# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 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_kp72
_database_code_depnum_ccdc_archive 'CCDC 1018601'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 O6'
_chemical_formula_weight         370.38

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           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                   56.225(4)
_cell_length_b                   4.6615(3)
_cell_length_c                   14.0454(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.729(4)
_cell_angle_gamma                90
_cell_volume                     3604.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6729
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            16772
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -69
_diffrn_reflns_limit_h_max       70
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.220
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3661
_reflns_number_gt                2393
_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)+(0.0490P)²+1.6968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3661
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.13142(2) 0.5006(3) 0.29439(9) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.02184(3) 0.6619(4) 0.35618(11) 0.0387(4) Uani 1 1 d . . . . .
H1 H 0.0115(5) 0.777(7) 0.331(2) 0.095(12) Uiso 1 1 d . . . . .
O3 O 0.02184(2) 1.0104(3) 0.20496(10) 0.0354(4) Uani 1 1 d . . . . .
O4 O 0.21983(2) 0.3468(3) 0.48005(8) 0.0243(3) Uani 1 1 d . . . . .
O5 O 0.22176(2) 0.6154(3) 0.64798(8) 0.0228(3) Uani 1 1 d . . . . .
O6 O 0.18396(2) 0.9126(3) 0.68457(9) 0.0292(4) Uani 1 1 d . . . . .
C1 C 0.13225(3) 0.5492(4) 0.38065(13) 0.0235(5) Uani 1 1 d . . . . .
C2 C 0.10948(3) 0.5639(4) 0.42000(13) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.10899(4) 0.4425(5) 0.50602(14) 0.0309(5) Uani 1 1 d . . . . .
H3 H 0.1235 0.3621 0.5428 0.037 Uiso 1 1 calc R U . . .
C4 C 0.08640(4) 0.4297(5) 0.54589(14) 0.0400(6) Uani 1 1 d . . . . .
H4A H 0.0852 0.6051 0.5843 0.048 Uiso 1 1 calc R U . . .
H4B H 0.0872 0.2626 0.5900 0.048 Uiso 1 1 calc R U . . .
C5 C 0.06404(4) 0.4043(4) 0.46564(14) 0.0292(5) Uani 1 1 d . . . . .
H5A H 0.0630 0.2070 0.4390 0.035 Uiso 1 1 calc R U . . .
H5B H 0.0494 0.4393 0.4928 0.035 Uiso 1 1 calc R U . . .
C6 C 0.06468(3) 0.6155(4) 0.38498(13) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.04357(3) 0.7337(4) 0.33207(14) 0.0259(5) Uani 1 1 d . . . . .
C8 C 0.04426(3) 0.9214(4) 0.25494(14) 0.0257(5) Uani 1 1 d . . . . .
C9 C 0.06620(4) 1.0026(4) 0.23497(13) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.0667 1.1372 0.1847 0.032 Uiso 1 1 calc R U . . .
C10 C 0.08754(4) 0.8882(4) 0.28830(13) 0.0248(5) Uani 1 1 d . . . . .
H10 H 0.1027 0.9460 0.2744 0.030 Uiso 1 1 calc R U . . .
C11 C 0.08711(3) 0.6903(4) 0.36174(12) 0.0203(4) Uani 1 1 d . . . . .
C12 C 0.15611(3) 0.5814(4) 0.44991(12) 0.0207(4) Uani 1 1 d . . . . .
C13 C 0.17648(3) 0.4456(4) 0.42842(13) 0.0207(4) Uani 1 1 d . . . . .
H13 H 0.1752 0.3397 0.3698 0.025 Uiso 1 1 calc R U . . .
