#------------------------------------------------------------------------------
#$Date: 2023-08-30 01:56:13 +0300 (Wed, 30 Aug 2023) $
#$Revision: 285899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/38/7713819.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7713819
loop_
_publ_author_name
'Carbonel, Halen'
'Mikulski, Timothy D.'
'Nugraha, Kahargyan'
'Johnston, James'
'Wang, Yichun'
'Brown, Seth N.'
_publ_section_title
;
 Optically active bis(aminophenols) and their metal complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02436A
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C48 H56 N2 O2, C7 H8, C H4 O'
_chemical_formula_sum            'C56 H68 N2 O3'
_chemical_formula_weight         817.12
_chemical_name_common            '(R)-BiniqH4 . CH3OH . PhCH3'
_chemical_name_systematic
'(R)-2,2'-bis-N-(2-hydroxy-3,5-di-tert-butylphenyl)amino-1,1'-binaphthyl methanol toluene solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-07-14 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.041(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.1059(14)
_cell_length_b                   9.4304(9)
_cell_length_c                   17.6428(16)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.341
_cell_measurement_theta_min      2.360
_cell_volume                     2458.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            82110
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         1.617
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             884
_exptl_crystal_recrystallization_method
'Crystals formed on diffusion of methanol into a toluene solution of the compound.'
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         9921
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.239
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0888
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0502P)²+5.0527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2183
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                7691
_reflns_number_total             9921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt02436a2.cif
_cod_data_source_block           biniqh4
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7713819
_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.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.7770(4) 0.3064(5) 0.4580(3) 0.0346(12) Uani 1 1 d . . . . .
H1O H 0.7788 0.3157 0.4110 0.041 Uiso 1 1 calc R U . . .
N1 N 0.6999(4) 0.1567(6) 0.3291(3) 0.0255(13) Uani 1 1 d . . . . .
O2 O 0.9269(4) 0.4855(6) 0.1901(3) 0.0373(13) Uani 1 1 d . . . . .
N2 N 0.7639(4) 0.3545(6) 0.1471(3) 0.0232(12) Uani 1 1 d . . . . .
C11 C 0.7367(4) 0.1808(7) 0.4686(4) 0.0246(14) Uani 1 1 d . . . . .
C12 C 0.6950(4) 0.1016(7) 0.4036(4) 0.0241(14) Uani 1 1 d . . . . .
C13 C 0.6556(4) -0.0283(7) 0.4116(4) 0.0256(15) Uani 1 1 d . . . . .
C14 C 0.6566(5) -0.0831(7) 0.4855(4) 0.0266(15) Uani 1 1 d . . . . .
C15 C 0.6969(4) -0.0015(7) 0.5487(4) 0.0238(14) Uani 1 1 d . . . . .
C16 C 0.7374(4) 0.1303(7) 0.5432(4) 0.0244(14) Uani 1 1 d . . . . .
C17 C 0.7832(5) 0.2139(8) 0.6155(4) 0.0316(16) Uani 1 1 d . . . . .
C18 C 0.6139(5) -0.2280(8) 0.4946(5) 0.0364(18) Uani 1 1 d . . . . .
C21 C 0.8809(4) 0.5013(7) 0.1150(4) 0.0197(13) Uani 1 1 d . . . . .
C22 C 0.7980(4) 0.4347(6) 0.0905(4) 0.0205(13) Uani 1 1 d . . . . .
C23 C 0.7502(4) 0.4488(6) 0.0150(4) 0.0191(13) Uani 1 1 d . . . . .
C24 C 0.7833(4) 0.5286(6) -0.0382(4) 0.0178(13) Uani 1 1 d . . . . .
C25 C 0.8668(4) 0.5972(7) -0.0119(4) 0.0210(13) Uani 1 1 d . . . . .
C26 C 0.9173(4) 0.5848(7) 0.0641(4) 0.0201(13) Uani 1 1 d . . . . .
C27 C 1.0091(4) 0.6599(7) 0.0894(4) 0.0250(14) Uani 1 1 d . . . . .
