# Electronic Supplementary Material (ESI) 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2295945'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C41 H22 O'
_chemical_formula_sum            'C41 H22 O'
_chemical_formula_weight         530.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0168(4)
_cell_length_b                   42.038(2)
_cell_length_c                   15.3836(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.965(3)
_cell_angle_gamma                90
_cell_volume                     5134.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7431
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.76

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            110110
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.651
_diffrn_reflns_theta_max         25.051
_diffrn_reflns_theta_full        25.051
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9071
_reflns_number_gt                5589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Intrinsic Phasing (Bruker)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to 
ideal positions and refined isotropically using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+2.7178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9071
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.4300(2) 0.44928(5) 0.43400(12) 0.0338(5) Uani 1 1 d . . . . .
O2 O 0.1957(3) 0.48691(5) 0.57839(13) 0.0388(5) Uani 1 1 d . . . . .
C52 C 0.6436(3) 0.41452(6) 0.62788(16) 0.0208(6) Uani 1 1 d . . . . .
C67 C 0.4860(3) 0.33227(6) 0.53435(17) 0.0221(7) Uani 1 1 d . . . . .
C53 C 0.5582(3) 0.38664(6) 0.58102(17) 0.0220(7) Uani 1 1 d . . . . .
C81 C 0.3515(3) 0.37698(7) 0.44966(17) 0.0226(7) Uani 1 1 d . . . . .
C28 C 0.5061(3) 0.43139(6) 0.88080(17) 0.0235(7) Uani 1 1 d . . . . .
C41 C 0.2194(3) 0.43918(7) 0.66896(17) 0.0237(7) Uani 1 1 d . . . . .
C43 C 0.6027(3) 0.44177(6) 0.57443(17) 0.0229(7) Uani 1 1 d . . . . .
C24 C 0.2599(3) 0.38944(7) 0.97164(17) 0.0237(7) Uani 1 1 d . . . . .
C64 C 0.4759(3) 0.29089(7) 0.36986(18) 0.0269(7) Uani 1 1 d . . . . .
H64 H 0.470598 0.313227 0.360584 0.032 Uiso 1 1 calc R U . . .
C82 C 0.4615(3) 0.39733(6) 0.50504(17) 0.0229(7) Uani 1 1 d . . . . .
C29 C 0.6099(3) 0.40744(7) 0.92928(17) 0.0248(7) Uani 1 1 d . . . . .
C12 C 0.1568(3) 0.40871(7) 0.65546(17) 0.0225(7) Uani 1 1 d . . . . .
C54 C 0.5747(3) 0.35328(6) 0.59663(17) 0.0227(7) Uani 1 1 d . . . . .
C65 C 0.5115(3) 0.27910(6) 0.45597(18) 0.0240(7) Uani 1 1 d . . . . .
C27 C 0.3689(3) 0.42460(6) 0.81194(17) 0.0214(7) Uani 1 1 d . . . . .
C13 C 0.1838(3) 0.38577(6) 0.72424(17) 0.0231(7) Uani 1 1 d . . . . .
C25 C 0.2469(3) 0.37677(6) 0.88292(17) 0.0231(7) Uani 1 1 d . . . . .
C66 C 0.5401(3) 0.29958(6) 0.53336(18) 0.0243(7) Uani 1 1 d . . . . .
C26 C 0.2689(3) 0.39575(6) 0.80686(17) 0.0221(7) Uani 1 1 d . . . . .
C39 C 0.3891(3) 0.47973(7) 0.76096(18) 0.0267(7) Uani 1 1 d . . . . .
H39 H 0.363955 0.495416 0.716614 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2025(3) 0.34461(7) 0.86993(19) 0.0264(7) Uani 1 1 d . . . . .
C69 C 0.2059(3) 0.32559(7) 0.43389(18) 0.0265(7) Uani 1 1 d . . . . .
C42 C 0.4879(3) 0.43205(7) 0.49499(18) 0.0247(7) Uani 1 1 d . . . . .
C57 C 0.6300(3) 0.28675(7) 0.61005(18) 0.0270(7) Uani 1 1 d . . . . .
C40 C 0.3274(3) 0.44797(7) 0.74655(18) 0.0247(7) Uani 1 1 d . . . . .
C19 C 0.2739(3) 0.36782(7) 1.04301(18) 0.0285(7) Uani 1 1 d . . . . .
C50 C 0.8092(3) 0.44860(7) 0.73327(17) 0.0233(7) Uani 1 1 d . . . . .
C60 C 0.5309(3) 0.24584(7) 0.46644(19) 0.0280(7) Uani 1 1 d . . . . .
C68 C 0.3466(3) 0.34464(6) 0.47315(17) 0.0227(7) Uani 1 1 d . . . . .
C11 C 0.0504(3) 0.40713(7) 0.56764(17) 0.0254(7) Uani 1 1 d . . . . .
C23 C 0.2442(3) 0.42208(7) 0.98997(18) 0.0248(7) Uani 1 1 d . . . . .
H23 H 0.226720 0.436863 0.942877 0.030 Uiso 1 1 calc R U . . .
C80 C 0.2472(3) 0.38824(7) 0.37413(17) 0.0267(7) Uani 1 1 d . . . . .
H80 H 0.249857 0.410042 0.358126 0.032 Uiso 1 1 calc R U . . .
C55 C 0.6820(3) 0.33970(7) 0.66889(18) 0.0275(7) Uani 1 1 d . . . . .
H55 H 0.742529 0.353291 0.711437 0.033 Uiso 1 1 calc R U . . .
C37 C 0.5475(3) 0.46346(7) 0.89871(18) 0.0267(7) Uani 1 1 d . . . . .
C51 C 0.7440(3) 0.41796(6) 0.70633(17) 0.0237(7) Uani 1 1 d . . . . .
H51 H 0.770661 0.400007 0.743134 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1489(3) 0.33334(7) 0.78398(19) 0.0302(7) Uani 1 1 d . . . . .
H15 H 0.126767 0.311316 0.774525 0.036 Uiso 1 1 calc R U . . .
C79 C 0.1429(4) 0.36761(7) 0.32455(18) 0.0310(8) Uani 1 1 d . . . . .
H79 H 0.085657 0.374447 0.269507 0.037 Uiso 1 1 calc R U . . .
C70 C 0.1463(3) 0.29709(7) 0.47323(19) 0.0290(7) Uani 1 1 d . . . . .
C38 C 0.4831(3) 0.48733(7) 0.83787(19) 0.0293(7) Uani 1 1 d . . . . .
H38 H 0.506713 0.509051 0.851517 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0545(4) 0.43784(7) 0.52980(19) 0.0283(7) Uani 1 1 d . . . . .
C78 C 0.1181(4) 0.33613(7) 0.35343(18) 0.0303(7) Uani 1 1 d . . . . .
C14 C 0.1287(3) 0.35368(7) 0.71501(19) 0.0287(7) Uani 1 1 d . . . . .
H14 H 0.076635 0.346333 0.659387 0.034 Uiso 1 1 calc R U . . .
C49 C 0.9121(3) 0.45310(7) 0.81415(18) 0.0279(7) Uani 1 1 d . . . . .
H49 H 0.940423 0.435395 0.851675 0.033 Uiso 1 1 calc R U . . .
C10 C -0.0470(3) 0.38402(7) 0.52279(17) 0.0270(7) Uani 1 1 d . . . . .
H10 H -0.051698 0.363343 0.547259 0.032 Uiso 1 1 calc R U . . .
C9 C -0.1411(4) 0.39100(8) 0.43958(18) 0.0311(7) Uani 1 1 d . . . . .
C30 C 0.6229(3) 0.37574(7) 0.89836(19) 0.0285(7) Uani 1 1 d . . . . .
H30 H 0.556496 0.369421 0.845194 0.034 Uiso 1 1 calc R U . . .
C45 C 0.7683(3) 0.47552(7) 0.67795(18) 0.0251(7) Uani 1 1 d . . . . .
