##############################################################################
#                                                                            #
# 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_global
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4992)
;
_journal_date_recd_electronic     2014-12-15
_journal_date_accepted     2015-01-26
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2015
_journal_volume     71
_journal_issue      2
_journal_page_first     165
_journal_page_last     168
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229615001692
_journal_coeditor_code     LG3154
_publ_contact_author_name     'Jiang-Yun Wang'
_publ_contact_author_address
;
Weifang Medical University
Weifang City
Shandong Province 261053
People's Republic of China
;
_publ_contact_author_email     wjy1980@wfmc.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     '13406643266'
_publ_section_title
;
Structural and spectroscopic studies of a
three-dimensional hydrogen-bonded copper(II) complex:
aqua[bis(pyridin-2-ylcarbonyl)amidato]cyanidocopper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Wang, Jiang-Yun'
;
Weifang Medical University
Weifang City
Shandong Province
People's Republic of China
;
_publ_section_synopsis
;
A copper(II) complex has been synthesized and characterized by single-crystal
X-ray diffraction, elemental analysis, IR, UV--vis and EPR spectra, and cyclic
voltammetric studies.
;
_shelxl_version_number       20.13
data_I
_database_code_depnum_ccdc_archive 'CCDC 1045587'
_chemical_name_systematic
;
Aqua[bis(pyridin-2-ylcarbonyl)amidato]cyanidocopper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Cu N4 O3'
_chemical_formula_sum     'C13 H10 Cu N4 O3'
_chemical_formula_iupac     '[Cu (C12 H8 N3 O2) (C N) (H2 O1)]'
_chemical_formula_weight     333.79
_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     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.3171(13)
_cell_length_b     9.8692(18)
_cell_length_c     10.2416(18)
_cell_angle_alpha     68.401(3)
_cell_angle_beta     84.964(3)
_cell_angle_gamma     70.617(3)
_cell_volume     648.2(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1997
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     26.36
_cell_measurement_temperature     294(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.710
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     338
_exptl_absorpt_coefficient_mu     1.701
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.581697
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details     ?
_diffrn_ambient_temperature     294.15
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3682
_diffrn_reflns_av_R_equivalents     0.0174
_diffrn_reflns_theta_min     2.140
_diffrn_reflns_theta_max     26.373
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     12
_refine_special_details     ?
_reflns_number_total     2605
_reflns_number_gt     2231
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0411
_refine_ls_R_factor_gt     0.0320
_refine_ls_wR_factor_gt     0.0762
_refine_ls_wR_factor_ref     0.0811
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     2605
_refine_ls_number_parameters     196
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0405P)²+0.2346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     other
_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     0.305
_refine_diff_density_min     -0.288
_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'
    '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
;
SMART (Bruker, 2000)
;
_computing_cell_refinement
;
SMART (Bruker, 2000)
;
_computing_data_reduction
;
SMART (Bruker, 2000)
;
_computing_structure_solution
;
SIR2004 (Burla et al.,  2007)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_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 0.60371(4) 0.76908(4) 0.59014(3) 0.02966(12) Uani d 1 . .
    O O1 0.3725(3) 0.6810(2) 0.29753(19) 0.0406(5) Uani d 1 . .
    O O2 0.1901(3) 0.5917(2) 0.55606(19) 0.0368(4) Uani d 1 . .
    O O3 0.8448(3) 0.5231(2) 0.6740(2) 0.0345(4) Uani d 1 . .
    H H3A 0.949(3) 0.533(4) 0.636(3) 0.052 Uiso d 1 . .
    H H3B 0.814(4) 0.458(3) 0.653(3) 0.052 Uiso d 1 . .
    C C13 0.7333(4) 0.8695(3) 0.6675(3) 0.0403(7) Uani d 1 . .
    N N1 0.7051(3) 0.8215(3) 0.3929(2) 0.0317(5) Uani d 1 . .
    N N2 0.4349(3) 0.7034(2) 0.5062(2) 0.0276(5) Uani d 1 . .
    N N3 0.4310(3) 0.7145(3) 0.7534(2) 0.0307(5) Uani d 1 . .
    N N4 0.8022(5) 0.9232(4) 0.7220(4) 0.0681(9) Uani d 1 . .
    C C1 0.8486(4) 0.8816(3) 0.3425(3) 0.0389(6) Uani d 1 . .
    H H1 0.9105 0.9066 0.4017 0.047 Uiso calc 1 . .
    C C2 0.9067(4) 0.9073(4) 0.2063(3) 0.0469(7) Uani d 1 . .
    H H2 1.0081 0.9469 0.1749 0.056 Uiso calc 1 . .
    C C3 0.8137(5) 0.8740(4) 0.1178(3) 0.0482(8) Uani d 1 . .
