#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/57/2015709.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_2015709
loop_
_publ_author_name
'Fen Sun'
'Yan-Tuan Li'
'Zhi-Yong Wu'
'Yu-Lan Song'
'Man Jiang'
_publ_section_title
;{μ-N,N'-Bis[3-(dimethylamino)propyl]oxamidato(2--)-κ⁶N,N',O':N'',N''',O}bis[(1H-imidazole-κN³)(methanol-κO)copper(II)]
 bis(perchlorate)
;
_journal_coeditor_code           SQ3043
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m584
_journal_page_last               m586
_journal_paper_doi               10.1107/S0108270106042624
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac
'[Cu2 (C12 H24 N4 O2) (C3 H4 N2)2 (C H4 O)2] (Cl1 O4)2'
_chemical_formula_moiety         'C20 H40 Cu2 N8 O4 2+, 2Cl1 O4 -'
_chemical_formula_sum            'C20 H40 Cl2 Cu2 N8 O12'
_chemical_formula_weight         782.60
_chemical_name_systematic
;
{μ-N,N'-Bis[3-(dimethylamino)propyl]oxamidato(2-)-
κ⁶N,N',O':N'',N''',O}bis[(1H-imidazole-\kN³)(methanol-\kO)copper(II)]
bis(perchlorate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.328(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.023(3)
_cell_length_b                   13.084(3)
_cell_length_c                   12.317(3)
_cell_measurement_reflns_used    2584
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.8005
_cell_measurement_theta_min      2.598
_cell_volume                     1578.0(7)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8761
_diffrn_reflns_theta_full        26.14
_diffrn_reflns_theta_max         26.14
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0446
_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)+(0.0512P)²+1.6075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2201
_reflns_number_total             3121
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3043.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2015709
_cod_database_fobs_code          2015709
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C C1 0.2616(6) 0.3469(4) -0.0329(5) 0.0623(14) Uani d . 1
H H1A 0.2697 0.4193 -0.0209 0.093 Uiso calc R 1
H H1B 0.2044 0.3336 -0.1045 0.093 Uiso calc R 1
H H1C 0.3504 0.3180 -0.0296 0.093 Uiso calc R 1
C C2 0.2874(5) 0.3248(4) 0.1634(4) 0.0590(13) Uani d . 1
H H2A 0.3799 0.3052 0.1643 0.089 Uiso calc R 1
H H2B 0.2552 0.2882 0.2204 0.089 Uiso calc R 1
H H2C 0.2836 0.3969 0.1767 0.089 Uiso calc R 1
C C3 0.0653(5) 0.3491(3) 0.0559(5) 0.0568(13) Uani d . 1
H H3A 0.0424 0.3341 0.1268 0.068 Uiso calc R 1
H H3B 0.0757 0.4227 0.0516 0.068 Uiso calc R 1
C C4 -0.0506(5) 0.3170(4) -0.0339(5) 0.0588(14) Uani d . 1
H H4A -0.0194 0.3140 -0.1032 0.071 Uiso calc R 1
H H4B -0.1214 0.3687 -0.0422 0.071 Uiso calc R 1
C C5 -0.1120(4) 0.2155(3) -0.0152(4) 0.0388(10) Uani d . 1
H H5A -0.1481 0.2187 0.0518 0.047 Uiso calc R 1
