# 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 2018

####################################################################### 
# 
# 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_20161028
_database_code_depnum_ccdc_archive 'CCDC 1845477'
_audit_update_record             
;
2018-05-26 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H10 O10'
_chemical_formula_moiety         'C14 H10 O10'
_chemical_formula_weight         338.23
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   4.60137(12)
_cell_length_b                   7.6252(2)
_cell_length_c                   9.3955(2)
_cell_angle_alpha                101.9580(19)
_cell_angle_beta                 96.9215(17)
_cell_angle_gamma                103.4610(19)
_cell_volume                     308.666(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1950
_cell_measurement_theta_min      4.89
_cell_measurement_theta_max      67.80
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             174.00
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.932

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            3360
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         4.889
_diffrn_reflns_theta_full        68.170
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1107
_reflns_number_gt                934
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1092
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1107
_refine_ls_number_parameters     117
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0756P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 1.2615(2) -0.01599(15) 0.39510(11) 0.0193(3) Uani 1 1 d . . .
H1 H 1.3020 -0.1192 0.3860 0.023 Uiso 1 1 calc R . .
O2 O 0.6140(2) 0.29891(15) 0.19468(11) 0.0170(3) Uani 1 1 d . . .
O4 O 1.0525(2) 0.28377(16) 0.41043(11) 0.0180(3) Uani 1 1 d . . .
H4 H 1.1859 0.2615 0.4681 0.022 Uiso 1 1 calc R . .
O9 O 0.3077(2) 0.45476(15) 0.11562(11) 0.0189(3) Uani 1 1 d . . .
C2 C 0.9406(3) 0.1358(2) 0.29287(16) 0.0167(4) Uani 1 1 d . . .
C3 C 0.6093(3) -0.0072(2) 0.05748(16) 0.0164(4) Uani 1 1 d . . .
C4 C 0.7197(4) 0.1416(2) 0.18110(17) 0.0161(4) Uani 1 1 d . . .
C5 C 0.7156(4) -0.1653(2) 0.04649(16) 0.0170(4) Uani 1 1 d . . .
C6 C 1.0450(3) -0.0255(2) 0.28067(16) 0.0174(4) Uani 1 1 d . . .
C7 C 0.9339(4) -0.1764(2) 0.15865(16) 0.0173(4) Uani 1 1 d . . .
H7 H 1.0052 -0.2847 0.1519 0.021 Uiso 1 1 calc R . .
C8 C 0.3956(4) 0.3156(2) 0.08813(17) 0.0168(4) Uani 1 1 d . . .
O3 O 0.4190(3) 0.66647(16) 0.39724(12) 0.0195(3) Uani 1 1 d . . .
H10 H 0.293(5) 0.612(3) 0.433(2) 0.038(6) Uiso 1 1 d . . .
H11 H 0.409(5) 0.602(4) 0.314(3) 0.049(7) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C6 1.3526(18) . ?
O1 H1 0.8400 . ?
O2 C8 1.3777(19) . ?
O2 C4 1.384(2) . ?
O4 C2 1.3543(19) . ?
O4 H4 0.8400 . ?
O9 C8 1.211(2) . ?
C2 C4 1.386(2) . ?
C2 C6 1.410(2) . ?
C3 C4 1.392(2) . ?
C3 C5 1.392(2) . ?
C3 C3 1.424(3) 2_655 ?
C5 C7 1.396(2) . ?
C5 C8 1.465(2) 2_655 ?
C6 C7 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C5 1.465(2) 2_655 ?
O3 H10 0.79(2) . ?
O3 H11 0.82(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
C6 O1 H1 109.5 . . ?
C8 O2 C4 122.04(13) . . ?
C2 O4 H4 109.5 . . ?
O4 C2 C4 119.92(15) . . ?
O4 C2 C6 121.38(14) . . ?
C4 C2 C6 118.70(15) . . ?
C4 C3 C5 120.13(16) . . ?
