# 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_4b_CCDC1527913
_database_code_depnum_ccdc_archive 'CCDC 1527913'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2014/6, manual editing plus enCIFer'
_audit_creation_date             '14 June 2017'
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C23 H20 O4), 0.25(H2 O)'
_chemical_formula_sum            'C23 H20.50 O4.25'
_chemical_formula_weight         364.89

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   21.8983(8)
_cell_length_b                   21.8983(8)
_cell_length_c                   21.2428(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8821.9(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6017
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             3465
_exptl_transmission_factor_min   0.6716
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
 SADABS V2012/1 (Bruker 2001) 
;

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

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17177
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.722
_diffrn_reflns_theta_max         29.116
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5224
_reflns_number_gt                3580
_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       'APEX2 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2015)'


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

_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)+(0.1185P)²+7.3942P] 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         5224
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1786
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.44480(10) 0.49228(10) 0.44308(9) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.45630(11) 0.56541(10) 0.43237(10) 0.0305(4) Uani 1 1 d . . . . .
H2A H 0.4545 0.5857 0.4735 0.037 Uiso 1 1 calc R U . . .
H2B H 0.4171 0.5617 0.4063 0.037 Uiso 1 1 calc R U . . .
C3 C 0.52629(10) 0.61613(9) 0.39999(9) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.5643 0.6251 0.4310 0.030 Uiso 1 1 calc R U . . .
C4 C 0.54111(9) 0.58296(9) 0.34008(8) 0.0214(4) Uani 1 1 d . . . . .
C5 C 0.53992(9) 0.51358(9) 0.36094(8) 0.0221(4) Uani 1 1 d . . . . .
H5 H 0.5779 0.5279 0.3932 0.027 Uiso 1 1 calc R U . . .
C6 C 0.47055(10) 0.46128(9) 0.39363(9) 0.0266(4) Uani 1 1 d . . . . .
H6A H 0.4335 0.4386 0.3611 0.032 Uiso 1 1 calc R U . . .
H6B H 0.4768 0.4238 0.4134 0.032 Uiso 1 1 calc R U . . .
C7 C 0.61700(9) 0.63427(9) 0.32002(9) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.63039(10) 0.66006(10) 0.25808(10) 0.0301(4) Uani 1 1 d . . . . .
H8 H 0.6778 0.6895 0.2449 0.036 Uiso 1 1 calc R U . . .
C9 C 0.57737(13) 0.64403(11) 0.21637(10) 0.0356(5) Uani 1 1 d . . . . .
O4 O 0.50688(9) 0.60011(9) 0.23134(7) 0.0419(4) Uani 1 1 d . . . . .
C11 C 0.48674(10) 0.56843(10) 0.28928(9) 0.0259(4) Uani 1 1 d . . . . .
C12 C 0.5771(3) 0.6675(2) 0.14942(17) 0.0441(9) Uani 0.6667 1 d . . P A 1
H12A H 0.5285 0.6448 0.1338 0.066 Uiso 0.6667 1 calc R U P A 1
H12B H 0.5977 0.7188 0.1484 0.066 Uiso 0.6667 1 calc R U P A 1
H12C H 0.6050 0.6540 0.1227 0.066 Uiso 0.6667 1 calc R U P A 1
C12' C 0.6223(5) 0.6916(4) 0.1598(4) 0.0499(19) Uani 0.3333 1 d . . P A 2
H12D H 0.5909 0.6860 0.1246 0.075 Uiso 0.3333 1 calc R U P A 2
H12E H 0.6477 0.7411 0.1731 0.075 Uiso 0.3333 1 calc R U P A 2
H12F H 0.6562 0.6773 0.1464 0.075 Uiso 0.3333 1 calc R U P A 2
C13 C 0.55804(10) 0.47869(9) 0.30770(8) 0.0233(4) Uani 1 1 d . . . . .
C14 C 0.51072(10) 0.44144(10) 0.25950(9) 0.0285(4) Uani 1 1 d . . . . .
H14 H 0.4658 0.4383 0.2588 0.034 Uiso 1 1 calc R U . . .
C15 C 0.52831(12) 0.40888(11) 0.21247(10) 0.0369(5) Uani 1 1 d . . . . .
H15 H 0.4954 0.3834 0.1801 0.044 Uiso 1 1 calc R U . . .
C16 C 0.59364(13) 0.41335(12) 0.21262(11) 0.0424(5) Uani 1 1 d . . . . .
H16 H 0.6058 0.3915 0.1801 0.051 Uiso 1 1 calc R U . . .
C17 C 0.64112(12) 0.44976(13) 0.26031(11) 0.0421(5) Uani 1 1 d . . . . .
H17 H 0.6859 0.4526 0.2609 0.051 Uiso 1 1 calc R U . . .
C18 C 0.62311(11) 0.48230(11) 0.30749(10) 0.0318(4) Uani 1 1 d . . . . .
H18 H 0.6560 0.5073 0.3400 0.038 Uiso 1 1 calc R U . . .
C19 C 0.53396(10) 0.68761(10) 0.38531(9) 0.0272(4) Uani 1 1 d . . . . .
C20 C 0.48286(12) 0.69560(12) 0.35348(11) 0.0380(5) Uani 1 1 d . . . . .
H20 H 0.4400 0.6550 0.3414 0.046 Uiso 1 1 calc R U . . .
C21 C 0.49390(14) 0.76233(13) 0.33920(12) 0.0444(6) Uani 1 1 d . . . . .
H21 H 0.4584 0.7669 0.3175 0.053 Uiso 1 1 calc R U . . .
C22 C 0.55570(13) 0.82195(12) 0.35615(11) 0.0403(5) Uani 1 1 d . . . . .
H22 H 0.5634 0.8674 0.3456 0.048 Uiso 1 1 calc R U . . .
C23 C 0.60589(12) 0.81468(11) 0.38850(12) 0.0399(5) Uani 1 1 d . . . . .
H23 H 0.6483 0.8555 0.4010 0.048 Uiso 1 1 calc R U . . .
C24 C 0.59527(11) 0.74815(11) 0.40314(11) 0.0340(5) Uani 1 1 d . . . . .
H24 H 0.6305 0.7441 0.4257 0.041 Uiso 1 1 calc R U . . .
O1 O 0.41192(8) 0.45758(8) 0.48850(7) 0.0347(4) Uani 1 1 d . . . . .
O2 O 0.66513(7) 0.65319(7) 0.35759(7) 0.0320(3) Uani 1 1 d . . . . .
O3 O 0.42430(7) 0.52976(8) 0.29768(7) 0.0353(4) Uani 1 1 d . . . . .
O1W O 0.3333 0.6667 0.2544(5) 0.094(3) Uani 0.5 3 d S T P . .
O2W O 0.3333 0.6667 0.2006(8) 0.077(4) Uani 0.25 3 d S T P . .


