#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:59:08 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281378 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/82/1568285.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_1568285
loop_
_publ_author_name
'Hu, Yuan'
'Huang, Jin-Yu'
'Yan, Ru-Jie'
'Chen, Zhi-Chao'
'Ouyang, Qin'
'Du, Wei'
'Chen, Ying-Chun'
_publ_section_title
;
 Diastereodivergent cis- and trans-fused [4 + 2] annulations
 of cyclic 1,3-dienes and 1-azadienes via ligand-controlled
 palladium catalysis.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1896
_journal_page_last               1901
_journal_paper_doi               10.1039/d2sc06813c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C26 H21 N O'
_chemical_formula_sum            'C26 H21 N O'
_chemical_formula_weight         363.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-11-15 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.454(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7659(11)
_cell_length_b                   13.1580(15)
_cell_length_c                   27.887(3)
_cell_measurement_reflns_used    7030
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      27.472
_cell_measurement_theta_min      2.713
_cell_volume                     3884.8(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      149.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.1161
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            36992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.145
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1609 before and 0.0986 after correction.
The Ratio of minimum to maximum transmission is 0.6033.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0681
_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)+(0.0884P)²+0.3651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5667
_reflns_number_total             8881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06813c2.cif
_cod_data_source_block           25
_cod_depositor_comments
'Adding full bibliography for 1568280--1568287.cif.'
_cod_database_code               1568285
_shelx_shelxl_version_number     2014/7
_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   0.997
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C16(H16), C33(H33), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C48(H48),
  C49(H49), C50(H50), C51(H51)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.40968(14) 0.22483(11) 0.38304(5) 0.0302(4) Uani 1 1 d . . . . .
O2 O 0.55897(14) 0.74825(10) 0.11713(6) 0.0303(4) Uani 1 1 d . . . . .
N1 N 0.6526(2) 0.43600(16) 0.29463(8) 0.0448(5) Uani 1 1 d . . . . .
N2 N 0.36217(18) 0.50736(15) 0.20783(7) 0.0367(5) Uani 1 1 d . . . . .
C1 C 0.2871(2) 0.58138(17) 0.39160(9) 0.0364(5) Uani 1 1 d . . . . .
H1 H 0.2493 0.6434 0.3989 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3119(2) 0.56424(17) 0.34516(9) 0.0353(5) Uani 1 1 d . . . . .
H2 H 0.2903 0.6144 0.3206 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3678(2) 0.47461(16) 0.33452(8) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.3845 0.4634 0.3026 0.035 Uiso 1 1 calc R U . . .
C4 C 0.39986(19) 0.40049(15) 0.37035(8) 0.0259(5) Uani 1 1 d . . . . .
C5 C 0.4561(2) 0.30270(16) 0.35908(7) 0.0269(5) Uani 1 1 d . . . . .
C6 C 0.4687(2) 0.12575(15) 0.38047(8) 0.0299(5) Uani 1 1 d . . . . .
H6 H 0.5539 0.1255 0.4019 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3835(2) 0.05241(16) 0.40002(8) 0.0313(5) Uani 1 1 d . . . . .
H7 H 0.2956 0.0559 0.3872 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4223(2) -0.01683(16) 0.43382(8) 0.0305(5) Uani 1 1 d . . . . .
H8 H 0.5096 -0.0166 0.4477 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3434(2) -0.09424(16) 0.45203(8) 0.0288(5) Uani 1 1 d . . . . .
C10 C 0.2125(2) -0.10086(17) 0.43648(8) 0.0335(5) Uani 1 1 d . . . . .
H10 H 0.1709 -0.0538 0.4131 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1434(2) -0.17474(17) 0.45466(8) 0.0337(5) Uani 1 1 d . . . . .
H11 H 0.0545 -0.1778 0.4439 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2020(2) -0.24455(17) 0.48838(9) 0.0356(5) Uani 1 1 d . . . . .
H12 H 0.1538 -0.2956 0.5007 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3177(2) 0.50800(18) 0.42724(9) 0.0361(5) Uani 1 1 d . . . . .
H13 H 0.3008 0.5197 0.4591 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3727(2) 0.41771(17) 0.41676(8) 0.0308(5) Uani 1 1 d . . . . .
