##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2009-07-09
_journal_date_accepted     2009-08-12
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue      9
_journal_page_first     m361
_journal_page_last     m366
_journal_paper_category     FM
_journal_coeditor_code     GT3009
_publ_contact_author_name     'Zora Popovic'
_publ_contact_author_address
;
Laboratory of General and Inorganic Chemistry
Department of Chemistry
Faculty of Science
University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
_publ_contact_author_email     zpopovic@chem.pmf.hr
_publ_contact_author_fax     '00385 1 4606341'
_publ_contact_author_phone     '00385 1 4606354'
_publ_section_title
;
Uncommon isonicotinamide supramolecular synthons in copper(II) complexes
directed by nitrate and perchlorate anions
;
loop_
    _publ_author_name
    _publ_author_address
    'Đaković, Marijana'
;
Laboratory of General and Inorganic Chemistry
Department of Chemistry
Faculty of Science
University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
    'Popović, Zora'
;
Laboratory of General and Inorganic Chemistry
Department of Chemistry
Faculty of Science
University of Zagreb
Horvatovac 102a
HR-10000 Zagreb
Croatia
;
data_I
_chemical_name_systematic
;
trans-Diaquabis(nitrato-κO)bis(pyridine-4-carboxamide-
κN¹)copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 Cu N6 O10'
_chemical_formula_sum     'C12 H16 Cu N6 O10'
_chemical_formula_structural     ?
_chemical_formula_iupac     '[Cu (N O3)2 (C6 H6 N2 O)2 (H2 O)2]'
_chemical_formula_weight     467.86
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,1/2+y,1/2-z
    3 -x,-y,-z
    4 x,1/2-y,1/2+z
_cell_length_a     7.5367(2)
_cell_length_b     9.8819(3)
_cell_length_c     11.7402(4)
_cell_angle_alpha     90
_cell_angle_beta     96.280(3)
_cell_angle_gamma     90
_cell_volume     869.13(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8118
_cell_measurement_theta_min     3.9572
_cell_measurement_theta_max     32.3327
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     prism
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.59
_exptl_crystal_size_mid     0.02
_exptl_crystal_size_min     0.01
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.788
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     478
_exptl_absorpt_coefficient_mu     1.328
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlisPro; Oxford Diffraction, 2007)'
_exptl_absorpt_correction_T_min     0.874
_exptl_absorpt_correction_T_max     0.987
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector
;
_diffrn_measurement_method     CCD
_diffrn_detector_area_resol_mean     16.3426
_diffrn_reflns_number     11568
_diffrn_reflns_av_R_equivalents     0.0126
_diffrn_reflns_av_sigmaI/netI     0.0112
_diffrn_reflns_theta_min     4.06
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger.
;
_reflns_number_total     2536
_reflns_number_gt     2188
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0291
_refine_ls_R_factor_gt     0.0241
_refine_ls_wR_factor_gt     0.0666
_refine_ls_wR_factor_ref     0.0692
_refine_ls_goodness_of_fit_ref     1.089
_refine_ls_restrained_S_all     1.089
_refine_ls_number_reflns     2536
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0400P)²+0.1821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.369
_refine_diff_density_min     -0.333
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    Cu Cu 0.3201 1.2651 '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'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_cell_refinement     'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_data_reduction     'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al.,
2002)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cu Cu1 0.50000 0.50000 0.50000 0.02330(10)
                                             Uani . . 1.000
    O O1 0.30452(15) -0.16759(9) 0.62031(9) 0.0368(3) Uani . . 1.000
    O O2 0.36171(13) 0.56244(10) 0.62446(8) 0.0269(3) Uani . . 1.000
    O O3 0.22364(14) 0.55983(12) 0.37130(11) 0.0443(3) Uani . . 1.000
    O O4 0.03110(19) 0.43502(14) 0.27264(12) 0.0600(5) Uani . . 1.000
    O O5 -0.05722(18) 0.59372(12) 0.37737(16) 0.0637(5) Uani . . 1.000
    N N1 0.40841(14) 0.31276(10) 0.51679(9) 0.0236(3) Uani . . 1.000
    N N2 0.13123(18) -0.15006(13) 0.45228(13) 0.0383(4) Uani . . 1.000
    N N3 0.06714(16) 0.52869(12) 0.34056(11) 0.0320(3) Uani . . 1.000
