# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_B_DAC_EtOAc
_database_code_depnum_ccdc_archive 'CCDC 2470279'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine"
_chemical_name_common            'BINOL +  DACH comme synonyms'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2, 0.5(C4 H8 O2), C6 H14 N2'
_chemical_formula_sum            'C28 H32 N2 O3'
_chemical_formula_weight         444.55

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                   8.1693(10)
_cell_length_b                   9.2052(9)
_cell_length_c                   16.684(2)
_cell_angle_alpha                96.026(9)
_cell_angle_beta                 95.209(10)
_cell_angle_gamma                102.224(9)
_cell_volume                     1211.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3710
_cell_measurement_theta_min      3.1250
_cell_measurement_theta_max      26.5270

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.94746
_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       
;
'100 images, ΔΦ 2.0° '
'100 images, ΔΦ 2.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18971
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_max         26.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4925
_reflns_number_gt                4085
_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 space'
_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)+(0.0508P)²+0.3517P] where P=(Fo²+2Fc²)/3'
_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         4925
_refine_ls_number_parameters     343
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.061
_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 0.56678(15) 0.48448(12) 0.87586(7) 0.0516(3) Uani 1 1 d . . . . .
H1 H 0.617(3) 0.4563(15) 0.8320(12) 0.077 Uiso 1 1 calc R U . . .
C2 C 0.51174(17) 0.61106(15) 0.86461(8) 0.0376(3) Uani 1 1 d . . . . .
C3 C 0.47767(18) 0.69249(17) 0.93562(9) 0.0422(3) Uani 1 1 d . . . . .
H3 H 0.494070 0.658054 0.985525 0.051 Uiso 1 1 calc R U . . .
C4 C 0.42107(18) 0.82089(16) 0.93153(9) 0.0422(3) Uani 1 1 d . . . . .
H4 H 0.396721 0.871444 0.978650 0.051 Uiso 1 1 calc R U . . .
C5 C 0.39866(16) 0.87875(15) 0.85707(9) 0.0385(3) Uani 1 1 d . . . . .
C6 C 0.34718(19) 1.01574(17) 0.85180(11) 0.0482(4) Uani 1 1 d . . . . .
H6 H 0.322538 1.067872 0.898347 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3332(2) 1.07231(18) 0.77980(12) 0.0543(4) Uani 1 1 d . . . . .
H7 H 0.300268 1.162667 0.777562 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3685(2) 0.99400(18) 0.70922(11) 0.0514(4) Uani 1 1 d . . . . .
H8 H 0.359837 1.033296 0.660275 0.062 Uiso 1 1 calc R U . . .
C9 C 0.41580(18) 0.85966(16) 0.71151(9) 0.0430(3) Uani 1 1 d . . . . .
H9 H 0.437088 0.808456 0.663883 0.052 Uiso 1 1 calc R U . . .
C10 C 0.43262(16) 0.79800(14) 0.78545(8) 0.0351(3) Uani 1 1 d . . . . .
C11 C 0.48457(16) 0.65916(14) 0.78979(8) 0.0339(3) Uani 1 1 d . . . . .
C12 C 0.51037(17) 0.56950(15) 0.71394(8) 0.0352(3) Uani 1 1 d . . . . .
C13 C 0.66621(18) 0.60868(16) 0.68001(9) 0.0406(3) Uani 1 1 d . . . . .
C14 C 0.80028(19) 0.72760(18) 0.71715(10) 0.0490(4) Uani 1 1 d . . . . .
H14 H 0.786017 0.785169 0.764154 0.059 Uiso 1 1 calc R U . . .
C15 C 0.9499(2) 0.7593(2) 0.68524(13) 0.0681(5) Uani 1 1 d . . . . .
H15 H 1.036276 0.837301 0.711087 0.082 Uiso 1 1 calc R U . . .
C16 C 0.9751(3) 0.6762(3) 0.61445(14) 0.0797(6) Uani 1 1 d . . . . .
H16 H 1.077530 0.698796 0.593216 0.096 Uiso 1 1 calc R U . . .
C17 C 0.8497(3) 0.5627(3) 0.57682(12) 0.0712(5) Uani 1 1 d . . . . .
H17 H 0.867061 0.509052 0.529122 0.085 Uiso 1 1 calc R U . . .
C18 C 0.6926(2) 0.52288(19) 0.60784(9) 0.0496(4) Uani 1 1 d . . . . .
C19 C 0.5627(2) 0.4014(2) 0.57168(10) 0.0581(4) Uani 1 1 d . . . . .
H19 H 0.578034 0.345179 0.524409 0.070 Uiso 1 1 calc R U . . .
C20 C 0.4148(2) 0.36437(18) 0.60456(10) 0.0525(4) Uani 1 1 d . . . . .
H20 H 0.331283 0.282914 0.579890 0.063 Uiso 1 1 calc R U . . .
C21 C 0.38773(18) 0.44927(16) 0.67609(9) 0.0399(3) Uani 1 1 d . . . . .
O22 O 0.23606(14) 0.40053(13) 0.70304(8) 0.0550(3) Uani 1 1 d . . . . .
H22 H 0.2235(12) 0.469(2) 0.7482(14) 0.083 Uiso 1 1 calc R U . . .
N31 N -0.25668(19) 0.33330(17) 0.77014(9) 0.0494(3) Uani 1 1 d . . . . .
H31A H -0.214(2) 0.380(2) 0.7320(12) 0.059 Uiso 1 1 d . U . . .
H31B H -0.334(2) 0.253(2) 0.7459(11) 0.059 Uiso 1 1 d . U . . .
C32 C -0.12160(17) 0.28169(15) 0.81647(9) 0.0381(3) Uani 1 1 d . . . . .
H32 H -0.054335 0.238629 0.778625 0.046 Uiso 1 1 calc R U . . .
C33 C -0.20352(19) 0.16171(17) 0.86571(11) 0.0488(4) Uani 1 1 d . . . . .
H33A H -0.280170 0.201118 0.898565 0.059 Uiso 1 1 calc R U . . .
H33B H -0.268967 0.076279 0.828988 0.059 Uiso 1 1 calc R U . . .
C34 C -0.0736(2) 0.11036(19) 0.92071(12) 0.0586(4) Uani 1 1 d . . . . .
H34A H -0.131112 0.039943 0.953877 0.070 Uiso 1 1 calc R U . . .
H34B H -0.006084 0.059089 0.887694 0.070 Uiso 1 1 calc R U . . .
C35 C 0.0405(2) 0.2413(2) 0.97506(11) 0.0598(4) Uani 1 1 d . . . . .
H35A H 0.127432 0.206165 1.006019 0.072 Uiso 1 1 calc R U . . .
H35B H -0.024645 0.284406 1.013052 0.072 Uiso 1 1 calc R U . . .
C36 C 0.12257(19) 0.36087(18) 0.92580(10) 0.0475(4) Uani 1 1 d . . . . .
H36A H 0.189545 0.445775 0.962387 0.057 Uiso 1 1 calc R U . . .
H36B H 0.197622 0.320808 0.892206 0.057 Uiso 1 1 calc R U . . .
C37 C -0.00823(17) 0.41321(15) 0.87211(9) 0.0387(3) Uani 1 1 d . . . . .
H37 H -0.077979 0.460551 0.906733 0.046 Uiso 1 1 calc R U . . .
N38 N 0.07810(18) 0.52507(16) 0.82355(10) 0.0496(3) Uani 1 1 d . . . . .
H38A H 0.004(2) 0.567(2) 0.7971(11) 0.059 Uiso 1 1 d . U . . .
H38B H 0.155(2) 0.601(2) 0.8581(11) 0.059 Uiso 1 1 d . U . . .
C41 C 1.0998(12) 0.9673(9) 0.4676(5) 0.0803(18) Uani 0.5 1 d . U P A 1
O42 O 1.2143(7) 1.0214(6) 0.5168(3) 0.1451(18) Uani 0.5 1 d . U P A 1
C43 C 1.1065(8) 0.8792(7) 0.3900(3) 0.1005(17) Uani 0.5 1 d . U P A 1
H43A H 1.217643 0.861230 0.387883 0.151 Uiso 0.5 1 calc R U P A 1
H43B H 1.080031 0.933352 0.346273 0.151 Uiso 0.5 1 calc R U P A 1
H43C H 1.026075 0.785137 0.385083 0.151 Uiso 0.5 1 calc R U P A 1
O44 O 0.9412(5) 0.9791(4) 0.4797(2) 0.0896(10) Uani 0.5 1 d . U P A 1
C45 C 0.9264(16) 1.0677(14) 0.5563(6) 0.119(3) Uani 0.5 1 d . U P A 1
H45A H 0.967102 1.173922 0.554071 0.143 Uiso 0.5 1 calc R U P A 1
H45B H 0.989785 1.038652 0.601629 0.143 Uiso 0.5 1 calc R U P A 1
C46 C 0.7412(11) 1.0315(11) 0.5639(5) 0.158(3) Uani 0.5 1 d . U P A 1
H46A H 0.682371 1.071114 0.521931 0.238 Uiso 0.5 1 calc R U P A 1
H46B H 0.721876 1.075595 0.615997 0.238 Uiso 0.5 1 calc R U P A 1
H46C H 0.700772 0.924809 0.558800 0.238 Uiso 0.5 1 calc R U P A 1


_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 1.3593(17) . ?
O1 H1 0.91(2) . ?
C2 C11 1.3824(19) . ?
C2 C3 1.4158(19) . ?
C3 C4 1.363(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.420(2) . ?
C5 C10 1.4207(19) . ?
C6 C7 1.363(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.400(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.4360(18) . ?
C11 C12 1.4932(18) . ?
C12 C21 1.377(2) . ?
C12 C13 1.4320(19) . ?
C13 C14 1.417(2) . ?
C13 C18 1.428(2) . ?
C14 C15 1.365(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.352(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.418(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.407(3) . ?
C19 C20 1.365(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.417(2) . ?
C20 H20 0.9300 . ?
C21 O22 1.3589(18) . ?
O22 H22 0.96(2) . ?
N31 C32 1.4781(19) . ?
N31 H31A 0.86(2) . ?
N31 H31B 0.90(2) . ?
C32 C37 1.523(2) . ?
C32 C33 1.523(2) . ?
C32 H32 0.9800 . ?
C33 C34 1.523(2) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.511(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.521(2) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.520(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 N38 1.4783(19) . ?
C37 H37 0.9800 . ?
N38 H38A 0.89(2) . ?
N38 H38B 0.94(2) . ?
C41 O42 1.172(9) . ?
C41 O44 1.354(11) . ?
C41 C43 1.465(9) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
O44 C45 1.471(9) . ?
C45 C46 1.499(15) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?

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 124.11(13) . . ?
O1 C2 C3 115.54(12) . . ?
C11 C2 C3 120.33(13) . . ?
C4 C3 C2 120.63(13) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.31(13) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 122.36(14) . . ?
C4 C5 C10 118.51(13) . . ?
C6 C5 C10 119.12(14) . . ?
C7 C6 C5 121.25(15) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.83(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.70(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.96(15) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 118.13(13) . . ?
C9 C10 C11 122.11(13) . . ?
C5 C10 C11 119.76(12) . . ?
C2 C11 C10 119.30(12) . . ?
C2 C11 C12 120.83(12) . . ?
C10 C11 C12 119.86(12) . . ?
C21 C12 C13 119.22(13) . . ?
C21 C12 C11 121.39(12) . . ?
C13 C12 C11 119.39(12) . . ?
C14 C13 C18 117.81(14) . . ?
C14 C13 C12 122.35(13) . . ?
C18 C13 C12 119.80(14) . . ?
C15 C14 C13 121.26(17) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.90(19) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.63(17) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 122.04(18) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 123.12(16) . . ?
C19 C18 C13 118.52(14) . . ?
C17 C18 C13 118.35(16) . . ?
C20 C19 C18 121.34(15) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 120.42(15) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O22 C21 C12 124.53(13) . . ?
O22 C21 C20 114.76(13) . . ?
C12 C21 C20 120.70(14) . . ?
C21 O22 H22 109.5 . . ?
C32 N31 H31A 108.3(13) . . ?
C32 N31 H31B 108.7(12) . . ?
H31A N31 H31B 106.8(17) . . ?
N31 C32 C37 109.86(12) . . ?
N31 C32 C33 108.31(12) . . ?
C37 C32 C33 110.59(12) . . ?
N31 C32 H32 109.4 . . ?
C37 C32 H32 109.4 . . ?
C33 C32 H32 109.4 . . ?
C34 C33 C32 112.04(13) . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C35 C34 C33 111.36(14) . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C36 111.20(14) . . ?
C34 C35 H35A 109.4 . . ?
C36 C35 H35A 109.4 . . ?
C34 C35 H35B 109.4 . . ?
C36 C35 H35B 109.4 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C35 111.59(13) . . ?
C37 C36 H36A 109.3 . . ?
C35 C36 H36A 109.3 . . ?
C37 C36 H36B 109.3 . . ?
C35 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
N38 C37 C36 109.39(12) . . ?
N38 C37 C32 110.17(12) . . ?
C36 C37 C32 110.91(12) . . ?
N38 C37 H37 108.8 . . ?
C36 C37 H37 108.8 . . ?
C32 C37 H37 108.8 . . ?
C37 N38 H38A 110.9(12) . . ?
C37 N38 H38B 109.4(11) . . ?
H38A N38 H38B 107.9(16) . . ?
O42 C41 O44 121.0(8) . . ?
O42 C41 C43 126.3(9) . . ?
O44 C41 C43 112.7(6) . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 O44 C45 115.3(6) . . ?
O44 C45 C46 104.1(8) . . ?
O44 C45 H45A 110.9 . . ?
C46 C45 H45A 110.9 . . ?
O44 C45 H45B 110.9 . . ?
C46 C45 H45B 110.9 . . ?
H45A C45 H45B 108.9 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.70(13) . . . . ?
C11 C2 C3 C4 -1.4(2) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C3 C4 C5 C6 -177.09(13) . . . . ?
C3 C4 C5 C10 1.5(2) . . . . ?
C4 C5 C6 C7 177.25(14) . . . . ?
C10 C5 C6 C7 -1.3(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C5 0.2(2) . . . . ?
C8 C9 C10 C11 -178.94(13) . . . . ?
C4 C5 C10 C9 -177.72(12) . . . . ?
C6 C5 C10 C9 0.93(19) . . . . ?
C4 C5 C10 C11 1.45(18) . . . . ?
C6 C5 C10 C11 -179.91(12) . . . . ?
O1 C2 C11 C10 -177.54(12) . . . . ?
C3 C2 C11 C10 4.3(2) . . . . ?
O1 C2 C11 C12 1.8(2) . . . . ?
C3 C2 C11 C12 -176.39(12) . . . . ?
C9 C10 C11 C2 174.81(12) . . . . ?
C5 C10 C11 C2 -4.32(19) . . . . ?
C9 C10 C11 C12 -4.53(19) . . . . ?
C5 C10 C11 C12 176.35(11) . . . . ?
C2 C11 C12 C21 82.28(17) . . . . ?
C10 C11 C12 C21 -98.39(15) . . . . ?
C2 C11 C12 C13 -97.37(16) . . . . ?
C10 C11 C12 C13 81.96(16) . . . . ?
C21 C12 C13 C14 -177.75(13) . . . . ?
C11 C12 C13 C14 1.9(2) . . . . ?
C21 C12 C13 C18 -0.1(2) . . . . ?
C11 C12 C13 C18 179.52(12) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C12 C13 C14 C15 177.55(15) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C19 -177.3(2) . . . . ?
C16 C17 C18 C13 1.6(3) . . . . ?
C14 C13 C18 C19 177.98(14) . . . . ?
C12 C13 C18 C19 0.2(2) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C12 C13 C18 C17 -178.66(15) . . . . ?
C17 C18 C19 C20 178.32(17) . . . . ?
C13 C18 C19 C20 -0.5(2) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C13 C12 C21 O22 179.20(13) . . . . ?
C11 C12 C21 O22 -0.4(2) . . . . ?
C13 C12 C21 C20 0.3(2) . . . . ?
C11 C12 C21 C20 -179.37(13) . . . . ?
C19 C20 C21 O22 -179.58(15) . . . . ?
C19 C20 C21 C12 -0.6(2) . . . . ?
N31 C32 C33 C34 -175.50(13) . . . . ?
C37 C32 C33 C34 -55.06(17) . . . . ?
C32 C33 C34 C35 54.7(2) . . . . ?
C33 C34 C35 C36 -54.4(2) . . . . ?
C34 C35 C36 C37 55.62(19) . . . . ?
C35 C36 C37 N38 -177.99(13) . . . . ?
C35 C36 C37 C32 -56.27(17) . . . . ?
N31 C32 C37 N38 -63.69(15) . . . . ?
C33 C32 C37 N38 176.81(12) . . . . ?
N31 C32 C37 C36 175.05(12) . . . . ?
C33 C32 C37 C36 55.55(15) . . . . ?
O42 C41 O44 C45 2.0(15) . . . . ?
C43 C41 O44 C45 -179.5(5) . . . . ?
C41 O44 C45 C46 -166.4(5) . . . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.030


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
####################################################################### 
# 
# 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_B_DAC_ACN
_database_code_depnum_ccdc_archive 'CCDC 2470281'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine"
_chemical_name_common            'BINOL +  DACH'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2, C6 H14 N2'
_chemical_formula_sum            'C26 H28 N2 O2'
_chemical_formula_weight         400.50

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.1707(5)
_cell_length_b                   29.731(2)
_cell_length_c                   9.0449(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.667(6)
_cell_angle_gamma                90
_cell_volume                     2151.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2997
_cell_measurement_theta_min      2.6560
_cell_measurement_theta_max      23.8780

