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

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

data_Werz_MG498F2_a
_database_code_depnum_ccdc_archive 'CCDC 2454075'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2025-05-26 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V143 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C32 H32 N4 O2'
_chemical_formula_moiety         'C32 H32 N4 O2'
_chemical_formula_weight         504.61
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_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, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.7218(6)
_cell_length_b                   16.3416(11)
_cell_length_c                   18.7045(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2665.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9695
_cell_measurement_theta_min      3.5915
_cell_measurement_theta_max      74.544
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature by gas-phase diffusion of heptaneinto a solution of the compound dissolved in chloroform.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.163
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6179
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.811
_shelx_estimated_absorpt_T_max   0.904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.1
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            121929
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_theta_min         3.591
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5441
_reflns_number_gt                5422
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_max     0.996
_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.
;
_computing_data_collection       
'Bruker BIS 8.5.5.6/2024-10-24 and APEX6 2024.9-1'
_computing_cell_refinement       'SAINT V8.41'
_computing_data_reduction        'SAINT V8.41'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.4937P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5441
_refine_ls_number_parameters     347
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_abs_structure_details 
;
 Flack x determined using 2605 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.47237(16) 0.60296(7) 0.30002(7) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.22928(18) 0.42572(8) 0.45778(8) 0.0374(3) Uani 1 1 d . . . . .
N1 N 0.49273(16) 0.73854(8) 0.32614(7) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.56119(16) 0.79638(8) 0.36947(7) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.30980(15) 0.30681(8) 0.50656(7) 0.0183(3) Uani 1 1 d . . . . .
N4 N 0.39624(15) 0.26854(8) 0.55846(7) 0.0194(3) Uani 1 1 d . . . . .
C1 C 0.54378(18) 0.57633(9) 0.51088(8) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.5128(2) 0.66377(9) 0.47922(8) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.402799 0.675889 0.471624 0.026 Uiso 1 1 calc R U . . .
H2B H 0.563534 0.708430 0.506046 0.026 Uiso 1 1 calc R U . . .
C3 C 0.59898(19) 0.63839(9) 0.41005(8) 0.0208(3) Uani 1 1 d . . . . .
H3 H 0.705858 0.660526 0.409444 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5960(2) 0.54799(10) 0.43506(9) 0.0237(3) Uani 1 1 d . . . . .
H4A H 0.697881 0.521315 0.434545 0.028 Uiso 1 1 calc R U . . .
H4B H 0.519041 0.514057 0.409846 0.028 Uiso 1 1 calc R U . . .
C5 C 0.40874(17) 0.53255(9) 0.54575(8) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.306755 0.553135 0.529224 0.020 Uiso 1 1 calc R U . . .
C6 C 0.41779(17) 0.43761(9) 0.55010(8) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.525665 0.418862 0.542363 0.021 Uiso 1 1 calc R U . . .
C7 C 0.38210(17) 0.44261(9) 0.63160(8) 0.0177(3) Uani 1 1 d . . . . .
H7A H 0.272984 0.433184 0.643634 0.021 Uiso 1 1 calc R U . . .
H7B H 0.450323 0.408557 0.661674 0.021 Uiso 1 1 calc R U . . .
C8 C 0.42823(17) 0.53457(9) 0.62883(8) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.59949(17) 0.54979(8) 0.63500(9) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.68995(19) 0.54355(10) 0.69606(9) 0.0221(3) Uani 1 1 d . . . . .
H10 H 0.646652 0.526554 0.740230 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8451(2) 0.56270(10) 0.69114(10) 0.0268(4) Uani 1 1 d . . . . .
H11 H 0.908379 0.558602 0.732310 0.032 Uiso 1 1 calc R U . . .
C12 C 0.90823(18) 0.58781(10) 0.62640(11) 0.0285(4) Uani 1 1 d . . . . .
H12 H 1.014025 0.601346 0.623928 0.034 Uiso 1 1 calc R U . . .
C13 C 0.81813(19) 0.59325(10) 0.56547(10) 0.0254(3) Uani 1 1 d . . . . .
H13 H 0.861867 0.609953 0.521300 0.030 Uiso 1 1 calc R U . . .
C14 C 0.66286(18) 0.57397(9) 0.56975(8) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.51746(19) 0.65534(10) 0.34074(8) 0.0209(3) Uani 1 1 d . . . . .
C16 C 0.3131(2) 0.72793(11) 0.21900(9) 0.0258(3) Uani 1 1 d . . . . .
H16A H 0.244729 0.765620 0.193620 0.039 Uiso 1 1 calc R U . . .
H16B H 0.252079 0.685611 0.242837 0.039 Uiso 1 1 calc R U . . .
H16C H 0.383255 0.702201 0.184795 0.039 Uiso 1 1 calc R U . . .
C17 C 0.40335(18) 0.77415(10) 0.27343(8) 0.0199(3) Uani 1 1 d . . . . .
C18 C 0.41637(19) 0.85619(10) 0.28376(9) 0.0216(3) Uani 1 1 d . . . . .
H18 H 0.368280 0.898078 0.256606 0.026 Uiso 1 1 calc R U . . .
C19 C 0.51603(19) 0.86707(10) 0.34317(9) 0.0218(3) Uani 1 1 d . . . . .
C20 C 0.5718(2) 0.94526(10) 0.37558(10) 0.0293(4) Uani 1 1 d . . . . .
H20A H 0.652152 0.968794 0.345260 0.044 Uiso 1 1 calc R U . . .
H20B H 0.613536 0.934274 0.423276 0.044 Uiso 1 1 calc R U . . .
H20C H 0.486354 0.983930 0.379444 0.044 Uiso 1 1 calc R U . . .
C21 C 0.31065(18) 0.39226(9) 0.50117(9) 0.0208(3) Uani 1 1 d . . . . .
C22 C 0.4448(2) 0.12685(10) 0.59486(10) 0.0299(4) Uani 1 1 d . . . . .
H22A H 0.499591 0.087140 0.565047 0.045 Uiso 1 1 calc R U . . .
H22B H 0.365639 0.098584 0.622657 0.045 Uiso 1 1 calc R U . . .
H22C H 0.517285 0.153441 0.627472 0.045 Uiso 1 1 calc R U . . .
C23 C 0.37165(19) 0.18981(9) 0.54833(9) 0.0215(3) Uani 1 1 d . . . . .
C24 C 0.27112(19) 0.17631(10) 0.48964(9) 0.0229(3) Uani 1 1 d . . . . .
H24 H 0.237725 0.124831 0.471916 0.027 Uiso 1 1 calc R U . . .
C25 C 0.23206(18) 0.25102(10) 0.46384(9) 0.0210(3) Uani 1 1 d . . . . .
C26 C 0.13035(19) 0.27330(11) 0.40292(9) 0.0277(4) Uani 1 1 d . . . . .
H26A H 0.188576 0.305290 0.367889 0.042 Uiso 1 1 calc R U . . .
H26B H 0.043970 0.305909 0.420551 0.042 Uiso 1 1 calc R U . . .
H26C H 0.091589 0.223366 0.380221 0.042 Uiso 1 1 calc R U . . .
C27 C 0.33595(17) 0.59426(9) 0.67279(8) 0.0176(3) Uani 1 1 d . . . . .
C28 C 0.28523(18) 0.57336(10) 0.74139(9) 0.0225(3) Uani 1 1 d . . . . .
H28 H 0.311107 0.521584 0.761073 0.027 Uiso 1 1 calc R U . . .
C29 C 0.1973(2) 0.62791(11) 0.78079(9) 0.0273(4) Uani 1 1 d . . . . .
H29 H 0.163018 0.613065 0.827218 0.033 Uiso 1 1 calc R U . . .
C30 C 0.15904(19) 0.70393(11) 0.75300(10) 0.0272(3) Uani 1 1 d . . . . .
H30 H 0.096750 0.740430 0.779814 0.033 Uiso 1 1 calc R U . . .
C31 C 0.21217(19) 0.72645(10) 0.68582(9) 0.0243(3) Uani 1 1 d . . . . .
H31 H 0.188350 0.778874 0.666884 0.029 Uiso 1 1 calc R U . . .
C32 C 0.30059(18) 0.67166(9) 0.64639(8) 0.0207(3) Uani 1 1 d . . . . .
H32 H 0.337471 0.687404 0.600617 0.025 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.211(2) . ?
O2 C21 1.209(2) . ?
N1 N2 1.3809(19) . ?
N1 C17 1.385(2) . ?
N1 C15 1.403(2) . ?
N2 C19 1.316(2) . ?
N3 N4 1.3791(18) . ?
N3 C25 1.389(2) . ?
N3 C21 1.4001(19) . ?
N4 C23 1.318(2) . ?
C1 C14 1.514(2) . ?
C1 C5 1.525(2) . ?
C1 C4 1.560(2) . ?
C1 C2 1.5701(19) . ?
C2 C3 1.553(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C15 1.504(2) . ?
C3 C4 1.550(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5556(19) . ?
C5 C8 1.563(2) . ?
C5 H5 1.0000 . ?
C6 C21 1.503(2) . ?
C6 C7 1.558(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.5565(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C27 1.508(2) . ?
C8 C9 1.519(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H13 0.9500 . ?
C16 C17 1.492(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.359(2) . ?
C18 C19 1.422(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.496(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 C23 1.491(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.422(2) . ?
C24 C25 1.356(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.489(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.393(2) . ?
C27 C28 1.399(2) . ?
C28 C29 1.388(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(2) . ?
C31 H31 0.9500 . ?
C32 H32 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
N2 N1 C17 111.93(12) . . ?
N2 N1 C15 118.84(13) . . ?
C17 N1 C15 129.21(13) . . ?
C19 N2 N1 104.60(13) . . ?
N4 N3 C25 111.97(13) . . ?
N4 N3 C21 120.01(12) . . ?
C25 N3 C21 128.01(14) . . ?
C23 N4 N3 104.62(12) . . ?
C14 C1 C5 101.93(12) . . ?
C14 C1 C4 116.96(13) . . ?
C5 C1 C4 118.37(13) . . ?
C14 C1 C2 114.55(13) . . ?
C5 C1 C2 117.10(13) . . ?
C4 C1 C2 88.71(11) . . ?
C3 C2 C1 89.30(11) . . ?
C3 C2 H2A 113.8 . . ?
C1 C2 H2A 113.8 . . ?
C3 C2 H2B 113.8 . . ?
C1 C2 H2B 113.8 . . ?
H2A C2 H2B 111.0 . . ?
C15 C3 C4 115.32(13) . . ?
C15 C3 C2 116.12(13) . . ?
C4 C3 C2 89.71(11) . . ?
C15 C3 H3 111.4 . . ?
C4 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
C3 C4 C1 89.79(11) . . ?
C3 C4 H4A 113.7 . . ?
C1 C4 H4A 113.7 . . ?
C3 C4 H4B 113.7 . . ?
C1 C4 H4B 113.7 . . ?
H4A C4 H4B 110.9 . . ?
C1 C5 C6 116.82(12) . . ?
C1 C5 C8 109.35(12) . . ?
C6 C5 C8 87.91(11) . . ?
C1 C5 H5 113.4 . . ?
C6 C5 H5 113.4 . . ?
C8 C5 H5 113.4 . . ?
C21 C6 C5 115.35(12) . . ?
C21 C6 C7 119.83(13) . . ?
C5 C6 C7 89.35(11) . . ?
C21 C6 H6 110.2 . . ?
C5 C6 H6 110.2 . . ?
C7 C6 H6 110.2 . . ?
C8 C7 C6 88.07(11) . . ?
C8 C7 H7A 114.0 . . ?
C6 C7 H7A 114.0 . . ?
C8 C7 H7B 114.0 . . ?
C6 C7 H7B 114.0 . . ?
H7A C7 H7B 111.2 . . ?
C27 C8 C9 112.17(12) . . ?
C27 C8 C7 117.92(12) . . ?
C9 C8 C7 114.19(12) . . ?
C27 C8 C5 119.83(12) . . ?
C9 C8 C5 100.72(12) . . ?
C7 C8 C5 89.12(11) . . ?
C10 C9 C14 120.89(14) . . ?
C10 C9 C8 127.44(14) . . ?
C14 C9 C8 111.66(13) . . ?
C11 C10 C9 118.71(16) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.56(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.62(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.28(16) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 119.93(15) . . ?
C13 C14 C1 128.27(15) . . ?
C9 C14 C1 111.79(13) . . ?
O1 C15 N1 120.82(15) . . ?
O1 C15 C3 124.41(15) . . ?
N1 C15 C3 114.76(13) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N1 105.44(13) . . ?
C18 C17 C16 129.82(15) . . ?
N1 C17 C16 124.74(14) . . ?
C17 C18 C19 106.59(14) . . ?
C17 C18 H18 126.7 . . ?
C19 C18 H18 126.7 . . ?
N2 C19 C18 111.43(14) . . ?
N2 C19 C20 120.07(15) . . ?
C18 C19 C20 128.49(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 N3 119.76(14) . . ?
O2 C21 C6 123.42(14) . . ?
N3 C21 C6 116.81(13) . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 C24 111.27(14) . . ?
N4 C23 C22 121.33(15) . . ?
C24 C23 C22 127.40(15) . . ?
C25 C24 C23 106.85(14) . . ?
C25 C24 H24 126.6 . . ?
C23 C24 H24 126.6 . . ?
C24 C25 N3 105.27(14) . . ?
C24 C25 C26 129.94(15) . . ?
N3 C25 C26 124.78(15) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 118.48(14) . . ?
C32 C27 C8 120.81(13) . . ?
C28 C27 C8 120.71(14) . . ?
C29 C28 C27 120.32(16) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.61(15) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.73(15) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 119.57(16) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C27 C32 C31 121.24(15) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?

