 
data_PO19032_019
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C28 H30 O4' 
_chemical_formula_weight          430.52

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0039   0.0019
 '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'   0.0130   0.0073
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_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'
 
_cell_length_a                    10.154(2)
_cell_length_b                    10.568(2)
_cell_length_c                    20.499(4)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2199.7(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     43589
_cell_measurement_theta_min       0.401
_cell_measurement_theta_max       33.749
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.300          
_exptl_crystal_F_000              920
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.075
_exptl_crystal_size_mid           0.062
_exptl_crystal_size_min           0.034
_exptl_absorpt_coefficient_mu     0.100
_shelx_estimated_absorpt_T_min    0.993
_shelx_estimated_absorpt_T_max    0.997
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.698
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'HKL3000sm Scalepack'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.700
_diffrn_radiation_type            synchrotron
_diffrn_source                    'PLSII 2D bending magnet'
_diffrn_measurement_device_type   'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method        'omega scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             23422
_diffrn_reflns_av_unetI/netI      0.0741
_diffrn_reflns_av_R_equivalents   0.0894
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          1.957
_diffrn_reflns_theta_max          29.999
_diffrn_reflns_theta_full         24.835
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.994
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.994
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              6664
_reflns_number_gt                 4140
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.782
_reflns_Friedel_fraction_max      0.995
_reflns_Friedel_fraction_full     0.998
 
_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        'PAL BL2D-SMDC Program'
_computing_cell_refinement        'HKL3000sm'
_computing_data_reduction         'HKL3000sm'
_computing_structure_solution     SHELXS
_computing_structure_refinement   SHELXL
_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)+(0.0935P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.5(5)
_chemical_absolute_configuration  syn
_refine_ls_number_reflns          6664
_refine_ls_number_parameters      419
_refine_ls_number_restraints      229
_refine_ls_R_factor_all           0.1031
_refine_ls_R_factor_gt            0.0667
_refine_ls_wR_factor_ref          0.1965
_refine_ls_wR_factor_gt           0.1747
_refine_ls_goodness_of_fit_ref    1.089
_refine_ls_restrained_S_all       1.086
_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 0.4416(3) 0.7728(3) 0.23881(11) 0.0572(7) Uani 1 1 d . . . . .
C2 C 0.4252(4) 0.6905(4) 0.27952(16) 0.0456(8) Uani 1 1 d . . . . .
C3 C 0.3652(5) 0.5609(4) 0.26719(17) 0.0558(10) Uani 1 1 d . . . . .
H3A H 0.422004 0.510818 0.237591 0.067 Uiso 1 1 calc R U . . .
H3AB H 0.277036 0.569371 0.247056 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3548(4) 0.4965(4) 0.33369(16) 0.0466(9) Uani 1 1 d . . . . .
H4A H 0.430295 0.439263 0.341530 0.056 Uiso 1 1 calc R U . . .
H4AB H 0.271808 0.447923 0.337650 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3568(3) 0.6096(3) 0.38082(16) 0.0383(7) Uani 1 1 d . . . . .
H5 H 0.269660 0.652810 0.376130 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4590(3) 0.6984(3) 0.35128(14) 0.0383(7) Uani 1 1 d . . . . .
C7 C 0.6031(3) 0.6494(4) 0.35495(16) 0.0437(8) Uani 1 1 d . . . . .
H7A H 0.629090 0.640138 0.400743 0.066 Uiso 1 1 calc R U . . .
H7B H 0.661803 0.709931 0.333382 0.066 Uiso 1 1 calc R U . . .
H7C H 0.609234 0.567172 0.333045 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4474(4) 0.8286(3) 0.38239(15) 0.0439(8) Uani 1 1 d . . . . .
H8A H 0.360138 0.865533 0.372327 0.053 Uiso 1 1 calc R U . . .
H8AB H 0.515934 0.885439 0.364404 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4644(4) 0.8171(3) 0.45668(14) 0.0409(8) Uani 1 1 d . . . . .
H9A H 0.448156 0.900799 0.476834 0.049 Uiso 1 1 calc R U . . .