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.03073
_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       
;
'130 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18727
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.677
_diffrn_reflns_theta_max         25.255
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3860
_reflns_number_gt                2505
_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 space'
_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)+(0.0460P)²+1.4404P] where P=(Fo²+2Fc²)/3'
_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         3860
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0831
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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 0.3225(3) 0.33359(8) 0.4614(2) 0.0580(7) Uani 1 1 d . . . . .
H1 H 0.289(3) 0.3543(13) 0.518(3) 0.087 Uiso 1 1 calc R U . . .
C3 C 0.5324(4) 0.27986(11) 0.4666(4) 0.0553(9) Uani 1 1 d . . . . .
H3 H 0.462853 0.265853 0.385642 0.066 Uiso 1 1 calc R U . . .
C2 C 0.4785(4) 0.31955(11) 0.5279(3) 0.0440(8) Uani 1 1 d . . . . .
C4 C 0.6844(4) 0.26192(11) 0.5244(4) 0.0563(9) Uani 1 1 d . . . . .
H4 H 0.717143 0.235696 0.482369 0.068 Uiso 1 1 calc R U . . .
C5 C 0.7937(4) 0.28214(11) 0.6466(4) 0.0502(8) Uani 1 1 d . . . . .
C6 C 0.9509(5) 0.26367(14) 0.7120(5) 0.0719(11) Uani 1 1 d . . . . .
H6 H 0.984137 0.236721 0.675023 0.086 Uiso 1 1 calc R U . . .
C7 C 1.0536(5) 0.28445(16) 0.8273(5) 0.0840(13) Uani 1 1 d . . . . .
H7 H 1.156086 0.271563 0.869629 0.101 Uiso 1 1 calc R U . . .
C8 C 1.0069(4) 0.32522(14) 0.8834(4) 0.0723(12) Uani 1 1 d . . . . .
H8 H 1.079363 0.339687 0.961523 0.087 Uiso 1 1 calc R U . . .
C9 C 0.8559(4) 0.34381(12) 0.8242(4) 0.0511(9) Uani 1 1 d . . . . .
H9 H 0.826413 0.370971 0.862600 0.061 Uiso 1 1 calc R U . . .
C10 C 0.7430(4) 0.32280(10) 0.7057(3) 0.0418(8) Uani 1 1 d . . . . .
C11 C 0.5820(4) 0.34167(10) 0.6441(3) 0.0378(7) Uani 1 1 d . . . . .
C12 C 0.5314(3) 0.38433(10) 0.7080(3) 0.0364(7) Uani 1 1 d . . . . .
C13 C 0.4742(3) 0.38383(10) 0.8476(3) 0.0363(7) Uani 1 1 d . . . . .
C14 C 0.4686(4) 0.34374(11) 0.9306(3) 0.0437(8) Uani 1 1 d . . . . .
H14 H 0.496721 0.316594 0.891126 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4228(4) 0.34413(12) 1.0676(4) 0.0500(9) Uani 1 1 d . . . . .
H15 H 0.422814 0.317420 1.121133 0.060 Uiso 1 1 calc R U . . .
C16 C 0.3759(4) 0.38416(13) 1.1282(4) 0.0529(9) Uani 1 1 d . . . . .
H16 H 0.345324 0.384125 1.221847 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3751(4) 0.42321(12) 1.0498(3) 0.0484(8) Uani 1 1 d . . . . .
H17 H 0.340181 0.449641 1.088904 0.058 Uiso 1 1 calc R U . . .
C18 C 0.4268(3) 0.42428(11) 0.9092(3) 0.0394(7) Uani 1 1 d . . . . .
C19 C 0.4352(4) 0.46478(10) 0.8290(3) 0.0443(8) Uani 1 1 d . . . . .
H19 H 0.401050 0.491546 0.866597 0.053 Uiso 1 1 calc R U . . .
C20 C 0.4925(4) 0.46526(10) 0.6979(4) 0.0451(8) Uani 1 1 d . . . . .
H20 H 0.498798 0.492302 0.647692 0.054 Uiso 1 1 calc R U . . .
C21 C 0.5427(4) 0.42473(11) 0.6374(3) 0.0408(7) Uani 1 1 d . . . . .
O22 O 0.5996(3) 0.42933(8) 0.5062(2) 0.0543(6) Uani 1 1 d . . . . .
H22 H 0.649(4) 0.4022(12) 0.484(2) 0.081 Uiso 1 1 calc R U . . .
N31 N 0.1190(4) 0.39632(12) 0.5655(3) 0.0562(8) Uani 1 1 d . . . . .
H31A H 0.051(4) 0.3803(12) 0.613(4) 0.067 Uiso 1 1 d . U . . .
H31B H 0.183(4) 0.4125(12) 0.631(4) 0.067 Uiso 1 1 d . U . . .
C32 C 0.0175(4) 0.42414(11) 0.4458(3) 0.0432(8) Uani 1 1 d . . . . .
H32 H -0.062510 0.441491 0.490081 0.052 Uiso 1 1 calc R U . . .
C33 C 0.1305(4) 0.45686(12) 0.3845(4) 0.0526(9) Uani 1 1 d . . . . .
H33A H 0.183468 0.476779 0.465076 0.063 Uiso 1 1 calc R U . . .
H33B H 0.217804 0.440162 0.350275 0.063 Uiso 1 1 calc R U . . .
C34 C 0.0353(4) 0.48469(12) 0.2551(4) 0.0597(10) Uani 1 1 d . . . . .
H34A H 0.113245 0.503266 0.214395 0.072 Uiso 1 1 calc R U . . .
H34B H -0.041704 0.504467 0.292336 0.072 Uiso 1 1 calc R U . . .
C35 C -0.0613(4) 0.45525(13) 0.1307(4) 0.0595(10) Uani 1 1 d . . . . .
H35A H 0.016231 0.438304 0.084144 0.071 Uiso 1 1 calc R U . . .
H35B H -0.128382 0.473994 0.053823 0.071 Uiso 1 1 calc R U . . .
C36 C -0.1742(4) 0.42296(12) 0.1938(3) 0.0521(9) Uani 1 1 d . . . . .
H36A H -0.259491 0.440029 0.229838 0.063 Uiso 1 1 calc R U . . .
H36B H -0.229855 0.403326 0.113575 0.063 Uiso 1 1 calc R U . . .
C37 C -0.0792(4) 0.39455(11) 0.3219(3) 0.0435(8) Uani 1 1 d . . . . .
H37 H -0.001458 0.374741 0.283460 0.052 Uiso 1 1 calc R U . . .
N38 N -0.2003(4) 0.36716(11) 0.3826(4) 0.0573(8) Uani 1 1 d . . . . .
H38A H -0.275(4) 0.3538(12) 0.302(4) 0.069 Uiso 1 1 d . U . . .
H38B H -0.148(4) 0.3440(12) 0.442(4) 0.069 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.361(4) . ?
O1 H1 0.88(4) . ?
C3 C4 1.355(5) . ?
C3 C2 1.411(4) . ?
C3 H3 0.9300 . ?
C2 C11 1.376(4) . ?
C4 C5 1.408(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 C10 1.417(4) . ?
C6 C7 1.349(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.411(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.435(4) . ?
C11 C12 1.487(4) . ?
C12 C21 1.372(4) . ?
C12 C13 1.432(4) . ?
C13 C18 1.412(4) . ?
C13 C14 1.414(4) . ?
C14 C15 1.365(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.396(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.419(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.415(4) . ?
C19 C20 1.360(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.418(4) . ?
C20 H20 0.9300 . ?
C21 O22 1.366(3) . ?
O22 H22 0.94(4) . ?
N31 C32 1.477(4) . ?
N31 H31A 0.90(4) . ?
N31 H31B 0.86(4) . ?
C32 C37 1.515(4) . ?
C32 C33 1.520(4) . ?
C32 H32 0.9800 . ?
C33 C34 1.514(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.515(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.520(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.514(4) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 N38 1.471(4) . ?
C37 H37 0.9800 . ?
N38 H38A 0.94(4) . ?
N38 H38B 0.92(4) . ?

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 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
O1 C2 C11 124.6(3) . . ?
O1 C2 C3 115.0(3) . . ?
C11 C2 C3 120.5(3) . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 122.8(3) . . ?
C4 C5 C10 118.2(3) . . ?
C6 C5 C10 118.9(3) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.4(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 117.9(3) . . ?
C9 C10 C11 122.0(3) . . ?
C5 C10 C11 120.1(3) . . ?
C2 C11 C10 118.9(3) . . ?
C2 C11 C12 121.9(3) . . ?
C10 C11 C12 119.2(3) . . ?
C21 C12 C13 119.0(3) . . ?
C21 C12 C11 121.0(3) . . ?
C13 C12 C11 120.0(3) . . ?
C18 C13 C14 117.8(3) . . ?
C18 C13 C12 120.2(3) . . ?
C14 C13 C12 121.9(3) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C19 118.5(3) . . ?
C13 C18 C17 119.3(3) . . ?
C19 C18 C17 122.2(3) . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
O22 C21 C12 124.0(3) . . ?
O22 C21 C20 115.2(3) . . ?
C12 C21 C20 120.8(3) . . ?
C21 O22 H22 109.5 . . ?
C32 N31 H31A 110(2) . . ?
C32 N31 H31B 112(2) . . ?
H31A N31 H31B 108(3) . . ?
N31 C32 C37 110.4(3) . . ?
N31 C32 C33 109.5(3) . . ?
C37 C32 C33 111.5(2) . . ?
N31 C32 H32 108.5 . . ?
C37 C32 H32 108.5 . . ?
C33 C32 H32 108.5 . . ?
C34 C33 C32 112.1(3) . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 C35 111.6(3) . . ?
C33 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C36 110.5(3) . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C37 C36 C35 112.5(3) . . ?
C37 C36 H36A 109.1 . . ?
C35 C36 H36A 109.1 . . ?
C37 C36 H36B 109.1 . . ?
C35 C36 H36B 109.1 . . ?
H36A C36 H36B 107.8 . . ?
N38 C37 C36 108.3(3) . . ?
N38 C37 C32 109.6(2) . . ?
C36 C37 C32 110.6(3) . . ?
N38 C37 H37 109.4 . . ?
C36 C37 H37 109.4 . . ?
C32 C37 H37 109.4 . . ?
C37 N38 H38A 109(2) . . ?
C37 N38 H38B 111(2) . . ?
H38A N38 H38B 107(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
C4 C3 C2 O1 -178.9(3) . . . . ?
C4 C3 C2 C11 2.3(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
C3 C4 C5 C10 -1.9(5) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
C10 C5 C6 C7 -1.1(6) . . . . ?
C5 C6 C7 C8 -0.8(7) . . . . ?
C6 C7 C8 C9 1.3(7) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C5 -1.9(5) . . . . ?
C8 C9 C10 C11 178.9(3) . . . . ?
C4 C5 C10 C9 -177.5(3) . . . . ?
C6 C5 C10 C9 2.4(5) . . . . ?
C4 C5 C10 C11 1.8(5) . . . . ?
C6 C5 C10 C11 -178.3(3) . . . . ?
O1 C2 C11 C10 179.0(3) . . . . ?
C3 C2 C11 C10 -2.3(4) . . . . ?
O1 C2 C11 C12 -0.6(5) . . . . ?
C3 C2 C11 C12 178.0(3) . . . . ?
C9 C10 C11 C2 179.5(3) . . . . ?
C5 C10 C11 C2 0.3(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C5 C10 C11 C12 179.9(3) . . . . ?
C2 C11 C12 C21 -80.4(4) . . . . ?
C10 C11 C12 C21 99.9(3) . . . . ?
C2 C11 C12 C13 101.4(3) . . . . ?
C10 C11 C12 C13 -78.3(4) . . . . ?
C21 C12 C13 C18 1.5(4) . . . . ?
C11 C12 C13 C18 179.7(2) . . . . ?
C21 C12 C13 C14 -176.3(3) . . . . ?
C11 C12 C13 C14 1.9(4) . . . . ?
C18 C13 C14 C15 -1.5(4) . . . . ?
C12 C13 C14 C15 176.3(3) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 -2.2(5) . . . . ?
C14 C13 C18 C19 178.6(3) . . . . ?
C12 C13 C18 C19 0.8(4) . . . . ?
C14 C13 C18 C17 -0.3(4) . . . . ?
C12 C13 C18 C17 -178.2(3) . . . . ?
C16 C17 C18 C13 2.2(4) . . . . ?
C16 C17 C18 C19 -176.7(3) . . . . ?
C13 C18 C19 C20 -2.0(4) . . . . ?
C17 C18 C19 C20 176.9(3) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C13 C12 C21 O22 178.2(3) . . . . ?
C11 C12 C21 O22 0.0(4) . . . . ?
C13 C12 C21 C20 -2.5(4) . . . . ?
C11 C12 C21 C20 179.3(3) . . . . ?
C19 C20 C21 O22 -179.4(3) . . . . ?
C19 C20 C21 C12 1.3(4) . . . . ?
N31 C32 C33 C34 176.8(3) . . . . ?
C37 C32 C33 C34 54.4(4) . . . . ?
C32 C33 C34 C35 -54.4(4) . . . . ?
C33 C34 C35 C36 54.3(4) . . . . ?
C34 C35 C36 C37 -55.5(4) . . . . ?
C35 C36 C37 N38 175.7(3) . . . . ?
C35 C36 C37 C32 55.5(4) . . . . ?
N31 C32 C37 N38 64.5(3) . . . . ?
C33 C32 C37 N38 -173.6(3) . . . . ?
N31 C32 C37 C36 -176.2(3) . . . . ?
C33 C32 C37 C36 -54.2(3) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_jdm_rBIN_rDACHmeOH
_database_code_depnum_ccdc_archive 'CCDC 2470284'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine"
_chemical_name_common            'BINOL +  DACH'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 O2, C6 H15 N2, C H4 O'
_chemical_formula_sum            'C27 H32 N2 O3'
_chemical_formula_weight         432.54

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                   10.2697(12)
_cell_length_b                   11.140(2)
_cell_length_c                   11.3987(17)
_cell_angle_alpha                108.518(16)
_cell_angle_beta                 101.580(12)
_cell_angle_gamma                101.228(14)
_cell_volume                     1163.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2679
_cell_measurement_theta_min      3.2410
_cell_measurement_theta_max      26.0340

