#------------------------------------------------------------------------------
#$Date: 2025-09-02 01:13:42 +0300 (Tue, 02 Sep 2025) $
#$Revision: 301960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/55/1575583.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_1575583
loop_
_publ_author_name
'Zhong, Guofu'
'Fan, Lin'
'Wang, Pengyang'
'He, Chang'
'Chen, Xiaoyu'
'Dai, Linlong'
'Xiong, Daokai'
_publ_section_title
;
 Regiodivergent Lewis Acid Catalysis of Bicyclo[1.1.0]butanes with
 2-Naphthols
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC05468K
_journal_year                    2025
_chemical_formula_moiety         'C27 H20 O'
_chemical_formula_sum            'C27 H20 O'
_chemical_formula_weight         360.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-14 deposited with the CCDC.	2025-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.794(4)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   33.532(4)
_cell_length_b                   9.7242(12)
_cell_length_c                   23.877(2)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      22.83
_cell_measurement_theta_min      2.18
_cell_volume                     7781.8(15)
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2024)'
_computing_data_collection       'APEX6 V2024.9-0 (Bruker, 2024)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            88660
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.064
_diffrn_source                   TXS
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1462 before and 0.0780 after correction.
The Ratio of minimum to maximum transmission is 0.9493.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             3040
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00104(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0309P)²+5.9668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5171
_reflns_number_total             7124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc05468k2.cif
_cod_data_source_block           mo_250112lu_lgpz0655399_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               1575583
_shelx_shelxl_version_number     2019/3
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C35(H35A,H35B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
 C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53),
  C54(H54)
;
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.34624(4) 0.72450(17) 0.50865(7) 0.0699(4) Uani 1 1 d . . . . .
C1 C 0.56540(6) 0.6544(2) 0.64095(9) 0.0560(5) Uani 1 1 d . . . . .
H1 H 0.586119 0.632958 0.666264 0.067 Uiso 1 1 calc R U . . .
C2 C 0.55682(6) 0.7898(2) 0.62840(8) 0.0530(5) Uani 1 1 d . . . . .
H2 H 0.571895 0.859827 0.645057 0.064 Uiso 1 1 calc R U . . .
C3 C 0.52592(5) 0.82158(19) 0.59119(8) 0.0471(4) Uani 1 1 d . . . . .
H3 H 0.520187 0.913142 0.583077 0.057 Uiso 1 1 calc R U . . .
C4 C 0.50331(5) 0.71841(17) 0.56575(7) 0.0394(4) Uani 1 1 d . . . . .
C5 C 0.46908(5) 0.75383(17) 0.52658(7) 0.0392(4) Uani 1 1 d . . . . .
C6 C 0.47468(5) 0.78085(17) 0.46399(7) 0.0383(4) Uani 1 1 d . . . . .
C7 C 0.43641(5) 0.81132(17) 0.44452(7) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.42754(6) 0.83938(18) 0.38835(8) 0.0449(4) Uani 1 1 d . . . . .
H8 H 0.401534 0.857602 0.375821 0.054 Uiso 1 1 calc R U . . .
C9 C 0.45851(6) 0.8392(2) 0.35206(8) 0.0497(5) Uani 1 1 d . . . . .
H9 H 0.453191 0.858197 0.314384 0.060 Uiso 1 1 calc R U . . .
C10 C 0.49804(6) 0.81126(19) 0.37007(8) 0.0473(4) Uani 1 1 d . . . . .
C11 C 0.50705(5) 0.77892(17) 0.42766(7) 0.0405(4) Uani 1 1 d . . . . .
C12 C 0.54710(5) 0.74753(19) 0.44403(8) 0.0481(5) Uani 1 1 d . . . . .
H12 H 0.553256 0.723439 0.480990 0.058 Uiso 1 1 calc R U . . .
C13 C 0.57659(6) 0.7524(2) 0.40608(10) 0.0618(6) Uani 1 1 d . . . . .
