# 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 2020

####################################################################### 
# 
# 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_sa69
_audit_block_doi                 10.5517/ccdc.csd.cc240t88
_database_code_depnum_ccdc_archive 'CCDC 1966989'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 O8'
_chemical_formula_sum            'C24 H28 O8'
_chemical_formula_weight         444.46

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/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                   14.2917(15)
_cell_length_b                   5.5579(6)
_cell_length_c                   14.5639(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.471(7)
_cell_angle_gamma                90
_cell_volume                     1076.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10460
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      28.16

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9314
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.418
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2478
_reflns_number_gt                2140
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0557P)²+0.4691P] 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
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2478
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.55719(9) 0.5895(2) 0.47647(9) 0.0183(3) Uani 1 1 d . . . . .
H1 H 0.5337 0.6903 0.4153 0.022 Uiso 1 1 calc R U . . .
C2 C 0.50340(9) 0.3428(2) 0.45572(9) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.5519 0.2093 0.4855 0.022 Uiso 1 1 calc R U . . .
C3 C 0.44141(9) 0.2904(2) 0.34955(10) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.42339(8) 0.4283(2) 0.28169(8) 0.0299(3) Uani 1 1 d . . . . .
C4 C 0.34555(12) -0.0072(3) 0.24071(11) 0.0283(3) Uani 1 1 d . . . . .
H4A H 0.3242 -0.1747 0.2409 0.042 Uiso 1 1 calc R U . . .
H4B H 0.3846 0.0078 0.1979 0.042 Uiso 1 1 calc R U . . .
H4C H 0.2862 0.0969 0.2160 0.042 Uiso 1 1 calc R U . . .
O4 O 0.40694(8) 0.06393(18) 0.33979(7) 0.0242(3) Uani 1 1 d . . . . .
C11 C 0.67043(9) 0.5875(2) 0.52057(9) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.72462(9) 0.7619(2) 0.49064(9) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.6894 0.8830 0.4450 0.023 Uiso 1 1 calc R U . . .
C13 C 0.82873(10) 0.7590(3) 0.52694(10) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.88099(9) 0.5804(3) 0.59467(10) 0.0215(3) Uani 1 1 d . . . . .
C15 C 0.82791(10) 0.4134(3) 0.62648(11) 0.0254(3) Uani 1 1 d . . . . .
H15 H 0.8629 0.2961 0.6741 0.030 Uiso 1 1 calc R U . . .
C16 C 0.72304(10) 0.4168(3) 0.58888(10) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.6872 0.2998 0.6106 0.029 Uiso 1 1 calc R U . . .
O17 O 0.88796(7) 0.9166(2) 0.50099(8) 0.0300(3) Uani 1 1 d . . . . .
C17 C 0.83901(12) 1.0827(3) 0.42367(12) 0.0311(3) Uani 1 1 d . . . . .
H17A H 0.8894 1.1854 0.4121 0.047 Uiso 1 1 calc R U . . .
H17B H 0.7925 1.1828 0.4425 0.047 Uiso 1 1 calc R U . . .
H17C H 0.8015 0.9941 0.3632 0.047 Uiso 1 1 calc R U . . .
O18 O 0.98322(7) 0.5866(2) 0.62328(8) 0.0303(3) Uani 1 1 d . . . . .
C18 C 1.03654(11) 0.3842(3) 0.67674(16) 0.0407(4) Uani 1 1 d . . . . .
H18A H 1.1088 0.4082 0.6934 0.061 Uiso 1 1 calc R U . . .
H18B H 1.0149 0.2391 0.6362 0.061 Uiso 1 1 calc R U . . .
H18C H 1.0227 0.3656 0.7375 0.061 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
C1 C11 1.5070(16) . ?
C1 C2 1.5469(18) . ?
C1 C2 1.5788(18) 3_666 ?
C1 H1 1.0000 . ?
C2 C3 1.5026(18) . ?
C2 C1 1.5788(18) 3_666 ?
C2 H2 1.0000 . ?
C3 O3 1.2020(17) . ?
C3 O4 1.3399(16) . ?
C4 O4 1.4427(17) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 C16 1.3812(19) . ?
C11 C12 1.4058(18) . ?
C12 C13 1.3848(18) . ?
C12 H12 0.9500 . ?
C13 O17 1.3642(16) . ?
C13 C14 1.406(2) . ?
C14 O18 1.3652(15) . ?
C14 C15 1.381(2) . ?
C15 C16 1.3950(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O17 C17 1.4257(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O18 C18 1.421(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C11 C1 C2 117.13(11) . . ?
C11 C1 C2 118.99(11) . 3_666 ?
C2 C1 C2 89.21(10) . 3_666 ?
C11 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C2 C1 H1 110.0 3_666 . ?
C3 C2 C1 115.89(11) . . ?
C3 C2 C1 115.98(10) . 3_666 ?
C1 C2 C1 90.79(10) . 3_666 ?
C3 C2 H2 110.9 . . ?
C1 C2 H2 110.9 . . ?
C1 C2 H2 110.9 3_666 . ?
O3 C3 O4 123.52(12) . . ?
O3 C3 C2 126.19(12) . . ?
O4 C3 C2 110.29(11) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 O4 C4 115.39(11) . . ?
C16 C11 C12 118.72(11) . . ?
C16 C11 C1 121.92(11) . . ?
C12 C11 C1 119.36(11) . . ?
C13 C12 C11 120.70(12) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O17 C13 C12 125.16(13) . . ?
O17 C13 C14 115.06(11) . . ?
C12 C13 C14 119.77(12) . . ?
O18 C14 C15 124.91(13) . . ?
O18 C14 C13 115.51(12) . . ?
C15 C14 C13 119.58(12) . . ?
C14 C15 C16 120.16(13) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 121.02(13) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C13 O17 C17 117.37(11) . . ?
O17 C17 H17A 109.5 . . ?
O17 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O17 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 O18 C18 116.54(12) . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C11 C1 C2 C3 -117.91(12) . . . . ?
C2 C1 C2 C3 119.58(13) 3_666 . . . ?
C11 C1 C2 C1 122.51(13) . . . 3_666 ?
C2 C1 C2 C1 0.000(0) 3_666 . . 3_666 ?
C1 C2 C3 O3 -6.59(19) . . . . ?
C1 C2 C3 O3 98.10(16) 3_666 . . . ?
C1 C2 C3 O4 173.93(10) . . . . ?
C1 C2 C3 O4 -81.38(14) 3_666 . . . ?
O3 C3 O4 C4 0.12(19) . . . . ?
C2 C3 O4 C4 179.61(11) . . . . ?
C2 C1 C11 C16 -36.30(18) . . . . ?
C2 C1 C11 C16 69.13(18) 3_666 . . . ?
C2 C1 C11 C12 142.80(12) . . . . ?
C2 C1 C11 C12 -111.77(14) 3_666 . . . ?
C16 C11 C12 C13 1.7(2) . . . . ?
C1 C11 C12 C13 -177.48(12) . . . . ?
C11 C12 C13 O17 178.54(13) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
O17 C13 C14 O18 -1.31(18) . . . . ?
C12 C13 C14 O18 177.52(12) . . . . ?
O17 C13 C14 C15 179.32(13) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
O18 C14 C15 C16 -176.96(14) . . . . ?
C13 C14 C15 C16 2.3(2) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C1 C11 C16 C15 177.95(14) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
C12 C13 O17 C17 -6.3(2) . . . . ?
C14 C13 O17 C17 172.46(13) . . . . ?
C15 C14 O18 C18 10.6(2) . . . . ?
C13 C14 O18 C18 -168.73(14) . . . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-3

