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#$Date: 2024-07-05 20:46:09 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293219 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/31/7063142.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_7063142
loop_
_publ_author_name
'Wang, Fei'
'Zhang, Yi'
'Zhou, Wei'
'Long, Zhiqing'
'Xiong, Shenglun'
'Zhang, Qinpeng'
'Sessler, Jonathan L.'
'He, Qing'
_publ_section_title
;
 “One-pot” synthesis of oligopyrrolic dialdehydes
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8153
_journal_page_last               8157
_journal_paper_doi               10.1039/D4NJ00933A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C22 H26 N4 O2'
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47
_chemical_name_systematic        WF-2
_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             2022-02-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.99(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.852(15)
_cell_length_b                   8.3792(16)
_cell_length_c                   16.947(4)
_cell_measurement_reflns_used    174
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      43.12
_cell_measurement_theta_min      6.34
_cell_volume                     4054(2)
_computing_cell_refinement       'SAINT V8.40C (?, 2016)'
_computing_data_reduction        'SAINT V8.40C (?, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.1291
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11024
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        63.870
_diffrn_reflns_theta_max         63.870
_diffrn_reflns_theta_min         3.096
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_preparation       'THF ANN nhexane'
_exptl_crystal_recrystallization_method 'nhexane to THF'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.0028(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.2199
_refine_ls_R_factor_gt           0.1445
_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)+(0.2800P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3864
_refine_ls_wR_factor_ref         0.4465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1537
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00933a2.cif
_cod_data_source_block           cu_20211202_wf_2_0m
_cod_depositor_comments
'Adding full bibliography for 7063139--7063144.cif.'
_cod_database_code               7063142
_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   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C3
 1.51 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C19(H19A,H19B), C16(H16A,H16B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C12(H12), C1(H1A), C22(H22), C11(H11)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C8(H8A,H8B,H8C)
;
_olex2_submission_original_sample_id WF-2
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.4836(2) 1.1440(6) 0.4270(4) 0.0609(17) Uani 1 1 d . . . . .
O1 O 0.4757(2) 0.3704(6) 0.5634(3) 0.0603(17) Uani 1 1 d . . . . .
N4 N 0.5769(3) 1.0251(7) 0.4821(4) 0.0489(18) Uani 1 1 d . . . . .
H4 H 0.558121 0.958051 0.496834 0.059 Uiso 1 1 calc R U . . .
N1 N 0.5718(3) 0.4609(7) 0.5889(4) 0.0495(18) Uani 1 1 d . . . . .
H1 H 0.553509 0.534839 0.559196 0.059 Uiso 1 1 calc R U . . .
N2 N 0.6863(3) 0.5559(8) 0.5757(5) 0.062(2) Uani 1 1 d . . . . .
N3 N 0.6882(3) 0.8179(7) 0.5185(5) 0.062(2) Uani 1 1 d . . . . .
C9 C 0.6192(3) 0.4619(8) 0.6119(5) 0.050(2) Uani 1 1 d . . . . .
C18 C 0.6038(3) 1.2404(8) 0.4308(5) 0.047(2) Uani 1 1 d . . . . .
C15 C 0.6421(3) 1.1356(9) 0.4644(5) 0.053(2) Uani 1 1 d . . . . .
C21 C 0.5636(3) 1.1691(9) 0.4426(5) 0.052(2) Uani 1 1 d . . . . .
C2 C 0.5569(3) 0.3266(8) 0.6194(5) 0.048(2) Uani 1 1 d . . . . .
C6 C 0.6357(3) 0.3258(8) 0.6606(5) 0.054(2) Uani 1 1 d . . . . .
C12 C 0.6229(3) 0.7403(8) 0.5619(5) 0.052(2) Uani 1 1 d . . . . .
H12 H 0.593597 0.764493 0.570441 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6235(3) 1.0031(8) 0.4945(5) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.5951(3) 0.0934(8) 0.7144(5) 0.057(2) Uani 1 1 d D . . . .
H4A H 0.625411 0.036448 0.725879 0.068 Uiso 1 1 calc R U . . .
H4B H 0.570320 0.021849 0.681281 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6459(3) 0.8508(9) 0.5280(5) 0.053(2) Uani 1 1 d . . . . .
C10 C 0.6443(3) 0.5891(9) 0.5839(5) 0.056(2) Uani 1 1 d . . . . .
C3 C 0.5969(3) 0.2412(9) 0.6660(5) 0.056(2) Uani 1 1 d D . . . .
C19 C 0.6050(4) 1.3932(8) 0.3854(5) 0.059(2) Uani 1 1 d . . . . .
H19A H 0.637800 1.430993 0.398744 0.070 Uiso 1 1 calc R U . . .
H19B H 0.586695 1.475274 0.404484 0.070 Uiso 1 1 calc R U . . .
C1 C 0.5085(4) 0.2874(9) 0.6052(5) 0.056(2) Uani 1 1 d . . . . .
H1A H 0.501026 0.192263 0.629174 0.067 Uiso 1 1 calc R U . . .
C22 C 0.5165(3) 1.2206(9) 0.4172(5) 0.053(2) Uani 1 1 d . . . . .
