# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2290358'
loop_
_audit_author_name
_audit_author_address
'Riccardo Pedrazzani'
;University of Bologna
Italy
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 O2'
_chemical_formula_weight         418.51

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'
O O 0.0492 0.0322 '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'

_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                   6.0915(3)
_cell_length_b                   10.7543(4)
_cell_length_c                   17.1562(8)
_cell_angle_alpha                100.087(3)
_cell_angle_beta                 92.581(3)
_cell_angle_gamma                102.264(2)
_cell_volume                     1077.32(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9701
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      72.32


_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.10
_exptl_absorpt_coefficient_mu    0.617
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3803
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.625
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_full        66.575
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3803
_reflns_number_gt                3164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0041(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3803
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_restrained_S_all      1.258
_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 -1.1438(3) -2.05363(13) -0.18339(8) 0.0366(4) Uani 1 1 d . . . . .
O2 O -1.8375(2) -2.03610(13) -0.30158(8) 0.0318(4) Uani 1 1 d . . . . .
H31 H -1.895751 -2.049224 -0.259451 0.048 Uiso 1 1 calc R U . . .
C18 C -1.4661(4) -2.27375(18) -0.32511(12) 0.0327(5) Uani 1 1 d . . . . .
H18 H -1.327073 -2.221623 -0.334789 0.039 Uiso 1 1 calc R U . . .
C20 C -1.0700(4) -1.86294(18) -0.42371(11) 0.0310(5) Uani 1 1 d . . . . .
H20 H -1.033681 -1.931856 -0.401615 0.037 Uiso 1 1 calc R U . . .
C3 C -1.6231(3) -2.07010(17) -0.30189(11) 0.0277(5) Uani 1 1 d . . . . .
C15 C -1.8653(4) -2.42656(19) -0.29427(12) 0.0364(5) Uani 1 1 d . . . . .
H15 H -2.002059 -2.478833 -0.282874 0.044 Uiso 1 1 calc R U . . .
C4 C -1.5215(4) -2.02469(17) -0.37516(11) 0.0290(5) Uani 1 1 d . . . . .
H4A H -1.639929 -2.038620 -0.419252 0.035 Uiso 1 1 calc R U . . .
H4B H -1.405128 -2.072248 -0.393366 0.035 Uiso 1 1 calc R U . . .
C22 C -0.9807(4) -1.70652(19) -0.50776(12) 0.0366(5) Uani 1 1 d . . . . .
H22 H -0.884090 -1.668443 -0.543291 0.044 Uiso 1 1 calc R U . . .
C11 C -1.4684(4) -2.26156(19) -0.02595(13) 0.0420(6) Uani 1 1 d . . . . .
H11 H -1.403074 -2.322588 -0.004775 0.050 Uiso 1 1 calc R U . . .
C5 C -1.4171(4) -1.88010(17) -0.34754(11) 0.0277(5) Uani 1 1 d . . . . .
H5 H -1.541209 -1.832795 -0.338623 0.033 Uiso 1 1 calc R U . . .
C25 C -1.2212(4) -1.74776(17) -0.21279(11) 0.0282(5) Uani 1 1 d . . . . .
C27 C -1.2980(4) -1.54234(19) -0.15111(13) 0.0379(5) Uani 1 1 d . . . . .
H27 H -1.398232 -1.485371 -0.143807 0.046 Uiso 1 1 calc R U . . .
C7 C -1.4673(4) -2.11506(17) -0.11762(11) 0.0281(5) Uani 1 1 d . . . . .
C30 C -1.0054(4) -1.70851(19) -0.17397(12) 0.0344(5) Uani 1 1 d . . . . .
H30 H -0.903977 -1.764698 -0.181649 0.041 Uiso 1 1 calc R U . . .
C6 C -1.2961(3) -1.87901(17) -0.26600(11) 0.0265(4) Uani 1 1 d . . . . .
H6 H -1.158537 -1.914052 -0.276409 0.032 Uiso 1 1 calc R U . . .
C9 C -1.7594(4) -2.1435(2) -0.02911(12) 0.0379(5) Uani 1 1 d . . . . .
H9 H -1.893395 -2.122933 -0.009556 0.045 Uiso 1 1 calc R U . . .
