#------------------------------------------------------------------------------
#$Date: 2023-09-19 09:57:25 +0300 (Tue, 19 Sep 2023) $
#$Revision: 286400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107511.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_8107511
loop_
_publ_author_name
'Zeng-Bing, Zhao'
'Xue-Ping, Li'
'Shu-Cheng, Yang'
'Bing-Qi, Yang'
'Ze-Tao, Wang'
'Lan-Xing, Cheng'
'Xi-Shi, Tai'
_publ_section_title
;
 The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3
 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate,
 C23H17N3O5Cu
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              615
_journal_page_last               617
_journal_paper_doi               10.1515/ncrs-2023-0118
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C23 H15 Cu N3 O4, H2 O'
_chemical_formula_sum            'C23 H17 Cu N3 O5'
_chemical_formula_weight         478.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 105.4330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.49510(10)
_cell_length_b                   8.69660(10)
_cell_length_c                   21.1454(2)
_cell_measurement_reflns_used    12409
_cell_measurement_temperature    294.10(10)
_cell_measurement_theta_max      75.5200
_cell_measurement_theta_min      3.9820
_cell_volume                     2037.65(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.10(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    100.00 171.00   0.50    1.00    --  109.26  61.00 120.00  142
  2  ω     82.00 120.00   0.50    1.00    --  109.26 149.00 150.00   76
  3  ω    113.00 145.00   0.50    1.00    --  109.26 123.00 -12.00   64
  4  ω     98.00 131.00   0.50    1.00    --  109.26 125.00 -90.00   66
  5  ω    -30.00  26.00   0.50    0.32    --   43.18 -19.00 120.00  112
  6  ω     35.00  60.00   0.50    1.00    --  109.26 -61.00  30.00   50
  7  ω     35.00 106.00   0.50    1.00    --  109.26 -77.00  60.00  142
  8  ω     35.00  70.00   0.50    1.00    --  109.26 -61.00  60.00   70
  9  ω     38.00  70.00   0.50    1.00    --  109.26 -61.00 -30.00   64
 10  ω     40.00  66.00   0.50    1.00    --  109.26 -61.00 -60.00   52
 11  ω     43.00  71.00   0.50    1.00    --  109.26 -61.00 -90.00   56
 12  ω     35.00  92.00   0.50    1.00    --  109.26 -77.00-120.00  114
 13  ω    -21.00  42.00   0.50    0.32    --   43.18 -37.00-150.00  126
 14  ω     41.00  66.00   0.50    0.32    --   43.18-123.00 -93.00   50
 15  ω     39.00 107.00   0.50    1.00    --  109.26-125.00-120.00  136
 16  ω     72.00 101.00   0.50    1.00    --  109.26-123.00 -93.00   58
 17  ω     64.00  89.00   0.50    1.00    --  109.26-149.00 103.00   50
 18  ω     55.00  80.00   0.50    0.32    --   43.18-149.00 103.00   50
 19  ω    -51.00 -16.00   0.50    1.00    --  -90.25  45.00 150.00   70
 20  ω    -49.00 -15.00   0.50    1.00    --  -90.25  45.00 120.00   68
 21  ω   -102.00 -25.00   0.50    0.32    --  -43.18 149.00 150.00  154
 22  ω    -61.00 -35.00   0.50    0.32    --  -43.18 123.00 -12.00   52
 23  ω    -51.00 -14.00   0.50    1.00    --  -90.25  45.00  30.00   74
 24  ω    -80.00 -55.00   0.50    0.32    --  -43.18 -57.00 -60.00   50
 25  ω   -116.00 -14.00   0.50    0.32    --  -43.18 -77.00  90.00  204
 26  ω   -111.00 -86.00   0.50    0.32    --  -43.18 -57.00 -60.00   50
 27  ω   -113.00 -86.00   0.50    1.00    --  -90.25 -61.00-180.00   54
 28  ω   -143.00-117.00   0.50    1.00    --  -90.25 -61.00-180.00   52
 29  ω   -133.00 -75.00   0.50    1.00    --  -90.25-123.00 -93.00  116
 30  ω   -122.00 -96.00   0.50    1.00    --  -90.25-149.00 103.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0818385000
_diffrn_orient_matrix_UB_12      0.0342862000
_diffrn_orient_matrix_UB_13      0.0453315000
_diffrn_orient_matrix_UB_21      -0.1030657000
_diffrn_orient_matrix_UB_22      0.0455590000
_diffrn_orient_matrix_UB_23      -0.0600529000
_diffrn_orient_matrix_UB_31      -0.0448116000
_diffrn_orient_matrix_UB_32      -0.1677490000
_diffrn_orient_matrix_UB_33      -0.0070433000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14284
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.722
_diffrn_reflns_theta_min         4.002
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0039(2)
_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   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+0.7197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3836
_reflns_number_total             4042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0118_suppl_001.cif
_cod_data_source_block           1-1
_cod_database_code               8107511
_chemical_oxdiff_formula         'C H O N Cu'
_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   0.820
_shelx_estimated_absorpt_t_min   0.765
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.85 with sigma of 0.02
 H1A-H1B
 1.34 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.647
loop_
_space_group_symop_operation_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_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
Cu1 Cu 0.31393(2) 0.69233(2) 0.50148(2) 0.02713(10) Uani 1 1 d . . . . .