C4 C3 C3 118.79(19) . 2_655 ?
C5 C3 C3 121.07(19) . 2_655 ?
O2 C4 C2 118.53(15) . . ?
O2 C4 C3 120.91(15) . . ?
C2 C4 C3 120.56(16) . . ?
C3 C5 C7 120.57(15) . . ?
C3 C5 C8 118.62(15) . 2_655 ?
C7 C5 C8 120.74(15) . 2_655 ?
O1 C6 C7 124.71(15) . . ?
O1 C6 C2 113.85(14) . . ?
C7 C6 C2 121.43(14) . . ?
C6 C7 C5 118.60(15) . . ?
C6 C7 H7 120.7 . . ?
C5 C7 H7 120.7 . . ?
O9 C8 O2 116.29(13) . . ?
O9 C8 C5 125.24(15) . 2_655 ?
O2 C8 C5 118.46(14) . 2_655 ?
H10 O3 H11 107(2) . . ?

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
C8 O2 C4 C2 179.75(13) . . . . ?
C8 O2 C4 C3 0.3(2) . . . . ?
O4 C2 C4 O2 -1.4(2) . . . . ?
C6 C2 C4 O2 178.91(12) . . . . ?
O4 C2 C4 C3 178.03(13) . . . . ?
C6 C2 C4 C3 -1.7(3) . . . . ?
C5 C3 C4 O2 -179.24(13) . . . . ?
C3 C3 C4 O2 1.8(3) 2_655 . . . ?
C5 C3 C4 C2 1.3(3) . . . . ?
C3 C3 C4 C2 -177.65(16) 2_655 . . . ?
C4 C3 C5 C7 -0.1(3) . . . . ?
C3 C3 C5 C7 178.83(16) 2_655 . . . ?
C4 C3 C5 C8 -177.31(13) . . . 2_655 ?
C3 C3 C5 C8 1.7(3) 2_655 . . 2_655 ?
O4 C2 C6 O1 -0.1(2) . . . . ?
C4 C2 C6 O1 179.60(13) . . . . ?
O4 C2 C6 C7 -178.87(14) . . . . ?
C4 C2 C6 C7 0.8(3) . . . . ?
O1 C6 C7 C5 -178.31(13) . . . . ?
C2 C6 C7 C5 0.4(3) . . . . ?
C3 C5 C7 C6 -0.7(3) . . . . ?
C8 C5 C7 C6 176.42(13) 2_655 . . . ?
C4 O2 C8 O9 175.86(13) . . . . ?
C4 O2 C8 C5 -3.0(2) . . . 2_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O1 . . 2_856 2.6963(15) 0.840 2.547 91.0 no
O1 H1 O3 . . 1_645 2.6872(18) 0.840 1.854 170.9 no
O4 H4 O1 . . . 2.6628(18) 0.840 2.206 114.2 no
O4 H4 O3 . . 2_766 2.7478(15) 0.840 1.975 152.5 no
O3 H10 O4 . . 2_666 3.0266(17) 0.79(2) 2.45(2) 132(2) no
O3 H11 O9 . . . 2.7181(14) 0.82(2) 1.90(2) 169(2) no
####################################################################### 
# 
# 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_20161226
_database_code_depnum_ccdc_archive 'CCDC 1845478'
_audit_update_record             
;
2018-05-26 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C30 H30 O12'
_chemical_formula_moiety         'C30 H30 O12'
_chemical_formula_weight         582.56
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.4510(3)
_cell_length_b                   14.8082(7)
_cell_length_c                   17.0789(7)
_cell_angle_alpha                84.393(2)
_cell_angle_beta                 85.111(2)
_cell_angle_gamma                87.553(2)
_cell_volume                     1366.18(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5644
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    300
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612.00
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.453
_exptl_absorpt_correction_T_max  0.928

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      300
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18740
_diffrn_reflns_av_unetI/netI     0.1482
_diffrn_reflns_av_R_equivalents  0.1421
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.000
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4906
_reflns_number_gt                1487
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1966
_refine_ls_R_factor_gt           0.1047
_refine_ls_wR_factor_ref         0.3152
_refine_ls_wR_factor_gt          0.2367
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4906
_refine_ls_number_parameters     379
_refine_ls_goodness_of_fit_ref   0.848
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1518P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O1 O 1.3959(7) 0.6368(2) 0.6386(2) 0.0694(11) Uani 1 1 d . . .
