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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/90/1559057.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_1559057
loop_
_publ_author_name
'Zhu, Zhou-Hao'
'Ding, Yi-Xuan'
'Wu, Bo'
'Zhou, Yong-Gui'
_publ_section_title
;
 Design and Synthesis of Chiral and Regenerable [2.2]Paracyclophane-Based
 NAD(P)H Models and Application in Biomimetic Reduction of Flavonoids
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04188B
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C29 H28 O4'
_chemical_formula_weight         440.51
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-05-27 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.433(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7052(7)
_cell_length_b                   16.6173(11)
_cell_length_c                   15.6111(10)
_cell_measurement_reflns_used    5787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      125.891
_cell_measurement_theta_min      5.932
_cell_volume                     2402.0(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1263
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34394
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.490
_diffrn_reflns_theta_min         2.967
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       0.0028(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         9016
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1051P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2229
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                5353
_reflns_number_total             9016
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04188b2.cif
_cod_data_source_block           cu_d8v19496_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559057
_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   0.905
_shelx_estimated_absorpt_t_max   0.939
_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 0.5138(6) 0.4056(4) 0.4378(3) 0.0965(16) Uani 1 1 d . . . . .
O2 O 0.8574(5) 0.5239(3) 0.6042(3) 0.0782(13) Uani 1 1 d . . . . .
O3 O 0.8498(8) 0.2838(4) 0.5733(4) 0.112(2) Uani 1 1 d . . . . .
O4 O 0.8633(6) 0.3872(4) 0.4883(4) 0.0932(16) Uani 1 1 d . . . . .
C1 C 0.7739(8) 0.5610(4) 0.5281(4) 0.0734(18) Uani 1 1 d . . . . .
C2 C 0.8173(11) 0.6344(5) 0.5050(5) 0.095(3) Uani 1 1 d . . . . .
H2 H 0.9034 0.6569 0.5403 0.114 Uiso 1 1 calc R U . . .
C3 C 0.7360(14) 0.6748(6) 0.4311(6) 0.111(3) Uani 1 1 d . . . . .
H3 H 0.7673 0.7243 0.4162 0.133 Uiso 1 1 calc R U . . .
C4 C 0.6062(12) 0.6424(6) 0.3778(6) 0.099(3) Uani 1 1 d . . . . .
H4 H 0.5479 0.6711 0.3292 0.119 Uiso 1 1 calc R U . . .
C5 C 0.5666(9) 0.5688(5) 0.3979(5) 0.086(2) Uani 1 1 d . . . . .
H5 H 0.4823 0.5461 0.3607 0.103 Uiso 1 1 calc R U . . .
C6 C 0.6494(8) 0.5245(4) 0.4740(4) 0.0697(17) Uani 1 1 d . . . . .
C7 C 0.6112(7) 0.4424(5) 0.4893(4) 0.0717(18) Uani 1 1 d . . . . .
C8 C 0.7065(7) 0.4012(4) 0.5760(4) 0.0629(15) Uani 1 1 d . . . . .
C9 C 0.7814(7) 0.4676(4) 0.6432(4) 0.0661(16) Uani 1 1 d . . . . .
H9 H 0.7051 0.4977 0.6585 0.079 Uiso 1 1 calc R U . . .
C10 C 0.8849(7) 0.4384(4) 0.7302(4) 0.0654(16) Uani 1 1 d . . . . .
C11 C 1.0252(7) 0.4123(5) 0.7368(5) 0.0755(19) Uani 1 1 d . . . . .
H11 H 1.0563 0.4140 0.6859 0.091 Uiso 1 1 calc R U . . .
C12 C 1.1172(7) 0.3845(5) 0.8153(5) 0.0788(19) Uani 1 1 d . . . . .
H12 H 1.2099 0.3681 0.8176 0.095 Uiso 1 1 calc R U . . .
C13 C 1.0723(7) 0.3804(4) 0.8931(4) 0.0711(17) Uani 1 1 d . . . . .
C14 C 1.1631(9) 0.3512(6) 0.9765(5) 0.092(2) Uani 1 1 d . . . . .
H14 H 1.2562 0.3339 0.9813 0.110 Uiso 1 1 calc R U . . .
C15 C 1.1134(11) 0.3487(7) 1.0495(6) 0.112(3) Uani 1 1 d . . . . .
H15 H 1.1723 0.3282 1.1035 0.135 Uiso 1 1 calc R U . . .
