# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_RpB
_database_code_depnum_ccdc_archive 'CCDC 1976941'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
(R)-2-hydroxy-2?-(2-pyridylmethyloxy)-3-formyl-1,1?-binaphthalene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 N O3'
_chemical_formula_sum            'C27 H19 N O3'
_chemical_formula_weight         405.43

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                   7.1378(2)
_cell_length_b                   9.8466(2)
_cell_length_c                   14.7942(3)
_cell_angle_alpha                88.9786(16)
_cell_angle_beta                 79.0044(17)
_cell_angle_gamma                74.6213(19)
_cell_volume                     983.56(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9128
_cell_measurement_theta_min      3.0060
_cell_measurement_theta_max      28.8780

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_T_min  0.90546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_oxdiff_exptl_absorpt_empirical_full_max 1.478
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            15510
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         28.818
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             7323
_reflns_number_gt                6806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.625
_reflns_Friedel_fraction_max     0.548
_reflns_Friedel_fraction_full    0.731

_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       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_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)+(0.0537P)²+0.1283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 2500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7323
_refine_ls_number_parameters     567
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1980(2) 0.46945(16) -0.05341(11) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.3144(3) 0.3618(2) -0.09149(15) 0.0153(5) Uani 1 1 d . . . . .
H1 H 0.344387 0.357020 -0.156927 0.018 Uiso 1 1 calc R U . . .
C2 C 0.4096(3) 0.2407(2) -0.04289(15) 0.0129(4) Uani 1 1 d . . . . .
C3 C 0.5350(3) 0.1242(2) -0.09316(15) 0.0141(4) Uani 1 1 d . . . . .
H2 H 0.557779 0.124609 -0.158549 0.017 Uiso 1 1 calc R U . . .
C4 C 0.6298(3) 0.0049(2) -0.04934(14) 0.0133(4) Uani 1 1 d . . . . .
C5 C 0.7653(4) -0.1144(2) -0.10021(15) 0.0159(5) Uani 1 1 d . . . . .
H3 H 0.786017 -0.116635 -0.165595 0.019 Uiso 1 1 calc R U . . .
C6 C 0.8654(4) -0.2252(2) -0.05671(16) 0.0195(5) Uani 1 1 d . . . . .
H4 H 0.957770 -0.302871 -0.091559 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8312(3) -0.2241(2) 0.04064(15) 0.0184(4) Uani 1 1 d . . . . .
H5 H 0.901709 -0.301453 0.070755 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6979(4) -0.1132(2) 0.09245(15) 0.0161(5) Uani 1 1 d . . . . .
H6 H 0.673486 -0.116376 0.157758 0.019 Uiso 1 1 calc R U . . .
C9 C 0.5962(3) 0.0063(2) 0.04910(15) 0.0130(4) Uani 1 1 d . . . . .
C10 C 0.4654(3) 0.1268(2) 0.10123(14) 0.0132(4) Uani 1 1 d . . . . .
C11 C 0.3745(3) 0.2408(2) 0.05555(15) 0.0141(5) Uani 1 1 d . . . . .
O2 O 0.2514(3) 0.35619(18) 0.10545(11) 0.0184(4) Uani 1 1 d . . . . .
H7 H 0.212(4) 0.419(3) 0.0681(17) 0.017(6) Uiso 1 1 d . . . . .
C12 C 0.4263(3) 0.1308(2) 0.20433(14) 0.0131(4) Uani 1 1 d . . . . .
C13 C 0.2777(3) 0.0721(2) 0.25471(15) 0.0150(5) Uani 1 1 d . . . . .
C14 C 0.1655(3) 0.0022(2) 0.21072(15) 0.0165(5) Uani 1 1 d . . . . .
H8 H 0.192940 -0.008923 0.145466 0.020 Uiso 1 1 calc R U . . .
C15 C 0.0194(4) -0.0489(2) 0.26129(17) 0.0203(5) Uani 1 1 d . . . . .
H9 H -0.054679 -0.093756 0.230675 0.024 Uiso 1 1 calc R U . . .