H13 H 0.602679 0.731844 0.417513 0.074 Uiso 1 1 calc R U . . .
C14 C 0.56818(7) 0.7879(2) 0.35020(10) 0.0691(6) Uani 1 1 d . . . . .
H14 H 0.588684 0.792715 0.324928 0.083 Uiso 1 1 calc R U . . .
C15 C 0.53009(7) 0.8152(2) 0.33288(9) 0.0630(6) Uani 1 1 d . . . . .
H15 H 0.524867 0.837166 0.295463 0.076 Uiso 1 1 calc R U . . .
C16 C 0.41207(5) 0.79904(18) 0.49723(7) 0.0419(4) Uani 1 1 d . . . . .
C17 C 0.43007(5) 0.66444(19) 0.52237(8) 0.0465(4) Uani 1 1 d . . . . .
H17A H 0.431062 0.587860 0.496423 0.056 Uiso 1 1 calc R U . . .
H17B H 0.419504 0.637324 0.558081 0.056 Uiso 1 1 calc R U . . .
C18 C 0.44066(5) 0.87566(19) 0.54029(8) 0.0455(4) Uani 1 1 d . . . . .
H18A H 0.449691 0.965325 0.528194 0.055 Uiso 1 1 calc R U . . .
H18B H 0.431612 0.877399 0.578479 0.055 Uiso 1 1 calc R U . . .
C19 C 0.36760(5) 0.8200(2) 0.49542(7) 0.0474(5) Uani 1 1 d . . . . .
C20 C 0.35004(5) 0.9556(2) 0.47929(7) 0.0472(5) Uani 1 1 d . . . . .
C21 C 0.30858(6) 0.9674(3) 0.47514(8) 0.0581(5) Uani 1 1 d . . . . .
H21 H 0.292715 0.890446 0.480685 0.070 Uiso 1 1 calc R U . . .
C22 C 0.29103(7) 1.0920(3) 0.46292(9) 0.0690(7) Uani 1 1 d . . . . .
H22 H 0.263375 1.099166 0.460492 0.083 Uiso 1 1 calc R U . . .
C23 C 0.31421(7) 1.2062(3) 0.45428(9) 0.0700(6) Uani 1 1 d . . . . .
H23 H 0.302205 1.290574 0.446599 0.084 Uiso 1 1 calc R U . . .
C24 C 0.35514(7) 1.1958(2) 0.45698(10) 0.0672(6) Uani 1 1 d . . . . .
H24 H 0.370792 1.272670 0.450376 0.081 Uiso 1 1 calc R U . . .
C25 C 0.37293(6) 1.0712(2) 0.46947(9) 0.0589(5) Uani 1 1 d . . . . .
H25 H 0.400615 1.064770 0.471324 0.071 Uiso 1 1 calc R U . . .
C26 C 0.51226(6) 0.58333(19) 0.57879(8) 0.0495(5) Uani 1 1 d . . . . .
H26 H 0.497238 0.512869 0.562358 0.059 Uiso 1 1 calc R U . . .
C27 C 0.54331(6) 0.5517(2) 0.61602(9) 0.0572(5) Uani 1 1 d . . . . .
H27 H 0.549218 0.460250 0.624149 0.069 Uiso 1 1 calc R U . . .
O2 O 0.11093(5) 0.53290(17) 0.73838(7) 0.0765(5) Uani 1 1 d . . . . .
C28 C 0.34231(7) 0.4148(2) 0.87557(11) 0.0735(7) Uani 1 1 d . . . . .
H28 H 0.364924 0.413671 0.899134 0.088 Uiso 1 1 calc R U . . .
C29 C 0.30559(7) 0.4176(2) 0.89769(10) 0.0658(6) Uani 1 1 d . . . . .
H29 H 0.303362 0.418392 0.936409 0.079 Uiso 1 1 calc R U . . .