C14 C 0.19863(3) 0.4664(4) 0.49331(13) 0.0208(4) Uani 1 1 d . . . . .
C15 C 0.20040(3) 0.6199(4) 0.58007(12) 0.0198(4) Uani 1 1 d . . . . .
C16 C 0.18020(3) 0.7647(4) 0.59878(12) 0.0221(4) Uani 1 1 d . . . . .
C17 C 0.15804(3) 0.7467(4) 0.53402(12) 0.0227(5) Uani 1 1 d . . . . .
H17 H 0.1443 0.8462 0.5468 0.027 Uiso 1 1 calc R U . . .
C18 C 0.02154(4) 1.2066(5) 0.12601(15) 0.0392(6) Uani 1 1 d . . . . .
H18A H 0.0308 1.3791 0.1502 0.059 Uiso 1 1 calc R U . . .
H18B H 0.0047 1.2595 0.0977 0.059 Uiso 1 1 calc R U . . .
H18C H 0.0289 1.1150 0.0762 0.059 Uiso 1 1 calc R U . . .
C19 C 0.21907(4) 0.1785(4) 0.39452(13) 0.0276(5) Uani 1 1 d . . . . .
H19A H 0.2080 0.0158 0.3947 0.041 Uiso 1 1 calc R U . . .
H19B H 0.2354 0.1071 0.3933 0.041 Uiso 1 1 calc R U . . .
H19C H 0.2132 0.2969 0.3369 0.041 Uiso 1 1 calc R U . . .
C20 C 0.23640(4) 0.8680(4) 0.64730(14) 0.0291(5) Uani 1 1 d . . . . .
H20A H 0.2416 0.8814 0.5850 0.044 Uiso 1 1 calc R U . . .
H20B H 0.2507 0.8565 0.7002 0.044 Uiso 1 1 calc R U . . .
H20C H 0.2269 1.0382 0.6562 0.044 Uiso 1 1 calc R U . . .
C21 C 0.16425(4) 1.0788(4) 0.70488(14) 0.0297(5) Uani 1 1 d . . . . .
H21A H 0.1594 1.2217 0.6534 0.045 Uiso 1 1 calc R U . . .
H21B H 0.1694 1.1763 0.7675 0.045 Uiso 1 1 calc R U . . .
H21C H 0.1505 0.9524 0.7076 0.045 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 1.224(2) . ?
O2 C7 1.374(2) . ?
O3 C8 1.376(2) . ?
O3 C18 1.435(2) . ?
O4 C14 1.363(2) . ?
O4 C19 1.428(2) . ?
O5 C15 1.373(2) . ?
O5 C20 1.438(2) . ?
O6 C16 1.367(2) . ?
O6 C21 1.428(2) . ?
C1 C2 1.495(3) . ?
C1 C12 1.496(3) . ?
C2 C3 1.340(3) . ?
C2 C11 1.477(3) . ?
C3 C4 1.490(3) . ?
C4 C5 1.513(3) . ?
C5 C6 1.507(3) . ?
C6 C7 1.381(3) . ?
C6 C11 1.409(3) . ?
C7 C8 1.399(3) . ?
C8 C9 1.372(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.388(3) . ?
C12 C13 1.395(3) . ?
C12 C17 1.396(2) . ?
C13 C14 1.389(3) . ?
C14 C15 1.399(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.388(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
C8 O3 C18 116.88(15) . . ?
C14 O4 C19 117.53(14) . . ?
C15 O5 C20 113.81(14) . . ?
C16 O6 C21 117.56(14) . . ?
O1 C1 C2 120.74(17) . . ?
O1 C1 C12 120.71(17) . . ?
C2 C1 C12 118.48(15) . . ?
C3 C2 C11 119.78(17) . . ?
C3 C2 C1 119.37(18) . . ?
C11 C2 C1 120.68(16) . . ?
C2 C3 C4 122.13(19) . . ?
C3 C4 C5 111.46(16) . . ?
C6 C5 C4 111.45(16) . . ?
C7 C6 C11 119.25(17) . . ?
C7 C6 C5 121.06(17) . . ?
C11 C6 C5 119.68(17) . . ?
O2 C7 C6 118.73(18) . . ?
O2 C7 C8 120.61(18) . . ?
C6 C7 C8 120.66(17) . . ?
C9 C8 O3 125.48(18) . . ?
C9 C8 C7 119.90(18) . . ?
O3 C8 C7 114.62(17) . . ?
C8 C9 C10 119.92(18) . . ?
C9 C10 C11 120.89(18) . . ?
C10 C11 C6 119.24(17) . . ?
C10 C11 C2 122.37(17) . . ?
C6 C11 C2 118.33(16) . . ?
C13 C12 C17 120.51(17) . . ?
C13 C12 C1 118.77(16) . . ?
C17 C12 C1 120.72(17) . . ?
C14 C13 C12 119.51(17) . . ?
O4 C14 C13 125.05(16) . . ?
O4 C14 C15 114.76(16) . . ?
C13 C14 C15 120.19(17) . . ?
O5 C15 C16 120.55(16) . . ?
O5 C15 C14 119.64(16) . . ?
C16 C15 C14 119.75(17) . . ?
O6 C16 C17 124.43(17) . . ?
O6 C16 C15 115.17(16) . . ?
C17 C16 C15 120.37(17) . . ?
C16 C17 C12 119.53(17) . . ?