C16 C -0.0231(4) -0.0358(2) 0.35880(16) 0.0207(5) Uani 1 1 d . . . . .
H10 H -0.126175 -0.070631 0.393171 0.025 Uiso 1 1 calc R U . . .
C17 C 0.0844(4) 0.0268(2) 0.40304(15) 0.0194(5) Uani 1 1 d . . . . .
H11 H 0.057143 0.033370 0.468464 0.023 Uiso 1 1 calc R U . . .
C18 C 0.2365(3) 0.0824(2) 0.35314(14) 0.0159(5) Uani 1 1 d . . . . .
C19 C 0.3469(3) 0.1499(2) 0.39781(15) 0.0178(5) Uani 1 1 d . . . . .
H12 H 0.320948 0.157119 0.463208 0.021 Uiso 1 1 calc R U . . .
C20 C 0.4897(3) 0.2047(2) 0.34906(15) 0.0170(5) Uani 1 1 d . . . . .
H13 H 0.562140 0.249639 0.380652 0.020 Uiso 1 1 calc R U . . .
C21 C 0.5312(3) 0.1952(2) 0.25190(15) 0.0154(5) Uani 1 1 d . . . . .
O3 O 0.6719(2) 0.24986(18) 0.19860(10) 0.0179(4) Uani 1 1 d . . . . .
C22 C 0.7988(4) 0.3065(2) 0.24170(16) 0.0158(5) Uani 1 1 d . . . . .
H14 H 0.924863 0.298195 0.197676 0.019 Uiso 1 1 calc R U . . .
H15 H 0.829616 0.249512 0.295432 0.019 Uiso 1 1 calc R U . . .
C23 C 0.7104(4) 0.4589(2) 0.27356(14) 0.0176(5) Uani 1 1 d . . . . .
N1 N 0.8385(4) 0.5132(2) 0.30772(14) 0.0240(5) Uani 1 1 d . . . . .
C24 C 0.7748(5) 0.6485(3) 0.33728(18) 0.0336(7) Uani 1 1 d . . . . .
H16 H 0.862893 0.687680 0.362209 0.040 Uiso 1 1 calc R U . . .
C25 C 0.5909(5) 0.7335(3) 0.33374(19) 0.0365(7) Uani 1 1 d . . . . .
H17 H 0.553521 0.829139 0.354928 0.044 Uiso 1 1 calc R U . . .
C26 C 0.4615(5) 0.6778(3) 0.29902(18) 0.0351(7) Uani 1 1 d . . . . .
H18 H 0.332406 0.734496 0.296348 0.042 Uiso 1 1 calc R U . . .
C27 C 0.5211(4) 0.5361(3) 0.26731(16) 0.0243(5) Uani 1 1 d . . . . .
H19 H 0.434671 0.494977 0.242576 0.029 Uiso 1 1 calc R U . . .
O4 O 0.3921(2) 0.73329(17) 0.97352(11) 0.0209(4) Uani 1 1 d . . . . .
C28 C 0.4928(4) 0.6301(2) 1.00557(15) 0.0167(5) Uani 1 1 d . . . . .
H20 H 0.474187 0.625587 1.070760 0.020 Uiso 1 1 calc R U . . .
C29 C 0.6392(3) 0.5134(2) 0.95131(14) 0.0139(5) Uani 1 1 d . . . . .
C30 C 0.7356(3) 0.3997(2) 0.99528(14) 0.0126(4) Uani 1 1 d . . . . .
H21 H 0.710157 0.400753 1.060713 0.015 Uiso 1 1 calc R U . . .
C31 C 0.8713(3) 0.2812(2) 0.94598(14) 0.0128(4) Uani 1 1 d . . . . .
C32 C 0.9666(3) 0.1623(2) 0.99088(15) 0.0138(5) Uani 1 1 d . . . . .
H22 H 0.940392 0.161778 1.056280 0.017 Uiso 1 1 calc R U . . .
C33 C 1.0962(3) 0.0474(2) 0.94163(16) 0.0150(4) Uani 1 1 d . . . . .