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
C17 N1 N2 C19 -0.78(17) . . . . ?
C15 N1 N2 C19 -179.41(14) . . . . ?
C25 N3 N4 C23 -0.36(17) . . . . ?
C21 N3 N4 C23 -179.19(14) . . . . ?
C14 C1 C2 C3 107.41(14) . . . . ?
C5 C1 C2 C3 -133.31(14) . . . . ?
C4 C1 C2 C3 -11.82(12) . . . . ?
C1 C2 C3 C15 130.18(14) . . . . ?
C1 C2 C3 C4 11.89(13) . . . . ?
C15 C3 C4 C1 -130.96(14) . . . . ?
C2 C3 C4 C1 -11.97(13) . . . . ?
C14 C1 C4 C3 -105.21(14) . . . . ?
C5 C1 C4 C3 132.22(14) . . . . ?
C2 C1 C4 C3 11.84(12) . . . . ?
C14 C1 C5 C6 -77.33(15) . . . . ?
C4 C1 C5 C6 52.52(19) . . . . ?
C2 C1 C5 C6 156.86(13) . . . . ?
C14 C1 C5 C8 20.39(15) . . . . ?
C4 C1 C5 C8 150.24(13) . . . . ?
C2 C1 C5 C8 -105.42(15) . . . . ?
C1 C5 C6 C21 -108.64(16) . . . . ?
C8 C5 C6 C21 140.68(13) . . . . ?
C1 C5 C6 C7 128.33(13) . . . . ?
C8 C5 C6 C7 17.65(11) . . . . ?
C21 C6 C7 C8 -136.88(13) . . . . ?
C5 C6 C7 C8 -17.73(11) . . . . ?
C6 C7 C8 C27 141.35(13) . . . . ?
C6 C7 C8 C9 -83.72(14) . . . . ?
C6 C7 C8 C5 17.64(11) . . . . ?
C1 C5 C8 C27 102.50(14) . . . . ?
C6 C5 C8 C27 -139.75(13) . . . . ?
C1 C5 C8 C9 -20.96(15) . . . . ?
C6 C5 C8 C9 96.80(11) . . . . ?
C1 C5 C8 C7 -135.43(12) . . . . ?
C6 C5 C8 C7 -17.67(11) . . . . ?
C27 C8 C9 C10 63.6(2) . . . . ?
C7 C8 C9 C10 -73.9(2) . . . . ?
C5 C8 C9 C10 -167.81(14) . . . . ?
C27 C8 C9 C14 -115.11(14) . . . . ?
C7 C8 C9 C14 107.38(14) . . . . ?
C5 C8 C9 C14 13.49(15) . . . . ?
C14 C9 C10 C11 0.6(2) . . . . ?
C8 C9 C10 C11 -177.96(14) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C12 C13 C14 C1 179.36(15) . . . . ?
C10 C9 C14 C13 -0.9(2) . . . . ?
C8 C9 C14 C13 177.94(13) . . . . ?
C10 C9 C14 C1 179.90(13) . . . . ?
C8 C9 C14 C1 -1.30(17) . . . . ?
C5 C1 C14 C13 168.94(15) . . . . ?
C4 C1 C14 C13 38.2(2) . . . . ?
C2 C1 C14 C13 -63.6(2) . . . . ?
C5 C1 C14 C9 -11.90(15) . . . . ?
C4 C1 C14 C9 -142.61(13) . . . . ?
C2 C1 C14 C9 115.58(14) . . . . ?
N2 N1 C15 O1 -172.57(14) . . . . ?
C17 N1 C15 O1 9.1(3) . . . . ?
N2 N1 C15 C3 8.8(2) . . . . ?
C17 N1 C15 C3 -169.60(15) . . . . ?
C4 C3 C15 O1 -11.4(2) . . . . ?
C2 C3 C15 O1 -114.46(18) . . . . ?
C4 C3 C15 N1 167.21(13) . . . . ?
C2 C3 C15 N1 64.16(18) . . . . ?
N2 N1 C17 C18 0.19(17) . . . . ?
C15 N1 C17 C18 178.64(15) . . . . ?
N2 N1 C17 C16 -179.12(14) . . . . ?
C15 N1 C17 C16 -0.7(3) . . . . ?
N1 C17 C18 C19 0.44(17) . . . . ?
C16 C17 C18 C19 179.70(16) . . . . ?
N1 N2 C19 C18 1.05(18) . . . . ?
N1 N2 C19 C20 -178.22(15) . . . . ?
C17 C18 C19 N2 -0.98(19) . . . . ?
C17 C18 C19 C20 178.22(17) . . . . ?
N4 N3 C21 O2 -176.58(16) . . . . ?
C25 N3 C21 O2 4.8(3) . . . . ?
N4 N3 C21 C6 4.6(2) . . . . ?
C25 N3 C21 C6 -174.05(14) . . . . ?
C5 C6 C21 O2 4.6(2) . . . . ?
C7 C6 C21 O2 109.52(19) . . . . ?
C5 C6 C21 N3 -176.58(13) . . . . ?
C7 C6 C21 N3 -71.67(18) . . . . ?
N3 N4 C23 C24 0.67(17) . . . . ?
N3 N4 C23 C22 -179.46(14) . . . . ?
N4 C23 C24 C25 -0.75(18) . . . . ?
C22 C23 C24 C25 179.39(16) . . . . ?
C23 C24 C25 N3 0.48(17) . . . . ?
C23 C24 C25 C26 179.88(16) . . . . ?
N4 N3 C25 C24 -0.09(17) . . . . ?
C21 N3 C25 C24 178.62(15) . . . . ?
N4 N3 C25 C26 -179.54(14) . . . . ?
C21 N3 C25 C26 -0.8(2) . . . . ?
C9 C8 C27 C32 82.98(17) . . . . ?
C7 C8 C27 C32 -141.24(15) . . . . ?
C5 C8 C27 C32 -34.7(2) . . . . ?
C9 C8 C27 C28 -96.38(16) . . . . ?
C7 C8 C27 C28 39.4(2) . . . . ?
C5 C8 C27 C28 145.90(14) . . . . ?
C32 C27 C28 C29 2.2(2) . . . . ?
C8 C27 C28 C29 -178.46(14) . . . . ?
C27 C28 C29 C30 -0.3(2) . . . . ?
C28 C29 C30 C31 -1.5(3) . . . . ?
C29 C30 C31 C32 1.4(2) . . . . ?
C28 C27 C32 C31 -2.3(2) . . . . ?
C8 C27 C32 C31 178.35(14) . . . . ?
C30 C31 C32 C27 0.5(2) . . . . ?

####################################################################### 
# 
# 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_Werz_MG507F1R_APEX_a
_database_code_depnum_ccdc_archive 'CCDC 2465273'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V143 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C42 H32 O2'
_chemical_formula_moiety         'C42 H32 O2'
_chemical_formula_weight         568.67
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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, -z'