_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 1.216(2) . ?
C1 C6 1.505(3) . ?
C1 C2 1.509(3) . ?
C2 C3 1.534(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C19 1.521(3) . ?
C3 C4 1.578(2) . ?
C3 H3 1.0000 . ?
C4 C11 1.518(2) . ?
C4 C7 1.529(2) . ?
C4 C5 1.570(2) . ?
C5 C13 1.524(2) . ?
C5 C6 1.537(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.218(2) . ?
C7 C8 1.404(3) . ?
C8 C9 1.360(3) . ?
C8 H8 0.9500 . ?
C9 O4 1.387(3) . ?
C9 C12 1.513(4) . ?
C9 C12' 1.573(8) . ?
O4 C11 1.373(2) . ?
C11 O3 1.209(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13 C18 1.387(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.387(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.390(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O1W O2W 1.143(17) . ?
O2W O2W 1.44(4) 13_565 ?

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 C6 120.66(17) . . ?
O1 C1 C2 121.01(18) . . ?
C6 C1 C2 118.18(16) . . ?
C1 C2 C3 114.35(15) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C19 C3 C2 113.17(15) . . ?
C19 C3 C4 111.48(15) . . ?
C2 C3 C4 112.92(15) . . ?
C19 C3 H3 106.2 . . ?
C2 C3 H3 106.2 . . ?
C4 C3 H3 106.2 . . ?
C11 C4 C7 113.97(15) . . ?
C11 C4 C5 111.47(14) . . ?
C7 C4 C5 106.01(13) . . ?
C11 C4 C3 110.46(14) . . ?
C7 C4 C3 106.53(14) . . ?
C5 C4 C3 108.06(14) . . ?
C13 C5 C6 111.71(14) . . ?
C13 C5 C4 113.14(14) . . ?
C6 C5 C4 112.36(14) . . ?
C13 C5 H5 106.3 . . ?
C6 C5 H5 106.3 . . ?
C4 C5 H5 106.3 . . ?
C1 C6 C5 115.65(15) . . ?
C1 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C1 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
O2 C7 C8 120.41(17) . . ?
O2 C7 C4 120.34(17) . . ?
C8 C7 C4 119.24(16) . . ?
C9 C8 C7 121.82(17) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 O4 122.70(17) . . ?
C8 C9 C12 132.3(3) . . ?
O4 C9 C12 105.0(2) . . ?
C8 C9 C12' 99.0(4) . . ?
O4 C9 C12' 138.2(4) . . ?
C11 O4 C9 121.39(16) . . ?
O3 C11 O4 116.84(17) . . ?
O3 C11 C4 122.41(17) . . ?
O4 C11 C4 120.74(16) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C12' H12D 109.5 . . ?
C9 C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C9 C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C18 C13 C14 118.23(17) . . ?
C18 C13 C5 119.43(17) . . ?
C14 C13 C5 122.32(16) . . ?
C15 C14 C13 120.86(19) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 121.17(19) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C24 C19 C20 117.88(18) . . ?
C24 C19 C3 118.92(17) . . ?
C20 C19 C3 123.18(18) . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.0(2) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 121.0(2) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
O1W O2W O2W 180.0 . 13_565 ?

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 C3 147.77(19) . . . . ?
C6 C1 C2 C3 -36.6(2) . . . . ?
C1 C2 C3 C19 175.60(16) . . . . ?
C1 C2 C3 C4 47.8(2) . . . . ?
C19 C3 C4 C11 -63.67(19) . . . . ?
C2 C3 C4 C11 65.04(19) . . . . ?
C19 C3 C4 C7 60.60(18) . . . . ?
C2 C3 C4 C7 -170.68(15) . . . . ?
C19 C3 C4 C5 174.15(14) . . . . ?
C2 C3 C4 C5 -57.14(19) . . . . ?
C11 C4 C5 C13 61.92(19) . . . . ?
C7 C4 C5 C13 -62.63(18) . . . . ?
C3 C4 C5 C13 -176.52(14) . . . . ?
C11 C4 C5 C6 -65.72(19) . . . . ?
C7 C4 C5 C6 169.73(14) . . . . ?
C3 C4 C5 C6 55.84(18) . . . . ?
O1 C1 C6 C5 -148.19(18) . . . . ?
C2 C1 C6 C5 36.1(2) . . . . ?
C13 C5 C6 C1 -174.75(15) . . . . ?
C4 C5 C6 C1 -46.3(2) . . . . ?
C11 C4 C7 O2 176.04(16) . . . . ?
C5 C4 C7 O2 -61.0(2) . . . . ?
C3 C4 C7 O2 54.0(2) . . . . ?
C11 C4 C7 C8 -3.1(2) . . . . ?
C5 C4 C7 C8 119.90(17) . . . . ?
C3 C4 C7 C8 -125.16(17) . . . . ?
O2 C7 C8 C9 -175.13(18) . . . . ?
C4 C7 C8 C9 4.0(3) . . . . ?
C7 C8 C9 O4 -1.5(3) . . . . ?
C7 C8 C9 C12 176.2(3) . . . . ?
C7 C8 C9 C12' 175.1(3) . . . . ?
C8 C9 O4 C11 -1.9(3) . . . . ?
C12 C9 O4 C11 179.8(2) . . . . ?
C12' C9 O4 C11 -176.8(5) . . . . ?
C9 O4 C11 O3 -178.38(18) . . . . ?
C9 O4 C11 C4 2.6(3) . . . . ?
C7 C4 C11 O3 -179.08(17) . . . . ?
C5 C4 C11 O3 61.0(2) . . . . ?
C3 C4 C11 O3 -59.2(2) . . . . ?
C7 C4 C11 O4 -0.1(2) . . . . ?
C5 C4 C11 O4 -120.04(18) . . . . ?
C3 C4 C11 O4 119.80(18) . . . . ?
C6 C5 C13 C18 -125.22(18) . . . . ?
C4 C5 C13 C18 106.79(19) . . . . ?
C6 C5 C13 C14 53.2(2) . . . . ?
C4 C5 C13 C14 -74.8(2) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C5 C13 C14 C15 -178.49(17) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C5 C13 C18 C17 178.62(19) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C2 C3 C19 C24 130.1(2) . . . . ?
C4 C3 C19 C24 -101.3(2) . . . . ?
C2 C3 C19 C20 -51.3(3) . . . . ?
C4 C3 C19 C20 77.3(2) . . . . ?
C24 C19 C20 C21 1.1(3) . . . . ?
C3 C19 C20 C21 -177.5(2) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C20 C19 C24 C23 -1.3(3) . . . . ?
C3 C19 C24 C23 177.4(2) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?

