# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_c2c
_audit_block_doi                 10.5517/ccxk8qf
_database_code_depnum_ccdc_archive 'CCDC 850755'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/cg3003349 2012
_audit_update_record             
;
2011-10-25 deposited with the CCDC.	2025-05-04 downloaded from the CCDC.
;
#TrackingRef '7821_web_deposit_cif_file_0_BangboYan_1319579187.YanWKU01.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H30 Ca3 O24'
_chemical_formula_weight         750.66

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'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'c 2/c'

loop_
_symmetry_equiv_pos_as_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                   6.72570(10)
_cell_length_b                   20.8422(4)
_cell_length_c                   20.1942(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.5070(10)
_cell_angle_gamma                90.00
_cell_volume                     2791.91(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1560
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8787
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46626
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         36.40
_reflns_number_total             6750
_reflns_number_gt                5059
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0238P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6750
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca 0.88711(6) 0.871849(14) 0.007552(16) 0.01882(7) Uani 1 1 d . . .
Ca2 Ca 1.0000 0.875142(19) 0.2500 0.01702(8) Uani 1 2 d S . .
O1 O 0.95288(19) 1.28268(5) 0.12264(6) 0.0217(2) Uani 1 1 d . . .
O2 O 1.0061(2) 1.19043(6) 0.07377(7) 0.0298(3) Uani 1 1 d . . .
O3 O 0.9926(2) 0.98527(5) 0.30377(6) 0.0251(3) Uani 1 1 d . . .
O4 O 0.9427(2) 0.76780(5) 0.19615(6) 0.0285(3) Uani 1 1 d . . .
O5 O 0.7880(2) 0.56223(6) 0.07632(6) 0.0272(3) Uani 1 1 d . . .
O6 O 0.91914(18) 0.47177(5) 0.12180(6) 0.0212(2) Uani 1 1 d . . .
C1 C 1.0000 1.22084(9) 0.2500 0.0161(4) Uani 1 2 d S . .
H1 H 1.0000 1.2695(12) 0.2500 0.012(6) Uiso 1 2 d S . .
C2 C 0.9840(2) 1.18754(6) 0.18933(8) 0.0160(2) Uani 1 1 d . . .
C3 C 0.9827(3) 1.12076(6) 0.18998(9) 0.0161(3) Uani 1 1 d . . .
H3 H 0.974(3) 1.1006(10) 0.1494(13) 0.027(5) Uiso 1 1 d . . .
C4 C 1.0000 1.08697(9) 0.2500 0.0154(3) Uani 1 2 d S . .
C5 C 0.9798(2) 1.22251(7) 0.12378(8) 0.0173(3) Uani 1 1 d . . .
C6 C 1.0000 1.01510(9) 0.2500 0.0159(4) Uani 1 2 d S . .
C7 C 1.0000 0.66606(9) 0.2500 0.0159(3) Uani 1 2 d S . .
C8 C 0.9473(2) 0.63260(7) 0.19039(8) 0.0166(3) Uani 1 1 d . . .
H8 H 0.905(3) 0.6517(9) 0.1516(10) 0.012(4) Uiso 1 1 d . . .
C9 C 0.9461(2) 0.56579(6) 0.18979(7) 0.0144(2) Uani 1 1 d . . .
C10 C 1.0000 0.53249(9) 0.2500 0.0155(3) Uani 1 2 d S . .
H10 H 1.0000 0.4845(13) 0.2500 0.025(7) Uiso 1 2 d S . .
C11 C 1.0000 0.73798(9) 0.2500 0.0166(4) Uani 1 2 d S . .
C12 C 0.8784(2) 0.53146(7) 0.12481(8) 0.0166(3) Uani 1 1 d . . .
O1W O 1.1947(2) 0.92872(6) 0.00336(8) 0.0272(3) Uani 1 1 d . . .
H1WA H 1.191(5) 0.9602(15) -0.0248(17) 0.066(10) Uiso 1 1 d . . .
H1WB H 1.267(6) 0.9414(14) 0.0427(17) 0.062(9) Uiso 1 1 d . . .
O2W O 0.7995(2) 0.96243(7) 0.07484(7) 0.0264(3) Uani 1 1 d . . .