_cell_length_a                   10.793(10)
_cell_length_b                   11.439(10)
_cell_length_c                   14.225(13)
_cell_angle_alpha                67.520(19)
_cell_angle_beta                 69.114(15)
_cell_angle_gamma                69.485(12)
_cell_volume                     1469(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6013
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.434
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature by slow diffusion of heptane into asolution of the compound dissolved in chloroform by the aid of layering.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5417
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.987
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            28054
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_theta_min         1.603
_diffrn_reflns_theta_max         26.594
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6085
_reflns_number_gt                4113
_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 BIS 2018.9.0.3/05-Dec-2018 and APEX6_2024.9-1'
_computing_cell_refinement       'SAINT V8.41'
_computing_data_reduction        'SAINT V8.41'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+1.4473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6085
_refine_ls_number_parameters     543
_refine_ls_number_restraints     2582
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 -0.0216(2) 0.6023(2) 0.67393(17) 0.0591(6) Uani 1 1 d . . . . .
O2 O 0.4387(2) 0.63455(17) 0.16038(15) 0.0462(5) Uani 1 1 d . . . . .
C1 C 0.2875(2) 0.49334(19) 0.44466(18) 0.0254(5) Uani 1 1 d . . . . .
C4 C 0.6347(3) 0.2496(2) 0.3810(2) 0.0377(6) Uani 1 1 d . . . . .
H4 H 0.720814 0.243083 0.330410 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6082(3) 0.1410(2) 0.4649(2) 0.0417(7) Uani 1 1 d . . . . .
H5 H 0.676205 0.060652 0.471178 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4833(2) 0.1484(2) 0.5399(2) 0.0373(6) Uani 1 1 d . . . . .
H6 H 0.464832 0.073632 0.596838 0.045 Uiso 1 1 calc R U . . .
C7 C 0.3850(2) 0.2679(2) 0.5300(2) 0.0292(5) Uani 1 1 d . . . . .
C8 C 0.2421(2) 0.2957(2) 0.60120(19) 0.0274(5) Uani 1 1 d D . . . .
C9 C 0.2377(3) 0.3207(2) 0.7021(2) 0.0370(6) Uani 1 1 d . . . . .
H9A H 0.326363 0.284918 0.720984 0.044 Uiso 1 1 calc R U . . .
H9B H 0.162732 0.292995 0.763347 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2064(3) 0.4704(2) 0.64613(19) 0.0321(5) Uani 1 1 d . . . . .
H10 H 0.289204 0.504162 0.624814 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1883(2) 0.44698(19) 0.55219(18) 0.0257(5) Uani 1 1 d . . . . .
H11 H 0.090760 0.473325 0.549237 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2339(2) 0.5460(2) 0.34357(18) 0.0273(5) Uani 1 1 d . . . . .
H12A H 0.287303 0.496578 0.291880 0.033 Uiso 1 1 calc R U . . .
H12B H 0.134755 0.553941 0.359029 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2687(2) 0.6775(2) 0.31359(18) 0.0271(5) Uani 1 1 d . . . . .
H13 H 0.185154 0.751965 0.313338 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3142(2) 0.6300(2) 0.41780(19) 0.0280(5) Uani 1 1 d . . . . .
H14A H 0.253797 0.678795 0.468823 0.034 Uiso 1 1 calc R U . . .
H14B H 0.411362 0.626590 0.406087 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0832(3) 0.5530(2) 0.7037(2) 0.0420(7) Uani 1 1 d D . . . .
C16 C 0.3829(2) 0.7071(2) 0.21584(19) 0.0298(5) Uani 1 1 d . . . . .
C2 C 0.4109(2) 0.3769(2) 0.44562(19) 0.0264(5) Uani 1 1 d . . . . .
C3 C 0.5362(2) 0.3682(2) 0.3704(2) 0.0311(5) Uani 1 1 d . . . . .
H3 H 0.554298 0.442230 0.312408 0.037 Uiso 1 1 calc R U . . .
C1_1 C 0.169(2) 0.1952(19) 0.6181(18) 0.029(2) Uani 0.486(3) 1 d D U P A 1
C2_1 C 0.102(2) 0.2062(15) 0.5472(15) 0.031(2) Uani 0.486(3) 1 d D U P A 1
H2_1 H 0.101430 0.278719 0.485464 0.038 Uiso 0.486(3) 1 calc R U P A 1
C3_1 C 0.0340(16) 0.1120(12) 0.5651(11) 0.029(2) Uani 0.486(3) 1 d D U P A 1
H3_1 H -0.011679 0.120098 0.516083 0.035 Uiso 0.486(3) 1 calc R U P A 1
C4_1 C 0.0349(15) 0.0071(12) 0.6555(10) 0.033(2) Uani 0.486(3) 1 d D U P A 1
H4_1 H -0.010191 -0.057582 0.668609 0.040 Uiso 0.486(3) 1 calc R U P A 1
C5_1 C 0.1012(16) -0.0042(14) 0.7271(12) 0.036(2) Uani 0.486(3) 1 d D U P A 1
H5_1 H 0.099729 -0.075725 0.789600 0.043 Uiso 0.486(3) 1 calc R U P A 1
C6_1 C 0.169(2) 0.0879(17) 0.7083(16) 0.034(2) Uani 0.486(3) 1 d D U P A 1
H6_1 H 0.216648 0.078175 0.756883 0.040 Uiso 0.486(3) 1 calc R U P A 1
C1_2 C 0.158(2) 0.2069(17) 0.6143(17) 0.030(2) Uani 0.514(3) 1 d D U P A 2
C2_2 C 0.101(2) 0.2269(14) 0.5333(13) 0.028(2) Uani 0.514(3) 1 d D U P A 2
H2_2 H 0.108769 0.301114 0.473127 0.034 Uiso 0.514(3) 1 calc R U P A 2
C3_2 C 0.0342(17) 0.1391(12) 0.5403(11) 0.034(2) Uani 0.514(3) 1 d D U P A 2
H3_2 H -0.003705 0.154197 0.484618 0.041 Uiso 0.514(3) 1 calc R U P A 2
C4_2 C 0.0214(13) 0.0296(11) 0.6272(10) 0.032(2) Uani 0.514(3) 1 d D U P A 2
H4_2 H -0.025469 -0.029370 0.631225 0.039 Uiso 0.514(3) 1 calc R U P A 2
C5_2 C 0.0777(15) 0.0077(14) 0.7074(12) 0.039(2) Uani 0.514(3) 1 d D U P A 2
H5_2 H 0.071657 -0.067935 0.766419 0.047 Uiso 0.514(3) 1 calc R U P A 2
C6_2 C 0.1436(18) 0.0963(17) 0.7019(16) 0.036(2) Uani 0.514(3) 1 d D U P A 2
H6_2 H 0.179579 0.081577 0.758593 0.043 Uiso 0.514(3) 1 calc R U P A 2
C1_3 C 0.0621(6) 0.5936(6) 0.7957(5) 0.0270(13) Uani 0.486(3) 1 d D U P A 1
C2_3 C -0.0529(5) 0.6898(4) 0.8285(4) 0.0293(11) Uani 0.486(3) 1 d D U P A 1
H2_3 H -0.125254 0.726215 0.794633 0.035 Uiso 0.486(3) 1 calc R U P A 1
C3_3 C -0.0594(5) 0.7303(4) 0.9095(4) 0.0301(11) Uani 0.486(3) 1 d D U P A 1
H3_3 H -0.136920 0.794813 0.931886 0.036 Uiso 0.486(3) 1 calc R U P A 1
C4_3 C 0.0481(7) 0.6771(7) 0.9604(6) 0.0291(13) Uani 0.486(3) 1 d D U P A 1
C5_3 C 0.0456(5) 0.7207(5) 1.0424(4) 0.0340(11) Uani 0.486(3) 1 d D U P A 1
H5_3 H -0.028451 0.788877 1.062844 0.041 Uiso 0.486(3) 1 calc R U P A 1
C6_3 C 0.1491(6) 0.6653(7) 1.0918(5) 0.0373(13) Uani 0.486(3) 1 d D U P A 1
H6_3 H 0.145859 0.695573 1.146435 0.045 Uiso 0.486(3) 1 calc R U P A 1
C7_3 C 0.2604(6) 0.5640(5) 1.0635(4) 0.0371(12) Uani 0.486(3) 1 d D U P A 1
H7_3 H 0.330943 0.525880 1.099244 0.045 Uiso 0.486(3) 1 calc R U P A 1
C8_3 C 0.2664(5) 0.5208(5) 0.9839(4) 0.0317(11) Uani 0.486(3) 1 d D U P A 1
H8_3 H 0.341538 0.452654 0.964656 0.038 Uiso 0.486(3) 1 calc R U P A 1
C9_3 C 0.1614(5) 0.5768(5) 0.9300(4) 0.0273(11) Uani 0.486(3) 1 d D U P A 1
C10_3 C 0.1666(6) 0.5384(5) 0.8444(4) 0.0274(11) Uani 0.486(3) 1 d D U P A 1
H10_3 H 0.243056 0.473835 0.820940 0.033 Uiso 0.486(3) 1 calc R U P A 1
C1_4 C 0.1156(6) 0.5595(5) 0.8010(5) 0.0266(13) Uani 0.514(3) 1 d D U P A 2
C2_4 C 0.2280(5) 0.4822(5) 0.8459(4) 0.0282(11) Uani 0.514(3) 1 d D U P A 2
H2_4 H 0.291620 0.413570 0.818661 0.034 Uiso 0.514(3) 1 calc R U P A 2
C3_4 C 0.2463(5) 0.5046(4) 0.9276(4) 0.0317(10) Uani 0.514(3) 1 d D U P A 2
H3_4 H 0.322295 0.451939 0.956006 0.038 Uiso 0.514(3) 1 calc R U P A 2
C4_4 C 0.1523(5) 0.6060(5) 0.9698(4) 0.0311(11) Uani 0.514(3) 1 d D U P A 2
C5_4 C 0.1739(6) 0.6348(6) 1.0506(5) 0.0373(13) Uani 0.514(3) 1 d D U P A 2
H5_4 H 0.249283 0.583058 1.079990 0.045 Uiso 0.514(3) 1 calc R U P A 2
C6_4 C 0.0846(6) 0.7382(5) 1.0860(4) 0.0380(12) Uani 0.514(3) 1 d D U P A 2
H6_4 H 0.099629 0.758205 1.139356 0.046 Uiso 0.514(3) 1 calc R U P A 2
C7_4 C -0.0296(5) 0.8156(5) 1.0440(4) 0.0380(12) Uani 0.514(3) 1 d D U P A 2
H7_4 H -0.089750 0.887307 1.068753 0.046 Uiso 0.514(3) 1 calc R U P A 2
C8_4 C -0.0530(5) 0.7866(4) 0.9678(4) 0.0345(11) Uani 0.514(3) 1 d D U P A 2
H8_4 H -0.131100 0.836915 0.941477 0.041 Uiso 0.514(3) 1 calc R U P A 2
C9_4 C 0.0377(7) 0.6827(7) 0.9278(5) 0.0307(13) Uani 0.514(3) 1 d D U P A 2
C10_4 C 0.0205(5) 0.6554(4) 0.8450(4) 0.0272(10) Uani 0.514(3) 1 d D U P A 2
H10_4 H -0.058098 0.703845 0.818867 0.033 Uiso 0.514(3) 1 calc R U P A 2
C1_6 C 0.4300(2) 0.8259(2) 0.19134(18) 0.0285(5) Uani 1 1 d D U . . .
C2_6 C 0.5486(2) 0.8477(2) 0.10774(19) 0.0321(5) Uani 1 1 d D U . . .
H2_6 H 0.595453 0.787557 0.067775 0.039 Uiso 1 1 calc R U . . .
C3_6 C 0.5956(3) 0.9548(2) 0.0846(2) 0.0358(6) Uani 1 1 d D U . . .
H3_6 H 0.675823 0.967071 0.029409 0.043 Uiso 1 1 calc R U . . .
C4_6 C 0.5272(3) 1.0475(2) 0.1412(2) 0.0337(6) Uani 1 1 d D U . . .
C5_6 C 0.5728(3) 1.1602(2) 0.1181(2) 0.0442(7) Uani 1 1 d D U . . .
H5_6 H 0.651059 1.176074 0.061734 0.053 Uiso 1 1 calc R U . . .
C6_6 C 0.5056(4) 1.2455(3) 0.1761(3) 0.0570(8) Uani 1 1 d D U . . .
H6_6 H 0.537287 1.320275 0.160156 0.068 Uiso 1 1 calc R U . . .
C7_6 C 0.3899(4) 1.2234(3) 0.2591(3) 0.0650(10) Uani 1 1 d D U . . .
H7_6 H 0.344632 1.282741 0.299831 0.078 Uiso 1 1 calc R U . . .
C8_6 C 0.3410(3) 1.1175(3) 0.2824(3) 0.0524(8) Uani 1 1 d D U . . .
H8_6 H 0.261384 1.104755 0.338167 0.063 Uiso 1 1 calc R U . . .
C9_6 C 0.4083(3) 1.0270(2) 0.2238(2) 0.0353(6) Uani 1 1 d D U . . .
C10_6 C 0.3628(2) 0.9147(2) 0.2472(2) 0.0326(5) Uani 1 1 d D U . . .
H10_6 H 0.283603 0.900453 0.303017 0.039 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.220(4) . ?
O2 C16 1.219(3) . ?
C1 C2 1.518(3) . ?
C1 C11 1.542(3) . ?
C1 C12 1.566(3) . ?
C1 C14 1.567(3) . ?
C4 C5 1.386(4) . ?
C4 C3 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(3) . ?
C6 H6 0.9500 . ?
C7 C2 1.391(3) . ?
C7 C8 1.514(3) . ?
C8 C1_2 1.508(10) . ?
C8 C1_1 1.514(9) . ?
C8 C9 1.549(4) . ?
C8 C11 1.575(3) . ?
C9 C10 1.557(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.505(4) . ?
C10 C11 1.546(3) . ?
C10 H10 1.0000 . ?
C11 H11 1.0000 . ?
C12 C13 1.542(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C16 1.510(3) . ?
C13 C14 1.566(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C1_3 1.470(7) . ?
C15 C1_4 1.578(7) . ?
C16 C1_6 1.491(3) . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C1_1 C2_1 1.386(10) . ?
C1_1 C6_1 1.396(10) . ?
C2_1 C3_1 1.403(9) . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.383(8) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.385(9) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.382(9) . ?
C5_1 H5_1 0.9500 . ?
C6_1 H6_1 0.9500 . ?
C1_2 C2_2 1.399(10) . ?
C1_2 C6_2 1.403(9) . ?
C2_2 C3_2 1.387(9) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.390(7) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.380(8) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.395(9) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_3 C10_3 1.369(7) . ?
C1_3 C2_3 1.411(7) . ?
C2_3 C3_3 1.369(6) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.417(7) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C9_3 1.420(7) . ?
C4_3 C5_3 1.422(7) . ?
C5_3 C6_3 1.367(7) . ?
C5_3 H5_3 0.9500 . ?
C6_3 C7_3 1.408(8) . ?
C6_3 H6_3 0.9500 . ?
C7_3 C8_3 1.373(7) . ?
C7_3 H7_3 0.9500 . ?
C8_3 C9_3 1.420(7) . ?
C8_3 H8_3 0.9500 . ?
C9_3 C10_3 1.422(7) . ?
C10_3 H10_3 0.9500 . ?
C1_4 C10_4 1.388(6) . ?
C1_4 C2_4 1.424(7) . ?
C2_4 C3_4 1.372(6) . ?
C2_4 H2_4 0.9500 . ?
C3_4 C4_4 1.417(6) . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.421(7) . ?
C4_4 C9_4 1.422(7) . ?
C5_4 C6_4 1.375(7) . ?
C5_4 H5_4 0.9500 . ?
C6_4 C7_4 1.420(7) . ?
C6_4 H6_4 0.9500 . ?
C7_4 C8_4 1.371(6) . ?
C7_4 H7_4 0.9500 . ?
C8_4 C9_4 1.414(7) . ?
C8_4 H8_4 0.9500 . ?
C9_4 C10_4 1.413(7) . ?
C10_4 H10_4 0.9500 . ?
C1_6 C10_6 1.370(3) . ?
C1_6 C2_6 1.424(3) . ?
C2_6 C3_6 1.369(3) . ?
C2_6 H2_6 0.9500 . ?
C3_6 C4_6 1.413(3) . ?
C3_6 H3_6 0.9500 . ?
C4_6 C9_6 1.416(4) . ?
C4_6 C5_6 1.421(3) . ?
C5_6 C6_6 1.360(4) . ?
C5_6 H5_6 0.9500 . ?
C6_6 C7_6 1.400(4) . ?
C6_6 H6_6 0.9500 . ?
C7_6 C8_6 1.368(4) . ?
C7_6 H7_6 0.9500 . ?
C8_6 C9_6 1.412(4) . ?
C8_6 H8_6 0.9500 . ?
C9_6 C10_6 1.415(3) . ?
C10_6 H10_6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 102.52(18) . . ?
C2 C1 C12 114.67(19) . . ?
C11 C1 C12 118.2(2) . . ?
C2 C1 C14 117.13(19) . . ?
C11 C1 C14 116.23(18) . . ?
C12 C1 C14 88.80(16) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 120.6(2) . . ?
C2 C7 C8 112.18(19) . . ?
C6 C7 C8 127.1(2) . . ?
C1_2 C8 C7 113.6(10) . . ?
C1_1 C8 C7 110.3(11) . . ?
C1_2 C8 C9 116.9(9) . . ?
C1_1 C8 C9 115.8(9) . . ?
C7 C8 C9 113.5(2) . . ?
C1_2 C8 C11 118.2(8) . . ?
C1_1 C8 C11 123.9(9) . . ?
C7 C8 C11 102.09(18) . . ?
C9 C8 C11 89.46(17) . . ?
C8 C9 C10 89.85(18) . . ?
C8 C9 H9A 113.7 . . ?
C10 C9 H9A 113.7 . . ?
C8 C9 H9B 113.7 . . ?
C10 C9 H9B 113.7 . . ?
H9A C9 H9B 110.9 . . ?
C15 C10 C11 115.9(2) . . ?
C15 C10 C9 116.2(2) . . ?
C11 C10 C9 90.22(18) . . ?
C15 C10 H10 111.0 . . ?
C11 C10 H10 111.0 . . ?
C9 C10 H10 111.0 . . ?
C1 C11 C10 115.82(19) . . ?
C1 C11 C8 109.25(18) . . ?
C10 C11 C8 89.28(17) . . ?
C1 C11 H11 113.4 . . ?
C10 C11 H11 113.4 . . ?
C8 C11 H11 113.4 . . ?
C13 C12 C1 91.11(17) . . ?
C13 C12 H12A 113.4 . . ?
C1 C12 H12A 113.4 . . ?
C13 C12 H12B 113.4 . . ?
C1 C12 H12B 113.4 . . ?
H12A C12 H12B 110.7 . . ?
C16 C13 C12 116.32(19) . . ?
C16 C13 C14 113.1(2) . . ?
C12 C13 C14 89.73(16) . . ?
C16 C13 H13 112.0 . . ?
C12 C13 H13 112.0 . . ?
C14 C13 H13 112.0 . . ?
C13 C14 C1 90.17(16) . . ?
C13 C14 H14A 113.6 . . ?
C1 C14 H14A 113.6 . . ?
C13 C14 H14B 113.6 . . ?
C1 C14 H14B 113.6 . . ?
H14A C14 H14B 110.9 . . ?
O1 C15 C1_3 107.8(3) . . ?
O1 C15 C10 121.1(2) . . ?
C1_3 C15 C10 131.0(3) . . ?
O1 C15 C1_4 129.5(3) . . ?
C10 C15 C1_4 109.4(3) . . ?
O2 C16 C1_6 120.6(2) . . ?
O2 C16 C13 121.6(2) . . ?
C1_6 C16 C13 117.7(2) . . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1 112.4(2) . . ?
C3 C2 C1 127.4(2) . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C2_1 C1_1 C6_1 119.0(9) . . ?
C2_1 C1_1 C8 122.3(13) . . ?
C6_1 C1_1 C8 118.7(13) . . ?
C1_1 C2_1 C3_1 121.1(9) . . ?
C1_1 C2_1 H2_1 119.5 . . ?
C3_1 C2_1 H2_1 119.5 . . ?
C4_1 C3_1 C2_1 118.8(9) . . ?
C4_1 C3_1 H3_1 120.6 . . ?
C2_1 C3_1 H3_1 120.6 . . ?
C3_1 C4_1 C5_1 120.5(8) . . ?
C3_1 C4_1 H4_1 119.8 . . ?
C5_1 C4_1 H4_1 119.8 . . ?
C6_1 C5_1 C4_1 120.5(8) . . ?
C6_1 C5_1 H5_1 119.8 . . ?
C4_1 C5_1 H5_1 119.8 . . ?
C5_1 C6_1 C1_1 120.2(9) . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C1_1 C6_1 H6_1 119.9 . . ?
C2_2 C1_2 C6_2 117.8(9) . . ?
C2_2 C1_2 C8 119.8(12) . . ?
C6_2 C1_2 C8 122.2(12) . . ?
C3_2 C2_2 C1_2 120.4(9) . . ?
C3_2 C2_2 H2_2 119.8 . . ?
C1_2 C2_2 H2_2 119.8 . . ?
C2_2 C3_2 C4_2 121.3(9) . . ?
C2_2 C3_2 H3_2 119.3 . . ?
C4_2 C3_2 H3_2 119.3 . . ?
C5_2 C4_2 C3_2 119.1(7) . . ?
C5_2 C4_2 H4_2 120.5 . . ?
C3_2 C4_2 H4_2 120.5 . . ?
C4_2 C5_2 C6_2 120.1(8) . . ?
C4_2 C5_2 H5_2 120.0 . . ?
C6_2 C5_2 H5_2 120.0 . . ?
C5_2 C6_2 C1_2 121.3(9) . . ?
C5_2 C6_2 H6_2 119.3 . . ?
C1_2 C6_2 H6_2 119.3 . . ?
C10_3 C1_3 C2_3 121.2(5) . . ?
C10_3 C1_3 C15 115.6(5) . . ?
C2_3 C1_3 C15 123.1(5) . . ?
C3_3 C2_3 C1_3 119.5(5) . . ?
C3_3 C2_3 H2_3 120.2 . . ?
C1_3 C2_3 H2_3 120.2 . . ?
C2_3 C3_3 C4_3 120.8(5) . . ?
C2_3 C3_3 H3_3 119.6 . . ?
C4_3 C3_3 H3_3 119.6 . . ?
C3_3 C4_3 C9_3 119.7(5) . . ?
C3_3 C4_3 C5_3 121.7(5) . . ?
C9_3 C4_3 C5_3 118.6(5) . . ?
C6_3 C5_3 C4_3 120.4(5) . . ?
C6_3 C5_3 H5_3 119.8 . . ?
C4_3 C5_3 H5_3 119.8 . . ?
C5_3 C6_3 C7_3 121.3(6) . . ?
C5_3 C6_3 H6_3 119.4 . . ?
C7_3 C6_3 H6_3 119.4 . . ?
C8_3 C7_3 C6_3 119.6(5) . . ?
C8_3 C7_3 H7_3 120.2 . . ?
C6_3 C7_3 H7_3 120.2 . . ?
C7_3 C8_3 C9_3 120.7(5) . . ?
C7_3 C8_3 H8_3 119.6 . . ?
C9_3 C8_3 H8_3 119.6 . . ?
C8_3 C9_3 C4_3 119.4(5) . . ?
C8_3 C9_3 C10_3 122.4(5) . . ?
C4_3 C9_3 C10_3 118.2(5) . . ?
C1_3 C10_3 C9_3 120.5(5) . . ?
C1_3 C10_3 H10_3 119.8 . . ?
C9_3 C10_3 H10_3 119.8 . . ?
C10_4 C1_4 C2_4 118.4(5) . . ?
C10_4 C1_4 C15 113.3(5) . . ?
C2_4 C1_4 C15 128.3(4) . . ?
C3_4 C2_4 C1_4 121.4(5) . . ?
C3_4 C2_4 H2_4 119.3 . . ?
C1_4 C2_4 H2_4 119.3 . . ?
C2_4 C3_4 C4_4 120.2(5) . . ?
C2_4 C3_4 H3_4 119.9 . . ?
C4_4 C3_4 H3_4 119.9 . . ?
C3_4 C4_4 C5_4 120.8(5) . . ?
C3_4 C4_4 C9_4 119.3(5) . . ?
C5_4 C4_4 C9_4 119.8(5) . . ?
C6_4 C5_4 C4_4 119.4(5) . . ?
C6_4 C5_4 H5_4 120.3 . . ?
C4_4 C5_4 H5_4 120.3 . . ?
C5_4 C6_4 C7_4 121.2(5) . . ?
C5_4 C6_4 H6_4 119.4 . . ?
C7_4 C6_4 H6_4 119.4 . . ?
C8_4 C7_4 C6_4 119.8(4) . . ?
C8_4 C7_4 H7_4 120.1 . . ?
C6_4 C7_4 H7_4 120.1 . . ?
C7_4 C8_4 C9_4 120.8(5) . . ?
C7_4 C8_4 H8_4 119.6 . . ?
C9_4 C8_4 H8_4 119.6 . . ?
C10_4 C9_4 C8_4 122.0(5) . . ?
C10_4 C9_4 C4_4 119.0(5) . . ?
C8_4 C9_4 C4_4 119.0(5) . . ?
C1_4 C10_4 C9_4 121.5(5) . . ?
C1_4 C10_4 H10_4 119.2 . . ?
C9_4 C10_4 H10_4 119.2 . . ?
C10_6 C1_6 C2_6 118.9(2) . . ?
C10_6 C1_6 C16 122.0(2) . . ?
C2_6 C1_6 C16 119.1(2) . . ?
C3_6 C2_6 C1_6 120.4(2) . . ?
C3_6 C2_6 H2_6 119.8 . . ?
C1_6 C2_6 H2_6 119.8 . . ?
C2_6 C3_6 C4_6 121.4(2) . . ?
C2_6 C3_6 H3_6 119.3 . . ?
C4_6 C3_6 H3_6 119.3 . . ?
C3_6 C4_6 C9_6 118.5(2) . . ?
C3_6 C4_6 C5_6 122.5(2) . . ?
C9_6 C4_6 C5_6 118.9(2) . . ?
C6_6 C5_6 C4_6 120.6(3) . . ?
C6_6 C5_6 H5_6 119.7 . . ?
C4_6 C5_6 H5_6 119.7 . . ?
C5_6 C6_6 C7_6 120.2(3) . . ?
C5_6 C6_6 H6_6 119.9 . . ?
C7_6 C6_6 H6_6 119.9 . . ?
C8_6 C7_6 C6_6 120.9(3) . . ?
C8_6 C7_6 H7_6 119.5 . . ?
C6_6 C7_6 H7_6 119.5 . . ?
C7_6 C8_6 C9_6 120.3(3) . . ?
C7_6 C8_6 H8_6 119.9 . . ?
C9_6 C8_6 H8_6 119.9 . . ?
C8_6 C9_6 C10_6 121.9(2) . . ?
C8_6 C9_6 C4_6 119.0(2) . . ?
C10_6 C9_6 C4_6 119.1(2) . . ?
C1_6 C10_6 C9_6 121.7(2) . . ?
C1_6 C10_6 H10_6 119.2 . . ?
C9_6 C10_6 H10_6 119.2 . . ?

