# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_cu_th119_rycek
_database_code_depnum_ccdc_archive 'CCDC 2376335'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-08-07 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H22 O4'
_chemical_formula_sum            'C29 H22 O4'
_chemical_formula_weight         434.46
_chemical_compound_source        'synthesized by the authors'


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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4717(5)
_cell_length_b                   12.7788(7)
_cell_length_c                   18.5575(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.343(2)
_cell_angle_gamma                90
_cell_volume                     2209.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      4.8448
_cell_measurement_theta_max      68.3069

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.695
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31736
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.845
_diffrn_reflns_theta_max         68.301
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4039
_reflns_number_gt                3844
_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 Instrument Service v8.5.1.2 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_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)+(0.0368P)²+0.8408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4039
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38339(8) 0.52132(6) 0.66416(4) 0.02450(18) Uani 1 1 d . . . . .
O2 O 0.69686(9) 1.14574(6) 0.76940(4) 0.02688(19) Uani 1 1 d . . . . .
O3 O 0.00415(9) 0.13591(6) 0.61489(5) 0.02818(19) Uani 1 1 d . . . . .
O4 O -0.03390(8) 0.87652(6) 0.73893(4) 0.02548(19) Uani 1 1 d . . . . .
H4 H 0.020515 0.910200 0.776813 0.038 Uiso 1 1 d R U . . .
C1 C 0.32562(11) 0.56202(9) 0.39382(6) 0.0228(2) Uani 1 1 d . . . . .
H1 H 0.332974 0.556898 0.343553 0.027 Uiso 1 1 calc R U . . .
C2 C 0.27479(11) 0.47773(9) 0.42879(6) 0.0212(2) Uani 1 1 d . . . . .
H2 H 0.247282 0.415353 0.402078 0.025 Uiso 1 1 calc R U . . .
C3 C 0.26348(11) 0.48330(8) 0.50289(6) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.30303(11) 0.57594(8) 0.54176(6) 0.0178(2) Uani 1 1 d . . . . .
C5 C 0.35373(11) 0.66198(8) 0.50598(6) 0.0193(2) Uani 1 1 d . . . . .
C6 C 0.36559(11) 0.65341(9) 0.43188(6) 0.0220(2) Uani 1 1 d . . . . .
H6 H 0.401213 0.710647 0.407815 0.026 Uiso 1 1 calc R U . . .
C7 C 0.40114(11) 0.75613(9) 0.54498(6) 0.0215(2) Uani 1 1 d . . . . .
C8 C 0.44648(12) 0.83420(9) 0.57756(6) 0.0232(2) Uani 1 1 d . . . . .
C9 C 0.50438(12) 0.92079(8) 0.62224(6) 0.0219(2) Uani 1 1 d . . . . .
C10 C 0.46202(12) 0.93828(9) 0.69004(6) 0.0246(2) Uani 1 1 d . . . . .
H10 H 0.388023 0.896698 0.703768 0.030 Uiso 1 1 calc R U . . .
C11 C 0.52645(12) 1.01494(9) 0.73680(6) 0.0248(2) Uani 1 1 d . . . . .
H11 H 0.496150 1.026304 0.782274 0.030 Uiso 1 1 calc R U . . .
C12 C 0.63610(11) 1.07602(8) 0.71765(6) 0.0209(2) Uani 1 1 d . . . . .
C13 C 0.67639(12) 1.06243(9) 0.64970(6) 0.0242(2) Uani 1 1 d . . . . .
H13 H 0.748553 1.105508 0.635631 0.029 Uiso 1 1 calc R U . . .
C14 C 0.61013(12) 0.98532(9) 0.60265(6) 0.0257(2) Uani 1 1 d . . . . .
H14 H 0.637380 0.976366 0.556206 0.031 Uiso 1 1 calc R U . . .
C15 C 0.20282(11) 0.39160(8) 0.53601(5) 0.0183(2) Uani 1 1 d . . . . .
C16 C 0.25176(11) 0.29096(8) 0.52553(6) 0.0208(2) Uani 1 1 d . . . . .
H16 H 0.329399 0.281959 0.500043 0.025 Uiso 1 1 calc R U . . .
C17 C 0.18961(12) 0.20321(8) 0.55152(6) 0.0228(2) Uani 1 1 d . . . . .
H17 H 0.225454 0.135244 0.544513 0.027 Uiso 1 1 calc R U . . .
C18 C 0.07483(11) 0.21606(9) 0.58775(6) 0.0212(2) Uani 1 1 d . . . . .
C19 C 0.02488(11) 0.31627(9) 0.59933(6) 0.0207(2) Uani 1 1 d . . . . .
H19 H -0.052956 0.325070 0.624701 0.025 Uiso 1 1 calc R U . . .
C20 C 0.08863(11) 0.40275(8) 0.57391(5) 0.0191(2) Uani 1 1 d . . . . .
H20 H 0.054420 0.470749 0.582294 0.023 Uiso 1 1 calc R U . . .
C21 C 0.30621(11) 0.58182(8) 0.62348(6) 0.0180(2) Uani 1 1 d . . . . .
C22 C 0.21802(11) 0.66087(8) 0.65289(6) 0.0177(2) Uani 1 1 d . . . . .
C23 C 0.25580(11) 0.69230(8) 0.72621(6) 0.0204(2) Uani 1 1 d . . . . .