C30 C 0.27051(6) 0.4193(2) 0.86297(8) 0.0515(5) Uani 1 1 d . . . . .
C31 C 0.27463(5) 0.41812(18) 0.80350(8) 0.0442(4) Uani 1 1 d . . . . .
C32 C 0.23897(5) 0.41846(17) 0.77088(7) 0.0414(4) Uani 1 1 d . . . . .
C33 C 0.20196(5) 0.41895(18) 0.79522(7) 0.0423(4) Uani 1 1 d . . . . .
C34 C 0.17300(5) 0.42050(18) 0.74478(8) 0.0439(4) Uani 1 1 d . . . . .
C35 C 0.19358(5) 0.3111(2) 0.70693(8) 0.0464(4) Uani 1 1 d . . . . .
H35A H 0.200098 0.224844 0.725436 0.056 Uiso 1 1 calc R U . . .
H35B H 0.180656 0.296952 0.670477 0.056 Uiso 1 1 calc R U . . .
C36 C 0.22807(5) 0.42003(18) 0.70811(7) 0.0411(4) Uani 1 1 d . . . . .
C37 C 0.25951(5) 0.42142(18) 0.66521(7) 0.0424(4) Uani 1 1 d . . . . .
C38 C 0.27615(6) 0.3004(2) 0.64606(8) 0.0505(5) Uani 1 1 d . . . . .
H38 H 0.267742 0.216561 0.660230 0.061 Uiso 1 1 calc R U . . .
C39 C 0.30514(6) 0.3031(2) 0.60607(9) 0.0583(5) Uani 1 1 d . . . . .
H39 H 0.316206 0.221322 0.593654 0.070 Uiso 1 1 calc R U . . .
C40 C 0.31758(6) 0.4267(2) 0.58467(9) 0.0598(5) Uani 1 1 d . . . . .
H40 H 0.336875 0.428473 0.557526 0.072 Uiso 1 1 calc R U . . .
C41 C 0.30147(6) 0.5475(2) 0.60347(9) 0.0605(6) Uani 1 1 d . . . . .
H41 H 0.310052 0.631132 0.589298 0.073 Uiso 1 1 calc R U . . .
C42 C 0.27250(6) 0.5449(2) 0.64341(8) 0.0523(5) Uani 1 1 d . . . . .
H42 H 0.261623 0.626985 0.655778 0.063 Uiso 1 1 calc R U . . .
C43 C 0.19381(6) 0.5294(2) 0.70787(8) 0.0512(5) Uani 1 1 d . . . . .
H43A H 0.200565 0.614786 0.726893 0.061 Uiso 1 1 calc R U . . .
H43B H 0.180884 0.545371 0.671545 0.061 Uiso 1 1 calc R U . . .
C44 C 0.12874(6) 0.4283(2) 0.75265(8) 0.0498(5) Uani 1 1 d . . . . .
C45 C 0.10676(5) 0.3103(2) 0.77637(8) 0.0476(4) Uani 1 1 d . . . . .
C46 C 0.12550(6) 0.1901(2) 0.79310(9) 0.0580(5) Uani 1 1 d . . . . .
H46 H 0.153080 0.182920 0.791131 0.070 Uiso 1 1 calc R U . . .
C47 C 0.10382(7) 0.0803(2) 0.81275(10) 0.0675(6) Uani 1 1 d . . . . .
H47 H 0.116809 -0.000296 0.823626 0.081 Uiso 1 1 calc R U . . .
C48 C 0.06308(7) 0.0902(3) 0.81623(10) 0.0679(6) Uani 1 1 d . . . . .
H48 H 0.048453 0.015940 0.829064 0.081 Uiso 1 1 calc R U . . .
C49 C 0.04406(6) 0.2097(3) 0.80075(9) 0.0678(6) Uani 1 1 d . . . . .
H49 H 0.016543 0.216799 0.803644 0.081 Uiso 1 1 calc R U . . .
