#------------------------------------------------------------------------------
#$Date: 2022-09-20 10:32:02 +0200 (mar 20 de sep de 2022) $
#$Revision: 277994 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/56/1565610.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_1565610
loop_
_publ_author_name
'Huang, Yan-Ju'
'Zhang, Jun'
_publ_section_title
;
 Synthesis and characterization a series of Norfloxacin-transition metal
 complexes
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119244
_journal_paper_doi               10.1016/j.ica.2019.119244
_journal_volume                  501
_journal_year                    2020
_chemical_formula_moiety         'C32 H36 Cu F2 N6 O6, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C32 H40 Cl2 Cu F2 N6 O8'
_chemical_formula_weight         809.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                106.3120(10)
_cell_angle_beta                 100.0060(10)
_cell_angle_gamma                96.7970(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4830(4)
_cell_length_b                   13.5406(6)
_cell_length_c                   13.8231(6)
_cell_measurement_reflns_used    13174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.303
_cell_measurement_theta_min      3.057
_cell_volume                     1651.16(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13174
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         3.057
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs,bruker(2008)
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             838
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+0.9936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6337
_reflns_number_total             7491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-501-119244.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 

2022-09-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C64 H80 Cl4 Cu2 F4 N12 O16'
_cod_original_formula_weight         1618.28
_cod_original_formula_moiety         '2(C32 H36 Cu F2 N6 O6), 4(Cl), 4(H2 O)'
_cod_original_formula_units_Z            1
_cod_database_code               1565610
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 OW2(HW2A,HW2B), OW1(HW1A,HW1B)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C13(H13A,H13B), N6(H6A,H6B), C12(H12A,H12B), N3(H3A,H3B),
 C10(H10A,H10B), C28(H28A,H28B), C27(H27A,H27B), C30(H30A,H30B), C14(H14A,H14B),
  C11(H11A,H11B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C25(H25), C3(H3), C19(H19), C22(H22), C6(H6)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C15(H15A,H15B,H15C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 -0.5000 -1.0000 2.5000 0.02696(10) Uani 1 2 d S T P . .
Cu2 Cu 0.0000 -0.5000 2.0000 0.02875(10) Uani 1 2 d S T P . .
Cl2 Cl -0.80583(5) -1.02059(4) 2.40079(4) 0.03904(13) Uani 1 1 d . . . . .
Cl1 Cl -0.30375(6) -0.52700(5) 1.89830(5) 0.04810(15) Uani 1 1 d . . . . .
O2 O -0.50340(16) -0.86045(11) 2.58266(9) 0.0306(3) Uani 1 1 d . . . . .
N1 N -0.55615(17) -0.68705(11) 2.32418(11) 0.0245(3) Uani 1 1 d . . . . .
O6 O 0.01626(17) -0.63551(11) 1.91464(10) 0.0324(3) Uani 1 1 d . . . . .
F2 F -0.16345(16) -0.55629(10) 2.44184(10) 0.0426(3) Uani 1 1 d . . . . .
O5 O 0.11812(17) -0.77492(11) 1.89129(10) 0.0344(3) Uani 1 1 d . . . . .
C29 C 0.0793(2) -0.76544(17) 2.54062(14) 0.0316(4) Uani 1 1 d . . . . .
H29A H 0.1677 -0.7553 2.5157 0.038 Uiso 1 1 calc R . . . .
H29B H 0.0348 -0.8387 2.5114 0.038 Uiso 1 1 calc R . . . .
C9 C -0.48935(19) -0.74463(13) 2.15843(13) 0.0237(3) Uani 1 1 d . . . . .
H9 H -0.5195 -0.6869 2.1429 0.028 Uiso 1 1 calc R . . . .
F1 F -0.32623(14) -0.96688(10) 2.04989(9) 0.0367(3) Uani 1 1 d . . . . .
O1 O -0.44805(14) -0.95026(10) 2.38841(10) 0.0257(3) Uani 1 1 d . . . . .
O4 O -0.04828(15) -0.55727(10) 2.10730(10) 0.0273(3) Uani 1 1 d . . . . .
