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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jdm_Rbin_DADPEtol
_database_code_depnum_ccdc_archive 'CCDC 2295235'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2024-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(R)-(+)-1,1?-Bi(2-naphthol) ; (1R,2R)-N,N?-Dimethyl-1,2-diphenylethane-1,2-diamine'
_chemical_name_common            'R-Binol ; (R,R)-DADPE'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2, C14 H16 N2'
_chemical_formula_sum            'C34 H30 N2 O2'
_chemical_formula_weight         498.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'

_cell_length_a                   13.32025(13)
_cell_length_b                   13.32025(13)
_cell_length_c                   31.8915(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5658.48(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    13479
_cell_measurement_theta_min      3.0990
_cell_measurement_theta_max      26.5000

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.95306
_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       
;
'216 images, ΔΦ 0.75° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37467
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.125
_diffrn_reflns_theta_max         26.616
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5837
_reflns_number_gt                5287
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.998

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

_computing_data_collection       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)+(0.0486P)²+0.8270P] 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 2036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5837
_refine_ls_number_parameters     382
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.101
_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 0.35595(15) 0.67923(13) 0.30631(5) 0.0622(5) Uani 1 1 d . . . . .
H1 H 0.393833 0.707026 0.289699 0.093 Uiso 1 1 calc R U . . .
C2 C 0.34982(17) 0.57988(17) 0.29686(6) 0.0460(5) Uani 1 1 d . . . . .
C3 C 0.2871(2) 0.5222(2) 0.32316(7) 0.0565(6) Uani 1 1 d . . . . .
H3 H 0.254152 0.552973 0.345434 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2741(2) 0.4225(2) 0.31643(8) 0.0598(6) Uani 1 1 d . . . . .
H4 H 0.232580 0.385888 0.334182 0.072 Uiso 1 1 calc R U . . .
C5 C 0.32282(19) 0.37363(18) 0.28280(8) 0.0537(5) Uani 1 1 d . . . . .
C6 C 0.3096(2) 0.2706(2) 0.27409(10) 0.0719(8) Uani 1 1 d . . . . .
H6 H 0.268534 0.232509 0.291516 0.086 Uiso 1 1 calc R U . . .
C7 C 0.3550(3) 0.2255(2) 0.24102(12) 0.0836(10) Uani 1 1 d . . . . .
H7 H 0.343957 0.157887 0.235519 0.100 Uiso 1 1 calc R U . . .
C8 C 0.4191(3) 0.2821(2) 0.21513(11) 0.0810(9) Uani 1 1 d . . . . .
H8 H 0.450886 0.251267 0.192578 0.097 Uiso 1 1 calc R U . . .
C9 C 0.4351(2) 0.38153(19) 0.22273(9) 0.0638(7) Uani 1 1 d . . . . .
H9 H 0.478370 0.417316 0.205415 0.077 Uiso 1 1 calc R U . . .
C10 C 0.38713(16) 0.43148(16) 0.25639(7) 0.0462(5) Uani 1 1 d . . . . .
C11 C 0.40078(15) 0.53612(16) 0.26399(6) 0.0414(4) Uani 1 1 d . . . . .
O21 O 0.25400(12) 0.46660(17) 0.01187(6) 0.0672(5) Uani 1 1 d . . . . .
H21 H 0.2714(10) 0.444(3) -0.0138(12) 0.101 Uiso 1 1 calc R U . . .
C22 C 0.33624(17) 0.46786(18) 0.03705(7) 0.0488(5) Uani 1 1 d . . . . .
C23 C 0.3185(2) 0.4892(2) 0.07968(8) 0.0619(7) Uani 1 1 d . . . . .
H23 H 0.253108 0.500423 0.088816 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3948(2) 0.4936(2) 0.10747(7) 0.0603(6) Uani 1 1 d . . . . .
H24 H 0.381205 0.507938 0.135450 0.072 Uiso 1 1 calc R U . . .
C25 C 0.49482(19) 0.47690(16) 0.09471(7) 0.0499(5) Uani 1 1 d . . . . .
C26 C 0.5771(2) 0.4833(2) 0.12262(8) 0.0630(7) Uani 1 1 d . . . . .
H26 H 0.565430 0.499041 0.150608 0.076 Uiso 1 1 calc R U . . .
C27 C 0.6722(2) 0.4670(2) 0.10956(10) 0.0722(8) Uani 1 1 d . . . . .
H27 H 0.725235 0.471729 0.128435 0.087 Uiso 1 1 calc R U . . .
C28 C 0.6908(2) 0.4429(2) 0.06747(10) 0.0665(7) Uani 1 1 d . . . . .
H28 H 0.756178 0.430370 0.058699 0.080 Uiso 1 1 calc R U . . .
C29 C 0.61402(17) 0.43762(18) 0.03920(8) 0.0533(5) Uani 1 1 d . . . . .
