#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:56:07 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272732 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061090.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_7061090
loop_
_publ_author_name
'Wang, Rui'
'Zhang, Wei'
'Tang, Ying'
'Qi, Ze-Hui'
'Yu, Yuan-Hui'
'Tan, Hong-Bo'
'Tang, Dian-Yong'
'Xu, Zhi-Gang'
'Chen, Zhong-Zhu'
_publ_section_title
;
 A four-component domino reaction for the synthesis of novel bridgehead
 nitrogen-containing pyrido[1,2-d][1,4]diazepines
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              592
_journal_page_last               598
_journal_paper_doi               10.1039/D1NJ04233E
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C28 H33 N2 O6'
_chemical_formula_weight         493.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-07-26 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                103.629(2)
_cell_angle_beta                 93.336(2)
_cell_angle_gamma                100.024(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1765(12)
_cell_length_b                   11.7233(18)
_cell_length_c                   14.474(2)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.54
_cell_volume                     1320.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6688
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.024
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0495
_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)+(0.0839P)²+0.3953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3410
_reflns_number_total             4598
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj04233e2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7061088--7061090.cif.'
_cod_database_code               7061090
_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_min   0.978
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O4 O 0.15153(19) 0.33959(11) 0.58573(10) 0.0512(4) Uani 1 1 d . . . . .
O3 O 0.1954(2) 0.36660(12) 0.44105(10) 0.0574(4) Uani 1 1 d . . . . .
N1 N 0.20745(18) 0.71763(12) 0.68378(10) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.3237(2) 0.91901(13) 0.50760(11) 0.0666(5) Uani 1 1 d . . . . .
N2 N 0.4328(2) 0.81182(15) 0.85021(11) 0.0503(4) Uani 1 1 d . . . . .
H2 H 0.4512 0.8075 0.9083 0.060 Uiso 1 1 calc R U . . .
O5 O 0.5789(3) 0.70737(19) 0.97004(12) 0.0869(6) Uani 1 1 d . . . . .
C14 C 0.1632(2) 0.59743(14) 0.65532(12) 0.0342(4) Uani 1 1 d . . . . .
O1 O 0.3077(3) 0.96017(17) 0.34372(15) 0.0887(6) Uani 1 1 d . . . . .
H1 H 0.3065 0.9748 0.4019 0.133 Uiso 1 1 calc R U . . .
C10 C 0.2086(2) 0.53886(15) 0.56685(12) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.2632(2) 0.61035(16) 0.50256(13) 0.0386(4) Uani 1 1 d . . . . .
H9 H 0.2601 0.5735 0.4380 0.046 Uiso 1 1 calc R U . . .
C16 C 0.3409(2) 0.78050(15) 0.63991(12) 0.0383(4) Uani 1 1 d . . . . .
H16 H 0.3315 0.8649 0.6528 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3188(2) 0.72953(16) 0.53307(13) 0.0388(4) Uani 1 1 d . . . . .
C23 C 0.1536(2) 0.79491(15) 0.76800(12) 0.0372(4) Uani 1 1 d . . . . .
H23 H 0.0987 0.7434 0.8060 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5238(2) 0.75604(16) 0.78514(13) 0.0414(4) Uani 1 1 d . . . . .
C11 C 0.1827(2) 0.40926(16) 0.52478(13) 0.0392(4) Uani 1 1 d . . . . .
C28 C 0.3068(2) 0.87836(16) 0.83006(13) 0.0422(5) Uani 1 1 d . . . . .
H28 H 0.3554 0.9351 0.7944 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3422(3) 0.81455(17) 0.47301(14) 0.0456(5) Uani 1 1 d . . . . .
C24 C 0.0290(3) 0.86751(18) 0.74041(14) 0.0484(5) Uani 1 1 d . . . . .
H24A H -0.0690 0.8138 0.7034 0.058 Uiso 1 1 calc R U . . .
H24B H 0.0794 0.9178 0.7012 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0559(3) 0.53559(16) 0.71646(15) 0.0478(5) Uani 1 1 d . . . . .
H15A H 0.1175 0.5452 0.7772 0.072 Uiso 1 1 calc R U . . .
H15B H 0.0234 0.4520 0.6853 0.072 Uiso 1 1 calc R U . . .
H15C H -0.0420 0.5700 0.7260 0.072 Uiso 1 1 calc R U . . .
C6 C 0.3848(3) 0.78111(19) 0.37381(14) 0.0503(5) Uani 1 1 d . . . . .
C17 C 0.5139(2) 0.77360(18) 0.68498(14) 0.0475(5) Uani 1 1 d . . . . .