    C C1 0.31556(17) 0.25377(13) 0.42638(11) 0.0273(3) Uani . . 1.000
    C C2 0.25586(18) 0.12175(13) 0.42877(11) 0.0282(3) Uani . . 1.000
    C C3 0.29348(15) 0.04659(12) 0.52803(11) 0.0231(3) Uani . . 1.000
    C C4 0.38775(17) 0.10782(12) 0.62195(11) 0.0262(3) Uani . . 1.000
    C C5 0.44300(18) 0.24101(12) 0.61363(11) 0.0268(3) Uani . . 1.000
    C C6 0.24200(16) -0.10063(12) 0.53697(12) 0.0265(3) Uani . . 1.000
    H H1 0.29030 0.30360 0.35940 0.0330 Uiso calc R 1.000
    H H2 0.19130 0.08390 0.36460 0.0340 Uiso calc R 1.000
    H H4 0.41380 0.06010 0.69000 0.0310 Uiso calc R 1.000
    H H5 0.50590 0.28180 0.67710 0.0320 Uiso calc R 1.000
    H H12N 0.097(3) -0.231(3) 0.451(2) 0.067(7) Uiso . . 1.000
    H H12O 0.339(3) 0.642(2) 0.6212(16) 0.043(5) Uiso . . 1.000
    H H22N 0.097(3) -0.105(2) 0.3935(18) 0.045(5) Uiso . . 1.000
    H H22O 0.282(3) 0.520(2) 0.629(2) 0.047(6) Uiso . . 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cu1 O2 . . 1.9840(10)
                        yes
    Cu1 O3 . . 2.5070(10)
                        yes
    Cu1 N1 . . 1.9920(10)
                        yes
    Cu1 O2 . 3_666 1.9840(10)
                            no
    Cu1 O3 . 3_666 2.5070(10)
                            no
    Cu1 N1 . 3_666 1.9920(10)
                            no
    O1 C6 . . 1.231(2) no
    O3 N3 . . 1.234(2) no
    O4 N3 . . 1.233(2) no
    O5 N3 . . 1.252(2) no
    O2 H12O . . 0.81(2) no
    O2 H22O . . 0.74(2) no
    N1 C1 . . 1.339(2) no
    N1 C5 . . 1.341(2) no
    N2 C6 . . 1.320(2) no
    N2 H22N . . 0.84(2) no
    N2 H12N . . 0.84(3) no
    C1 C2 . . 1.3813(18) no
    C2 C3 . . 1.3848(18) no
    C3 C6 . . 1.5123(17) no
    C3 C4 . . 1.3840(18) no
    C4 C5 . . 1.3871(17) no
    C1 H1 . . 0.9300 no
    C2 H2 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C5 H5 . . 0.9300 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cu1 O1 3.9257(10) . 1_565 no
    Cu1 O5 3.8882(14) . 1_655 no
    Cu1 O1 3.9257(10) . 3_656 no
    Cu1 O5 3.8882(14) . 3_566 no
    Cu1 H4 3.6700 . 2_656 no
    Cu1 H4 3.6700 . 4_554 no
    O1 Cu1 3.9257(10) . 1_545 no
    O1 O2 2.7020(13) . 1_545 no
    O1 Cu1 3.9257(10) . 3_656 no
    O1 N1 3.1767(15) . 3_656 no
    O1 C1 3.0932(17) . 3_656 no
    O2 O3 3.0398(16) . . no
    O2 N1 2.8119(14) . . no
    O2 C5 3.2400(16) . . no
    O2 O1 2.7020(13) . 1_565 no
    O2 C1 3.1446(16) . 3_666 no
    O2 O5 2.7636(16) . 3_566 no
    O2 C4 3.3765(16) . 2_656 no
    O2 N1 2.8109(14) . 3_666 no
    O3 N1 3.2090(16) . . no
    O3 C1 3.1540(18) . . no
    O3 N2 3.1229(18) . 1_565 no
    O3 O2 3.0398(16) . . no
    O3 C5 3.1812(17) . 3_666 no
    O3 N1 3.1945(15) . 3_666 no
    O4 C4 3.4021(19) . 4_554 no
    O4 C1 3.1962(19) . . no
    O4 N2 2.910(2) . 2_555 no
    O5 N2 2.9880(19) . 1_565 no
    O5 Cu1 3.8882(14) . 3_566 no
    O5 N1 3.1817(18) . 3_566 no
    O5 C5 3.3465(19) . 3_566 no
    O5 Cu1 3.8882(14) . 1_455 no
    O5 O2 2.7636(16) . 3_566 no
    O1 H12O 1.90(2) . 1_545 no
    O1 H5 2.6800 . 2_646 no
    O1 H4 2.5000 . . no
    O2 H4 2.6100 . 2_656 no
    O3 H1 2.5900 . . no
    O3 H5 2.6800 . 3_666 no
    O3 H12N 2.50(3) . 1_565 no
    O4 H2 2.6400 . 2_555 no
    O4 H22O 2.77(2) . 3_566 no
    O4 H1 2.4700 . . no
    O4 H22N 2.12(2) . 2_555 no
    O5 H12N 2.21(3) . 1_565 no
    O5 H2 2.9100 . 2_555 no
    O5 H22O 2.03(2) . 3_566 no
    N1 O2 2.8119(14) . . no
    N1 O3 3.2090(16) . . no
    N1 O3 3.1945(15) . 3_666 no
    N1 O1 3.1767(15) . 3_656 no
    N1 O2 2.8109(14) . 3_666 no
    N1 O5 3.1817(18) . 3_566 no
    N2 O5 2.9880(19) . 1_545 no
    N2 C3 3.3921(18) . 3_556 no
    N2 O3 3.1229(18) . 1_545 no
    N2 C2 3.3810(19) . 3_556 no
    N2 O4 2.910(2) . 2_545 no
    N3 C1 3.3895(18) . . no
    N1 H22O 2.67(2) . . no
    N1 H12O 2.67(2) . 3_666 no
    N2 H2 2.5900 . . no
    N3 H1 2.7800 . . no
    N3 H12N 2.70(3) . 1_565 no
    N3 H22O 2.74(2) . 3_566 no
    C1 O4 3.1962(19) . . no
    C1 N3 3.3895(18) . . no
    C1 O1 3.0932(17) . 3_656 no
    C2 N2 3.3810(19) . 3_556 no
    C3 N2 3.3921(18) . 3_556 no
    C3 C3 3.3793(16) . 3_656 no
    C3 C4 3.4822(17) . 3_656 no
    C4 C3 3.4822(17) . 3_656 no
    C4 C6 3.5230(18) . 3_656 no
    C4 O2 3.3765(16) . 2_646 no
    C4 O4 3.4021(19) . 4_555 no
    C5 C6 3.4066(18) . 3_656 no
    C5 O5 3.3465(19) . 3_566 no
    C6 C5 3.4066(18) . 3_656 no
    C6 C4 3.5230(18) . 3_656 no