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81288
_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° '
'60 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16245
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0364
_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         3.251
_diffrn_reflns_theta_max         26.299
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4618
_reflns_number_gt                3566
_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)+(0.0634P)²+0.5584P] where P=(Fo²+2Fc²)/3'
_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         4618
_refine_ls_number_parameters     381
_refine_ls_number_restraints     224
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.123
_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 0.77636(14) 0.59575(13) 0.57793(13) 0.0472(4) Uani 1 1 d . . . . .
C2 C 0.7757(2) 0.65950(19) 0.69885(19) 0.0428(5) Uani 1 1 d . . . . .
C3 C 0.8343(2) 0.7991(2) 0.7558(2) 0.0554(6) Uani 1 1 d . . . . .
H3 H 0.870865 0.842849 0.707401 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8383(3) 0.8699(2) 0.8784(2) 0.0576(6) Uani 1 1 d . . . . .
H4 H 0.877927 0.960600 0.912253 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7837(2) 0.8085(2) 0.9552(2) 0.0485(5) Uani 1 1 d . . . . .
C6 C 0.7873(3) 0.8801(2) 1.0832(2) 0.0615(6) Uani 1 1 d . . . . .
H6 H 0.828940 0.970532 1.119196 0.074 Uiso 1 1 calc R U . . .
C7 C 0.7310(3) 0.8193(3) 1.1549(2) 0.0673(7) Uani 1 1 d . . . . .
H7 H 0.733087 0.868082 1.238701 0.081 Uiso 1 1 calc R U . . .
C8 C 0.6699(3) 0.6830(3) 1.1023(2) 0.0638(6) Uani 1 1 d . . . . .
H8 H 0.631482 0.641541 1.151398 0.077 Uiso 1 1 calc R U . . .
C9 C 0.6661(2) 0.6102(2) 0.9791(2) 0.0518(5) Uani 1 1 d . . . . .
H9 H 0.625430 0.519684 0.946121 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7226(2) 0.66956(19) 0.90085(19) 0.0425(5) Uani 1 1 d . . . . .
C11 C 0.71972(19) 0.59599(18) 0.77151(19) 0.0401(4) Uani 1 1 d . . . . .
C12 C 0.65358(19) 0.45028(18) 0.71430(18) 0.0390(4) Uani 1 1 d . . . . .
C13 C 0.7257(2) 0.36011(18) 0.74035(18) 0.0392(4) Uani 1 1 d . . . . .
C14 C 0.8641(2) 0.4026(2) 0.8177(2) 0.0486(5) Uani 1 1 d . . . . .
H14 H 0.909670 0.492237 0.854755 0.058 Uiso 1 1 calc R U . . .
C15 C 0.9324(2) 0.3145(2) 0.8390(2) 0.0598(6) Uani 1 1 d . . . . .
H15 H 1.023515 0.344779 0.890474 0.072 Uiso 1 1 calc R U . . .
C16 C 0.8661(3) 0.1787(2) 0.7839(3) 0.0605(6) Uani 1 1 d . . . . .
H16 H 0.913622 0.119311 0.798202 0.073 Uiso 1 1 calc R U . . .
C17 C 0.7333(3) 0.1342(2) 0.7100(2) 0.0542(6) Uani 1 1 d . . . . .
H17 H 0.690050 0.044061 0.674532 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6588(2) 0.22183(19) 0.68559(19) 0.0434(5) Uani 1 1 d . . . . .
C19 C 0.5209(2) 0.1781(2) 0.6072(2) 0.0509(5) Uani 1 1 d . . . . .
H19 H 0.474880 0.088636 0.572830 0.061 Uiso 1 1 calc R U . . .
C20 C 0.4545(2) 0.2642(2) 0.5810(2) 0.0514(5) Uani 1 1 d . . . . .
H20 H 0.364478 0.232879 0.526912 0.062 Uiso 1 1 calc R U . . .
C21 C 0.5201(2) 0.4012(2) 0.63492(19) 0.0434(5) Uani 1 1 d . . . . .
O22 O 0.45123(16) 0.48691(15) 0.61154(17) 0.0588(4) Uani 1 1 d . . . . .
H22 H 0.372(3) 0.4401(16) 0.537(3) 0.088 Uiso 1 1 calc R U . . .
N31 N 0.7560(15) 0.3404(14) 0.4533(6) 0.046(2) Uani 0.510(5) 1 d D U P A 1
H31A H 0.695296 0.283553 0.469554 0.069 Uiso 0.510(5) 1 calc R U P A 1
H31B H 0.760106 0.422326 0.501121 0.069 Uiso 0.510(5) 1 calc R U P A 1
H31C H 0.839136 0.327142 0.472200 0.069 Uiso 0.510(5) 1 calc R U P A 1
C32 C 0.7119(6) 0.3207(4) 0.3146(4) 0.0464(13) Uani 0.510(5) 1 d D U P A 1
H32 H 0.633414 0.356342 0.296537 0.056 Uiso 0.510(5) 1 calc R U P A 1
C33 C 0.8355(10) 0.3875(10) 0.2771(7) 0.090(4) Uani 0.510(5) 1 d D U P A 1
H33A H 0.850696 0.482120 0.313773 0.108 Uiso 0.510(5) 1 calc R U P A 1
H33B H 0.917669 0.368076 0.316490 0.108 Uiso 0.510(5) 1 calc R U P A 1
C34 C 0.8199(6) 0.3469(8) 0.1323(6) 0.073(2) Uani 0.510(5) 1 d D U P A 1
H34A H 0.861655 0.422908 0.114764 0.088 Uiso 0.510(5) 1 calc R U P A 1
H34B H 0.868177 0.280799 0.105996 0.088 Uiso 0.510(5) 1 calc R U P A 1
C35 C 0.6685(6) 0.2920(7) 0.0549(6) 0.0777(19) Uani 0.510(5) 1 d D U P A 1
H35A H 0.658322 0.264714 -0.036912 0.093 Uiso 0.510(5) 1 calc R U P A 1
H35B H 0.617540 0.356258 0.079197 0.093 Uiso 0.510(5) 1 calc R U P A 1
C36 C 0.6183(12) 0.1707(10) 0.0926(6) 0.102(4) Uani 0.510(5) 1 d D U P A 1
H36A H 0.518456 0.151309 0.074078 0.122 Uiso 0.510(5) 1 calc R U P A 1
H36B H 0.637593 0.096095 0.033983 0.122 Uiso 0.510(5) 1 calc R U P A 1
C37 C 0.6746(6) 0.1739(4) 0.2316(4) 0.0554(14) Uani 0.510(5) 1 d D U P A 1
H37 H 0.757713 0.142823 0.238192 0.066 Uiso 0.510(5) 1 calc R U P A 1
N38 N 0.5744(10) 0.1007(7) 0.2751(9) 0.080(2) Uani 0.510(5) 1 d D U P A 1
H38A H 0.499(5) 0.130(7) 0.276(10) 0.121 Uiso 0.510(5) 1 d D U P A 1
H38B H 0.566(8) 0.021(4) 0.220(6) 0.121 Uiso 0.510(5) 1 d D U P A 1
N31B N 0.7768(16) 0.3214(15) 0.4480(6) 0.050(3) Uani 0.490(5) 1 d D U P A 2
H31D H 0.711587 0.266861 0.462306 0.074 Uiso 0.490(5) 1 calc R U P A 2
H31E H 0.770814 0.403369 0.480738 0.074 Uiso 0.490(5) 1 calc R U P A 2
H31F H 0.859749 0.317219 0.485388 0.074 Uiso 0.490(5) 1 calc R U P A 2
C32B C 0.7571(5) 0.2825(6) 0.3076(5) 0.0519(14) Uani 0.490(5) 1 d D U P A 2
H32B H 0.806464 0.216402 0.280075 0.062 Uiso 0.490(5) 1 calc R U P A 2
C33B C 0.8175(10) 0.4034(7) 0.2766(6) 0.056(2) Uani 0.490(5) 1 d D U P A 2
H33C H 0.795061 0.479490 0.329327 0.067 Uiso 0.490(5) 1 calc R U P A 2
H33D H 0.917479 0.422091 0.298660 0.067 Uiso 0.490(5) 1 calc R U P A 2
C34B C 0.7615(8) 0.3816(5) 0.1341(6) 0.0699(19) Uani 0.490(5) 1 d D U P A 2
H34C H 0.829779 0.433390 0.108551 0.084 Uiso 0.490(5) 1 calc R U P A 2
H34D H 0.678518 0.410918 0.121881 0.084 Uiso 0.490(5) 1 calc R U P A 2
C35B C 0.7276(7) 0.2347(5) 0.0490(5) 0.0677(16) Uani 0.490(5) 1 d D U P A 2
H35C H 0.803125 0.197960 0.070713 0.081 Uiso 0.490(5) 1 calc R U P A 2
H35D H 0.705812 0.220941 -0.041958 0.081 Uiso 0.490(5) 1 calc R U P A 2
C36B C 0.5980(11) 0.1755(11) 0.0857(6) 0.089(4) Uani 0.490(5) 1 d D U P A 2
H36C H 0.518594 0.194071 0.040161 0.107 Uiso 0.490(5) 1 calc R U P A 2
H36D H 0.580893 0.080511 0.054761 0.107 Uiso 0.490(5) 1 calc R U P A 2
C37B C 0.6069(5) 0.2255(5) 0.2304(4) 0.0519(13) Uani 0.490(5) 1 d D U P A 2
H37B H 0.562915 0.297391 0.247532 0.062 Uiso 0.490(5) 1 calc R U P A 2
N38B N 0.5363(13) 0.1266(12) 0.2715(13) 0.120(5) Uani 0.490(5) 1 d D U P A 2
H38C H 0.463(7) 0.066(7) 0.210(6) 0.180 Uiso 0.490(5) 1 d D U P A 2
H38D H 0.597(5) 0.093(9) 0.311(11) 0.180 Uiso 0.490(5) 1 d D U P A 2
O41 O 0.9802(2) 0.7186(2) 0.5102(2) 0.0775(6) Uani 1 1 d . . . . .
H41 H 0.901(3) 0.678(3) 0.533(3) 0.116 Uiso 1 1 calc R U . . .
C42 C 0.9466(5) 0.8062(5) 0.4577(5) 0.1305(17) Uani 1 1 d . . . . .
H42A H 0.875131 0.759981 0.377648 0.196 Uiso 1 1 calc R U . . .
H42B H 1.026792 0.852033 0.442234 0.196 Uiso 1 1 calc R U . . .
H42C H 0.914092 0.868455 0.516091 0.196 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.337(2) . ?
C2 C11 1.387(3) . ?
C2 C3 1.429(3) . ?
C3 C4 1.357(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(3) . ?
C5 C10 1.425(3) . ?
C6 C7 1.361(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.415(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.432(3) . ?
C11 C12 1.497(3) . ?
C12 C21 1.376(3) . ?
C12 C13 1.427(3) . ?
C13 C14 1.412(3) . ?
C13 C18 1.428(3) . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.404(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.412(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.410(3) . ?
C19 C20 1.352(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.414(3) . ?
C20 H20 0.9300 . ?
C21 O22 1.353(2) . ?
O22 H22 0.97(3) . ?
N31 C32 1.485(6) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
N31 H31C 0.8900 . ?
C32 C37 1.531(5) . ?
C32 C33 1.549(6) . ?
C32 H32 0.9800 . ?
C33 C34 1.531(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.519(6) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.569(6) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.560(6) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 N38 1.450(6) . ?
C37 H37 0.9800 . ?
N38 H38A 0.90(2) . ?
N38 H38B 0.88(2) . ?
N31B C32B 1.479(6) . ?
N31B H31D 0.8900 . ?
N31B H31E 0.8900 . ?
N31B H31F 0.8900 . ?
C32B C37B 1.509(5) . ?
C32B C33B 1.545(6) . ?
C32B H32B 0.9800 . ?
C33B C34B 1.532(6) . ?
C33B H33C 0.9700 . ?
C33B H33D 0.9700 . ?
C34B C35B 1.541(6) . ?
C34B H34C 0.9700 . ?
C34B H34D 0.9700 . ?
C35B C36B 1.562(7) . ?
C35B H35C 0.9700 . ?
C35B H35D 0.9700 . ?
C36B C37B 1.541(6) . ?
C36B H36C 0.9700 . ?
C36B H36D 0.9700 . ?
C37B N38B 1.453(6) . ?
C37B H37B 0.9800 . ?
N38B H38C 0.89(2) . ?
N38B H38D 0.91(2) . ?
O41 C42 1.360(4) . ?
O41 H41 0.97(4) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 C11 122.81(18) . . ?
O1 C2 C3 118.84(18) . . ?
C11 C2 C3 118.34(19) . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 C10 118.4(2) . . ?
C6 C5 C10 119.5(2) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.5(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 117.40(19) . . ?
C9 C10 C11 122.75(18) . . ?
C5 C10 C11 119.85(18) . . ?
C2 C11 C10 120.27(18) . . ?
C2 C11 C12 120.12(18) . . ?
C10 C11 C12 119.60(17) . . ?
C21 C12 C13 118.77(18) . . ?
C21 C12 C11 119.69(17) . . ?
C13 C12 C11 121.54(17) . . ?
C14 C13 C12 122.07(18) . . ?
C14 C13 C18 117.86(18) . . ?
C12 C13 C18 120.06(18) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 121.3(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 122.54(19) . . ?
C19 C18 C13 118.36(18) . . ?
C17 C18 C13 119.09(19) . . ?
C20 C19 C18 121.09(19) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
O22 C21 C12 118.72(18) . . ?
O22 C21 C20 120.38(19) . . ?
C12 C21 C20 120.88(19) . . ?
C21 O22 H22 109.5 . . ?
C32 N31 H31A 109.5 . . ?
C32 N31 H31B 109.5 . . ?
H31A N31 H31B 109.5 . . ?
C32 N31 H31C 109.5 . . ?
H31A N31 H31C 109.5 . . ?
H31B N31 H31C 109.5 . . ?
N31 C32 C37 109.9(6) . . ?
N31 C32 C33 109.4(6) . . ?
C37 C32 C33 105.4(5) . . ?
N31 C32 H32 110.7 . . ?
C37 C32 H32 110.7 . . ?
C33 C32 H32 110.7 . . ?
C34 C33 C32 115.9(5) . . ?
C34 C33 H33A 108.3 . . ?
C32 C33 H33A 108.3 . . ?
C34 C33 H33B 108.3 . . ?
C32 C33 H33B 108.3 . . ?
H33A C33 H33B 107.4 . . ?
C35 C34 C33 111.0(6) . . ?
C35 C34 H34A 109.4 . . ?
C33 C34 H34A 109.4 . . ?
C35 C34 H34B 109.4 . . ?
C33 C34 H34B 109.4 . . ?
H34A C34 H34B 108.0 . . ?
C34 C35 C36 102.8(6) . . ?
C34 C35 H35A 111.2 . . ?
C36 C35 H35A 111.2 . . ?
C34 C35 H35B 111.2 . . ?
C36 C35 H35B 111.2 . . ?
H35A C35 H35B 109.1 . . ?
C37 C36 C35 121.5(5) . . ?
C37 C36 H36A 106.9 . . ?
C35 C36 H36A 106.9 . . ?
C37 C36 H36B 106.9 . . ?
C35 C36 H36B 106.9 . . ?
H36A C36 H36B 106.7 . . ?
N38 C37 C32 109.1(5) . . ?
N38 C37 C36 114.4(6) . . ?
C32 C37 C36 102.7(5) . . ?
N38 C37 H37 110.1 . . ?
C32 C37 H37 110.1 . . ?
C36 C37 H37 110.1 . . ?
C37 N38 H38A 113(3) . . ?
C37 N38 H38B 97(5) . . ?
H38A N38 H38B 119(5) . . ?
C32B N31B H31D 109.5 . . ?
C32B N31B H31E 109.5 . . ?
H31D N31B H31E 109.5 . . ?
C32B N31B H31F 109.5 . . ?
H31D N31B H31F 109.5 . . ?
H31E N31B H31F 109.5 . . ?
N31B C32B C37B 112.8(7) . . ?
N31B C32B C33B 110.1(6) . . ?
C37B C32B C33B 107.9(5) . . ?
N31B C32B H32B 108.7 . . ?
C37B C32B H32B 108.7 . . ?
C33B C32B H32B 108.7 . . ?
C34B C33B C32B 112.3(5) . . ?
C34B C33B H33C 109.1 . . ?
C32B C33B H33C 109.1 . . ?
C34B C33B H33D 109.1 . . ?
C32B C33B H33D 109.1 . . ?
H33C C33B H33D 107.9 . . ?
C33B C34B C35B 110.5(5) . . ?
C33B C34B H34C 109.5 . . ?
C35B C34B H34C 109.5 . . ?
C33B C34B H34D 109.5 . . ?
C35B C34B H34D 109.5 . . ?
H34C C34B H34D 108.1 . . ?
C34B C35B C36B 100.8(6) . . ?
C34B C35B H35C 111.6 . . ?
C36B C35B H35C 111.6 . . ?
C34B C35B H35D 111.6 . . ?
C36B C35B H35D 111.6 . . ?
H35C C35B H35D 109.4 . . ?
C37B C36B C35B 116.2(5) . . ?
C37B C36B H36C 108.2 . . ?
C35B C36B H36C 108.2 . . ?
C37B C36B H36D 108.2 . . ?
C35B C36B H36D 108.2 . . ?
H36C C36B H36D 107.4 . . ?
N38B C37B C32B 111.1(6) . . ?
N38B C37B C36B 114.2(6) . . ?
C32B C37B C36B 108.9(5) . . ?
N38B C37B H37B 107.5 . . ?
C32B C37B H37B 107.5 . . ?
C36B C37B H37B 107.5 . . ?
C37B N38B H38C 114(4) . . ?
C37B N38B H38D 111(4) . . ?
H38C N38B H38D 115(5) . . ?
C42 O41 H41 109.5 . . ?
O41 C42 H42A 109.5 . . ?
O41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.4(2) . . . . ?
C11 C2 C3 C4 1.0(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 179.7(2) . . . . ?
C3 C4 C5 C10 -0.5(3) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
C10 C5 C6 C7 -1.4(4) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
C8 C9 C10 C11 -179.8(2) . . . . ?
C4 C5 C10 C9 -178.9(2) . . . . ?
C6 C5 C10 C9 0.9(3) . . . . ?
C4 C5 C10 C11 0.8(3) . . . . ?
C6 C5 C10 C11 -179.4(2) . . . . ?
O1 C2 C11 C10 179.74(18) . . . . ?
C3 C2 C11 C10 -0.7(3) . . . . ?
O1 C2 C11 C12 -1.3(3) . . . . ?
C3 C2 C11 C12 178.24(18) . . . . ?
C9 C10 C11 C2 179.48(19) . . . . ?
C5 C10 C11 C2 -0.2(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C5 C10 C11 C12 -179.11(17) . . . . ?
C2 C11 C12 C21 -80.6(2) . . . . ?
C10 C11 C12 C21 98.3(2) . . . . ?
C2 C11 C12 C13 99.6(2) . . . . ?
C10 C11 C12 C13 -81.5(2) . . . . ?
C21 C12 C13 C14 178.08(19) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C21 C12 C13 C18 -0.7(3) . . . . ?
C11 C12 C13 C18 179.13(17) . . . . ?
C12 C13 C14 C15 -178.4(2) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 178.9(2) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C14 C13 C18 C19 -179.39(18) . . . . ?
C12 C13 C18 C19 -0.6(3) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
C12 C13 C18 C17 178.39(18) . . . . ?
C17 C18 C19 C20 -177.0(2) . . . . ?
C13 C18 C19 C20 1.9(3) . . . . ?
C18 C19 C20 C21 -1.9(3) . . . . ?
C13 C12 C21 O22 179.21(17) . . . . ?
C11 C12 C21 O22 -0.6(3) . . . . ?
C13 C12 C21 C20 0.7(3) . . . . ?
C11 C12 C21 C20 -179.13(18) . . . . ?
C19 C20 C21 O22 -177.9(2) . . . . ?
C19 C20 C21 C12 0.6(3) . . . . ?
N31 C32 C33 C34 164.7(10) . . . . ?
C37 C32 C33 C34 46.6(11) . . . . ?
C32 C33 C34 C35 22.3(12) . . . . ?
C33 C34 C35 C36 -59.9(10) . . . . ?
C34 C35 C36 C37 35.8(13) . . . . ?
N31 C32 C37 N38 53.1(9) . . . . ?
C33 C32 C37 N38 170.9(7) . . . . ?
N31 C32 C37 C36 174.9(8) . . . . ?
C33 C32 C37 C36 -67.3(8) . . . . ?
C35 C36 C37 N38 145.9(10) . . . . ?
C35 C36 C37 C32 27.9(12) . . . . ?
N31B C32B C33B C34B -161.8(9) . . . . ?
C37B C32B C33B C34B -38.4(9) . . . . ?
C32B C33B C34B C35B -30.5(10) . . . . ?
C33B C34B C35B C36B 70.3(9) . . . . ?
C34B C35B C36B C37B -43.8(11) . . . . ?
N31B C32B C37B N38B -47.8(10) . . . . ?
C33B C32B C37B N38B -169.6(8) . . . . ?
N31B C32B C37B C36B -174.4(9) . . . . ?
C33B C32B C37B C36B 63.8(8) . . . . ?
C35B C36B C37B N38B -145.4(10) . . . . ?
C35B C36B C37B C32B -20.6(12) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_jdm_alex_B_DAC_benzene
_database_code_depnum_ccdc_archive 'CCDC 2470280'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine"
_chemical_name_common            'BINOL +  DACH'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2, C6 H14 N2, C6 H6'
_chemical_formula_sum            'C32 H34 N2 O2'
_chemical_formula_weight         478.61

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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

_cell_length_a                   12.3993(15)
_cell_length_b                   14.0194(10)
_cell_length_c                   15.3719(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2672.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1540
_cell_measurement_theta_min      3.1580
_cell_measurement_theta_max      21.8830

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83528
_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       
;
'100 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7721
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.194
_diffrn_reflns_theta_max         23.226
_diffrn_reflns_theta_full        23.226
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1896
_reflns_number_gt                1231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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)+(0.0615P)²+0.3028P] where P=(Fo²+2Fc²)/3'
_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 391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1896
_refine_ls_number_parameters     172
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.114
_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 0.5378(4) 0.3527(3) 0.4822(3) 0.0692(14) Uani 1 1 d . . . . .
H1 H 0.531(5) 0.381(4) 0.530(5) 0.104 Uiso 1 1 calc R U . . .
C2 C 0.6019(5) 0.4059(4) 0.4287(4) 0.0517(16) Uani 1 1 d . . . . .
C4 C 0.6640(6) 0.4198(5) 0.2808(4) 0.068(2) Uani 1 1 d . . . . .
H4 H 0.664594 0.397626 0.223759 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6039(6) 0.3745(4) 0.3411(4) 0.0643(19) Uani 1 1 d . . . . .
H3 H 0.563094 0.321798 0.324978 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7260(5) 0.5005(4) 0.3034(4) 0.0585(17) Uani 1 1 d . . . . .
C6 C 0.7898(6) 0.5508(5) 0.2422(5) 0.078(2) Uani 1 1 d . . . . .
H6 H 0.792392 0.529351 0.184978 0.094 Uiso 1 1 calc R U . . .
C7 C 0.8470(7) 0.6290(6) 0.2644(6) 0.094(3) Uani 1 1 d . . . . .
H7 H 0.885100 0.662854 0.222426 0.112 Uiso 1 1 calc R U . . .
C9 C 0.7879(6) 0.6125(5) 0.4127(4) 0.0686(19) Uani 1 1 d . . . . .
H9 H 0.788079 0.634622 0.469716 0.082 Uiso 1 1 calc R U . . .
C8 C 0.8484(7) 0.6584(5) 0.3514(6) 0.090(2) Uani 1 1 d . . . . .
H8 H 0.891158 0.709973 0.367624 0.108 Uiso 1 1 calc R U . . .
C10 C 0.7250(5) 0.5320(4) 0.3909(4) 0.0515(16) Uani 1 1 d . . . . .
C11 C 0.6613(5) 0.4834(4) 0.4534(3) 0.0488(15) Uani 1 1 d . . . . .
N21 N 0.4770(5) 0.3871(4) 0.6526(3) 0.0627(16) Uani 1 1 d . . . . .
H21A H 0.514(6) 0.444(5) 0.676(4) 0.094 Uiso 1 1 d . U . . .
H21B H 0.399(6) 0.383(5) 0.660(4) 0.094 Uiso 1 1 d . U . . .
C22 C 0.5132(5) 0.3019(3) 0.7008(3) 0.0519(16) Uani 1 1 d . . . . .
H22 H 0.591734 0.297303 0.694515 0.062 Uiso 1 1 calc R U . . .
C23 C 0.4640(7) 0.2136(4) 0.6601(4) 0.071(2) Uani 1 1 d . . . . .
H23A H 0.386358 0.215346 0.667338 0.086 Uiso 1 1 calc R U . . .
H23B H 0.479463 0.213048 0.598213 0.086 Uiso 1 1 calc R U . . .
C24 C 0.5079(8) 0.1237(4) 0.7010(4) 0.086(2) Uani 1 1 d . . . . .
H24A H 0.584197 0.118280 0.687952 0.104 Uiso 1 1 calc R U . . .
H24B H 0.471620 0.068819 0.676136 0.104 Uiso 1 1 calc R U . . .
C31 C 0.8028(12) 0.000000 0.500000 0.107(4) Uani 1 2 d S TU P . .
H31 H 0.877803 0.000001 0.500003 0.129 Uiso 1 2 calc R U P . .
C32 C 0.7498(9) 0.0826(8) 0.4986(6) 0.118(3) Uani 1 1 d . U . . .
H32 H 0.788350 0.139501 0.499204 0.142 Uiso 1 1 calc R U . . .
C33 C 0.6372(10) 0.0852(8) 0.4963(6) 0.129(3) Uani 1 1 d . U . . .
H33 H 0.599529 0.142455 0.492473 0.155 Uiso 1 1 calc R U . . .
C34 C 0.5857(14) 0.000000 0.500000 0.136(5) Uani 1 2 d S TU P . .
H34 H 0.510728 0.000001 0.500000 0.163 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.365(7) . ?
O1 H1 0.85(7) . ?
C2 C11 1.367(8) . ?
C2 C3 1.415(8) . ?
C4 C3 1.349(8) . ?
C4 C5 1.411(8) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C5 C10 1.417(8) . ?
C5 C6 1.418(8) . ?
C6 C7 1.349(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(11) . ?
C7 H7 0.9300 . ?
C9 C8 1.367(9) . ?
C9 C10 1.412(9) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.418(8) . ?
C11 C11 1.507(11) 4_566 ?
N21 C22 1.476(7) . ?
N21 H21A 0.98(7) . ?
N21 H21B 0.98(8) . ?
C22 C23 1.515(8) . ?
C22 C22 1.549(10) 3_656 ?
C22 H22 0.9800 . ?
C23 C24 1.509(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C24 1.519(11) 3_656 ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C31 C32 1.332(11) . ?
C31 C32 1.332(11) 4_556 ?
C31 H31 0.9300 . ?
C32 C33 1.397(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.356(13) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?

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 125.5(5) . . ?
O1 C2 C3 114.4(5) . . ?
C11 C2 C3 120.1(5) . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C3 C2 121.2(6) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C5 C10 118.6(5) . . ?
C4 C5 C6 122.7(6) . . ?
C10 C5 C6 118.7(6) . . ?
C7 C6 C5 122.0(7) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 119.2(7) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C8 C9 C10 121.1(7) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C8 C7 120.9(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C9 C10 C5 118.0(5) . . ?
C9 C10 C11 122.1(6) . . ?
C5 C10 C11 119.9(6) . . ?
C2 C11 C10 119.6(5) . . ?
C2 C11 C11 120.7(5) . 4_566 ?
C10 C11 C11 119.7(5) . 4_566 ?
C22 N21 H21A 109(4) . . ?
C22 N21 H21B 101(4) . . ?
H21A N21 H21B 117(6) . . ?
N21 C22 C23 109.4(5) . . ?
N21 C22 C22 115.2(4) . 3_656 ?
C23 C22 C22 108.5(4) . 3_656 ?
N21 C22 H22 107.8 . . ?
C23 C22 H22 107.8 . . ?
C22 C22 H22 107.8 3_656 . ?
C24 C23 C22 111.4(6) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C24 111.5(5) . 3_656 ?
C23 C24 H24A 109.3 . . ?
C24 C24 H24A 109.3 3_656 . ?
C23 C24 H24B 109.3 . . ?
C24 C24 H24B 109.3 3_656 . ?
H24A C24 H24B 108.0 . . ?
C32 C31 C32 120.8(15) . 4_556 ?
C32 C31 H31 119.6 . . ?
C32 C31 H31 119.6 4_556 . ?
C31 C32 C33 121.1(12) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C32 116.5(13) . . ?
C34 C33 H33 121.8 . . ?
C32 C33 H33 121.8 . . ?
C33 C34 C33 123.9(18) . 4_556 ?
C33 C34 H34 118.1 . . ?
C33 C34 H34 118.1 4_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 -0.6(10) . . . . ?
O1 C2 C3 C4 -179.7(6) . . . . ?
C11 C2 C3 C4 0.1(10) . . . . ?
C3 C4 C5 C10 1.0(9) . . . . ?
C3 C4 C5 C6 -179.6(6) . . . . ?
C4 C5 C6 C7 178.7(7) . . . . ?
C10 C5 C6 C7 -1.8(10) . . . . ?
C5 C6 C7 C8 3.6(12) . . . . ?
C10 C9 C8 C7 2.2(12) . . . . ?
C6 C7 C8 C9 -3.8(13) . . . . ?
C8 C9 C10 C5 -0.4(10) . . . . ?
C8 C9 C10 C11 -179.8(6) . . . . ?
C4 C5 C10 C9 179.6(6) . . . . ?
C6 C5 C10 C9 0.2(8) . . . . ?
C4 C5 C10 C11 -0.9(9) . . . . ?
C6 C5 C10 C11 179.6(6) . . . . ?
O1 C2 C11 C10 179.7(6) . . . . ?
C3 C2 C11 C10 -0.1(9) . . . . ?
O1 C2 C11 C11 0.7(9) . . . 4_566 ?
C3 C2 C11 C11 -179.0(5) . . . 4_566 ?
C9 C10 C11 C2 179.9(6) . . . . ?
C5 C10 C11 C2 0.5(9) . . . . ?
C9 C10 C11 C11 -1.1(8) . . . 4_566 ?
C5 C10 C11 C11 179.5(5) . . . 4_566 ?
N21 C22 C23 C24 174.0(6) . . . . ?
C22 C22 C23 C24 -59.6(8) 3_656 . . . ?
C22 C23 C24 C24 55.5(11) . . . 3_656 ?
C32 C31 C32 C33 -1.7(7) 4_556 . . . ?
C31 C32 C33 C34 3.2(13) . . . . ?
C32 C33 C34 C33 -1.5(6) . . . 4_556 ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
####################################################################### 
# 
# 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_jdm_RBIN_RRDACH
_database_code_depnum_ccdc_archive 'CCDC 2470282'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine"
_chemical_name_common            'BINOL +  DACH'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2, C6 H14 N2'
_chemical_formula_sum            'C26 H28 N2 O2'
_chemical_formula_weight         400.50