H17A H 0.5534 0.7083 0.6436 0.057 Uiso 1 1 calc R U . . .
H17B H 0.5907 0.8468 0.6854 0.057 Uiso 1 1 calc R U . . .
C19 C 0.6301(3) 0.68718(19) 0.80879(15) 0.0526(5) Uani 1 1 d . . . . .
H19 H 0.6887 0.6493 0.7614 0.063 Uiso 1 1 calc R U . . .
O6 O 0.7771(3) 0.6081(2) 0.91149(15) 0.1144(9) Uani 1 1 d . . . . .
C26 C 0.1281(3) 1.02303(18) 0.89624(16) 0.0581(6) Uani 1 1 d . . . . .
H26A H 0.1838 1.0816 0.8652 0.070 Uiso 1 1 calc R U . . .
H26B H 0.0906 1.0659 0.9545 0.070 Uiso 1 1 calc R U . . .
C27 C 0.2513(3) 0.94942(19) 0.92146(14) 0.0546(6) Uani 1 1 d . . . . .
H27A H 0.1993 0.8950 0.9572 0.066 Uiso 1 1 calc R U . . .
H27B H 0.3476 1.0018 0.9612 0.066 Uiso 1 1 calc R U . . .
C25 C -0.0226(3) 0.9456(2) 0.83035(16) 0.0588(6) Uani 1 1 d . . . . .
H25A H -0.0932 0.9966 0.8118 0.071 Uiso 1 1 calc R U . . .
H25B H -0.0871 0.8946 0.8646 0.071 Uiso 1 1 calc R U . . .
C1 C 0.3622(3) 0.8569(2) 0.31278(17) 0.0666(7) Uani 1 1 d . . . . .
C12 C 0.1312(3) 0.21152(17) 0.54534(18) 0.0604(6) Uani 1 1 d . . . . .
H12A H 0.2288 0.1934 0.5143 0.072 Uiso 1 1 calc R U . . .
H12B H 0.0343 0.1836 0.4982 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4518(3) 0.6795(2) 0.33694(16) 0.0621(6) Uani 1 1 d . . . . .
H5 H 0.4725 0.6303 0.3764 0.075 Uiso 1 1 calc R U . . .
C20 C 0.6554(3) 0.6708(2) 0.90217(18) 0.0687(7) Uani 1 1 d . . . . .
C13 C 0.1090(4) 0.1519(2) 0.6250(2) 0.0825(8) Uani 1 1 d . . . . .
H13A H 0.0942 0.0668 0.6002 0.124 Uiso 1 1 calc R U . . .
H13B H 0.0125 0.1708 0.6554 0.124 Uiso 1 1 calc R U . . .
H13C H 0.2061 0.1794 0.6708 0.124 Uiso 1 1 calc R U . . .
C2 C 0.3968(4) 0.8256(4) 0.2188(2) 0.0925(10) Uani 1 1 d . . . . .
H2A H 0.3787 0.8743 0.1784 0.111 Uiso 1 1 calc R U . . .
C4 C 0.4874(4) 0.6513(3) 0.2434(2) 0.0889(9) Uani 1 1 d . . . . .
H4 H 0.5315 0.5834 0.2199 0.107 Uiso 1 1 calc R U . . .
C3 C 0.4573(5) 0.7242(4) 0.1845(2) 0.1036(12) Uani 1 1 d . . . . .
H3 H 0.4785 0.7039 0.1209 0.124 Uiso 1 1 calc R U . . .
C21 C 0.7931(7) 0.5665(6) 1.0022(3) 0.1479(19) Uani 1 1 d . . . . .
H21 H 0.7347 0.4972 1.0147 0.178 Uiso 1 1 calc R U . . .
C22 C 0.9120(11) 0.6528(5) 1.0618(4) 0.199(3) Uani 1 1 d . . . . .
H22A H 1.0062 0.6717 1.0277 0.298 Uiso 1 1 calc R U . . .
H22B H 0.9471 0.6241 1.1151 0.298 Uiso 1 1 calc R U . . .
H22C H 0.8665 0.7232 1.0844 0.298 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'
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 O4 C12 116.22(15) . . ?
C14 N1 C16 119.80(14) . . ?
C14 N1 C23 125.71(14) . . ?
C16 N1 C23 113.70(13) . . ?
C18 N2 C28 125.36(16) . . ?
C18 N2 H2 117.3 . . ?
C28 N2 H2 117.3 . . ?
N1 C14 C10 118.28(15) . . ?
N1 C14 C15 117.53(15) . . ?
C10 C14 C15 123.98(15) . . ?
C1 O1 H1 109.5 . . ?
C14 C10 C9 117.68(15) . . ?