H29 H 0.627831 0.422392 0.011331 0.064 Uiso 1 1 calc R U . . .
C30 C 0.51380(16) 0.45504(15) 0.05180(7) 0.0432(4) Uani 1 1 d . . . . .
C31 C 0.43230(16) 0.45146(15) 0.02276(6) 0.0413(4) Uani 1 1 d . . . . .
C41 C 0.5718(2) 0.1910(2) 0.11235(9) 0.0609(6) Uani 1 1 d . . . . .
H41 H 0.575506 0.235435 0.089926 0.073 Uiso 1 1 calc R U . . .
C42 C 0.6449(2) 0.1931(2) 0.14289(11) 0.0758(8) Uani 1 1 d . . . . .
H42 H 0.697721 0.238452 0.140745 0.091 Uiso 1 1 calc R U . . .
C43 C 0.6402(2) 0.1291(3) 0.17633(10) 0.0766(9) Uani 1 1 d . . . . .
H43 H 0.689226 0.131428 0.197070 0.092 Uiso 1 1 calc R U . . .
C44 C 0.5629(2) 0.0615(2) 0.17915(9) 0.0702(7) Uani 1 1 d . . . . .
H44 H 0.559508 0.017701 0.201824 0.084 Uiso 1 1 calc R U . . .
C45 C 0.4900(2) 0.05819(19) 0.14839(8) 0.0566(6) Uani 1 1 d . . . . .
H45 H 0.438203 0.011571 0.150372 0.068 Uiso 1 1 calc R U . . .
C46 C 0.49301(17) 0.12363(16) 0.11454(6) 0.0453(5) Uani 1 1 d . . . . .
C47 C 0.40899(16) 0.12369(16) 0.08254(7) 0.0453(5) Uani 1 1 d . . . . .
H47 H 0.348521 0.096295 0.095784 0.054 Uiso 1 1 calc R U . . .
N48 N 0.38712(16) 0.22765(14) 0.06845(7) 0.0523(5) Uani 1 1 d G . . . .
H48A H 0.407663 0.265882 0.088338 0.063 Uiso 1 1 d G U . . .
H48B H 0.324811 0.227298 0.061585 0.063 Uiso 1 1 d G U . . .
C49 C 0.43280(17) 0.06055(16) 0.04316(7) 0.0466(5) Uani 1 1 d D . . . .
H49 H 0.493908 0.085274 0.029507 0.056 Uiso 0.42(3) 1 calc R U P A 1
H49B H 0.489262 0.093683 0.029131 0.056 Uiso 0.58(3) 1 calc R U P A 2
N50 N 0.34587(16) 0.06869(16) 0.01433(6) 0.0545(5) Uani 1 1 d G . . . .
H50A H 0.337045 0.012470 0.001714 0.065 Uiso 1 1 d G U . . .
H50B H 0.355396 0.122489 0.000069 0.065 Uiso 1 1 d G U . . .
C51 C 0.4444(11) -0.0485(5) 0.0549(5) 0.050(3) Uani 0.42(3) 1 d DG U P A 1
C52 C 0.5401(12) -0.0897(8) 0.0522(5) 0.069(3) Uani 0.42(3) 1 d G U P A 1
H52 H 0.594805 -0.048847 0.046155 0.083 Uiso 0.42(3) 1 calc R U P A 1
C53 C 0.5539(15) -0.1921(8) 0.0583(4) 0.079(3) Uani 0.42(3) 1 d G U P A 1
H53 H 0.617833 -0.219708 0.056485 0.095 Uiso 0.42(3) 1 calc R U P A 1
C54 C 0.4720(17) -0.2532(4) 0.0673(3) 0.075(4) Uani 0.42(3) 1 d G U P A 1
H54 H 0.481271 -0.321698 0.071452 0.090 Uiso 0.42(3) 1 calc R U P A 1
C55 C 0.3764(15) -0.2119(7) 0.0701(4) 0.083(3) Uani 0.42(3) 1 d G U P A 1
H55 H 0.321681 -0.252829 0.076091 0.100 Uiso 0.42(3) 1 calc R U P A 1
C56 C 0.3626(11) -0.1096(8) 0.0639(5) 0.066(3) Uani 0.42(3) 1 d G U P A 1
H56 H 0.298652 -0.081969 0.065761 0.080 Uiso 0.42(3) 1 calc R U P A 1
C51B C 0.4650(8) -0.0484(4) 0.0507(4) 0.0505(19) Uani 0.58(3) 1 d DG U P A 2
C52B C 0.5664(8) -0.0727(6) 0.0510(4) 0.0673(19) Uani 0.58(3) 1 d G U P A 2
H52B H 0.614340 -0.023024 0.046600 0.081 Uiso 0.58(3) 1 calc R U P A 2
C53B C 0.5963(10) -0.1713(7) 0.0580(3) 0.089(3) Uani 0.58(3) 1 d G U P A 2
H53B H 0.664217 -0.187543 0.058272 0.107 Uiso 0.58(3) 1 calc R U P A 2
C54B C 0.5247(13) -0.2455(4) 0.0647(2) 0.082(3) Uani 0.58(3) 1 d G U P A 2
H54B H 0.544731 -0.311449 0.069366 0.098 Uiso 0.58(3) 1 calc R U P A 2
C55B C 0.4233(12) -0.2212(4) 0.0643(3) 0.080(3) Uani 0.58(3) 1 d G U P A 2
H55B H 0.375367 -0.270838 0.068789 0.096 Uiso 0.58(3) 1 calc R U P A 2
C56B C 0.3934(9) -0.1226(6) 0.0573(3) 0.067(2) Uani 0.58(3) 1 d G U P A 2
H56B H 0.325488 -0.106319 0.057116 0.080 Uiso 0.58(3) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.360(3) . ?