C44 C 0.6617(3) 0.47121(7) 0.59713(18) 0.0266(7) Uani 1 1 d . . . . .
H44 H 0.632082 0.488802 0.559374 0.032 Uiso 1 1 calc R U . . .
C71 C 0.1895(3) 0.28883(7) 0.56227(19) 0.0285(7) Uani 1 1 d . . . . .
H71 H 0.262899 0.302374 0.599356 0.034 Uiso 1 1 calc R U . . .
C1 C 0.1608(4) 0.45902(8) 0.59102(19) 0.0298(7) Uani 1 1 d . . . . .
C4 C -0.1346(3) 0.42180(8) 0.40294(18) 0.0315(8) Uani 1 1 d . . . . .
C22 C 0.2536(3) 0.43286(7) 1.07486(18) 0.0291(7) Uani 1 1 d . . . . .
H22 H 0.240389 0.454904 1.085665 0.035 Uiso 1 1 calc R U . . .
C56 C 0.6988(3) 0.30790(7) 0.67784(18) 0.0289(7) Uani 1 1 d . . . . .
H56 H 0.757936 0.299450 0.730574 0.035 Uiso 1 1 calc R U . . .
C46 C 0.8326(3) 0.50551(7) 0.70630(19) 0.0309(7) Uani 1 1 d . . . . .
H46 H 0.805796 0.523583 0.669965 0.037 Uiso 1 1 calc R U . . .
C63 C 0.4488(4) 0.27087(7) 0.29904(19) 0.0336(8) Uani 1 1 d . . . . .
H63 H 0.425165 0.279430 0.241496 0.040 Uiso 1 1 calc R U . . .
C59 C 0.5939(4) 0.23345(7) 0.55107(19) 0.0330(8) Uani 1 1 d . . . . .
H59 H 0.595880 0.211107 0.560476 0.040 Uiso 1 1 calc R U . . .
C31 C 0.7295(4) 0.35419(7) 0.9438(2) 0.0355(8) Uani 1 1 d . . . . .
H31 H 0.738014 0.333334 0.921098 0.043 Uiso 1 1 calc R U . . .
C34 C 0.7192(4) 0.41631(7) 1.00595(18) 0.0306(7) Uani 1 1 d . . . . .
C8 C -0.2395(4) 0.36757(8) 0.39101(19) 0.0366(8) Uani 1 1 d . . . . .
H8 H -0.247833 0.346944 0.415255 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2557(4) 0.33464(7) 1.0263(2) 0.0329(8) Uani 1 1 d . . . . .
H18 H 0.274962 0.319975 1.073653 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2111(4) 0.32383(7) 0.9435(2) 0.0324(8) Uani 1 1 d . . . . .
H17 H 0.185071 0.301939 0.934268 0.039 Uiso 1 1 calc R U . . .
C36 C 0.6559(4) 0.47156(7) 0.97673(19) 0.0323(8) Uani 1 1 d . . . . .
H36 H 0.675631 0.493343 0.991135 0.039 Uiso 1 1 calc R U . . .
C62 C 0.4558(4) 0.23810(7) 0.3110(2) 0.0356(8) Uani 1 1 d . . . . .
H62 H 0.430194 0.224305 0.262024 0.043 Uiso 1 1 calc R U . . .
C20 C 0.2912(4) 0.37978(8) 1.12905(19) 0.0336(8) Uani 1 1 d . . . . .
H20 H 0.309370 0.365410 1.177090 0.040 Uiso 1 1 calc R U . . .
C3 C -0.0352(4) 0.44546(7) 0.45077(19) 0.0341(8) Uani 1 1 d . . . . .
H3 H -0.031124 0.466409 0.428027 0.041 Uiso 1 1 calc R U . . .
C58 C 0.6506(4) 0.25315(7) 0.6176(2) 0.0334(8) Uani 1 1 d . . . . .
H58 H 0.705685 0.244433 0.670958 0.040 Uiso 1 1 calc R U . . .
C72 C 0.1289(4) 0.26182(7) 0.5970(2) 0.0359(8) Uani 1 1 d . . . . .
H72 H 0.159768 0.257073 0.657519 0.043 Uiso 1 1 calc R U . . .
C48 C 0.9724(3) 0.48283(7) 0.83964(19) 0.0301(7) Uani 1 1 d . . . . .
H48 H 1.041296 0.485488 0.894572 0.036 Uiso 1 1 calc R U . . .
C21 C 0.2823(4) 0.41181(8) 1.14511(19) 0.0335(8) Uani 1 1 d . . . . .
H21 H 0.295653 0.419533 1.203693 0.040 Uiso 1 1 calc R U . . .
C75 C 0.0284(4) 0.27715(7) 0.4216(2) 0.0350(8) Uani 1 1 d . . . . .
C61 C 0.4990(4) 0.22588(7) 0.3922(2) 0.0328(8) Uani 1 1 d . . . . .
H61 H 0.508028 0.203475 0.399523 0.039 Uiso 1 1 calc R U . . .
C47 C 0.9326(4) 0.50910(7) 0.78503(19) 0.0331(8) Uani 1 1 d . . . . .
H47 H 0.975329 0.529518 0.802739 0.040 Uiso 1 1 calc R U . . .
C33 C 0.8220(4) 0.39306(8) 1.0531(2) 0.0385(8) Uani 1 1 d . . . . .
H33 H 0.889643 0.398788 1.106521 0.046 Uiso 1 1 calc R U . . .
C35 C 0.7314(4) 0.44894(8) 1.03065(19) 0.0337(8) Uani 1 1 d . . . . .
H35 H 0.793111 0.454829 1.085507 0.040 Uiso 1 1 calc R U . . .
C32 C 0.8260(4) 0.36254(8) 1.0234(2) 0.0405(8) Uani 1 1 d . . . . .
H32 H 0.893791 0.347051 1.056525 0.049 Uiso 1 1 calc R U . . .
C73 C 0.0223(4) 0.24128(8) 0.5441(2) 0.0422(9) Uani 1 1 d . . . . .
H73 H -0.014341 0.221970 0.567340 0.051 Uiso 1 1 calc R U . . .
C74 C -0.0288(4) 0.24921(7) 0.4585(2) 0.0426(9) Uani 1 1 d . . . . .
H74 H -0.104542 0.235580 0.423082 0.051 Uiso 1 1 calc R U . . .
C77 C -0.0011(4) 0.31568(8) 0.3038(2) 0.0413(9) Uani 1 1 d . . . . .
H77 H -0.055146 0.322385 0.247925 0.050 Uiso 1 1 calc R U . . .
C7 C -0.3233(4) 0.37422(9) 0.3091(2) 0.0423(9) Uani 1 1 d . . . . .
H7 H -0.386762 0.358009 0.276697 0.051 Uiso 1 1 calc R U . . .
C76 C -0.0383(4) 0.28685(8) 0.3351(2) 0.0452(9) Uani 1 1 d . . . . .
H76 H -0.110256 0.272840 0.298811 0.054 Uiso 1 1 calc R U . . .
C5 C -0.2237(4) 0.42812(8) 0.3188(2) 0.0417(9) Uani 1 1 d . . . . .
H5 H -0.219499 0.448747 0.293990 0.050 Uiso 1 1 calc R U . . .
C6 C -0.3162(4) 0.40464(9) 0.2729(2) 0.0463(9) Uani 1 1 d . . . . .
H6 H -0.375582 0.409020 0.216396 0.056 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C42 1.225(3) . ?
O2 C1 1.227(3) . ?
C52 C51 1.362(4) . ?
C52 C43 1.421(4) . ?
C52 C53 1.492(4) . ?
C67 C54 1.419(4) . ?
C67 C66 1.441(4) . ?
C67 C68 1.454(4) . ?
C53 C82 1.385(4) . ?
C53 C54 1.426(4) . ?
C81 C68 1.409(4) . ?
C81 C80 1.416(4) . ?