    H H3 0.8497 0.8921 0.0252 0.058 Uiso calc 1 . .
    C C4 0.6647(4) 0.8127(4) 0.1683(3) 0.0412(7) Uani d 1 . .
    H H4 0.5993 0.7893 0.1099 0.049 Uiso calc 1 . .
    C C5 0.6154(4) 0.7873(3) 0.3057(3) 0.0292(5) Uani d 1 . .
    C C6 0.4578(4) 0.7179(3) 0.3682(3) 0.0290(5) Uani d 1 . .
    C C7 0.3023(3) 0.6442(3) 0.5876(2) 0.0272(5) Uani d 1 . .
    C C8 0.3054(3) 0.6505(3) 0.7324(3) 0.0282(5) Uani d 1 . .
    C C9 0.1851(4) 0.5971(4) 0.8342(3) 0.0393(7) Uani d 1 . .
    H H9 0.0998 0.5531 0.8169 0.047 Uiso calc 1 . .
    C C10 0.1937(5) 0.6103(4) 0.9639(3) 0.0472(8) Uani d 1 . .
    H H10 0.1146 0.5743 1.0351 0.057 Uiso calc 1 . .
    C C11 0.3190(5) 0.6764(4) 0.9862(3) 0.0464(7) Uani d 1 . .
    H H11 0.3251 0.6872 1.0720 0.056 Uiso calc 1 . .
    C C12 0.4364(4) 0.7267(4) 0.8794(3) 0.0406(7) Uani d 1 . .
    H H12 0.5226 0.7708 0.8951 0.049 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 O3 . 2.373(2) y
    Cu1 C13 . 1.960(3) y
    Cu1 N1 . 2.030(2) y
    Cu1 N2 . 1.9525(19) y
    Cu1 N3 . 2.025(2) y
    O1 C6 . 1.212(3) ?
    O2 C7 . 1.225(3) ?
    O3 H3A . 0.842(10) ?
    O3 H3B . 0.844(10) ?
    C13 N4 . 1.136(4) ?
    N1 C1 . 1.347(3) ?
    N1 C5 . 1.347(3) ?
    N2 C6 . 1.368(3) ?
    N2 C7 . 1.362(3) ?
    N3 C8 . 1.346(3) ?
    N3 C12 . 1.344(3) ?
    C1 H1 . 0.9300 ?
    C1 C2 . 1.378(4) ?
    C2 H2 . 0.9300 ?
    C2 C3 . 1.367(4) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.389(4) ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.374(4) ?
    C5 C6 . 1.510(3) ?
    C7 C8 . 1.509(3) ?
    C8 C9 . 1.372(4) ?
    C9 H9 . 0.9300 ?
    C9 C10 . 1.390(4) ?
    C10 H10 . 0.9300 ?
    C10 C11 . 1.364(4) ?
    C11 H11 . 0.9300 ?
    C11 C12 . 1.378(4) ?
    C12 H12 . 0.9300 ?
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
    C13 Cu1 O3 . . 95.40(10) y
    C13 Cu1 N1 . . 99.84(11) y
    C13 Cu1 N3 . . 97.04(10) y
    N1 Cu1 O3 . . 93.16(8) y
    N2 Cu1 O3 . . 94.84(8) y
    N2 Cu1 C13 . . 169.60(11) y
    N2 Cu1 N1 . . 81.37(8) y
    N2 Cu1 N3 . . 80.55(8) y
    N3 Cu1 O3 . . 93.37(8) y
    N3 Cu1 N1 . . 161.22(8) y
    Cu1 O3 H3A . . 107(2) ?
    Cu1 O3 H3B . . 111(2) ?
    H3A O3 H3B . . 110.3(16) ?
    N4 C13 Cu1 . . 174.7(3) ?
    C1 N1 Cu1 . . 128.32(19) ?
    C5 N1 Cu1 . . 113.39(16) ?
    C5 N1 C1 . . 118.3(2) ?
    C6 N2 Cu1 . . 117.99(16) ?
    C7 N2 Cu1 . . 118.71(15) ?
    C7 N2 C6 . . 123.3(2) ?
    C8 N3 Cu1 . . 114.11(15) ?
    C12 N3 Cu1 . . 127.77(19) ?
    C12 N3 C8 . . 118.0(2) ?
    N1 C1 H1 . . 118.9 ?
    N1 C1 C2 . . 122.2(3) ?
    C2 C1 H1 . . 118.9 ?
    C1 C2 H2 . . 120.4 ?
    C3 C2 C1 . . 119.3(3) ?
    C3 C2 H2 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    C2 C3 C4 . . 119.1(3) ?
    C4 C3 H3 . . 120.4 ?