H23 H 1.159513 -0.031901 0.972533 0.018 Uiso 1 1 calc R U . . .
C34 C 1.1343(3) 0.0487(2) 0.84453(14) 0.0161(4) Uani 1 1 d . . . . .
H24 H 1.224291 -0.030551 0.810253 0.019 Uiso 1 1 calc R U . . .
C35 C 1.0440(3) 0.1622(2) 0.79864(15) 0.0141(5) Uani 1 1 d . . . . .
H25 H 1.072215 0.160183 0.733202 0.017 Uiso 1 1 calc R U . . .
C36 C 0.9090(3) 0.2824(2) 0.84761(14) 0.0117(4) Uani 1 1 d . . . . .
C37 C 0.8111(3) 0.4018(2) 0.80186(14) 0.0118(4) Uani 1 1 d . . . . .
C38 C 0.6781(3) 0.5139(2) 0.85266(14) 0.0132(4) Uani 1 1 d . . . . .
O5 O 0.5822(3) 0.62508(17) 0.80804(11) 0.0184(4) Uani 1 1 d . . . . .
H26 H 0.508(4) 0.682(3) 0.852(2) 0.028(8) Uiso 1 1 d . . . . .
C39 C 0.8550(3) 0.4037(2) 0.69890(14) 0.0130(4) Uani 1 1 d . . . . .
C40 C 1.0056(3) 0.4637(2) 0.65217(14) 0.0123(4) Uani 1 1 d . . . . .
C41 C 1.1174(3) 0.5273(2) 0.69996(15) 0.0141(4) Uani 1 1 d . . . . .
H27 H 1.087522 0.534392 0.765370 0.017 Uiso 1 1 calc R U . . .
C42 C 1.2681(3) 0.5787(2) 0.65279(16) 0.0163(5) Uani 1 1 d . . . . .
H28 H 1.342523 0.619543 0.685827 0.020 Uiso 1 1 calc R U . . .
C43 C 1.3132(3) 0.5710(2) 0.55520(16) 0.0180(5) Uani 1 1 d . . . . .
H29 H 1.418617 0.605677 0.523096 0.022 Uiso 1 1 calc R U . . .
C44 C 1.2051(3) 0.5137(2) 0.50707(15) 0.0168(5) Uani 1 1 d . . . . .
H30 H 1.233694 0.511442 0.441631 0.020 Uiso 1 1 calc R U . . .
C45 C 1.0509(3) 0.4575(2) 0.55381(14) 0.0142(4) Uani 1 1 d . . . . .
C46 C 0.9438(3) 0.3922(2) 0.50513(14) 0.0157(5) Uani 1 1 d . . . . .
H31 H 0.972810 0.388216 0.439682 0.019 Uiso 1 1 calc R U . . .
C47 C 0.7994(3) 0.3348(2) 0.55068(14) 0.0159(5) Uani 1 1 d . . . . .
H32 H 0.728824 0.291080 0.517135 0.019 Uiso 1 1 calc R U . . .
C48 C 0.7555(3) 0.3408(2) 0.64844(14) 0.0132(4) Uani 1 1 d . . . . .
O6 O 0.6153(2) 0.28195(16) 0.69875(10) 0.0159(3) Uani 1 1 d . . . . .
C49 C 0.4872(3) 0.2297(2) 0.65358(16) 0.0149(4) Uani 1 1 d . . . . .
H33 H 0.471516 0.281758 0.596458 0.018 Uiso 1 1 calc R U . . .
H34 H 0.355065 0.248490 0.694162 0.018 Uiso 1 1 calc R U . . .
C50 C 0.5616(3) 0.0741(2) 0.62938(14) 0.0138(5) Uani 1 1 d . . . . .
N2 N 0.4265(3) 0.0211(2) 0.60260(13) 0.0176(4) Uani 1 1 d . . . . .
C51 C 0.4774(4) -0.1172(3) 0.58161(17) 0.0224(5) Uani 1 1 d . . . . .
H35 H 0.382884 -0.155827 0.561756 0.027 Uiso 1 1 calc R U . . .
