# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_KP75
_database_code_depnum_ccdc_archive 'CCDC 1046343'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2016-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H28 O5'
_chemical_formula_weight         384.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7350(5)
_cell_length_b                   9.4232(5)
_cell_length_c                   18.5619(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.544(2)
_cell_angle_gamma                90
_cell_volume                     2003.60(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5525
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      29.62

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.902
_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            13077
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.436
_diffrn_reflns_theta_max         29.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5627
_reflns_number_gt                3948
_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)+(0.0500P)²+0.7356P] 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         5627
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.31726(10) 1.43828(12) 0.40249(6) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.48607(9) 1.33573(12) 0.34121(6) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.08573(9) 0.94968(12) 0.07705(6) 0.0279(3) Uani 1 1 d . . . . .
O4 O 0.02511(8) 0.67695(11) 0.05890(5) 0.0233(2) Uani 1 1 d . . . . .
O5 O 0.08192(9) 0.48986(11) 0.16996(6) 0.0267(2) Uani 1 1 d . . . . .
C1 C 0.31803(12) 1.00927(16) 0.34809(7) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.22722(12) 1.06428(17) 0.37672(8) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.1648 1.0036 0.3819 0.028 Uiso 1 1 calc R U . . .
C3 C 0.22516(12) 1.20490(17) 0.39792(8) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.1638 1.2391 0.4192 0.028 Uiso 1 1 calc R U . . .
C4 C 0.31342(12) 1.29514(16) 0.38781(8) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.40422(11) 1.24217(16) 0.35767(7) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.40943(11) 1.09961(16) 0.33869(7) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.51147(12) 1.04695(17) 0.30873(8) 0.0240(3) Uani 1 1 d . . . . .
H7A H 0.5388 1.1246 0.2807 0.029 Uiso 1 1 calc R U . . .
H7B H 0.4848 0.9681 0.2739 0.029 Uiso 1 1 calc R U . . .
C8 C 0.61510(13) 0.99482(18) 0.36941(9) 0.0302(4) Uani 1 1 d . . . . .
H8A H 0.6875 1.0059 0.3507 0.036 Uiso 1 1 calc R U . . .
H8B H 0.6218 1.0582 0.4127 0.036 Uiso 1 1 calc R U . . .
C9 C 0.60975(13) 0.84243(19) 0.39580(9) 0.0319(4) Uani 1 1 d . . . . .
H9A H 0.6791 0.8246 0.4359 0.038 Uiso 1 1 calc R U . . .
H9B H 0.6147 0.7779 0.3545 0.038 Uiso 1 1 calc R U . . .
C10 C 0.49969(13) 0.80451(18) 0.42418(8) 0.0278(3) Uani 1 1 d . . . . .
H10A H 0.5170 0.7232 0.4586 0.033 Uiso 1 1 calc R U . . .
H10B H 0.4775 0.8862 0.4517 0.033 Uiso 1 1 calc R U . . .
C11 C 0.39945(12) 0.76688(17) 0.36192(8) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.3938 0.6709 0.3459 0.029 Uiso 1 1 calc R U . . .
C12 C 0.31763(12) 0.85636(16) 0.32716(7) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.22890(11) 0.81073(17) 0.26054(7) 0.0208(3) Uani 1 1 d . . . . .
C14 C 0.19055(12) 0.90844(16) 0.20426(8) 0.0212(3) Uani 1 1 d . . . . .
H14 H 0.2106 1.0058 0.2117 0.025 Uiso 1 1 calc R U . . .
C15 C 0.12263(12) 0.86321(17) 0.13695(8) 0.0210(3) Uani 1 1 d . . . . .
C16 C 0.09067(11) 0.72124(16) 0.12634(7) 0.0203(3) Uani 1 1 d . . . . .
C17 C 0.12217(12) 0.62547(16) 0.18445(8) 0.0208(3) Uani 1 1 d . . . . .
C18 C 0.19211(12) 0.66960(16) 0.25140(8) 0.0225(3) Uani 1 1 d . . . . .
H18 H 0.2147 0.6038 0.2907 0.027 Uiso 1 1 calc R U . . .
C19 C 0.23275(15) 1.4928(2) 0.43966(10) 0.0363(4) Uani 1 1 d . . . . .
H19A H 0.2443 1.5953 0.4469 0.054 Uiso 1 1 calc R U . . .
H19B H 0.1543 1.4748 0.4100 0.054 Uiso 1 1 calc R U . . .
H19C H 0.2414 1.4461 0.4877 0.054 Uiso 1 1 calc R U . . .
C20 C 0.56996(14) 1.3882(2) 0.40284(10) 0.0346(4) Uani 1 1 d . . . . .
H20A H 0.6235 1.4531 0.3855 0.052 Uiso 1 1 calc R U . . .
H20B H 0.5298 1.4390 0.4362 0.052 Uiso 1 1 calc R U . . .
H20C H 0.6142 1.3086 0.4292 0.052 Uiso 1 1 calc R U . . .
C21 C 0.09476(15) 1.09863(18) 0.08926(9) 0.0315(4) Uani 1 1 d . . . . .
H21A H 0.0658 1.1486 0.0426 0.047 Uiso 1 1 calc R U . . .
H21B H 0.0481 1.1259 0.1249 0.047 Uiso 1 1 calc R U . . .
H21C H 0.1766 1.1241 0.1088 0.047 Uiso 1 1 calc R U . . .
C22 C 0.09630(13) 0.63066(18) 0.00954(8) 0.0277(4) Uani 1 1 d . . . . .
H22A H 0.0461 0.6005 -0.0373 0.042 Uiso 1 1 calc R U . . .
H22B H 0.1463 0.7090 0.0005 0.042 Uiso 1 1 calc R U . . .
H22C H 0.1451 0.5509 0.0317 0.042 Uiso 1 1 calc R U . . .
C23 C 0.10233(17) 0.39316(18) 0.23068(9) 0.0361(4) Uani 1 1 d . . . . .
H23A H 0.0700 0.3000 0.2139 0.054 Uiso 1 1 calc R U . . .
H23B H 0.1865 0.3844 0.2505 0.054 Uiso 1 1 calc R U . . .
H23C H 0.0645 0.4288 0.2693 0.054 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 C4 1.3749(19) . ?
O1 C19 1.4217(19) . ?
O2 C5 1.3859(17) . ?
O2 C20 1.426(2) . ?
O3 C15 1.3706(18) . ?
O3 C21 1.4221(19) . ?
O4 C16 1.3838(16) . ?
O4 C22 1.4353(17) . ?
O5 C17 1.3686(18) . ?
O5 C23 1.428(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.410(2) . ?
C1 C12 1.492(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.384(2) . ?
C4 C5 1.399(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.5094(19) . ?
C7 C8 1.547(2) . ?
C8 C9 1.523(2) . ?
C9 C10 1.539(2) . ?
C10 C11 1.5015(19) . ?
C11 C12 1.334(2) . ?
C12 C13 1.4964(19) . ?
C13 C14 1.392(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.3947(19) . ?
C15 C16 1.392(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.3957(19) . ?