C81 C82 1.424(4) . ?
C28 C37 1.406(4) . ?
C28 C27 1.446(4) . ?
C28 C29 1.446(4) . ?
C41 C12 1.381(4) . ?
C41 C40 1.423(4) . ?
C41 C1 1.483(4) . ?
C43 C44 1.353(4) . ?
C43 C42 1.482(4) . ?
C24 C23 1.410(4) . ?
C24 C19 1.418(4) . ?
C24 C25 1.455(4) . ?
C64 C63 1.370(4) . ?
C64 C65 1.406(4) . ?
C64 H64 0.9500 . ?
C82 C42 1.486(4) . ?
C29 C34 1.418(4) . ?
C29 C30 1.424(4) . ?
C12 C13 1.426(4) . ?
C12 C11 1.496(4) . ?
C54 C55 1.427(4) . ?
C65 C60 1.413(4) . ?
C65 C66 1.462(4) . ?
C27 C40 1.413(4) . ?
C27 C26 1.450(4) . ?
C13 C26 1.420(4) . ?
C13 C14 1.421(4) . ?
C25 C16 1.406(4) . ?
C25 C26 1.447(4) . ?
C66 C57 1.403(4) . ?
C39 C38 1.350(4) . ?
C39 C40 1.430(4) . ?
C39 H39 0.9500 . ?
C16 C15 1.414(4) . ?
C16 C17 1.424(4) . ?
C69 C78 1.408(4) . ?
C69 C68 1.446(4) . ?
C69 C70 1.453(4) . ?
C57 C58 1.425(4) . ?
C57 C56 1.422(4) . ?
C19 C20 1.405(4) . ?
C19 C18 1.422(4) . ?
C50 C49 1.407(4) . ?
C50 C45 1.427(4) . ?
C50 C51 1.430(4) . ?
C60 C61 1.411(4) . ?
C60 C59 1.428(4) . ?
C11 C10 1.371(4) . ?
C11 C2 1.419(4) . ?
C23 C22 1.374(4) . ?
C23 H23 0.9500 . ?
C80 C79 1.362(4) . ?
C80 H80 0.9500 . ?
C55 C56 1.349(4) . ?
C55 H55 0.9500 . ?
C37 C38 1.420(4) . ?
C37 C36 1.423(4) . ?
C51 H51 0.9500 . ?
C15 C14 1.355(4) . ?
C15 H15 0.9500 . ?
C79 C78 1.419(4) . ?
C79 H79 0.9500 . ?
C70 C71 1.409(4) . ?
C70 C75 1.421(4) . ?
C38 H38 0.9500 . ?
C2 C3 1.362(4) . ?
C2 C1 1.478(4) . ?
C78 C77 1.426(4) . ?
C14 H14 0.9500 . ?
C49 C48 1.377(4) . ?
C49 H49 0.9500 . ?
C10 C9 1.423(4) . ?
C10 H10 0.9500 . ?
C9 C8 1.410(4) . ?
C9 C4 1.416(4) . ?
C30 C31 1.369(4) . ?
C30 H30 0.9500 . ?
C45 C46 1.408(4) . ?
C45 C44 1.419(4) . ?
C44 H44 0.9500 . ?
C71 C72 1.373(4) . ?
C71 H71 0.9500 . ?
C4 C5 1.414(4) . ?
C4 C3 1.415(4) . ?
C22 C21 1.391(4) . ?
C22 H22 0.9500 . ?
C56 H56 0.9500 . ?
C46 C47 1.365(4) . ?
C46 H46 0.9500 . ?
C63 C62 1.390(4) . ?
C63 H63 0.9500 . ?
C59 C58 1.346(4) . ?
C59 H59 0.9500 . ?
C31 C32 1.399(4) . ?
C31 H31 0.9500 . ?
C34 C33 1.413(4) . ?
C34 C35 1.423(4) . ?
C8 C7 1.371(4) . ?
C8 H8 0.9500 . ?
C18 C17 1.354(4) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C36 C35 1.349(4) . ?
C36 H36 0.9500 . ?
C62 C61 1.352(4) . ?
C62 H62 0.9500 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9500 . ?
C3 H3 0.9500 . ?
C58 H58 0.9500 . ?
C72 C73 1.395(4) . ?
C72 H72 0.9500 . ?
C48 C47 1.397(4) . ?
C48 H48 0.9500 . ?
C21 H21 0.9500 . ?
C75 C74 1.409(4) . ?
C75 C76 1.422(4) . ?
C61 H61 0.9500 . ?
C47 H47 0.9500 . ?
C33 C32 1.364(4) . ?
C33 H33 0.9500 . ?
C35 H35 0.9500 . ?
C32 H32 0.9500 . ?
C73 C74 1.364(4) . ?
C73 H73 0.9500 . ?
C74 H74 0.9500 . ?
C77 C76 1.353(4) . ?
C77 H77 0.9500 . ?
C7 C6 1.399(5) . ?
C7 H7 0.9500 . ?
C76 H76 0.9500 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C51 C52 C43 119.2(2) . . ?
C51 C52 C53 133.4(3) . . ?
C43 C52 C53 107.5(2) . . ?
C54 C67 C66 118.5(2) . . ?
C54 C67 C68 118.9(2) . . ?
C66 C67 C68 122.6(2) . . ?
C82 C53 C54 119.3(2) . . ?
C82 C53 C52 108.6(2) . . ?
C54 C53 C52 131.7(2) . . ?
C68 C81 C80 119.9(2) . . ?
C68 C81 C82 117.6(2) . . ?
C80 C81 C82 122.4(3) . . ?
C37 C28 C27 117.9(2) . . ?
C37 C28 C29 117.6(2) . . ?
C27 C28 C29 124.4(2) . . ?
C12 C41 C40 122.2(3) . . ?
C12 C41 C1 109.4(2) . . ?
C40 C41 C1 128.3(3) . . ?
C44 C43 C52 122.9(2) . . ?
C44 C43 C42 128.3(3) . . ?
C52 C43 C42 108.8(2) . . ?
C23 C24 C19 117.9(2) . . ?
C23 C24 C25 123.2(2) . . ?
C19 C24 C25 118.6(2) . . ?
C63 C64 C65 121.5(3) . . ?
C63 C64 H64 119.3 . . ?
C65 C64 H64 119.3 . . ?
C53 C82 C81 122.5(3) . . ?
C53 C82 C42 109.6(2) . . ?
C81 C82 C42 127.8(2) . . ?
C34 C29 C30 117.3(3) . . ?
C34 C29 C28 119.4(3) . . ?
C30 C29 C28 122.9(2) . . ?
C41 C12 C13 120.1(2) . . ?
C41 C12 C11 109.1(2) . . ?
C13 C12 C11 130.5(2) . . ?
C67 C54 C53 118.2(2) . . ?
C67 C54 C55 117.9(3) . . ?
C53 C54 C55 123.8(2) . . ?
C64 C65 C60 117.4(2) . . ?
C64 C65 C66 123.2(2) . . ?
C60 C65 C66 119.2(2) . . ?
C40 C27 C28 117.7(2) . . ?
C40 C27 C26 118.0(2) . . ?
C28 C27 C26 124.3(2) . . ?
C26 C13 C14 118.3(2) . . ?
C26 C13 C12 118.0(2) . . ?
C14 C13 C12 123.7(2) . . ?
C16 C25 C26 118.2(2) . . ?
C16 C25 C24 118.0(2) . . ?
C26 C25 C24 123.8(2) . . ?
C57 C66 C67 118.6(2) . . ?
C57 C66 C65 117.6(2) . . ?
C67 C66 C65 123.8(2) . . ?
C13 C26 C25 117.6(2) . . ?
C13 C26 C27 119.3(2) . . ?
C25 C26 C27 123.1(2) . . ?
C38 C39 C40 119.7(3) . . ?
C38 C39 H39 120.1 . . ?
C40 C39 H39 120.1 . . ?
