# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_alex_2BINOL-PRO
_database_code_depnum_ccdc_archive 'CCDC 2352967'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2, 2(C5 H9 N O2)'
_chemical_formula_sum            'C30 H32 N2 O6'
_chemical_formula_weight         516.57

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                   10.4050(9)
_cell_length_b                   10.991(2)
_cell_length_c                   12.216(3)
_cell_angle_alpha                109.33(2)
_cell_angle_beta                 91.872(12)
_cell_angle_gamma                104.146(13)
_cell_volume                     1268.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1643
_cell_measurement_theta_min      3.1020
_cell_measurement_theta_max      24.9760

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'60 images, ΔΦ 3.0° '
'53 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14967
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4586
_reflns_number_gt                2896
_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       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;




_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)+(0.0450P)²+0.6186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     412
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.100
_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 0.1604(2) 0.5785(2) 0.3888(2) 0.0427(6) Uani 1 1 d . . . . .
H1 H 0.181959 0.508878 0.378090 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2239(3) 0.6429(3) 0.3194(3) 0.0336(8) Uani 1 1 d . . . . .
C3 C 0.2401(3) 0.7817(4) 0.3607(3) 0.0422(9) Uani 1 1 d . . . . .
H3 H 0.205450 0.821256 0.428628 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3054(4) 0.8585(4) 0.3025(3) 0.0459(9) Uani 1 1 d . . . . .
H4 H 0.317144 0.950594 0.331559 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3560(3) 0.7997(3) 0.1979(3) 0.0371(8) Uani 1 1 d . . . . .
C6 C 0.4283(3) 0.8793(4) 0.1385(3) 0.0491(10) Uani 1 1 d . . . . .
H6 H 0.440948 0.971578 0.167810 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4795(4) 0.8237(4) 0.0397(4) 0.0559(11) Uani 1 1 d . . . . .
H7 H 0.527423 0.877611 0.001838 0.067 Uiso 1 1 calc R U . . .
C8 C 0.4601(4) 0.6846(4) -0.0057(3) 0.0515(10) Uani 1 1 d . . . . .
H8 H 0.494661 0.646615 -0.074210 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3911(3) 0.6041(4) 0.0495(3) 0.0404(9) Uani 1 1 d . . . . .
H9 H 0.379921 0.512091 0.018451 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3363(3) 0.6592(3) 0.1537(3) 0.0307(8) Uani 1 1 d . . . . .
C11 C 0.2674(3) 0.5784(3) 0.2157(3) 0.0296(7) Uani 1 1 d . . . . .
O12 O 0.3856(2) 0.4600(2) 0.34311(19) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.450113 0.433564 0.354978 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3128(3) 0.3759(3) 0.2392(3) 0.0314(8) Uani 1 1 d . . . . .
C14 C 0.3014(3) 0.2374(3) 0.2027(3) 0.0344(8) Uani 1 1 d . . . . .
H14 H 0.345743 0.204106 0.248738 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2260(3) 0.1523(3) 0.1009(3) 0.0397(9) Uani 1 1 d . . . . .
H15 H 0.219448 0.061217 0.077906 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1573(3) 0.2004(3) 0.0295(3) 0.0346(8) Uani 1 1 d . . . . .
C17 C 0.0780(3) 0.1142(3) -0.0766(3) 0.0436(9) Uani 1 1 d . . . . .
H17 H 0.071834 0.023127 -0.101356 0.052 Uiso 1 1 calc R U . . .
C18 C 0.0110(4) 0.1610(4) -0.1431(3) 0.0486(10) Uani 1 1 d . . . . .
H18 H -0.041050 0.102355 -0.212466 0.058 Uiso 1 1 calc R U . . .
C19 C 0.0204(3) 0.2986(4) -0.1070(3) 0.0455(9) Uani 1 1 d . . . . .
H19 H -0.026075 0.330739 -0.152629 0.055 Uiso 1 1 calc R U . . .
C20 C 0.0971(3) 0.3856(3) -0.0054(3) 0.0371(8) Uani 1 1 d . . . . .
H20 H 0.102603 0.476401 0.016793 0.044 Uiso 1 1 calc R U . . .
C21 C 0.1683(3) 0.3405(3) 0.0666(3) 0.0292(7) Uani 1 1 d . . . . .
C22 C 0.2496(3) 0.4299(3) 0.1740(3) 0.0280(7) Uani 1 1 d . . . . .
N31 N 0.8574(2) 0.3751(3) 0.3575(2) 0.0380(7) Uani 1 1 d . . . . .
H31A H 0.839962 0.448934 0.404638 0.046 Uiso 1 1 calc R U . . .
H31B H 0.932282 0.367051 0.388214 0.046 Uiso 1 1 calc R U . . .
C32 C 0.8724(4) 0.3828(4) 0.2391(3) 0.0518(10) Uani 1 1 d . . . . .
H32A H 0.810459 0.426750 0.217820 0.062 Uiso 1 1 calc R U . . .
H32B H 0.962755 0.430573 0.235045 0.062 Uiso 1 1 calc R U . . .
C33 C 0.8409(4) 0.2404(4) 0.1626(4) 0.0666(13) Uani 1 1 d . . . . .
H33A H 0.918228 0.206019 0.163360 0.080 Uiso 1 1 calc R U . . .
H33B H 0.812342 0.229684 0.082771 0.080 Uiso 1 1 calc R U . . .
C34 C 0.7296(4) 0.1689(4) 0.2132(3) 0.0567(11) Uani 1 1 d . . . . .
H34A H 0.737337 0.079973 0.204214 0.068 Uiso 1 1 calc R U . . .
H34B H 0.643505 0.160430 0.174129 0.068 Uiso 1 1 calc R U . . .
C35 C 0.7435(3) 0.2543(3) 0.3432(3) 0.0376(8) Uani 1 1 d . . . . .
H35 H 0.766487 0.205242 0.391494 0.045 Uiso 1 1 calc R U . . .
C36 C 0.6156(3) 0.2955(4) 0.3770(3) 0.0372(8) Uani 1 1 d . . . . .
O37 O 0.6108(2) 0.4092(3) 0.3778(2) 0.0474(7) Uani 1 1 d . . . . .
O38 O 0.5257(2) 0.2112(3) 0.3966(2) 0.0540(7) Uani 1 1 d . . . . .