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

_cell_length_a                   9.85511(18)
_cell_length_b                   15.3092(3)
_cell_length_c                   28.2920(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4268.53(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12770
_cell_measurement_theta_min      3.0070
_cell_measurement_theta_max      26.0490

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.60486
_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      150(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       
;
'220 images, ΔΦ 1.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37239
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.990
_diffrn_reflns_theta_max         26.152
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8486
_reflns_number_gt                7460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.997
_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)+(0.0237P)²+1.6451P] where P=(Fo²+2Fc²)/3'
_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 2995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         8486
_refine_ls_number_parameters     565
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.058
_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 0.23905(17) 0.58282(11) 0.72248(6) 0.0231(4) Uani 1 1 d . . . . .
H1 H 0.219829 0.533267 0.733327 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2096(2) 0.64483(15) 0.75526(9) 0.0204(5) Uani 1 1 d . . . . .
C3 C 0.2392(3) 0.73173(17) 0.74147(10) 0.0276(6) Uani 1 1 d . . . . .
H3 H 0.274933 0.742944 0.710879 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2167(3) 0.79922(17) 0.77176(10) 0.0295(6) Uani 1 1 d . . . . .
H4 H 0.237614 0.857075 0.762049 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1628(3) 0.78487(16) 0.81746(10) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.1368(3) 0.85411(17) 0.84952(11) 0.0313(7) Uani 1 1 d . . . . .
H6 H 0.158602 0.912256 0.840592 0.038 Uiso 1 1 calc R U . . .
C7 C 0.0812(3) 0.83899(18) 0.89289(11) 0.0328(7) Uani 1 1 d . . . . .
H7 H 0.061980 0.886394 0.913502 0.039 Uiso 1 1 calc R U . . .
C8 C 0.0525(3) 0.75291(18) 0.90694(10) 0.0299(6) Uani 1 1 d . . . . .
H8 H 0.014743 0.742275 0.937294 0.036 Uiso 1 1 calc R U . . .
C9 C 0.0784(3) 0.68409(16) 0.87723(9) 0.0240(6) Uani 1 1 d . . . . .
H9 H 0.059438 0.626297 0.887509 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1330(2) 0.69763(15) 0.83155(9) 0.0203(5) Uani 1 1 d . . . . .
C11 C 0.1571(2) 0.62720(15) 0.79939(9) 0.0186(5) Uani 1 1 d . . . . .
C12 C 0.1307(3) 0.53463(15) 0.81368(8) 0.0198(5) Uani 1 1 d . . . . .
C13 C 0.2445(3) 0.47859(15) 0.82352(8) 0.0222(5) Uani 1 1 d . . . . .
C14 C 0.3805(3) 0.50784(17) 0.82117(10) 0.0288(6) Uani 1 1 d . . . . .
H14 H 0.398336 0.567324 0.813915 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4867(3) 0.4524(2) 0.82910(12) 0.0395(7) Uani 1 1 d . . . . .
H15 H 0.577058 0.473707 0.827408 0.047 Uiso 1 1 calc R U . . .
C16 C 0.4633(3) 0.3640(2) 0.83975(12) 0.0411(8) Uani 1 1 d . . . . .
H16 H 0.537643 0.325566 0.844519 0.049 Uiso 1 1 calc R U . . .
C17 C 0.3342(3) 0.33374(18) 0.84320(10) 0.0367(7) Uani 1 1 d . . . . .
H17 H 0.319210 0.274199 0.851083 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2213(3) 0.38926(16) 0.83527(9) 0.0258(6) Uani 1 1 d . . . . .
C19 C 0.0861(3) 0.35793(16) 0.83745(10) 0.0298(6) Uani 1 1 d . . . . .
H19 H 0.069409 0.298897 0.846007 0.036 Uiso 1 1 calc R U . . .
C20 C -0.0198(3) 0.41163(16) 0.82739(9) 0.0276(6) Uani 1 1 d . . . . .
H20 H -0.109637 0.389257 0.828299 0.033 Uiso 1 1 calc R U . . .
C21 C 0.0019(3) 0.50086(16) 0.81553(9) 0.0216(5) Uani 1 1 d . . . . .
O22 O -0.11368(18) 0.54650(11) 0.80587(7) 0.0273(4) Uani 1 1 d . . . . .
H22 H -0.093647 0.598381 0.799190 0.041 Uiso 1 1 calc R U . . .
O31 O 0.8810(2) 0.77817(11) 0.53910(7) 0.0332(5) Uani 1 1 d . . . . .
H31 H 0.889363 0.824590 0.523549 0.050 Uiso 1 1 calc R U . . .
C32 C 0.8389(3) 0.71326(16) 0.51008(9) 0.0244(6) Uani 1 1 d . . . . .
C33 C 0.8128(3) 0.72787(18) 0.46156(10) 0.0287(6) Uani 1 1 d . . . . .
H33 H 0.822320 0.784904 0.448757 0.034 Uiso 1 1 calc R U . . .
C34 C 0.7740(3) 0.66032(19) 0.43302(10) 0.0300(6) Uani 1 1 d . . . . .
H34 H 0.758323 0.670949 0.400390 0.036 Uiso 1 1 calc R U . . .
C35 C 0.7568(3) 0.57460(17) 0.45116(9) 0.0244(6) Uani 1 1 d . . . . .
C36 C 0.7227(3) 0.50212(19) 0.42212(10) 0.0309(6) Uani 1 1 d . . . . .
H36 H 0.712791 0.510253 0.389007 0.037 Uiso 1 1 calc R U . . .
C37 C 0.7040(3) 0.42095(19) 0.44106(11) 0.0340(7) Uani 1 1 d . . . . .
H37 H 0.682884 0.372867 0.421147 0.041 Uiso 1 1 calc R U . . .
C38 C 0.7160(3) 0.40877(17) 0.49021(10) 0.0284(6) Uani 1 1 d . . . . .
H38 H 0.699551 0.352733 0.503437 0.034 Uiso 1 1 calc R U . . .
C39 C 0.7512(3) 0.47663(15) 0.51910(10) 0.0229(5) Uani 1 1 d . . . . .
H39 H 0.759165 0.467045 0.552157 0.027 Uiso 1 1 calc R U . . .
C40 C 0.7761(2) 0.56143(15) 0.50041(9) 0.0193(5) Uani 1 1 d . . . . .
C41 C 0.8206(2) 0.63160(15) 0.52961(9) 0.0195(5) Uani 1 1 d . . . . .
C42 C 0.8541(3) 0.61680(15) 0.58033(9) 0.0192(5) Uani 1 1 d . . . . .
C43 C 0.7501(3) 0.60999(15) 0.61539(9) 0.0200(5) Uani 1 1 d . . . . .
C44 C 0.6108(3) 0.62157(16) 0.60401(10) 0.0247(6) Uani 1 1 d . . . . .
H44 H 0.585245 0.634438 0.572392 0.030 Uiso 1 1 calc R U . . .
C45 C 0.5130(3) 0.61433(18) 0.63827(11) 0.0319(7) Uani 1 1 d . . . . .
H45 H 0.420386 0.622678 0.630140 0.038 Uiso 1 1 calc R U . . .
C46 C 0.5479(3) 0.59477(18) 0.68515(11) 0.0319(7) Uani 1 1 d . . . . .
H46 H 0.479021 0.589127 0.708435 0.038 Uiso 1 1 calc R U . . .
C47 C 0.6811(3) 0.58383(17) 0.69732(10) 0.0282(6) Uani 1 1 d . . . . .
H47 H 0.703995 0.569945 0.729056 0.034 Uiso 1 1 calc R U . . .
C48 C 0.7853(3) 0.59295(15) 0.66320(9) 0.0215(5) Uani 1 1 d . . . . .
C49 C 0.9245(3) 0.58555(16) 0.67525(9) 0.0229(5) Uani 1 1 d . . . . .
H49 H 0.949481 0.574543 0.707130 0.027 Uiso 1 1 calc R U . . .
C50 C 1.0228(3) 0.59400(16) 0.64179(9) 0.0239(6) Uani 1 1 d . . . . .
H50 H 1.115619 0.590086 0.650616 0.029 Uiso 1 1 calc R U . . .
C51 C 0.9877(2) 0.60857(16) 0.59395(9) 0.0206(5) Uani 1 1 d . . . . .
O52 O 1.09593(18) 0.61370(12) 0.56448(6) 0.0282(4) Uani 1 1 d . . . . .
H52 H 1.068764 0.622331 0.536726 0.042 Uiso 1 1 calc R U . . .
N61 N 0.8488(2) 0.71642(14) 0.77411(8) 0.0248(5) Uani 1 1 d D . . . .
H61A H 0.797(3) 0.7098(19) 0.7471(7) 0.037 Uiso 1 1 d D U . . .
H61B H 0.924(2) 0.7460(18) 0.7685(11) 0.037 Uiso 1 1 d D U . . .
C62 C 0.7694(3) 0.76315(15) 0.81029(9) 0.0214(5) Uani 1 1 d D . . . .
H62 H 0.825345 0.765309 0.839754 0.026 Uiso 1 1 calc R U . . .
C63 C 0.6409(3) 0.71106(17) 0.82145(10) 0.0315(6) Uani 1 1 d . . . . .
H63A H 0.583856 0.707534 0.792702 0.038 Uiso 1 1 calc R U . . .
H63B H 0.666410 0.650828 0.830560 0.038 Uiso 1 1 calc R U . . .
C64 C 0.5590(3) 0.7524(2) 0.86122(12) 0.0389(7) Uani 1 1 d . . . . .
H64A H 0.611187 0.748583 0.891051 0.047 Uiso 1 1 calc R U . . .
H64B H 0.473446 0.719388 0.865516 0.047 Uiso 1 1 calc R U . . .
C65 C 0.5259(3) 0.8480(2) 0.85084(12) 0.0377(7) Uani 1 1 d . . . . .
H65A H 0.461202 0.851353 0.824142 0.045 Uiso 1 1 calc R U . . .
H65B H 0.482286 0.874659 0.878869 0.045 Uiso 1 1 calc R U . . .
C66 C 0.6543(3) 0.89880(17) 0.83851(10) 0.0286(6) Uani 1 1 d . . . . .
H66A H 0.629585 0.959535 0.830142 0.034 Uiso 1 1 calc R U . . .
H66B H 0.714327 0.900948 0.866548 0.034 Uiso 1 1 calc R U . . .
C67 C 0.7309(3) 0.85757(16) 0.79745(9) 0.0207(5) Uani 1 1 d D . . . .
H67 H 0.667982 0.855271 0.769752 0.025 Uiso 1 1 calc R U . . .
N68 N 0.8464(2) 0.91438(14) 0.78456(8) 0.0238(5) Uani 1 1 d D . . . .
H68A H 0.892(3) 0.8910(18) 0.7596(8) 0.036 Uiso 1 1 d D U . . .
H68B H 0.902(3) 0.915(2) 0.8096(8) 0.036 Uiso 1 1 d D U . . .
N71 N 0.0834(2) 0.44236(14) 0.99022(10) 0.0304(5) Uani 1 1 d D . . . .
H71A H 0.052(3) 0.458(2) 0.9617(8) 0.046 Uiso 1 1 d D U . . .
H71B H 0.021(3) 0.447(2) 1.0128(9) 0.046 Uiso 1 1 d D U . . .
C72 C 0.1954(2) 0.50320(16) 1.00226(9) 0.0212(5) Uani 1 1 d D . . . .
H72 H 0.233799 0.484845 1.033435 0.025 Uiso 1 1 calc R U . . .
C73 C 0.1433(3) 0.59659(16) 1.00734(10) 0.0255(6) Uani 1 1 d . . . . .
H73A H 0.076979 0.598919 1.033585 0.031 Uiso 1 1 calc R U . . .
H73B H 0.095520 0.613533 0.977962 0.031 Uiso 1 1 calc R U . . .
C74 C 0.2568(3) 0.66209(17) 1.01697(11) 0.0341(7) Uani 1 1 d . . . . .
H74A H 0.218803 0.721884 1.018419 0.041 Uiso 1 1 calc R U . . .
H74B H 0.299750 0.649001 1.047803 0.041 Uiso 1 1 calc R U . . .
C75 C 0.3627(3) 0.65690(18) 0.97783(11) 0.0340(7) Uani 1 1 d . . . . .
H75A H 0.321114 0.673907 0.947325 0.041 Uiso 1 1 calc R U . . .
H75B H 0.437723 0.697989 0.984650 0.041 Uiso 1 1 calc R U . . .
C76 C 0.4178(3) 0.56456(18) 0.97436(10) 0.0297(6) Uani 1 1 d . . . . .
H76A H 0.465652 0.550066 1.004118 0.036 Uiso 1 1 calc R U . . .
H76B H 0.484936 0.561982 0.948364 0.036 Uiso 1 1 calc R U . . .
C77 C 0.3078(3) 0.49613(16) 0.96546(9) 0.0218(5) Uani 1 1 d D . . . .
H77 H 0.268351 0.505200 0.933262 0.026 Uiso 1 1 calc R U . . .
N78 N 0.3717(2) 0.40864(15) 0.96775(8) 0.0266(5) Uani 1 1 d D . . . .
H78A H 0.444(2) 0.4073(18) 0.9484(10) 0.040 Uiso 1 1 d D U . . .
H78B H 0.311(3) 0.3685(17) 0.9573(10) 0.040 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.359(3) . ?
O1 H1 0.8400 . ?
C2 C11 1.378(4) . ?
C2 C3 1.417(3) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(4) . ?
C5 C10 1.425(3) . ?
C6 C7 1.364(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.415(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.431(3) . ?
C11 C12 1.497(3) . ?
C12 C21 1.372(4) . ?
C12 C13 1.439(4) . ?
C13 C14 1.415(4) . ?
C13 C18 1.426(3) . ?
C14 C15 1.367(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.358(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.418(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.418(4) . ?
C19 C20 1.359(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.423(3) . ?
C20 H20 0.9500 . ?
C21 O22 1.364(3) . ?
O22 H22 0.8400 . ?
O31 C32 1.354(3) . ?
O31 H31 0.8400 . ?
C32 C41 1.379(3) . ?
C32 C33 1.414(4) . ?
C33 C34 1.367(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.419(4) . ?
C34 H34 0.9500 . ?
C35 C40 1.421(4) . ?
C35 C36 1.421(4) . ?
C36 C37 1.366(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.408(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.367(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.423(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.424(3) . ?
C41 C42 1.490(3) . ?
C42 C51 1.378(4) . ?
C42 C43 1.430(3) . ?
C43 C48 1.420(3) . ?
C43 C44 1.421(4) . ?
C44 C45 1.372(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.402(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.367(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.417(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.418(4) . ?
C49 C50 1.361(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.415(4) . ?
C50 H50 0.9500 . ?
C51 O52 1.356(3) . ?
O52 H52 0.8400 . ?
N61 C62 1.474(3) . ?
N61 H61A 0.922(19) . ?
N61 H61B 0.89(2) . ?
C62 C63 1.530(4) . ?
C62 C67 1.538(3) . ?
C62 H62 1.0000 . ?
C63 C64 1.522(4) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.529(4) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 C66 1.526(4) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 C67 1.522(4) . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C67 N68 1.478(3) . ?
C67 H67 1.0000 . ?
N68 H68A 0.91(2) . ?
N68 H68B 0.89(2) . ?
N71 C72 1.484(3) . ?
N71 H71A 0.90(2) . ?
N71 H71B 0.89(2) . ?
C72 C77 1.524(3) . ?
C72 C73 1.526(3) . ?
C72 H72 1.0000 . ?
C73 C74 1.527(4) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 C75 1.523(4) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C75 C76 1.518(4) . ?
C75 H75A 0.9900 . ?
C75 H75B 0.9900 . ?
C76 C77 1.529(4) . ?
C76 H76A 0.9900 . ?
C76 H76B 0.9900 . ?
C77 N78 1.482(3) . ?
C77 H77 1.0000 . ?
N78 H78A 0.90(2) . ?
N78 H78B 0.90(2) . ?