H H5B -0.1871 0.2006 -0.0771 0.047 Uiso calc R 1
C C6 -0.0540(3) 0.0401(3) -0.0059(3) 0.0279(8) Uani d . 1
C C7 0.1968(6) 0.1677(5) -0.2865(5) 0.0837(19) Uani d . 1
H H7A 0.1378 0.2249 -0.3102 0.126 Uiso calc R 1
H H7B 0.1777 0.1146 -0.3414 0.126 Uiso calc R 1
H H7C 0.2902 0.1888 -0.2775 0.126 Uiso calc R 1
C C8 0.4833(4) 0.1298(3) 0.0125(4) 0.0410(10) Uani d . 1
H H8 0.4697 0.1572 -0.0587 0.049 Uiso calc R 1
C C9 0.5817(4) 0.0574(4) 0.1675(4) 0.0498(12) Uani d . 1
H H9 0.6465 0.0264 0.2230 0.060 Uiso calc R 1
C C10 0.4510(4) 0.0777(3) 0.1705(4) 0.0438(10) Uani d . 1
H H10 0.4094 0.0628 0.2292 0.053 Uiso calc R 1
N N1 0.2003(3) 0.3002(3) 0.0540(3) 0.0408(9) Uani d . 1
N N2 -0.0104(3) 0.1337(2) -0.0044(3) 0.0301(7) Uani d . 1
N N3 0.3891(3) 0.1240(2) 0.0729(3) 0.0357(8) Uani d . 1
N N4 0.6003(3) 0.0906(3) 0.0685(3) 0.0486(10) Uani d . 1
H H4 0.6752 0.0872 0.0453 0.058 Uiso calc R 1
O O1 -0.1776(2) 0.00981(19) -0.0161(2) 0.0338(6) Uani d . 1
O O2 0.1744(4) 0.1308(3) -0.1849(3) 0.0718(11) Uani d . 1
H H2 0.1020 0.0814 -0.2122 0.09(2) Uiso d R 1
O O3 0.1643(4) 0.0997(3) 0.2507(3) 0.0724(11) Uani d . 1
O O4 0.0299(5) 0.2255(3) 0.3026(4) 0.0907(13) Uani d . 1
O O5 0.0946(5) 0.0904(4) 0.4181(3) 0.1060(16) Uani d . 1
O O6 -0.0636(4) 0.0703(4) 0.2521(4) 0.1058(16) Uani d . 1
Cl Cl1 0.05644(11) 0.12021(8) 0.30697(9) 0.0456(3) Uani d . 1
Cu Cu1 0.18881(4) 0.14413(3) 0.02921(4) 0.03355(17) Uani d . 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 N2 . 97.01(12) y
N1 Cu1 N3 . 94.04(13) y
N1 Cu1 O1 3 176.09(13) y
N2 Cu1 N3 . 167.84(13) y
N2 Cu1 O1 3 82.95(11) y
N3 Cu1 O1 3 85.68(11) y
C1 N1 C2 . 108.4(4) ?
C1 N1 C3 . 110.5(4) ?
C1 N1 Cu1 . 108.7(3) ?
C2 N1 C3 . 104.5(4) ?
C2 N1 Cu1 . 110.7(3) ?
C3 N1 Cu1 . 113.8(2) ?
C5 N2 C6 . 117.6(3) y
C5 N2 Cu1 . 128.9(2) y
C6 N2 Cu1 . 113.2(2) y
C8 N3 C10 . 105.9(3) ?
C8 N3 Cu1 . 130.0(3) ?
C10 N3 Cu1 . 122.6(3) ?
C8 N4 C9 . 108.5(3) ?
C8 N4 H4 . 125.7 ?
C9 N4 H4 . 125.7 ?
N1 C1 H1A . 109.5 ?
N1 C1 H1B . 109.5 ?
N1 C1 H1C . 109.5 ?
H1A C1 H1B . 109.5 ?
H1A C1 H1C . 109.5 ?
H1B C1 H1C . 109.5 ?
N1 C2 H2A . 109.5 ?
N1 C2 H2B . 109.5 ?
N1 C2 H2C . 109.5 ?
H2A C2 H2B . 109.5 ?
H2A C2 H2C . 109.5 ?
H2B C2 H2C . 109.5 ?
N1 C3 H3A . 108.4 ?
N1 C3 H3B . 108.4 ?
N1 C3 C4 . 115.6(4) ?
C4 C3 H3A . 108.4 ?
C4 C3 H3B . 108.4 ?
H3A C3 H3B . 107.5 ?
C3 C4 C5 . 114.7(4) ?
C3 C4 H4A . 108.6 ?
C3 C4 H4B . 108.6 ?
C5 C4 H4A . 108.6 ?
C5 C4 H4B . 108.6 ?
H4A C4 H4B . 107.6 ?
N2 C5 C4 . 111.1(3) ?
N2 C5 H5A . 109.4 ?
N2 C5 H5B . 109.4 ?
C4 C5 H5A . 109.4 ?
C4 C5 H5B . 109.4 ?
H5A C5 H5B . 108.0 ?
N2 C6 C6 3 115.3(4) ?
N2 C6 O1 . 127.4(3) ?
O1 C6 C6 3 117.2(4) ?
O2 C7 H7A . 109.5 ?
O2 C7 H7B . 109.5 ?
O2 C7 H7C . 109.5 ?
H7A C7 H7B . 109.5 ?
H7A C7 H7C . 109.5 ?
H7B C7 H7C . 109.5 ?