N41 N 0.3303(3) 0.2957(3) 0.5322(3) 0.0379(9) Uani 0.907(4) 1 d D . P A 1
H41A H 0.391987 0.278106 0.485121 0.045 Uiso 0.907(4) 1 calc R U P A 1
H41B H 0.320096 0.375467 0.537435 0.045 Uiso 0.907(4) 1 calc R U P A 1
C42 C 0.3733(4) 0.2971(5) 0.6503(4) 0.0606(13) Uani 0.907(4) 1 d D . P A 1
H42A H 0.468078 0.304009 0.659635 0.073 Uiso 0.907(4) 1 calc R U P A 1
H42B H 0.355577 0.372013 0.710987 0.073 Uiso 0.907(4) 1 calc R U P A 1
C43 C 0.2947(6) 0.1699(8) 0.6563(6) 0.087(2) Uani 0.907(4) 1 d D . P A 1
H43A H 0.282895 0.177410 0.736494 0.105 Uiso 0.907(4) 1 calc R U P A 1
H43B H 0.337148 0.098948 0.622512 0.105 Uiso 0.907(4) 1 calc R U P A 1
C44 C 0.1621(4) 0.1440(6) 0.5851(5) 0.0837(19) Uani 0.907(4) 1 d D . P A 1
H44A H 0.114696 0.049584 0.557370 0.100 Uiso 0.907(4) 1 calc R U P A 1
H44B H 0.106066 0.194863 0.631152 0.100 Uiso 0.907(4) 1 calc R U P A 1
C45 C 0.2004(3) 0.1901(4) 0.4837(3) 0.0401(10) Uani 0.907(4) 1 d D . P A 1
H45 H 0.216250 0.115203 0.420025 0.048 Uiso 0.907(4) 1 calc R U P A 1
C46 C 0.0948(4) 0.2418(4) 0.4373(4) 0.0376(11) Uani 0.907(4) 1 d D . P A 1
O47 O 0.1166(6) 0.3649(4) 0.4611(8) 0.0469(13) Uani 0.907(4) 1 d D . P A 1
O48 O -0.0087(3) 0.1546(3) 0.3845(3) 0.0712(11) Uani 0.907(4) 1 d D . P A 1
N41B N 0.308(3) 0.164(3) 0.497(2) 0.054(7) Uani 0.093(4) 1 d D U P A 2
H41C H 0.246144 0.093745 0.448357 0.065 Uiso 0.093(4) 1 calc R U P A 2
H41D H 0.377511 0.182368 0.459415 0.065 Uiso 0.093(4) 1 calc R U P A 2
C42B C 0.350(5) 0.134(4) 0.601(3) 0.067(10) Uani 0.093(4) 1 d D U P A 2
H42C H 0.340123 0.038651 0.580880 0.081 Uiso 0.093(4) 1 calc R U P A 2
H42D H 0.442012 0.182339 0.631951 0.081 Uiso 0.093(4) 1 calc R U P A 2
C43B C 0.259(6) 0.179(5) 0.685(4) 0.075(11) Uani 0.093(4) 1 d D U P A 2
H43C H 0.297703 0.197459 0.764302 0.090 Uiso 0.093(4) 1 calc R U P A 2
H43D H 0.174056 0.111396 0.668488 0.090 Uiso 0.093(4) 1 calc R U P A 2
C44B C 0.243(4) 0.305(4) 0.668(2) 0.063(8) Uani 0.093(4) 1 d D U P A 2
H44C H 0.313070 0.382290 0.716763 0.076 Uiso 0.093(4) 1 calc R U P A 2
H44D H 0.157138 0.319175 0.688991 0.076 Uiso 0.093(4) 1 calc R U P A 2
C45B C 0.252(3) 0.283(3) 0.540(2) 0.051(8) Uani 0.093(4) 1 d D U P A 2
H45B H 0.316429 0.360574 0.533327 0.061 Uiso 0.093(4) 1 calc R U P A 2
C46B C 0.119(4) 0.261(3) 0.469(3) 0.044(8) Uani 0.093(4) 1 d D U P A 2
O47B O 0.093(7) 0.364(4) 0.463(8) 0.0469(13) Uani 0.093(4) 1 d D U P A 2
O48B O 0.072(3) 0.146(3) 0.397(3) 0.063(8) Uani 0.093(4) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.365(4) . ?
O1 H1 0.8200 . ?
C2 C11 1.382(4) . ?
C2 C3 1.404(5) . ?
C3 C4 1.352(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 C10 1.416(4) . ?
C6 C7 1.351(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.431(4) . ?
C11 C22 1.501(4) . ?
O12 C13 1.363(4) . ?
O12 H12 0.8200 . ?
C13 C22 1.374(4) . ?
C13 C14 1.410(4) . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.414(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(4) . ?
C16 C21 1.428(4) . ?
C17 C18 1.350(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.405(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.411(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.439(4) . ?
N31 C32 1.488(4) . ?
N31 C35 1.504(4) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
C32 C33 1.480(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.505(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.535(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.534(4) . ?
C35 H35 0.9800 . ?
C36 O38 1.237(4) . ?
C36 O37 1.259(4) . ?
N41 C42 1.491(5) . ?
N41 C45 1.500(4) . ?
N41 H41A 0.8900 . ?
N41 H41B 0.8900 . ?
C42 C43 1.463(7) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.520(7) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.516(6) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.526(5) . ?
C45 H45 0.9800 . ?
C46 O48 1.239(5) . ?
C46 O47 1.246(5) . ?
N41B C42B 1.489(11) . ?
N41B C45B 1.499(10) . ?
N41B H41C 0.8900 . ?
N41B H41D 0.8900 . ?
C42B C43B 1.464(12) . ?
C42B H42C 0.9700 . ?
C42B H42D 0.9700 . ?
C43B C44B 1.516(13) . ?
C43B H43C 0.9700 . ?
C43B H43D 0.9700 . ?
C44B C45B 1.517(11) . ?
C44B H44C 0.9700 . ?
C44B H44D 0.9700 . ?
C45B C46B 1.529(11) . ?
C45B H45B 0.9800 . ?
C46B O48B 1.244(11) . ?
C46B O47B 1.251(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
O1 C2 C11 123.6(3) . . ?
O1 C2 C3 114.4(3) . . ?
C11 C2 C3 122.0(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 C10 119.3(3) . . ?
C6 C5 C10 119.7(3) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 117.7(3) . . ?
C5 C10 C11 120.1(3) . . ?
C9 C10 C11 122.2(3) . . ?
C2 C11 C10 117.6(3) . . ?
C2 C11 C22 120.8(3) . . ?
C10 C11 C22 121.5(3) . . ?
C13 O12 H12 109.5 . . ?
O12 C13 C22 118.1(3) . . ?
O12 C13 C14 120.0(3) . . ?
C22 C13 C14 121.9(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 C21 119.2(3) . . ?
C15 C16 C21 118.7(3) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 117.6(3) . . ?
C20 C21 C22 122.5(3) . . ?
C16 C21 C22 119.9(3) . . ?
C13 C22 C21 118.1(3) . . ?
C13 C22 C11 119.7(3) . . ?
C21 C22 C11 122.1(3) . . ?
C32 N31 C35 107.0(2) . . ?
C32 N31 H31A 110.3 . . ?
C35 N31 H31A 110.3 . . ?
C32 N31 H31B 110.3 . . ?
C35 N31 H31B 110.3 . . ?
H31A N31 H31B 108.6 . . ?
C33 C32 N31 103.2(3) . . ?
C33 C32 H32A 111.1 . . ?
N31 C32 H32A 111.1 . . ?
C33 C32 H32B 111.1 . . ?
N31 C32 H32B 111.1 . . ?
H32A C32 H32B 109.1 . . ?
C32 C33 C34 104.9(3) . . ?
C32 C33 H33A 110.8 . . ?
C34 C33 H33A 110.8 . . ?
C32 C33 H33B 110.8 . . ?
C34 C33 H33B 110.8 . . ?
H33A C33 H33B 108.8 . . ?
C33 C34 C35 106.3(3) . . ?
C33 C34 H34A 110.5 . . ?
C35 C34 H34A 110.5 . . ?
C33 C34 H34B 110.5 . . ?
C35 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?
N31 C35 C36 110.8(3) . . ?
N31 C35 C34 104.1(3) . . ?
C36 C35 C34 111.9(3) . . ?
N31 C35 H35 110.0 . . ?
C36 C35 H35 110.0 . . ?
C34 C35 H35 110.0 . . ?
O38 C36 O37 126.7(3) . . ?
O38 C36 C35 116.2(3) . . ?
O37 C36 C35 117.0(3) . . ?
C42 N41 C45 108.7(3) . . ?
