##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_journal_date_recd_electronic     2016-04-01
_journal_date_accepted     2016-06-02
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      7
_journal_page_first     544
_journal_page_last     548
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616008913
_journal_coeditor_code     FA3386
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'F. R. G. Bergamini'
;
Department of Inorganic Chemistry
Institute of Chemistry
University of Campinas--UNICAMP
PO Box 6154
Campinas
SP 13083-970
Brazil
;
 bergamini.frg@gmail.com
    'P. P. Corbi'
;
Department of Inorganic Chemistry
Institute of Chemistry
University of Campinas--UNICAMP
PO Box 6154
Campinas
SP 13083-970
Brazil
;
 ppcorbi@iqm.unicamp.br
_publ_section_title
;
A novel binuclear copper complex incorporating a nalidixic acid derivative
displaying a one-dimensional coordination polymeric structure
;
loop_
    _publ_author_name
    _publ_author_address
    'F. R. G. Bergamini'
;
Department of Inorganic Chemistry
Institute of Chemistry
University of Campinas--UNICAMP
PO Box 6154
Campinas
SP 13083-970
Brazil
;
    'M. A. Ribeiro'
;
Department of Inorganic Chemistry
Institute of Chemistry
University of Campinas--UNICAMP
PO Box 6154
Campinas
SP 13083-970
Brazil
;
    'P. C. M. L. Miranda'
;
Department of Organic Chemistry
University of Campinas
PO Box 6154
Campinas
SP 13083-970
Brazil
;
    'A. L. B. Formiga'
;
Department of Inorganic Chemistry
Institute of Chemistry
University of Campinas--UNICAMP
PO Box 6154
Campinas
SP 13083-970
Brazil
;
    'P. P. Corbi'
;
Department of Inorganic Chemistry
Institute of Chemistry
University of Campinas--UNICAMP
PO Box 6154
Campinas
SP 13083-970
Brazil
;
_publ_section_synopsis
;
In the structure of a polymeric copper(II) complex with a carbonyl hydrazone
derivative of nalidixic acid, square-pyramidal and octahedral CuII ions
alternate along the polymer chain.
;
_database_code_depnum_ccdc_archive     'CCDC 1483258'
_chemical_name_systematic
;\
catena-Poly[[copper(II)-di-μ-chlorido-copper(II)-{μ-1-ethyl-\
N'-[(1H-imidazol-3-yl)methylidene]-7-methyl-4-oxo-\
1,4-dihydro-1,8-naphthyridine-3-carbohydrazidato}-[dimethanolcopper(II)]-\
{μ-1-ethyl-N'-[(1H-imidazol-3-yl)methylidene]-7-methyl-4-oxo-\
1,4-dihydro-1,8-naphthyridine-3-carbohydrazidato}] dichloride
methanol tetrasolvate]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H15 Cl Cu1.5 N6 O2, Cl, 2(C H4 O)'
_chemical_formula_sum     'C18 H23 Cl2 Cu1.50 N6 O4'
_chemical_formula_iupac
                         '[Cu3 (C16 H15 N6 O2)2 Cl2 (C1 H4 O1)2] Cl2, 4C1 H4 O1'
_chemical_formula_weight     1107.26
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C 2/c'
_space_group_name_Hall     '-C 2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     18.5958(11)
_cell_length_b     16.6608(10)
_cell_length_c     14.2394(9)
_cell_angle_alpha     90
_cell_angle_beta     93.692(2)
_cell_angle_gamma     90
_cell_volume     4402.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9900
_cell_measurement_theta_min     2.83
_cell_measurement_theta_max     28.20
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     green
_exptl_crystal_size_max     0.257
_exptl_crystal_size_mid     0.168
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.671
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     2260
_exptl_absorpt_coefficient_mu     1.744
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.6912
_exptl_absorpt_correction_T_max     0.7457
_exptl_special_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0498 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.9269.
The λ/2 correction factor is 0.00150.