C25 C16 C15 119.6(3) . . ?
C25 C16 C17 119.6(3) . . ?
C15 C16 C17 120.9(3) . . ?
C78 C69 C68 117.3(3) . . ?
C78 C69 C70 118.2(3) . . ?
C68 C69 C70 124.4(2) . . ?
O1 C42 C43 126.5(3) . . ?
O1 C42 C82 128.0(3) . . ?
C43 C42 C82 105.4(2) . . ?
C66 C57 C58 119.3(3) . . ?
C66 C57 C56 118.6(3) . . ?
C58 C57 C56 122.1(3) . . ?
C27 C40 C41 118.2(2) . . ?
C27 C40 C39 119.8(2) . . ?
C41 C40 C39 122.0(3) . . ?
C20 C19 C24 119.2(3) . . ?
C20 C19 C18 121.0(3) . . ?
C24 C19 C18 119.6(3) . . ?
C49 C50 C45 118.6(2) . . ?
C49 C50 C51 121.6(3) . . ?
C45 C50 C51 119.8(2) . . ?
C61 C60 C65 119.4(3) . . ?
C61 C60 C59 121.5(3) . . ?
C65 C60 C59 119.0(3) . . ?
C81 C68 C69 118.4(2) . . ?
C81 C68 C67 117.7(2) . . ?
C69 C68 C67 123.9(2) . . ?
C10 C11 C2 118.8(3) . . ?
C10 C11 C12 134.4(3) . . ?
C2 C11 C12 106.7(2) . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C79 C80 C81 119.6(3) . . ?
C79 C80 H80 120.2 . . ?
C81 C80 H80 120.2 . . ?
C56 C55 C54 121.1(3) . . ?
C56 C55 H55 119.4 . . ?
C54 C55 H55 119.4 . . ?
C28 C37 C38 119.6(3) . . ?
C28 C37 C36 119.7(3) . . ?
C38 C37 C36 120.7(3) . . ?
C52 C51 C50 120.0(2) . . ?
C52 C51 H51 120.0 . . ?
C50 C51 H51 120.0 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C80 C79 C78 121.3(3) . . ?
C80 C79 H79 119.3 . . ?
C78 C79 H79 119.3 . . ?
C71 C70 C75 117.0(3) . . ?
C71 C70 C69 123.9(3) . . ?
C75 C70 C69 119.0(3) . . ?
C39 C38 C37 121.2(3) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C3 C2 C11 122.7(3) . . ?
C3 C2 C1 127.9(3) . . ?
C11 C2 C1 109.3(2) . . ?
C69 C78 C79 119.6(3) . . ?
C69 C78 C77 119.8(3) . . ?
C79 C78 C77 120.5(3) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C48 C49 C50 120.9(3) . . ?
C48 C49 H49 119.6 . . ?
C50 C49 H49 119.6 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C4 118.5(3) . . ?
C8 C9 C10 121.4(3) . . ?
C4 C9 C10 120.2(3) . . ?
C31 C30 C29 121.2(3) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C46 C45 C44 122.4(3) . . ?
C46 C45 C50 118.8(3) . . ?
C44 C45 C50 118.8(2) . . ?
C43 C44 C45 119.3(3) . . ?
C43 C44 H44 120.4 . . ?
C45 C44 H44 120.4 . . ?
C72 C71 C70 122.0(3) . . ?
C72 C71 H71 119.0 . . ?
C70 C71 H71 119.0 . . ?
O2 C1 C2 126.8(3) . . ?
O2 C1 C41 127.7(3) . . ?
C2 C1 C41 105.5(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 C9 119.6(3) . . ?
C3 C4 C9 119.0(3) . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C55 C56 C57 121.4(3) . . ?
C55 C56 H56 119.3 . . ?
C57 C56 H56 119.3 . . ?
C47 C46 C45 121.2(3) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C64 C63 C62 120.3(3) . . ?
C64 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
C58 C59 C60 120.6(3) . . ?
C58 C59 H59 119.7 . . ?
C60 C59 H59 119.7 . . ?
C30 C31 C32 120.7(3) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C33 C34 C29 119.7(3) . . ?
C33 C34 C35 121.0(3) . . ?
C29 C34 C35 119.2(3) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C35 C36 C37 121.3(3) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C61 C62 C63 120.0(3) . . ?
C61 C62 H62 120.0 . . ?
C63 C62 H62 120.0 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C59 C58 C57 121.7(3) . . ?
C59 C58 H58 119.2 . . ?
C57 C58 H58 119.2 . . ?
C71 C72 C73 120.4(3) . . ?
C71 C72 H72 119.8 . . ?
C73 C72 H72 119.8 . . ?
C49 C48 C47 120.3(3) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C74 C75 C70 119.6(3) . . ?
C74 C75 C76 121.0(3) . . ?
C70 C75 C76 119.2(3) . . ?
C62 C61 C60 121.1(3) . . ?
C62 C61 H61 119.4 . . ?
C60 C61 H61 119.4 . . ?
C46 C47 C48 120.2(3) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C32 C33 C34 121.1(3) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C33 C32 C31 119.6(3) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C74 C73 C72 119.3(3) . . ?
C74 C73 H73 120.3 . . ?
C72 C73 H73 120.3 . . ?
C73 C74 C75 121.5(3) . . ?
C73 C74 H74 119.3 . . ?
C75 C74 H74 119.3 . . ?
C76 C77 C78 120.9(3) . . ?
C76 C77 H77 119.5 . . ?
C78 C77 H77 119.5 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C77 C76 C75 121.2(3) . . ?
C77 C76 H76 119.4 . . ?
C75 C76 H76 119.4 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2295946'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H20 O'
_chemical_formula_sum            'C37 H20 O'
_chemical_formula_weight         480.53

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5109(11)
_cell_length_b                   8.9771(7)
_cell_length_c                   16.8196(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.427(4)
_cell_angle_gamma                90
_cell_volume                     2295.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9602
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.09

_exptl_crystal_description       shunk
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            156291
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         30.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6760
_reflns_number_gt                5354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Intrinsic Phasing (Bruker)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to 
ideal positions and refined isotropically using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+3.6320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6760
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.1992
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.46894(14) 0.2983(2) 0.40429(13) 0.0414(5) Uani 1 1 d . . . . .
C34 C 0.15817(15) 0.0226(2) 0.57557(13) 0.0190(4) Uani 1 1 d . . . . .
C30 C 0.25286(14) 0.2188(3) 0.72126(14) 0.0215(4) Uani 1 1 d . . . . .
C33 C 0.24169(14) 0.0601(2) 0.55485(13) 0.0187(4) Uani 1 1 d . . . . .
C32 C 0.28822(14) 0.1983(2) 0.57932(13) 0.0199(4) Uani 1 1 d . . . . .
C35 C 0.09644(14) 0.1307(2) 0.59545(13) 0.0199(4) Uani 1 1 d . . . . .
C31 C 0.27898(14) 0.2822(2) 0.65021(14) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.13501(17) -0.1298(2) 0.57713(15) 0.0255(5) Uani 1 1 d . . . . .
C18 C 0.37486(15) 0.1529(3) 0.47624(14) 0.0248(5) Uani 1 1 d . . . . .
C25 C 0.22706(15) 0.3159(3) 0.77891(15) 0.0253(5) Uani 1 1 d . . . . .
C20 C 0.37653(16) 0.4043(3) 0.54020(16) 0.0286(5) Uani 1 1 d . . . . .
H20 H 0.415043 0.441889 0.507553 0.034 Uiso 1 1 calc R U . . .
C4 C 0.01853(18) -0.0719(3) 0.64955(17) 0.0326(6) Uani 1 1 d . . . . .
H4 H -0.022460 -0.104197 0.681062 0.039 Uiso 1 1 calc R U . . .
C23 C 0.27612(17) 0.5293(3) 0.71246(17) 0.0308(5) Uani 1 1 d . . . . .
