# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shi06_new
_database_code_depnum_ccdc_archive 'CCDC 1904252'
loop_
_audit_author_name
_audit_author_address
Shi
;Colorado State University
United States of America
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Cl2 O6'
_chemical_formula_weight         463.29

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   12.9425(9)
_cell_length_b                   15.6165(11)
_cell_length_c                   10.6618(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.551(3)
_cell_angle_gamma                90
_cell_volume                     2111.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9295
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.88

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.346
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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            18659
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.069
_diffrn_reflns_theta_max         27.951
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2541
_reflns_number_gt                2125
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0489P)²+2.2231P] 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         2541
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.94801(10) 0.22017(8) 0.36688(12) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.94856(10) 0.29573(8) 0.27641(12) 0.0118(3) Uani 1 1 d . . . . .
C3 C 0.94025(10) 0.37880(8) 0.35573(13) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.83576(10) 0.41663(8) 0.30983(13) 0.0145(3) Uani 1 1 d . . . . .
C5 C 0.79203(11) 0.48787(9) 0.35872(14) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.8308 0.5193 0.4289 0.023 Uiso 1 1 calc R U . . .
C6 C 0.69009(12) 0.51120(10) 0.30133(15) 0.0235(3) Uani 1 1 d . . . . .
H6 H 0.6578 0.5591 0.3327 0.028 Uiso 1 1 calc R U . . .
C7 C 0.63488(11) 0.46444(10) 0.19762(15) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.5653 0.4815 0.1590 0.029 Uiso 1 1 calc R U . . .
C8 C 0.67900(11) 0.39357(10) 0.14941(14) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.6405 0.3623 0.0789 0.025 Uiso 1 1 calc R U . . .
C9 C 0.78107(10) 0.36957(9) 0.20719(13) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.84441(10) 0.29581(9) 0.17260(13) 0.0146(3) Uani 1 1 d . . . . .
H10A H 0.8598 0.3038 0.0861 0.018 Uiso 1 1 calc R U . . .
H10B H 0.8058 0.2412 0.1743 0.018 Uiso 1 1 calc R U . . .
C11 C 0.85329(14) 0.15646(10) 0.50936(17) 0.0280(4) Uani 1 1 d . . . . .
H11A H 0.8458 0.1012 0.4648 0.042 Uiso 1 1 calc R U . . .
H11B H 0.7912 0.1669 0.5467 0.042 Uiso 1 1 calc R U . . .
H11C H 0.9166 0.1555 0.5775 0.042 Uiso 1 1 calc R U . . .
O1 O 1.01397(8) 0.16520(7) 0.39014(10) 0.0198(2) Uani 1 1 d . . . . .
O2 O 0.86271(8) 0.22406(7) 0.41935(10) 0.0221(2) Uani 1 1 d . . . . .
O3 O 1.00927(8) 0.40499(7) 0.44031(11) 0.0261(3) Uani 1 1 d . . . . .
C12 C 0.5000 0.11000(15) 0.2500 0.0283(5) Uani 1 2 d S T P . .
H12A H 0.5037 0.0727 0.3259 0.034 Uiso 0.5 1 calc R U P . .
H12B H 0.4963 0.0727 0.1741 0.034 Uiso 0.5 1 calc R U P . .
Cl1 Cl 0.61353(5) 0.17316(4) 0.26970(8) 0.0703(2) Uani 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
C1 O1 1.2010(17) . ?
C1 O2 1.3352(16) . ?
C1 C2 1.5249(18) . ?
C2 C2 1.546(2) 2_755 ?
C2 C10 1.5635(18) . ?
C2 C3 1.5640(18) . ?
C3 O3 1.2066(17) . ?
C3 C4 1.4671(18) . ?
C4 C9 1.3887(19) . ?
C4 C5 1.3956(19) . ?
C5 C6 1.387(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.390(2) . ?
C8 C9 1.3926(19) . ?
C9 C10 1.5019(19) . ?
C11 O2 1.4483(18) . ?
C12 Cl1 1.7471(14) . ?
C12 Cl1 1.7471(14) 2_655 ?

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
O1 C1 O2 124.00(12) . . ?
O1 C1 C2 126.20(12) . . ?
O2 C1 C2 109.80(11) . . ?
C1 C2 C2 110.11(9) . 2_755 ?
C1 C2 C10 109.62(10) . . ?
C2 C2 C10 115.18(13) 2_755 . ?