H9AB H 0.556604 0.792996 0.466301 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3714(3) 0.7192(3) 0.48795(15) 0.0358(7) Uani 1 1 d . . . . .
H10 H 0.279915 0.751808 0.481279 0.043 Uiso 1 1 calc R U . A 1
C11 C 0.3777(3) 0.5892(3) 0.45331(15) 0.0346(7) Uani 1 1 d . . . . .
H11 H 0.467747 0.553149 0.459893 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2782(4) 0.4999(3) 0.48425(16) 0.0401(7) Uani 1 1 d . . . . .
H12A H 0.189066 0.537630 0.481630 0.048 Uiso 1 1 calc R U . . .
H12B H 0.277065 0.418919 0.459991 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3130(4) 0.4752(3) 0.55512(16) 0.0437(8) Uani 1 1 d . . . . .
H13A H 0.381792 0.408845 0.556875 0.052 Uiso 1 1 calc R U . B 1
H13B H 0.234146 0.442022 0.577780 0.052 Uiso 1 1 calc R U . B 1
C14 C 0.3629(5) 0.5927(4) 0.5920(2) 0.0355(13) Uani 0.814(4) 1 d G . P C 1
C15 C 0.3907(6) 0.7077(5) 0.56209(17) 0.0357(15) Uani 0.814(4) 1 d G . P C 1
C16 C 0.4381(5) 0.8084(4) 0.5989(2) 0.0402(14) Uani 0.814(4) 1 d G . P C 1
H16 H 0.457047 0.886961 0.578416 0.048 Uiso 0.814(4) 1 calc R U P C 1
C17 C 0.4576(4) 0.7941(3) 0.6656(2) 0.0409(11) Uani 0.814(4) 1 d G . P C 1
H17 H 0.489923 0.862980 0.690721 0.049 Uiso 0.814(4) 1 calc R U P C 1
C18 C 0.4298(4) 0.6792(4) 0.69552(16) 0.0408(11) Uani 0.814(4) 1 d G . P C 1
C19 C 0.3825(4) 0.5785(3) 0.6587(2) 0.0402(12) Uani 0.814(4) 1 d G . P C 1
H19 H 0.363476 0.499904 0.679198 0.048 Uiso 0.814(4) 1 calc R U P C 1
O20 O 0.4384(3) 0.6610(3) 0.76359(13) 0.0450(8) Uani 0.814(4) 1 d . . P C 1
C21 C 0.5571(5) 0.6693(5) 0.7919(3) 0.0402(13) Uani 0.814(4) 1 d . . P C 1
O22 O 0.6576(3) 0.6864(4) 0.76018(14) 0.0488(9) Uani 0.814(4) 1 d . . P C 1
C23 C 0.5518(4) 0.6552(4) 0.8618(2) 0.0392(9) Uani 0.814(4) 1 d . . P C 1
H23 H 0.468992 0.645587 0.882787 0.047 Uiso 0.814(4) 1 calc R U P C 1
C24 C 0.6636(4) 0.6555(4) 0.89807(19) 0.0341(9) Uani 0.814(4) 1 d . . P C 1
O25 O 0.7845(3) 0.6695(3) 0.87179(14) 0.0431(8) Uani 0.814(4) 1 d . . P C 1
H25 H 0.779(5) 0.674(6) 0.827(3) 0.065 Uiso 0.814(4) 1 d . U P C 1
C26 C 0.6705(4) 0.6418(4) 0.97060(14) 0.0341(10) Uani 0.814(4) 1 d G . P C 1
C27 C 0.5641(4) 0.6727(5) 1.0102(2) 0.0368(12) Uani 0.814(4) 1 d G . P C 1
H27 H 0.483698 0.700119 0.991166 0.044 Uiso 0.814(4) 1 calc R U P C 1
C28 C 0.5753(5) 0.6634(7) 1.07759(19) 0.0374(14) Uani 0.814(4) 1 d G . P C 1
H28 H 0.502617 0.684501 1.104647 0.045 Uiso 0.814(4) 1 calc R U P C 1
C29 C 0.6930(6) 0.6232(8) 1.10541(14) 0.0414(18) Uani 0.814(4) 1 d G . P C 1
C30 C 0.7993(5) 0.5923(7) 1.0658(2) 0.0474(16) Uani 0.814(4) 1 d G . P C 1
H30 H 0.879729 0.564838 1.084845 0.057 Uiso 0.814(4) 1 calc R U P C 1
C31 C 0.7881(4) 0.6016(5) 0.9984(2) 0.0423(13) Uani 0.814(4) 1 d G . P C 1