C50 C 0.06550(6) 0.3192(2) 0.78092(9) 0.0590(5) Uani 1 1 d . . . . .
H50 H 0.052324 0.399766 0.770463 0.071 Uiso 1 1 calc R U . . .
C51 C 0.19802(6) 0.4208(2) 0.85298(8) 0.0509(5) Uani 1 1 d . . . . .
H51 H 0.173016 0.421982 0.868771 0.061 Uiso 1 1 calc R U . . .
C52 C 0.23225(7) 0.4209(2) 0.88584(8) 0.0576(5) Uani 1 1 d . . . . .
H52 H 0.230177 0.422147 0.924588 0.069 Uiso 1 1 calc R U . . .
C53 C 0.31368(6) 0.41552(19) 0.78220(9) 0.0519(5) Uani 1 1 d . . . . .
H53 H 0.316952 0.415208 0.743666 0.062 Uiso 1 1 calc R U . . .
C54 C 0.34635(6) 0.4135(2) 0.81737(10) 0.0640(6) Uani 1 1 d . . . . .
H54 H 0.371684 0.411218 0.802608 0.077 Uiso 1 1 calc R U . . .
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'
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
C2 C1 H1 120.1 . . ?
C27 C1 H1 120.1 . . ?
C27 C1 C2 119.73(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.12(18) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.66(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.33(15) . . ?
C26 C4 C3 118.52(17) . . ?
C26 C4 C5 121.11(16) . . ?
C4 C5 C6 122.19(15) . . ?
C4 C5 C17 122.20(14) . . ?
C4 C5 C18 120.29(14) . . ?
C6 C5 C17 99.17(13) . . ?
C6 C5 C18 99.69(13) . . ?
C18 C5 C17 85.45(13) . . ?
C7 C6 C5 102.91(14) . . ?
C7 C6 C11 121.32(16) . . ?
C11 C6 C5 135.76(16) . . ?
C6 C7 C8 122.27(16) . . ?
C6 C7 C16 102.75(14) . . ?
C8 C7 C16 134.94(16) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 C7 117.70(17) . . ?
C9 C8 H8 121.2 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 122.07(17) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 120.26(17) . . ?
C9 C10 C15 121.96(18) . . ?
C15 C10 C11 117.78(18) . . ?
C6 C11 C10 116.34(16) . . ?
C6 C11 C12 124.94(17) . . ?
C12 C11 C10 118.71(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.60(19) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C7 C16 C17 99.98(14) . . ?
C7 C16 C18 99.88(13) . . ?
C17 C16 C18 85.70(13) . . ?
C19 C16 C7 121.40(15) . . ?
C19 C16 C17 119.86(15) . . ?
C19 C16 C18 122.56(15) . . ?
C5 C17 H17A 114.9 . . ?
C5 C17 H17B 114.9 . . ?
C16 C17 C5 82.60(13) . . ?
C16 C17 H17A 114.9 . . ?
C16 C17 H17B 114.9 . . ?
H17A C17 H17B 111.9 . . ?
C5 C18 C16 82.35(13) . . ?
C5 C18 H18A 114.9 . . ?
C5 C18 H18B 114.9 . . ?
C16 C18 H18A 114.9 . . ?
C16 C18 H18B 114.9 . . ?
H18A C18 H18B 112.0 . . ?
O1 C19 C16 118.60(18) . . ?
O1 C19 C20 120.66(17) . . ?
C20 C19 C16 120.72(16) . . ?
C21 C20 C19 118.42(18) . . ?
C25 C20 C19 123.05(17) . . ?
C25 C20 C21 118.51(19) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.9(2) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.7(2) . . ?
C24 C25 H25 119.6 . . ?
C4 C26 H26 119.6 . . ?
C4 C26 C27 120.73(18) . . ?
C27 C26 H26 119.6 . . ?
C1 C27 C26 120.24(18) . . ?
C1 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 H28 119.9 . . ?
