# 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 2019

####################################################################### 
# 
# 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_eb15
_database_code_depnum_ccdc_archive 'CCDC 1886558'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O4'
_chemical_formula_sum            'C34 H42 N0 O2'
_chemical_formula_weight         482.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   13.1690(6)
_cell_length_b                   6.8675(3)
_cell_length_c                   15.9197(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.802(2)
_cell_angle_gamma                90
_cell_volume                     1409.31(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4636
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      65.05

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.524
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5891
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.836
_diffrn_reflns_theta_max         65.042
_diffrn_reflns_theta_full        65.042
_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 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2352
_reflns_number_gt                2144
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.960

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0894P)²+2.4797P] 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 849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2352
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.7570(3) 0.3092(7) 0.6586(2) 0.0565(12) Uani 1 1 d . . . . .
C1 C 0.5400(3) 0.6033(9) 0.5403(3) 0.0394(12) Uani 1 1 d . . . . .
C2 C 0.6083(3) 0.4469(9) 0.5620(3) 0.0396(12) Uani 1 1 d . . . . .
H2 H 0.6024 0.3357 0.5258 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6854(4) 0.4537(9) 0.6368(3) 0.0438(13) Uani 1 1 d . . . . .
C4 C 0.6918(4) 0.6148(10) 0.6929(3) 0.0515(15) Uani 1 1 d . . . . .
C5 C 0.6248(4) 0.7690(11) 0.6698(3) 0.0554(16) Uani 1 1 d . . . . .
H5 H 0.6297 0.8802 0.7059 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5498(4) 0.7634(10) 0.5941(3) 0.0493(14) Uani 1 1 d . . . . .
H6 H 0.5046 0.8714 0.5791 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7694(4) 0.1738(9) 0.5940(3) 0.0468(13) Uani 1 1 d . . . . .
H7A H 0.7087 0.0881 0.5812 0.070 Uiso 1 1 calc R U . . .
H7B H 0.8319 0.0956 0.6142 0.070 Uiso 1 1 calc R U . . .
H7C H 0.7762 0.2443 0.5419 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7691(4) 0.6291(11) 0.7758(3) 0.0549(16) Uani 1 1 d . . . . .
C9 C 0.8305(5) 0.8276(10) 0.8026(4) 0.0579(16) Uani 1 1 d . . . . .
H9 H 0.8239 0.9470 0.7659 0.069 Uiso 1 1 calc R U . . .
C10 C 0.8830(4) 0.6427(9) 0.7840(3) 0.0546(16) Uani 1 1 d . . . . .
C11 C 0.9356(5) 0.6307(18) 0.7097(5) 0.115(4) Uani 1 1 d . . . . .
H11A H 0.8888 0.6791 0.6580 0.172 Uiso 1 1 calc R U . . .
H11B H 0.9538 0.4949 0.7009 0.172 Uiso 1 1 calc R U . . .
H11C H 0.9987 0.7101 0.7213 0.172 Uiso 1 1 calc R U . . .
C12 C 0.9288(6) 0.5530(11) 0.8716(4) 0.078(2) Uani 1 1 d . . . . .
H12A H 0.9352 0.4097 0.8684 0.094 Uiso 1 1 calc R U . . .
H12B H 0.9970 0.6103 0.8975 0.094 Uiso 1 1 calc R U . . .
C13 C 0.8463(5) 0.8294(11) 0.9028(4) 0.0679(19) Uani 1 1 d . . . . .
H13A H 0.9126 0.8915 0.9303 0.081 Uiso 1 1 calc R U . . .
H13B H 0.7881 0.8938 0.9225 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8475(6) 0.6115(9) 0.9175(4) 0.070(2) Uani 1 1 d . . . . .
H14 H 0.8590 0.5699 0.9789 0.085 Uiso 1 1 calc R U . . .
C15 C 0.7447(5) 0.5375(9) 0.8591(3) 0.0541(16) Uani 1 1 d . . . . .
C16 C 0.6458(5) 0.6107(12) 0.8799(3) 0.0679(19) Uani 1 1 d . . . . .
H16A H 0.6390 0.7505 0.8675 0.102 Uiso 1 1 calc R U . . .
H16B H 0.6465 0.5885 0.9408 0.102 Uiso 1 1 calc R U . . .
H16C H 0.5870 0.5413 0.8449 0.102 Uiso 1 1 calc R U . . .
C17 C 0.7497(7) 0.3225(10) 0.8498(4) 0.077(2) Uani 1 1 d . . . . .
H17A H 0.6904 0.2782 0.8063 0.115 Uiso 1 1 calc R U . . .
H17B H 0.7478 0.2604 0.9048 0.115 Uiso 1 1 calc R U . . .
H17C H 0.8143 0.2872 0.8320 0.115 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 C3 1.364(7) . ?
O1 C7 1.421(7) . ?
C1 C6 1.383(8) . ?
C1 C2 1.398(7) . ?
C1 C1 1.484(8) 2_656 ?
C2 C3 1.399(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(8) . ?
C4 C5 1.380(8) . ?
C4 C8 1.495(6) . ?
C5 C6 1.395(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C10 1.482(8) . ?
C8 C15 1.559(9) . ?
C8 C9 1.598(9) . ?
C9 C10 1.504(8) . ?
C9 C13 1.566(8) . ?
C9 H9 1.0000 . ?
C10 C11 1.490(10) . ?
C10 C12 1.531(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.470(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.515(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.562(8) . ?
C14 H14 1.0000 . ?
C15 C17 1.487(9) . ?
C15 C16 1.495(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C3 O1 C7 117.9(4) . . ?
C6 C1 C2 119.0(4) . . ?
C6 C1 C1 119.7(3) . 2_656 ?
C2 C1 C1 121.4(3) . 2_656 ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O1 C3 C2 122.4(5) . . ?
O1 C3 C4 117.4(4) . . ?
C2 C3 C4 120.2(5) . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 C8 117.9(5) . . ?
C3 C4 C8 123.4(5) . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 121.1(5) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C4 125.1(5) . . ?
C10 C8 C15 109.4(4) . . ?
C4 C8 C15 120.2(5) . . ?
C10 C8 C9 58.3(4) . . ?
C4 C8 C9 120.4(6) . . ?
C15 C8 C9 107.4(4) . . ?
C10 C9 C13 103.7(5) . . ?
C10 C9 C8 57.0(4) . . ?
C13 C9 C8 103.5(5) . . ?
C10 C9 H9 124.5 . . ?
C13 C9 H9 124.5 . . ?
C8 C9 H9 124.5 . . ?
C8 C10 C11 123.6(4) . . ?
C8 C10 C9 64.7(4) . . ?
C11 C10 C9 120.6(7) . . ?
C8 C10 C12 104.9(6) . . ?
C11 C10 C12 122.7(6) . . ?
C9 C10 C12 105.8(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C10 98.7(5) . . ?
C14 C12 H12A 112.0 . . ?
C10 C12 H12A 112.0 . . ?
C14 C12 H12B 112.0 . . ?
C10 C12 H12B 112.0 . . ?
H12A C12 H12B 109.7 . . ?
C14 C13 C9 98.3(5) . . ?
C14 C13 H13A 112.1 . . ?
C9 C13 H13A 112.1 . . ?
C14 C13 H13B 112.1 . . ?
C9 C13 H13B 112.1 . . ?
H13A C13 H13B 109.7 . . ?
C12 C14 C13 100.3(7) . . ?
C12 C14 C15 104.3(5) . . ?
C13 C14 C15 104.4(4) . . ?
C12 C14 H14 115.3 . . ?
C13 C14 H14 115.3 . . ?
C15 C14 H14 115.3 . . ?
C17 C15 C16 114.5(7) . . ?
C17 C15 C8 107.1(5) . . ?
C16 C15 C8 113.1(4) . . ?
C17 C15 C14 109.4(5) . . ?
C16 C15 C14 116.6(5) . . ?
C8 C15 C14 94.1(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 C1 C2 C3 -0.2(7) . . . . ?
C1 C1 C2 C3 177.7(5) 2_656 . . . ?
C7 O1 C3 C2 15.7(7) . . . . ?
C7 O1 C3 C4 -163.9(5) . . . . ?
C1 C2 C3 O1 -176.8(5) . . . . ?
C1 C2 C3 C4 2.8(7) . . . . ?
O1 C3 C4 C5 175.8(5) . . . . ?
C2 C3 C4 C5 -3.8(8) . . . . ?
O1 C3 C4 C8 -3.0(8) . . . . ?
C2 C3 C4 C8 177.4(5) . . . . ?
C3 C4 C5 C6 2.2(9) . . . . ?
C8 C4 C5 C6 -178.9(6) . . . . ?
C2 C1 C6 C5 -1.4(8) . . . . ?
C1 C1 C6 C5 -179.3(6) 2_656 . . . ?
C4 C5 C6 C1 0.4(9) . . . . ?
C5 C4 C8 C10 -113.4(7) . . . . ?
C3 C4 C8 C10 65.5(9) . . . . ?
C5 C4 C8 C15 95.2(8) . . . . ?
C3 C4 C8 C15 -85.9(7) . . . . ?
C5 C4 C8 C9 -42.8(7) . . . . ?
C3 C4 C8 C9 136.1(6) . . . . ?
C4 C8 C9 C10 -114.9(6) . . . . ?
C15 C8 C9 C10 102.4(5) . . . . ?
C10 C8 C9 C13 -97.7(5) . . . . ?
C4 C8 C9 C13 147.4(5) . . . . ?
C15 C8 C9 C13 4.7(6) . . . . ?
C4 C8 C10 C11 -4.2(12) . . . . ?
C15 C8 C10 C11 149.8(8) . . . . ?
C9 C8 C10 C11 -111.3(9) . . . . ?
C4 C8 C10 C9 107.1(7) . . . . ?
C15 C8 C10 C9 -98.9(5) . . . . ?
C4 C8 C10 C12 -152.2(7) . . . . ?
C15 C8 C10 C12 1.7(6) . . . . ?
C9 C8 C10 C12 100.7(5) . . . . ?
C13 C9 C10 C8 97.3(6) . . . . ?
C13 C9 C10 C11 -147.1(6) . . . . ?
C8 C9 C10 C11 115.5(5) . . . . ?
C13 C9 C10 C12 -2.0(7) . . . . ?
C8 C9 C10 C12 -99.4(6) . . . . ?
C8 C10 C12 C14 -32.5(6) . . . . ?
C11 C10 C12 C14 179.1(7) . . . . ?
C9 C10 C12 C14 34.9(6) . . . . ?
C10 C9 C13 C14 -30.4(7) . . . . ?
C8 C9 C13 C14 28.3(6) . . . . ?
C10 C12 C14 C13 -55.2(5) . . . . ?
C10 C12 C14 C15 52.7(6) . . . . ?
C9 C13 C14 C12 53.8(5) . . . . ?
C9 C13 C14 C15 -54.0(7) . . . . ?
C10 C8 C15 C17 -84.2(7) . . . . ?
C4 C8 C15 C17 71.3(7) . . . . ?
C9 C8 C15 C17 -146.0(5) . . . . ?
C10 C8 C15 C16 148.7(5) . . . . ?
C4 C8 C15 C16 -55.8(8) . . . . ?
C9 C8 C15 C16 87.0(6) . . . . ?
C10 C8 C15 C14 27.5(6) . . . . ?
C4 C8 C15 C14 -177.0(6) . . . . ?
C9 C8 C15 C14 -34.2(5) . . . . ?
C12 C14 C15 C17 60.2(7) . . . . ?
C13 C14 C15 C17 165.0(6) . . . . ?
C12 C14 C15 C16 -167.9(6) . . . . ?
C13 C14 C15 C16 -63.1(8) . . . . ?
C12 C14 C15 C8 -49.5(6) . . . . ?
C13 C14 C15 C8 55.3(6) . . . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_eb127
_database_code_depnum_ccdc_archive 'CCDC 1886561'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H46 O4'
_chemical_formula_weight         518.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.2984(6)
_cell_length_b                   14.6289(7)
_cell_length_c                   7.9467(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1429.71(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13860
_cell_measurement_theta_min      6.050
_cell_measurement_theta_max      72.192

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.602
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5647
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13860
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.050
_diffrn_reflns_theta_max         72.192
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2776
_reflns_number_gt                2715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0607P)²+0.1944P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1117 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     185
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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 0.10838(11) -0.02465(9) 0.57790(17) 0.0203(3) Uani 1 1 d D . . . .
H1 H 0.041(2) -0.012(3) 0.603(6) 0.025(13) Uiso 0.5 1 d D . P . .
H1X H 0.109(4) -0.061(3) 0.497(5) 0.022(12) Uiso 0.5 1 d D . P . .
O2 O -0.09645(11) 0.23860(9) 0.01511(16) 0.0213(3) Uani 1 1 d . . . . .
C1 C 0.16387(15) 0.05334(12) 0.5113(2) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.09340(15) 0.09725(12) 0.3717(2) 0.0159(4) Uani 1 1 d . . . . .
C3 C 0.01106(15) 0.05086(11) 0.2836(2) 0.0156(4) Uani 1 1 d . . . . .
C4 C -0.05254(15) 0.09698(12) 0.1628(2) 0.0169(4) Uani 1 1 d . . . . .
H4 H -0.1077 0.0645 0.1043 0.020 Uiso 1 1 calc R U . . .
C5 C -0.03629(15) 0.18878(12) 0.1276(2) 0.0170(4) Uani 1 1 d . . . . .
C6 C -0.18454(17) 0.19289(14) -0.0650(3) 0.0266(5) Uani 1 1 d . . . . .
H6A H -0.1561 0.1447 -0.1384 0.040 Uiso 1 1 calc R U . . .
H6B H -0.2262 0.2368 -0.1322 0.040 Uiso 1 1 calc R U . . .
H6C H -0.2320 0.1657 0.0206 0.040 Uiso 1 1 calc R U . . .
C7 C 0.04546(15) 0.23533(12) 0.2117(2) 0.0184(4) Uani 1 1 d . . . . .
H7 H 0.0586 0.2981 0.1883 0.022 Uiso 1 1 calc R U . . .
C8 C 0.10775(15) 0.18979(12) 0.3299(2) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.1634 0.2230 0.3860 0.022 Uiso 1 1 calc R U . . .
C9 C 0.28359(16) 0.02312(13) 0.4533(3) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.35685(17) 0.06995(14) 0.5883(3) 0.0250(5) Uani 1 1 d . . . . .
H10 H 0.4348 0.0755 0.5539 0.030 Uiso 1 1 calc R U . . .
C11 C 0.29972(17) 0.16253(13) 0.6128(3) 0.0234(4) Uani 1 1 d . . . . .
H11A H 0.2959 0.1988 0.5077 0.028 Uiso 1 1 calc R U . . .
H11B H 0.3325 0.1994 0.7041 0.028 Uiso 1 1 calc R U . . .
C12 C 0.18887(16) 0.12066(12) 0.6626(2) 0.0199(4) Uani 1 1 d . . . . .
C13 C 0.22748(19) 0.06207(14) 0.8141(2) 0.0269(5) Uani 1 1 d . . . . .
H13A H 0.2317 0.0996 0.9176 0.032 Uiso 1 1 calc R U . . .
H13B H 0.1771 0.0104 0.8340 0.032 Uiso 1 1 calc R U . . .
C14 C 0.34100(19) 0.02700(15) 0.7633(3) 0.0306(5) Uani 1 1 d . . . . .
H14A H 0.3974 0.0482 0.8432 0.037 Uiso 1 1 calc R U . . .
H14B H 0.3426 -0.0406 0.7575 0.037 Uiso 1 1 calc R U . . .
C15 C 0.09625(18) 0.18298(14) 0.7176(3) 0.0255(4) Uani 1 1 d . . . . .
H15A H 0.1186 0.2179 0.8170 0.038 Uiso 1 1 calc R U . . .
H15B H 0.0323 0.1459 0.7452 0.038 Uiso 1 1 calc R U . . .
H15C H 0.0782 0.2252 0.6260 0.038 Uiso 1 1 calc R U . . .
C16 C 0.29710(18) -0.08115(13) 0.4478(3) 0.0269(5) Uani 1 1 d . . . . .
H16A H 0.2498 -0.1066 0.3603 0.040 Uiso 1 1 calc R U . . .
H16B H 0.2772 -0.1072 0.5572 0.040 Uiso 1 1 calc R U . . .
H16C H 0.3730 -0.0963 0.4224 0.040 Uiso 1 1 calc R U . . .
C17 C 0.31565(17) 0.05871(14) 0.2786(3) 0.0270(5) Uani 1 1 d . . . . .
H17A H 0.3890 0.0374 0.2507 0.041 Uiso 1 1 calc R U . . .
H17B H 0.3144 0.1257 0.2789 0.041 Uiso 1 1 calc R U . . .
H17C H 0.2640 0.0358 0.1947 0.041 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 1.431(2) . ?
O1 H1 0.87(2) . ?
O1 H1X 0.83(2) . ?
O2 C5 1.371(2) . ?
O2 C6 1.423(2) . ?
C1 C2 1.547(2) . ?
C1 C12 1.584(2) . ?
C1 C9 1.605(3) . ?
C2 C8 1.405(3) . ?
C2 C3 1.406(3) . ?
C3 C4 1.410(3) . ?
C3 C3 1.513(3) 2 ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.386(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C17 1.534(3) . ?
C9 C16 1.535(3) . ?
C9 C10 1.559(3) . ?
C10 C11 1.538(3) . ?
C10 C14 1.539(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.546(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C15 1.523(3) . ?
C12 C13 1.552(3) . ?
C13 C14 1.541(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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 H1 112(3) . . ?
C1 O1 H1X 103(3) . . ?
H1 O1 H1X 108(5) . . ?
C5 O2 C6 116.92(14) . . ?
O1 C1 C2 109.21(15) . . ?
O1 C1 C12 107.93(14) . . ?
C2 C1 C12 113.25(14) . . ?
O1 C1 C9 108.91(14) . . ?
C2 C1 C9 114.97(15) . . ?
C12 C1 C9 102.19(15) . . ?
C8 C2 C3 115.95(16) . . ?
C8 C2 C1 119.95(16) . . ?
C3 C2 C1 124.07(15) . . ?
C2 C3 C4 120.51(15) . . ?
C2 C3 C3 127.18(17) . 2 ?
C4 C3 C3 111.77(15) . 2 ?
C5 C4 C3 121.40(17) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
O2 C5 C7 116.41(15) . . ?
O2 C5 C4 124.68(17) . . ?
C7 C5 C4 118.90(16) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 119.50(16) . . ?
C8 C7 H7 120.2 . . ?
C5 C7 H7 120.2 . . ?
C7 C8 C2 123.73(17) . . ?
C7 C8 H8 118.1 . . ?
C2 C8 H8 118.1 . . ?
C17 C9 C16 106.48(17) . . ?
C17 C9 C10 108.95(16) . . ?
C16 C9 C10 113.18(16) . . ?
C17 C9 C1 113.72(16) . . ?
C16 C9 C1 112.41(16) . . ?
C10 C9 C1 102.21(15) . . ?
C11 C10 C14 100.79(17) . . ?
C11 C10 C9 102.12(15) . . ?
C14 C10 C9 111.67(16) . . ?
C11 C10 H10 113.7 . . ?
C14 C10 H10 113.7 . . ?
C9 C10 H10 113.7 . . ?
C10 C11 C12 94.95(14) . . ?
C10 C11 H11A 112.7 . . ?
C12 C11 H11A 112.7 . . ?
C10 C11 H11B 112.7 . . ?
C12 C11 H11B 112.7 . . ?
H11A C11 H11B 110.2 . . ?
C15 C12 C11 119.72(16) . . ?
C15 C12 C13 109.68(16) . . ?
C11 C12 C13 98.49(16) . . ?
C15 C12 C1 116.40(16) . . ?
C11 C12 C1 102.89(15) . . ?
C13 C12 C1 107.74(15) . . ?
C14 C13 C12 104.94(17) . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C10 C14 C13 102.45(16) . . ?
C10 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
C10 C14 H14B 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C1 C2 C8 156.68(16) . . . . ?
C12 C1 C2 C8 36.4(2) . . . . ?
C9 C1 C2 C8 -80.6(2) . . . . ?
O1 C1 C2 C3 -21.3(2) . . . . ?
C12 C1 C2 C3 -141.64(17) . . . . ?
C9 C1 C2 C3 101.4(2) . . . . ?
C8 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 177.36(16) . . . . ?
C8 C2 C3 C3 170.17(15) . . . 2 ?
C1 C2 C3 C3 -11.7(3) . . . 2 ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C3 C4 C5 -172.36(16) 2 . . . ?
C6 O2 C5 C7 -176.56(16) . . . . ?
C6 O2 C5 C4 2.8(3) . . . . ?
C3 C4 C5 O2 -178.37(16) . . . . ?
C3 C4 C5 C7 1.0(3) . . . . ?
O2 C5 C7 C8 178.54(16) . . . . ?
C4 C5 C7 C8 -0.9(3) . . . . ?
C5 C7 C8 C2 -0.1(3) . . . . ?
C3 C2 C8 C7 0.9(3) . . . . ?
C1 C2 C8 C7 -177.32(17) . . . . ?
O1 C1 C9 C17 133.61(16) . . . . ?
C2 C1 C9 C17 10.7(2) . . . . ?
C12 C1 C9 C17 -112.38(17) . . . . ?
O1 C1 C9 C16 12.5(2) . . . . ?
C2 C1 C9 C16 -110.37(19) . . . . ?
C12 C1 C9 C16 126.54(17) . . . . ?
O1 C1 C9 C10 -109.14(16) . . . . ?
C2 C1 C9 C10 127.97(16) . . . . ?
C12 C1 C9 C10 4.87(16) . . . . ?
C17 C9 C10 C11 81.59(19) . . . . ?
C16 C9 C10 C11 -160.16(17) . . . . ?
C1 C9 C10 C11 -39.03(18) . . . . ?
C17 C9 C10 C14 -171.46(17) . . . . ?
C16 C9 C10 C14 -53.2(2) . . . . ?
C1 C9 C10 C14 67.91(19) . . . . ?
C14 C10 C11 C12 -57.82(17) . . . . ?
C9 C10 C11 C12 57.35(17) . . . . ?
C10 C11 C12 C15 175.24(17) . . . . ?
C10 C11 C12 C13 56.73(16) . . . . ?
C10 C11 C12 C1 -53.77(16) . . . . ?
O1 C1 C12 C15 -81.75(19) . . . . ?
C2 C1 C12 C15 39.3(2) . . . . ?
C9 C1 C12 C15 163.52(15) . . . . ?
O1 C1 C12 C11 145.29(15) . . . . ?
C2 C1 C12 C11 -93.69(18) . . . . ?
C9 C1 C12 C11 30.56(17) . . . . ?
O1 C1 C12 C13 41.9(2) . . . . ?
C2 C1 C12 C13 162.88(16) . . . . ?
C9 C1 C12 C13 -72.87(18) . . . . ?
C15 C12 C13 C14 -161.97(16) . . . . ?
C11 C12 C13 C14 -36.11(18) . . . . ?
C1 C12 C13 C14 70.42(19) . . . . ?
C11 C10 C14 C13 35.55(18) . . . . ?
C9 C10 C14 C13 -72.25(19) . . . . ?
C12 C13 C14 C10 0.64(19) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_eb-aja4
_database_code_depnum_ccdc_archive 'CCDC 1886565'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H40 N O2 P, C6 H12'
_chemical_formula_sum            'C39 H52 N O2 P'
_chemical_formula_weight         597.78