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
C4 O1 C19 117.05(13) . . ?
C5 O2 C20 115.76(12) . . ?
C15 O3 C21 117.25(12) . . ?
C16 O4 C22 112.51(10) . . ?
C17 O5 C23 116.68(12) . . ?
C2 C1 C6 119.28(14) . . ?
C2 C1 C12 120.02(13) . . ?
C6 C1 C12 120.69(12) . . ?
C3 C2 C1 121.86(13) . . ?
C2 C3 C4 119.33(13) . . ?
O1 C4 C3 124.69(13) . . ?
O1 C4 C5 115.74(13) . . ?
C3 C4 C5 119.51(14) . . ?
O2 C5 C6 119.14(12) . . ?
O2 C5 C4 119.07(14) . . ?
C6 C5 C4 121.62(13) . . ?
C5 C6 C1 118.33(12) . . ?
C5 C6 C7 119.47(13) . . ?
C1 C6 C7 122.20(14) . . ?
C6 C7 C8 113.40(12) . . ?
C9 C8 C7 116.92(13) . . ?
C8 C9 C10 115.17(13) . . ?
C11 C10 C9 111.52(13) . . ?
C12 C11 C10 125.74(15) . . ?
C11 C12 C1 121.55(13) . . ?
C11 C12 C13 121.10(14) . . ?
C1 C12 C13 117.06(12) . . ?
C14 C13 C18 119.84(13) . . ?
C14 C13 C12 118.93(13) . . ?
C18 C13 C12 121.00(13) . . ?
C13 C14 C15 119.92(14) . . ?
O3 C15 C16 115.38(12) . . ?
O3 C15 C14 124.30(14) . . ?
C16 C15 C14 120.30(14) . . ?
O4 C16 C15 119.85(13) . . ?
O4 C16 C17 120.45(13) . . ?
C15 C16 C17 119.67(12) . . ?
O5 C17 C16 115.50(12) . . ?
O5 C17 C18 124.35(13) . . ?
C16 C17 C18 120.14(14) . . ?
C17 C18 C13 119.88(14) . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_KP76
_database_code_depnum_ccdc_archive 'CCDC 1046344'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2016-09-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 O5'
_chemical_formula_weight         370.43

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.6410(12)
_cell_length_b                   11.1239(8)
_cell_length_c                   20.5570(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3805.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9721
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      29.58

