# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_ajtr2_a
_database_code_depnum_ccdc_archive 'CCDC 1872402'
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-07-11 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 H30 O6'
_chemical_formula_weight         486.54

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      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                   8.6582(4)
_cell_length_b                   8.9482(4)
_cell_length_c                   9.1287(4)
_cell_angle_alpha                99.800(2)
_cell_angle_beta                 94.649(2)
_cell_angle_gamma                108.311(2)
_cell_volume                     654.76(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6767
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.41

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             258
_exptl_transmission_factor_min   0.933
_exptl_transmission_factor_max   0.949
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.69
_exptl_crystal_size_min          0.59
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            14982
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         26.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2683
_reflns_number_gt                2160
_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)+(0.0567P)²+0.1503P] 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         2683
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.30132(13) 0.28262(13) 0.66296(12) 0.0448(3) Uani 1 1 d . . . . .
O2 O 0.85059(12) 0.21078(13) 0.33544(11) 0.0434(3) Uani 1 1 d . . . . .
O3 O 0.36934(13) 0.17320(14) 0.19364(12) 0.0477(3) Uani 1 1 d . . . . .
C12 C 0.60414(16) 0.03439(16) 0.39209(14) 0.0316(3) Uani 1 1 d . . . . .
C16 C 0.38250(16) 0.07702(16) 0.52091(15) 0.0317(3) Uani 1 1 d . . . . .
C11 C 0.48878(16) 0.11333(16) 0.41424(15) 0.0315(3) Uani 1 1 d . . . . .
C20 C 0.48495(18) 0.24277(18) 0.32793(16) 0.0378(3) Uani 1 1 d . . . . .
H20A H 0.453858 0.325127 0.389642 0.045 Uiso 1 1 calc R U . . .
H20B H 0.593397 0.292783 0.302714 0.045 Uiso 1 1 calc R U . . .
C17 C 0.71365(17) 0.06902(18) 0.27252(15) 0.0363(3) Uani 1 1 d . . . . .
H17A H 0.751412 -0.020926 0.240525 0.044 Uiso 1 1 calc R U . . .
H17B H 0.653333 0.085458 0.185869 0.044 Uiso 1 1 calc R U . . .
C10 C 0.24869(17) 0.15069(18) 0.53805(16) 0.0366(3) Uani 1 1 d . . . . .
H10A H 0.224906 0.187349 0.447472 0.044 Uiso 1 1 calc R U . . .
H10B H 0.149088 0.070882 0.553560 0.044 Uiso 1 1 calc R U . . .
C5 C 0.95790(19) 0.2533(2) 0.22897(18) 0.0444(4) Uani 1 1 d . . . . .
H5A H 0.897281 0.263676 0.139303 0.053 Uiso 1 1 calc R U . . .
H5B H 1.006156 0.170217 0.200861 0.053 Uiso 1 1 calc R U . . .
C4 C 1.08655(19) 0.4053(2) 0.29501(18) 0.0440(4) Uani 1 1 d . . . . .
C6 C 0.0420(2) 0.2311(2) 0.75759(18) 0.0439(4) Uani 1 1 d . . . . .
C7 C 0.1721(2) 0.3438(2) 0.6983(2) 0.0505(4) Uani 1 1 d . . . . .
H7A H 0.124730 0.367001 0.608454 0.061 Uiso 1 1 calc R U . . .
H7B H 0.217633 0.443959 0.772015 0.061 Uiso 1 1 calc R U . . .
C1 C -0.0635(2) 0.1391(2) 0.8017(2) 0.0551(5) Uani 1 1 d . . . . .
H1 H -0.147178 0.066066 0.836611 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5240(2) 0.2969(2) 0.01379(18) 0.0512(4) Uani 1 1 d . . . . .
C9 C 0.3832(2) 0.2825(2) 0.0937(2) 0.0545(5) Uani 1 1 d . . . . .
H9A H 0.393002 0.387701 0.150856 0.065 Uiso 1 1 calc R U . . .
H9B H 0.283803 0.245637 0.021434 0.065 Uiso 1 1 calc R U . . .
C3 C 1.1879(3) 0.5281(2) 0.3484(2) 0.0658(5) Uani 1 1 d . . . . .
H3 H 1.268772 0.626120 0.391018 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6350(3) 0.3082(3) -0.0523(2) 0.0748(6) Uani 1 1 d . . . . .
H2 H 0.723816 0.317216 -0.105165 0.090 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 C10 1.4216(18) . ?
O1 C7 1.4281(19) . ?
O2 C5 1.4152(17) . ?
O2 C17 1.4288(18) . ?
O3 C20 1.4290(18) . ?
O3 C9 1.4319(18) . ?
C12 C11 1.402(2) . ?
C12 C16 1.4017(19) 2_656 ?
C12 C17 1.5115(18) . ?
C16 C11 1.4021(18) . ?
C16 C10 1.5085(19) . ?
C11 C20 1.5146(18) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C4 1.454(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.165(3) . ?
C6 C1 1.172(2) . ?
C6 C7 1.466(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 H1 0.9300 . ?
C8 C2 1.163(3) . ?
C8 C9 1.453(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?

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 O1 C7 112.03(12) . . ?
C5 O2 C17 111.37(11) . . ?
C20 O3 C9 111.96(12) . . ?
C11 C12 C16 120.47(12) . 2_656 ?
C11 C12 C17 119.56(12) . . ?
C16 C12 C17 119.96(12) 2_656 . ?
C12 C16 C11 119.70(12) 2_656 . ?
C12 C16 C10 119.56(12) 2_656 . ?
C11 C16 C10 120.68(12) . . ?
C12 C11 C16 119.80(12) . . ?
C12 C11 C20 119.78(12) . . ?
C16 C11 C20 120.36(12) . . ?
O3 C20 C11 109.62(12) . . ?
O3 C20 H20A 109.7 . . ?
C11 C20 H20A 109.7 . . ?
O3 C20 H20B 109.7 . . ?
C11 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
O2 C17 C12 107.89(11) . . ?
O2 C17 H17A 110.1 . . ?
C12 C17 H17A 110.1 . . ?
O2 C17 H17B 110.1 . . ?
C12 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
O1 C10 C16 109.22(11) . . ?
O1 C10 H10A 109.8 . . ?
C16 C10 H10A 109.8 . . ?
O1 C10 H10B 109.8 . . ?
C16 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
O2 C5 C4 108.85(13) . . ?
O2 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
O2 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C3 C4 C5 179.01(19) . . ?
C1 C6 C7 178.45(19) . . ?
O1 C7 C6 112.63(13) . . ?
O1 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
O1 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C6 C1 H1 180.0 . . ?
C2 C8 C9 178.91(19) . . ?
O3 C9 C8 112.54(14) . . ?
O3 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
O3 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C4 C3 H3 180.0 . . ?
C8 C2 H2 180.0 . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.069