H14 H 0.3922 0.3671 0.4413 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4825(2) 0.10498(16) 0.32821(8) 0.0321(5) Uani 1 1 d . . . . .
H15A H 0.3985 0.1078 0.3068 0.039 Uiso 1 1 calc R U . . .
H15B H 0.5175 0.0360 0.3258 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5699(2) 0.18324(16) 0.31120(8) 0.0300(5) Uani 1 1 d . . . . .
H16 H 0.6589 0.1663 0.3264 0.036 Uiso 1 1 calc R U . . .
C17 C 0.5387(2) 0.28784(16) 0.32906(8) 0.0279(5) Uani 1 1 d . . . . .
C18 C 0.5987(2) 0.37277(17) 0.31039(8) 0.0313(5) Uani 1 1 d . . . . .
C19 C 0.55932(19) 0.18119(16) 0.25609(8) 0.0268(5) Uani 1 1 d . . . . .
C20 C 0.6356(2) 0.11803(16) 0.23440(8) 0.0300(5) Uani 1 1 d . . . . .
H20 H 0.6959 0.0760 0.2542 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6254(2) 0.11506(17) 0.18416(9) 0.0340(5) Uani 1 1 d . . . . .
H21 H 0.6786 0.0713 0.1699 0.041 Uiso 1 1 calc R U . . .
C22 C 0.5385(2) 0.17514(17) 0.15497(8) 0.0350(5) Uani 1 1 d . . . . .
H22 H 0.5319 0.1733 0.1205 0.042 Uiso 1 1 calc R U . . .
C23 C 0.4608(2) 0.23821(17) 0.17588(8) 0.0362(5) Uani 1 1 d . . . . .
H23 H 0.4007 0.2800 0.1558 0.043 Uiso 1 1 calc R U . . .
C24 C 0.4703(2) 0.24066(17) 0.22598(8) 0.0336(5) Uani 1 1 d . . . . .
H24 H 0.4156 0.2834 0.2401 0.040 Uiso 1 1 calc R U . . .
C25 C 0.4009(2) -0.16542(16) 0.48625(8) 0.0318(5) Uani 1 1 d . . . . .
H25 H 0.4896 -0.1627 0.4974 0.038 Uiso 1 1 calc R U . . .
C26 C 0.3305(2) -0.23964(17) 0.50404(9) 0.0360(5) Uani 1 1 d . . . . .
H26 H 0.3711 -0.2875 0.5272 0.043 Uiso 1 1 calc R U . . .
C27 C 0.7743(2) 1.19499(18) 0.01818(8) 0.0350(5) Uani 1 1 d . . . . .
H27 H 0.8045 1.2535 0.0040 0.042 Uiso 1 1 calc R U . . .
C28 C 0.8578(2) 1.12743(18) 0.04458(8) 0.0355(5) Uani 1 1 d . . . . .
H28 H 0.9461 1.1393 0.0485 0.043 Uiso 1 1 calc R U . . .
C29 C 0.8138(2) 1.04220(18) 0.06550(8) 0.0329(5) Uani 1 1 d . . . . .
H29 H 0.8728 0.9962 0.0833 0.040 Uiso 1 1 calc R U . . .
C30 C 0.6855(2) 1.02263(16) 0.06094(7) 0.0267(5) Uani 1 1 d . . . . .
C31 C 0.6405(2) 0.93289(16) 0.08430(7) 0.0282(5) Uani 1 1 d . . . . .
H31 H 0.6978 0.8779 0.0922 0.034 Uiso 1 1 calc R U . . .
C32 C 0.5274(2) 0.92287(16) 0.09509(8) 0.0296(5) Uani 1 1 d . . . . .
H32 H 0.4701 0.9773 0.0858 0.035 Uiso 1 1 calc R U . . .
C33 C 0.4789(2) 0.83543(16) 0.12032(8) 0.0288(5) Uani 1 1 d . . . . .
H33 H 0.3914 0.8190 0.1031 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4750(2) 0.85581(16) 0.17354(8) 0.0302(5) Uani 1 1 d . . . . .
H34A H 0.4278 0.9194 0.1766 0.036 Uiso 1 1 calc R U . . .
H34B H 0.5619 0.8642 0.1920 0.036 Uiso 1 1 calc R U . . .