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 124.2(2) . . ?
O1 C2 C3 115.1(2) . . ?
C11 C2 C3 120.7(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 122.4(2) . . ?
C4 C5 C10 118.6(2) . . ?
C6 C5 C10 119.0(2) . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 118.1(2) . . ?
C9 C10 C11 122.3(2) . . ?
C5 C10 C11 119.6(2) . . ?
C2 C11 C10 119.4(2) . . ?
C2 C11 C12 119.7(2) . . ?
C10 C11 C12 120.9(2) . . ?
C21 C12 C13 119.3(2) . . ?
C21 C12 C11 121.9(2) . . ?
C13 C12 C11 118.8(2) . . ?
C14 C13 C18 117.8(2) . . ?
C14 C13 C12 122.7(2) . . ?
C18 C13 C12 119.5(2) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 121.3(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 C13 119.0(2) . . ?
C17 C18 C13 119.1(3) . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
O22 C21 C12 124.9(2) . . ?
O22 C21 C20 114.5(2) . . ?
C12 C21 C20 120.6(2) . . ?
C21 O22 H22 109.5 . . ?
C32 O31 H31 109.5 . . ?
O31 C32 C41 117.5(2) . . ?
O31 C32 C33 121.9(2) . . ?
C41 C32 C33 120.6(2) . . ?
C34 C33 C32 120.3(2) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 121.3(2) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C34 C35 C40 118.0(2) . . ?
C34 C35 C36 122.8(2) . . ?
C40 C35 C36 119.2(2) . . ?
C37 C36 C35 121.0(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 119.8(3) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C39 C38 C37 120.8(3) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 C40 121.0(2) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C35 C40 C39 118.1(2) . . ?
C35 C40 C41 120.2(2) . . ?
C39 C40 C41 121.7(2) . . ?
C32 C41 C40 119.5(2) . . ?
C32 C41 C42 119.7(2) . . ?
C40 C41 C42 120.8(2) . . ?
C51 C42 C43 119.0(2) . . ?
C51 C42 C41 119.7(2) . . ?
C43 C42 C41 121.3(2) . . ?
C48 C43 C44 118.3(2) . . ?
C48 C43 C42 119.9(2) . . ?
C44 C43 C42 121.7(2) . . ?
C45 C44 C43 120.6(3) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C44 C45 C46 120.9(3) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C47 C46 C45 120.0(3) . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 C48 120.8(3) . . ?
C46 C47 H47 119.6 . . ?
C48 C47 H47 119.6 . . ?
C47 C48 C49 122.0(2) . . ?
C47 C48 C43 119.4(2) . . ?
C49 C48 C43 118.7(2) . . ?
C50 C49 C48 120.9(2) . . ?
C50 C49 H49 119.5 . . ?
C48 C49 H49 119.5 . . ?
C49 C50 C51 120.4(2) . . ?
C49 C50 H50 119.8 . . ?
C51 C50 H50 119.8 . . ?
O52 C51 C42 125.1(2) . . ?
O52 C51 C50 113.9(2) . . ?
C42 C51 C50 121.0(2) . . ?
C51 O52 H52 109.5 . . ?
C62 N61 H61A 109.7(17) . . ?
C62 N61 H61B 109(2) . . ?
H61A N61 H61B 112(2) . . ?
N61 C62 C63 109.3(2) . . ?
N61 C62 C67 115.0(2) . . ?
C63 C62 C67 109.6(2) . . ?
N61 C62 H62 107.6 . . ?
C63 C62 H62 107.6 . . ?
C67 C62 H62 107.6 . . ?
C64 C63 C62 112.0(2) . . ?
C64 C63 H63A 109.2 . . ?
C62 C63 H63A 109.2 . . ?
C64 C63 H63B 109.2 . . ?
C62 C63 H63B 109.2 . . ?
H63A C63 H63B 107.9 . . ?
C63 C64 C65 111.6(2) . . ?
C63 C64 H64A 109.3 . . ?
C65 C64 H64A 109.3 . . ?
C63 C64 H64B 109.3 . . ?
C65 C64 H64B 109.3 . . ?
H64A C64 H64B 108.0 . . ?
C66 C65 C64 110.8(2) . . ?
C66 C65 H65A 109.5 . . ?
C64 C65 H65A 109.5 . . ?
C66 C65 H65B 109.5 . . ?
C64 C65 H65B 109.5 . . ?
H65A C65 H65B 108.1 . . ?
C67 C66 C65 112.0(2) . . ?
C67 C66 H66A 109.2 . . ?
C65 C66 H66A 109.2 . . ?
C67 C66 H66B 109.2 . . ?
C65 C66 H66B 109.2 . . ?
H66A C66 H66B 107.9 . . ?
N68 C67 C66 109.0(2) . . ?
N68 C67 C62 114.9(2) . . ?
C66 C67 C62 109.4(2) . . ?
N68 C67 H67 107.8 . . ?
C66 C67 H67 107.8 . . ?
C62 C67 H67 107.8 . . ?
C67 N68 H68A 110.0(17) . . ?
C67 N68 H68B 106(2) . . ?
H68A N68 H68B 108(3) . . ?
C72 N71 H71A 107(2) . . ?
C72 N71 H71B 107(2) . . ?
H71A N71 H71B 113(3) . . ?
N71 C72 C77 109.8(2) . . ?
N71 C72 C73 111.1(2) . . ?
C77 C72 C73 112.0(2) . . ?
N71 C72 H72 107.9 . . ?
C77 C72 H72 107.9 . . ?
C73 C72 H72 107.9 . . ?
C72 C73 C74 112.7(2) . . ?
C72 C73 H73A 109.1 . . ?
C74 C73 H73A 109.1 . . ?
C72 C73 H73B 109.1 . . ?
C74 C73 H73B 109.1 . . ?
H73A C73 H73B 107.8 . . ?
C75 C74 C73 109.7(2) . . ?
C75 C74 H74A 109.7 . . ?
C73 C74 H74A 109.7 . . ?
C75 C74 H74B 109.7 . . ?
C73 C74 H74B 109.7 . . ?
H74A C74 H74B 108.2 . . ?
C76 C75 C74 109.9(2) . . ?
C76 C75 H75A 109.7 . . ?
C74 C75 H75A 109.7 . . ?
C76 C75 H75B 109.7 . . ?
C74 C75 H75B 109.7 . . ?
H75A C75 H75B 108.2 . . ?
C75 C76 C77 113.3(2) . . ?
C75 C76 H76A 108.9 . . ?
C77 C76 H76A 108.9 . . ?
C75 C76 H76B 108.9 . . ?
C77 C76 H76B 108.9 . . ?
H76A C76 H76B 107.7 . . ?
N78 C77 C72 110.1(2) . . ?
N78 C77 C76 108.1(2) . . ?
C72 C77 C76 110.8(2) . . ?
N78 C77 H77 109.3 . . ?
C72 C77 H77 109.3 . . ?
C76 C77 H77 109.3 . . ?
C77 N78 H78A 109.4(18) . . ?
C77 N78 H78B 109(2) . . ?
H78A N78 H78B 108(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 C2 C3 C4 -178.6(2) . . . . ?
C11 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C3 C4 C5 C10 0.4(4) . . . . ?
C4 C5 C6 C7 178.1(3) . . . . ?
C10 C5 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 C8 1.9(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C5 1.2(4) . . . . ?
C8 C9 C10 C11 -178.1(2) . . . . ?
C4 C5 C10 C9 -179.7(2) . . . . ?
C6 C5 C10 C9 0.0(4) . . . . ?
C4 C5 C10 C11 -0.4(4) . . . . ?
C6 C5 C10 C11 179.3(2) . . . . ?
O1 C2 C11 C10 178.5(2) . . . . ?
C3 C2 C11 C10 -0.2(4) . . . . ?
O1 C2 C11 C12 0.6(4) . . . . ?
C3 C2 C11 C12 -178.1(2) . . . . ?
C9 C10 C11 C2 179.5(2) . . . . ?
C5 C10 C11 C2 0.3(3) . . . . ?
C9 C10 C11 C12 -2.6(4) . . . . ?
C5 C10 C11 C12 178.2(2) . . . . ?
C2 C11 C12 C21 -105.2(3) . . . . ?
C10 C11 C12 C21 76.9(3) . . . . ?
C2 C11 C12 C13 71.7(3) . . . . ?
C10 C11 C12 C13 -106.1(3) . . . . ?
C21 C12 C13 C14 178.3(2) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C21 C12 C13 C18 -0.4(4) . . . . ?
C11 C12 C13 C18 -177.4(2) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
C12 C13 C14 C15 -177.7(3) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?
C14 C13 C18 C19 -179.4(2) . . . . ?
C12 C13 C18 C19 -0.6(4) . . . . ?
C14 C13 C18 C17 -1.1(4) . . . . ?
C12 C13 C18 C17 177.7(2) . . . . ?
C17 C18 C19 C20 -176.7(3) . . . . ?
C13 C18 C19 C20 1.6(4) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C13 C12 C21 O22 -178.4(2) . . . . ?
C11 C12 C21 O22 -1.4(4) . . . . ?
C13 C12 C21 C20 0.5(4) . . . . ?
C11 C12 C21 C20 177.4(2) . . . . ?
C19 C20 C21 O22 179.4(2) . . . . ?
C19 C20 C21 C12 0.4(4) . . . . ?
O31 C32 C33 C34 178.2(2) . . . . ?
C41 C32 C33 C34 -2.5(4) . . . . ?
C32 C33 C34 C35 1.0(4) . . . . ?
C33 C34 C35 C40 2.3(4) . . . . ?
C33 C34 C35 C36 -177.0(3) . . . . ?
C34 C35 C36 C37 -178.5(3) . . . . ?
C40 C35 C36 C37 2.2(4) . . . . ?
C35 C36 C37 C38 1.2(4) . . . . ?
C36 C37 C38 C39 -2.4(4) . . . . ?
C37 C38 C39 C40 0.2(4) . . . . ?
C34 C35 C40 C39 176.5(2) . . . . ?
C36 C35 C40 C39 -4.2(3) . . . . ?
C34 C35 C40 C41 -4.3(4) . . . . ?
C36 C35 C40 C41 175.1(2) . . . . ?
C38 C39 C40 C35 3.1(4) . . . . ?
C38 C39 C40 C41 -176.2(2) . . . . ?
O31 C32 C41 C40 179.8(2) . . . . ?
C33 C32 C41 C40 0.5(4) . . . . ?
O31 C32 C41 C42 -3.2(4) . . . . ?
C33 C32 C41 C42 177.5(2) . . . . ?
C35 C40 C41 C32 2.9(4) . . . . ?
C39 C40 C41 C32 -177.9(2) . . . . ?
C35 C40 C41 C42 -174.0(2) . . . . ?
C39 C40 C41 C42 5.2(4) . . . . ?
C32 C41 C42 C51 -76.6(3) . . . . ?
C40 C41 C42 C51 100.3(3) . . . . ?
C32 C41 C42 C43 104.1(3) . . . . ?
C40 C41 C42 C43 -79.0(3) . . . . ?
C51 C42 C43 C48 -1.5(3) . . . . ?
C41 C42 C43 C48 177.9(2) . . . . ?
C51 C42 C43 C44 177.3(2) . . . . ?
C41 C42 C43 C44 -3.4(3) . . . . ?
C48 C43 C44 C45 -1.5(4) . . . . ?
C42 C43 C44 C45 179.7(2) . . . . ?
C43 C44 C45 C46 -0.5(4) . . . . ?
C44 C45 C46 C47 0.9(4) . . . . ?
C45 C46 C47 C48 0.7(4) . . . . ?
C46 C47 C48 C49 177.3(2) . . . . ?
C46 C47 C48 C43 -2.7(4) . . . . ?
C44 C43 C48 C47 3.1(3) . . . . ?
C42 C43 C48 C47 -178.2(2) . . . . ?
C44 C43 C48 C49 -177.0(2) . . . . ?
C42 C43 C48 C49 1.8(3) . . . . ?
C47 C48 C49 C50 179.6(2) . . . . ?
C43 C48 C49 C50 -0.4(4) . . . . ?
C48 C49 C50 C51 -1.3(4) . . . . ?
C43 C42 C51 O52 -179.9(2) . . . . ?
C41 C42 C51 O52 0.7(4) . . . . ?
C43 C42 C51 C50 -0.3(4) . . . . ?
C41 C42 C51 C50 -179.6(2) . . . . ?
C49 C50 C51 O52 -178.6(2) . . . . ?
C49 C50 C51 C42 1.7(4) . . . . ?
N61 C62 C63 C64 175.8(2) . . . . ?
C67 C62 C63 C64 -57.3(3) . . . . ?
C62 C63 C64 C65 54.5(3) . . . . ?
C63 C64 C65 C66 -52.6(4) . . . . ?
C64 C65 C66 C67 55.6(3) . . . . ?
C65 C66 C67 N68 174.7(2) . . . . ?
C65 C66 C67 C62 -58.8(3) . . . . ?
N61 C62 C67 N68 -54.8(3) . . . . ?
C63 C62 C67 N68 -178.4(2) . . . . ?
N61 C62 C67 C66 -177.8(2) . . . . ?
C63 C62 C67 C66 58.6(3) . . . . ?
N71 C72 C73 C74 -176.7(2) . . . . ?
C77 C72 C73 C74 -53.5(3) . . . . ?
C72 C73 C74 C75 56.6(3) . . . . ?
C73 C74 C75 C76 -57.5(3) . . . . ?
C74 C75 C76 C77 57.4(3) . . . . ?
N71 C72 C77 N78 -66.1(3) . . . . ?
C73 C72 C77 N78 169.9(2) . . . . ?
N71 C72 C77 C76 174.4(2) . . . . ?
C73 C72 C77 C76 50.4(3) . . . . ?
C75 C76 C77 N78 -174.2(2) . . . . ?
C75 C76 C77 C72 -53.6(3) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_jdm_rBIN_RRDACHEtOH
_database_code_depnum_ccdc_archive 'CCDC 2470283'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine"
_chemical_name_common            'BINOL +  DACH'
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C20 H13 O2), 4(C6 H15 N2), 3(C2 H6 O), H2 O'
_chemical_formula_sum            'C110 H132 N8 O12'
_chemical_formula_weight         1758.23

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           1
_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'

_cell_length_a                   10.3936(12)
_cell_length_b                   11.2508(9)
_cell_length_c                   20.951(2)
_cell_angle_alpha                87.176(7)
_cell_angle_beta                 89.274(8)
_cell_angle_gamma                76.533(8)
_cell_volume                     2379.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4597
_cell_measurement_theta_min      2.9000
_cell_measurement_theta_max      25.3920