C25 C 0.03507(18) -0.75899(13) 2.33746(13) 0.0215(3) Uani 1 1 d . . . . .
H25 H 0.0752 -0.8133 2.3536 0.026 Uiso 1 1 calc R . . . .
O3 O -0.56091(19) -0.70418(12) 2.61000(11) 0.0417(4) Uani 1 1 d . . . . .
N4 N 0.10990(15) -0.80498(11) 2.17328(11) 0.0206(3) Uani 1 1 d . . . . .
C13 C -0.5336(2) -0.74053(15) 1.95475(14) 0.0276(4) Uani 1 1 d . . . . .
H13A H -0.4822 -0.6689 1.9845 0.033 Uiso 1 1 calc R . . . .
H13B H -0.6227 -0.7459 1.9798 0.033 Uiso 1 1 calc R . . . .
C16 C -0.53399(18) -0.78308(14) 2.55178(12) 0.0241(3) Uani 1 1 d . . . . .
C5 C -0.45371(17) -0.84448(13) 2.27990(12) 0.0189(3) Uani 1 1 d . . . . .
C32 C 0.07008(18) -0.70553(13) 1.94720(12) 0.0222(3) Uani 1 1 d . . . . .
N6 N -0.0199(2) -0.74672(16) 2.69635(13) 0.0433(5) Uani 1 1 d . . . . .
H6A H -0.0627 -0.8136 2.6745 0.052 Uiso 1 1 calc R . . . .
H6B H 0.0025 -0.7262 2.7651 0.052 Uiso 1 1 calc R . . . .
C24 C -0.02994(17) -0.69567(13) 2.40798(12) 0.0209(3) Uani 1 1 d . . . . .
C12 C -0.5694(2) -0.76887(16) 1.83853(14) 0.0312(4) Uani 1 1 d . . . . .
H12A H -0.6278 -0.8384 1.8093 0.037 Uiso 1 1 calc R . . . .
H12B H -0.6259 -0.7201 1.8179 0.037 Uiso 1 1 calc R . . . .
N3 N -0.43411(19) -0.76596(15) 1.79822(12) 0.0352(4) Uani 1 1 d . . . . .
H3A H -0.4573 -0.7871 1.7295 0.042 Uiso 1 1 calc R . . . .
H3B H -0.3861 -0.7005 1.8191 0.042 Uiso 1 1 calc R . . . .
C10 C -0.30664(19) -0.80347(16) 1.95004(14) 0.0286(4) Uani 1 1 d . . . . .
H10A H -0.2468 -0.8495 1.9728 0.034 Uiso 1 1 calc R . . . .
H10B H -0.2531 -0.7324 1.9793 0.034 Uiso 1 1 calc R . . . .
C28 C 0.1157(2) -0.73625(19) 2.65690(15) 0.0388(5) Uani 1 1 d . . . . .
H28A H 0.1783 -0.7815 2.6781 0.047 Uiso 1 1 calc R . . . .
H28B H 0.1677 -0.6647 2.6859 0.047 Uiso 1 1 calc R . . . .
C27 C -0.1217(3) -0.68345(19) 2.66085(16) 0.0411(5) Uani 1 1 d . . . . .
H27A H -0.0788 -0.6099 2.6893 0.049 Uiso 1 1 calc R . . . .
H27B H -0.2109 -0.6941 2.6848 0.049 Uiso 1 1 calc R . . . .
C31 C 0.0300(3) -0.98978(16) 2.15651(18) 0.0438(5) Uani 1 1 d . . . . .
H31A H -0.0161 -1.0019 2.0857 0.066 Uiso 1 1 calc GR . . . .
H31B H -0.0387 -0.9724 2.1993 0.066 Uiso 1 1 calc GR . . . .
H31C H 0.0640 -1.0518 2.1641 0.066 Uiso 1 1 calc GR . . . .
C17 C -0.00267(17) -0.63701(13) 2.12247(12) 0.0193(3) Uani 1 1 d . . . . .
N5 N -0.02059(16) -0.70117(12) 2.50746(11) 0.0242(3) Uani 1 1 d . . . . .
C21 C -0.01911(17) -0.66154(12) 2.21575(12) 0.0193(3) Uani 1 1 d . . . . .