H23 H 0.288247 0.633034 0.712020 0.037 Uiso 1 1 calc R U . . .
C10 C 0.35063(15) 0.0048(3) 0.47209(14) 0.0239(5) Uani 1 1 d . . . . .
C22 C 0.30124(16) 0.4353(3) 0.65200(16) 0.0261(5) Uani 1 1 d . . . . .
C37 C 0.03797(17) 0.3816(3) 0.59387(16) 0.0305(5) Uani 1 1 d . . . . .
H37 H 0.037823 0.482076 0.576090 0.037 Uiso 1 1 calc R U . . .
C21 C 0.35009(16) 0.4932(3) 0.59550(17) 0.0293(5) Uani 1 1 d . . . . .
H21 H 0.364285 0.596235 0.596790 0.035 Uiso 1 1 calc R U . . .
C19 C 0.34654(15) 0.2532(3) 0.53073(14) 0.0227(4) Uani 1 1 d . . . . .
C1 C -0.02026(18) 0.3376(3) 0.64313(18) 0.0369(6) Uani 1 1 d . . . . .
H1 H -0.056194 0.409299 0.662482 0.044 Uiso 1 1 calc R U . . .
C29 C 0.25852(15) 0.0650(3) 0.73945(14) 0.0235(5) Uani 1 1 d . . . . .
H29 H 0.280452 -0.001207 0.704088 0.028 Uiso 1 1 calc R U . . .
C3 C 0.03044(16) 0.0843(3) 0.63727(15) 0.0257(5) Uani 1 1 d . . . . .
C11 C 0.40082(16) -0.0753(3) 0.41723(14) 0.0268(5) Uani 1 1 d . . . . .
C8 C 0.24775(18) -0.1942(3) 0.50233(15) 0.0287(5) Uani 1 1 d . . . . .
H8 H 0.272345 -0.264992 0.471203 0.034 Uiso 1 1 calc R U . . .
C27 C 0.20081(17) 0.1052(3) 0.86071(15) 0.0327(6) Uani 1 1 d . . . . .
H27 H 0.180542 0.066031 0.906175 0.039 Uiso 1 1 calc R U . . .
C36 C 0.09547(15) 0.2814(2) 0.57079(14) 0.0219(4) Uani 1 1 d . . . . .
H36 H 0.135031 0.313843 0.537864 0.026 Uiso 1 1 calc R U . . .
C17 C 0.43692(17) 0.1804(3) 0.41996(15) 0.0302(5) Uani 1 1 d . . . . .
C26 C 0.19893(16) 0.2555(3) 0.84682(16) 0.0315(6) Uani 1 1 d . . . . .
H26 H 0.178283 0.320315 0.883613 0.038 Uiso 1 1 calc R U . . .
C14 C 0.50306(19) -0.1519(4) 0.30451(18) 0.0406(7) Uani 1 1 d . . . . .
H14 H 0.535700 -0.179090 0.264554 0.049 Uiso 1 1 calc R U . . .
C28 C 0.23293(17) 0.0092(3) 0.80726(15) 0.0285(5) Uani 1 1 d . . . . .
H28 H 0.236962 -0.094680 0.818072 0.034 Uiso 1 1 calc R U . . .
C5 C 0.06538(18) -0.1734(3) 0.61649(17) 0.0321(6) Uani 1 1 d . . . . .
H5 H 0.051687 -0.276129 0.619489 0.039 Uiso 1 1 calc R U . . .
C9 C 0.28095(15) -0.0451(2) 0.50917(14) 0.0216(4) Uani 1 1 d . . . . .
C16 C 0.45009(16) 0.0320(3) 0.38531(16) 0.0309(5) Uani 1 1 d . . . . .
C24 C 0.23575(17) 0.4739(3) 0.76981(16) 0.0304(5) Uani 1 1 d . . . . .
H24 H 0.212793 0.539853 0.804598 0.037 Uiso 1 1 calc R U . . .
C2 C -0.02510(17) 0.1908(3) 0.66323(18) 0.0349(6) Uani 1 1 d . . . . .
H2 H -0.066210 0.160055 0.694959 0.042 Uiso 1 1 calc R U . . .
C7 C 0.18192(19) -0.2359(3) 0.53951(17) 0.0307(5) Uani 1 1 d . . . . .
H7 H 0.166676 -0.338235 0.540514 0.037 Uiso 1 1 calc R U . . .
C12 C 0.40583(17) -0.2230(3) 0.39559(15) 0.0304(5) Uani 1 1 d . . . . .
H12 H 0.375495 -0.298062 0.418901 0.037 Uiso 1 1 calc R U . . .
C15 C 0.50158(18) -0.0049(4) 0.32904(16) 0.0371(6) Uani 1 1 d . . . . .
H15 H 0.534823 0.068957 0.308051 0.045 Uiso 1 1 calc R U . . .
C13 C 0.45720(19) -0.2592(3) 0.33796(17) 0.0366(6) Uani 1 1 d . . . . .
H13 H 0.460386 -0.360007 0.321680 0.044 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.220(3) . ?
C34 C6 1.416(3) . ?
C34 C33 1.446(3) . ?
C34 C35 1.448(3) . ?
C30 C29 1.413(3) . ?
C30 C25 1.419(3) . ?
C30 C31 1.452(3) . ?
C33 C9 1.427(3) . ?
C33 C32 1.453(3) . ?
C32 C19 1.422(3) . ?
C32 C31 1.442(3) . ?
C35 C36 1.414(3) . ?
C35 C3 1.415(3) . ?
C31 C22 1.416(3) . ?
C6 C7 1.421(3) . ?
C6 C5 1.429(3) . ?
C18 C10 1.380(3) . ?
C18 C19 1.415(3) . ?
C18 C17 1.498(3) . ?
C25 C26 1.409(4) . ?
C25 C24 1.436(4) . ?
C20 C21 1.350(4) . ?
C20 C19 1.432(3) . ?
C20 H20 0.9500 . ?
C4 C5 1.352(4) . ?
C4 C3 1.435(4) . ?
C4 H4 0.9500 . ?
C23 C24 1.345(4) . ?
C23 C22 1.434(4) . ?
C23 H23 0.9500 . ?
C10 C9 1.423(3) . ?
C10 C11 1.503(3) . ?
C22 C21 1.426(4) . ?
C37 C36 1.376(3) . ?
C37 C1 1.398(4) . ?
C37 H37 0.9500 . ?
C21 H21 0.9500 . ?
C1 C2 1.367(4) . ?
C1 H1 0.9500 . ?
C29 C28 1.374(3) . ?
C29 H29 0.9500 . ?
C3 C2 1.413(4) . ?
C11 C12 1.381(4) . ?
C11 C16 1.401(4) . ?
C8 C7 1.352(4) . ?
C8 C9 1.431(3) . ?
C8 H8 0.9500 . ?
C27 C26 1.368(4) . ?
C27 C28 1.406(4) . ?
C27 H27 0.9500 . ?
C36 H36 0.9500 . ?
C17 C16 1.484(4) . ?
C26 H26 0.9500 . ?
C14 C13 1.381(4) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C28 H28 0.9500 . ?
C5 H5 0.9500 . ?
C16 C15 1.394(4) . ?
C24 H24 0.9500 . ?
C2 H2 0.9500 . ?
C7 H7 0.9500 . ?
C12 C13 1.409(4) . ?
C12 H12 0.9500 . ?
C15 H15 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C34 C33 118.12(19) . . ?
C6 C34 C35 117.5(2) . . ?
C33 C34 C35 124.40(18) . . ?
C29 C30 C25 117.8(2) . . ?
C29 C30 C31 123.1(2) . . ?
C25 C30 C31 119.0(2) . . ?
C9 C33 C34 118.31(19) . . ?
C9 C33 C32 118.43(19) . . ?
C34 C33 C32 123.26(19) . . ?
C19 C32 C31 118.2(2) . . ?
C19 C32 C33 118.0(2) . . ?