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.94435
_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       
;
'120 images, ΔΦ 2.0° '
'120 images, ΔΦ 2.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41911
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0535
_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       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.561
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             17196
_reflns_number_gt                10464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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)+(0.0856P)²+0.7211P] where P=(Fo²+2Fc²)/3'
_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 3762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         17196
_refine_ls_number_parameters     1227
_refine_ls_number_restraints     1172
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.3013(6) 0.2822(5) 0.8241(3) 0.0500(14) Uani 1 1 d D U . . .
H1A H 0.283898 0.275444 0.783093 0.075 Uiso 1 1 calc R U . . .
H1B H 0.264746 0.231348 0.848083 0.075 Uiso 1 1 calc R U . . .
H1C H 0.388426 0.263208 0.830077 0.075 Uiso 1 1 calc R U . . .
C2 C 0.2452(6) 0.4112(5) 0.8426(3) 0.0416(15) Uani 1 1 d D U . . .
H2 H 0.151182 0.434285 0.831183 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3152(8) 0.4966(6) 0.8070(4) 0.066(2) Uani 1 1 d D U . . .
H3A H 0.304801 0.492000 0.761260 0.079 Uiso 1 1 calc R U . . .
H3AB H 0.408852 0.474580 0.816922 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2537(11) 0.6260(7) 0.8276(5) 0.098(3) Uani 1 1 d D U . . .
H4A H 0.299841 0.682594 0.806464 0.117 Uiso 1 1 calc R U . . .
H4AB H 0.162018 0.649139 0.813993 0.117 Uiso 1 1 calc R U . . .
C5 C 0.2597(10) 0.6368(7) 0.8986(5) 0.097(3) Uani 1 1 d D U . . .
H5A H 0.216304 0.719357 0.909432 0.117 Uiso 1 1 calc R U . . .
H5AB H 0.351408 0.621457 0.911874 0.117 Uiso 1 1 calc R U . . .
C6 C 0.1937(9) 0.5474(7) 0.9339(4) 0.083(2) Uani 1 1 d D U . . .
H6A H 0.100305 0.566762 0.923325 0.100 Uiso 1 1 calc R U . . .
H6AB H 0.201868 0.554115 0.979525 0.100 Uiso 1 1 calc R U . . .
C7 C 0.2579(7) 0.4144(6) 0.9157(3) 0.0512(16) Uani 1 1 d D U . . .
H7 H 0.351908 0.395093 0.927077 0.061 Uiso 1 1 calc R U . . .
N8 N 0.1963(7) 0.3228(6) 0.9463(3) 0.084(2) Uani 1 1 d D U . . .
H8A H 0.110(3) 0.351(5) 0.939(4) 0.126 Uiso 1 1 d D U . . .
H8B H 0.207(7) 0.327(6) 0.9877(12) 0.126 Uiso 1 1 d D U . . .
N11 N 0.6528(6) 0.3332(5) 0.6558(3) 0.0577(16) Uani 1 1 d . U . . .
H11A H 0.702031 0.369057 0.629609 0.087 Uiso 1 1 calc R U . . .
H11B H 0.682172 0.331277 0.695631 0.087 Uiso 1 1 calc R U . . .
H11C H 0.568990 0.375420 0.653728 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6615(6) 0.2052(6) 0.6362(3) 0.0489(15) Uani 1 1 d . U . . .
H12 H 0.600054 0.209608 0.600641 0.059 Uiso 1 1 calc R U . . .
C13 C 0.6196(9) 0.1277(7) 0.6901(4) 0.066(2) Uani 1 1 d . U . . .
H13A H 0.530912 0.166061 0.704038 0.080 Uiso 1 1 calc R U . . .
H13B H 0.678936 0.121324 0.726108 0.080 Uiso 1 1 calc R U . . .
C14 C 0.6223(8) 0.0000(7) 0.6675(4) 0.076(2) Uani 1 1 d . U . . .
H14A H 0.597317 -0.050109 0.702396 0.091 Uiso 1 1 calc R U . . .
H14B H 0.559540 0.005692 0.633000 0.091 Uiso 1 1 calc R U . . .
C15 C 0.7612(8) -0.0584(6) 0.6446(4) 0.069(2) Uani 1 1 d . U . . .
H15A H 0.822523 -0.069013 0.680040 0.082 Uiso 1 1 calc R U . . .
H15B H 0.762740 -0.138471 0.629014 0.082 Uiso 1 1 calc R U . . .
C16 C 0.8046(8) 0.0208(7) 0.5915(4) 0.064(2) Uani 1 1 d . U . . .
H16A H 0.894377 -0.016751 0.578729 0.077 Uiso 1 1 calc R U . . .
H16B H 0.747727 0.025472 0.554648 0.077 Uiso 1 1 calc R U . . .
C17 C 0.7990(6) 0.1486(6) 0.6125(3) 0.0561(16) Uani 1 1 d D U . . .
H17 H 0.861278 0.142905 0.647877 0.067 Uiso 1 1 calc R U . . .
N18 N 0.8325(10) 0.2310(8) 0.5617(4) 0.099(3) Uani 1 1 d D U . . .
H18A H 0.918(3) 0.197(6) 0.553(3) 0.148 Uiso 1 1 d D U . . .
H18B H 0.784(8) 0.216(8) 0.5273(16) 0.148 Uiso 1 1 d D U . . .
N21 N -0.1217(12) 0.7613(10) 0.4470(5) 0.137(4) Uani 1 1 d D U . . .
H21A H -0.071(5) 0.686(3) 0.449(5) 0.206 Uiso 1 1 d D U . . .
H21B H -0.188(7) 0.766(10) 0.416(3) 0.206 Uiso 1 1 d D U . . .
C22 C -0.0375(8) 0.8343(7) 0.4126(3) 0.0657(19) Uani 1 1 d D U . . .
H22 H 0.051070 0.810024 0.431480 0.079 Uiso 1 1 calc R U . . .
C23 C -0.0857(10) 0.9714(9) 0.4183(5) 0.093(3) Uani 1 1 d . U . . .
H23A H -0.175229 0.996839 0.401769 0.111 Uiso 1 1 calc R U . . .
H23B H -0.088534 0.989687 0.463090 0.111 Uiso 1 1 calc R U . . .
C24 C -0.0021(9) 1.0428(7) 0.3837(4) 0.080(2) Uani 1 1 d . U . . .
H24A H 0.085439 1.024228 0.402584 0.096 Uiso 1 1 calc R U . . .
H24B H -0.040326 1.129573 0.387118 0.096 Uiso 1 1 calc R U . . .
C25 C 0.0080(10) 1.0116(7) 0.3139(4) 0.088(3) Uani 1 1 d . U . . .
H25A H 0.065777 1.056196 0.291496 0.105 Uiso 1 1 calc R U . . .
H25B H -0.078709 1.035677 0.294201 0.105 Uiso 1 1 calc R U . . .
C26 C 0.0636(12) 0.8732(9) 0.3086(5) 0.103(3) Uani 1 1 d . U . . .
H26A H 0.068762 0.852865 0.264027 0.123 Uiso 1 1 calc R U . . .
H26B H 0.151954 0.849639 0.326509 0.123 Uiso 1 1 calc R U . . .
C27 C -0.0244(7) 0.8063(6) 0.3438(3) 0.0542(17) Uani 1 1 d . U . . .
H27 H -0.112616 0.833062 0.324610 0.065 Uiso 1 1 calc R U . . .
N28 N 0.0194(7) 0.6729(5) 0.3369(3) 0.0602(17) Uani 1 1 d . U . . .
H28A H 0.004222 0.655267 0.297088 0.090 Uiso 1 1 calc R U . . .
H28B H -0.025243 0.634312 0.364129 0.090 Uiso 1 1 calc R U . . .
H28C H 0.105515 0.648616 0.345188 0.090 Uiso 1 1 calc R U . . .
N31 N 1.3829(7) 0.7094(6) 0.1779(3) 0.0668(18) Uani 1 1 d D U . . .
H31A H 1.411752 0.767575 0.155676 0.100 Uiso 1 1 calc R U . . .
H31B H 1.410646 0.705560 0.218127 0.100 Uiso 1 1 calc R U . . .
H31C H 1.294916 0.726850 0.177169 0.100 Uiso 1 1 calc R U . . .
C32 C 1.4359(11) 0.5888(7) 0.1488(4) 0.095(3) Uani 1 1 d D U . . .
H32 H 1.525264 0.563503 0.166769 0.114 Uiso 1 1 calc R U . . .
C33 C 1.4623(13) 0.6031(10) 0.0792(5) 0.133(4) Uani 1 1 d D U . . .
H33A H 1.532149 0.646469 0.072181 0.159 Uiso 1 1 calc R U . . .
H33B H 1.383309 0.649120 0.057333 0.159 Uiso 1 1 calc R U . . .
C34 C 1.5047(12) 0.4734(11) 0.0539(6) 0.126(4) Uani 1 1 d D U . . .
H34A H 1.492002 0.480739 0.007922 0.151 Uiso 1 1 calc R U . . .
H34B H 1.598977 0.444467 0.061337 0.151 Uiso 1 1 calc R U . . .
C35 C 1.4415(15) 0.3784(11) 0.0786(6) 0.147(5) Uani 1 1 d D U . . .
H35A H 1.488969 0.300994 0.062521 0.176 Uiso 1 1 calc R U . . .
H35B H 1.352219 0.395481 0.061742 0.176 Uiso 1 1 calc R U . . .
C36 C 1.4343(13) 0.3645(9) 0.1489(5) 0.131(4) Uani 1 1 d D U . . .
H36A H 1.522268 0.333231 0.166453 0.157 Uiso 1 1 calc R U . . .
H36B H 1.380762 0.306955 0.161037 0.157 Uiso 1 1 calc R U . . .
C37 C 1.3712(10) 0.4924(8) 0.1760(4) 0.093(3) Uani 1 1 d D U . . .
H37 H 1.278729 0.514911 0.162053 0.112 Uiso 1 1 calc R U . . .
N38 N 1.3702(12) 0.4884(10) 0.2436(4) 0.154(4) Uani 1 1 d D U . . .
H38A H 1.362(13) 0.413(5) 0.2580(12) 0.231 Uiso 1 1 d D U . . .
H38B H 1.439(8) 0.514(11) 0.2572(13) 0.231 Uiso 1 1 d D U . . .
O41 O -0.0539(5) 0.1983(5) 0.7449(2) 0.0584(14) Uani 1 1 d . U . . .
H41 H -0.119683 0.233736 0.764200 0.088 Uiso 1 1 calc R U . . .
C42 C 0.0384(7) 0.1380(7) 0.7872(3) 0.0438(16) Uani 1 1 d . U . . .
C43 C 0.0117(8) 0.1417(8) 0.8534(3) 0.0541(19) Uani 1 1 d . U . . .
H43 H -0.067863 0.189239 0.867819 0.065 Uiso 1 1 calc R U . . .
C44 C 0.1007(8) 0.0769(7) 0.8961(3) 0.0522(18) Uani 1 1 d . U . . .
H44 H 0.080627 0.080008 0.939507 0.063 Uiso 1 1 calc R U . . .
C45 C 0.2237(7) 0.0043(6) 0.8764(3) 0.0458(16) Uani 1 1 d . U . . .
C46 C 0.3176(9) -0.0628(7) 0.9196(4) 0.061(2) Uani 1 1 d . U . . .
H46 H 0.298330 -0.063743 0.963083 0.074 Uiso 1 1 calc R U . . .
C47 C 0.4382(9) -0.1276(9) 0.8985(4) 0.071(2) Uani 1 1 d . U . . .
H47 H 0.500752 -0.170352 0.927719 0.085 Uiso 1 1 calc R U . . .
C48 C 0.4672(8) -0.1293(7) 0.8332(4) 0.062(2) Uani 1 1 d . U . . .
H48 H 0.548462 -0.174341 0.819160 0.074 Uiso 1 1 calc R U . . .
C49 C 0.3769(7) -0.0651(7) 0.7897(4) 0.0525(18) Uani 1 1 d . U . . .
H49 H 0.398044 -0.066987 0.746436 0.063 Uiso 1 1 calc R U . . .
C50 C 0.2518(7) 0.0042(6) 0.8092(3) 0.0413(15) Uani 1 1 d . U . . .
C51 C 0.1572(7) 0.0713(6) 0.7650(3) 0.0405(15) Uani 1 1 d . U . . .
C52 C 0.1828(6) 0.0734(6) 0.6952(3) 0.0400(15) Uani 1 1 d . U . . .
C53 C 0.1664(6) -0.0271(7) 0.6587(3) 0.0463(17) Uani 1 1 d . U . . .
C54 C 0.1279(7) -0.1307(7) 0.6870(4) 0.0540(19) Uani 1 1 d . U . . .
H54 H 0.112422 -0.133447 0.730765 0.065 Uiso 1 1 calc R U . . .
C55 C 0.1123(8) -0.2276(8) 0.6524(4) 0.066(2) Uani 1 1 d . U . . .
H55 H 0.087647 -0.294666 0.672252 0.079 Uiso 1 1 calc R U . . .
C56 C 0.1351(8) -0.2218(9) 0.5853(4) 0.070(2) Uani 1 1 d . U . . .
H56 H 0.122605 -0.284477 0.560472 0.083 Uiso 1 1 calc R U . . .
C57 C 0.1738(7) -0.1277(8) 0.5582(4) 0.062(2) Uani 1 1 d . U . . .
H57 H 0.190088 -0.127799 0.514455 0.074 Uiso 1 1 calc R U . . .
C58 C 0.1923(7) -0.0264(7) 0.5916(3) 0.0471(17) Uani 1 1 d . U . . .
C59 C 0.2305(7) 0.0745(7) 0.5623(3) 0.0567(19) Uani 1 1 d . U . . .
H59 H 0.246195 0.076598 0.518501 0.068 Uiso 1 1 calc R U . . .
C60 C 0.2450(7) 0.1703(7) 0.5973(3) 0.0574(19) Uani 1 1 d . U . . .
H60 H 0.269718 0.236631 0.576584 0.069 Uiso 1 1 calc R U . . .
C61 C 0.2232(6) 0.1710(7) 0.6648(3) 0.0442(17) Uani 1 1 d . U . . .
O62 O 0.2404(4) 0.2656(4) 0.6959(2) 0.0475(12) Uani 1 1 d . U . . .
O71 O -0.2688(4) 0.3476(4) 0.7851(2) 0.0448(11) Uani 1 1 d . U . . .
C72 C -0.2486(6) 0.4432(6) 0.8163(3) 0.0386(15) Uani 1 1 d . U . . .
C73 C -0.2708(7) 0.4451(7) 0.8832(3) 0.0543(19) Uani 1 1 d . U . . .
H73 H -0.301858 0.381676 0.903342 0.065 Uiso 1 1 calc R U . . .
C74 C -0.2488(8) 0.5355(8) 0.9192(4) 0.058(2) Uani 1 1 d . U . . .
H74 H -0.263834 0.532503 0.963067 0.069 Uiso 1 1 calc R U . . .
C75 C -0.2035(7) 0.6336(7) 0.8904(3) 0.0507(18) Uani 1 1 d . U . . .
C76 C -0.1762(8) 0.7278(8) 0.9268(4) 0.061(2) Uani 1 1 d . U . . .
H76 H -0.189075 0.725922 0.970807 0.074 Uiso 1 1 calc R U . . .
C77 C -0.1306(9) 0.8221(8) 0.8971(4) 0.071(2) Uani 1 1 d . U . . .
H77 H -0.111158 0.883017 0.921174 0.086 Uiso 1 1 calc R U . . .
C78 C -0.1136(8) 0.8261(7) 0.8312(4) 0.064(2) Uani 1 1 d . U . . .
H78 H -0.086139 0.891726 0.811299 0.077 Uiso 1 1 calc R U . . .
C79 C -0.1364(7) 0.7362(7) 0.7957(3) 0.0530(18) Uani 1 1 d . U . . .
H79 H -0.122997 0.741033 0.751762 0.064 Uiso 1 1 calc R U . . .
C80 C -0.1799(6) 0.6349(6) 0.8230(3) 0.0398(15) Uani 1 1 d . U . . .
C81 C -0.2028(6) 0.5393(6) 0.7879(3) 0.0366(14) Uani 1 1 d . U . . .
C82 C -0.1792(6) 0.5408(6) 0.7167(3) 0.0368(15) Uani 1 1 d . U . . .
C83 C -0.2800(6) 0.5983(6) 0.6727(3) 0.0378(15) Uani 1 1 d . U . . .
C84 C -0.4097(7) 0.6552(7) 0.6939(3) 0.0483(17) Uani 1 1 d . U . . .
H84 H -0.428884 0.655384 0.737389 0.058 Uiso 1 1 calc R U . . .
C85 C -0.5054(7) 0.7090(7) 0.6512(4) 0.060(2) Uani 1 1 d . U . . .
H85 H -0.589508 0.745515 0.665761 0.071 Uiso 1 1 calc R U . . .
C86 C -0.4786(8) 0.7104(8) 0.5840(4) 0.068(2) Uani 1 1 d . U . . .
H86 H -0.544669 0.746496 0.554888 0.082 Uiso 1 1 calc R U . . .
C87 C -0.3556(8) 0.6584(7) 0.5638(4) 0.0560(19) Uani 1 1 d . U . . .
H87 H -0.337875 0.660050 0.520169 0.067 Uiso 1 1 calc R U . . .
C88 C -0.2532(7) 0.6018(6) 0.6059(3) 0.0418(16) Uani 1 1 d . U . . .
C89 C -0.1262(7) 0.5450(7) 0.5847(3) 0.0484(17) Uani 1 1 d . U . . .
H89 H -0.107311 0.546800 0.541174 0.058 Uiso 1 1 calc R U . . .
C90 C -0.0299(7) 0.4873(7) 0.6267(3) 0.0486(18) Uani 1 1 d . U . . .
H90 H 0.052863 0.449098 0.611252 0.058 Uiso 1 1 calc R U . . .
C91 C -0.0534(6) 0.4845(6) 0.6930(3) 0.0403(15) Uani 1 1 d . U . . .
O92 O 0.0406(5) 0.4336(5) 0.7347(2) 0.0579(14) Uani 1 1 d . U . . .
H92 H 0.108470 0.403010 0.715407 0.087 Uiso 1 1 calc R U . . .
O101 O 0.4568(5) 0.7270(4) 0.3053(2) 0.0496(12) Uani 1 1 d . U . . .
C102 C 0.4777(6) 0.8237(6) 0.3353(3) 0.0432(16) Uani 1 1 d . U . . .
C103 C 0.4613(8) 0.8275(7) 0.4026(3) 0.0548(19) Uani 1 1 d . U . . .
H103 H 0.435533 0.763051 0.424719 0.066 Uiso 1 1 calc R U . . .
C104 C 0.4815(8) 0.9201(7) 0.4352(4) 0.0574(19) Uani 1 1 d . U . . .
H104 H 0.470108 0.918211 0.479330 0.069 Uiso 1 1 calc R U . . .
C105 C 0.5203(7) 1.0227(7) 0.4043(3) 0.0483(17) Uani 1 1 d . U . . .
C106 C 0.5394(8) 1.1220(8) 0.4389(4) 0.066(2) Uani 1 1 d . U . . .
H106 H 0.526316 1.122829 0.482890 0.079 Uiso 1 1 calc R U . . .
C107 C 0.5779(9) 1.2181(8) 0.4061(4) 0.070(2) Uani 1 1 d . U . . .
H107 H 0.592213 1.283620 0.428167 0.084 Uiso 1 1 calc R U . . .
C108 C 0.5947(8) 1.2162(8) 0.3412(4) 0.063(2) Uani 1 1 d . U . . .