H22 H 0.509848 1.321388 0.390687 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5852(4) 0.1319(11) 0.7961(6) 0.073(3) Uani 1 1 d . . . . .
H5A H 0.555964 0.192462 0.785077 0.109 Uiso 1 1 calc R U . . .
H5B H 0.611043 0.195538 0.830915 0.109 Uiso 1 1 calc R U . . .
H5C H 0.582360 0.032332 0.824577 0.109 Uiso 1 1 calc R U . . .
C16 C 0.6916(3) 1.1647(9) 0.4628(6) 0.062(2) Uani 1 1 d . . . . .
H16A H 0.713359 1.104340 0.508368 0.075 Uiso 1 1 calc R U . . .
H16B H 0.698988 1.279600 0.472406 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7065(4) 0.6738(9) 0.5447(6) 0.068(3) Uani 1 1 d . . . . .
H11 H 0.737068 0.653290 0.540887 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6859(3) 0.2828(10) 0.7001(6) 0.068(3) Uani 1 1 d . . . . .
H7A H 0.703213 0.291678 0.658606 0.082 Uiso 1 1 calc R U . . .
H7B H 0.687737 0.170387 0.718732 0.082 Uiso 1 1 calc R U . . .
C20 C 0.5847(4) 1.3734(10) 0.2896(6) 0.076(3) Uani 1 1 d . . . . .
H20A H 0.590118 1.471567 0.262261 0.114 Uiso 1 1 calc R U . . .
H20B H 0.550953 1.352552 0.275290 0.114 Uiso 1 1 calc R U . . .
H20C H 0.600252 1.283878 0.271218 0.114 Uiso 1 1 calc R U . . .
C17 C 0.6998(4) 1.1152(11) 0.3810(6) 0.072(3) Uani 1 1 d . . . . .
H17A H 0.678900 1.176242 0.335738 0.108 Uiso 1 1 calc R U . . .
H17B H 0.693321 1.000968 0.371742 0.108 Uiso 1 1 calc R U . . .
H17C H 0.732437 1.136669 0.383304 0.108 Uiso 1 1 calc R U . . .
C8 C 0.7093(5) 0.3886(14) 0.7733(9) 0.112(5) Uani 1 1 d . . . . .
H8A H 0.703669 0.500882 0.757287 0.168 Uiso 1 1 calc R U . . .
H8B H 0.743073 0.367818 0.791072 0.168 Uiso 1 1 calc R U . . .
H8C H 0.696234 0.365393 0.818828 0.168 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 0.0181 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'
N N 0.0311 0.0180 '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
C21 N4 H4 125.4 . . ?
C14 N4 H4 125.4 . . ?
C14 N4 C21 109.3(7) . . ?
C9 N1 H1 125.5 . . ?
C9 N1 C2 108.9(7) . . ?
C2 N1 H1 125.5 . . ?
C10 N2 C11 115.6(7) . . ?
C11 N3 C13 116.6(7) . . ?
N1 C9 C6 108.7(7) . . ?
N1 C9 C10 120.3(7) . . ?
C6 C9 C10 131.0(9) . . ?
C15 C18 C19 126.5(8) . . ?
C21 C18 C15 107.4(7) . . ?
C21 C18 C19 125.9(8) . . ?
C18 C15 C16 124.8(7) . . ?
C14 C15 C18 106.1(8) . . ?
C14 C15 C16 129.0(8) . . ?
N4 C21 C18 107.7(7) . . ?
N4 C21 C22 122.3(8) . . ?
C18 C21 C22 129.9(7) . . ?
N1 C2 C3 108.2(8) . . ?
N1 C2 C1 123.3(7) . . ?
C3 C2 C1 128.5(7) . . ?
C9 C6 C7 126.1(8) . . ?
C3 C6 C9 107.2(8) . . ?
C3 C6 C7 126.6(7) . . ?
C13 C12 H12 120.9 . . ?
C13 C12 C10 118.1(8) . . ?
C10 C12 H12 120.9 . . ?
N4 C14 C15 109.4(7) . . ?
N4 C14 C13 120.4(7) . . ?
C15 C14 C13 129.9(9) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.6(7) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
N3 C13 C12 120.8(7) . . ?
N3 C13 C14 117.8(7) . . ?
C12 C13 C14 121.3(8) . . ?
N2 C10 C9 118.1(7) . . ?
N2 C10 C12 121.6(8) . . ?
C12 C10 C9 120.2(9) . . ?
C2 C3 C4 124.4(8) . . ?
C6 C3 C2 106.9(7) . . ?
C6 C3 C4 128.6(8) . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C18 C19 C20 112.4(7) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
O1 C1 C2 123.8(7) . . ?
O1 C1 H1A 118.1 . . ?
C2 C1 H1A 118.1 . . ?
O2 C22 C21 124.4(7) . . ?
O2 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 112.9(8) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
N2 C11 N3 127.3(9) . . ?
N2 C11 H11 116.4 . . ?
N3 C11 H11 116.4 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C6 C7 C8 112.8(9) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O2 C22 1.223(10) . ?
O1 C1 1.241(10) . ?
