# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_rm2111b
_database_code_depnum_ccdc_archive 'CCDC 2072872'
loop_
_audit_author_name
_audit_author_address
'Rebecca Melen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O3'
_chemical_formula_weight         330.36

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   29.133(2)
_cell_length_b                   5.3113(3)
_cell_length_c                   22.5850(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.704(8)
_cell_angle_gamma                90
_cell_volume                     3329.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2328
_cell_measurement_theta_min      4.1000
_cell_measurement_theta_max      73.9720

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.697
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_T_min  0.93827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14074
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.109
_diffrn_reflns_theta_max         76.602
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3476
_reflns_number_gt                2114
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0509P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3476
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.868
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53309(8) -0.1942(4) 0.05753(9) 0.0371(5) Uani 1 1 d . . . . .
H1A H 0.551568 -0.100394 0.035110 0.056 Uiso 1 1 calc R U . . .
H1B H 0.509342 -0.301346 0.028301 0.056 Uiso 1 1 calc R U . . .
H1C H 0.555004 -0.299453 0.089482 0.056 Uiso 1 1 calc R U . . .
C2 C 0.53678(7) 0.1440(3) 0.12859(8) 0.0283(4) Uani 1 1 d . . . . .
C3 C 0.51170(7) 0.3201(4) 0.15376(8) 0.0315(4) Uani 1 1 d . . . . .
H3 H 0.477495 0.317000 0.141699 0.038 Uiso 1 1 calc R U . . .
C4 C 0.53679(7) 0.4967(4) 0.19585(8) 0.0297(4) Uani 1 1 d . . . . .
H4 H 0.519325 0.615270 0.212041 0.036 Uiso 1 1 calc R U . . .
C5 C 0.58697(7) 0.5071(4) 0.21549(8) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.61123(7) 0.3288(4) 0.19045(8) 0.0283(4) Uani 1 1 d . . . . .
H6 H 0.645459 0.328984 0.203512 0.034 Uiso 1 1 calc R U . . .
C7 C 0.58670(7) 0.1510(4) 0.14696(8) 0.0300(4) Uani 1 1 d . . . . .
H7 H 0.604103 0.034962 0.129965 0.036 Uiso 1 1 calc R U . . .
C8 C 0.66094(7) 0.7883(4) 0.26070(8) 0.0284(4) Uani 1 1 d . . . . .
C9 C 0.73072(9) 1.0162(5) 0.31223(11) 0.0508(6) Uani 1 1 d . . . . .
H9A H 0.751632 0.878181 0.307398 0.076 Uiso 1 1 calc R U . . .
H9B H 0.745682 1.102913 0.351693 0.076 Uiso 1 1 calc R U . . .
H9C H 0.726178 1.135357 0.277799 0.076 Uiso 1 1 calc R U . . .
C10 C 0.61271(7) 0.6984(4) 0.26306(8) 0.0277(4) Uani 1 1 d . . . . .
C11 C 0.60301(7) 0.7118(4) 0.32575(8) 0.0278(4) Uani 1 1 d . . . . .
C12 C 0.58324(7) 0.8867(4) 0.28737(8) 0.0306(4) Uani 1 1 d . . . . .
H12 H 0.563629 1.033258 0.279471 0.037 Uiso 1 1 calc R U . . .
C13 C 0.61549(7) 0.5868(4) 0.38566(8) 0.0282(4) Uani 1 1 d . . . . .
C14 C 0.59596(7) 0.6811(4) 0.43244(9) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.573648 0.816760 0.423322 0.038 Uiso 1 1 calc R U . . .
C15 C 0.60966(7) 0.5747(4) 0.49009(9) 0.0335(4) Uani 1 1 d . . . . .
H15 H 0.596657 0.637964 0.520948 0.040 Uiso 1 1 calc R U . . .
C16 C 0.64275(7) 0.3724(4) 0.50508(8) 0.0305(4) Uani 1 1 d . . . . .
C17 C 0.66151(7) 0.2746(4) 0.45836(8) 0.0302(4) Uani 1 1 d . . . . .
C18 C 0.64675(7) 0.3873(4) 0.39852(8) 0.0308(4) Uani 1 1 d . . . . .
H18 H 0.658774 0.323264 0.366848 0.037 Uiso 1 1 calc R U . . .
