##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2009-03-24
_journal_date_accepted     2009-04-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     m578
_journal_page_last     m578
_journal_paper_category     QM
_journal_coeditor_code     RK2135
_publ_contact_author_name     'Dr Chu-Chieh Lin'
_publ_contact_author_address
;
Department of Chemistry
National Chung Hsing University
Taichung 402
Taiwan, R.O.C.
;
_publ_contact_author_email     cchlin@mail.nchu.edu.tw
_publ_contact_author_fax     '886-4-22862547'
_publ_contact_author_phone     '886-4-22840411ext718'
_publ_section_title
;\
(2,2'-Bipyridine)(2-{1-[2-(dimethylamino)ethylimino]ethyl}-4-methoxyphenolato)\
copper(II) perchlorate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tsai, Yueh-Hsuan' ?
;
Department of Chemistry,
National Chung Hsing University,
Taichung 402,
Taiwan
Republic of China
;
    'Hung, Wen-Chou' ?
;
Department of Chemistry,
National Chung Hsing University,
Taichung 402,
Taiwan
Republic of China
;
    'Lin, Chu-Chieh' ?
;
Department of Chemistry,
National Chung Hsing University,
Taichung 402,
Taiwan
Republic of China
;
data_I
_chemical_name_systematic
;
(2,2'-Bipyridine)(2-{1-[2-(dimethylamino)ethylimino]ethyl}-4-
methoxyphenolato)copper(II) perchlorate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H27 Cu N4 O2 +, Cl O4 -'
_chemical_formula_sum     'C23 H27 Cl Cu N4 O6'
_chemical_formula_iupac     '[Cu (C13 H19 N2 O2) (C10 H8 N2)] Cl O4'
_chemical_formula_weight     554.49
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.1588(10)
_cell_length_b     18.2163(17)
_cell_length_c     13.3764(13)
_cell_angle_alpha     90.00
_cell_angle_beta     92.610(2)
_cell_angle_gamma     90.00
_cell_volume     2472.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4710
_cell_measurement_theta_min     2.2975
_cell_measurement_theta_max     25.563
_cell_measurement_temperature     293(2)
_exptl_crystal_description     parallelpiped
_exptl_crystal_colour     green
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.489
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1148
_exptl_absorpt_coefficient_mu     1.037
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.7193
_exptl_absorpt_correction_T_max     0.8599
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine--focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13946
_diffrn_reflns_av_R_equivalents     0.0367
_diffrn_reflns_av_sigmaI/netI     0.0400
_diffrn_reflns_theta_min     1.89
_diffrn_reflns_theta_max     26.01
_diffrn_reflns_theta_full     26.01
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections. The weighted
 R--factor wR and goodness of fit S are based on
 F², conventional R--factors R are based on F,
 with F set to zero for negative F². The threshold expression
 of F² > σ(F²) is used only for calculating
 R--factors(gt) etc. and is not relevant to the choice of
 reflections for refinement. R--factors based on F² are
 statistically about twice as large as those based on F, and
 R--factors based on ALL data will be even larger.
;
_reflns_number_total     4859
_reflns_number_gt     3488
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0605
_refine_ls_R_factor_gt     0.0377
_refine_ls_wR_factor_gt     0.0935
_refine_ls_wR_factor_ref     0.1049
_refine_ls_goodness_of_fit_ref     0.981
_refine_ls_restrained_S_all     0.981
_refine_ls_number_reflns     4859
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                   'calc w=1/[σ²(Fo²)+(0.06P)²] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.332
_refine_diff_density_min     -0.300
_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 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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cu' 'Cu' 0.3201 1.2651
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SMART (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cu Cu 0.62390(3) 0.172001(16) 0.82971(2) 0.04095(12) Uani d . 1 . .
    O O1 0.6832(2) 0.15346(10) 0.96441(14) 0.0532(5) Uani d . 1 . .
    O O2 0.9049(3) -0.10697(14) 1.0997(2) 0.1017(10) Uani d . 1 . .
    N N1 0.5494(2) 0.07290(12) 0.81586(16) 0.0457(5) Uani d . 1 . .
    N N2 0.4979(2) 0.19843(13) 0.70841(18) 0.0528(6) Uani d . 1 . .
    N N3 0.8094(2) 0.16361(12) 0.75071(17) 0.0469(6) Uani d . 1 . .