O2 O 0.9926(7) 0.4215(2) 0.8525(2) 0.0710(11) Uani 1 1 d . . .
O3 O 1.1938(7) 0.6252(3) 0.5335(2) 0.0835(13) Uani 1 1 d . . .
O4 O 1.1922(7) 0.4343(3) 0.9582(2) 0.0797(12) Uani 1 1 d . . .
O5 O 1.8649(7) 0.6659(3) 0.8552(2) 0.0708(11) Uani 1 1 d . . .
O6 O 1.7847(7) 0.7070(3) 0.7017(2) 0.0704(11) Uani 1 1 d . . .
O7 O 0.5297(7) 0.3949(3) 0.6302(2) 0.0722(11) Uani 1 1 d . . .
O8 O 0.6048(7) 0.3477(3) 0.7870(2) 0.0700(11) Uani 1 1 d . . .
O9 O 1.6305(8) 0.7447(3) 0.9431(2) 0.0782(12) Uani 1 1 d . . .
O10 O 1.6260(8) 0.8324(3) 0.7563(2) 0.0824(13) Uani 1 1 d . . .
O11 O 0.7016(8) 0.2535(3) 0.6389(2) 0.0755(12) Uani 1 1 d . . .
O12 O 0.9043(8) 0.2387(3) 0.8048(2) 0.0793(12) Uani 1 1 d . . .
C1 C 1.6594(11) 0.6295(4) 0.8283(3) 0.0654(15) Uani 1 1 d . . .
C2 C 1.6165(10) 0.6527(4) 0.7485(3) 0.0621(15) Uani 1 1 d . . .
C3 C 1.4305(11) 0.6131(4) 0.7181(3) 0.0640(15) Uani 1 1 d . . .
C4 C 1.2113(11) 0.5986(4) 0.6020(4) 0.0722(17) Uani 1 1 d . . .
C5 C 1.0586(10) 0.5314(4) 0.6489(3) 0.0614(14) Uani 1 1 d . . .
C6 C 0.8732(11) 0.4905(4) 0.6156(3) 0.0677(16) Uani 1 1 d . . .
H8 H 0.8464 0.5049 0.5627 0.081 Uiso 1 1 calc R . .
C7 C 0.7290(11) 0.4281(4) 0.6618(3) 0.0646(15) Uani 1 1 d . . .
C8 C 0.7718(11) 0.4048(4) 0.7414(3) 0.0655(15) Uani 1 1 d . . .
C9 C 0.9559(11) 0.4442(4) 0.7731(3) 0.0663(15) Uani 1 1 d . . .
C10 C 1.1754(11) 0.4602(4) 0.8895(3) 0.0698(16) Uani 1 1 d . . .
C11 C 1.3281(11) 0.5284(4) 0.8430(3) 0.0656(15) Uani 1 1 d . . .
C12 C 1.5154(10) 0.5688(4) 0.8759(3) 0.0681(16) Uani 1 1 d . . .
H16 H 1.5427 0.5552 0.9289 0.082 Uiso 1 1 calc R . .
C13 C 1.2866(10) 0.5504(4) 0.7627(3) 0.0623(15) Uani 1 1 d . . .
C14 C 1.1025(10) 0.5062(4) 0.7287(3) 0.0624(15) Uani 1 1 d . . .
C15 C 1.8309(14) 0.7225(4) 0.9158(4) 0.0719(17) Uani 1 1 d . . .
