#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/00/2230045.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230045
loop_
_publ_author_name
'Wang, Yu-Min'
'Lin, Xiao-Hui'
'Chen, Zhen'
'Jiang, Hong-Li'
'Zhang, Chang-Jun'
_publ_section_title
;
 [(E)-N'-(5-Chloro-2-oxidobenzylidene-κO)-3,4,5-trimethoxybenzohydrazidato-κ²N',O](pyridine-κN)copper(II)
;
_journal_coeditor_code           JH2271
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m526
_journal_paper_doi               10.1107/S1600536811009901
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C17 H15 Cl N2 O5) (C5 H5 N)]'
_chemical_formula_moiety         'C22 H20 Cl1 Cu1 N3 O5'
_chemical_formula_sum            'C22 H20 Cl Cu N3 O5'
_chemical_formula_weight         505.40
_chemical_name_systematic
;
[(E)-N'-(5-Chloro-2-oxidobenzylidene-κO)-3,4,5-
trimethoxybenzohydrazidato-κ²N',O](pyridine-
κN)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.108(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.274(4)
_cell_length_b                   7.5763(18)
_cell_length_c                   20.753(5)
_cell_measurement_reflns_used    3527
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.87
_cell_volume                     2216.0(10)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11265
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    1.145
_exptl_absorpt_correction_T_max  0.8748
_exptl_absorpt_correction_T_min  0.8118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.8080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                3184
_reflns_number_total             3908
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2271.cif
_cod_data_source_block           I
_cod_original_cell_volume        2216.1(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C22 H20 Cl1 Cu1 N3 O5'
_cod_database_code               2230045
_cod_database_fobs_code          2230045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 Cu1 0.54442(2) 0.14856(4) 0.056192(13) 0.03244(11) Uani d . 1 . .
Cl Cl1 0.26557(6) 0.62229(10) -0.21238(3) 0.0569(2) Uani d . 1 . .
O O1 0.52842(12) 0.1751(2) -0.03651(8) 0.0393(4) Uani d . 1 . .
O O2 0.54254(12) 0.1224(2) 0.14894(8) 0.0364(4) Uani d . 1 . .
O O3 0.5244(2) -0.0473(3) 0.38634(10) 0.0825(8) Uani d . 1 . .
O O4 0.41727(15) 0.2050(3) 0.42842(8) 0.0565(5) Uani d . 1 . .
O O5 0.33613(15) 0.4566(3) 0.34986(9) 0.0655(6) Uani d . 1 . .
N N1 0.67522(14) 0.0438(3) 0.05888(9) 0.0324(4) Uani d . 1 . .
N N2 0.43295(14) 0.2875(3) 0.06254(9) 0.0312(4) Uani d . 1 . .
N N3 0.40808(14) 0.2968(3) 0.12482(9) 0.0352(5) Uani d . 1 . .
C C1 0.46948(17) 0.2826(3) -0.07312(11) 0.0337(5) Uani d . 1 . .
C C2 0.39692(17) 0.3819(3) -0.04970(11) 0.0315(5) Uani d . 1 . .
C C3 0.33515(18) 0.4867(3) -0.09362(12) 0.0370(6) Uani d . 1 . .
H H3 0.2878 0.5516 -0.0784 0.044 Uiso calc R 1 . .
C C4 0.34372(18) 0.4943(3) -0.15816(12) 0.0386(6) Uani d . 1 . .
C C5 0.4148(2) 0.3997(3) -0.18158(12) 0.0421(6) Uani d . 1 . .
H H5 0.4209 0.4063 -0.2255 0.051 Uiso calc R 1 . .
C C6 0.47585(19) 0.2969(3) -0.13977(12) 0.0399(6) Uani d . 1 . .
H H6 0.5231 0.2346 -0.1561 0.048 Uiso calc R 1 . .
C C7 0.38229(18) 0.3777(3) 0.01742(12) 0.0346(6) Uani d . 1 . .
H H7 0.3329 0.4448 0.0289 0.042 Uiso calc R 1 . .
C C8 0.47163(17) 0.2079(3) 0.16524(11) 0.0328(5) Uani d . 1 . .
C C9 0.45815(17) 0.2063(3) 0.23496(11) 0.0333(5) Uani d . 1 . .