;
_diffrn_ambient_temperature     150.0
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     34794
_diffrn_reflns_av_R_equivalents     0.0294
_diffrn_reflns_theta_min     1.643
_diffrn_reflns_theta_max     28.313
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     5471
_reflns_number_gt     4751
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0343
_refine_ls_R_factor_gt     0.0274
_refine_ls_wR_factor_gt     0.0703
_refine_ls_wR_factor_ref     0.0739
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     5471
_refine_ls_number_parameters     294
_refine_ls_number_restraints     25
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0356P)²+7.5985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.543
_refine_diff_density_min     -0.513
_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'
    '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'
    '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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cu Cu1 0.47615(2) 0.68901(2) 0.36649(2) 0.01472(6) Uani d 1 . .
    Cl Cl1 0.64032(3) 0.05663(3) 0.32933(5) 0.04294(16) Uani d 1 . .
    Cu Cu2 0.2500 0.7500 0.5000 0.01651(8) Uani d 1 . .
    Cl Cl2 0.41153(2) 0.67586(3) 0.19402(3) 0.01953(10) Uani d 1 . .
    O O2 0.28293(7) 0.64150(7) 0.49541(9) 0.0181(3) Uani d 1 . .
    C C18 0.22719(13) 0.73844(17) 0.26149(16) 0.0379(6) Uani d 1 . .
    H H18A 0.1956 0.7328 0.2040 0.057 Uiso calc 1 . .
    H H18B 0.2632 0.6954 0.2642 0.057 Uiso calc 1 . .
    H H18C 0.2516 0.7905 0.2612 0.057 Uiso calc 1 . .
    C C5 0.34270(9) 0.63378(10) 0.45766(12) 0.0142(3) Uani d 1 . .
    C C10 0.32155(10) 0.49200(11) 0.47609(13) 0.0191(4) Uani d 1 . .
    H H10 0.2781 0.5089 0.5016 0.023 Uiso calc 1 . .
    N N6 0.40462(9) 0.30580(9) 0.42752(11) 0.0200(3) Uani d 1 . .
    C C7 0.43359(9) 0.52754(11) 0.41004(12) 0.0143(3) Uani d 1 . .
    O O1 0.48136(7) 0.57491(8) 0.38402(9) 0.0199(3) Uani d 1 . .
    N N2 0.48830(8) 0.80569(9) 0.37265(11) 0.0169(3) Uani d 1 . .
    C C2 0.54366(10) 0.85055(12) 0.35118(13) 0.0210(4) Uani d 1 . .
    H H2 0.5879 0.8299 0.3317 0.025 Uiso calc 1 . .
    N N1 0.52919(9) 0.92866(10) 0.36055(13) 0.0254(4) Uani d 1 . .
    H H1 0.5587 0.9685 0.3500 0.030 Uiso calc 1 . .
    C C1 0.46128(11) 0.93587(12) 0.38905(15) 0.0239(4) Uani d 1 . .
    H H1A 0.4364 0.9843 0.4010 0.029 Uiso calc 1 . .
    C C3 0.43578(10) 0.85916(11) 0.39719(13) 0.0184(4) Uani d 1 . .
    C C4 0.36732(10) 0.83710(11) 0.42980(13) 0.0185(4) Uani d 1 . .
    H H4 0.3357 0.8803 0.4412 0.022 Uiso calc 1 . .
    N N3 0.34300(8) 0.76657(9) 0.44565(11) 0.0158(3) Uani d 1 . .
    C C6 0.36748(9) 0.55065(10) 0.44654(12) 0.0145(3) Uani d 1 . .
    N N5 0.33399(8) 0.41321(9) 0.47135(12) 0.0206(3) Uani d 1 . .
    C C9 0.39648(10) 0.38588(11) 0.43381(12) 0.0170(3) Uani d 1 . .
    C C13 0.46479(11) 0.27836(12) 0.39315(13) 0.0214(4) Uani d 1 . .