C35 C 0.4103(2) 0.76664(15) 0.19457(8) 0.0264(5) Uani 1 1 d . . . . .
H35 H 0.3172 0.7730 0.1829 0.032 Uiso 1 1 calc R U . . .
C36 C 0.43494(19) 0.76991(15) 0.24985(8) 0.0249(4) Uani 1 1 d . . . . .
C37 C 0.3574(2) 0.82874(15) 0.27337(8) 0.0280(5) Uani 1 1 d . . . . .
H37 H 0.2888 0.8647 0.2547 0.034 Uiso 1 1 calc R U . . .
C38 C 0.3786(2) 0.83575(16) 0.32370(8) 0.0307(5) Uani 1 1 d . . . . .
H38 H 0.3242 0.8758 0.3393 0.037 Uiso 1 1 calc R U . . .
C39 C 0.4790(2) 0.78445(17) 0.35134(8) 0.0332(5) Uani 1 1 d . . . . .
H39 H 0.4940 0.7894 0.3859 0.040 Uiso 1 1 calc R U . . .
C40 C 0.7199(2) 0.40570(19) 0.09757(10) 0.0434(6) Uani 1 1 d . . . . .
H40 H 0.7634 0.3486 0.0879 0.052 Uiso 1 1 calc R U . . .
C41 C 0.6788(2) 0.48211(19) 0.06450(10) 0.0443(6) Uani 1 1 d . . . . .
H41 H 0.6936 0.4772 0.0320 0.053 Uiso 1 1 calc R U . . .
C42 C 0.6163(2) 0.56559(18) 0.07853(9) 0.0366(5) Uani 1 1 d . . . . .
H42 H 0.5891 0.6184 0.0558 0.044 Uiso 1 1 calc R U . . .
C43 C 0.5929(2) 0.57245(15) 0.12622(8) 0.0268(5) Uani 1 1 d . . . . .
C44 C 0.6346(2) 0.49487(16) 0.15899(9) 0.0312(5) Uani 1 1 d . . . . .
H44 H 0.6195 0.4988 0.1915 0.037 Uiso 1 1 calc R U . . .
C45 C 0.6977(2) 0.41216(17) 0.14473(9) 0.0385(6) Uani 1 1 d . . . . .
H45 H 0.7259 0.3595 0.1674 0.046 Uiso 1 1 calc R U . . .
C46 C 0.5301(2) 0.66396(15) 0.14120(8) 0.0274(5) Uani 1 1 d . . . . .
C47 C 0.45364(19) 0.66804(15) 0.17457(7) 0.0255(4) Uani 1 1 d . . . . .
C48 C 0.6459(2) 1.17643(17) 0.01258(8) 0.0327(5) Uani 1 1 d . . . . .
H48 H 0.5877 1.2225 -0.0056 0.039 Uiso 1 1 calc R U . . .
C49 C 0.6013(2) 1.09114(16) 0.03333(8) 0.0290(5) Uani 1 1 d . . . . .
H49 H 0.5130 1.0789 0.0288 0.035 Uiso 1 1 calc R U . . .
C50 C 0.5573(2) 0.72599(16) 0.32835(8) 0.0321(5) Uani 1 1 d . . . . .
H50 H 0.6261 0.6904 0.3472 0.039 Uiso 1 1 calc R U . . .
C51 C 0.5359(2) 0.71902(17) 0.27794(8) 0.0307(5) Uani 1 1 d . . . . .
H51 H 0.5906 0.6791 0.2624 0.037 Uiso 1 1 calc R U . . .
C52 C 0.4075(2) 0.57705(17) 0.19281(8) 0.0275(5) Uani 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
C5 O1 C6 116.44(16) . . ?
C46 O2 C33 115.04(16) . . ?
C2 C1 H1 120.1 . . ?
C13 C1 H1 120.1 . . ?
C13 C1 C2 119.8(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.91(19) . . ?
C3 C4 C14 119.0(2) . . ?
C14 C4 C5 120.02(19) . . ?
O1 C5 C4 110.38(17) . . ?
C17 C5 O1 122.57(19) . . ?
C17 C5 C4 127.03(19) . . ?
O1 C6 H6 109.6 . . ?
O1 C6 C7 104.86(17) . . ?