C19 C 0.65863(8) 0.2638(4) 0.56540(9) 0.0363(5) Uani 1 1 d . . . . .
H19 H 0.647020 0.328826 0.597345 0.044 Uiso 1 1 calc R U . . .
C20 C 0.69026(8) 0.0678(4) 0.57801(9) 0.0387(5) Uani 1 1 d . . . . .
H20 H 0.700159 -0.003534 0.618491 0.046 Uiso 1 1 calc R U . . .
C21 C 0.70855(9) -0.0307(4) 0.53148(10) 0.0421(5) Uani 1 1 d . . . . .
H21 H 0.730650 -0.167306 0.540811 0.051 Uiso 1 1 calc R U . . .
C22 C 0.69439(8) 0.0708(4) 0.47312(9) 0.0381(5) Uani 1 1 d . . . . .
H22 H 0.706761 0.003827 0.442055 0.046 Uiso 1 1 calc R U . . .
O1 O 0.50874(5) -0.0208(3) 0.08636(6) 0.0359(3) Uani 1 1 d . . . . .
O2 O 0.67744(5) 0.7569(3) 0.21792(6) 0.0381(3) Uani 1 1 d . . . . .
O3 O 0.68484(6) 0.9166(3) 0.31193(6) 0.0423(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.434(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.367(2) . ?
C2 C7 1.386(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C5 C10 1.503(3) . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O2 1.214(2) . ?
C8 O3 1.341(2) . ?
C8 C10 1.500(3) . ?
C9 O3 1.436(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.525(3) . ?
C10 C11 1.527(2) . ?
C11 C12 1.281(3) . ?
C11 C13 1.451(2) . ?
C12 H12 0.9500 . ?
C13 C18 1.369(3) . ?
C13 C14 1.434(2) . ?
C14 C15 1.363(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(3) . ?
C15 H15 0.9500 . ?
C16 C19 1.421(3) . ?
C16 C17 1.426(3) . ?
C17 C22 1.416(3) . ?
C17 C18 1.420(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.362(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.415(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.367(3) . ?
C21 H21 0.9500 . ?
C22 H22 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 125.16(17) . . ?
O1 C2 C3 115.69(17) . . ?
C7 C2 C3 119.15(17) . . ?
C4 C3 C2 119.97(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 122.16(18) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 116.99(18) . . ?
C4 C5 C10 120.10(17) . . ?
C6 C5 C10 122.88(17) . . ?
C7 C6 C5 122.00(18) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C2 C7 C6 119.73(18) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O2 C8 O3 121.95(18) . . ?
O2 C8 C10 125.88(17) . . ?
O3 C8 C10 112.16(15) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C5 117.31(15) . . ?
C8 C10 C12 116.11(16) . . ?
C5 C10 C12 119.18(17) . . ?
C8 C10 C11 117.21(16) . . ?
C5 C10 C11 120.11(16) . . ?
C12 C10 C11 49.64(11) . . ?
C12 C11 C13 153.66(18) . . ?
C12 C11 C10 65.08(13) . . ?
C13 C11 C10 141.14(17) . . ?
C11 C12 C10 65.28(13) . . ?
C11 C12 H12 147.4 . . ?
C10 C12 H12 147.4 . . ?
C18 C13 C14 120.08(17) . . ?
C18 C13 C11 120.92(17) . . ?
C14 C13 C11 118.96(17) . . ?
C15 C14 C13 119.50(18) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.59(17) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C19 122.49(18) . . ?
C15 C16 C17 119.11(17) . . ?
C19 C16 C17 118.39(18) . . ?
C22 C17 C18 122.26(17) . . ?
C22 C17 C16 119.23(17) . . ?
C18 C17 C16 118.51(18) . . ?
C13 C18 C17 121.17(17) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C16 120.86(19) . . ?
C20 C19 H19 119.6 . . ?
C16 C19 H19 119.6 . . ?
C19 C20 C21 120.75(19) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 120.8(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C2 O1 C1 117.05(16) . . ?