H2WA H 0.876(5) 0.9729(12) 0.1112(15) 0.041(7) Uiso 1 1 d . . .
H2WB H 0.695(7) 0.9682(18) 0.0820(19) 0.084(12) Uiso 1 1 d . . .
O3W O 0.5400(2) 0.84072(6) 0.01123(7) 0.0275(3) Uani 1 1 d . . .
H3WA H 0.501(4) 0.8198(13) 0.0464(13) 0.040(7) Uiso 1 1 d . . .
H3WB H 0.443(5) 0.8633(12) -0.0016(13) 0.041(7) Uiso 1 1 d . . .
O4W O 0.9321(3) 0.77395(6) 0.06372(8) 0.0332(3) Uani 1 1 d . . .
H4WA H 0.945(4) 0.7669(11) 0.1058(15) 0.038(7) Uiso 1 1 d . . .
H4WB H 0.968(5) 0.7448(14) 0.0466(14) 0.054(9) Uiso 1 1 d . . .
O5W O 1.1453(2) 0.87274(6) 0.14172(9) 0.0328(3) Uani 1 1 d . . .
H5WA H 1.210(5) 0.9010(14) 0.1414(14) 0.042(8) Uiso 1 1 d . . .
H5WB H 1.220(5) 0.8398(13) 0.1384(13) 0.046(8) Uiso 1 1 d . . .
O6W O 0.6658(2) 0.87908(7) 0.19549(9) 0.0335(3) Uani 1 1 d . . .
H6WA H 0.597(4) 0.9052(14) 0.1756(13) 0.041(7) Uiso 1 1 d . . .
H6WB H 0.617(4) 0.8485(12) 0.1752(13) 0.029(6) Uiso 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
Ca1 O2 2.2994(13) 5_775 ?
Ca1 O4W 2.3299(14) . ?
Ca1 O5 2.3417(12) 7_665 ?
Ca1 O1W 2.3980(14) . ?
Ca1 O3W 2.4360(14) . ?
Ca1 O2W 2.4540(14) . ?
Ca1 O5W 2.9667(19) . ?
Ca1 H4WB 2.79(3) . ?
Ca2 O6W 2.3354(15) 2_755 ?
Ca2 O6W 2.3354(15) . ?
Ca2 O4 2.4895(12) 2_755 ?
Ca2 O4 2.4896(12) . ?
Ca2 O5W 2.5385(16) 2_755 ?
Ca2 O5W 2.5386(16) . ?
Ca2 O3 2.5432(12) . ?
Ca2 O3 2.5432(12) 2_755 ?
Ca2 C11 2.8588(19) . ?
Ca2 C6 2.9170(19) . ?
O1 C5 1.2669(18) . ?
O2 C5 1.2479(19) . ?
O2 Ca1 2.2994(13) 5_775 ?
O3 C6 1.2592(15) . ?
O4 C11 1.2567(15) . ?
O5 C12 1.2424(19) . ?
O5 Ca1 2.3417(12) 7_665 ?
O6 C12 1.2776(18) . ?
C1 C2 1.3966(18) 2_755 ?
C1 C2 1.3967(18) . ?
C1 H1 1.01(3) . ?
C2 C3 1.3920(18) . ?
C2 C5 1.507(2) . ?
C3 C4 1.3899(19) . ?
C3 H3 0.91(2) . ?
C4 C3 1.3899(19) 2_755 ?
C4 C6 1.498(3) . ?
C6 O3 1.2593(15) 2_755 ?
C7 C8 1.3857(18) 2_755 ?
C7 C8 1.3857(18) . ?
C7 C11 1.499(3) . ?
C8 C9 1.3925(19) . ?
C8 H8 0.88(2) . ?
C9 C10 1.3949(17) . ?
C9 C12 1.498(2) . ?
C10 C9 1.3949(17) 2_755 ?
C10 H10 1.00(3) . ?
C11 O4 1.2567(15) 2_755 ?
O1W H1WA 0.87(3) . ?
O1W H1WB 0.90(4) . ?
O2W H2WA 0.85(3) . ?
O2W H2WB 0.75(5) . ?
O3W H3WA 0.91(3) . ?
O3W H3WB 0.81(3) . ?
O4W H4WA 0.85(3) . ?
O4W H4WB 0.76(3) . ?