C16 C 0.9780(12) 0.3760(8) 1.0445(6) 0.124(4) Uani 1 1 d . . . . .
H16 H 0.9473 0.3749 1.0955 0.149 Uiso 1 1 calc R U . . .
C17 C 0.8878(10) 0.4048(7) 0.9662(5) 0.101(3) Uani 1 1 d . . . . .
H17 H 0.7960 0.4229 0.9638 0.121 Uiso 1 1 calc R U . . .
C18 C 0.9338(8) 0.4074(5) 0.8885(4) 0.0708(17) Uani 1 1 d . . . . .
C19 C 0.8401(7) 0.4363(4) 0.8055(4) 0.0684(17) Uani 1 1 d . . . . .
H19 H 0.7478 0.4540 0.8024 0.082 Uiso 1 1 calc R U . . .
C20 C 0.6146(9) 0.3458(5) 0.6152(5) 0.0782(19) Uani 1 1 d . . . . .
H20A H 0.5695 0.3057 0.5704 0.094 Uiso 1 1 calc R U . . .
H20B H 0.6779 0.3177 0.6664 0.094 Uiso 1 1 calc R U . . .
C21 C 0.5001(9) 0.3867(6) 0.6441(6) 0.098(3) Uani 1 1 d . . . . .
H21 H 0.4468 0.4261 0.6061 0.117 Uiso 1 1 calc R U . . .
C22 C 0.4672(12) 0.3728(7) 0.7177(7) 0.123(4) Uani 1 1 d . . . . .
H22A H 0.5175 0.3340 0.7579 0.147 Uiso 1 1 calc R U . . .
H22B H 0.3933 0.4017 0.7301 0.147 Uiso 1 1 calc R U . . .
C23 C 0.8156(7) 0.3493(5) 0.5482(4) 0.0663(16) Uani 1 1 d . . . . .
C24 C 0.9622(8) 0.3465(5) 0.4477(5) 0.081(2) Uani 1 1 d . . . . .
H24 H 0.9978 0.2963 0.4797 0.097 Uiso 1 1 calc R U . . .
C25 C 0.8807(11) 0.3292(7) 0.3519(6) 0.111(3) Uani 1 1 d . . . . .
H25A H 0.8067 0.2893 0.3496 0.133 Uiso 1 1 calc R U . . .
H25B H 0.8333 0.3780 0.3235 0.133 Uiso 1 1 calc R U . . .
C26 C 0.9788(17) 0.2990(9) 0.3018(7) 0.145(5) Uani 1 1 d . . . . .
H26A H 0.9246 0.2919 0.2391 0.174 Uiso 1 1 calc R U . . .
H26B H 1.0172 0.2470 0.3257 0.174 Uiso 1 1 calc R U . . .
C27 C 1.1029(16) 0.3570(10) 0.3092(8) 0.154(6) Uani 1 1 d . . . . .
H27A H 1.1685 0.3346 0.2792 0.185 Uiso 1 1 calc R U . . .
H27B H 1.0659 0.4076 0.2804 0.185 Uiso 1 1 calc R U . . .
C28 C 1.1802(13) 0.3708(12) 0.4049(10) 0.178(7) Uani 1 1 d . . . . .
H28A H 1.2583 0.4086 0.4096 0.213 Uiso 1 1 calc R U . . .
H28B H 1.2223 0.3205 0.4320 0.213 Uiso 1 1 calc R U . . .
C29 C 1.0834(10) 0.4032(9) 0.4557(7) 0.132(4) Uani 1 1 d . . . . .
H29A H 1.1378 0.4100 0.5185 0.158 Uiso 1 1 calc R U . . .
H29B H 1.0459 0.4553 0.4318 0.158 Uiso 1 1 calc R U . . .
O5 O 0.3759(6) 0.5806(3) 0.1803(3) 0.0898(16) Uani 1 1 d . . . . .
O6 O 0.5463(5) 0.4687(3) 0.0024(3) 0.0649(11) Uani 1 1 d . . . . .
O7 O 0.5774(6) 0.7143(4) 0.0753(4) 0.0993(17) Uani 1 1 d . . . . .
O8 O 0.6828(4) 0.5961(3) 0.1228(3) 0.0743(12) Uani 1 1 d . . . . .
C30 C 0.5316(7) 0.4277(4) 0.0747(4) 0.0615(15) Uani 1 1 d . . . . .
C31 C 0.5837(8) 0.3503(4) 0.0871(5) 0.0732(18) Uani 1 1 d . . . . .