C8 O3 C9 115.44(15) . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_rm2112c1
_database_code_depnum_ccdc_archive 'CCDC 2072873'
loop_
_audit_author_name
_audit_author_address
'Rebecca Melen'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 O2'
_chemical_formula_weight         350.39

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   26.0464(11)
_cell_length_b                   18.2137(8)
_cell_length_c                   7.6051(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3607.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5478
_cell_measurement_theta_min      4.1300
_cell_measurement_theta_max      75.8020

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.636
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34640
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.173
_diffrn_reflns_theta_max         77.677
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             7272
_reflns_number_gt                5412
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.899
_reflns_Friedel_fraction_full    0.919

_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0512P)²+0.7851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7272
_refine_ls_number_parameters     489
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62592(16) 0.9423(2) 0.9776(6) 0.0359(9) Uani 1 1 d . . . . .
C2 C 0.64845(16) 1.0022(2) 1.0667(6) 0.0395(9) Uani 1 1 d . . . . .
H2 H 0.683177 0.999138 1.104157 0.047 Uiso 1 1 calc R U . . .
C3 C 0.62122(17) 1.0641(2) 1.0994(6) 0.0411(10) Uani 1 1 d . . . . .
H3 H 0.637548 1.104349 1.155695 0.049 Uiso 1 1 calc R U . . .
C4 C 0.56856(16) 1.0698(2) 1.0511(6) 0.0373(9) Uani 1 1 d . . . . .
C5 C 0.53892(18) 1.1334(2) 1.0853(7) 0.0462(10) Uani 1 1 d . . . . .
H5 H 0.554222 1.174350 1.142091 0.055 Uiso 1 1 calc R U . . .
C6 C 0.48839(18) 1.1361(2) 1.0371(7) 0.0472(11) Uani 1 1 d . . . . .
H6 H 0.468829 1.179015 1.060324 0.057 Uiso 1 1 calc R U . . .
C7 C 0.46498(18) 1.0753(2) 0.9529(7) 0.0460(10) Uani 1 1 d . . . . .
H7 H 0.429763 1.077461 0.920855 0.055 Uiso 1 1 calc R U . . .
C8 C 0.49290(17) 1.0139(2) 0.9179(6) 0.0410(9) Uani 1 1 d . . . . .
H8 H 0.476941 0.973451 0.860910 0.049 Uiso 1 1 calc R U . . .
C9 C 0.54511(16) 1.0093(2) 0.9650(6) 0.0351(8) Uani 1 1 d . . . . .
C10 C 0.57485(15) 0.94595(19) 0.9299(5) 0.0348(8) Uani 1 1 d . . . . .
H10 H 0.559404 0.905234 0.872465 0.042 Uiso 1 1 calc R U . . .
C11 C 0.65742(16) 0.8804(2) 0.9301(6) 0.0380(9) Uani 1 1 d . . . . .
C12 C 0.70240(16) 0.8507(2) 0.9217(7) 0.0428(10) Uani 1 1 d . . . . .
H12 H 0.737581 0.852760 0.954254 0.051 Uiso 1 1 calc R U . . .
C13 C 0.66002(14) 0.8098(2) 0.8233(6) 0.0333(8) Uani 1 1 d . . . . .
C14 C 0.66041(15) 0.8198(2) 0.6281(6) 0.0352(9) Uani 1 1 d . . . . .
C15 C 0.6365(2) 0.7689(3) 0.3542(6) 0.0524(12) Uani 1 1 d . . . . .
H15A H 0.618512 0.813336 0.315217 0.079 Uiso 1 1 calc R U . . .
H15B H 0.619067 0.725546 0.306734 0.079 Uiso 1 1 calc R U . . .
H15C H 0.671997 0.770115 0.311778 0.079 Uiso 1 1 calc R U . . .
C16 C 0.63966(15) 0.7383(2) 0.8940(5) 0.0340(8) Uani 1 1 d . . . . .
C17 C 0.58964(15) 0.7328(2) 0.9518(6) 0.0380(9) Uani 1 1 d . . . . .
H17 H 0.567902 0.774578 0.946079 0.046 Uiso 1 1 calc R U . . .
C18 C 0.57008(17) 0.6664(2) 1.0192(6) 0.0421(10) Uani 1 1 d . . . . .
H18 H 0.535632 0.664278 1.059960 0.050 Uiso 1 1 calc R U . . .
C19 C 0.60015(17) 0.6052(2) 1.0265(6) 0.0419(9) Uani 1 1 d . . . . .