C28 C 0.7285(4) 0.5438(7) -0.1211(4) 0.0240(14) Uani 1 1 d . . . . .
C31 C 0.6175(4) 0.2413(6) 0.2061(4) 0.0180(13) Uani 1 1 d . . . . .
C32 C 0.6302(4) 0.2387(6) 0.2858(4) 0.0208(14) Uani 1 1 d . . . . .
C33 C 0.5749(5) 0.3237(7) 0.3239(4) 0.0245(15) Uani 1 1 d . . . . .
C34 C 0.5098(4) 0.4098(7) 0.2828(4) 0.0259(15) Uani 1 1 d . . . . .
C35 C 0.4273(4) 0.5042(7) 0.1567(4) 0.0262(15) Uani 1 1 d . . . . .
C36 C 0.4149(5) 0.5099(8) 0.0786(5) 0.0305(16) Uani 1 1 d . . . . .
C37 C 0.4681(4) 0.4268(7) 0.0390(4) 0.0272(15) Uani 1 1 d . . . . .
C38 C 0.5330(4) 0.3374(7) 0.0799(4) 0.0200(13) Uani 1 1 d . . . . .
C39 C 0.5491(4) 0.3300(6) 0.1617(4) 0.0179(13) Uani 1 1 d . . . . .
C310 C 0.4949(4) 0.4166(7) 0.2009(4) 0.0203(13) Uani 1 1 d . . . . .
C41 C 0.6747(4) 0.1509(6) 0.1661(3) 0.0155(12) Uani 1 1 d . . . . .
C42 C 0.7429(4) 0.2107(6) 0.1350(3) 0.0183(13) Uani 1 1 d . . . . .
C43 C 0.7946(4) 0.1265(7) 0.0945(4) 0.0233(14) Uani 1 1 d . . . . .
C44 C 0.7796(4) -0.0165(7) 0.0856(4) 0.0240(14) Uani 1 1 d . . . . .
C45 C 0.6962(5) -0.2309(7) 0.1105(4) 0.0276(16) Uani 1 1 d . . . . .
C46 C 0.6307(5) -0.2922(8) 0.1409(5) 0.0321(16) Uani 1 1 d . . . . .
C47 C 0.5779(5) -0.2112(8) 0.1808(4) 0.0298(16) Uani 1 1 d . . . . .
C48 C 0.5903(4) -0.0675(7) 0.1889(4) 0.0205(13) Uani 1 1 d . . . . .
C49 C 0.6592(4) 0.0014(7) 0.1584(3) 0.0178(12) Uani 1 1 d . . . . .
C410 C 0.7127(4) -0.0827(7) 0.1185(3) 0.0187(13) Uani 1 1 d . . . . .
C171 C 0.8844(6) 0.2260(11) 0.6167(5) 0.050(2) Uani 1 1 d . . . . .
H17A H 0.8931 0.2727 0.5692 0.075 Uiso 1 1 calc R U . . .
H17B H 0.9112 0.1310 0.6200 0.075 Uiso 1 1 calc R U . . .
H17C H 0.9138 0.2820 0.6618 0.075 Uiso 1 1 calc R U . . .
C172 C 0.7727(6) 0.1412(10) 0.6897(4) 0.044(2) Uani 1 1 d . . . . .
H17D H 0.8027 0.1978 0.7343 0.066 Uiso 1 1 calc R U . . .
H17E H 0.8005 0.0469 0.6925 0.066 Uiso 1 1 calc R U . . .
H17F H 0.7083 0.1319 0.6904 0.066 Uiso 1 1 calc R U . . .
C173 C 0.7424(6) 0.3627(9) 0.6141(5) 0.044(2) Uani 1 1 d . . . . .
H17G H 0.7484 0.4113 0.5663 0.066 Uiso 1 1 calc R U . . .
H17H H 0.7744 0.4167 0.6590 0.066 Uiso 1 1 calc R U . . .
H17I H 0.6782 0.3555 0.6160 0.066 Uiso 1 1 calc R U . . .