C14 C10 C11 127.45(16) . . ?
C9 C10 C11 114.14(15) . . ?
C8 C9 C10 121.88(16) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
N1 C16 C8 109.82(14) . . ?
N1 C16 C17 110.33(15) . . ?
C8 C16 C17 112.04(15) . . ?
N1 C16 H16 108.2 . . ?
C8 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C9 C8 C7 126.34(17) . . ?
C9 C8 C16 116.01(16) . . ?
C7 C8 C16 117.31(15) . . ?
N1 C23 C24 112.43(15) . . ?
N1 C23 C28 109.79(14) . . ?
C24 C23 C28 110.43(15) . . ?
N1 C23 H23 108.0 . . ?
C24 C23 H23 108.0 . . ?
C28 C23 H23 108.0 . . ?
N2 C18 C19 121.40(18) . . ?
N2 C18 C17 119.81(18) . . ?
C19 C18 C17 118.74(17) . . ?
O3 C11 O4 121.27(16) . . ?
O3 C11 C10 122.80(17) . . ?
O4 C11 C10 115.85(15) . . ?
N2 C28 C27 111.94(16) . . ?
N2 C28 C23 111.21(15) . . ?
C27 C28 C23 109.33(16) . . ?
N2 C28 H28 108.1 . . ?
C27 C28 H28 108.1 . . ?
C23 C28 H28 108.1 . . ?
O2 C7 C8 118.12(18) . . ?
O2 C7 C6 119.20(18) . . ?
C8 C7 C6 122.68(18) . . ?
C23 C24 C25 110.12(16) . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C7 123.37(19) . . ?
C1 C6 C7 118.9(2) . . ?
C18 C17 C16 117.11(16) . . ?
C18 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
C18 C19 C20 123.05(19) . . ?
C18 C19 H19 118.5 . . ?
C20 C19 H19 118.5 . . ?
C20 O6 C21 117.1(2) . . ?
C27 C26 C25 112.00(17) . . ?
C27 C26 H26A 109.2 . . ?
C25 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
C25 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 C28 109.62(17) . . ?
C26 C27 H27A 109.7 . . ?
C28 C27 H27A 109.7 . . ?
C26 C27 H27B 109.7 . . ?
C28 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C26 C25 C24 111.89(18) . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
O1 C1 C2 118.3(3) . . ?
O1 C1 C6 121.9(2) . . ?
C2 C1 C6 119.8(3) . . ?
O4 C12 C13 107.65(19) . . ?
O4 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O4 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
O5 C20 O6 120.9(2) . . ?
O5 C20 C19 126.1(2) . . ?
O6 C20 C19 113.0(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C22 C21 O6 104.9(5) . . ?
C22 C21 H21 127.6 . . ?
O6 C21 H21 127.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O4 C11 1.343(2) . ?
O4 C12 1.453(2) . ?
O3 C11 1.215(2) . ?
N1 C14 1.348(2) . ?
N1 C16 1.469(2) . ?
N1 C23 1.477(2) . ?
O2 C7 1.248(2) . ?
N2 C18 1.352(2) . ?
N2 C28 1.452(2) . ?
N2 H2 0.8600 . ?
O5 C20 1.227(3) . ?
C14 C10 1.407(2) . ?
C14 C15 1.500(2) . ?
O1 C1 1.349(3) . ?
O1 H1 0.8200 . ?
C10 C9 1.433(2) . ?
C10 C11 1.470(2) . ?
C9 C8 1.348(2) . ?
C9 H9 0.9300 . ?
C16 C8 1.509(2) . ?
C16 C17 1.546(3) . ?
C16 H16 0.9800 . ?
C8 C7 1.465(3) . ?
C23 C24 1.529(3) . ?
C23 C28 1.537(3) . ?
C23 H23 0.9800 . ?
C18 C19 1.365(3) . ?
C18 C17 1.511(3) . ?
C28 C27 1.527(3) . ?
C28 H28 0.9800 . ?
C7 C6 1.475(3) . ?
C24 C25 1.532(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C6 C5 1.402(3) . ?
C6 C1 1.419(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C20 1.418(3) . ?
C19 H19 0.9300 . ?
O6 C20 1.354(3) . ?
O6 C21 1.511(5) . ?
C26 C27 1.517(3) . ?
C26 C25 1.522(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C1 C2 1.383(4) . ?
C12 C13 1.487(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 C4 1.377(3) . ?
C5 H5 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 C3 1.364(5) . ?
C2 H2A 0.9300 . ?
C4 C3 1.382(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C21 C22 1.364(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
C16 N1 C14 C10 -18.7(2) . . . . ?