O2 O 0.35438(10) 0.88309(13) 0.55588(5) 0.0359(3) Uani 1 1 d . . . . .
O3 O 0.27938(10) 0.78347(13) 0.41591(5) 0.0358(3) Uani 1 1 d . . . . .
O4 O 0.14795(14) 0.91025(19) 0.33800(6) 0.0599(4) Uani 1 1 d . . . . .
O5 O 0.44476(13) 0.96187(16) 0.65749(6) 0.0523(3) Uani 1 1 d . . . . .
N1 N 0.40494(11) 0.60110(14) 0.58195(6) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.32574(11) 0.47022(15) 0.47109(6) 0.0291(3) Uani 1 1 d . . . . .
N3 N 0.11438(11) 0.74380(15) 0.48496(6) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.14561(16) 0.5263(2) 0.59442(9) 0.0434(4) Uani 1 1 d . . . . .
H1 H 0.166756 0.485694 0.558340 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1835(2) 0.4529(3) 0.65453(11) 0.0562(5) Uani 1 1 d . . . . .
H2 H 0.229845 0.363998 0.658569 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1522(3) 0.5120(3) 0.70865(12) 0.0734(7) Uani 1 1 d . . . . .
H3 H 0.178576 0.464186 0.749310 0.088 Uiso 1 1 calc R U . . .
C4 C 0.0815(3) 0.6426(4) 0.70150(13) 0.0819(8) Uani 1 1 d . . . . .
H4 H 0.059201 0.681619 0.737519 0.098 Uiso 1 1 calc R U . . .
C5 C 0.0437(2) 0.7159(3) 0.64193(12) 0.0645(6) Uani 1 1 d . . . . .
H5 H -0.004049 0.803477 0.638039 0.077 Uiso 1 1 calc R U . . .
C6 C 0.07661(16) 0.6596(2) 0.58703(10) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.03748(15) 0.7376(2) 0.52264(9) 0.0397(4) Uani 1 1 d . . . . .
C8 C -0.07694(17) 0.8064(2) 0.50218(13) 0.0545(5) Uani 1 1 d . . . . .
H8 H -0.128311 0.804839 0.529523 0.065 Uiso 1 1 calc R U . . .
C9 C -0.11293(17) 0.8757(2) 0.44187(13) 0.0608(6) Uani 1 1 d . . . . .
H9 H -0.189514 0.918760 0.427476 0.073 Uiso 1 1 calc R U . . .
C10 C -0.03443(16) 0.8809(2) 0.40300(11) 0.0510(5) Uani 1 1 d . . . . .
H10 H -0.057188 0.926054 0.361663 0.061 Uiso 1 1 calc R U . . .
C11 C 0.07992(15) 0.81704(18) 0.42682(9) 0.0367(4) Uani 1 1 d . . . . .
C12 C 0.17479(16) 0.8378(2) 0.38969(8) 0.0368(4) Uani 1 1 d . . . . .