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'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.6897(4)
_cell_length_b                   15.7992(5)
_cell_length_c                   18.4623(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3118.07(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18022
_cell_measurement_theta_min      1.696
_cell_measurement_theta_max      26.996


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18022
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.696
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6803
_reflns_number_gt                5210
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2014)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2017)'


_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)+(0.0907P)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 1808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6803
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
P1 P 0.61268(11) 0.29440(6) 0.29440(6) 0.0280(3) Uani 1 1 d . . . . .
O1 O 0.7511(2) 0.25980(15) 0.29901(13) 0.0224(6) Uani 1 1 d . . . . .
O2 O 0.6084(3) 0.38052(15) 0.34378(13) 0.0218(6) Uani 1 1 d . . . . .
N1 N 0.4616(4) 0.1860(3) 0.3877(2) 0.0498(11) Uani 1 1 d . . . . .
C1 C 0.8560(3) 0.2640(2) 0.35018(18) 0.0177(8) Uani 1 1 d . . . . .
C2 C 0.8847(4) 0.3556(2) 0.36798(18) 0.0184(8) Uani 1 1 d . . . . .
C3 C 0.8712(3) 0.4237(2) 0.31837(19) 0.0193(8) Uani 1 1 d . . . . .
C4 C 0.8004(4) 0.4282(2) 0.24672(19) 0.0196(8) Uani 1 1 d . . . . .
C5 C 0.6754(4) 0.4559(2) 0.2381(2) 0.0224(8) Uani 1 1 d . . . . .
C6 C 0.5802(4) 0.4572(2) 0.3012(2) 0.0204(8) Uani 1 1 d . . . . .
C7 C 0.4356(4) 0.4566(2) 0.2825(2) 0.0260(9) Uani 1 1 d . . . . .
C8 C 0.4060(4) 0.5519(2) 0.2817(2) 0.0303(9) Uani 1 1 d . . . . .
H8A H 0.4533 0.5827 0.2438 0.036 Uiso 1 1 calc R U . . .
H8B H 0.3154 0.5635 0.2767 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4543(4) 0.5703(2) 0.3573(2) 0.0284(9) Uani 1 1 d . . . . .
H9 H 0.4465 0.6311 0.3717 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5911(4) 0.5392(2) 0.3520(2) 0.0227(9) Uani 1 1 d . . . . .
C11 C 0.6515(4) 0.5206(3) 0.42611(19) 0.0256(9) Uani 1 1 d . . . . .
H11A H 0.7399 0.5063 0.4192 0.038 Uiso 1 1 calc R U . . .
H11B H 0.6083 0.4730 0.4491 0.038 Uiso 1 1 calc R U . . .
H11C H 0.6448 0.5707 0.4571 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6677(4) 0.6114(2) 0.3168(2) 0.0280(9) Uani 1 1 d . . . . .
H12A H 0.6685 0.6606 0.3491 0.042 Uiso 1 1 calc R U . . .
H12B H 0.6296 0.6272 0.2704 0.042 Uiso 1 1 calc R U . . .
H12C H 0.7537 0.5922 0.3085 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3732(4) 0.5100(2) 0.4032(2) 0.0301(9) Uani 1 1 d . . . . .
H13A H 0.2899 0.5348 0.4133 0.036 Uiso 1 1 calc R U . . .
H13B H 0.4147 0.4956 0.4495 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3630(4) 0.4317(3) 0.3527(2) 0.0306(10) Uani 1 1 d . . . . .
H14A H 0.2744 0.4190 0.3415 0.037 Uiso 1 1 calc R U . . .
H14B H 0.4013 0.3813 0.3757 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3868(5) 0.4030(3) 0.2194(2) 0.0379(10) Uani 1 1 d . . . . .
H15A H 0.2998 0.4182 0.2091 0.057 Uiso 1 1 calc R U . . .
H15B H 0.3914 0.3429 0.2323 0.057 Uiso 1 1 calc R U . . .
H15C H 0.4382 0.4134 0.1763 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6383(4) 0.4847(3) 0.1692(2) 0.0279(9) Uani 1 1 d . . . . .
H16 H 0.5566 0.5074 0.1633 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7167(4) 0.4810(3) 0.1099(2) 0.0311(10) Uani 1 1 d . . . . .
H17 H 0.6892 0.5014 0.0642 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8353(4) 0.4475(2) 0.1173(2) 0.0291(10) Uani 1 1 d . . . . .
H18 H 0.8880 0.4408 0.0762 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8764(4) 0.4238(2) 0.1856(2) 0.0240(8) Uani 1 1 d . . . . .
H19 H 0.9597 0.4038 0.1909 0.029 Uiso 1 1 calc R U . . .
C20 C 0.9368(4) 0.4981(2) 0.3315(2) 0.0230(8) Uani 1 1 d . . . . .
H20 H 0.9365 0.5407 0.2951 0.028 Uiso 1 1 calc R U . . .
C21 C 1.0030(4) 0.5136(2) 0.3952(2) 0.0249(9) Uani 1 1 d . . . . .
H21 H 1.0461 0.5654 0.4026 0.030 Uiso 1 1 calc R U . . .
C22 C 1.0038(4) 0.4511(2) 0.4469(2) 0.0241(9) Uani 1 1 d . . . . .
H22 H 1.0425 0.4611 0.4925 0.029 Uiso 1 1 calc R U . . .
C23 C 0.9481(4) 0.3733(2) 0.4328(2) 0.0231(9) Uani 1 1 d . . . . .
H23 H 0.9532 0.3303 0.4686 0.028 Uiso 1 1 calc R U . . .
C24 C 0.8335(4) 0.2012(2) 0.4151(2) 0.0237(8) Uani 1 1 d . . . . .
C25 C 0.9683(4) 0.1696(2) 0.4302(2) 0.0254(9) Uani 1 1 d . . . . .
H25A H 1.0254 0.2159 0.4448 0.030 Uiso 1 1 calc R U . . .
H25B H 0.9709 0.1234 0.4664 0.030 Uiso 1 1 calc R U . . .
C26 C 0.9932(4) 0.1383(2) 0.3530(2) 0.0240(8) Uani 1 1 d . . . . .
H26 H 1.0783 0.1132 0.3465 0.029 Uiso 1 1 calc R U . . .
C27 C 0.9721(4) 0.2204(2) 0.3078(2) 0.0217(8) Uani 1 1 d . . . . .
C28 C 1.0932(4) 0.2720(2) 0.3112(2) 0.0266(9) Uani 1 1 d . . . . .
H28A H 1.1616 0.2392 0.2897 0.040 Uiso 1 1 calc R U . . .
H28B H 1.1132 0.2848 0.3618 0.040 Uiso 1 1 calc R U . . .
H28C H 1.0823 0.3249 0.2843 0.040 Uiso 1 1 calc R U . . .
C29 C 0.9431(4) 0.2037(2) 0.2275(2) 0.0278(9) Uani 1 1 d . . . . .
H29A H 0.9234 0.2574 0.2034 0.042 Uiso 1 1 calc R U . . .
H29B H 0.8714 0.1654 0.2236 0.042 Uiso 1 1 calc R U . . .
H29C H 1.0161 0.1779 0.2042 0.042 Uiso 1 1 calc R U . . .
C30 C 0.8872(4) 0.0743(2) 0.3437(2) 0.0259(9) Uani 1 1 d . . . . .
H30A H 0.9088 0.0192 0.3660 0.031 Uiso 1 1 calc R U . . .
H30B H 0.8671 0.0656 0.2919 0.031 Uiso 1 1 calc R U . . .
C31 C 0.7775(4) 0.1170(2) 0.3840(2) 0.0258(9) Uani 1 1 d . . . . .
H31A H 0.7464 0.0803 0.4235 0.031 Uiso 1 1 calc R U . . .
H31B H 0.7077 0.1291 0.3503 0.031 Uiso 1 1 calc R U . . .
C32 C 0.7552(4) 0.2344(3) 0.4780(2) 0.0293(9) Uani 1 1 d . . . . .
H32A H 0.7074 0.1877 0.4993 0.044 Uiso 1 1 calc R U . . .
H32B H 0.6975 0.2779 0.4603 0.044 Uiso 1 1 calc R U . . .
H32C H 0.8105 0.2588 0.5148 0.044 Uiso 1 1 calc R U . . .
C33 C 0.5259(4) 0.2296(2) 0.3604(2) 0.0252(9) Uani 1 1 d . . . . .
C1A C 0.7555(7) 0.2420(4) 0.0397(4) 0.079(2) Uani 1 1 d . . . . .
H1A1 H 0.8194 0.2826 0.0224 0.094 Uiso 1 1 calc R U . . .
H1A2 H 0.7488 0.2504 0.0927 0.094 Uiso 1 1 calc R U . . .
C2A C 0.7827(7) 0.1668(4) -0.0368(3) 0.0660(18) Uani 1 1 d . . . . .
H2A1 H 0.8156 0.1104 -0.0503 0.079 Uiso 1 1 calc R U . . .
H2A2 H 0.8347 0.2095 -0.0619 0.079 Uiso 1 1 calc R U . . .
C3A C 0.7974(7) 0.1764(4) 0.0318(4) 0.078(2) Uani 1 1 d . . . . .
H3A1 H 0.7513 0.1329 0.0596 0.094 Uiso 1 1 calc R U . . .
H3A2 H 0.8869 0.1750 0.0455 0.094 Uiso 1 1 calc R U . . .
C4A C 0.6420(7) 0.2692(4) 0.0106(4) 0.075(2) Uani 1 1 d . . . . .
H4A1 H 0.5866 0.2885 0.0503 0.090 Uiso 1 1 calc R U . . .
H4A2 H 0.6572 0.3178 -0.0221 0.090 Uiso 1 1 calc R U . . .
C5A C 0.5860(10) 0.2080(6) -0.0258(5) 0.103(3) Uani 1 1 d . . . . .
H5A1 H 0.5476 0.1670 0.0081 0.124 Uiso 1 1 calc R U . . .
H5A2 H 0.5192 0.2318 -0.0569 0.124 Uiso 1 1 calc R U . . .
C6A C 0.6636(9) 0.1732(6) -0.0626(4) 0.090(2) Uani 1 1 d . . . . .
H6A1 H 0.6675 0.2033 -0.1096 0.108 Uiso 1 1 calc R U . . .
H6A2 H 0.6333 0.1152 -0.0727 0.108 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
P1 O1 1.580(3) . ?
P1 O2 1.638(3) . ?
P1 C33 1.842(5) . ?
O1 C1 1.467(4) . ?
O2 C6 1.476(4) . ?
N1 C33 1.097(5) . ?
C1 C2 1.514(5) . ?
C1 C24 1.575(5) . ?
C1 C27 1.622(5) . ?
C2 C23 1.404(5) . ?
C2 C3 1.421(5) . ?
C3 C20 1.390(5) . ?
C3 C4 1.525(5) . ?
C4 C19 1.391(5) . ?
C4 C5 1.415(6) . ?
C5 C16 1.408(5) . ?
C5 C6 1.547(5) . ?
C6 C7 1.584(5) . ?
C6 C10 1.604(5) . ?
C7 C15 1.533(6) . ?
C7 C8 1.538(5) . ?
C7 C14 1.562(6) . ?
C8 C9 1.517(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.541(6) . ?
C9 C10 1.546(6) . ?
C9 H9 1.0000 . ?
C10 C11 1.542(5) . ?
C10 C12 1.547(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.553(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.380(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.395(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C32 1.525(5) . ?
C24 C25 1.549(6) . ?
C24 C31 1.567(5) . ?
C25 C26 1.531(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C30 1.529(5) . ?
C26 C27 1.558(5) . ?
C26 H26 1.0000 . ?
C27 C28 1.531(5) . ?
C27 C29 1.538(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.543(6) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C1A C3A 1.138(9) . ?
C1A C4A 1.394(10) . ?
C1A C2A 1.868(10) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A C3A 1.285(9) . ?
C2A C6A 1.363(10) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.321(10) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.205(11) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?

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 P1 O2 106.46(14) . . ?
O1 P1 C33 104.09(16) . . ?
O2 P1 C33 94.56(15) . . ?
C1 O1 P1 137.2(2) . . ?
C6 O2 P1 113.0(2) . . ?
O1 C1 C2 109.8(3) . . ?
O1 C1 C24 110.2(3) . . ?
C2 C1 C24 117.9(3) . . ?
O1 C1 C27 104.8(3) . . ?
C2 C1 C27 110.8(3) . . ?
C24 C1 C27 102.4(3) . . ?
C23 C2 C3 116.6(3) . . ?
C23 C2 C1 118.3(3) . . ?
C3 C2 C1 124.3(3) . . ?
C20 C3 C2 118.5(3) . . ?
C20 C3 C4 111.3(3) . . ?
C2 C3 C4 130.1(3) . . ?
C19 C4 C5 118.3(3) . . ?
C19 C4 C3 114.3(3) . . ?
C5 C4 C3 125.5(3) . . ?
C16 C5 C4 117.9(3) . . ?
C16 C5 C6 119.3(3) . . ?
C4 C5 C6 122.7(3) . . ?
O2 C6 C5 104.8(3) . . ?
O2 C6 C7 108.1(3) . . ?
C5 C6 C7 118.6(3) . . ?
O2 C6 C10 109.7(3) . . ?
C5 C6 C10 113.8(3) . . ?
C7 C6 C10 101.7(3) . . ?
C15 C7 C8 117.7(4) . . ?
C15 C7 C14 108.8(3) . . ?
C8 C7 C14 98.8(3) . . ?
C15 C7 C6 120.0(3) . . ?
C8 C7 C6 101.4(3) . . ?
C14 C7 C6 107.8(3) . . ?
C9 C8 C7 96.2(3) . . ?
C9 C8 H8A 112.5 . . ?
C7 C8 H8A 112.5 . . ?
C9 C8 H8B 112.5 . . ?
C7 C8 H8B 112.5 . . ?
H8A C8 H8B 110.0 . . ?
C8 C9 C13 101.3(3) . . ?
C8 C9 C10 101.7(3) . . ?
C13 C9 C10 111.8(3) . . ?
C8 C9 H9 113.6 . . ?
C13 C9 H9 113.6 . . ?
C10 C9 H9 113.6 . . ?
C11 C10 C9 113.6(3) . . ?
C11 C10 C12 106.9(3) . . ?
C9 C10 C12 107.1(3) . . ?
C11 C10 C6 113.3(3) . . ?
C9 C10 C6 103.0(3) . . ?
C12 C10 C6 112.9(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 101.7(3) . . ?
C9 C13 H13A 111.4 . . ?
C14 C13 H13A 111.4 . . ?
C9 C13 H13B 111.4 . . ?
C14 C13 H13B 111.4 . . ?
H13A C13 H13B 109.3 . . ?
C13 C14 C7 105.2(3) . . ?
C13 C14 H14A 110.7 . . ?
C7 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C7 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 122.1(4) . . ?
C17 C16 H16 119.0 . . ?
C5 C16 H16 119.0 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C4 122.6(4) . . ?
C18 C19 H19 118.7 . . ?
C4 C19 H19 118.7 . . ?
C3 C20 C21 123.4(3) . . ?
C3 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C22 C21 C20 117.7(3) . . ?
C22 C21 H21 121.2 . . ?
C20 C21 H21 121.2 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C2 122.9(3) . . ?
C22 C23 H23 118.5 . . ?
C2 C23 H23 118.5 . . ?
C32 C24 C25 118.9(3) . . ?
C32 C24 C31 111.2(3) . . ?
C25 C24 C31 98.5(3) . . ?
C32 C24 C1 116.5(3) . . ?
C25 C24 C1 101.4(3) . . ?
C31 C24 C1 108.3(3) . . ?
C26 C25 C24 95.6(3) . . ?
C26 C25 H25A 112.6 . . ?
C24 C25 H25A 112.6 . . ?
C26 C25 H25B 112.6 . . ?
C24 C25 H25B 112.6 . . ?
H25A C25 H25B 110.1 . . ?
C30 C26 C25 100.9(3) . . ?
C30 C26 C27 112.5(3) . . ?
C25 C26 C27 101.8(3) . . ?
C30 C26 H26 113.5 . . ?
C25 C26 H26 113.5 . . ?
C27 C26 H26 113.5 . . ?
C28 C27 C29 107.5(3) . . ?
C28 C27 C26 107.4(3) . . ?
C29 C27 C26 113.8(3) . . ?
C28 C27 C1 113.6(3) . . ?
C29 C27 C1 112.6(3) . . ?
C26 C27 C1 101.9(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 C31 102.7(3) . . ?
C26 C30 H30A 111.2 . . ?
C31 C30 H30A 111.2 . . ?
C26 C30 H30B 111.2 . . ?
C31 C30 H30B 111.2 . . ?
H30A C30 H30B 109.1 . . ?
C30 C31 C24 104.9(3) . . ?
C30 C31 H31A 110.8 . . ?
C24 C31 H31A 110.8 . . ?
C30 C31 H31B 110.8 . . ?
C24 C31 H31B 110.8 . . ?
H31A C31 H31B 108.8 . . ?
C24 C32 H32A 109.5 . . ?
C24 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C24 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N1 C33 P1 165.8(4) . . ?
C3A C1A C4A 125.0(8) . . ?
C3A C1A C2A 42.5(5) . . ?
C4A C1A C2A 92.3(5) . . ?
C3A C1A H1A1 106.1 . . ?
C4A C1A H1A1 106.1 . . ?
C2A C1A H1A1 93.5 . . ?
C3A C1A H1A2 106.1 . . ?
C4A C1A H1A2 106.1 . . ?
C2A C1A H1A2 147.5 . . ?
H1A1 C1A H1A2 106.3 . . ?
C3A C2A C6A 116.8(7) . . ?
C3A C2A C1A 36.8(4) . . ?
C6A C2A C1A 94.1(5) . . ?
C3A C2A H2A1 108.1 . . ?
C6A C2A H2A1 108.1 . . ?
C1A C2A H2A1 144.9 . . ?
C3A C2A H2A2 108.1 . . ?
C6A C2A H2A2 108.1 . . ?
C1A C2A H2A2 90.4 . . ?
H2A1 C2A H2A2 107.3 . . ?
C1A C3A C2A 100.7(8) . . ?
C1A C3A H3A1 111.6 . . ?
C2A C3A H3A1 111.6 . . ?
C1A C3A H3A2 111.6 . . ?
C2A C3A H3A2 111.6 . . ?
H3A1 C3A H3A2 109.4 . . ?
C5A C4A C1A 111.4(7) . . ?
C5A C4A H4A1 109.3 . . ?
C1A C4A H4A1 109.3 . . ?
C5A C4A H4A2 109.3 . . ?
C1A C4A H4A2 109.3 . . ?
H4A1 C4A H4A2 108.0 . . ?
C6A C5A C4A 108.0(10) . . ?
C6A C5A H5A1 110.1 . . ?
C4A C5A H5A1 110.1 . . ?
C6A C5A H5A2 110.1 . . ?
C4A C5A H5A2 110.1 . . ?
H5A1 C5A H5A2 108.4 . . ?
C5A C6A C2A 118.7(8) . . ?
C5A C6A H6A1 107.6 . . ?
C2A C6A H6A1 107.6 . . ?
C5A C6A H6A2 107.6 . . ?
C2A C6A H6A2 107.6 . . ?
H6A1 C6A H6A2 107.1 . . ?

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
O2 P1 O1 C1 26.4(3) . . . . ?
C33 P1 O1 C1 -72.8(3) . . . . ?
O1 P1 O2 C6 116.5(2) . . . . ?
C33 P1 O2 C6 -137.4(3) . . . . ?
P1 O1 C1 C2 -53.8(4) . . . . ?
P1 O1 C1 C24 77.6(4) . . . . ?
P1 O1 C1 C27 -172.9(2) . . . . ?
O1 C1 C2 C23 157.7(3) . . . . ?
C24 C1 C2 C23 30.5(5) . . . . ?
C27 C1 C2 C23 -87.1(4) . . . . ?
O1 C1 C2 C3 -33.5(5) . . . . ?
C24 C1 C2 C3 -160.7(4) . . . . ?
C27 C1 C2 C3 81.8(4) . . . . ?
C23 C2 C3 C20 9.8(5) . . . . ?
C1 C2 C3 C20 -159.2(4) . . . . ?
C23 C2 C3 C4 -175.0(4) . . . . ?
C1 C2 C3 C4 16.0(6) . . . . ?
C20 C3 C4 C19 72.1(4) . . . . ?
C2 C3 C4 C19 -103.3(4) . . . . ?
C20 C3 C4 C5 -91.8(4) . . . . ?
C2 C3 C4 C5 92.7(5) . . . . ?
C19 C4 C5 C16 -5.6(5) . . . . ?
C3 C4 C5 C16 157.8(3) . . . . ?
C19 C4 C5 C6 175.6(3) . . . . ?
C3 C4 C5 C6 -21.0(5) . . . . ?
P1 O2 C6 C5 -52.0(3) . . . . ?
P1 O2 C6 C7 75.4(3) . . . . ?
P1 O2 C6 C10 -174.5(2) . . . . ?
C16 C5 C6 O2 143.7(3) . . . . ?
C4 C5 C6 O2 -37.5(4) . . . . ?
C16 C5 C6 C7 23.0(5) . . . . ?
C4 C5 C6 C7 -158.2(3) . . . . ?
C16 C5 C6 C10 -96.4(4) . . . . ?
C4 C5 C6 C10 82.4(4) . . . . ?
O2 C6 C7 C15 -80.6(4) . . . . ?
C5 C6 C7 C15 38.5(5) . . . . ?
C10 C6 C7 C15 164.0(3) . . . . ?
O2 C6 C7 C8 147.9(3) . . . . ?
C5 C6 C7 C8 -93.1(4) . . . . ?
C10 C6 C7 C8 32.4(4) . . . . ?
O2 C6 C7 C14 44.7(4) . . . . ?
C5 C6 C7 C14 163.7(3) . . . . ?
C10 C6 C7 C14 -70.8(3) . . . . ?
C15 C7 C8 C9 171.7(4) . . . . ?
C14 C7 C8 C9 55.0(4) . . . . ?
C6 C7 C8 C9 -55.3(4) . . . . ?
C7 C8 C9 C13 -58.1(4) . . . . ?
C7 C8 C9 C10 57.3(3) . . . . ?
C8 C9 C10 C11 -159.8(3) . . . . ?
C13 C9 C10 C11 -52.4(4) . . . . ?
C8 C9 C10 C12 82.4(3) . . . . ?
C13 C9 C10 C12 -170.3(3) . . . . ?
C8 C9 C10 C6 -36.9(3) . . . . ?
C13 C9 C10 C6 70.5(4) . . . . ?
O2 C6 C10 C11 11.1(4) . . . . ?
C5 C6 C10 C11 -105.9(4) . . . . ?
C7 C6 C10 C11 125.4(3) . . . . ?
O2 C6 C10 C9 -112.0(3) . . . . ?
C5 C6 C10 C9 130.9(3) . . . . ?
C7 C6 C10 C9 2.3(3) . . . . ?
O2 C6 C10 C12 132.8(3) . . . . ?
C5 C6 C10 C12 15.8(5) . . . . ?
C7 C6 C10 C12 -112.9(4) . . . . ?
C8 C9 C13 C14 36.8(4) . . . . ?
C10 C9 C13 C14 -70.7(4) . . . . ?
C9 C13 C14 C7 -1.8(4) . . . . ?
C15 C7 C14 C13 -156.3(3) . . . . ?
C8 C7 C14 C13 -33.0(4) . . . . ?
C6 C7 C14 C13 72.0(4) . . . . ?
C4 C5 C16 C17 4.6(6) . . . . ?
C6 C5 C16 C17 -176.6(4) . . . . ?
C5 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C19 -4.6(6) . . . . ?
C17 C18 C19 C4 3.5(6) . . . . ?
C5 C4 C19 C18 1.7(5) . . . . ?
C3 C4 C19 C18 -163.5(3) . . . . ?
C2 C3 C20 C21 -8.3(6) . . . . ?
C4 C3 C20 C21 175.7(3) . . . . ?
C3 C20 C21 C22 0.7(6) . . . . ?
C20 C21 C22 C23 4.8(6) . . . . ?
C21 C22 C23 C2 -2.8(6) . . . . ?
C3 C2 C23 C22 -4.6(6) . . . . ?
C1 C2 C23 C22 165.0(4) . . . . ?
O1 C1 C24 C32 -85.4(4) . . . . ?
C2 C1 C24 C32 41.6(5) . . . . ?
C27 C1 C24 C32 163.5(3) . . . . ?
O1 C1 C24 C25 143.8(3) . . . . ?
C2 C1 C24 C25 -89.1(4) . . . . ?
C27 C1 C24 C25 32.8(3) . . . . ?
O1 C1 C24 C31 40.8(4) . . . . ?
C2 C1 C24 C31 167.8(3) . . . . ?
C27 C1 C24 C31 -70.3(3) . . . . ?
C32 C24 C25 C26 175.1(3) . . . . ?
C31 C24 C25 C26 55.1(3) . . . . ?
C1 C24 C25 C26 -55.7(3) . . . . ?
C24 C25 C26 C30 -58.1(3) . . . . ?
C24 C25 C26 C27 57.9(3) . . . . ?
C30 C26 C27 C28 -170.4(3) . . . . ?
C25 C26 C27 C28 82.4(3) . . . . ?
C30 C26 C27 C29 -51.6(4) . . . . ?
C25 C26 C27 C29 -158.8(3) . . . . ?
C30 C26 C27 C1 69.9(4) . . . . ?
C25 C26 C27 C1 -37.3(3) . . . . ?
O1 C1 C27 C28 132.1(3) . . . . ?
C2 C1 C27 C28 13.8(4) . . . . ?
C24 C1 C27 C28 -112.8(3) . . . . ?
O1 C1 C27 C29 9.6(4) . . . . ?
C2 C1 C27 C29 -108.7(3) . . . . ?
C24 C1 C27 C29 124.7(3) . . . . ?
O1 C1 C27 C26 -112.7(3) . . . . ?
C2 C1 C27 C26 129.0(3) . . . . ?
C24 C1 C27 C26 2.4(3) . . . . ?
C25 C26 C30 C31 37.2(4) . . . . ?
C27 C26 C30 C31 -70.6(4) . . . . ?
C26 C30 C31 C24 -1.9(4) . . . . ?
C32 C24 C31 C30 -159.0(3) . . . . ?
C25 C24 C31 C30 -33.3(4) . . . . ?
C1 C24 C31 C30 71.7(4) . . . . ?
O1 P1 C33 N1 -117.2(15) . . . . ?
O2 P1 C33 N1 134.5(15) . . . . ?
C4A C1A C2A C3A -143.7(9) . . . . ?
C3A C1A C2A C6A 131.2(9) . . . . ?
C4A C1A C2A C6A -12.5(6) . . . . ?
C4A C1A C3A C2A 46.3(11) . . . . ?
C6A C2A C3A C1A -57.3(10) . . . . ?
C3A C1A C4A C5A 2.1(13) . . . . ?
C2A C1A C4A C5A 31.4(8) . . . . ?
C1A C4A C5A C6A -44.1(11) . . . . ?
C4A C5A C6A C2A 33.5(12) . . . . ?
C3A C2A C6A C5A 18.9(13) . . . . ?
C1A C2A C6A C5A -11.4(10) . . . . ?