O1 H1 0.8200 . ?
C2 C11 1.378(3) . ?
C2 C3 1.412(3) . ?
C3 C4 1.356(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(4) . ?
C5 C10 1.427(3) . ?
C6 C7 1.356(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.415(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.426(3) . ?
C11 C11 1.486(4) 8_665 ?
O21 C22 1.358(3) . ?
O21 H21 0.90(4) . ?
C22 C31 1.376(3) . ?
C22 C23 1.409(3) . ?
C23 C24 1.350(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.411(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.414(3) . ?
C25 C30 1.422(3) . ?
C26 C27 1.352(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.402(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.365(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.413(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.428(3) . ?
C31 C31 1.496(4) 6 ?
C41 C42 1.377(4) . ?
C41 C46 1.382(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.367(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.372(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.381(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.388(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.515(3) . ?
C47 N48 1.485(3) . ?
C47 C49 1.544(3) . ?
C47 H47 0.9800 . ?
N48 H48A 0.8583 . ?
N48 H48B 0.8583 . ?
C49 N50 1.482(3) . ?
C49 C51 1.508(6) . ?
C49 C51B 1.532(5) . ?
C49 H49 0.9800 . ?
C49 H49B 0.9800 . ?
N50 H50A 0.8583 . ?
N50 H50B 0.8582 . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C52 C53 1.3900 . ?
C52 H52 0.9300 . ?
C53 C54 1.3900 . ?
C53 H53 0.9300 . ?
C54 C55 1.3900 . ?
C54 H54 0.9300 . ?
C55 C56 1.3900 . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C51B C52B 1.3900 . ?
C51B C56B 1.3900 . ?
C52B C53B 1.3900 . ?
C52B H52B 0.9300 . ?
C53B C54B 1.3900 . ?
C53B H53B 0.9300 . ?
C54B C55B 1.3900 . ?
C54B H54B 0.9300 . ?
C55B C56B 1.3900 . ?
C55B H55B 0.9300 . ?
C56B H56B 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 123.4(2) . . ?
O1 C2 C3 115.7(2) . . ?
C11 C2 C3 120.9(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.7(2) . . ?
C6 C5 C10 118.9(2) . . ?
C4 C5 C10 118.3(2) . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 122.1(2) . . ?
C9 C10 C5 117.7(2) . . ?
C11 C10 C5 120.2(2) . . ?
C2 C11 C10 118.7(2) . . ?
C2 C11 C11 119.74(19) . 8_665 ?
C10 C11 C11 121.50(18) . 8_665 ?
C22 O21 H21 109.5 . . ?
O21 C22 C31 123.5(2) . . ?
O21 C22 C23 115.9(2) . . ?
C31 C22 C23 120.5(2) . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C26 122.7(2) . . ?
C24 C25 C30 118.6(2) . . ?
C26 C25 C30 118.7(2) . . ?
C27 C26 C25 121.5(2) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 120.8(2) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 118.4(2) . . ?
C29 C30 C31 121.89(19) . . ?
C25 C30 C31 119.7(2) . . ?
C22 C31 C30 119.13(19) . . ?
C22 C31 C31 120.5(2) . 6 ?
C30 C31 C31 120.37(19) . 6 ?
C42 C41 C46 121.0(3) . . ?
C42 C41 H41 119.5 . . ?
C46 C41 H41 119.5 . . ?
C43 C42 C41 120.4(3) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 119.7(3) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C43 C44 C45 120.2(3) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C44 C45 C46 120.8(3) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 118.0(2) . . ?
C41 C46 C47 121.8(2) . . ?
C45 C46 C47 120.2(2) . . ?
N48 C47 C46 110.45(17) . . ?
N48 C47 C49 107.58(17) . . ?
C46 C47 C49 113.32(18) . . ?
N48 C47 H47 108.5 . . ?
C46 C47 H47 108.5 . . ?
