#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221673.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_2221673
loop_
_publ_author_name
'Yu, Zhao-Wen'
'Chang, Ling'
'Song, Peng'
'He, Min-Hui'
_publ_section_title
;Aqua(3-formyl-2-oxidobenzoato-κ²O¹,O²)(1,10-phenanthroline-κ²N,N')copper(II)
 dimethylformamide solvate
;
_journal_coeditor_code           GK2199
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m485
_journal_paper_doi               10.1107/S1600536809011659
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'[Cu (C8 H4 O4) (C12 H8 N2) (H2 O)], C3 H7 N O'
_chemical_formula_moiety         'C20 H14 Cu N2 O5, C3 H7 N O'
_chemical_formula_sum            'C23 H21 Cu N3 O6'
_chemical_formula_weight         498.97
_chemical_name_systematic
;
Aqua(3-formyl-2-oxidobenzoato-κ²O¹,O²)(1,10-
phenanthroline-κ²N,N')copper(II) dimethylformamide solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.8340(10)
_cell_angle_beta                 109.7640(10)
_cell_angle_gamma                98.6040(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6936(6)
_cell_length_b                   10.9020(12)
_cell_length_c                   11.2800(7)
_cell_measurement_reflns_used    4490
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.31
_cell_volume                     1054.09(15)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5440
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.475
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0360
_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)+(0.0719P)²+0.6371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                3452
_reflns_number_total             3687
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2199.cif
_cod_data_source_block           I
_cod_database_code               2221673
_cod_database_fobs_code          2221673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.16328(3) 0.00556(3) 0.42283(3) 0.03264(14) Uani d . 1 . .
O O1W 0.3462(2) 0.1436(2) 0.3911(2) 0.0530(5) Uani d . 1 . .
H H1WA 0.3993 0.2098 0.4581 0.064 Uiso d R 1 . .
H H1WB 0.4065 0.1074 0.3640 0.064 Uiso d R 1 . .
N N1 0.1623(2) -0.1462(2) 0.2786(2) 0.0327(4) Uani d . 1 . .
N N2 -0.0089(2) 0.0216(2) 0.2678(2) 0.0308(4) Uani d . 1 . .
O O1 0.0712(3) 0.4672(2) 0.7470(2) 0.0664(7) Uani d . 1 . .
O O2 0.1357(2) 0.13957(18) 0.54916(17) 0.0398(4) Uani d . 1 . .
O O3 0.3000(2) -0.0508(2) 0.55253(18) 0.0448(5) Uani d . 1 . .
O O4 0.4950(2) -0.0174(2) 0.73640(19) 0.0488(5) Uani d . 1 . .
C C1 0.2529(3) -0.2267(3) 0.2873(3) 0.0398(6) Uani d . 1 . .
H H1 0.3279 -0.2160 0.3693 0.048 Uiso calc R 1 . .
C C2 0.2386(4) -0.3274(3) 0.1765(3) 0.0464(7) Uani d . 1 . .
H H2 0.3035 -0.3824 0.1859 0.056 Uiso calc R 1 . .
C C3 0.1309(3) -0.3448(3) 0.0559(3) 0.0443(6) Uani d . 1 . .
H H3 0.1210 -0.4118 -0.0176 0.053 Uiso calc R 1 . .
C C4 0.0332(3) -0.2596(2) 0.0429(2) 0.0359(6) Uani d . 1 . .
C C5 -0.0824(3) -0.2675(3) -0.0794(3) 0.0459(7) Uani d . 1 . .
H H5 -0.0983 -0.3331 -0.1561 0.055 Uiso calc R 1 . .
C C6 -0.1692(3) -0.1811(3) -0.0857(3) 0.0449(7) Uani d . 1 . .
H H6 -0.2427 -0.1875 -0.1669 0.054 Uiso calc R 1 . .
C C7 -0.1500(3) -0.0799(3) 0.0307(2) 0.0364(6) Uani d . 1 . .
C C8 -0.2360(3) 0.0125(3) 0.0314(3) 0.0445(6) Uani d . 1 . .
H H8 -0.3119 0.0107 -0.0465 0.053 Uiso calc R 1 . .
C C9 -0.2064(3) 0.1058(3) 0.1490(3) 0.0460(7) Uani d . 1 . .
H H9 -0.2626 0.1677 0.1510 0.055 Uiso calc R 1 . .
C C10 -0.0924(3) 0.1080(3) 0.2656(3) 0.0376(6) Uani d . 1 . .
H H10 -0.0742 0.1719 0.3442 0.045 Uiso calc R 1 . .
