585
-2 -1 0 0.0653

_exptl_crystal_recrystallization_method 
'The material was recrystallised from dichloromethane by slow cooling'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_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
-1.0000 -0.0000 -0.0000 0.0059 -0.0320 0.0252
1.0000 0.0000 0.0000 -0.0059 0.0320 -0.0252
1.0000 0.0000 -1.0000 -0.0279 0.0451 0.0193
-1.0000 -0.0000 1.0000 0.0279 -0.0451 -0.0193
0.0000 1.0000 -0.0000 0.0743 0.0346 0.0266
-0.0000 -1.0000 0.0000 -0.0743 -0.0346 -0.0266
-2.0000 1.0000 -0.0000 0.0861 -0.0294 0.0769
2.0000 -1.0000 0.0000 -0.0861 0.0294 -0.0769
-1.0000 -1.0000 -2.0000 -0.1125 -0.0404 0.0876
1.0000 1.0000 2.0000 0.1125 0.0404 -0.0876
2.0000 1.0000 -0.0000 0.0626 0.0986 -0.0238
-2.0000 -1.0000 0.0000 -0.0626 -0.0986 0.0238

_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.9973
_diffrn_reflns_Laue_measured_fraction_max 0.9659
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25275
_diffrn_reflns_point_group_measured_fraction_full 0.9973
_diffrn_reflns_point_group_measured_fraction_max 0.9659
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9659
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  49.00   1.00   30.00    --   19.09 -70.00  34.00  101
  2  ω    -11.00  91.00   1.00   30.00    --   19.09  70.00 165.00  102
  3  ω    -42.00  14.00   1.00   30.00    --  -17.68 -77.00 -90.00   56
  4  ω    -40.00  55.00   1.00   30.00    --  -17.68  38.00 -60.00   95
  5  ω     -8.00  89.00   1.00   30.00    --   19.09  57.00 -60.00   97
  6  ω   -103.00 -58.00   1.00   30.00    --  -17.68 178.00-150.00   45
  7  ω     -3.00  92.00   1.00   30.00    --   19.09  38.00  60.00   95
  8  ω    -15.00  59.00   1.00   30.00    --   19.09 -99.00 120.00   74
  9  ω    -15.00  37.00   1.00   30.00    --   19.09 -99.00 -90.00   52
 10  ω    -15.00  59.00   1.00   30.00    --   19.09 -99.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0058823000
_diffrn_orient_matrix_UB_12      0.0743223000
_diffrn_orient_matrix_UB_13      0.0220279000
_diffrn_orient_matrix_UB_21      0.0320107000
_diffrn_orient_matrix_UB_22      0.0346012000
_diffrn_orient_matrix_UB_23      -0.0130823000
_diffrn_orient_matrix_UB_31      -0.0251819000
_diffrn_orient_matrix_UB_32      0.0265845000
_diffrn_orient_matrix_UB_33      -0.0445210000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              25
_reflns_limit_h_min              -27
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                3083
_reflns_number_total             3569
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.2517
_refine_diff_density_min         -0.2710
_refine_diff_density_rms         0.0673
_refine_ls_d_res_high            0.6601
_refine_ls_d_res_low             6.2848
_refine_ls_goodness_of_fit_ref   1.0922
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.0922
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0070P)²+0.3672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0465
_refine_special_details          
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         PBE
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2022-06-02_20-17-48
;
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     direct
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.28453(3) 0.15982(7) 0.22224(4) 0.01737(11) Uani 1.000000 .
H1 H 0.2911(5) 0.1073(13) 0.1658(7) 0.038(3) Uani 1.000000 .
O2 O 0.69748(2) 0.03340(6) 0.45608(3) 0.01592(11) Uani 1.000000 .
C1 C 0.35278(3) 0.17632(8) 0.29335(4) 0.01197(12) Uani 1.000000 .
C2 C 0.34738(4) 0.28224(8) 0.36877(5) 0.01496(14) Uani 1.000000 .
H2 H 0.2927(4) 0.3422(10) 0.3631(6) 0.034(2) Uani 1.000000 .