    C1 H12O 2.91(2) . 3_666 no
    C2 H22N 2.55(2) . . no
    C4 H1 3.0900 . 4_555 no
    C5 H22O 3.03(2) . . no
    C6 H12O 2.80(2) . 1_545 no
    H1 O3 2.5900 . . no
    H1 O4 2.4700 . . no
    H1 N3 2.7800 . . no
    H1 C4 3.0900 . 4_554 no
    H2 N2 2.5900 . . no
    H2 H22N 2.0400 . . no
    H2 O4 2.6400 . 2_545 no
    H2 O5 2.9100 . 2_545 no
    H4 O1 2.5000 . . no
    H4 Cu1 3.6700 . 2_646 no
    H4 O2 2.6100 . 2_646 no
    H4 Cu1 3.6700 . 4_555 no
    H5 O1 2.6800 . 2_656 no
    H5 O3 2.6800 . 3_666 no
    H12N O3 2.50(3) . 1_545 no
    H12N O5 2.21(3) . 1_545 no
    H12N N3 2.70(3) . 1_545 no
    H12O O1 1.90(2) . 1_565 no
    H12O C6 2.80(2) . 1_565 no
    H12O C1 2.91(2) . 3_666 no
    H22N C2 2.55(2) . . no
    H22N H2 2.0400 . . no
    H22N O4 2.12(2) . 2_545 no
    H22O C5 3.03(2) . . no
    H22O O4 2.77(2) . 3_566 no
    H22O O5 2.03(2) . 3_566 no
    H22O N3 2.74(2) . 3_566 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 Cu1 O3 . . . 84.36(4) yes
    O2 Cu1 N1 . . . 90.02(4) yes
    O2 Cu1 O2 . . 3_666 180.00 no
    O2 Cu1 O3 . . 3_666 95.64(4) yes
    O2 Cu1 N1 . . 3_666 89.98(4) yes
    O3 Cu1 N1 . . . 90.27(4) yes
    O2 Cu1 O3 3_666 . . 95.64(4) no
    O3 Cu1 O3 . . 3_666 180.00 no
    O3 Cu1 N1 . . 3_666 89.73(4) yes
    O2 Cu1 N1 3_666 . . 89.98(4) no
    O3 Cu1 N1 3_666 . . 89.73(4) no
    N1 Cu1 N1 . . 3_666 180.00 no
    O2 Cu1 O3 3_666 . 3_666 84.36(4) no
    O2 Cu1 N1 3_666 . 3_666 90.02(4) no
    O3 Cu1 N1 3_666 . 3_666 90.27(4) no
    Cu1 O3 N3 . . . 145.29(10) no
    H12O O2 H22O . . . 113(2) no
    Cu1 O2 H12O . . . 113.3(14) no
    Cu1 O2 H22O . . . 111.9(17) no
    Cu1 N1 C1 . . . 118.85(8) no
    C1 N1 C5 . . . 118.56(11) no
    Cu1 N1 C5 . . . 122.52(8) no
    O4 N3 O5 . . . 119.25(14) no
    O3 N3 O5 . . . 119.92(13) no
    O3 N3 O4 . . . 120.82(13) no
    H12N N2 H22N . . . 115(2) no
    C6 N2 H22N . . . 122.4(14) no
    C6 N2 H12N . . . 122.2(16) no
    N1 C1 C2 . . . 122.56(12) no
    C1 C2 C3 . . . 119.11(12) no
    C2 C3 C4 . . . 118.42(11) no
    C2 C3 C6 . . . 122.95(11) no
    C4 C3 C6 . . . 118.59(11) no
    C3 C4 C5 . . . 119.38(12) no
    N1 C5 C4 . . . 121.96(12) no
    N2 C6 C3 . . . 116.72(12) no
    O1 C6 N2 . . . 123.72(12) no
    O1 C6 C3 . . . 119.56(12) no
    N1 C1 H1 . . . 119.00 no
    C2 C1 H1 . . . 119.00 no
    C1 C2 H2 . . . 120.00 no
    C3 C2 H2 . . . 120.00 no
    C3 C4 H4 . . . 120.00 no
    C5 C4 H4 . . . 120.00 no
    N1 C5 H5 . . . 119.00 no
    C4 C5 H5 . . . 119.00 no
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
    O2 Cu1 O3 N3 . . . . -70.56(17) no
    N1 Cu1 O3 N3 . . . . 19.44(18) no
    O2 Cu1 O3 N3 3_666 . . . 109.44(17) no
    N1 Cu1 O3 N3 3_666 . . . -160.56(18) no
    O2 Cu1 N1 C1 . . . . 120.76(10) no
    O2 Cu1 N1 C5 . . . . -62.36(10) no
    O3 Cu1 N1 C1 . . . . 36.39(10) no
    O3 Cu1 N1 C5 . . . . -146.73(10) no
    O2 Cu1 N1 C1 3_666 . . . -59.24(10) no
    O2 Cu1 N1 C5 3_666 . . . 117.64(10) no
    O3 Cu1 N1 C1 3_666 . . . -143.61(10) no
    O3 Cu1 N1 C5 3_666 . . . 33.28(10) no
    Cu1 O3 N3 O4 . . . . -78.4(2) no
    Cu1 O3 N3 O5 . . . . 102.54(19) no
    Cu1 N1 C1 C2 . . . . 176.33(10) no
    C5 N1 C1 C2 . . . . -0.68(19) no
    Cu1 N1 C5 C4 . . . . -175.96(10) no
    C1 N1 C5 C4 . . . . 0.93(19) no
    N1 C1 C2 C3 . . . . -0.3(2) no
    C1 C2 C3 C4 . . . . 0.93(19) no
    C1 C2 C3 C6 . . . . -176.81(12) no
    C6 C3 C4 C5 . . . . 177.15(11) no
    C2 C3 C6 O1 . . . . 167.95(13) no
    C2 C3 C6 N2 . . . . -11.57(18) no
    C4 C3 C6 O1 . . . . -9.79(18) no
    C4 C3 C6 N2 . . . . 170.69(12) no
    C2 C3 C4 C5 . . . . -0.69(18) no
    C3 C4 C5 N1 . . . . -0.3(2) no
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
    O2 H12O O1 1_565 0.81(2) 1.90(2) 2.7020(10)
                                              175(2) yes
    O2 H22O O5 3_566 0.74(2) 2.03(2) 2.764(2) 174(2) yes
    N2 H12N O3 1_545 0.84(3) 2.50(3) 3.123(2) 132(2) yes
    N2 H22N O4 2_545 0.84(2) 2.12(2) 2.910(2) 158(2) yes
    N2 H12N O5 1_545 0.84(3) 2.21(3) 2.988(2) 154(2) yes
    C1 H1 O3 . 0.93 2.59 3.154(2) 120 no
    C1 H1 O4 . 0.93 2.47 3.196(2) 135 no
data_II
_chemical_name_systematic
;
trans-Diaquatetrakis(pyridine-4-carboxamide-κN¹)copper(II)
bis(perchlorate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H28 Cu N8 O6 2+ , 2Cl O4 -'
_chemical_formula_sum     'C24 H28 Cl2 Cu N8 O14'
_chemical_formula_structural     ?