C42 N41 H41A 110.0 . . ?
C45 N41 H41A 110.0 . . ?
C42 N41 H41B 110.0 . . ?
C45 N41 H41B 110.0 . . ?
H41A N41 H41B 108.3 . . ?
C43 C42 N41 105.4(4) . . ?
C43 C42 H42A 110.7 . . ?
N41 C42 H42A 110.7 . . ?
C43 C42 H42B 110.7 . . ?
N41 C42 H42B 110.7 . . ?
H42A C42 H42B 108.8 . . ?
C42 C43 C44 103.5(4) . . ?
C42 C43 H43A 111.1 . . ?
C44 C43 H43A 111.1 . . ?
C42 C43 H43B 111.1 . . ?
C44 C43 H43B 111.1 . . ?
H43A C43 H43B 109.0 . . ?
C45 C44 C43 104.2(4) . . ?
C45 C44 H44A 110.9 . . ?
C43 C44 H44A 110.9 . . ?
C45 C44 H44B 110.9 . . ?
C43 C44 H44B 110.9 . . ?
H44A C44 H44B 108.9 . . ?
N41 C45 C44 103.6(3) . . ?
N41 C45 C46 112.7(3) . . ?
C44 C45 C46 113.5(3) . . ?
N41 C45 H45 108.9 . . ?
C44 C45 H45 108.9 . . ?
C46 C45 H45 108.9 . . ?
O48 C46 O47 126.8(4) . . ?
O48 C46 C45 114.8(4) . . ?
O47 C46 C45 118.3(4) . . ?
C42B N41B C45B 107.9(10) . . ?
C42B N41B H41C 110.1 . . ?
C45B N41B H41C 110.1 . . ?
C42B N41B H41D 110.1 . . ?
C45B N41B H41D 110.1 . . ?
H41C N41B H41D 108.4 . . ?
C43B C42B N41B 104.0(13) . . ?
C43B C42B H42C 110.9 . . ?
N41B C42B H42C 110.9 . . ?
C43B C42B H42D 110.9 . . ?
N41B C42B H42D 110.9 . . ?
H42C C42B H42D 109.0 . . ?
C42B C43B C44B 103.9(13) . . ?
C42B C43B H43C 111.0 . . ?
C44B C43B H43C 111.0 . . ?
C42B C43B H43D 111.0 . . ?
C44B C43B H43D 111.0 . . ?
H43C C43B H43D 109.0 . . ?
C43B C44B C45B 105.6(11) . . ?
C43B C44B H44C 110.6 . . ?
C45B C44B H44C 110.6 . . ?
C43B C44B H44D 110.6 . . ?
C45B C44B H44D 110.6 . . ?
H44C C44B H44D 108.8 . . ?
N41B C45B C44B 104.5(9) . . ?
N41B C45B C46B 112.5(13) . . ?
C44B C45B C46B 114.2(15) . . ?
N41B C45B H45B 108.5 . . ?
C44B C45B H45B 108.5 . . ?
C46B C45B H45B 108.5 . . ?
O48B C46B O47B 125(2) . . ?
O48B C46B C45B 114.4(15) . . ?
O47B C46B C45B 116.4(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 177.7(3) . . . . ?
C11 C2 C3 C4 -3.4(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C3 C4 C5 C10 0.7(5) . . . . ?
C4 C5 C6 C7 178.5(4) . . . . ?
C10 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C4 C5 C10 C9 -178.7(3) . . . . ?
C6 C5 C10 C9 -0.1(5) . . . . ?
C4 C5 C10 C11 -0.9(5) . . . . ?
C6 C5 C10 C11 177.7(3) . . . . ?
C8 C9 C10 C5 -0.1(5) . . . . ?
C8 C9 C10 C11 -177.9(3) . . . . ?
O1 C2 C11 C10 -178.1(3) . . . . ?
C3 C2 C11 C10 3.1(4) . . . . ?
O1 C2 C11 C22 -1.6(4) . . . . ?
C3 C2 C11 C22 179.6(3) . . . . ?
C5 C10 C11 C2 -1.0(4) . . . . ?
C9 C10 C11 C2 176.7(3) . . . . ?
C5 C10 C11 C22 -177.5(3) . . . . ?
C9 C10 C11 C22 0.2(4) . . . . ?
O12 C13 C14 C15 178.1(3) . . . . ?
C22 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 -179.9(3) . . . . ?
C14 C15 C16 C21 -0.2(5) . . . . ?
C15 C16 C17 C18 178.8(3) . . . . ?
C21 C16 C17 C18 -0.9(5) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
C15 C16 C21 C20 -179.1(3) . . . . ?
C17 C16 C21 C22 -179.4(3) . . . . ?
C15 C16 C21 C22 0.9(4) . . . . ?
O12 C13 C22 C21 -177.5(2) . . . . ?
C14 C13 C22 C21 0.9(4) . . . . ?
O12 C13 C22 C11 2.8(4) . . . . ?
C14 C13 C22 C11 -178.8(3) . . . . ?
C20 C21 C22 C13 178.7(3) . . . . ?
C16 C21 C22 C13 -1.2(4) . . . . ?
C20 C21 C22 C11 -1.6(4) . . . . ?
C16 C21 C22 C11 178.5(3) . . . . ?
C2 C11 C22 C13 -63.2(4) . . . . ?
C10 C11 C22 C13 113.2(3) . . . . ?
C2 C11 C22 C21 117.2(3) . . . . ?
C10 C11 C22 C21 -66.5(4) . . . . ?
C35 N31 C32 C33 -35.9(4) . . . . ?
N31 C32 C33 C34 37.5(4) . . . . ?
C32 C33 C34 C35 -25.6(4) . . . . ?
C32 N31 C35 C36 -100.7(3) . . . . ?
C32 N31 C35 C34 19.7(4) . . . . ?
C33 C34 C35 N31 3.6(4) . . . . ?
C33 C34 C35 C36 123.3(4) . . . . ?
N31 C35 C36 O38 -162.7(3) . . . . ?
C34 C35 C36 O38 81.6(4) . . . . ?
N31 C35 C36 O37 19.8(4) . . . . ?
C34 C35 C36 O37 -95.9(4) . . . . ?
C45 N41 C42 C43 16.8(5) . . . . ?
N41 C42 C43 C44 -33.8(6) . . . . ?
C42 C43 C44 C45 38.6(6) . . . . ?
C42 N41 C45 C44 7.2(4) . . . . ?
C42 N41 C45 C46 130.3(4) . . . . ?
C43 C44 C45 N41 -27.6(5) . . . . ?
C43 C44 C45 C46 -150.2(5) . . . . ?
N41 C45 C46 O48 172.1(4) . . . . ?
C44 C45 C46 O48 -70.4(5) . . . . ?
N41 C45 C46 O47 -11.8(7) . . . . ?
C44 C45 C46 O47 105.6(7) . . . . ?
C45B N41B C42B C43B 29(4) . . . . ?
N41B C42B C43B C44B -38(4) . . . . ?
C42B C43B C44B C45B 33(4) . . . . ?
C42B N41B C45B C44B -9(3) . . . . ?
C42B N41B C45B C46B -133(3) . . . . ?
C43B C44B C45B N41B -14(3) . . . . ?
C43B C44B C45B C46B 109(3) . . . . ?
N41B C45B C46B O48B 7(4) . . . . ?
C44B C45B C46B O48B -111(4) . . . . ?
N41B C45B C46B O47B -151(6) . . . . ?