C29 C28 C54 120.3(2) . . ?
C54 C28 H28 119.9 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.3(2) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C31 118.42(19) . . ?
C52 C30 C29 121.47(19) . . ?
C52 C30 C31 120.11(18) . . ?
C32 C31 C30 116.27(17) . . ?
C32 C31 C53 125.41(17) . . ?
C53 C31 C30 118.32(17) . . ?
C31 C32 C36 135.60(16) . . ?
C33 C32 C31 121.64(16) . . ?
C33 C32 C36 102.76(15) . . ?
C32 C33 C34 103.04(15) . . ?
C32 C33 C51 122.02(17) . . ?
C51 C33 C34 134.93(17) . . ?
C33 C34 C35 99.64(14) . . ?
C33 C34 C43 99.69(15) . . ?
C43 C34 C35 85.52(13) . . ?
C44 C34 C33 120.60(15) . . ?
C44 C34 C35 124.05(16) . . ?
C44 C34 C43 119.87(15) . . ?
C34 C35 H35A 114.9 . . ?
C34 C35 H35B 114.9 . . ?
H35A C35 H35B 111.9 . . ?
C36 C35 C34 82.49(13) . . ?
C36 C35 H35A 114.9 . . ?
C36 C35 H35B 114.9 . . ?
C32 C36 C35 99.44(14) . . ?
C32 C36 C43 99.37(14) . . ?
C37 C36 C32 121.30(15) . . ?
C37 C36 C35 122.03(15) . . ?
C37 C36 C43 121.70(15) . . ?
C43 C36 C35 85.30(14) . . ?
C38 C37 C36 121.26(16) . . ?
C42 C37 C36 120.21(16) . . ?
C42 C37 C38 118.53(16) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 C37 120.68(18) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.03(19) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.1 . . ?
C41 C40 C39 119.89(18) . . ?
C41 C40 H40 120.1 . . ?
C40 C41 H41 120.0 . . ?
C40 C41 C42 120.09(19) . . ?
C42 C41 H41 120.0 . . ?
C37 C42 H42 119.6 . . ?
C41 C42 C37 120.77(19) . . ?
C41 C42 H42 119.6 . . ?
C34 C43 C36 82.99(13) . . ?
C34 C43 H43A 114.8 . . ?
C34 C43 H43B 114.8 . . ?
C36 C43 H43A 114.8 . . ?
C36 C43 H43B 114.8 . . ?
H43A C43 H43B 111.9 . . ?
O2 C44 C34 118.87(18) . . ?
O2 C44 C45 120.33(18) . . ?
C45 C44 C34 120.80(16) . . ?
C46 C45 C44 122.52(17) . . ?
C46 C45 C50 118.27(19) . . ?
C50 C45 C44 119.19(18) . . ?
C45 C46 H46 119.6 . . ?
C45 C46 C47 120.85(19) . . ?
C47 C46 H46 119.6 . . ?
C46 C47 H47 120.0 . . ?
C48 C47 C46 120.1(2) . . ?
C48 C47 H47 120.0 . . ?
C47 C48 H48 120.1 . . ?
C49 C48 C47 119.8(2) . . ?
C49 C48 H48 120.1 . . ?
C48 C49 H49 119.8 . . ?
C48 C49 C50 120.3(2) . . ?
C50 C49 H49 119.8 . . ?
C45 C50 H50 119.7 . . ?
C49 C50 C45 120.6(2) . . ?
C49 C50 H50 119.7 . . ?
C33 C51 H51 121.2 . . ?
C52 C51 C33 117.67(18) . . ?
C52 C51 H51 121.2 . . ?
C30 C52 H52 118.9 . . ?
C51 C52 C30 122.30(18) . . ?
C51 C52 H52 118.9 . . ?
C31 C53 H53 119.6 . . ?
C54 C53 C31 120.9(2) . . ?
C54 C53 H53 119.6 . . ?
C28 C54 H54 119.6 . . ?