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
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C5 C6 C7 C8 178.3(2) . . . . ?
C2 C7 C8 C1_2 122.7(8) . . . . ?
C6 C7 C8 C1_2 -54.7(9) . . . . ?
C2 C7 C8 C1_1 127.8(8) . . . . ?
C6 C7 C8 C1_1 -49.6(9) . . . . ?
C2 C7 C8 C9 -100.4(2) . . . . ?
C6 C7 C8 C9 82.2(3) . . . . ?
C2 C7 C8 C11 -5.7(2) . . . . ?
C6 C7 C8 C11 176.9(2) . . . . ?
C1_2 C8 C9 C10 -129.8(10) . . . . ?
C1_1 C8 C9 C10 -136.1(11) . . . . ?
C7 C8 C9 C10 94.8(2) . . . . ?
C11 C8 C9 C10 -8.16(18) . . . . ?
C8 C9 C10 C15 127.6(2) . . . . ?
C8 C9 C10 C11 8.32(18) . . . . ?
C2 C1 C11 C10 86.3(2) . . . . ?
C12 C1 C11 C10 -146.56(19) . . . . ?
C14 C1 C11 C10 -42.8(3) . . . . ?
C2 C1 C11 C8 -12.6(2) . . . . ?
C12 C1 C11 C8 114.6(2) . . . . ?
C14 C1 C11 C8 -141.67(19) . . . . ?
C15 C10 C11 C1 121.2(2) . . . . ?
C9 C10 C11 C1 -119.3(2) . . . . ?
C15 C10 C11 C8 -127.7(2) . . . . ?
C9 C10 C11 C8 -8.18(18) . . . . ?
C1_2 C8 C11 C1 -114.0(11) . . . . ?
C1_1 C8 C11 C1 -113.4(12) . . . . ?
C7 C8 C11 C1 11.4(2) . . . . ?
C9 C8 C11 C1 125.4(2) . . . . ?
C1_2 C8 C11 C10 128.8(11) . . . . ?
C1_1 C8 C11 C10 129.4(12) . . . . ?
C7 C8 C11 C10 -105.8(2) . . . . ?
C9 C8 C11 C10 8.22(18) . . . . ?
C2 C1 C12 C13 -116.2(2) . . . . ?
C11 C1 C12 C13 122.68(19) . . . . ?
C14 C1 C12 C13 3.31(17) . . . . ?
C1 C12 C13 C16 112.5(2) . . . . ?
C1 C12 C13 C14 -3.32(17) . . . . ?
C16 C13 C14 C1 -115.37(19) . . . . ?
C12 C13 C14 C1 3.31(17) . . . . ?
C2 C1 C14 C13 114.0(2) . . . . ?
C11 C1 C14 C13 -124.4(2) . . . . ?
C12 C1 C14 C13 -3.26(17) . . . . ?
C11 C10 C15 O1 -3.1(3) . . . . ?
C9 C10 C15 O1 -107.2(3) . . . . ?
C11 C10 C15 C1_3 179.1(4) . . . . ?
C9 C10 C15 C1_3 75.0(4) . . . . ?
C11 C10 C15 C1_4 176.3(3) . . . . ?
C9 C10 C15 C1_4 72.2(3) . . . . ?
C12 C13 C16 O2 4.3(3) . . . . ?
C14 C13 C16 O2 106.1(3) . . . . ?
C12 C13 C16 C1_6 -173.18(19) . . . . ?
C14 C13 C16 C1_6 -71.3(2) . . . . ?
C6 C7 C2 C3 -0.6(4) . . . . ?
C8 C7 C2 C3 -178.2(2) . . . . ?
C6 C7 C2 C1 175.3(2) . . . . ?
C8 C7 C2 C1 -2.3(3) . . . . ?
C11 C1 C2 C7 9.3(2) . . . . ?
C12 C1 C2 C7 -120.1(2) . . . . ?
C14 C1 C2 C7 137.8(2) . . . . ?
C11 C1 C2 C3 -175.1(2) . . . . ?
C12 C1 C2 C3 55.5(3) . . . . ?
C14 C1 C2 C3 -46.6(3) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -175.5(2) . . . . ?
C5 C4 C3 C2 0.7(4) . . . . ?
C7 C8 C1_1 C2_1 -83.8(15) . . . . ?
C9 C8 C1_1 C2_1 145.6(12) . . . . ?
C11 C8 C1_1 C2_1 37(2) . . . . ?
C7 C8 C1_1 C6_1 96.3(17) . . . . ?
C9 C8 C1_1 C6_1 -34(2) . . . . ?
C11 C8 C1_1 C6_1 -142.5(14) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.3(15) . . . . ?
C8 C1_1 C2_1 C3_1 -180(2) . . . . ?
C1_1 C2_1 C3_1 C4_1 0.2(12) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.2(17) . . . . ?
C3_1 C4_1 C5_1 C6_1 -1.2(19) . . . . ?
C4_1 C5_1 C6_1 C1_1 2(2) . . . . ?
C2_1 C1_1 C6_1 C5_1 -1(2) . . . . ?
C8 C1_1 C6_1 C5_1 178.7(18) . . . . ?
C7 C8 C1_2 C2_2 -76.1(14) . . . . ?
C9 C8 C1_2 C2_2 148.6(10) . . . . ?
C11 C8 C1_2 C2_2 43.5(17) . . . . ?
C7 C8 C1_2 C6_2 98.1(18) . . . . ?
C9 C8 C1_2 C6_2 -37(2) . . . . ?
C11 C8 C1_2 C6_2 -142.4(15) . . . . ?
C6_2 C1_2 C2_2 C3_2 -0.3(14) . . . . ?
C8 C1_2 C2_2 C3_2 174.1(19) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.0(12) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.6(16) . . . . ?
C3_2 C4_2 C5_2 C6_2 1.5(18) . . . . ?
C4_2 C5_2 C6_2 C1_2 -2(2) . . . . ?
C2_2 C1_2 C6_2 C5_2 1(2) . . . . ?
C8 C1_2 C6_2 C5_2 -173.0(18) . . . . ?
O1 C15 C1_3 C10_3 175.0(4) . . . . ?
C10 C15 C1_3 C10_3 -6.9(7) . . . . ?
O1 C15 C1_3 C2_3 -9.2(6) . . . . ?
C10 C15 C1_3 C2_3 168.8(3) . . . . ?
C10_3 C1_3 C2_3 C3_3 1.1(6) . . . . ?
C15 C1_3 C2_3 C3_3 -174.4(5) . . . . ?
C1_3 C2_3 C3_3 C4_3 0.2(6) . . . . ?
C2_3 C3_3 C4_3 C9_3 -2.6(10) . . . . ?
C2_3 C3_3 C4_3 C5_3 177.9(6) . . . . ?
C3_3 C4_3 C5_3 C6_3 178.3(6) . . . . ?
C9_3 C4_3 C5_3 C6_3 -1.2(10) . . . . ?
C4_3 C5_3 C6_3 C7_3 0.0(9) . . . . ?
C5_3 C6_3 C7_3 C8_3 0.7(9) . . . . ?
C6_3 C7_3 C8_3 C9_3 -0.1(8) . . . . ?
C7_3 C8_3 C9_3 C4_3 -1.1(8) . . . . ?
C7_3 C8_3 C9_3 C10_3 177.5(5) . . . . ?
C3_3 C4_3 C9_3 C8_3 -177.8(6) . . . . ?
C5_3 C4_3 C9_3 C8_3 1.8(10) . . . . ?
C3_3 C4_3 C9_3 C10_3 3.6(10) . . . . ?
C5_3 C4_3 C9_3 C10_3 -176.9(6) . . . . ?
C2_3 C1_3 C10_3 C9_3 0.1(8) . . . . ?
C15 C1_3 C10_3 C9_3 175.9(4) . . . . ?
C8_3 C9_3 C10_3 C1_3 179.1(5) . . . . ?
C4_3 C9_3 C10_3 C1_3 -2.4(9) . . . . ?
O1 C15 C1_4 C10_4 -13.9(6) . . . . ?
C10 C15 C1_4 C10_4 166.7(4) . . . . ?
O1 C15 C1_4 C2_4 166.9(4) . . . . ?
C10 C15 C1_4 C2_4 -12.4(6) . . . . ?
C10_4 C1_4 C2_4 C3_4 -2.8(6) . . . . ?
C15 C1_4 C2_4 C3_4 176.3(4) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.3(5) . . . . ?
C2_4 C3_4 C4_4 C5_4 -176.7(4) . . . . ?
C2_4 C3_4 C4_4 C9_4 1.1(8) . . . . ?
C3_4 C4_4 C5_4 C6_4 176.6(5) . . . . ?
C9_4 C4_4 C5_4 C6_4 -1.1(9) . . . . ?
C4_4 C5_4 C6_4 C7_4 0.8(8) . . . . ?
C5_4 C6_4 C7_4 C8_4 0.7(8) . . . . ?
C6_4 C7_4 C8_4 C9_4 -1.9(8) . . . . ?
C7_4 C8_4 C9_4 C10_4 -176.3(6) . . . . ?
C7_4 C8_4 C9_4 C4_4 1.6(10) . . . . ?
C3_4 C4_4 C9_4 C10_4 0.1(10) . . . . ?
C5_4 C4_4 C9_4 C10_4 177.9(6) . . . . ?
C3_4 C4_4 C9_4 C8_4 -177.8(6) . . . . ?
C5_4 C4_4 C9_4 C8_4 0.0(10) . . . . ?
C2_4 C1_4 C10_4 C9_4 4.1(8) . . . . ?
C15 C1_4 C10_4 C9_4 -175.2(5) . . . . ?
C8_4 C9_4 C10_4 C1_4 175.1(6) . . . . ?
C4_4 C9_4 C10_4 C1_4 -2.8(10) . . . . ?
O2 C16 C1_6 C10_6 174.8(2) . . . . ?
C13 C16 C1_6 C10_6 -7.7(3) . . . . ?
O2 C16 C1_6 C2_6 -5.5(3) . . . . ?
C13 C16 C1_6 C2_6 172.02(19) . . . . ?
C10_6 C1_6 C2_6 C3_6 0.8(3) . . . . ?
C16 C1_6 C2_6 C3_6 -178.9(2) . . . . ?
C1_6 C2_6 C3_6 C4_6 -1.1(3) . . . . ?
C2_6 C3_6 C4_6 C9_6 0.5(4) . . . . ?
C2_6 C3_6 C4_6 C5_6 -179.3(2) . . . . ?
C3_6 C4_6 C5_6 C6_6 -178.6(3) . . . . ?
C9_6 C4_6 C5_6 C6_6 1.6(4) . . . . ?
C4_6 C5_6 C6_6 C7_6 -0.3(5) . . . . ?
C5_6 C6_6 C7_6 C8_6 -1.1(6) . . . . ?
C6_6 C7_6 C8_6 C9_6 1.1(6) . . . . ?
C7_6 C8_6 C9_6 C10_6 178.4(3) . . . . ?
C7_6 C8_6 C9_6 C4_6 0.3(5) . . . . ?
C3_6 C4_6 C9_6 C8_6 178.6(3) . . . . ?
C5_6 C4_6 C9_6 C8_6 -1.6(4) . . . . ?
C3_6 C4_6 C9_6 C10_6 0.4(4) . . . . ?
C5_6 C4_6 C9_6 C10_6 -179.8(2) . . . . ?
C2_6 C1_6 C10_6 C9_6 0.0(4) . . . . ?
C16 C1_6 C10_6 C9_6 179.7(2) . . . . ?
C8_6 C9_6 C10_6 C1_6 -178.8(3) . . . . ?
C4_6 C9_6 C10_6 C1_6 -0.6(4) . . . . ?