C1 C2 C3 106.87(10) . . ?
C2 C2 C3 110.76(8) 2_755 . ?
C10 C2 C3 103.84(10) . . ?
O3 C3 C4 127.43(13) . . ?
O3 C3 C2 124.37(12) . . ?
C4 C3 C2 108.20(11) . . ?
C9 C4 C5 122.37(12) . . ?
C9 C4 C3 109.88(12) . . ?
C5 C4 C3 127.74(13) . . ?
C6 C5 C4 117.75(14) . . ?
C5 C6 C7 120.17(14) . . ?
C8 C7 C6 121.75(13) . . ?
C7 C8 C9 118.31(14) . . ?
C4 C9 C8 119.66(13) . . ?
C4 C9 C10 112.47(11) . . ?
C8 C9 C10 127.87(13) . . ?
C9 C10 C2 105.21(11) . . ?
C1 O2 C11 115.52(11) . . ?
Cl1 C12 Cl1 111.26(13) . 2_655 ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ys217
_database_code_depnum_ccdc_archive 'CCDC 1904257'
loop_
_audit_author_name
_audit_author_address
Shi
;Colorado State University
United States of America
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 O6'
_chemical_formula_sum            'C24 H22 O6'
_chemical_formula_weight         406.41

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                   8.8734(3)
_cell_length_b                   16.0071(5)
_cell_length_c                   14.1890(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.720(2)
_cell_angle_gamma                90
_cell_volume                     1980.20(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9425
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      36.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   0.7037
_exptl_transmission_factor_max   0.7472
_exptl_crystal_size_max          0.716
_exptl_crystal_size_mid          0.696
_exptl_crystal_size_min          0.328
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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            173511
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.937
_diffrn_reflns_theta_max         36.702
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9831
_reflns_number_gt                8222
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0565P)²+0.5256P] 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         9831
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 1.15272(7) 0.29977(4) 0.49526(4) 0.01885(10) Uani 1 1 d . . . . .
O2 O 1.30840(7) 0.26229(4) 0.30455(5) 0.02337(12) Uani 1 1 d . . . . .
O3 O 1.31129(6) 0.14067(3) 0.38321(4) 0.01738(10) Uani 1 1 d . . . . .
O4 O 0.72509(6) 0.22126(3) 0.25144(4) 0.01769(10) Uani 1 1 d . . . . .
O5 O 1.05072(7) 0.18152(3) 0.16044(4) 0.01794(10) Uani 1 1 d . . . . .
O6 O 0.96682(8) 0.30887(4) 0.10975(4) 0.02294(12) Uani 1 1 d . . . . .
C1 C 1.07619(7) 0.24207(4) 0.45649(5) 0.01205(10) Uani 1 1 d . . . . .
C2 C 0.97525(7) 0.18637(4) 0.49847(4) 0.01125(10) Uani 1 1 d . . . . .
C3 C 0.93352(8) 0.19287(4) 0.58872(5) 0.01383(10) Uani 1 1 d . . . . .
H3 H 0.9681 0.2379 0.6308 0.017 Uiso 1 1 calc R U . . .
C4 C 0.83951(8) 0.13075(4) 0.61398(5) 0.01498(11) Uani 1 1 d . . . . .
H4 H 0.8076 0.1332 0.6742 0.018 Uiso 1 1 calc R U . . .
C5 C 0.79125(7) 0.06421(4) 0.55107(5) 0.01367(10) Uani 1 1 d . . . . .
H5 H 0.7268 0.0225 0.5701 0.016 Uiso 1 1 calc R U . . .
C6 C 0.83428(7) 0.05686(4) 0.46165(4) 0.01106(10) Uani 1 1 d . . . . .
C7 C 0.92822(7) 0.12027(4) 0.43610(4) 0.01000(9) Uani 1 1 d . . . . .
C8 C 0.99368(7) 0.12584(4) 0.34561(4) 0.01089(9) Uani 1 1 d . . . . .
H8A H 0.9112 0.1223 0.2883 0.013 Uiso 1 1 calc R U . . .
H8B H 1.0680 0.0802 0.3430 0.013 Uiso 1 1 calc R U . . .
C9 C 1.07463(7) 0.21231(4) 0.35063(4) 0.01047(9) Uani 1 1 d . . . . .
C10 C 0.78248(8) -0.01466(4) 0.39507(5) 0.01484(11) Uani 1 1 d . . . . .