H31 H 0.6279 0.3280 0.0474 0.088 Uiso 1 1 calc R U . . .
C32 C 0.5701(10) 0.3058(5) 0.1587(5) 0.085(2) Uani 1 1 d . . . . .
H32 H 0.6031 0.2530 0.1663 0.103 Uiso 1 1 calc R U . . .
C33 C 0.5082(10) 0.3390(5) 0.2188(5) 0.086(2) Uani 1 1 d . . . . .
H33 H 0.5019 0.3091 0.2678 0.103 Uiso 1 1 calc R U . . .
C34 C 0.4561(8) 0.4153(5) 0.2070(4) 0.0736(18) Uani 1 1 d . . . . .
H34 H 0.4117 0.4365 0.2471 0.088 Uiso 1 1 calc R U . . .
C35 C 0.4683(7) 0.4629(4) 0.1348(4) 0.0609(15) Uani 1 1 d . . . . .
C36 C 0.4207(7) 0.5459(4) 0.1253(4) 0.0625(15) Uani 1 1 d . . . . .
C37 C 0.4345(6) 0.5921(4) 0.0431(4) 0.0577(14) Uani 1 1 d . . . . .
C38 C 0.4403(7) 0.5312(4) -0.0302(3) 0.0596(14) Uani 1 1 d . . . . .
H38 H 0.3458 0.5048 -0.0502 0.072 Uiso 1 1 calc R U . . .
C39 C 0.4687(7) 0.5657(4) -0.1124(4) 0.0616(15) Uani 1 1 d . . . . .
C40 C 0.6040(8) 0.5949(5) -0.1112(4) 0.0767(19) Uani 1 1 d . . . . .
H40 H 0.6787 0.5944 -0.0574 0.092 Uiso 1 1 calc R U . . .
C41 C 0.6298(9) 0.6237(5) -0.1858(5) 0.083(2) Uani 1 1 d . . . . .
H41 H 0.7213 0.6424 -0.1832 0.100 Uiso 1 1 calc R U . . .
C42 C 0.5163(10) 0.6255(5) -0.2689(4) 0.080(2) Uani 1 1 d . . . . .
C43 C 0.5382(12) 0.6558(5) -0.3491(5) 0.099(3) Uani 1 1 d . . . . .
H43 H 0.6280 0.6755 -0.3489 0.119 Uiso 1 1 calc R U . . .
C44 C 0.424(2) 0.6556(7) -0.4272(6) 0.131(5) Uani 1 1 d . . . . .
H44 H 0.4372 0.6757 -0.4797 0.157 Uiso 1 1 calc R U . . .
C45 C 0.2903(18) 0.6258(8) -0.4286(6) 0.130(4) Uani 1 1 d . . . . .
H45 H 0.2150 0.6259 -0.4820 0.156 Uiso 1 1 calc R U . . .
C46 C 0.2681(11) 0.5972(6) -0.3545(4) 0.103(3) Uani 1 1 d . . . . .
H46 H 0.1776 0.5770 -0.3569 0.124 Uiso 1 1 calc R U . . .
C47 C 0.3803(9) 0.5968(5) -0.2717(4) 0.0759(19) Uani 1 1 d . . . . .
C48 C 0.3576(8) 0.5666(4) -0.1922(4) 0.0684(16) Uani 1 1 d . . . . .
H48 H 0.2670 0.5472 -0.1937 0.082 Uiso 1 1 calc R U . . .
C49 C 0.3070(7) 0.6490(4) 0.0075(4) 0.0662(16) Uani 1 1 d . . . . .
H49A H 0.3055 0.6869 0.0545 0.079 Uiso 1 1 calc R U . . .
H49B H 0.3212 0.6795 -0.0422 0.079 Uiso 1 1 calc R U . . .
C50 C 0.1642(8) 0.6076(5) -0.0236(5) 0.081(2) Uani 1 1 d . . . . .
C51 C 0.0652(10) 0.6212(7) -0.0984(7) 0.119(3) Uani 1 1 d . . . . .
H51A H 0.0802 0.6596 -0.1380 0.143 Uiso 1 1 calc R U . . .
H51B H -0.0211 0.5926 -0.1127 0.143 Uiso 1 1 calc R U . . .
C52 C 0.5714(7) 0.6423(4) 0.0796(4) 0.0661(16) Uani 1 1 d . . . . .
C53 C 0.8159(7) 0.6334(5) 0.1772(4) 0.0720(17) Uani 1 1 d . . . . .