C23 N1 C14 C10 172.14(16) . . . . ?
C16 N1 C14 C15 166.38(17) . . . . ?
C23 N1 C14 C15 -2.8(3) . . . . ?
N1 C14 C10 C9 -14.5(2) . . . . ?
C15 C14 C10 C9 160.13(18) . . . . ?
N1 C14 C10 C11 175.98(17) . . . . ?
C15 C14 C10 C11 -9.4(3) . . . . ?
C14 C10 C9 C8 20.0(3) . . . . ?
C11 C10 C9 C8 -169.02(17) . . . . ?
C14 N1 C16 C8 43.9(2) . . . . ?
C23 N1 C16 C8 -145.69(15) . . . . ?
C14 N1 C16 C17 -80.10(19) . . . . ?
C23 N1 C16 C17 90.33(18) . . . . ?
C10 C9 C8 C7 -165.52(18) . . . . ?
C10 C9 C8 C16 7.5(3) . . . . ?
N1 C16 C8 C9 -37.0(2) . . . . ?
C17 C16 C8 C9 86.0(2) . . . . ?
N1 C16 C8 C7 136.68(17) . . . . ?
C17 C16 C8 C7 -100.3(2) . . . . ?
C14 N1 C23 C24 -108.3(2) . . . . ?
C16 N1 C23 C24 81.92(19) . . . . ?
C14 N1 C23 C28 128.31(18) . . . . ?
C16 N1 C23 C28 -41.4(2) . . . . ?
C28 N2 C18 C19 -174.54(19) . . . . ?
C28 N2 C18 C17 8.0(3) . . . . ?
C12 O4 C11 O3 -1.1(3) . . . . ?
C12 O4 C11 C10 -178.05(17) . . . . ?
C14 C10 C11 O3 165.10(19) . . . . ?
C9 C10 C11 O3 -4.8(3) . . . . ?
C14 C10 C11 O4 -18.0(3) . . . . ?
C9 C10 C11 O4 172.13(16) . . . . ?
C18 N2 C28 C27 -169.23(18) . . . . ?
C18 N2 C28 C23 68.1(2) . . . . ?
N1 C23 C28 N2 -50.6(2) . . . . ?
C24 C23 C28 N2 -175.13(16) . . . . ?
N1 C23 C28 C27 -174.72(15) . . . . ?
C24 C23 C28 C27 60.8(2) . . . . ?
C9 C8 C7 O2 149.6(2) . . . . ?
C16 C8 C7 O2 -23.3(3) . . . . ?
C9 C8 C7 C6 -29.8(3) . . . . ?
C16 C8 C7 C6 157.29(18) . . . . ?
N1 C23 C24 C25 179.90(16) . . . . ?
C28 C23 C24 C25 -57.1(2) . . . . ?
O2 C7 C6 C5 162.1(2) . . . . ?
C8 C7 C6 C5 -18.6(3) . . . . ?
O2 C7 C6 C1 -15.9(3) . . . . ?
C8 C7 C6 C1 163.48(19) . . . . ?
N2 C18 C17 C16 -38.3(2) . . . . ?
C19 C18 C17 C16 144.19(19) . . . . ?
N1 C16 C17 C18 -25.0(2) . . . . ?
C8 C16 C17 C18 -147.72(16) . . . . ?
N2 C18 C19 C20 -1.2(3) . . . . ?
C17 C18 C19 C20 176.3(2) . . . . ?
C25 C26 C27 C28 57.0(2) . . . . ?
N2 C28 C27 C26 176.45(17) . . . . ?
C23 C28 C27 C26 -59.9(2) . . . . ?
C27 C26 C25 C24 -54.2(3) . . . . ?
C23 C24 C25 C26 53.6(2) . . . . ?
C5 C6 C1 O1 -176.1(2) . . . . ?
C7 C6 C1 O1 2.0(3) . . . . ?
C5 C6 C1 C2 3.7(3) . . . . ?
C7 C6 C1 C2 -178.2(2) . . . . ?
C11 O4 C12 C13 176.4(2) . . . . ?
C1 C6 C5 C4 -2.9(3) . . . . ?
C7 C6 C5 C4 179.1(2) . . . . ?
C21 O6 C20 O5 10.7(5) . . . . ?
C21 O6 C20 C19 -169.3(4) . . . . ?
C18 C19 C20 O5 5.6(4) . . . . ?
C18 C19 C20 O6 -174.3(2) . . . . ?
O1 C1 C2 C3 177.9(3) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C5 C4 C3 C2 1.7(5) . . . . ?
C20 O6 C21 C22 -94.8(5) . . . . ?