C31 C32 C33 123.74(19) . . ?
C36 C35 C3 117.4(2) . . ?
C36 C35 C34 122.8(2) . . ?
C3 C35 C34 119.6(2) . . ?
C22 C31 C32 117.5(2) . . ?
C22 C31 C30 118.0(2) . . ?
C32 C31 C30 124.4(2) . . ?
C34 C6 C7 119.0(2) . . ?
C34 C6 C5 119.4(2) . . ?
C7 C6 C5 121.6(2) . . ?
C10 C18 C19 122.0(2) . . ?
C10 C18 C17 109.2(2) . . ?
C19 C18 C17 128.7(2) . . ?
C26 C25 C30 119.5(2) . . ?
C26 C25 C24 121.1(2) . . ?
C30 C25 C24 119.2(2) . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C24 C23 C22 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C18 C10 C9 120.3(2) . . ?
C18 C10 C11 108.8(2) . . ?
C9 C10 C11 130.5(2) . . ?
C31 C22 C21 120.0(2) . . ?
C31 C22 C23 119.2(2) . . ?
C21 C22 C23 120.9(2) . . ?
C36 C37 C1 120.9(2) . . ?
C36 C37 H37 119.5 . . ?
C1 C37 H37 119.5 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C18 C19 C32 117.8(2) . . ?
C18 C19 C20 122.6(2) . . ?
C32 C19 C20 119.6(2) . . ?
C2 C1 C37 119.5(2) . . ?
C2 C1 H1 120.2 . . ?
C37 C1 H1 120.2 . . ?
C28 C29 C30 121.3(2) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C2 C3 C35 120.0(2) . . ?
C2 C3 C4 120.9(2) . . ?
C35 C3 C4 119.1(2) . . ?
C12 C11 C16 119.7(2) . . ?
C12 C11 C10 133.2(2) . . ?
C16 C11 C10 107.1(2) . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C26 C27 C28 119.6(2) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C37 C36 C35 120.8(2) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
O1 C17 C16 126.9(2) . . ?
O1 C17 C18 128.3(3) . . ?
C16 C17 C18 104.8(2) . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C29 C28 C27 120.3(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C4 C5 C6 121.6(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C10 C9 C33 118.0(2) . . ?
C10 C9 C8 123.5(2) . . ?
C33 C9 C8 118.5(2) . . ?
C15 C16 C11 121.7(3) . . ?
C15 C16 C17 128.5(3) . . ?
C11 C16 C17 109.8(2) . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C11 C12 C13 118.1(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?

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
C6 C34 C33 C9 22.8(3) . . . . ?
C35 C34 C33 C9 -157.6(2) . . . . ?
C6 C34 C33 C32 -156.2(2) . . . . ?
C35 C34 C33 C32 23.4(3) . . . . ?
C9 C33 C32 C19 27.0(3) . . . . ?
C34 C33 C32 C19 -154.0(2) . . . . ?
C9 C33 C32 C31 -152.6(2) . . . . ?
C34 C33 C32 C31 26.4(3) . . . . ?
C6 C34 C35 C36 -158.1(2) . . . . ?
C33 C34 C35 C36 22.3(3) . . . . ?
C6 C34 C35 C3 18.2(3) . . . . ?
C33 C34 C35 C3 -161.4(2) . . . . ?
C19 C32 C31 C22 22.4(3) . . . . ?
C33 C32 C31 C22 -157.9(2) . . . . ?
C19 C32 C31 C30 -154.3(2) . . . . ?
C33 C32 C31 C30 25.4(3) . . . . ?
C29 C30 C31 C22 -157.4(2) . . . . ?
C25 C30 C31 C22 17.3(3) . . . . ?
C29 C30 C31 C32 19.3(3) . . . . ?
C25 C30 C31 C32 -166.0(2) . . . . ?
C33 C34 C6 C7 -15.7(3) . . . . ?
C35 C34 C6 C7 164.7(2) . . . . ?
C33 C34 C6 C5 164.2(2) . . . . ?
C35 C34 C6 C5 -15.4(3) . . . . ?
C29 C30 C25 C26 -7.0(3) . . . . ?
C31 C30 C25 C26 178.0(2) . . . . ?
C29 C30 C25 C24 168.9(2) . . . . ?
C31 C30 C25 C24 -6.1(3) . . . . ?
C19 C18 C10 C9 14.1(4) . . . . ?
C17 C18 C10 C9 -169.4(2) . . . . ?
C19 C18 C10 C11 -172.4(2) . . . . ?
C17 C18 C10 C11 4.1(3) . . . . ?
C32 C31 C22 C21 -14.6(3) . . . . ?
C30 C31 C22 C21 162.3(2) . . . . ?
C32 C31 C22 C23 167.1(2) . . . . ?
C30 C31 C22 C23 -16.0(3) . . . . ?
C24 C23 C22 C31 3.3(4) . . . . ?
C24 C23 C22 C21 -175.0(2) . . . . ?
C19 C20 C21 C22 7.8(4) . . . . ?
C31 C22 C21 C20 -0.6(4) . . . . ?
C23 C22 C21 C20 177.7(2) . . . . ?
C10 C18 C19 C32 -2.9(3) . . . . ?
C17 C18 C19 C32 -178.6(2) . . . . ?
C10 C18 C19 C20 175.1(2) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C31 C32 C19 C18 162.2(2) . . . . ?
C33 C32 C19 C18 -17.4(3) . . . . ?
C31 C32 C19 C20 -15.8(3) . . . . ?
C33 C32 C19 C20 164.6(2) . . . . ?
C21 C20 C19 C18 -177.3(2) . . . . ?
C21 C20 C19 C32 0.6(4) . . . . ?
C36 C37 C1 C2 -5.3(4) . . . . ?
C25 C30 C29 C28 5.4(3) . . . . ?
C31 C30 C29 C28 -179.9(2) . . . . ?
C36 C35 C3 C2 -9.2(3) . . . . ?
C34 C35 C3 C2 174.4(2) . . . . ?
C36 C35 C3 C4 168.1(2) . . . . ?
C34 C35 C3 C4 -8.3(3) . . . . ?
C5 C4 C3 C2 172.5(3) . . . . ?
C5 C4 C3 C35 -4.8(4) . . . . ?
C18 C10 C11 C12 175.8(3) . . . . ?
C9 C10 C11 C12 -11.6(4) . . . . ?
C18 C10 C11 C16 -4.0(3) . . . . ?
C9 C10 C11 C16 168.6(2) . . . . ?
C1 C37 C36 C35 0.8(4) . . . . ?
C3 C35 C36 C37 6.4(3) . . . . ?
C34 C35 C36 C37 -177.3(2) . . . . ?
C10 C18 C17 O1 176.2(3) . . . . ?
C19 C18 C17 O1 -7.6(4) . . . . ?
C10 C18 C17 C16 -2.7(3) . . . . ?
C19 C18 C17 C16 173.5(2) . . . . ?
C28 C27 C26 C25 1.2(4) . . . . ?
C30 C25 C26 C27 3.8(4) . . . . ?
C24 C25 C26 C27 -171.9(2) . . . . ?
C30 C29 C28 C27 -0.4(4) . . . . ?
C26 C27 C28 C29 -3.0(4) . . . . ?
C3 C4 C5 C6 7.7(4) . . . . ?
C34 C6 C5 C4 2.7(4) . . . . ?
C7 C6 C5 C4 -177.4(3) . . . . ?
C18 C10 C9 C33 -4.2(3) . . . . ?
C11 C10 C9 C33 -176.1(2) . . . . ?
C18 C10 C9 C8 175.2(2) . . . . ?
C11 C10 C9 C8 3.2(4) . . . . ?
C34 C33 C9 C10 164.9(2) . . . . ?
C32 C33 C9 C10 -16.0(3) . . . . ?
C34 C33 C9 C8 -14.4(3) . . . . ?
C32 C33 C9 C8 164.6(2) . . . . ?
