#------------------------------------------------------------------------------
#$Date: 2022-08-20 01:18:40 +0300 (Sat, 20 Aug 2022) $
#$Revision: 277328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567502.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_1567502
loop_
_publ_author_name
'Hamsath, Akil'
'Lederberg, Oren L.'
'Cui, Qi'
'Shieh, Meg'
'Lam, Yannie'
'Brummett, Brock J.'
'Xu, Shi'
'Robinson, Jerome R.'
'Xian, Ming'
_publ_section_title
;
 Intramolecular tetrazine-acryloyl cycloaddition: chemistry and
 applications
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04331A
_journal_year                    2022
_chemical_formula_moiety         '2(C16 H11 N3 O2)'
_chemical_formula_sum            'C32 H22 N6 O4'
_chemical_formula_weight         554.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-27 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0961(4)
_cell_length_b                   9.9627(3)
_cell_length_c                   22.3275(6)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.49
_cell_volume                     2460.87(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            62503
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.240
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0532 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.9588.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0387
_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)+(0.0512P)²+1.0574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5025
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04331a3.cif
_cod_data_source_block           mx20220725_0m
_cod_database_code               1567502
_shelx_shelxl_version_number     2018/3
_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   0.994
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), N4(H4), C21(H21), C22(H22), C23(H23), C24(H24), C29(H29), C30(H30),
 C31(H31), C32(H32)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.40812(9) 0.66920(10) 0.46901(4) 0.0317(2) Uani 1 1 d . . . . .
O2 O 0.55475(8) 0.74147(9) 0.53334(4) 0.02454(19) Uani 1 1 d . . . . .
N1 N 0.64398(10) 1.03432(10) 0.41175(5) 0.0231(2) Uani 1 1 d . . . . .
H1 H 0.690370 1.101584 0.424680 0.028 Uiso 1 1 calc R U . . .
N2 N 0.60305(9) 1.03025(10) 0.35169(5) 0.0227(2) Uani 1 1 d . . . . .
N3 N 0.38737(9) 0.85663(11) 0.25580(5) 0.0234(2) Uani 1 1 d . . . . .
C1 C 0.49042(11) 0.74944(12) 0.47823(5) 0.0217(2) Uani 1 1 d . . . . .
C2 C 0.52293(10) 0.85079(12) 0.43711(5) 0.0194(2) Uani 1 1 d . . . . .
C3 C 0.61524(10) 0.93812(12) 0.45176(5) 0.0192(2) Uani 1 1 d . . . . .
C4 C 0.68320(10) 0.92813(12) 0.50990(5) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.78173(11) 1.01024(13) 0.52918(6) 0.0241(3) Uani 1 1 d . . . . .
H5 H 0.806695 1.079676 0.503726 0.029 Uiso 1 1 calc R U . . .
C6 C 0.84258(12) 0.99065(14) 0.58492(6) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.910093 1.045336 0.597305 0.034 Uiso 1 1 calc R U . . .
C7 C 0.80484(12) 0.89071(14) 0.62289(6) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.846441 0.878356 0.661300 0.035 Uiso 1 1 calc R U . . .
C8 C 0.70746(12) 0.80921(14) 0.60532(6) 0.0269(3) Uani 1 1 d . . . . .
H8 H 0.681524 0.741644 0.631458 0.032 Uiso 1 1 calc R U . . .
C9 C 0.64821(11) 0.82792(12) 0.54875(5) 0.0215(2) Uani 1 1 d . . . . .
C10 C 0.45199(11) 0.85950(13) 0.37736(5) 0.0221(2) Uani 1 1 d . . . . .
H10A H 0.370462 0.895817 0.382682 0.027 Uiso 1 1 calc R U . . .
H10B H 0.442455 0.768703 0.359600 0.027 Uiso 1 1 calc R U . . .
C11 C 0.51608(10) 0.94927(12) 0.33574(5) 0.0198(2) Uani 1 1 d . . . . .
C12 C 0.48127(11) 0.93856(12) 0.27040(5) 0.0205(2) Uani 1 1 d . . . . .
