##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'by CrystalStructure 4.2.2'
_journal_date_recd_electronic     2016-11-05
_journal_date_accepted     2016-11-07
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HM
_journal_paper_doi     10.1107/S241431461601779X
_journal_coeditor_code     BT4032
_publ_contact_author_name     'Hideki Ohtsu'
_publ_contact_author_address
;
Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku,
Toyama 930-8555,
Japan
;
_publ_contact_author_email     'ohtsu@sci.u-toyama.ac.jp'
_publ_contact_author_fax     '+81-76-445-6549'
_publ_contact_author_phone     '+81-76-445-6580'
_publ_section_title
;\
[2-(2,2'-Bipyridin-6-yl-κ²N¹,N^1'^)benzo[b][1,5]\
naphthyridine-κN¹]dichloridozinc
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tezuka, Yosuke' .
;
Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku,
Toyama 930-8555,
Japan
;
    'Tsuge, Kiyoshi' .
;
Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku,
Toyama 930-8555,
Japan
;
    'Ohtsu, Hideki' .
;
Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku,
Toyama 930-8555,
Japan
;
_publ_section_synopsis
;
In the title complex bearing a new NAD⁺/NADH-analogous ligand bbn,
[Zn(C₂₂H₁₄N₄)Cl₂], the zinc(II) ion has a distorted
trigonal--bipyramidal environment, coordinated by three N atoms from the bbn
ligand and two Cl⁻ ions.
;
_database_code_depnum_ccdc_archive     'CCDC 1511041'
data_I
_chemical_name_systematic
;\
[2-(2,2'-Bipyridin-6-yl-κ²N¹,N^1'^)benzo[b]\
[1,5]naphthyridine-κN¹]dichloridozinc
;
_chemical_formula_moiety     'C22 H14 Cl2 N4 Zn'
_chemical_formula_sum     'C22 H14 Cl2 N4 Zn'
_chemical_formula_iupac     '[Zn Cl2 (C22 H14 N4)]'
_chemical_formula_weight     470.67
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_id
    _space_group_symop_operation_xyz
    1 '+X,+Y,+Z'
    2 '1/2-X,1/2+Y,1/2-Z'
    3 '-X,-Y,-Z'
    4 '-1/2+X,-1/2-Y,-1/2+Z'
_cell_length_a     10.8040(2)
_cell_length_b     13.6433(3)
_cell_length_c     13.2159(3)
_cell_angle_alpha     90.0000
_cell_angle_beta     97.8812(7)
_cell_angle_gamma     90.0000
_cell_volume     1929.65(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     16370
_cell_measurement_theta_min     3.02
_cell_measurement_theta_max     27.44
_cell_measurement_temperature     173
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.080
_exptl_crystal_size_mid     0.080
_exptl_crystal_size_min     0.070
_exptl_crystal_density_diffrn     1.620
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     952.00
_exptl_absorpt_coefficient_mu     1.566
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_absorpt_correction_T_min     0.718
_exptl_absorpt_correction_T_max     0.896
_diffrn_ambient_temperature     173
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.000
_diffrn_reflns_number     18736
_diffrn_reflns_av_R_equivalents     0.0256
_diffrn_reflns_theta_min     3.014
_diffrn_reflns_theta_max     27.440
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
    Refinement was performed using all reflections. The weighted
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total     4400
_reflns_number_gt     4050
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.0415
_refine_ls_R_factor_gt     0.0381
_refine_ls_wR_factor_gt     0.0955
_refine_ls_wR_factor_ref     0.0972
_refine_ls_goodness_of_fit_ref     1.119
_refine_ls_number_reflns     4400
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0424P)²+2.0040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_diff_density_max     0.95
_refine_diff_density_min     -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'H' 'H' 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
    'N' 'N' 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'Zn' 'Zn' 0.2839 1.4301
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'Cl' 'Cl' 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2001)
;
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2001)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2001)
;
_computing_structure_solution
;
SIR2011 (Burla et al.,  2012)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
CrystalStructure (Rigaku, 2016), Mercury (Macrae et al.,
2008) and
CrystalMaker (Palmer, 2007)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2016) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Zn ZN1 0.14600(3) 0.22246(2) 0.60516(2) 0.02931(10) Uani d 1 . .