C52 C 0.6605(4) -0.2073(2) 0.58719(17) 0.0241(5) Uani 1 1 d . . . . .
H36 H 0.690027 -0.305077 0.572247 0.029 Uiso 1 1 calc R U . . .
C53 C 0.7988(4) -0.1506(3) 0.61512(17) 0.0232(5) Uani 1 1 d . . . . .
H37 H 0.925672 -0.208992 0.619932 0.028 Uiso 1 1 calc R U . . .
C54 C 0.7492(4) -0.0070(2) 0.63603(16) 0.0190(5) Uani 1 1 d . . . . .
H38 H 0.842117 0.034774 0.654538 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.228(3) . ?
C1 C2 1.458(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 C11 1.430(3) . ?
C3 C4 1.406(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.426(3) . ?
C4 C9 1.430(3) . ?
C5 C6 1.361(3) . ?
C5 H3 0.9500 . ?
C6 C7 1.414(3) . ?
C6 H4 0.9500 . ?
C7 C8 1.373(3) . ?
C7 H5 0.9500 . ?
C8 C9 1.421(3) . ?
C8 H6 0.9500 . ?
C9 C10 1.430(3) . ?
C10 C11 1.376(3) . ?
C10 C12 1.497(3) . ?
C11 O2 1.364(3) . ?
O2 H7 0.85(3) . ?
C12 C21 1.388(3) . ?
C12 C13 1.423(3) . ?
C13 C18 1.430(3) . ?
C13 C14 1.430(3) . ?
C14 C15 1.366(3) . ?
C14 H8 0.9500 . ?
C15 C16 1.417(3) . ?
C15 H9 0.9500 . ?
C16 C17 1.361(3) . ?
C16 H10 0.9500 . ?
C17 C18 1.421(3) . ?
C17 H11 0.9500 . ?
C18 C19 1.411(3) . ?
C19 C20 1.359(3) . ?
C19 H12 0.9500 . ?
C20 C21 1.411(3) . ?
C20 H13 0.9500 . ?
C21 O3 1.375(3) . ?
O3 C22 1.427(3) . ?
C22 C23 1.511(3) . ?
C22 H14 0.9900 . ?
C22 H15 0.9900 . ?
C23 N1 1.350(3) . ?
C23 C27 1.382(4) . ?
N1 C24 1.340(3) . ?
C24 C25 1.367(5) . ?
C24 H16 0.9500 . ?
C25 C26 1.370(4) . ?
C25 H17 0.9500 . ?
C26 C27 1.408(4) . ?
C26 H18 0.9500 . ?
C27 H19 0.9500 . ?
O4 C28 1.224(3) . ?
C28 C29 1.461(3) . ?
C28 H20 0.9500 . ?
C29 C30 1.373(3) . ?
C29 C38 1.433(3) . ?
C30 C31 1.412(3) . ?
C30 H21 0.9500 . ?
C31 C32 1.413(3) . ?
C31 C36 1.429(3) . ?
C32 C33 1.372(3) . ?
C32 H22 0.9500 . ?
C33 C34 1.410(3) . ?
C33 H23 0.9500 . ?
C34 C35 1.372(3) . ?
C34 H24 0.9500 . ?
C35 C36 1.420(3) . ?
C35 H25 0.9500 . ?
C36 C37 1.430(3) . ?
C37 C38 1.373(3) . ?
C37 C39 1.496(3) . ?
C38 O5 1.361(3) . ?
O5 H26 0.86(3) . ?
C39 C48 1.377(3) . ?
C39 C40 1.421(3) . ?
C40 C41 1.424(3) . ?
C40 C45 1.428(3) . ?
C41 C42 1.374(3) . ?
C41 H27 0.9500 . ?
C42 C43 1.417(3) . ?
C42 H28 0.9500 . ?
C43 C44 1.370(3) . ?
C43 H29 0.9500 . ?
C44 C45 1.419(3) . ?
C44 H30 0.9500 . ?
C45 C46 1.416(3) . ?
C46 C47 1.366(3) . ?
C46 H31 0.9500 . ?
C47 C48 1.419(3) . ?
