# 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 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1530676'
_audit_update_record             
;
2017-02-02 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 O4'
_chemical_formula_sum            'C22 H28 O4'
_chemical_formula_weight         356.44

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.243(8)
_cell_length_b                   12.671(9)
_cell_length_c                   9.346(8)
_cell_angle_alpha                90
_cell_angle_beta                 117.356(10)
_cell_angle_gamma                90
_cell_volume                     972.2(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    1232
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8259
_diffrn_reflns_av_unetI/netI     0.1623
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.028
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_point_group_measured_fraction_full 0.807
_reflns_number_total             3158
_reflns_number_gt                1461
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.534
_reflns_Friedel_fraction_max     0.580
_reflns_Friedel_fraction_full    0.607

_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       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0246P)²] 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_abs_structure_details 
;
 Flack x determined using 372 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3158
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_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
C1 C 0.8690(8) 0.4538(4) 0.7003(6) 0.0407(15) Uani 1 1 d . . . . .
C2 C 0.9873(8) 0.4649(4) 0.8612(6) 0.0449(16) Uani 1 1 d . . . . .
C3 C 0.9719(9) 0.5435(5) 0.9540(6) 0.056(2) Uani 1 1 d . . . . .
H3 H 1.0521 0.5526 1.0597 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8355(9) 0.6102(5) 0.8900(7) 0.066(2) Uani 1 1 d . . . . .
H4 H 0.8237 0.6616 0.9549 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7185(9) 0.6002(5) 0.7314(7) 0.063(2) Uani 1 1 d . . . . .
H5 H 0.6284 0.6446 0.6879 0.075 Uiso 1 1 calc R U . . .
C6 C 0.7396(8) 0.5213(5) 0.6383(7) 0.0461(16) Uani 1 1 d . . . . .
C7 C 0.5009(8) 0.5780(5) 0.4025(7) 0.064(2) Uani 1 1 d . . . . .
H7A H 0.4364 0.5592 0.2914 0.095 Uiso 1 1 calc R U . . .
H7B H 0.5443 0.6477 0.4094 0.095 Uiso 1 1 calc R U . . .
H7C H 0.4340 0.5766 0.4564 0.095 Uiso 1 1 calc R U . . .
C8 C 0.7949(7) 0.2814(4) 0.6021(6) 0.0496(17) Uani 1 1 d . . . . .
H8A H 0.6799 0.2987 0.5530 0.060 Uiso 1 1 calc R U . . .
H8B H 0.8271 0.2561 0.7105 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8237(8) 0.1973(4) 0.5063(7) 0.0462(17) Uani 1 1 d . . . . .
C10 C 0.7347(7) 0.1891(5) 0.3452(7) 0.0477(17) Uani 1 1 d . . . . .
H10 H 0.7500 0.1291 0.2964 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6118(7) 0.2694(5) 0.2368(6) 0.0534(18) Uani 1 1 d . . . . .
H11A H 0.5986 0.3243 0.3023 0.064 Uiso 1 1 calc R U . . .
H11B H 0.5071 0.2353 0.1758 0.064 Uiso 1 1 calc R U . . .
C12 C 0.6680(7) 0.3198(5) 0.1185(5) 0.0421(16) Uani 1 1 d . . . . .
C13 C 0.8442(7) 0.3434(4) 0.2130(5) 0.0384(15) Uani 1 1 d . . . . .
H13 H 0.8740 0.3737 0.3133 0.046 Uiso 1 1 calc R U . . .
C14 C 0.9645(7) 0.3285(5) 0.1781(6) 0.0439(16) Uani 1 1 d . . . . .
H14 H 0.9393 0.3049 0.0750 0.053 Uiso 1 1 calc R U . . .
C15 C 1.1384(7) 0.3466(4) 0.2921(6) 0.0386(15) Uani 1 1 d . . . . .
C16 C 1.1876(6) 0.3164(4) 0.4653(6) 0.0363(14) Uani 1 1 d . . . . .