C3 C 0.41056(4) 0.30523(8) 0.44582(5) 0.01423(13) Uani 1.000000 .
H3 H 0.4083(4) 0.3832(10) 0.5053(5) 0.033(2) Uani 1.000000 .
C4 C 0.48215(4) 0.22908(7) 0.44910(4) 0.01095(12) Uani 1.000000 .
C5 C 0.54634(4) 0.25722(8) 0.52977(5) 0.01286(13) Uani 1.000000 .
H5 H 0.5390(4) 0.3345(9) 0.5873(5) 0.029(2) Uani 1.000000 .
C6 C 0.61730(4) 0.18903(8) 0.53573(5) 0.01281(13) Uani 1.000000 .
H6 H 0.6652(4) 0.2112(9) 0.5972(5) 0.030(2) Uani 1.000000 .
C7 C 0.62584(3) 0.09483(8) 0.45704(4) 0.01113(12) Uani 1.000000 .
C8 C 0.56495(3) 0.06537(7) 0.37518(4) 0.00917(12) Uani 1.000000 .
C9 C 0.48938(3) 0.12757(7) 0.37111(4) 0.00888(12) Uani 1.000000 .
C10 C 0.42107(3) 0.09526(7) 0.29348(4) 0.00925(12) Uani 1.000000 .
C11 C 0.41678(3) -0.02199(8) 0.20967(4) 0.00919(12) Uani 1.000000 .
H11 H 0.3564(4) -0.0592(9) 0.1851(5) 0.0203(18) Uani 1.000000 .
C12 C 0.45971(3) -0.18063(7) 0.23311(4) 0.00992(12) Uani 1.000000 .
C13 C 0.41967(4) -0.32787(8) 0.21679(5) 0.01365(13) Uani 1.000000 .
H13 H 0.3567(4) -0.3271(9) 0.1924(6) 0.032(2) Uani 1.000000 .
C14 C 0.45955(4) -0.47507(9) 0.23347(5) 0.01731(14) Uani 1.000000 .
H14 H 0.4289(5) -0.5881(9) 0.2206(6) 0.038(2) Uani 1.000000 .
C15 C 0.75698(4) 0.02721(11) 0.54505(5) 0.01748(14) Uani 1.000000 .
H15a H 0.8010(5) -0.0480(13) 0.5311(6) 0.053(3) Uani 1.000000 .
H15b H 0.7354(5) -0.0250(11) 0.6015(6) 0.042(2) Uani 1.000000 .
H15c H 0.7800(5) 0.1492(11) 0.5672(6) 0.045(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.954(10) . ?
O1 C1 1.3697(7) . ?
O2 C7 1.3826(7) . ?
O2 C15 1.4244(8) . ?
C1 C2 1.4130(9) . ?
C1 C10 1.3927(8) . ?
C2 H2 1.080(7) . ?
C2 C3 1.3634(9) . ?
C3 H3 1.077(7) . ?
C3 C4 1.4164(9) . ?
C4 C5 1.4116(9) . ?
C4 C9 1.4301(8) . ?
C5 H5 1.078(7) . ?
C5 C6 1.3706(9) . ?
C6 H6 1.066(7) . ?
C6 C7 1.4115(9) . ?
C7 C8 1.3900(8) . ?
C8 C9 1.4334(8) . ?
C8 C11 1.5238(8) 2_655 ?
C9 C10 1.4380(8) . ?
C10 C11 1.5272(8) . ?
C11 H11 1.087(6) . ?
C11 C12 1.5060(8) . ?
C12 C12 1.3920(12) 2_655 ?
C12 C13 1.3951(9) . ?
C13 H13 1.086(7) . ?
C13 C14 1.3935(10) . ?
C14 C14 1.3970(14) 2_655 ?
C14 H14 1.070(8) . ?
C15 H15a 1.063(9) . ?
C15 H15b 1.077(8) . ?
C15 H15c 1.099(8) . ?

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 H1 112.7(5) . . ?
C15 O2 C7 118.34(5) . . ?
C2 C1 O1 113.50(5) . . ?