_refine_diff_density_max         0.798
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_eb013
_database_code_depnum_ccdc_archive 'CCDC 1886559'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H41 N O4'

_chemical_formula_sum            'C32 H41 N O4'
_chemical_formula_weight         503.66

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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0376(5)
_cell_length_b                   12.5422(9)
_cell_length_c                   13.6773(8)
_cell_angle_alpha                97.302(3)
_cell_angle_beta                 98.335(4)
_cell_angle_gamma                94.869(4)
_cell_volume                     1345.65(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9194
_cell_measurement_theta_min      1.520
_cell_measurement_theta_max      27.492

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9194
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.520
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6151
_reflns_number_gt                3579
_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       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXt  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2017)'


_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)+(0.0819P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6151
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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 0.1265(2) 0.57245(14) 0.57352(12) 0.0398(5) Uani 1 1 d . . . . .
O2 O -0.0714(2) 0.67821(15) 0.58888(12) 0.0393(5) Uani 1 1 d . . . . .
O3 O 0.4199(2) 0.69083(12) 0.19906(12) 0.0207(4) Uani 1 1 d . . . . .
O4 O 0.42602(18) 0.88952(13) 0.32654(11) 0.0213(4) Uani 1 1 d . . . . .
N1 N 0.0394(2) 0.64213(16) 0.54393(14) 0.0299(5) Uani 1 1 d . . . . .
C1 C 0.0680(3) 0.68391(17) 0.45214(15) 0.0188(5) Uani 1 1 d . . . . .
C2 C 0.1744(3) 0.63377(17) 0.39565(15) 0.0187(5) Uani 1 1 d . . . . .
H2 H 0.2227 0.5721 0.4161 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2135(2) 0.67105(16) 0.30881(15) 0.0159(5) Uani 1 1 d . . . . .
C4 C 0.3392(3) 0.61311(17) 0.25021(15) 0.0176(5) Uani 1 1 d . . . . .
C5 C 0.2558(3) 0.50592(17) 0.17691(15) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.3775(3) 0.42163(18) 0.20778(15) 0.0232(5) Uani 1 1 d . . . . .
H6 H 0.3274 0.3450 0.1865 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4194(3) 0.45276(17) 0.32120(15) 0.0224(5) Uani 1 1 d . . . . .
H7A H 0.5063 0.4107 0.3523 0.027 Uiso 1 1 calc R U . . .
H7B H 0.3181 0.4479 0.3544 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4886(3) 0.57077(17) 0.31738(15) 0.0188(5) Uani 1 1 d . . . . .
C9 C 0.6278(3) 0.54788(19) 0.25214(17) 0.0267(6) Uani 1 1 d . . . . .
H9A H 0.7333 0.5342 0.2937 0.032 Uiso 1 1 calc R U . . .
H9B H 0.6528 0.6097 0.2163 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5518(3) 0.44565(19) 0.17757(17) 0.0299(6) Uani 1 1 d . . . . .
H10A H 0.5416 0.4605 0.1077 0.036 Uiso 1 1 calc R U . . .
H10B H 0.6213 0.3849 0.1855 0.036 Uiso 1 1 calc R U . . .
C11 C 0.5644(3) 0.64279(18) 0.41457(15) 0.0240(5) Uani 1 1 d . . . . .
H11A H 0.6613 0.6112 0.4473 0.036 Uiso 1 1 calc R U . . .
H11B H 0.4789 0.6487 0.4587 0.036 Uiso 1 1 calc R U . . .
H11C H 0.6017 0.7148 0.4002 0.036 Uiso 1 1 calc R U . . .
C12 C 0.0770(3) 0.46862(18) 0.19405(16) 0.0238(5) Uani 1 1 d . . . . .
H12A H 0.0032 0.5256 0.1824 0.036 Uiso 1 1 calc R U . . .
H12B H 0.0807 0.4536 0.2629 0.036 Uiso 1 1 calc R U . . .
H12C H 0.0328 0.4028 0.1478 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2446(3) 0.52025(18) 0.06657(15) 0.0260(5) Uani 1 1 d . . . . .
H13A H 0.2098 0.4502 0.0249 0.039 Uiso 1 1 calc R U . . .
H13B H 0.3555 0.5491 0.0539 0.039 Uiso 1 1 calc R U . . .
H13C H 0.1614 0.5706 0.0504 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1364(2) 0.76208(16) 0.28140(14) 0.0163(5) Uani 1 1 d . . . . .
C15 C 0.1420(3) 0.80736(16) 0.18453(15) 0.0167(5) Uani 1 1 d . . . . .
C16 C 0.2531(3) 0.89404(17) 0.16780(15) 0.0184(5) Uani 1 1 d . . . . .
C17 C 0.3931(3) 0.95587(16) 0.25012(15) 0.0175(5) Uani 1 1 d . . . . .
C18 C 0.3391(3) 1.06790(17) 0.30000(16) 0.0219(5) Uani 1 1 d . . . . .
C19 C 0.4918(3) 1.14826(18) 0.29368(17) 0.0277(6) Uani 1 1 d . . . . .
H19 H 0.4667 1.2253 0.3014 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5388(3) 1.10928(18) 0.19172(17) 0.0284(6) Uani 1 1 d . . . . .
H20A H 0.6438 1.1491 0.1794 0.034 Uiso 1 1 calc R U . . .
H20B H 0.4458 1.1107 0.1360 0.034 Uiso 1 1 calc R U . . .
C21 C 0.5642(3) 0.99369(18) 0.21437(16) 0.0230(5) Uani 1 1 d . . . . .
C22 C 0.6991(3) 1.02301(19) 0.30894(17) 0.0300(6) Uani 1 1 d . . . . .
H22A H 0.6965 0.9654 0.3521 0.036 Uiso 1 1 calc R U . . .
H22B H 0.8137 1.0337 0.2909 0.036 Uiso 1 1 calc R U . . .
C23 C 0.6503(3) 1.12920(19) 0.36204(18) 0.0326(6) Uani 1 1 d . . . . .
H23A H 0.6262 1.1209 0.4298 0.039 Uiso 1 1 calc R U . . .
H23B H 0.7410 1.1891 0.3670 0.039 Uiso 1 1 calc R U . . .
C24 C 0.6241(3) 0.9148(2) 0.13611(18) 0.0312(6) Uani 1 1 d . . . . .
H24A H 0.5409 0.9032 0.0749 0.047 Uiso 1 1 calc R U . . .
H24B H 0.6368 0.8457 0.1614 0.047 Uiso 1 1 calc R U . . .
H24C H 0.7332 0.9445 0.1217 0.047 Uiso 1 1 calc R U . . .
C25 C 0.1793(3) 1.10278(18) 0.24290(17) 0.0279(6) Uani 1 1 d . . . . .
H25A H 0.1523 1.1707 0.2780 0.042 Uiso 1 1 calc R U . . .
H25B H 0.0849 1.0467 0.2387 0.042 Uiso 1 1 calc R U . . .
H25C H 0.1983 1.1133 0.1754 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3052(3) 1.06414(19) 0.40728(16) 0.0308(6) Uani 1 1 d . . . . .
H26A H 0.2944 1.1373 0.4389 0.046 Uiso 1 1 calc R U . . .
H26B H 0.3993 1.0349 0.4454 0.046 Uiso 1 1 calc R U . . .
H26C H 0.2002 1.0178 0.4060 0.046 Uiso 1 1 calc R U . . .
C27 C 0.2304(3) 0.92428(18) 0.07130(15) 0.0228(5) Uani 1 1 d . . . . .
H27 H 0.3061 0.9805 0.0570 0.027 Uiso 1 1 calc R U . . .
C28 C 0.1022(3) 0.87533(18) -0.00325(16) 0.0250(5) Uani 1 1 d . . . . .
H28 H 0.0913 0.8979 -0.0674 0.030 Uiso 1 1 calc R U . . .
C29 C -0.0098(3) 0.79387(18) 0.01520(16) 0.0250(5) Uani 1 1 d . . . . .
H29 H -0.1000 0.7612 -0.0352 0.030 Uiso 1 1 calc R U . . .
C30 C 0.0109(3) 0.76043(17) 0.10786(15) 0.0214(5) Uani 1 1 d . . . . .
H30 H -0.0659 0.7038 0.1203 0.026 Uiso 1 1 calc R U . . .
C31 C 0.0269(3) 0.80986(17) 0.34020(15) 0.0207(5) Uani 1 1 d . . . . .
H31 H -0.0261 0.8700 0.3197 0.025 Uiso 1 1 calc R U . . .
C32 C -0.0071(3) 0.77308(18) 0.42672(16) 0.0233(5) Uani 1 1 d . . . . .
H32 H -0.0792 0.8078 0.4670 0.028 Uiso 1 1 calc R U . . .
H1X H 0.357(3) 0.7041(18) 0.1593(17) 0.019(7) Uiso 1 1 d . . . . .
H2X H 0.445(3) 0.834(2) 0.2932(17) 0.031(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.237(2) . ?
O2 N1 1.238(2) . ?
O3 C4 1.435(2) . ?
O3 H1X 0.73(2) . ?
O4 C17 1.426(2) . ?
O4 H2X 0.82(2) . ?
N1 C1 1.461(3) . ?
C1 C2 1.372(3) . ?
C1 C32 1.374(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C14 1.410(3) . ?
C3 C4 1.550(3) . ?
C4 C8 1.575(3) . ?
C4 C5 1.603(3) . ?
C5 C13 1.533(3) . ?
C5 C12 1.534(3) . ?
C5 C6 1.556(3) . ?
C6 C7 1.531(3) . ?
C6 C10 1.534(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.546(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C11 1.523(3) . ?
C8 C9 1.553(3) . ?
C9 C10 1.553(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C31 1.397(3) . ?
C14 C15 1.511(3) . ?
C15 C30 1.405(3) . ?
C15 C16 1.411(3) . ?
C16 C27 1.410(3) . ?
C16 C17 1.548(3) . ?
C17 C21 1.581(3) . ?
C17 C18 1.604(3) . ?
C18 C25 1.531(3) . ?
C18 C26 1.537(3) . ?
C18 C19 1.540(3) . ?
C19 C23 1.523(3) . ?
C19 C20 1.529(3) . ?
C19 H19 1.0000 . ?
C20 C21 1.544(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C24 1.523(3) . ?
C21 C22 1.546(3) . ?
C22 C23 1.543(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.378(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 H1X 108.3(19) . . ?
C17 O4 H2X 100.4(17) . . ?
O1 N1 O2 122.8(2) . . ?
O1 N1 C1 118.84(19) . . ?
O2 N1 C1 118.40(18) . . ?
C2 C1 C32 122.3(2) . . ?
C2 C1 N1 118.11(19) . . ?
C32 C1 N1 119.60(19) . . ?
C1 C2 C3 121.75(19) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C14 116.63(18) . . ?
C2 C3 C4 119.22(17) . . ?
C14 C3 C4 124.13(18) . . ?
O3 C4 C3 107.71(16) . . ?
O3 C4 C8 104.81(16) . . ?
C3 C4 C8 114.65(16) . . ?
O3 C4 C5 112.58(16) . . ?
C3 C4 C5 114.16(17) . . ?
C8 C4 C5 102.62(16) . . ?
C13 C5 C12 107.22(17) . . ?
C13 C5 C6 112.99(17) . . ?
C12 C5 C6 109.36(18) . . ?
C13 C5 C4 112.41(17) . . ?
C12 C5 C4 112.99(17) . . ?
C6 C5 C4 101.91(16) . . ?
C7 C6 C10 100.79(18) . . ?
C7 C6 C5 102.53(16) . . ?
C10 C6 C5 111.61(19) . . ?
C7 C6 H6 113.6 . . ?
C10 C6 H6 113.6 . . ?
C5 C6 H6 113.6 . . ?
C6 C7 C8 95.13(16) . . ?
C6 C7 H7A 112.7 . . ?
C8 C7 H7A 112.7 . . ?
C6 C7 H7B 112.7 . . ?
C8 C7 H7B 112.7 . . ?
H7A C7 H7B 110.2 . . ?
C11 C8 C7 118.95(17) . . ?
C11 C8 C9 110.30(18) . . ?
C7 C8 C9 98.69(18) . . ?
C11 C8 C4 116.76(17) . . ?
C7 C8 C4 102.66(17) . . ?
C9 C8 C4 107.52(17) . . ?
C8 C9 C10 104.53(18) . . ?
C8 C9 H9A 110.8 . . ?
C10 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C6 C10 C9 102.38(17) . . ?
C6 C10 H10A 111.3 . . ?
C9 C10 H10A 111.3 . . ?
C6 C10 H10B 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C31 C14 C3 119.85(19) . . ?
C31 C14 C15 113.91(17) . . ?
C3 C14 C15 125.76(18) . . ?
C30 C15 C16 119.32(19) . . ?
C30 C15 C14 113.37(19) . . ?
C16 C15 C14 127.10(18) . . ?
C27 C16 C15 116.81(19) . . ?
C27 C16 C17 120.3(2) . . ?
C15 C16 C17 122.89(18) . . ?
O4 C17 C16 108.32(16) . . ?
O4 C17 C21 109.70(16) . . ?
C16 C17 C21 115.77(17) . . ?
O4 C17 C18 108.03(16) . . ?
C16 C17 C18 112.62(15) . . ?
C21 C17 C18 102.08(16) . . ?
C25 C18 C26 106.16(19) . . ?
C25 C18 C19 109.22(18) . . ?
C26 C18 C19 113.25(19) . . ?
C25 C18 C17 113.72(17) . . ?
C26 C18 C17 112.55(17) . . ?
C19 C18 C17 102.08(17) . . ?
C23 C19 C20 100.48(19) . . ?
C23 C19 C18 112.17(19) . . ?
C20 C19 C18 103.16(18) . . ?
C23 C19 H19 113.3 . . ?
C20 C19 H19 113.3 . . ?
C18 C19 H19 113.3 . . ?
C19 C20 C21 94.75(18) . . ?
C19 C20 H20A 112.8 . . ?
C21 C20 H20A 112.8 . . ?
C19 C20 H20B 112.8 . . ?
C21 C20 H20B 112.8 . . ?
H20A C20 H20B 110.2 . . ?
C24 C21 C20 118.72(19) . . ?
C24 C21 C22 111.40(18) . . ?
C20 C21 C22 98.50(18) . . ?
C24 C21 C17 116.21(18) . . ?
C20 C21 C17 103.11(17) . . ?
C22 C21 C17 106.92(18) . . ?
C23 C22 C21 104.56(17) . . ?
C23 C22 H22A 110.8 . . ?
C21 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
C19 C23 C22 102.50(18) . . ?
C19 C23 H23A 111.3 . . ?
C22 C23 H23A 111.3 . . ?
C19 C23 H23B 111.3 . . ?
C22 C23 H23B 111.3 . . ?
H23A C23 H23B 109.2 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C16 122.5(2) . . ?
C28 C27 H27 118.7 . . ?
C16 C27 H27 118.7 . . ?
C29 C28 C27 120.1(2) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 119.0(2) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C29 C30 C15 122.1(2) . . ?
C29 C30 H30 118.9 . . ?
C15 C30 H30 118.9 . . ?
C32 C31 C14 122.5(2) . . ?
C32 C31 H31 118.7 . . ?
C14 C31 H31 118.7 . . ?
C1 C32 C31 117.0(2) . . ?
C1 C32 H32 121.5 . . ?
C31 C32 H32 121.5 . . ?

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 N1 C1 C2 8.6(3) . . . . ?
O2 N1 C1 C2 -171.4(2) . . . . ?
O1 N1 C1 C32 -169.4(2) . . . . ?
O2 N1 C1 C32 10.5(3) . . . . ?
C32 C1 C2 C3 0.4(3) . . . . ?
N1 C1 C2 C3 -177.60(18) . . . . ?
C1 C2 C3 C14 -0.8(3) . . . . ?
C1 C2 C3 C4 177.98(19) . . . . ?
C2 C3 C4 O3 -152.15(18) . . . . ?
C14 C3 C4 O3 26.5(3) . . . . ?
C2 C3 C4 C8 -35.9(3) . . . . ?
C14 C3 C4 C8 142.73(19) . . . . ?
C2 C3 C4 C5 82.1(2) . . . . ?
C14 C3 C4 C5 -99.3(2) . . . . ?
O3 C4 C5 C13 -13.2(2) . . . . ?
C3 C4 C5 C13 110.0(2) . . . . ?
C8 C4 C5 C13 -125.34(18) . . . . ?
O3 C4 C5 C12 -134.74(17) . . . . ?
C3 C4 C5 C12 -11.5(2) . . . . ?
C8 C4 C5 C12 113.14(18) . . . . ?
O3 C4 C5 C6 108.04(18) . . . . ?
C3 C4 C5 C6 -128.76(18) . . . . ?
C8 C4 C5 C6 -4.1(2) . . . . ?
C13 C5 C6 C7 159.13(18) . . . . ?
C12 C5 C6 C7 -81.5(2) . . . . ?
C4 C5 C6 C7 38.3(2) . . . . ?
C13 C5 C6 C10 52.0(2) . . . . ?
C12 C5 C6 C10 171.35(17) . . . . ?
C4 C5 C6 C10 -68.8(2) . . . . ?
C10 C6 C7 C8 58.31(18) . . . . ?
C5 C6 C7 C8 -56.93(19) . . . . ?
C6 C7 C8 C11 -175.70(18) . . . . ?
C6 C7 C8 C9 -56.64(17) . . . . ?
C6 C7 C8 C4 53.63(18) . . . . ?
O3 C4 C8 C11 79.3(2) . . . . ?
C3 C4 C8 C11 -38.5(3) . . . . ?
C5 C4 C8 C11 -162.88(18) . . . . ?
O3 C4 C8 C7 -148.68(16) . . . . ?
C3 C4 C8 C7 93.5(2) . . . . ?
C5 C4 C8 C7 -30.9(2) . . . . ?
O3 C4 C8 C9 -45.2(2) . . . . ?
C3 C4 C8 C9 -163.05(18) . . . . ?
C5 C4 C8 C9 72.6(2) . . . . ?
C11 C8 C9 C10 160.58(17) . . . . ?
C7 C8 C9 C10 35.2(2) . . . . ?
C4 C8 C9 C10 -71.1(2) . . . . ?
C7 C6 C10 C9 -36.4(2) . . . . ?
C5 C6 C10 C9 71.8(2) . . . . ?
C8 C9 C10 C6 0.3(2) . . . . ?
C2 C3 C14 C31 -0.2(3) . . . . ?
C4 C3 C14 C31 -178.85(19) . . . . ?
C2 C3 C14 C15 -171.64(19) . . . . ?
C4 C3 C14 C15 9.7(3) . . . . ?
C31 C14 C15 C30 -83.5(2) . . . . ?
C3 C14 C15 C30 88.4(2) . . . . ?
C31 C14 C15 C16 91.1(3) . . . . ?
C3 C14 C15 C16 -97.0(3) . . . . ?
C30 C15 C16 C27 -3.5(3) . . . . ?
C14 C15 C16 C27 -177.92(19) . . . . ?
C30 C15 C16 C17 175.60(17) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C27 C16 C17 O4 -160.95(18) . . . . ?
C15 C16 C17 O4 19.9(3) . . . . ?
C27 C16 C17 C21 -37.3(3) . . . . ?
C15 C16 C17 C21 143.6(2) . . . . ?
C27 C16 C17 C18 79.6(2) . . . . ?
C15 C16 C17 C18 -99.5(2) . . . . ?
O4 C17 C18 C25 -131.74(19) . . . . ?
C16 C17 C18 C25 -12.2(3) . . . . ?
C21 C17 C18 C25 112.7(2) . . . . ?
O4 C17 C18 C26 -11.0(2) . . . . ?
C16 C17 C18 C26 108.6(2) . . . . ?
C21 C17 C18 C26 -126.58(19) . . . . ?
O4 C17 C18 C19 110.76(18) . . . . ?
C16 C17 C18 C19 -129.66(18) . . . . ?
C21 C17 C18 C19 -4.85(19) . . . . ?
C25 C18 C19 C23 171.01(19) . . . . ?
C26 C18 C19 C23 52.9(3) . . . . ?
C17 C18 C19 C23 -68.3(2) . . . . ?
C25 C18 C19 C20 -81.7(2) . . . . ?
C26 C18 C19 C20 160.21(17) . . . . ?
C17 C18 C19 C20 38.97(19) . . . . ?
C23 C19 C20 C21 58.9(2) . . . . ?
C18 C19 C20 C21 -57.00(18) . . . . ?
C19 C20 C21 C24 -177.0(2) . . . . ?
C19 C20 C21 C22 -56.80(19) . . . . ?
C19 C20 C21 C17 52.89(19) . . . . ?
O4 C17 C21 C24 83.8(2) . . . . ?
C16 C17 C21 C24 -39.1(2) . . . . ?
C18 C17 C21 C24 -161.83(17) . . . . ?
O4 C17 C21 C20 -144.56(17) . . . . ?
C16 C17 C21 C20 92.51(19) . . . . ?
C18 C17 C21 C20 -30.18(19) . . . . ?
O4 C17 C21 C22 -41.3(2) . . . . ?
C16 C17 C21 C22 -164.23(17) . . . . ?
C18 C17 C21 C22 73.08(18) . . . . ?
C24 C21 C22 C23 160.5(2) . . . . ?
C20 C21 C22 C23 35.0(2) . . . . ?
C17 C21 C22 C23 -71.6(2) . . . . ?
C20 C19 C23 C22 -37.3(2) . . . . ?
C18 C19 C23 C22 71.7(2) . . . . ?
C21 C22 C23 C19 1.0(2) . . . . ?
C15 C16 C27 C28 2.5(3) . . . . ?
C17 C16 C27 C28 -176.70(18) . . . . ?
C16 C27 C28 C29 0.2(3) . . . . ?
C27 C28 C29 C30 -1.7(3) . . . . ?
C28 C29 C30 C15 0.5(3) . . . . ?
C16 C15 C30 C29 2.2(3) . . . . ?
C14 C15 C30 C29 177.31(19) . . . . ?
C3 C14 C31 C32 1.5(3) . . . . ?
C15 C14 C31 C32 173.99(19) . . . . ?
C2 C1 C32 C31 0.9(3) . . . . ?
N1 C1 C32 C31 178.91(18) . . . . ?
C14 C31 C32 C1 -1.9(3) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_eb79
_database_code_depnum_ccdc_archive 'CCDC 1886564'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H46 O4'
_chemical_formula_sum            'C34 H46 O4'
_chemical_formula_weight         518.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   7.7206(15)
_cell_length_b                   11.737(2)
_cell_length_c                   16.646(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.16(3)
_cell_angle_gamma                90
_cell_volume                     1474.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13366
_cell_measurement_theta_min      4.645
_cell_measurement_theta_max      72.165