C21 C -0.9313(4) -1.80746(19) -0.47578(12) 0.0347(5) Uani 1 1 d . . . . .
H21 H -0.801195 -1.839010 -0.489631 0.042 Uiso 1 1 calc R U . . .
C23 C -1.1706(4) -1.66062(18) -0.48819(12) 0.0361(5) Uani 1 1 d . . . . .
H23 H -1.205167 -1.591439 -0.510436 0.043 Uiso 1 1 calc R U . . .
C17 C -1.4875(4) -2.40630(19) -0.33113(13) 0.0378(5) Uani 1 1 d . . . . .
H17 H -1.364263 -2.444351 -0.345322 0.045 Uiso 1 1 calc R U . . .
C8 C -1.6639(4) -2.08643(19) -0.08962(12) 0.0326(5) Uani 1 1 d . . . . .
H8 H -1.733073 -2.027828 -0.111839 0.039 Uiso 1 1 calc R U . . .
C26 C -1.3660(4) -1.66284(18) -0.20017(12) 0.0318(5) Uani 1 1 d . . . . .
H26 H -1.514434 -1.688267 -0.225794 0.038 Uiso 1 1 calc R U . . .
C14 C -1.8449(4) -2.29395(18) -0.28850(12) 0.0323(5) Uani 1 1 d . . . . .
H14 H -1.967772 -2.256311 -0.273148 0.039 Uiso 1 1 calc R U . . .
C2 C -1.4615(3) -1.97875(17) -0.22964(11) 0.0273(5) Uani 1 1 d . . . . .
H2 H -1.555891 -1.930306 -0.195276 0.033 Uiso 1 1 calc R U . . .
C29 C -0.9364(4) -1.5882(2) -0.12412(13) 0.0412(6) Uani 1 1 d . . . . .
H29 H -0.788745 -1.562799 -0.097861 0.049 Uiso 1 1 calc R U . . .
C12 C -1.3704(4) -2.20442(18) -0.08568(12) 0.0352(5) Uani 1 1 d . . . . .
H12 H -1.236908 -2.225644 -0.105242 0.042 Uiso 1 1 calc R U . . .
C1 C -1.3413(4) -2.04932(17) -0.17729(11) 0.0281(5) Uani 1 1 d . . . . .
C24 C -1.3097(4) -1.71596(18) -0.43610(11) 0.0316(5) Uani 1 1 d . . . . .
H24 H -1.439159 -1.683613 -0.422409 0.038 Uiso 1 1 calc R U . . .
C19 C -1.2634(3) -1.81855(17) -0.40324(11) 0.0270(4) Uani 1 1 d . . . . .
C13 C -1.6456(3) -2.21585(17) -0.30505(11) 0.0268(5) Uani 1 1 d . . . . .
C28 C -1.0824(4) -1.5054(2) -0.11268(13) 0.0407(6) Uani 1 1 d . . . . .
H28 H -1.035086 -1.423244 -0.078523 0.049 Uiso 1 1 calc R U . . .
C10 C -1.6618(4) -2.22998(19) 0.00312(13) 0.0404(6) Uani 1 1 d . . . . .
H10 H -1.727281 -2.267671 0.045131 0.048 Uiso 1 1 calc R U . . .
C16 C -1.6885(4) -2.48287(19) -0.31644(13) 0.0383(5) Uani 1 1 d . . . . .
H16 H -1.704726 -2.573845 -0.321584 0.046 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 C1 1.222(2) . ?
O2 C3 1.429(2) . ?
C18 C17 1.388(3) . ?
C18 C13 1.396(3) . ?
C20 C21 1.381(3) . ?
C20 C19 1.399(3) . ?
C3 C4 1.536(3) . ?
C3 C13 1.535(2) . ?
C3 C2 1.589(3) . ?
C15 C16 1.380(3) . ?
C15 C14 1.390(3) . ?
C4 C5 1.530(3) . ?
C22 C23 1.383(3) . ?
C22 C21 1.379(3) . ?
C11 C10 1.384(3) . ?
C11 C12 1.380(3) . ?
C5 C19 1.506(3) . ?
C5 C6 1.549(3) . ?
C25 C30 1.392(3) . ?
C25 C26 1.396(3) . ?