C C10 0.50005(19) 0.0761(4) 0.27666(12) 0.0423(6) Uani d . 1 . .
H H10 0.5382 -0.0089 0.2615 0.051 Uiso calc R 1 . .
C C11 0.4850(2) 0.0729(4) 0.34094(12) 0.0464(7) Uani d . 1 . .
C C12 0.42910(18) 0.2013(4) 0.36393(11) 0.0411(6) Uani d . 1 . .
C C13 0.38825(18) 0.3340(4) 0.32232(12) 0.0410(6) Uani d . 1 . .
C C14 0.40278(18) 0.3369(3) 0.25749(12) 0.0393(6) Uani d . 1 . .
H H14 0.3757 0.4253 0.2295 0.047 Uiso calc R 1 . .
C C15 0.5491(3) -0.2135(5) 0.36663(18) 0.0856(12) Uani d . 1 . .
H H15A 0.4979 -0.2609 0.3360 0.128 Uiso calc R 1 . .
H H15B 0.5616 -0.2899 0.4039 0.128 Uiso calc R 1 . .
H H15C 0.6049 -0.2046 0.3464 0.128 Uiso calc R 1 . .
C C16 0.3549(3) 0.0777(6) 0.44687(19) 0.1005(15) Uani d . 1 . .
H H16A 0.2959 0.0819 0.4174 0.151 Uiso calc R 1 . .
H H16B 0.3437 0.1018 0.4904 0.151 Uiso calc R 1 . .
H H16C 0.3826 -0.0374 0.4454 0.151 Uiso calc R 1 . .
C C17 0.2831(3) 0.5821(5) 0.30812(17) 0.0887(13) Uani d . 1 . .
H H17A 0.3257 0.6550 0.2883 0.133 Uiso calc R 1 . .
H H17B 0.2469 0.6545 0.3331 0.133 Uiso calc R 1 . .
H H17C 0.2409 0.5216 0.2747 0.133 Uiso calc R 1 . .
C C18 0.71659(18) 0.0346(4) 0.00516(12) 0.0414(6) Uani d . 1 . .
H H18 0.6856 0.0849 -0.0332 0.050 Uiso calc R 1 . .
C C19 0.80282(19) -0.0460(4) 0.00440(13) 0.0497(7) Uani d . 1 . .
H H19 0.8296 -0.0487 -0.0336 0.060 Uiso calc R 1 . .
C C20 0.8487(2) -0.1221(4) 0.06053(14) 0.0481(7) Uani d . 1 . .
H H20 0.9064 -0.1793 0.0610 0.058 Uiso calc R 1 . .
C C21 0.80784(19) -0.1126(4) 0.11634(13) 0.0447(7) Uani d . 1 . .
H H21 0.8378 -0.1629 0.1551 0.054 Uiso calc R 1 . .
C C22 0.72216(18) -0.0276(3) 0.11392(12) 0.0368(6) Uani d . 1 . .
H H22 0.6957 -0.0192 0.1520 0.044 Uiso calc R 1 . .
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'
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 Cu1 N2 . . 92.45(7) ?
O1 Cu1 O2 . . 172.44(7) ?
N2 Cu1 O2 . . 81.20(7) ?
O1 Cu1 N1 . . 91.82(7) ?
N2 Cu1 N1 . . 168.60(8) ?
O2 Cu1 N1 . . 95.18(7) ?
C1 O1 Cu1 . . 127.39(15) ?
C8 O2 Cu1 . . 110.09(14) ?
C11 O3 C15 . . 119.9(2) ?
C12 O4 C16 . . 115.6(2) ?
C13 O5 C17 . . 118.1(2) ?
C22 N1 C18 . . 117.3(2) ?
C22 N1 Cu1 . . 121.05(16) ?
C18 N1 Cu1 . . 121.52(17) ?
C7 N2 N3 . . 116.9(2) ?
C7 N2 Cu1 . . 127.97(16) ?
N3 N2 Cu1 . . 115.09(14) ?
C8 N3 N2 . . 108.26(19) ?
O1 C1 C6 . . 118.6(2) ?
O1 C1 C2 . . 124.0(2) ?
C6 C1 C2 . . 117.3(2) ?
C3 C2 C1 . . 119.4(2) ?
C3 C2 C7 . . 117.8(2) ?
C1 C2 C7 . . 122.8(2) ?