C10 C1 O1 124.01(6) . . ?
C10 C1 C2 122.47(6) . . ?
H2 C2 C1 118.2(4) . . ?
C3 C2 C1 119.49(6) . . ?
C3 C2 H2 122.3(4) . . ?
H3 C3 C2 121.5(4) . . ?
C4 C3 C2 120.67(6) . . ?
C4 C3 H3 117.8(4) . . ?
C5 C4 C3 118.89(6) . . ?
C9 C4 C3 120.39(6) . . ?
C9 C4 C5 120.72(6) . . ?
H5 C5 C4 118.9(4) . . ?
C6 C5 C4 121.27(6) . . ?
C6 C5 H5 119.9(4) . . ?
H6 C6 C5 120.4(4) . . ?
C7 C6 C5 118.36(6) . . ?
C7 C6 H6 121.2(4) . . ?
C6 C7 O2 120.74(5) . . ?
C8 C7 O2 116.44(5) . . ?
C8 C7 C6 122.75(6) . . ?
C9 C8 C7 119.20(5) . . ?
C11 C8 C7 117.90(5) 2_655 . ?
C11 C8 C9 122.75(5) 2_655 . ?
C8 C9 C4 117.49(5) . . ?
C10 C9 C4 118.37(5) . . ?
C10 C9 C8 124.13(5) . . ?
C9 C10 C1 118.34(6) . . ?
C11 C10 C1 116.42(5) . . ?
C11 C10 C9 125.24(5) . . ?
C10 C11 C8 110.80(5) . 2_655 ?
H11 C11 C8 106.5(4) . 2_655 ?
H11 C11 C10 105.4(4) . . ?
C12 C11 C8 112.33(5) . 2_655 ?
C12 C11 C10 117.27(5) . . ?
C12 C11 H11 103.4(4) . . ?
C12 C12 C11 119.74(3) 2_655 . ?
C13 C12 C11 120.48(5) . . ?
H13 C13 C12 119.4(4) . . ?
C14 C13 C12 120.66(6) . . ?
C14 C13 H13 120.0(4) . . ?
C14 C14 C13 119.63(4) 2_655 . ?
H14 C14 C13 120.7(4) . . ?
H15a C15 O2 105.3(4) . . ?
H15b C15 O2 110.7(4) . . ?
H15b C15 H15a 110.2(7) . . ?
H15c C15 O2 110.9(4) . . ?
H15c C15 H15a 110.3(7) . . ?
H15c C15 H15b 109.3(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.954(10) 1.913(10) 2.8599(7) 171.5(9) 2_655

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 C2 C3 177.81(6) . . . . ?
O1 C1 C10 C9 178.05(6) . . . . ?
O1 C1 C10 C11 -1.88(7) . . . . ?
O2 C7 C6 C5 175.14(6) . . . . ?
O2 C7 C8 C9 -179.23(5) . . . . ?
O2 C7 C8 C11 -3.55(7) . . . 2_655 ?
C1 C2 C3 C4 2.48(8) . . . . ?
C1 C10 C9 C4 5.91(7) . . . . ?
C1 C10 C9 C8 -173.56(5) . . . . ?
C1 C10 C11 C8 89.58(6) . . . 2_655 ?
C1 C10 C11 C12 -139.64(5) . . . . ?
C2 C3 C4 C5 179.43(6) . . . . ?
C2 C3 C4 C9 0.43(8) . . . . ?
C3 C4 C5 C6 -178.76(6) . . . . ?
C3 C4 C9 C8 174.86(6) . . . . ?
C3 C4 C9 C10 -4.65(7) . . . . ?
C4 C5 C6 C7 2.66(8) . . . . ?
C4 C9 C8 C7 5.09(7) . . . . ?
C4 C9 C8 C11 -170.37(5) . . . 2_655 ?
C4 C9 C10 C11 -174.17(5) . . . . ?
C5 C6 C7 C8 -1.61(8) . . . . ?
C6 C7 C8 C9 -2.35(7) . . . . ?
C6 C7 C8 C11 173.33(6) . . . 2_655 ?