O5W H5WA 0.73(3) . ?
O5W H5WB 0.86(3) . ?
O6W H6WA 0.78(3) . ?
O6W H6WB 0.80(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
O2 Ca1 O4W 79.78(5) 5_775 . ?
O2 Ca1 O5 89.64(5) 5_775 7_665 ?
O4W Ca1 O5 151.07(5) . 7_665 ?
O2 Ca1 O1W 83.15(5) 5_775 . ?
O4W Ca1 O1W 114.00(6) . . ?
O5 Ca1 O1W 91.04(5) 7_665 . ?
O2 Ca1 O3W 106.58(5) 5_775 . ?
O4W Ca1 O3W 78.45(5) . . ?
O5 Ca1 O3W 78.96(5) 7_665 . ?
O1W Ca1 O3W 165.82(5) . . ?
O2 Ca1 O2W 164.07(5) 5_775 . ?
O4W Ca1 O2W 115.33(5) . . ?
O5 Ca1 O2W 79.11(5) 7_665 . ?
O1W Ca1 O2W 85.80(5) . . ?
O3W Ca1 O2W 82.47(5) . . ?
O2 Ca1 O5W 116.81(5) 5_775 . ?
O4W Ca1 O5W 63.36(5) . . ?
O5 Ca1 O5W 143.64(4) 7_665 . ?
O1W Ca1 O5W 69.57(5) . . ?
O3W Ca1 O5W 113.15(5) . . ?
O2W Ca1 O5W 69.35(4) . . ?
O2 Ca1 H4WB 66.2(6) 5_775 . ?
O4W Ca1 H4WB 13.6(6) . . ?
O5 Ca1 H4WB 144.3(6) 7_665 . ?
O1W Ca1 H4WB 110.5(7) . . ?
O3W Ca1 H4WB 83.2(7) . . ?
O2W Ca1 H4WB 128.8(6) . . ?
O5W Ca1 H4WB 72.0(6) . . ?
O6W Ca2 O6W 175.97(7) 2_755 . ?
O6W Ca2 O4 76.01(5) 2_755 2_755 ?
O6W Ca2 O4 107.76(5) . 2_755 ?
O6W Ca2 O4 107.76(5) 2_755 . ?
O6W Ca2 O4 76.01(5) . . ?
O4 Ca2 O4 52.04(6) 2_755 . ?
O6W Ca2 O5W 94.13(6) 2_755 2_755 ?
O6W Ca2 O5W 85.95(6) . 2_755 ?
O4 Ca2 O5W 70.12(4) 2_755 2_755 ?
O4 Ca2 O5W 107.74(5) . 2_755 ?
O6W Ca2 O5W 85.95(6) 2_755 . ?
O6W Ca2 O5W 94.13(6) . . ?
O4 Ca2 O5W 107.74(5) 2_755 . ?
O4 Ca2 O5W 70.12(4) . . ?
O5W Ca2 O5W 177.74(6) 2_755 . ?
O6W Ca2 O3 81.49(5) 2_755 . ?
O6W Ca2 O3 94.84(5) . . ?
O4 Ca2 O3 129.57(4) 2_755 . ?
O4 Ca2 O3 170.08(5) . . ?
O5W Ca2 O3 67.21(4) 2_755 . ?
O5W Ca2 O3 115.02(4) . . ?
O6W Ca2 O3 94.84(5) 2_755 2_755 ?
O6W Ca2 O3 81.49(5) . 2_755 ?
O4 Ca2 O3 170.07(5) 2_755 2_755 ?
O4 Ca2 O3 129.57(4) . 2_755 ?
O5W Ca2 O3 115.02(4) 2_755 2_755 ?
O5W Ca2 O3 67.21(4) . 2_755 ?
O3 Ca2 O3 51.01(6) . 2_755 ?
O6W Ca2 C11 92.02(3) 2_755 . ?
O6W Ca2 C11 92.02(3) . . ?
O4 Ca2 C11 26.02(3) 2_755 . ?
O4 Ca2 C11 26.02(3) . . ?
O5W Ca2 C11 88.87(3) 2_755 . ?
O5W Ca2 C11 88.87(3) . . ?
O3 Ca2 C11 154.49(3) . . ?
O3 Ca2 C11 154.49(3) 2_755 . ?