C49 C47 H47 108.5 . . ?
C47 N48 H48A 105.5 . . ?
C47 N48 H48B 105.2 . . ?
H48A N48 H48B 120.0 . . ?
N50 C49 C51 107.8(6) . . ?
N50 C49 C51B 112.7(4) . . ?
N50 C49 C47 107.69(18) . . ?
C51 C49 C47 110.1(7) . . ?
C51B C49 C47 116.5(5) . . ?
N50 C49 H49 110.4 . . ?
C51 C49 H49 110.4 . . ?
C47 C49 H49 110.4 . . ?
N50 C49 H49B 106.5 . . ?
C51B C49 H49B 106.5 . . ?
C47 C49 H49B 106.5 . . ?
C49 N50 H50A 109.5 . . ?
C49 N50 H50B 105.9 . . ?
H50A N50 H50B 120.0 . . ?
C52 C51 C56 120.0 . . ?
C52 C51 C49 117.3(7) . . ?
C56 C51 C49 122.3(7) . . ?
C53 C52 C51 120.0 . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C55 120.0 . . ?
C53 C54 H54 120.0 . . ?
C55 C54 H54 120.0 . . ?
C56 C55 C54 120.0 . . ?
C56 C55 H55 120.0 . . ?
C54 C55 H55 120.0 . . ?
C55 C56 C51 120.0 . . ?
C55 C56 H56 120.0 . . ?
C51 C56 H56 120.0 . . ?
C52B C51B C56B 120.0 . . ?
C52B C51B C49 119.6(5) . . ?
C56B C51B C49 120.4(5) . . ?
C51B C52B C53B 120.0 . . ?
C51B C52B H52B 120.0 . . ?
C53B C52B H52B 120.0 . . ?
C54B C53B C52B 120.0 . . ?
C54B C53B H53B 120.0 . . ?
C52B C53B H53B 120.0 . . ?
C53B C54B C55B 120.0 . . ?
C53B C54B H54B 120.0 . . ?
C55B C54B H54B 120.0 . . ?
C56B C55B C54B 120.0 . . ?
C56B C55B H55B 120.0 . . ?
C54B C55B H55B 120.0 . . ?
C55B C56B C51B 120.0 . . ?
C55B C56B H56B 120.0 . . ?
C51B C56B H56B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.1(2) . . . . ?
C11 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -178.5(3) . . . . ?
C3 C4 C5 C10 0.8(4) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C10 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 1.5(5) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
C8 C9 C10 C11 -178.1(3) . . . . ?
C8 C9 C10 C5 1.3(4) . . . . ?
C6 C5 C10 C9 -0.4(4) . . . . ?
C4 C5 C10 C9 -179.7(2) . . . . ?
C6 C5 C10 C11 179.0(2) . . . . ?
C4 C5 C10 C11 -0.3(3) . . . . ?
O1 C2 C11 C10 -178.7(2) . . . . ?
C3 C2 C11 C10 1.4(3) . . . . ?
O1 C2 C11 C11 -2.0(3) . . . 8_665 ?
C3 C2 C11 C11 178.1(2) . . . 8_665 ?
C9 C10 C11 C2 178.6(2) . . . . ?
C5 C10 C11 C2 -0.8(3) . . . . ?
C9 C10 C11 C11 2.0(3) . . . 8_665 ?
C5 C10 C11 C11 -177.4(2) . . . 8_665 ?
O21 C22 C23 C24 -179.2(3) . . . . ?
C31 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 178.4(3) . . . . ?
C23 C24 C25 C30 -0.1(4) . . . . ?
C24 C25 C26 C27 -179.9(3) . . . . ?
C30 C25 C26 C27 -1.4(4) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
C26 C27 C28 C29 1.3(4) . . . . ?
C27 C28 C29 C30 -0.8(4) . . . . ?
C28 C29 C30 C25 -0.8(3) . . . . ?
C28 C29 C30 C31 179.1(2) . . . . ?
C24 C25 C30 C29 -179.6(2) . . . . ?
C26 C25 C30 C29 1.9(3) . . . . ?
C24 C25 C30 C31 0.6(3) . . . . ?
C26 C25 C30 C31 -178.0(2) . . . . ?
O21 C22 C31 C30 179.6(2) . . . . ?
C23 C22 C31 C30 0.8(3) . . . . ?
O21 C22 C31 C31 0.9(3) . . . 6 ?
C23 C22 C31 C31 -177.9(2) . . . 6 ?
C29 C30 C31 C22 179.2(2) . . . . ?
C25 C30 C31 C22 -1.0(3) . . . . ?
C29 C30 C31 C31 -2.1(3) . . . 6 ?
C25 C30 C31 C31 177.74(18) . . . 6 ?
C46 C41 C42 C43 -0.7(5) . . . . ?
C41 C42 C43 C44 0.8(5) . . . . ?
