#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/41/2214109.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_2214109
loop_
_publ_author_name
'Tian-Fu Liu'
_publ_section_title
;μ-Oxalato-κ⁴O¹,O²:O^1'^,O^2'^-bis{[N,N'-bis(pyridin-2-ylmethylene)propane-1,2-diamine-κ⁴-N,N',N'',N''']copper(II)}
 bis(perchlorate)
;
_journal_coeditor_code           CF2095
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1856
_journal_page_last               m1858
_journal_paper_doi               10.1107/S1600536807022659
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 (C2 O4) (C15 H16 N4)2] (Cl O4)2'
_chemical_formula_moiety         'C32 H32 Cu2 N8 O4 +, 2(Cl O4 -)'
_chemical_formula_sum            'C32 H32 Cl2 Cu2 N8 O12'
_chemical_formula_weight         918.64
_chemical_name_systematic
;
μ-Oxalato-κ⁴O¹,O²:O^1'^,O^2'^-bis{[N,N'-bis(pyridin-2-
ylmethylene)propane-1,2-diamine-κ⁴-
N,N',N'',N''']copper(II)} bis(perchlorate)
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 97.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.339(2)
_cell_length_b                   9.2995(19)
_cell_length_c                   19.395(4)
_cell_measurement_reflns_used    16951
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.12
_cell_volume                     2026.3(7)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection
'PROCESS-AUTO (Molecular Structure Corporation, 1994)'
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'XP (Siemens, 1990)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16951
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.451
_refine_ls_extinction_coef       0.0062(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0557
_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)+(0.0777P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                2290
_reflns_number_total             4599
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2095.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2214109
_cod_database_fobs_code          2214109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
Cu Cu 0.19634(4) 0.37228(5) 0.58356(2) 0.0448(2) Uani d . 1
Cl Cl1 0.0000 0.7640(2) 0.7500 0.0983(7) Uani d S 1
Cl Cl2 0.5000 0.0344(3) 0.7500 0.1450(13) Uani d S 1
O O1 0.0168(2) 0.6062(3) 0.42796(13) 0.0486(7) Uani d . 1
O O2 0.1566(2) 0.5045(3) 0.50385(13) 0.0483(7) Uani d . 1
O O3 0.0830(14) 0.8442(12) 0.7554(6) 0.490(14) Uani d . 1
O O4 -0.0034(6) 0.6869(9) 0.6933(3) 0.252(4) Uani d . 1
O O5 0.5969(6) -0.0293(8) 0.7532(7) 0.321(7) Uani d . 1
O O6 0.4778(16) 0.1456(14) 0.7154(11) 0.568(18) Uani d . 1
N N1 0.1779(3) 0.1861(4) 0.52937(16) 0.0484(8) Uani d . 1
N N2 0.2104(3) 0.2341(4) 0.66415(15) 0.0490(8) Uani d . 1
N N3 0.2147(3) 0.5295(4) 0.65839(17) 0.0593(10) Uani d . 1
N N4 0.3959(3) 0.4299(5) 0.5920(2) 0.0673(11) Uani d . 1
C C1 0.1838(5) 0.1677(5) 0.4610(2) 0.0670(14) Uani d . 1
H H1 0.1950 0.2475 0.4338 0.080 Uiso calc R 1
C C2 0.1737(5) 0.0342(6) 0.4306(3) 0.0780(15) Uani d . 1
H H2 0.1817 0.0235 0.3837 0.094 Uiso calc R 1
C C3 0.1521(5) -0.0808(5) 0.4688(3) 0.0692(14) Uani d . 1
H H3 0.1443 -0.1716 0.4487 0.083 Uiso calc R 1
C C4 0.1417(4) -0.0629(5) 0.5385(3) 0.0667(13) Uani d . 1
H H4 0.1253 -0.1411 0.5655 0.080 Uiso calc R 1
C C5 0.1562(4) 0.0738(5) 0.5676(2) 0.0507(10) Uani d . 1
C C6 0.1453(4) 0.1036(5) 0.6429(2) 0.0657(13) Uani d . 1
H H6 0.1035 0.0475 0.6710 0.079 Uiso calc R 1
C C7 0.1703(4) 0.3177(5) 0.7227(2) 0.0596(12) Uani d . 1
H H7 0.0856 0.3401 0.7105 0.071 Uiso calc R 1
C C8 0.2397(4) 0.4573(5) 0.7264(2) 0.0623(13) Uani d . 1
H H8A 0.2160 0.5184 0.7626 0.075 Uiso calc R 1
H H8B 0.3243 0.4379 0.7372 0.075 Uiso calc R 1
