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#$Date: 2016-03-25 08:53:21 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179710 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/13/7001385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7001385
loop_
_publ_author_name
'Potapov, Andrei S.'
'Nudnova, Evgenia A.'
'Domina, Galina A.'
'Kirpotina, Liliya N.'
'Quinn, Mark T.'
'Khlebnikov, Andrei I.'
'Schepetkin, Igor A.'
_publ_section_title
;
 Synthesis, characterization and potent superoxide dismutase-like
 activity of novel bis(pyrazole)--2,2′-bipyridyl mixed ligand
 copper(ii) complexes
;
_journal_issue                   23
_journal_name_full               'Dalton Transactions'
_journal_page_first              4488
_journal_page_last               4498
_journal_paper_doi               10.1039/b900869a
_journal_year                    2009
_chemical_formula_moiety         'C14 H22 Cu N6 O7'
_chemical_formula_sum            'C14 H22 Cu N6 O7'
_chemical_formula_weight         449.92
_chemical_name_common
Bis(2-(3,5-dimethylpyrazol-1-yl)ethyl)etherdinitratocopper
_chemical_name_systematic
;
Bis[2-(3,5-dimethylpyrazol-1-yl)ethyl]etherdinitratocopper
;
_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                 107.1200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.4261(7)
_cell_length_b                   10.3459(3)
_cell_length_c                   11.1392(3)
_cell_measurement_reflns_used    8268
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.23
_cell_volume                     1919.29(11)
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'Crystal Structure'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-spider'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9186
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_T_max  0.7175
_exptl_absorpt_correction_T_min  0.6413
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0281P)²+1.3954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                2087
_reflns_number_total             2202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900869a.txt
_cod_data_source_block           cpl
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7001385
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.0000 0.32730(2) 0.2500 0.01803(8) Uani 1 2 d S . .
O1 O 0.0000 0.55018(13) 0.2500 0.0233(3) Uani 1 2 d S . .
O2 O -0.07395(6) 0.31693(9) 0.35784(9) 0.0245(2) Uani 1 1 d . . .
O3 O -0.16100(7) 0.18453(11) 0.39483(12) 0.0370(3) Uani 1 1 d . . .
O4 O -0.08541(7) 0.12169(10) 0.28233(10) 0.0309(2) Uani 1 1 d . . .
N1 N 0.09430(7) 0.33652(11) 0.40514(10) 0.0207(2) Uani 1 1 d . . .
N2 N 0.14507(7) 0.44051(11) 0.43282(10) 0.0203(2) Uani 1 1 d . . .
N5 N -0.10810(7) 0.20399(12) 0.34393(11) 0.0248(3) Uani 1 1 d . . .
C1 C 0.07571(10) 0.13372(14) 0.51290(14) 0.0287(3) Uani 1 1 d . . .
H1A H 0.0578 0.0933 0.4297 0.043 Uiso 1 1 calc R . .
H1B H 0.0291 0.1512 0.5426 0.043 Uiso 1 1 calc R . .
H1C H 0.1126 0.0753 0.5718 0.043 Uiso 1 1 calc R . .
C2 C 0.11771(8) 0.25750(13) 0.50469(12) 0.0219(3) Uani 1 1 d . . .
C3 C 0.18352(8) 0.31107(14) 0.59454(13) 0.0236(3) Uani 1 1 d . . .
H3A H 0.2118 0.2743 0.6733 0.028 Uiso 1 1 calc R . .
C4 C 0.19950(8) 0.42760(14) 0.54693(12) 0.0219(3) Uani 1 1 d . . .
C5 C 0.26063(9) 0.52849(16) 0.60251(14) 0.0299(3) Uani 1 1 d . . .
H5A H 0.2943 0.5022 0.6865 0.036 Uiso 1 1 d R . .
H5B H 0.2326 0.6098 0.6119 0.036 Uiso 1 1 d R . .
H5C H 0.2937 0.5436 0.5479 0.036 Uiso 1 1 d R . .
C6 C 0.14198(8) 0.54207(14) 0.34089(13) 0.0233(3) Uani 1 1 d . . .
H6A H 0.1437 0.5018 0.2611 0.028 Uiso 1 1 calc R . .
H6B H 0.1902 0.5973 0.3714 0.028 Uiso 1 1 calc R . .
C7 C 0.06801(8) 0.62613(13) 0.31529(13) 0.0234(3) Uani 1 1 d . . .
H7A H 0.0613 0.6582 0.3954 0.028 Uiso 1 1 calc R . .
H7B H 0.0733 0.7015 0.2636 0.028 Uiso 1 1 calc R . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu N1 174.55(6) . 2 ?
N1 Cu O2 90.61(4) . 2 ?
N1 Cu O2 89.68(4) 2 2 ?
N1 Cu O2 89.68(4) . . ?
N1 Cu O2 90.61(4) 2 . ?
O2 Cu O2 173.87(6) 2 . ?
N1 Cu O1 87.28(3) . . ?