H31 H 0.860813 0.580456 0.971364 0.051 Uiso 0.814(4) 1 calc R U P C 1
C32 C 0.7121(6) 0.6167(7) 1.1793(3) 0.0459(14) Uani 0.814(4) 1 d . . P C 1
H32A H 0.705325 0.701949 1.197792 0.069 Uiso 0.814(4) 1 calc R U P C 1
H32B H 0.799290 0.581580 1.188986 0.069 Uiso 0.814(4) 1 calc R U P C 1
H32C H 0.644119 0.562408 1.198430 0.069 Uiso 0.814(4) 1 calc R U P C 1
C14B C 0.384(2) 0.5715(17) 0.5892(9) 0.029(5) Uani 0.186(4) 1 d G U P C 2
C15B C 0.406(2) 0.688(2) 0.5600(7) 0.022(4) Uani 0.186(4) 1 d G U P C 2
C16B C 0.461(2) 0.7865(16) 0.5959(9) 0.022(4) Uani 0.186(4) 1 d G U P C 2
H16A H 0.475895 0.866358 0.575946 0.026 Uiso 0.186(4) 1 calc R U P C 2
C17B C 0.4943(17) 0.7678(14) 0.6609(9) 0.040(5) Uani 0.186(4) 1 d G U P C 2
H17B H 0.532073 0.834889 0.685459 0.048 Uiso 0.186(4) 1 calc R U P C 2
C18B C 0.4723(16) 0.6510(16) 0.6901(7) 0.039(5) Uani 0.186(4) 1 d G U P C 2
C19B C 0.4170(17) 0.5528(13) 0.6542(9) 0.030(4) Uani 0.186(4) 1 d G U P C 2
H19B H 0.402035 0.472956 0.674185 0.037 Uiso 0.186(4) 1 calc R U P C 2
O20B O 0.5307(18) 0.6161(16) 0.7475(7) 0.060(4) Uani 0.186(4) 1 d . U P C 2
C21B C 0.592(4) 0.702(3) 0.7900(16) 0.058(5) Uani 0.186(4) 1 d D U P C 2
O22B O 0.583(3) 0.811(2) 0.7846(10) 0.099(7) Uani 0.186(4) 1 d . U P C 2
C23B C 0.6539(19) 0.641(2) 0.8469(8) 0.043(4) Uani 0.186(4) 1 d D U P C 2
H23C H 0.736954 0.685604 0.857998 0.052 Uiso 0.186(4) 1 calc R U P C 2
H23D H 0.674904 0.552107 0.836819 0.052 Uiso 0.186(4) 1 calc R U P C 2
C24B C 0.5572(19) 0.6479(18) 0.9056(8) 0.036(3) Uani 0.186(4) 1 d . U P C 2
O25B O 0.4463(15) 0.6726(18) 0.8964(7) 0.062(4) Uani 0.186(4) 1 d . U P C 2
C26B C 0.6165(16) 0.638(2) 0.9743(7) 0.034(4) Uani 0.186(4) 1 d G U P C 2
C27B C 0.7414(15) 0.591(2) 0.9879(8) 0.029(4) Uani 0.186(4) 1 d G U P C 2
H27B H 0.795739 0.560751 0.953432 0.035 Uiso 0.186(4) 1 calc R U P C 2
C28B C 0.7869(19) 0.588(3) 1.0518(10) 0.031(4) Uani 0.186(4) 1 d G U P C 2
H28B H 0.872333 0.555841 1.061064 0.037 Uiso 0.186(4) 1 calc R U P C 2
C29B C 0.707(3) 0.632(4) 1.1022(7) 0.035(5) Uani 0.186(4) 1 d G U P C 2
C30B C 0.583(2) 0.679(3) 1.0886(9) 0.036(5) Uani 0.186(4) 1 d G U P C 2
H30B H 0.528243 0.708640 1.122999 0.043 Uiso 0.186(4) 1 calc R U P C 2
C31B C 0.5370(15) 0.682(3) 1.0246(11) 0.039(5) Uani 0.186(4) 1 d G U P C 2
H31B H 0.451646 0.713552 1.015366 0.047 Uiso 0.186(4) 1 calc R U P C 2
C32B C 0.760(3) 0.627(4) 1.1726(18) 0.060(8) Uani 0.186(4) 1 d . U P C 2
H32D H 0.776399 0.538922 1.185122 0.090 Uiso 0.186(4) 1 calc R U P C 2
H32E H 0.695546 0.664592 1.202250 0.090 Uiso 0.186(4) 1 calc R U P C 2
H32F H 0.843032 0.674807 1.175234 0.090 Uiso 0.186(4) 1 calc R U P C 2
 
 
_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 1.217(4) . ?