O6W Ca2 C6 87.98(3) 2_755 . ?
O6W Ca2 C6 87.98(3) . . ?
O4 Ca2 C6 153.98(3) 2_755 . ?
O4 Ca2 C6 153.98(3) . . ?
O5W Ca2 C6 91.13(3) 2_755 . ?
O5W Ca2 C6 91.13(3) . . ?
O3 Ca2 C6 25.51(3) . . ?
O3 Ca2 C6 25.51(3) 2_755 . ?
C11 Ca2 C6 180.0 . . ?
C5 O2 Ca1 169.47(13) . 5_775 ?
C6 O3 Ca2 94.07(10) . . ?
C11 O4 Ca2 93.62(10) . . ?
C12 O5 Ca1 174.37(11) . 7_665 ?
C2 C1 C2 120.41(18) 2_755 . ?
C2 C1 H1 119.80(9) 2_755 . ?
C2 C1 H1 119.80(9) . . ?
C3 C2 C1 119.23(15) . . ?
C3 C2 C5 119.51(14) . . ?
C1 C2 C5 121.17(12) . . ?
C4 C3 C2 121.00(15) . . ?
C4 C3 H3 122.2(14) . . ?
C2 C3 H3 116.8(14) . . ?
C3 C4 C3 119.12(17) . 2_755 ?
C3 C4 C6 120.44(9) . . ?
C3 C4 C6 120.44(9) 2_755 . ?
O2 C5 O1 123.69(15) . . ?
O2 C5 C2 117.85(13) . . ?
O1 C5 C2 118.46(13) . . ?
O3 C6 O3 120.84(18) . 2_755 ?
O3 C6 C4 119.58(9) . . ?
O3 C6 C4 119.58(9) 2_755 . ?
O3 C6 Ca2 60.42(9) . . ?
O3 C6 Ca2 60.42(9) 2_755 . ?
C4 C6 Ca2 180.0 . . ?
C8 C7 C8 119.56(18) 2_755 . ?
C8 C7 C11 120.22(9) 2_755 . ?
C8 C7 C11 120.22(9) . . ?
C7 C8 C9 120.74(14) . . ?
C7 C8 H8 122.9(12) . . ?
C9 C8 H8 116.2(12) . . ?
C8 C9 C10 119.31(14) . . ?
C8 C9 C12 119.06(13) . . ?
C10 C9 C12 121.57(12) . . ?
C9 C10 C9 120.33(17) 2_755 . ?
C9 C10 H10 119.84(9) 2_755 . ?
C9 C10 H10 119.84(9) . . ?
O4 C11 O4 120.71(18) . 2_755 ?
O4 C11 C7 119.64(9) . . ?
O4 C11 C7 119.65(9) 2_755 . ?
O4 C11 Ca2 60.36(9) . . ?
O4 C11 Ca2 60.35(9) 2_755 . ?
C7 C11 Ca2 180.0 . . ?
O5 C12 O6 123.10(14) . . ?
O5 C12 C9 118.84(13) . . ?
O6 C12 C9 118.06(13) . . ?
Ca1 O1W H1WA 118(2) . . ?
Ca1 O1W H1WB 117(2) . . ?
H1WA O1W H1WB 108(3) . . ?
Ca1 O2W H2WA 120.6(19) . . ?
Ca1 O2W H2WB 123(3) . . ?
H2WA O2W H2WB 104(4) . . ?
Ca1 O3W H3WA 123.8(18) . . ?
Ca1 O3W H3WB 124.1(19) . . ?
H3WA O3W H3WB 102(2) . . ?
Ca1 O4W H4WA 128.2(16) . . ?
Ca1 O4W H4WB 120(2) . . ?
H4WA O4W H4WB 109(3) . . ?
Ca2 O5W Ca1 122.43(6) . . ?
Ca2 O5W H5WA 108(2) . . ?
Ca1 O5W H5WA 105(2) . . ?
Ca2 O5W H5WB 113.4(18) . . ?
Ca1 O5W H5WB 100.7(18) . . ?
H5WA O5W H5WB 107(3) . . ?
Ca2 O6W H6WA 135(2) . . ?
Ca2 O6W H6WB 119.9(18) . . ?
H6WA O6W H6WB 98(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        36.40
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.078