C7 C8 C9 C10 179.4(2) . . . . ?
C7 C8 C9 C33 -1.3(4) . . . . ?
C12 C11 C16 C15 2.9(4) . . . . ?
C10 C11 C16 C15 -177.3(2) . . . . ?
C12 C11 C16 C17 -177.6(2) . . . . ?
C10 C11 C16 C17 2.3(3) . . . . ?
O1 C17 C16 C15 0.7(5) . . . . ?
C18 C17 C16 C15 179.6(3) . . . . ?
O1 C17 C16 C11 -178.8(3) . . . . ?
C18 C17 C16 C11 0.1(3) . . . . ?
C22 C23 C24 C25 8.4(4) . . . . ?
C26 C25 C24 C23 168.9(2) . . . . ?
C30 C25 C24 C23 -6.8(4) . . . . ?
C37 C1 C2 C3 2.4(4) . . . . ?
C35 C3 C2 C1 4.9(4) . . . . ?
C4 C3 C2 C1 -172.3(3) . . . . ?
C9 C8 C7 C6 8.9(4) . . . . ?
C34 C6 C7 C8 -0.1(4) . . . . ?
C5 C6 C7 C8 180.0(3) . . . . ?
C16 C11 C12 C13 -3.5(4) . . . . ?
C10 C11 C12 C13 176.7(2) . . . . ?
C13 C14 C15 C16 -2.6(4) . . . . ?
C11 C16 C15 C14 0.2(4) . . . . ?
C17 C16 C15 C14 -179.2(3) . . . . ?
C15 C14 C13 C12 1.9(4) . . . . ?
C11 C12 C13 C14 1.2(4) . . . . ?

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.075

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2295947'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H24 O'
_chemical_formula_sum            'C45 H24 O'
_chemical_formula_weight         580.64

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.6528(7)
_cell_length_b                   13.9671(9)
_cell_length_c                   18.2044(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2708.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9643
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.65

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7203
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            201477
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.838
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6779
_reflns_number_gt                6613
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refined as a 2-component inversion twin. The absolute structure cannot be 
determined reliably considering the absence of heavy atoms and the radiation source.
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to 
ideal positions and refined isotropically using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+1.4325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6779
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C18 C 0.3182(2) 0.08482(16) 0.97442(13) 0.0169(4) Uani 1 1 d . . . . .
C45 C 0.1047(2) -0.32183(17) 1.08753(13) 0.0191(4) Uani 1 1 d . . . . .
C30 C -0.0397(2) -0.07825(17) 0.88280(13) 0.0171(4) Uani 1 1 d . . . . .
C35 C -0.0568(2) -0.02438(18) 0.81719(14) 0.0199(5) Uani 1 1 d . . . . .
C29 C 0.0011(2) -0.02936(17) 0.94929(13) 0.0168(4) Uani 1 1 d . . . . .
C24 C 0.2621(2) -0.06275(16) 0.90665(12) 0.0159(4) Uani 1 1 d . . . . .
C25 C 0.2213(2) -0.16219(17) 0.90232(13) 0.0170(4) Uani 1 1 d . . . . .
C23 C 0.3031(2) -0.01637(16) 0.97359(12) 0.0149(4) Uani 1 1 d . . . . .
C38 C -0.0060(2) 0.07171(18) 0.95031(14) 0.0211(5) Uani 1 1 d . . . . .
C20 C 0.3850(2) 0.07958(18) 1.10174(13) 0.0223(5) Uani 1 1 d . . . . .
H20 H 0.408853 0.111644 1.145592 0.027 Uiso 1 1 calc R U . . .
C9 C 0.1710(2) -0.31779(17) 0.95977(13) 0.0179(4) Uani 1 1 d . . . . .
C15 C 0.2703(2) -0.00995(18) 0.84072(13) 0.0195(5) Uani 1 1 d . . . . .
C44 C 0.0813(2) -0.22177(17) 1.08842(13) 0.0185(4) Uani 1 1 d . . . . .
C22 C 0.3403(2) -0.06775(17) 1.03722(12) 0.0179(4) Uani 1 1 d . . . . .
H22 H 0.337000 -0.135722 1.036951 0.021 Uiso 1 1 calc R U . . .
C41 C 0.0242(2) -0.02588(18) 1.08340(13) 0.0210(5) Uani 1 1 d . . . . .
C26 C 0.1632(2) -0.21593(16) 0.96163(12) 0.0170(4) Uani 1 1 d . . . . .
C17 C 0.3057(2) 0.13796(17) 0.90756(14) 0.0212(5) Uani 1 1 d . . . . .
H17 H 0.308983 0.205919 0.908483 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2572(2) -0.1555(2) 0.76930(14) 0.0243(5) Uani 1 1 d . . . . .
H13 H 0.266622 -0.187576 0.723613 0.029 Uiso 1 1 calc R U . . .
C27 C 0.0938(2) -0.17110(16) 1.02107(13) 0.0175(4) Uani 1 1 d . . . . .
C19 C 0.3540(2) 0.13101(17) 1.04018(13) 0.0205(5) Uani 1 1 d . . . . .
H19 H 0.356654 0.198962 1.041805 0.025 Uiso 1 1 calc R U . . .
C37 C -0.0220(2) 0.12330(18) 0.88282(15) 0.0252(5) Uani 1 1 d . . . . .
H37 H -0.019943 0.191291 0.883390 0.030 Uiso 1 1 calc R U . . .
C28 C 0.0396(2) -0.07643(17) 1.01637(13) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.1389(2) -0.36998(16) 1.02459(13) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.2307(2) -0.31206(19) 0.83174(14) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.242311 -0.344112 0.786224 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2365(2) -0.20962(18) 0.83443(13) 0.0198(5) Uani 1 1 d . . . . .
C14 C 0.2637(2) -0.0587(2) 0.77180(13) 0.0240(5) Uani 1 1 d . . . . .
H14 H 0.263908 -0.022949 0.727407 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2089(2) -0.36332(18) 0.89301(14) 0.0225(5) Uani 1 1 d . . . . .
H10 H 0.218901 -0.430892 0.891899 0.027 Uiso 1 1 calc R U . . .
C21 C 0.3811(2) -0.02084(18) 1.09943(13) 0.0209(5) Uani 1 1 d . . . . .
H21 H 0.406863 -0.056781 1.141094 0.025 Uiso 1 1 calc R U . . .
C36 C -0.0398(2) 0.07733(19) 0.81879(15) 0.0243(5) Uani 1 1 d . . . . .
H36 H -0.041184 0.112627 0.774187 0.029 Uiso 1 1 calc R U . . .
C16 C 0.2890(2) 0.09143(19) 0.84298(14) 0.0223(5) Uani 1 1 d . . . . .
H16 H 0.289861 0.126762 0.798388 0.027 Uiso 1 1 calc R U . . .
O1 O 0.0664(2) -0.37766(15) 1.21321(10) 0.0290(4) Uani 1 1 d . . . . .
C34 C -0.0970(2) -0.0709(2) 0.75244(14) 0.0254(5) Uani 1 1 d . . . . .
H34 H -0.104230 -0.035185 0.708217 0.030 Uiso 1 1 calc R U . . .
C39 C -0.0015(2) 0.12294(18) 1.01818(15) 0.0252(5) Uani 1 1 d . . . . .
H39 H -0.001904 0.190956 1.018002 0.030 Uiso 1 1 calc R U . . .
C40 C 0.0033(2) 0.07503(19) 1.08273(15) 0.0254(5) Uani 1 1 d . . . . .
H40 H -0.007279 0.108640 1.127677 0.031 Uiso 1 1 calc R U . . .
C32 C -0.1176(2) -0.21915(19) 0.81818(14) 0.0242(5) Uani 1 1 d . . . . .
H32 H -0.141144 -0.284738 0.818897 0.029 Uiso 1 1 calc R U . . .
C42 C 0.0306(2) -0.07550(19) 1.15172(14) 0.0229(5) Uani 1 1 d . . . . .