C30 C 0.1564(2) -0.90111(13) 2.18843(14) 0.0266(4) Uani 1 1 d . . . . .
H30A H 0.2012 -0.8876 2.2606 0.032 Uiso 1 1 calc R . . . .
H30B H 0.2286 -0.9205 2.1481 0.032 Uiso 1 1 calc R . . . .
C18 C 0.06403(17) -0.70680(13) 2.05429(12) 0.0201(3) Uani 1 1 d . . . . .
C4 C -0.49902(18) -0.75815(13) 2.25414(12) 0.0203(3) Uani 1 1 d . . . . .
C8 C -0.43571(17) -0.81549(13) 2.08640(12) 0.0209(3) Uani 1 1 d . . . . .
N2 N -0.44274(15) -0.81128(12) 1.98634(11) 0.0230(3) Uani 1 1 d . . . . .
C20 C 0.04142(17) -0.74258(12) 2.24252(12) 0.0188(3) Uani 1 1 d . . . . .
C3 C -0.56547(19) -0.70211(14) 2.41442(13) 0.0240(3) Uani 1 1 d . . . . .
H3 H -0.5996 -0.6518 2.4613 0.029 Uiso 1 1 calc R . . . .
C14 C -0.5949(2) -0.59198(15) 2.30026(16) 0.0350(4) Uani 1 1 d . . . . .
H14A H -0.6591 -0.6139 2.2324 0.042 Uiso 1 1 calc R . . . .
H14B H -0.5067 -0.5505 2.2962 0.042 Uiso 1 1 calc R . . . .
OW2 O -0.3442(2) -0.4848(2) 2.15425(17) 0.0666(5) Uani 1 1 d . . . . .
HW2A H -0.3062 -0.4852 2.1028 0.100 Uiso 1 1 d G . . . .
HW2B H -0.4316 -0.4753 2.1411 0.100 Uiso 1 1 d G . . . .
C19 C 0.11531(18) -0.78718(13) 2.08324(12) 0.0207(3) Uani 1 1 d . . . . .
H19 H 0.1568 -0.8326 2.0370 0.025 Uiso 1 1 calc R . . . .
C22 C -0.09279(19) -0.60136(13) 2.28455(13) 0.0239(3) Uani 1 1 d . . . . .
H22 H -0.1385 -0.5497 2.2671 0.029 Uiso 1 1 calc R . . . .
C11 C -0.3387(2) -0.83341(18) 1.83383(15) 0.0358(4) Uani 1 1 d . . . . .
H11A H -0.2484 -0.8257 1.8105 0.043 Uiso 1 1 calc R . . . .
H11B H -0.3860 -0.9060 1.8045 0.043 Uiso 1 1 calc R . . . .
C26 C -0.1553(2) -0.71466(16) 2.54477(14) 0.0290(4) Uani 1 1 d . . . . .
H26A H -0.2034 -0.7872 2.5165 0.035 Uiso 1 1 calc R . . . .
H26B H -0.2206 -0.6719 2.5216 0.035 Uiso 1 1 calc R . . . .
C7 C -0.38209(19) -0.89777(14) 2.11765(13) 0.0234(3) Uani 1 1 d . . . . .
C2 C -0.52818(18) -0.78684(13) 2.44319(12) 0.0217(3) Uani 1 1 d . . . . .
C23 C -0.0971(2) -0.61855(14) 2.37564(13) 0.0250(3) Uani 1 1 d . . . . .
OW1 O -0.1575(2) -1.0143(2) 2.35066(16) 0.0638(5) Uani 1 1 d . . . . .
HW1A H -0.0688 -1.0215 2.3615 0.096 Uiso 1 1 d G . . . .
HW1B H -0.1882 -1.0070 2.4060 0.096 Uiso 1 1 d G . . . .
C15 C -0.6664(3) -0.52313(17) 2.37389(19) 0.0444(5) Uani 1 1 d . . . . .
H15A H -0.6876 -0.4653 2.3501 0.067 Uiso 1 1 calc GR . . . .
H15B H -0.6024 -0.4974 2.4409 0.067 Uiso 1 1 calc GR . . . .