C16 C 2.0736(11) 0.7514(4) 0.9375(3) 0.0795(18) Uani 1 1 d . . .
H1B H 2.1887 0.7533 0.8908 0.095 Uiso 1 1 calc R . .
H2A H 2.1357 0.7057 0.9761 0.095 Uiso 1 1 calc R . .
C17 C 2.0693(12) 0.8418(4) 0.9704(3) 0.0827(18) Uani 1 1 d . . .
H3B H 2.2302 0.8520 0.9875 0.099 Uiso 1 1 calc R . .
H4A H 1.9505 0.8417 1.0160 0.099 Uiso 1 1 calc R . .
C18 C 2.0017(14) 0.9181(5) 0.9092(4) 0.118(3) Uani 1 1 d . . .
H5C H 2.1206 0.9189 0.8643 0.141 Uiso 1 1 calc R . .
H6A H 2.0004 0.9751 0.9317 0.141 Uiso 1 1 calc R . .
H7B H 1.8413 0.9087 0.8929 0.141 Uiso 1 1 calc R . .
C19 C 1.7869(12) 0.7981(5) 0.7163(4) 0.0729(17) Uani 1 1 d . . .
C20 C 2.0168(11) 0.8398(4) 0.6763(4) 0.0824(18) Uani 1 1 d . . .
H9B H 2.0386 0.8229 0.6226 0.099 Uiso 1 1 calc R . .
H10A H 2.1570 0.8146 0.7035 0.099 Uiso 1 1 calc R . .
C21 C 2.0160(11) 0.9435(4) 0.6740(3) 0.0803(18) Uani 1 1 d . . .
H11A H 1.9724 0.9610 0.7268 0.096 Uiso 1 1 calc R . .
H12B H 2.1808 0.9639 0.6576 0.096 Uiso 1 1 calc R . .
C22 C 1.8376(11) 0.9905(4) 0.6185(3) 0.0888(19) Uani 1 1 d . . .
H13A H 1.8446 1.0550 0.6193 0.107 Uiso 1 1 calc R . .
H14C H 1.6734 0.9717 0.6352 0.107 Uiso 1 1 calc R . .
H15B H 1.8818 0.9744 0.5659 0.107 Uiso 1 1 calc R . .
C23 C 0.5321(13) 0.3029(5) 0.6205(3) 0.0751(18) Uani 1 1 d . . .
C24 C 0.3011(11) 0.2790(4) 0.5887(4) 0.0847(19) Uani 1 1 d . . .
H17A H 0.2689 0.3215 0.5435 0.102 Uiso 1 1 calc R . .
H18B H 0.1652 0.2848 0.6286 0.102 Uiso 1 1 calc R . .
C25 C 0.3131(11) 0.1824(4) 0.5636(4) 0.0826(19) Uani 1 1 d . . .
H19A H 0.3554 0.1408 0.6083 0.099 Uiso 1 1 calc R . .
H20B H 0.1502 0.1678 0.5508 0.099 Uiso 1 1 calc R . .
C26 C 0.4933(12) 0.1661(4) 0.4945(3) 0.0877(19) Uani 1 1 d . . .
H21B H 0.6564 0.1784 0.5068 0.105 Uiso 1 1 calc R . .
H22C H 0.4507 0.2054 0.4492 0.105 Uiso 1 1 calc R . .
H23A H 0.4880 0.1040 0.4832 0.105 Uiso 1 1 calc R . .
C27 C 0.6955(14) 0.2636(4) 0.8172(3) 0.0694(16) Uani 1 1 d . . .
C28 C 0.4908(11) 0.2137(4) 0.8647(3) 0.0772(17) Uani 1 1 d . . .
H24B H 0.3366 0.2318 0.8422 0.093 Uiso 1 1 calc R . .
H25A H 0.4792 0.2314 0.9181 0.093 Uiso 1 1 calc R . .