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
C19 H19C O6 0.98 2.61 3.226(2) 121.0 6_565
C20 H20B O5 0.98 2.66 3.519(2) 147.0 4_556
C20 H20C O6 0.98 2.59 3.104(2) 112.8 .
C18 H18B O2 0.98 2.56 3.281(3) 130.2 2_565
O2 H1 O3 0.81(3) 2.26(3) 2.674(2) 112(3) .
O2 H1 O3 0.81(3) 2.14(3) 2.924(2) 162(3) 2
C19 H19C O6 0.98 2.61 3.226(2) 121.0 6_565
C20 H20B O5 0.98 2.66 3.519(2) 147.0 4_556
C20 H20C O6 0.98 2.59 3.104(2) 112.8 .
C18 H18B O2 0.98 2.56 3.281(3) 130.2 2_565
O2 H1 O3 0.81(3) 2.26(3) 2.674(2) 112(3) .
O2 H1 O3 0.81(3) 2.14(3) 2.924(2) 162(3) 2

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050

_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_KP90
_database_code_depnum_ccdc_archive 'CCDC 1842517'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.37

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                   12.1996(5)
_cell_length_b                   6.7253(2)
_cell_length_c                   20.3499(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.1342(15)
_cell_angle_gamma                90
_cell_volume                     1665.28(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.187
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            29603
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.191
_diffrn_reflns_theta_max         28.360
_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             4152
_reflns_number_gt                3406
_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-2014 (Sheldrick, 2014)'
_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)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.671
_refine_ls_restrained_S_all      1.671
_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 0.03387(8) 1.14021(14) -0.17670(5) 0.0259(2) Uani 1 1 d . . . . .
H1 H 0.0158(14) 1.092(2) -0.2170(10) 0.049(5) Uiso 1 1 d . . . . .
O2 O 0.11915(8) 0.82738(14) -0.23449(4) 0.0280(2) Uani 1 1 d . . . . .
O3 O 0.56131(7) 0.60228(12) 0.09235(5) 0.0231(2) Uani 1 1 d . . . . .
O4 O 0.46634(7) 0.39069(12) 0.18516(4) 0.0209(2) Uani 1 1 d . . . . .
O5 O 0.25621(7) 0.44354(14) 0.20816(4) 0.0260(2) Uani 1 1 d . . . . .
C1 C 0.10043(9) 1.01370(17) -0.13910(6) 0.0187(3) Uani 1 1 d . . . . .
C2 C 0.14635(10) 0.84649(18) -0.16833(6) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.21304(11) 0.71906(19) -0.13054(7) 0.0259(3) Uani 1 1 d . . . . .
H3 H 0.2441 0.6057 -0.1499 0.031 Uiso 1 1 calc R U . . .
C4 C 0.23437(11) 0.75817(18) -0.06377(6) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.2796 0.6692 -0.0377 0.028 Uiso 1 1 calc R U . . .
C5 C 0.19111(9) 0.92427(16) -0.03419(6) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.12253(9) 1.05450(17) -0.07276(6) 0.0177(3) Uani 1 1 d . . . . .
C7 C 0.06944(11) 1.23243(19) -0.04287(7) 0.0275(3) Uani 1 1 d . . . . .
H7A H -0.0110 1.2104 -0.0456 0.033 Uiso 1 1 calc R U . . .
H7B H 0.0834 1.3501 -0.0703 0.033 Uiso 1 1 calc R U . . .
C8 C 0.10613(12) 1.28144(19) 0.02788(7) 0.0280(3) Uani 1 1 d . . . . .
H8A H 0.1492 1.4062 0.0283 0.034 Uiso 1 1 calc R U . . .
H8B H 0.0399 1.3075 0.0519 0.034 Uiso 1 1 calc R U . . .
C9 C 0.17335(10) 1.12740(18) 0.06492(6) 0.0218(3) Uani 1 1 d . . . . .
H9 H 0.1882 1.1452 0.1110 0.026 Uiso 1 1 calc R U . . .
C10 C 0.21394(9) 0.96555(17) 0.03703(6) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.28183(10) 0.81749(17) 0.07755(6) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.39149(10) 0.78640(17) 0.06513(6) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.4239 0.8618 0.0322 0.023 Uiso 1 1 calc R U . . .
C13 C 0.45323(10) 0.64472(17) 0.10116(6) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.40559(9) 0.53213(17) 0.14917(6) 0.0177(3) Uani 1 1 d . . . . .
C15 C 0.29602(10) 0.56355(17) 0.16137(6) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.23467(10) 0.70893(18) 0.12613(6) 0.0194(3) Uani 1 1 d . . . . .
H16 H 0.1607 0.7334 0.1355 0.023 Uiso 1 1 calc R U . . .
C17 C 0.17371(13) 0.6739(2) -0.26762(7) 0.0340(4) Uani 1 1 d . . . . .
H17A H 0.2534 0.6898 -0.2596 0.051 Uiso 1 1 calc R U . . .
H17B H 0.1536 0.6820 -0.3150 0.051 Uiso 1 1 calc R U . . .
H17C H 0.1517 0.5441 -0.2510 0.051 Uiso 1 1 calc R U . . .
C18 C 0.61370(11) 0.7191(2) 0.04545(7) 0.0290(3) Uani 1 1 d . . . . .
H18A H 0.5785 0.6947 0.0014 0.044 Uiso 1 1 calc R U . . .
H18B H 0.6916 0.6827 0.0462 0.044 Uiso 1 1 calc R U . . .
H18C H 0.6071 0.8602 0.0564 0.044 Uiso 1 1 calc R U . . .
C19 C 0.47978(11) 0.21105(18) 0.14903(6) 0.0261(3) Uani 1 1 d . . . . .
H19A H 0.4075 0.1601 0.1329 0.039 Uiso 1 1 calc R U . . .
H19B H 0.5174 0.1119 0.1778 0.039 Uiso 1 1 calc R U . . .
H19C H 0.5236 0.2380 0.1115 0.039 Uiso 1 1 calc R U . . .
C20 C 0.14383(11) 0.4734(2) 0.22187(7) 0.0336(4) Uani 1 1 d . . . . .
H20A H 0.1335 0.6112 0.2358 0.050 Uiso 1 1 calc R U . . .
H20B H 0.1251 0.3830 0.2571 0.050 Uiso 1 1 calc R U . . .
H20C H 0.0961 0.4463 0.1821 0.050 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 1.3709(14) . ?
O2 C2 1.3694(15) . ?
O2 C17 1.4242(16) . ?
O3 C13 1.3734(14) . ?
O3 C18 1.4227(15) . ?
O4 C14 1.3829(13) . ?
O4 C19 1.4299(15) . ?
O5 C15 1.3638(15) . ?
O5 C20 1.4329(15) . ?
C1 C6 1.3849(17) . ?
C1 C2 1.4072(17) . ?
C2 C3 1.3774(18) . ?
C3 C4 1.3902(18) . ?
C4 C5 1.3908(16) . ?
C5 C6 1.4101(16) . ?
C5 C10 1.4822(16) . ?
C6 C7 1.5093(16) . ?
C7 C8 1.5130(18) . ?
C8 C9 1.4916(17) . ?
C9 C10 1.3389(17) . ?
C10 C11 1.5029(16) . ?
C11 C16 1.3869(17) . ?
C11 C12 1.3950(17) . ?
C12 C13 1.3904(17) . ?
C13 C14 1.3955(17) . ?
C14 C15 1.3932(17) . ?
C15 C16 1.3975(16) . ?