C17 C 1.1222(7) 0.2319(4) 0.4878(6) 0.0434(16) Uani 1 1 d . . . . .
H17 H 1.0601 0.1938 0.3943 0.052 Uiso 1 1 calc R U . . .
C18 C 1.1286(8) 0.1838(5) 0.6389(6) 0.0526(18) Uani 1 1 d . . . . .
H18A H 1.1438 0.2388 0.7168 0.063 Uiso 1 1 calc R U . . .
H18B H 1.2195 0.1351 0.6868 0.063 Uiso 1 1 calc R U . . .
C19 C 0.9698(8) 0.1256(4) 0.5951(6) 0.0501(18) Uani 1 1 d . . . . .
H19A H 0.9618 0.0654 0.5277 0.060 Uiso 1 1 calc R U . . .
H19B H 0.9694 0.0994 0.6925 0.060 Uiso 1 1 calc R U . . .
C20 C 0.5705(7) 0.4237(5) 0.0539(6) 0.060(2) Uani 1 1 d . . . . .
H20A H 0.6022 0.4566 -0.0199 0.090 Uiso 1 1 calc R U . . .
H20B H 0.5929 0.4706 0.1423 0.090 Uiso 1 1 calc R U . . .
H20C H 0.4561 0.4082 -0.0005 0.090 Uiso 1 1 calc R U . . .
C21 C 0.6347(8) 0.2453(5) -0.0219(6) 0.062(2) Uani 1 1 d . . . . .
H21A H 0.6949 0.1811 0.0186 0.093 Uiso 1 1 calc R U . . .
H21B H 0.6678 0.2784 -0.0945 0.093 Uiso 1 1 calc R U . . .
H21C H 0.5204 0.2296 -0.0780 0.093 Uiso 1 1 calc R U . . .
C22 C 1.3119(7) 0.3855(5) 0.5936(5) 0.060(2) Uani 1 1 d . . . . .
H22A H 1.3328 0.3595 0.6978 0.090 Uiso 1 1 calc R U . . .
H22B H 1.2712 0.4564 0.5806 0.090 Uiso 1 1 calc R U . . .
H22C H 1.4111 0.3847 0.5843 0.090 Uiso 1 1 calc R U . . .
O1 O 0.8882(5) 0.3746(3) 0.6081(4) 0.0442(10) Uani 1 1 d . . . . .
O2 O 1.1151(5) 0.3965(3) 0.9189(4) 0.0619(13) Uani 1 1 d . . . . .
H2 H 1.1523 0.3916 1.0169 0.093 Uiso 1 1 calc R U . . .
O6 O 0.6307(5) 0.5050(3) 0.4770(4) 0.0594(12) Uani 1 1 d . . . . .
O15 O 1.2357(5) 0.3853(3) 0.2519(4) 0.0569(13) 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 C6 1.365(8) . ?
C1 O1 1.385(6) . ?
C1 C2 1.402(7) . ?
C2 O2 1.361(7) . ?
C2 C3 1.370(7) . ?
C3 C4 1.404(8) . ?
C4 C5 1.382(7) . ?
C5 C6 1.396(8) . ?
C6 O6 1.391(6) . ?
C7 O6 1.418(7) . ?
C8 O1 1.448(6) . ?
C8 C9 1.493(7) . ?
C9 C10 1.348(7) . ?
C9 C19 1.519(8) . ?
C10 C11 1.515(8) . ?
C11 C12 1.558(7) . ?
C12 C13 1.483(7) . ?
C12 C21 1.529(7) . ?
C12 C20 1.553(7) . ?
C13 C14 1.309(7) . ?
C14 C15 1.482(7) . ?
C15 O15 1.226(6) . ?
C15 C16 1.516(7) . ?
C16 C17 1.293(7) . ?
C16 C22 1.503(7) . ?
C17 C18 1.514(7) . ?
C18 C19 1.521(8) . ?

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 C1 O1 121.9(5) . . ?