C44B C45B C46B O47B 90(6) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: cooling from ethanol solution'
####################################################################### 
# 
# 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_alex_RSBin_DLpro
_database_code_depnum_ccdc_archive 'CCDC 2352968'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H14 O2), C5 H9 N O2'
_chemical_formula_sum            'C45 H37 N O6'
_chemical_formula_weight         687.75

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.12901(14)
_cell_length_b                   13.7793(2)
_cell_length_c                   27.6456(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3477.58(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    22668
_cell_measurement_theta_min      2.9430
_cell_measurement_theta_max      25.9920

_exptl_crystal_description       block
_exptl_crystal_colour            volourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.94403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'90 images, ΔΦ 3.0° '
'49 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49534
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.056
_diffrn_reflns_theta_max         26.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6821
_reflns_number_gt                6484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     dual
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;



_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)+(0.0306P)²+0.9988P] where P=(Fo²+2Fc²)/3'
_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 2691 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.29(19)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6821
_refine_ls_number_parameters     668
_refine_ls_number_restraints     254
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8581(2) 0.40257(16) 0.61295(7) 0.0523(5) Uani 1 1 d . . . . .
H1 H 0.875985 0.387825 0.584822 0.078 Uiso 1 1 calc R U . . .
C2 C 0.7140(3) 0.42783(18) 0.61703(9) 0.0387(5) Uani 1 1 d . . . . .
C3 C 0.6442(3) 0.3969(2) 0.65977(9) 0.0479(7) Uani 1 1 d . . . . .
H3 H 0.696178 0.360373 0.682256 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5021(4) 0.4197(2) 0.66857(10) 0.0506(7) Uani 1 1 d . . . . .
H4 H 0.458192 0.399395 0.697199 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4201(3) 0.4739(2) 0.63465(10) 0.0434(6) Uani 1 1 d . . . . .
C6 C 0.2706(4) 0.4974(2) 0.64178(12) 0.0578(8) Uani 1 1 d . . . . .
H6 H 0.224336 0.477383 0.670027 0.069 Uiso 1 1 calc R U . . .
C7 C 0.1929(4) 0.5487(3) 0.60831(13) 0.0644(9) Uani 1 1 d . . . . .
H7 H 0.094262 0.562119 0.613419 0.077 Uiso 1 1 calc R U . . .
C8 C 0.2629(4) 0.5810(3) 0.56607(13) 0.0619(8) Uani 1 1 d . . . . .
H8 H 0.210790 0.617373 0.543577 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4068(3) 0.5595(2) 0.55763(11) 0.0486(7) Uani 1 1 d . . . . .
H9 H 0.450882 0.580659 0.529192 0.058 Uiso 1 1 calc R U . . .
C10 C 0.4900(3) 0.50541(19) 0.59157(9) 0.0379(5) Uani 1 1 d . . . . .
C11 C 0.6412(3) 0.48361(18) 0.58361(9) 0.0356(5) Uani 1 1 d . . . . .
C12 C 0.7215(3) 0.52510(18) 0.54125(9) 0.0375(5) Uani 1 1 d . . . . .
C13 C 0.8026(3) 0.61323(19) 0.54631(10) 0.0416(6) Uani 1 1 d . . . . .
C14 C 0.8041(4) 0.6671(2) 0.58970(12) 0.0548(7) Uani 1 1 d . . . . .
H14 H 0.749100 0.646120 0.616015 0.066 Uiso 1 1 calc R U . . .
C15 C 0.8860(5) 0.7501(2) 0.59337(15) 0.0730(10) Uani 1 1 d . . . . .
H15 H 0.883902 0.785963 0.621839 0.088 Uiso 1 1 calc R U . . .
C16 C 0.9735(4) 0.7815(3) 0.55444(17) 0.0759(11) Uani 1 1 d . . . . .
H16 H 1.032441 0.836078 0.557920 0.091 Uiso 1 1 calc R U . . .
C17 C 0.9720(4) 0.7328(2) 0.51218(16) 0.0656(9) Uani 1 1 d . . . . .
H17 H 1.028727 0.755030 0.486520 0.079 Uiso 1 1 calc R U . . .
C18 C 0.8856(3) 0.6486(2) 0.50626(12) 0.0488(7) Uani 1 1 d . . . . .
C19 C 0.8788(3) 0.5981(2) 0.46170(11) 0.0552(8) Uani 1 1 d . . . . .
H19 H 0.930971 0.621361 0.435234 0.066 Uiso 1 1 calc R U . . .
C20 C 0.7977(3) 0.5167(2) 0.45706(10) 0.0523(7) Uani 1 1 d . . . . .
H20 H 0.793842 0.484606 0.427492 0.063 Uiso 1 1 calc R U . . .
C21 C 0.7189(3) 0.4802(2) 0.49685(9) 0.0419(6) Uani 1 1 d . . . . .
O22 O 0.6425(2) 0.39666(15) 0.48827(7) 0.0536(5) Uani 1 1 d . . . . .
H22 H 0.601097 0.379445 0.513142 0.080 Uiso 1 1 calc R U . . .
O31 O 0.6413(3) 0.1814(2) 0.70786(13) 0.0683(10) Uani 0.772(4) 1 d D . P A 1
H31 H 0.569686 0.214205 0.700568 0.102 Uiso 0.772(4) 1 calc R U P A 1
C32 C 0.6089(7) 0.0855(4) 0.7022(4) 0.0452(12) Uani 0.772(4) 1 d D . P A 1
C33 C 0.7269(8) 0.0201(5) 0.7107(3) 0.0558(15) Uani 0.772(4) 1 d D . P A 1
H33 H 0.818393 0.044058 0.719495 0.067 Uiso 0.772(4) 1 calc R U P A 1
C34 C 0.7069(6) -0.0761(4) 0.7062(2) 0.0574(12) Uani 0.772(4) 1 d D . P A 1
H34 H 0.783851 -0.118256 0.712818 0.069 Uiso 0.772(4) 1 calc R U P A 1
C35 C 0.5696(11) -0.1141(5) 0.6914(7) 0.053(2) Uani 0.772(4) 1 d D . P A 1
C36 C 0.5455(8) -0.2149(4) 0.6863(2) 0.0747(16) Uani 0.772(4) 1 d D . P A 1