####################################################################### 
# 
# 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_Werz_MG528_a
_database_code_depnum_ccdc_archive 'CCDC 2473002'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2025-07-15 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V143 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_moiety         'C22 H20 O4'
_chemical_formula_weight         348.38
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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, -z'

_cell_length_a                   6.5073(13)
_cell_length_b                   7.6713(14)
_cell_length_c                   18.211(4)
_cell_angle_alpha                99.787(7)
_cell_angle_beta                 92.633(7)
_cell_angle_gamma                99.396(9)
_cell_volume                     881.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9802
_cell_measurement_theta_min      2.736
_cell_measurement_theta_max      28.153
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature by gas-phase diffusion of heptaneinto a solution of the compound dissolved in dichloromethane.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.661347
_exptl_absorpt_correction_T_max  0.745687
_exptl_absorpt_process_details   
;TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1: Krause, L., 
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            4419
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         28.407
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4419
_reflns_number_gt                3750
_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 BIS 8.5.5.6/2024-10-24 and APEX6 2024.9-1'
_computing_cell_refinement       'SAINT V8.41'
_computing_data_reduction        'SAINT V8.41'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.4251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4419
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_twin_special_details            
'The data was integrated as a 2-component twin.'
_twin_individual_id              2
_twin_individual_twin_matrix_11  -0.06067
_twin_individual_twin_matrix_12  0.00165
_twin_individual_twin_matrix_13  0.98597
_twin_individual_twin_matrix_21  1.00611
_twin_individual_twin_matrix_22  -0.00697
_twin_individual_twin_matrix_23  0.08388
_twin_individual_twin_matrix_31  0.04804
_twin_individual_twin_matrix_32  1.00254
_twin_individual_twin_matrix_33  -0.03542

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'

_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_
_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 1.03338(15) 0.66875(14) 0.58476(6) 0.0257(2) Uani 1 1 d . . . . .
H1 H 1.0947(19) 0.6305(19) 0.5438(11) 0.039 Uiso 1 1 calc R U . . .
O2 O 0.77696(16) 0.44326(14) 0.53325(6) 0.0279(2) Uani 1 1 d . . . . .
O3 O 0.45525(18) 0.05096(15) 0.59008(6) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.29941(18) 0.13243(16) 0.49250(6) 0.0337(3) Uani 1 1 d . . . . .
H4 H 0.389(3) 0.064(3) 0.4661(7) 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4518(2) 0.50650(18) 0.70283(7) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.6770(2) 0.46254(19) 0.69509(8) 0.0241(3) Uani 1 1 d . . . . .
H6A H 0.761105 0.481735 0.743370 0.029 Uiso 1 1 calc R U . . .
H6B H 0.680014 0.342093 0.665649 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7296(2) 0.61743(19) 0.65044(8) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.798485 0.732077 0.683271 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4918(2) 0.60999(19) 0.63594(8) 0.0231(3) Uani 1 1 d . . . . .
H8A H 0.433039 0.538697 0.586799 0.028 Uiso 1 1 calc R U . . .
H8B H 0.449244 0.729529 0.644034 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8477(2) 0.57041(19) 0.58343(8) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.4253(2) 0.63574(18) 0.77342(7) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.5768(2) 0.6900(2) 0.83286(8) 0.0285(3) Uani 1 1 d . . . . .
H11 H 0.705200 0.646246 0.830218 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5421(3) 0.8079(2) 0.89614(9) 0.0352(4) Uani 1 1 d . . . . .
H12 H 0.647063 0.844195 0.936320 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3563(3) 0.8727(2) 0.90111(9) 0.0351(4) Uani 1 1 d . . . . .
H13 H 0.332584 0.951205 0.944954 0.042 Uiso 1 1 calc R U . . .
C14 C 0.2044(3) 0.8226(2) 0.84188(9) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.077183 0.868156 0.844581 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2400(2) 0.70524(19) 0.77846(8) 0.0259(3) Uani 1 1 d . . . . .
H15 H 0.136225 0.671763 0.737820 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2803(2) 0.34588(18) 0.68718(8) 0.0234(3) Uani 1 1 d . . . . .
C17 C 0.1890(2) 0.23386(19) 0.61146(8) 0.0268(3) Uani 1 1 d . . . . .
H17 H 0.109282 0.302842 0.581894 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0428(2) 0.1188(2) 0.65841(9) 0.0307(3) Uani 1 1 d . . . . .
H18A H -0.107748 0.121604 0.649462 0.037 Uiso 1 1 calc R U . . .
H18B H 0.068716 -0.005618 0.655784 0.037 Uiso 1 1 calc R U . . .
C19 C 0.1493(2) 0.24954(19) 0.72669(8) 0.0258(3) Uani 1 1 d . . . . .
C20 C 0.3280(2) 0.13096(19) 0.56418(8) 0.0267(3) Uani 1 1 d . . . . .
C21 C 0.1077(2) 0.25905(19) 0.80573(9) 0.0276(3) Uani 1 1 d . . . . .
C22 C 0.2670(3) 0.3185(2) 0.86267(9) 0.0324(3) Uani 1 1 d . . . . .
H22 H 0.406972 0.349025 0.850296 0.039 Uiso 1 1 calc R U . . .
C23 C 0.2239(3) 0.3335(2) 0.93693(10) 0.0418(4) Uani 1 1 d . . . . .
H23 H 0.333919 0.375888 0.975089 0.050 Uiso 1 1 calc R U . . .
C24 C 0.0209(3) 0.2870(3) 0.95591(11) 0.0444(4) Uani 1 1 d . . . . .
H24 H -0.008547 0.298606 1.006952 0.053 Uiso 1 1 calc R U . . .
C25 C -0.1381(3) 0.2239(2) 0.90036(11) 0.0412(4) Uani 1 1 d . . . . .
H25 H -0.277188 0.191263 0.913284 0.049 Uiso 1 1 calc R U . . .
C26 C -0.0961(2) 0.2078(2) 0.82536(10) 0.0335(3) Uani 1 1 d . . . . .
H26 H -0.206056 0.161862 0.787437 0.040 Uiso 1 1 calc R U . . .


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 C9 1.3129(17) . ?
O1 H1 0.89(2) . ?
O2 C9 1.2288(17) . ?
O3 C20 1.2302(18) . ?
O4 C20 1.3122(18) . ?
O4 H4 0.94(2) . ?
C5 C16 1.4992(19) . ?
C5 C10 1.5194(18) . ?
C5 C6 1.5632(18) . ?
C5 C8 1.5724(19) . ?
C6 C7 1.5528(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.4957(18) . ?
C7 C8 1.5475(19) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.390(2) . ?
C10 C15 1.3962(19) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C19 1.350(2) . ?
C16 C17 1.5323(19) . ?
C17 C20 1.5021(19) . ?
C17 C18 1.572(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.517(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C21 1.469(2) . ?
C21 C22 1.394(2) . ?
C21 C26 1.401(2) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(2) . ?
C25 H25 0.9500 . ?
C26 H26 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
C9 O1 H1 109.5 . . ?
C20 O4 H4 109.5 . . ?
C16 C5 C10 112.40(11) . . ?
C16 C5 C6 114.72(11) . . ?
C10 C5 C6 115.05(11) . . ?
C16 C5 C8 115.10(11) . . ?
C10 C5 C8 110.50(11) . . ?
C6 C5 C8 86.68(9) . . ?
C7 C6 C5 89.73(10) . . ?
C7 C6 H6A 113.7 . . ?
C5 C6 H6A 113.7 . . ?
C7 C6 H6B 113.7 . . ?
C5 C6 H6B 113.7 . . ?
H6A C6 H6B 110.9 . . ?
C9 C7 C8 116.58(12) . . ?
C9 C7 C6 113.94(11) . . ?
C8 C7 C6 87.92(10) . . ?
C9 C7 H7 112.1 . . ?
C8 C7 H7 112.1 . . ?
C6 C7 H7 112.1 . . ?
C7 C8 C5 89.59(10) . . ?
C7 C8 H8A 113.7 . . ?
C5 C8 H8A 113.7 . . ?
C7 C8 H8B 113.7 . . ?
C5 C8 H8B 113.7 . . ?
H8A C8 H8B 111.0 . . ?
O2 C9 O1 123.58(12) . . ?
O2 C9 C7 121.37(12) . . ?
O1 C9 C7 114.96(12) . . ?
C11 C10 C15 118.31(13) . . ?
C11 C10 C5 123.40(12) . . ?
C15 C10 C5 118.28(12) . . ?
C10 C11 C12 120.52(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.61(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.79(14) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.49(14) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 121.27(14) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C19 C16 C5 137.48(13) . . ?
C19 C16 C17 94.00(12) . . ?
C5 C16 C17 128.50(12) . . ?
C20 C17 C16 118.60(12) . . ?
C20 C17 C18 114.52(12) . . ?
C16 C17 C18 85.40(11) . . ?
C20 C17 H17 111.9 . . ?
C16 C17 H17 111.9 . . ?
C18 C17 H17 111.9 . . ?
C19 C18 C17 86.22(11) . . ?
C19 C18 H18A 114.3 . . ?
C17 C18 H18A 114.3 . . ?
C19 C18 H18B 114.3 . . ?
C17 C18 H18B 114.3 . . ?
H18A C18 H18B 111.4 . . ?
C16 C19 C21 136.04(14) . . ?
C16 C19 C18 94.32(12) . . ?
C21 C19 C18 129.61(13) . . ?
O3 C20 O4 123.04(13) . . ?
O3 C20 C17 123.18(14) . . ?
O4 C20 C17 113.78(13) . . ?
C22 C21 C26 118.45(15) . . ?
C22 C21 C19 121.61(13) . . ?
C26 C21 C19 119.94(14) . . ?
C23 C22 C21 120.87(16) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.28(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.71(16) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.41(16) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.22(16) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?