C181 C 0.5122(6) -0.2184(11) 0.4628(7) 0.067(3) Uani 1 1 d . . . . .
H18A H 0.5009 -0.1866 0.4087 0.100 Uiso 1 1 calc R U . . .
H18B H 0.4855 -0.1505 0.4936 0.100 Uiso 1 1 calc R U . . .
H18C H 0.4847 -0.3119 0.4655 0.100 Uiso 1 1 calc R U . . .
C182 C 0.6301(6) -0.2776(9) 0.5791(5) 0.046(2) Uani 1 1 d . . . . .
H18D H 0.6016 -0.3703 0.5816 0.069 Uiso 1 1 calc R U . . .
H18E H 0.6038 -0.2088 0.6097 0.069 Uiso 1 1 calc R U . . .
H18F H 0.6953 -0.2853 0.6000 0.069 Uiso 1 1 calc R U . . .
C183 C 0.6565(7) -0.3397(9) 0.4500(5) 0.052(2) Uani 1 1 d . . . . .
H18G H 0.6478 -0.3118 0.3955 0.079 Uiso 1 1 calc R U . . .
H18H H 0.6276 -0.4318 0.4538 0.079 Uiso 1 1 calc R U . . .
H18I H 0.7214 -0.3470 0.4724 0.079 Uiso 1 1 calc R U . . .
C271 C 1.0332(5) 0.7470(10) 0.0222(5) 0.046(2) Uani 1 1 d . . . . .
H27A H 1.0357 0.6838 -0.0214 0.069 Uiso 1 1 calc R U . . .
H27B H 1.0923 0.7923 0.0398 0.069 Uiso 1 1 calc R U . . .
H27C H 0.9870 0.8199 0.0057 0.069 Uiso 1 1 calc R U . . .
C272 C 1.0848(5) 0.5508(9) 0.1151(5) 0.042(2) Uani 1 1 d . . . . .
H27D H 1.0861 0.4848 0.0725 0.063 Uiso 1 1 calc R U . . .
H27E H 1.0734 0.4981 0.1600 0.063 Uiso 1 1 calc R U . . .
H27F H 1.1431 0.5999 0.1292 0.063 Uiso 1 1 calc R U . . .
C273 C 1.0060(5) 0.7634(8) 0.1555(4) 0.0339(17) Uani 1 1 d . . . . .
H27G H 0.9575 0.8326 0.1386 0.051 Uiso 1 1 calc R U . . .
H27H H 1.0642 0.8130 0.1698 0.051 Uiso 1 1 calc R U . . .
H27I H 0.9945 0.7110 0.2004 0.051 Uiso 1 1 calc R U . . .
C281 C 0.7797(6) 0.6212(11) -0.1733(4) 0.047(2) Uani 1 1 d . . . . .
H28A H 0.7419 0.6277 -0.2256 0.070 Uiso 1 1 calc R U . . .
H28B H 0.8354 0.5694 -0.1752 0.070 Uiso 1 1 calc R U . . .
H28C H 0.7949 0.7168 -0.1530 0.070 Uiso 1 1 calc R U . . .
C282 C 0.6401(5) 0.6214(9) -0.1196(4) 0.0364(18) Uani 1 1 d . . . . .
H28D H 0.6069 0.5700 -0.0860 0.055 Uiso 1 1 calc R U . . .
H28E H 0.6031 0.6262 -0.1722 0.055 Uiso 1 1 calc R U . . .
H28F H 0.6535 0.7176 -0.0995 0.055 Uiso 1 1 calc R U . . .
C283 C 0.7053(6) 0.3953(9) -0.1557(4) 0.040(2) Uani 1 1 d . . . . .
H28G H 0.6717 0.3424 -0.1230 0.060 Uiso 1 1 calc R U . . .
H28H H 0.7614 0.3446 -0.1580 0.060 Uiso 1 1 calc R U . . .
H28I H 0.6682 0.4042 -0.2081 0.060 Uiso 1 1 calc R U . . .