C7 C8 C9 C10 -175.43(5) . . . . ?
C7 C8 C11 C10 -107.55(6) . . 2_655 2_655 ?
C7 C8 C11 C12 119.14(6) . . 2_655 2_655 ?
C8 C9 C10 C11 6.36(7) . . . . ?
C8 C11 C10 C9 -90.34(5) 2_655 . . . ?
C8 C11 C12 C12 65.15(6) . 2_655 2_655 . ?
C8 C11 C12 C13 -111.72(5) 2_655 . . . ?
C9 C10 C11 C12 40.44(7) . . . . ?
C10 C11 C12 C12 -64.92(6) . . . 2_655 ?
C10 C11 C12 C13 118.21(6) . . . . ?
C11 C12 C12 C11 6.84(6) . . 2_655 2_655 ?
C11 C12 C12 C13 -176.27(7) . . 2_655 2_655 ?
C11 C12 C13 C14 176.53(6) . . . . ?
C12 C12 C13 C14 -0.33(9) 2_655 . . . ?
C12 C13 C14 C14 -0.24(7) . . . 2_655 ?
C13 C14 C14 C13 0.52(6) . . 2_655 2_655 ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K73B53c
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.833
_vrf_PLAT414_NM22011             
;
PROBLEM: Short Intra D-H..H-X       H1       ..H11      .       1.77 Ang.  
RESPONSE: NoSpherA2 used, H atom positions freely refined.
;
####################################################################### 
# 
# 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_nm21004
_database_code_depnum_ccdc_archive 'CCDC 2286805'
loop_
_audit_author_name
_audit_author_address
'Gary Stephen Nichol'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2024-08-12 downloaded from the CCDC.
;

_vrf_PLAT414_nm21004             
;
PROBLEM: Short Intra D-H..H-X       H3       ..H21      .       1.76 Ang.
RESPONSE: H atom treatment is discussed in _refine_special_details.
;
_vrf_PLAT414_nm21004_2           
;
PROBLEM: Short Intra D-H..H-X       H4       ..H28      .       1.84 Ang.
RESPONSE: H atom treatment is discussed in _refine_special_details.
;
# Added during the CSD deposition process: Friday 04 August 2023 01:18 PM
# end Validation Reply Form

_audit_creation_date             2021-11-15
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
loop_
_audit_author_email
''
g.s.nichol@ed.ac.uk
_chemical_formula_moiety         'C28 H18 O4, C3 H8 O'
_chemical_formula_sum            'C31 H26 O5'
_chemical_formula_weight         478.549
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   10.2376(7)
_cell_length_b                   10.4837(6)
_cell_length_c                   12.0766(7)
_cell_angle_alpha                107.559(3)
_cell_angle_beta                 103.934(3)
_cell_angle_gamma                103.550(3)
_cell_volume                     1131.50(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      36.10
_cell_measurement_theta_min      2.26
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1030 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.9640.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       plate
_exptl_crystal_F_000             504.271
_exptl_crystal_recrystallization_method 
'The material was recrystallised from isopropanol by slow evaporation'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.153
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9936
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            94416
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9936
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         36.38
_diffrn_reflns_theta_min         2.16
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9936
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              16
_reflns_limit_k_min              -17
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                8328
_reflns_number_total             10949
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       APEX4
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.6082
_refine_diff_density_min         -0.3189
_refine_diff_density_rms         0.0798
_refine_ls_d_res_high            0.5992
_refine_ls_d_res_low             9.4293
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     559
_refine_ls_number_reflns         10949
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.0587
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.0726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          
;
All H atoms were identified from a difference Fourier map and refined freely, with the exception of H30 which was controlled by means of a RIGU restraint.
;
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 H30, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_primary     iterative
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.71903(5) 0.36111(5) 0.10338(4) 0.01943(9) Uani 1.000000 . .
H1 H 0.7171(13) 0.2899(13) 0.0307(12) 0.044(3) Uani 1.000000 . .
O2 O 0.59949(5) 1.03715(4) 0.30873(4) 0.01853(9) Uani 1.000000 . .