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
C16 C5 C6 C7 134.55(12) . . . . ?
C10 C5 C6 C7 -92.74(12) . . . . ?
C8 C5 C6 C7 18.37(10) . . . . ?
C5 C6 C7 C9 -136.93(12) . . . . ?
C5 C6 C7 C8 -18.66(10) . . . . ?
C9 C7 C8 C5 134.38(12) . . . . ?
C6 C7 C8 C5 18.54(10) . . . . ?
C16 C5 C8 C7 -134.25(11) . . . . ?
C10 C5 C8 C7 97.11(12) . . . . ?
C6 C5 C8 C7 -18.44(10) . . . . ?
C8 C7 C9 O2 -42.07(19) . . . . ?
C6 C7 C9 O2 58.16(18) . . . . ?
C8 C7 C9 O1 141.16(13) . . . . ?
C6 C7 C9 O1 -118.61(13) . . . . ?
C16 C5 C10 C11 123.84(14) . . . . ?
C6 C5 C10 C11 -9.95(19) . . . . ?
C8 C5 C10 C11 -106.07(15) . . . . ?
C16 C5 C10 C15 -56.96(16) . . . . ?
C6 C5 C10 C15 169.25(12) . . . . ?
C8 C5 C10 C15 73.14(15) . . . . ?
C15 C10 C11 C12 1.2(2) . . . . ?
C5 C10 C11 C12 -179.58(14) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 C14 C15 C10 0.4(2) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
C5 C10 C15 C14 179.25(13) . . . . ?
C10 C5 C16 C19 -28.2(2) . . . . ?
C6 C5 C16 C19 105.74(19) . . . . ?
C8 C5 C16 C19 -155.91(16) . . . . ?
C10 C5 C16 C17 149.62(13) . . . . ?
C6 C5 C16 C17 -76.43(17) . . . . ?
C8 C5 C16 C17 21.93(19) . . . . ?
C19 C16 C17 C20 -117.35(14) . . . . ?
C5 C16 C17 C20 64.1(2) . . . . ?
C19 C16 C17 C18 -1.85(11) . . . . ?
C5 C16 C17 C18 179.61(14) . . . . ?
C20 C17 C18 C19 121.06(13) . . . . ?
C16 C17 C18 C19 1.65(10) . . . . ?
C5 C16 C19 C21 1.9(3) . . . . ?
C17 C16 C19 C21 -176.38(17) . . . . ?
C5 C16 C19 C18 -179.78(16) . . . . ?
C17 C16 C19 C18 1.92(12) . . . . ?
C17 C18 C19 C16 -1.87(11) . . . . ?
C17 C18 C19 C21 176.60(15) . . . . ?
C16 C17 C20 O3 40.0(2) . . . . ?
C18 C17 C20 O3 -58.6(2) . . . . ?
C16 C17 C20 O4 -140.81(14) . . . . ?
C18 C17 C20 O4 120.66(15) . . . . ?
C16 C19 C21 C22 -34.6(3) . . . . ?
C18 C19 C21 C22 147.56(16) . . . . ?
C16 C19 C21 C26 145.31(17) . . . . ?
C18 C19 C21 C26 -32.5(2) . . . . ?
C26 C21 C22 C23 -2.6(2) . . . . ?
C19 C21 C22 C23 177.36(15) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C24 C25 C26 C21 -1.3(3) . . . . ?
C22 C21 C26 C25 2.8(2) . . . . ?
C19 C21 C26 C25 -177.18(14) . . . . ?

####################################################################### 
# 
# 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_WerzMGBCannulated_a
_database_code_depnum_ccdc_archive 'CCDC 2476077'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2025-07-25 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V143 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C24 H24 O4'
_chemical_formula_moiety         'C24 H24 O4'
_chemical_formula_weight         376.43
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3477(18)
_cell_length_b                   14.523(3)
_cell_length_c                   15.319(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1857.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9695
_cell_measurement_theta_min      2.779
_cell_measurement_theta_max      36.024
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature by gas-phase diffusion of n-heptaneinto a solution of the compound dissolved in chloroform.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            193462
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         40.345
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11588
_reflns_number_gt                10136
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.996
_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 BIS 8.5.5.6/2024-10-24 and APEX6 2024.9-1'
_computing_cell_refinement       'SAINT V8.41'
_computing_data_reduction        'SAINT V8.41'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.1527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         11588
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_abs_structure_details 
;
 Flack x determined using 4092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_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 0.29313(10) 0.85192(6) -0.01286(6) 0.02431(15) Uani 1 1 d . . . . .
O2 O 0.03243(10) 0.89019(5) -0.01753(5) 0.01850(13) Uani 1 1 d . . . . .
O3 O 0.43829(11) 0.91818(5) 0.22653(6) 0.02362(16) Uani 1 1 d . . . . .
O4 O 0.56895(9) 0.79379(5) 0.17518(5) 0.01795(13) Uani 1 1 d . . . . .
C1 C 0.19744(11) 0.74218(6) 0.21586(6) 0.01384(13) Uani 1 1 d . . . . .
C2 C 0.22830(11) 0.70884(6) 0.12002(6) 0.01578(14) Uani 1 1 d . . . . .
H2A H 0.338881 0.720371 0.099381 0.019 Uiso 1 1 calc R U . . .
H2B H 0.196981 0.643998 0.109691 0.019 Uiso 1 1 calc R U . . .
C3 C 0.10528(11) 0.77921(6) 0.08573(6) 0.01488(14) Uani 1 1 d . . . . .
H3 H 0.001013 0.748801 0.071513 0.018 Uiso 1 1 calc R U . . .
C4 C 0.10021(12) 0.82494(6) 0.17784(6) 0.01542(14) Uani 1 1 d . . . . .
H4A H -0.009162 0.830568 0.202244 0.019 Uiso 1 1 calc R U . . .
H4B H 0.157753 0.884459 0.180926 0.019 Uiso 1 1 calc R U . . .
C5 C 0.09279(11) 0.67732(6) 0.26895(6) 0.01445(14) Uani 1 1 d . . . . .
C6 C -0.05376(12) 0.64532(7) 0.23720(6) 0.01652(14) Uani 1 1 d . . . . .
H6 H -0.087319 0.661900 0.180066 0.020 Uiso 1 1 calc R U . . .
C7 C -0.15142(12) 0.58925(7) 0.28854(7) 0.01753(15) Uani 1 1 d . . . . .
H7 H -0.250945 0.567819 0.266379 0.021 Uiso 1 1 calc R U . . .
C8 C -0.10292(12) 0.56483(7) 0.37209(7) 0.01776(15) Uani 1 1 d . . . . .
H8 H -0.170289 0.527815 0.407685 0.021 Uiso 1 1 calc R U . . .
C9 C 0.04472(12) 0.59470(6) 0.40363(6) 0.01690(15) Uani 1 1 d . . . . .
H9 H 0.078780 0.576647 0.460268 0.020 Uiso 1 1 calc R U . . .
C10 C 0.14292(11) 0.65083(6) 0.35282(6) 0.01419(13) Uani 1 1 d . . . . .
C11 C 0.30348(11) 0.68792(6) 0.38378(6) 0.01436(13) Uani 1 1 d . . . . .
C12 C 0.42445(11) 0.67773(6) 0.30670(6) 0.01528(14) Uani 1 1 d . . . . .
H12A H 0.538256 0.684077 0.323849 0.018 Uiso 1 1 calc R U . . .
H12B H 0.407202 0.622430 0.270100 0.018 Uiso 1 1 calc R U . . .
C13 C 0.34847(11) 0.76717(6) 0.26952(6) 0.01444(14) Uani 1 1 d . . . . .
C14 C 0.30247(12) 0.79364(6) 0.36454(6) 0.01559(14) Uani 1 1 d . . . . .
H14A H 0.195974 0.823028 0.370254 0.019 Uiso 1 1 calc R U . . .
H14B H 0.385873 0.828860 0.396094 0.019 Uiso 1 1 calc R U . . .
C15 C 0.15726(12) 0.84239(6) 0.01359(6) 0.01571(14) Uani 1 1 d . . . . .
C16 C 0.06612(16) 0.95130(8) -0.08956(7) 0.02366(19) Uani 1 1 d . . . . .
H16A H 0.103897 0.915341 -0.139624 0.035 Uiso 1 1 calc R U . . .
H16B H 0.148993 0.995475 -0.072258 0.035 Uiso 1 1 calc R U . . .
H16C H -0.031645 0.984557 -0.105677 0.035 Uiso 1 1 calc R U . . .
C17 C 0.45400(11) 0.83523(6) 0.22252(6) 0.01626(14) Uani 1 1 d . . . . .
C18 C 0.66341(13) 0.85516(8) 0.12139(8) 0.02195(18) Uani 1 1 d . . . . .
H18A H 0.752179 0.820849 0.095041 0.033 Uiso 1 1 calc R U . . .
H18B H 0.706227 0.905135 0.157503 0.033 Uiso 1 1 calc R U . . .
H18C H 0.595789 0.881058 0.075221 0.033 Uiso 1 1 calc R U . . .
C19 C 0.34898(11) 0.65349(6) 0.47256(6) 0.01507(14) Uani 1 1 d . . . . .
C20 C 0.44159(12) 0.57376(6) 0.48130(6) 0.01702(15) Uani 1 1 d . . . . .
H20 H 0.488053 0.546281 0.431046 0.020 Uiso 1 1 calc R U . . .
C21 C 0.46628(13) 0.53427(7) 0.56315(7) 0.01893(16) Uani 1 1 d . . . . .
H21 H 0.528640 0.479824 0.568327 0.023 Uiso 1 1 calc R U . . .
C22 C 0.39982(13) 0.57441(7) 0.63733(7) 0.01942(16) Uani 1 1 d . . . . .
H22 H 0.413852 0.546439 0.692865 0.023 Uiso 1 1 calc R U . . .
C23 C 0.31262(13) 0.65582(7) 0.62966(6) 0.01964(16) Uani 1 1 d . . . . .
H23 H 0.270168 0.684577 0.680326 0.024 Uiso 1 1 calc R U . . .
C24 C 0.28748(13) 0.69523(7) 0.54763(6) 0.01788(15) Uani 1 1 d . . . . .
H24 H 0.228144 0.750819 0.542823 0.021 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.2123(13) . ?
O2 C15 1.3399(12) . ?
O2 C16 1.4436(13) . ?
O3 C17 1.2133(12) . ?
O4 C17 1.3449(12) . ?
O4 C18 1.4475(13) . ?
C1 C5 1.5205(13) . ?
C1 C13 1.5482(13) . ?
C1 C4 1.5629(13) . ?
C1 C2 1.5673(13) . ?
C2 C3 1.5412(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C15 1.5004(13) . ?
C3 C4 1.5601(13) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.3961(13) . ?
C5 C10 1.4050(13) . ?
C6 C7 1.3951(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.3885(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.3930(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.3936(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.5203(13) . ?
C11 C19 1.4980(13) . ?
C11 C12 1.5608(13) . ?
C11 C14 1.5634(13) . ?
C12 C13 1.5536(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.5071(13) . ?
C13 C14 1.5537(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.3978(13) . ?
C19 C20 1.3986(13) . ?
C20 C21 1.3940(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.3925(15) . ?
C21 H21 0.9500 . ?
C22 C23 1.3934(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.3967(14) . ?
C23 H23 0.9500 . ?
C24 H24 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
C15 O2 C16 116.04(9) . . ?
C17 O4 C18 114.84(8) . . ?
C5 C1 C13 109.22(7) . . ?
C5 C1 C4 112.17(8) . . ?
C13 C1 C4 116.14(7) . . ?
C5 C1 C2 113.83(7) . . ?
C13 C1 C2 115.84(8) . . ?
C4 C1 C2 88.50(7) . . ?
C3 C2 C1 90.28(7) . . ?
C3 C2 H2A 113.6 . . ?
C1 C2 H2A 113.6 . . ?
C3 C2 H2B 113.6 . . ?
C1 C2 H2B 113.6 . . ?
H2A C2 H2B 110.9 . . ?
C15 C3 C2 117.64(8) . . ?
C15 C3 C4 114.44(8) . . ?
C2 C3 C4 89.54(7) . . ?
C15 C3 H3 111.2 . . ?
C2 C3 H3 111.2 . . ?
C4 C3 H3 111.2 . . ?
C3 C4 C1 89.75(7) . . ?
C3 C4 H4A 113.7 . . ?
C1 C4 H4A 113.7 . . ?
C3 C4 H4B 113.7 . . ?
C1 C4 H4B 113.7 . . ?
H4A C4 H4B 110.9 . . ?
C6 C5 C10 119.24(8) . . ?
C6 C5 C1 121.56(8) . . ?
C10 C5 C1 119.18(8) . . ?
C7 C6 C5 120.65(9) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.90(9) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 119.87(9) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.59(9) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 119.72(9) . . ?
C9 C10 C11 123.47(8) . . ?
C5 C10 C11 116.80(8) . . ?
C19 C11 C10 112.86(8) . . ?
C19 C11 C12 119.42(8) . . ?
C10 C11 C12 107.51(8) . . ?
C19 C11 C14 120.03(8) . . ?
C10 C11 C14 106.52(7) . . ?
C12 C11 C14 87.36(7) . . ?
C13 C12 C11 86.22(7) . . ?
C13 C12 H12A 114.3 . . ?
C11 C12 H12A 114.3 . . ?
C13 C12 H12B 114.3 . . ?
C11 C12 H12B 114.3 . . ?
H12A C12 H12B 111.4 . . ?
C17 C13 C1 112.09(8) . . ?
C17 C13 C12 119.00(8) . . ?
C1 C13 C12 109.34(7) . . ?
C17 C13 C14 115.45(8) . . ?
C1 C13 C14 110.74(8) . . ?
C12 C13 C14 87.95(7) . . ?
C13 C14 C11 86.12(7) . . ?
C13 C14 H14A 114.3 . . ?
C11 C14 H14A 114.3 . . ?
C13 C14 H14B 114.3 . . ?
C11 C14 H14B 114.3 . . ?
H14A C14 H14B 111.4 . . ?
O1 C15 O2 123.33(9) . . ?
O1 C15 C3 125.91(9) . . ?
O2 C15 C3 110.73(8) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 123.27(9) . . ?
O3 C17 C13 124.32(9) . . ?
O4 C17 C13 112.41(8) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.90(9) . . ?
C24 C19 C11 120.60(8) . . ?
C20 C19 C11 120.23(8) . . ?
C21 C20 C19 120.56(9) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.19(9) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.63(9) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 120.14(9) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.49(9) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 103.16(8) . . . . ?
C13 C1 C2 C3 -128.97(8) . . . . ?
C4 C1 C2 C3 -10.49(7) . . . . ?
C1 C2 C3 C15 128.07(8) . . . . ?
C1 C2 C3 C4 10.50(7) . . . . ?
C15 C3 C4 C1 -130.92(8) . . . . ?
C2 C3 C4 C1 -10.53(7) . . . . ?
C5 C1 C4 C3 -104.84(8) . . . . ?
C13 C1 C4 C3 128.58(8) . . . . ?
C2 C1 C4 C3 10.36(7) . . . . ?
C13 C1 C5 C6 178.38(8) . . . . ?
C4 C1 C5 C6 48.15(11) . . . . ?
C2 C1 C5 C6 -50.43(12) . . . . ?
C13 C1 C5 C10 0.01(11) . . . . ?
C4 C1 C5 C10 -130.21(9) . . . . ?
C2 C1 C5 C10 131.21(9) . . . . ?
C10 C5 C6 C7 1.34(14) . . . . ?
C1 C5 C6 C7 -177.03(9) . . . . ?
C5 C6 C7 C8 0.00(15) . . . . ?
C6 C7 C8 C9 -1.44(15) . . . . ?
C7 C8 C9 C10 1.54(15) . . . . ?
C8 C9 C10 C5 -0.19(14) . . . . ?
C8 C9 C10 C11 178.45(9) . . . . ?
C6 C5 C10 C9 -1.23(13) . . . . ?
C1 C5 C10 C9 177.17(8) . . . . ?
C6 C5 C10 C11 -179.96(8) . . . . ?
C1 C5 C10 C11 -1.56(12) . . . . ?
C9 C10 C11 C19 3.21(12) . . . . ?
C5 C10 C11 C19 -178.11(8) . . . . ?
C9 C10 C11 C12 136.99(9) . . . . ?
C5 C10 C11 C12 -44.33(10) . . . . ?
C9 C10 C11 C14 -130.54(9) . . . . ?
C5 C10 C11 C14 48.14(10) . . . . ?
C19 C11 C12 C13 -149.36(8) . . . . ?
C10 C11 C12 C13 80.43(8) . . . . ?
C14 C11 C12 C13 -26.06(7) . . . . ?
C5 C1 C13 C17 -177.15(7) . . . . ?
C4 C1 C13 C17 -49.11(10) . . . . ?
C2 C1 C13 C17 52.74(10) . . . . ?
C5 C1 C13 C12 48.67(9) . . . . ?
C4 C1 C13 C12 176.71(7) . . . . ?
C2 C1 C13 C12 -81.45(9) . . . . ?
C5 C1 C13 C14 -46.64(9) . . . . ?
C4 C1 C13 C14 81.41(9) . . . . ?
C2 C1 C13 C14 -176.75(7) . . . . ?
C11 C12 C13 C17 144.39(8) . . . . ?
C11 C12 C13 C1 -85.06(8) . . . . ?
C11 C12 C13 C14 26.23(7) . . . . ?
C17 C13 C14 C11 -147.54(8) . . . . ?
C1 C13 C14 C11 83.74(8) . . . . ?
C12 C13 C14 C11 -26.18(7) . . . . ?
C19 C11 C14 C13 148.83(9) . . . . ?
C10 C11 C14 C13 -81.42(8) . . . . ?
C12 C11 C14 C13 26.06(7) . . . . ?
C16 O2 C15 O1 3.67(14) . . . . ?
C16 O2 C15 C3 -177.91(8) . . . . ?
C2 C3 C15 O1 -10.35(15) . . . . ?
C4 C3 C15 O1 92.83(12) . . . . ?
C2 C3 C15 O2 171.28(8) . . . . ?
C4 C3 C15 O2 -85.54(10) . . . . ?
C18 O4 C17 O3 -6.27(15) . . . . ?
C18 O4 C17 C13 173.82(8) . . . . ?
C1 C13 C17 O3 86.98(12) . . . . ?
C12 C13 C17 O3 -143.71(10) . . . . ?
C14 C13 C17 O3 -41.08(14) . . . . ?
C1 C13 C17 O4 -93.11(9) . . . . ?
C12 C13 C17 O4 36.20(12) . . . . ?
C14 C13 C17 O4 138.83(8) . . . . ?
C10 C11 C19 C24 -81.93(11) . . . . ?
C12 C11 C19 C24 150.29(9) . . . . ?
C14 C11 C19 C24 44.94(13) . . . . ?
C10 C11 C19 C20 92.04(11) . . . . ?
C12 C11 C19 C20 -35.74(13) . . . . ?
C14 C11 C19 C20 -141.09(9) . . . . ?
C24 C19 C20 C21 2.80(15) . . . . ?
C11 C19 C20 C21 -171.27(9) . . . . ?
C19 C20 C21 C22 -0.53(15) . . . . ?
C20 C21 C22 C23 -1.97(16) . . . . ?
C21 C22 C23 C24 2.15(16) . . . . ?
C22 C23 C24 C19 0.15(16) . . . . ?
C20 C19 C24 C23 -2.61(15) . . . . ?
C11 C19 C24 C23 171.44(10) . . . . ?