    C3 C4 H4 . . 120.5 ?
    C5 C4 C3 . . 118.9(3) ?
    C5 C4 H4 . . 120.5 ?
    N1 C5 C4 . . 122.2(2) ?
    N1 C5 C6 . . 116.1(2) ?
    C4 C5 C6 . . 121.7(2) ?
    O1 C6 N2 . . 128.6(2) ?
    O1 C6 C5 . . 120.2(2) ?
    N2 C6 C5 . . 111.1(2) ?
    O2 C7 N2 . . 128.3(2) ?
    O2 C7 C8 . . 120.9(2) ?
    N2 C7 C8 . . 110.8(2) ?
    N3 C8 C7 . . 115.4(2) ?
    N3 C8 C9 . . 122.6(2) ?
    C9 C8 C7 . . 122.0(2) ?
    C8 C9 H9 . . 120.8 ?
    C8 C9 C10 . . 118.4(3) ?
    C10 C9 H9 . . 120.8 ?
    C9 C10 H10 . . 120.2 ?
    C11 C10 C9 . . 119.6(3) ?
    C11 C10 H10 . . 120.2 ?
    C10 C11 H11 . . 120.6 ?
    C10 C11 C12 . . 118.9(3) ?
    C12 C11 H11 . . 120.6 ?
    N3 C12 C11 . . 122.5(3) ?
    N3 C12 H12 . . 118.7 ?
    C11 C12 H12 . . 118.7 ?
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
    Cu1 N1 C1 C2 . . . . 178.0(2) ?
    Cu1 N1 C5 C4 . . . . -179.3(2) ?
    Cu1 N1 C5 C6 . . . . 0.2(3) ?
    Cu1 N2 C6 O1 . . . . 178.0(2) ?
    Cu1 N2 C6 C5 . . . . -0.8(3) ?
    Cu1 N2 C7 O2 . . . . -176.8(2) ?
    Cu1 N2 C7 C8 . . . . 3.5(3) ?
    Cu1 N3 C8 C7 . . . . -5.4(3) ?
    Cu1 N3 C8 C9 . . . . 175.8(2) ?
    Cu1 N3 C12 C11 . . . . -175.7(2) ?
    O2 C7 C8 N3 . . . . -178.2(2) ?
    O2 C7 C8 C9 . . . . 0.5(4) ?
    N1 C1 C2 C3 . . . . 1.4(5) ?
    N1 C5 C6 O1 . . . . -178.5(2) ?
    N1 C5 C6 N2 . . . . 0.4(3) ?
    N2 C7 C8 N3 . . . . 1.4(3) ?
    N2 C7 C8 C9 . . . . -179.8(2) ?
    N3 C8 C9 C10 . . . . 0.1(4) ?
    C1 N1 C5 C4 . . . . -0.4(4) ?
    C1 N1 C5 C6 . . . . 179.1(2) ?
    C1 C2 C3 C4 . . . . -1.0(5) ?
    C2 C3 C4 C5 . . . . -0.1(5) ?
    C3 C4 C5 N1 . . . . 0.8(5) ?
    C3 C4 C5 C6 . . . . -178.7(3) ?
    C4 C5 C6 O1 . . . . 1.0(4) ?
    C4 C5 C6 N2 . . . . 179.9(3) ?
    C5 N1 C1 C2 . . . . -0.7(4) ?
    C6 N2 C7 O2 . . . . 2.4(4) ?
    C6 N2 C7 C8 . . . . -177.2(2) ?
    C7 N2 C6 O1 . . . . -1.3(4) ?
    C7 N2 C6 C5 . . . . 179.9(2) ?
    C7 C8 C9 C10 . . . . -178.5(3) ?
    C8 N3 C12 C11 . . . . 0.0(4) ?
    C8 C9 C10 C11 . . . . 0.5(5) ?
    C9 C10 C11 C12 . . . . -0.9(5) ?
    C10 C11 C12 N3 . . . . 0.6(5) ?
    C12 N3 C8 C7 . . . . 178.3(2) ?
    C12 N3 C8 C9 . . . . -0.4(4) ?
loop_
    _geom_hbond_atom_site_label_d
    _geom_hbond_atom_site_label_h
    _geom_hbond_atom_site_label_a
    _geom_hbond_site_symmetry_d
    _geom_hbond_site_symmetry_h
    _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 H3B O1 1_555 1_555 2_666 0.85(3) 2.15(3) 2.878(3) 144(3) y
    O3 H3B O2 1_555 1_555 2_666 0.85(3) 2.37(3) 3.027(3) 135(3) y
    O3 H3A O2 1_555 1_555 1_655 0.84(3) 2.05(3) 2.881(3) 169(3) y