H2 H 0.6072(14) 1.1175(15) 0.2887(12) 0.053(3) Uani 1.000000 . .
O3 O 0.39260(5) 0.89931(5) 0.37912(5) 0.02086(9) Uani 1.000000 . .
H3 H 0.4814(11) 0.9552(11) 0.3760(12) 0.039(3) Uani 1.000000 . .
O4 O 0.62616(5) 0.27508(4) 0.26601(4) 0.01762(8) Uani 1.000000 . .
H4 H 0.6641(13) 0.3006(12) 0.2103(12) 0.044(3) Uani 1.000000 . .
C1 C 0.70380(6) 0.48158(6) 0.08708(5) 0.01422(9) Uani 1.000000 . .
C2 C 0.69746(6) 0.58897(5) 0.18486(5) 0.01172(9) Uani 1.000000 . .
C3 C 0.67333(5) 0.71103(5) 0.16534(5) 0.01132(9) Uani 1.000000 . .
C4 C 0.64924(5) 0.82135(5) 0.25385(5) 0.01127(9) Uani 1.000000 . .
C5 C 0.62732(6) 0.93493(5) 0.22496(5) 0.01322(9) Uani 1.000000 . .
C6 C 0.63115(6) 0.94849(6) 0.11287(5) 0.01577(10) Uani 1.000000 . .
H6 H 0.6143(11) 1.0386(10) 0.0940(8) 0.037(3) Uani 1.000000 . .
C7 C 0.65299(6) 0.84348(6) 0.02718(5) 0.01572(10) Uani 1.000000 . .
H7 H 0.6546(10) 0.8489(10) -0.0596(8) 0.034(2) Uani 1.000000 . .
C8 C 0.67128(6) 0.72289(6) 0.04990(5) 0.01336(9) Uani 1.000000 . .
C9 C 0.68469(6) 0.61283(6) -0.04417(5) 0.01554(10) Uani 1.000000 . .
H9 H 0.6839(10) 0.6260(10) -0.1279(8) 0.035(2) Uani 1.000000 . .
C10 C 0.69716(6) 0.49212(6) -0.02782(5) 0.01645(10) Uani 1.000000 . .
H10 H 0.7035(11) 0.4067(10) -0.1009(9) 0.037(2) Uani 1.000000 . .
C11 C 0.39375(6) 0.76936(6) 0.38060(5) 0.01442(10) Uani 1.000000 . .
C12 C 0.50500(6) 0.71703(5) 0.36977(5) 0.01147(9) Uani 1.000000 . .
C13 C 0.48348(5) 0.57118(5) 0.35377(5) 0.01117(9) Uani 1.000000 . .
C14 C 0.57975(6) 0.49785(5) 0.32287(5) 0.01137(9) Uani 1.000000 . .
C15 C 0.54320(6) 0.35458(5) 0.30272(5) 0.01315(9) Uani 1.000000 . .
C16 C 0.41918(6) 0.27925(6) 0.31737(5) 0.01495(10) Uani 1.000000 . .
H16 H 0.3978(10) 0.1703(10) 0.3037(9) 0.035(2) Uani 1.000000 . .
C17 C 0.32682(6) 0.34765(6) 0.34721(5) 0.01486(10) Uani 1.000000 . .
H17 H 0.2301(10) 0.2919(10) 0.3544(9) 0.035(2) Uani 1.000000 . .
C18 C 0.35495(6) 0.49205(6) 0.36349(5) 0.01314(9) Uani 1.000000 . .
C19 C 0.25182(6) 0.55613(6) 0.38664(5) 0.01676(10) Uani 1.000000 . .
H19 H 0.1591(9) 0.4926(9) 0.3954(9) 0.033(2) Uani 1.000000 . .
C20 C 0.26936(6) 0.69155(6) 0.39337(6) 0.01773(10) Uani 1.000000 . .
H20 H 0.1907(10) 0.7417(11) 0.4075(11) 0.046(3) Uani 1.000000 . .
C21 C 0.64285(5) 0.82134(5) 0.37846(5) 0.01110(9) Uani 1.000000 . .