C2 C6 1.513(4) . ?
C2 C3 1.520(6) . ?
C3 C4 1.527(5) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.537(5) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C11 1.516(4) . ?
C5 C6 1.525(5) . ?
C5 H5 1.0000 . ?
C6 C8 1.522(5) . ?
C6 C7 1.554(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.537(4) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.541(5) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C15 1.537(4) . ?
C10 C11 1.548(4) . ?
C10 C15B 1.552(14) . ?
C10 H10 1.0000 . ?
C11 C12 1.522(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.518(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14B 1.428(15) . ?
C13 C14 1.540(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 O20 1.411(4) . ?
C19 H19 0.9500 . ?
O20 C21 1.342(6) . ?
C21 O22 1.224(7) . ?
C21 C23 1.441(7) . ?
C23 C24 1.357(6) . ?
C23 H23 0.9500 . ?
C24 O25 1.348(5) . ?
C24 C26 1.495(5) . ?
O25 H25 0.91(5) . ?
C26 C27 1.3900 . ?
C26 C31 1.3900 . ?
C27 C28 1.3900 . ?
C27 H27 0.9500 . ?
C28 C29 1.3900 . ?
C28 H28 0.9500 . ?
C29 C30 1.3900 . ?
C29 C32 1.528(7) . ?
C30 C31 1.3900 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C14B C15B 1.3900 . ?
C14B C19B 1.3900 . ?
C15B C16B 1.3900 . ?
C16B C17B 1.3900 . ?
C16B H16A 0.9500 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B O20B 1.37(2) . ?
C18B C19B 1.3900 . ?
C19B H19B 0.9500 . ?
O20B C21B 1.40(4) . ?
C21B O22B 1.16(4) . ?
C21B C23B 1.47(2) . ?
C23B C24B 1.55(3) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B O25B 1.17(2) . ?
C24B C26B 1.53(2) . ?
C26B C27B 1.3900 . ?
C26B C31B 1.3900 . ?
C27B C28B 1.3900 . ?
C27B H27B 0.9500 . ?
C28B C29B 1.3900 . ?
C28B H28B 0.9500 . ?
C29B C30B 1.3900 . ?
C29B C32B 1.54(4) . ?
C30B C31B 1.3900 . ?
C30B H30B 0.9500 . ?
C31B H31B 0.9500 . ?
C32B H32D 0.9800 . ?
C32B H32E 0.9800 . ?
C32B H32F 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
O1 C2 C6 126.6(3) . . ?
O1 C2 C3 125.8(3) . . ?
C6 C2 C3 107.6(3) . . ?
C2 C3 C4 106.3(3) . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3AB 110.5 . . ?
C4 C3 H3AB 110.5 . . ?
H3A C3 H3AB 108.7 . . ?
C3 C4 C5 102.4(3) . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4AB 111.3 . . ?
C5 C4 H4AB 111.3 . . ?
H4A C4 H4AB 109.2 . . ?
C11 C5 C6 112.4(3) . . ?