H19 H 0.586670 0.560859 1.073316 0.050 Uiso 1 1 calc R U . . .
C20 C 0.65131(16) 0.6075(2) 0.9646(6) 0.0374(9) Uani 1 1 d . . . . .
C21 C 0.68233(19) 0.5435(2) 0.9617(7) 0.0471(11) Uani 1 1 d . . . . .
H21 H 0.668857 0.498529 1.004901 0.057 Uiso 1 1 calc R U . . .
C22 C 0.73087(18) 0.5456(2) 0.8981(7) 0.0489(11) Uani 1 1 d . . . . .
H22 H 0.751212 0.502286 0.897554 0.059 Uiso 1 1 calc R U . . .
C23 C 0.75130(19) 0.6119(2) 0.8328(7) 0.0464(10) Uani 1 1 d . . . . .
H23 H 0.785401 0.613010 0.788575 0.056 Uiso 1 1 calc R U . . .
C24 C 0.72253(15) 0.6746(2) 0.8325(6) 0.0398(9) Uani 1 1 d . . . . .
H24 H 0.736940 0.718816 0.788124 0.048 Uiso 1 1 calc R U . . .
C25 C 0.67157(15) 0.6748(2) 0.8973(6) 0.0350(8) Uani 1 1 d . . . . .
C26 C 0.61139(14) 0.46444(19) 0.4347(6) 0.0320(8) Uani 1 1 d . . . . .
C27 C 0.63132(16) 0.5264(2) 0.5245(6) 0.0351(8) Uani 1 1 d . . . . .
H27 H 0.665032 0.524510 0.571972 0.042 Uiso 1 1 calc R U . . .
C28 C 0.60277(15) 0.5886(2) 0.5436(6) 0.0374(9) Uani 1 1 d . . . . .
H28 H 0.617079 0.630271 0.600640 0.045 Uiso 1 1 calc R U . . .
C29 C 0.55180(15) 0.5913(2) 0.4786(5) 0.0329(8) Uani 1 1 d . . . . .
C30 C 0.52043(17) 0.6541(2) 0.5053(6) 0.0392(9) Uani 1 1 d . . . . .
H30 H 0.533964 0.695546 0.565368 0.047 Uiso 1 1 calc R U . . .
C31 C 0.47118(17) 0.6555(2) 0.4457(7) 0.0433(10) Uani 1 1 d . . . . .
H31 H 0.450618 0.697887 0.464259 0.052 Uiso 1 1 calc R U . . .
C32 C 0.45054(17) 0.5945(2) 0.3567(7) 0.0437(10) Uani 1 1 d . . . . .
H32 H 0.416151 0.595946 0.315234 0.052 Uiso 1 1 calc R U . . .
C33 C 0.47986(16) 0.5332(2) 0.3298(6) 0.0376(9) Uani 1 1 d . . . . .
H33 H 0.465550 0.492227 0.269943 0.045 Uiso 1 1 calc R U . . .
C34 C 0.53120(15) 0.5300(2) 0.3899(5) 0.0324(8) Uani 1 1 d . . . . .
C35 C 0.56264(15) 0.4667(2) 0.3681(5) 0.0328(8) Uani 1 1 d . . . . .
H35 H 0.549555 0.425394 0.306449 0.039 Uiso 1 1 calc R U . . .
C36 C 0.64414(14) 0.39967(19) 0.4241(6) 0.0338(8) Uani 1 1 d . . . . .
C37 C 0.68711(16) 0.3682(2) 0.4628(7) 0.0399(9) Uani 1 1 d . . . . .
H37 H 0.719418 0.371255 0.520305 0.048 Uiso 1 1 calc R U . . .
C38 C 0.65029(14) 0.3229(2) 0.3529(5) 0.0321(8) Uani 1 1 d . . . . .
C39 C 0.66385(15) 0.3170(2) 0.1619(6) 0.0343(8) Uani 1 1 d . . . . .
C40 C 0.65503(18) 0.2491(3) -0.0995(6) 0.0475(11) Uani 1 1 d . . . . .
H40A H 0.646468 0.293462 -0.166188 0.071 Uiso 1 1 calc R U . . .
H40B H 0.635500 0.207417 -0.146098 0.071 Uiso 1 1 calc R U . . .