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.584
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5626
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13366
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.645
_diffrn_reflns_theta_max         72.165
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             5526
_reflns_number_gt                5337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    0.935

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0455P)²+0.3416P] 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 2327 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5526
_refine_ls_number_parameters     351
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.6487(2) -0.18518(13) 0.62826(9) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.3396(2) -0.12207(14) 0.66439(9) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.4105 -0.1758 0.6624 0.028 Uiso 1 1 calc R U . . .
O3 O 1.1765(2) -0.07045(14) 0.32286(9) 0.0173(3) Uani 1 1 d . . . . .
O4 O 1.20851(19) 0.07789(14) 0.21028(9) 0.0169(3) Uani 1 1 d . . . . .
H4 H 1.2579 0.0278 0.2433 0.025 Uiso 1 1 calc R U . . .
C1 C 0.6269(3) -0.09080(18) 0.57839(12) 0.0136(4) Uani 1 1 d . . . . .
C2 C 0.5222(3) -0.00175(19) 0.59953(13) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.4342(3) -0.01640(19) 0.67422(12) 0.0127(4) Uani 1 1 d . . . . .
C4 C 0.5774(3) -0.0058(2) 0.75940(13) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.5060(3) 0.0973(2) 0.80165(14) 0.0199(5) Uani 1 1 d . . . . .
H5 H 0.5996 0.1379 0.8423 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4193(3) 0.1716(2) 0.72794(14) 0.0198(5) Uani 1 1 d . . . . .
H6A H 0.5049 0.1980 0.6953 0.024 Uiso 1 1 calc R U . . .
H6B H 0.3532 0.2371 0.7440 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2963(3) 0.0764(2) 0.68466(14) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.2068(3) 0.0395(2) 0.75599(14) 0.0207(5) Uani 1 1 d . . . . .
H8A H 0.0976 0.0843 0.7549 0.025 Uiso 1 1 calc R U . . .
H8B H 0.1755 -0.0424 0.7514 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3450(3) 0.0629(2) 0.83611(14) 0.0223(5) Uani 1 1 d . . . . .
H9A H 0.3066 0.1253 0.8683 0.027 Uiso 1 1 calc R U . . .
H9B H 0.3691 -0.0062 0.8708 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1504(3) 0.1021(2) 0.60966(15) 0.0254(5) Uani 1 1 d . . . . .
H10A H 0.0845 0.1698 0.6204 0.038 Uiso 1 1 calc R U . . .
H10B H 0.0695 0.0370 0.5984 0.038 Uiso 1 1 calc R U . . .
H10C H 0.2034 0.1161 0.5620 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5909(3) -0.1157(2) 0.81044(14) 0.0236(5) Uani 1 1 d . . . . .
H11A H 0.6476 -0.1753 0.7837 0.035 Uiso 1 1 calc R U . . .
H11B H 0.4718 -0.1406 0.8145 0.035 Uiso 1 1 calc R U . . .
H11C H 0.6618 -0.1014 0.8656 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7642(3) 0.0254(2) 0.74920(14) 0.0231(5) Uani 1 1 d . . . . .
H12A H 0.8417 0.0356 0.8035 0.035 Uiso 1 1 calc R U . . .
H12B H 0.7596 0.0965 0.7179 0.035 Uiso 1 1 calc R U . . .
H12C H 0.8108 -0.0358 0.7197 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5122(3) 0.0956(2) 0.55126(13) 0.0156(4) Uani 1 1 d . . . . .
H13 H 0.4482 0.1593 0.5649 0.019 Uiso 1 1 calc R U . . .
C14 C 0.5921(3) 0.1040(2) 0.48354(13) 0.0166(4) Uani 1 1 d . . . . .
H14 H 0.5812 0.1724 0.4524 0.020 Uiso 1 1 calc R U . . .
C15 C 0.6871(3) 0.01326(19) 0.46149(13) 0.0148(4) Uani 1 1 d . . . . .
C16 C 0.7065(3) -0.0840(2) 0.51077(13) 0.0142(4) Uani 1 1 d . . . . .
H16 H 0.7746 -0.1463 0.4981 0.017 Uiso 1 1 calc R U . . .
C17 C 0.7688(3) 0.01878(18) 0.38830(12) 0.0141(4) Uani 1 1 d . . . . .
C18 C 0.9354(3) -0.02863(19) 0.39043(12) 0.0139(4) Uani 1 1 d . . . . .
H18 H 0.9962 -0.0659 0.4389 0.017 Uiso 1 1 calc R U . . .
C19 C 1.0138(3) -0.02216(19) 0.32263(13) 0.0137(4) Uani 1 1 d . . . . .
C20 C 1.2658(3) -0.1292(2) 0.39529(14) 0.0199(5) Uani 1 1 d . . . . .
H20A H 1.2828 -0.0772 0.4424 0.030 Uiso 1 1 calc R U . . .
H20B H 1.3813 -0.1560 0.3875 0.030 Uiso 1 1 calc R U . . .
H20C H 1.1943 -0.1945 0.4055 0.030 Uiso 1 1 calc R U . . .
C21 C 0.9322(3) 0.03492(19) 0.24966(12) 0.0132(4) Uani 1 1 d . . . . .
C22 C 1.0288(3) 0.04539(19) 0.17744(12) 0.0143(4) Uani 1 1 d . . . . .
C23 C 1.0125(3) -0.0694(2) 0.12357(13) 0.0179(5) Uani 1 1 d . . . . .
C24 C 0.9250(3) -0.0249(2) 0.03613(13) 0.0222(5) Uani 1 1 d . . . . .
H24 H 0.8609 -0.0853 -0.0010 0.027 Uiso 1 1 calc R U . . .
C25 C 0.8042(3) 0.0708(2) 0.05456(13) 0.0221(5) Uani 1 1 d . . . . .
H25A H 0.7122 0.0432 0.0833 0.026 Uiso 1 1 calc R U . . .
H25B H 0.7488 0.1144 0.0049 0.026 Uiso 1 1 calc R U . . .
C26 C 0.9531(3) 0.13777(19) 0.11167(13) 0.0172(5) Uani 1 1 d . . . . .
C27 C 1.0871(3) 0.1494(2) 0.05387(14) 0.0223(5) Uani 1 1 d . . . . .
H27A H 1.0634 0.2195 0.0203 0.027 Uiso 1 1 calc R U . . .
H27B H 1.2103 0.1523 0.0863 0.027 Uiso 1 1 calc R U . . .
C28 C 1.0588(4) 0.0425(2) -0.00152(14) 0.0269(5) Uani 1 1 d . . . . .
H28A H 1.0093 0.0626 -0.0596 0.032 Uiso 1 1 calc R U . . .
H28B H 1.1705 -0.0004 0.0019 0.032 Uiso 1 1 calc R U . . .
C29 C 0.9164(3) 0.2553(2) 0.14307(15) 0.0214(5) Uani 1 1 d . . . . .
H29A H 0.8653 0.3044 0.0964 0.032 Uiso 1 1 calc R U . . .
H29B H 1.0274 0.2888 0.1733 0.032 Uiso 1 1 calc R U . . .
H29C H 0.8328 0.2484 0.1797 0.032 Uiso 1 1 calc R U . . .
C30 C 1.1923(4) -0.1267(2) 0.12754(15) 0.0252(5) Uani 1 1 d . . . . .
H30A H 1.2310 -0.1635 0.1811 0.038 Uiso 1 1 calc R U . . .
H30B H 1.2795 -0.0692 0.1201 0.038 Uiso 1 1 calc R U . . .
H30C H 1.1813 -0.1840 0.0839 0.038 Uiso 1 1 calc R U . . .
C31 C 0.8892(4) -0.1586(2) 0.14914(15) 0.0247(5) Uani 1 1 d . . . . .
H31A H 0.8800 -0.2246 0.1124 0.037 Uiso 1 1 calc R U . . .
H31B H 0.7714 -0.1253 0.1456 0.037 Uiso 1 1 calc R U . . .
H31C H 0.9374 -0.1829 0.2058 0.037 Uiso 1 1 calc R U . . .
C32 C 0.7627(3) 0.07649(19) 0.24846(13) 0.0159(4) Uani 1 1 d . . . . .
H32 H 0.6992 0.1110 0.1994 0.019 Uiso 1 1 calc R U . . .
C33 C 0.6815(3) 0.07006(19) 0.31562(13) 0.0164(4) Uani 1 1 d . . . . .
H33 H 0.5663 0.1008 0.3118 0.020 Uiso 1 1 calc R U . . .
C34 C 0.8006(3) -0.2559(2) 0.62895(14) 0.0211(5) Uani 1 1 d . . . . .
H34A H 0.7818 -0.3010 0.5783 0.032 Uiso 1 1 calc R U . . .
H34B H 0.8178 -0.3072 0.6765 0.032 Uiso 1 1 calc R U . . .
H34C H 0.9058 -0.2079 0.6326 0.032 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 1.373(3) . ?
O1 C34 1.435(3) . ?
O2 C3 1.431(3) . ?
O2 H2 0.8400 . ?
O3 C19 1.377(3) . ?
O3 C20 1.433(3) . ?
O4 C22 1.432(3) . ?
O4 H4 0.8400 . ?
C1 C16 1.393(3) . ?
C1 C2 1.411(3) . ?
C2 C13 1.389(3) . ?
C2 C3 1.547(3) . ?
C3 C7 1.558(3) . ?
C3 C4 1.608(3) . ?
C4 C12 1.532(3) . ?
C4 C11 1.536(3) . ?
C4 C5 1.558(3) . ?
C5 C9 1.529(3) . ?
C5 C6 1.538(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.543(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.525(3) . ?
C7 C8 1.556(3) . ?
C8 C9 1.547(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.398(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 C17 1.487(3) . ?
C16 H16 0.9500 . ?
C17 C33 1.392(3) . ?
C17 C18 1.395(3) . ?
C18 C19 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C21 1.414(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C32 1.393(3) . ?
C21 C22 1.547(3) . ?
C22 C26 1.564(3) . ?
C22 C23 1.608(3) . ?
C23 C30 1.531(3) . ?
C23 C31 1.535(3) . ?
C23 C24 1.560(3) . ?
C24 C25 1.532(4) . ?
C24 C28 1.536(3) . ?
C24 H24 1.0000 . ?
C25 C26 1.544(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C29 1.523(3) . ?
C26 C27 1.560(3) . ?
C27 C28 1.545(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
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 . ?
C32 C33 1.394(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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 C34 117.86(17) . . ?
C3 O2 H2 109.5 . . ?
C19 O3 C20 118.49(16) . . ?
C22 O4 H4 109.5 . . ?
O1 C1 C16 121.04(19) . . ?
O1 C1 C2 116.77(17) . . ?
C16 C1 C2 122.18(19) . . ?
C13 C2 C1 115.44(18) . . ?
C13 C2 C3 125.19(19) . . ?
C1 C2 C3 119.33(18) . . ?
O2 C3 C2 107.72(16) . . ?
O2 C3 C7 105.90(16) . . ?
C2 C3 C7 115.97(17) . . ?
O2 C3 C4 114.02(17) . . ?
C2 C3 C4 111.33(16) . . ?
C7 C3 C4 101.92(17) . . ?
C12 C4 C11 107.85(19) . . ?
C12 C4 C5 107.14(19) . . ?
C11 C4 C5 113.09(17) . . ?
C12 C4 C3 114.14(17) . . ?
C11 C4 C3 112.13(19) . . ?
C5 C4 C3 102.43(17) . . ?
C9 C5 C6 101.40(18) . . ?
C9 C5 C4 110.90(19) . . ?
C6 C5 C4 102.47(17) . . ?
C9 C5 H5 113.6 . . ?
C6 C5 H5 113.6 . . ?
C4 C5 H5 113.6 . . ?
C5 C6 C7 94.80(18) . . ?
C5 C6 H6A 112.8 . . ?
C7 C6 H6A 112.8 . . ?
C5 C6 H6B 112.8 . . ?
C7 C6 H6B 112.8 . . ?
H6A C6 H6B 110.2 . . ?
C10 C7 C6 121.0(2) . . ?
C10 C7 C8 108.02(18) . . ?
C6 C7 C8 100.01(17) . . ?
C10 C7 C3 116.83(19) . . ?
C6 C7 C3 100.98(17) . . ?
C8 C7 C3 108.34(18) . . ?
C9 C8 C7 105.77(18) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C5 C9 C8 101.02(17) . . ?
C5 C9 H9A 111.6 . . ?
C8 C9 H9A 111.6 . . ?
C5 C9 H9B 111.6 . . ?
C8 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 C14 123.0(2) . . ?
C2 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 118.05(19) . . ?
C14 C15 C17 121.55(19) . . ?
C16 C15 C17 120.40(19) . . ?
C1 C16 C15 120.7(2) . . ?
C1 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C33 C17 C18 118.00(19) . . ?
C33 C17 C15 121.33(19) . . ?
C18 C17 C15 120.66(19) . . ?
C19 C18 C17 120.94(19) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O3 C19 C18 121.86(19) . . ?
O3 C19 C21 116.02(17) . . ?
C18 C19 C21 122.12(19) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C32 C21 C19 115.20(18) . . ?
C32 C21 C22 124.49(19) . . ?
C19 C21 C22 120.30(18) . . ?
O4 C22 C21 108.14(16) . . ?
O4 C22 C26 105.76(17) . . ?
C21 C22 C26 115.39(18) . . ?
O4 C22 C23 113.06(18) . . ?
C21 C22 C23 111.89(17) . . ?
C26 C22 C23 102.51(16) . . ?
C30 C23 C31 107.3(2) . . ?
C30 C23 C24 113.45(19) . . ?
C31 C23 C24 108.35(19) . . ?
C30 C23 C22 112.34(19) . . ?
C31 C23 C22 113.40(17) . . ?
C24 C23 C22 101.99(18) . . ?
C25 C24 C28 101.2(2) . . ?
C25 C24 C23 102.76(18) . . ?
C28 C24 C23 110.9(2) . . ?
C25 C24 H24 113.6 . . ?
C28 C24 H24 113.6 . . ?
C23 C24 H24 113.6 . . ?
C24 C25 C26 95.22(18) . . ?
C24 C25 H25A 112.7 . . ?
C26 C25 H25A 112.7 . . ?
C24 C25 H25B 112.7 . . ?
C26 C25 H25B 112.7 . . ?
H25A C25 H25B 110.2 . . ?
C29 C26 C25 120.3(2) . . ?
C29 C26 C27 109.16(18) . . ?
C25 C26 C27 99.75(18) . . ?
C29 C26 C22 117.19(18) . . ?
C25 C26 C22 101.42(17) . . ?
C27 C26 C22 107.08(18) . . ?
C28 C27 C26 105.57(19) . . ?
C28 C27 H27A 110.6 . . ?
C26 C27 H27A 110.6 . . ?
C28 C27 H27B 110.6 . . ?
C26 C27 H27B 110.6 . . ?
H27A C27 H27B 108.8 . . ?
C24 C28 C27 101.41(19) . . ?
C24 C28 H28A 111.5 . . ?
C27 C28 H28A 111.5 . . ?
C24 C28 H28B 111.5 . . ?
C27 C28 H28B 111.5 . . ?
H28A C28 H28B 109.3 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 C31 H31A 109.5 . . ?
C23 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C23 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C32 C33 123.32(19) . . ?
C21 C32 H32 118.3 . . ?
C33 C32 H32 118.3 . . ?
C17 C33 C32 120.24(19) . . ?
C17 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
O1 C34 H34A 109.5 . . ?
O1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C34 O1 C1 C16 22.5(3) . . . . ?
C34 O1 C1 C2 -157.03(19) . . . . ?
O1 C1 C2 C13 175.90(18) . . . . ?
C16 C1 C2 C13 -3.6(3) . . . . ?
O1 C1 C2 C3 -2.0(3) . . . . ?
C16 C1 C2 C3 178.51(19) . . . . ?
C13 C2 C3 O2 130.6(2) . . . . ?
C1 C2 C3 O2 -51.8(2) . . . . ?
C13 C2 C3 C7 12.2(3) . . . . ?
C1 C2 C3 C7 -170.17(18) . . . . ?
C13 C2 C3 C4 -103.7(2) . . . . ?
C1 C2 C3 C4 73.9(2) . . . . ?
O2 C3 C4 C12 126.7(2) . . . . ?
C2 C3 C4 C12 4.6(3) . . . . ?
C7 C3 C4 C12 -119.7(2) . . . . ?
O2 C3 C4 C11 3.7(2) . . . . ?
C2 C3 C4 C11 -118.44(19) . . . . ?
C7 C3 C4 C11 117.30(19) . . . . ?
O2 C3 C4 C5 -117.85(19) . . . . ?
C2 C3 C4 C5 120.02(19) . . . . ?
C7 C3 C4 C5 -4.2(2) . . . . ?
C12 C4 C5 C9 -164.07(19) . . . . ?
C11 C4 C5 C9 -45.4(3) . . . . ?
C3 C4 C5 C9 75.5(2) . . . . ?
C12 C4 C5 C6 88.4(2) . . . . ?
C11 C4 C5 C6 -152.90(19) . . . . ?
C3 C4 C5 C6 -32.0(2) . . . . ?
C9 C5 C6 C7 -59.10(19) . . . . ?
C4 C5 C6 C7 55.57(19) . . . . ?
C5 C6 C7 C10 171.06(19) . . . . ?
C5 C6 C7 C8 52.88(18) . . . . ?
C5 C6 C7 C3 -58.20(18) . . . . ?
O2 C3 C7 C10 -68.3(2) . . . . ?
C2 C3 C7 C10 51.1(3) . . . . ?
C4 C3 C7 C10 172.15(19) . . . . ?
O2 C3 C7 C6 158.40(16) . . . . ?
C2 C3 C7 C6 -82.2(2) . . . . ?
C4 C3 C7 C6 38.88(19) . . . . ?
O2 C3 C7 C8 53.9(2) . . . . ?
C2 C3 C7 C8 173.27(17) . . . . ?
C4 C3 C7 C8 -65.6(2) . . . . ?
C10 C7 C8 C9 -157.1(2) . . . . ?
C6 C7 C8 C9 -29.7(2) . . . . ?
C3 C7 C8 C9 75.5(2) . . . . ?
C6 C5 C9 C8 40.7(2) . . . . ?
C4 C5 C9 C8 -67.6(2) . . . . ?
C7 C8 C9 C5 -6.4(2) . . . . ?
C1 C2 C13 C14 3.2(3) . . . . ?
C3 C2 C13 C14 -179.1(2) . . . . ?
C2 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -2.6(3) . . . . ?
C13 C14 C15 C17 178.15(19) . . . . ?
O1 C1 C16 C15 -178.50(19) . . . . ?
C2 C1 C16 C15 1.0(3) . . . . ?
C14 C15 C16 C1 2.2(3) . . . . ?
C17 C15 C16 C1 -178.56(19) . . . . ?
C14 C15 C17 C33 -39.6(3) . . . . ?
C16 C15 C17 C33 141.2(2) . . . . ?
C14 C15 C17 C18 141.0(2) . . . . ?
C16 C15 C17 C18 -38.2(3) . . . . ?
C33 C17 C18 C19 1.7(3) . . . . ?
C15 C17 C18 C19 -179.0(2) . . . . ?
C20 O3 C19 C18 0.3(3) . . . . ?
C20 O3 C19 C21 179.8(2) . . . . ?
C17 C18 C19 O3 -178.6(2) . . . . ?
C17 C18 C19 C21 1.8(3) . . . . ?
O3 C19 C21 C32 175.83(19) . . . . ?
C18 C19 C21 C32 -4.6(3) . . . . ?
O3 C19 C21 C22 -2.8(3) . . . . ?
C18 C19 C21 C22 176.8(2) . . . . ?
C32 C21 C22 O4 136.5(2) . . . . ?
C19 C21 C22 O4 -45.1(3) . . . . ?
C32 C21 C22 C26 18.3(3) . . . . ?
C19 C21 C22 C26 -163.21(19) . . . . ?
C32 C21 C22 C23 -98.4(3) . . . . ?
C19 C21 C22 C23 80.1(2) . . . . ?
O4 C22 C23 C30 6.8(2) . . . . ?
C21 C22 C23 C30 -115.6(2) . . . . ?
C26 C22 C23 C30 120.2(2) . . . . ?
O4 C22 C23 C31 128.7(2) . . . . ?
C21 C22 C23 C31 6.3(3) . . . . ?
C26 C22 C23 C31 -117.9(2) . . . . ?
O4 C22 C23 C24 -115.00(19) . . . . ?
C21 C22 C23 C24 122.60(19) . . . . ?
C26 C22 C23 C24 -1.6(2) . . . . ?
C30 C23 C24 C25 -154.9(2) . . . . ?
C31 C23 C24 C25 86.0(2) . . . . ?
C22 C23 C24 C25 -33.8(2) . . . . ?
C30 C23 C24 C28 -47.5(3) . . . . ?
C31 C23 C24 C28 -166.6(2) . . . . ?
C22 C23 C24 C28 73.6(2) . . . . ?
C28 C24 C25 C26 -58.78(19) . . . . ?
C23 C24 C25 C26 55.9(2) . . . . ?
C24 C25 C26 C29 172.44(19) . . . . ?
C24 C25 C26 C27 53.37(19) . . . . ?
C24 C25 C26 C22 -56.43(19) . . . . ?
O4 C22 C26 C29 -72.2(2) . . . . ?
C21 C22 C26 C29 47.2(3) . . . . ?
C23 C22 C26 C29 169.09(19) . . . . ?
O4 C22 C26 C25 154.75(17) . . . . ?
C21 C22 C26 C25 -85.8(2) . . . . ?
C23 C22 C26 C25 36.1(2) . . . . ?
O4 C22 C26 C27 50.7(2) . . . . ?
C21 C22 C26 C27 170.18(18) . . . . ?
C23 C22 C26 C27 -68.0(2) . . . . ?
C29 C26 C27 C28 -157.2(2) . . . . ?
C25 C26 C27 C28 -30.3(2) . . . . ?
C22 C26 C27 C28 75.0(2) . . . . ?
C25 C24 C28 C27 39.9(2) . . . . ?
C23 C24 C28 C27 -68.5(2) . . . . ?
C26 C27 C28 C24 -5.5(2) . . . . ?
C19 C21 C32 C33 4.2(3) . . . . ?
C22 C21 C32 C33 -177.3(2) . . . . ?
C18 C17 C33 C32 -2.1(3) . . . . ?
C15 C17 C33 C32 178.5(2) . . . . ?
C21 C32 C33 C17 -0.9(3) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_eb144c
_database_code_depnum_ccdc_archive 'CCDC 1886563'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H52 N O2 P'
_chemical_formula_sum            'C38 H52 N O2 P'
_chemical_formula_weight         585.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.8372(4)
_cell_length_b                   15.9591(5)
_cell_length_c                   16.7437(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3163.07(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22938
_cell_measurement_theta_min      4.651
_cell_measurement_theta_max      72.263