C13 C 0.41126(14) 0.86093(19) 0.61610(8) 0.0336(3) Uani 1 1 d . . . . .
C14 C 0.44073(14) 0.69335(18) 0.63365(7) 0.0314(3) Uani 1 1 d . . . . .
C15 C 0.50221(16) 0.6338(2) 0.69410(8) 0.0422(4) Uani 1 1 d . . . . .
H15 H 0.525871 0.696696 0.730877 0.051 Uiso 1 1 calc R U . . .
C16 C 0.52730(17) 0.4780(2) 0.69803(8) 0.0456(4) Uani 1 1 d . . . . .
H16 H 0.568397 0.435456 0.738106 0.055 Uiso 1 1 calc R U . . .
C17 C 0.49225(15) 0.3842(2) 0.64331(8) 0.0393(4) Uani 1 1 d . . . . .
H17 H 0.510545 0.279876 0.645931 0.047 Uiso 1 1 calc R U . . .
C18 C 0.42889(13) 0.45057(17) 0.58430(7) 0.0293(3) Uani 1 1 d . . . . .
C19 C 0.38409(12) 0.37454(17) 0.52000(7) 0.0286(3) Uani 1 1 d . . . . .
C20 C 0.39977(15) 0.21976(19) 0.50862(9) 0.0359(3) Uani 1 1 d . . . . .
H20 H 0.439737 0.155274 0.542555 0.043 Uiso 1 1 calc R U . . .
C21 C 0.35448(15) 0.1634(2) 0.44548(9) 0.0408(4) Uani 1 1 d . . . . .
H21 H 0.363411 0.059974 0.436686 0.049 Uiso 1 1 calc R U . . .
C22 C 0.29628(15) 0.2610(2) 0.39588(9) 0.0408(4) Uani 1 1 d . . . . .
H22 H 0.266151 0.224558 0.353305 0.049 Uiso 1 1 calc R U . . .
C23 C 0.28325(14) 0.4148(2) 0.41042(8) 0.0350(3) Uani 1 1 d . . . . .
H23 H 0.243866 0.480891 0.376999 0.042 Uiso 1 1 calc R U . . .
O1 O 0.67360(18) 1.0861(4) 0.74113(10) 0.0981(8) Uani 1 1 d D . . . .
H1A H 0.612(3) 1.034(5) 0.721(2) 0.147 Uiso 1 1 d D U . . .
H1B H 0.719(3) 1.071(5) 0.7163(18) 0.147 Uiso 1 1 d D 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'
Cu Cu -1.9646 0.5888 '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
O2 Cu1 N2 159.34(5) . .
O2 Cu1 N3 89.75(5) . .
O3 Cu1 O2 99.08(5) . .
O3 Cu1 N2 96.20(5) . .
O3 Cu1 N3 80.00(5) . .
N1 Cu1 O2 81.05(5) . .
N1 Cu1 O3 159.40(5) . .
N1 Cu1 N2 79.77(5) . .
N1 Cu1 N3 120.57(5) . .
N2 Cu1 N3 106.60(5) . .
C13 O2 Cu1 115.17(10) . .
C12 O3 Cu1 119.92(11) . .
C14 N1 Cu1 117.17(10) . .
C14 N1 C18 123.03(13) . .
C18 N1 Cu1 119.81(10) . .
C19 N2 Cu1 113.51(10) . .
C23 N2 Cu1 127.10(11) . .
C23 N2 C19 119.39(14) . .
C7 N3 Cu1 134.43(11) . .
C7 N3 C11 118.78(14) . .
C11 N3 Cu1 105.86(10) . .
C2 C1 H1 119.4 . .
C2 C1 C6 121.23(18) . .
C6 C1 H1 119.4 . .
C1 C2 H2 120.0 . .
C1 C2 C3 120.0(2) . .
C3 C2 H2 120.0 . .
C2 C3 H3 120.4 . .
C4 C3 C2 119.2(2) . .
C4 C3 H3 120.4 . .
C3 C4 H4 119.5 . .
C5 C4 C3 121.0(2) . .
C5 C4 H4 119.5 . .
C4 C5 H5 119.7 . .
C4 C5 C6 120.5(2) . .
C6 C5 H5 119.7 . .