_chemical_formula_iupac     '[Cu (C6 H6 N2 O)4 (H2 O)2] (Cl O4)2'
_chemical_formula_weight     786.99
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,y,1/2-z
    3 -x,-y,-z
    4 x,-y,1/2+z
    5 1/2+x,1/2+y,z
    6 1/2-x,1/2+y,1/2-z
    7 1/2-x,1/2-y,-z
    8 1/2+x,1/2-y,1/2+z
_cell_length_a     18.7783(3)
_cell_length_b     9.5648(2)
_cell_length_c     18.2630(2)
_cell_angle_alpha     90
_cell_angle_beta     92.0900(10)
_cell_angle_gamma     90
_cell_volume     3278.05(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     19308
_cell_measurement_theta_min     3.8844
_cell_measurement_theta_max     32.5464
_cell_measurement_temperature     296
_cell_special_details
;
;
_exptl_crystal_description     block
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.598
_exptl_crystal_size_mid     0.379
_exptl_crystal_size_min     0.301
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.595
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1612
_exptl_absorpt_coefficient_mu     0.908
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlisPro; Oxford Diffraction, 2007)'
_exptl_absorpt_correction_T_min     0.628
_exptl_absorpt_correction_T_max     0.761
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector
;
_diffrn_measurement_method     'CCD'
_diffrn_detector_area_resol_mean     16.3426
_diffrn_reflns_number     26135
_diffrn_reflns_av_R_equivalents     0.0191
_diffrn_reflns_av_sigmaI/netI     0.0110
_diffrn_reflns_theta_min     3.89
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger.
;
_reflns_number_total     3576
_reflns_number_gt     3224
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0355
_refine_ls_R_factor_gt     0.0322
_refine_ls_wR_factor_gt     0.0871
_refine_ls_wR_factor_ref     0.0886
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.068
_refine_ls_number_reflns     3576
_refine_ls_number_parameters     293
_refine_ls_number_restraints     366
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0447P)²+4.2502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.008
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.550
_refine_diff_density_min     -0.286
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    Cu Cu 0.3201 1.2651 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_cell_refinement     'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_data_reduction     'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al.,
2002)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cu Cu1 0.50000 0.72025(4) 0.25000 0.03070(10)
                                                Uani . . 1.000
    O O1 0.86429(7) 0.59773(18) 0.26184(8) 0.0452(5) Uani . . 1.000
    O O2 0.51757(8) 0.7558(2) -0.13161(8) 0.0496(5) Uani . . 1.000
    O O3 0.50000 0.9727(2) 0.25000 0.0425(7) Uani . . 1.000
    O O4 0.50000 0.4430(3) 0.25000 0.0521(8) Uani . . 1.000
    N N1 0.60582(8) 0.70161(17) 0.27427(8) 0.0299(4) Uani . . 1.000
    N N2 0.86383(10) 0.7166(3) 0.36739(12) 0.0568(7) Uani . . 1.000
    N N3 0.52221(8) 0.73432(17) 0.14158(8) 0.0304(4) Uani . . 1.000
    N N4 0.62382(10) 0.8543(2) -0.10376(10) 0.0438(6) Uani . . 1.000
    C C1 0.64038(9) 0.7839(2) 0.32302(10) 0.0291(5) Uani . . 1.000
    C C2 0.71289(9) 0.7734(2) 0.33833(10) 0.0292(5) Uani . . 1.000
    C C3 0.75209(9) 0.6763(2) 0.30062(9) 0.0290(5) Uani . . 1.000
    C C4 0.71630(10) 0.5920(2) 0.24991(12) 0.0422(6) Uani . . 1.000