C29 C 0.5242(12) 0.1099(4) 0.8679(3) 0.0796(18) Uani 1 1 d . . .
H27B H 0.6916 0.0922 0.8795 0.096 Uiso 1 1 calc R . .
H28A H 0.4134 0.0822 0.9101 0.096 Uiso 1 1 calc R . .
C30 C 0.4722(13) 0.0759(4) 0.7904(3) 0.094(2) Uani 1 1 d . . .
H26B H 0.5836 0.1025 0.7488 0.113 Uiso 1 1 calc R . .
H29C H 0.3057 0.0925 0.7793 0.113 Uiso 1 1 calc R . .
H30A H 0.4943 0.0110 0.7939 0.113 Uiso 1 1 calc R . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C3 1.395(6) . ?
O1 C4 1.395(6) . ?
O2 C9 1.395(6) . ?
O2 C10 1.395(6) . ?
O3 C4 1.208(6) . ?
O4 C10 1.208(6) . ?
O5 C15 1.390(7) . ?
O5 C1 1.395(6) . ?
O6 C2 1.393(6) . ?
O6 C19 1.396(7) . ?
O7 C7 1.382(6) . ?
O7 C23 1.388(7) . ?
O8 C27 1.388(6) . ?
O8 C8 1.402(6) . ?
O9 C15 1.196(7) . ?
O10 C19 1.192(6) . ?
O11 C23 1.198(6) . ?
O12 C27 1.189(6) . ?
C1 C12 1.376(7) . ?
C1 C2 1.409(7) . ?
C2 C3 1.358(7) . ?
C3 C13 1.371(7) . ?
C4 C5 1.458(8) . ?
C5 C6 1.390(7) . ?
C5 C14 1.416(7) . ?
C6 C7 1.381(7) . ?
C6 H8 0.9300 . ?
C7 C8 1.406(7) . ?
C8 C9 1.358(7) . ?
C9 C14 1.371(7) . ?
C10 C11 1.465(8) . ?
C11 C12 1.390(7) . ?
C11 C13 1.414(7) . ?
C12 H16 0.9300 . ?
C13 C14 1.415(7) . ?
C15 C16 1.494(8) . ?
C16 C17 1.500(7) . ?
C16 H1B 0.9700 . ?
C16 H2A 0.9700 . ?
C17 C18 1.518(8) . ?
C17 H3B 0.9700 . ?
C17 H4A 0.9700 . ?
C18 H5C 0.9600 . ?
C18 H6A 0.9600 . ?
C18 H7B 0.9600 . ?
C19 C20 1.502(8) . ?
C20 C21 1.532(8) . ?
C20 H9B 0.9700 . ?
C20 H10A 0.9700 . ?
C21 C22 1.517(7) . ?
C21 H11A 0.9700 . ?
C21 H12B 0.9700 . ?
C22 H13A 0.9600 . ?
C22 H14C 0.9600 . ?
C22 H15B 0.9600 . ?
C23 C24 1.483(8) . ?
C24 C25 1.530(7) . ?
C24 H17A 0.9700 . ?
C24 H18B 0.9700 . ?
C25 C26 1.502(8) . ?
C25 H19A 0.9700 . ?
C25 H20B 0.9700 . ?
C26 H21B 0.9600 . ?
C26 H22C 0.9600 . ?
C26 H23A 0.9600 . ?
C27 C28 1.500(8) . ?
C28 C29 1.536(7) . ?
C28 H24B 0.9700 . ?
C28 H25A 0.9700 . ?
C29 C30 1.516(7) . ?
C29 H27B 0.9700 . ?
C29 H28A 0.9700 . ?
C30 H26B 0.9600 . ?
C30 H29C 0.9600 . ?
C30 H30A 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
C3 O1 C4 121.3(5) . . ?
C9 O2 C10 122.2(5) . . ?
C15 O5 C1 119.0(5) . . ?
C2 O6 C19 116.9(5) . . ?
C7 O7 C23 118.1(5) . . ?