C51 C 0.9460(14) 0.055(2) 0.3440(12) 0.135(7) Uani 1 1 d . U . . .
C52 C 0.9937(15) 0.121(2) 0.2931(13) 0.140(8) Uani 1 1 d . U . . .
H52 H 0.9812 0.0901 0.2406 0.169 Uiso 1 1 calc R U . . .
C53 C 1.0608(15) 0.232(2) 0.3152(13) 0.133(7) Uani 1 1 d . U . . .
H53 H 1.0911 0.2760 0.2792 0.159 Uiso 1 1 calc R U . . .
C54 C 1.0773(14) 0.271(2) 0.3942(17) 0.163(8) Uani 1 1 d . U . . .
H54 H 1.1229 0.3393 0.4123 0.196 Uiso 1 1 calc R U . . .
C55 C 1.0294(12) 0.212(3) 0.4482(14) 0.150(8) Uani 1 1 d . U . . .
H55 H 1.0398 0.2465 0.4999 0.180 Uiso 1 1 calc R U . . .
C56 C 0.9631(12) 0.097(2) 0.4228(8) 0.124(7) Uani 1 1 d . U . . .
H56 H 0.9330 0.0517 0.4585 0.149 Uiso 1 1 calc R U . . .
C57 C 0.8847(9) -0.0506(17) 0.3167(11) 0.122(7) Uani 1 1 d . . . . .
H57A H 0.8424 -0.0171 0.2703 0.183 Uiso 1 1 calc R U . . .
H57B H 0.8511 -0.0755 0.3567 0.183 Uiso 1 1 calc R U . . .
H57C H 0.9170 -0.1343 0.3038 0.183 Uiso 1 1 calc R U . . .
O6 O 0.8530(5) 0.3995(8) 0.3281(5) 0.073(2) Uani 1 1 d . . . . .
H6 H 0.9015 0.3535 0.3334 0.088 Uiso 1 1 calc R U . . .
C6 C 0.8707(14) 0.533(2) 0.3624(12) 0.179(12) Uani 1 1 d . . . . .
H6A H 0.8887 0.5227 0.4187 0.269 Uiso 1 1 calc R U . . .
H6B H 0.8161 0.5920 0.3496 0.269 Uiso 1 1 calc R U . . .
H6C H 0.9197 0.5790 0.3427 0.269 Uiso 1 1 calc R U . . .
H1N H 0.731(6) 0.100(9) 0.304(5) 0.05(2) Uiso 1 1 d . . . . .
H2O H 0.901(6) 0.431(10) 0.211(5) 0.04(3) Uiso 1 1 d . . . . .
H2N H 0.738(5) 0.402(8) 0.177(4) 0.03(2) Uiso 1 1 d . . . . .
H13 H 0.623(5) -0.077(8) 0.360(4) 0.03(2) Uiso 1 1 d . . . . .
H15 H 0.700(4) -0.032(7) 0.597(4) 0.012(15) Uiso 1 1 d . . . . .
H23 H 0.691(4) 0.399(7) -0.001(3) 0.011(15) Uiso 1 1 d . . . . .
H25 H 0.894(4) 0.665(8) -0.048(4) 0.023(17) Uiso 1 1 d . . . . .
H33 H 0.584(4) 0.319(6) 0.376(4) 0.009(15) Uiso 1 1 d . . . . .
H34 H 0.480(4) 0.469(8) 0.315(4) 0.023(18) Uiso 1 1 d . . . . .
H35 H 0.394(6) 0.559(11) 0.184(5) 0.06(3) Uiso 1 1 d . . . . .
H36 H 0.371(6) 0.554(10) 0.051(5) 0.05(3) Uiso 1 1 d . . . . .
H37 H 0.453(5) 0.429(7) -0.016(4) 0.026(19) Uiso 1 1 d . . . . .
H38 H 0.564(4) 0.276(7) 0.053(4) 0.012(16) Uiso 1 1 d . . . . .
H43 H 0.837(5) 0.174(8) 0.074(4) 0.026(19) Uiso 1 1 d . . . . .