C11 C5 C4 120.5(3) . . ?
C6 C5 C4 103.8(3) . . ?
C11 C5 H5 106.4 . . ?
C6 C5 H5 106.4 . . ?
C4 C5 H5 106.4 . . ?
C2 C6 C8 116.1(3) . . ?
C2 C6 C5 101.4(3) . . ?
C8 C6 C5 109.7(3) . . ?
C2 C6 C7 104.0(3) . . ?
C8 C6 C7 110.7(3) . . ?
C5 C6 C7 114.6(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C9 109.6(3) . . ?
C6 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C6 C8 H8AB 109.8 . . ?
C9 C8 H8AB 109.8 . . ?
H8A C8 H8AB 108.2 . . ?
C8 C9 C10 113.4(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9AB 108.9 . . ?
C10 C9 H9AB 108.9 . . ?
H9A C9 H9AB 107.7 . . ?
C15 C10 C9 112.7(3) . . ?
C15 C10 C11 112.2(3) . . ?
C9 C10 C11 112.3(3) . . ?
C9 C10 C15B 113.6(9) . . ?
C11 C10 C15B 103.9(8) . . ?
C15 C10 H10 106.3 . . ?
C9 C10 H10 106.3 . . ?
C11 C10 H10 106.3 . . ?
C5 C11 C12 113.8(3) . . ?
C5 C11 C10 108.5(3) . . ?
C12 C11 C10 109.4(3) . . ?
C5 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
C13 C12 C11 110.5(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14B C13 C12 117.5(9) . . ?
C12 C13 C14 114.1(3) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 120.0 . . ?
C15 C14 C13 123.7(3) . . ?
C19 C14 C13 116.3(3) . . ?
C14 C15 C16 120.0 . . ?
C14 C15 C10 118.7(3) . . ?
C16 C15 C10 121.3(3) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 O20 122.9(3) . . ?
C19 C18 O20 116.9(3) . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C21 O20 C18 118.3(4) . . ?
O22 C21 O20 121.9(5) . . ?
O22 C21 C23 125.1(5) . . ?
O20 C21 C23 113.0(4) . . ?
C24 C23 C21 120.8(4) . . ?
C24 C23 H23 119.6 . . ?
C21 C23 H23 119.6 . . ?
O25 C24 C23 122.9(4) . . ?
O25 C24 C26 111.4(3) . . ?
C23 C24 C26 125.7(4) . . ?
C24 O25 H25 111(3) . . ?
C27 C26 C31 120.0 . . ?
C27 C26 C24 121.4(3) . . ?
C31 C26 C24 118.5(3) . . ?
C26 C27 C28 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 C32 118.0(4) . . ?
C28 C29 C32 122.0(4) . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C26 120.0 . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C15B C14B C19B 120.0 . . ?
C15B C14B C13 120.2(13) . . ?
C19B C14B C13 119.4(13) . . ?
C14B C15B C16B 120.0 . . ?
C14B C15B C10 124.1(13) . . ?
C16B C15B C10 115.9(13) . . ?
C17B C16B C15B 120.0 . . ?
C17B C16B H16A 120.0 . . ?
C15B C16B H16A 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
O20B C18B C17B 122.7(14) . . ?
O20B C18B C19B 115.4(13) . . ?
C17B C18B C19B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C14B C19B H19B 120.0 . . ?
C18B O20B C21B 123.5(18) . . ?
O22B C21B O20B 123(3) . . ?
O22B C21B C23B 123(3) . . ?
O20B C21B C23B 114(3) . . ?
C21B C23B C24B 109(2) . . ?
C21B C23B H23C 109.9 . . ?
C24B C23B H23C 109.9 . . ?
C21B C23B H23D 109.9 . . ?
C24B C23B H23D 109.9 . . ?
H23C C23B H23D 108.3 . . ?
O25B C24B C26B 122.8(17) . . ?
O25B C24B C23B 119.5(17) . . ?
C26B C24B C23B 117.3(15) . . ?
C27B C26B C31B 120.0 . . ?
C27B C26B C24B 124.5(14) . . ?
C31B C26B C24B 115.5(14) . . ?