C4 C3 C2 . . 121.0(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 120.3(2) ?
C3 C4 Cl1 . . 120.5(2) ?
C5 C4 Cl1 . . 119.17(19) ?
C6 C5 C4 . . 119.8(2) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 122.2(2) ?
C5 C6 H6 . . 118.9 ?
C1 C6 H6 . . 118.9 ?
N2 C7 C2 . . 124.4(2) ?
N2 C7 H7 . . 117.8 ?
C2 C7 H7 . . 117.8 ?
O2 C8 N3 . . 125.3(2) ?
O2 C8 C9 . . 118.5(2) ?
N3 C8 C9 . . 116.1(2) ?
C10 C9 C14 . . 120.6(2) ?
C10 C9 C8 . . 120.2(2) ?
C14 C9 C8 . . 119.2(2) ?
C9 C10 C11 . . 119.8(2) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
O3 C11 C10 . . 124.5(3) ?
O3 C11 C12 . . 115.2(2) ?
C10 C11 C12 . . 120.2(2) ?
O4 C12 C11 . . 120.9(2) ?
O4 C12 C13 . . 119.0(2) ?
C11 C12 C13 . . 120.0(2) ?
O5 C13 C12 . . 115.6(2) ?
O5 C13 C14 . . 124.4(2) ?
C12 C13 C14 . . 119.9(2) ?
C9 C14 C13 . . 119.5(2) ?
C9 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O5 C17 H17A . . 109.5 ?
O5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N1 C18 C19 . . 122.9(2) ?
N1 C18 H18 . . 118.5 ?
C19 C18 H18 . . 118.5 ?
C20 C19 C18 . . 119.0(2) ?
C20 C19 H19 . . 120.5 ?
C18 C19 H19 . . 120.5 ?
C19 C20 C21 . . 119.0(3) ?
C19 C20 H20 . . 120.5 ?
C21 C20 H20 . . 120.5 ?
C22 C21 C20 . . 119.0(2) ?
C22 C21 H21 . . 120.5 ?
C20 C21 H21 . . 120.5 ?
N1 C22 C21 . . 122.7(2) ?
N1 C22 H22 . . 118.6 ?
C21 C22 H22 . . 118.6 ?
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
Cu1 O1 . 1.9119(16) ?
Cu1 N2 . 1.930(2) ?
Cu1 O2 . 1.9394(16) ?
Cu1 N1 . 2.021(2) ?
Cl1 C4 . 1.747(3) ?
O1 C1 . 1.321(3) ?
O2 C8 . 1.291(3) ?
O3 C11 . 1.366(3) ?
O3 C15 . 1.386(4) ?
O4 C12 . 1.375(3) ?
O4 C16 . 1.406(4) ?
O5 C13 . 1.370(3) ?
O5 C17 . 1.421(4) ?
N1 C22 . 1.343(3) ?
N1 C18 . 1.344(3) ?
N2 C7 . 1.285(3) ?
N2 N3 . 1.395(2) ?
N3 C8 . 1.319(3) ?
C1 C6 . 1.405(3) ?
C1 C2 . 1.426(3) ?
C2 C3 . 1.408(3) ?
C2 C7 . 1.441(3) ?
C3 C4 . 1.365(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.391(4) ?
C5 C6 . 1.371(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.490(3) ?
C9 C10 . 1.384(4) ?
C9 C14 . 1.393(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.390(4) ?
C12 C13 . 1.392(4) ?
C13 C14 . 1.394(3) ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 C19 . 1.376(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.370(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.378(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.376(4) ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
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
N2 Cu1 O1 C1 . . . . 10.7(2) ?
N1 Cu1 O1 C1 . . . . -158.7(2) ?
N2 Cu1 O2 C8 . . . . -0.24(15) ?
N1 Cu1 O2 C8 . . . . 168.87(15) ?
O1 Cu1 N1 C22 . . . . -171.09(18) ?
N2 Cu1 N1 C22 . . . . 76.9(4) ?
O2 Cu1 N1 C22 . . . . 6.06(19) ?
O1 Cu1 N1 C18 . . . . 5.5(2) ?
N2 Cu1 N1 C18 . . . . -106.5(4) ?
O2 Cu1 N1 C18 . . . . -177.36(19) ?
O1 Cu1 N2 C7 . . . . -8.4(2) ?