C13 C 0.54565(11) 1.00264(13) 0.22719(6) 0.0242(3) Uani 1 1 d . . . . .
H13 H 0.608414 1.064411 0.238750 0.029 Uiso 1 1 calc R U . . .
C14 C 0.51585(12) 0.97404(13) 0.16718(6) 0.0272(3) Uani 1 1 d . . . . .
H14 H 0.559456 1.014311 0.136906 0.033 Uiso 1 1 calc R U . . .
C15 C 0.42165(12) 0.88597(13) 0.15169(6) 0.0271(3) Uani 1 1 d . . . . .
H15 H 0.400783 0.863151 0.110891 0.033 Uiso 1 1 calc R U . . .
C16 C 0.35898(12) 0.83232(13) 0.19721(6) 0.0254(3) Uani 1 1 d . . . . .
H16 H 0.292235 0.775176 0.186487 0.030 Uiso 1 1 calc R U . . .
O3 O -0.14087(9) 0.22620(10) 0.41953(4) 0.0319(2) Uani 1 1 d . . . . .
O4 O -0.07539(8) 0.37915(9) 0.35815(4) 0.0255(2) Uani 1 1 d . . . . .
N4 N 0.20795(9) 0.47421(11) 0.48337(5) 0.0229(2) Uani 1 1 d . . . . .
H4 H 0.259569 0.536223 0.473794 0.027 Uiso 1 1 calc R U . . .
N5 N 0.22665(9) 0.41314(10) 0.53853(4) 0.0216(2) Uani 1 1 d . . . . .
N6 N 0.10736(10) 0.15226(11) 0.62260(5) 0.0259(2) Uani 1 1 d . . . . .
C17 C -0.06536(11) 0.31208(12) 0.41256(5) 0.0221(2) Uani 1 1 d . . . . .
C18 C 0.03238(10) 0.34736(12) 0.45518(5) 0.0190(2) Uani 1 1 d . . . . .
C19 C 0.11400(10) 0.44408(12) 0.44274(5) 0.0187(2) Uani 1 1 d . . . . .
C20 C 0.10059(10) 0.51606(12) 0.38603(5) 0.0194(2) Uani 1 1 d . . . . .
C21 C 0.17617(11) 0.62086(13) 0.36962(5) 0.0229(2) Uani 1 1 d . . . . .
H21 H 0.243201 0.647026 0.396086 0.027 Uiso 1 1 calc R U . . .
C22 C 0.15376(12) 0.68615(13) 0.31530(6) 0.0249(3) Uani 1 1 d . . . . .
H22 H 0.205777 0.756276 0.304376 0.030 Uiso 1 1 calc R U . . .
C23 C 0.05496(12) 0.64921(13) 0.27655(5) 0.0245(3) Uani 1 1 d . . . . .
H23 H 0.039176 0.695332 0.239537 0.029 Uiso 1 1 calc R U . . .
C24 C -0.02028(11) 0.54603(13) 0.29151(5) 0.0238(3) Uani 1 1 d . . . . .
H24 H -0.087192 0.520378 0.264852 0.029 Uiso 1 1 calc R U . . .
C25 C 0.00315(11) 0.48033(12) 0.34598(5) 0.0206(2) Uani 1 1 d . . . . .
C26 C 0.04457(11) 0.27065(12) 0.51316(5) 0.0204(2) Uani 1 1 d . . . . .
H26A H 0.054727 0.173921 0.504742 0.024 Uiso 1 1 calc R U . . .
H26B H -0.029717 0.281756 0.534531 0.024 Uiso 1 1 calc R U . . .
C27 C 0.15229(10) 0.32093(12) 0.55223(5) 0.0194(2) Uani 1 1 d . . . . .
C28 C 0.17520(10) 0.25965(12) 0.61234(5) 0.0202(2) Uani 1 1 d . . . . .
C29 C 0.26000(11) 0.31214(13) 0.65555(6) 0.0245(3) Uani 1 1 d . . . . .
H29 H 0.309003 0.386378 0.646317 0.029 Uiso 1 1 calc R U . . .