N4 H4 0.8800 . ?
N4 C21 1.381(9) . ?
N4 C14 1.356(11) . ?
N1 H1 0.8800 . ?
N1 C9 1.354(11) . ?
N1 C2 1.366(9) . ?
N2 C10 1.332(11) . ?
N2 C11 1.340(11) . ?
N3 C13 1.349(11) . ?
N3 C11 1.346(10) . ?
C9 C6 1.410(10) . ?
C9 C10 1.459(11) . ?
C18 C15 1.422(11) . ?
C18 C21 1.405(12) . ?
C18 C19 1.499(11) . ?
C15 C14 1.403(11) . ?
C15 C16 1.508(12) . ?
C21 C22 1.414(12) . ?
C2 C3 1.417(12) . ?
C2 C1 1.433(12) . ?
C6 C3 1.384(12) . ?
C6 C7 1.496(13) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(12) . ?
C12 C10 1.419(10) . ?
C14 C13 1.475(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.496(10) . ?
C4 C5 1.532(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.568(13) . ?
C1 H1A 0.9500 . ?
C22 H22 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.533(13) . ?
C11 H11 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.518(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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
N4 C21 C22 O2 -0.4(12) . . . . ?
N4 C14 C13 N3 162.3(8) . . . . ?
N4 C14 C13 C12 -12.6(12) . . . . ?
N1 C9 C6 C3 0.5(9) . . . . ?
N1 C9 C6 C7 -178.6(8) . . . . ?
N1 C9 C10 N2 -151.4(8) . . . . ?
N1 C9 C10 C12 25.1(11) . . . . ?
N1 C2 C3 C6 -1.6(9) . . . . ?
N1 C2 C3 C4 175.3(7) . . . . ?
N1 C2 C1 O1 0.8(12) . . . . ?
C9 N1 C2 C3 1.9(8) . . . . ?
C9 N1 C2 C1 -179.0(7) . . . . ?
C9 C6 C3 C2 0.7(9) . . . . ?
C9 C6 C3 C4 -176.0(8) . . . . ?
C9 C6 C7 C8 72.5(12) . . . . ?
C18 C15 C14 N4 -1.1(9) . . . . ?
C18 C15 C14 C13 173.0(8) . . . . ?
C18 C15 C16 C17 -82.8(10) . . . . ?
C18 C21 C22 O2 175.7(8) . . . . ?
C15 C18 C21 N4 -0.1(9) . . . . ?
C15 C18 C21 C22 -176.7(8) . . . . ?
C15 C18 C19 C20 101.3(11) . . . . ?
C15 C14 C13 N3 -11.3(13) . . . . ?
C15 C14 C13 C12 173.8(8) . . . . ?
C21 N4 C14 C15 1.1(9) . . . . ?
C21 N4 C14 C13 -173.7(7) . . . . ?
C21 C18 C15 C14 0.7(9) . . . . ?
C21 C18 C15 C16 178.5(8) . . . . ?
C21 C18 C19 C20 -73.8(11) . . . . ?
C2 N1 C9 C6 -1.5(8) . . . . ?
C2 N1 C9 C10 176.9(7) . . . . ?
C6 C9 C10 N2 26.6(13) . . . . ?
C6 C9 C10 C12 -156.9(8) . . . . ?
C14 N4 C21 C18 -0.6(8) . . . . ?
C14 N4 C21 C22 176.3(7) . . . . ?
C14 C15 C16 C17 94.4(10) . . . . ?
C13 N3 C11 N2 3.5(15) . . . . ?
C13 C12 C10 N2 2.9(13) . . . . ?
C13 C12 C10 C9 -173.5(8) . . . . ?
C10 N2 C11 N3 -2.8(14) . . . . ?
C10 C9 C6 C3 -177.7(8) . . . . ?
C10 C9 C6 C7 3.3(14) . . . . ?
C10 C12 C13 N3 -2.2(12) . . . . ?
C10 C12 C13 C14 172.6(7) . . . . ?
C3 C2 C1 O1 179.8(8) . . . . ?
C3 C6 C7 C8 -106.3(11) . . . . ?
C19 C18 C15 C14 -175.1(7) . . . . ?
C19 C18 C15 C16 2.6(13) . . . . ?
C19 C18 C21 N4 175.8(7) . . . . ?
C19 C18 C21 C22 -0.8(13) . . . . ?
C1 C2 C3 C6 179.4(7) . . . . ?
C1 C2 C3 C4 -3.8(13) . . . . ?
C5 C4 C3 C2 -77.6(11) . . . . ?
C5 C4 C3 C6 98.5(11) . . . . ?
C16 C15 C14 N4 -178.7(8) . . . . ?
C16 C15 C14 C13 -4.6(15) . . . . ?
C11 N2 C10 C9 175.8(8) . . . . ?
C11 N2 C10 C12 -0.6(12) . . . . ?
C11 N3 C13 C12 -0.8(13) . . . . ?
C11 N3 C13 C14 -175.8(8) . . . . ?
C7 C6 C3 C2 179.7(8) . . . . ?
C7 C6 C3 C4 3.0(15) . . . . ?