    C C12 0.51965(11) 0.32959(12) 0.36530(13) 0.0218(4) Uani d 1 . .
    H H12 0.5629 0.3080 0.3437 0.026 Uiso calc 1 . .
    C C11 0.51000(10) 0.41102(12) 0.36973(12) 0.0187(4) Uani d 1 . .
    H H11 0.5460 0.4464 0.3497 0.022 Uiso calc 1 . .
    C C8 0.44637(9) 0.44187(11) 0.40417(12) 0.0155(3) Uani d 1 . .
    C C14 0.47078(13) 0.18882(12) 0.38232(15) 0.0287(5) Uani d 1 . .
    H H14A 0.4522 0.1623 0.4372 0.043 Uiso calc 1 . .
    H H14B 0.5214 0.1741 0.3775 0.043 Uiso calc 1 . .
    H H14C 0.4426 0.1718 0.3253 0.043 Uiso calc 1 . .
    N N4 0.38150(8) 0.69624(9) 0.42930(10) 0.0137(3) Uani d 1 . .
    O O3 0.18547(8) 0.73350(9) 0.34110(11) 0.0269(3) Uani d 1 . .
    H H3 0.1699 0.6865 0.3462 0.040 Uiso calc 1 . .
    O O4 0.72490(11) -0.01627(17) 0.16711(16) 0.0682(7) Uani d 1 . .
    H H4A 0.6959 -0.0077 0.2089 0.102 Uiso calc 1 . .
    C C17 0.79330(15) -0.03305(19) 0.20971(18) 0.0463(6) Uani d 1 . .
    H H17A 0.7883 -0.0541 0.2732 0.069 Uiso calc 1 . .
    H H17B 0.8221 0.0163 0.2135 0.069 Uiso calc 1 . .
    H H17C 0.8174 -0.0730 0.1722 0.069 Uiso calc 1 . .
    C C15A 0.2775(4) 0.3515(7) 0.4911(7) 0.0275(5) Uani d 0.326(4) A 1
    H H15A 0.2700 0.3163 0.4353 0.033 Uiso calc 0.326(4) A 1
    H H15B 0.2962 0.3176 0.5443 0.033 Uiso calc 0.326(4) A 1
    C C16A 0.2070(3) 0.3846(4) 0.5139(5) 0.0275(5) Uani d 0.326(4) A 1
    H H16A 0.1871 0.4170 0.4610 0.041 Uiso calc 0.326(4) A 1
    H H16B 0.2133 0.4183 0.5703 0.041 Uiso calc 0.326(4) A 1
    H H16C 0.1739 0.3405 0.5257 0.041 Uiso calc 0.326(4) A 1
    C C15B 0.2817(2) 0.3587(3) 0.5150(3) 0.0275(5) Uani d 0.674(4) A 2
    H H15C 0.2727 0.3778 0.5790 0.033 Uiso calc 0.674(4) A 2
    H H15D 0.3019 0.3038 0.5203 0.033 Uiso calc 0.674(4) A 2
    C C16B 0.21244(16) 0.35759(19) 0.4550(2) 0.0275(5) Uani d 0.674(4) A 2
    H H16D 0.2212 0.3362 0.3927 0.041 Uiso calc 0.674(4) A 2
    H H16E 0.1935 0.4123 0.4486 0.041 Uiso calc 0.674(4) A 2
    H H16F 0.1774 0.3235 0.4846 0.041 Uiso calc 0.674(4) A 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    Cu1 Cl2 2_655 2.3206(5) ?
    Cu1 Cl2 . 2.6727(5) ?
    Cu1 O1 . 1.9190(13) ?
    Cu1 N4 . 2.0285(14) ?
    Cu2 O2 . 1.9110(12) ?
    Cu2 O2 7_566 1.9110(12) ?
    Cu2 N3 7_566 1.9593(15) ?
    Cl2 Cu1 2_655 2.3206(5) ?
    O2 C5 . 1.272(2) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C18 O3 . 1.417(3) ?