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.026
_shelx_estimated_absorpt_T_min   0.748
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5789
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22938
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.651
_diffrn_reflns_theta_max         72.263
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6173
_reflns_number_gt                6002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0513P)²+1.0816P] 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 2531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.110(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6173
_refine_ls_number_parameters     579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.05267(5) 0.03064(4) 0.63747(4) 0.01351(15) Uani 1 1 d . . . . .
O1 O -0.01861(15) -0.01404(12) 0.69514(11) 0.0209(4) Uani 1 1 d . . . . .
O2 O 0.14283(14) 0.09097(11) 0.67626(11) 0.0181(4) Uani 1 1 d . . . . .
N1 N 0.12884(18) -0.03445(15) 0.58377(13) 0.0184(4) Uani 1 1 d . . . . .
C1 C 0.1347(2) 0.17501(16) 0.70848(15) 0.0142(5) Uani 1 1 d . . . . .
C2 C 0.03580(19) 0.22171(16) 0.66954(14) 0.0136(5) Uani 1 1 d . . . . .
C3 C -0.02819(19) 0.19088(16) 0.60458(15) 0.0143(5) Uani 1 1 d . . . . .
C4 C -0.01617(19) 0.10319(16) 0.56667(14) 0.0145(5) Uani 1 1 d . . . . .
C5 C -0.1260(2) 0.06080(16) 0.53469(15) 0.0152(5) Uani 1 1 d . . . . .
C6 C -0.2336(2) 0.06115(16) 0.56368(15) 0.0154(5) Uani 1 1 d . . . . .
C7 C -0.3287(2) 0.00402(16) 0.52692(16) 0.0185(5) Uani 1 1 d . . . . .
C8 C -0.4383(2) 0.03581(19) 0.56670(18) 0.0232(6) Uani 1 1 d . . . . .
C9 C -0.3901(2) 0.03830(17) 0.65050(18) 0.0225(6) Uani 1 1 d . . . . .
C10 C -0.28931(19) 0.09969(16) 0.63933(16) 0.0177(5) Uani 1 1 d . . . . .
C11 C -0.2210(2) 0.1054(2) 0.71692(17) 0.0257(6) Uani 1 1 d . . . . .
C12 C -0.3396(2) 0.18799(17) 0.62340(19) 0.0227(6) Uani 1 1 d . . . . .
C13 C -0.3473(3) -0.05246(19) 0.66060(19) 0.0301(7) Uani 1 1 d . . . . .
H13A H -0.4076 -0.0893 0.6818 0.036 Uiso 1 1 calc R U . . .
H13B H -0.2814 -0.0547 0.6970 0.036 Uiso 1 1 calc R U . . .
C14 C -0.3136(3) -0.07857(17) 0.57428(18) 0.0256(6) Uani 1 1 d . . . . .
C15 C -0.3449(2) -0.00312(18) 0.43629(18) 0.0237(6) Uani 1 1 d . . . . .
C16 C -0.1026(2) 0.00639(18) 0.46562(17) 0.0208(5) Uani 1 1 d . . . . .
C17 C -0.0163(2) 0.0165(2) 0.41452(16) 0.0252(6) Uani 1 1 d . . . . .
C18 C 0.0664(2) 0.08200(18) 0.42784(16) 0.0224(6) Uani 1 1 d . . . . .
C19 C 0.0687(2) 0.12059(16) 0.49858(15) 0.0170(5) Uani 1 1 d . . . . .
C20 C -0.0993(2) 0.24638(17) 0.56320(16) 0.0173(5) Uani 1 1 d . . . . .
C21 C -0.1155(2) 0.32794(17) 0.58831(16) 0.0192(5) Uani 1 1 d . . . . .
C22 C -0.0641(2) 0.35564(17) 0.65787(16) 0.0184(5) Uani 1 1 d . . . . .
C23 C 0.0104(2) 0.30239(16) 0.69733(15) 0.0166(5) Uani 1 1 d . . . . .
C24 C 0.1314(2) 0.17014(17) 0.80298(15) 0.0173(5) Uani 1 1 d . . . . .
C25 C 0.2069(2) 0.24457(17) 0.82793(16) 0.0201(5) Uani 1 1 d . . . . .
C26 C 0.3089(2) 0.21823(18) 0.77700(17) 0.0219(6) Uani 1 1 d . . . . .
C27 C 0.2574(2) 0.21555(17) 0.69157(16) 0.0176(5) Uani 1 1 d . . . . .
C28 C 0.2546(2) 0.30439(18) 0.65688(18) 0.0225(6) Uani 1 1 d . . . . .
C29 C 0.3281(2) 0.16365(19) 0.63311(18) 0.0236(6) Uani 1 1 d . . . . .
C30 C 0.3306(3) 0.1300(2) 0.81022(18) 0.0273(6) Uani 1 1 d . . . . .
C31 C 0.2101(3) 0.09741(18) 0.82874(17) 0.0239(6) Uani 1 1 d . . . . .
C32 C 0.0152(2) 0.1643(2) 0.84020(16) 0.0242(6) Uani 1 1 d . . . . .
C33 C 0.1813(2) -0.11021(16) 0.61868(15) 0.0163(5) Uani 1 1 d . . . . .
C34 C 0.2852(2) -0.08949(18) 0.66922(18) 0.0223(6) Uani 1 1 d . . . . .
C35 C 0.3425(3) -0.1694(2) 0.70023(19) 0.0274(6) Uani 1 1 d . . . . .
C36 C 0.3758(2) -0.22683(19) 0.6316(2) 0.0272(6) Uani 1 1 d . . . . .
C37 C 0.2729(3) -0.24894(19) 0.58155(19) 0.0274(6) Uani 1 1 d . . . . .
C38 C 0.2122(3) -0.1703(2) 0.55126(18) 0.0276(6) Uani 1 1 d . . . . .
H1 H 0.339(3) 0.106(2) 0.653(2) 0.026(8) Uiso 1 1 d . . . . .
H2 H 0.338(3) -0.062(2) 0.637(2) 0.018(7) Uiso 1 1 d . . . . .
H3 H -0.168(3) 0.364(2) 0.560(2) 0.027(9) Uiso 1 1 d . . . . .
H4 H -0.311(3) -0.053(2) 0.413(2) 0.018(8) Uiso 1 1 d . . . . .
H5 H 0.175(3) 0.303(2) 0.814(2) 0.023(8) Uiso 1 1 d . . . . .
H6 H 0.024(3) 0.1661(19) 0.900(2) 0.016(7) Uiso 1 1 d . . . . .
H7 H 0.218(3) 0.346(2) 0.690(2) 0.019(8) Uiso 1 1 d . . . . .
H8 H -0.187(3) 0.052(2) 0.729(2) 0.032(9) Uiso 1 1 d . . . . .
H9 H 0.404(3) 0.186(2) 0.627(2) 0.027(9) Uiso 1 1 d . . . . .
H10 H -0.497(3) -0.006(2) 0.561(2) 0.023(8) Uiso 1 1 d . . . . .
H11 H -0.135(3) 0.2234(19) 0.5152(19) 0.014(7) Uiso 1 1 d . . . . .
H12 H 0.051(3) 0.323(2) 0.745(2) 0.021(8) Uiso 1 1 d . . . . .
H13 H 0.195(3) 0.045(2) 0.8043(19) 0.017(8) Uiso 1 1 d . . . . .
H14 H -0.011(3) -0.023(2) 0.375(2) 0.030(9) Uiso 1 1 d . . . . .
H15 H 0.332(3) 0.323(2) 0.646(2) 0.025(8) Uiso 1 1 d . . . . .
H16 H -0.024(3) 0.113(2) 0.822(2) 0.029(9) Uiso 1 1 d . . . . .
H17 H 0.369(3) 0.091(2) 0.772(2) 0.020(8) Uiso 1 1 d . . . . .
H18 H 0.222(2) 0.2429(19) 0.8875(19) 0.014(7) Uiso 1 1 d . . . . .
H19 H 0.127(3) 0.1598(18) 0.5105(18) 0.009(7) Uiso 1 1 d . . . . .
H20 H 0.222(3) 0.307(2) 0.604(2) 0.029(9) Uiso 1 1 d . . . . .
H21 H -0.272(3) 0.121(2) 0.762(2) 0.031(9) Uiso 1 1 d . . . . .
H22 H 0.126(3) -0.1351(18) 0.6532(19) 0.012(7) Uiso 1 1 d . . . . .
H23 H -0.369(3) -0.123(2) 0.551(2) 0.035(10) Uiso 1 1 d . . . . .
H24 H 0.215(2) -0.2821(19) 0.6172(19) 0.012(7) Uiso 1 1 d . . . . .
H25 H 0.199(2) 0.0861(19) 0.8863(19) 0.015(7) Uiso 1 1 d . . . . .
H26 H -0.364(3) 0.190(2) 0.566(3) 0.036(10) Uiso 1 1 d . . . . .
H27 H -0.284(3) 0.228(2) 0.635(2) 0.035(10) Uiso 1 1 d . . . . .
H28 H 0.418(3) -0.156(2) 0.730(3) 0.042(11) Uiso 1 1 d . . . . .
H29 H -0.082(3) 0.409(2) 0.679(2) 0.021(8) Uiso 1 1 d . . . . .
H30 H 0.377(3) 0.257(2) 0.777(2) 0.031(9) Uiso 1 1 d . . . . .
H31 H -0.461(3) 0.089(2) 0.548(2) 0.023(8) Uiso 1 1 d . . . . .
H32 H 0.258(3) -0.052(3) 0.717(3) 0.042(11) Uiso 1 1 d . . . . .
H33 H -0.158(3) 0.146(2) 0.713(2) 0.036(10) Uiso 1 1 d . . . . .
H35 H -0.441(3) 0.056(2) 0.696(2) 0.030(9) Uiso 1 1 d . . . . .
H36 H 0.290(3) -0.283(2) 0.537(2) 0.028(9) Uiso 1 1 d . . . . .
H37 H 0.286(3) -0.201(2) 0.736(2) 0.036(10) Uiso 1 1 d . . . . .
H38 H -0.406(3) 0.198(2) 0.662(2) 0.024(8) Uiso 1 1 d . . . . .
H39 H 0.120(3) 0.095(2) 0.388(2) 0.024(8) Uiso 1 1 d . . . . .
H41 H 0.290(4) 0.165(3) 0.576(3) 0.047(12) Uiso 1 1 d . . . . .
H42 H 0.409(3) -0.280(2) 0.652(2) 0.033(9) Uiso 1 1 d . . . . .
H43 H 0.173(3) -0.009(2) 0.544(2) 0.038(10) Uiso 1 1 d . . . . .
H44 H -0.031(3) 0.213(2) 0.823(2) 0.028(9) Uiso 1 1 d . . . . .
H1A H -0.148(3) -0.037(2) 0.4584(19) 0.018(8) Uiso 1 1 d . . . . .
H2A H -0.234(3) -0.098(2) 0.570(2) 0.020(8) Uiso 1 1 d . . . . .
H3A H -0.428(3) -0.005(3) 0.425(3) 0.044(11) Uiso 1 1 d . . . . .
H4A H 0.376(3) 0.134(2) 0.861(2) 0.027(9) Uiso 1 1 d . . . . .
H7A H 0.265(3) -0.140(2) 0.515(2) 0.031(9) Uiso 1 1 d . . . . .
H9A H 0.432(4) -0.201(3) 0.595(3) 0.056(13) Uiso 1 1 d . . . . .
H10A H -0.308(3) 0.046(3) 0.407(2) 0.039(11) Uiso 1 1 d . . . . .
H1B H 0.141(4) -0.180(3) 0.524(3) 0.047(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4673(19) . ?
P1 O2 1.5773(18) . ?
P1 N1 1.643(2) . ?
P1 C4 1.846(2) . ?
O2 C1 1.449(3) . ?
N1 C33 1.480(3) . ?
N1 H43 0.93(4) . ?
C1 C2 1.534(3) . ?
C1 C24 1.585(3) . ?
C1 C27 1.615(3) . ?
C2 C23 1.402(4) . ?
C2 C3 1.414(3) . ?
C3 C20 1.405(3) . ?
C3 C4 1.543(3) . ?
C4 C19 1.544(3) . ?
C4 C5 1.561(3) . ?
C5 C6 1.363(4) . ?
C5 C16 1.473(4) . ?
C6 C10 1.555(4) . ?
C6 C7 1.574(3) . ?
C7 C15 1.534(4) . ?
C7 C8 1.544(4) . ?
C7 C14 1.549(4) . ?
C8 C9 1.515(4) . ?
C8 H10 0.97(3) . ?
C8 H31 0.95(4) . ?
C9 C13 1.544(4) . ?
C9 C10 1.555(3) . ?
C9 H35 1.01(4) . ?
C10 C11 1.533(4) . ?
C10 C12 1.553(4) . ?
C11 H8 0.96(4) . ?
C11 H21 1.00(4) . ?
C11 H33 0.99(4) . ?
C12 H26 1.01(4) . ?
C12 H27 0.93(4) . ?
C12 H38 1.03(4) . ?
C13 C14 1.556(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H23 1.04(4) . ?
C14 H2A 0.99(3) . ?
C15 H4 0.97(3) . ?
C15 H3A 1.01(4) . ?
C15 H10A 1.02(4) . ?
C16 C17 1.342(4) . ?
C16 H1A 0.88(3) . ?
C17 C18 1.450(4) . ?
C17 H14 0.92(4) . ?
C18 C19 1.335(4) . ?
C18 H39 0.94(4) . ?
C19 H19 0.95(3) . ?
C20 C21 1.381(4) . ?
C20 H11 0.98(3) . ?
C21 C22 1.387(4) . ?
C21 H3 0.98(4) . ?
C22 C23 1.391(4) . ?
C22 H29 0.95(3) . ?
C23 H12 0.98(4) . ?
C24 C32 1.513(4) . ?
C24 C25 1.544(4) . ?
C24 C31 1.549(4) . ?
C25 C26 1.536(4) . ?
C25 H5 1.03(3) . ?
C25 H18 1.01(3) . ?
C26 C30 1.536(4) . ?
C26 C27 1.555(4) . ?
C26 H30 1.01(4) . ?
C27 C29 1.531(4) . ?
C27 C28 1.533(4) . ?
C28 H7 0.97(3) . ?
C28 H15 0.98(4) . ?
C28 H20 0.96(4) . ?
C29 H1 0.98(4) . ?
C29 H9 0.97(4) . ?
C29 H41 1.06(5) . ?
C30 C31 1.550(4) . ?
C30 H17 1.01(3) . ?
C30 H4A 1.00(4) . ?
C31 H13 0.95(3) . ?
C31 H25 0.99(3) . ?
C32 H6 1.01(3) . ?
C32 H16 0.99(4) . ?
C32 H44 1.00(4) . ?
C33 C38 1.525(4) . ?
C33 C34 1.529(3) . ?
C33 H22 0.96(3) . ?
C34 C35 1.536(4) . ?
C34 H2 0.94(3) . ?
C34 H32 1.05(4) . ?
C35 C36 1.522(4) . ?
C35 H28 1.05(4) . ?
C35 H37 1.04(4) . ?
C36 C37 1.519(4) . ?
C36 H42 0.99(4) . ?
C36 H9A 1.00(5) . ?
C37 C38 1.533(4) . ?
C37 H24 1.05(3) . ?
C37 H36 0.94(4) . ?
C38 H7A 1.00(4) . ?
C38 H1B 0.97(5) . ?

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 P1 O2 114.50(11) . . ?
O1 P1 N1 111.62(12) . . ?
O2 P1 N1 103.88(11) . . ?
O1 P1 C4 118.26(11) . . ?
O2 P1 C4 100.38(11) . . ?
N1 P1 C4 106.70(11) . . ?
C1 O2 P1 132.35(15) . . ?
C33 N1 P1 122.06(17) . . ?
C33 N1 H43 114(2) . . ?
P1 N1 H43 115(2) . . ?
O2 C1 C2 109.99(19) . . ?
O2 C1 C24 109.2(2) . . ?
C2 C1 C24 115.4(2) . . ?
O2 C1 C27 104.24(19) . . ?
C2 C1 C27 114.7(2) . . ?
C24 C1 C27 102.54(19) . . ?
C23 C2 C3 117.4(2) . . ?
C23 C2 C1 118.0(2) . . ?
C3 C2 C1 124.6(2) . . ?
C20 C3 C2 118.8(2) . . ?
C20 C3 C4 115.1(2) . . ?
C2 C3 C4 125.6(2) . . ?
C3 C4 C19 101.6(2) . . ?
C3 C4 C5 117.22(19) . . ?
C19 C4 C5 111.5(2) . . ?
C3 C4 P1 110.20(16) . . ?
C19 C4 P1 107.44(16) . . ?
C5 C4 P1 108.43(17) . . ?
C6 C5 C16 117.3(2) . . ?
C6 C5 C4 130.9(2) . . ?
C16 C5 C4 111.6(2) . . ?
C5 C6 C10 133.5(2) . . ?
C5 C6 C7 121.8(2) . . ?
C10 C6 C7 104.2(2) . . ?
C15 C7 C8 110.2(2) . . ?
C15 C7 C14 117.2(2) . . ?
C8 C7 C14 99.0(2) . . ?
C15 C7 C6 121.3(2) . . ?
C8 C7 C6 104.0(2) . . ?
C14 C7 C6 102.1(2) . . ?
C9 C8 C7 95.2(2) . . ?
C9 C8 H10 112(2) . . ?
C7 C8 H10 109(2) . . ?
C9 C8 H31 113(2) . . ?
C7 C8 H31 113(2) . . ?
H10 C8 H31 113(3) . . ?
C8 C9 C13 101.6(2) . . ?
C8 C9 C10 101.2(2) . . ?
C13 C9 C10 110.7(2) . . ?
C8 C9 H35 119(2) . . ?
C13 C9 H35 112(2) . . ?
C10 C9 H35 111(2) . . ?
C11 C10 C12 107.1(2) . . ?
C11 C10 C6 119.4(2) . . ?
C12 C10 C6 112.4(2) . . ?
C11 C10 C9 109.9(2) . . ?
C12 C10 C9 107.4(2) . . ?
C6 C10 C9 100.0(2) . . ?
C10 C11 H8 111(2) . . ?
C10 C11 H21 110(2) . . ?
H8 C11 H21 108(3) . . ?
C10 C11 H33 112(2) . . ?
H8 C11 H33 106(3) . . ?
H21 C11 H33 110(3) . . ?
C10 C12 H26 108(2) . . ?
C10 C12 H27 108(2) . . ?
H26 C12 H27 112(3) . . ?
C10 C12 H38 109.2(19) . . ?
H26 C12 H38 112(3) . . ?
H27 C12 H38 107(3) . . ?
C9 C13 C14 103.5(2) . . ?
C9 C13 H13A 111.1 . . ?
C14 C13 H13A 111.1 . . ?
C9 C13 H13B 111.1 . . ?
C14 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
C7 C14 C13 102.6(2) . . ?
C7 C14 H23 108(2) . . ?
C13 C14 H23 112(2) . . ?
C7 C14 H2A 109.7(19) . . ?
C13 C14 H2A 113(2) . . ?
H23 C14 H2A 112(3) . . ?
C7 C15 H4 113.7(19) . . ?
C7 C15 H3A 108(2) . . ?
H4 C15 H3A 108(3) . . ?
C7 C15 H10A 111(2) . . ?
H4 C15 H10A 105(3) . . ?
H3A C15 H10A 111(3) . . ?
C17 C16 C5 125.0(3) . . ?
C17 C16 H1A 118(2) . . ?
C5 C16 H1A 117(2) . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H14 115(2) . . ?
C18 C17 H14 124(2) . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H39 121(2) . . ?
C17 C18 H39 120(2) . . ?
C18 C19 C4 124.0(2) . . ?
C18 C19 H19 120.2(18) . . ?
C4 C19 H19 115.8(18) . . ?
C21 C20 C3 121.8(2) . . ?
C21 C20 H11 122.8(18) . . ?
C3 C20 H11 115.4(18) . . ?
C20 C21 C22 119.7(2) . . ?
C20 C21 H3 120(2) . . ?
C22 C21 H3 120(2) . . ?
C21 C22 C23 118.8(2) . . ?
C21 C22 H29 120(2) . . ?
C23 C22 H29 121(2) . . ?
C22 C23 C2 122.6(2) . . ?
C22 C23 H12 118.8(19) . . ?
C2 C23 H12 118.4(19) . . ?
C32 C24 C25 117.5(2) . . ?
C32 C24 C31 112.7(2) . . ?
C25 C24 C31 98.8(2) . . ?
C32 C24 C1 115.9(2) . . ?
C25 C24 C1 102.6(2) . . ?
C31 C24 C1 107.4(2) . . ?
C26 C25 C24 95.4(2) . . ?
C26 C25 H5 114.4(19) . . ?
C24 C25 H5 114.6(19) . . ?
C26 C25 H18 113.6(17) . . ?
C24 C25 H18 110.4(17) . . ?
H5 C25 H18 108(3) . . ?
C25 C26 C30 100.5(2) . . ?
C25 C26 C27 102.2(2) . . ?
C30 C26 C27 111.9(2) . . ?
C25 C26 H30 117(2) . . ?
C30 C26 H30 115(2) . . ?
C27 C26 H30 110(2) . . ?
C29 C27 C28 105.7(2) . . ?
C29 C27 C26 112.9(2) . . ?
C28 C27 C26 109.4(2) . . ?
C29 C27 C1 112.7(2) . . ?
C28 C27 C1 114.7(2) . . ?
C26 C27 C1 101.6(2) . . ?
C27 C28 H7 115.2(19) . . ?
C27 C28 H15 109(2) . . ?
H7 C28 H15 109(3) . . ?
C27 C28 H20 114(2) . . ?
H7 C28 H20 108(3) . . ?
H15 C28 H20 101(3) . . ?
C27 C29 H1 111(2) . . ?
C27 C29 H9 112(2) . . ?
H1 C29 H9 105(3) . . ?
C27 C29 H41 109(2) . . ?
H1 C29 H41 112(3) . . ?
H9 C29 H41 107(3) . . ?
C26 C30 C31 103.0(2) . . ?
C26 C30 H17 114.3(19) . . ?
C31 C30 H17 109.6(18) . . ?
C26 C30 H4A 110(2) . . ?
C31 C30 H4A 110(2) . . ?
H17 C30 H4A 110(3) . . ?
C24 C31 C30 104.3(2) . . ?
C24 C31 H13 115.4(19) . . ?
C30 C31 H13 112.3(19) . . ?
C24 C31 H25 109.1(18) . . ?
C30 C31 H25 112.3(17) . . ?
H13 C31 H25 104(3) . . ?
C24 C32 H6 108.1(18) . . ?
C24 C32 H16 111(2) . . ?
H6 C32 H16 112(3) . . ?
C24 C32 H44 109(2) . . ?
H6 C32 H44 109(3) . . ?
H16 C32 H44 108(3) . . ?
N1 C33 C38 108.8(2) . . ?
N1 C33 C34 112.3(2) . . ?
C38 C33 C34 110.7(2) . . ?
N1 C33 H22 106.8(18) . . ?
C38 C33 H22 110.4(18) . . ?
C34 C33 H22 107.8(18) . . ?
C33 C34 C35 111.3(2) . . ?
C33 C34 H2 108(2) . . ?
C35 C34 H2 107.5(19) . . ?
C33 C34 H32 108(2) . . ?
C35 C34 H32 111(2) . . ?
H2 C34 H32 112(3) . . ?
C36 C35 C34 111.0(2) . . ?
C36 C35 H28 105(2) . . ?
C34 C35 H28 112(2) . . ?
C36 C35 H37 108(2) . . ?
C34 C35 H37 109(2) . . ?
H28 C35 H37 112(3) . . ?
C37 C36 C35 110.4(2) . . ?
C37 C36 H42 108(2) . . ?
C35 C36 H42 111(2) . . ?
C37 C36 H9A 107(3) . . ?
C35 C36 H9A 113(3) . . ?
H42 C36 H9A 107(3) . . ?
C36 C37 C38 111.6(3) . . ?
C36 C37 H24 109.0(16) . . ?
C38 C37 H24 107.2(16) . . ?
C36 C37 H36 113(2) . . ?
C38 C37 H36 108(2) . . ?
H24 C37 H36 107(3) . . ?
C33 C38 C37 112.5(2) . . ?
C33 C38 H7A 107(2) . . ?
C37 C38 H7A 108(2) . . ?
C33 C38 H1B 104(3) . . ?
C37 C38 H1B 116(3) . . ?
H7A C38 H1B 110(3) . . ?