N3 C8 N4 . 110.0(4) ?
N3 C8 H8 . 125.0 ?
N4 C8 H8 . 125.0 ?
N4 C9 C10 . 106.6(4) ?
N4 C9 H9 . 126.7 ?
C10 C9 H9 . 126.7 ?
N3 C10 C9 . 108.9(4) ?
N3 C10 H10 . 125.5 ?
C9 C10 H10 . 125.5 ?
C6 O1 Cu1 3 110.6(2) y
C7 O2 H2 . 99.8 ?
O3 Cl1 O4 . 108.9(2) ?
O3 Cl1 O5 . 110.2(2) ?
O3 Cl1 O6 . 109.7(3) ?
O4 Cl1 O5 . 108.8(3) ?
O4 Cl1 O6 . 107.5(3) ?
O5 Cl1 O6 . 111.6(3) ?
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 N1 . 2.064(3) y
Cu1 N2 . 1.955(3) y
Cu1 N3 . 1.982(3) y
Cu1 O1 3 2.022(3) y
C1 N1 . 1.475(6) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 N1 . 1.477(6) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 C4 . 1.484(7) ?
C3 N1 . 1.501(5) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.502(6) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 N2 . 1.463(5) y
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 N2 . 1.299(5) y
C6 O1 . 1.282(4) y
C6 C6 3 1.492(7) y
C7 O2 . 1.403(7) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 N3 . 1.323(5) ?
C8 N4 . 1.329(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.344(6) ?
C9 N4 . 1.345(6) ?
C9 H9 . 0.9300 ?
C10 N3 . 1.371(5) ?
C10 H10 . 0.9300 ?
N4 H4 . 0.8600 ?
O2 H2 . 0.9767 ?
O3 Cl1 . 1.429(3) ?
O4 Cl1 . 1.402(4) ?
O5 Cl1 . 1.396(4) ?
O6 Cl1 . 1.408(4) ?
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
O2 H2 O6 3 0.98 2.06 2.907(6) 143.8
N4 H4 O1 1_655 0.86 2.06 2.855(4) 153.1
C8 H8 O4 4_665 0.93 2.47 3.317(6) 152.3
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_4
_geom_torsion
N1 C3 C4 C5 . . 79.1(6)
C3 C4 C5 N2 . . -59.5(6)
N3 C8 N4 C9 . . 0.7(5)
C8 N4 C9 C10 . . -0.3(5)
N4 C9 C10 N3 . . -0.2(5)
C4 C3 N1 C1 . . 76.8(5)
C4 C3 N1 C2 . . -166.8(4)
C4 C3 N1 Cu1 . . -45.9(5)
O1 C6 N2 C5 . . 0.2(6)
C6 C6 N2 C5 3 . -179.8(4)
O1 C6 N2 Cu1 . . 173.7(3)
C6 C6 N2 Cu1 3 . -6.3(5)
C4 C5 N2 C6 . . -169.1(4)
C4 C5 N2 Cu1 . . 18.5(5)
N4 C8 N3 C10 . . -0.8(4)
N4 C8 N3 Cu1 . . -167.3(3)
C9 C10 N3 C8 . . 0.6(5)
C9 C10 N3 Cu1 . . 168.3(3)
N2 C6 O1 Cu1 . 3 174.0(3)
C6 C6 O1 Cu1 3 3 -6.0(5)
C6 N2 Cu1 N3 . . -13.5(8)
C5 N2 Cu1 N3 . . 159.2(6)
C6 N2 Cu1 O1 . 3 7.4(3)
C5 N2 Cu1 O1 . 3 -180.0(3)
C6 N2 Cu1 N1 . . -168.7(3)
C5 N2 Cu1 N1 . . 4.0(3)
C8 N3 Cu1 N2 . . 117.9(7)
C10 N3 Cu1 N2 . . -46.6(8)
C8 N3 Cu1 O1 . 3 97.1(3)
C10 N3 Cu1 O1 . 3 -67.4(3)
C8 N3 Cu1 N1 . . -86.8(3)
C10 N3 Cu1 N1 . . 108.7(3)
C1 N1 Cu1 N2 . . -115.2(3)
C2 N1 Cu1 N2 . . 125.8(3)
C3 N1 Cu1 N2 . . 8.4(3)
C1 N1 Cu1 N3 . . 69.8(3)
C2 N1 Cu1 N3 . . -49.1(3)
C3 N1 Cu1 N3 . . -166.5(3)