    C C5 0.64385(10) 0.6060(2) 0.23870(12) 0.0415(6) Uani . . 1.000
    C C6 0.83190(9) 0.6607(2) 0.30921(10) 0.0328(5) Uani . . 1.000
    C C7 0.48811(9) 0.6605(2) 0.08878(10) 0.0309(5) Uani . . 1.000
    C C8 0.49993(10) 0.6802(2) 0.01542(10) 0.0309(5) Uani . . 1.000
    C C9 0.54994(9) 0.7774(2) -0.00557(10) 0.0292(5) Uani . . 1.000
    C C10 0.58565(10) 0.8534(2) 0.04902(10) 0.0379(6) Uani . . 1.000
    C C11 0.57035(10) 0.8293(2) 0.12105(10) 0.0376(6) Uani . . 1.000
    C C12 0.56315(10) 0.7950(2) -0.08577(10) 0.0329(5) Uani . . 1.000
    Cl Cl1A 0.69927(19) 0.5135(3) 0.49694(15) 0.0479(6) Uani . . 0.589(5)
    O O5A 0.6754(2) 0.6556(4) 0.49695(19) 0.0714(14) Uani . . 0.589(5)
    O O6A 0.6667(6) 0.4473(8) 0.4366(4) 0.134(4) Uani . . 0.589(5)
    O O7A 0.6828(6) 0.4541(8) 0.5639(3) 0.165(4) Uani . . 0.589(5)
    O O8A 0.7737(2) 0.5235(8) 0.4980(5) 0.125(3) Uani . . 0.589(5)
    Cl Cl1 0.7030(3) 0.4756(4) 0.4947(3) 0.0542(9) Uani . . 0.411(5)
    O O5 0.7303(3) 0.3427(5) 0.5109(4) 0.091(2) Uani . . 0.411(5)
    O O6 0.6567(4) 0.4681(9) 0.4335(4) 0.076(3) Uani . . 0.411(5)
    O O7 0.7585(4) 0.5677(9) 0.4841(6) 0.135(4) Uani . . 0.411(5)
    O O8 0.6623(4) 0.5193(11) 0.5543(5) 0.136(5) Uani . . 0.411(5)
    H H1 0.61460 0.85090 0.34770 0.0350 Uiso calc R 1.000
    H H2 0.73500 0.83080 0.37350 0.0350 Uiso calc R 1.000
    H H4 0.74120 0.52600 0.22350 0.0510 Uiso calc R 1.000
    H H5 0.62030 0.54710 0.20530 0.0500 Uiso calc R 1.000
    H H7 0.45520 0.59340 0.10210 0.0370 Uiso calc R 1.000
    H H8 0.47450 0.62840 -0.01980 0.0370 Uiso calc R 1.000
    H H10 0.61950 0.91980 0.03710 0.0450 Uiso calc R 1.000
    H H11 0.59440 0.88110 0.15720 0.0450 Uiso calc R 1.000
    H H12 0.8414(15) 0.749(3) 0.4032(13) 0.062(9) Uiso . . 1.000
    H H13 0.9083(10) 0.719(3) 0.3694(16) 0.059(8) Uiso . . 1.000
    H H14 0.6587(12) 0.867(3) -0.0738(13) 0.057(8) Uiso . . 1.000
    H H15 0.6328(14) 0.859(3) -0.1499(10) 0.050(7) Uiso . . 1.000
    H H16 0.5343(14) 1.023(3) 0.2425(15) 0.056(8) Uiso . . 1.000
    H H17 0.4964(18) 0.386(3) 0.2185(16) 0.068(10) Uiso . . 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cu1 O3 . . 2.415(2) yes
    Cu1 O4 . . 2.652(3) yes
    Cu1 N1 . . 2.0280(15) yes
    Cu1 N3 . . 2.0428(15) yes
    Cu1 N1 . 2_655 2.0280(15) no
    Cu1 N3 . 2_655 2.0428(15) no
    Cl1 O5 . . 1.398(7) no
    Cl1 O6 . . 1.393(9) no
    Cl1 O7 . . 1.384(9) no
    Cl1 O8 . . 1.416(10) no
    Cl1A O6A . . 1.393(9) no
    Cl1A O7A . . 1.393(7) no
    Cl1A O8A . . 1.400(5) no
    Cl1A O5A . . 1.431(5) no
    O1 C6 . . 1.233(2) no
    O2 C12 . . 1.234(2) no
    O3 H16 . 2_655 0.82(3) no
    O3 H16 . . 0.82(3) no
    O4 H17 . . 0.79(3) no
    O4 H17 . 2_655 0.79(3) no
    N1 C1 . . 1.338(2) no
    N1 C5 . . 1.342(3) no
    N2 C6 . . 1.315(3) no
    N3 C7 . . 1.339(2) no
    N3 C11 . . 1.345(2) no
    N4 C12 . . 1.325(3) no
    N2 H13 . . 0.835(19) no
    N2 H12 . . 0.85(3) no
    N4 H15 . . 0.867(19) no
    N4 H14 . . 0.85(2) no
    C1 C2 . . 1.384(2) no
    C2 C3 . . 1.384(3) no
    C3 C4 . . 1.384(3) no
    C3 C6 . . 1.509(2) no
    C4 C5 . . 1.375(3) no
    C7 C8 . . 1.379(3) no
    C8 C9 . . 1.385(3) no
    C9 C10 . . 1.387(3) no
    C9 C12 . . 1.504(3) no
    C10 C11 . . 1.376(3) no
    C1 H1 . . 0.9300 no
    C2 H2 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C8 H8 . . 0.9300 no
    C10 H10 . . 0.9300 no