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 P1 O2 C1 -80.4(2) . . . . ?
N1 P1 O2 C1 157.7(2) . . . . ?
C4 P1 O2 C1 47.4(2) . . . . ?
O1 P1 N1 C33 -39.1(2) . . . . ?
O2 P1 N1 C33 84.8(2) . . . . ?
C4 P1 N1 C33 -169.7(2) . . . . ?
P1 O2 C1 C2 -25.7(3) . . . . ?
P1 O2 C1 C24 101.8(2) . . . . ?
P1 O2 C1 C27 -149.17(18) . . . . ?
O2 C1 C2 C23 175.8(2) . . . . ?
C24 C1 C2 C23 51.8(3) . . . . ?
C27 C1 C2 C23 -67.1(3) . . . . ?
O2 C1 C2 C3 -7.6(3) . . . . ?
C24 C1 C2 C3 -131.6(2) . . . . ?
C27 C1 C2 C3 109.5(3) . . . . ?
C23 C2 C3 C20 10.5(3) . . . . ?
C1 C2 C3 C20 -166.1(2) . . . . ?
C23 C2 C3 C4 -178.1(2) . . . . ?
C1 C2 C3 C4 5.3(4) . . . . ?
C20 C3 C4 C19 78.7(2) . . . . ?
C2 C3 C4 C19 -92.9(3) . . . . ?
C20 C3 C4 C5 -43.0(3) . . . . ?
C2 C3 C4 C5 145.4(2) . . . . ?
C20 C3 C4 P1 -167.59(18) . . . . ?
C2 C3 C4 P1 20.8(3) . . . . ?
O1 P1 C4 C3 86.77(19) . . . . ?
O2 P1 C4 C3 -38.48(18) . . . . ?
N1 P1 C4 C3 -146.51(16) . . . . ?
O1 P1 C4 C19 -163.38(16) . . . . ?
O2 P1 C4 C19 71.37(18) . . . . ?
N1 P1 C4 C19 -36.7(2) . . . . ?
O1 P1 C4 C5 -42.7(2) . . . . ?
O2 P1 C4 C5 -167.99(16) . . . . ?
N1 P1 C4 C5 83.97(18) . . . . ?
C3 C4 C5 C6 -37.1(4) . . . . ?
C19 C4 C5 C6 -153.6(3) . . . . ?
P1 C4 C5 C6 88.4(3) . . . . ?
C3 C4 C5 C16 148.7(2) . . . . ?
C19 C4 C5 C16 32.3(3) . . . . ?
P1 C4 C5 C16 -85.8(2) . . . . ?
C16 C5 C6 C10 171.4(3) . . . . ?
C4 C5 C6 C10 -2.5(5) . . . . ?
C16 C5 C6 C7 1.8(4) . . . . ?
C4 C5 C6 C7 -172.1(2) . . . . ?
C5 C6 C7 C15 -45.5(4) . . . . ?
C10 C6 C7 C15 142.3(2) . . . . ?
C5 C6 C7 C8 -170.2(2) . . . . ?
C10 C6 C7 C8 17.6(3) . . . . ?
C5 C6 C7 C14 87.3(3) . . . . ?
C10 C6 C7 C14 -85.0(2) . . . . ?
C15 C7 C8 C9 -177.7(2) . . . . ?
C14 C7 C8 C9 58.8(2) . . . . ?
C6 C7 C8 C9 -46.2(2) . . . . ?
C7 C8 C9 C13 -55.3(2) . . . . ?
C7 C8 C9 C10 58.7(2) . . . . ?
C5 C6 C10 C11 -33.4(4) . . . . ?
C7 C6 C10 C11 137.5(2) . . . . ?
C5 C6 C10 C12 93.3(3) . . . . ?
C7 C6 C10 C12 -95.8(2) . . . . ?
C5 C6 C10 C9 -153.1(3) . . . . ?
C7 C6 C10 C9 17.8(2) . . . . ?
C8 C9 C10 C11 -175.0(2) . . . . ?
C13 C9 C10 C11 -67.9(3) . . . . ?
C8 C9 C10 C12 68.9(3) . . . . ?
C13 C9 C10 C12 175.9(2) . . . . ?
C8 C9 C10 C6 -48.6(2) . . . . ?
C13 C9 C10 C6 58.4(3) . . . . ?
C8 C9 C13 C14 30.9(3) . . . . ?
C10 C9 C13 C14 -75.9(3) . . . . ?
C15 C7 C14 C13 -158.4(2) . . . . ?
C8 C7 C14 C13 -40.0(3) . . . . ?
C6 C7 C14 C13 66.5(3) . . . . ?
C9 C13 C14 C7 6.1(3) . . . . ?
C6 C5 C16 C17 157.9(3) . . . . ?
C4 C5 C16 C17 -27.0(4) . . . . ?
C5 C16 C17 C18 3.7(4) . . . . ?
C16 C17 C18 C19 13.1(4) . . . . ?
C17 C18 C19 C4 -3.4(4) . . . . ?
C3 C4 C19 C18 -145.5(2) . . . . ?
C5 C4 C19 C18 -19.8(3) . . . . ?
P1 C4 C19 C18 98.8(3) . . . . ?
C2 C3 C20 C21 -5.6(4) . . . . ?
C4 C3 C20 C21 -177.8(2) . . . . ?
C3 C20 C21 C22 -2.5(4) . . . . ?
C20 C21 C22 C23 5.2(4) . . . . ?
C21 C22 C23 C2 0.1(4) . . . . ?
C3 C2 C23 C22 -8.0(4) . . . . ?
C1 C2 C23 C22 168.8(2) . . . . ?
O2 C1 C24 C32 -90.9(3) . . . . ?
C2 C1 C24 C32 33.6(3) . . . . ?
C27 C1 C24 C32 159.0(2) . . . . ?
O2 C1 C24 C25 139.7(2) . . . . ?
C2 C1 C24 C25 -95.9(2) . . . . ?
C27 C1 C24 C25 29.6(2) . . . . ?
O2 C1 C24 C31 36.1(3) . . . . ?
C2 C1 C24 C31 160.6(2) . . . . ?
C27 C1 C24 C31 -74.0(2) . . . . ?
C32 C24 C25 C26 178.3(2) . . . . ?
C31 C24 C25 C26 56.9(2) . . . . ?
C1 C24 C25 C26 -53.3(2) . . . . ?
C24 C25 C26 C30 -57.4(2) . . . . ?
C24 C25 C26 C27 58.0(2) . . . . ?
C25 C26 C27 C29 -160.7(2) . . . . ?
C30 C26 C27 C29 -54.1(3) . . . . ?
C25 C26 C27 C28 81.9(2) . . . . ?
C30 C26 C27 C28 -171.4(2) . . . . ?
C25 C26 C27 C1 -39.7(2) . . . . ?
C30 C26 C27 C1 67.0(3) . . . . ?
O2 C1 C27 C29 13.2(3) . . . . ?
C2 C1 C27 C29 -107.1(2) . . . . ?
C24 C1 C27 C29 127.0(2) . . . . ?
O2 C1 C27 C28 134.2(2) . . . . ?
C2 C1 C27 C28 13.9(3) . . . . ?
C24 C1 C27 C28 -112.0(2) . . . . ?
O2 C1 C27 C26 -107.9(2) . . . . ?
C2 C1 C27 C26 131.7(2) . . . . ?
C24 C1 C27 C26 5.8(2) . . . . ?
C25 C26 C30 C31 35.1(3) . . . . ?
C27 C26 C30 C31 -72.6(3) . . . . ?
C32 C24 C31 C30 -160.9(2) . . . . ?
C25 C24 C31 C30 -36.0(3) . . . . ?
C1 C24 C31 C30 70.2(3) . . . . ?
C26 C30 C31 C24 0.8(3) . . . . ?
P1 N1 C33 C38 161.9(2) . . . . ?
P1 N1 C33 C34 -75.2(3) . . . . ?
N1 C33 C34 C35 -176.3(2) . . . . ?
C38 C33 C34 C35 -54.5(3) . . . . ?
C33 C34 C35 C36 57.3(3) . . . . ?
C34 C35 C36 C37 -57.3(3) . . . . ?
C35 C36 C37 C38 55.6(3) . . . . ?
N1 C33 C38 C37 177.0(2) . . . . ?
C34 C33 C38 C37 53.2(3) . . . . ?
C36 C37 C38 C33 -54.2(4) . . . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_eb177_1
_database_code_depnum_ccdc_archive 'CCDC 1886562'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H45 Cl F O2 P Pd'
_chemical_formula_sum            'C35 H45 Cl F O2 P Pd'
_chemical_formula_weight         689.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.359(2)
_cell_length_b                   11.810(2)
_cell_length_c                   25.612(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3133.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    47892
_cell_measurement_theta_min      3.451
_cell_measurement_theta_max      72.547

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.332
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5078
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47892
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.451
_diffrn_reflns_theta_max         72.547
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6102
_reflns_number_gt                6000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.967

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0381P)²+0.6232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2504 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.087(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6102
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0581
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.43655(2) 0.46936(2) 0.73962(2) 0.01466(8) Uani 1 1 d . . . . .
Cl1 Cl 0.64146(7) 0.38294(7) 0.74260(4) 0.02425(17) Uani 1 1 d . . . . .
P1 P 0.38430(7) 0.40967(6) 0.65861(3) 0.01128(15) Uani 1 1 d . . . . .
O2 O 0.2372(2) 0.37817(17) 0.65964(8) 0.0125(4) Uani 1 1 d . . . . .
F2 F 0.45337(19) 0.29520(15) 0.64495(7) 0.0176(4) Uani 1 1 d . . . . .
O1 O 0.4159(2) 0.46650(18) 0.60395(8) 0.0128(4) Uani 1 1 d . . . . .
C1 C 0.4242(4) 0.5253(4) 0.82112(14) 0.0347(9) Uani 1 1 d . . . . .
H1A H 0.4153 0.4480 0.8175 0.042 Uiso 0.4 1 d R U P A .
H1B H 0.4822 0.5555 0.8451 0.042 Uiso 0.4 1 d R U P . .
H1C H 0.4859 0.5696 0.8044 0.042 Uiso 0.6 1 d R U P . .
H1D H 0.4444 0.4888 0.8522 0.042 Uiso 0.6 1 d R U P . .
C2A C 0.3557(8) 0.5938(8) 0.7924(3) 0.0211(18) Uani 0.4 1 d . . P A 1
H2A H 0.3680 0.6710 0.7974 0.025 Uiso 0.4 1 d R U P A 1
C2B C 0.2999(7) 0.5140(7) 0.7989(3) 0.0362(16) Uani 0.6 1 d . . P A 2
H2B H 0.2395 0.4693 0.8162 0.043 Uiso 0.6 1 d R U P A 2
C3 C 0.2648(4) 0.5623(4) 0.75508(17) 0.0333(9) Uani 1 1 d . . . . .
H3A H 0.2495 0.4864 0.7485 0.040 Uiso 0.4 1 d R U P A .
H3B H 0.2209 0.6179 0.7365 0.040 Uiso 0.4 1 d R U P . .
H3C H 0.3238 0.6073 0.7372 0.040 Uiso 0.6 1 d R U P . .
H3D H 0.1819 0.5524 0.7419 0.040 Uiso 0.6 1 d R U P . .
C4 C 0.4255(3) 0.5884(2) 0.59359(11) 0.0121(6) Uani 1 1 d . . . . .
C5 C 0.4603(3) 0.6021(3) 0.53273(12) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.6010(3) 0.6468(3) 0.53381(14) 0.0205(7) Uani 1 1 d . . . . .
H11 H 0.6285 0.6839 0.5005 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6955(4) 0.5576(3) 0.55362(15) 0.0249(8) Uani 1 1 d . . . . .
H2 H 0.7860 0.5815 0.5480 0.030 Uiso 1 1 calc R U . . .
H3 H 0.6812 0.4838 0.5362 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6632(3) 0.5508(3) 0.61269(13) 0.0192(7) Uani 1 1 d . . . . .
H9 H 0.6345 0.4736 0.6223 0.023 Uiso 1 1 calc R U . . .
H10 H 0.7393 0.5711 0.6341 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5526(3) 0.6377(3) 0.62061(12) 0.0150(6) Uani 1 1 d . . . . .
C10 C 0.5955(3) 0.7276(3) 0.58050(14) 0.0198(7) Uani 1 1 d . . . . .
H5 H 0.5308 0.7885 0.5759 0.024 Uiso 1 1 calc R U . . .
H4 H 0.6808 0.7608 0.5889 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5530(4) 0.6767(3) 0.67771(13) 0.0185(6) Uani 1 1 d . . . . .
H8 H 0.6116 0.7413 0.6816 0.028 Uiso 1 1 calc R U . . .
H7 H 0.5821 0.6144 0.7001 0.028 Uiso 1 1 calc R U . . .
H6 H 0.4655 0.6993 0.6879 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3781(4) 0.6926(3) 0.50543(14) 0.0215(7) Uani 1 1 d . . . . .
H13 H 0.4112 0.7053 0.4701 0.032 Uiso 1 1 calc R U . . .
H14 H 0.3823 0.7634 0.5253 0.032 Uiso 1 1 calc R U . . .
H12 H 0.2883 0.6668 0.5035 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4474(4) 0.4924(3) 0.50115(13) 0.0239(7) Uani 1 1 d . . . . .
H15 H 0.3560 0.4722 0.4981 0.036 Uiso 1 1 calc R U . . .
H16 H 0.4939 0.4313 0.5189 0.036 Uiso 1 1 calc R U . . .
H17 H 0.4840 0.5036 0.4662 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2936(3) 0.6382(3) 0.60882(12) 0.0134(6) Uani 1 1 d . . . . .
C15 C 0.2898(3) 0.7462(3) 0.63142(13) 0.0168(6) Uani 1 1 d . . . . .
H18 H 0.3684 0.7868 0.6353 0.020 Uiso 1 1 calc R U . . .
C16 C 0.1762(4) 0.7965(3) 0.64831(15) 0.0223(7) Uani 1 1 d . . . . .
H19 H 0.1780 0.8693 0.6641 0.027 Uiso 1 1 calc R U . . .
C17 C 0.0607(4) 0.7400(3) 0.64209(15) 0.0245(7) Uani 1 1 d . . . . .
H42 H -0.0174 0.7721 0.6547 0.029 Uiso 1 1 calc R U . . .
C18 C 0.0602(4) 0.6359(3) 0.61724(14) 0.0216(7) Uani 1 1 d . . . . .
H41 H -0.0201 0.5991 0.6116 0.026 Uiso 1 1 calc R U . . .
C19 C 0.1736(3) 0.5827(3) 0.60010(12) 0.0140(6) Uani 1 1 d . . . . .
C20 C 0.1493(3) 0.4846(3) 0.56317(13) 0.0154(6) Uani 1 1 d . . . . .
C21 C 0.1470(3) 0.3662(3) 0.57228(12) 0.0145(6) Uani 1 1 d . . . . .
C22 C 0.1516(3) 0.3111(3) 0.62635(12) 0.0131(6) Uani 1 1 d . . . . .
C23 C 0.0126(3) 0.3127(3) 0.65460(14) 0.0193(7) Uani 1 1 d . . . . .
C24 C 0.0019(4) 0.3973(3) 0.69950(15) 0.0276(8) Uani 1 1 d . . . . .
H21 H 0.0071 0.4745 0.6857 0.041 Uiso 1 1 calc R U . . .
H22 H 0.0726 0.3846 0.7242 0.041 Uiso 1 1 calc R U . . .
H23 H -0.0810 0.3869 0.7174 0.041 Uiso 1 1 calc R U . . .
C25 C -0.0017(4) 0.1883(3) 0.67370(16) 0.0269(8) Uani 1 1 d . . . . .
H24 H -0.0926 0.1662 0.6819 0.032 Uiso 1 1 calc R U . . .
C26 C 0.0939(4) 0.1599(4) 0.71696(18) 0.0335(9) Uani 1 1 d . . . . .
H26 H 0.0728 0.0865 0.7336 0.040 Uiso 1 1 calc R U . . .
H25 H 0.0952 0.2197 0.7440 0.040 Uiso 1 1 calc R U . . .
C27 C 0.2241(4) 0.1539(3) 0.68762(14) 0.0231(7) Uani 1 1 d . . . . .
H27 H 0.2625 0.0774 0.6907 0.028 Uiso 1 1 calc R U . . .
H28 H 0.2858 0.2100 0.7018 0.028 Uiso 1 1 calc R U . . .
C28 C 0.1902(3) 0.1813(3) 0.62956(14) 0.0182(7) Uani 1 1 d . . . . .
C29 C 0.2903(4) 0.1353(3) 0.59137(15) 0.0247(8) Uani 1 1 d . . . . .
H31 H 0.2479 0.0855 0.5660 0.037 Uiso 1 1 calc R U . . .
H29 H 0.3560 0.0925 0.6106 0.037 Uiso 1 1 calc R U . . .
H30 H 0.3315 0.1985 0.5730 0.037 Uiso 1 1 calc R U . . .
C30 C 0.0562(4) 0.1239(3) 0.62766(16) 0.0259(7) Uani 1 1 d . . . . .
H32 H 0.0100 0.1390 0.5945 0.031 Uiso 1 1 calc R U . . .
H33 H 0.0610 0.0413 0.6340 0.031 Uiso 1 1 calc R U . . .
C31 C -0.0995(3) 0.3370(3) 0.61665(17) 0.0252(8) Uani 1 1 d . . . . .
H34 H -0.1818 0.3288 0.6351 0.038 Uiso 1 1 calc R U . . .
H35 H -0.0962 0.2833 0.5875 0.038 Uiso 1 1 calc R U . . .
H36 H -0.0917 0.4144 0.6032 0.038 Uiso 1 1 calc R U . . .
C32 C 0.1201(4) 0.2962(3) 0.52945(15) 0.0224(7) Uani 1 1 d . . . . .
H40 H 0.1214 0.2166 0.5346 0.027 Uiso 1 1 calc R U . . .
C33 C 0.0917(4) 0.3367(3) 0.47994(15) 0.0301(9) Uani 1 1 d . . . . .
H39 H 0.0793 0.2859 0.4516 0.036 Uiso 1 1 calc R U . . .
C34 C 0.0818(4) 0.4523(4) 0.47257(15) 0.0315(9) Uani 1 1 d . . . . .
H37 H 0.0564 0.4825 0.4398 0.038 Uiso 1 1 calc R U . . .
C35 C 0.1098(3) 0.5228(3) 0.51393(14) 0.0236(7) Uani 1 1 d . . . . .
H38 H 0.1017 0.6022 0.5088 0.028 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
Pd1 C3 2.127(4) . ?
Pd1 C2B 2.142(7) . ?
Pd1 C2A 2.165(8) . ?
Pd1 C1 2.193(4) . ?
Pd1 P1 2.2569(10) . ?
Pd1 Cl1 2.3565(9) . ?
Pd1 H1A 2.0230 . ?
Pd1 H1C 2.1021 . ?
Pd1 H3A 1.9611 . ?
Pd1 H3C 2.0057 . ?
P1 F2 1.5691(19) . ?
P1 O2 1.569(2) . ?
P1 O1 1.587(2) . ?
O2 C22 1.463(4) . ?
O1 C4 1.468(3) . ?
C1 C2A 1.304(11) . ?
C1 C2B 1.415(9) . ?
C1 H1A 0.9229 . ?
C1 H1B 0.9307 . ?
C1 H1C 0.9300 . ?
C1 H1D 0.9300 . ?
C2A C3 1.391(9) . ?
C2A H2A 0.9300 . ?
C2B C3 1.310(9) . ?
C2B H2B 0.9300 . ?
C3 H3A 0.9263 . ?
C3 H3B 0.9302 . ?
C3 H3C 0.9300 . ?
C3 H3D 0.9300 . ?
C4 C14 1.538(4) . ?
C4 C9 1.597(4) . ?
C4 C5 1.608(4) . ?
C5 C13 1.533(5) . ?
C5 C12 1.536(5) . ?
C5 C6 1.550(5) . ?
C6 C7 1.525(5) . ?
C6 C10 1.531(5) . ?
C6 H11 1.0000 . ?
C7 C8 1.552(5) . ?
C7 H2 0.9900 . ?
C7 H3 0.9900 . ?
C8 C9 1.551(4) . ?
C8 H9 0.9900 . ?
C8 H10 0.9900 . ?
C9 C11 1.533(4) . ?
C9 C10 1.543(4) . ?
C10 H5 0.9900 . ?
C10 H4 0.9900 . ?
C11 H8 0.9800 . ?
C11 H7 0.9800 . ?
C11 H6 0.9800 . ?
C12 H13 0.9800 . ?
C12 H14 0.9800 . ?
C12 H12 0.9800 . ?
C13 H15 0.9800 . ?
C13 H16 0.9800 . ?
C13 H17 0.9800 . ?
C14 C15 1.401(5) . ?
C14 C19 1.423(4) . ?
C15 C16 1.386(5) . ?
C15 H18 0.9500 . ?
C16 C17 1.379(6) . ?
C16 H19 0.9500 . ?
C17 C18 1.384(5) . ?
C17 H42 0.9500 . ?
C18 C19 1.403(5) . ?
C18 H41 0.9500 . ?
C19 C20 1.517(5) . ?
C20 C35 1.401(5) . ?
C20 C21 1.417(5) . ?
C21 C32 1.401(5) . ?
C21 C22 1.531(4) . ?
C22 C28 1.586(4) . ?
C22 C23 1.612(5) . ?
C23 C24 1.527(5) . ?
C23 C31 1.541(5) . ?
C23 C25 1.555(5) . ?
C24 H21 0.9800 . ?
C24 H22 0.9800 . ?
C24 H23 0.9800 . ?
C25 C26 1.523(6) . ?
C25 C30 1.526(6) . ?
C25 H24 1.0000 . ?
C26 C27 1.545(6) . ?
C26 H26 0.9900 . ?
C26 H25 0.9900 . ?
C27 C28 1.562(5) . ?
C27 H27 0.9900 . ?
C27 H28 0.9900 . ?
C28 C29 1.525(5) . ?
C28 C30 1.545(5) . ?
C29 H31 0.9800 . ?
C29 H29 0.9800 . ?
C29 H30 0.9800 . ?
C30 H32 0.9900 . ?
C30 H33 0.9900 . ?
C31 H34 0.9800 . ?
C31 H35 0.9800 . ?
C31 H36 0.9800 . ?
C32 C33 1.387(5) . ?
C32 H40 0.9500 . ?
C33 C34 1.383(6) . ?
C33 H39 0.9500 . ?
C34 C35 1.378(6) . ?
C34 H37 0.9500 . ?
C35 H38 0.9500 . ?