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
C2 H2B O3 0.99 2.44 2.956(3) 112.0 .
C6 H6A O2 0.99 2.43 3.319(2) 149.0 18_545
C6 H6A O3 0.99 2.50 2.991(2) 110.5 .
C12 H12C O2 0.98 2.55 3.416(4) 147.7 8_654
C12' H12F O2 0.98 2.64 3.215(8) 117.3 8_654

_refine_diff_density_max         0.889
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_4e_CCDC1527914
_database_code_depnum_ccdc_archive 'CCDC 1527914'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2014/6, manual editing plus enCIFer'
_audit_creation_date             '14 June 2017'
#=============================================================================

#=============================================================================
# GENERAL AND CHEMICAL DATA
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 O6'
_chemical_formula_sum            'C25 H24 O6'
_chemical_formula_weight         420.44

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'


#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   14.1989(3)
_cell_length_b                   6.32060(10)
_cell_length_c                   24.2710(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.751(2)
_cell_angle_gamma                90
_cell_volume                     2163.11(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2535
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      28.51

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.866081
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?


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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.715
_diffrn_radiation_type           synchrotron
_diffrn_source                   
'Swiss Norwegian beamline @ ESRF, Grenoble, France'
_diffrn_measurement_device_type  
'Pilatus 2M, Dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'π scans'
_diffrn_detector_area_resol_mean .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            30603
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.536
_diffrn_reflns_theta_max         25.512
_diffrn_reflns_theta_full        25.404
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3923
_reflns_number_gt                3869
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Pylatus software, SNBL@ESRF (Dyadkin 2013)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_refinement_gui        'shelXle (Huebschle, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