    C11 H11 . . 0.9300 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cu1 O4 2.652(3) . . no
    Cl1 O5 3.295(6) . 7_656 no
    Cl1 H14 3.10(2) . 6_645 no
    Cl1A H12 3.03(3) . 7_666 no
    Cl1A H2 3.0200 . 7_666 no
    O1 O3 2.8305(16) . 6_645 no
    O1 O3 2.8305(16) . 5_545 no
    O1 N4 2.940(2) . 7_665 no
    O1 C1 3.378(3) . 6_645 no
    O2 N2 2.898(2) . 8_464 no
    O2 O4 2.889(3) . 3_665 no
    O2 O4 2.889(3) . 4_564 no
    O3 C11 3.066(2) . . no
    O3 O1 2.8305(16) . 5_455 no
    O3 N3 3.058(2) . . no
    O3 O1 2.8305(16) . 6_655 no
    O3 N3 3.058(2) . 2_655 no
    O3 C11 3.066(2) . 2_655 no
    O4 C5 3.132(2) . . no
    O4 O2 2.889(3) . 4_565 no
    O4 N1 3.194(3) . 2_655 no
    O4 O2 2.889(3) . 3_665 no
    O4 N1 3.194(3) . . no
    O4 C5 3.132(2) . 2_655 no
    O5 O5 1.968(7) . 7_656 no
    O5 N4 3.171(6) . 6_645 no
    O5 Cl1 3.295(6) . 7_656 no
    O5 C10 3.394(6) . 4_565 no
    O5A C2 3.210(4) . . no
    O5A C8 3.300(4) . 2_655 no
    O5A N2 2.882(4) . 7_666 no
    O5A O8A 3.215(8) . 7_666 no
    O5A C7 3.396(4) . 2_655 no
    O6 C7 3.296(8) . 2_655 no
    O6 C9 3.307(8) . 4_565 no
    O6 C12 3.082(8) . 4_565 no
    O6 N4 3.213(9) . 4_565 no
    O6A C12 3.043(9) . 4_565 no
    O6A N4 3.077(8) . 4_565 no
    O6A C9 3.273(10) . 4_565 no
    O7 C2 3.395(10) . . no
    O7A C5 3.351(6) . 4_565 no
    O8 N2 2.953(10) . 7_666 no
    O8A O5A 3.215(8) . 7_666 no
    O8A N4 3.128(7) . 6_645 no
    O8A C10 3.244(6) . 6_645 no
    O1 H11 2.6500 . 6_645 no
    O1 H16 2.04(3) . 6_645 no
    O1 H4 2.4900 . . no
    O1 H15 2.089(19) . 7_665 no
    O2 H13 2.067(19) . 8_464 no
    O2 H8 2.5400 . . no
    O2 H17 2.10(3) . 3_665 no
    O3 H11 2.6500 . 2_655 no
    O3 H11 2.6500 . . no
    O4 H5 2.6300 . 2_655 no
    O4 H5 2.6300 . . no
    O5 H14 2.84(3) . 4_565 no
    O5 H14 2.36(2) . 6_645 no
    O5A H2 2.8600 . 7_666 no
    O5A H12 2.07(3) . 7_666 no
    O5A H8 2.8700 . 2_655 no
    O6 H7 2.4800 . 2_655 no
    O6A H7 2.7500 . 2_655 no
    O7 H12 2.79(3) . . no
    O7 H2 2.7700 . 7_666 no
    O7 H10 2.7300 . 6_645 no
    O7A H5 2.8800 . 4_565 no
    O7A H2 2.7900 . 7_666 no
    O8 H8 2.8200 . 2_655 no
    O8 H12 2.35(3) . 7_666 no
    O8 H2 2.7100 . 7_666 no
    O8A H10 2.3500 . 6_645 no
    O8A H2 2.7400 . 7_666 no
    O8A H14 2.38(3) . 6_645 no
    N1 O4 3.194(3) . . no
    N1 N3 2.856(2) . . no
    N1 C7 3.137(2) . 2_655 no
    N1 C11 3.103(2) . . no
    N1 N3 2.917(2) . 2_655 no
    N2 O5A 2.882(4) . 7_666 no
    N2 O2 2.898(2) . 8_565 no
    N2 O8 2.953(10) . 7_666 no
    N3 C1 3.179(2) . 2_655 no
    N3 N1 2.856(2) . . no
    N3 N1 2.917(2) . 2_655 no
    N3 C5 3.094(3) . . no
    N3 O3 3.058(2) . . no
    N4 O5 3.171(6) . 6_655 no
    N4 O6 3.213(9) . 4_564 no
    N4 O8A 3.128(7) . 6_655 no
    N4 O1 2.940(2) . 7_665 no
    N4 O6A 3.077(8) . 4_564 no
    N1 H11 2.7400 . . no
    N1 H7 2.7700 . 2_655 no
    N2 H2 2.6600 . . no
    N3 H5 2.7900 . . no
    N3 H1 2.8100 . 2_655 no
    N4 H10 2.6500 . . no
    C1 O1 3.378(3) . 6_655 no
    C1 C7 3.177(2) . 2_655 no
    C2 O5A 3.210(4) . . no
    C2 O7 3.395(10) . . no
    C5 O7A 3.351(6) . 4_564 no
    C5 C11 3.297(3) . . no
    C7 C1 3.177(2) . 2_655 no
    C7 O6 3.296(8) . 2_655 no
    C7 O5A 3.396(4) . 2_655 no
    C8 C8 3.493(3) . 3_665 no
    C8 O5A 3.300(4) . 2_655 no
    C9 O6A 3.273(10) . 4_564 no
    C9 O6 3.307(8) . 4_564 no
    C10 O8A 3.244(6) . 6_655 no
    C10 O5 3.394(6) . 4_564 no