C42 C43 C44 C45 -0.1(5) . . . . ?
C43 C44 C45 C46 -0.7(4) . . . . ?
C42 C41 C46 C45 -0.2(4) . . . . ?
C42 C41 C46 C47 176.7(2) . . . . ?
C44 C45 C46 C41 0.9(4) . . . . ?
C44 C45 C46 C47 -176.0(2) . . . . ?
C41 C46 C47 N48 -34.6(3) . . . . ?
C45 C46 C47 N48 142.2(2) . . . . ?
C41 C46 C47 C49 86.2(3) . . . . ?
C45 C46 C47 C49 -97.0(2) . . . . ?
N48 C47 C49 N50 -56.5(2) . . . . ?
C46 C47 C49 N50 -178.92(18) . . . . ?
N48 C47 C49 C51 -173.8(6) . . . . ?
C46 C47 C49 C51 63.8(6) . . . . ?
N48 C47 C49 C51B 175.9(5) . . . . ?
C46 C47 C49 C51B 53.5(5) . . . . ?
N50 C49 C51 C52 131.9(7) . . . . ?
C47 C49 C51 C52 -110.9(8) . . . . ?
N50 C49 C51 C56 -41.2(10) . . . . ?
C47 C49 C51 C56 75.9(10) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
C49 C51 C52 C53 -173.3(12) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
C49 C51 C56 C55 173.0(13) . . . . ?
N50 C49 C51B C52B 137.5(5) . . . . ?
C47 C49 C51B C52B -97.4(6) . . . . ?
N50 C49 C51B C56B -42.8(8) . . . . ?
C47 C49 C51B C56B 82.3(7) . . . . ?
C56B C51B C52B C53B 0.0 . . . . ?
C49 C51B C52B C53B 179.7(9) . . . . ?
C51B C52B C53B C54B 0.0 . . . . ?
C52B C53B C54B C55B 0.0 . . . . ?
C53B C54B C55B C56B 0.0 . . . . ?
C54B C55B C56B C51B 0.0 . . . . ?
C52B C51B C56B C55B 0.0 . . . . ?
C49 C51B C56B C55B -179.7(9) . . . . ?

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.025


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_B_DADPE_ben150k
_database_code_depnum_ccdc_archive 'CCDC 2295236'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2024-03-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_jdm_B_DADPE_ben150k 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The current compount crystallizes as a benzene solvate and 
presents a solvent channel along the C-axis. Although the crystals look
stable even at room temperature only diffraction up to 2A was visible at
ambient conditions, flash cooling fresh crystals at 150K improved 
resolution, but only up to 1.10A, evaporation of benzene from the crystal
probably results in the lower observed crystallinity. 
;
_vrf_PLAT089_jdm_B_DADPE_ben150k 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.51 Note
RESPONSE: A direct result of the lower resolution. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
'(R)-(+)-1,1?-Bi(2-naphthol) ; (1R,2R)-N,N?-Dimethyl-1,2-diphenylethane-1,2-diamine benzene solvate'
_chemical_name_common            'R-Binol (R,R)-DADPE benzene solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C14 H16 N2, 0.72(C20 H14 O2), 0.56(C10 H7 O), 2.72(C6 H6) [+ solvent]'
_chemical_formula_sum            'C50.27 H46.27 N2 O2'
_chemical_formula_weight         710.46

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      tetragonal
_space_group_IT_number           97
_space_group_name_H-M_alt        'I 4 2 2'
_space_group_name_Hall           'I 4 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'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'

_cell_length_a                   23.5398(17)
_cell_length_b                   23.5398(17)
_cell_length_c                   15.3506(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8506.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1236
_cell_measurement_theta_min      2.9190
_cell_measurement_theta_max      18.6400

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             3023