H40C H 0.691862 0.239043 -0.110282 0.071 Uiso 1 1 calc R U . . .
C41 C 0.62236(14) 0.25899(19) 0.4362(5) 0.0306(8) Uani 1 1 d . . . . .
C42 C 0.57279(15) 0.2665(2) 0.4929(6) 0.0365(9) Uani 1 1 d . . . . .
H42 H 0.555556 0.311855 0.475441 0.044 Uiso 1 1 calc R U . . .
C43 C 0.54663(15) 0.2081(2) 0.5768(6) 0.0397(9) Uani 1 1 d . . . . .
H43 H 0.512305 0.214888 0.615805 0.048 Uiso 1 1 calc R U . . .
C44 C 0.57022(16) 0.1428(2) 0.6019(6) 0.0381(9) Uani 1 1 d . . . . .
H44 H 0.552107 0.103834 0.657182 0.046 Uiso 1 1 calc R U . . .
C45 C 0.62160(15) 0.1316(2) 0.5466(6) 0.0350(8) Uani 1 1 d . . . . .
C46 C 0.64756(17) 0.0642(2) 0.5727(6) 0.0432(10) Uani 1 1 d . . . . .
H46 H 0.630023 0.024794 0.628264 0.052 Uiso 1 1 calc R U . . .
C47 C 0.69693(18) 0.0546(2) 0.5202(7) 0.0468(11) Uani 1 1 d . . . . .
H47 H 0.713282 0.008495 0.537197 0.056 Uiso 1 1 calc R U . . .
C48 C 0.72393(16) 0.1127(2) 0.4406(7) 0.0452(10) Uani 1 1 d . . . . .
H48 H 0.758680 0.106135 0.406066 0.054 Uiso 1 1 calc R U . . .
C49 C 0.69994(15) 0.1790(2) 0.4128(6) 0.0367(9) Uani 1 1 d . . . . .
H49 H 0.718433 0.217591 0.357562 0.044 Uiso 1 1 calc R U . . .
C50 C 0.64845(14) 0.19120(19) 0.4643(5) 0.0319(8) Uani 1 1 d . . . . .
O1 O 0.68033(13) 0.87078(16) 0.5526(5) 0.0504(8) Uani 1 1 d . . . . .
O2 O 0.63625(12) 0.76574(16) 0.5441(4) 0.0455(7) Uani 1 1 d . . . . .
O3 O 0.69194(13) 0.35964(17) 0.0865(5) 0.0532(9) Uani 1 1 d . . . . .
O4 O 0.64220(10) 0.25985(15) 0.0829(4) 0.0378(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.381(6) . ?
C1 C2 1.413(6) . ?
C1 C11 1.440(6) . ?
C2 C3 1.354(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.424(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(6) . ?
C4 C9 1.421(6) . ?
C5 C6 1.367(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.417(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.361(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.415(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.292(6) . ?
C11 C13 1.522(5) . ?
C12 C13 1.527(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.496(6) . ?
C13 C16 1.505(5) . ?
C14 O1 1.208(5) . ?
C14 O2 1.332(5) . ?
C15 O2 1.446(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.379(6) . ?
C16 C25 1.426(5) . ?
C17 C18 1.408(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.364(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.414(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.418(6) . ?
C20 C25 1.430(5) . ?
C21 C22 1.354(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.411(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.366(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.416(6) . ?
C24 H24 0.9500 . ?
C26 C35 1.368(5) . ?
C26 C27 1.417(5) . ?
C26 C36 1.458(5) . ?
C27 C28 1.364(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.418(6) . ?
C28 H28 0.9500 . ?
C29 C34 1.411(5) . ?
C29 C30 1.420(6) . ?
C30 C31 1.361(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.407(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.369(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.414(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.424(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.292(6) . ?
C36 C38 1.508(5) . ?
C37 C38 1.516(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.499(6) . ?
C38 C41 1.512(5) . ?
C39 O3 1.212(5) . ?
C39 O4 1.327(5) . ?
C40 O4 1.440(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.368(5) . ?
C41 C50 1.425(5) . ?
C42 C43 1.414(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.353(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.417(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.416(5) . ?
C45 C50 1.434(5) . ?
C46 C47 1.358(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.408(6) . ?
C47 H47 0.9500 . ?
C48 C49 1.376(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.415(5) . ?