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

_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)+(0.0402P)²+3.8383P] 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         3923
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.31216(15) 0.2708(3) 0.29257(9) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
O2 O 0.27037(16) 0.2435(4) 0.37779(9) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
O3 O 0.42672(16) 0.8695(4) 0.32236(9) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
C1 C 0.3050(3) 0.3566(8) 0.34409(17) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
C2 C 0.33128(16) 0.5933(4) 0.35506(9) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
C3 C 0.3925(3) 0.6907(6) 0.31300(17) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
C4 C 0.4019(2) 0.5665(6) 0.26217(12) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
H4A H 0.4385 0.6224 0.2352 0.030 Uiso 0.804(3) 1 calc R U P A 1
C5 C 0.3595(2) 0.3748(6) 0.25301(13) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
C6 C 0.3540(2) 0.2483(5) 0.20042(11) 0.0249(2) Uiso 0.804(3) 1 d . U P A 1
H6A H 0.3934 0.3152 0.1748 0.037 Uiso 0.804(3) 1 calc R U P A 1
H6B H 0.2881 0.2427 0.1832 0.037 Uiso 0.804(3) 1 calc R U P A 1
H6C H 0.3770 0.1044 0.2089 0.037 Uiso 0.804(3) 1 calc R U P A 1
O1' O 0.3968(6) 0.6692(16) 0.2642(3) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
O2' O 0.4312(7) 0.9025(15) 0.3375(4) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
O3' O 0.2904(6) 0.2346(16) 0.3659(4) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
C1' C 0.3936(13) 0.726(3) 0.3193(7) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
C2' C 0.33128(16) 0.5933(4) 0.35506(9) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
C3' C 0.3174(12) 0.373(3) 0.3381(7) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
C4' C 0.3351(9) 0.314(2) 0.2810(5) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
H4B H 0.3245 0.1730 0.2683 0.030 Uiso 0.196(3) 1 calc R U P A 2
C5' C 0.3673(9) 0.465(2) 0.2466(5) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
C6' C 0.3687(8) 0.4489(19) 0.1831(5) 0.0249(2) Uiso 0.196(3) 1 d . U P A 2
H6D H 0.3647 0.2999 0.1719 0.037 Uiso 0.196(3) 1 calc R U P A 2
H6E H 0.4278 0.5100 0.1731 0.037 Uiso 0.196(3) 1 calc R U P A 2
H6F H 0.3146 0.5265 0.1642 0.037 Uiso 0.196(3) 1 calc R U P A 2
O4 O 0.19436(12) 0.8870(3) 0.48451(7) 0.0353(4) Uani 1 1 d . . . . .
O5 O 0.02137(11) 0.5094(3) 0.13399(7) 0.0310(4) Uani 1 1 d . . . . .
O6 O 0.78542(11) 0.5035(3) 0.42701(8) 0.0364(4) Uani 1 1 d . . . . .
C7 C 0.37802(15) 0.6086(4) 0.41848(9) 0.0259(5) Uani 1 1 d . . . . .
H7A H 0.3551 0.4822 0.4378 0.031 Uiso 1 1 calc R U . A 1
C8 C 0.34214(16) 0.8052(4) 0.44807(9) 0.0287(5) Uani 1 1 d . . . . .
H8A H 0.3726 0.8093 0.4869 0.034 Uiso 1 1 calc R U . . .
H8B H 0.3606 0.9350 0.4292 0.034 Uiso 1 1 calc R U . . .
C9 C 0.23336(16) 0.8007(4) 0.44770(9) 0.0268(5) Uani 1 1 d . . . . .
C10 C 0.17715(15) 0.6925(4) 0.39755(9) 0.0252(5) Uani 1 1 d . . . . .
H10A H 0.1134 0.7570 0.3902 0.030 Uiso 1 1 calc R U . . .
H10B H 0.1693 0.5403 0.4055 0.030 Uiso 1 1 calc R U . . .
C11 C 0.23117(14) 0.7186(3) 0.34575(9) 0.0201(4) Uani 1 1 d . . . . .
H11 H 0.2475 0.8722 0.3439 0.024 Uiso 1 1 calc R U . A 1
C12 C 0.17240(14) 0.6655(3) 0.28987(9) 0.0199(4) Uani 1 1 d . . . . .
C13 C 0.17761(15) 0.7999(4) 0.24395(9) 0.0239(5) Uani 1 1 d . . . . .
H13 H 0.2151 0.9244 0.2487 0.029 Uiso 1 1 calc R U . . .
C14 C 0.12881(15) 0.7555(4) 0.19103(9) 0.0252(5) Uani 1 1 d . . . . .
H14 H 0.1336 0.8487 0.1608 0.030 Uiso 1 1 calc R U . . .
C15 C 0.07298(14) 0.5708(4) 0.18380(9) 0.0238(5) Uani 1 1 d . . . . .
C16 C 0.06564(15) 0.4342(4) 0.22943(9) 0.0238(5) Uani 1 1 d . . . . .
H16 H 0.0276 0.3104 0.2246 0.029 Uiso 1 1 calc R U . . .
C17 C 0.11441(14) 0.4812(4) 0.28167(9) 0.0225(5) Uani 1 1 d . . . . .
H17 H 0.1087 0.3891 0.3120 0.027 Uiso 1 1 calc R U . . .
C18 C 0.02017(17) 0.6529(4) 0.08701(10) 0.0328(6) Uani 1 1 d . . . . .
H18A H -0.0044 0.7909 0.0970 0.049 Uiso 1 1 calc R U . . .
H18B H -0.0207 0.5947 0.0553 0.049 Uiso 1 1 calc R U . . .
H18C H 0.0847 0.6697 0.0772 0.049 Uiso 1 1 calc R U . . .
C19 C 0.48758(15) 0.5881(4) 0.42289(9) 0.0247(5) Uani 1 1 d . . . . .
C20 C 0.52824(16) 0.3997(4) 0.40395(10) 0.0291(5) Uani 1 1 d . . . . .
H20 H 0.4879 0.2878 0.3896 0.035 Uiso 1 1 calc R U . . .
C21 C 0.62735(17) 0.3763(4) 0.40608(11) 0.0316(5) Uani 1 1 d . . . . .
H21 H 0.6531 0.2504 0.3926 0.038 Uiso 1 1 calc R U . . .
C22 C 0.68866(15) 0.5394(4) 0.42827(9) 0.0262(5) Uani 1 1 d . . . . .
C23 C 0.65037(16) 0.7259(4) 0.44869(9) 0.0260(5) Uani 1 1 d . . . . .
H23 H 0.6909 0.8350 0.4645 0.031 Uiso 1 1 calc R U . . .
C24 C 0.55019(16) 0.7478(4) 0.44517(9) 0.0261(5) Uani 1 1 d . . . . .
H24 H 0.5245 0.8745 0.4583 0.031 Uiso 1 1 calc R U . . .
C25 C 0.84942(18) 0.6638(5) 0.45197(14) 0.0482(8) Uani 1 1 d . . . . .
H25A H 0.8374 0.7976 0.4320 0.072 Uiso 1 1 calc R U . . .
H25B H 0.9151 0.6195 0.4500 0.072 Uiso 1 1 calc R U . . .
H25C H 0.8392 0.6830 0.4909 0.072 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 1.378(5) . ?
O1 C5 1.399(4) . ?
O2 C1 1.232(4) . ?
O3 C3 1.240(5) . ?
C1 C2 1.557(5) . ?
C2 C3 1.544(5) . ?
C2 C7 1.606(3) . ?
C2 C11 1.620(3) . ?
C3 C4 1.482(5) . ?
C4 C5 1.359(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.500(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O1' C1' 1.390(17) . ?
O1' C5' 1.408(17) . ?
O2' C1' 1.292(18) . ?
O3' C3' 1.20(2) . ?
C1' C2' 1.555(19) . ?
C2' C3' 1.46(2) . ?
C2' C7 1.606(3) . ?
C2' C11 1.620(3) . ?
C3' C4' 1.49(2) . ?
C4' C5' 1.382(18) . ?
C4' H4B 0.9500 . ?
C5' C6' 1.546(16) . ?
C6' H6D 0.9800 . ?
C6' H6E 0.9800 . ?
C6' H6F 0.9800 . ?
O4 C9 1.232(3) . ?
O5 C15 1.393(3) . ?
O5 C18 1.456(3) . ?
O6 C22 1.396(3) . ?
O6 C25 1.445(3) . ?
C7 C8 1.551(3) . ?
C7 C19 1.552(3) . ?
C7 H7A 1.0000 . ?
C8 C9 1.544(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.536(3) . ?
C10 C11 1.557(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.543(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.410(3) . ?
C12 C17 1.426(3) . ?
C13 C14 1.414(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.410(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.418(3) . ?
C16 C17 1.403(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.410(3) . ?
C19 C20 1.423(3) . ?
C20 C21 1.410(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.414(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.412(3) . ?