C28B C27B C26B 120.0 . . ?
C28B C27B H27B 120.0 . . ?
C26B C27B H27B 120.0 . . ?
C27B C28B C29B 120.0 . . ?
C27B C28B H28B 120.0 . . ?
C29B C28B H28B 120.0 . . ?
C30B C29B C28B 120.0 . . ?
C30B C29B C32B 121(2) . . ?
C28B C29B C32B 119(2) . . ?
C29B C30B C31B 120.0 . . ?
C29B C30B H30B 120.0 . . ?
C31B C30B H30B 120.0 . . ?
C30B C31B C26B 120.0 . . ?
C30B C31B H31B 120.0 . . ?
C26B C31B H31B 120.0 . . ?
C29B C32B H32D 109.5 . . ?
C29B C32B H32E 109.5 . . ?
H32D C32B H32E 109.5 . . ?
C29B C32B H32F 109.5 . . ?
H32D C32B H32F 109.5 . . ?
H32E C32B H32F 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 C2 C3 C4 -175.3(4) . . . . ?
C6 C2 C3 C4 4.2(4) . . . . ?
C2 C3 C4 C5 21.8(4) . . . . ?
C3 C4 C5 C11 -166.8(3) . . . . ?
C3 C4 C5 C6 -40.0(4) . . . . ?
O1 C2 C6 C8 32.1(6) . . . . ?
C3 C2 C6 C8 -147.4(3) . . . . ?
O1 C2 C6 C5 150.9(4) . . . . ?
C3 C2 C6 C5 -28.5(4) . . . . ?
O1 C2 C6 C7 -89.9(4) . . . . ?
C3 C2 C6 C7 90.7(4) . . . . ?
C11 C5 C6 C2 174.1(3) . . . . ?
C4 C5 C6 C2 42.3(3) . . . . ?
C11 C5 C6 C8 -62.6(4) . . . . ?
C4 C5 C6 C8 165.6(3) . . . . ?
C11 C5 C6 C7 62.7(3) . . . . ?
C4 C5 C6 C7 -69.1(3) . . . . ?
C2 C6 C8 C9 171.5(3) . . . . ?
C5 C6 C8 C9 57.3(4) . . . . ?
C7 C6 C8 C9 -70.2(4) . . . . ?
C6 C8 C9 C10 -53.2(4) . . . . ?
C8 C9 C10 C15 179.3(3) . . . . ?
C8 C9 C10 C11 51.4(4) . . . . ?
C8 C9 C10 C15B 169.0(10) . . . . ?
C6 C5 C11 C12 -179.4(3) . . . . ?
C4 C5 C11 C12 -56.6(4) . . . . ?
C6 C5 C11 C10 58.6(4) . . . . ?
C4 C5 C11 C10 -178.6(3) . . . . ?
C15 C10 C11 C5 179.6(3) . . . . ?
C9 C10 C11 C5 -52.2(4) . . . . ?
C15B C10 C11 C5 -175.4(10) . . . . ?
C15 C10 C11 C12 54.9(4) . . . . ?
C9 C10 C11 C12 -176.9(3) . . . . ?
C15B C10 C11 C12 59.9(10) . . . . ?
C5 C11 C12 C13 174.9(3) . . . . ?
C10 C11 C12 C13 -63.6(4) . . . . ?
C11 C12 C13 C14B 27.8(11) . . . . ?
C11 C12 C13 C14 39.7(4) . . . . ?
C12 C13 C14 C15 -8.1(4) . . . . ?
C12 C13 C14 C19 173.2(3) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 C16 -178.7(4) . . . . ?
C19 C14 C15 C10 178.5(4) . . . . ?
C13 C14 C15 C10 -0.2(4) . . . . ?
C9 C10 C15 C14 -151.3(3) . . . . ?
C11 C10 C15 C14 -23.3(4) . . . . ?
C9 C10 C15 C16 27.2(4) . . . . ?
C11 C10 C15 C16 155.2(3) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C10 C15 C16 C17 -178.4(5) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C16 C17 C18 O20 -175.3(4) . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
O20 C18 C19 C14 175.6(4) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C13 C14 C19 C18 178.8(4) . . . . ?