H53 H 0.7935 0.6856 0.1989 0.086 Uiso 1 1 calc R U . . .
C54 C 0.9218(8) 0.6449(6) 0.1268(5) 0.088(2) Uani 1 1 d . . . . .
H54A H 0.8829 0.6822 0.0777 0.106 Uiso 1 1 calc R U . . .
H54B H 0.9390 0.5939 0.1015 0.106 Uiso 1 1 calc R U . . .
C55 C 1.0637(9) 0.6776(6) 0.1883(6) 0.096(2) Uani 1 1 d . . . . .
H55A H 1.1329 0.6825 0.1549 0.115 Uiso 1 1 calc R U . . .
H55B H 1.0478 0.7308 0.2092 0.115 Uiso 1 1 calc R U . . .
C56 C 1.1242(10) 0.6238(6) 0.2673(7) 0.107(3) Uani 1 1 d . . . . .
H56A H 1.1504 0.5725 0.2470 0.128 Uiso 1 1 calc R U . . .
H56B H 1.2110 0.6479 0.3071 0.128 Uiso 1 1 calc R U . . .
C57 C 1.0177(10) 0.6106(8) 0.3170(6) 0.121(4) Uani 1 1 d . . . . .
H57A H 0.9998 0.6612 0.3430 0.145 Uiso 1 1 calc R U . . .
H57B H 1.0573 0.5731 0.3658 0.145 Uiso 1 1 calc R U . . .
C58 C 0.8767(9) 0.5779(6) 0.2565(5) 0.097(2) Uani 1 1 d . . . . .
H58A H 0.8079 0.5727 0.2902 0.116 Uiso 1 1 calc R U . . .
H58B H 0.8925 0.5249 0.2352 0.116 Uiso 1 1 calc R U . . .
H50 H 0.146(10) 0.564(7) 0.014(6) 0.13(3) 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C1 O2 C9 114.6(5) . . ?
C23 O4 C24 120.0(6) . . ?
O2 C1 C2 118.6(7) . . ?
O2 C1 C6 120.8(6) . . ?
C2 C1 C6 120.5(7) . . ?
C3 C2 C1 120.9(9) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.4(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.8(9) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.4(8) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 116.8(7) . . ?
C1 C6 C7 121.9(6) . . ?
C5 C6 C7 121.0(7) . . ?
O1 C7 C6 123.7(7) . . ?
O1 C7 C8 120.0(7) . . ?
C6 C7 C8 116.3(6) . . ?
C23 C8 C20 108.1(6) . . ?
C23 C8 C9 111.8(5) . . ?
C20 C8 C9 111.7(5) . . ?
C23 C8 C7 106.5(5) . . ?
C20 C8 C7 110.3(6) . . ?
C9 C8 C7 108.3(5) . . ?
O2 C9 C10 107.7(5) . . ?
O2 C9 C8 112.0(5) . . ?
C10 C9 C8 115.7(6) . . ?
O2 C9 H9 107.0 . . ?
C10 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C19 C10 C11 118.7(6) . . ?
C19 C10 C9 119.0(6) . . ?
C11 C10 C9 122.3(6) . . ?
C12 C11 C10 122.0(6) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C18 C13 C12 118.8(6) . . ?
C18 C13 C14 118.7(7) . . ?
C12 C13 C14 122.6(7) . . ?
C15 C14 C13 119.8(8) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.0(8) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 121.1(9) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.9(8) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 119.5(6) . . ?
C13 C18 C19 119.7(6) . . ?
C17 C18 C19 120.7(6) . . ?
C10 C19 C18 120.6(6) . . ?
C10 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C8 115.2(7) . . ?
C21 C20 H20A 108.5 . . ?
C8 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C8 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C20 126.3(10) . . ?
C22 C21 H21 116.9 . . ?
C20 C21 H21 116.9 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
O3 C23 O4 123.8(7) . . ?
O3 C23 C8 125.5(6) . . ?
O4 C23 C8 110.6(6) . . ?
O4 C24 C29 106.0(8) . . ?
O4 C24 C25 107.6(7) . . ?
C29 C24 C25 112.1(8) . . ?
O4 C24 H24 110.3 . . ?
C29 C24 H24 110.3 . . ?
C25 C24 H24 110.3 . . ?
C26 C25 C24 111.1(9) . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 111.3(11) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C28 C27 C26 109.1(10) . . ?
C28 C27 H27A 109.9 . . ?
C26 C27 H27A 109.9 . . ?