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
C3 Pd1 C2B 35.7(2) . . ?
C3 Pd1 C2A 37.8(3) . . ?
C3 Pd1 C1 67.58(17) . . ?
C2B Pd1 C1 38.1(2) . . ?
C2A Pd1 C1 34.8(3) . . ?
C3 Pd1 P1 97.57(11) . . ?
C2B Pd1 P1 124.7(2) . . ?
C2A Pd1 P1 133.9(2) . . ?
C1 Pd1 P1 162.74(12) . . ?
C3 Pd1 Cl1 166.07(11) . . ?
C2B Pd1 Cl1 132.8(2) . . ?
C2A Pd1 Cl1 128.5(2) . . ?
C1 Pd1 Cl1 98.75(12) . . ?
P1 Pd1 Cl1 96.35(3) . . ?
C3 Pd1 H1A 77.9 . . ?
C2B Pd1 H1A 42.2 . . ?
C2A Pd1 H1A 55.1 . . ?
C1 Pd1 H1A 24.9 . . ?
P1 Pd1 H1A 147.3 . . ?
Cl1 Pd1 H1A 90.7 . . ?
C3 Pd1 H1C 76.4 . . ?
C2B Pd1 H1C 57.5 . . ?
C2A Pd1 H1C 38.6 . . ?
C1 Pd1 H1C 24.9 . . ?
P1 Pd1 H1C 163.8 . . ?
Cl1 Pd1 H1C 90.0 . . ?
H1A Pd1 H1C 47.0 . . ?
C3 Pd1 H3A 25.8 . . ?
C2B Pd1 H3A 40.5 . . ?
C2A Pd1 H3A 58.4 . . ?
C1 Pd1 H3A 78.5 . . ?
P1 Pd1 H3A 84.4 . . ?
Cl1 Pd1 H3A 158.5 . . ?
H1A Pd1 H3A 77.9 . . ?
H1C Pd1 H3A 95.2 . . ?
C3 Pd1 H3C 25.8 . . ?
C2B Pd1 H3C 55.7 . . ?
C2A Pd1 H3C 40.7 . . ?
C1 Pd1 H3C 75.5 . . ?
P1 Pd1 H3C 94.9 . . ?
Cl1 Pd1 H3C 151.3 . . ?
H1A Pd1 H3C 93.9 . . ?
H1C Pd1 H3C 73.0 . . ?
H3A Pd1 H3C 49.1 . . ?
F2 P1 O2 104.03(11) . . ?
F2 P1 O1 94.20(11) . . ?
O2 P1 O1 108.40(12) . . ?
F2 P1 Pd1 111.39(8) . . ?
O2 P1 Pd1 106.96(9) . . ?
O1 P1 Pd1 129.00(9) . . ?
C22 O2 P1 135.0(2) . . ?
C4 O1 P1 126.04(19) . . ?
C2A C1 Pd1 71.4(4) . . ?
C2B C1 Pd1 69.0(3) . . ?
C2A C1 H1A 120.2 . . ?
C2B C1 H1A 77.0 . . ?
Pd1 C1 H1A 67.2 . . ?
C2A C1 H1B 119.2 . . ?
C2B C1 H1B 152.9 . . ?
Pd1 C1 H1B 134.9 . . ?
H1A C1 H1B 120.7 . . ?
C2A C1 H1C 76.4 . . ?
C2B C1 H1C 119.6 . . ?
Pd1 C1 H1C 72.1 . . ?
H1A C1 H1C 125.5 . . ?
H1B C1 H1C 69.2 . . ?
C2A C1 H1D 153.4 . . ?
C2B C1 H1D 120.4 . . ?
Pd1 C1 H1D 131.5 . . ?
H1A C1 H1D 69.5 . . ?
H1B C1 H1D 57.7 . . ?
H1C C1 H1D 120.0 . . ?
C1 C2A C3 126.2(7) . . ?
C1 C2A Pd1 73.8(4) . . ?
C3 C2A Pd1 69.6(4) . . ?
C1 C2A H1C 39.8 . . ?
C3 C2A H1C 137.9 . . ?
Pd1 C2A H1C 68.3 . . ?
C1 C2A H2A 117.1 . . ?
C3 C2A H2A 116.8 . . ?
Pd1 C2A H2A 134.3 . . ?
H1C C2A H2A 92.1 . . ?
C1 C2A H3C 137.5 . . ?
C3 C2A H3C 38.0 . . ?
Pd1 C2A H3C 63.8 . . ?
H1C C2A H3C 116.7 . . ?
H2A C2A H3C 93.3 . . ?
C3 C2B C1 123.8(6) . . ?
C3 C2B Pd1 71.5(3) . . ?
C1 C2B Pd1 72.9(3) . . ?
C3 C2B H1A 135.8 . . ?
C1 C2B H1A 36.7 . . ?
Pd1 C2B H1A 64.7 . . ?
C3 C2B H2B 117.9 . . ?
C1 C2B H2B 118.3 . . ?
Pd1 C2B H2B 129.9 . . ?
H1A C2B H2B 95.1 . . ?
C3 C2B H3A 39.2 . . ?
C1 C2B H3A 135.8 . . ?
Pd1 C2B H3A 63.0 . . ?
H1A C2B H3A 117.2 . . ?
H2B C2B H3A 93.1 . . ?
C2B C3 Pd1 72.7(4) . . ?
C2A C3 Pd1 72.5(4) . . ?
C2B C3 H3A 77.4 . . ?
C2A C3 H3A 120.0 . . ?
Pd1 C3 H3A 67.0 . . ?
C2B C3 H3B 151.9 . . ?
C2A C3 H3B 119.7 . . ?
Pd1 C3 H3B 132.7 . . ?
H3A C3 H3B 120.4 . . ?
C2B C3 H3C 119.2 . . ?
C2A C3 H3C 75.0 . . ?
Pd1 C3 H3C 69.8 . . ?
H3A C3 H3C 125.2 . . ?
H3B C3 H3C 70.5 . . ?
C2B C3 H3D 120.8 . . ?
C2A C3 H3D 155.1 . . ?
Pd1 C3 H3D 129.7 . . ?
H3A C3 H3D 69.8 . . ?
H3B C3 H3D 56.7 . . ?
H3C C3 H3D 120.0 . . ?
O1 C4 C14 105.6(2) . . ?
O1 C4 C9 109.6(2) . . ?
C14 C4 C9 118.9(2) . . ?
O1 C4 C5 106.8(2) . . ?
C14 C4 C5 114.0(3) . . ?
C9 C4 C5 101.5(2) . . ?
C13 C5 C12 107.4(3) . . ?
C13 C5 C6 112.3(3) . . ?
C12 C5 C6 107.0(3) . . ?
C13 C5 C4 114.0(3) . . ?
C12 C5 C4 112.7(3) . . ?
C6 C5 C4 103.2(3) . . ?
C7 C6 C10 101.2(3) . . ?
C7 C6 C5 112.0(3) . . ?
C10 C6 C5 101.1(3) . . ?
C7 C6 H11 113.7 . . ?
C10 C6 H11 113.7 . . ?
C5 C6 H11 113.7 . . ?
C6 C7 C8 102.8(3) . . ?
C6 C7 H2 111.2 . . ?
C8 C7 H2 111.2 . . ?
C6 C7 H3 111.2 . . ?
C8 C7 H3 111.2 . . ?
H2 C7 H3 109.1 . . ?
C9 C8 C7 104.6(3) . . ?
C9 C8 H9 110.8 . . ?
C7 C8 H9 110.8 . . ?
C9 C8 H10 110.8 . . ?
C7 C8 H10 110.8 . . ?
H9 C8 H10 108.9 . . ?
C11 C9 C10 115.3(3) . . ?
C11 C9 C8 108.8(3) . . ?
C10 C9 C8 98.9(3) . . ?
C11 C9 C4 121.7(3) . . ?
C10 C9 C4 101.5(2) . . ?
C8 C9 C4 108.1(3) . . ?
C6 C10 C9 95.8(2) . . ?
C6 C10 H5 112.6 . . ?
C9 C10 H5 112.6 . . ?
C6 C10 H4 112.6 . . ?
C9 C10 H4 112.6 . . ?
H5 C10 H4 110.1 . . ?
C9 C11 H8 109.5 . . ?
C9 C11 H7 109.5 . . ?
H8 C11 H7 109.5 . . ?
C9 C11 H6 109.5 . . ?
H8 C11 H6 109.5 . . ?
H7 C11 H6 109.5 . . ?
C5 C12 H13 109.5 . . ?
C5 C12 H14 109.5 . . ?
H13 C12 H14 109.5 . . ?
C5 C12 H12 109.5 . . ?
H13 C12 H12 109.5 . . ?
H14 C12 H12 109.5 . . ?
C5 C13 H15 109.5 . . ?
C5 C13 H16 109.5 . . ?
H15 C13 H16 109.5 . . ?
C5 C13 H17 109.5 . . ?
H15 C13 H17 109.5 . . ?
H16 C13 H17 109.5 . . ?
C15 C14 C19 117.4(3) . . ?
C15 C14 C4 118.5(3) . . ?
C19 C14 C4 124.1(3) . . ?
C16 C15 C14 122.9(3) . . ?
C16 C15 H18 118.6 . . ?
C14 C15 H18 118.6 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H19 120.2 . . ?
C15 C16 H19 120.2 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H42 120.5 . . ?
C18 C17 H42 120.5 . . ?
C17 C18 C19 122.6(3) . . ?
C17 C18 H41 118.7 . . ?
C19 C18 H41 118.7 . . ?
C18 C19 C14 118.4(3) . . ?
C18 C19 C20 113.5(3) . . ?
C14 C19 C20 126.5(3) . . ?
C35 C20 C21 117.5(3) . . ?
C35 C20 C19 111.3(3) . . ?
C21 C20 C19 130.8(3) . . ?
C32 C21 C20 117.1(3) . . ?
C32 C21 C22 117.6(3) . . ?
C20 C21 C22 124.6(3) . . ?
O2 C22 C21 108.4(2) . . ?
O2 C22 C28 109.9(2) . . ?
C21 C22 C28 117.8(3) . . ?
O2 C22 C23 105.9(2) . . ?
C21 C22 C23 111.9(3) . . ?
C28 C22 C23 102.3(2) . . ?
C24 C23 C31 107.4(3) . . ?
C24 C23 C25 112.0(3) . . ?
C31 C23 C25 107.6(3) . . ?
C24 C23 C22 114.2(3) . . ?
C31 C23 C22 113.1(3) . . ?
C25 C23 C22 102.4(3) . . ?
C23 C24 H21 109.5 . . ?
C23 C24 H22 109.5 . . ?
H21 C24 H22 109.5 . . ?
C23 C24 H23 109.5 . . ?
H21 C24 H23 109.5 . . ?
H22 C24 H23 109.5 . . ?
C26 C25 C30 101.4(3) . . ?
C26 C25 C23 112.0(3) . . ?
C30 C25 C23 101.0(3) . . ?
C26 C25 H24 113.7 . . ?
C30 C25 H24 113.7 . . ?
C23 C25 H24 113.7 . . ?
C25 C26 C27 102.9(3) . . ?
C25 C26 H26 111.2 . . ?
C27 C26 H26 111.2 . . ?
C25 C26 H25 111.2 . . ?
C27 C26 H25 111.2 . . ?
H26 C26 H25 109.1 . . ?
C26 C27 C28 104.9(3) . . ?
C26 C27 H27 110.8 . . ?
C28 C27 H27 110.8 . . ?
C26 C27 H28 110.8 . . ?
C28 C27 H28 110.8 . . ?
H27 C27 H28 108.8 . . ?
C29 C28 C30 115.7(3) . . ?
C29 C28 C27 112.6(3) . . ?
C30 C28 C27 98.1(3) . . ?
C29 C28 C22 118.8(3) . . ?
C30 C28 C22 101.3(3) . . ?
C27 C28 C22 107.8(3) . . ?
C28 C29 H31 109.5 . . ?
C28 C29 H29 109.5 . . ?
H31 C29 H29 109.5 . . ?
C28 C29 H30 109.5 . . ?
H31 C29 H30 109.5 . . ?
H29 C29 H30 109.5 . . ?
C25 C30 C28 96.3(3) . . ?
C25 C30 H32 112.5 . . ?
C28 C30 H32 112.5 . . ?
C25 C30 H33 112.5 . . ?
C28 C30 H33 112.5 . . ?
H32 C30 H33 110.0 . . ?
C23 C31 H34 109.5 . . ?
C23 C31 H35 109.5 . . ?
H34 C31 H35 109.5 . . ?
C23 C31 H36 109.5 . . ?
H34 C31 H36 109.5 . . ?
H35 C31 H36 109.5 . . ?
C33 C32 C21 123.7(3) . . ?
C33 C32 H40 118.1 . . ?
C21 C32 H40 118.1 . . ?
C34 C33 C32 118.7(3) . . ?
C34 C33 H39 120.6 . . ?
C32 C33 H39 120.6 . . ?
C35 C34 C33 118.4(3) . . ?
C35 C34 H37 120.8 . . ?
C33 C34 H37 120.8 . . ?
C34 C35 C20 124.0(3) . . ?
C34 C35 H38 118.0 . . ?
C20 C35 H38 118.0 . . ?

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
F2 P1 O2 C22 -44.2(3) . . . . ?
O1 P1 O2 C22 55.2(3) . . . . ?
Pd1 P1 O2 C22 -162.2(2) . . . . ?
F2 P1 O1 C4 -155.0(3) . . . . ?
O2 P1 O1 C4 98.7(3) . . . . ?
Pd1 P1 O1 C4 -33.0(3) . . . . ?
Pd1 C1 C2A C3 48.6(6) . . . . ?
Pd1 C1 C2B C3 -52.9(6) . . . . ?
C1 C2B C3 Pd1 53.5(6) . . . . ?
C1 C2A C3 Pd1 -50.2(7) . . . . ?
P1 O1 C4 C14 -58.7(3) . . . . ?
P1 O1 C4 C9 70.5(3) . . . . ?
P1 O1 C4 C5 179.55(19) . . . . ?
O1 C4 C5 C13 11.4(4) . . . . ?
C14 C4 C5 C13 -104.8(3) . . . . ?
C9 C4 C5 C13 126.1(3) . . . . ?
O1 C4 C5 C12 134.3(3) . . . . ?
C14 C4 C5 C12 18.1(4) . . . . ?
C9 C4 C5 C12 -111.0(3) . . . . ?
O1 C4 C5 C6 -110.7(3) . . . . ?
C14 C4 C5 C6 133.1(3) . . . . ?
C9 C4 C5 C6 4.0(3) . . . . ?
C13 C5 C6 C7 -54.9(4) . . . . ?
C12 C5 C6 C7 -172.5(3) . . . . ?
C4 C5 C6 C7 68.4(3) . . . . ?
C13 C5 C6 C10 -161.9(3) . . . . ?
C12 C5 C6 C10 80.5(3) . . . . ?
C4 C5 C6 C10 -38.6(3) . . . . ?
C10 C6 C7 C8 35.3(3) . . . . ?
C5 C6 C7 C8 -71.6(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C11 -155.3(3) . . . . ?
C7 C8 C9 C10 -34.6(3) . . . . ?
C7 C8 C9 C4 70.7(3) . . . . ?
O1 C4 C9 C11 -86.2(3) . . . . ?
C14 C4 C9 C11 35.3(4) . . . . ?
C5 C4 C9 C11 161.2(3) . . . . ?
O1 C4 C9 C10 144.1(3) . . . . ?
C14 C4 C9 C10 -94.4(3) . . . . ?
C5 C4 C9 C10 31.5(3) . . . . ?
O1 C4 C9 C8 40.6(3) . . . . ?
C14 C4 C9 C8 162.1(3) . . . . ?
C5 C4 C9 C8 -72.0(3) . . . . ?
C7 C6 C10 C9 -57.0(3) . . . . ?
C5 C6 C10 C9 58.3(3) . . . . ?
C11 C9 C10 C6 171.2(3) . . . . ?
C8 C9 C10 C6 55.4(3) . . . . ?
C4 C9 C10 C6 -55.3(3) . . . . ?
O1 C4 C14 C15 144.4(3) . . . . ?
C9 C4 C14 C15 20.9(4) . . . . ?
C5 C4 C14 C15 -98.7(3) . . . . ?
O1 C4 C14 C19 -37.4(4) . . . . ?
C9 C4 C14 C19 -160.9(3) . . . . ?
C5 C4 C14 C19 79.5(4) . . . . ?
C19 C14 C15 C16 4.3(5) . . . . ?
C4 C14 C15 C16 -177.4(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 C18 -2.4(5) . . . . ?
C16 C17 C18 C19 3.0(6) . . . . ?
C17 C18 C19 C14 0.2(5) . . . . ?
C17 C18 C19 C20 -166.4(3) . . . . ?
C15 C14 C19 C18 -3.6(4) . . . . ?
C4 C14 C19 C18 178.2(3) . . . . ?
C15 C14 C19 C20 161.0(3) . . . . ?
C4 C14 C19 C20 -17.2(5) . . . . ?
C18 C19 C20 C35 72.8(4) . . . . ?
C14 C19 C20 C35 -92.5(4) . . . . ?
C18 C19 C20 C21 -99.5(4) . . . . ?
C14 C19 C20 C21 95.2(4) . . . . ?
C35 C20 C21 C32 7.5(5) . . . . ?
C19 C20 C21 C32 179.4(3) . . . . ?
C35 C20 C21 C22 -163.1(3) . . . . ?
C19 C20 C21 C22 8.9(6) . . . . ?
P1 O2 C22 C21 -62.6(3) . . . . ?
P1 O2 C22 C28 67.4(3) . . . . ?
P1 O2 C22 C23 177.2(2) . . . . ?
C32 C21 C22 O2 153.1(3) . . . . ?
C20 C21 C22 O2 -36.5(4) . . . . ?
C32 C21 C22 C28 27.5(4) . . . . ?
C20 C21 C22 C28 -162.0(3) . . . . ?
C32 C21 C22 C23 -90.6(4) . . . . ?
C20 C21 C22 C23 79.9(4) . . . . ?
O2 C22 C23 C24 10.9(4) . . . . ?
C21 C22 C23 C24 -107.0(3) . . . . ?
C28 C22 C23 C24 126.0(3) . . . . ?
O2 C22 C23 C31 134.1(3) . . . . ?
C21 C22 C23 C31 16.2(4) . . . . ?
C28 C22 C23 C31 -110.8(3) . . . . ?
O2 C22 C23 C25 -110.4(3) . . . . ?
C21 C22 C23 C25 131.7(3) . . . . ?
C28 C22 C23 C25 4.8(3) . . . . ?
C24 C23 C25 C26 -54.7(4) . . . . ?
C31 C23 C25 C26 -172.5(3) . . . . ?
C22 C23 C25 C26 68.1(4) . . . . ?
C24 C23 C25 C30 -161.8(3) . . . . ?
C31 C23 C25 C30 80.4(3) . . . . ?
C22 C23 C25 C30 -39.0(3) . . . . ?
C30 C25 C26 C27 34.7(4) . . . . ?
C23 C25 C26 C27 -72.2(4) . . . . ?
C25 C26 C27 C28 0.7(4) . . . . ?
C26 C27 C28 C29 -157.2(3) . . . . ?
C26 C27 C28 C30 -34.9(3) . . . . ?
C26 C27 C28 C22 69.8(3) . . . . ?
O2 C22 C28 C29 -89.3(3) . . . . ?
C21 C22 C28 C29 35.4(4) . . . . ?
C23 C22 C28 C29 158.5(3) . . . . ?
O2 C22 C28 C30 142.7(3) . . . . ?
C21 C22 C28 C30 -92.5(3) . . . . ?
C23 C22 C28 C30 30.6(3) . . . . ?
O2 C22 C28 C27 40.3(3) . . . . ?
C21 C22 C28 C27 165.0(3) . . . . ?
C23 C22 C28 C27 -71.9(3) . . . . ?
C26 C25 C30 C28 -56.9(3) . . . . ?
C23 C25 C30 C28 58.5(3) . . . . ?
C29 C28 C30 C25 175.3(3) . . . . ?
C27 C28 C30 C25 55.3(3) . . . . ?
C22 C28 C30 C25 -54.8(3) . . . . ?
C20 C21 C32 C33 -2.4(6) . . . . ?
C22 C21 C32 C33 168.8(4) . . . . ?
C21 C32 C33 C34 -3.8(6) . . . . ?
C32 C33 C34 C35 4.6(6) . . . . ?
C33 C34 C35 C20 0.8(6) . . . . ?
C21 C20 C35 C34 -7.0(6) . . . . ?
C19 C20 C35 C34 179.5(4) . . . . ?