H21 H 0.6429(9) 0.9257(9) 0.4301(8) 0.025(2) Uani 1.000000 . .
C22 C 0.77796(5) 0.81436(5) 0.45704(5) 0.01193(9) Uani 1.000000 . .
C23 C 0.86553(6) 0.92914(6) 0.56606(5) 0.01519(10) Uani 1.000000 . .
H23 H 0.8338(10) 1.0220(9) 0.5950(9) 0.032(2) Uani 1.000000 . .
C24 C 0.99182(6) 0.92407(6) 0.63758(6) 0.01837(11) Uani 1.000000 . .
H24 H 1.0567(10) 1.0138(10) 0.7201(9) 0.038(2) Uani 1.000000 . .
C25 C 1.03186(6) 0.80391(7) 0.59952(6) 0.01862(11) Uani 1.000000 . .
H25 H 1.1286(10) 0.7962(11) 0.6510(9) 0.043(3) Uani 1.000000 . .
C26 C 0.94461(6) 0.68976(6) 0.49066(5) 0.01565(10) Uani 1.000000 . .
H26 H 0.9763(10) 0.5956(9) 0.4628(10) 0.036(3) Uani 1.000000 . .
C27 C 0.81710(5) 0.69401(6) 0.41959(5) 0.01219(9) Uani 1.000000 . .
C28 C 0.71880(6) 0.56664(5) 0.30621(5) 0.01181(9) Uani 1.000000 . .
H28 H 0.7726(9) 0.4886(9) 0.2985(8) 0.027(2) Uani 1.000000 . .
O5 O 0.73267(5) 0.15252(5) -0.08409(5) 0.02559(10) Uani 1.000000 . .
H5 H 0.6760(14) 0.1313(15) -0.1706(13) 0.062(4) Uani 1.000000 . .
C29 C 0.95622(9) 0.17507(11) 0.05072(8) 0.03571(17) Uani 1.000000 . .
H29a H 0.9717(10) 0.2822(10) 0.1061(8) 0.036(3) Uani 1.000000 . .
H29b H 0.9012(13) 0.0984(16) 0.0838(12) 0.077(5) Uani 1.000000 . .
H29c H 1.0661(12) 0.1726(17) 0.0612(13) 0.082(5) Uani 1.000000 . .
C30 C 0.87320(7) 0.14695(7) -0.08069(6) 0.02360(12) Uani 1.000000 . U
H30 H 0.8694(10) 0.0393(9) -0.1363(9) 0.041(3) Uani 1.000000 . U
C31 C 0.94280(8) 0.25193(9) -0.12940(8) 0.03197(15) Uani 1.000000 . .
H31a H 0.8736(14) 0.2324(15) -0.2246(11) 0.074(4) Uani 1.000000 . .
H31b H 0.9578(14) 0.3586(12) -0.0671(11) 0.059(3) Uani 1.000000 . .
H31c H 1.0459(11) 0.2437(14) -0.1313(12) 0.064(4) Uani 1.000000 . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3733(7) . ?
O2 C5 1.3715(7) . ?
O3 C11 1.3706(7) . ?
O4 C15 1.3793(7) . ?
C1 C2 1.3911(7) . ?
C1 C10 1.4117(8) . ?
C2 C3 1.4339(7) . ?
C2 C28 1.5254(7) . ?
C3 C4 1.4338(7) . ?
C3 C8 1.4321(7) . ?
C4 C5 1.3885(7) . ?
C4 C21 1.5220(7) . ?
C5 C6 1.4118(8) . ?
C6 C7 1.3683(8) . ?
C7 C8 1.4156(7) . ?
C8 C9 1.4140(8) . ?
C9 C10 1.3678(8) . ?
C11 C12 1.3916(7) . ?
C11 C20 1.4124(8) . ?
C12 C13 1.4378(7) . ?
C12 C21 1.5279(7) . ?
C13 C14 1.4354(7) . ?
C13 C18 1.4336(7) . ?
C14 C15 1.3883(7) . ?
C14 C28 1.5270(7) . ?