O1 C6 C15 109.15(17) . . ?
C7 C6 H6 109.6 . . ?
C7 C6 C15 113.97(18) . . ?
C15 C6 H6 109.6 . . ?
C6 C7 H7 117.7 . . ?
C8 C7 C6 124.6(2) . . ?
C8 C7 H7 117.7 . . ?
C7 C8 H8 116.8 . . ?
C7 C8 C9 126.5(2) . . ?
C9 C8 H8 116.8 . . ?
C10 C9 C8 123.1(2) . . ?
C25 C9 C8 119.1(2) . . ?
C25 C9 C10 117.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.2 . . ?
C26 C12 C11 119.6(2) . . ?
C26 C12 H12 120.2 . . ?
C1 C13 H13 119.9 . . ?
C1 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C4 C14 H14 119.8 . . ?
C13 C14 C4 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 C16 110.51(18) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16 108.3 . . ?
C17 C16 C15 108.84(17) . . ?
C17 C16 H16 108.3 . . ?
C19 C16 C15 111.38(17) . . ?
C19 C16 H16 108.3 . . ?
C19 C16 C17 111.49(17) . . ?
C5 C17 C16 123.16(19) . . ?
C5 C17 C18 120.4(2) . . ?
C18 C17 C16 116.39(18) . . ?
N1 C18 C17 175.3(3) . . ?
C20 C19 C16 120.75(19) . . ?
C20 C19 C24 118.1(2) . . ?
C24 C19 C16 121.07(19) . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.7(2) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(2) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C9 C25 H25 119.5 . . ?
C26 C25 C9 120.9(2) . . ?
C26 C25 H25 119.5 . . ?
C12 C26 C25 120.3(2) . . ?
C12 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 H27 120.4 . . ?
C28 C27 C48 119.2(2) . . ?
C48 C27 H27 120.4 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.5(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.3 . . ?
C28 C29 C30 121.4(2) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C31 120.67(19) . . ?
C29 C30 C49 117.6(2) . . ?
C49 C30 C31 121.71(19) . . ?
C30 C31 H31 117.4 . . ?
C32 C31 C30 125.13(19) . . ?
C32 C31 H31 117.4 . . ?
C31 C32 H32 116.4 . . ?
C31 C32 C33 127.19(19) . . ?
C33 C32 H32 116.4 . . ?
O2 C33 C32 108.58(17) . . ?
O2 C33 H33 108.6 . . ?
O2 C33 C34 108.85(17) . . ?
C32 C33 H33 108.6 . . ?
C32 C33 C34 113.55(18) . . ?
C34 C33 H33 108.6 . . ?
C33 C34 H34A 109.8 . . ?
C33 C34 H34B 109.8 . . ?
C33 C34 C35 109.51(17) . . ?
H34A C34 H34B 108.2 . . ?
C35 C34 H34A 109.8 . . ?
C35 C34 H34B 109.8 . . ?
C34 C35 H35 108.0 . . ?
C36 C35 C34 111.05(17) . . ?
C36 C35 H35 108.0 . . ?
C36 C35 C47 112.88(17) . . ?
C47 C35 C34 108.79(16) . . ?
C47 C35 H35 108.0 . . ?
C37 C36 C35 119.15(18) . . ?
C37 C36 C51 118.6(2) . . ?
C51 C36 C35 122.24(18) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 C36 120.9(2) . . ?
C38 C37 H37 119.5 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0(2) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 120.2 . . ?
C50 C39 C38 119.6(2) . . ?
C50 C39 H39 120.2 . . ?
C41 C40 H40 120.0 . . ?
C45 C40 H40 120.0 . . ?
C45 C40 C41 120.1(2) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 C40 120.2(2) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 120.0 . . ?
C41 C42 C43 120.1(2) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 C46 119.43(19) . . ?
C44 C43 C42 119.0(2) . . ?
C44 C43 C46 121.49(19) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 C43 120.5(2) . . ?
C45 C44 H44 119.8 . . ?
C40 C45 H45 119.9 . . ?
C44 C45 C40 120.2(2) . . ?
C44 C45 H45 119.9 . . ?
O2 C46 C43 111.53(18) . . ?
C47 C46 O2 121.99(19) . . ?
C47 C46 C43 126.48(19) . . ?