C47 H32 0.9500 . ?
C48 O6 1.378(3) . ?
O6 C49 1.429(3) . ?
C49 C50 1.507(3) . ?
C49 H33 0.9900 . ?
C49 H34 0.9900 . ?
C50 N2 1.335(3) . ?
C50 C54 1.386(3) . ?
N2 C51 1.338(3) . ?
C51 C52 1.388(4) . ?
C51 H35 0.9500 . ?
C52 C53 1.383(4) . ?
C52 H36 0.9500 . ?
C53 C54 1.389(3) . ?
C53 H37 0.9500 . ?
C54 H38 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 124.3(2) . . ?
O1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C11 119.7(2) . . ?
C3 C2 C1 119.13(19) . . ?
C11 C2 C1 121.1(2) . . ?
C2 C3 C4 121.17(19) . . ?
C2 C3 H2 119.4 . . ?
C4 C3 H2 119.4 . . ?
C3 C4 C5 121.89(19) . . ?
C3 C4 C9 118.86(19) . . ?
C5 C4 C9 119.2(2) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H3 119.4 . . ?
C4 C5 H3 119.4 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H4 120.2 . . ?
C7 C6 H4 120.2 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H5 119.4 . . ?
C6 C7 H5 119.4 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H6 119.8 . . ?
C9 C8 H6 119.8 . . ?
C8 C9 C10 121.7(2) . . ?
C8 C9 C4 118.27(19) . . ?
C10 C9 C4 120.0(2) . . ?
C11 C10 C9 119.24(18) . . ?
C11 C10 C12 119.6(2) . . ?
C9 C10 C12 121.1(2) . . ?
O2 C11 C10 119.11(19) . . ?
O2 C11 C2 119.9(2) . . ?
C10 C11 C2 121.0(2) . . ?
C11 O2 H7 108.1(17) . . ?
C21 C12 C13 119.24(18) . . ?
C21 C12 C10 120.33(19) . . ?
C13 C12 C10 120.41(19) . . ?
C12 C13 C18 119.6(2) . . ?
C12 C13 C14 122.54(19) . . ?
C18 C13 C14 117.9(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H8 119.6 . . ?
C13 C14 H8 119.6 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H9 119.6 . . ?
C16 C15 H9 119.6 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H10 120.1 . . ?
C15 C16 H10 120.1 . . ?
C16 C17 C18 121.2(2) . . ?
C16 C17 H11 119.4 . . ?
C18 C17 H11 119.4 . . ?
C19 C18 C17 121.95(19) . . ?
C19 C18 C13 118.7(2) . . ?
C17 C18 C13 119.4(2) . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 H12 119.4 . . ?
C18 C19 H12 119.4 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H13 119.8 . . ?
C21 C20 H13 119.8 . . ?
O3 C21 C12 115.92(18) . . ?
O3 C21 C20 123.4(2) . . ?
C12 C21 C20 120.7(2) . . ?
C21 O3 C22 119.56(16) . . ?
O3 C22 C23 113.48(19) . . ?
O3 C22 H14 108.9 . . ?
C23 C22 H14 108.9 . . ?
O3 C22 H15 108.9 . . ?
C23 C22 H15 108.9 . . ?
H14 C22 H15 107.7 . . ?
N1 C23 C27 123.3(2) . . ?
N1 C23 C22 112.4(2) . . ?
C27 C23 C22 124.3(2) . . ?
C24 N1 C23 117.1(2) . . ?
N1 C24 C25 124.0(3) . . ?
N1 C24 H16 118.0 . . ?
C25 C24 H16 118.0 . . ?
C24 C25 C26 118.6(2) . . ?
C24 C25 H17 120.7 . . ?
C26 C25 H17 120.7 . . ?
C25 C26 C27 119.5(3) . . ?
C25 C26 H18 120.2 . . ?
C27 C26 H18 120.2 . . ?
C23 C27 C26 117.4(3) . . ?
C23 C27 H19 121.3 . . ?
C26 C27 H19 121.3 . . ?
O4 C28 C29 125.0(2) . . ?