    Cl CL1 0.35323(6) 0.19462(5) 0.60386(5) 0.04174(16) Uani d 1 . .
    Cl CL2 0.00807(7) 0.17449(5) 0.47109(5) 0.03958(16) Uani d 1 . .
    N N1 0.10596(19) 0.10447(16) 0.70834(14) 0.0311(4) Uani d 1 . .
    N N2 0.09581(19) 0.29423(16) 0.73276(16) 0.0323(4) Uani d 1 . .
    N N3 0.15042(19) 0.38149(15) 0.56697(16) 0.0317(4) Uani d 1 . .
    N N4 0.2032(2) 0.56306(16) 0.3716(2) 0.0424(5) Uani d 1 . .
    C C1 0.1099(2) 0.00880(19) 0.68850(19) 0.0342(5) Uani d 1 . .
    H H1 0.132729 -0.011245 0.624729 0.041 Uiso calc 1 . .
    C C2 0.0824(3) -0.0629(2) 0.7564(2) 0.0387(6) Uani d 1 . .
    H H2 0.087495 -0.130494 0.740161 0.046 Uiso calc 1 . .
    C C3 0.0476(3) -0.0333(2) 0.8480(2) 0.0423(6) Uani d 1 . .
    H H3 0.028589 -0.080493 0.896416 0.051 Uiso calc 1 . .
    C C4 0.0406(3) 0.0652(2) 0.86885(19) 0.0406(6) Uani d 1 . .
    H H4 0.014766 0.086496 0.931137 0.049 Uiso calc 1 . .
    C C5 0.0715(2) 0.1336(2) 0.79818(18) 0.0324(5) Uani d 1 . .
    C C6 0.0691(2) 0.2413(2) 0.81226(19) 0.0351(5) Uani d 1 . .
    C C7 0.0414(3) 0.2863(2) 0.9013(2) 0.0470(7) Uani d 1 . .
    H H7 0.021399 0.248685 0.957327 0.056 Uiso calc 1 . .
    C C8 0.0440(3) 0.3871(3) 0.9053(2) 0.0526(8) Uani d 1 . .
    H H8 0.026562 0.419459 0.965325 0.063 Uiso calc 1 . .
    C C9 0.0717(3) 0.4421(2) 0.8232(2) 0.0454(7) Uani d 1 . .
    H H9 0.073696 0.511692 0.826419 0.055 Uiso calc 1 . .
    C C10 0.0967(2) 0.3928(2) 0.7355(2) 0.0358(5) Uani d 1 . .
    C C11 0.1253(2) 0.44115(18) 0.6410(2) 0.0341(5) Uani d 1 . .
    C C12 0.1246(2) 0.54527(19) 0.6295(2) 0.0386(6) Uani d 1 . .
    H H12 0.105882 0.586341 0.683423 0.046 Uiso calc 1 . .
    C C13 0.1508(2) 0.58476(19) 0.5410(2) 0.0418(6) Uani d 1 . .
    H H13 0.150643 0.653960 0.533003 0.050 Uiso calc 1 . .
    C C14 0.2521(3) 0.5421(2) 0.2008(3) 0.0526(8) Uani d 1 . .
    H H14 0.254409 0.611196 0.192511 0.063 Uiso calc 1 . .
    C C15 0.2746(3) 0.4838(3) 0.1234(2) 0.0535(8) Uani d 1 . .
    H H15 0.294094 0.512598 0.062067 0.064 Uiso calc 1 . .
    C C16 0.2700(3) 0.3804(3) 0.1316(2) 0.0472(7) Uani d 1 . .