    N N4 0.6989(2) 0.27569(11) 0.84447(15) 0.0412(5) Uani d . 1 . .
    C C1 0.7293(3) 0.08881(15) 0.9916(2) 0.0455(6) Uani d . 1 . .
    C C2 0.8227(3) 0.08568(17) 1.0724(2) 0.0583(8) Uani d . 1 . .
    H H2A 0.8483 0.1293 1.1039 0.070 Uiso calc R 1 . .
    C C3 0.8779(4) 0.02114(19) 1.1069(2) 0.0681(9) Uani d . 1 . .
    H H3A 0.9395 0.0215 1.1605 0.082 Uiso calc R 1 . .
    C C4 0.8411(4) -0.04469(18) 1.0612(2) 0.0665(9) Uani d . 1 . .
    C C5 0.7497(3) -0.04455(16) 0.9842(2) 0.0576(8) Uani d . 1 . .
    H H5A 0.7257 -0.0890 0.9544 0.069 Uiso calc R 1 . .
    C C6 0.6895(3) 0.02080(15) 0.94751(19) 0.0439(6) Uani d . 1 . .
    C C7 0.5849(3) 0.01591(15) 0.8687(2) 0.0447(7) Uani d . 1 . .
    C C8 0.5192(3) -0.05759(16) 0.8497(2) 0.0605(8) Uani d . 1 . .
    H H8A 0.5193 -0.0850 0.9111 0.079(10) Uiso calc R 1 . .
    H H8B 0.5666 -0.0844 0.8011 0.102(13) Uiso calc R 1 . .
    H H8C 0.4300 -0.0500 0.8250 0.098(13) Uiso calc R 1 . .
    C C9 0.4456(3) 0.06785(18) 0.7363(2) 0.0629(8) Uani d . 1 . .
    H H9A 0.3599 0.0752 0.7639 0.075 Uiso calc R 1 . .
    H H9B 0.4469 0.0197 0.7054 0.075 Uiso calc R 1 . .
    C C10 0.4709(3) 0.12658(16) 0.6597(2) 0.0603(8) Uani d . 1 . .
    H H10A 0.5457 0.1125 0.6214 0.072 Uiso calc R 1 . .
    H H10B 0.3947 0.1309 0.6137 0.072 Uiso calc R 1 . .
    C C11 0.3779(4) 0.2319(2) 0.7440(3) 0.0901(13) Uani d . 1 . .
    H H11A 0.3197 0.2441 0.6879 0.135 Uiso calc R 1 . .
    H H11B 0.4002 0.2758 0.7809 0.135 Uiso calc R 1 . .
    H H11C 0.3349 0.1980 0.7867 0.135 Uiso calc R 1 . .
    C C12 0.5537(4) 0.24885(18) 0.6336(2) 0.0728(10) Uani d . 1 . .
    H H12A 0.4889 0.2579 0.5805 0.109 Uiso calc R 1 . .
    H H12B 0.6301 0.2267 0.6066 0.109 Uiso calc R 1 . .
    H H12C 0.5781 0.2944 0.6654 0.109 Uiso calc R 1 . .
    C C13 0.8909(5) -0.1720(2) 1.0445(3) 0.1034(15) Uani d . 1 . .
    H H13A 0.9394 -0.2106 1.0783 0.155 Uiso calc R 1 . .
    H H13B 0.9244 -0.1648 0.9792 0.155 Uiso calc R 1 . .
    H H13C 0.7994 -0.1852 1.0380 0.155 Uiso calc R 1 . .
    C C14 0.8536(3) 0.10711(16) 0.6971(2) 0.0578(8) Uani d . 1 . .
    H H14A 0.8076 0.0630 0.6976 0.069 Uiso calc R 1 . .
    C C15 0.9634(3) 0.11167(19) 0.6418(2) 0.0630(9) Uani d . 1 . .
    H H15A 0.9903 0.0718 0.6045 0.076 Uiso calc R 1 . .
    C C16 1.0329(3) 0.1763(2) 0.6427(3) 0.0689(9) Uani d . 1 . .
    H H16A 1.1076 0.1809 0.6055 0.083 Uiso calc R 1 . .
    C C17 0.9908(3) 0.23447(17) 0.6995(2) 0.0572(8) Uani d . 1 . .
    H H17A 1.0379 0.2783 0.7021 0.069 Uiso calc R 1 . .