O4 C28 H20 117.5 . . ?
C29 C28 H20 117.5 . . ?
C30 C29 C38 119.6(2) . . ?
C30 C29 C28 119.60(19) . . ?
C38 C29 C28 120.7(2) . . ?
C29 C30 C31 121.86(19) . . ?
C29 C30 H21 119.1 . . ?
C31 C30 H21 119.1 . . ?
C30 C31 C32 122.05(19) . . ?
C30 C31 C36 118.1(2) . . ?
C32 C31 C36 119.80(19) . . ?
C33 C32 C31 121.1(2) . . ?
C33 C32 H22 119.4 . . ?
C31 C32 H22 119.4 . . ?
C32 C33 C34 119.2(2) . . ?
C32 C33 H23 120.4 . . ?
C34 C33 H23 120.4 . . ?
C35 C34 C33 121.3(2) . . ?
C35 C34 H24 119.4 . . ?
C33 C34 H24 119.4 . . ?
C34 C35 C36 120.91(19) . . ?
C34 C35 H25 119.5 . . ?
C36 C35 H25 119.5 . . ?
C35 C36 C31 117.7(2) . . ?
C35 C36 C37 122.28(18) . . ?
C31 C36 C37 120.01(19) . . ?
C38 C37 C36 119.81(18) . . ?
C38 C37 C39 120.5(2) . . ?
C36 C37 C39 119.65(19) . . ?
O5 C38 C37 119.10(19) . . ?
O5 C38 C29 120.36(19) . . ?
C37 C38 C29 120.5(2) . . ?
C38 O5 H26 103.5(18) . . ?
C48 C39 C40 119.37(18) . . ?
C48 C39 C37 119.87(19) . . ?
C40 C39 C37 120.69(19) . . ?
C39 C40 C41 122.34(18) . . ?
C39 C40 C45 119.38(19) . . ?
C41 C40 C45 118.26(19) . . ?
C42 C41 C40 120.9(2) . . ?
C42 C41 H27 119.5 . . ?
C40 C41 H27 119.5 . . ?
C41 C42 C43 120.4(2) . . ?
C41 C42 H28 119.8 . . ?
C43 C42 H28 119.8 . . ?
C44 C43 C42 120.1(2) . . ?
C44 C43 H29 119.9 . . ?
C42 C43 H29 119.9 . . ?
C43 C44 C45 120.8(2) . . ?
C43 C44 H30 119.6 . . ?
C45 C44 H30 119.6 . . ?
C46 C45 C44 121.46(19) . . ?
C46 C45 C40 119.05(19) . . ?
C44 C45 C40 119.47(19) . . ?
C47 C46 C45 121.13(19) . . ?
C47 C46 H31 119.4 . . ?
C45 C46 H31 119.4 . . ?
C46 C47 C48 119.5(2) . . ?
C46 C47 H32 120.2 . . ?
C48 C47 H32 120.2 . . ?
C39 C48 O6 115.88(18) . . ?
C39 C48 C47 121.5(2) . . ?
O6 C48 C47 122.57(19) . . ?
C48 O6 C49 120.20(17) . . ?
O6 C49 C50 113.46(19) . . ?
O6 C49 H33 108.9 . . ?
C50 C49 H33 108.9 . . ?
O6 C49 H34 108.9 . . ?
C50 C49 H34 108.9 . . ?
H33 C49 H34 107.7 . . ?
N2 C50 C54 123.0(2) . . ?
N2 C50 C49 113.06(19) . . ?
C54 C50 C49 123.9(2) . . ?
C50 N2 C51 117.4(2) . . ?
N2 C51 C52 123.7(2) . . ?
N2 C51 H35 118.1 . . ?
C52 C51 H35 118.1 . . ?
C53 C52 C51 118.1(2) . . ?
C53 C52 H36 121.0 . . ?
C51 C52 H36 121.0 . . ?
C52 C53 C54 118.9(2) . . ?
C52 C53 H37 120.5 . . ?
C54 C53 H37 120.5 . . ?
C50 C54 C53 118.8(2) . . ?
C50 C54 H38 120.6 . . ?