C23 C24 1.422(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C1 O1 C5 122.0(3) . . ?
O2 C1 O1 116.9(4) . . ?
O2 C1 C2 123.4(3) . . ?
O1 C1 C2 119.5(3) . . ?
C3 C2 C1 114.3(2) . . ?
C3 C2 C7 114.1(2) . . ?
C1 C2 C7 106.6(2) . . ?
C3 C2 C11 105.4(2) . . ?
C1 C2 C11 104.9(2) . . ?
C7 C2 C11 111.18(17) . . ?
O3 C3 C4 124.3(4) . . ?
O3 C3 C2 118.7(3) . . ?
C4 C3 C2 116.9(3) . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C4 C5 O1 123.1(3) . . ?
C4 C5 C6 126.3(3) . . ?
O1 C5 C6 110.6(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1' O1' C5' 119.1(11) . . ?
O2' C1' O1' 119.4(16) . . ?
O2' C1' C2' 121.0(12) . . ?
O1' C1' C2' 118.9(11) . . ?
C3' C2' C1' 115.1(7) . . ?
C3' C2' C7 110.8(7) . . ?
C1' C2' C7 107.7(6) . . ?
C3' C2' C11 109.9(7) . . ?
C1' C2' C11 101.9(7) . . ?
C7 C2' C11 111.18(17) . . ?
O3' C3' C2' 125.6(13) . . ?
O3' C3' C4' 116.2(16) . . ?
C2' C3' C4' 118.1(11) . . ?
C5' C4' C3' 119.6(13) . . ?
C5' C4' H4B 120.2 . . ?
C3' C4' H4B 120.2 . . ?
C4' C5' O1' 123.8(11) . . ?
C4' C5' C6' 126.9(13) . . ?
O1' C5' C6' 109.0(11) . . ?
C5' C6' H6D 109.5 . . ?
C5' C6' H6E 109.5 . . ?
H6D C6' H6E 109.5 . . ?
C5' C6' H6F 109.5 . . ?
H6D C6' H6F 109.5 . . ?
H6E C6' H6F 109.5 . . ?
C15 O5 C18 117.55(18) . . ?
C22 O6 C25 116.67(19) . . ?
C8 C7 C19 114.58(19) . . ?
C8 C7 C2' 111.77(18) . . ?
C19 C7 C2' 111.03(17) . . ?
C8 C7 C2 111.77(18) . . ?
C19 C7 C2 111.03(17) . . ?
C8 C7 H7A 106.3 . . ?
C19 C7 H7A 106.3 . . ?
C2 C7 H7A 106.3 . . ?
C9 C8 C7 111.45(19) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O4 C9 C10 122.4(2) . . ?
O4 C9 C8 121.5(2) . . ?
C10 C9 C8 116.05(18) . . ?
C9 C10 C11 109.48(17) . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 114.82(17) . . ?
C12 C11 C2 113.03(17) . . ?
C10 C11 C2 110.07(17) . . ?
C12 C11 C2' 113.03(17) . . ?
C10 C11 C2' 110.07(17) . . ?
C12 C11 H11 106.1 . . ?
C10 C11 H11 106.1 . . ?
C2 C11 H11 106.1 . . ?
C13 C12 C17 117.69(19) . . ?
C13 C12 C11 119.35(19) . . ?
C17 C12 C11 122.94(19) . . ?
C12 C13 C14 122.2(2) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O5 C15 C14 124.7(2) . . ?
O5 C15 C16 115.38(19) . . ?
C14 C15 C16 119.9(2) . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 121.0(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 117.5(2) . . ?
C24 C19 C7 123.2(2) . . ?
C20 C19 C7 119.3(2) . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
O6 C22 C23 124.3(2) . . ?
O6 C22 C21 115.9(2) . . ?
C23 C22 C21 119.8(2) . . ?
C22 C23 C24 118.9(2) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C19 C24 C23 122.3(2) . . ?
C19 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C5 O1 C1 O2 -172.9(3) . . . . ?
C5 O1 C1 C2 12.9(5) . . . . ?
O2 C1 C2 C3 167.7(4) . . . . ?
O1 C1 C2 C3 -18.4(5) . . . . ?
O2 C1 C2 C7 40.7(4) . . . . ?
O1 C1 C2 C7 -145.4(3) . . . . ?
O2 C1 C2 C11 -77.3(4) . . . . ?
O1 C1 C2 C11 96.6(3) . . . . ?
C1 C2 C3 O3 -171.0(3) . . . . ?
C7 C2 C3 O3 -48.0(4) . . . . ?
C11 C2 C3 O3 74.3(4) . . . . ?
C1 C2 C3 C4 12.2(5) . . . . ?
C7 C2 C3 C4 135.2(3) . . . . ?
C11 C2 C3 C4 -102.5(3) . . . . ?
O3 C3 C4 C5 -177.2(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 O1 -6.5(5) . . . . ?
C3 C4 C5 C6 171.8(3) . . . . ?
C1 O1 C5 C4 0.1(5) . . . . ?
C1 O1 C5 C6 -178.5(3) . . . . ?
C5' O1' C1' O2' 171.7(13) . . . . ?
C5' O1' C1' C2' -18.0(19) . . . . ?
O2' C1' C2' C3' -162.2(14) . . . . ?
O1' C1' C2' C3' 27.6(18) . . . . ?
O2' C1' C2' C7 -38.2(16) . . . . ?
O1' C1' C2' C7 151.7(12) . . . . ?
O2' C1' C2' C11 78.9(15) . . . . ?
O1' C1' C2' C11 -91.3(13) . . . . ?
C1' C2' C3' O3' 162.8(15) . . . . ?
C7 C2' C3' O3' 40.4(18) . . . . ?
C11 C2' C3' O3' -82.9(17) . . . . ?
C1' C2' C3' C4' -19.1(18) . . . . ?
C7 C2' C3' C4' -141.6(11) . . . . ?
C11 C2' C3' C4' 95.2(12) . . . . ?
O3' C3' C4' C5' -179.4(13) . . . . ?
C2' C3' C4' C5' 2(2) . . . . ?
C3' C4' C5' O1' 8.8(19) . . . . ?
C3' C4' C5' C6' -165.5(13) . . . . ?
C1' O1' C5' C4' -0.3(18) . . . . ?
C1' O1' C5' C6' 174.8(11) . . . . ?
C3' C2' C7 C8 -146.4(6) . . . . ?
C1' C2' C7 C8 87.0(7) . . . . ?
C11 C2' C7 C8 -23.9(3) . . . . ?
C3' C2' C7 C19 84.3(7) . . . . ?
C1' C2' C7 C19 -42.3(7) . . . . ?
C11 C2' C7 C19 -153.20(19) . . . . ?
C3 C2 C7 C8 95.2(3) . . . . ?
C1 C2 C7 C8 -137.7(2) . . . . ?
C11 C2 C7 C8 -23.9(3) . . . . ?
C3 C2 C7 C19 -34.1(3) . . . . ?
C1 C2 C7 C19 93.0(2) . . . . ?
C11 C2 C7 C19 -153.20(19) . . . . ?
C19 C7 C8 C9 -173.39(18) . . . . ?
C2' C7 C8 C9 59.2(2) . . . . ?
C2 C7 C8 C9 59.2(2) . . . . ?
C7 C8 C9 O4 151.8(2) . . . . ?
C7 C8 C9 C10 -31.1(3) . . . . ?
O4 C9 C10 C11 146.8(2) . . . . ?
C8 C9 C10 C11 -30.3(3) . . . . ?
C9 C10 C11 C12 -166.02(18) . . . . ?
C9 C10 C11 C2 65.1(2) . . . . ?
C9 C10 C11 C2' 65.1(2) . . . . ?
C3 C2 C11 C12 69.6(2) . . . . ?
C1 C2 C11 C12 -51.5(3) . . . . ?
C7 C2 C11 C12 -166.31(18) . . . . ?
C3 C2 C11 C10 -160.6(2) . . . . ?
C1 C2 C11 C10 78.4(2) . . . . ?
C7 C2 C11 C10 -36.4(2) . . . . ?
C3' C2' C11 C12 -43.3(7) . . . . ?
C1' C2' C11 C12 79.2(6) . . . . ?
C7 C2' C11 C12 -166.31(18) . . . . ?
C3' C2' C11 C10 86.5(7) . . . . ?
C1' C2' C11 C10 -151.0(6) . . . . ?
C7 C2' C11 C10 -36.4(2) . . . . ?
C10 C11 C12 C13 136.4(2) . . . . ?
C2 C11 C12 C13 -96.2(2) . . . . ?
C2' C11 C12 C13 -96.2(2) . . . . ?
C10 C11 C12 C17 -45.6(3) . . . . ?
C2 C11 C12 C17 81.8(2) . . . . ?
C2' C11 C12 C17 81.8(2) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 177.24(19) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C18 O5 C15 C14 -4.1(3) . . . . ?
C18 O5 C15 C16 175.05(19) . . . . ?
C13 C14 C15 O5 179.8(2) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
O5 C15 C16 C17 -179.76(19) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C12 -0.4(3) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
C11 C12 C17 C16 -177.00(19) . . . . ?
C8 C7 C19 C24 -8.3(3) . . . . ?
C2' C7 C19 C24 119.5(2) . . . . ?
C2 C7 C19 C24 119.5(2) . . . . ?
C8 C7 C19 C20 171.5(2) . . . . ?
C2' C7 C19 C20 -60.8(3) . . . . ?
C2 C7 C19 C20 -60.8(3) . . . . ?
C24 C19 C20 C21 -1.6(3) . . . . ?
C7 C19 C20 C21 178.6(2) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
C25 O6 C22 C23 4.5(3) . . . . ?
C25 O6 C22 C21 -177.1(2) . . . . ?
C20 C21 C22 O6 -178.2(2) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
O6 C22 C23 C24 176.9(2) . . . . ?
C21 C22 C23 C24 -1.6(3) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
C7 C19 C24 C23 -179.9(2) . . . . ?
C22 C23 C24 C19 1.2(3) . . . . ?