H44 H 0.820(6) -0.071(9) 0.057(5) 0.05(2) Uiso 1 1 d . . . . .
H45 H 0.729(5) -0.277(9) 0.089(5) 0.03(2) Uiso 1 1 d . . . . .
H46 H 0.619(5) -0.387(9) 0.140(4) 0.03(2) Uiso 1 1 d . . . . .
H47 H 0.531(5) -0.249(9) 0.201(5) 0.04(2) Uiso 1 1 d . . . . .
H48 H 0.557(4) -0.010(8) 0.212(4) 0.019(17) Uiso 1 1 d . . . . .
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'
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
C11 O1 H1O 109.5 . . ?
C32 N1 C12 121.7(5) . . ?
C32 N1 H1N 119(5) . . ?
C12 N1 H1N 111(5) . . ?
C21 O2 H2O 109(6) . . ?
C42 N2 C22 120.6(5) . . ?
C42 N2 H2N 119(5) . . ?
C22 N2 H2N 116(5) . . ?
O1 C11 C16 120.7(6) . . ?
O1 C11 C12 119.2(6) . . ?
C16 C11 C12 120.2(6) . . ?
C13 C12 C11 121.2(6) . . ?
C13 C12 N1 121.4(6) . . ?
C11 C12 N1 117.3(6) . . ?
C12 C13 C14 120.1(6) . . ?
C12 C13 H13 116(4) . . ?
C14 C13 H13 124(4) . . ?
C15 C14 C13 117.6(6) . . ?
C15 C14 C18 122.2(6) . . ?
C13 C14 C18 120.2(6) . . ?
C14 C15 C16 124.2(6) . . ?
C14 C15 H15 121(4) . . ?
C16 C15 H15 115(4) . . ?
C15 C16 C11 116.9(6) . . ?
C15 C16 C17 121.7(6) . . ?
C11 C16 C17 121.4(6) . . ?
C172 C17 C171 107.8(7) . . ?
C172 C17 C173 108.4(6) . . ?
C171 C17 C173 109.3(7) . . ?
C172 C17 C16 112.0(6) . . ?
C171 C17 C16 109.0(6) . . ?
C173 C17 C16 110.3(6) . . ?
C181 C18 C182 108.7(7) . . ?
C181 C18 C14 108.8(7) . . ?
C182 C18 C14 112.8(7) . . ?
C181 C18 C183 110.5(8) . . ?
C182 C18 C183 106.8(7) . . ?
C14 C18 C183 109.1(6) . . ?
O2 C21 C22 119.7(6) . . ?
O2 C21 C26 119.8(5) . . ?
C22 C21 C26 120.5(6) . . ?
C23 C22 C21 120.9(6) . . ?
C23 C22 N2 122.1(6) . . ?
C21 C22 N2 117.0(6) . . ?
C24 C23 C22 121.2(6) . . ?
C24 C23 H23 120(3) . . ?
C22 C23 H23 119(3) . . ?
C23 C24 C25 117.1(6) . . ?
C23 C24 C28 120.1(5) . . ?
C25 C24 C28 122.8(6) . . ?
C26 C25 C24 123.3(6) . . ?
C26 C25 H25 115(4) . . ?
C24 C25 H25 121(4) . . ?
C21 C26 C25 117.0(5) . . ?
C21 C26 C27 121.8(6) . . ?
C25 C26 C27 121.1(5) . . ?
C273 C27 C272 110.0(6) . . ?
C273 C27 C26 110.3(5) . . ?
C272 C27 C26 110.3(6) . . ?
C273 C27 C271 107.2(6) . . ?
C272 C27 C271 107.6(6) . . ?
C26 C27 C271 111.4(6) . . ?
C281 C28 C282 109.9(6) . . ?
C281 C28 C24 112.7(6) . . ?
C282 C28 C24 109.2(5) . . ?
C281 C28 C283 107.6(6) . . ?
C282 C28 C283 108.3(6) . . ?
C24 C28 C283 109.1(6) . . ?