C C11 -0.0379(3) -0.0707(2) 0.1520(2) 0.0302(5) Uani d . 1 . .
C C12 0.0550(3) -0.1618(2) 0.1578(2) 0.0307(5) Uani d . 1 . .
C C13 0.0912(4) 0.3653(3) 0.6920(3) 0.0460(7) Uani d . 1 . .
H H13 0.0230 0.3205 0.6056 0.055 Uiso calc R 1 . .
C C14 0.2124(3) 0.3076(2) 0.7494(3) 0.0353(6) Uani d . 1 . .
C C15 0.3105(3) 0.3681(3) 0.8826(3) 0.0432(6) Uani d . 1 . .
H H15 0.2961 0.4433 0.9314 0.052 Uiso calc R 1 . .
C C16 0.4270(4) 0.3178(3) 0.9413(3) 0.0503(7) Uani d . 1 . .
H H16 0.4925 0.3591 1.0292 0.060 Uiso calc R 1 . .
C C17 0.4463(3) 0.2053(3) 0.8687(3) 0.0413(6) Uani d . 1 . .
H H17 0.5252 0.1713 0.9100 0.050 Uiso calc R 1 . .
C C18 0.3532(3) 0.1408(2) 0.7370(2) 0.0314(5) Uani d . 1 . .
C C19 0.2317(3) 0.1921(2) 0.6732(2) 0.0308(5) Uani d . 1 . .
C C20 0.3865(3) 0.0178(3) 0.6722(2) 0.0340(5) Uani d . 1 . .
C C21 0.2290(5) 0.4426(5) 0.4552(4) 0.0845(12) Uani d . 1 . .
H H21A 0.2696 0.3733 0.4216 0.127 Uiso calc R 1 . .
H H21B 0.2083 0.4936 0.3956 0.127 Uiso calc R 1 . .
H H21C 0.1370 0.4063 0.4626 0.127 Uiso calc R 1 . .
C C22 0.3128(7) 0.6469(4) 0.6359(6) 0.1041(18) Uani d . 1 . .
H H22A 0.4044 0.6995 0.7088 0.156 Uiso calc R 1 . .
H H22B 0.2323 0.6350 0.6666 0.156 Uiso calc R 1 . .
H H22C 0.2869 0.6897 0.5692 0.156 Uiso calc R 1 . .
N N3 0.3350(3) 0.5228(3) 0.5809(2) 0.0490(6) Uani d . 1 . .
C C23 0.4569(4) 0.4849(4) 0.6420(4) 0.0633(9) Uani d . 1 . .
H H23 0.5258 0.5400 0.7245 0.076 Uiso calc R 1 . .
O O5 0.4840(3) 0.3805(2) 0.5953(3) 0.0700(7) Uani d . 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'
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
O2 Cu1 O3 . . 94.58(8) ?
O2 Cu1 N1 . . 172.36(8) ?
O3 Cu1 N1 . . 89.63(8) ?
O2 Cu1 N2 . . 93.28(8) ?
O3 Cu1 N2 . . 166.80(9) ?
N1 Cu1 N2 . . 81.45(8) ?
O2 Cu1 O1W . . 95.02(8) ?
O3 Cu1 O1W . . 96.84(9) ?
N1 Cu1 O1W . . 90.80(8) ?
N2 Cu1 O1W . . 93.03(8) ?
Cu1 O1W H1WA . . 114.5 ?
Cu1 O1W H1WB . . 115.6 ?
H1WA O1W H1WB . . 107.7 ?
C1 N1 C12 . . 118.3(2) ?
C1 N1 Cu1 . . 128.79(18) ?
C12 N1 Cu1 . . 112.92(16) ?
C10 N2 C11 . . 117.8(2) ?
C10 N2 Cu1 . . 129.47(18) ?
C11 N2 Cu1 . . 112.70(16) ?
C19 O2 Cu1 . . 123.98(16) ?
C20 O3 Cu1 . . 126.98(17) ?
N1 C1 C2 . . 121.9(3) ?
N1 C1 H1 . . 119.1 ?
C2 C1 H1 . . 119.1 ?
C3 C2 C1 . . 120.3(3) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 119.2(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C12 C4 C3 . . 116.9(2) ?
C12 C4 C5 . . 119.1(2) ?
C3 C4 C5 . . 124.0(2) ?
C6 C5 C4 . . 121.1(2) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 121.1(2) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C11 C7 C8 . . 117.1(2) ?
C11 C7 C6 . . 118.8(2) ?
C8 C7 C6 . . 124.1(2) ?