C28 C27 H27B 109.9 . . ?
C26 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
C27 C28 C29 112.5(10) . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
C29 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C24 C29 C28 109.5(11) . . ?
C24 C29 H29A 109.8 . . ?
C28 C29 H29A 109.8 . . ?
C24 C29 H29B 109.8 . . ?
C28 C29 H29B 109.8 . . ?
H29A C29 H29B 108.2 . . ?
C30 O6 C38 114.3(5) . . ?
C52 O8 C53 119.6(6) . . ?
O6 C30 C31 117.4(6) . . ?
O6 C30 C35 121.6(5) . . ?
C31 C30 C35 121.0(6) . . ?
C30 C31 C32 119.7(7) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.4(7) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.3(7) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 121.0(7) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C30 C35 C34 117.5(6) . . ?
C30 C35 C36 121.4(5) . . ?
C34 C35 C36 121.0(6) . . ?
O5 C36 C35 123.2(6) . . ?
O5 C36 C37 119.5(6) . . ?
C35 C36 C37 117.2(5) . . ?
C49 C37 C52 108.5(5) . . ?
C49 C37 C36 110.5(5) . . ?
C52 C37 C36 104.2(5) . . ?
C49 C37 C38 110.1(5) . . ?
C52 C37 C38 114.5(5) . . ?
C36 C37 C38 108.9(5) . . ?
O6 C38 C39 106.4(5) . . ?
O6 C38 C37 113.1(4) . . ?
C39 C38 C37 116.0(5) . . ?
O6 C38 H38 106.9 . . ?
C39 C38 H38 106.9 . . ?
C37 C38 H38 107.0 . . ?
C48 C39 C40 119.1(5) . . ?
C48 C39 C38 118.7(6) . . ?
C40 C39 C38 122.2(5) . . ?
C41 C40 C39 121.9(7) . . ?
C41 C40 H40 119.1 . . ?
C39 C40 H40 119.1 . . ?
C40 C41 C42 119.9(7) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C47 C42 C43 118.9(8) . . ?
C47 C42 C41 119.2(6) . . ?
C43 C42 C41 121.9(9) . . ?
C44 C43 C42 118.9(11) . . ?
C44 C43 H43 120.5 . . ?
C42 C43 H43 120.5 . . ?
C43 C44 C45 121.1(9) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.5 . . ?
C46 C45 C44 120.8(11) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C47 121.0(11) . . ?
C45 C46 H46 119.5 . . ?
C47 C46 H46 119.5 . . ?
C42 C47 C48 119.3(6) . . ?
C42 C47 C46 119.3(7) . . ?
C48 C47 C46 121.5(8) . . ?
C39 C48 C47 120.6(7) . . ?
C39 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C50 C49 C37 114.0(6) . . ?
C50 C49 H49A 108.8 . . ?
C37 C49 H49A 108.8 . . ?
C50 C49 H49B 108.8 . . ?
C37 C49 H49B 108.8 . . ?
H49A C49 H49B 107.7 . . ?
C51 C50 C49 125.4(9) . . ?
C51 C50 H50 116(6) . . ?
C49 C50 H50 118(6) . . ?
C50 C51 H51A 120.0 . . ?
C50 C51 H51B 120.0 . . ?
H51A C51 H51B 120.0 . . ?
O7 C52 O8 123.8(6) . . ?
O7 C52 C37 125.1(6) . . ?
O8 C52 C37 110.9(6) . . ?
O8 C53 C54 112.4(6) . . ?
O8 C53 C58 106.2(6) . . ?
C54 C53 C58 110.5(6) . . ?
O8 C53 H53 109.2 . . ?
C54 C53 H53 109.2 . . ?
C58 C53 H53 109.2 . . ?
C53 C54 C55 110.5(6) . . ?
C53 C54 H54A 109.5 . . ?
C55 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C55 C54 H54B 109.5 . . ?
H54A C54 H54B 108.1 . . ?
C56 C55 C54 111.4(8) . . ?
C56 C55 H55A 109.3 . . ?
C54 C55 H55A 109.4 . . ?
C56 C55 H55B 109.4 . . ?
C54 C55 H55B 109.3 . . ?
H55A C55 H55B 108.0 . . ?
C57 C56 C55 110.9(8) . . ?
C57 C56 H56A 109.5 . . ?
C55 C56 H56A 109.5 . . ?
C57 C56 H56B 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 108.0 . . ?
C56 C57 C58 111.6(7) . . ?
C56 C57 H57A 109.3 . . ?