C27 O8 C8 117.2(5) . . ?
C12 C1 O5 121.4(5) . . ?
C12 C1 C2 121.6(6) . . ?
O5 C1 C2 116.8(5) . . ?
C3 C2 O6 122.2(5) . . ?
C3 C2 C1 118.9(5) . . ?
O6 C2 C1 118.4(5) . . ?
C2 C3 C13 121.6(5) . . ?
C2 C3 O1 117.3(5) . . ?
C13 C3 O1 121.1(5) . . ?
O3 C4 O1 115.9(6) . . ?
O3 C4 C5 126.1(6) . . ?
O1 C4 C5 118.0(5) . . ?
C6 C5 C14 119.5(5) . . ?
C6 C5 C4 120.7(5) . . ?
C14 C5 C4 119.8(6) . . ?
C7 C6 C5 119.3(5) . . ?
C7 C6 H8 120.3 . . ?
C5 C6 H8 120.3 . . ?
C6 C7 O7 118.7(5) . . ?
C6 C7 C8 120.5(6) . . ?
O7 C7 C8 120.6(5) . . ?
C9 C8 O8 122.4(5) . . ?
C9 C8 C7 119.7(6) . . ?
O8 C8 C7 117.6(5) . . ?
C8 C9 C14 121.2(5) . . ?
C8 C9 O2 118.9(5) . . ?
C14 C9 O2 119.9(5) . . ?
O4 C10 O2 116.2(5) . . ?
O4 C10 C11 125.6(6) . . ?
O2 C10 C11 118.2(5) . . ?
C12 C11 C13 120.3(6) . . ?
C12 C11 C10 121.1(5) . . ?
C13 C11 C10 118.6(6) . . ?
C1 C12 C11 118.4(5) . . ?
C1 C12 H16 120.8 . . ?
C11 C12 H16 120.8 . . ?
C3 C13 C11 119.2(6) . . ?
C3 C13 C14 120.8(5) . . ?
C11 C13 C14 119.9(6) . . ?
C9 C14 C13 121.2(5) . . ?
C9 C14 C5 119.7(5) . . ?
C13 C14 C5 119.0(6) . . ?
O9 C15 O5 122.2(6) . . ?
O9 C15 C16 127.3(6) . . ?
O5 C15 C16 110.4(6) . . ?
C15 C16 C17 115.4(6) . . ?
C15 C16 H1B 108.4 . . ?
C17 C16 H1B 108.4 . . ?
C15 C16 H2A 108.4 . . ?
C17 C16 H2A 108.4 . . ?
H1B C16 H2A 107.5 . . ?
C16 C17 C18 111.1(5) . . ?
C16 C17 H3B 109.4 . . ?
C18 C17 H3B 109.4 . . ?
C16 C17 H4A 109.4 . . ?
C18 C17 H4A 109.4 . . ?
H3B C17 H4A 108.0 . . ?
C17 C18 H5C 109.5 . . ?
C17 C18 H6A 109.5 . . ?
H5C C18 H6A 109.5 . . ?
C17 C18 H7B 109.5 . . ?
H5C C18 H7B 109.5 . . ?
H6A C18 H7B 109.5 . . ?
O10 C19 O6 122.0(6) . . ?
O10 C19 C20 128.5(6) . . ?
O6 C19 C20 109.5(6) . . ?
C19 C20 C21 114.2(5) . . ?
C19 C20 H9B 108.7 . . ?
C21 C20 H9B 108.7 . . ?
C19 C20 H10A 108.7 . . ?
C21 C20 H10A 108.7 . . ?
H9B C20 H10A 107.6 . . ?
C22 C21 C20 112.9(5) . . ?
C22 C21 H11A 109.0 . . ?
C20 C21 H11A 109.0 . . ?
C22 C21 H12B 109.0 . . ?
C20 C21 H12B 109.0 . . ?
H11A C21 H12B 107.8 . . ?