C9 C8 C7 . . 119.0(2) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
C8 C9 C10 . . 120.3(3) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
N2 C10 C9 . . 122.1(2) ?
N2 C10 H10 . . 119.0 ?
C9 C10 H10 . . 119.0 ?
N2 C11 C7 . . 123.8(2) ?
N2 C11 C12 . . 116.4(2) ?
C7 C11 C12 . . 119.8(2) ?
N1 C12 C4 . . 123.4(2) ?
N1 C12 C11 . . 116.5(2) ?
C4 C12 C11 . . 120.1(2) ?
O1 C13 C14 . . 125.5(3) ?
O1 C13 H13 . . 117.2 ?
C14 C13 H13 . . 117.2 ?
C15 C14 C19 . . 120.6(3) ?
C15 C14 C13 . . 118.5(2) ?
C19 C14 C13 . . 121.0(2) ?
C16 C15 C14 . . 120.7(3) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 119.3(3) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C16 C17 C18 . . 122.8(3) ?
C16 C17 H17 . . 118.6 ?
C18 C17 H17 . . 118.6 ?
C17 C18 C19 . . 118.9(2) ?
C17 C18 C20 . . 116.5(2) ?
C19 C18 C20 . . 124.5(2) ?
O2 C19 C14 . . 117.8(2) ?
O2 C19 C18 . . 124.5(2) ?
C14 C19 C18 . . 117.7(2) ?
O4 C20 O3 . . 120.9(2) ?
O4 C20 C18 . . 119.2(2) ?
O3 C20 C18 . . 119.9(2) ?
N3 C21 H21A . . 109.5 ?
N3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N3 C22 H22A . . 109.5 ?
N3 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N3 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C23 N3 C21 . . 119.7(3) ?
C23 N3 C22 . . 121.6(4) ?
C21 N3 C22 . . 118.5(4) ?
O5 C23 N3 . . 123.8(3) ?
O5 C23 H23 . . 118.1 ?
N3 C23 H23 . . 118.1 ?
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 O2 . 1.9012(18) ?
Cu1 O3 . 1.9071(18) ?
Cu1 N1 . 2.020(2) ?
Cu1 N2 . 2.033(2) ?
Cu1 O1W . 2.329(2) ?
O1W H1WA . 0.8500 ?
O1W H1WB . 0.8500 ?
N1 C1 . 1.328(3) ?
N1 C12 . 1.359(3) ?
N2 C10 . 1.330(3) ?
N2 C11 . 1.356(3) ?
O1 C13 . 1.215(4) ?
O2 C19 . 1.315(3) ?
O3 C20 . 1.284(3) ?
O4 C20 . 1.231(3) ?
C1 C2 . 1.403(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.354(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.420(4) ?
C3 H3 . 0.9300 ?
C4 C12 . 1.395(3) ?
C4 C5 . 1.427(4) ?
C5 C6 . 1.352(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.434(4) ?
C6 H6 . 0.9300 ?
C7 C11 . 1.400(3) ?
C7 C8 . 1.401(4) ?
C8 C9 . 1.374(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.394(4) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.435(4) ?
C13 C14 . 1.448(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.403(4) ?
C14 C19 . 1.421(3) ?
C15 C16 . 1.366(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.379(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.386(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.426(4) ?
C18 C20 . 1.502(3) ?
C21 N3 . 1.408(5) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 N3 . 1.428(5) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
N3 C23 . 1.332(5) ?
C23 O5 . 1.240(4) ?
C23 H23 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1W H1WB O4 2_656 0.85 1.91 2.741(3) 167
O1W H1WA O5 . 0.85 1.96 2.794(3) 167
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
O3 Cu1 N1 C1 . . . . -11.6(2) ?
N2 Cu1 N1 C1 . . . . 178.2(2) ?
O1W Cu1 N1 C1 . . . . 85.2(2) ?
O3 Cu1 N1 C12 . . . . 170.25(17) ?
N2 Cu1 N1 C12 . . . . 0.02(16) ?
O1W Cu1 N1 C12 . . . . -92.91(17) ?
O2 Cu1 N2 C10 . . . . 6.0(2) ?
O3 Cu1 N2 C10 . . . . 132.5(3) ?
N1 Cu1 N2 C10 . . . . -179.5(2) ?
O1W Cu1 N2 C10 . . . . -89.2(2) ?
O2 Cu1 N2 C11 . . . . -174.44(16) ?
O3 Cu1 N2 C11 . . . . -48.0(4) ?
N1 Cu1 N2 C11 . . . . -0.01(15) ?
O1W Cu1 N2 C11 . . . . 90.35(16) ?