C53 C54 C28 120.8(2) . . ?
C53 C54 H54 119.6 . . ?
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 C19 1.221(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(3) . ?
C1 C27 1.369(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(2) . ?
C4 C5 1.498(2) . ?
C4 C26 1.381(2) . ?
C5 C6 1.535(2) . ?
C5 C17 1.571(2) . ?
C5 C18 1.562(2) . ?
C6 C7 1.383(2) . ?
C6 C11 1.411(2) . ?
C7 C8 1.392(2) . ?
C7 C16 1.526(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.407(3) . ?
C10 C11 1.433(3) . ?
C10 C15 1.416(3) . ?
C11 C12 1.420(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.356(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.554(2) . ?
C16 C18 1.571(2) . ?
C16 C19 1.504(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.490(3) . ?
C20 C21 1.395(3) . ?
C20 C25 1.386(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.382(3) . ?
C27 H27 0.9300 . ?
O2 C44 1.222(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.355(3) . ?
C28 C54 1.400(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.418(3) . ?
C30 C31 1.431(3) . ?
C30 C52 1.410(3) . ?
C31 C32 1.406(3) . ?
C31 C53 1.420(3) . ?
C32 C33 1.386(2) . ?
C32 C36 1.532(2) . ?
C33 C34 1.523(3) . ?
C33 C51 1.390(3) . ?
C34 C35 1.569(2) . ?
C34 C43 1.557(3) . ?
C34 C44 1.504(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.568(2) . ?
C36 C37 1.493(2) . ?
C36 C43 1.565(3) . ?
C37 C38 1.386(2) . ?
C37 C42 1.384(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.384(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.376(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.374(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.383(3) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.486(3) . ?
C45 C46 1.380(3) . ?
C45 C50 1.394(3) . ?
C46 H46 0.9300 . ?
C46 C47 1.382(3) . ?
C47 H47 0.9300 . ?
C47 C48 1.375(3) . ?
C48 H48 0.9300 . ?
C48 C49 1.371(3) . ?
C49 H49 0.9300 . ?
C49 C50 1.377(3) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C51 C52 1.370(3) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
C53 C54 1.360(3) . ?
C54 H54 0.9300 . ?
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 C19 C20 C21 -5.3(3) . . . . ?
O1 C19 C20 C25 173.20(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C1 C27 C26 -0.6(3) . . . . ?
C2 C3 C4 C5 178.31(17) . . . . ?
C2 C3 C4 C26 0.4(3) . . . . ?
C3 C4 C5 C6 86.2(2) . . . . ?
C3 C4 C5 C17 -145.53(18) . . . . ?
C3 C4 C5 C18 -40.5(2) . . . . ?
C3 C4 C26 C27 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.02(15) . . . . ?
C4 C5 C6 C11 1.8(3) . . . . ?
C4 C5 C17 C16 159.17(16) . . . . ?
C4 C5 C18 C16 -160.44(16) . . . . ?
C4 C26 C27 C1 0.7(3) . . . . ?
C5 C4 C26 C27 -178.44(18) . . . . ?
C5 C6 C7 C8 -178.23(16) . . . . ?
C5 C6 C7 C16 -0.13(16) . . . . ?
C5 C6 C11 C10 179.55(18) . . . . ?
C5 C6 C11 C12 -0.4(3) . . . . ?
C6 C5 C17 C16 -63.16(13) . . . . ?
C6 C5 C18 C16 63.04(13) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C6 C7 C16 C17 -43.79(16) . . . . ?
C6 C7 C16 C18 43.54(16) . . . . ?
C6 C7 C16 C19 -178.19(16) . . . . ?
C6 C11 C12 C13 -178.00(18) . . . . ?
C7 C6 C11 C10 0.5(2) . . . . ?
C7 C6 C11 C12 -179.40(17) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C7 C16 C17 C5 63.62(14) . . . . ?