####################################################################### 
# 
# 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_Werz_MG537
_database_code_depnum_ccdc_archive 'CCDC 2476959'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2025-07-29 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V143 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C23 H20 Br2 O4'
_chemical_formula_moiety         'C23 H20 Br2 O4'
_chemical_formula_weight         520.21
_chemical_melting_point          ?
_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                   20.433(5)
_cell_length_b                   9.030(2)
_cell_length_c                   11.857(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.600(14)
_cell_angle_gamma                90
_cell_volume                     2096.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9618
_cell_measurement_theta_min      2.484
_cell_measurement_theta_max      30.5545
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature by gas-phase diffusion of n-hexaneinto a solution of the compound dissolved in dichloromethane.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    3.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.331
_shelx_estimated_absorpt_T_max   0.582
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            258244
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_theta_min         1.792
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5185
_reflns_number_gt                5117
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
'Bruker BIS 8.5.5.6/2024-10-24 and APEX6 2024.9-1'
_computing_cell_refinement       'SAINT V8.41'
_computing_data_reduction        'SAINT V8.41'
_computing_structure_solution    'SHELXD (G. Sheldrick)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+9.5843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5185
_refine_ls_number_parameters     323
_refine_ls_number_restraints     315
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.016
_refine_diff_density_min         -1.388
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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
Br1 Br 1.02155(3) 0.05401(6) 0.22138(5) 0.03933(13) Uani 1 1 d . . . . .
Br2 Br 0.49808(3) -0.36411(6) 0.69184(5) 0.04490(14) Uani 1 1 d . . . . .
O1 O 0.78624(19) -0.1704(4) 0.7536(3) 0.0415(9) Uani 1 1 d . . . . .
O2 O 0.8165(2) 0.0420(4) 0.8499(3) 0.0406(9) Uani 1 1 d . . . . .
C1 C 0.7652(2) 0.0604(4) 0.6458(4) 0.0256(8) Uani 1 1 d . . . . .
C2 C 0.7677(2) -0.0208(5) 0.5314(4) 0.0271(9) Uani 1 1 d . . . . .
H2A H 0.779197 -0.127320 0.542545 0.033 Uiso 1 1 calc R U . . .
H2B H 0.726662 -0.005049 0.463866 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8261(2) 0.0748(4) 0.5300(4) 0.0259(8) Uani 1 1 d . . . . .
C4 C 0.8238(2) 0.1566(5) 0.6284(4) 0.0290(9) Uani 1 1 d . . . . .
H4 H 0.848546 0.239164 0.668829 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7899(2) -0.0374(5) 0.7532(4) 0.0296(9) Uani 1 1 d . . . . .
C6 C 0.8431(4) -0.0428(7) 0.9569(5) 0.0585(19) Uani 1 1 d . . . . .
H6A H 0.805275 -0.090484 0.978331 0.088 Uiso 1 1 calc R U . . .
H6B H 0.867490 0.023425 1.020577 0.088 Uiso 1 1 calc R U . . .
H6C H 0.874586 -0.118643 0.944232 0.088 Uiso 1 1 calc R U . . .
C7 C 0.8720(2) 0.0735(4) 0.4561(4) 0.0258(8) Uani 1 1 d . . . . .
C8 C 0.8619(2) -0.0287(5) 0.3641(4) 0.0278(8) Uani 1 1 d . . . . .
H8 H 0.824237 -0.094730 0.349429 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9057(2) -0.0357(5) 0.2938(4) 0.0303(9) Uani 1 1 d . . . . .
H9 H 0.898510 -0.106278 0.231969 0.036 Uiso 1 1 calc R U . . .
C10 C 0.9603(2) 0.0622(5) 0.3153(4) 0.0285(9) Uani 1 1 d . . . . .
C11 C 0.9720(2) 0.1648(5) 0.4065(4) 0.0330(10) Uani 1 1 d . . . . .
H11 H 1.009863 0.230279 0.420897 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9282(2) 0.1707(5) 0.4759(4) 0.0303(9) Uani 1 1 d . . . . .
H12 H 0.935962 0.241232 0.537776 0.036 Uiso 1 1 calc R U . . .
C13 C 0.6967(2) 0.1366(4) 0.6435(4) 0.0241(7) Uani 0.898(8) 1 d D U P A 1
C14 C 0.6697(3) 0.2485(5) 0.5406(4) 0.0244(11) Uani 0.898(8) 1 d D U P A 1
H14A H 0.704150 0.276563 0.500411 0.029 Uiso 0.898(8) 1 calc R U P A 1
H14B H 0.626499 0.217233 0.483035 0.029 Uiso 0.898(8) 1 calc R U P A 1
C15 C 0.6599(3) 0.3648(5) 0.6285(4) 0.0258(9) Uani 0.898(8) 1 d D U P A 1
H15 H 0.611212 0.369794 0.629733 0.031 Uiso 0.898(8) 1 calc R U P A 1
C16 C 0.7040(4) 0.2676(5) 0.7325(5) 0.0306(15) Uani 0.898(8) 1 d D U P A 1
H16A H 0.751450 0.303136 0.765454 0.037 Uiso 0.898(8) 1 calc R U P A 1
H16B H 0.682051 0.249037 0.795612 0.037 Uiso 0.898(8) 1 calc R U P A 1
C17 C 0.6886(4) 0.5170(6) 0.6217(5) 0.0278(10) Uani 0.898(8) 1 d D U P A 1
O3 O 0.7065(4) 0.5644(6) 0.5412(4) 0.0657(18) Uani 0.898(8) 1 d D U P A 1
O4 O 0.6934(3) 0.5951(5) 0.7185(4) 0.0311(10) Uani 0.898(8) 1 d D U P A 1
H4A H 0.710(4) 0.667(8) 0.715(3) 0.047 Uiso 0.898(8) 1 calc DR U P A 1
C13A C 0.6967(2) 0.1366(4) 0.6435(4) 0.0241(7) Uani 0.102(8) 1 d D U P A 2
C14A C 0.688(3) 0.262(3) 0.549(2) 0.024(4) Uani 0.102(8) 1 d D U P A 2
H14C H 0.716475 0.248304 0.494839 0.029 Uiso 0.102(8) 1 calc R U P A 2
H14D H 0.640271 0.284674 0.506125 0.029 Uiso 0.102(8) 1 calc R U P A 2
C15A C 0.7196(18) 0.370(2) 0.652(3) 0.027(3) Uani 0.102(8) 1 d D U P A 2
H15A H 0.770654 0.369295 0.675565 0.033 Uiso 0.102(8) 1 calc R U P A 2
C16A C 0.689(4) 0.264(3) 0.730(4) 0.026(4) Uani 0.102(8) 1 d D U P A 2
H16C H 0.718350 0.251559 0.811450 0.032 Uiso 0.102(8) 1 calc R U P A 2
H16D H 0.641246 0.286067 0.727321 0.032 Uiso 0.102(8) 1 calc R U P A 2
C17A C 0.691(4) 0.524(3) 0.642(3) 0.031(5) Uani 0.102(8) 1 d D U P A 2
O3A O 0.665(2) 0.586(3) 0.552(3) 0.035(6) Uani 0.102(8) 1 d D U P A 2
O4A O 0.683(3) 0.569(5) 0.744(3) 0.041(8) Uani 0.102(8) 1 d D U P A 2
H4AA H 0.66(3) 0.52(5) 0.76(3) 0.061 Uiso 0.102(8) 1 calc DR U P A 2
C18 C 0.6451(2) 0.0190(5) 0.6532(4) 0.0242(8) Uani 1 1 d . . . . .
C19 C 0.6014(2) -0.0471(5) 0.5540(4) 0.0267(8) Uani 1 1 d . . . . .
H19 H 0.601900 -0.014888 0.478008 0.032 Uiso 1 1 calc R U . . .
C20 C 0.5568(2) -0.1596(5) 0.5642(5) 0.0320(9) Uani 1 1 d . . . . .
H20 H 0.526712 -0.203098 0.495973 0.038 Uiso 1 1 calc R U . . .
C21 C 0.5571(2) -0.2070(5) 0.6751(4) 0.0293(9) Uani 1 1 d . . . . .
C22 C 0.6000(2) -0.1454(5) 0.7755(4) 0.0289(9) Uani 1 1 d . . . . .
H22 H 0.599818 -0.179796 0.851146 0.035 Uiso 1 1 calc R U . . .
C23 C 0.6434(2) -0.0323(4) 0.7637(4) 0.0271(8) Uani 1 1 d . . . . .
H23 H 0.672702 0.011581 0.832528 0.033 Uiso 1 1 calc R U . . .