    C11 C5 3.297(3) . . no
    C12 O6 3.082(8) . 4_564 no
    C12 O6A 3.043(9) . 4_564 no
    C1 H7 2.9300 . 2_655 no
    C2 H12 2.66(3) . . no
    C2 H4 2.8200 . 6_655 no
    C6 H16 3.02(3) . 6_645 no
    C6 H11 3.0600 . 6_645 no
    C6 H15 3.013(19) . 7_665 no
    C7 H1 2.9200 . 2_655 no
    C8 H8 2.9900 . 3_665 no
    C10 H14 2.68(2) . . no
    C11 H16 2.99(3) . . no
    C12 H13 3.00(2) . 8_464 no
    H1 C7 2.9200 . 2_655 no
    H1 N3 2.8100 . 2_655 no
    H2 Cl1A 3.0200 . 7_666 no
    H2 O5A 2.8600 . 7_666 no
    H2 H12 2.2000 . . no
    H2 N2 2.6600 . . no
    H2 O7A 2.7900 . 7_666 no
    H2 O8A 2.7400 . 7_666 no
    H2 O7 2.7700 . 7_666 no
    H2 O8 2.7100 . 7_666 no
    H4 C2 2.8200 . 6_645 no
    H4 O1 2.4900 . . no
    H5 O4 2.6300 . . no
    H5 N3 2.7900 . . no
    H5 O7A 2.8800 . 4_564 no
    H7 O6A 2.7500 . 2_655 no
    H7 O6 2.4800 . 2_655 no
    H7 C1 2.9300 . 2_655 no
    H7 N1 2.7700 . 2_655 no
    H8 O5A 2.8700 . 2_655 no
    H8 O2 2.5400 . . no
    H8 O8 2.8200 . 2_655 no
    H8 C8 2.9900 . 3_665 no
    H10 H14 2.2400 . . no
    H10 N4 2.6500 . . no
    H10 O8A 2.3500 . 6_655 no
    H10 O7 2.7300 . 6_655 no
    H11 O3 2.6500 . . no
    H11 C6 3.0600 . 6_655 no
    H11 N1 2.7400 . . no
    H11 H16 2.3800 . . no
    H11 O1 2.6500 . 6_655 no
    H12 Cl1A 3.03(3) . 7_666 no
    H12 O5A 2.07(3) . 7_666 no
    H12 O8 2.35(3) . 7_666 no
    H12 O7 2.79(3) . . no
    H12 C2 2.66(3) . . no
    H12 H2 2.2000 . . no
    H13 C12 3.00(2) . 8_565 no
    H13 O2 2.067(19) . 8_565 no
    H14 Cl1 3.10(2) . 6_655 no
    H14 O8A 2.38(3) . 6_655 no
    H14 C10 2.68(2) . . no
    H14 H10 2.2400 . . no
    H14 O5 2.84(3) . 4_564 no
    H14 O5 2.36(2) . 6_655 no
    H15 O1 2.089(19) . 7_665 no
    H15 C6 3.013(19) . 7_665 no
    H16 C6 3.02(3) . 6_655 no
    H16 O1 2.04(3) . 6_655 no
    H16 C11 2.99(3) . . no
    H16 H11 2.3800 . . no
    H17 O2 2.10(3) . 3_665 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 Cu1 O4 . . . 180.00 yes
    O3 Cu1 N1 . . . 95.04(5) yes
    O3 Cu1 N3 . . . 86.22(5) yes
    O3 Cu1 N1 . . 2_655 95.04(5) no
    O3 Cu1 N3 . . 2_655 86.22(5) no
    O4 Cu1 N1 . . . 84.96(5) yes
    O4 Cu1 N3 . . . 93.78(5) yes
    O4 Cu1 N1 . . 2_655 84.96(5) no
    O4 Cu1 N3 . . 2_655 93.78(5) no
    N1 Cu1 N3 . . . 89.12(6) yes
    N1 Cu1 N1 . . 2_655 169.91(7) no
    N1 Cu1 N3 . . 2_655 91.55(6) no
    N1 Cu1 N3 2_655 . . 91.55(6) yes
    N3 Cu1 N3 . . 2_655 172.45(7) no
    N1 Cu1 N3 2_655 . 2_655 89.12(6) no
    O6 Cl1 O7 . . . 111.8(6) no
    O6 Cl1 O8 . . . 107.1(6) no
    O7 Cl1 O8 . . . 110.5(6) no
    O5 Cl1 O8 . . . 108.1(6) no
    O5 Cl1 O6 . . . 109.7(5) no
    O5 Cl1 O7 . . . 109.7(6) no
    O5A Cl1A O8A . . . 104.3(4) no
    O6A Cl1A O7A . . . 113.8(5) no
    O6A Cl1A O8A . . . 116.8(6) no
    O7A Cl1A O8A . . . 105.6(6) no
    O5A Cl1A O7A . . . 107.9(4) no
    O5A Cl1A O6A . . . 107.7(4) no
    Cu1 O3 H16 . . 2_655 126.0(19) no
    Cu1 O3 H16 . . . 126.0(19) no
    H16 O3 H16 . . 2_655 108(3) no
    Cu1 O4 H17 . . 2_655 133(2) no
    Cu1 O4 H17 . . . 133(2) no
    H17 O4 H17 . . 2_655 93(3) no
    Cu1 N1 C1 . . . 122.77(12) no
    C1 N1 C5 . . . 117.97(16) no
    Cu1 N1 C5 . . . 119.24(13) no
    C7 N3 C11 . . . 117.65(15) no
    Cu1 N3 C7 . . . 123.65(12) no
    Cu1 N3 C11 . . . 118.55(12) no
    H12 N2 H13 . . . 119(3) no
    C6 N2 H13 . . . 118(2) no
    C6 N2 H12 . . . 123.1(19) no
    C12 N4 H15 . . . 117.6(17) no