H36 H 0.621411 -0.257877 0.692968 0.090 Uiso 0.772(4) 1 calc R U P A 1
C37 C 0.4132(8) -0.2501(4) 0.6719(2) 0.0880(18) Uani 0.772(4) 1 d D . P A 1
H37 H 0.399473 -0.316579 0.668180 0.106 Uiso 0.772(4) 1 calc R U P A 1
C38 C 0.2984(10) -0.1858(5) 0.6627(6) 0.075(2) Uani 0.772(4) 1 d D . P A 1
H38 H 0.208822 -0.210118 0.652132 0.090 Uiso 0.772(4) 1 calc R U P A 1
C39 C 0.3145(8) -0.0887(4) 0.6688(3) 0.0538(15) Uani 0.772(4) 1 d D . P A 1
H39 H 0.234834 -0.047819 0.663814 0.065 Uiso 0.772(4) 1 calc R U P A 1
C40 C 0.4514(5) -0.0486(3) 0.68254(17) 0.0426(10) Uani 0.772(4) 1 d D . P A 1
C41 C 0.4732(4) 0.0531(3) 0.68797(12) 0.0380(8) Uani 0.772(4) 1 d D . P A 1
C42 C 0.3530(4) 0.1247(3) 0.68038(13) 0.0367(8) Uani 0.772(4) 1 d D . P A 1
C43 C 0.2376(5) 0.1343(3) 0.71531(15) 0.0391(10) Uani 0.772(4) 1 d D . P A 1
C44 C 0.2292(5) 0.0756(3) 0.75743(14) 0.0468(10) Uani 0.772(4) 1 d D . P A 1
H44 H 0.300747 0.028715 0.762726 0.056 Uiso 0.772(4) 1 calc R U P A 1
C45 C 0.1205(8) 0.0860(6) 0.7898(2) 0.0577(18) Uani 0.772(4) 1 d D . P A 1
H45 H 0.117553 0.046018 0.816918 0.069 Uiso 0.772(4) 1 calc R U P A 1
C46 C 0.0122(15) 0.1562(9) 0.7833(5) 0.062(2) Uani 0.772(4) 1 d D . P A 1
H46 H -0.061109 0.163695 0.806311 0.074 Uiso 0.772(4) 1 calc R U P A 1
C47 C 0.0135(17) 0.2139(9) 0.7431(4) 0.056(2) Uani 0.772(4) 1 d D . P A 1
H47 H -0.060093 0.259744 0.738702 0.068 Uiso 0.772(4) 1 calc R U P A 1
C48 C 0.1258(16) 0.2044(8) 0.7082(4) 0.043(2) Uani 0.772(4) 1 d D . P A 1
C49 C 0.1287(17) 0.2624(9) 0.6657(4) 0.045(2) Uani 0.772(4) 1 d D . P A 1
H49 H 0.055349 0.308126 0.660594 0.054 Uiso 0.772(4) 1 calc R U P A 1
C50 C 0.2361(15) 0.2521(8) 0.6327(4) 0.0416(18) Uani 0.772(4) 1 d D . P A 1
H50 H 0.235442 0.289792 0.604755 0.050 Uiso 0.772(4) 1 calc R U P A 1
C51 C 0.3498(5) 0.1841(3) 0.64038(16) 0.0367(12) Uani 0.772(4) 1 d D . P A 1
O52 O 0.4611(4) 0.1763(3) 0.60743(15) 0.0474(9) Uani 0.772(4) 1 d D . P A 1
H52 H 0.446334 0.213795 0.584927 0.071 Uiso 0.772(4) 1 calc R U P A 1
O31B O 0.1307(11) -0.0764(8) 0.6489(4) 0.078(4) Uani 0.228(4) 1 d D U P A 2
H31B H 0.102936 -0.019964 0.651306 0.117 Uiso 0.228(4) 1 calc R U P A 2
C32B C 0.2757(19) -0.0815(12) 0.6598(12) 0.051(5) Uani 0.228(4) 1 d D U P A 2
C33B C 0.335(3) -0.1772(14) 0.6592(19) 0.072(8) Uani 0.228(4) 1 d D U P A 2
H33B H 0.277276 -0.229399 0.649527 0.086 Uiso 0.228(4) 1 calc R U P A 2
C34B C 0.4738(18) -0.1910(11) 0.6727(7) 0.073(4) Uani 0.228(4) 1 d D U P A 2
H34B H 0.514348 -0.252822 0.670981 0.088 Uiso 0.228(4) 1 calc R U P A 2
C35B C 0.560(4) -0.1126(15) 0.690(3) 0.063(9) Uani 0.228(4) 1 d D U P A 2
C36B C 0.7072(18) -0.1268(14) 0.7039(8) 0.079(5) Uani 0.228(4) 1 d D U P A 2
H36B H 0.746637 -0.189022 0.703991 0.095 Uiso 0.228(4) 1 calc R U P A 2
C37B C 0.791(2) -0.0502(15) 0.7174(8) 0.091(5) Uani 0.228(4) 1 d D U P A 2
H37B H 0.888987 -0.060184 0.725827 0.109 Uiso 0.228(4) 1 calc R U P A 2
C38B C 0.733(3) 0.0434(17) 0.7189(16) 0.079(8) Uani 0.228(4) 1 d D U P A 2
H38B H 0.786935 0.093826 0.732290 0.095 Uiso 0.228(4) 1 calc R U P A 2
C39B C 0.597(3) 0.0611(14) 0.7008(17) 0.071(7) Uani 0.228(4) 1 d D U P A 2
H39B H 0.565400 0.124847 0.696660 0.085 Uiso 0.228(4) 1 calc R U P A 2
C40B C 0.5026(12) -0.0162(10) 0.6881(6) 0.049(4) Uani 0.228(4) 1 d D U P A 2
C41B C 0.3550(11) -0.0022(7) 0.6744(4) 0.045(3) Uani 0.228(4) 1 d D U P A 2
C42B C 0.2858(14) 0.0953(8) 0.6756(4) 0.040(3) Uani 0.228(4) 1 d D U P A 2
C43B C 0.1825(16) 0.1155(10) 0.7135(4) 0.043(4) Uani 0.228(4) 1 d D U P A 2
C44B C 0.1609(16) 0.0516(11) 0.7530(4) 0.046(3) Uani 0.228(4) 1 d D U P A 2
H44B H 0.210178 -0.007457 0.753390 0.055 Uiso 0.228(4) 1 calc R U P A 2
C45B C 0.072(2) 0.0739(18) 0.7897(7) 0.057(6) Uani 0.228(4) 1 d D U P A 2
H45B H 0.067817 0.033931 0.816796 0.068 Uiso 0.228(4) 1 calc R U P A 2
C46B C -0.015(5) 0.157(3) 0.7875(14) 0.053(7) Uani 0.228(4) 1 d D U P A 2
H46B H -0.087563 0.167227 0.810659 0.063 Uiso 0.228(4) 1 calc R U P A 2
C47B C 0.005(5) 0.223(3) 0.7514(14) 0.050(6) Uani 0.228(4) 1 d D U P A 2
H47B H -0.046418 0.281698 0.751971 0.060 Uiso 0.228(4) 1 calc R U P A 2
C48B C 0.104(5) 0.204(3) 0.7132(13) 0.038(6) Uani 0.228(4) 1 d D U P A 2
C49B C 0.124(6) 0.268(3) 0.6734(16) 0.044(7) Uani 0.228(4) 1 d D U P A 2
H49B H 0.065873 0.323412 0.671042 0.053 Uiso 0.228(4) 1 calc R U P A 2
C50B C 0.225(6) 0.250(3) 0.6391(16) 0.050(8) Uani 0.228(4) 1 d D U P A 2
H50B H 0.241252 0.295620 0.614809 0.060 Uiso 0.228(4) 1 calc R U P A 2
C51B C 0.3068(19) 0.1628(11) 0.6399(6) 0.044(5) Uani 0.228(4) 1 d D U P A 2
O52B O 0.4109(18) 0.1462(12) 0.6050(6) 0.064(4) Uani 0.228(4) 1 d D U P A 2
H52B H 0.431914 0.197473 0.591654 0.096 Uiso 0.228(4) 1 calc R U P A 2
N61 N 0.2114(3) 0.38224(17) 0.48114(8) 0.0467(5) Uani 1 1 d . . . . .
H61A H 0.121223 0.365830 0.490196 0.056 Uiso 1 1 calc R U . . .
H61B H 0.262329 0.398296 0.507402 0.056 Uiso 1 1 calc R U . . .
C62 C 0.2061(4) 0.4654(2) 0.44695(12) 0.0557(7) Uani 1 1 d . . . . .
H62A H 0.206365 0.526794 0.464100 0.067 Uiso 1 1 calc R U . . .