H42 H 0.022192 -0.040804 1.196335 0.027 Uiso 1 1 calc R U . . .
C31 C -0.0757(2) -0.17605(17) 0.88165(14) 0.0198(4) Uani 1 1 d . . . . .
H31 H -0.070724 -0.212567 0.925585 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1433(2) -0.47543(17) 1.03992(14) 0.0215(5) Uani 1 1 d . . . . .
C43 C 0.0484(2) -0.17108(19) 1.15387(13) 0.0219(5) Uani 1 1 d . . . . .
H43 H 0.039124 -0.204721 1.198899 0.026 Uiso 1 1 calc R U . . .
C33 C -0.1258(3) -0.1668(2) 0.75222(15) 0.0275(5) Uani 1 1 d . . . . .
H33 H -0.150913 -0.197540 0.708035 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1156(2) -0.48807(18) 1.11503(15) 0.0245(5) Uani 1 1 d . . . . .
C1 C 0.0917(2) -0.39256(18) 1.14910(14) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.1119(3) -0.57706(19) 1.14789(16) 0.0281(5) Uani 1 1 d . . . . .
H3 H 0.094245 -0.583696 1.198791 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1662(3) -0.55507(18) 0.99711(16) 0.0265(5) Uani 1 1 d . . . . .
H6 H 0.184802 -0.548565 0.946319 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1350(3) -0.65701(19) 1.10391(18) 0.0311(6) Uani 1 1 d . . . . .
H4 H 0.132506 -0.719313 1.124796 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1613(3) -0.64583(18) 1.03001(17) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.176577 -0.700983 1.000804 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C18 C19 1.412(3) . ?
C18 C23 1.423(3) . ?
C18 C17 1.432(3) . ?
C45 C8 1.378(3) . ?
C45 C44 1.420(3) . ?
C45 C1 1.500(3) . ?
C30 C31 1.419(3) . ?
C30 C35 1.423(3) . ?
C30 C29 1.456(3) . ?
C35 C34 1.412(4) . ?
C35 C36 1.432(3) . ?
C29 C38 1.414(3) . ?
C29 C28 1.446(3) . ?
C24 C15 1.411(3) . ?
C24 C23 1.448(3) . ?
C24 C25 1.457(3) . ?
C25 C12 1.411(3) . ?
C25 C26 1.454(3) . ?
C23 C22 1.419(3) . ?
C38 C39 1.429(3) . ?
C38 C37 1.434(3) . ?
C20 C19 1.371(3) . ?
C20 C21 1.404(3) . ?
C20 H20 0.9500 . ?
C9 C26 1.426(3) . ?
C9 C8 1.428(3) . ?
C9 C10 1.430(3) . ?
C15 C14 1.429(3) . ?
C15 C16 1.431(3) . ?
C44 C27 1.422(3) . ?
C44 C43 1.430(3) . ?
C22 C21 1.379(3) . ?
C22 H22 0.9500 . ?
C41 C28 1.419(3) . ?
C41 C42 1.425(3) . ?
C41 C40 1.427(4) . ?
C26 C27 1.452(3) . ?
C17 C16 1.355(4) . ?
C17 H17 0.9500 . ?
C13 C14 1.354(4) . ?
C13 C12 1.424(3) . ?
C13 H13 0.9500 . ?
C27 C28 1.445(3) . ?
C19 H19 0.9500 . ?
C37 C36 1.344(4) . ?
C37 H37 0.9500 . ?
C8 C7 1.500(3) . ?
C11 C10 1.346(4) . ?
C11 C12 1.433(3) . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C21 H21 0.9500 . ?
C36 H36 0.9500 . ?
C16 H16 0.9500 . ?
O1 C1 1.216(3) . ?
C34 C33 1.375(4) . ?
C34 H34 0.9500 . ?
C39 C40 1.353(4) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C32 C31 1.377(3) . ?
C32 C33 1.408(4) . ?
C32 H32 0.9500 . ?
C42 C43 1.349(4) . ?
C42 H42 0.9500 . ?
C31 H31 0.9500 . ?
C7 C6 1.380(4) . ?
C7 C2 1.410(4) . ?
C43 H43 0.9500 . ?
C33 H33 0.9500 . ?
C2 C3 1.380(3) . ?
C2 C1 1.493(4) . ?
C3 C4 1.396(4) . ?
C3 H3 0.9500 . ?
C6 C5 1.403(4) . ?
C6 H6 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 C18 C23 119.6(2) . . ?
C19 C18 C17 120.6(2) . . ?
C23 C18 C17 119.7(2) . . ?
C8 C45 C44 122.4(2) . . ?
C8 C45 C1 108.9(2) . . ?
C44 C45 C1 128.6(2) . . ?
C31 C30 C35 117.5(2) . . ?
C31 C30 C29 123.0(2) . . ?
C35 C30 C29 119.2(2) . . ?
C34 C35 C30 119.7(2) . . ?
C34 C35 C36 120.7(2) . . ?
C30 C35 C36 119.4(2) . . ?
C38 C29 C28 117.3(2) . . ?
C38 C29 C30 117.6(2) . . ?
C28 C29 C30 125.0(2) . . ?
C15 C24 C23 117.6(2) . . ?
C15 C24 C25 118.1(2) . . ?
C23 C24 C25 124.2(2) . . ?
C12 C25 C26 117.2(2) . . ?
C12 C25 C24 117.4(2) . . ?
C26 C25 C24 125.4(2) . . ?
C22 C23 C18 117.5(2) . . ?
C22 C23 C24 123.0(2) . . ?
C18 C23 C24 119.2(2) . . ?
C29 C38 C39 120.6(2) . . ?
C29 C38 C37 119.8(2) . . ?
C39 C38 C37 119.5(2) . . ?
C19 C20 C21 119.5(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C26 C9 C8 118.4(2) . . ?
C26 C9 C10 118.7(2) . . ?
C8 C9 C10 122.9(2) . . ?
C24 C15 C14 119.6(2) . . ?
C24 C15 C16 120.1(2) . . ?
C14 C15 C16 120.2(2) . . ?
C45 C44 C27 117.6(2) . . ?
C45 C44 C43 122.7(2) . . ?
C27 C44 C43 119.7(2) . . ?
C21 C22 C23 121.2(2) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C28 C41 C42 120.2(2) . . ?
C28 C41 C40 120.1(2) . . ?
C42 C41 C40 119.7(2) . . ?
C9 C26 C27 118.5(2) . . ?
C9 C26 C25 118.2(2) . . ?
C27 C26 C25 123.2(2) . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C44 C27 C28 118.0(2) . . ?
C44 C27 C26 118.4(2) . . ?
C28 C27 C26 123.6(2) . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C36 C37 C38 121.3(2) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C41 C28 C27 116.8(2) . . ?
C41 C28 C29 117.8(2) . . ?
C27 C28 C29 125.4(2) . . ?
C45 C8 C9 120.1(2) . . ?
C45 C8 C7 109.4(2) . . ?
C9 C8 C7 130.4(2) . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C25 C12 C13 119.8(2) . . ?
C25 C12 C11 119.6(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C37 C36 C35 120.6(2) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C33 C34 C35 121.2(2) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C40 C39 C38 120.3(2) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 120.1(2) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
C31 C32 C33 120.6(2) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C43 C42 C41 120.9(2) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C32 C31 C30 121.4(2) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C6 C7 C2 118.9(2) . . ?
C6 C7 C8 133.8(2) . . ?
C2 C7 C8 107.3(2) . . ?
C42 C43 C44 120.0(2) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C34 C33 C32 119.3(2) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C3 C2 C7 122.6(3) . . ?
C3 C2 C1 128.3(3) . . ?
C7 C2 C1 109.1(2) . . ?
O1 C1 C2 126.1(2) . . ?
O1 C1 C45 128.7(2) . . ?
C2 C1 C45 105.2(2) . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.054