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
C6 H6A O3 0.98 2.57 3.315(4) 132.9 2_645
C6' H6E O2' 0.98 2.16 2.957(15) 137.6 2_645
C8 H8B O2 0.99 2.57 3.349(3) 135.1 1_565
C8 H8B O2' 0.99 2.56 3.159(9) 119.2 .
C8 H8B O3' 0.99 2.57 3.397(10) 141.6 1_565
C10 H10A O5 0.99 2.51 3.469(3) 163.9 2
C10 H10B O2 0.99 2.50 3.192(3) 126.5 .
C23 H23 O4 0.95 2.61 3.554(3) 175.0 3_676

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_4f_CCDC1527915
_database_code_depnum_ccdc_archive 'CCDC 1527915'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2014/6, manual editing plus enCIFer'
_audit_creation_date             '14 June 2017'
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H36 O4'
_chemical_formula_sum            'C31 H36 O4'
_chemical_formula_weight         472.60

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   22.418(4)
_cell_length_b                   9.8837(17)
_cell_length_c                   11.914(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.040(5)
_cell_angle_gamma                90
_cell_volume                     2636.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9806
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      29.15

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   0.7088
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
 SADABS V2012/1 (Bruker 2001) 
;

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

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            56127
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4820
_reflns_number_gt                3915
_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       'APEX2 2012.4 (Bruker, 2012b)'
_computing_cell_refinement       'SAINT V8.27b (Bruker, 2012a)'
_computing_data_reduction        'SAINT V8.27b (Bruker, 2012a)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2015)'


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

_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)+(0.0919P)²+3.0223P] 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         4820
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1963
_refine_ls_wR_factor_gt          0.1838
_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