C21 C22 H13A 109.5 . . ?
C21 C22 H14C 109.5 . . ?
H13A C22 H14C 109.5 . . ?
C21 C22 H15B 109.5 . . ?
H13A C22 H15B 109.5 . . ?
H14C C22 H15B 109.5 . . ?
O11 C23 O7 121.2(6) . . ?
O11 C23 C24 128.2(7) . . ?
O7 C23 C24 110.6(6) . . ?
C23 C24 C25 112.5(6) . . ?
C23 C24 H17A 109.1 . . ?
C25 C24 H17A 109.1 . . ?
C23 C24 H18B 109.1 . . ?
C25 C24 H18B 109.1 . . ?
H17A C24 H18B 107.8 . . ?
C26 C25 C24 115.4(5) . . ?
C26 C25 H19A 108.4 . . ?
C24 C25 H19A 108.4 . . ?
C26 C25 H20B 108.4 . . ?
C24 C25 H20B 108.4 . . ?
H19A C25 H20B 107.5 . . ?
C25 C26 H21B 109.5 . . ?
C25 C26 H22C 109.5 . . ?
H21B C26 H22C 109.5 . . ?
C25 C26 H23A 109.5 . . ?
H21B C26 H23A 109.5 . . ?
H22C C26 H23A 109.5 . . ?
O12 C27 O8 122.7(6) . . ?
O12 C27 C28 128.2(6) . . ?
O8 C27 C28 109.1(6) . . ?
C27 C28 C29 113.7(5) . . ?
C27 C28 H24B 108.8 . . ?
C29 C28 H24B 108.8 . . ?
C27 C28 H25A 108.8 . . ?
C29 C28 H25A 108.8 . . ?
H24B C28 H25A 107.7 . . ?
C30 C29 C28 111.1(5) . . ?
C30 C29 H27B 109.4 . . ?
C28 C29 H27B 109.4 . . ?
C30 C29 H28A 109.4 . . ?
C28 C29 H28A 109.4 . . ?
H27B C29 H28A 108.0 . . ?
C29 C30 H26B 109.5 . . ?
C29 C30 H29C 109.5 . . ?
H26B C30 H29C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
H26B C30 H30A 109.5 . . ?
H29C C30 H30A 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
C15 O5 C1 C12 -65.5(7) . . . . ?
C15 O5 C1 C2 118.8(5) . . . . ?
C19 O6 C2 C3 116.6(6) . . . . ?
C19 O6 C2 C1 -71.3(6) . . . . ?
C12 C1 C2 C3 -0.9(9) . . . . ?
O5 C1 C2 C3 174.8(4) . . . . ?
C12 C1 C2 O6 -173.3(5) . . . . ?
O5 C1 C2 O6 2.4(7) . . . . ?
O6 C2 C3 C13 171.2(5) . . . . ?
C1 C2 C3 C13 -0.9(9) . . . . ?
O6 C2 C3 O1 -7.0(8) . . . . ?
C1 C2 C3 O1 -179.1(5) . . . . ?
C4 O1 C3 C2 179.2(5) . . . . ?
C4 O1 C3 C13 1.1(8) . . . . ?
C3 O1 C4 O3 178.5(5) . . . . ?
C3 O1 C4 C5 -1.5(7) . . . . ?
O3 C4 C5 C6 0.6(9) . . . . ?
O1 C4 C5 C6 -179.4(5) . . . . ?
O3 C4 C5 C14 179.3(6) . . . . ?
O1 C4 C5 C14 -0.7(8) . . . . ?
C14 C5 C6 C7 2.3(8) . . . . ?
C4 C5 C6 C7 -179.0(5) . . . . ?
C5 C6 C7 O7 173.5(5) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C23 O7 C7 C6 116.0(6) . . . . ?
C23 O7 C7 C8 -69.3(7) . . . . ?
C27 O8 C8 C9 -69.3(7) . . . . ?