C32 C31 C39 120.0(5) . . ?
C32 C31 C41 120.1(5) . . ?
C39 C31 C41 120.0(5) . . ?
C31 C32 N1 119.7(6) . . ?
C31 C32 C33 120.1(6) . . ?
N1 C32 C33 120.2(6) . . ?
C34 C33 C32 120.9(6) . . ?
C34 C33 H33 121(4) . . ?
C32 C33 H33 118(4) . . ?
C33 C34 C310 120.9(6) . . ?
C33 C34 H34 113(4) . . ?
C310 C34 H34 125(4) . . ?
C36 C35 C310 121.1(7) . . ?
C36 C35 H35 122(6) . . ?
C310 C35 H35 117(6) . . ?
C35 C36 C37 120.8(7) . . ?
C35 C36 H36 122(6) . . ?
C37 C36 H36 117(6) . . ?
C38 C37 C36 119.8(7) . . ?
C38 C37 H37 123(4) . . ?
C36 C37 H37 117(4) . . ?
C37 C38 C39 121.1(6) . . ?
C37 C38 H38 119(4) . . ?
C39 C38 H38 120(4) . . ?
C38 C39 C31 122.6(6) . . ?
C38 C39 C310 118.1(5) . . ?
C31 C39 C310 119.3(5) . . ?
C35 C310 C34 122.2(6) . . ?
C35 C310 C39 119.0(6) . . ?
C34 C310 C39 118.8(6) . . ?
C42 C41 C49 118.9(5) . . ?
C42 C41 C31 120.5(5) . . ?
C49 C41 C31 120.6(5) . . ?
C41 C42 N2 119.8(6) . . ?
C41 C42 C43 120.6(6) . . ?
N2 C42 C43 119.5(6) . . ?
C44 C43 C42 121.1(6) . . ?
C44 C43 H43 123(5) . . ?
C42 C43 H43 116(5) . . ?
C43 C44 C410 120.3(6) . . ?
C43 C44 H44 117(5) . . ?
C410 C44 H44 123(5) . . ?
C46 C45 C410 120.7(7) . . ?
C46 C45 H45 122(6) . . ?
C410 C45 H45 118(6) . . ?
C45 C46 C47 120.6(7) . . ?
C45 C46 H46 125(5) . . ?
C47 C46 H46 115(5) . . ?
C48 C47 C46 120.9(7) . . ?
C48 C47 H47 116(5) . . ?
C46 C47 H47 123(5) . . ?
C47 C48 C49 120.4(6) . . ?
C47 C48 H48 125(4) . . ?
C49 C48 H48 115(4) . . ?
C410 C49 C48 118.0(6) . . ?
C410 C49 C41 120.0(5) . . ?
C48 C49 C41 122.0(6) . . ?
C44 C410 C49 119.1(6) . . ?
C44 C410 C45 121.4(6) . . ?
C49 C410 C45 119.5(6) . . ?
C17 C171 H17A 109.5 . . ?
C17 C171 H17B 109.5 . . ?
H17A C171 H17B 109.5 . . ?
C17 C171 H17C 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?
C17 C172 H17D 109.5 . . ?
C17 C172 H17E 109.5 . . ?
H17D C172 H17E 109.5 . . ?
C17 C172 H17F 109.5 . . ?
H17D C172 H17F 109.5 . . ?
H17E C172 H17F 109.5 . . ?
C17 C173 H17G 109.5 . . ?
C17 C173 H17H 109.5 . . ?
H17G C173 H17H 109.5 . . ?
C17 C173 H17I 109.5 . . ?
H17G C173 H17I 109.5 . . ?
H17H C173 H17I 109.5 . . ?
C18 C181 H18A 109.5 . . ?
C18 C181 H18B 109.5 . . ?
H18A C181 H18B 109.5 . . ?
C18 C181 H18C 109.5 . . ?
H18A C181 H18C 109.5 . . ?
H18B C181 H18C 109.5 . . ?
C18 C182 H18D 109.5 . . ?
C18 C182 H18E 109.5 . . ?