C7 C16 C18 C5 -63.45(14) . . . . ?
C7 C16 C19 O1 118.5(2) . . . . ?
C7 C16 C19 C20 -63.2(2) . . . . ?
C8 C7 C16 C17 133.9(2) . . . . ?
C8 C7 C16 C18 -138.7(2) . . . . ?
C8 C7 C16 C19 -0.5(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C8 C9 C10 C15 -178.08(19) . . . . ?
C9 C10 C11 C6 -1.6(3) . . . . ?
C9 C10 C11 C12 178.28(17) . . . . ?
C9 C10 C15 C14 -179.8(2) . . . . ?
C10 C11 C12 C13 2.1(3) . . . . ?
C11 C6 C7 C8 1.1(3) . . . . ?
C11 C6 C7 C16 179.17(15) . . . . ?
C11 C10 C15 C14 0.8(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -1.4(4) . . . . ?
C13 C14 C15 C10 1.0(4) . . . . ?
C15 C10 C11 C6 177.73(17) . . . . ?
C15 C10 C11 C12 -2.3(3) . . . . ?
C16 C7 C8 C9 -178.88(18) . . . . ?
C16 C19 C20 C21 176.37(17) . . . . ?
C16 C19 C20 C25 -5.1(3) . . . . ?
C17 C5 C6 C7 43.29(16) . . . . ?
C17 C5 C6 C11 -135.9(2) . . . . ?
C17 C5 C18 C16 -35.51(12) . . . . ?
C17 C16 C18 C5 35.95(12) . . . . ?
C17 C16 C19 O1 -7.3(3) . . . . ?
C17 C16 C19 C20 171.07(16) . . . . ?
C18 C5 C6 C7 -43.62(16) . . . . ?
C18 C5 C6 C11 137.2(2) . . . . ?
C18 C5 C17 C16 35.94(12) . . . . ?
C18 C16 C17 C5 -35.67(12) . . . . ?
C18 C16 C19 O1 -112.6(2) . . . . ?
C18 C16 C19 C20 65.8(2) . . . . ?
C19 C16 C17 C5 -161.06(16) . . . . ?
C19 C16 C18 C5 158.93(17) . . . . ?
C19 C20 C21 C22 176.99(18) . . . . ?
C19 C20 C25 C24 -177.21(19) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C20 C25 C24 1.3(3) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C20 0.1(3) . . . . ?
C25 C20 C21 C22 -1.6(3) . . . . ?
C26 C4 C5 C6 -95.9(2) . . . . ?
C26 C4 C5 C17 32.3(3) . . . . ?
C26 C4 C5 C18 137.33(18) . . . . ?
C27 C1 C2 C3 0.5(3) . . . . ?
O2 C44 C45 C46 -180.0(2) . . . . ?
O2 C44 C45 C50 1.5(3) . . . . ?
C28 C29 C30 C31 -0.1(3) . . . . ?
C28 C29 C30 C52 179.4(2) . . . . ?
C29 C28 C54 C53 0.2(4) . . . . ?
C29 C30 C31 C32 179.36(18) . . . . ?
C29 C30 C31 C53 -0.1(3) . . . . ?
C29 C30 C52 C51 -179.1(2) . . . . ?
C30 C31 C32 C33 -0.4(3) . . . . ?
C30 C31 C32 C36 178.75(18) . . . . ?
C30 C31 C53 C54 0.3(3) . . . . ?
C31 C30 C52 C51 0.3(3) . . . . ?
C31 C32 C33 C34 179.50(16) . . . . ?
C31 C32 C33 C51 0.8(3) . . . . ?
C31 C32 C36 C35 137.0(2) . . . . ?
C31 C32 C36 C37 0.1(3) . . . . ?
C31 C32 C36 C43 -136.2(2) . . . . ?
C31 C53 C54 C28 -0.4(3) . . . . ?
C32 C31 C53 C54 -179.08(19) . . . . ?