C25 C6 1.507(3) . ?
C27 C28 1.388(3) . ?
C27 C26 1.385(3) . ?
C7 C8 1.384(3) . ?
C7 C12 1.403(3) . ?
C7 C1 1.494(3) . ?
C30 C29 1.390(3) . ?
C6 C2 1.545(2) . ?
C9 C8 1.385(3) . ?
C9 C10 1.382(3) . ?
C23 C24 1.383(3) . ?
C17 C16 1.383(3) . ?
C14 C13 1.393(3) . ?
C2 C1 1.528(3) . ?
C29 C28 1.383(3) . ?
C24 C19 1.397(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 C18 C13 121.1(2) . . ?
C21 C20 C19 120.60(18) . . ?
O2 C3 C4 104.32(15) . . ?
O2 C3 C13 111.85(16) . . ?
C4 C3 C13 112.68(15) . . ?
O2 C3 C2 108.79(15) . . ?
C4 C3 C2 103.49(15) . . ?
C13 C3 C2 114.88(15) . . ?
C16 C15 C14 120.5(2) . . ?
C3 C4 C5 105.09(15) . . ?
C23 C22 C21 120.11(19) . . ?
C10 C11 C12 120.0(2) . . ?
C19 C5 C4 115.34(15) . . ?
C19 C5 C6 113.56(17) . . ?
C4 C5 C6 101.37(14) . . ?
C30 C25 C26 118.08(19) . . ?
C30 C25 C6 120.63(18) . . ?
C26 C25 C6 121.28(19) . . ?
C28 C27 C26 119.5(2) . . ?
C8 C7 C12 119.45(18) . . ?
C8 C7 C1 123.46(17) . . ?
C12 C7 C1 116.98(19) . . ?
C29 C30 C25 120.9(2) . . ?
C25 C6 C2 114.14(15) . . ?
C25 C6 C5 115.39(14) . . ?
C2 C6 C5 104.33(16) . . ?
C8 C9 C10 120.7(2) . . ?
C20 C21 C22 120.4(2) . . ?
C22 C23 C24 119.67(18) . . ?
C16 C17 C18 119.9(2) . . ?
C7 C8 C9 119.8(2) . . ?
C27 C26 C25 121.4(2) . . ?
C15 C14 C13 120.5(2) . . ?
C1 C2 C6 112.76(17) . . ?
C1 C2 C3 114.95(14) . . ?
C6 C2 C3 106.17(14) . . ?
C28 C29 C30 120.1(2) . . ?
C11 C12 C7 120.2(2) . . ?
O1 C1 C7 119.14(17) . . ?
O1 C1 C2 121.33(17) . . ?
C7 C1 C2 119.53(18) . . ?
C23 C24 C19 121.2(2) . . ?
C20 C19 C24 118.08(17) . . ?
C20 C19 C5 120.81(16) . . ?
C24 C19 C5 121.11(18) . . ?
C14 C13 C18 118.22(17) . . ?
C14 C13 C3 121.19(18) . . ?
C18 C13 C3 120.59(17) . . ?
C27 C28 C29 120.0(2) . . ?
C11 C10 C9 119.85(19) . . ?
C15 C16 C17 119.71(18) . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057



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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2290359'
loop_
_audit_author_name
_audit_author_address
'Riccardo Pedrazzani'
;University of Bologna
Italy
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H34 O3'
_chemical_formula_weight         478.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   20.7540(16)
_cell_length_b                   5.9450(5)
_cell_length_c                   24.1084(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.709(2)
_cell_angle_gamma                90
_cell_volume                     2744.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7426
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      30.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_T_max  0.7488
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31699
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4793
_reflns_number_gt                3894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0795P)²+3.5909P] 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         4793
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.2272
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48571(13) 0.3105(4) 0.80918(10) 0.0425(6) Uani 1 1 d . . . . .
H1A H 0.503550 0.292540 0.845713 0.064 Uiso 1 1 calc R U . . .
O2 O 0.41246(15) 0.1854(4) 0.69455(12) 0.0518(7) Uani 1 1 d . . . . .
H2A H 0.439816 0.163634 0.729256 0.078 Uiso 1 1 calc R U . . .