H15C H -0.7551 -0.5623 2.3781 0.067 Uiso 1 1 calc GR . . . .
C6 C -0.38999(18) -0.91248(13) 2.20961(13) 0.0223(3) Uani 1 1 d . . . . .
H6 H -0.3533 -0.9676 2.2265 0.027 Uiso 1 1 calc R . . . .
C1 C -0.47568(17) -0.86561(13) 2.37390(12) 0.0190(3) Uani 1 1 d . . . . .
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'
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'
F F 0.0171 0.0103 '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'
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
O6 Cu2 O4 91.67(5) 2_549 2_549
O6 Cu2 O4 88.33(5) 2_549 .
O6 Cu2 O4 91.67(5) . .
O6 Cu2 O4 88.33(5) . 2_549
O4 Cu2 O4 180.00(6) . 2_549
C16 O2 Cu1 127.97(11) . .
C4 N1 C14 119.29(14) . .
C3 N1 C4 119.18(14) . .
C3 N1 C14 121.37(15) . .
C32 O6 Cu2 125.42(11) . .
H29A C29 H29B 108.1 . .
C28 C29 H29A 109.6 . .
C28 C29 H29B 109.6 . .
N5 C29 H29A 109.6 . .
N5 C29 H29B 109.6 . .
N5 C29 C28 110.22(17) . .
C4 C9 H9 119.3 . .
C8 C9 H9 119.3 . .
C8 C9 C4 121.45(15) . .
C1 O1 Cu1 123.97(11) . .
C17 O4 Cu2 122.62(11) . .
C24 C25 H25 119.3 . .
C24 C25 C20 121.30(15) . .
C20 C25 H25 119.3 . .
C20 N4 C30 121.55(13) . .
C19 N4 C30 118.02(14) . .
C19 N4 C20 119.70(14) . .
H13A C13 H13B 108.2 . .
C12 C13 H13A 109.7 . .
C12 C13 H13B 109.7 . .
N2 C13 H13A 109.7 . .
N2 C13 H13B 109.7 . .
N2 C13 C12 109.68(15) . .
O2 C16 C2 118.84(15) . .
O3 C16 O2 121.87(15) . .
O3 C16 C2 119.20(16) . .
C4 C5 C6 117.92(14) . .
C4 C5 C1 121.47(14) . .
C6 C5 C1 120.58(14) . .
O6 C32 C18 118.65(15) . .
O5 C32 O6 121.92(15) . .
O5 C32 C18 119.28(15) . .
H6A N6 H6B 108.0 . .
C28 N6 H6A 109.4 . .
C28 N6 H6B 109.4 . .
C27 N6 H6A 109.4 . .
C27 N6 H6B 109.4 . .
C27 N6 C28 111.33(16) . .
C25 C24 C23 116.33(14) . .
N5 C24 C25 122.30(15) . .
N5 C24 C23 121.18(15) . .
C13 C12 H12A 109.5 . .
C13 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
N3 C12 C13 110.54(15) . .
N3 C12 H12A 109.5 . .
N3 C12 H12B 109.5 . .
C12 N3 H3A 109.3 . .
C12 N3 H3B 109.3 . .
H3A N3 H3B 107.9 . .
C11 N3 C12 111.76(15) . .
C11 N3 H3A 109.3 . .
C11 N3 H3B 109.3 . .
H10A C10 H10B 108.1 . .
N2 C10 H10A 109.6 . .
N2 C10 H10B 109.6 . .
N2 C10 C11 110.13(15) . .
C11 C10 H10A 109.6 . .
C11 C10 H10B 109.6 . .
C29 C28 H28A 109.6 . .
C29 C28 H28B 109.6 . .
N6 C28 C29 110.09(16) . .
N6 C28 H28A 109.6 . .
N6 C28 H28B 109.6 . .
H28A C28 H28B 108.2 . .
N6 C27 H27A 109.7 . .
N6 C27 H27B 109.7 . .
N6 C27 C26 109.70(17) . .
H27A C27 H27B 108.2 . .
C26 C27 H27A 109.7 . .
C26 C27 H27B 109.7 . .
H31A C31 H31B 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
O4 C17 C21 118.63(15) . .