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.28300
_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       
;
'90 images, ΔΦ 3.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11492
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.915
_diffrn_reflns_theta_max         18.849
_diffrn_reflns_theta_full        18.849
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1682
_reflns_number_gt                1187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       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          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+38.0000P] 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 350 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         1682
_refine_ls_number_parameters     280
_refine_ls_number_restraints     408
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.1165
_refine_ls_wR_factor_ref         0.2667
_refine_ls_wR_factor_gt          0.2486
_refine_ls_goodness_of_fit_ref   1.248
_refine_ls_restrained_S_all      1.180
_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 0.446(2) 0.922(3) 0.409(2) 0.080(6) Uani 0.72(4) 1 d D . P A 3
H1 H 0.436234 0.920341 0.461812 0.119 Uiso 0.72(4) 1 calc R U P A 3
C2 C 0.5486(10) 0.8426(9) 0.2854(11) 0.069(7) Uani 0.72(4) 1 d DG U P A 3
H2 H 0.561867 0.841038 0.226994 0.082 Uiso 0.72(4) 1 calc R U P A 3
C3 C 0.5058(9) 0.8804(8) 0.3081(15) 0.069(7) Uani 0.72(4) 1 d DG U P A 3
H3 H 0.489755 0.904736 0.265297 0.083 Uiso 0.72(4) 1 calc R U P A 3
C4 C 0.4863(8) 0.8827(9) 0.3936(17) 0.076(7) Uani 0.72(4) 1 d DG U P A 3
C5 C 0.5098(8) 0.8471(9) 0.4563(13) 0.072(7) Uani 0.72(4) 1 d DG U P A 3
C6 C 0.5526(8) 0.8092(9) 0.4335(10) 0.073(7) Uani 0.72(4) 1 d DG U P A 3
C7 C 0.5720(9) 0.8070(9) 0.3481(10) 0.070(7) Uani 0.72(4) 1 d DG U P A 3
C8 C 0.6149(11) 0.7691(10) 0.3253(12) 0.091(10) Uani 0.72(4) 1 d DG U P A 3
H8 H 0.628124 0.767610 0.266932 0.110 Uiso 0.72(4) 1 calc R U P A 3
C9 C 0.6383(12) 0.7336(11) 0.3880(16) 0.133(13) Uani 0.72(4) 1 d DG U P A 3
H9 H 0.667555 0.707693 0.372471 0.159 Uiso 0.72(4) 1 calc R U P A 3
C10 C 0.6189(11) 0.7358(11) 0.4735(14) 0.135(13) Uani 0.72(4) 1 d DG U P A 3
H10 H 0.634873 0.711473 0.516316 0.163 Uiso 0.72(4) 1 calc R U P A 3
C11 C 0.5760(10) 0.7736(10) 0.4962(10) 0.100(10) Uani 0.72(4) 1 d DG U P A 3
H11 H 0.562761 0.775169 0.554624 0.120 Uiso 0.72(4) 1 calc R U P A 3
O1B O 0.450(6) 0.921(8) 0.390(7) 0.080(6) Uani 0.28(4) 1 d D . P A 4
H1B H 0.439746 0.921603 0.441820 0.119 Uiso 0.28(4) 1 calc R U P A 4
C2B C 0.570(2) 0.856(2) 0.285(3) 0.069(7) Uani 0.28(4) 1 d DG U P A 4
H2B H 0.586962 0.854765 0.228341 0.082 Uiso 0.28(4) 1 calc R U P A 4
C3B C 0.522(2) 0.888(2) 0.300(4) 0.069(7) Uani 0.28(4) 1 d DG U P A 4
H3B H 0.505460 0.909218 0.253718 0.083 Uiso 0.28(4) 1 calc R U P A 4
C4B C 0.498(2) 0.889(3) 0.382(5) 0.076(7) Uani 0.28(4) 1 d DG U P A 4
C5B C 0.522(2) 0.858(3) 0.450(4) 0.072(7) Uani 0.28(4) 1 d DG U P A 4
C6B C 0.571(2) 0.826(2) 0.435(3) 0.073(7) Uani 0.28(4) 1 d DG U P A 4
C7B C 0.595(2) 0.8247(19) 0.352(3) 0.070(7) Uani 0.28(4) 1 d DG U P A 4
C8B C 0.643(2) 0.792(2) 0.337(3) 0.091(10) Uani 0.28(4) 1 d DG U P A 4
H8B H 0.659633 0.791449 0.280791 0.110 Uiso 0.28(4) 1 calc R U P A 4
C9B C 0.667(3) 0.761(3) 0.405(4) 0.133(13) Uani 0.28(4) 1 d DG U P A 4
H9B H 0.700473 0.739310 0.394466 0.159 Uiso 0.28(4) 1 calc R U P A 4