C19 C 0.52641(14) 0.6229(5) 0.66817(14) 0.0310(7) Uani 1 1 d . . . . .
C2 C 0.44637(15) 0.5714(5) 0.72840(13) 0.0289(7) Uani 1 1 d . . . . .
H2 H 0.428918 0.725118 0.717780 0.035 Uiso 1 1 calc R U . . .
C3 C 0.51972(15) 0.5617(5) 0.72650(13) 0.0303(7) Uani 1 1 d . . . . .
H3 H 0.537411 0.408140 0.736929 0.036 Uiso 1 1 calc R U . . .
C7 C 0.40020(17) 0.5837(6) 0.81296(14) 0.0354(7) Uani 1 1 d . . . . .
C6 C 0.38985(16) 0.4118(5) 0.68800(15) 0.0355(7) Uani 1 1 d . . . . .
H6 H 0.350822 0.419659 0.701268 0.043 Uiso 1 1 calc R U . . .
C13 C 0.36109(15) 0.4755(6) 0.62213(15) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.46294(16) 0.5404(5) 0.79606(14) 0.0346(7) Uani 1 1 d . . . . .
C4 C 0.56233(16) 0.7171(6) 0.78008(15) 0.0373(8) Uani 1 1 d . . . . .
H4 H 0.555789 0.872044 0.765056 0.045 Uiso 1 1 calc R U . . .
C20 C 0.50408(19) 0.8261(6) 0.64004(16) 0.0469(9) Uani 1 1 d . . . . .
H20 H 0.483802 0.930845 0.656999 0.056 Uiso 1 1 calc R U . . .
C24 C 0.55691(18) 0.4723(6) 0.64190(16) 0.0450(9) Uani 1 1 d . . . . .
H24 H 0.572481 0.334022 0.660230 0.054 Uiso 1 1 calc R U . . .
C25 C 0.63955(17) 0.6682(6) 0.80408(14) 0.0412(8) Uani 1 1 d . . . . .
C5 C 0.52548(18) 0.6962(6) 0.82555(15) 0.0419(8) Uani 1 1 d . . . . .
H5A H 0.557233 0.633181 0.863333 0.050 Uiso 1 1 calc R U . . .
H5B H 0.510108 0.842616 0.833310 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3638(2) 0.7829(6) 0.79855(18) 0.0502(10) Uani 1 1 d . . . . .
H12 H 0.379406 0.896541 0.780332 0.060 Uiso 1 1 calc R U . . .
C8 C 0.37524(19) 0.4188(7) 0.84015(17) 0.0491(9) Uani 1 1 d . . . . .
H8 H 0.398430 0.281654 0.850281 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3647(2) 0.3318(8) 0.57888(17) 0.0554(10) Uani 1 1 d . . . . .
H18 H 0.385547 0.191464 0.589851 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3283(2) 0.6808(7) 0.60350(19) 0.0592(11) Uani 1 1 d . . . . .
H14 H 0.324230 0.779114 0.631962 0.071 Uiso 1 1 calc R U . . .
C21 C 0.5114(2) 0.8762(7) 0.58698(18) 0.0579(11) Uani 1 1 d . . . . .
H21 H 0.495730 1.013714 0.568263 0.069 Uiso 1 1 calc R U . . .
C22 C 0.5418(2) 0.7244(8) 0.56156(17) 0.0614(12) Uani 1 1 d . . . . .
H22 H 0.546651 0.758861 0.525758 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2808(2) 0.6537(8) 0.83755(19) 0.0607(11) Uani 1 1 d . . . . .
H10 H 0.241020 0.676866 0.845677 0.073 Uiso 1 1 calc R U . . .
C9 C 0.3163(2) 0.4556(8) 0.85239(19) 0.0611(11) Uani 1 1 d . . . . .
H9 H 0.300693 0.343482 0.871046 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3047(2) 0.8184(7) 0.81043(19) 0.0589(11) Uani 1 1 d . . . . .
H11 H 0.280910 0.954487 0.800023 0.071 Uiso 1 1 calc R U . . .
C30 C 0.6673(2) 0.4698(8) 0.83353(19) 0.0606(11) Uani 1 1 d . . . . .
H30 H 0.638081 0.365844 0.840869 0.073 Uiso 1 1 calc R U . . .