C15 C16 1.4105(8) . ?
C16 C17 1.3654(8) . ?
C17 C18 1.4150(7) . ?
C18 C19 1.4161(8) . ?
C19 C20 1.3632(8) . ?
C21 C22 1.5088(7) . ?
C22 C23 1.3983(7) . ?
C22 C27 1.3918(7) . ?
C23 C24 1.3938(8) . ?
C24 C25 1.3962(9) . ?
C25 C26 1.3938(8) . ?
C26 C27 1.3975(7) . ?
C27 C28 1.5081(7) . ?
O5 C30 1.4448(8) . ?
C29 C30 1.5095(10) . ?
C30 C31 1.5133(10) . ?

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 O1 118.72(5) . . ?
C10 C1 O1 118.58(5) . . ?
C10 C1 C2 122.69(5) . . ?
C3 C2 C1 118.56(5) . . ?
C28 C2 C1 116.23(4) . . ?
C28 C2 C3 125.20(4) . . ?
C4 C3 C2 123.98(4) . . ?
C8 C3 C2 118.17(5) . . ?
C8 C3 C4 117.85(4) . . ?
C5 C4 C3 118.96(5) . . ?
C21 C4 C3 124.10(4) . . ?
C21 C4 C5 116.93(5) . . ?
C4 C5 O2 118.30(5) . . ?
C6 C5 O2 118.94(5) . . ?
C6 C5 C4 122.75(5) . . ?
C7 C6 C5 118.88(5) . . ?
C8 C7 C6 120.83(5) . . ?
C7 C8 C3 120.63(5) . . ?
C9 C8 C3 120.43(5) . . ?
C9 C8 C7 118.93(5) . . ?
C10 C9 C8 120.86(5) . . ?
C9 C10 C1 119.01(5) . . ?
C12 C11 O3 124.06(5) . . ?
C20 C11 O3 113.36(5) . . ?
C20 C11 C12 122.57(5) . . ?
C13 C12 C11 118.24(5) . . ?
C21 C12 C11 116.82(4) . . ?
C21 C12 C13 124.93(5) . . ?
C14 C13 C12 123.96(5) . . ?
C18 C13 C12 118.14(5) . . ?
C18 C13 C14 117.83(4) . . ?
C15 C14 C13 118.63(5) . . ?
C28 C14 C13 123.94(4) . . ?
C28 C14 C15 117.40(5) . . ?
C14 C15 O4 122.03(5) . . ?
C16 C15 O4 114.99(5) . . ?
C16 C15 C14 122.97(5) . . ?
C17 C16 C15 119.02(5) . . ?
C18 C17 C16 120.61(5) . . ?
C17 C18 C13 120.82(5) . . ?
C19 C18 C13 120.54(5) . . ?
C19 C18 C17 118.63(5) . . ?
C20 C19 C18 120.58(5) . . ?
C19 C20 C11 119.37(5) . . ?
C12 C21 C4 113.41(4) . . ?
C22 C21 C4 112.63(4) . . ?
C22 C21 C12 114.97(4) . . ?
C23 C22 C21 120.41(5) . . ?
C27 C22 C21 119.80(5) . . ?
C27 C22 C23 119.78(5) . . ?
C24 C23 C22 120.53(5) . . ?
C25 C24 C23 119.74(5) . . ?
C26 C25 C24 119.63(5) . . ?
C27 C26 C25 120.70(5) . . ?
C26 C27 C22 119.61(5) . . ?
C28 C27 C22 119.95(5) . . ?
C28 C27 C26 120.38(5) . . ?
C14 C28 C2 113.70(4) . . ?
C27 C28 C2 115.21(4) . . ?
C27 C28 C14 112.12(4) . . ?
C29 C30 O5 107.32(6) . . ?
C31 C30 O5 110.01(6) . . ?
C31 C30 C29 113.16(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
O1 C1 C2 C3 -176.46(5) . . . . ?
O1 C1 C2 C28 4.17(6) . . . . ?
O1 C1 C10 C9 -178.78(5) . . . . ?
O2 C5 C4 C3 177.77(5) . . . . ?