H18D C182 H18E 109.5 . . ?
C18 C182 H18F 109.5 . . ?
H18D C182 H18F 109.5 . . ?
H18E C182 H18F 109.5 . . ?
C18 C183 H18G 109.5 . . ?
C18 C183 H18H 109.5 . . ?
H18G C183 H18H 109.5 . . ?
C18 C183 H18I 109.5 . . ?
H18G C183 H18I 109.5 . . ?
H18H C183 H18I 109.5 . . ?
C27 C271 H27A 109.5 . . ?
C27 C271 H27B 109.5 . . ?
H27A C271 H27B 109.5 . . ?
C27 C271 H27C 109.5 . . ?
H27A C271 H27C 109.5 . . ?
H27B C271 H27C 109.5 . . ?
C27 C272 H27D 109.5 . . ?
C27 C272 H27E 109.5 . . ?
H27D C272 H27E 109.5 . . ?
C27 C272 H27F 109.5 . . ?
H27D C272 H27F 109.5 . . ?
H27E C272 H27F 109.5 . . ?
C27 C273 H27G 109.5 . . ?
C27 C273 H27H 109.5 . . ?
H27G C273 H27H 109.5 . . ?
C27 C273 H27I 109.5 . . ?
H27G C273 H27I 109.5 . . ?
H27H C273 H27I 109.5 . . ?
C28 C281 H28A 109.5 . . ?
C28 C281 H28B 109.5 . . ?
H28A C281 H28B 109.5 . . ?
C28 C281 H28C 109.5 . . ?
H28A C281 H28C 109.5 . . ?
H28B C281 H28C 109.5 . . ?
C28 C282 H28D 109.5 . . ?
C28 C282 H28E 109.5 . . ?
H28D C282 H28E 109.5 . . ?
C28 C282 H28F 109.5 . . ?
H28D C282 H28F 109.5 . . ?
H28E C282 H28F 109.5 . . ?
C28 C283 H28G 109.5 . . ?
C28 C283 H28H 109.5 . . ?
H28G C283 H28H 109.5 . . ?
C28 C283 H28I 109.5 . . ?
H28G C283 H28I 109.5 . . ?
H28H C283 H28I 109.5 . . ?
C57 C51 C52 119(2) . . ?
C57 C51 C56 121(2) . . ?
C52 C51 C56 119(2) . . ?
C51 C52 C53 125(2) . . ?
C51 C52 H52 117.7 . . ?
C53 C52 H52 117.7 . . ?
C54 C53 C52 115(2) . . ?
C54 C53 H53 122.6 . . ?
C52 C53 H53 122.6 . . ?
C53 C54 C55 124(2) . . ?
C53 C54 H54 118.2 . . ?
C55 C54 H54 118.2 . . ?
C54 C55 C56 119(2) . . ?
C54 C55 H55 120.4 . . ?
C56 C55 H55 120.4 . . ?
C51 C56 C55 118(2) . . ?
C51 C56 H56 120.9 . . ?
C55 C56 H56 120.9 . . ?
C51 C57 H57A 109.5 . . ?
C51 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C51 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C6 O6 H6 109.5 . . ?
O6 C6 H6A 109.5 . . ?
O6 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O6 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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 C11 1.363(8) . ?
O1 H1O 0.8400 . ?
N1 C32 1.398(8) . ?
N1 C12 1.430(8) . ?
N1 H1N 0.89(9) . ?
O2 C21 1.369(8) . ?
O2 H2O 0.78(9) . ?
N2 C42 1.399(8) . ?
N2 C22 1.432(8) . ?
N2 H2N 0.85(8) . ?
C11 C16 1.397(9) . ?
C11 C12 1.403(9) . ?
C12 C13 1.382(10) . ?
C13 C14 1.399(10) . ?
C13 H13 1.04(8) . ?
C14 C15 1.387(10) . ?
C14 C18 1.534(10) . ?
C15 C16 1.397(10) . ?
C15 H15 0.90(7) . ?
C16 C17 1.537(9) . ?