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.966
_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            80769
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3865
_reflns_number_gt                3206
_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)+(0.0418P)²+1.6747P] 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         3865
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.62534(6) 0.37516(10) 0.27576(5) 0.0326(2) Uani 1 1 d . . . . .
O2 O 0.67093(6) 0.17398(9) 0.21609(5) 0.0319(2) Uani 1 1 d . . . . .
O3 O 0.21315(6) 0.24318(8) 0.12518(5) 0.0297(2) Uani 1 1 d . . . . .
O4 O 0.13391(6) 0.36548(9) 0.03176(5) 0.0322(2) Uani 1 1 d . . . . .
O5 O 0.20584(6) 0.54462(9) -0.03416(5) 0.0326(2) Uani 1 1 d . . . . .
C1 C 0.59327(8) 0.34825(12) 0.21593(6) 0.0254(3) Uani 1 1 d . . . . .
C2 C 0.61610(8) 0.24375(12) 0.18313(6) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.58391(8) 0.21814(12) 0.12265(6) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.5982 0.1463 0.1005 0.033 Uiso 1 1 calc R U . . .
C4 C 0.53039(8) 0.29913(12) 0.09490(6) 0.0278(3) Uani 1 1 d . . . . .
H4 H 0.5086 0.2821 0.0532 0.033 Uiso 1 1 calc R U . . .
C5 C 0.50789(8) 0.40437(12) 0.12650(6) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.53790(8) 0.42806(12) 0.18930(6) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.51102(8) 0.53415(13) 0.23009(7) 0.0289(3) Uani 1 1 d . . . . .
H7A H 0.5060 0.5077 0.2759 0.035 Uiso 1 1 calc R U . . .
H7B H 0.4570 0.5595 0.2152 0.035 Uiso 1 1 calc R U . . .
C8 C 0.56752(9) 0.64331(14) 0.22752(7) 0.0344(3) Uani 1 1 d . . . . .
H8A H 0.5595 0.6913 0.2675 0.041 Uiso 1 1 calc R U . . .
H8B H 0.6237 0.6139 0.2278 0.041 Uiso 1 1 calc R U . . .
C9 C 0.55670(9) 0.72561(14) 0.16908(7) 0.0358(3) Uani 1 1 d . . . . .
H9A H 0.5998 0.7869 0.1696 0.043 Uiso 1 1 calc R U . . .
H9B H 0.5047 0.7682 0.1734 0.043 Uiso 1 1 calc R U . . .
C10 C 0.55834(9) 0.66063(14) 0.10292(7) 0.0333(3) Uani 1 1 d . . . . .
H10A H 0.5746 0.7183 0.0687 0.040 Uiso 1 1 calc R U . . .
H10B H 0.5990 0.5957 0.1043 0.040 Uiso 1 1 calc R U . . .
C11 C 0.47789(8) 0.60767(13) 0.08571(7) 0.0294(3) Uani 1 1 d . . . . .
H11 H 0.4395 0.6610 0.0673 0.035 Uiso 1 1 calc R U . . .
C12 C 0.45460(8) 0.49329(12) 0.09364(6) 0.0257(3) Uani 1 1 d . . . . .
C13 C 0.37276(8) 0.45413(12) 0.07392(6) 0.0255(3) Uani 1 1 d . . . . .
C14 C 0.33454(8) 0.36093(12) 0.10704(6) 0.0258(3) Uani 1 1 d . . . . .
H14 H 0.3630 0.3167 0.1392 0.031 Uiso 1 1 calc R U . . .
C15 C 0.25482(8) 0.33220(12) 0.09326(6) 0.0251(3) Uani 1 1 d . . . . .
C16 C 0.21222(8) 0.39611(12) 0.04628(6) 0.0258(3) Uani 1 1 d . . . . .
C17 C 0.25156(8) 0.48724(12) 0.01190(6) 0.0260(3) Uani 1 1 d . . . . .
C18 C 0.33127(8) 0.51523(12) 0.02491(6) 0.0267(3) Uani 1 1 d . . . . .
H18 H 0.3576 0.5760 0.0005 0.032 Uiso 1 1 calc R U . . .
C19 C 0.69574(10) 0.06524(14) 0.18534(8) 0.0388(4) Uani 1 1 d . . . . .
H19A H 0.6487 0.0143 0.1774 0.058 Uiso 1 1 calc R U . . .
H19B H 0.7336 0.0227 0.2136 0.058 Uiso 1 1 calc R U . . .
H19C H 0.7219 0.0841 0.1439 0.058 Uiso 1 1 calc R U . . .
C20 C 0.26085(9) 0.15114(12) 0.15441(7) 0.0314(3) Uani 1 1 d . . . . .
H20A H 0.3031 0.1263 0.1241 0.047 Uiso 1 1 calc R U . . .
H20B H 0.2268 0.0819 0.1648 0.047 Uiso 1 1 calc R U . . .
H20C H 0.2854 0.1820 0.1944 0.047 Uiso 1 1 calc R U . . .
C21 C 0.07609(9) 0.44405(15) 0.06133(8) 0.0370(4) Uani 1 1 d . . . . .
H21A H 0.0825 0.4419 0.1087 0.056 Uiso 1 1 calc R U . . .
H21B H 0.0218 0.4176 0.0498 0.056 Uiso 1 1 calc R U . . .
H21C H 0.0845 0.5263 0.0457 0.056 Uiso 1 1 calc R U . . .
C22 C 0.24464(10) 0.63922(13) -0.06921(7) 0.0356(3) Uani 1 1 d . . . . .
H22A H 0.2626 0.7013 -0.0387 0.053 Uiso 1 1 calc R U . . .
H22B H 0.2068 0.6744 -0.1004 0.053 Uiso 1 1 calc R U . . .
H22C H 0.2911 0.6068 -0.0926 0.053 Uiso 1 1 calc R U . . .
H1 H 0.6497(11) 0.3113(17) 0.2913(9) 0.050(5) 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
O1 C1 1.3737(16) . ?
O2 C2 1.3762(16) . ?
O2 C19 1.4259(17) . ?
O3 C15 1.3756(16) . ?
O3 C20 1.4281(16) . ?
O4 C16 1.3796(16) . ?
O4 C21 1.4350(18) . ?
O5 C17 1.3722(16) . ?
O5 C22 1.4294(17) . ?
C1 C6 1.3917(19) . ?
C1 C2 1.3966(19) . ?
C2 C3 1.3834(19) . ?
C3 C4 1.3894(19) . ?
C4 C5 1.3902(19) . ?
C5 C6 1.4090(18) . ?
C5 C12 1.4902(19) . ?
C6 C7 1.5153(18) . ?
C7 C8 1.537(2) . ?
C8 C9 1.521(2) . ?
C9 C10 1.540(2) . ?
C10 C11 1.505(2) . ?
C11 C12 1.340(2) . ?
C12 C13 1.4863(18) . ?
C13 C14 1.3940(19) . ?
C13 C18 1.3977(19) . ?
C14 C15 1.3936(19) . ?
C15 C16 1.3930(19) . ?
C16 C17 1.3984(19) . ?
C17 C18 1.3885(19) . ?