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.157

####################################################################### 
# 
# 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_eb-ox
_database_code_depnum_ccdc_archive 'CCDC 1886560'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universit?t zu K?ln
Germany
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2019-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H42 O2'
_chemical_formula_sum            'C34 H42 O2'
_chemical_formula_weight         482.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.4531(13)
_cell_length_b                   16.561(6)
_cell_length_c                   22.022(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2718.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      72.10

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.543
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5097
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26381
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.339
_diffrn_reflns_theta_max         72.347
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5335
_reflns_number_gt                5157
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.992
_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       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0684P)²+0.4299P] 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 2143 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5335
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.1292(2) 0.05408(9) 0.18948(6) 0.0173(3) Uani 1 1 d . . . . .
O2 O 0.3126(2) 0.16334(9) 0.55303(6) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.1089(3) 0.02611(12) 0.24795(9) 0.0127(4) Uani 1 1 d . . . . .
C2 C 0.1920(3) 0.06831(11) 0.29558(9) 0.0109(4) Uani 1 1 d . . . . .
C3 C 0.1514(3) 0.04366(11) 0.35582(8) 0.0102(4) Uani 1 1 d . . . . .
C4 C 0.2363(3) 0.10226(12) 0.39715(9) 0.0111(4) Uani 1 1 d . . . . .
C5 C 0.2278(3) 0.10654(12) 0.46050(9) 0.0131(4) Uani 1 1 d . . . . .
H5 H 0.1557 0.0696 0.4827 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3259(3) 0.16530(12) 0.49045(9) 0.0135(4) Uani 1 1 d . . . . .
C7 C 0.4200(4) 0.21909(15) 0.58572(10) 0.0258(5) Uani 1 1 d . . . . .
H7A H 0.5465 0.2109 0.5752 0.039 Uiso 1 1 calc R U . . .
H7B H 0.4035 0.2106 0.6294 0.039 Uiso 1 1 calc R U . . .
H7C H 0.3844 0.2743 0.5752 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4275(3) 0.22119(12) 0.45859(9) 0.0142(4) Uani 1 1 d . . . . .
H8 H 0.4939 0.2615 0.4795 0.017 Uiso 1 1 calc R U . . .
C9 C 0.4307(3) 0.21729(12) 0.39508(9) 0.0144(4) Uani 1 1 d . . . . .
H9 H 0.5006 0.2553 0.3731 0.017 Uiso 1 1 calc R U . . .
C10 C 0.3338(3) 0.15900(12) 0.36336(9) 0.0115(4) Uani 1 1 d . . . . .
C11 C 0.3244(3) 0.14037(11) 0.29487(8) 0.0110(4) Uani 1 1 d . . . . .
C12 C 0.2627(3) 0.21401(12) 0.25338(9) 0.0132(4) Uani 1 1 d . . . . .
C13 C 0.3621(3) 0.19796(12) 0.19303(9) 0.0165(4) Uani 1 1 d . . . . .
H13A H 0.3231 0.1473 0.1731 0.020 Uiso 1 1 calc R U . . .
H13B H 0.3530 0.2437 0.1643 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5480(3) 0.19093(13) 0.22182(9) 0.0173(4) Uani 1 1 d . . . . .
H14 H 0.6463 0.1816 0.1917 0.021 Uiso 1 1 calc R U . . .
C15 C 0.5210(3) 0.11969(12) 0.26692(9) 0.0149(4) Uani 1 1 d . . . . .
C16 C 0.6701(3) 0.11171(13) 0.31434(10) 0.0178(4) Uani 1 1 d . . . . .
H16A H 0.6372 0.0702 0.3440 0.027 Uiso 1 1 calc R U . . .
H16B H 0.6864 0.1635 0.3351 0.027 Uiso 1 1 calc R U . . .
H16C H 0.7823 0.0963 0.2942 0.027 Uiso 1 1 calc R U . . .
C17 C 0.5257(3) 0.03937(13) 0.23149(10) 0.0190(4) Uani 1 1 d . . . . .
H17A H 0.6453 0.0316 0.2139 0.029 Uiso 1 1 calc R U . . .
H17B H 0.4362 0.0409 0.1989 0.029 Uiso 1 1 calc R U . . .
H17C H 0.4986 -0.0054 0.2591 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5613(3) 0.27316(13) 0.25496(10) 0.0186(4) Uani 1 1 d . . . . .
H18A H 0.6119 0.3152 0.2280 0.022 Uiso 1 1 calc R U . . .
H18B H 0.6364 0.2689 0.2919 0.022 Uiso 1 1 calc R U . . .
C19 C 0.3628(3) 0.29189(12) 0.27134(9) 0.0156(4) Uani 1 1 d . . . . .
H19A H 0.3495 0.3031 0.3153 0.019 Uiso 1 1 calc R U . . .
H19B H 0.3177 0.3388 0.2480 0.019 Uiso 1 1 calc R U . . .
C20 C 0.0596(3) 0.22474(12) 0.25153(9) 0.0161(4) Uani 1 1 d . . . . .
H20A H 0.0121 0.2244 0.2930 0.024 Uiso 1 1 calc R U . . .
H20B H 0.0058 0.1804 0.2284 0.024 Uiso 1 1 calc R U . . .
H20C H 0.0305 0.2763 0.2320 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0490(3) -0.02548(11) 0.36918(9) 0.0115(4) Uani 1 1 d . . . . .
C22 C -0.0209(3) -0.06659(11) 0.31973(9) 0.0133(4) Uani 1 1 d . . . . .
H22 H -0.0892 -0.1141 0.3268 0.016 Uiso 1 1 calc R U . . .
C23 C 0.0047(3) -0.04124(12) 0.26018(9) 0.0141(4) Uani 1 1 d . . . . .
H23 H -0.0494 -0.0702 0.2278 0.017 Uiso 1 1 calc R U . . .
C24 C 0.0160(3) -0.06219(11) 0.43040(9) 0.0124(4) Uani 1 1 d . . . . .
C25 C 0.0884(3) -0.14762(12) 0.44295(9) 0.0157(4) Uani 1 1 d . . . . .
C26 C 0.1596(3) -0.07610(12) 0.47846(9) 0.0148(4) Uani 1 1 d . . . . .
H26 H 0.2852 -0.0560 0.4734 0.018 Uiso 1 1 calc R U . . .
C27 C 0.0666(3) -0.07743(13) 0.53994(10) 0.0202(5) Uani 1 1 d . . . . .
H27A H 0.0521 -0.0227 0.5574 0.024 Uiso 1 1 calc R U . . .
H27B H 0.1281 -0.1130 0.5694 0.024 Uiso 1 1 calc R U . . .
C28 C -0.1124(3) -0.11323(13) 0.51757(10) 0.0198(5) Uani 1 1 d . . . . .
H28 H -0.2063 -0.1221 0.5493 0.024 Uiso 1 1 calc R U . . .
C29 C -0.1660(3) -0.05680(12) 0.46384(9) 0.0163(4) Uani 1 1 d . . . . .
C30 C -0.2177(3) 0.02888(13) 0.48395(11) 0.0209(5) Uani 1 1 d . . . . .
H30A H -0.2191 0.0647 0.4486 0.031 Uiso 1 1 calc R U . . .
H30B H -0.1298 0.0487 0.5135 0.031 Uiso 1 1 calc R U . . .
H30C H -0.3370 0.0279 0.5026 0.031 Uiso 1 1 calc R U . . .
C31 C -0.3232(3) -0.09111(13) 0.42694(11) 0.0213(5) Uani 1 1 d . . . . .
H31A H -0.4263 -0.0998 0.4538 0.032 Uiso 1 1 calc R U . . .
H31B H -0.2876 -0.1426 0.4086 0.032 Uiso 1 1 calc R U . . .
H31C H -0.3561 -0.0529 0.3949 0.032 Uiso 1 1 calc R U . . .
C32 C -0.0440(3) -0.18928(13) 0.48494(10) 0.0208(5) Uani 1 1 d . . . . .
H32A H 0.0155 -0.2274 0.5131 0.025 Uiso 1 1 calc R U . . .
H32B H -0.1404 -0.2174 0.4623 0.025 Uiso 1 1 calc R U . . .
C33 C 0.2021(3) -0.19344(13) 0.39859(10) 0.0199(5) Uani 1 1 d . . . . .
H33A H 0.2788 -0.2316 0.4206 0.030 Uiso 1 1 calc R U . . .
H33B H 0.2772 -0.1556 0.3757 0.030 Uiso 1 1 calc R U . . .
H33C H 0.1246 -0.2232 0.3704 0.030 Uiso 1 1 calc R U . . .
C34 C 0.0537(4) 0.00872(16) 0.14103(10) 0.0290(6) Uani 1 1 d . . . . .
H34A H 0.1049 -0.0458 0.1410 0.044 Uiso 1 1 calc R U . . .
H34B H 0.0809 0.0353 0.1023 0.044 Uiso 1 1 calc R U . . .
H34C H -0.0766 0.0054 0.1463 0.044 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 1.377(2) . ?
O1 C34 1.421(3) . ?
O2 C6 1.382(2) . ?
O2 C7 1.418(3) . ?
C1 C23 1.385(3) . ?
C1 C2 1.405(3) . ?
C2 C3 1.421(3) . ?
C2 C11 1.548(3) . ?
C3 C21 1.407(3) . ?
C3 C4 1.473(3) . ?
C4 C5 1.398(3) . ?
C4 C10 1.402(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C8 1.387(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.400(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.541(3) . ?
C11 C12 1.592(3) . ?
C11 C15 1.626(3) . ?
C12 C20 1.524(3) . ?
C12 C19 1.542(3) . ?
C12 C13 1.545(3) . ?
C13 C14 1.528(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C18 1.548(3) . ?
C14 C15 1.555(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.531(3) . ?
C15 C17 1.543(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.554(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.386(3) . ?
C21 C24 1.499(3) . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C26 1.523(3) . ?
C24 C25 1.539(3) . ?
C24 C29 1.546(3) . ?
C25 C33 1.499(3) . ?
C25 C26 1.515(3) . ?
C25 C32 1.518(3) . ?
C26 C27 1.521(3) . ?
C26 H26 1.0000 . ?
C27 C28 1.541(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C32 1.537(3) . ?
C28 C29 1.560(3) . ?
C28 H28 1.0000 . ?
C29 C31 1.535(3) . ?
C29 C30 1.535(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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 C34 118.74(17) . . ?
C6 O2 C7 116.78(17) . . ?
O1 C1 C23 120.97(18) . . ?
O1 C1 C2 118.85(17) . . ?
C23 C1 C2 120.17(18) . . ?
C1 C2 C3 117.42(17) . . ?
C1 C2 C11 131.07(17) . . ?
C3 C2 C11 111.50(16) . . ?
C21 C3 C2 122.99(18) . . ?
C21 C3 C4 129.77(18) . . ?
C2 C3 C4 107.24(17) . . ?
C5 C4 C10 121.26(18) . . ?
C5 C4 C3 129.09(19) . . ?
C10 C4 C3 109.65(17) . . ?
C6 C5 C4 119.16(18) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
O2 C6 C5 114.89(18) . . ?
O2 C6 C8 124.00(19) . . ?
C5 C6 C8 121.11(18) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C9 118.93(18) . . ?
C6 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 121.60(19) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C4 117.85(18) . . ?
C9 C10 C11 130.77(18) . . ?
C4 C10 C11 111.20(17) . . ?
C10 C11 C2 100.00(15) . . ?
C10 C11 C12 114.94(15) . . ?
C2 C11 C12 114.35(16) . . ?
C10 C11 C15 111.81(16) . . ?
C2 C11 C15 114.55(15) . . ?
C12 C11 C15 101.79(15) . . ?
C20 C12 C19 112.94(17) . . ?
C20 C12 C13 118.25(18) . . ?
C19 C12 C13 97.62(16) . . ?
C20 C12 C11 113.04(17) . . ?
C19 C12 C11 110.73(16) . . ?
C13 C12 C11 102.92(16) . . ?
C14 C13 C12 95.22(16) . . ?
C14 C13 H13A 112.7 . . ?
C12 C13 H13A 112.7 . . ?
C14 C13 H13B 112.7 . . ?
C12 C13 H13B 112.7 . . ?
H13A C13 H13B 110.2 . . ?
C13 C14 C18 100.77(17) . . ?
C13 C14 C15 101.85(17) . . ?
C18 C14 C15 112.00(16) . . ?
C13 C14 H14 113.6 . . ?
C18 C14 H14 113.6 . . ?
C15 C14 H14 113.6 . . ?
C16 C15 C17 104.71(17) . . ?
C16 C15 C14 114.02(18) . . ?
C17 C15 C14 109.16(17) . . ?
C16 C15 C11 114.48(16) . . ?
C17 C15 C11 113.19(17) . . ?
C14 C15 C11 101.46(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C19 102.94(17) . . ?
C14 C18 H18A 111.2 . . ?
C19 C18 H18A 111.2 . . ?
C14 C18 H18B 111.2 . . ?
C19 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
C12 C19 C18 103.54(16) . . ?
C12 C19 H19A 111.1 . . ?
C18 C19 H19A 111.1 . . ?
C12 C19 H19B 111.1 . . ?
C18 C19 H19B 111.1 . . ?
H19A C19 H19B 109.0 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C3 116.06(18) . . ?
C22 C21 C24 116.47(17) . . ?
C3 C21 C24 127.37(18) . . ?
C21 C22 C23 122.77(19) . . ?
C21 C22 H22 118.6 . . ?
C23 C22 H22 118.6 . . ?
C1 C23 C22 120.24(18) . . ?
C1 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C21 C24 C26 124.82(17) . . ?
C21 C24 C25 118.46(17) . . ?
C26 C24 C25 59.31(13) . . ?
C21 C24 C29 123.29(17) . . ?
C26 C24 C29 107.12(16) . . ?
C25 C24 C29 105.98(16) . . ?
C33 C25 C26 122.29(19) . . ?
C33 C25 C32 122.29(19) . . ?
C26 C25 C32 105.57(17) . . ?
C33 C25 C24 123.12(18) . . ?
C26 C25 C24 59.80(13) . . ?
C32 C25 C24 107.39(17) . . ?
C25 C26 C27 106.77(17) . . ?
C25 C26 C24 60.89(13) . . ?
C27 C26 C24 107.48(18) . . ?
C25 C26 H26 122.0 . . ?
C27 C26 H26 122.0 . . ?
C24 C26 H26 122.0 . . ?
C26 C27 C28 96.63(17) . . ?
C26 C27 H27A 112.4 . . ?
C28 C27 H27A 112.4 . . ?
C26 C27 H27B 112.4 . . ?
C28 C27 H27B 112.4 . . ?
H27A C27 H27B 110.0 . . ?
C32 C28 C27 100.25(18) . . ?
C32 C28 C29 102.79(17) . . ?
C27 C28 C29 103.53(17) . . ?
C32 C28 H28 116.0 . . ?
C27 C28 H28 116.0 . . ?
C29 C28 H28 116.0 . . ?
C31 C29 C30 107.66(18) . . ?
C31 C29 C24 113.34(17) . . ?
C30 C29 C24 114.25(17) . . ?
C31 C29 C28 112.05(18) . . ?
C30 C29 C28 113.53(18) . . ?
C24 C29 C28 95.85(17) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C25 C32 C28 97.35(17) . . ?
C25 C32 H32A 112.3 . . ?
C28 C32 H32A 112.3 . . ?
C25 C32 H32B 112.3 . . ?
C28 C32 H32B 112.3 . . ?
H32A C32 H32B 109.9 . . ?
C25 C33 H33A 109.5 . . ?
C25 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C25 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O1 C34 H34A 109.5 . . ?
O1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
C34 O1 C1 C23 -5.2(3) . . . . ?
C34 O1 C1 C2 176.4(2) . . . . ?
O1 C1 C2 C3 172.76(18) . . . . ?
C23 C1 C2 C3 -5.6(3) . . . . ?
O1 C1 C2 C11 -6.6(3) . . . . ?
C23 C1 C2 C11 175.0(2) . . . . ?
C1 C2 C3 C21 7.1(3) . . . . ?
C11 C2 C3 C21 -173.43(18) . . . . ?
C1 C2 C3 C4 -173.39(17) . . . . ?
C11 C2 C3 C4 6.1(2) . . . . ?
C21 C3 C4 C5 -4.0(4) . . . . ?
C2 C3 C4 C5 176.5(2) . . . . ?
C21 C3 C4 C10 176.60(19) . . . . ?
C2 C3 C4 C10 -2.9(2) . . . . ?
C10 C4 C5 C6 -3.6(3) . . . . ?
C3 C4 C5 C6 177.09(19) . . . . ?
C7 O2 C6 C5 176.01(19) . . . . ?
C7 O2 C6 C8 -4.3(3) . . . . ?
C4 C5 C6 O2 -178.36(18) . . . . ?
C4 C5 C6 C8 2.0(3) . . . . ?
O2 C6 C8 C9 -180.0(2) . . . . ?
C5 C6 C8 C9 -0.3(3) . . . . ?
C6 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C4 -1.9(3) . . . . ?
C8 C9 C10 C11 -176.5(2) . . . . ?
C5 C4 C10 C9 3.6(3) . . . . ?
C3 C4 C10 C9 -177.03(17) . . . . ?
C5 C4 C10 C11 179.15(18) . . . . ?
C3 C4 C10 C11 -1.4(2) . . . . ?
C9 C10 C11 C2 179.5(2) . . . . ?
C4 C10 C11 C2 4.7(2) . . . . ?
C9 C10 C11 C12 -57.5(3) . . . . ?
C4 C10 C11 C12 127.62(18) . . . . ?
C9 C10 C11 C15 57.9(3) . . . . ?
C4 C10 C11 C15 -116.99(18) . . . . ?
C1 C2 C11 C10 172.9(2) . . . . ?
C3 C2 C11 C10 -6.5(2) . . . . ?
C1 C2 C11 C12 49.5(3) . . . . ?
C3 C2 C11 C12 -129.89(17) . . . . ?
C1 C2 C11 C15 -67.4(3) . . . . ?
C3 C2 C11 C15 113.15(18) . . . . ?
C10 C11 C12 C20 -82.0(2) . . . . ?
C2 C11 C12 C20 32.9(2) . . . . ?
C15 C11 C12 C20 157.00(16) . . . . ?
C10 C11 C12 C19 45.9(2) . . . . ?
C2 C11 C12 C19 160.79(17) . . . . ?
C15 C11 C12 C19 -75.13(18) . . . . ?
C10 C11 C12 C13 149.35(18) . . . . ?
C2 C11 C12 C13 -95.78(19) . . . . ?
C15 C11 C12 C13 28.30(19) . . . . ?
C20 C12 C13 C14 -178.78(17) . . . . ?
C19 C12 C13 C14 60.00(17) . . . . ?
C11 C12 C13 C14 -53.39(18) . . . . ?
C12 C13 C14 C18 -56.28(17) . . . . ?
C12 C13 C14 C15 59.15(18) . . . . ?
C13 C14 C15 C16 -165.23(17) . . . . ?
C18 C14 C15 C16 -58.3(2) . . . . ?
C13 C14 C15 C17 78.1(2) . . . . ?
C18 C14 C15 C17 -175.02(18) . . . . ?
C13 C14 C15 C11 -41.64(18) . . . . ?
C18 C14 C15 C11 65.3(2) . . . . ?
C10 C11 C15 C16 7.7(2) . . . . ?
C2 C11 C15 C16 -105.19(19) . . . . ?
C12 C11 C15 C16 130.86(17) . . . . ?
C10 C11 C15 C17 127.57(18) . . . . ?
C2 C11 C15 C17 14.7(2) . . . . ?
C12 C11 C15 C17 -109.23(18) . . . . ?
C10 C11 C15 C14 -115.61(17) . . . . ?
C2 C11 C15 C14 131.53(17) . . . . ?
C12 C11 C15 C14 7.58(18) . . . . ?
C13 C14 C18 C19 30.64(18) . . . . ?
C15 C14 C18 C19 -77.0(2) . . . . ?
C20 C12 C19 C18 -166.60(17) . . . . ?
C13 C12 C19 C18 -41.50(18) . . . . ?
C11 C12 C19 C18 65.5(2) . . . . ?
C14 C18 C19 C12 7.06(19) . . . . ?
C2 C3 C21 C22 -3.8(3) . . . . ?
C4 C3 C21 C22 176.81(19) . . . . ?
C2 C3 C21 C24 172.39(19) . . . . ?
C4 C3 C21 C24 -7.0(3) . . . . ?
C3 C21 C22 C23 -1.0(3) . . . . ?
C24 C21 C22 C23 -177.62(19) . . . . ?
O1 C1 C23 C22 -177.14(19) . . . . ?
C2 C1 C23 C22 1.2(3) . . . . ?
C21 C22 C23 C1 2.3(3) . . . . ?
C22 C21 C24 C26 130.9(2) . . . . ?
C3 C21 C24 C26 -45.2(3) . . . . ?
C22 C21 C24 C25 60.2(3) . . . . ?
C3 C21 C24 C25 -115.9(2) . . . . ?
C22 C21 C24 C29 -76.7(2) . . . . ?
C3 C21 C24 C29 107.1(2) . . . . ?
C21 C24 C25 C33 4.7(3) . . . . ?
C26 C24 C25 C33 -111.0(2) . . . . ?
C29 C24 C25 C33 148.3(2) . . . . ?
C21 C24 C25 C26 115.7(2) . . . . ?
C29 C24 C25 C26 -100.73(17) . . . . ?
C21 C24 C25 C32 -146.07(19) . . . . ?
C26 C24 C25 C32 98.24(19) . . . . ?
C29 C24 C25 C32 -2.5(2) . . . . ?
C33 C25 C26 C27 -146.63(19) . . . . ?
C32 C25 C26 C27 -0.3(2) . . . . ?
C24 C25 C26 C27 101.03(18) . . . . ?
C33 C25 C26 C24 112.3(2) . . . . ?
C32 C25 C26 C24 -101.34(18) . . . . ?
C21 C24 C26 C25 -105.2(2) . . . . ?
C29 C24 C26 C25 98.75(17) . . . . ?
C21 C24 C26 C27 154.96(18) . . . . ?
C25 C24 C26 C27 -99.84(18) . . . . ?
C29 C24 C26 C27 -1.1(2) . . . . ?
C25 C26 C27 C28 -32.5(2) . . . . ?
C24 C26 C27 C28 31.56(19) . . . . ?
C26 C27 C28 C32 53.90(18) . . . . ?
C26 C27 C28 C29 -52.05(19) . . . . ?
C21 C24 C29 C31 57.0(3) . . . . ?
C26 C24 C29 C31 -146.52(17) . . . . ?
C25 C24 C29 C31 -84.4(2) . . . . ?
C21 C24 C29 C30 -66.8(2) . . . . ?
C26 C24 C29 C30 89.7(2) . . . . ?
C25 C24 C29 C30 151.79(18) . . . . ?
C21 C24 C29 C28 174.06(18) . . . . ?
C26 C24 C29 C28 -29.44(19) . . . . ?
C25 C24 C29 C28 32.70(19) . . . . ?
C32 C28 C29 C31 65.1(2) . . . . ?
C27 C28 C29 C31 169.09(18) . . . . ?
C32 C28 C29 C30 -172.70(18) . . . . ?
C27 C28 C29 C30 -68.7(2) . . . . ?
C32 C28 C29 C24 -53.04(19) . . . . ?
C27 C28 C29 C24 50.98(18) . . . . ?
C33 C25 C32 C28 179.4(2) . . . . ?
C26 C25 C32 C28 33.1(2) . . . . ?
C24 C25 C32 C28 -29.5(2) . . . . ?
C27 C28 C32 C25 -54.57(19) . . . . ?
C29 C28 C32 C25 52.0(2) . . . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.132