C49 H49 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
C10 C1 C2 119.3(4) . . ?
C10 C1 C11 121.4(4) . . ?
C2 C1 C11 119.2(4) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.2(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C9 119.0(4) . . ?
C5 C4 C3 122.6(4) . . ?
C9 C4 C3 118.4(4) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.0(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 121.9(4) . . ?
C8 C9 C4 119.1(4) . . ?
C10 C9 C4 119.0(4) . . ?
C1 C10 C9 121.2(4) . . ?
C1 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C1 149.0(4) . . ?
C12 C11 C13 65.1(3) . . ?
C1 C11 C13 145.1(4) . . ?
C11 C12 C13 64.7(3) . . ?
C11 C12 H12 147.6 . . ?
C13 C12 H12 147.6 . . ?
C14 C13 C16 117.5(3) . . ?
C14 C13 C11 115.3(3) . . ?
C16 C13 C11 121.6(4) . . ?
C14 C13 C12 115.0(4) . . ?
C16 C13 C12 120.1(4) . . ?
C11 C13 C12 50.2(3) . . ?
O1 C14 O2 122.9(4) . . ?
O1 C14 C13 124.6(4) . . ?
O2 C14 C13 112.5(4) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C25 119.0(4) . . ?
C17 C16 C13 120.7(4) . . ?
C25 C16 C13 120.2(3) . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 120.6(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 121.2(4) . . ?
C19 C20 C25 119.5(4) . . ?
C21 C20 C25 119.2(4) . . ?
C22 C21 C20 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 121.0(4) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C16 122.8(4) . . ?
C24 C25 C20 118.0(4) . . ?
C16 C25 C20 119.2(4) . . ?
C35 C26 C27 119.6(4) . . ?
C35 C26 C36 123.2(4) . . ?
C27 C26 C36 117.2(3) . . ?
C28 C27 C26 120.9(4) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 120.2(4) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C34 C29 C30 119.1(4) . . ?
C34 C29 C28 119.7(4) . . ?
C30 C29 C28 121.1(4) . . ?
C31 C30 C29 120.7(4) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.4(4) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 120.2(4) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 120.8(4) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C29 C34 C33 118.8(4) . . ?
C29 C34 C35 118.5(4) . . ?
C33 C34 C35 122.7(4) . . ?
C26 C35 C34 121.0(4) . . ?
C26 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C37 C36 C26 148.6(4) . . ?
C37 C36 C38 65.0(3) . . ?
C26 C36 C38 146.4(4) . . ?
C36 C37 C38 64.4(3) . . ?
C36 C37 H37 147.8 . . ?
C38 C37 H37 147.8 . . ?
C39 C38 C36 116.1(3) . . ?
C39 C38 C41 117.6(3) . . ?
C36 C38 C41 120.9(3) . . ?
C39 C38 C37 115.1(3) . . ?
C36 C38 C37 50.6(2) . . ?
C41 C38 C37 119.5(4) . . ?
O3 C39 O4 123.0(4) . . ?
O3 C39 C38 123.7(4) . . ?
O4 C39 C38 113.3(3) . . ?
O4 C40 H40A 109.5 . . ?
O4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C50 119.3(4) . . ?
C42 C41 C38 120.6(3) . . ?
C50 C41 C38 120.0(3) . . ?
C41 C42 C43 121.5(4) . . ?
C41 C42 H42 119.3 . . ?
C43 C42 H42 119.3 . . ?
C44 C43 C42 120.4(4) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 120.8(4) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 122.2(4) . . ?
C44 C45 C50 118.8(4) . . ?
C46 C45 C50 119.0(4) . . ?
C47 C46 C45 121.5(4) . . ?
C47 C46 H46 119.2 . . ?
C45 C46 H46 119.2 . . ?
C46 C47 C48 120.2(4) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C49 C48 C47 119.9(4) . . ?
C49 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?
C48 C49 C50 121.7(4) . . ?
C48 C49 H49 119.1 . . ?
C50 C49 H49 119.1 . . ?
C49 C50 C41 123.1(3) . . ?
C49 C50 C45 117.7(3) . . ?
C41 C50 C45 119.2(3) . . ?
C14 O2 C15 116.6(4) . . ?
C39 O4 C40 116.4(3) . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044