O4 C17 C18 125.33(14) . .
C18 C17 C21 116.04(14) . .
C29 N5 C26 110.72(14) . .
C24 N5 C29 116.69(14) . .
C24 N5 C26 118.73(14) . .
C20 C21 C17 121.67(15) . .
C20 C21 C22 118.04(14) . .
C22 C21 C17 120.24(14) . .
N4 C30 C31 111.30(16) . .
N4 C30 H30A 109.4 . .
N4 C30 H30B 109.4 . .
C31 C30 H30A 109.4 . .
C31 C30 H30B 109.4 . .
H30A C30 H30B 108.0 . .
C17 C18 C32 124.39(15) . .
C19 C18 C32 116.31(15) . .
C19 C18 C17 119.03(14) . .
N1 C4 C9 120.29(14) . .
N1 C4 C5 119.17(14) . .
C9 C4 C5 120.53(15) . .
C9 C8 N2 122.31(15) . .
C9 C8 C7 116.44(14) . .
N2 C8 C7 121.10(15) . .
C13 N2 C10 110.59(14) . .
C8 N2 C13 116.08(14) . .
C8 N2 C10 118.06(14) . .
C25 C20 C21 120.62(15) . .
N4 C20 C25 120.89(14) . .
N4 C20 C21 118.48(14) . .
N1 C3 H3 117.6 . .
N1 C3 C2 124.74(16) . .
C2 C3 H3 117.6 . .
N1 C14 H14A 108.1 . .
N1 C14 H14B 108.1 . .
N1 C14 C15 116.87(17) . .
H14A C14 H14B 107.3 . .
C15 C14 H14A 108.1 . .
C15 C14 H14B 108.1 . .
HW2A OW2 HW2B 109.5 . .
N4 C19 C18 124.74(15) . .
N4 C19 H19 117.6 . .
C18 C19 H19 117.6 . .
C21 C22 H22 119.9 . .
C23 C22 C21 120.13(15) . .
C23 C22 H22 119.9 . .
N3 C11 C10 109.99(16) . .
N3 C11 H11A 109.7 . .
N3 C11 H11B 109.7 . .
C10 C11 H11A 109.7 . .
C10 C11 H11B 109.7 . .
H11A C11 H11B 108.2 . .
C27 C26 H26A 109.6 . .
C27 C26 H26B 109.6 . .
N5 C26 C27 110.19(16) . .
N5 C26 H26A 109.6 . .
N5 C26 H26B 109.6 . .
H26A C26 H26B 108.1 . .
F1 C7 C8 117.84(14) . .
F1 C7 C6 118.97(15) . .
C6 C7 C8 123.13(15) . .
C3 C2 C16 115.78(15) . .
C3 C2 C1 119.51(14) . .
C1 C2 C16 124.46(15) . .
F2 C23 C24 118.00(15) . .
C22 C23 F2 118.57(15) . .
C22 C23 C24 123.37(16) . .
HW1A OW1 HW1B 109.5 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C5 C6 H6 119.9 . .
C7 C6 C5 120.26(15) . .
C7 C6 H6 119.9 . .
O1 C1 C5 119.24(15) . .
O1 C1 C2 125.26(14) . .
C2 C1 C5 115.50(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9213(14) .
Cu1 O2 1.9214(14) 2_43:
Cu1 O1 1.9609(11) .
Cu1 O1 1.9608(12) 2_43:
Cu2 O6 1.9227(14) .
Cu2 O6 1.9228(14) 2_549
Cu2 O4 1.9517(12) .
Cu2 O4 1.9517(12) 2_549
O2 C16 1.282(2) .
N1 C4 1.393(2) .
N1 C3 1.335(2) .
N1 C14 1.487(2) .
O6 C32 1.279(2) .
F2 C23 1.355(2) .
O5 C32 1.226(2) .
C29 H29A 0.9700 .
C29 H29B 0.9700 .
C29 C28 1.509(3) .
C29 N5 1.460(2) .
C9 H9 0.9300 .
C9 C4 1.402(2) .
C9 C8 1.388(2) .
F1 C7 1.3532(19) .