C17 C18 O20 C21 -65.5(5) . . . . ?
C19 C18 O20 C21 119.0(4) . . . . ?
C18 O20 C21 O22 -3.3(8) . . . . ?
C18 O20 C21 C23 177.1(4) . . . . ?
O22 C21 C23 C24 -2.5(8) . . . . ?
O20 C21 C23 C24 177.1(4) . . . . ?
C21 C23 C24 O25 0.4(7) . . . . ?
C21 C23 C24 C26 180.0(4) . . . . ?
O25 C24 C26 C27 155.8(3) . . . . ?
C23 C24 C26 C27 -23.8(6) . . . . ?
O25 C24 C26 C31 -21.8(5) . . . . ?
C23 C24 C26 C31 158.6(4) . . . . ?
C31 C26 C27 C28 0.0 . . . . ?
C24 C26 C27 C28 -177.5(5) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C27 C28 C29 C32 177.4(7) . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C32 C29 C30 C31 -177.5(7) . . . . ?
C29 C30 C31 C26 0.0 . . . . ?
C27 C26 C31 C30 0.0 . . . . ?
C24 C26 C31 C30 177.6(4) . . . . ?
C12 C13 C14B C15B 7.0(13) . . . . ?
C12 C13 C14B C19B 179.7(8) . . . . ?
C19B C14B C15B C16B 0.0 . . . . ?
C13 C14B C15B C16B 172.6(18) . . . . ?
C19B C14B C15B C10 -179.7(19) . . . . ?
C13 C14B C15B C10 -7.1(14) . . . . ?
C9 C10 C15B C14B -148.9(9) . . . . ?
C11 C10 C15B C14B -26.5(14) . . . . ?
C9 C10 C15B C16B 31.4(14) . . . . ?
C11 C10 C15B C16B 153.8(9) . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C10 C15B C16B C17B 179.7(17) . . . . ?
C15B C16B C17B C18B 0.0 . . . . ?
C16B C17B C18B O20B 163.5(17) . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
O20B C18B C19B C14B -164.7(16) . . . . ?
C17B C18B C19B C14B 0.0 . . . . ?
C15B C14B C19B C18B 0.0 . . . . ?
C13 C14B C19B C18B -172.7(17) . . . . ?
C17B C18B O20B C21B 16(3) . . . . ?
C19B C18B O20B C21B 180(2) . . . . ?
C18B O20B C21B O22B 11(6) . . . . ?
C18B O20B C21B C23B -177(2) . . . . ?
O22B C21B C23B C24B 76(5) . . . . ?
O20B C21B C23B C24B -97(3) . . . . ?
C21B C23B C24B O25B 15(3) . . . . ?
C21B C23B C24B C26B -158(2) . . . . ?
O25B C24B C26B C27B 170.1(19) . . . . ?
C23B C24B C26B C27B -18(3) . . . . ?
O25B C24B C26B C31B -11(3) . . . . ?
C23B C24B C26B C31B 161.1(16) . . . . ?
C31B C26B C27B C28B 0.0 . . . . ?
C24B C26B C27B C28B 179(2) . . . . ?
C26B C27B C28B C29B 0.0 . . . . ?
C27B C28B C29B C30B 0.0 . . . . ?
C27B C28B C29B C32B 180(3) . . . . ?
C28B C29B C30B C31B 0.0 . . . . ?
C32B C29B C30B C31B -180(3) . . . . ?
C29B C30B C31B C26B 0.0 . . . . ?
C27B C26B C31B C30B 0.0 . . . . ?
C24B C26B C31B C30B -179(2) . . . . ?
 
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 
 _geom_hbond_publ_flag
O25 H25 O1  0.91(5) 2.21(5) 2.839(4) 126(4) 4_566 yes
O25 H25 O22  0.91(5) 1.86(5) 2.632(4) 141(4) . yes
 
_refine_diff_density_max    0.363
_refine_diff_density_min   -0.362
_refine_diff_density_rms    0.058





