H62B H 0.119908 0.462105 0.426491 0.067 Uiso 1 1 calc R U . . .
C63 C 0.3440(4) 0.4525(2) 0.41788(12) 0.0614(8) Uani 1 1 d . . . . .
H63A H 0.337585 0.486591 0.387251 0.074 Uiso 1 1 calc R U . . .
H63B H 0.428686 0.476014 0.435538 0.074 Uiso 1 1 calc R U . . .
C64 C 0.3527(4) 0.3448(2) 0.41023(11) 0.0564(8) Uani 1 1 d . . . . .
H64A H 0.453790 0.324361 0.406675 0.068 Uiso 1 1 calc R U . . .
H64B H 0.298911 0.326089 0.381444 0.068 Uiso 1 1 calc R U . . .
C65 C 0.2838(3) 0.29878(19) 0.45559(9) 0.0402(6) Uani 1 1 d . . . . .
H65 H 0.209208 0.251505 0.445818 0.048 Uiso 1 1 calc R U . . .
C66 C 0.3936(3) 0.2501(2) 0.48942(9) 0.0399(6) Uani 1 1 d . . . . .
O67 O 0.4176(2) 0.29037(15) 0.52946(7) 0.0496(5) Uani 1 1 d . . . . .
O68 O 0.4548(2) 0.17485(14) 0.47429(7) 0.0474(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.365(3) . ?
O1 H1 0.8200 . ?
C2 C11 1.374(4) . ?
C2 C3 1.409(4) . ?
C3 C4 1.357(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(4) . ?
C5 C10 1.419(4) . ?
C6 C7 1.363(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.418(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.430(4) . ?
C11 C12 1.495(3) . ?
C12 C21 1.374(4) . ?
C12 C13 1.429(4) . ?
C13 C14 1.411(4) . ?
C13 C18 1.427(4) . ?
C14 C15 1.370(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.347(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.416(5) . ?
C19 C20 1.351(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.407(4) . ?
C20 H20 0.9300 . ?
C21 O22 1.367(3) . ?
O22 H22 0.8200 . ?
O31 C32 1.363(6) . ?
O31 H31 0.8200 . ?
C32 C41 1.374(6) . ?
C32 C33 1.425(7) . ?
C33 C34 1.344(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.418(11) . ?
C34 H34 0.9300 . ?
C35 C36 1.413(9) . ?
C35 C40 1.428(6) . ?
C36 C37 1.362(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.396(10) . ?
C37 H37 0.9300 . ?
C38 C39 1.358(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.418(7) . ?
C39 H39 0.9300 . ?
C40 C41 1.424(5) . ?
C41 C42 1.491(5) . ?
C42 C51 1.376(5) . ?
C42 C43 1.435(5) . ?
C43 C48 1.419(7) . ?
C43 C44 1.420(5) . ?
C44 C45 1.344(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.395(7) . ?
C45 H45 0.9300 . ?
C46 C47 1.365(7) . ?
C46 H46 0.9300 . ?
C47 C48 1.415(8) . ?
C47 H47 0.9300 . ?
C48 C49 1.421(6) . ?
C49 C50 1.347(7) . ?
C49 H49 0.9300 . ?
C50 C51 1.415(7) . ?
C50 H50 0.9300 . ?
C51 O52 1.369(5) . ?
O52 H52 0.8200 . ?
O31B C32B 1.359(13) . ?
O31B H31B 0.8200 . ?
C32B C41B 1.372(13) . ?
C32B C33B 1.424(15) . ?
C33B C34B 1.337(15) . ?
C33B H33B 0.9300 . ?
C34B C35B 1.417(18) . ?
C34B H34B 0.9300 . ?
C35B C36B 1.414(15) . ?
C35B C40B 1.429(12) . ?
C36B C37B 1.358(15) . ?
C36B H36B 0.9300 . ?
C37B C38B 1.397(16) . ?
C37B H37B 0.9300 . ?
C38B C39B 1.362(16) . ?
C38B H38B 0.9300 . ?
C39B C40B 1.412(13) . ?
C39B H39B 0.9300 . ?
C40B C41B 1.413(11) . ?
C41B C42B 1.485(10) . ?
C42B C51B 1.370(11) . ?
C42B C43B 1.435(11) . ?
C43B C48B 1.419(12) . ?
C43B C44B 1.417(11) . ?
C44B C45B 1.337(12) . ?
C44B H44B 0.9300 . ?
C45B C46B 1.396(13) . ?
C45B H45B 0.9300 . ?
C46B C47B 1.367(13) . ?
C46B H46B 0.9300 . ?
C47B C48B 1.411(13) . ?
C47B H47B 0.9300 . ?
C48B C49B 1.421(12) . ?
C49B C50B 1.346(12) . ?
C49B H49B 0.9300 . ?
C50B C51B 1.419(12) . ?
C50B H50B 0.9300 . ?
C51B O52B 1.374(11) . ?
O52B H52B 0.8200 . ?
N61 C62 1.486(4) . ?
N61 C65 1.502(3) . ?
N61 H61A 0.8900 . ?
N61 H61B 0.8900 . ?
C62 C63 1.504(5) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 C64 1.501(5) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 C65 1.540(4) . ?
C64 H64A 0.9700 . ?
C64 H64B 0.9700 . ?
C65 C66 1.526(4) . ?
C65 H65 0.9800 . ?
C66 O68 1.250(3) . ?
C66 O67 1.257(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
O1 C2 C11 123.6(2) . . ?
O1 C2 C3 115.4(2) . . ?
C11 C2 C3 121.0(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 C10 118.7(3) . . ?
C6 C5 C10 118.7(3) . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 118.4(3) . . ?
C9 C10 C11 121.7(2) . . ?
C5 C10 C11 119.9(2) . . ?
C2 C11 C10 118.8(2) . . ?
C2 C11 C12 120.2(2) . . ?
C10 C11 C12 120.9(2) . . ?
C21 C12 C13 118.6(2) . . ?
C21 C12 C11 121.3(2) . . ?
C13 C12 C11 120.2(2) . . ?
C14 C13 C18 118.4(3) . . ?
C14 C13 C12 122.4(3) . . ?
C18 C13 C12 119.3(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 121.9(3) . . ?
C17 C18 C13 119.1(3) . . ?
C19 C18 C13 118.9(3) . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
O22 C21 C12 122.9(2) . . ?
O22 C21 C20 115.2(2) . . ?
C12 C21 C20 121.9(3) . . ?
C21 O22 H22 109.5 . . ?
C32 O31 H31 109.5 . . ?
O31 C32 C41 122.9(4) . . ?
O31 C32 C33 115.5(5) . . ?
C41 C32 C33 121.6(5) . . ?
C34 C33 C32 120.3(6) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.8(5) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 121.9(5) . . ?
C36 C35 C40 119.1(7) . . ?
C34 C35 C40 119.0(6) . . ?
C37 C36 C35 121.2(6) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C36 C37 C38 119.6(6) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 121.4(7) . . ?
C39 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C38 C39 C40 120.9(6) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C39 C40 C41 122.3(4) . . ?
C39 C40 C35 117.8(5) . . ?
C41 C40 C35 119.9(5) . . ?
C32 C41 C40 118.4(4) . . ?
C32 C41 C42 119.3(4) . . ?
C40 C41 C42 122.3(3) . . ?
C51 C42 C43 118.1(3) . . ?
C51 C42 C41 121.5(3) . . ?
C43 C42 C41 120.5(3) . . ?
C48 C43 C44 117.6(4) . . ?
C48 C43 C42 119.8(4) . . ?