    C C18 0.8784(3) 0.22671(14) 0.75206(19) 0.0415(6) Uani d . 1 . .
    C C19 0.8210(3) 0.28739(14) 0.81221(18) 0.0402(6) Uani d . 1 . .
    C C20 0.8879(3) 0.35225(16) 0.8336(2) 0.0531(7) Uani d . 1 . .
    H H20A 0.9728 0.3592 0.8123 0.064 Uiso calc R 1 . .
    C C21 0.8265(3) 0.40656(17) 0.8872(2) 0.0611(8) Uani d . 1 . .
    H H21A 0.8702 0.4503 0.9025 0.073 Uiso calc R 1 . .
    C C22 0.7019(3) 0.39554(15) 0.9173(2) 0.0546(8) Uani d . 1 . .
    H H22A 0.6587 0.4319 0.9520 0.066 Uiso calc R 1 . .
    C C23 0.6409(3) 0.32963(14) 0.8954(2) 0.0480(7) Uani d . 1 . .
    H H23A 0.5561 0.3220 0.9166 0.058 Uiso calc R 1 . .
    Cl Cl 0.25347(7) 0.09143(4) 0.40216(5) 0.05096(19) Uani d . 1 . .
    O O3 0.2755(3) 0.16261(12) 0.4419(2) 0.0957(9) Uani d . 1 . .
    O O4 0.2085(3) 0.09639(16) 0.30025(18) 0.0956(9) Uani d . 1 . .
    O O5 0.1576(3) 0.05517(15) 0.4574(2) 0.0958(8) Uani d . 1 . .
    O O6 0.3729(2) 0.05090(16) 0.4085(2) 0.0970(9) Uani d . 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
    Cu O1 . 1.9037(19) ?
    Cu N1 . 1.963(2) ?
    Cu N4 . 2.043(2) ?
    Cu N2 . 2.077(2) ?
    Cu N3 . 2.207(2) ?
    O1 C1 . 1.313(3) ?
    O2 C4 . 1.393(4) ?
    O2 C13 . 1.400(4) ?
    N1 C7 . 1.298(3) ?
    N1 C9 . 1.466(3) ?
    N2 C11 . 1.462(4) ?
    N2 C10 . 1.482(4) ?
    N2 C12 . 1.490(4) ?
    N3 C14 . 1.343(3) ?
    N3 C18 . 1.346(3) ?
    N4 C19 . 1.348(3) ?
    N4 C23 . 1.347(3) ?
    C1 C2 . 1.407(4) ?
    C1 C6 . 1.423(4) ?
    C2 C3 . 1.373(4) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.389(4) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.355(4) ?
    C5 C6 . 1.416(4) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.465(4) ?
    C7 C8 . 1.512(4) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 C10 . 1.512(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C15 . 1.369(4) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.372(4) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.383(4) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.375(4) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.501(4) ?
    C19 C20 . 1.386(4) ?
    C20 C21 . 1.387(4) ?
    C20 H20A . 0.9300 ?
    C21 C22 . 1.360(4) ?
    C21 H21A . 0.9300 ?
    C22 C23 . 1.376(4) ?
    C22 H22A . 0.9300 ?
    C23 H23A . 0.9300 ?
    Cl O5 . 1.413(2) ?
    Cl O3 . 1.416(2) ?
    Cl O6 . 1.419(2) ?
    Cl O4 . 1.421(2) ?
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
    O1 Cu N1 . . 91.73(9) ?
    O1 Cu N4 . . 88.40(8) ?
    N1 Cu N4 . . 179.21(9) ?
    O1 Cu N2 . . 159.65(9) ?
    N1 Cu N2 . . 85.30(9) ?
    N4 Cu N2 . . 94.31(9) ?
    O1 Cu N3 . . 101.58(9) ?
    N1 Cu N3 . . 103.01(9) ?
    N4 Cu N3 . . 77.72(8) ?
    N2 Cu N3 . . 98.71(9) ?
    C1 O1 Cu . . 121.01(16) ?
    C4 O2 C13 . . 117.4(3) ?
    C7 N1 C9 . . 121.2(2) ?
    C7 N1 Cu . . 125.99(18) ?
    C9 N1 Cu . . 112.81(18) ?
    C11 N2 C10 . . 111.8(3) ?
    C11 N2 C12 . . 108.1(3) ?