C1 C6 C5 118.0(2) . .
C1 C6 C7 120.71(16) . .
C5 C6 C7 121.28(19) . .
N3 C7 C6 118.58(15) . .
N3 C7 C8 120.80(18) . .
C8 C7 C6 120.60(17) . .
C7 C8 H8 120.0 . .
C9 C8 C7 120.0(2) . .
C9 C8 H8 120.0 . .
C8 C9 H9 120.4 . .
C8 C9 C10 119.15(17) . .
C10 C9 H9 120.4 . .
C9 C10 H10 120.7 . .
C9 C10 C11 118.5(2) . .
C11 C10 H10 120.7 . .
N3 C11 C10 122.61(18) . .
N3 C11 C12 116.87(14) . .
C10 C11 C12 120.38(17) . .
O3 C12 C11 117.17(14) . .
O4 C12 O3 124.24(17) . .
O4 C12 C11 118.53(16) . .
O2 C13 C14 114.10(14) . .
O5 C13 O2 125.55(17) . .
O5 C13 C14 120.31(15) . .
N1 C14 C13 112.20(13) . .
N1 C14 C15 120.22(15) . .
C15 C14 C13 127.52(15) . .
C14 C15 H15 121.0 . .
C16 C15 C14 117.92(16) . .
C16 C15 H15 121.0 . .
C15 C16 H16 119.4 . .
C15 C16 C17 121.12(15) . .
C17 C16 H16 119.4 . .
C16 C17 H17 120.9 . .
C16 C17 C18 118.15(16) . .
C18 C17 H17 120.9 . .
N1 C18 C17 119.53(15) . .
N1 C18 C19 112.76(13) . .
C17 C18 C19 127.70(15) . .
N2 C19 C18 114.07(13) . .
N2 C19 C20 121.55(14) . .
C20 C19 C18 124.38(14) . .
C19 C20 H20 120.8 . .
C21 C20 C19 118.47(16) . .
C21 C20 H20 120.8 . .
C20 C21 H21 120.1 . .
C22 C21 C20 119.85(16) . .
C22 C21 H21 120.1 . .
C21 C22 H22 120.5 . .
C21 C22 C23 118.94(15) . .
C23 C22 H22 120.5 . .
N2 C23 C22 121.80(15) . .
N2 C23 H23 119.1 . .
C22 C23 H23 119.1 . .
H1A O1 H1B 101(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 2.0018(11) .
Cu1 O3 1.9176(11) .
Cu1 N1 1.9163(12) .
Cu1 N2 2.0515(13) .
Cu1 N3 2.2710(12) .
O2 C13 1.282(2) .
O3 C12 1.273(2) .
O4 C12 1.228(2) .
O5 C13 1.227(2) .
N1 C14 1.330(2) .
N1 C18 1.336(2) .
N2 C19 1.3574(19) .
N2 C23 1.335(2) .
N3 C7 1.339(2) .
N3 C11 1.347(2) .
C1 H1 0.9300 .
C1 C2 1.385(3) .
C1 C6 1.390(3) .
C2 H2 0.9300 .
C2 C3 1.386(3) .
C3 H3 0.9300 .
C3 C4 1.382(4) .
C4 H4 0.9300 .
C4 C5 1.375(4) .
C5 H5 0.9300 .
C5 C6 1.401(3) .
C6 C7 1.480(3) .
C7 C8 1.404(3) .
C8 H8 0.9300 .
C8 C9 1.371(3) .
C9 H9 0.9300 .
C9 C10 1.374(3) .
C10 H10 0.9300 .
C10 C11 1.392(2) .
C11 C12 1.515(3) .
C13 C14 1.520(2) .
C14 C15 1.386(2) .
C15 H15 0.9300 .
C15 C16 1.384(3) .
C16 H16 0.9300 .
C16 C17 1.385(3) .
C17 H17 0.9300 .
C17 C18 1.392(2) .
C18 C19 1.476(2) .
C19 C20 1.388(2) .
C20 H20 0.9300 .
C20 C21 1.387(3) .
C21 H21 0.9300 .
C21 C22 1.376(3) .
C22 H22 0.9300 .
C22 C23 1.389(2) .