    C12 N4 H14 . . . 123.6(16) no
    H14 N4 H15 . . . 117(2) no
    N1 C1 C2 . . . 122.78(17) no
    C1 C2 C3 . . . 119.04(17) no
    C2 C3 C4 . . . 118.03(16) no
    C2 C3 C6 . . . 123.99(16) no
    C4 C3 C6 . . . 117.94(16) no
    C3 C4 C5 . . . 119.79(18) no
    N1 C5 C4 . . . 122.36(18) no
    O1 C6 C3 . . . 119.28(16) no
    N2 C6 C3 . . . 117.77(17) no
    O1 C6 N2 . . . 122.95(17) no
    N3 C7 C8 . . . 122.54(17) no
    C7 C8 C9 . . . 119.69(17) no
    C8 C9 C10 . . . 117.88(17) no
    C10 C9 C12 . . . 123.29(16) no
    C8 C9 C12 . . . 118.83(16) no
    C9 C10 C11 . . . 119.15(17) no
    N3 C11 C10 . . . 123.07(17) no
    N4 C12 C9 . . . 117.61(17) no
    O2 C12 N4 . . . 122.92(18) no
    O2 C12 C9 . . . 119.47(17) no
    N1 C1 H1 . . . 119.00 no
    C2 C1 H1 . . . 119.00 no
    C1 C2 H2 . . . 120.00 no
    C3 C2 H2 . . . 120.00 no
    C5 C4 H4 . . . 120.00 no
    C3 C4 H4 . . . 120.00 no
    N1 C5 H5 . . . 119.00 no
    C4 C5 H5 . . . 119.00 no
    N3 C7 H7 . . . 119.00 no
    C8 C7 H7 . . . 119.00 no
    C7 C8 H8 . . . 120.00 no
    C9 C8 H8 . . . 120.00 no
    C9 C10 H10 . . . 120.00 no
    C11 C10 H10 . . . 120.00 no
    C10 C11 H11 . . . 118.00 no
    N3 C11 H11 . . . 118.00 no
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 . . . . 40.63(14) no
    O3 Cu1 N1 C5 . . . . -137.25(14) no
    O4 Cu1 N1 C1 . . . . -139.37(14) no
    O4 Cu1 N1 C5 . . . . 42.75(14) no
    N3 Cu1 N1 C1 . . . . 126.76(15) no
    N3 Cu1 N1 C5 . . . . -51.12(15) no
    N3 Cu1 N1 C1 2_655 . . . -45.71(15) no
    N3 Cu1 N1 C5 2_655 . . . 136.41(15) no
    O3 Cu1 N3 C7 . . . . -132.74(15) no
    O3 Cu1 N3 C11 . . . . 42.70(13) no
    O4 Cu1 N3 C7 . . . . 47.26(15) no
    O4 Cu1 N3 C11 . . . . -137.30(13) no
    N1 Cu1 N3 C7 . . . . 132.15(15) no
    N1 Cu1 N3 C11 . . . . -52.42(14) no
    N1 Cu1 N3 C7 2_655 . . . -37.79(15) no
    N1 Cu1 N3 C11 2_655 . . . 137.65(14) no
    Cu1 N1 C1 C2 . . . . -178.43(14) no
    C5 N1 C1 C2 . . . . -0.5(3) no
    Cu1 N1 C5 C4 . . . . 176.93(16) no
    C1 N1 C5 C4 . . . . -1.1(3) no
    C7 N3 C11 C10 . . . . 0.1(3) no
    Cu1 N3 C7 C8 . . . . 174.48(14) no
    C11 N3 C7 C8 . . . . -1.0(3) no
    Cu1 N3 C11 C10 . . . . -175.62(15) no
    N1 C1 C2 C3 . . . . 1.6(3) no
    C1 C2 C3 C6 . . . . 176.30(17) no
    C1 C2 C3 C4 . . . . -1.1(3) no
    C2 C3 C4 C5 . . . . -0.3(3) no
    C4 C3 C6 N2 . . . . -165.3(2) no
    C2 C3 C6 O1 . . . . -162.21(19) no
    C2 C3 C6 N2 . . . . 17.3(3) no
    C6 C3 C4 C5 . . . . -177.93(18) no
    C4 C3 C6 O1 . . . . 15.2(3) no
    C3 C4 C5 N1 . . . . 1.5(3) no
    N3 C7 C8 C9 . . . . 1.5(3) no
    C7 C8 C9 C10 . . . . -1.0(3) no
    C7 C8 C9 C12 . . . . 178.68(17) no
    C8 C9 C10 C11 . . . . 0.2(3) no
    C10 C9 C12 O2 . . . . -159.69(19) no
    C10 C9 C12 N4 . . . . 19.5(3) no
    C8 C9 C12 N4 . . . . -160.16(18) no
    C12 C9 C10 C11 . . . . -179.51(17) no
    C8 C9 C12 O2 . . . . 20.6(3) no
    C9 C10 C11 N3 . . . . 0.3(3) no
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
    N2 H12 O5A 7_666 0.85(3) 2.07(3) 2.882(4) 159(3) yes
    N2 H13 O2 8_565 0.84(2) 2.07(2) 2.898(2) 174(3) yes
    N4 H14 O8A 6_655 0.85(2) 2.38(3) 3.128(7) 148(3) yes
    N4 H15 O1 7_665 0.87(2) 2.09(2) 2.940(2) 167(2) yes
    O3 H16 O1 6_655 0.82(3) 2.04(3) 2.831(2) 163(3) yes
    O4 H17 O2 3_665 0.79(3) 2.10(3) 2.889(3) 176(3) yes
    C10 H10 O8A 6_655 0.93 2.35 3.244(6) 162 no