    C5 C6 . 1.472(2) ?
    C5 N4 . 1.343(2) ?
    C10 H10 . 0.9500 ?
    C10 C6 . 1.381(2) ?
    C10 N5 . 1.335(2) ?
    N6 C9 . 1.346(2) ?
    N6 C13 . 1.331(2) ?
    C7 O1 . 1.262(2) ?
    C7 C6 . 1.418(2) ?
    C7 C8 . 1.450(2) ?
    N2 C2 . 1.324(2) ?
    N2 C3 . 1.383(2) ?
    C2 H2 . 0.9500 ?
    C2 N1 . 1.337(3) ?
    N1 H1 . 0.8800 ?
    N1 C1 . 1.356(3) ?
    C1 H1A . 0.9500 ?
    C1 C3 . 1.371(3) ?
    C3 C4 . 1.431(2) ?
    C4 H4 . 0.9500 ?
    C4 N3 . 1.284(2) ?
    N3 N4 . 1.400(2) ?
    N5 C9 . 1.387(2) ?
    N5 C15A . 1.509(11) ?
    N5 C15B . 1.495(5) ?
    C9 C8 . 1.400(3) ?
    C13 C12 . 1.407(3) ?
    C13 C14 . 1.505(3) ?
    C12 H12 . 0.9500 ?
    C12 C11 . 1.371(3) ?
    C11 H11 . 0.9500 ?
    C11 C8 . 1.407(2) ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    O3 H3 . 0.8400 ?
    O4 H4A . 0.8400 ?
    O4 C17 . 1.402(3) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C15A H15A . 0.9900 ?
    C15A H15B . 0.9900 ?
    C15A C16A . 1.478(8) ?
    C16A H16A . 0.9800 ?
    C16A H16B . 0.9800 ?
    C16A H16C . 0.9800 ?
    C15B H15C . 0.9900 ?
    C15B H15D . 0.9900 ?
    C15B C16B . 1.499(4) ?
    C16B H16D . 0.9800 ?
    C16B H16E . 0.9800 ?
    C16B H16F . 0.9800 ?
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
    Cl2 Cu1 Cl2 2_655 . 90.757(16) ?
    O1 Cu1 Cl2 . 2_655 85.16(4) ?
    O1 Cu1 Cl2 . . 93.11(4) ?
    O1 Cu1 N4 . . 92.27(6) ?
    N4 Cu1 Cl2 . . 93.35(4) ?
    N4 Cu1 Cl2 . 2_655 175.27(4) ?
    O2 Cu2 O2 7_566 . 180.0 ?
    O2 Cu2 N3 . 7_566 99.97(6) ?
    O2 Cu2 N3 7_566 7_566 80.03(6) ?
    Cu1 Cl2 Cu1 2_655 . 88.356(16) ?
    C5 O2 Cu2 . . 113.63(11) ?
    H18A C18 H18B . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O3 C18 H18A . . 109.5 ?
    O3 C18 H18B . . 109.5 ?
    O3 C18 H18C . . 109.5 ?
    O2 C5 C6 . . 115.40(15) ?
    O2 C5 N4 . . 123.35(16) ?
    N4 C5 C6 . . 121.25(15) ?
    C6 C10 H10 . . 117.7 ?
    N5 C10 H10 . . 117.7 ?
    N5 C10 C6 . . 124.58(17) ?
    C13 N6 C9 . . 117.76(17) ?
    O1 C7 C6 . . 125.53(16) ?
    O1 C7 C8 . . 118.53(15) ?
    C6 C7 C8 . . 115.93(15) ?
    C7 O1 Cu1 . . 128.84(12) ?
    C2 N2 C3 . . 105.49(16) ?
    N2 C2 H2 . . 124.4 ?
    N2 C2 N1 . . 111.22(17) ?
    N1 C2 H2 . . 124.4 ?
    C2 N1 H1 . . 125.9 ?
    C2 N1 C1 . . 108.25(16) ?