O1 C1 1.267(2) .
O4 C17 1.266(2) .
C25 H25 0.9300 .
C25 C24 1.389(2) .
C25 C20 1.401(2) .
O3 C16 1.228(2) .
N4 C30 1.480(2) .
N4 C20 1.394(2) .
N4 C19 1.341(2) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C12 1.509(2) .
C13 N2 1.466(2) .
C16 C2 1.498(2) .
C5 C4 1.406(2) .
C5 C6 1.411(2) .
C5 C1 1.450(2) .
C32 C18 1.496(2) .
N6 H6A 0.8900 .
N6 H6B 0.8900 .
N6 C28 1.488(3) .
N6 C27 1.475(3) .
C24 N5 1.386(2) .
C24 C23 1.420(2) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 N3 1.486(3) .
N3 H3A 0.8900 .
N3 H3B 0.8900 .
N3 C11 1.480(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 N2 1.467(2) .
C10 C11 1.507(3) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C27 C26 1.505(3) .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C31 C30 1.500(3) .
C17 C21 1.448(2) .
C17 C18 1.425(2) .
N5 C26 1.469(2) .
C21 C20 1.405(2) .
C21 C22 1.410(2) .
C30 H30A 0.9700 .
C30 H30B 0.9700 .
C18 C19 1.372(2) .
C8 N2 1.391(2) .
C8 C7 1.419(2) .
C3 H3 0.9300 .
C3 C2 1.379(2) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.490(3) .
OW2 HW2A 0.8498 .
OW2 HW2B 0.8504 .
C19 H19 0.9300 .
C22 H22 0.9300 .
C22 C23 1.350(2) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C26 H26A 0.9700 .
C26 H26B 0.9700 .
C7 C6 1.354(2) .
C2 C1 1.422(2) .
OW1 HW1A 0.8501 .
OW1 HW1B 0.8499 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C6 H6 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cu1 O2 C16 O3 165.18(15) . . . .
Cu1 O2 C16 C2 -18.4(2) . . . .
Cu1 O1 C1 C5 -170.16(11) . . . .
Cu1 O1 C1 C2 9.7(2) . . . .
Cu2 O6 C32 O5 -157.29(14) . . . .
Cu2 O6 C32 C18 27.2(2) . . . .
Cu2 O4 C17 C21 167.80(11) . . . .
Cu2 O4 C17 C18 -12.6(2) . . . .
O2 C16 C2 C3 178.61(16) . . . .
O2 C16 C2 C1 -7.1(3) . . . .
N1 C3 C2 C16 174.50(17) . . . .
N1 C3 C2 C1 -0.1(3) . . . .
O6 C32 C18 C17 2.3(2) . . . .
O6 C32 C18 C19 176.22(16) . . . .
O5 C32 C18 C17 -173.34(16) . . . .
O5 C32 C18 C19 0.6(2) . . . .
C29 N5 C26 C27 59.8(2) . . . .
C9 C8 N2 C13 -11.0(2) . . . .
C9 C8 N2 C10 123.83(19) . . . .
C9 C8 C7 F1 -178.64(16) . . . .
C9 C8 C7 C6 4.2(3) . . . .
F1 C7 C6 C5 -177.12(16) . . . .
O4 C17 C21 C20 -173.70(15) . . . .
O4 C17 C21 C22 4.0(2) . . . .
O4 C17 C18 C32 -9.6(3) . . . .
O4 C17 C18 C19 176.59(16) . . . .
C25 C24 N5 C29 9.0(2) . . . .
C25 C24 N5 C26 -127.61(18) . . . .
C25 C24 C23 F2 179.09(16) . . . .
C25 C24 C23 C22 -3.8(3) . . . .
O3 C16 C2 C3 -4.9(2) . . . .
O3 C16 C2 C1 169.39(17) . . . .
C13 C12 N3 C11 55.1(2) . . . .
C16 C2 C1 O1 11.3(3) . . . .
C16 C2 C1 C5 -168.83(15) . . . .
C32 C18 C19 N4 -175.44(15) . . . .
N6 C27 C26 N5 -58.0(2) . . . .
C24 C25 C20 N4 178.47(15) . . . .
