#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/26/2232647.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232647
loop_
_publ_author_name
'Liu, Jia-Cheng'
'Guo, Guo-Zhe'
'Xiao, Chao-Hu'
'Song, Xue-Yan'
'Li, Meng'
_publ_section_title
;
 Bis{2-[bis(3,5-dimethyl-1H-pyrazol-1-yl-κN²)methyl]pyridine-κN}copper(II)
 dinitrate
;
_journal_coeditor_code           FF2036
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1691
_journal_paper_doi               10.1107/S1600536811045636
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C16 H19 N5)2] (N O3)2'
_chemical_formula_moiety         'C32 H38 Cu N10 2+, 2(N O3 -)'
_chemical_formula_sum            'C32 H38 Cu N12 O6'
_chemical_formula_weight         750.28
_chemical_name_systematic
;
Bis{2-[bis(3,5-dimethyl-1H-pyrazol-1-yl-κN²)methyl]pyridine-
κN}copper(II) dinitrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.348(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.819(6)
_cell_length_b                   10.918(3)
_cell_length_c                   17.592(4)
_cell_measurement_reflns_used    4634
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.20
_cell_volume                     3523.1(15)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12411
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.8988
_exptl_absorpt_correction_T_min  0.8590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1564
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+5.0393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                2601
_reflns_number_total             3266
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ff2036.cif
_cod_data_source_block           I
_cod_original_cell_volume        3523.0(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2232647
_cod_database_fobs_code          2232647
loop_
_symmetry_equiv_pos_as_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'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cu Cu1 0.5000 -0.01320(4) 0.7500 0.03860(15) Uani d S 1 2
C C1 0.48707(15) -0.2377(2) 0.8338(2) 0.0508(7) Uani d . 1 1
H H1 0.5351 -0.2502 0.8646 0.061 Uiso calc R 1 1
C C2 0.45590(17) -0.3194(3) 0.8536(2) 0.0595(8) Uani d . 1 1
H H2 0.4828 -0.3849 0.8980 0.071 Uiso calc R 1 1
C C3 0.38457(16) -0.3035(3) 0.8069(2) 0.0598(8) Uani d . 1 1
H H3 0.3621 -0.3586 0.8183 0.072 Uiso calc R 1 1
C C4 0.34694(15) -0.2046(2) 0.7430(2) 0.0492(6) Uani d . 1 1
H H4 0.2985 -0.1920 0.7102 0.059 Uiso calc R 1 1