C10B C 0.643(3) 0.763(3) 0.487(4) 0.135(13) Uani 0.28(4) 1 d DG U P A 4
H10B H 0.659812 0.741624 0.533521 0.163 Uiso 0.28(4) 1 calc R U P A 4
C11B C 0.595(3) 0.795(3) 0.502(3) 0.100(10) Uani 0.28(4) 1 d DG U P A 4
H11B H 0.578311 0.796077 0.558902 0.120 Uiso 0.28(4) 1 calc R U P A 4
C21 C 0.2919(15) 0.960(2) 0.563(4) 0.083(16) Uani 0.37(7) 1 d DG U P B 5
C22 C 0.2420(19) 0.986(3) 0.589(4) 0.089(19) Uani 0.37(7) 1 d G U P B 5
H22 H 0.241759 1.026207 0.600184 0.106 Uiso 0.37(7) 1 calc R U P B 5
C23 C 0.1925(16) 0.955(3) 0.600(4) 0.14(2) Uani 0.37(7) 1 d G U P B 5
H23 H 0.158448 0.973208 0.617783 0.162 Uiso 0.37(7) 1 calc R U P B 5
C24 C 0.1929(19) 0.897(3) 0.584(5) 0.14(3) Uani 0.37(7) 1 d G U P B 5
H24 H 0.159056 0.875304 0.591399 0.168 Uiso 0.37(7) 1 calc R U P B 5
C25 C 0.243(2) 0.870(2) 0.558(5) 0.16(3) Uani 0.37(7) 1 d G U P B 5
H25 H 0.242975 0.830400 0.547415 0.192 Uiso 0.37(7) 1 calc R U P B 5
C26 C 0.2922(19) 0.902(2) 0.548(5) 0.11(2) Uani 0.37(7) 1 d G U P B 5
H26 H 0.326287 0.883399 0.529816 0.132 Uiso 0.37(7) 1 calc R U P B 5
C21B C 0.3036(11) 0.9422(13) 0.556(2) 0.077(9) Uani 0.63(7) 1 d DG U P B 6
C22B C 0.2563(14) 0.9604(15) 0.602(2) 0.087(12) Uani 0.63(7) 1 d G U P B 6
H22B H 0.254910 0.997987 0.624431 0.104 Uiso 0.63(7) 1 calc R U P B 6
C23B C 0.2111(15) 0.9235(19) 0.616(2) 0.120(18) Uani 0.63(7) 1 d G U P B 6
H23B H 0.178787 0.935906 0.647821 0.144 Uiso 0.63(7) 1 calc R U P B 6
C24B C 0.2132(16) 0.8684(18) 0.583(3) 0.15(2) Uani 0.63(7) 1 d G U P B 6
H24B H 0.182290 0.843233 0.592939 0.184 Uiso 0.63(7) 1 calc R U P B 6
C25B C 0.2605(17) 0.8503(14) 0.537(3) 0.17(2) Uani 0.63(7) 1 d G U P B 6
H25B H 0.261915 0.812640 0.514667 0.205 Uiso 0.63(7) 1 calc R U P B 6
C26B C 0.3057(13) 0.8871(14) 0.523(3) 0.153(18) Uani 0.63(7) 1 d G U P B 6
H26B H 0.338039 0.874721 0.491276 0.183 Uiso 0.63(7) 1 calc R U P B 6
C27 C 0.3485(7) 0.9882(8) 0.5456(8) 0.081(5) Uani 1 1 d D U . . .
H27 H 0.350761 1.021532 0.585820 0.098 Uiso 1 1 calc R U . B 5
N28 N 0.4020(6) 0.9555(6) 0.5577(7) 0.080(4) Uani 1 1 d D . . . .
H28A H 0.399(3) 0.932(4) 0.603(6) 0.119 Uiso 1 1 d D U . . .
H28B H 0.430(5) 0.981(5) 0.561(9) 0.119 Uiso 1 1 d D U . . .
C31 C 0.3335(15) 0.8686(14) 0.241(2) 0.13(2) Uani 0.5 1 d G U P C -1
H31 H 0.355088 0.901701 0.253738 0.150 Uiso 0.5 1 calc R U P C -1
C32 C 0.3562(15) 0.8264(19) 0.188(2) 0.23(3) Uani 0.5 1 d G U P C -1
H32 H 0.393282 0.830657 0.164646 0.281 Uiso 0.5 1 calc R U P C -1
C33 C 0.3246(19) 0.7781(17) 0.169(3) 0.23(3) Uani 0.5 1 d G U P C -1
H33 H 0.340066 0.749224 0.133289 0.273 Uiso 0.5 1 calc R U P C -1
C34 C 0.2703(17) 0.7719(14) 0.204(2) 0.20(3) Uani 0.5 1 d G U P C -1
H34 H 0.248654 0.738834 0.191025 0.243 Uiso 0.5 1 calc R U P C -1
C35 C 0.2476(12) 0.8141(18) 0.257(3) 0.19(2) Uani 0.5 1 d G U P C -1
H35 H 0.210459 0.809877 0.280118 0.225 Uiso 0.5 1 calc R U P C -1
C36 C 0.2792(15) 0.8625(15) 0.275(3) 0.25(3) Uani 0.5 1 d G U P C -1
H36 H 0.263675 0.891311 0.311475 0.299 Uiso 0.5 1 calc R U P C -1
C41 C 0.5236(15) 0.667(2) 0.618(3) 0.34(3) Uani 0.86(4) 1 d G U P . .
H41 H 0.498971 0.682872 0.575436 0.404 Uiso 0.86(4) 1 calc R U P . .
C42 C 0.5307(18) 0.6934(13) 0.698(4) 0.33(3) Uani 0.86(4) 1 d G U P . .
H42 H 0.510850 0.727633 0.710319 0.391 Uiso 0.86(4) 1 calc R U P . .
C43 C 0.567(2) 0.670(3) 0.760(3) 0.48(5) Uani 0.86(4) 1 d G U P . .