C58 C57 H57A 109.3 . . ?
C56 C57 H57B 109.3 . . ?
C58 C57 H57B 109.3 . . ?
H57A C57 H57B 108.0 . . ?
C57 C58 C53 110.5(7) . . ?
C57 C58 H58A 109.5 . . ?
C53 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C53 C58 H58B 109.5 . . ?
H58A C58 H58B 108.1 . . ?
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 C7 1.208(8) . ?
O2 C1 1.368(8) . ?
O2 C9 1.435(8) . ?
O3 C23 1.170(9) . ?
O4 C23 1.320(8) . ?
O4 C24 1.466(8) . ?
C1 C2 1.374(10) . ?
C1 C6 1.389(9) . ?
C2 C3 1.363(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.346(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.452(11) . ?
C7 C8 1.551(10) . ?
C8 C23 1.526(9) . ?
C8 C20 1.531(9) . ?
C8 C9 1.545(9) . ?
C9 C10 1.508(9) . ?
C9 H9 0.9800 . ?
C10 C19 1.370(9) . ?
C10 C11 1.403(10) . ?
C11 C12 1.364(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.410(9) . ?
C12 H12 0.9300 . ?
C13 C18 1.398(10) . ?
C13 C14 1.420(10) . ?
C14 C15 1.366(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.359(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.426(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.483(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.302(11) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9300 . ?
C22 H22B 0.9300 . ?
C24 C29 1.482(14) . ?
C24 C25 1.495(11) . ?
C24 H24 0.9800 . ?
C25 C26 1.489(15) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.52(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.475(18) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.500(16) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
O5 C36 1.218(7) . ?
O6 C30 1.362(7) . ?
O6 C38 1.442(7) . ?
O7 C52 1.200(8) . ?
O8 C52 1.334(8) . ?
O8 C53 1.454(7) . ?
C30 C31 1.375(9) . ?
C30 C35 1.394(9) . ?
C31 C32 1.379(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.371(11) . ?
C32 H32 0.9300 . ?
C33 C34 1.357(11) . ?
C33 H33 0.9300 . ?
C34 C35 1.410(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.449(9) . ?
C36 C37 1.535(8) . ?
C37 C49 1.523(8) . ?
C37 C52 1.527(9) . ?
C37 C38 1.541(8) . ?
C38 C39 1.505(8) . ?
C38 H38 0.9800 . ?
C39 C48 1.383(8) . ?
C39 C40 1.395(10) . ?
C40 C41 1.351(9) . ?
C40 H40 0.9300 . ?
C41 C42 1.428(11) . ?
C41 H41 0.9300 . ?
C42 C47 1.392(11) . ?
C42 C43 1.424(10) . ?
C43 C44 1.380(17) . ?
C43 H43 0.9300 . ?
C44 C45 1.383(17) . ?
C44 H44 0.9300 . ?
C45 C46 1.325(14) . ?
C45 H45 0.9300 . ?
C46 C47 1.419(10) . ?
C46 H46 0.9300 . ?
C47 C48 1.415(9) . ?
C48 H48 0.9300 . ?
C49 C50 1.493(10) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.291(10) . ?
C50 H50 0.98(10) . ?
C51 H51A 0.9300 . ?
C51 H51B 0.9300 . ?
C53 C54 1.482(10) . ?
C53 C58 1.514(11) . ?
C53 H53 0.9800 . ?
C54 C55 1.524(11) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C56 1.493(13) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C56 C57 1.483(14) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C57 C58 1.512(11) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
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
C9 O2 C1 C2 155.8(7) . . . . ?
C9 O2 C1 C6 -25.6(9) . . . . ?
O2 C1 C2 C3 -178.3(8) . . . . ?
C6 C1 C2 C3 3.1(13) . . . . ?
C1 C2 C3 C4 0.5(15) . . . . ?
C2 C3 C4 C5 -3.5(14) . . . . ?
C3 C4 C5 C6 2.9(13) . . . . ?
O2 C1 C6 C5 177.9(6) . . . . ?
C2 C1 C6 C5 -3.5(10) . . . . ?
O2 C1 C6 C7 -7.4(10) . . . . ?
C2 C1 C6 C7 171.2(7) . . . . ?
C4 C5 C6 C1 0.5(11) . . . . ?
C4 C5 C6 C7 -174.3(7) . . . . ?
C1 C6 C7 O1 -170.8(7) . . . . ?
C5 C6 C7 O1 3.7(11) . . . . ?