C6 C1 C2 119.4(5) . . ?
O1 C1 C2 118.7(5) . . ?
O2 C2 C3 122.4(5) . . ?
O2 C2 C1 117.9(5) . . ?
C3 C2 C1 119.7(6) . . ?
C2 C3 C4 120.1(6) . . ?
C5 C4 C3 120.6(6) . . ?
C4 C5 C6 118.0(6) . . ?
C1 C6 O6 115.0(5) . . ?
C1 C6 C5 122.1(5) . . ?
O6 C6 C5 122.9(6) . . ?
O1 C8 C9 109.8(5) . . ?
C10 C9 C8 122.6(5) . . ?
C10 C9 C19 119.9(5) . . ?
C8 C9 C19 117.3(5) . . ?
C9 C10 C11 125.5(5) . . ?
C10 C11 C12 110.9(5) . . ?
C13 C12 C21 111.6(5) . . ?
C13 C12 C20 110.1(4) . . ?
C21 C12 C20 109.8(4) . . ?
C13 C12 C11 107.0(4) . . ?
C21 C12 C11 110.8(5) . . ?
C20 C12 C11 107.5(5) . . ?
C14 C13 C12 130.4(5) . . ?
C13 C14 C15 124.3(5) . . ?
O15 C15 C14 123.2(5) . . ?
O15 C15 C16 121.8(5) . . ?
C14 C15 C16 115.0(5) . . ?
C17 C16 C22 126.5(5) . . ?
C17 C16 C15 116.8(5) . . ?
C22 C16 C15 116.7(5) . . ?
C16 C17 C18 131.7(5) . . ?
C17 C18 C19 109.0(5) . . ?
C9 C19 C18 111.3(5) . . ?
C1 O1 C8 111.7(4) . . ?
C6 O6 C7 117.6(5) . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038

_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1530675'
_audit_update_record             
;
2017-02-02 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H28 O5'
_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                   14.688(16)
_cell_length_b                   10.009(10)
_cell_length_c                   15.310(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.284(15)
_cell_angle_gamma                90
_cell_volume                     2097(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3610
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-38
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16974
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.153
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4262
_reflns_number_gt                1845
_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       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0542P)²] 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         4262
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   0.712
_refine_ls_restrained_S_all      0.712
_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
C1 C 0.64511(16) 0.4817(2) 0.36286(13) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.74174(16) 0.4417(2) 0.38389(14) 0.0477(6) Uani 1 1 d . . . . .
H2 H 0.7638 0.3623 0.4162 0.057 Uiso 1 1 calc R U . . .
C3 C 0.80447(16) 0.5188(2) 0.35722(14) 0.0466(6) Uani 1 1 d . . . . .
C4 C 0.77124(17) 0.6384(2) 0.30802(14) 0.0449(6) Uani 1 1 d . . . . .
C5 C 0.67642(18) 0.6789(2) 0.28826(14) 0.0514(6) Uani 1 1 d . . . . .
H5 H 0.6546 0.7588 0.2566 0.062 Uiso 1 1 calc R U . . .
C6 C 0.61355(17) 0.6015(2) 0.31514(14) 0.0519(6) Uani 1 1 d . . . . .
H6 H 0.5495 0.6296 0.3013 0.062 Uiso 1 1 calc R U . . .
C7 C 0.57317(18) 0.3971(2) 0.38361(16) 0.0534(6) Uani 1 1 d . . . . .
C8 C 0.94001(18) 0.3696(2) 0.41696(19) 0.0758(8) Uani 1 1 d . . . . .
H8B H 1.0073 0.3639 0.4230 0.114 Uiso 1 1 calc R U . . .
H8C H 0.9044 0.2957 0.3804 0.114 Uiso 1 1 calc R U . . .
H8A H 0.9358 0.3669 0.4781 0.114 Uiso 1 1 calc R U . . .
C9 C 0.54500(15) 0.1940(2) 0.45053(15) 0.0600(7) Uani 1 1 d . . . . .