C23 C 0.5646(2) 0.5234(8) 0.58902(18) 0.0623(12) Uani 1 1 d . . . . .
H23 H 0.585493 0.420313 0.572117 0.075 Uiso 1 1 calc R U . . .
C29 C 0.7378(2) 0.4232(9) 0.8523(2) 0.0746(14) Uani 1 1 d . . . . .
H29 H 0.755402 0.288212 0.871729 0.089 Uiso 1 1 calc R U . . .
C17 C 0.3374(3) 0.3953(10) 0.5188(2) 0.0787(15) Uani 1 1 d . . . . .
H17 H 0.340650 0.297189 0.489913 0.094 Uiso 1 1 calc R U . . .
C15 C 0.3019(3) 0.7423(9) 0.5443(2) 0.0819(15) Uani 1 1 d . . . . .
H15 H 0.280995 0.882372 0.533045 0.098 Uiso 1 1 calc R U . . .
C16 C 0.3062(3) 0.5976(11) 0.5016(2) 0.0853(16) Uani 1 1 d . . . . .
H16 H 0.287779 0.638064 0.461191 0.102 Uiso 1 1 calc R U . . .
C28 C 0.7817(2) 0.5736(11) 0.8424(2) 0.0803(16) Uani 1 1 d . . . . .
H28 H 0.829173 0.542755 0.855483 0.096 Uiso 1 1 calc R U . . .
C27 C 0.7557(2) 0.7681(11) 0.8134(2) 0.0826(16) Uani 1 1 d . . . . .
H27 H 0.785432 0.870634 0.806319 0.099 Uiso 1 1 calc R U . . .
C26 C 0.6851(2) 0.8162(8) 0.7942(2) 0.0627(11) Uani 1 1 d . . . . .
H26 H 0.668146 0.950800 0.774263 0.075 Uiso 1 1 calc R U . . .
O1S O 0.5424(3) 0.1806(10) 0.92903(19) 0.142(2) Uani 1 1 d . . . . .
C2S C 0.5863(5) 0.1658(16) 0.9736(3) 0.135(3) Uani 1 1 d . . . . .
C1S C 0.6505(8) 0.268(4) 0.9851(7) 0.369(13) Uani 1 1 d . . . . .
H1S1 H 0.681600 0.236344 1.025681 0.554 Uiso 1 1 calc R U . . .
H1S2 H 0.670071 0.209481 0.957813 0.554 Uiso 1 1 calc R U . . .
H1S3 H 0.644206 0.427200 0.979616 0.554 Uiso 1 1 calc R U . . .
C3S C 0.6020(8) 0.002(3) 1.0198(6) 0.347(12) Uani 1 1 d . . . . .
H3S1 H 0.644502 0.042741 1.052540 0.520 Uiso 0.5 1 calc R U P . .
H3S2 H 0.564546 -0.004394 1.033815 0.520 Uiso 0.5 1 calc R U P . .
H3S3 H 0.607492 -0.142052 1.004350 0.520 Uiso 0.5 1 calc R U P . .
H3S4 H 0.566524 -0.111878 1.007930 0.520 Uiso 0.5 1 calc R U P . .
H3S5 H 0.646481 -0.064742 1.026655 0.520 Uiso 0.5 1 calc R U P . .
H3S6 H 0.603535 0.072915 1.056120 0.520 Uiso 0.5 1 calc R U P . .


_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 C1 1.441(4) . ?
O1 H1A 0.8200 . ?
O2 C6 1.414(4) . ?
O2 H2A 0.8200 . ?
C19 C20 1.375(5) . ?
C19 C24 1.383(4) . ?
C19 C3 1.510(4) . ?
C2 C6 1.531(4) . ?
C2 C3 1.542(4) . ?
C2 C1 1.543(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.556(4) . ?
C3 H3 0.9800 . ?
C7 C12 1.375(5) . ?
C7 C8 1.386(5) . ?
C7 C1 1.529(4) . ?
C6 C13 1.513(5) . ?
C6 H6 0.9800 . ?
C13 C18 1.372(5) . ?
C13 C14 1.385(5) . ?
C1 C5 1.528(5) . ?
C4 C25 1.507(5) . ?