C30 C 0.27150(12) 0.25436(14) 0.71199(6) 0.0272(3) Uani 1 1 d . . . . .
H30 H 0.327206 0.289450 0.742475 0.033 Uiso 1 1 calc R U . . .
C31 C 0.20051(12) 0.14462(14) 0.72329(6) 0.0279(3) Uani 1 1 d . . . . .
H31 H 0.205418 0.103324 0.761752 0.033 Uiso 1 1 calc R U . . .
C32 C 0.12221(12) 0.09663(14) 0.67710(6) 0.0303(3) Uani 1 1 d . . . . .
H32 H 0.075937 0.019032 0.684589 0.036 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
C9 O2 C1 121.19(9) . . ?
N2 N1 H1 118.7 . . ?
C3 N1 H1 118.7 . . ?
C3 N1 N2 122.57(10) . . ?
C11 N2 N1 118.03(10) . . ?
C16 N3 C12 117.69(11) . . ?
O1 C1 O2 116.31(11) . . ?
O1 C1 C2 125.28(11) . . ?
O2 C1 C2 118.41(10) . . ?
C1 C2 C10 118.13(10) . . ?
C3 C2 C1 121.23(11) . . ?
C3 C2 C10 120.63(11) . . ?
N1 C3 C4 120.09(10) . . ?
C2 C3 N1 120.00(11) . . ?
C2 C3 C4 119.90(11) . . ?
C5 C4 C3 124.82(11) . . ?
C9 C4 C3 116.97(11) . . ?
C9 C4 C5 118.20(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.48(12) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.98(12) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.77(12) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.87(12) . . ?
C9 C8 H8 120.6 . . ?
O2 C9 C4 122.29(11) . . ?
O2 C9 C8 116.03(11) . . ?
C8 C9 C4 121.68(11) . . ?
C2 C10 H10A 109.6 . . ?
C2 C10 H10B 109.6 . . ?
C2 C10 C11 110.05(10) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
N2 C11 C10 125.52(11) . . ?
N2 C11 C12 116.74(11) . . ?
C12 C11 C10 117.65(10) . . ?
N3 C12 C11 114.85(10) . . ?
N3 C12 C13 122.55(11) . . ?
C13 C12 C11 122.50(11) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.49(12) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.35(12) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 120.9 . . ?
C16 C15 C14 118.24(12) . . ?
C16 C15 H15 120.9 . . ?
N3 C16 C15 123.55(12) . . ?
N3 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C25 O4 C17 121.27(9) . . ?
N5 N4 H4 118.2 . . ?
C19 N4 H4 118.2 . . ?
C19 N4 N5 123.64(10) . . ?
C27 N5 N4 118.26(10) . . ?
C32 N6 C28 117.15(11) . . ?
O3 C17 O4 116.29(11) . . ?
O3 C17 C18 125.61(11) . . ?
O4 C17 C18 118.10(10) . . ?
C17 C18 C26 117.52(10) . . ?
C19 C18 C17 121.25(11) . . ?
C19 C18 C26 121.19(10) . . ?
N4 C19 C18 120.38(11) . . ?
N4 C19 C20 119.57(10) . . ?
C18 C19 C20 120.05(10) . . ?
C21 C20 C19 124.81(11) . . ?
C25 C20 C19 117.06(11) . . ?
C25 C20 C21 118.10(11) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.53(11) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.04(12) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.53(11) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.14(11) . . ?
C25 C24 H24 120.4 . . ?
O4 C25 C20 122.19(11) . . ?
O4 C25 C24 116.16(10) . . ?
C24 C25 C20 121.65(11) . . ?
C18 C26 H26A 109.6 . . ?
C18 C26 H26B 109.6 . . ?
C18 C26 C27 110.13(10) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.6 . . ?
C27 C26 H26B 109.6 . . ?
N5 C27 C26 126.36(11) . . ?
N5 C27 C28 116.23(10) . . ?
C28 C27 C26 117.41(10) . . ?
N6 C28 C27 115.21(10) . . ?
N6 C28 C29 122.63(11) . . ?
C29 C28 C27 122.15(11) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 118.93(12) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.82(12) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 H31 120.9 . . ?