C44 C43 C42 122.6(4) . . ?
C45 C44 C43 121.7(4) . . ?
C45 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?
C44 C45 C46 120.7(5) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C47 C46 C45 120.3(6) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C46 C47 C48 120.5(7) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C47 C48 C43 119.3(5) . . ?
C47 C48 C49 121.7(6) . . ?
C43 C48 C49 118.9(5) . . ?
C50 C49 C48 121.0(6) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C49 C50 C51 120.1(6) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
O52 C51 C42 118.2(4) . . ?
O52 C51 C50 119.8(4) . . ?
C42 C51 C50 122.0(4) . . ?
C51 O52 H52 109.5 . . ?
C32B O31B H31B 109.5 . . ?
O31B C32B C41B 122.5(13) . . ?
O31B C32B C33B 114.5(13) . . ?
C41B C32B C33B 122.8(12) . . ?
C34B C33B C32B 119.2(15) . . ?
C34B C33B H33B 120.4 . . ?
C32B C33B H33B 120.4 . . ?
C33B C34B C35B 120.7(14) . . ?
C33B C34B H34B 119.6 . . ?
C35B C34B H34B 119.6 . . ?
C36B C35B C34B 121.0(14) . . ?
C36B C35B C40B 119.1(16) . . ?
C34B C35B C40B 119.7(14) . . ?
C37B C36B C35B 120.5(15) . . ?
C37B C36B H36B 119.8 . . ?
C35B C36B H36B 119.8 . . ?
C36B C37B C38B 120.5(15) . . ?
C36B C37B H37B 119.7 . . ?
C38B C37B H37B 119.7 . . ?
C39B C38B C37B 120.4(17) . . ?
C39B C38B H38B 119.8 . . ?
C37B C38B H38B 119.8 . . ?
C38B C39B C40B 120.7(17) . . ?
C38B C39B H39B 119.7 . . ?
C40B C39B H39B 119.7 . . ?
C39B C40B C41B 122.9(13) . . ?
C39B C40B C35B 118.1(13) . . ?
C41B C40B C35B 119.0(12) . . ?
C32B C41B C40B 118.3(10) . . ?
C32B C41B C42B 120.2(11) . . ?
C40B C41B C42B 121.5(10) . . ?
C51B C42B C43B 119.1(9) . . ?
C51B C42B C41B 122.5(9) . . ?
C43B C42B C41B 118.2(9) . . ?
C48B C43B C44B 117.9(10) . . ?
C48B C43B C42B 119.8(10) . . ?
C44B C43B C42B 122.2(10) . . ?
C45B C44B C43B 121.9(12) . . ?
C45B C44B H44B 119.1 . . ?
C43B C44B H44B 119.1 . . ?
C44B C45B C46B 120.1(14) . . ?
C44B C45B H45B 119.9 . . ?
C46B C45B H45B 119.9 . . ?
C47B C46B C45B 120.3(15) . . ?
C47B C46B H46B 119.9 . . ?
C45B C46B H46B 119.9 . . ?
C46B C47B C48B 120.4(15) . . ?
C46B C47B H47B 119.8 . . ?
C48B C47B H47B 119.8 . . ?
C47B C48B C43B 118.8(12) . . ?
C47B C48B C49B 123.0(13) . . ?
C43B C48B C49B 118.1(13) . . ?
C50B C49B C48B 121.4(14) . . ?
C50B C49B H49B 119.3 . . ?
C48B C49B H49B 119.3 . . ?
C49B C50B C51B 120.4(15) . . ?
C49B C50B H50B 119.8 . . ?
C51B C50B H50B 119.8 . . ?
C42B C51B O52B 119.4(11) . . ?
C42B C51B C50B 120.9(11) . . ?
O52B C51B C50B 119.7(12) . . ?
C51B O52B H52B 109.5 . . ?
C62 N61 C65 107.8(2) . . ?
C62 N61 H61A 110.1 . . ?
C65 N61 H61A 110.1 . . ?
C62 N61 H61B 110.1 . . ?
C65 N61 H61B 110.1 . . ?
H61A N61 H61B 108.5 . . ?
N61 C62 C63 102.8(2) . . ?
N61 C62 H62A 111.2 . . ?
C63 C62 H62A 111.2 . . ?
N61 C62 H62B 111.2 . . ?
C63 C62 H62B 111.2 . . ?
H62A C62 H62B 109.1 . . ?
C64 C63 C62 103.7(3) . . ?
C64 C63 H63A 111.0 . . ?
C62 C63 H63A 111.0 . . ?
C64 C63 H63B 111.0 . . ?
C62 C63 H63B 111.0 . . ?
H63A C63 H63B 109.0 . . ?
C63 C64 C65 105.7(2) . . ?
C63 C64 H64A 110.6 . . ?
C65 C64 H64A 110.6 . . ?
C63 C64 H64B 110.6 . . ?
C65 C64 H64B 110.6 . . ?
H64A C64 H64B 108.7 . . ?
N61 C65 C66 109.7(2) . . ?
N61 C65 C64 104.3(2) . . ?
C66 C65 C64 114.3(2) . . ?
N61 C65 H65 109.5 . . ?
C66 C65 H65 109.5 . . ?
C64 C65 H65 109.5 . . ?
O68 C66 O67 125.6(3) . . ?
O68 C66 C65 116.9(2) . . ?
O67 C66 C65 117.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.3(3) . . . . ?
C11 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 178.5(3) . . . . ?
C3 C4 C5 C10 -1.0(4) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
C6 C7 C8 C9 1.7(5) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
C8 C9 C10 C11 -179.0(3) . . . . ?
C4 C5 C10 C9 179.8(3) . . . . ?
C6 C5 C10 C9 0.3(4) . . . . ?
C4 C5 C10 C11 -1.2(4) . . . . ?
C6 C5 C10 C11 179.4(3) . . . . ?
O1 C2 C11 C10 179.9(2) . . . . ?
C3 C2 C11 C10 -3.5(4) . . . . ?
O1 C2 C11 C12 -3.5(4) . . . . ?
C3 C2 C11 C12 173.1(3) . . . . ?
C9 C10 C11 C2 -177.6(2) . . . . ?
C5 C10 C11 C2 3.4(4) . . . . ?
C9 C10 C11 C12 5.8(4) . . . . ?
C5 C10 C11 C12 -173.2(2) . . . . ?
C2 C11 C12 C21 97.5(3) . . . . ?
C10 C11 C12 C21 -86.0(3) . . . . ?
C2 C11 C12 C13 -82.8(3) . . . . ?
C10 C11 C12 C13 93.8(3) . . . . ?
C21 C12 C13 C14 176.1(3) . . . . ?
C11 C12 C13 C14 -3.6(4) . . . . ?
C21 C12 C13 C18 -3.9(4) . . . . ?
C11 C12 C13 C18 176.3(2) . . . . ?
C18 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C15 178.5(3) . . . . ?
C13 C14 C15 C16 -1.9(5) . . . . ?
C14 C15 C16 C17 3.3(6) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C16 C17 C18 C19 177.9(3) . . . . ?
C16 C17 C18 C13 -2.0(5) . . . . ?
C14 C13 C18 C17 3.3(4) . . . . ?
C12 C13 C18 C17 -176.6(2) . . . . ?
C14 C13 C18 C19 -176.6(3) . . . . ?
C12 C13 C18 C19 3.4(4) . . . . ?
C17 C18 C19 C20 178.8(3) . . . . ?