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
Br1 C10 1.900(5) . ?
Br2 C21 1.909(4) . ?
O1 C5 1.203(5) . ?
O2 C5 1.330(6) . ?
O2 C6 1.449(6) . ?
C1 C5 1.513(6) . ?
C1 C4 1.539(6) . ?
C1 C13A 1.554(6) . ?
C1 C13 1.554(6) . ?
C1 C2 1.555(6) . ?
C2 C3 1.478(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.393(7) . ?
C3 C7 1.455(6) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.398(6) . ?
C7 C12 1.411(6) . ?
C8 C9 1.389(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(7) . ?
C11 C12 1.378(7) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.523(6) . ?
C13 C14 1.559(6) . ?
C13 C16 1.563(6) . ?
C14 C15 1.532(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.505(8) . ?
C15 C16 1.571(8) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O3 1.195(8) . ?
C17 O4 1.326(6) . ?
O4 H4A 0.74(7) . ?
C13A C18 1.523(6) . ?
C13A C14A 1.567(19) . ?
C13A C16A 1.573(19) . ?
C14A C15A 1.54(2) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C15A C17A 1.506(19) . ?
C15A C16A 1.58(2) . ?
C15A H15A 1.0000 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A O3A 1.19(2) . ?
C17A O4A 1.327(19) . ?
O4A H4AA 0.74(7) . ?
C18 C19 1.393(6) . ?
C18 C23 1.401(6) . ?
C19 C20 1.392(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(6) . ?
C22 C23 1.385(6) . ?
C22 H22 0.9500 . ?
C23 H23 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
C5 O2 C6 115.4(4) . . ?
C5 C1 C4 111.0(3) . . ?
C5 C1 C13A 110.8(4) . . ?
C4 C1 C13A 118.6(3) . . ?
C5 C1 C13 110.8(4) . . ?
C4 C1 C13 118.6(3) . . ?
C5 C1 C2 111.9(3) . . ?
C4 C1 C2 86.0(3) . . ?
C13A C1 C2 116.5(3) . . ?
C13 C1 C2 116.5(3) . . ?
C3 C2 C1 87.8(3) . . ?
C3 C2 H2A 114.0 . . ?
C1 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
C1 C2 H2B 114.0 . . ?
H2A C2 H2B 111.2 . . ?
C4 C3 C7 133.7(4) . . ?
C4 C3 C2 94.6(4) . . ?
C7 C3 C2 131.6(4) . . ?
C3 C4 C1 91.5(3) . . ?
C3 C4 H4 134.2 . . ?
C1 C4 H4 134.2 . . ?
O1 C5 O2 123.1(4) . . ?
O1 C5 C1 125.4(4) . . ?
O2 C5 C1 111.5(4) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 118.2(4) . . ?
C8 C7 C3 119.9(4) . . ?
C12 C7 C3 121.9(4) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.2(4) . . ?
C9 C10 Br1 119.7(4) . . ?
C11 C10 Br1 119.1(3) . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 120.9(4) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C1 109.2(3) . . ?
C18 C13 C14 114.4(4) . . ?
C1 C13 C14 114.6(4) . . ?
C18 C13 C16 114.3(4) . . ?
C1 C13 C16 114.3(4) . . ?
C14 C13 C16 89.0(3) . . ?
C15 C14 C13 89.9(3) . . ?
C15 C14 H14A 113.7 . . ?
C13 C14 H14A 113.7 . . ?
C15 C14 H14B 113.7 . . ?
C13 C14 H14B 113.7 . . ?
H14A C14 H14B 110.9 . . ?
C17 C15 C14 117.4(4) . . ?
C17 C15 C16 114.1(4) . . ?
C14 C15 C16 89.6(3) . . ?
C17 C15 H15 111.3 . . ?
C14 C15 H15 111.3 . . ?
C16 C15 H15 111.3 . . ?
C13 C16 C15 88.3(4) . . ?
C13 C16 H16A 113.9 . . ?
C15 C16 H16A 113.9 . . ?
C13 C16 H16B 113.9 . . ?
C15 C16 H16B 113.9 . . ?
H16A C16 H16B 111.1 . . ?
O3 C17 O4 122.5(6) . . ?
O3 C17 C15 125.6(5) . . ?
O4 C17 C15 111.9(5) . . ?
C17 O4 H4A 109.5 . . ?
C18 C13A C1 109.2(3) . . ?
C18 C13A C14A 128.5(19) . . ?
C1 C13A C14A 104(2) . . ?
C18 C13A C16A 105.1(19) . . ?
C1 C13A C16A 125(3) . . ?
C14A C13A C16A 85.5(15) . . ?
C15A C14A C13A 87.8(14) . . ?
C15A C14A H14C 114.0 . . ?
C13A C14A H14C 114.0 . . ?
C15A C14A H14D 114.0 . . ?
C13A C14A H14D 114.0 . . ?
H14C C14A H14D 111.2 . . ?
C17A C15A C14A 117(3) . . ?
C17A C15A C16A 113(3) . . ?
C14A C15A C16A 86.1(17) . . ?
C17A C15A H15A 112.6 . . ?
C14A C15A H15A 112.6 . . ?
C16A C15A H15A 112.6 . . ?
C13A C16A C15A 86.2(14) . . ?
C13A C16A H16C 114.3 . . ?
C15A C16A H16C 114.3 . . ?
C13A C16A H16D 114.3 . . ?
C15A C16A H16D 114.3 . . ?
H16C C16A H16D 111.4 . . ?
O3A C17A O4A 123(3) . . ?
O3A C17A C15A 124(2) . . ?
O4A C17A C15A 111(2) . . ?
C17A O4A H4AA 109.5 . . ?
C19 C18 C23 117.8(4) . . ?
C19 C18 C13A 121.8(4) . . ?
C23 C18 C13A 120.3(4) . . ?
C19 C18 C13 121.8(4) . . ?
C23 C18 C13 120.3(4) . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 118.9(4) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 121.7(4) . . ?
C22 C21 Br2 118.3(3) . . ?
C20 C21 Br2 119.9(3) . . ?
C21 C22 C23 118.5(4) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 C18 121.8(4) . . ?
C22 C23 H23 119.1 . . ?
C18 C23 H23 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
C5 C1 C2 C3 -108.2(4) . . . . ?
C4 C1 C2 C3 2.8(3) . . . . ?
C13A C1 C2 C3 122.9(4) . . . . ?
C13 C1 C2 C3 122.9(4) . . . . ?
C1 C2 C3 C4 -3.1(3) . . . . ?
C1 C2 C3 C7 172.8(5) . . . . ?
C7 C3 C4 C1 -172.7(5) . . . . ?
C2 C3 C4 C1 3.1(3) . . . . ?
C5 C1 C4 C3 108.9(4) . . . . ?
C13A C1 C4 C3 -121.1(4) . . . . ?
C13 C1 C4 C3 -121.1(4) . . . . ?
C2 C1 C4 C3 -3.0(3) . . . . ?
C6 O2 C5 O1 1.7(8) . . . . ?
C6 O2 C5 C1 -178.5(5) . . . . ?
C4 C1 C5 O1 -122.4(5) . . . . ?
C13A C1 C5 O1 103.7(6) . . . . ?
C13 C1 C5 O1 103.7(6) . . . . ?
C2 C1 C5 O1 -28.2(7) . . . . ?
C4 C1 C5 O2 57.8(5) . . . . ?
C13A C1 C5 O2 -76.1(5) . . . . ?
C13 C1 C5 O2 -76.1(5) . . . . ?
C2 C1 C5 O2 152.0(4) . . . . ?
C4 C3 C7 C8 177.4(5) . . . . ?
C2 C3 C7 C8 2.9(7) . . . . ?
C4 C3 C7 C12 -1.1(7) . . . . ?
C2 C3 C7 C12 -175.5(4) . . . . ?
C12 C7 C8 C9 0.2(6) . . . . ?
C3 C7 C8 C9 -178.3(4) . . . . ?
C7 C8 C9 C10 -0.6(7) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 Br1 179.5(3) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
Br1 C10 C11 C12 -179.4(3) . . . . ?
C10 C11 C12 C7 0.4(7) . . . . ?
C8 C7 C12 C11 -0.2(6) . . . . ?
C3 C7 C12 C11 178.3(4) . . . . ?
C5 C1 C13 C18 -54.2(4) . . . . ?
C4 C1 C13 C18 175.8(4) . . . . ?
C2 C1 C13 C18 75.2(4) . . . . ?
C5 C1 C13 C14 175.9(4) . . . . ?
C4 C1 C13 C14 45.9(5) . . . . ?
C2 C1 C13 C14 -54.6(5) . . . . ?
C5 C1 C13 C16 75.2(4) . . . . ?
C4 C1 C13 C16 -54.8(5) . . . . ?
C2 C1 C13 C16 -155.3(4) . . . . ?
C18 C13 C14 C15 102.7(4) . . . . ?
C1 C13 C14 C15 -130.0(4) . . . . ?
C16 C13 C14 C15 -13.6(4) . . . . ?
C13 C14 C15 C17 130.7(5) . . . . ?
C13 C14 C15 C16 13.6(4) . . . . ?
C18 C13 C16 C15 -103.1(4) . . . . ?
C1 C13 C16 C15 130.0(4) . . . . ?
C14 C13 C16 C15 13.3(4) . . . . ?
C17 C15 C16 C13 -133.7(5) . . . . ?
C14 C15 C16 C13 -13.5(4) . . . . ?
C14 C15 C17 O3 15.3(11) . . . . ?
C16 C15 C17 O3 118.2(9) . . . . ?
C14 C15 C17 O4 -163.4(5) . . . . ?
C16 C15 C17 O4 -60.4(7) . . . . ?
C5 C1 C13A C18 -54.2(4) . . . . ?
C4 C1 C13A C18 175.8(4) . . . . ?
C2 C1 C13A C18 75.2(4) . . . . ?
C5 C1 C13A C14A 165.5(12) . . . . ?
C4 C1 C13A C14A 35.5(13) . . . . ?
C2 C1 C13A C14A -65.0(13) . . . . ?
C5 C1 C13A C16A 71.0(14) . . . . ?
C4 C1 C13A C16A -59.0(14) . . . . ?
C2 C1 C13A C16A -159.6(14) . . . . ?
C18 C13A C14A C15A 134.1(18) . . . . ?
C1 C13A C14A C15A -96(2) . . . . ?
C16A C13A C14A C15A 28(3) . . . . ?
C13A C14A C15A C17A -142(3) . . . . ?
C13A C14A C15A C16A -28(3) . . . . ?
C18 C13A C16A C15A -156(2) . . . . ?
C1 C13A C16A C15A 77(3) . . . . ?
C14A C13A C16A C15A -28(3) . . . . ?
C17A C15A C16A C13A 146(3) . . . . ?
C14A C15A C16A C13A 28(3) . . . . ?
C14A C15A C17A O3A -28(8) . . . . ?
C16A C15A C17A O3A -126(7) . . . . ?
C14A C15A C17A O4A 137(6) . . . . ?
C16A C15A C17A O4A 40(7) . . . . ?
C1 C13A C18 C19 -90.7(5) . . . . ?
C14A C13A C18 C19 37(2) . . . . ?
C16A C13A C18 C19 134(3) . . . . ?
C1 C13A C18 C23 85.4(5) . . . . ?
C14A C13A C18 C23 -146.8(19) . . . . ?
C16A C13A C18 C23 -50(3) . . . . ?
C1 C13 C18 C19 -90.7(5) . . . . ?
C14 C13 C18 C19 39.3(5) . . . . ?
C16 C13 C18 C19 139.9(5) . . . . ?
C1 C13 C18 C23 85.4(5) . . . . ?
C14 C13 C18 C23 -144.6(4) . . . . ?
C16 C13 C18 C23 -44.0(6) . . . . ?
C23 C18 C19 C20 0.6(6) . . . . ?
C13A C18 C19 C20 176.8(4) . . . . ?
C13 C18 C19 C20 176.8(4) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C19 C20 C21 Br2 -178.6(3) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
Br2 C21 C22 C23 179.4(3) . . . . ?
C21 C22 C23 C18 -0.8(6) . . . . ?
C19 C18 C23 C22 0.2(6) . . . . ?
C13A C18 C23 C22 -176.0(4) . . . . ?
C13 C18 C23 C22 -176.0(4) . . . . ?