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 C19 116.88(11) . . ?
C15 O3 C20 115.89(11) . . ?
C16 O4 C21 113.03(11) . . ?
C17 O5 C22 116.09(11) . . ?
O1 C1 C6 118.07(12) . . ?
O1 C1 C2 120.53(12) . . ?
C6 C1 C2 121.40(12) . . ?
O2 C2 C3 125.67(12) . . ?
O2 C2 C1 114.33(11) . . ?
C3 C2 C1 120.00(12) . . ?
C2 C3 C4 118.93(12) . . ?
C3 C4 C5 121.79(12) . . ?
C4 C5 C6 119.35(12) . . ?
C4 C5 C12 120.49(12) . . ?
C6 C5 C12 120.13(12) . . ?
C1 C6 C5 118.41(12) . . ?
C1 C6 C7 118.32(12) . . ?
C5 C6 C7 123.24(12) . . ?
C6 C7 C8 114.57(11) . . ?
C9 C8 C7 115.49(12) . . ?
C8 C9 C10 114.38(12) . . ?
C11 C10 C9 112.05(12) . . ?
C12 C11 C10 126.89(13) . . ?
C11 C12 C13 120.66(13) . . ?
C11 C12 C5 120.88(12) . . ?
C13 C12 C5 118.32(12) . . ?
C14 C13 C18 119.23(12) . . ?
C14 C13 C12 120.18(12) . . ?
C18 C13 C12 120.46(12) . . ?
C15 C14 C13 120.36(12) . . ?
O3 C15 C16 116.20(12) . . ?
O3 C15 C14 123.22(12) . . ?
C16 C15 C14 120.56(12) . . ?
O4 C16 C15 120.31(12) . . ?
O4 C16 C17 120.79(12) . . ?
C15 C16 C17 118.82(12) . . ?
O5 C17 C18 123.93(12) . . ?
O5 C17 C16 115.24(12) . . ?
C18 C17 C16 120.83(12) . . ?
C17 C18 C13 120.11(13) . . ?

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 O2 0.879(19) 2.202(18) 2.6623(14) 112.3(15) .
O1 H1 O3 0.879(19) 2.152(19) 2.9046(14) 143.3(16) 6_656

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