C46 C47 C35 123.59(18) . . ?
C46 C47 C52 120.55(19) . . ?
C52 C47 C35 115.87(18) . . ?
C27 C48 H48 119.7 . . ?
C27 C48 C49 120.6(2) . . ?
C49 C48 H48 119.7 . . ?
C30 C49 H49 119.7 . . ?
C48 C49 C30 120.7(2) . . ?
C48 C49 H49 119.7 . . ?
C39 C50 H50 119.9 . . ?
C39 C50 C51 120.3(2) . . ?
C51 C50 H50 119.9 . . ?
C36 C51 H51 119.7 . . ?
C50 C51 C36 120.6(2) . . ?
C50 C51 H51 119.7 . . ?
N2 C52 C47 175.0(2) . . ?
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 C5 1.366(2) . ?
O1 C6 1.458(2) . ?
O2 C33 1.448(2) . ?
O2 C46 1.361(2) . ?
N1 C18 1.146(3) . ?
N2 C52 1.152(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C13 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C4 C5 1.480(3) . ?
C4 C14 1.396(3) . ?
C5 C17 1.341(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.501(3) . ?
C6 C15 1.516(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.323(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.474(3) . ?
C9 C10 1.400(3) . ?
C9 C25 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C26 1.374(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.527(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.522(3) . ?
C16 C19 1.520(3) . ?
C17 C18 1.435(3) . ?
C19 C20 1.382(3) . ?
C19 C24 1.394(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.378(3) . ?
C27 C48 1.385(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(3) . ?
C30 C31 1.472(3) . ?
C30 C49 1.405(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.313(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.492(3) . ?
C33 H33 1.0000 . ?
C33 C34 1.516(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.534(3) . ?
C35 H35 1.0000 . ?
C35 C36 1.517(3) . ?
C35 C47 1.519(3) . ?
C36 C37 1.387(3) . ?
C36 C51 1.391(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.384(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.384(3) . ?
C39 H39 0.9500 . ?
C39 C50 1.382(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.382(4) . ?
C40 C45 1.381(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.401(3) . ?
C43 C44 1.389(3) . ?
C43 C46 1.478(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.379(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.350(3) . ?
C47 C52 1.425(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.388(3) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C50 C51 1.386(3) . ?
C51 H51 0.9500 . ?
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 C5 C17 C16 11.9(3) . . . . ?
O1 C5 C17 C18 -170.82(19) . . . . ?
O1 C6 C7 C8 -130.7(2) . . . . ?
O1 C6 C15 C16 62.8(2) . . . . ?
O2 C33 C34 C35 -65.2(2) . . . . ?
O2 C46 C47 C35 -10.4(3) . . . . ?
O2 C46 C47 C52 168.95(18) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C13 C14 C4 1.1(3) . . . . ?
C2 C1 C13 C14 0.0(4) . . . . ?
C2 C3 C4 C5 178.03(19) . . . . ?
C2 C3 C4 C14 1.0(3) . . . . ?
C3 C4 C5 O1 -141.71(19) . . . . ?
C3 C4 C5 C17 36.7(3) . . . . ?
C3 C4 C14 C13 -1.5(3) . . . . ?
C4 C5 C17 C16 -166.42(19) . . . . ?
C4 C5 C17 C18 10.9(3) . . . . ?
C5 O1 C6 C7 -168.35(17) . . . . ?
C5 O1 C6 C15 -45.9(2) . . . . ?
C5 C4 C14 C13 -178.6(2) . . . . ?
C6 O1 C5 C4 -172.28(17) . . . . ?
C6 O1 C5 C17 9.2(3) . . . . ?
C6 C7 C8 C9 -176.1(2) . . . . ?
C6 C15 C16 C17 -42.2(2) . . . . ?
C6 C15 C16 C19 -165.51(18) . . . . ?
C7 C6 C15 C16 179.67(18) . . . . ?
C7 C8 C9 C10 -2.9(3) . . . . ?
C7 C8 C9 C25 176.7(2) . . . . ?
C8 C9 C10 C11 179.9(2) . . . . ?
C8 C9 C25 C26 -179.6(2) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C25 C26 C12 -0.2(3) . . . . ?
C10 C9 C25 C26 0.0(3) . . . . ?