    C1 N1 H1 . . 125.9 ?
    N1 C1 H1A . . 127.0 ?
    N1 C1 C3 . . 106.06(17) ?
    C3 C1 H1A . . 127.0 ?
    N2 C3 C4 . . 125.04(16) ?
    C1 C3 N2 . . 108.98(16) ?
    C1 C3 C4 . . 125.93(18) ?
    C3 C4 H4 . . 115.7 ?
    N3 C4 C3 . . 128.51(17) ?
    N3 C4 H4 . . 115.7 ?
    C4 N3 N4 . . 123.15(15) ?
    C10 C6 C5 . . 115.40(15) ?
    C10 C6 C7 . . 119.16(16) ?
    C7 C6 C5 . . 125.43(16) ?
    C10 N5 C9 . . 119.62(16) ?
    C10 N5 C15A . . 122.4(4) ?
    C10 N5 C15B . . 117.2(2) ?
    C9 N5 C15A . . 117.3(4) ?
    C9 N5 C15B . . 123.0(2) ?
    N6 C9 N5 . . 116.84(16) ?
    N6 C9 C8 . . 124.10(17) ?
    N5 C9 C8 . . 119.05(16) ?
    N6 C13 C12 . . 122.51(18) ?
    N6 C13 C14 . . 116.60(19) ?
    C12 C13 C14 . . 120.87(18) ?
    C13 C12 H12 . . 120.4 ?
    C11 C12 C13 . . 119.22(17) ?
    C11 C12 H12 . . 120.4 ?
    C12 C11 H11 . . 120.2 ?
    C12 C11 C8 . . 119.56(18) ?
    C8 C11 H11 . . 120.2 ?
    C9 C8 C7 . . 121.61(16) ?
    C9 C8 C11 . . 116.76(17) ?
    C11 C8 C7 . . 121.62(17) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C5 N4 Cu1 . . 125.78(12) ?
    C5 N4 N3 . . 107.93(14) ?
    N3 N4 Cu1 . . 126.19(11) ?
    C18 O3 H3 . . 109.5 ?
    C17 O4 H4A . . 109.5 ?
    O4 C17 H17A . . 109.5 ?
    O4 C17 H17B . . 109.5 ?
    O4 C17 H17C . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    N5 C15A H15A . . 108.5 ?
    N5 C15A H15B . . 108.5 ?
    H15A C15A H15B . . 107.5 ?
    C16A C15A N5 . . 115.1(8) ?
    C16A C15A H15A . . 108.5 ?
    C16A C15A H15B . . 108.5 ?
    C15A C16A H16A . . 109.5 ?
    C15A C16A H16B . . 109.5 ?
    C15A C16A H16C . . 109.5 ?
    H16A C16A H16B . . 109.5 ?
    H16A C16A H16C . . 109.5 ?
    H16B C16A H16C . . 109.5 ?
    N5 C15B H15C . . 109.8 ?
    N5 C15B H15D . . 109.8 ?
    N5 C15B C16B . . 109.2(3) ?
    H15C C15B H15D . . 108.3 ?
    C16B C15B H15C . . 109.8 ?
    C16B C15B H15D . . 109.8 ?
    C15B C16B H16D . . 109.5 ?
    C15B C16B H16E . . 109.5 ?
    C15B C16B H16F . . 109.5 ?
    H16D C16B H16E . . 109.5 ?
    H16D C16B H16F . . 109.5 ?
    H16E C16B H16F . . 109.5 ?
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
    Cu2 O2 C5 C6 . . . . -175.80(11) ?
    Cu2 O2 C5 N4 . . . . 4.2(2) ?
    O2 C5 C6 C10 . . . . 1.8(2) ?
    O2 C5 C6 C7 . . . . -177.27(16) ?
    O2 C5 N4 Cu1 . . . . -178.81(12) ?
    O2 C5 N4 N3 . . . . -2.3(2) ?
    C10 N5 C9 N6 . . . . -177.46(17) ?