C13 C18 C19 C20 -1.3(4) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C13 C12 C21 O22 -178.9(2) . . . . ?
C11 C12 C21 O22 0.8(4) . . . . ?
C13 C12 C21 C20 2.3(4) . . . . ?
C11 C12 C21 C20 -177.9(2) . . . . ?
C19 C20 C21 O22 -179.0(3) . . . . ?
C19 C20 C21 C12 -0.1(4) . . . . ?
O31 C32 C33 C34 179.9(8) . . . . ?
C41 C32 C33 C34 -1.7(15) . . . . ?
C32 C33 C34 C35 2.0(16) . . . . ?
C33 C34 C35 C36 180.0(12) . . . . ?
C33 C34 C35 C40 -2(2) . . . . ?
C34 C35 C36 C37 -179.7(11) . . . . ?
C40 C35 C36 C37 2(2) . . . . ?
C35 C36 C37 C38 -1.1(15) . . . . ?
C36 C37 C38 C39 -1.4(17) . . . . ?
C37 C38 C39 C40 3.0(19) . . . . ?
C38 C39 C40 C41 178.3(10) . . . . ?
C38 C39 C40 C35 -2.2(16) . . . . ?
C36 C35 C40 C39 0(2) . . . . ?
C34 C35 C40 C39 -178.8(12) . . . . ?
C36 C35 C40 C41 179.4(11) . . . . ?
C34 C35 C40 C41 1(2) . . . . ?
O31 C32 C41 C40 179.2(7) . . . . ?
C33 C32 C41 C40 1.0(12) . . . . ?
O31 C32 C41 C42 -2.8(11) . . . . ?
C33 C32 C41 C42 178.9(8) . . . . ?
C39 C40 C41 C32 179.0(7) . . . . ?
C35 C40 C41 C32 -0.5(12) . . . . ?
C39 C40 C41 C42 1.1(8) . . . . ?
C35 C40 C41 C42 -178.5(10) . . . . ?
C32 C41 C42 C51 74.4(7) . . . . ?
C40 C41 C42 C51 -107.7(5) . . . . ?
C32 C41 C42 C43 -104.7(6) . . . . ?
C40 C41 C42 C43 73.1(5) . . . . ?
C51 C42 C43 C48 -0.7(11) . . . . ?
C41 C42 C43 C48 178.5(10) . . . . ?
C51 C42 C43 C44 179.0(4) . . . . ?
C41 C42 C43 C44 -1.8(6) . . . . ?
C48 C43 C44 C45 -0.6(11) . . . . ?
C42 C43 C44 C45 179.7(5) . . . . ?
C43 C44 C45 C46 -0.6(13) . . . . ?
C44 C45 C46 C47 1(2) . . . . ?
C45 C46 C47 C48 -1(3) . . . . ?
C46 C47 C48 C43 0(3) . . . . ?
C46 C47 C48 C49 179(2) . . . . ?
C44 C43 C48 C47 1(2) . . . . ?
C42 C43 C48 C47 -179.4(13) . . . . ?
C44 C43 C48 C49 -178.2(14) . . . . ?
C42 C43 C48 C49 2(2) . . . . ?
C47 C48 C49 C50 -179.7(19) . . . . ?
C43 C48 C49 C50 -1(3) . . . . ?
C48 C49 C50 C51 -1(3) . . . . ?
C43 C42 C51 O52 178.9(4) . . . . ?
C41 C42 C51 O52 -0.3(6) . . . . ?
C43 C42 C51 C50 -1.0(11) . . . . ?
C41 C42 C51 C50 179.8(10) . . . . ?
C49 C50 C51 O52 -177.9(15) . . . . ?
C49 C50 C51 C42 2(2) . . . . ?
O31B C32B C33B C34B -175(4) . . . . ?
C41B C32B C33B C34B -1(7) . . . . ?
C32B C33B C34B C35B 3(7) . . . . ?
C33B C34B C35B C36B -180(5) . . . . ?
C33B C34B C35B C40B -6(9) . . . . ?
C34B C35B C36B C37B 176(5) . . . . ?
C40B C35B C36B C37B 2(9) . . . . ?
C35B C36B C37B C38B 2(6) . . . . ?
C36B C37B C38B C39B -9(6) . . . . ?
C37B C38B C39B C40B 11(7) . . . . ?
C38B C39B C40B C41B 173(3) . . . . ?
C38B C39B C40B C35B -7(7) . . . . ?
C36B C35B C40B C39B 0(9) . . . . ?
C34B C35B C40B C39B -174(5) . . . . ?
C36B C35B C40B C41B -179(5) . . . . ?
C34B C35B C40B C41B 6(9) . . . . ?
O31B C32B C41B C40B 176(2) . . . . ?
C33B C32B C41B C40B 2(5) . . . . ?
O31B C32B C41B C42B -4(4) . . . . ?
C33B C32B C41B C42B -178(3) . . . . ?
C39B C40B C41B C32B 176(3) . . . . ?
C35B C40B C41B C32B -4(5) . . . . ?
C39B C40B C41B C42B -4(3) . . . . ?
C35B C40B C41B C42B 175(4) . . . . ?
C32B C41B C42B C51B -101(2) . . . . ?
C40B C41B C42B C51B 79.8(19) . . . . ?
C32B C41B C42B C43B 73(2) . . . . ?
C40B C41B C42B C43B -106.2(16) . . . . ?
C51B C42B C43B C48B 0(4) . . . . ?
C41B C42B C43B C48B -174(3) . . . . ?
C51B C42B C43B C44B -176.4(16) . . . . ?
C41B C42B C43B C44B 9(2) . . . . ?
C48B C43B C44B C45B -1(4) . . . . ?
C42B C43B C44B C45B 175.4(18) . . . . ?
C43B C44B C45B C46B 7(4) . . . . ?
C44B C45B C46B C47B -10(8) . . . . ?
C45B C46B C47B C48B 7(10) . . . . ?
C46B C47B C48B C43B -1(9) . . . . ?
C46B C47B C48B C49B 177(7) . . . . ?
C44B C43B C48B C47B -2(7) . . . . ?
C42B C43B C48B C47B -179(4) . . . . ?
C44B C43B C48B C49B -179(5) . . . . ?
C42B C43B C48B C49B 4(7) . . . . ?
C47B C48B C49B C50B 176(7) . . . . ?
C43B C48B C49B C50B -6(10) . . . . ?
C48B C49B C50B C51B 5(12) . . . . ?
C43B C42B C51B O52B 176.7(15) . . . . ?
C41B C42B C51B O52B -9(3) . . . . ?
C43B C42B C51B C50B -2(4) . . . . ?
C41B C42B C51B C50B 172(4) . . . . ?
C49B C50B C51B C42B -1(9) . . . . ?
C49B C50B C51B O52B -179(6) . . . . ?
C65 N61 C62 C63 -33.2(3) . . . . ?
N61 C62 C63 C64 39.9(3) . . . . ?
C62 C63 C64 C65 -32.1(3) . . . . ?
C62 N61 C65 C66 136.2(2) . . . . ?
C62 N61 C65 C64 13.4(3) . . . . ?
C63 C64 C65 N61 11.8(3) . . . . ?
C63 C64 C65 C66 -108.0(3) . . . . ?
N61 C65 C66 O68 174.9(2) . . . . ?
C64 C65 C66 O68 -68.4(3) . . . . ?
N61 C65 C66 O67 -6.9(3) . . . . ?
C64 C65 C66 O67 109.8(3) . . . . ?

_refine_diff_density_max         0.117
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: cooling from ethanol solution'