C32 C33 C34 C35 43.49(17) . . . . ?
C32 C33 C34 C43 -43.56(17) . . . . ?
C32 C33 C34 C44 -177.03(16) . . . . ?
C32 C33 C51 C52 -0.6(3) . . . . ?
C32 C36 C37 C38 86.8(2) . . . . ?
C32 C36 C37 C42 -93.6(2) . . . . ?
C32 C36 C43 C34 -63.08(14) . . . . ?
C33 C32 C36 C35 -43.68(16) . . . . ?
C33 C32 C36 C37 179.41(16) . . . . ?
C33 C32 C36 C43 43.06(17) . . . . ?
C33 C34 C35 C36 -63.43(14) . . . . ?
C33 C34 C43 C36 63.36(14) . . . . ?
C33 C34 C44 O2 111.5(2) . . . . ?
C33 C34 C44 C45 -69.6(2) . . . . ?
C33 C51 C52 C30 0.0(3) . . . . ?
C34 C33 C51 C52 -178.79(19) . . . . ?
C34 C35 C36 C32 63.29(14) . . . . ?
C34 C35 C36 C37 -160.22(17) . . . . ?
C34 C35 C36 C43 -35.44(12) . . . . ?
C34 C44 C45 C46 1.2(3) . . . . ?
C34 C44 C45 C50 -177.38(18) . . . . ?
C35 C34 C43 C36 -35.67(13) . . . . ?
C35 C34 C44 O2 -119.1(2) . . . . ?
C35 C34 C44 C45 59.8(2) . . . . ?
C35 C36 C37 C38 -40.6(3) . . . . ?
C35 C36 C37 C42 139.00(19) . . . . ?
C35 C36 C43 C34 35.74(13) . . . . ?
C36 C32 C33 C34 0.09(17) . . . . ?
C36 C32 C33 C51 -178.60(16) . . . . ?
C36 C37 C38 C39 179.67(18) . . . . ?
C36 C37 C42 C41 -179.68(19) . . . . ?
C37 C36 C43 C34 160.81(17) . . . . ?
C37 C38 C39 C40 -0.3(3) . . . . ?
C38 C37 C42 C41 -0.1(3) . . . . ?
C38 C39 C40 C41 0.6(3) . . . . ?
C39 C40 C41 C42 -0.6(3) . . . . ?
C40 C41 C42 C37 0.4(3) . . . . ?
C42 C37 C38 C39 0.1(3) . . . . ?
C43 C34 C35 C36 35.66(13) . . . . ?
C43 C34 C44 O2 -12.9(3) . . . . ?
C43 C34 C44 C45 166.01(17) . . . . ?
C43 C36 C37 C38 -146.41(18) . . . . ?
C43 C36 C37 C42 33.2(3) . . . . ?
C44 C34 C35 C36 159.03(17) . . . . ?
C44 C34 C43 C36 -162.73(17) . . . . ?
C44 C45 C46 C47 -177.2(2) . . . . ?
C44 C45 C50 C49 177.53(19) . . . . ?
C45 C46 C47 C48 -0.5(4) . . . . ?
C46 C45 C50 C49 -1.1(3) . . . . ?
C46 C47 C48 C49 -0.7(4) . . . . ?
C47 C48 C49 C50 1.0(4) . . . . ?
C48 C49 C50 C45 -0.1(3) . . . . ?
C50 C45 C46 C47 1.3(3) . . . . ?
C51 C33 C34 C35 -138.1(2) . . . . ?
C51 C33 C34 C43 134.9(2) . . . . ?
C51 C33 C34 C44 1.4(3) . . . . ?
C52 C30 C31 C32 -0.1(3) . . . . ?
C52 C30 C31 C53 -179.58(18) . . . . ?
C53 C31 C32 C33 178.99(17) . . . . ?
C53 C31 C32 C36 -1.8(3) . . . . ?
C54 C28 C29 C30 0.0(4) . . . . ?