N1 Cu O1 87.28(3) 2 . ?
O2 Cu O1 93.07(3) 2 . ?
O2 Cu O1 93.07(3) . . ?
C7 O1 C7 113.31(14) . 2 ?
C7 O1 Cu 123.34(7) . . ?
C7 O1 Cu 123.34(7) 2 . ?
N5 O2 Cu 109.20(8) . . ?
C2 N1 N2 105.89(11) . . ?
C2 N1 Cu 131.00(10) . . ?
N2 N1 Cu 122.85(8) . . ?
C4 N2 N1 111.25(11) . . ?
C4 N2 C6 127.10(12) . . ?
N1 N2 C6 121.38(11) . . ?
O4 N5 O3 123.39(13) . . ?
O4 N5 O2 118.56(12) . . ?
O3 N5 O2 118.04(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 109.67(12) . . ?
N1 C2 C1 122.61(12) . . ?
C3 C2 C1 127.71(12) . . ?
C4 C3 C2 106.73(12) . . ?
C4 C3 H3A 126.6 . . ?
C2 C3 H3A 126.6 . . ?
N2 C4 C3 106.45(12) . . ?
N2 C4 C5 122.69(13) . . ?
C3 C4 C5 130.83(13) . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 H5C 109.8 . . ?
H5A C5 H5C 110.1 . . ?
H5B C5 H5C 109.4 . . ?
N2 C6 C7 113.63(11) . . ?
N2 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O1 C7 C6 108.25(11) . . ?
O1 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N1 2.0060(11) . ?
Cu N1 2.0060(11) 2 ?
Cu O2 2.0067(10) 2 ?
Cu O2 2.0067(10) . ?
Cu O1 2.3059(13) . ?
O1 C7 1.4295(15) . ?
O1 C7 1.4295(15) 2 ?
O2 N5 1.2996(15) . ?
O3 N5 1.2329(16) . ?
O4 N5 1.2296(17) . ?
N1 C2 1.3409(17) . ?
N1 N2 1.3691(15) . ?
N2 C4 1.3504(17) . ?
N2 C6 1.4571(17) . ?
C1 C2 1.491(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.396(2) . ?
C3 C4 1.378(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.490(2) . ?
C5 H5A 0.9853 . ?
C5 H5B 0.9941 . ?
C5 H5C 0.9669 . ?
C6 C7 1.5108(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu O1 C7 19.92(8) . . . . ?
N1 Cu O1 C7 -160.08(8) 2 . . . ?
O2 Cu O1 C7 -70.55(8) 2 . . . ?
O2 Cu O1 C7 109.45(8) . . . . ?
N1 Cu O1 C7 -160.08(8) . . . 2 ?
N1 Cu O1 C7 19.92(8) 2 . . 2 ?
O2 Cu O1 C7 109.45(8) 2 . . 2 ?
O2 Cu O1 C7 -70.55(8) . . . 2 ?
N1 Cu O2 N5 -113.56(9) . . . . ?
N1 Cu O2 N5 71.88(9) 2 . . . ?
O1 Cu O2 N5 159.19(8) . . . . ?
O2 Cu N1 C2 -118.73(12) 2 . . . ?
O2 Cu N1 C2 55.14(12) . . . . ?
O1 Cu N1 C2 148.23(12) . . . . ?
O2 Cu N1 N2 67.96(10) 2 . . . ?
O2 Cu N1 N2 -118.17(10) . . . . ?
O1 Cu N1 N2 -25.08(9) . . . . ?
C2 N1 N2 C4 0.19(14) . . . . ?
Cu N1 N2 C4 174.95(9) . . . . ?
C2 N1 N2 C6 174.67(12) . . . . ?
Cu N1 N2 C6 -10.58(16) . . . . ?
Cu O2 N5 O4 7.24(14) . . . . ?
Cu O2 N5 O3 -173.70(10) . . . . ?
N2 N1 C2 C3 -0.48(15) . . . . ?
Cu N1 C2 C3 -174.64(9) . . . . ?
N2 N1 C2 C1 178.30(12) . . . . ?
Cu N1 C2 C1 4.1(2) . . . . ?
N1 C2 C3 C4 0.59(15) . . . . ?
C1 C2 C3 C4 -178.12(13) . . . . ?
N1 N2 C4 C3 0.17(14) . . . . ?
C6 N2 C4 C3 -173.92(12) . . . . ?
N1 N2 C4 C5 -178.14(12) . . . . ?
C6 N2 C4 C5 7.8(2) . . . . ?
C2 C3 C4 N2 -0.45(14) . . . . ?
C2 C3 C4 C5 177.67(14) . . . . ?
C4 N2 C6 C7 -115.69(14) . . . . ?
N1 N2 C6 C7 70.77(16) . . . . ?
C7 O1 C7 C6 -160.47(13) 2 . . . ?
Cu O1 C7 C6 19.53(13) . . . . ?
N2 C6 C7 O1 -69.07(14) . . . . ?