    C10 N2 C12 . . 108.5(2) ?
    C11 N2 Cu . . 109.6(2) ?
    C10 N2 Cu . . 103.51(18) ?
    C12 N2 Cu . . 115.31(19) ?
    C14 N3 C18 . . 118.4(2) ?
    C14 N3 Cu . . 128.5(2) ?
    C18 N3 Cu . . 112.95(17) ?
    C19 N4 C23 . . 118.5(2) ?
    C19 N4 Cu . . 117.37(17) ?
    C23 N4 Cu . . 123.61(19) ?
    O1 C1 C2 . . 118.0(2) ?
    O1 C1 C6 . . 125.1(3) ?
    C2 C1 C6 . . 116.9(3) ?
    C3 C2 C1 . . 122.9(3) ?
    C3 C2 H2A . . 118.5 ?
    C1 C2 H2A . . 118.5 ?
    C2 C3 C4 . . 119.6(3) ?
    C2 C3 H3A . . 120.2 ?
    C4 C3 H3A . . 120.2 ?
    C5 C4 C3 . . 119.6(3) ?
    C5 C4 O2 . . 125.0(3) ?
    C3 C4 O2 . . 115.4(3) ?
    C4 C5 C6 . . 122.4(3) ?
    C4 C5 H5A . . 118.8 ?
    C6 C5 H5A . . 118.8 ?
    C5 C6 C1 . . 118.5(3) ?
    C5 C6 C7 . . 119.1(2) ?
    C1 C6 C7 . . 122.3(2) ?
    N1 C7 C6 . . 121.2(2) ?
    N1 C7 C8 . . 120.5(3) ?
    C6 C7 C8 . . 118.3(3) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N1 C9 C10 . . 108.0(2) ?
    N1 C9 H9A . . 110.1 ?
    C10 C9 H9A . . 110.1 ?
    N1 C9 H9B . . 110.1 ?
    C10 C9 H9B . . 110.1 ?
    H9A C9 H9B . . 108.4 ?
    N2 C10 C9 . . 111.1(3) ?
    N2 C10 H10A . . 109.4 ?
    C9 C10 H10A . . 109.4 ?
    N2 C10 H10B . . 109.4 ?
    C9 C10 H10B . . 109.4 ?
    H10A C10 H10B . . 108.0 ?
    N2 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 H12A . . 109.5 ?
    N2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    O2 C13 H13A . . 109.5 ?
    O2 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    O2 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N3 C14 C15 . . 122.8(3) ?
    N3 C14 H14A . . 118.6 ?
    C15 C14 H14A . . 118.6 ?
    C14 C15 C16 . . 118.6(3) ?
    C14 C15 H15A . . 120.7 ?
    C16 C15 H15A . . 120.7 ?
    C15 C16 C17 . . 119.3(3) ?
    C15 C16 H16A . . 120.3 ?
    C17 C16 H16A . . 120.3 ?
    C18 C17 C16 . . 119.1(3) ?
    C18 C17 H17A . . 120.4 ?
    C16 C17 H17A . . 120.4 ?
    N3 C18 C17 . . 121.7(2) ?
    N3 C18 C19 . . 114.9(2) ?
    C17 C18 C19 . . 123.4(3) ?
    N4 C19 C20 . . 121.2(2) ?
    N4 C19 C18 . . 116.2(2) ?
    C20 C19 C18 . . 122.6(2) ?
    C21 C20 C19 . . 119.1(3) ?
    C21 C20 H20A . . 120.4 ?
    C19 C20 H20A . . 120.4 ?
    C22 C21 C20 . . 119.6(3) ?
    C22 C21 H21A . . 120.2 ?
    C20 C21 H21A . . 120.2 ?
    C21 C22 C23 . . 118.8(3) ?
    C21 C22 H22A . . 120.6 ?
    C23 C22 H22A . . 120.6 ?
    N4 C23 C22 . . 122.8(3) ?
    N4 C23 H23A . . 118.6 ?
    C22 C23 H23A . . 118.6 ?
    O5 Cl O3 . . 109.42(18) ?
    O5 Cl O6 . . 109.47(17) ?
    O3 Cl O6 . . 109.50(18) ?
    O5 Cl O4 . . 109.41(17) ?
    O3 Cl O4 . . 109.93(18) ?
    O6 Cl O4 . . 109.10(17) ?