    H H16 0.285278 0.340550 0.075634 0.057 Uiso calc 1 . .
    C C17 0.2437(3) 0.3380(2) 0.2195(2) 0.0427(6) Uani d 1 . .
    H H17 0.240144 0.268636 0.224379 0.051 Uiso calc 1 . .
    C C18 0.1986(2) 0.35777(18) 0.3966(2) 0.0350(5) Uani d 1 . .
    H H18 0.197990 0.288697 0.405575 0.042 Uiso calc 1 . .
    C C19 0.1787(2) 0.52359(18) 0.4595(2) 0.0353(5) Uani d 1 . .
    C C20 0.1766(2) 0.41966(17) 0.47647(19) 0.0316(5) Uani d 1 . .
    C C21 0.2247(2) 0.5025(2) 0.2952(2) 0.0386(6) Uani d 1 . .
    C C22 0.2214(2) 0.39714(19) 0.3045(2) 0.0348(5) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    ZN1 N2 . 2.085(2) ?
    ZN1 N1 . 2.191(2) ?
    ZN1 N3 . 2.230(2) ?
    ZN1 CL2 . 2.2504(7) ?
    ZN1 CL1 . 2.2732(7) ?
    N1 C1 . 1.333(3) ?
    N1 C5 . 1.352(3) ?
    N2 C6 . 1.339(3) ?
    N2 C10 . 1.345(3) ?
    N3 C11 . 1.329(3) ?
    N3 C20 . 1.369(3) ?
    N4 C19 . 1.340(4) ?
    N4 C21 . 1.349(4) ?
    C1 C2 . 1.387(4) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.377(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.377(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.393(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.481(4) ?
    C6 C7 . 1.396(4) ?
    C7 C8 . 1.375(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.385(5) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.398(4) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.482(4) ?
    C11 C12 . 1.429(4) ?
    C12 C13 . 1.352(4) ?
    C12 H12 . 0.9500 ?
    C13 C19 . 1.427(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.344(5) ?
    C14 C21 . 1.427(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.417(5) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.363(4) ?
    C16 H16 . 0.9500 ?
    C17 C22 . 1.430(4) ?
    C17 H17 . 0.9500 ?
    C18 C22 . 1.383(4) ?
    C18 C20 . 1.397(4) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.436(3) ?
    C21 C22 . 1.444(4) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 ZN1 N1 . . 75.30(8) ?
    N2 ZN1 N3 . . 75.05(8) ?
    N1 ZN1 N3 . . 150.24(8) ?
    N2 ZN1 CL2 . . 123.76(6) ?
    N1 ZN1 CL2 . . 96.34(6) ?
    N3 ZN1 CL2 . . 97.88(5) ?
    N2 ZN1 CL1 . . 116.76(6) ?
    N1 ZN1 CL1 . . 99.25(6) ?
    N3 ZN1 CL1 . . 96.27(6) ?
    CL2 ZN1 CL1 . . 119.48(3) ?
    C1 N1 C5 . . 118.7(2) ?
    C1 N1 ZN1 . . 125.63(16) ?
    C5 N1 ZN1 . . 115.62(17) ?
    C6 N2 C10 . . 121.3(2) ?
    C6 N2 ZN1 . . 119.28(17) ?
    C10 N2 ZN1 . . 119.31(18) ?
    C11 N3 C20 . . 119.8(2) ?
    C11 N3 ZN1 . . 114.62(18) ?
    C20 N3 ZN1 . . 125.54(16) ?
    C19 N4 C21 . . 118.5(2) ?
    N1 C1 C2 . . 123.2(2) ?
    N1 C1 H1 . . 118.4 ?
    C2 C1 H1 . . 118.4 ?
    C3 C2 C1 . . 118.1(3) ?
    C3 C2 H2 . . 121.0 ?
    C1 C2 H2 . . 121.0 ?