H108 H 0.621544 1.280944 0.320063 0.076 Uiso 1 1 calc R U . . .
C109 C 0.5736(7) 1.1233(7) 0.3063(4) 0.0528(18) Uani 1 1 d . U . . .
H109 H 0.584751 1.126554 0.262223 0.063 Uiso 1 1 calc R U . . .
C110 C 0.5348(7) 1.0218(7) 0.3367(3) 0.0424(16) Uani 1 1 d . U . . .
C111 C 0.5143(6) 0.9237(6) 0.3033(3) 0.0435(16) Uani 1 1 d . U . . .
C112 C 0.5350(6) 0.9215(7) 0.2316(3) 0.0405(15) Uani 1 1 d . U . . .
C113 C 0.4373(7) 0.9884(6) 0.1888(3) 0.0440(16) Uani 1 1 d . U . . .
C114 C 0.3130(7) 1.0568(7) 0.2100(4) 0.0501(17) Uani 1 1 d . U . . .
H114 H 0.294503 1.058792 0.253563 0.060 Uiso 1 1 calc R U . . .
C115 C 0.2213(8) 1.1189(8) 0.1681(4) 0.062(2) Uani 1 1 d . U . . .
H115 H 0.140176 1.161633 0.183474 0.074 Uiso 1 1 calc R U . . .
C116 C 0.2448(9) 1.1209(8) 0.1024(4) 0.065(2) Uani 1 1 d . U . . .
H116 H 0.180724 1.165359 0.074346 0.078 Uiso 1 1 calc R U . . .
C117 C 0.3612(9) 1.0576(8) 0.0802(4) 0.062(2) Uani 1 1 d . U . . .
H117 H 0.377257 1.059975 0.036429 0.074 Uiso 1 1 calc R U . . .
C118 C 0.4612(8) 0.9868(7) 0.1218(3) 0.0519(18) Uani 1 1 d . U . . .
C119 C 0.5804(8) 0.9138(8) 0.0995(4) 0.062(2) Uani 1 1 d . U . . .
H119 H 0.595158 0.909812 0.055682 0.074 Uiso 1 1 calc R U . . .
C120 C 0.6740(8) 0.8492(8) 0.1400(4) 0.058(2) Uani 1 1 d . U . . .
H120 H 0.751698 0.801356 0.123855 0.070 Uiso 1 1 calc R U . . .
C121 C 0.6541(7) 0.8541(7) 0.2072(3) 0.0471(17) Uani 1 1 d . U . . .
O122 O 0.7464(5) 0.7942(5) 0.2492(2) 0.0644(14) Uani 1 1 d . U . . .
H122 H 0.798599 0.739901 0.231182 0.097 Uiso 1 1 calc R U . . .
O131 O 0.6536(5) 0.5616(5) 0.2619(2) 0.0606(14) Uani 1 1 d . U . . .
H131 H 0.587463 0.591548 0.282522 0.091 Uiso 1 1 calc R U . . .
C132 C 0.7548(7) 0.5064(7) 0.3032(3) 0.0456(17) Uani 1 1 d . U . . .
C133 C 0.7305(7) 0.5084(7) 0.3701(4) 0.0529(19) Uani 1 1 d . U . . .
H133 H 0.648099 0.548158 0.385390 0.063 Uiso 1 1 calc R U . . .
C134 C 0.8264(8) 0.4528(7) 0.4112(3) 0.0527(18) Uani 1 1 d . U . . .
H134 H 0.809181 0.452993 0.454908 0.063 Uiso 1 1 calc R U . . .
C135 C 0.9531(7) 0.3940(6) 0.3890(3) 0.0449(16) Uani 1 1 d . U . . .
C136 C 1.0575(8) 0.3371(7) 0.4312(4) 0.061(2) Uani 1 1 d . U . . .
H136 H 1.043292 0.336605 0.475124 0.074 Uiso 1 1 calc R U . . .
C137 C 1.1774(9) 0.2838(8) 0.4078(4) 0.067(2) Uani 1 1 d . U . . .
H137 H 1.244468 0.246120 0.436021 0.080 Uiso 1 1 calc R U . . .
C138 C 1.2031(8) 0.2837(8) 0.3436(4) 0.067(2) Uani 1 1 d . U . . .
H138 H 1.287157 0.247756 0.328782 0.081 Uiso 1 1 calc R U . . .
C139 C 1.1046(7) 0.3366(7) 0.3013(4) 0.0542(19) Uani 1 1 d . U . . .
H139 H 1.122918 0.336109 0.257712 0.065 Uiso 1 1 calc R U . . .
C140 C 0.9771(6) 0.3913(6) 0.3220(3) 0.0413(15) Uani 1 1 d . U . . .
C141 C 0.8735(7) 0.4502(6) 0.2787(3) 0.0388(15) Uani 1 1 d . U . . .
C142 C 0.8985(6) 0.4518(6) 0.2089(3) 0.0406(15) Uani 1 1 d . U . . .
C143 C 0.8734(7) 0.3545(7) 0.1712(3) 0.0448(16) Uani 1 1 d . U . . .
C144 C 0.8274(7) 0.2552(7) 0.2003(4) 0.057(2) Uani 1 1 d . U . . .
H144 H 0.814729 0.251132 0.244263 0.068 Uiso 1 1 calc R U . . .
C145 C 0.8013(9) 0.1645(8) 0.1637(4) 0.070(2) Uani 1 1 d . U . . .
H145 H 0.771136 0.099887 0.183034 0.084 Uiso 1 1 calc R U . . .
C146 C 0.8205(9) 0.1702(8) 0.0970(4) 0.075(2) Uani 1 1 d . U . . .
H146 H 0.803958 0.108749 0.072506 0.090 Uiso 1 1 calc R U . . .
C147 C 0.8625(8) 0.2641(8) 0.0688(4) 0.068(2) Uani 1 1 d . U . . .
H147 H 0.872228 0.267368 0.024556 0.081 Uiso 1 1 calc R U . . .
C148 C 0.8926(7) 0.3585(7) 0.1042(3) 0.0473(17) Uani 1 1 d . U . . .
C149 C 0.9393(8) 0.4566(8) 0.0761(3) 0.0582(19) Uani 1 1 d . U . . .
H149 H 0.954292 0.458958 0.032253 0.070 Uiso 1 1 calc R U . . .
C150 C 0.9630(8) 0.5473(7) 0.1106(3) 0.057(2) Uani 1 1 d . U . . .
H150 H 0.994723 0.610004 0.090103 0.068 Uiso 1 1 calc R U . . .
C151 C 0.9405(7) 0.5488(7) 0.1777(3) 0.0453(16) Uani 1 1 d . U . . .
O152 O 0.9610(5) 0.6411(4) 0.2104(2) 0.0505(12) Uani 1 1 d . U . . .
O161 O -0.4318(5) 0.2360(5) 0.8442(2) 0.0605(13) Uani 1 1 d . U . . .
H161 H -0.378693 0.266533 0.823880 0.091 Uiso 1 1 calc R U . . .
C162 C -0.3657(8) 0.1226(7) 0.8726(4) 0.066(2) Uani 1 1 d . U . . .
H62A H -0.273243 0.105852 0.860185 0.079 Uiso 1 1 calc R U . . .
H62B H -0.403398 0.058634 0.856696 0.079 Uiso 1 1 calc R U . . .
C163 C -0.3748(15) 0.1199(11) 0.9402(5) 0.124(5) Uani 1 1 d . U . . .
H63A H -0.328432 0.041132 0.957357 0.149 Uiso 1 1 calc R U . . .
H63B H -0.335935 0.182011 0.956210 0.149 Uiso 1 1 calc R U . . .
H63C H -0.466063 0.134802 0.952722 0.149 Uiso 1 1 calc R U . . .
O171 O 0.3831(6) 0.4136(7) 0.6391(3) 0.0896(19) Uani 1 1 d D U . . .
H71A H 0.319(9) 0.484(6) 0.638(8) 0.134 Uiso 0.678(14) 1 d D U P A 1
H71B H 0.345(9) 0.352(6) 0.653(5) 0.134 Uiso 1 1 d D U . B 1
C172 C 0.340(3) 0.479(3) 0.5885(13) 0.077(8) Uani 0.322(14) 1 d D U P A 2
H17A H 0.331210 0.563583 0.598577 0.093 Uiso 0.322(14) 1 calc R U P A 2
H17B H 0.250660 0.468993 0.581570 0.093 Uiso 0.322(14) 1 calc R U P A 2
C173 C 0.410(4) 0.462(3) 0.5262(13) 0.101(10) Uani 0.322(14) 1 d D U P A 2
H17C H 0.361421 0.519116 0.494598 0.152 Uiso 0.322(14) 1 calc R U P A 2
H17D H 0.496905 0.475264 0.530462 0.152 Uiso 0.322(14) 1 calc R U P A 2
H17E H 0.415737 0.379947 0.513324 0.152 Uiso 0.322(14) 1 calc R U P A 2
O181 O 0.2888(7) 0.6163(7) 0.3692(4) 0.109(2) Uani 1 1 d D U . . .
H181 H 0.340045 0.635200 0.342578 0.164 Uiso 1 1 calc DR U . A 1
H81B H 0.29(3) 0.536(8) 0.372(16) 0.164 Uiso 0.322(14) 1 d D U P A 2
C182 C 0.3545(14) 0.5177(13) 0.4068(7) 0.081(4) Uani 0.678(14) 1 d D U P A 1
H82A H 0.448208 0.515930 0.405534 0.097 Uiso 0.678(14) 1 calc R U P A 1
H82B H 0.342940 0.443495 0.388256 0.097 Uiso 0.678(14) 1 calc R U P A 1
C183 C 0.311(2) 0.5162(19) 0.4751(7) 0.139(7) Uani 0.678(14) 1 d D U P A 1
H18C H 0.362330 0.444439 0.497499 0.208 Uiso 0.678(14) 1 calc R U P A 1
H18D H 0.324743 0.587868 0.494562 0.208 Uiso 0.678(14) 1 calc R U P A 1
H18E H 0.219240 0.515270 0.477245 0.208 Uiso 0.678(14) 1 calc R U P A 1
O191 O 1.1194(5) 0.7636(6) 0.1520(3) 0.0787(17) Uani 1 1 d . U . . .
H191 H 1.071590 0.736213 0.177364 0.118 Uiso 1 1 calc R U . . .
C192 C 1.0461(10) 0.8723(9) 0.1213(5) 0.087(3) Uani 1 1 d . U . . .
H92A H 1.077639 0.941084 0.135770 0.104 Uiso 1 1 calc R U . . .
H92B H 0.953878 0.884038 0.133561 0.104 Uiso 1 1 calc R U . . .
C193 C 1.0564(16) 0.8708(12) 0.0521(5) 0.142(5) Uani 1 1 d . U . . .
H93A H 1.005012 0.946476 0.033495 0.213 Uiso 1 1 calc R U . . .
H93B H 1.147283 0.861030 0.039586 0.213 Uiso 1 1 calc R U . . .
H93C H 1.023523 0.803984 0.037377 0.213 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
N1 C2 1.501(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 C3 1.499(9) . ?
C2 C7 1.542(8) . ?
C2 H2 0.9800 . ?
C3 C4 1.529(10) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.502(11) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.504(11) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C6 C7 1.553(9) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C7 N8 1.455(8) . ?
C7 H7 0.9800 . ?
N8 H8A 0.89(3) . ?
N8 H8B 0.88(3) . ?
N11 C12 1.499(8) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
C12 C17 1.511(9) . ?
C12 C13 1.515(9) . ?
C12 H12 0.9800 . ?
C13 C14 1.528(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.523(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.521(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.512(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N18 1.469(10) . ?
C17 H17 0.9800 . ?
N18 H18A 0.90(3) . ?
N18 H18B 0.93(3) . ?
N21 C22 1.490(11) . ?
N21 H21A 0.88(3) . ?
N21 H21B 0.95(3) . ?
C22 C27 1.490(9) . ?
C22 C23 1.516(11) . ?
C22 H22 0.9800 . ?
C23 C24 1.476(11) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.518(11) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.539(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.482(11) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 N28 1.477(9) . ?
C27 H27 0.9800 . ?
N28 H28A 0.8900 . ?
N28 H28B 0.8900 . ?
N28 H28C 0.8900 . ?
N31 C32 1.497(8) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
N31 H31C 0.8900 . ?
C32 C33 1.488(11) . ?
C32 C37 1.490(11) . ?
C32 H32 0.9800 . ?
C33 C34 1.542(12) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.451(12) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.477(12) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.567(12) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 N38 1.414(10) . ?
C37 H37 0.9800 . ?
N38 H38A 0.90(2) . ?
N38 H38B 0.89(2) . ?
O41 C42 1.351(8) . ?
O41 H41 0.8200 . ?
C42 C51 1.376(9) . ?
C42 C43 1.411(9) . ?
C43 C44 1.353(11) . ?
C43 H43 0.9300 . ?
C44 C45 1.417(11) . ?
C44 H44 0.9300 . ?
C45 C46 1.399(10) . ?
C45 C50 1.434(9) . ?
C46 C47 1.375(12) . ?
C46 H46 0.9300 . ?
C47 C48 1.397(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.369(10) . ?
C48 H48 0.9300 . ?
C49 C50 1.418(10) . ?
C49 H49 0.9300 . ?
C50 C51 1.415(9) . ?
C51 C52 1.483(9) . ?
C52 C61 1.387(10) . ?
C52 C53 1.439(9) . ?
C53 C54 1.418(11) . ?
C53 C58 1.430(9) . ?
C54 C55 1.380(10) . ?
C54 H54 0.9300 . ?
C55 C56 1.423(12) . ?
C55 H55 0.9300 . ?
C56 C57 1.318(12) . ?
C56 H56 0.9300 . ?
C57 C58 1.417(11) . ?
C57 H57 0.9300 . ?
C58 C59 1.399(11) . ?
C59 C60 1.371(10) . ?
C59 H59 0.9300 . ?
C60 C61 1.430(9) . ?
C60 H60 0.9300 . ?
C61 O62 1.322(8) . ?
O71 C72 1.344(8) . ?
C72 C81 1.384(9) . ?
C72 C73 1.419(9) . ?
C73 C74 1.358(10) . ?
C73 H73 0.9300 . ?
C74 C75 1.404(11) . ?
C74 H74 0.9300 . ?
C75 C76 1.417(10) . ?
C75 C80 1.431(9) . ?
C76 C77 1.379(12) . ?
C76 H76 0.9300 . ?
C77 C78 1.389(12) . ?
C77 H77 0.9300 . ?
C78 C79 1.351(10) . ?
C78 H78 0.9300 . ?
C79 C80 1.414(10) . ?
C79 H79 0.9300 . ?
C80 C81 1.400(9) . ?
C81 C82 1.509(9) . ?
C82 C91 1.408(9) . ?
C82 C83 1.420(9) . ?
C83 C88 1.424(9) . ?
C83 C84 1.426(9) . ?
C84 C85 1.359(10) . ?
C84 H84 0.9300 . ?
C85 C86 1.431(12) . ?
C85 H85 0.9300 . ?
C86 C87 1.349(11) . ?
C86 H86 0.9300 . ?
C87 C88 1.403(10) . ?
C87 H87 0.9300 . ?
C88 C89 1.403(10) . ?
C89 C90 1.365(10) . ?
C89 H89 0.9300 . ?
C90 C91 1.408(9) . ?
C90 H90 0.9300 . ?
C91 O92 1.324(8) . ?
O92 H92 0.8200 . ?
O101 C102 1.344(8) . ?
C102 C111 1.407(10) . ?
C102 C103 1.421(9) . ?
C103 C104 1.331(10) . ?
C103 H103 0.9300 . ?
C104 C105 1.432(11) . ?
C104 H104 0.9300 . ?
C105 C106 1.415(10) . ?
C105 C110 1.421(9) . ?
C106 C107 1.386(12) . ?
C106 H106 0.9300 . ?
C107 C108 1.370(11) . ?
C107 H107 0.9300 . ?
C108 C109 1.365(10) . ?
C108 H108 0.9300 . ?
C109 C110 1.416(10) . ?
C109 H109 0.9300 . ?
C110 C111 1.395(9) . ?
C111 C112 1.514(9) . ?
C112 C121 1.397(10) . ?
C112 C113 1.416(9) . ?
C113 C114 1.420(10) . ?
C113 C118 1.422(9) . ?
C114 C115 1.348(10) . ?
C114 H114 0.9300 . ?
C115 C116 1.396(11) . ?
C115 H115 0.9300 . ?
C116 C117 1.343(12) . ?
C116 H116 0.9300 . ?
C117 C118 1.429(11) . ?
C117 H117 0.9300 . ?
C118 C119 1.407(11) . ?
C119 C120 1.351(11) . ?
C119 H119 0.9300 . ?
C120 C121 1.424(10) . ?
C120 H120 0.9300 . ?
C121 O122 1.345(9) . ?
O122 H122 0.8200 . ?
O131 C132 1.381(8) . ?
O131 H131 0.8200 . ?
C132 C141 1.355(10) . ?
C132 C133 1.422(10) . ?
C133 C134 1.345(10) . ?
C133 H133 0.9300 . ?
C134 C135 1.413(10) . ?
C134 H134 0.9300 . ?
C135 C136 1.419(10) . ?
C135 C140 1.424(9) . ?
C136 C137 1.349(11) . ?
C136 H136 0.9300 . ?
C137 C138 1.366(11) . ?
C137 H137 0.9300 . ?
C138 C139 1.370(10) . ?
C138 H138 0.9300 . ?
C139 C140 1.398(10) . ?
C139 H139 0.9300 . ?
C140 C141 1.433(9) . ?
C141 C142 1.484(9) . ?
C142 C151 1.397(10) . ?
C142 C143 1.454(9) . ?
C143 C148 1.416(9) . ?
C143 C144 1.422(10) . ?
C144 C145 1.383(10) . ?
C144 H144 0.9300 . ?
C145 C146 1.408(12) . ?
C145 H145 0.9300 . ?
C146 C147 1.343(12) . ?
C146 H146 0.9300 . ?
C147 C148 1.419(11) . ?
C147 H147 0.9300 . ?
C148 C149 1.406(11) . ?
C149 C150 1.349(10) . ?
C149 H149 0.9300 . ?
C150 C151 1.423(10) . ?
C150 H150 0.9300 . ?
C151 O152 1.330(8) . ?
O161 C162 1.406(9) . ?
O161 H161 0.8200 . ?
C162 C163 1.417(12) . ?
C162 H62A 0.9700 . ?
C162 H62B 0.9700 . ?
C163 H63A 0.9600 . ?
C163 H63B 0.9600 . ?
C163 H63C 0.9600 . ?
O171 C172 1.28(3) . ?
O171 H71A 0.91(3) . ?
O171 H71B 0.91(3) . ?
C172 C173 1.486(18) . ?
C172 H17A 0.9700 . ?
C172 H17B 0.9700 . ?
C173 H17C 0.9600 . ?
C173 H17D 0.9600 . ?
C173 H17E 0.9600 . ?
O181 C182 1.376(15) . ?
O181 H181 0.8200 . ?
O181 H81B 0.90(3) . ?
C182 C183 1.496(15) . ?
C182 H82A 0.9700 . ?
C182 H82B 0.9700 . ?
C183 H18C 0.9600 . ?
C183 H18D 0.9600 . ?
C183 H18E 0.9600 . ?
O191 C192 1.411(11) . ?
O191 H191 0.8200 . ?
C192 C193 1.454(14) . ?
C192 H92A 0.9700 . ?
C192 H92B 0.9700 . ?
C193 H93A 0.9600 . ?
C193 H93B 0.9600 . ?
C193 H93C 0.9600 . ?