C C5 0.38190(13) -0.1246(2) 0.72802(18) 0.0368(5) Uani d . 1 1
C C6 0.34211(13) -0.0120(2) 0.66153(19) 0.0389(5) Uani d . 1 1
H H6 0.2941 -0.0109 0.6403 0.047 Uiso calc R 1 1
C C7 0.26736(15) -0.0142(3) 0.4692(2) 0.0554(7) Uani d . 1 1
C C8 0.28709(17) -0.0194(3) 0.4136(2) 0.0611(8) Uani d . 1 1
H H8 0.2559 -0.0196 0.3423 0.073 Uiso calc R 1 1
C C9 0.36269(16) -0.0244(2) 0.4835(2) 0.0498(7) Uani d . 1 1
C C10 0.4118(2) -0.0301(4) 0.4627(3) 0.0755(10) Uani d . 1 1
H H10A 0.4604 -0.0078 0.5237 0.113 Uiso calc R 1 1
H H10B 0.3947 0.0257 0.4082 0.113 Uiso calc R 1 1
H H10C 0.4119 -0.1119 0.4427 0.113 Uiso calc R 1 1
C C11 0.19391(19) -0.0068(5) 0.4360(3) 0.1009(15) Uani d . 1 1
H H11A 0.1859 -0.0785 0.4588 0.151 Uiso calc R 1 1
H H11B 0.1570 -0.0018 0.3623 0.151 Uiso calc R 1 1
H H11C 0.1916 0.0647 0.4655 0.151 Uiso calc R 1 1
C C12 0.35339(18) 0.1970(3) 0.7337(2) 0.0553(7) Uani d . 1 1
C C13 0.4112(2) 0.2737(3) 0.7987(3) 0.0666(9) Uani d . 1 1
H H13 0.4104 0.3487 0.8230 0.080 Uiso calc R 1 1
C C14 0.47163(17) 0.2200(2) 0.8223(2) 0.0540(7) Uani d . 1 1
C C15 0.2759(2) 0.2089(3) 0.6840(4) 0.0882(12) Uani d . 1 1
H H15A 0.2455 0.2171 0.6110 0.132 Uiso calc R 1 1
H H15B 0.2705 0.2800 0.7105 0.132 Uiso calc R 1 1
H H15C 0.2617 0.1373 0.6985 0.132 Uiso calc R 1 1
C C16 0.54737(19) 0.2688(3) 0.8906(3) 0.0773(10) Uani d . 1 1
H H16A 0.5811 0.2021 0.9172 0.116 Uiso calc R 1 1
H H16B 0.5580 0.3130 0.9465 0.116 Uiso calc R 1 1
H H16C 0.5518 0.3228 0.8520 0.116 Uiso calc R 1 1
N N1 0.45132(11) -0.14066(18) 0.77218(15) 0.0392(5) Uani d . 1 1
N N2 0.38955(12) -0.0231(2) 0.57884(16) 0.0463(5) Uani d . 1 1
N N3 0.33024(11) -0.01645(19) 0.56902(16) 0.0416(5) Uani d . 1 1
N N4 0.37949(12) 0.09956(18) 0.71912(16) 0.0420(5) Uani d . 1 1
N N5 0.45224(12) 0.11305(19) 0.77316(17) 0.0448(5) Uani d . 1 1
N N6 0.35109(14) 0.5779(2) 0.41294(19) 0.0512(6) Uani d . 1 1
O O1 0.35080(16) 0.6715(3) 0.4505(2) 0.1132(11) Uani d . 1 1
O O2 0.29475(13) 0.5446(3) 0.3289(2) 0.0896(8) Uani d . 1 1
O O3 0.40686(15) 0.5216(2) 0.4542(2) 0.1047(10) Uani d . 1 1
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'
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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N5 Cu1 N5 2_656 . 94.48(12)
N5 Cu1 N1 2_656 . 179.57(9)
N5 Cu1 N1 . . 85.63(8)
N5 Cu1 N1 2_656 2_656 85.63(8)
N5 Cu1 N1 . 2_656 179.57(9)
N1 Cu1 N1 . 2_656 94.26(12)
N5 Cu1 N2 2_656 2_656 87.32(8)
N5 Cu1 N2 . 2_656 96.28(8)
N1 Cu1 N2 . 2_656 93.08(8)