C4 C5 1.565(5) . ?
C4 H4 0.9800 . ?
C20 C21 1.378(5) . ?
C20 H20 0.9300 . ?
C24 C23 1.379(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(5) . ?
C25 C30 1.383(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 C11 1.379(5) . ?
C12 H12 0.9300 . ?
C8 C9 1.381(5) . ?
C8 H8 0.9300 . ?
C18 C17 1.389(6) . ?
C18 H18 0.9300 . ?
C14 C15 1.365(6) . ?
C14 H14 0.9300 . ?
C21 C22 1.372(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.360(6) . ?
C22 H22 0.9300 . ?
C10 C9 1.361(6) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C30 C29 1.382(6) . ?
C30 H30 0.9300 . ?
C23 H23 0.9300 . ?
C29 C28 1.360(7) . ?
C29 H29 0.9300 . ?
C17 C16 1.353(8) . ?
C17 H17 0.9300 . ?
C15 C16 1.372(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C28 C27 1.351(8) . ?
C28 H28 0.9300 . ?
C27 C26 1.385(6) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
O1S C2S 1.112(7) . ?
C2S C1S 1.391(17) . ?
C2S C3S 1.418(12) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
C3S H3S1 0.9600 . ?
C3S H3S2 0.9600 . ?
C3S H3S3 0.9600 . ?
C3S H3S4 0.9600 . ?
C3S H3S5 0.9600 . ?
C3S H3S6 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C6 O2 H2A 109.5 . . ?
C20 C19 C24 118.0(3) . . ?
C20 C19 C3 122.4(3) . . ?
C24 C19 C3 119.6(3) . . ?
C6 C2 C3 118.7(2) . . ?
C6 C2 C1 113.7(2) . . ?
C3 C2 C1 102.0(2) . . ?
C6 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C19 C3 C2 117.7(2) . . ?
C19 C3 C4 113.8(3) . . ?
C2 C3 C4 101.8(2) . . ?
C19 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C12 C7 C8 117.3(3) . . ?
C12 C7 C1 121.3(3) . . ?
C8 C7 C1 121.3(3) . . ?
O2 C6 C13 109.6(3) . . ?
O2 C6 C2 112.3(3) . . ?
C13 C6 C2 114.0(3) . . ?
O2 C6 H6 106.8 . . ?
C13 C6 H6 106.8 . . ?
C2 C6 H6 106.8 . . ?
C18 C13 C14 117.8(4) . . ?
C18 C13 C6 121.8(3) . . ?
C14 C13 C6 120.4(3) . . ?
O1 C1 C5 109.0(3) . . ?
O1 C1 C7 110.0(3) . . ?
C5 C1 C7 115.6(3) . . ?
O1 C1 C2 105.4(2) . . ?
C5 C1 C2 102.8(2) . . ?
C7 C1 C2 113.4(3) . . ?
C25 C4 C3 112.6(3) . . ?
C25 C4 C5 116.8(3) . . ?
C3 C4 C5 105.0(2) . . ?
C25 C4 H4 107.3 . . ?
C3 C4 H4 107.3 . . ?
C5 C4 H4 107.3 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C23 C24 C19 121.2(4) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C26 C25 C30 117.1(3) . . ?
C26 C25 C4 120.6(3) . . ?
C30 C25 C4 122.2(3) . . ?
C1 C5 C4 106.2(3) . . ?
C1 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
C1 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C7 C12 C11 121.7(3) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C13 C18 C17 120.3(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C29 C30 C25 121.2(4) . . ?
C29 C30 H30 119.4 . . ?
C25 C30 H30 119.4 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C28 C29 C30 120.4(5) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C27 C28 C29 119.5(4) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C28 C27 C26 120.7(5) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C25 C26 C27 121.2(5) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
O1S C2S C1S 121.4(10) . . ?
O1S C2S C3S 131.9(10) . . ?
C1S C2S C3S 103.3(10) . . ?
C2S C1S H1S1 109.5 . . ?
C2S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
C2S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C2S C3S H3S1 109.5 . . ?
C2S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
C2S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
H3S4 C3S H3S5 109.5 . . ?
H3S4 C3S H3S6 109.5 . . ?
H3S5 C3S H3S6 109.5 . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050