C53 C54 H38 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.8(2) . . . . ?
O1 C1 C2 C11 -1.1(3) . . . . ?
C11 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -177.8(2) . . . . ?
C2 C3 C4 C9 -0.8(3) . . . . ?
C3 C4 C5 C6 175.7(2) . . . . ?
C9 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 1.7(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 -2.5(3) . . . . ?
C7 C8 C9 C10 -176.3(2) . . . . ?
C7 C8 C9 C4 2.8(3) . . . . ?
C3 C4 C9 C8 -178.0(2) . . . . ?
C5 C4 C9 C8 -0.9(3) . . . . ?
C3 C4 C9 C10 1.1(3) . . . . ?
C5 C4 C9 C10 178.17(19) . . . . ?
C8 C9 C10 C11 178.5(2) . . . . ?
C4 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C12 -1.4(3) . . . . ?
C4 C9 C10 C12 179.6(2) . . . . ?
C9 C10 C11 O2 -179.31(19) . . . . ?
C12 C10 C11 O2 0.5(3) . . . . ?
C9 C10 C11 C2 -0.2(3) . . . . ?
C12 C10 C11 C2 179.62(19) . . . . ?
C3 C2 C11 O2 179.63(19) . . . . ?
C1 C2 C11 O2 -0.5(3) . . . . ?
C3 C2 C11 C10 0.5(3) . . . . ?
C1 C2 C11 C10 -179.6(2) . . . . ?
C11 C10 C12 C21 -83.4(3) . . . . ?
C9 C10 C12 C21 96.4(3) . . . . ?
C11 C10 C12 C13 94.9(3) . . . . ?
C9 C10 C12 C13 -85.3(3) . . . . ?
C21 C12 C13 C18 1.0(3) . . . . ?
C10 C12 C13 C18 -177.3(2) . . . . ?
C21 C12 C13 C14 -179.0(2) . . . . ?
C10 C12 C13 C14 2.7(3) . . . . ?
C12 C13 C14 C15 -177.8(2) . . . . ?
C18 C13 C14 C15 2.1(3) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C16 C17 C18 C19 178.8(2) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C12 C13 C18 C19 -0.6(3) . . . . ?
C14 C13 C18 C19 179.4(2) . . . . ?
C12 C13 C18 C17 178.4(2) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C17 C18 C19 C20 -178.9(2) . . . . ?
C13 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C13 C12 C21 O3 -179.81(19) . . . . ?
C10 C12 C21 O3 -1.5(3) . . . . ?
C13 C12 C21 C20 -0.9(3) . . . . ?
C10 C12 C21 C20 177.4(2) . . . . ?
C19 C20 C21 O3 179.2(2) . . . . ?
C19 C20 C21 C12 0.4(3) . . . . ?
C12 C21 O3 C22 -174.33(19) . . . . ?
C20 C21 O3 C22 6.8(3) . . . . ?
C21 O3 C22 C23 -85.6(2) . . . . ?
O3 C22 C23 N1 -175.31(18) . . . . ?
O3 C22 C23 C27 3.6(3) . . . . ?
C27 C23 N1 C24 0.6(3) . . . . ?
C22 C23 N1 C24 179.5(2) . . . . ?
C23 N1 C24 C25 -0.8(4) . . . . ?
N1 C24 C25 C26 0.8(4) . . . . ?
C24 C25 C26 C27 -0.6(4) . . . . ?
N1 C23 C27 C26 -0.4(3) . . . . ?
C22 C23 C27 C26 -179.2(2) . . . . ?
C25 C26 C27 C23 0.4(3) . . . . ?
O4 C28 C29 C30 -176.5(2) . . . . ?
O4 C28 C29 C38 1.1(4) . . . . ?
C38 C29 C30 C31 -0.8(3) . . . . ?
C28 C29 C30 C31 176.9(2) . . . . ?
C29 C30 C31 C32 -178.2(2) . . . . ?
C29 C30 C31 C36 0.7(3) . . . . ?
C30 C31 C32 C33 179.18(19) . . . . ?