C32 C31 C30 118.17(12) . . ?
C32 C31 H31 120.9 . . ?
N6 C32 C31 124.24(13) . . ?
N6 C32 H32 117.9 . . ?
C31 C32 H32 117.9 . . ?
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 C1 1.2192(15) . ?
O2 C1 1.3764(14) . ?
O2 C9 1.3713(14) . ?
N1 H1 0.8800 . ?
N1 N2 1.3828(14) . ?
N1 C3 1.3647(16) . ?
N2 C11 1.2868(16) . ?
N3 C12 1.3437(16) . ?
N3 C16 1.3438(16) . ?
C1 C2 1.4295(17) . ?
C2 C3 1.3643(16) . ?
C2 C10 1.4983(16) . ?
C3 C4 1.4534(16) . ?
C4 C5 1.4061(17) . ?
C4 C9 1.3970(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3832(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3840(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.3908(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5070(16) . ?
C11 C12 1.4840(16) . ?
C12 C13 1.3982(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3848(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3825(19) . ?
C16 H16 0.9500 . ?
O3 C17 1.2160(15) . ?
O4 C17 1.3833(15) . ?
O4 C25 1.3733(14) . ?
N4 H4 0.8800 . ?
N4 N5 1.3750(14) . ?
N4 C19 1.3614(15) . ?
N5 C27 1.2873(16) . ?
N6 C28 1.3381(16) . ?
N6 C32 1.3358(16) . ?
C17 C18 1.4304(16) . ?
C18 C19 1.3656(16) . ?
C18 C26 1.5003(16) . ?
C19 C20 1.4528(16) . ?
C20 C21 1.4054(17) . ?
C20 C25 1.3950(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.3818(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.3925(18) . ?
C23 H23 0.9500 . ?
C23 C24 1.3813(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.3880(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5098(16) . ?
C27 C28 1.4785(16) . ?
C28 C29 1.3962(17) . ?
C29 H29 0.9500 . ?
C29 C30 1.3824(18) . ?
C30 H30 0.9500 . ?
C30 C31 1.3821(19) . ?
C31 H31 0.9500 . ?
C31 C32 1.3814(19) . ?
C32 H32 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 C1 C2 C3 178.74(12) . . . . ?
O1 C1 C2 C10 -0.77(19) . . . . ?
O2 C1 C2 C3 -0.09(17) . . . . ?
O2 C1 C2 C10 -179.60(10) . . . . ?
N1 N2 C11 C10 1.50(18) . . . . ?
N1 N2 C11 C12 -174.89(10) . . . . ?
N1 C3 C4 C5 -1.41(18) . . . . ?
N1 C3 C4 C9 179.54(11) . . . . ?
N2 N1 C3 C2 -15.09(17) . . . . ?
N2 N1 C3 C4 164.65(11) . . . . ?
N2 C11 C12 N3 -177.74(11) . . . . ?
N2 C11 C12 C13 5.81(17) . . . . ?
N3 C12 C13 C14 -3.97(18) . . . . ?
C1 O2 C9 C4 0.08(17) . . . . ?
C1 O2 C9 C8 -179.25(11) . . . . ?
C1 C2 C3 N1 -179.69(11) . . . . ?
C1 C2 C3 C4 0.58(18) . . . . ?
C1 C2 C10 C11 -167.24(10) . . . . ?
C2 C3 C4 C5 178.33(11) . . . . ?
C2 C3 C4 C9 -0.72(17) . . . . ?
C2 C10 C11 N2 -14.41(17) . . . . ?
C2 C10 C11 C12 161.95(10) . . . . ?
C3 N1 N2 C11 14.46(17) . . . . ?
C3 C2 C10 C11 13.25(16) . . . . ?
C3 C4 C5 C6 -178.39(12) . . . . ?
C3 C4 C9 O2 0.40(17) . . . . ?
C3 C4 C9 C8 179.70(11) . . . . ?
C4 C5 C6 C7 -1.3(2) . . . . ?
C5 C4 C9 O2 -178.71(11) . . . . ?