C23 H23 0.9300 .
O1 H1A 0.849(19) .
O1 H1B 0.846(19) .
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
Cu1 O2 C13 O5 179.73(14) . . . .
Cu1 O2 C13 C14 2.09(16) . . . .
Cu1 O3 C12 O4 173.13(14) . . . .
Cu1 O3 C12 C11 -4.0(2) . . . .
Cu1 N1 C14 C13 -5.59(16) . . . .
Cu1 N1 C14 C15 177.11(12) . . . .
Cu1 N1 C18 C17 -178.30(11) . . . .
Cu1 N1 C18 C19 2.98(16) . . . .
Cu1 N2 C19 C18 -1.18(15) . . . .
Cu1 N2 C19 C20 179.48(11) . . . .
Cu1 N2 C23 C22 -179.62(12) . . . .
Cu1 N3 C7 C6 -11.7(2) . . . .
Cu1 N3 C7 C8 167.07(13) . . . .
Cu1 N3 C11 C10 -173.40(14) . . . .
Cu1 N3 C11 C12 2.30(16) . . . .
O2 C13 C14 N1 2.13(19) . . . .
O2 C13 C14 C15 179.19(16) . . . .
O5 C13 C14 N1 -175.64(15) . . . .
O5 C13 C14 C15 1.4(3) . . . .
N1 C14 C15 C16 1.7(3) . . . .
N1 C18 C19 N2 -0.99(18) . . . .
N1 C18 C19 C20 178.32(14) . . . .
N2 C19 C20 C21 0.2(2) . . . .
N3 C7 C8 C9 2.5(3) . . . .
N3 C11 C12 O3 0.6(2) . . . .
N3 C11 C12 O4 -176.71(16) . . . .
C1 C2 C3 C4 1.1(4) . . . .
C1 C6 C7 N3 -38.5(2) . . . .
C1 C6 C7 C8 142.82(18) . . . .
C2 C1 C6 C5 -1.5(3) . . . .
C2 C1 C6 C7 179.54(17) . . . .
C2 C3 C4 C5 -1.1(4) . . . .
C3 C4 C5 C6 -0.2(4) . . . .
C4 C5 C6 C1 1.5(3) . . . .
C4 C5 C6 C7 -179.5(2) . . . .
C5 C6 C7 N3 142.66(19) . . . .
C5 C6 C7 C8 -36.1(3) . . . .
C6 C1 C2 C3 0.2(3) . . . .
C6 C7 C8 C9 -178.76(18) . . . .
C7 N3 C11 C10 -2.9(2) . . . .
C7 N3 C11 C12 172.83(14) . . . .
C7 C8 C9 C10 -1.9(3) . . . .
C8 C9 C10 C11 -0.9(3) . . . .
C9 C10 C11 N3 3.4(3) . . . .
C9 C10 C11 C12 -172.14(17) . . . .
C10 C11 C12 O3 176.39(16) . . . .
C10 C11 C12 O4 -0.9(3) . . . .
C11 N3 C7 C6 -178.86(15) . . . .
C11 N3 C7 C8 -0.1(2) . . . .
C13 C14 C15 C16 -175.15(16) . . . .
C14 N1 C18 C17 1.2(2) . . . .
C14 N1 C18 C19 -177.55(13) . . . .
C14 C15 C16 C17 0.1(3) . . . .
C15 C16 C17 C18 -1.2(3) . . . .
C16 C17 C18 N1 0.6(2) . . . .
C16 C17 C18 C19 179.14(15) . . . .
C17 C18 C19 N2 -179.59(15) . . . .
C17 C18 C19 C20 -0.3(2) . . . .
C18 N1 C14 C13 174.93(13) . . . .
C18 N1 C14 C15 -2.4(2) . . . .
C18 C19 C20 C21 -179.10(14) . . . .
C19 N2 C23 C22 0.5(2) . . . .
C19 C20 C21 C22 0.4(2) . . . .
C20 C21 C22 C23 -0.5(2) . . . .
C21 C22 C23 N2 0.1(2) . . . .
C23 N2 C19 C18 178.73(13) . . . .
C23 N2 C19 C20 -0.6(2) . . . .