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.28126(10) 0.6125(2) 0.1967(2) 0.0557(6) Uani 1 1 d . . . . .
O2 O 0.29291(8) 0.4828(2) 0.34610(16) 0.0478(5) Uani 1 1 d . . . . .
O3 O 0.24543(10) 0.2962(2) -0.01254(18) 0.0563(6) Uani 1 1 d . . . . .
O4 O 0.19777(9) -0.0197(2) 0.2520(2) 0.0567(6) Uani 1 1 d . . . . .
C1 C 0.25977(10) 0.3650(2) 0.1780(2) 0.0324(5) Uani 1 1 d . . . . .
C2 C 0.28009(10) 0.4877(3) 0.2464(2) 0.0349(6) Uani 1 1 d . . . . .
C3 C 0.26767(12) 0.6288(3) 0.0835(3) 0.0445(7) Uani 1 1 d . . . . .
C4 C 0.25722(11) 0.5225(3) 0.0131(2) 0.0380(6) Uani 1 1 d . . . . .
H4 H 0.2515 0.5389 -0.0653 0.046 Uiso 1 1 calc R U . . .
C5 C 0.25456(11) 0.3894(3) 0.0525(2) 0.0391(6) Uani 1 1 d . . . . .
C6 C 0.2669(2) 0.7724(4) 0.0508(6) 0.121(2) Uani 1 1 d . . . . .
H6A H 0.3069 0.8108 0.0640 0.182 Uiso 1 1 calc R U . . .
H6B H 0.2387 0.8216 0.0958 0.182 Uiso 1 1 calc R U . . .
H6C H 0.2545 0.7804 -0.0290 0.182 Uiso 1 1 calc R U . . .
C7 C 0.19603(11) 0.3330(3) 0.2242(3) 0.0404(6) Uani 1 1 d . . . . .
H7 H 0.2023 0.3243 0.3076 0.048 Uiso 1 1 calc R U . . .
C8 C 0.17140(12) 0.1987(3) 0.1827(3) 0.0507(7) Uani 1 1 d . . . . .
H8A H 0.1329 0.1809 0.2170 0.061 Uiso 1 1 calc R U . . .
H8B H 0.1637 0.2027 0.1001 0.061 Uiso 1 1 calc R U . . .
C9 C 0.21413(12) 0.0849(3) 0.2115(3) 0.0487(7) Uani 1 1 d . . . . .
C10 C 0.27699(12) 0.1073(3) 0.1784(3) 0.0495(7) Uani 1 1 d . . . . .
H10A H 0.2781 0.0982 0.0958 0.059 Uiso 1 1 calc R U . . .
H10B H 0.3028 0.0357 0.2130 0.059 Uiso 1 1 calc R U . . .
C11 C 0.30255(11) 0.2449(3) 0.2132(2) 0.0380(6) Uani 1 1 d . . . . .
H11 H 0.3056 0.2449 0.2972 0.046 Uiso 1 1 calc R U . . .
C12 C 0.15288(10) 0.4503(3) 0.2036(2) 0.0351(6) Uani 1 1 d . . . . .
C13 C 0.14594(11) 0.5427(3) 0.2885(2) 0.0397(6) Uani 1 1 d . . . . .
H13 H 0.1668 0.5293 0.3591 0.048 Uiso 1 1 calc R U . . .
C14 C 0.10929(11) 0.6545(3) 0.2734(2) 0.0375(6) Uani 1 1 d . . . . .
H14 H 0.1064 0.7173 0.3332 0.045 Uiso 1 1 calc R U . . .
C15 C 0.07648(10) 0.6773(2) 0.17272(19) 0.0301(5) Uani 1 1 d . . . . .
C16 C 0.08357(11) 0.5836(3) 0.0877(2) 0.0378(6) Uani 1 1 d . . . . .
H16 H 0.0623 0.5958 0.0173 0.045 Uiso 1 1 calc R U . . .
C17 C 0.12092(11) 0.4729(3) 0.1028(2) 0.0403(6) Uani 1 1 d . . . . .
H17 H 0.1247 0.4110 0.0426 0.048 Uiso 1 1 calc R U . . .
C18 C 0.03554(11) 0.8000(3) 0.1554(2) 0.0358(6) Uani 1 1 d . . . . .
C19 C 0.06552(14) 0.9008(3) 0.0792(3) 0.0554(8) Uani 1 1 d . . . . .
H19A H 0.1049 0.9254 0.1128 0.083 Uiso 1 1 calc R U . . .
H19B H 0.0407 0.9822 0.0705 0.083 Uiso 1 1 calc R U . . .
H19C H 0.0702 0.8596 0.0054 0.083 Uiso 1 1 calc R U . . .
C20 C 0.0250(2) 0.8713(4) 0.2658(3) 0.0806(13) Uani 1 1 d . . . . .
H20A H 0.0069 0.8079 0.3173 0.121 Uiso 1 1 calc R U . . .
H20B H -0.0018 0.9483 0.2516 0.121 Uiso 1 1 calc R U . . .
H20C H 0.0632 0.9036 0.2995 0.121 Uiso 1 1 calc R U . . .
C21 C -0.02461(12) 0.7577(3) 0.0995(3) 0.0536(8) Uani 1 1 d . . . . .
H21A H -0.0183 0.7194 0.0252 0.080 Uiso 1 1 calc R U . . .
H21B H -0.0507 0.8370 0.0914 0.080 Uiso 1 1 calc R U . . .
H21C H -0.0433 0.6898 0.1462 0.080 Uiso 1 1 calc R U . . .
C22 C 0.36584(10) 0.2648(2) 0.1758(2) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.40703(11) 0.3315(3) 0.2465(2) 0.0424(6) Uani 1 1 d . . . . .
H23 H 0.3945 0.3677 0.3152 0.051 Uiso 1 1 calc R U . . .
C24 C 0.46589(11) 0.3469(3) 0.2201(2) 0.0429(6) Uani 1 1 d . . . . .
H24 H 0.4926 0.3945 0.2705 0.051 Uiso 1 1 calc R U . . .
C25 C 0.48689(10) 0.2946(3) 0.1215(2) 0.0359(6) Uani 1 1 d . . . . .
C26 C 0.44539(12) 0.2303(3) 0.0501(3) 0.0485(7) Uani 1 1 d . . . . .
H26 H 0.4578 0.1947 -0.0189 0.058 Uiso 1 1 calc R U . . .
C27 C 0.38619(12) 0.2161(3) 0.0762(3) 0.0478(7) Uani 1 1 d . . . . .
H27 H 0.3590 0.1720 0.0244 0.057 Uiso 1 1 calc R U . . .
C28 C 0.55292(11) 0.3016(3) 0.0937(2) 0.0439(7) Uani 1 1 d . . . . .
C29 C 0.58829(16) 0.3974(6) 0.1724(4) 0.1050(18) Uani 1 1 d . . . . .
H29A H 0.5869 0.3647 0.2499 0.158 Uiso 1 1 calc R U . . .
H29B H 0.5708 0.4881 0.1669 0.158 Uiso 1 1 calc R U . . .
H29C H 0.6299 0.4009 0.1511 0.158 Uiso 1 1 calc R U . . .
C30 C 0.57832(17) 0.1605(5) 0.1064(5) 0.1032(18) Uani 1 1 d . . . . .
H30A H 0.5614 0.1030 0.0457 0.155 Uiso 1 1 calc R U . . .
H30B H 0.5681 0.1230 0.1791 0.155 Uiso 1 1 calc R U . . .
H30C H 0.6218 0.1641 0.1026 0.155 Uiso 1 1 calc R U . . .
C31 C 0.55947(14) 0.3507(4) -0.0253(3) 0.0618(9) Uani 1 1 d . . . . .
H31A H 0.6017 0.3481 -0.0428 0.093 Uiso 1 1 calc R U . . .
H31B H 0.5446 0.4437 -0.0325 0.093 Uiso 1 1 calc R U . . .
H31C H 0.5363 0.2921 -0.0777 0.093 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 C2 1.369(3) . ?
O1 C3 1.376(4) . ?
O2 C2 1.208(3) . ?
O3 C5 1.214(3) . ?
O4 C9 1.206(3) . ?
C1 C5 1.514(4) . ?
C1 C2 1.517(3) . ?
C1 C11 1.569(3) . ?
C1 C7 1.590(3) . ?
C3 C4 1.357(4) . ?
C3 C6 1.472(5) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.511(4) . ?
C7 C12 1.522(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.505(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.499(4) . ?
C10 C11 1.524(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C22 1.522(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.378(4) . ?
C12 C17 1.383(4) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 C18 1.528(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C20 1.520(4) . ?