H10A H 0.7192 -0.0528 0.4252 0.022 Uiso 1 1 calc R U . . .
H10B H 0.8723 -0.0447 0.3815 0.022 Uiso 1 1 calc R U . . .
H10C H 0.7222 0.0068 0.3350 0.022 Uiso 1 1 calc R U . . .
C11 C 1.24295(7) 0.20863(4) 0.34113(5) 0.01269(10) Uani 1 1 d . . . . .
C12 C 1.47562(8) 0.13554(5) 0.38878(6) 0.02035(13) Uani 1 1 d . . . . .
H12A H 1.5011 0.1518 0.3270 0.031 Uiso 1 1 calc R U . . .
H12B H 1.5099 0.0781 0.4040 0.031 Uiso 1 1 calc R U . . .
H12C H 1.5271 0.1732 0.4391 0.031 Uiso 1 1 calc R U . . .
C13 C 0.98915(7) 0.27790(4) 0.27769(5) 0.01163(10) Uani 1 1 d . . . . .
C14 C 0.81290(7) 0.27782(4) 0.28026(5) 0.01237(10) Uani 1 1 d . . . . .
C15 C 0.77517(8) 0.35856(4) 0.31912(5) 0.01330(10) Uani 1 1 d . . . . .
C16 C 0.63228(8) 0.38475(5) 0.33631(5) 0.01758(12) Uani 1 1 d . . . . .
H16 H 0.5464 0.3482 0.3273 0.021 Uiso 1 1 calc R U . . .
C17 C 0.62161(10) 0.46643(5) 0.36713(6) 0.02239(14) Uani 1 1 d . . . . .
H17 H 0.5265 0.4866 0.3795 0.027 Uiso 1 1 calc R U . . .
C18 C 0.74946(10) 0.51958(5) 0.38030(6) 0.02175(14) Uani 1 1 d . . . . .
H18 H 0.7387 0.5752 0.4015 0.026 Uiso 1 1 calc R U . . .
C19 C 0.89193(9) 0.49338(4) 0.36325(5) 0.01700(12) Uani 1 1 d . . . . .
C20 C 0.90234(8) 0.41093(4) 0.33167(5) 0.01317(10) Uani 1 1 d . . . . .
C21 C 1.03850(8) 0.36992(4) 0.30176(5) 0.01465(11) Uani 1 1 d . . . . .
H21A H 1.1289 0.3720 0.3545 0.018 Uiso 1 1 calc R U . . .
H21B H 1.0646 0.3982 0.2448 0.018 Uiso 1 1 calc R U . . .
C22 C 1.02801(11) 0.55105(5) 0.37631(6) 0.02397(15) Uani 1 1 d . . . . .
H22A H 0.9967 0.6070 0.3931 0.036 Uiso 1 1 calc R U . . .
H22B H 1.0680 0.5538 0.3165 0.036 Uiso 1 1 calc R U . . .
H22C H 1.1080 0.5299 0.4279 0.036 Uiso 1 1 calc R U . . .
C23 C 1.00146(8) 0.25879(4) 0.17363(5) 0.01406(11) Uani 1 1 d . . . . .
C24 C 1.06652(10) 0.16299(5) 0.06280(6) 0.02152(14) Uani 1 1 d . . . . .
H24A H 0.9668 0.1693 0.0201 0.032 Uiso 1 1 calc R U . . .
H24B H 1.1030 0.1055 0.0592 0.032 Uiso 1 1 calc R U . . .
H24C H 1.1404 0.2017 0.0430 0.032 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 1.2156(8) . ?
O2 C11 1.2069(8) . ?
O3 C11 1.3315(8) . ?
O3 C12 1.4478(9) . ?
O4 C14 1.2148(8) . ?
O5 C23 1.3365(9) . ?
O5 C24 1.4489(9) . ?
O6 C23 1.2063(9) . ?
C1 C2 1.4665(9) . ?
C1 C9 1.5733(9) . ?
C2 C7 1.3926(9) . ?
C2 C3 1.4015(9) . ?
C3 C4 1.3872(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.4045(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.3963(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.4033(9) . ?
C6 C10 1.5009(9) . ?
C7 C8 1.5071(9) . ?
C8 C9 1.5549(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.5256(9) . ?
C9 C13 1.5674(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C23 1.5316(9) . ?
C13 C21 1.5564(9) . ?