O2 Cu1 N2 C7 . . . . 175.7(2) ?
N1 Cu1 N2 C7 . . . . 103.5(4) ?
O1 Cu1 N2 N3 . . . . 175.03(16) ?
O2 Cu1 N2 N3 . . . . -0.85(15) ?
N1 Cu1 N2 N3 . . . . -73.0(4) ?
C7 N2 N3 C8 . . . . -175.3(2) ?
Cu1 N2 N3 C8 . . . . 1.7(2) ?
Cu1 O1 C1 C6 . . . . 172.93(17) ?
Cu1 O1 C1 C2 . . . . -9.2(3) ?
O1 C1 C2 C3 . . . . -177.2(2) ?
C6 C1 C2 C3 . . . . 0.7(3) ?
O1 C1 C2 C7 . . . . 1.6(4) ?
C6 C1 C2 C7 . . . . 179.5(2) ?
C1 C2 C3 C4 . . . . 0.1(4) ?
C7 C2 C3 C4 . . . . -178.8(2) ?
C2 C3 C4 C5 . . . . -0.8(4) ?
C2 C3 C4 Cl1 . . . . 179.08(18) ?
C3 C4 C5 C6 . . . . 0.7(4) ?
Cl1 C4 C5 C6 . . . . -179.1(2) ?
C4 C5 C6 C1 . . . . 0.1(4) ?
O1 C1 C6 C5 . . . . 177.2(2) ?
C2 C1 C6 C5 . . . . -0.8(4) ?
N3 N2 C7 C2 . . . . -179.1(2) ?
Cu1 N2 C7 C2 . . . . 4.4(4) ?
C3 C2 C7 N2 . . . . 179.7(2) ?
C1 C2 C7 N2 . . . . 0.9(4) ?
Cu1 O2 C8 N3 . . . . 1.5(3) ?
Cu1 O2 C8 C9 . . . . -179.27(16) ?
N2 N3 C8 O2 . . . . -2.2(3) ?
N2 N3 C8 C9 . . . . 178.60(19) ?
O2 C8 C9 C10 . . . . -20.0(3) ?
N3 C8 C9 C10 . . . . 159.3(2) ?
O2 C8 C9 C14 . . . . 160.2(2) ?
N3 C8 C9 C14 . . . . -20.5(3) ?
C14 C9 C10 C11 . . . . 1.6(4) ?
C8 C9 C10 C11 . . . . -178.2(2) ?
C15 O3 C11 C10 . . . . -27.1(5) ?
C15 O3 C11 C12 . . . . 155.1(3) ?
C9 C10 C11 O3 . . . . -178.7(3) ?
C9 C10 C11 C12 . . . . -0.9(4) ?
C16 O4 C12 C11 . . . . -76.1(4) ?
C16 O4 C12 C13 . . . . 107.2(3) ?
O3 C11 C12 O4 . . . . 1.2(4) ?
C10 C11 C12 O4 . . . . -176.8(2) ?
O3 C11 C12 C13 . . . . 177.8(3) ?
C10 C11 C12 C13 . . . . -0.2(4) ?
C17 O5 C13 C12 . . . . -172.3(3) ?
C17 O5 C13 C14 . . . . 8.6(4) ?
O4 C12 C13 O5 . . . . -1.9(4) ?
C11 C12 C13 O5 . . . . -178.6(3) ?
O4 C12 C13 C14 . . . . 177.3(2) ?
C11 C12 C13 C14 . . . . 0.6(4) ?
C10 C9 C14 C13 . . . . -1.2(4) ?
C8 C9 C14 C13 . . . . 178.7(2) ?
O5 C13 C14 C9 . . . . 179.2(3) ?
C12 C13 C14 C9 . . . . 0.1(4) ?
C22 N1 C18 C19 . . . . 1.0(4) ?
Cu1 N1 C18 C19 . . . . -175.7(2) ?
N1 C18 C19 C20 . . . . 0.7(4) ?
C18 C19 C20 C21 . . . . -1.2(4) ?
C19 C20 C21 C22 . . . . 0.3(4) ?
C18 N1 C22 C21 . . . . -2.0(4) ?
Cu1 N1 C22 C21 . . . . 174.66(19) ?
C20 C21 C22 N1 . . . . 1.5(4) ?