C24 C25 C20 C21 -0.4(3) . . . .
C24 N5 C26 C27 -161.22(17) . . . .
C12 C13 N2 C10 59.98(19) . . . .
C12 C13 N2 C8 -162.01(15) . . . .
C12 N3 C11 C10 -55.1(2) . . . .
C28 C29 N5 C24 161.13(16) . . . .
C28 C29 N5 C26 -58.9(2) . . . .
C28 N6 C27 C26 56.7(2) . . . .
C27 N6 C28 C29 -56.1(2) . . . .
C17 C21 C20 C25 174.38(15) . . . .
C17 C21 C20 N4 -4.6(2) . . . .
C17 C21 C22 C23 -174.27(16) . . . .
C17 C18 C19 N4 -1.2(3) . . . .
N5 C29 C28 N6 56.6(2) . . . .
N5 C24 C23 F2 -5.8(3) . . . .
N5 C24 C23 C22 171.28(18) . . . .
C21 C17 C18 C32 169.93(15) . . . .
C21 C17 C18 C19 -3.8(2) . . . .
C21 C22 C23 F2 177.18(16) . . . .
C21 C22 C23 C24 0.1(3) . . . .
C30 N4 C20 C25 10.4(2) . . . .
C30 N4 C20 C21 -170.66(15) . . . .
C30 N4 C19 C18 173.97(16) . . . .
C18 C17 C21 C20 6.7(2) . . . .
C18 C17 C21 C22 -175.62(15) . . . .
C4 N1 C3 C2 -3.0(3) . . . .
C4 N1 C14 C15 175.29(18) . . . .
C4 C9 C8 N2 171.38(16) . . . .
C4 C9 C8 C7 -4.3(3) . . . .
C4 C5 C6 C7 -4.1(3) . . . .
C4 C5 C1 O1 172.21(15) . . . .
C4 C5 C1 C2 -7.7(2) . . . .
C8 C9 C4 N1 -178.64(16) . . . .
C8 C9 C4 C5 0.2(3) . . . .
C8 C7 C6 C5 0.0(3) . . . .
N2 C13 C12 N3 -56.7(2) . . . .
N2 C10 C11 N3 57.3(2) . . . .
N2 C8 C7 F1 5.7(2) . . . .
N2 C8 C7 C6 -171.47(17) . . . .
C20 C25 C24 N5 -171.15(16) . . . .
C20 C25 C24 C23 3.9(2) . . . .
C20 N4 C30 C31 78.1(2) . . . .
C20 N4 C19 C18 3.6(3) . . . .
C20 C21 C22 C23 3.5(3) . . . .
C3 N1 C4 C9 179.39(16) . . . .
C3 N1 C4 C5 0.5(2) . . . .
C3 N1 C14 C15 -9.4(3) . . . .
C3 C2 C1 O1 -174.64(16) . . . .
C3 C2 C1 C5 5.2(2) . . . .
C14 N1 C4 C9 -5.2(3) . . . .
C14 N1 C4 C5 175.92(16) . . . .
C14 N1 C3 C2 -178.35(18) . . . .
C19 N4 C30 C31 -92.15(19) . . . .
C19 N4 C20 C25 -179.55(15) . . . .
C19 N4 C20 C21 -0.6(2) . . . .
C22 C21 C20 C25 -3.4(2) . . . .
C22 C21 C20 N4 177.70(15) . . . .
C11 C10 N2 C13 -60.6(2) . . . .
C11 C10 N2 C8 162.34(16) . . . .
C7 C8 N2 C13 164.47(16) . . . .
C7 C8 N2 C10 -60.7(2) . . . .
C23 C24 N5 C29 -165.80(17) . . . .
C23 C24 N5 C26 57.6(2) . . . .
C6 C5 C4 N1 -177.07(15) . . . .
C6 C5 C4 C9 4.1(2) . . . .
C6 C5 C1 O1 -5.7(2) . . . .
C6 C5 C1 C2 174.40(15) . . . .
C1 C5 C4 N1 5.0(2) . . . .
C1 C5 C4 C9 -173.92(16) . . . .
C1 C5 C6 C7 173.85(16) . . . .