H23 H 0.338295 0.663082 0.756135 0.024 Uiso 1 1 calc R U . . .
C24 C 0.17432(11) 0.76534(9) 0.75545(6) 0.0210(2) Uani 1 1 d . . . . .
H24 H 0.202707 0.788127 0.804650 0.025 Uiso 1 1 calc R U . . .
C25 C 0.05062(11) 0.80529(8) 0.71249(6) 0.0198(2) Uani 1 1 d . . . . .
C26 C 0.00945(11) 0.77265(8) 0.64004(6) 0.0207(2) Uani 1 1 d . . . . .
H26 H -0.076817 0.798269 0.611323 0.025 Uiso 1 1 calc R U . . .
C27 C 0.09447(11) 0.70295(8) 0.61013(6) 0.0192(2) Uani 1 1 d . . . . .
H27 H 0.068740 0.683476 0.560082 0.023 Uiso 1 1 calc R U . . .
C28 C 0.81593(14) 1.20551(10) 0.75565(7) 0.0326(3) Uani 1 1 d . . . . .
H28A H 0.852301 1.248967 0.798475 0.049 Uiso 1 1 calc R U . . .
H28B H 0.785573 1.250494 0.712906 0.049 Uiso 1 1 calc R U . . .
H28C H 0.891934 1.158244 0.746090 0.049 Uiso 1 1 calc R U . . .
C29 C 0.05957(17) 0.03272(10) 0.61090(8) 0.0384(3) Uani 1 1 d . . . . .
H29A H 0.001192 -0.016735 0.633300 0.058 Uiso 1 1 calc R U . . .
H29B H 0.158979 0.030279 0.637179 0.058 Uiso 1 1 calc R U . . .
H29C H 0.056625 0.013707 0.559496 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.2263(13) . ?
O2 C12 1.3596(13) . ?
O2 C28 1.4226(14) . ?
O3 C18 1.3682(13) . ?
O3 C29 1.4261(15) . ?
O4 C25 1.3605(13) . ?
O4 H4 0.9028 . ?
C1 C6 1.3821(16) . ?
C1 C2 1.3876(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.4001(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.4018(14) . ?
C3 C15 1.4860(14) . ?
C4 C5 1.4124(15) . ?
C4 C21 1.5134(14) . ?
C5 C6 1.4039(15) . ?
C5 C7 1.4339(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.2050(16) . ?
C8 C9 1.4315(16) . ?
C9 C14 1.3951(16) . ?
C9 C10 1.4055(16) . ?
C10 C11 1.3766(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3952(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3924(16) . ?
C13 C14 1.3894(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.3925(15) . ?
C15 C20 1.3992(15) . ?
C16 C17 1.3923(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3867(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3951(16) . ?
C19 C20 1.3823(15) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.4763(14) . ?
C22 C27 1.3982(15) . ?
C22 C23 1.4021(15) . ?
C23 C24 1.3826(15) . ?
C23 H23 0.9500 . ?
C24 C25 1.3905(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.3948(15) . ?
C26 C27 1.3822(15) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C28 118.28(9) . . ?
C18 O3 C29 117.65(9) . . ?
C25 O4 H4 108.0 . . ?
C6 C1 C2 120.20(10) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 120.93(10) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 119.20(10) . . ?
C2 C3 C15 118.01(9) . . ?
C4 C3 C15 122.73(9) . . ?
C3 C4 C5 119.84(9) . . ?
C3 C4 C21 120.86(9) . . ?
C5 C4 C21 119.02(9) . . ?
C6 C5 C4 119.56(10) . . ?
C6 C5 C7 119.14(10) . . ?
C4 C5 C7 121.20(9) . . ?
C1 C6 C5 120.26(10) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C5 177.40(11) . . ?
C7 C8 C9 174.56(12) . . ?
C14 C9 C10 118.23(10) . . ?
C14 C9 C8 121.62(10) . . ?
C10 C9 C8 120.02(10) . . ?
C11 C10 C9 120.79(10) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.24(10) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O2 C12 C13 124.84(10) . . ?
O2 C12 C11 115.26(10) . . ?
C13 C12 C11 119.90(10) . . ?
C14 C13 C12 119.42(10) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 121.33(10) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C16 C15 C20 118.10(10) . . ?
C16 C15 C3 120.49(9) . . ?
C20 C15 C3 121.25(9) . . ?
C17 C16 C15 121.55(10) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 119.32(10) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
O3 C18 C17 124.60(10) . . ?
O3 C18 C19 115.37(10) . . ?
C17 C18 C19 120.03(10) . . ?
C20 C19 C18 120.01(10) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.97(10) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
O1 C21 C22 121.21(9) . . ?
O1 C21 C4 119.21(9) . . ?
C22 C21 C4 119.58(9) . . ?
C27 C22 C23 118.84(10) . . ?
C27 C22 C21 121.65(9) . . ?
C23 C22 C21 119.47(9) . . ?
C24 C23 C22 120.73(10) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.68(10) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
O4 C25 C24 121.92(9) . . ?
O4 C25 C26 117.83(10) . . ?
C24 C25 C26 120.25(10) . . ?
C27 C26 C25 119.85(10) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C22 120.56(9) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O3 C29 H29A 109.5 . . ?
O3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037