    C10 N5 C9 C8 . . . . 1.9(3) ?
    C10 N5 C15A C16A . . . . 1.3(9) ?
    C10 N5 C15B C16B . . . . 72.4(4) ?
    N6 C9 C8 C7 . . . . 178.04(17) ?
    N6 C9 C8 C11 . . . . -2.9(3) ?
    N6 C13 C12 C11 . . . . -2.8(3) ?
    O1 C7 C6 C5 . . . . 1.8(3) ?
    O1 C7 C6 C10 . . . . -177.20(17) ?
    O1 C7 C8 C9 . . . . 178.52(16) ?
    O1 C7 C8 C11 . . . . -0.5(3) ?
    N2 C2 N1 C1 . . . . -0.3(2) ?
    N2 C3 C4 N3 . . . . 2.8(3) ?
    C2 N2 C3 C1 . . . . 0.4(2) ?
    C2 N2 C3 C4 . . . . -177.00(18) ?
    C2 N1 C1 C3 . . . . 0.5(2) ?
    N1 C1 C3 N2 . . . . -0.5(2) ?
    N1 C1 C3 C4 . . . . 176.82(18) ?
    C1 C3 C4 N3 . . . . -174.1(2) ?
    C3 N2 C2 N1 . . . . -0.1(2) ?
    C3 C4 N3 N4 . . . . -2.3(3) ?
    C4 N3 N4 Cu1 . . . . -6.7(2) ?
    C4 N3 N4 C5 . . . . 176.81(17) ?
    C6 C5 N4 Cu1 . . . . 1.2(2) ?
    C6 C5 N4 N3 . . . . 177.71(15) ?
    C6 C10 N5 C9 . . . . -0.6(3) ?
    C6 C10 N5 C15A . . . . -170.8(4) ?
    C6 C10 N5 C15B . . . . 174.3(2) ?
    C6 C7 O1 Cu1 . . . . -10.4(3) ?
    C6 C7 C8 C9 . . . . -0.6(2) ?
    C6 C7 C8 C11 . . . . -179.65(16) ?
    N5 C10 C6 C5 . . . . 179.52(18) ?
    N5 C10 C6 C7 . . . . -1.4(3) ?
    N5 C9 C8 C7 . . . . -1.3(3) ?
    N5 C9 C8 C11 . . . . 177.82(16) ?
    C9 N6 C13 C12 . . . . 1.1(3) ?
    C9 N6 C13 C14 . . . . -176.99(17) ?
    C9 N5 C15A C16A . . . . -169.1(5) ?
    C9 N5 C15B C16B . . . . -112.9(3) ?
    C13 N6 C9 N5 . . . . -178.89(16) ?
    C13 N6 C9 C8 . . . . 1.8(3) ?
    C13 C12 C11 C8 . . . . 1.6(3) ?
    C12 C11 C8 C7 . . . . -179.86(17) ?
    C12 C11 C8 C9 . . . . 1.1(3) ?
    C8 C7 O1 Cu1 . . . . 170.57(12) ?
    C8 C7 C6 C5 . . . . -179.10(16) ?
    C8 C7 C6 C10 . . . . 1.9(2) ?
    C14 C13 C12 C11 . . . . 175.23(18) ?
    N4 C5 C6 C10 . . . . -178.20(16) ?
    N4 C5 C6 C7 . . . . 2.7(3) ?
    C15A N5 C9 N6 . . . . -6.8(5) ?
    C15A N5 C9 C8 . . . . 172.5(4) ?
    C15B N5 C9 N6 . . . . 7.9(3) ?
    C15B N5 C9 C8 . . . . -172.7(2) ?
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
    _geom_hbond_publ_flag
    O3 H3 Cl1 3_455 ? ? 3.066(2) ? no
    N1 H1 Cl1 1_565 ? ? 3.022(2) ? no
    O4 H4A Cl1 ? ? ? 3.123(2) ? no
_shelxl_version_number     2014/6