C13 C14 1.5710(9) . ?
C14 C15 1.4680(9) . ?
C15 C20 1.3903(10) . ?
C15 C16 1.3993(10) . ?
C16 C17 1.3873(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.4024(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.3952(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.4023(10) . ?
C19 C22 1.5038(12) . ?
C20 C21 1.5039(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 O3 C12 116.16(6) . . ?
C23 O5 C24 114.57(6) . . ?
O1 C1 C2 127.60(6) . . ?
O1 C1 C9 124.54(6) . . ?
C2 C1 C9 107.82(5) . . ?
C7 C2 C3 122.56(6) . . ?
C7 C2 C1 109.72(5) . . ?
C3 C2 C1 127.67(6) . . ?
C4 C3 C2 117.17(6) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 120.42(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 122.60(6) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 116.73(6) . . ?
C5 C6 C10 122.19(6) . . ?
C7 C6 C10 121.08(6) . . ?
C2 C7 C6 120.51(6) . . ?
C2 C7 C8 112.27(5) . . ?
C6 C7 C8 127.19(5) . . ?
C7 C8 C9 105.17(5) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C11 C9 C8 114.40(5) . . ?
C11 C9 C13 109.21(5) . . ?
C8 C9 C13 113.79(5) . . ?
C11 C9 C1 105.14(5) . . ?
C8 C9 C1 103.61(5) . . ?
C13 C9 C1 110.17(5) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O3 123.98(6) . . ?
O2 C11 C9 124.60(6) . . ?
O3 C11 C9 111.32(5) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C23 C13 C21 109.45(5) . . ?
C23 C13 C9 112.97(5) . . ?
C21 C13 C9 114.03(5) . . ?
C23 C13 C14 105.78(5) . . ?
C21 C13 C14 103.67(5) . . ?
C9 C13 C14 110.23(5) . . ?
O4 C14 C15 127.29(6) . . ?
O4 C14 C13 124.87(6) . . ?
C15 C14 C13 107.79(5) . . ?
C20 C15 C16 122.50(6) . . ?
C20 C15 C14 110.03(6) . . ?
C16 C15 C14 127.35(6) . . ?
C17 C16 C15 117.03(7) . . ?
C17 C16 H16 121.5 . . ?
C15 C16 H16 121.5 . . ?
C16 C17 C18 120.85(7) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 122.08(7) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 117.00(7) . . ?
C18 C19 C22 121.79(7) . . ?
C20 C19 C22 121.20(7) . . ?
C15 C20 C19 120.55(6) . . ?
C15 C20 C21 112.10(6) . . ?
C19 C20 C21 127.24(6) . . ?
C20 C21 C13 105.48(5) . . ?
C20 C21 H21A 110.6 . . ?
C13 C21 H21A 110.6 . . ?
C20 C21 H21B 110.6 . . ?
C13 C21 H21B 110.6 . . ?
H21A C21 H21B 108.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C23 O5 123.64(7) . . ?
O6 C23 C13 122.53(6) . . ?
O5 C23 C13 113.81(6) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C1 C2 C7 -170.26(7) . . . . ?
C9 C1 C2 C7 7.61(7) . . . . ?
O1 C1 C2 C3 7.02(11) . . . . ?
C9 C1 C2 C3 -175.11(6) . . . . ?
C7 C2 C3 C4 -1.11(10) . . . . ?
C1 C2 C3 C4 -178.07(6) . . . . ?
C2 C3 C4 C5 0.77(10) . . . . ?
C3 C4 C5 C6 0.10(10) . . . . ?
C4 C5 C6 C7 -0.66(9) . . . . ?
C4 C5 C6 C10 179.80(6) . . . . ?
C3 C2 C7 C6 0.56(9) . . . . ?
C1 C2 C7 C6 178.00(5) . . . . ?
C3 C2 C7 C8 -177.60(6) . . . . ?
C1 C2 C7 C8 -0.16(7) . . . . ?
C5 C6 C7 C2 0.33(9) . . . . ?
C10 C6 C7 C2 179.88(6) . . . . ?
C5 C6 C7 C8 178.19(6) . . . . ?
C10 C6 C7 C8 -2.26(10) . . . . ?
C2 C7 C8 C9 -7.35(7) . . . . ?
C6 C7 C8 C9 174.64(6) . . . . ?
C7 C8 C9 C11 124.97(5) . . . . ?