H43 H 0.571623 0.688166 0.814669 0.571 Uiso 0.86(4) 1 calc R U P . .
C44 C 0.5958(16) 0.620(3) 0.742(4) 0.54(5) Uani 0.86(4) 1 d G U P . .
H44 H 0.620517 0.603937 0.784136 0.653 Uiso 0.86(4) 1 calc R U P . .
C45 C 0.5888(19) 0.5934(17) 0.662(5) 0.40(4) Uani 0.86(4) 1 d G U P . .
H45 H 0.608638 0.559175 0.649253 0.485 Uiso 0.86(4) 1 calc R U P . .
C46 C 0.553(2) 0.617(2) 0.600(3) 0.42(4) Uani 0.86(4) 1 d G U P . .
H46 H 0.547865 0.598642 0.544902 0.498 Uiso 0.86(4) 1 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 C4 1.347(18) . ?
O1 H1 0.8400 . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C5 1.42(4) 5_656 ?
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
O1B C4B 1.35(2) . ?
O1B H1B 0.8400 . ?
C2B C3B 1.3900 . ?
C2B C7B 1.3900 . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C5B C6B 1.3900 . ?
C5B C5B 1.86(10) 5_656 ?
C6B C7B 1.3900 . ?
C6B C11B 1.3900 . ?
C7B C8B 1.3900 . ?
C8B C9B 1.3900 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B H11B 0.9500 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C21 C27 1.52(2) . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C21B C22B 1.3900 . ?
C21B C26B 1.3900 . ?
C21B C27 1.52(2) . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9500 . ?
C23B C24B 1.3900 . ?
C23B H23B 0.9500 . ?
C24B C25B 1.3900 . ?
C24B H24B 0.9500 . ?
C25B C26B 1.3900 . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C27 N28 1.49(2) . ?
C27 C27 1.51(3) 6_576 ?
C27 H27 1.0000 . ?
N28 H28A 0.89(3) . ?
N28 H28B 0.89(3) . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C31 H31 0.9500 . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C34 H34 0.9500 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C41 H41 0.9500 . ?
C42 C43 1.3900 . ?
C42 H42 0.9500 . ?
C43 C44 1.3900 . ?
C43 H43 0.9500 . ?
C44 C45 1.3900 . ?
C44 H44 0.9500 . ?
C45 C46 1.3900 . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C3 C2 C7 120.0 . . ?
C3 C2 H2 120.0 . . ?
C7 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
O1 C4 C3 115.2(9) . . ?
O1 C4 C5 124.8(9) . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C11 120.0 . . ?
C5 C6 C11 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 C2 120.0 . . ?
C6 C7 C2 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 120.0 . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C4B O1B H1B 109.5 . . ?
C3B C2B C7B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C7B C2B H2B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
O1B C4B C5B 124.7(16) . . ?
O1B C4B C3B 115.2(16) . . ?
C5B C4B C3B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C7B C6B C5B 120.0 . . ?
C7B C6B C11B 120.0 . . ?
C5B C6B C11B 120.0 . . ?
C6B C7B C8B 120.0 . . ?
C6B C7B C2B 120.0 . . ?
C8B C7B C2B 120.0 . . ?
C9B C8B C7B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C11B C6B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C6B C11B H11B 120.0 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 C27 127(3) . . ?
C26 C21 C27 113(3) . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C22B C21B C26B 120.0 . . ?
C22B C21B C27 113(2) . . ?
C26B C21B C27 127(2) . . ?
C23B C22B C21B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C22B C23B C24B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C24B C23B H23B 120.0 . . ?
C25B C24B C23B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C23B C24B H24B 120.0 . . ?
C24B C25B C26B 120.0 . . ?
C24B C25B H25B 120.0 . . ?
C26B C25B H25B 120.0 . . ?
C25B C26B C21B 120.0 . . ?
C25B C26B H26B 120.0 . . ?
C21B C26B H26B 120.0 . . ?
N28 C27 C27 107.9(10) . 6_576 ?
N28 C27 C21 120(3) . . ?
C27 C27 C21 109(3) 6_576 . ?
N28 C27 C21B 102.0(18) . . ?
C27 C27 C21B 110.9(18) 6_576 . ?
N28 C27 H27 106.4 . . ?
C27 C27 H27 106.4 6_576 . ?
C21 C27 H27 106.4 . . ?
C27 N28 H28A 111(5) . . ?
C27 N28 H28B 106(10) . . ?
H28A N28 H28B 115(7) . . ?
C32 C31 C36 120.0 . . ?
C32 C31 H31 120.0 . . ?
C36 C31 H31 120.0 . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C42 C41 C46 120.0 . . ?
C42 C41 H41 120.0 . . ?
C46 C41 H41 120.0 . . ?
C43 C42 C41 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.0 . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 120.0 . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.0 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.0 . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.059



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: benzene'