C5 C4 C9 C8 0.58(18) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 O2 178.16(11) . . . . ?
C7 C8 C9 C4 -1.17(19) . . . . ?
C9 O2 C1 O1 -179.18(11) . . . . ?
C9 O2 C1 C2 -0.25(17) . . . . ?
C9 C4 C5 C6 0.65(18) . . . . ?
C10 C2 C3 N1 -0.19(17) . . . . ?
C10 C2 C3 C4 -179.93(10) . . . . ?
C10 C11 C12 N3 5.57(15) . . . . ?
C10 C11 C12 C13 -170.88(11) . . . . ?
C11 C12 C13 C14 172.21(11) . . . . ?
C12 N3 C16 C15 0.58(19) . . . . ?
C12 C13 C14 C15 1.64(18) . . . . ?
C13 C14 C15 C16 1.51(18) . . . . ?
C14 C15 C16 N3 -2.75(19) . . . . ?
C16 N3 C12 C11 -173.60(11) . . . . ?
C16 N3 C12 C13 2.84(18) . . . . ?
O3 C17 C18 C19 178.90(12) . . . . ?
O3 C17 C18 C26 1.10(19) . . . . ?
O4 C17 C18 C19 -0.21(18) . . . . ?
O4 C17 C18 C26 -178.01(10) . . . . ?
N4 N5 C27 C26 0.45(18) . . . . ?
N4 N5 C27 C28 -179.17(10) . . . . ?
N4 C19 C20 C21 -2.38(18) . . . . ?
N4 C19 C20 C25 179.57(11) . . . . ?
N5 N4 C19 C18 -0.86(18) . . . . ?
N5 N4 C19 C20 178.82(11) . . . . ?
N5 C27 C28 N6 -171.36(11) . . . . ?
N5 C27 C28 C29 9.86(17) . . . . ?
N6 C28 C29 C30 -2.49(19) . . . . ?
C17 O4 C25 C20 3.53(17) . . . . ?
C17 O4 C25 C24 -176.07(11) . . . . ?
C17 C18 C19 N4 -178.56(11) . . . . ?
C17 C18 C19 C20 1.77(17) . . . . ?
C17 C18 C26 C27 179.79(10) . . . . ?
C18 C19 C20 C21 177.30(11) . . . . ?
C18 C19 C20 C25 -0.76(17) . . . . ?
C18 C26 C27 N5 -1.87(17) . . . . ?
C18 C26 C27 C28 177.75(10) . . . . ?
C19 N4 N5 C27 1.07(18) . . . . ?
C19 C18 C26 C27 1.98(15) . . . . ?
C19 C20 C21 C22 -177.95(11) . . . . ?
C19 C20 C25 O4 -1.87(17) . . . . ?
C19 C20 C25 C24 177.71(11) . . . . ?
C20 C21 C22 C23 0.64(19) . . . . ?
C21 C20 C25 O4 179.94(11) . . . . ?
C21 C20 C25 C24 -0.48(18) . . . . ?
C21 C22 C23 C24 -1.00(19) . . . . ?
C22 C23 C24 C25 0.61(19) . . . . ?
C23 C24 C25 O4 179.74(11) . . . . ?
C23 C24 C25 C20 0.14(18) . . . . ?
C25 O4 C17 O3 178.38(11) . . . . ?
C25 O4 C17 C18 -2.43(17) . . . . ?
C25 C20 C21 C22 0.09(18) . . . . ?
C26 C18 C19 N4 -0.84(17) . . . . ?
C26 C18 C19 C20 179.49(10) . . . . ?
C26 C27 C28 N6 8.98(16) . . . . ?
C26 C27 C28 C29 -169.79(11) . . . . ?
C27 C28 C29 C30 176.19(11) . . . . ?
C28 N6 C32 C31 1.5(2) . . . . ?
C28 C29 C30 C31 1.44(19) . . . . ?
C29 C30 C31 C32 0.9(2) . . . . ?
C30 C31 C32 N6 -2.5(2) . . . . ?
C32 N6 C28 C27 -177.73(11) . . . . ?
C32 N6 C28 C29 1.04(19) . . . . ?