N1 Cu1 N2 2_656 2_656 83.31(8)
N5 Cu1 N2 2_656 . 96.28(8)
N5 Cu1 N2 . . 87.32(8)
N1 Cu1 N2 . . 83.31(8)
N1 Cu1 N2 2_656 . 93.08(8)
N2 Cu1 N2 2_656 . 174.72(11)
N1 C1 C2 . . 122.8(3)
N1 C1 H1 . . 118.6
C2 C1 H1 . . 118.6
C1 C2 C3 . . 119.2(3)
C1 C2 H2 . . 120.4
C3 C2 H2 . . 120.4
C2 C3 C4 . . 118.8(3)
C2 C3 H3 . . 120.6
C4 C3 H3 . . 120.6
C3 C4 C5 . . 119.2(3)
C3 C4 H4 . . 120.4
C5 C4 H4 . . 120.4
N1 C5 C4 . . 122.4(2)
N1 C5 C6 . . 117.9(2)
C4 C5 C6 . . 119.7(2)
N3 C6 N4 . . 111.33(19)
N3 C6 C5 . . 111.97(19)
N4 C6 C5 . . 111.4(2)
N3 C6 H6 . . 107.3
N4 C6 H6 . . 107.3
C5 C6 H6 . . 107.3
N3 C7 C8 . . 105.9(3)
N3 C7 C11 . . 123.1(3)
C8 C7 C11 . . 131.1(3)
C7 C8 C9 . . 107.0(3)
C7 C8 H8 . . 126.5
C9 C8 H8 . . 126.5
N2 C9 C8 . . 110.4(2)
N2 C9 C10 . . 121.0(3)
C8 C9 C10 . . 128.7(3)
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C7 C11 H11A . . 109.5
C7 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C7 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
N4 C12 C13 . . 105.8(3)
N4 C12 C15 . . 123.3(3)
C13 C12 C15 . . 130.8(3)
C12 C13 C14 . . 107.9(3)
C12 C13 H13 . . 126.1
C14 C13 H13 . . 126.1
N5 C14 C13 . . 109.3(3)
N5 C14 C16 . . 123.0(3)
C13 C14 C16 . . 127.7(3)
C12 C15 H15A . . 109.5
C12 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C12 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C14 C16 H16A . . 109.5
C14 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C14 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
C1 N1 C5 . . 117.7(2)
C1 N1 Cu1 . . 122.61(17)
C5 N1 Cu1 . . 119.60(15)
C9 N2 N3 . . 105.1(2)
C9 N2 Cu1 . . 141.70(19)
N3 N2 Cu1 . . 112.94(15)
C7 N3 N2 . . 111.6(2)
C7 N3 C6 . . 130.0(2)
N2 N3 C6 . . 118.4(2)
C12 N4 N5 . . 111.0(2)
C12 N4 C6 . . 128.9(2)
N5 N4 C6 . . 119.95(19)
C14 N5 N4 . . 106.0(2)
C14 N5 Cu1 . . 136.0(2)
N4 N5 Cu1 . . 117.58(15)
O3 N6 O2 . . 119.3(3)
O3 N6 O1 . . 121.5(3)
O2 N6 O1 . . 119.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N5 2_656 2.030(2)
Cu1 N5 . 2.030(2)
Cu1 N1 . 2.045(2)
Cu1 N1 2_656 2.045(2)
Cu1 N2 2_656 2.339(2)
Cu1 N2 . 2.339(2)
C1 N1 . 1.337(3)
C1 C2 . 1.370(4)
C1 H1 . 0.9300
C2 C3 . 1.371(4)
C2 H2 . 0.9300
C3 C4 . 1.374(4)
C3 H3 . 0.9300
C4 C5 . 1.376(3)
C4 H4 . 0.9300
C5 N1 . 1.341(3)
C5 C6 . 1.516(3)
C6 N3 . 1.446(3)
C6 N4 . 1.451(3)
C6 H6 . 0.9800
C7 N3 . 1.352(3)
C7 C8 . 1.359(4)
C7 C11 . 1.495(5)
C8 C9 . 1.388(4)
C8 H8 . 0.9300
C9 N2 . 1.324(3)
C9 C10 . 1.491(4)
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 N4 . 1.358(3)