C7 C8 C9 C13 -108.54(6) . . . . ?
C7 C8 C9 C1 11.09(6) . . . . ?
O1 C1 C9 C11 45.99(8) . . . . ?
C2 C1 C9 C11 -131.96(5) . . . . ?
O1 C1 C9 C8 166.37(6) . . . . ?
C2 C1 C9 C8 -11.58(6) . . . . ?
O1 C1 C9 C13 -71.55(8) . . . . ?
C2 C1 C9 C13 110.49(6) . . . . ?
C12 O3 C11 O2 3.66(11) . . . . ?
C12 O3 C11 C9 -172.86(6) . . . . ?
C8 C9 C11 O2 147.81(7) . . . . ?
C13 C9 C11 O2 18.98(9) . . . . ?
C1 C9 C11 O2 -99.21(8) . . . . ?
C8 C9 C11 O3 -35.70(8) . . . . ?
C13 C9 C11 O3 -164.53(5) . . . . ?
C1 C9 C11 O3 77.28(6) . . . . ?
C11 C9 C13 C23 57.44(7) . . . . ?
C8 C9 C13 C23 -71.73(7) . . . . ?
C1 C9 C13 C23 172.44(5) . . . . ?
C11 C9 C13 C21 -68.35(7) . . . . ?
C8 C9 C13 C21 162.48(5) . . . . ?
C1 C9 C13 C21 46.65(7) . . . . ?
C11 C9 C13 C14 175.54(5) . . . . ?
C8 C9 C13 C14 46.37(7) . . . . ?
C1 C9 C13 C14 -69.46(6) . . . . ?
C23 C13 C14 O4 53.23(8) . . . . ?
C21 C13 C14 O4 168.37(7) . . . . ?
C9 C13 C14 O4 -69.20(8) . . . . ?
C23 C13 C14 C15 -124.36(6) . . . . ?
C21 C13 C14 C15 -9.22(7) . . . . ?
C9 C13 C14 C15 113.22(6) . . . . ?
O4 C14 C15 C20 -171.63(7) . . . . ?
C13 C14 C15 C20 5.88(7) . . . . ?
O4 C14 C15 C16 4.24(12) . . . . ?
C13 C14 C15 C16 -178.24(6) . . . . ?
C20 C15 C16 C17 -0.12(11) . . . . ?
C14 C15 C16 C17 -175.53(7) . . . . ?
C15 C16 C17 C18 -0.11(12) . . . . ?
C16 C17 C18 C19 0.04(13) . . . . ?
C17 C18 C19 C20 0.26(11) . . . . ?
C17 C18 C19 C22 179.20(8) . . . . ?
C16 C15 C20 C19 0.43(10) . . . . ?
C14 C15 C20 C19 176.54(6) . . . . ?
C16 C15 C20 C21 -175.90(6) . . . . ?
C14 C15 C20 C21 0.21(8) . . . . ?
C18 C19 C20 C15 -0.48(10) . . . . ?
C22 C19 C20 C15 -179.43(7) . . . . ?
C18 C19 C20 C21 175.25(7) . . . . ?
C22 C19 C20 C21 -3.69(11) . . . . ?
C15 C20 C21 C13 -6.19(7) . . . . ?
C19 C20 C21 C13 177.77(6) . . . . ?
C23 C13 C21 C20 121.55(6) . . . . ?
C9 C13 C21 C20 -110.82(6) . . . . ?
C14 C13 C21 C20 9.05(6) . . . . ?
C24 O5 C23 O6 2.70(11) . . . . ?
C24 O5 C23 C13 -178.61(6) . . . . ?
C21 C13 C23 O6 -38.61(9) . . . . ?
C9 C13 C23 O6 -166.83(7) . . . . ?
C14 C13 C23 O6 72.51(8) . . . . ?
C21 C13 C23 O5 142.68(6) . . . . ?
C9 C13 C23 O5 14.46(8) . . . . ?
C14 C13 C23 O5 -106.20(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12C O6 0.98 2.59 3.2739(10) 126.8 4_666
C12 H12C O6 0.98 2.59 3.2739(10) 126.8 4_666
C12 H12C O6 0.98 2.59 3.2739(10) 126.8 4_666
C12 H12C O6 0.98 2.59 3.2739(10) 126.8 4_666
C12 H12C O6 0.98 2.59 3.2739(10) 126.8 4_666

_refine_diff_density_max         0.609
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-3