C18 C19 1.528(4) . ?
C18 C21 1.530(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.381(4) . ?
C22 C23 1.383(4) . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 C28 1.536(3) . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C30 1.510(5) . ?
C28 C31 1.513(4) . ?
C28 C29 1.525(5) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
C2 O1 C3 121.4(2) . . ?
C5 C1 C2 114.1(2) . . ?
C5 C1 C11 113.5(2) . . ?
C2 C1 C11 107.4(2) . . ?
C5 C1 C7 110.5(2) . . ?
C2 C1 C7 102.90(19) . . ?
C11 C1 C7 107.73(19) . . ?
O2 C2 O1 116.9(2) . . ?
O2 C2 C1 123.0(2) . . ?
O1 C2 C1 120.0(2) . . ?
C4 C3 O1 122.5(2) . . ?
C4 C3 C6 125.8(4) . . ?
O1 C3 C6 111.8(4) . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
O3 C5 C4 120.6(3) . . ?
O3 C5 C1 120.7(3) . . ?
C4 C5 C1 118.6(2) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 113.5(2) . . ?
C8 C7 C1 112.4(2) . . ?
C12 C7 C1 111.5(2) . . ?
C8 C7 H7 106.3 . . ?
C12 C7 H7 106.3 . . ?
C1 C7 H7 106.3 . . ?
C9 C8 C7 111.4(2) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O4 C9 C10 122.8(3) . . ?
O4 C9 C8 121.9(3) . . ?
C10 C9 C8 115.2(2) . . ?
C9 C10 C11 113.9(2) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C22 C11 C10 112.3(2) . . ?
C22 C11 C1 113.0(2) . . ?
C10 C11 C1 112.8(2) . . ?
C22 C11 H11 106.1 . . ?
C10 C11 H11 106.1 . . ?
C1 C11 H11 106.1 . . ?
C13 C12 C17 117.2(2) . . ?
C13 C12 C7 118.8(2) . . ?
C17 C12 C7 124.0(2) . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 116.4(2) . . ?
C16 C15 C18 121.5(2) . . ?
C14 C15 C18 122.1(2) . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C12 C17 C16 121.5(2) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C20 C18 C15 111.8(2) . . ?
C20 C18 C19 107.8(3) . . ?
C15 C18 C19 108.5(2) . . ?
C20 C18 C21 109.2(3) . . ?
C15 C18 C21 110.6(2) . . ?
C19 C18 C21 108.9(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 116.7(2) . . ?
C27 C22 C11 124.2(2) . . ?
C23 C22 C11 119.1(2) . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C26 C25 C24 116.4(2) . . ?
C26 C25 C28 120.9(2) . . ?
C24 C25 C28 122.7(2) . . ?
C25 C26 C27 122.0(3) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C22 C27 C26 121.4(3) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C30 C28 C31 109.6(3) . . ?
C30 C28 C29 109.3(4) . . ?
C31 C28 C29 107.7(3) . . ?
C30 C28 C25 107.5(2) . . ?
C31 C28 C25 111.0(2) . . ?
C29 C28 C25 111.8(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C3 O1 C2 O2 179.7(2) . . . . ?
C3 O1 C2 C1 -3.9(3) . . . . ?
C5 C1 C2 O2 -171.7(2) . . . . ?
C11 C1 C2 O2 -45.0(3) . . . . ?
C7 C1 C2 O2 68.6(3) . . . . ?
C5 C1 C2 O1 12.1(3) . . . . ?
C11 C1 C2 O1 138.8(2) . . . . ?
C7 C1 C2 O1 -107.7(2) . . . . ?
C2 O1 C3 C4 -5.6(4) . . . . ?
C2 O1 C3 C6 175.1(3) . . . . ?
O1 C3 C4 C5 5.5(4) . . . . ?
C6 C3 C4 C5 -175.2(3) . . . . ?
C3 C4 C5 O3 -179.6(3) . . . . ?
C3 C4 C5 C1 3.8(4) . . . . ?
C2 C1 C5 O3 171.5(2) . . . . ?
C11 C1 C5 O3 48.0(3) . . . . ?
C7 C1 C5 O3 -73.1(3) . . . . ?
C2 C1 C5 C4 -11.9(3) . . . . ?
C11 C1 C5 C4 -135.5(2) . . . . ?
C7 C1 C5 C4 103.4(3) . . . . ?
C5 C1 C7 C8 67.9(3) . . . . ?
C2 C1 C7 C8 -169.8(2) . . . . ?
C11 C1 C7 C8 -56.5(3) . . . . ?
C5 C1 C7 C12 -60.8(3) . . . . ?
C2 C1 C7 C12 61.4(3) . . . . ?
C11 C1 C7 C12 174.7(2) . . . . ?
C12 C7 C8 C9 -176.4(2) . . . . ?
C1 C7 C8 C9 55.8(3) . . . . ?
C7 C8 C9 O4 133.4(3) . . . . ?
C7 C8 C9 C10 -51.0(4) . . . . ?
O4 C9 C10 C11 -136.2(3) . . . . ?
C8 C9 C10 C11 48.2(4) . . . . ?
C9 C10 C11 C22 -178.7(2) . . . . ?
C9 C10 C11 C1 -49.8(3) . . . . ?
C5 C1 C11 C22 58.5(3) . . . . ?
C2 C1 C11 C22 -68.6(3) . . . . ?
C7 C1 C11 C22 -178.8(2) . . . . ?
C5 C1 C11 C10 -70.0(3) . . . . ?
C2 C1 C11 C10 162.9(2) . . . . ?
C7 C1 C11 C10 52.6(3) . . . . ?
C8 C7 C12 C13 135.9(3) . . . . ?
C1 C7 C12 C13 -95.9(3) . . . . ?
C8 C7 C12 C17 -46.0(4) . . . . ?
C1 C7 C12 C17 82.2(3) . . . . ?
C17 C12 C13 C14 -0.9(4) . . . . ?
C7 C12 C13 C14 177.3(2) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C13 C14 C15 C18 179.6(2) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C18 C15 C16 C17 179.6(2) . . . . ?
C13 C12 C17 C16 0.1(4) . . . . ?
C7 C12 C17 C16 -178.1(2) . . . . ?
C15 C16 C17 C12 0.1(4) . . . . ?
C16 C15 C18 C20 168.3(3) . . . . ?
C14 C15 C18 C20 -12.8(4) . . . . ?
C16 C15 C18 C19 -73.0(3) . . . . ?
C14 C15 C18 C19 105.9(3) . . . . ?
C16 C15 C18 C21 46.4(3) . . . . ?
C14 C15 C18 C21 -134.7(3) . . . . ?
C10 C11 C22 C27 35.8(4) . . . . ?
C1 C11 C22 C27 -93.0(3) . . . . ?
C10 C11 C22 C23 -141.8(3) . . . . ?
C1 C11 C22 C23 89.4(3) . . . . ?
C27 C22 C23 C24 -1.0(4) . . . . ?
C11 C22 C23 C24 176.7(2) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C23 C24 C25 C28 -175.6(3) . . . . ?
C24 C25 C26 C27 -1.2(4) . . . . ?
C28 C25 C26 C27 176.4(3) . . . . ?
C23 C22 C27 C26 1.7(4) . . . . ?
C11 C22 C27 C26 -175.9(3) . . . . ?
C25 C26 C27 C22 -0.6(5) . . . . ?
C26 C25 C28 C30 -70.0(4) . . . . ?
C24 C25 C28 C30 107.4(4) . . . . ?
C26 C25 C28 C31 49.8(4) . . . . ?
C24 C25 C28 C31 -132.8(3) . . . . ?
C26 C25 C28 C29 170.0(3) . . . . ?
C24 C25 C28 C29 -12.5(4) . . . . ?

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
C4 H4 O4 0.95 2.44 3.319(3) 153.9 4_565
C6 H6B O4 0.98 2.63 3.572(6) 160.2 1_565
C8 H8B O3 0.99 2.50 3.083(4) 117.0 .
C10 H10A O3 0.99 2.44 2.998(4) 115.6 .

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6