H9B H 0.5197 0.1353 0.3967 0.072 Uiso 1 1 calc R U . . .
H9A H 0.4904 0.2413 0.4575 0.072 Uiso 1 1 calc R U . . .
C10 C 0.59639(16) 0.1127(2) 0.53730(14) 0.0474(6) Uani 1 1 d . . . . .
C11 C 0.58050(17) 0.1583(2) 0.62484(15) 0.0581(7) Uani 1 1 d . . . . .
H11B H 0.5983 0.0867 0.6706 0.070 Uiso 1 1 calc R U . . .
H11A H 0.5118 0.1780 0.6096 0.070 Uiso 1 1 calc R U . . .
C12 C 0.64138(17) 0.2834(3) 0.66784(17) 0.0627(7) Uani 1 1 d . . . . .
H12A H 0.6160 0.3598 0.6273 0.075 Uiso 1 1 calc R U . . .
H12B H 0.6371 0.3024 0.7284 0.075 Uiso 1 1 calc R U . . .
C13 C 0.74505(16) 0.2599(2) 0.67910(13) 0.0497(6) Uani 1 1 d . . . . .
H13 H 0.7678 0.1738 0.6974 0.060 Uiso 1 1 calc R U . . .
C14 C 0.81066(17) 0.3433(2) 0.66699(13) 0.0475(6) Uani 1 1 d . . . . .
C15 C 0.90508(17) 0.2851(2) 0.67245(14) 0.0505(6) Uani 1 1 d . . . . .
C16 C 0.90260(16) 0.1520(2) 0.63045(14) 0.0524(6) Uani 1 1 d . . . . .
H16 H 0.9517 0.0904 0.6596 0.063 Uiso 1 1 calc R U . . .
C17 C 0.83013(15) 0.1194(2) 0.55073(13) 0.0435(5) Uani 1 1 d . . . . .
H17 H 0.7868 0.1888 0.5242 0.052 Uiso 1 1 calc R U . . .
C18 C 0.80583(17) -0.0092(2) 0.49608(14) 0.0485(6) Uani 1 1 d . . . . .
C19 C 0.69373(17) -0.0282(2) 0.46441(15) 0.0562(6) Uani 1 1 d . . . . .
H19A H 0.6618 0.0252 0.4088 0.067 Uiso 1 1 calc R U . . .
H19B H 0.6778 -0.1211 0.4480 0.067 Uiso 1 1 calc R U . . .
C20 C 0.65504(15) 0.0112(2) 0.53907(15) 0.0492(6) Uani 1 1 d . . . . .
H20 H 0.6745 -0.0417 0.5927 0.059 Uiso 1 1 calc R U . . .
C21 C 0.85939(19) -0.1286(2) 0.55432(17) 0.0727(8) Uani 1 1 d . . . . .
H21C H 0.9286 -0.1152 0.5736 0.109 Uiso 1 1 calc R U . . .
H21A H 0.8413 -0.2085 0.5173 0.109 Uiso 1 1 calc R U . . .
H21B H 0.8419 -0.1373 0.6087 0.109 Uiso 1 1 calc R U . . .
C22 C 0.83255(19) 0.0050(3) 0.40842(16) 0.0720(8) Uani 1 1 d . . . . .
H22A H 0.7987 0.0804 0.3723 0.108 Uiso 1 1 calc R U . . .
H22B H 0.8139 -0.0746 0.3712 0.108 Uiso 1 1 calc R U . . .
H22C H 0.9017 0.0182 0.4270 0.108 Uiso 1 1 calc R U . . .
C23 C 0.7968(2) 0.4906(2) 0.64942(18) 0.0750(8) Uani 1 1 d . . . . .
H23A H 0.8490 0.5380 0.6958 0.112 Uiso 1 1 calc R U . . .
H23B H 0.7355 0.5174 0.6530 0.112 Uiso 1 1 calc R U . . .