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 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C2 N1 110.0(5) . . ?
C3 C2 C7 112.7(5) . . ?
N1 C2 C7 107.8(5) . . ?
C3 C2 H2 108.7 . . ?
N1 C2 H2 108.7 . . ?
C7 C2 H2 108.7 . . ?
C2 C3 C4 107.5(6) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3AB 110.2 . . ?
C4 C3 H3AB 110.2 . . ?
H3A C3 H3AB 108.5 . . ?
C5 C4 C3 112.6(7) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4AB 109.1 . . ?
C3 C4 H4AB 109.1 . . ?
H4A C4 H4AB 107.8 . . ?
C4 C5 C6 111.2(6) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5AB 109.4 . . ?
C6 C5 H5AB 109.4 . . ?
H5A C5 H5AB 108.0 . . ?
C5 C6 C7 110.6(6) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6AB 109.5 . . ?
C7 C6 H6AB 109.5 . . ?
H6A C6 H6AB 108.1 . . ?
N8 C7 C2 109.2(5) . . ?
N8 C7 C6 113.8(6) . . ?
C2 C7 C6 106.7(6) . . ?
N8 C7 H7 109.0 . . ?
C2 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
C7 N8 H8A 105(2) . . ?
C7 N8 H8B 106(2) . . ?
H8A N8 H8B 105(5) . . ?
C12 N11 H11A 109.5 . . ?
C12 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
C12 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
N11 C12 C17 110.7(5) . . ?
N11 C12 C13 111.3(5) . . ?
C17 C12 C13 111.6(6) . . ?
N11 C12 H12 107.7 . . ?
C17 C12 H12 107.7 . . ?
C13 C12 H12 107.7 . . ?
C12 C13 C14 110.0(6) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 109.2(6) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 C14 110.9(6) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 111.6(6) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N18 C17 C12 107.9(6) . . ?
N18 C17 C16 113.7(6) . . ?
C12 C17 C16 109.8(5) . . ?
N18 C17 H17 108.4 . . ?
C12 C17 H17 108.4 . . ?
C16 C17 H17 108.4 . . ?
C17 N18 H18A 104(2) . . ?
C17 N18 H18B 103(2) . . ?
H18A N18 H18B 106(6) . . ?
C22 N21 H21A 103(2) . . ?
C22 N21 H21B 100(2) . . ?
H21A N21 H21B 109(7) . . ?
C27 C22 N21 111.1(7) . . ?
C27 C22 C23 109.2(6) . . ?
N21 C22 C23 113.9(7) . . ?
C27 C22 H22 107.5 . . ?
N21 C22 H22 107.5 . . ?
C23 C22 H22 107.5 . . ?
C24 C23 C22 113.5(7) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 109.7(7) . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24B 109.7 . . ?
C25 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C24 C25 C26 109.7(7) . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C27 C26 C25 109.2(8) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
N28 C27 C26 111.6(7) . . ?
N28 C27 C22 110.3(5) . . ?
C26 C27 C22 112.5(7) . . ?
N28 C27 H27 107.4 . . ?
C26 C27 H27 107.4 . . ?
C22 C27 H27 107.4 . . ?
C27 N28 H28A 109.5 . . ?
C27 N28 H28B 109.5 . . ?
H28A N28 H28B 109.5 . . ?
C27 N28 H28C 109.5 . . ?
H28A N28 H28C 109.5 . . ?
H28B N28 H28C 109.5 . . ?
C32 N31 H31A 109.5 . . ?
C32 N31 H31B 109.5 . . ?
H31A N31 H31B 109.5 . . ?
C32 N31 H31C 109.5 . . ?
H31A N31 H31C 109.5 . . ?
H31B N31 H31C 109.5 . . ?
C33 C32 C37 122.4(7) . . ?
C33 C32 N31 112.0(7) . . ?
C37 C32 N31 111.9(7) . . ?
C33 C32 H32 102.5 . . ?
C37 C32 H32 102.5 . . ?
N31 C32 H32 102.5 . . ?
C32 C33 C34 107.1(9) . . ?
C32 C33 H33A 110.3 . . ?
C34 C33 H33A 110.3 . . ?
C32 C33 H33B 110.3 . . ?
C34 C33 H33B 110.3 . . ?
H33A C33 H33B 108.6 . . ?
C35 C34 C33 119.6(9) . . ?
C35 C34 H34A 107.4 . . ?
C33 C34 H34A 107.4 . . ?
C35 C34 H34B 107.4 . . ?
C33 C34 H34B 107.4 . . ?
H34A C34 H34B 106.9 . . ?
C34 C35 C36 115.7(11) . . ?
C34 C35 H35A 108.4 . . ?
C36 C35 H35A 108.4 . . ?
C34 C35 H35B 108.4 . . ?
C36 C35 H35B 108.4 . . ?
H35A C35 H35B 107.4 . . ?
C35 C36 C37 108.8(8) . . ?
C35 C36 H36A 109.9 . . ?
C37 C36 H36A 109.9 . . ?
C35 C36 H36B 109.9 . . ?
C37 C36 H36B 109.9 . . ?
H36A C36 H36B 108.3 . . ?
N38 C37 C32 111.8(7) . . ?
N38 C37 C36 112.1(8) . . ?
C32 C37 C36 111.5(8) . . ?
N38 C37 H37 107.0 . . ?
C32 C37 H37 107.0 . . ?
C36 C37 H37 107.0 . . ?
C37 N38 H38A 109(2) . . ?
C37 N38 H38B 109(2) . . ?
H38A N38 H38B 118(6) . . ?
C42 O41 H41 109.5 . . ?
O41 C42 C51 119.2(6) . . ?
O41 C42 C43 120.2(6) . . ?
C51 C42 C43 120.6(7) . . ?
C44 C43 C42 120.7(7) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 121.5(7) . . ?
C43 C44 H44 119.2 . . ?
C45 C44 H44 119.2 . . ?
C46 C45 C44 122.6(7) . . ?
C46 C45 C50 120.0(7) . . ?
C44 C45 C50 117.4(7) . . ?
C47 C46 C45 120.6(8) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C46 C47 C48 120.2(8) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 H47 119.9 . . ?
C49 C48 C47 120.4(8) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C48 C49 C50 121.5(7) . . ?
C48 C49 H49 119.3 . . ?
C50 C49 H49 119.3 . . ?
C51 C50 C49 122.3(6) . . ?
C51 C50 C45 120.5(6) . . ?
C49 C50 C45 117.2(7) . . ?
C42 C51 C50 119.3(6) . . ?
C42 C51 C52 118.7(6) . . ?
C50 C51 C52 122.0(6) . . ?
C61 C52 C53 119.8(6) . . ?
C61 C52 C51 120.6(6) . . ?
C53 C52 C51 119.6(6) . . ?
C54 C53 C58 117.4(7) . . ?
C54 C53 C52 122.7(6) . . ?
C58 C53 C52 119.9(7) . . ?
C55 C54 C53 123.0(7) . . ?
C55 C54 H54 118.5 . . ?
C53 C54 H54 118.5 . . ?
C54 C55 C56 117.9(8) . . ?
C54 C55 H55 121.0 . . ?
C56 C55 H55 121.0 . . ?
C57 C56 C55 120.1(8) . . ?
C57 C56 H56 119.9 . . ?
C55 C56 H56 119.9 . . ?
C56 C57 C58 124.2(8) . . ?
C56 C57 H57 117.9 . . ?
C58 C57 H57 117.9 . . ?
C59 C58 C57 123.9(7) . . ?
C59 C58 C53 118.8(7) . . ?
C57 C58 C53 117.3(7) . . ?
C60 C59 C58 120.9(7) . . ?
C60 C59 H59 119.6 . . ?
C58 C59 H59 119.6 . . ?
C59 C60 C61 121.7(7) . . ?
C59 C60 H60 119.1 . . ?
C61 C60 H60 119.1 . . ?
O62 C61 C52 122.4(6) . . ?
O62 C61 C60 118.7(6) . . ?
C52 C61 C60 118.9(7) . . ?
O71 C72 C81 124.3(6) . . ?
O71 C72 C73 118.5(6) . . ?
C81 C72 C73 117.1(6) . . ?
C74 C73 C72 122.9(7) . . ?
C74 C73 H73 118.6 . . ?
C72 C73 H73 118.6 . . ?
C73 C74 C75 120.2(7) . . ?
C73 C74 H74 119.9 . . ?
C75 C74 H74 119.9 . . ?
C74 C75 C76 121.7(7) . . ?
C74 C75 C80 118.6(6) . . ?
C76 C75 C80 119.7(7) . . ?
C77 C76 C75 120.2(7) . . ?
C77 C76 H76 119.9 . . ?
C75 C76 H76 119.9 . . ?
C76 C77 C78 119.9(8) . . ?
C76 C77 H77 120.0 . . ?
C78 C77 H77 120.0 . . ?
C79 C78 C77 121.0(8) . . ?
C79 C78 H78 119.5 . . ?
C77 C78 H78 119.5 . . ?
C78 C79 C80 122.2(7) . . ?
C78 C79 H79 118.9 . . ?
C80 C79 H79 118.9 . . ?
C81 C80 C79 123.8(6) . . ?
C81 C80 C75 119.3(6) . . ?
C79 C80 C75 116.9(6) . . ?
C72 C81 C80 122.0(6) . . ?
C72 C81 C82 118.5(6) . . ?
C80 C81 C82 119.5(6) . . ?
C91 C82 C83 118.9(6) . . ?
C91 C82 C81 119.2(6) . . ?
C83 C82 C81 121.8(6) . . ?
C82 C83 C88 120.4(6) . . ?
C82 C83 C84 121.3(6) . . ?
C88 C83 C84 118.2(6) . . ?
C85 C84 C83 120.6(7) . . ?
C85 C84 H84 119.7 . . ?
C83 C84 H84 119.7 . . ?
C84 C85 C86 120.9(7) . . ?
C84 C85 H85 119.5 . . ?
C86 C85 H85 119.5 . . ?
C87 C86 C85 118.7(7) . . ?
C87 C86 H86 120.7 . . ?
C85 C86 H86 120.7 . . ?
C86 C87 C88 122.6(7) . . ?
C86 C87 H87 118.7 . . ?
C88 C87 H87 118.7 . . ?
C87 C88 C89 122.6(7) . . ?
C87 C88 C83 118.9(7) . . ?
C89 C88 C83 118.5(6) . . ?
C90 C89 C88 121.2(6) . . ?
C90 C89 H89 119.4 . . ?
C88 C89 H89 119.4 . . ?
C89 C90 C91 121.3(7) . . ?
C89 C90 H90 119.3 . . ?
C91 C90 H90 119.3 . . ?
O92 C91 C90 122.1(6) . . ?
O92 C91 C82 118.3(6) . . ?
C90 C91 C82 119.6(6) . . ?
C91 O92 H92 109.5 . . ?
O101 C102 C111 123.3(6) . . ?
O101 C102 C103 119.2(6) . . ?
C111 C102 C103 117.4(6) . . ?
C104 C103 C102 122.2(7) . . ?
C104 C103 H103 118.9 . . ?
C102 C103 H103 118.9 . . ?
C103 C104 C105 121.9(7) . . ?
C103 C104 H104 119.1 . . ?
C105 C104 H104 119.1 . . ?
C106 C105 C110 121.4(7) . . ?
C106 C105 C104 121.7(7) . . ?
C110 C105 C104 116.8(7) . . ?
C107 C106 C105 118.9(8) . . ?
C107 C106 H106 120.6 . . ?
C105 C106 H106 120.6 . . ?
C108 C107 C106 119.8(8) . . ?
C108 C107 H107 120.1 . . ?
C106 C107 H107 120.1 . . ?
C109 C108 C107 122.7(8) . . ?
C109 C108 H108 118.6 . . ?
C107 C108 H108 118.6 . . ?
C108 C109 C110 120.6(7) . . ?
C108 C109 H109 119.7 . . ?
C110 C109 H109 119.7 . . ?
C111 C110 C109 122.7(6) . . ?
C111 C110 C105 120.7(6) . . ?
C109 C110 C105 116.6(6) . . ?
C110 C111 C102 121.0(6) . . ?
C110 C111 C112 120.3(6) . . ?
C102 C111 C112 118.7(6) . . ?
C121 C112 C113 119.2(6) . . ?
C121 C112 C111 119.4(6) . . ?
C113 C112 C111 121.4(6) . . ?
C112 C113 C114 122.3(6) . . ?
C112 C113 C118 120.0(7) . . ?
C114 C113 C118 117.7(7) . . ?
C115 C114 C113 121.1(7) . . ?
C115 C114 H114 119.5 . . ?
C113 C114 H114 119.5 . . ?
C114 C115 C116 121.8(8) . . ?
C114 C115 H115 119.1 . . ?
C116 C115 H115 119.1 . . ?
C117 C116 C115 119.1(8) . . ?
C117 C116 H116 120.5 . . ?
C115 C116 H116 120.5 . . ?
C116 C117 C118 122.0(7) . . ?
C116 C117 H117 119.0 . . ?
C118 C117 H117 119.0 . . ?
C119 C118 C113 118.6(7) . . ?
C119 C118 C117 123.1(7) . . ?
C113 C118 C117 118.3(7) . . ?
C120 C119 C118 121.8(7) . . ?
C120 C119 H119 119.1 . . ?
C118 C119 H119 119.1 . . ?
C119 C120 C121 120.3(7) . . ?
C119 C120 H120 119.9 . . ?
C121 C120 H120 119.9 . . ?
O122 C121 C112 117.8(6) . . ?
O122 C121 C120 122.1(7) . . ?
C112 C121 C120 120.0(7) . . ?
C121 O122 H122 109.5 . . ?
C132 O131 H131 109.5 . . ?
C141 C132 O131 119.1(6) . . ?
C141 C132 C133 122.0(7) . . ?
O131 C132 C133 118.9(6) . . ?
C134 C133 C132 120.0(7) . . ?
C134 C133 H133 120.0 . . ?
C132 C133 H133 120.0 . . ?
C133 C134 C135 120.9(7) . . ?
C133 C134 H134 119.6 . . ?
C135 C134 H134 119.6 . . ?
C134 C135 C136 122.3(7) . . ?
C134 C135 C140 119.0(7) . . ?
C136 C135 C140 118.6(7) . . ?
C137 C136 C135 120.2(8) . . ?
C137 C136 H136 119.9 . . ?
C135 C136 H136 119.9 . . ?
C136 C137 C138 121.9(8) . . ?
C136 C137 H137 119.1 . . ?
C138 C137 H137 119.1 . . ?
C137 C138 C139 119.8(8) . . ?
C137 C138 H138 120.1 . . ?
C139 C138 H138 120.1 . . ?
C138 C139 C140 121.5(7) . . ?
C138 C139 H139 119.2 . . ?
C140 C139 H139 119.2 . . ?
C139 C140 C135 118.0(7) . . ?
C139 C140 C141 122.6(6) . . ?
C135 C140 C141 119.4(6) . . ?
C132 C141 C140 118.6(6) . . ?
C132 C141 C142 121.4(6) . . ?
C140 C141 C142 120.0(6) . . ?
C151 C142 C143 118.9(6) . . ?
C151 C142 C141 121.0(6) . . ?
C143 C142 C141 120.0(6) . . ?
C148 C143 C144 118.7(6) . . ?
C148 C143 C142 120.0(7) . . ?
C144 C143 C142 121.3(6) . . ?
C145 C144 C143 120.6(8) . . ?
C145 C144 H144 119.7 . . ?
C143 C144 H144 119.7 . . ?
C144 C145 C146 119.8(8) . . ?
C144 C145 H145 120.1 . . ?
C146 C145 H145 120.1 . . ?
C147 C146 C145 120.3(8) . . ?
C147 C146 H146 119.8 . . ?
C145 C146 H146 119.8 . . ?
C146 C147 C148 122.1(8) . . ?
C146 C147 H147 119.0 . . ?
C148 C147 H147 119.0 . . ?
C149 C148 C143 118.2(6) . . ?
C149 C148 C147 123.4(7) . . ?
C143 C148 C147 118.4(7) . . ?
C150 C149 C148 122.3(7) . . ?
C150 C149 H149 118.9 . . ?
C148 C149 H149 118.9 . . ?
C149 C150 C151 121.2(7) . . ?
C149 C150 H150 119.4 . . ?
C151 C150 H150 119.4 . . ?
O152 C151 C142 120.5(6) . . ?
O152 C151 C150 120.2(6) . . ?
C142 C151 C150 119.3(6) . . ?
C162 O161 H161 109.5 . . ?
O161 C162 C163 112.4(8) . . ?
O161 C162 H62A 109.1 . . ?
C163 C162 H62A 109.1 . . ?
O161 C162 H62B 109.1 . . ?
C163 C162 H62B 109.1 . . ?
H62A C162 H62B 107.9 . . ?
C162 C163 H63A 109.5 . . ?
C162 C163 H63B 109.5 . . ?
H63A C163 H63B 109.5 . . ?
C162 C163 H63C 109.5 . . ?
H63A C163 H63C 109.5 . . ?
H63B C163 H63C 109.5 . . ?
H71A O171 H71B 107(6) . . ?
O171 C172 C173 122(2) . . ?
O171 C172 H17A 106.8 . . ?
C173 C172 H17A 106.8 . . ?
O171 C172 H17B 106.8 . . ?
C173 C172 H17B 106.8 . . ?
H17A C172 H17B 106.6 . . ?
C172 C173 H17C 109.5 . . ?
C172 C173 H17D 109.5 . . ?
H17C C173 H17D 109.5 . . ?
C172 C173 H17E 109.5 . . ?
H17C C173 H17E 109.5 . . ?
H17D C173 H17E 109.5 . . ?
C182 O181 H181 109.5 . . ?
O181 C182 C183 115.4(13) . . ?
O181 C182 H82A 108.4 . . ?
C183 C182 H82A 108.4 . . ?
O181 C182 H82B 108.4 . . ?
C183 C182 H82B 108.4 . . ?
H82A C182 H82B 107.5 . . ?
C182 C183 H18C 109.5 . . ?
C182 C183 H18D 109.5 . . ?
H18C C183 H18D 109.5 . . ?
C182 C183 H18E 109.5 . . ?
H18C C183 H18E 109.5 . . ?
H18D C183 H18E 109.5 . . ?
C192 O191 H191 109.5 . . ?
O191 C192 C193 112.7(10) . . ?
O191 C192 H92A 109.1 . . ?
C193 C192 H92A 109.1 . . ?
O191 C192 H92B 109.1 . . ?
C193 C192 H92B 109.1 . . ?
H92A C192 H92B 107.8 . . ?
C192 C193 H93A 109.5 . . ?
C192 C193 H93B 109.5 . . ?
H93A C193 H93B 109.5 . . ?
C192 C193 H93C 109.5 . . ?
H93A C193 H93C 109.5 . . ?
H93B C193 H93C 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
N1 C2 C3 C4 179.9(6) . . . . ?
C7 C2 C3 C4 -59.8(8) . . . . ?
C2 C3 C4 C5 56.5(10) . . . . ?
C3 C4 C5 C6 -56.7(11) . . . . ?
C4 C5 C6 C7 57.1(10) . . . . ?
C3 C2 C7 N8 -175.7(6) . . . . ?
N1 C2 C7 N8 -54.1(7) . . . . ?
C3 C2 C7 C6 60.8(7) . . . . ?
N1 C2 C7 C6 -177.6(5) . . . . ?
C5 C6 C7 N8 -178.0(7) . . . . ?
C5 C6 C7 C2 -57.5(8) . . . . ?
N11 C12 C13 C14 176.9(6) . . . . ?
C17 C12 C13 C14 -58.9(8) . . . . ?
C12 C13 C14 C15 58.2(9) . . . . ?
C13 C14 C15 C16 -57.5(9) . . . . ?
C14 C15 C16 C17 57.0(9) . . . . ?
N11 C12 C17 N18 -54.1(8) . . . . ?
C13 C12 C17 N18 -178.6(6) . . . . ?
N11 C12 C17 C16 -178.5(6) . . . . ?
C13 C12 C17 C16 56.9(8) . . . . ?
C15 C16 C17 N18 -176.6(7) . . . . ?
C15 C16 C17 C12 -55.6(8) . . . . ?
C27 C22 C23 C24 -54.9(10) . . . . ?
N21 C22 C23 C24 -179.7(9) . . . . ?
C22 C23 C24 C25 56.3(11) . . . . ?
C23 C24 C25 C26 -57.2(11) . . . . ?
C24 C25 C26 C27 58.6(11) . . . . ?
C25 C26 C27 N28 176.3(8) . . . . ?
C25 C26 C27 C22 -59.1(11) . . . . ?
N21 C22 C27 N28 -52.2(9) . . . . ?
C23 C22 C27 N28 -178.6(7) . . . . ?
N21 C22 C27 C26 -177.5(9) . . . . ?
C23 C22 C27 C26 56.1(9) . . . . ?
C37 C32 C33 C34 -38.2(14) . . . . ?
N31 C32 C33 C34 -175.3(9) . . . . ?
C32 C33 C34 C35 37.7(16) . . . . ?
C33 C34 C35 C36 -49.5(17) . . . . ?
C34 C35 C36 C37 52.2(15) . . . . ?
C33 C32 C37 N38 173.4(11) . . . . ?
N31 C32 C37 N38 -49.4(12) . . . . ?
C33 C32 C37 C36 46.9(13) . . . . ?
N31 C32 C37 C36 -175.9(8) . . . . ?
C35 C36 C37 N38 -175.5(10) . . . . ?
C35 C36 C37 C32 -49.2(13) . . . . ?
O41 C42 C43 C44 176.7(7) . . . . ?
C51 C42 C43 C44 -2.1(11) . . . . ?
C42 C43 C44 C45 0.7(11) . . . . ?
C43 C44 C45 C46 179.6(7) . . . . ?
C43 C44 C45 C50 1.3(10) . . . . ?
C44 C45 C46 C47 -177.0(7) . . . . ?
C50 C45 C46 C47 1.2(11) . . . . ?
C45 C46 C47 C48 -1.5(13) . . . . ?
C46 C47 C48 C49 1.0(13) . . . . ?
C47 C48 C49 C50 -0.3(12) . . . . ?
C48 C49 C50 C51 179.9(7) . . . . ?
C48 C49 C50 C45 0.0(10) . . . . ?
C46 C45 C50 C51 179.6(6) . . . . ?
C44 C45 C50 C51 -2.0(9) . . . . ?
C46 C45 C50 C49 -0.5(9) . . . . ?
C44 C45 C50 C49 177.9(6) . . . . ?
O41 C42 C51 C50 -177.5(6) . . . . ?
C43 C42 C51 C50 1.3(10) . . . . ?
O41 C42 C51 C52 3.3(10) . . . . ?
C43 C42 C51 C52 -177.9(6) . . . . ?
C49 C50 C51 C42 -179.1(6) . . . . ?
C45 C50 C51 C42 0.7(9) . . . . ?
C49 C50 C51 C52 0.1(10) . . . . ?
C45 C50 C51 C52 180.0(6) . . . . ?
C42 C51 C52 C61 80.1(8) . . . . ?
C50 C51 C52 C61 -99.1(8) . . . . ?
C42 C51 C52 C53 -100.3(8) . . . . ?
C50 C51 C52 C53 80.5(8) . . . . ?
C61 C52 C53 C54 178.7(7) . . . . ?
C51 C52 C53 C54 -0.8(10) . . . . ?
C61 C52 C53 C58 0.3(9) . . . . ?
C51 C52 C53 C58 -179.3(6) . . . . ?
C58 C53 C54 C55 -1.3(11) . . . . ?
C52 C53 C54 C55 -179.8(7) . . . . ?
C53 C54 C55 C56 -0.5(12) . . . . ?
C54 C55 C56 C57 2.1(13) . . . . ?
C55 C56 C57 C58 -1.7(13) . . . . ?
C56 C57 C58 C59 -178.4(8) . . . . ?
C56 C57 C58 C53 -0.3(11) . . . . ?
C54 C53 C58 C59 180.0(7) . . . . ?
C52 C53 C58 C59 -1.5(10) . . . . ?
C54 C53 C58 C57 1.8(10) . . . . ?
C52 C53 C58 C57 -179.7(6) . . . . ?
C57 C58 C59 C60 179.2(7) . . . . ?
C53 C58 C59 C60 1.1(11) . . . . ?
C58 C59 C60 C61 0.6(12) . . . . ?
C53 C52 C61 O62 -179.7(6) . . . . ?
C51 C52 C61 O62 -0.1(10) . . . . ?
C53 C52 C61 C60 1.3(10) . . . . ?
C51 C52 C61 C60 -179.1(6) . . . . ?
C59 C60 C61 O62 179.2(6) . . . . ?
C59 C60 C61 C52 -1.8(11) . . . . ?
O71 C72 C73 C74 177.7(7) . . . . ?
C81 C72 C73 C74 -0.2(11) . . . . ?
C72 C73 C74 C75 0.8(13) . . . . ?
C73 C74 C75 C76 -178.3(7) . . . . ?
C73 C74 C75 C80 -0.7(12) . . . . ?
C74 C75 C76 C77 179.4(8) . . . . ?
C80 C75 C76 C77 1.8(12) . . . . ?
C75 C76 C77 C78 1.2(13) . . . . ?
C76 C77 C78 C79 -2.5(14) . . . . ?
C77 C78 C79 C80 0.8(13) . . . . ?
C78 C79 C80 C81 -179.1(7) . . . . ?
C78 C79 C80 C75 2.1(11) . . . . ?
C74 C75 C80 C81 0.2(10) . . . . ?
C76 C75 C80 C81 177.8(7) . . . . ?
C74 C75 C80 C79 179.0(7) . . . . ?
C76 C75 C80 C79 -3.4(10) . . . . ?
O71 C72 C81 C80 -178.1(6) . . . . ?
C73 C72 C81 C80 -0.3(10) . . . . ?
O71 C72 C81 C82 2.7(10) . . . . ?
C73 C72 C81 C82 -179.5(6) . . . . ?
C79 C80 C81 C72 -178.4(6) . . . . ?
C75 C80 C81 C72 0.3(10) . . . . ?
C79 C80 C81 C82 0.8(10) . . . . ?
C75 C80 C81 C82 179.5(6) . . . . ?
C72 C81 C82 C91 -90.6(7) . . . . ?
C80 C81 C82 C91 90.3(8) . . . . ?
C72 C81 C82 C83 89.8(8) . . . . ?
C80 C81 C82 C83 -89.3(8) . . . . ?
C91 C82 C83 C88 -1.7(10) . . . . ?
C81 C82 C83 C88 177.9(6) . . . . ?
C91 C82 C83 C84 179.1(6) . . . . ?
C81 C82 C83 C84 -1.3(10) . . . . ?
C82 C83 C84 C85 -179.5(6) . . . . ?
C88 C83 C84 C85 1.3(10) . . . . ?
C83 C84 C85 C86 -0.2(12) . . . . ?
C84 C85 C86 C87 -0.8(13) . . . . ?
C85 C86 C87 C88 0.7(13) . . . . ?
C86 C87 C88 C89 178.4(7) . . . . ?
C86 C87 C88 C83 0.4(11) . . . . ?
C82 C83 C88 C87 179.5(6) . . . . ?
C84 C83 C88 C87 -1.4(9) . . . . ?
C82 C83 C88 C89 1.4(10) . . . . ?
C84 C83 C88 C89 -179.4(6) . . . . ?
C87 C88 C89 C90 -177.9(7) . . . . ?
C83 C88 C89 C90 0.1(10) . . . . ?
C88 C89 C90 C91 -1.3(11) . . . . ?
C89 C90 C91 O92 -177.0(7) . . . . ?
C89 C90 C91 C82 0.9(11) . . . . ?
C83 C82 C91 O92 178.5(6) . . . . ?
C81 C82 C91 O92 -1.1(9) . . . . ?
C83 C82 C91 C90 0.6(10) . . . . ?
C81 C82 C91 C90 -179.0(6) . . . . ?
O101 C102 C103 C104 179.5(7) . . . . ?
C111 C102 C103 C104 -1.1(11) . . . . ?
C102 C103 C104 C105 0.5(12) . . . . ?
C103 C104 C105 C106 178.8(7) . . . . ?
C103 C104 C105 C110 0.7(12) . . . . ?
C110 C105 C106 C107 -2.4(12) . . . . ?
C104 C105 C106 C107 179.5(8) . . . . ?
C105 C106 C107 C108 1.0(13) . . . . ?
C106 C107 C108 C109 0.8(14) . . . . ?
C107 C108 C109 C110 -1.1(13) . . . . ?
C108 C109 C110 C111 -178.9(7) . . . . ?
C108 C109 C110 C105 -0.3(11) . . . . ?
C106 C105 C110 C111 -179.4(7) . . . . ?
C104 C105 C110 C111 -1.2(10) . . . . ?
C106 C105 C110 C109 2.1(11) . . . . ?
C104 C105 C110 C109 -179.8(7) . . . . ?
C109 C110 C111 C102 179.1(7) . . . . ?
C105 C110 C111 C102 0.6(10) . . . . ?
C109 C110 C111 C112 0.8(10) . . . . ?
C105 C110 C111 C112 -177.7(6) . . . . ?
O101 C102 C111 C110 180.0(6) . . . . ?
C103 C102 C111 C110 0.6(10) . . . . ?
O101 C102 C111 C112 -1.7(10) . . . . ?
C103 C102 C111 C112 178.9(6) . . . . ?
C110 C111 C112 C121 98.4(8) . . . . ?
C102 C111 C112 C121 -80.0(8) . . . . ?
C110 C111 C112 C113 -80.3(8) . . . . ?
C102 C111 C112 C113 101.4(8) . . . . ?
C121 C112 C113 C114 178.7(6) . . . . ?
C111 C112 C113 C114 -2.6(10) . . . . ?
C121 C112 C113 C118 -0.3(10) . . . . ?
C111 C112 C113 C118 178.4(6) . . . . ?
C112 C113 C114 C115 -179.5(7) . . . . ?
C118 C113 C114 C115 -0.5(10) . . . . ?
C113 C114 C115 C116 -1.2(12) . . . . ?
C114 C115 C116 C117 1.0(13) . . . . ?
C115 C116 C117 C118 0.9(12) . . . . ?
C112 C113 C118 C119 2.8(10) . . . . ?
C114 C113 C118 C119 -176.2(6) . . . . ?
C112 C113 C118 C117 -178.7(6) . . . . ?
C114 C113 C118 C117 2.3(10) . . . . ?
C116 C117 C118 C119 175.9(8) . . . . ?
C116 C117 C118 C113 -2.6(11) . . . . ?
C113 C118 C119 C120 -2.5(11) . . . . ?
C117 C118 C119 C120 179.0(7) . . . . ?
C118 C119 C120 C121 -0.3(12) . . . . ?
C113 C112 C121 O122 178.3(6) . . . . ?
C111 C112 C121 O122 -0.4(10) . . . . ?
C113 C112 C121 C120 -2.5(10) . . . . ?
C111 C112 C121 C120 178.8(6) . . . . ?
C119 C120 C121 O122 -178.0(7) . . . . ?
C119 C120 C121 C112 2.9(11) . . . . ?
C141 C132 C133 C134 -0.4(11) . . . . ?
O131 C132 C133 C134 178.4(7) . . . . ?
C132 C133 C134 C135 1.3(11) . . . . ?
C133 C134 C135 C136 178.4(7) . . . . ?
C133 C134 C135 C140 -1.8(11) . . . . ?
C134 C135 C136 C137 -179.0(7) . . . . ?
C140 C135 C136 C137 1.2(11) . . . . ?
C135 C136 C137 C138 0.7(13) . . . . ?
C136 C137 C138 C139 -1.4(14) . . . . ?
C137 C138 C139 C140 0.0(13) . . . . ?
C138 C139 C140 C135 2.0(11) . . . . ?
C138 C139 C140 C141 178.2(7) . . . . ?
C134 C135 C140 C139 177.7(6) . . . . ?
C136 C135 C140 C139 -2.5(10) . . . . ?
C134 C135 C140 C141 1.3(10) . . . . ?
C136 C135 C140 C141 -178.9(6) . . . . ?
O131 C132 C141 C140 -178.9(6) . . . . ?
C133 C132 C141 C140 -0.1(10) . . . . ?
O131 C132 C141 C142 3.0(10) . . . . ?
C133 C132 C141 C142 -178.3(6) . . . . ?
C139 C140 C141 C132 -176.6(6) . . . . ?
C135 C140 C141 C132 -0.4(9) . . . . ?
C139 C140 C141 C142 1.6(10) . . . . ?
C135 C140 C141 C142 177.8(6) . . . . ?
C132 C141 C142 C151 86.0(8) . . . . ?
C140 C141 C142 C151 -92.2(8) . . . . ?
C132 C141 C142 C143 -91.1(8) . . . . ?
C140 C141 C142 C143 90.8(7) . . . . ?
C151 C142 C143 C148 0.5(10) . . . . ?
C141 C142 C143 C148 177.6(6) . . . . ?
C151 C142 C143 C144 -178.4(7) . . . . ?
C141 C142 C143 C144 -1.3(10) . . . . ?
C148 C143 C144 C145 -0.3(11) . . . . ?
C142 C143 C144 C145 178.7(7) . . . . ?
C143 C144 C145 C146 0.1(13) . . . . ?
C144 C145 C146 C147 -0.8(14) . . . . ?
C145 C146 C147 C148 1.7(14) . . . . ?
C144 C143 C148 C149 -179.4(7) . . . . ?
C142 C143 C148 C149 1.6(10) . . . . ?
C144 C143 C148 C147 1.1(10) . . . . ?
C142 C143 C148 C147 -177.8(6) . . . . ?
C146 C147 C148 C149 178.7(8) . . . . ?
C146 C147 C148 C143 -1.9(12) . . . . ?
C143 C148 C149 C150 -1.6(11) . . . . ?
C147 C148 C149 C150 177.8(8) . . . . ?
C148 C149 C150 C151 -0.6(12) . . . . ?
C143 C142 C151 O152 178.2(6) . . . . ?
C141 C142 C151 O152 1.1(10) . . . . ?
C143 C142 C151 C150 -2.7(10) . . . . ?
C141 C142 C151 C150 -179.8(6) . . . . ?
C149 C150 C151 O152 -178.0(7) . . . . ?
C149 C150 C151 C142 2.8(12) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