C27 O8 C8 C7 116.9(5) . . . . ?
C6 C7 C8 C9 0.2(9) . . . . ?
O7 C7 C8 C9 -174.3(5) . . . . ?
C6 C7 C8 O8 174.1(4) . . . . ?
O7 C7 C8 O8 -0.4(8) . . . . ?
O8 C8 C9 C14 -174.0(5) . . . . ?
C7 C8 C9 C14 -0.4(9) . . . . ?
O8 C8 C9 O2 5.2(8) . . . . ?
C7 C8 C9 O2 178.8(5) . . . . ?
C10 O2 C9 C8 -179.0(5) . . . . ?
C10 O2 C9 C14 0.2(8) . . . . ?
C9 O2 C10 O4 -178.9(5) . . . . ?
C9 O2 C10 C11 1.6(7) . . . . ?
O4 C10 C11 C12 1.3(9) . . . . ?
O2 C10 C11 C12 -179.3(5) . . . . ?
O4 C10 C11 C13 179.3(6) . . . . ?
O2 C10 C11 C13 -1.3(8) . . . . ?
O5 C1 C12 C11 -173.8(5) . . . . ?
C2 C1 C12 C11 1.7(8) . . . . ?
C13 C11 C12 C1 -0.7(8) . . . . ?
C10 C11 C12 C1 177.2(5) . . . . ?
C2 C3 C13 C11 1.9(9) . . . . ?
O1 C3 C13 C11 179.9(5) . . . . ?
C2 C3 C13 C14 -176.5(5) . . . . ?
O1 C3 C13 C14 1.6(8) . . . . ?
C12 C11 C13 C3 -1.0(8) . . . . ?
C10 C11 C13 C3 -179.0(5) . . . . ?
C12 C11 C13 C14 177.3(5) . . . . ?
C10 C11 C13 C14 -0.7(8) . . . . ?
C8 C9 C14 C13 176.9(5) . . . . ?
O2 C9 C14 C13 -2.2(8) . . . . ?
C8 C9 C14 C5 1.5(9) . . . . ?
O2 C9 C14 C5 -177.7(5) . . . . ?
C3 C13 C14 C9 -179.2(5) . . . . ?
C11 C13 C14 C9 2.5(8) . . . . ?
C3 C13 C14 C5 -3.7(8) . . . . ?
C11 C13 C14 C5 178.0(5) . . . . ?
C6 C5 C14 C9 -2.4(8) . . . . ?
C4 C5 C14 C9 178.8(5) . . . . ?
C6 C5 C14 C13 -178.0(5) . . . . ?
C4 C5 C14 C13 3.2(8) . . . . ?
C1 O5 C15 O9 -3.8(8) . . . . ?
C1 O5 C15 C16 178.1(5) . . . . ?
O9 C15 C16 C17 -26.3(9) . . . . ?
O5 C15 C16 C17 151.8(5) . . . . ?
C15 C16 C17 C18 -64.7(7) . . . . ?
C2 O6 C19 O10 -13.3(8) . . . . ?
C2 O6 C19 C20 165.5(5) . . . . ?
O10 C19 C20 C21 -13.0(9) . . . . ?
O6 C19 C20 C21 168.3(5) . . . . ?
C19 C20 C21 C22 -70.4(7) . . . . ?
C7 O7 C23 O11 0.0(8) . . . . ?
C7 O7 C23 C24 178.1(5) . . . . ?
O11 C23 C24 C25 -12.0(9) . . . . ?
O7 C23 C24 C25 170.1(5) . . . . ?
C23 C24 C25 C26 -66.5(7) . . . . ?
C8 O8 C27 O12 -1.1(8) . . . . ?
C8 O8 C27 C28 179.3(4) . . . . ?
O12 C27 C28 C29 -27.0(9) . . . . ?
O8 C27 C28 C29 152.5(5) . . . . ?
C27 C28 C29 C30 -74.5(6) . . . . ?