C1 C6 C7 C8 7.3(9) . . . . ?
C5 C6 C7 C8 -178.2(6) . . . . ?
O1 C7 C8 C23 79.8(8) . . . . ?
C6 C7 C8 C23 -98.4(7) . . . . ?
O1 C7 C8 C20 -37.3(8) . . . . ?
C6 C7 C8 C20 144.5(6) . . . . ?
O1 C7 C8 C9 -159.8(6) . . . . ?
C6 C7 C8 C9 22.0(7) . . . . ?
C1 O2 C9 C10 -174.8(6) . . . . ?
C1 O2 C9 C8 57.0(7) . . . . ?
C23 C8 C9 O2 63.8(7) . . . . ?
C20 C8 C9 O2 -174.9(6) . . . . ?
C7 C8 C9 O2 -53.2(7) . . . . ?
C23 C8 C9 C10 -60.1(7) . . . . ?
C20 C8 C9 C10 61.3(8) . . . . ?
C7 C8 C9 C10 -177.1(5) . . . . ?
O2 C9 C10 C19 133.1(6) . . . . ?
C8 C9 C10 C19 -100.9(7) . . . . ?
O2 C9 C10 C11 -47.8(8) . . . . ?
C8 C9 C10 C11 78.3(8) . . . . ?
C19 C10 C11 C12 0.5(11) . . . . ?
C9 C10 C11 C12 -178.6(7) . . . . ?
C10 C11 C12 C13 0.7(12) . . . . ?
C11 C12 C13 C18 -1.7(11) . . . . ?
C11 C12 C13 C14 179.4(8) . . . . ?
C18 C13 C14 C15 1.1(12) . . . . ?
C12 C13 C14 C15 -179.9(8) . . . . ?
C13 C14 C15 C16 -1.8(16) . . . . ?
C14 C15 C16 C17 1.5(19) . . . . ?
C15 C16 C17 C18 -0.4(18) . . . . ?
C12 C13 C18 C17 -179.1(8) . . . . ?
C14 C13 C18 C17 -0.1(12) . . . . ?
C12 C13 C18 C19 1.5(11) . . . . ?
C14 C13 C18 C19 -179.5(7) . . . . ?
C16 C17 C18 C13 -0.2(15) . . . . ?
C16 C17 C18 C19 179.1(10) . . . . ?
C11 C10 C19 C18 -0.6(11) . . . . ?
C9 C10 C19 C18 178.5(7) . . . . ?
C13 C18 C19 C10 -0.4(11) . . . . ?
C17 C18 C19 C10 -179.8(8) . . . . ?
C23 C8 C20 C21 -178.8(6) . . . . ?
C9 C8 C20 C21 57.7(9) . . . . ?
C7 C8 C20 C21 -62.7(8) . . . . ?
C8 C20 C21 C22 -137.0(9) . . . . ?
C24 O4 C23 O3 1.6(11) . . . . ?
C24 O4 C23 C8 -176.1(6) . . . . ?
C20 C8 C23 O3 -18.7(10) . . . . ?
C9 C8 C23 O3 104.7(9) . . . . ?
C7 C8 C23 O3 -137.2(8) . . . . ?
C20 C8 C23 O4 158.9(6) . . . . ?
C9 C8 C23 O4 -77.7(6) . . . . ?
C7 C8 C23 O4 40.4(7) . . . . ?
C23 O4 C24 C29 -130.7(8) . . . . ?
C23 O4 C24 C25 109.2(8) . . . . ?
O4 C24 C25 C26 171.5(10) . . . . ?
C29 C24 C25 C26 55.3(13) . . . . ?
C24 C25 C26 C27 -55.1(13) . . . . ?
C25 C26 C27 C28 56.1(15) . . . . ?
C26 C27 C28 C29 -57.8(18) . . . . ?
O4 C24 C29 C28 -172.5(9) . . . . ?
C25 C24 C29 C28 -55.4(12) . . . . ?
C27 C28 C29 C24 57.9(18) . . . . ?
C38 O6 C30 C31 154.0(6) . . . . ?
C38 O6 C30 C35 -27.0(8) . . . . ?
O6 C30 C31 C32 -179.3(7) . . . . ?
C35 C30 C31 C32 1.7(10) . . . . ?
C30 C31 C32 C33 -1.6(12) . . . . ?
C31 C32 C33 C34 1.8(13) . . . . ?
C32 C33 C34 C35 -2.0(12) . . . . ?