H23C H 0.7970 0.5107 0.5882 0.112 Uiso 1 1 calc R U . . .
O3 O 0.89956(12) 0.49075(16) 0.37201(12) 0.0687(5) Uani 1 1 d . . . . .
O4 O 0.83101(12) 0.71518(15) 0.27916(10) 0.0650(5) Uani 1 1 d . . . . .
H4 H 0.8829 0.6760 0.2895 0.097 Uiso 1 1 calc R U . . .
O7A O 0.61296(10) 0.28965(16) 0.43550(10) 0.0578(5) Uani 1 1 d . . . . .
O7B O 0.48656(13) 0.41784(19) 0.35433(14) 0.0949(7) Uani 1 1 d . . . . .
O15 O 0.98215(12) 0.34716(18) 0.70888(11) 0.0715(5) 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 C6 1.393(3) . ?
C1 C2 1.395(3) . ?
C1 C7 1.476(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 O3 1.361(3) . ?
C3 C4 1.405(3) . ?
C4 O4 1.356(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O7B 1.203(3) . ?
C7 O7A 1.339(3) . ?
C8 O3 1.415(3) . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8A 0.9600 . ?
C9 O7A 1.460(3) . ?
C9 C10 1.507(3) . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C10 C20 1.326(3) . ?
C10 C11 1.512(3) . ?
C11 C12 1.541(3) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 C13 1.488(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.338(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.479(3) . ?
C14 C23 1.499(3) . ?
C15 O15 1.233(3) . ?
C15 C16 1.474(3) . ?
C16 C17 1.336(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.505(3) . ?
C17 H17 0.9300 . ?
C18 C21 1.528(3) . ?
C18 C22 1.535(3) . ?
C18 C19 1.550(3) . ?
C19 C20 1.502(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 0.9300 . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O4 H4 0.8200 . ?

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 C1 C2 119.0(2) . . ?
C6 C1 C7 118.6(2) . . ?
C2 C1 C7 122.2(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O3 C3 C2 126.4(2) . . ?
O3 C3 C4 113.6(2) . . ?
C2 C3 C4 119.9(2) . . ?
O4 C4 C5 119.1(2) . . ?
O4 C4 C3 121.2(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O7B C7 O7A 122.3(2) . . ?
O7B C7 C1 124.3(2) . . ?
O7A C7 C1 113.3(2) . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
O7A C9 C10 109.93(18) . . ?
O7A C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
O7A C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
H9B C9 H9A 108.2 . . ?
C20 C10 C9 123.1(2) . . ?
C20 C10 C11 121.4(2) . . ?
C9 C10 C11 115.4(2) . . ?
C10 C11 C12 111.84(18) . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
H11B C11 H11A 107.9 . . ?
C13 C12 C11 109.4(2) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 130.1(2) . . ?
C14 C13 H13 115.0 . . ?
C12 C13 H13 115.0 . . ?
C13 C14 C15 117.0(2) . . ?
C13 C14 C23 125.5(2) . . ?
C15 C14 C23 117.5(2) . . ?
O15 C15 C16 121.8(2) . . ?
O15 C15 C14 121.0(2) . . ?
C16 C15 C14 117.2(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 131.8(2) . . ?
C16 C17 H17 114.1 . . ?
C18 C17 H17 114.1 . . ?
C17 C18 C21 112.12(19) . . ?
C17 C18 C22 108.81(19) . . ?
C21 C18 C22 110.0(2) . . ?
C17 C18 C19 106.83(18) . . ?
C21 C18 C19 110.5(2) . . ?
C22 C18 C19 108.51(18) . . ?
C20 C19 C18 112.46(18) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C10 C20 C19 127.4(2) . . ?
C10 C20 H20 116.3 . . ?
C19 C20 H20 116.3 . . ?
C18 C21 H21C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 O3 C8 118.84(18) . . ?
C4 O4 H4 109.5 . . ?
C7 O7A C9 116.35(19) . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