    C4 C3 C2 . . 119.5(3) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 119.7(2) ?
    C3 C4 H4 . . 120.2 ?
    C5 C4 H4 . . 120.2 ?
    N1 C5 C4 . . 120.8(2) ?
    N1 C5 C6 . . 114.4(2) ?
    C4 C5 C6 . . 124.8(2) ?
    N2 C6 C7 . . 121.2(3) ?
    N2 C6 C5 . . 115.3(2) ?
    C7 C6 C5 . . 123.5(3) ?
    C8 C7 C6 . . 117.8(3) ?
    C8 C7 H7 . . 121.1 ?
    C6 C7 H7 . . 121.1 ?
    C7 C8 C9 . . 121.2(3) ?
    C7 C8 H8 . . 119.4 ?
    C9 C8 H8 . . 119.4 ?
    C8 C9 C10 . . 118.3(3) ?
    C8 C9 H9 . . 120.8 ?
    C10 C9 H9 . . 120.8 ?
    N2 C10 C9 . . 120.1(3) ?
    N2 C10 C11 . . 115.1(2) ?
    C9 C10 C11 . . 124.8(3) ?
    N3 C11 C12 . . 122.0(3) ?
    N3 C11 C10 . . 115.8(2) ?
    C12 C11 C10 . . 122.2(2) ?
    C13 C12 C11 . . 119.3(3) ?
    C13 C12 H12 . . 120.4 ?
    C11 C12 H12 . . 120.4 ?
    C12 C13 C19 . . 120.7(2) ?
    C12 C13 H13 . . 119.6 ?
    C19 C13 H13 . . 119.6 ?
    C15 C14 C21 . . 121.5(3) ?
    C15 C14 H14 . . 119.2 ?
    C21 C14 H14 . . 119.2 ?
    C14 C15 C16 . . 121.3(3) ?
    C14 C15 H15 . . 119.4 ?
    C16 C15 H15 . . 119.4 ?
    C17 C16 C15 . . 120.1(3) ?
    C17 C16 H16 . . 120.0 ?
    C15 C16 H16 . . 120.0 ?
    C16 C17 C22 . . 120.5(3) ?
    C16 C17 H17 . . 119.7 ?
    C22 C17 H17 . . 119.7 ?
    C22 C18 C20 . . 120.0(2) ?
    C22 C18 H18 . . 120.0 ?
    C20 C18 H18 . . 120.0 ?
    N4 C19 C13 . . 120.5(2) ?
    N4 C19 C20 . . 122.8(2) ?
    C13 C19 C20 . . 116.7(2) ?
    N3 C20 C18 . . 120.5(2) ?
    N3 C20 C19 . . 121.4(2) ?
    C18 C20 C19 . . 118.1(2) ?
    N4 C21 C14 . . 120.0(3) ?
    N4 C21 C22 . . 122.5(2) ?
    C14 C21 C22 . . 117.5(3) ?
    C18 C22 C17 . . 122.8(2) ?
    C18 C22 C21 . . 118.1(2) ?
    C17 C22 C21 . . 119.1(2) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 N1 C1 C2 . . . . -1.1(4) ?
    ZN1 N1 C1 C2 . . . . -179.35(19) ?
    N1 C1 C2 C3 . . . . 1.0(4) ?
    C1 C2 C3 C4 . . . . 0.4(4) ?
    C2 C3 C4 C5 . . . . -1.5(4) ?
    C1 N1 C5 C4 . . . . 0.0(3) ?
    ZN1 N1 C5 C4 . . . . 178.34(19) ?
    C1 N1 C5 C6 . . . . -179.5(2) ?
    ZN1 N1 C5 C6 . . . . -1.2(3) ?
    C3 C4 C5 N1 . . . . 1.3(4) ?
    C3 C4 C5 C6 . . . . -179.2(2) ?
    C10 N2 C6 C7 . . . . -0.1(4) ?