C17 C172 1.515(11) . ?
C17 C171 1.529(11) . ?
C17 C173 1.530(11) . ?
C18 C181 1.524(12) . ?
C18 C182 1.533(11) . ?
C18 C183 1.535(11) . ?
C21 C22 1.388(8) . ?
C21 C26 1.391(8) . ?
C22 C23 1.383(9) . ?
C23 C24 1.376(9) . ?
C23 H23 1.00(6) . ?
C24 C25 1.406(9) . ?
C24 C28 1.529(9) . ?
C25 C26 1.404(9) . ?
C25 H25 1.05(7) . ?
C26 C27 1.537(8) . ?
C27 C273 1.528(10) . ?
C27 C272 1.534(10) . ?
C27 C271 1.547(10) . ?
C28 C281 1.508(10) . ?
C28 C282 1.529(9) . ?
C28 C283 1.539(10) . ?
C31 C32 1.379(9) . ?
C31 C39 1.430(8) . ?
C31 C41 1.491(8) . ?
C32 C33 1.424(9) . ?
C33 C34 1.362(10) . ?
C33 H33 0.91(6) . ?
C34 C310 1.416(10) . ?
C34 H34 0.98(7) . ?
C35 C36 1.352(11) . ?
C35 C310 1.415(9) . ?
C35 H35 0.93(9) . ?
C36 C37 1.408(11) . ?
C36 H36 0.85(9) . ?
C37 C38 1.378(9) . ?
C37 H37 0.94(7) . ?
C38 C39 1.414(9) . ?
C38 H38 0.94(6) . ?
C39 C310 1.433(8) . ?
C41 C42 1.385(8) . ?
C41 C49 1.431(8) . ?
C42 C43 1.409(9) . ?
C43 C44 1.370(10) . ?
C43 H43 0.92(7) . ?
C44 C410 1.411(9) . ?
C44 H44 1.01(9) . ?
C45 C46 1.350(10) . ?
C45 C410 1.422(9) . ?
C45 H45 0.81(8) . ?
C46 C47 1.397(11) . ?
C46 H46 0.91(8) . ?
C47 C48 1.371(10) . ?
C47 H47 0.93(8) . ?
C48 C49 1.425(9) . ?
C48 H48 0.89(7) . ?
C49 C410 1.419(8) . ?
C171 H17A 0.9800 . ?
C171 H17B 0.9800 . ?
C171 H17C 0.9800 . ?
C172 H17D 0.9800 . ?
C172 H17E 0.9800 . ?
C172 H17F 0.9800 . ?
C173 H17G 0.9800 . ?
C173 H17H 0.9800 . ?
C173 H17I 0.9800 . ?
C181 H18A 0.9800 . ?
C181 H18B 0.9800 . ?
C181 H18C 0.9800 . ?
C182 H18D 0.9800 . ?
C182 H18E 0.9800 . ?
C182 H18F 0.9800 . ?
C183 H18G 0.9800 . ?
C183 H18H 0.9800 . ?
C183 H18I 0.9800 . ?
C271 H27A 0.9800 . ?
C271 H27B 0.9800 . ?
C271 H27C 0.9800 . ?
C272 H27D 0.9800 . ?
C272 H27E 0.9800 . ?
C272 H27F 0.9800 . ?
C273 H27G 0.9800 . ?
C273 H27H 0.9800 . ?
C273 H27I 0.9800 . ?
C281 H28A 0.9800 . ?
C281 H28B 0.9800 . ?
C281 H28C 0.9800 . ?
C282 H28D 0.9800 . ?
C282 H28E 0.9800 . ?
C282 H28F 0.9800 . ?
C283 H28G 0.9800 . ?
C283 H28H 0.9800 . ?
C283 H28I 0.9800 . ?
C51 C57 1.38(2) . ?
C51 C52 1.41(2) . ?
C51 C56 1.42(2) . ?
C52 C53 1.46(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.41(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.42(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.48(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
O6 C6 1.401(16) . ?
O6 H6 0.8400 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