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
C2 O2 C17 116.43(10) . . ?
C13 O3 C18 117.05(9) . . ?
C14 O4 C19 112.69(9) . . ?
C15 O5 C20 116.55(9) . . ?
O1 C1 C6 119.14(11) . . ?
O1 C1 C2 119.86(11) . . ?
C6 C1 C2 120.99(11) . . ?
O2 C2 C3 125.59(11) . . ?
O2 C2 C1 114.52(10) . . ?
C3 C2 C1 119.89(12) . . ?
C2 C3 C4 119.29(12) . . ?
C3 C4 C5 121.66(11) . . ?
C4 C5 C6 119.10(11) . . ?
C4 C5 C10 121.55(10) . . ?
C6 C5 C10 119.34(10) . . ?
C1 C6 C5 119.05(11) . . ?
C1 C6 C7 119.39(10) . . ?
C5 C6 C7 121.52(11) . . ?
C6 C7 C8 116.75(10) . . ?
C9 C8 C7 116.34(11) . . ?
C10 C9 C8 123.85(12) . . ?
C9 C10 C5 121.17(11) . . ?
C9 C10 C11 120.80(11) . . ?
C5 C10 C11 118.00(10) . . ?
C16 C11 C12 120.18(11) . . ?
C16 C11 C10 119.96(11) . . ?
C12 C11 C10 119.85(11) . . ?
C13 C12 C11 119.83(11) . . ?
O3 C13 C12 124.21(11) . . ?
O3 C13 C14 115.52(10) . . ?
C12 C13 C14 120.26(11) . . ?
O4 C14 C15 119.63(11) . . ?
O4 C14 C13 120.64(10) . . ?
C15 C14 C13 119.73(11) . . ?
O5 C15 C14 115.41(10) . . ?
O5 C15 C16 124.60(11) . . ?
C14 C15 C16 119.99(11) . . ?
C11 C16 C15 119.99(11) . . ?

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
O1 H1 O4 0.90(2) 2.04(2) 2.8794(13) 155.2(15) 4_575
O1 H1 O2 0.90(2) 2.222(17) 2.6587(13) 109.5(13) .

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3