    ZN1 N2 C6 C7 . . . . 176.6(2) ?
    C10 N2 C6 C5 . . . . 179.9(2) ?
    ZN1 N2 C6 C5 . . . . -3.3(3) ?
    N1 C5 C6 N2 . . . . 2.9(3) ?
    C4 C5 C6 N2 . . . . -176.6(2) ?
    N1 C5 C6 C7 . . . . -177.1(3) ?
    C4 C5 C6 C7 . . . . 3.4(4) ?
    N2 C6 C7 C8 . . . . -0.9(4) ?
    C5 C6 C7 C8 . . . . 179.1(3) ?
    C6 C7 C8 C9 . . . . 0.8(5) ?
    C7 C8 C9 C10 . . . . 0.2(5) ?
    C6 N2 C10 C9 . . . . 1.2(4) ?
    ZN1 N2 C10 C9 . . . . -175.60(19) ?
    C6 N2 C10 C11 . . . . -178.8(2) ?
    ZN1 N2 C10 C11 . . . . 4.5(3) ?
    C8 C9 C10 N2 . . . . -1.2(4) ?
    C8 C9 C10 C11 . . . . 178.7(3) ?
    C20 N3 C11 C12 . . . . 0.0(3) ?
    ZN1 N3 C11 C12 . . . . 179.77(18) ?
    C20 N3 C11 C10 . . . . 179.3(2) ?
    ZN1 N3 C11 C10 . . . . -0.9(3) ?
    N2 C10 C11 N3 . . . . -2.2(3) ?
    C9 C10 C11 N3 . . . . 177.9(2) ?
    N2 C10 C11 C12 . . . . 177.2(2) ?
    C9 C10 C11 C12 . . . . -2.8(4) ?
    N3 C11 C12 C13 . . . . -0.3(4) ?
    C10 C11 C12 C13 . . . . -179.6(2) ?
    C11 C12 C13 C19 . . . . 0.2(4) ?
    C21 C14 C15 C16 . . . . 1.1(5) ?
    C14 C15 C16 C17 . . . . -0.8(5) ?
    C15 C16 C17 C22 . . . . -0.4(5) ?
    C21 N4 C19 C13 . . . . -177.6(2) ?
    C21 N4 C19 C20 . . . . 1.3(4) ?
    C12 C13 C19 N4 . . . . 179.3(2) ?
    C12 C13 C19 C20 . . . . 0.3(4) ?
    C11 N3 C20 C18 . . . . -177.6(2) ?
    ZN1 N3 C20 C18 . . . . 2.6(3) ?
    C11 N3 C20 C19 . . . . 0.5(3) ?
    ZN1 N3 C20 C19 . . . . -179.22(17) ?
    C22 C18 C20 N3 . . . . 178.1(2) ?
    C22 C18 C20 C19 . . . . -0.1(4) ?
    N4 C19 C20 N3 . . . . -179.6(2) ?
    C13 C19 C20 N3 . . . . -0.7(3) ?
    N4 C19 C20 C18 . . . . -1.4(4) ?
    C13 C19 C20 C18 . . . . 177.5(2) ?
    C19 N4 C21 C14 . . . . -179.5(2) ?
    C19 N4 C21 C22 . . . . 0.3(4) ?
    C15 C14 C21 N4 . . . . 179.6(3) ?
    C15 C14 C21 C22 . . . . -0.3(4) ?
    C20 C18 C22 C17 . . . . -179.5(2) ?
    C20 C18 C22 C21 . . . . 1.6(4) ?
    C16 C17 C22 C18 . . . . -177.7(3) ?
    C16 C17 C22 C21 . . . . 1.2(4) ?
    N4 C21 C22 C18 . . . . -1.8(4) ?
    C14 C21 C22 C18 . . . . 178.1(3) ?
    N4 C21 C22 C17 . . . . 179.3(2) ?
    C14 C21 C22 C17 . . . . -0.9(4) ?