C12 C13 . 1.363(4)
C12 C15 . 1.488(4)
C13 C14 . 1.388(4)
C13 H13 . 0.9300
C14 N5 . 1.334(3)
C14 C16 . 1.490(4)
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
N2 N3 . 1.363(3)
N4 N5 . 1.369(3)
N6 O3 . 1.211(3)
N6 O2 . 1.219(3)
N6 O1 . 1.220(3)
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
C2 H2 O3 2_646 0.93 2.39 3.245(4) 153 y
C8 H8 O2 4_545 0.93 2.46 3.338(4) 158 y
C15 H15c O2 7_556 0.96 2.29 3.202(6) 159 y
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
N1 C1 C2 C3 . 1.4(5)
C1 C2 C3 C4 . -1.0(5)
C2 C3 C4 C5 . -0.2(4)
C3 C4 C5 N1 . 1.3(4)
C3 C4 C5 C6 . -177.2(3)
N1 C5 C6 N3 . 67.1(3)
C4 C5 C6 N3 . -114.3(3)
N1 C5 C6 N4 . -58.3(3)
C4 C5 C6 N4 . 120.3(2)
N3 C7 C8 C9 . -0.2(3)
C11 C7 C8 C9 . 179.6(4)
C7 C8 C9 N2 . 0.3(3)
C7 C8 C9 C10 . -179.5(3)
N4 C12 C13 C14 . -0.1(3)
C15 C12 C13 C14 . -179.6(3)
C12 C13 C14 N5 . 0.3(3)
C12 C13 C14 C16 . -179.8(3)
C2 C1 N1 C5 . -0.4(4)
C2 C1 N1 Cu1 . 176.1(2)
C4 C5 N1 C1 . -1.0(4)
C6 C5 N1 C1 . 177.6(2)
C4 C5 N1 Cu1 . -177.61(19)
C6 C5 N1 Cu1 . 1.0(3)
N5 Cu1 N1 C1 . -133.1(2)
N1 Cu1 N1 C1 2_656 46.47(18)
N2 Cu1 N1 C1 2_656 -37.0(2)
N2 Cu1 N1 C1 . 139.1(2)
N5 Cu1 N1 C5 . 43.32(18)
N1 Cu1 N1 C5 2_656 -137.1(2)
N2 Cu1 N1 C5 2_656 139.39(18)
N2 Cu1 N1 C5 . -44.48(18)
C8 C9 N2 N3 . -0.4(3)
C10 C9 N2 N3 . 179.5(3)
C8 C9 N2 Cu1 . -173.9(2)
C10 C9 N2 Cu1 . 5.9(5)
N5 Cu1 N2 C9 2_656 40.4(3)
N5 Cu1 N2 C9 . 134.6(3)
N1 Cu1 N2 C9 . -139.5(3)
N1 Cu1 N2 C9 2_656 -45.6(3)
N5 Cu1 N2 N3 2_656 -132.84(17)
N5 Cu1 N2 N3 . -38.62(17)
N1 Cu1 N2 N3 . 47.29(16)
N1 Cu1 N2 N3 2_656 141.22(17)
C8 C7 N3 N2 . 0.0(3)
C11 C7 N3 N2 . -179.8(3)
C8 C7 N3 C6 . 179.4(2)
C11 C7 N3 C6 . -0.4(5)
C9 N2 N3 C7 . 0.2(3)
Cu1 N2 N3 C7 . 175.91(18)
C9 N2 N3 C6 . -179.3(2)
Cu1 N2 N3 C6 . -3.6(3)
N4 C6 N3 C7 . -114.3(3)
C5 C6 N3 C7 . 120.3(3)
N4 C6 N3 N2 . 65.1(3)
C5 C6 N3 N2 . -60.3(3)
C13 C12 N4 N5 . -0.1(3)
C15 C12 N4 N5 . 179.4(3)
C13 C12 N4 C6 . 176.1(2)
C15 C12 N4 C6 . -4.4(4)
N3 C6 N4 C12 . 110.1(3)
C5 C6 N4 C12 . -124.1(3)
N3 C6 N4 N5 . -74.0(3)
C5 C6 N4 N5 . 51.8(3)
C13 C14 N5 N4 . -0.4(3)
C16 C14 N5 N4 . 179.8(3)
C13 C14 N5 Cu1 . 171.5(2)
C16 C14 N5 Cu1 . -8.3(5)
C12 N4 N5 C14 . 0.3(3)
C6 N4 N5 C14 . -176.3(2)
C12 N4 N5 Cu1 . -173.37(17)
C6 N4 N5 Cu1 . 10.0(3)
N5 Cu1 N5 C14 2_656 -40.8(2)
N1 Cu1 N5 C14 . 139.7(3)
N2 Cu1 N5 C14 2_656 47.0(3)
N2 Cu1 N5 C14 . -136.9(3)
N5 Cu1 N5 N4 2_656 130.4(2)
N1 Cu1 N5 N4 . -49.17(17)
N2 Cu1 N5 N4 2_656 -141.80(17)
N2 Cu1 N5 N4 . 34.32(17)