O3 Cu1 O2 C19 . . . . 21.4(2) ?
N2 Cu1 O2 C19 . . . . -169.2(2) ?
O1W Cu1 O2 C19 . . . . -75.9(2) ?
O2 Cu1 O3 C20 . . . . -26.0(2) ?
N1 Cu1 O3 C20 . . . . 160.4(2) ?
N2 Cu1 O3 C20 . . . . -152.3(3) ?
O1W Cu1 O3 C20 . . . . 69.7(2) ?
C12 N1 C1 C2 . . . . -1.1(4) ?
Cu1 N1 C1 C2 . . . . -179.2(2) ?
N1 C1 C2 C3 . . . . 0.3(4) ?
C1 C2 C3 C4 . . . . 0.3(4) ?
C2 C3 C4 C12 . . . . -0.2(4) ?
C2 C3 C4 C5 . . . . 178.9(3) ?
C12 C4 C5 C6 . . . . 0.8(4) ?
C3 C4 C5 C6 . . . . -178.3(3) ?
C4 C5 C6 C7 . . . . -1.1(4) ?
C5 C6 C7 C11 . . . . 0.7(4) ?
C5 C6 C7 C8 . . . . -179.9(3) ?
C11 C7 C8 C9 . . . . 0.0(4) ?
C6 C7 C8 C9 . . . . -179.4(3) ?
C7 C8 C9 C10 . . . . 0.0(4) ?
C11 N2 C10 C9 . . . . -0.2(4) ?
Cu1 N2 C10 C9 . . . . 179.35(19) ?
C8 C9 C10 N2 . . . . 0.1(4) ?
C10 N2 C11 C7 . . . . 0.2(3) ?
Cu1 N2 C11 C7 . . . . -179.38(18) ?
C10 N2 C11 C12 . . . . 179.6(2) ?
Cu1 N2 C11 C12 . . . . 0.0(3) ?
C8 C7 C11 N2 . . . . -0.1(4) ?
C6 C7 C11 N2 . . . . 179.4(2) ?
C8 C7 C11 C12 . . . . -179.5(2) ?
C6 C7 C11 C12 . . . . 0.0(3) ?
C1 N1 C12 C4 . . . . 1.3(4) ?
Cu1 N1 C12 C4 . . . . 179.64(18) ?
C1 N1 C12 C11 . . . . -178.4(2) ?
Cu1 N1 C12 C11 . . . . 0.0(3) ?
C3 C4 C12 N1 . . . . -0.6(4) ?
C5 C4 C12 N1 . . . . -179.8(2) ?
C3 C4 C12 C11 . . . . 179.0(2) ?
C5 C4 C12 C11 . . . . -0.1(4) ?
N2 C11 C12 N1 . . . . 0.0(3) ?
C7 C11 C12 N1 . . . . 179.4(2) ?
N2 C11 C12 C4 . . . . -179.7(2) ?
C7 C11 C12 C4 . . . . -0.3(3) ?
O1 C13 C14 C15 . . . . 4.5(5) ?
O1 C13 C14 C19 . . . . -175.7(3) ?
C19 C14 C15 C16 . . . . 0.5(4) ?
C13 C14 C15 C16 . . . . -179.7(3) ?
C14 C15 C16 C17 . . . . -0.9(5) ?
C15 C16 C17 C18 . . . . 0.8(5) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
C16 C17 C18 C20 . . . . -178.7(3) ?
Cu1 O2 C19 C14 . . . . 168.07(16) ?
Cu1 O2 C19 C18 . . . . -12.3(3) ?
C15 C14 C19 O2 . . . . 179.7(2) ?
C13 C14 C19 O2 . . . . -0.1(4) ?
C15 C14 C19 C18 . . . . 0.1(4) ?
C13 C14 C19 C18 . . . . -179.7(2) ?
C17 C18 C19 O2 . . . . -179.8(2) ?
C20 C18 C19 O2 . . . . -1.5(4) ?
C17 C18 C19 C14 . . . . -0.2(3) ?
C20 C18 C19 C14 . . . . 178.1(2) ?
Cu1 O3 C20 O4 . . . . -162.1(2) ?
Cu1 O3 C20 C18 . . . . 19.6(3) ?
C17 C18 C20 O4 . . . . -2.0(4) ?
C19 C18 C20 O4 . . . . 179.7(2) ?
C17 C18 C20 O3 . . . . 176.3(2) ?
C19 C18 C20 O3 . . . . -2.0(4) ?
C21 N3 C23 O5 . . . . -0.7(6) ?
C22 N3 C23 O5 . . . . -176.8(4) ?