C36 C31 C32 C33 0.4(3) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C35 -0.2(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 0.2(3) . . . . ?
C34 C35 C36 C37 -179.4(2) . . . . ?
C30 C31 C36 C35 -179.29(19) . . . . ?
C32 C31 C36 C35 -0.4(3) . . . . ?
C30 C31 C36 C37 0.4(3) . . . . ?
C32 C31 C36 C37 179.21(19) . . . . ?
C35 C36 C37 C38 178.4(2) . . . . ?
C31 C36 C37 C38 -1.3(3) . . . . ?
C35 C36 C37 C39 -1.8(3) . . . . ?
C31 C36 C37 C39 178.54(19) . . . . ?
C36 C37 C38 O5 -178.26(18) . . . . ?
C39 C37 C38 O5 2.0(3) . . . . ?
C36 C37 C38 C29 1.1(3) . . . . ?
C39 C37 C38 C29 -178.65(19) . . . . ?
C30 C29 C38 O5 179.25(19) . . . . ?
C28 C29 C38 O5 1.6(3) . . . . ?
C30 C29 C38 C37 -0.1(3) . . . . ?
C28 C29 C38 C37 -177.8(2) . . . . ?
C38 C37 C39 C48 -95.4(3) . . . . ?
C36 C37 C39 C48 84.8(3) . . . . ?
C38 C37 C39 C40 87.7(3) . . . . ?
C36 C37 C39 C40 -92.1(2) . . . . ?
C48 C39 C40 C41 -178.5(2) . . . . ?
C37 C39 C40 C41 -1.6(3) . . . . ?
C48 C39 C40 C45 -0.1(3) . . . . ?
C37 C39 C40 C45 176.9(2) . . . . ?
C39 C40 C41 C42 177.0(2) . . . . ?
C45 C40 C41 C42 -1.5(3) . . . . ?
C40 C41 C42 C43 0.9(3) . . . . ?
C41 C42 C43 C44 0.8(3) . . . . ?
C42 C43 C44 C45 -1.9(3) . . . . ?
C43 C44 C45 C46 -177.1(2) . . . . ?
C43 C44 C45 C40 1.3(3) . . . . ?
C39 C40 C45 C46 0.3(3) . . . . ?
C41 C40 C45 C46 178.8(2) . . . . ?
C39 C40 C45 C44 -178.1(2) . . . . ?
C41 C40 C45 C44 0.4(3) . . . . ?
C44 C45 C46 C47 178.1(2) . . . . ?
C40 C45 C46 C47 -0.3(3) . . . . ?
C45 C46 C47 C48 0.1(3) . . . . ?
C40 C39 C48 O6 178.38(19) . . . . ?
C37 C39 C48 O6 1.4(3) . . . . ?
C40 C39 C48 C47 -0.1(3) . . . . ?
C37 C39 C48 C47 -177.1(2) . . . . ?
C46 C47 C48 C39 0.1(3) . . . . ?
C46 C47 C48 O6 -178.3(2) . . . . ?
C39 C48 O6 C49 172.31(18) . . . . ?
C47 C48 O6 C49 -9.2(3) . . . . ?
C48 O6 C49 C50 94.4(2) . . . . ?
O6 C49 C50 N2 168.69(17) . . . . ?
O6 C49 C50 C54 -9.9(3) . . . . ?
C54 C50 N2 C51 0.1(3) . . . . ?
C49 C50 N2 C51 -178.5(2) . . . . ?
C50 N2 C51 C52 0.7(4) . . . . ?
N2 C51 C52 C53 -0.7(4) . . . . ?
C51 C52 C53 C54 -0.2(4) . . . . ?
N2 C50 C54 C53 -0.9(3) . . . . ?
C49 C50 C54 C53 177.6(2) . . . . ?
C52 C53 C54 C50 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O6 0.95 2.56 3.393(3) 146.1 1_554 yes
O2 H7 O1 0.85(3) 1.87(3) 2.633(2) 149(2) . yes
O5 H26 O4 0.86(3) 1.84(3) 2.651(2) 155(3) . yes

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043