O2 C5 C4 C21 -1.00(6) . . . . ?
O2 C5 C6 C7 -177.30(5) . . . . ?
O3 C11 C12 C13 -170.63(5) . . . . ?
O3 C11 C12 C21 10.54(6) . . . . ?
O3 C11 C20 C19 174.98(5) . . . . ?
O4 C15 C14 C13 176.32(5) . . . . ?
O4 C15 C14 C28 -1.61(6) . . . . ?
O4 C15 C16 C17 -176.59(5) . . . . ?
C1 C2 C3 C4 172.98(5) . . . . ?
C1 C2 C3 C8 -6.18(6) . . . . ?
C1 C2 C28 C14 -93.34(5) . . . . ?
C1 C2 C28 C27 135.26(5) . . . . ?
C1 C10 C9 C8 -3.19(7) . . . . ?
C2 C3 C4 C5 179.88(5) . . . . ?
C2 C3 C4 C21 -1.45(6) . . . . ?
C2 C3 C8 C7 -177.74(5) . . . . ?
C2 C3 C8 C9 3.52(6) . . . . ?
C2 C28 C14 C13 -75.42(5) . . . . ?
C2 C28 C14 C15 102.39(5) . . . . ?
C2 C28 C27 C22 66.39(5) . . . . ?
C2 C28 C27 C26 -116.50(5) . . . . ?
C3 C4 C5 C6 -1.59(6) . . . . ?
C3 C4 C21 C12 -74.27(5) . . . . ?
C3 C4 C21 C22 58.48(5) . . . . ?
C3 C8 C7 C6 -2.66(6) . . . . ?
C3 C8 C9 C10 1.23(6) . . . . ?
C4 C5 C6 C7 2.06(6) . . . . ?
C4 C21 C12 C11 -92.17(5) . . . . ?
C4 C21 C12 C13 89.08(5) . . . . ?
C4 C21 C22 C23 113.52(5) . . . . ?
C4 C21 C22 C27 -65.24(5) . . . . ?
C5 C6 C7 C8 0.11(6) . . . . ?
C6 C7 C8 C9 176.10(5) . . . . ?
C7 C8 C9 C10 -177.53(5) . . . . ?
C11 C12 C13 C14 170.16(5) . . . . ?
C11 C12 C13 C18 -6.78(6) . . . . ?
C11 C12 C21 C22 136.22(5) . . . . ?
C11 C20 C19 C18 -1.83(7) . . . . ?
C12 C13 C14 C15 -176.25(5) . . . . ?
C12 C13 C14 C28 1.54(6) . . . . ?
C12 C13 C18 C17 179.24(5) . . . . ?
C12 C13 C18 C19 0.80(6) . . . . ?
C12 C21 C22 C23 -114.50(5) . . . . ?
C12 C21 C22 C27 66.74(5) . . . . ?
C13 C14 C15 C16 -3.35(6) . . . . ?
C13 C14 C28 C27 57.48(5) . . . . ?
C13 C18 C17 C16 -2.43(6) . . . . ?
C13 C18 C19 C20 3.59(6) . . . . ?
C14 C15 C16 C17 3.10(6) . . . . ?
C14 C28 C27 C22 -65.75(5) . . . . ?
C14 C28 C27 C26 111.35(5) . . . . ?
C15 C16 C17 C18 -0.13(6) . . . . ?
C16 C17 C18 C19 176.03(5) . . . . ?
C17 C18 C19 C20 -174.87(5) . . . . ?
C21 C22 C23 C24 -178.74(5) . . . . ?
C21 C22 C27 C26 178.00(5) . . . . ?
C21 C22 C27 C28 -4.88(5) . . . . ?
C22 C23 C24 C25 0.56(6) . . . . ?
C22 C27 C26 C25 0.95(6) . . . . ?
C23 C24 C25 C26 -0.39(7) . . . . ?
C24 C25 C26 C27 -0.37(7) . . . . ?
C25 C26 C27 C28 -176.16(5) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id K48A197
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
C30 H30 0.004000 -0.000893 0.001678 0.011309