C10 C11 C12 C26 0.3(3) . . . . ?
C11 C12 C26 C25 0.0(4) . . . . ?
C13 C1 C2 C3 -0.5(4) . . . . ?
C14 C4 C5 O1 35.3(3) . . . . ?
C14 C4 C5 C17 -146.3(2) . . . . ?
C15 C6 C7 C8 110.0(3) . . . . ?
C15 C16 C17 C5 6.3(3) . . . . ?
C15 C16 C17 C18 -171.09(19) . . . . ?
C15 C16 C19 C20 -89.5(2) . . . . ?
C15 C16 C19 C24 88.8(2) . . . . ?
C16 C19 C20 C21 179.3(2) . . . . ?
C16 C19 C24 C23 -179.7(2) . . . . ?
C17 C16 C19 C20 148.8(2) . . . . ?
C17 C16 C19 C24 -33.0(3) . . . . ?
C19 C16 C17 C5 129.6(2) . . . . ?
C19 C16 C17 C18 -47.8(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C19 C24 C23 -1.5(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 1.0(4) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
C25 C9 C10 C11 0.4(3) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C27 C48 C49 C30 0.8(3) . . . . ?
C28 C27 C48 C49 0.2(3) . . . . ?
C28 C29 C30 C31 -178.7(2) . . . . ?
C28 C29 C30 C49 1.5(3) . . . . ?
C29 C30 C31 C32 158.2(2) . . . . ?
C29 C30 C49 C48 -1.6(3) . . . . ?
C30 C31 C32 C33 -177.6(2) . . . . ?
C31 C30 C49 C48 178.53(19) . . . . ?
C31 C32 C33 O2 -18.8(3) . . . . ?
C31 C32 C33 C34 102.4(3) . . . . ?
C32 C33 C34 C35 173.71(17) . . . . ?
C33 O2 C46 C43 165.51(18) . . . . ?
C33 O2 C46 C47 -14.9(3) . . . . ?
C33 C34 C35 C36 164.87(17) . . . . ?
C33 C34 C35 C47 40.0(2) . . . . ?
C34 C35 C36 C37 85.3(2) . . . . ?
C34 C35 C36 C51 -92.2(2) . . . . ?
C34 C35 C47 C46 -4.1(3) . . . . ?
C34 C35 C47 C52 176.58(18) . . . . ?
C35 C36 C37 C38 -178.40(19) . . . . ?
C35 C36 C51 C50 178.3(2) . . . . ?
C36 C35 C47 C46 -127.8(2) . . . . ?
C36 C35 C47 C52 52.8(2) . . . . ?
C36 C37 C38 C39 0.6(3) . . . . ?
C37 C36 C51 C50 0.9(3) . . . . ?
C37 C38 C39 C50 -0.3(3) . . . . ?
C38 C39 C50 C51 0.3(3) . . . . ?
C39 C50 C51 C36 -0.6(3) . . . . ?
C40 C41 C42 C43 -0.8(4) . . . . ?
C41 C40 C45 C44 0.0(4) . . . . ?
C41 C42 C43 C44 0.6(3) . . . . ?
C41 C42 C43 C46 177.8(2) . . . . ?
C42 C43 C44 C45 -0.2(3) . . . . ?
C42 C43 C46 O2 -31.3(3) . . . . ?
C42 C43 C46 C47 149.2(2) . . . . ?
C43 C44 C45 C40 -0.1(4) . . . . ?
C43 C46 C47 C35 169.09(19) . . . . ?
C43 C46 C47 C52 -11.6(3) . . . . ?
C44 C43 C46 O2 145.8(2) . . . . ?
C44 C43 C46 C47 -33.7(3) . . . . ?
C45 C40 C41 C42 0.5(4) . . . . ?
C46 O2 C33 C32 176.33(17) . . . . ?
C46 O2 C33 C34 52.3(2) . . . . ?
C46 C43 C44 C45 -177.3(2) . . . . ?
C47 C35 C36 C37 -152.27(19) . . . . ?
C47 C35 C36 C51 30.3(3) . . . . ?
C48 C27 C28 C29 -0.3(3) . . . . ?
C49 C30 C31 C32 -22.0(3) . . . . ?
C51 C36 C37 C38 -0.9(3) . . . . ?