O6 C30 C35 C34 179.2(6) . . . . ?
C31 C30 C35 C34 -1.8(9) . . . . ?
O6 C30 C35 C36 -2.6(9) . . . . ?
C31 C30 C35 C36 176.3(6) . . . . ?
C33 C34 C35 C30 2.0(10) . . . . ?
C33 C34 C35 C36 -176.2(7) . . . . ?
C30 C35 C36 O5 -173.8(6) . . . . ?
C34 C35 C36 O5 4.2(10) . . . . ?
C30 C35 C36 C37 3.6(9) . . . . ?
C34 C35 C36 C37 -178.3(5) . . . . ?
O5 C36 C37 C49 -39.3(8) . . . . ?
C35 C36 C37 C49 143.2(6) . . . . ?
O5 C36 C37 C52 77.2(7) . . . . ?
C35 C36 C37 C52 -100.4(6) . . . . ?
O5 C36 C37 C38 -160.3(6) . . . . ?
C35 C36 C37 C38 22.2(7) . . . . ?
C30 O6 C38 C39 -176.7(5) . . . . ?
C30 O6 C38 C37 54.8(7) . . . . ?
C49 C37 C38 O6 -172.1(5) . . . . ?
C52 C37 C38 O6 65.3(7) . . . . ?
C36 C37 C38 O6 -50.8(6) . . . . ?
C49 C37 C38 C39 64.6(7) . . . . ?
C52 C37 C38 C39 -58.0(7) . . . . ?
C36 C37 C38 C39 -174.1(5) . . . . ?
O6 C38 C39 C48 124.1(6) . . . . ?
C37 C38 C39 C48 -109.2(7) . . . . ?
O6 C38 C39 C40 -54.2(8) . . . . ?
C37 C38 C39 C40 72.5(8) . . . . ?
C48 C39 C40 C41 -0.2(11) . . . . ?
C38 C39 C40 C41 178.1(7) . . . . ?
C39 C40 C41 C42 0.5(12) . . . . ?
C40 C41 C42 C47 -0.4(11) . . . . ?
C40 C41 C42 C43 179.6(7) . . . . ?
C47 C42 C43 C44 -0.2(11) . . . . ?
C41 C42 C43 C44 179.8(8) . . . . ?
C42 C43 C44 C45 -0.6(15) . . . . ?
C43 C44 C45 C46 0.5(18) . . . . ?
C44 C45 C46 C47 0.5(17) . . . . ?
C43 C42 C47 C48 -179.9(7) . . . . ?
C41 C42 C47 C48 0.1(11) . . . . ?
C43 C42 C47 C46 1.1(11) . . . . ?
C41 C42 C47 C46 -178.9(7) . . . . ?
C45 C46 C47 C42 -1.3(13) . . . . ?
C45 C46 C47 C48 179.7(9) . . . . ?
C40 C39 C48 C47 -0.1(10) . . . . ?
C38 C39 C48 C47 -178.5(6) . . . . ?
C42 C47 C48 C39 0.2(10) . . . . ?
C46 C47 C48 C39 179.1(7) . . . . ?
C52 C37 C49 C50 -175.3(6) . . . . ?
C36 C37 C49 C50 -61.6(7) . . . . ?
C38 C37 C49 C50 58.7(7) . . . . ?
C37 C49 C50 C51 -132.8(9) . . . . ?
C53 O8 C52 O7 7.5(10) . . . . ?
C53 O8 C52 C37 -168.2(5) . . . . ?
C49 C37 C52 O7 -4.3(9) . . . . ?
C36 C37 C52 O7 -122.1(8) . . . . ?
C38 C37 C52 O7 119.1(8) . . . . ?
C49 C37 C52 O8 171.3(5) . . . . ?
C36 C37 C52 O8 53.6(6) . . . . ?
C38 C37 C52 O8 -65.2(7) . . . . ?
C52 O8 C53 C54 -94.0(8) . . . . ?
C52 O8 C53 C58 145.1(6) . . . . ?
O8 C53 C54 C55 -175.3(7) . . . . ?
C58 C53 C54 C55 -56.9(9) . . . . ?
C53 C54 C55 C56 56.6(10) . . . . ?
C54 C55 C56 C57 -55.5(11) . . . . ?
C55 C56 C57 C58 55.6(12) . . . . ?
C56 C57 C58 C53 -56.2(12) . . . . ?
O8 C53 C58 C57 179.0(7) . . . . ?
C54 C53 C58 C57 56.9(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306733