C C9 0.3108(6) 0.6321(6) 0.6465(3) 0.0835(17) Uani d . 1
H H9 0.3062 0.7313 0.6517 0.100 Uiso calc R 1
C C10 0.4174(5) 0.5531(7) 0.6247(3) 0.0796(17) Uani d . 1
C C11 0.5314(7) 0.6157(9) 0.6344(4) 0.119(3) Uani d . 1
H H11 0.5449 0.7028 0.6577 0.143 Uiso calc R 1
C C12 0.6208(9) 0.5454(15) 0.6090(5) 0.164(6) Uani d . 1
H H12 0.6975 0.5830 0.6150 0.197 Uiso calc R 1
C C13 0.5975(7) 0.4225(13) 0.5755(4) 0.151(5) Uani d . 1
H H13 0.6579 0.3753 0.5566 0.181 Uiso calc R 1
C C14 0.4847(5) 0.3632(7) 0.5683(3) 0.0913(19) Uani d . 1
H H14 0.4713 0.2748 0.5462 0.110 Uiso calc R 1
C C15 0.1864(5) 0.2355(6) 0.7919(2) 0.0821(16) Uani d . 1
H H15A 0.1403 0.1487 0.7870 0.123 Uiso calc R 1
H H15B 0.1602 0.2944 0.8275 0.123 Uiso calc R 1
H H15C 0.2690 0.2120 0.8045 0.123 Uiso calc R 1
C C16 0.0480(3) 0.5328(4) 0.47980(18) 0.0395(9) 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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Cu N2 . . 171.47(12) yes
O2 Cu N1 . . 97.43(12) yes
N2 Cu N1 . . 81.31(13) yes
O2 Cu N3 . . 95.76(13) yes
N2 Cu N3 . . 85.18(14) yes
N1 Cu N3 . . 166.43(14) yes
O2 Cu N4 . . 91.63(12) yes
N2 Cu N4 . . 96.84(13) yes
N1 Cu N4 . . 105.48(16) yes
N3 Cu N4 . . 77.26(16) yes
O2 Cu O1 . 3_566 75.88(10) yes
N2 Cu O1 . 3_566 95.65(12) yes
N1 Cu O1 . 3_566 89.51(12) yes
N3 Cu O1 . 3_566 90.62(12) yes
N4 Cu O1 . 3_566 161.76(13) yes
O3 Cl1 O3 2_556 . 102.7(17) ?
O3 Cl1 O4 2_556 . 109.6(8) ?
O3 Cl1 O4 . . 110.4(7) ?
O3 Cl1 O4 2_556 2_556 110.4(7) ?
O3 Cl1 O4 . 2_556 109.6(8) ?
O4 Cl1 O4 . 2_556 113.6(8) ?
O6 Cl2 O6 2_656 . 67(2) ?
O6 Cl2 O5 2_656 2_656 122.6(9) ?
O6 Cl2 O5 . 2_656 104.9(10) ?
O6 Cl2 O5 2_656 . 104.9(9) ?
O6 Cl2 O5 . . 122.6(9) ?
O5 Cl2 O5 2_656 . 123.1(7) ?
C16 O1 Cu . 3_566 107.3(2) ?
C16 O2 Cu . . 121.1(2) ?
Cl2 O6 O6 . 2_656 56.5(11) ?
C5 N1 C1 . . 119.2(4) ?
C5 N1 Cu . . 113.5(3) ?
C1 N1 Cu . . 127.3(3) ?
C6 N2 C7 . . 117.0(4) ?
C6 N2 Cu . . 109.2(2) ?
C7 N2 Cu . . 104.9(2) ?
C8 N3 C9 . . 112.0(3) ?
C8 N3 Cu . . 107.3(3) ?
C9 N3 Cu . . 110.7(3) ?
C10 N4 C14 . . 118.5(5) ?
C10 N4 Cu . . 110.6(4) ?
C14 N4 Cu . . 130.8(4) ?
N1 C1 C2 . . 121.8(4) ?
N1 C1 H1 . . 119.1 ?
C2 C1 H1 . . 119.1 ?
C3 C2 C1 . . 119.5(4) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 119.4(5) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C3 C4 C5 . . 119.0(5) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
N1 C5 C4 . . 121.0(4) ?
N1 C5 C6 . . 116.3(4) ?
C4 C5 C6 . . 122.7(4) ?
N2 C6 C5 . . 108.9(4) ?
N2 C6 H6 . . 125.5 ?
C5 C6 H6 . . 125.5 ?
N2 C7 C8 . . 105.7(3) ?
N2 C7 C15 . . 113.1(4) ?
C8 C7 C15 . . 112.7(4) ?
N2 C7 H7 . . 108.4 ?
C8 C7 H7 . . 108.4 ?
C15 C7 H7 . . 108.4 ?
N3 C8 C7 . . 108.2(3) ?
N3 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
N3 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.4 ?
N3 C9 C10 . . 111.0(4) ?
N3 C9 H9 . . 124.5 ?
C10 C9 H9 . . 124.5 ?
N4 C10 C11 . . 122.2(7) ?
N4 C10 C9 . . 116.8(5) ?
C11 C10 C9 . . 120.8(7) ?
C12 C11 C10 . . 118.1(9) ?
C12 C11 H11 . . 121.0 ?
C10 C11 H11 . . 121.0 ?
C13 C12 C11 . . 119.1(10) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 C14 . . 121.0(11) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
N4 C14 C13 . . 121.1(8) ?
N4 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C7 C15 H15A . . 109.5 ?
C7 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C7 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O1 C16 O2 . . 124.6(3) yes
O1 C16 C16 . 3_566 119.3(4) yes
O2 C16 C16 . 3_566 116.1(4) yes
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
Cu O2 . 1.979(3) yes
Cu N2 . 2.013(3) yes
Cu N1 . 2.021(3) yes
Cu N3 . 2.051(3) yes
Cu N4 . 2.309(4) yes
Cu O1 3_566 2.405(3) yes
Cl1 O3 2_556 1.194(9) ?
Cl1 O3 . 1.194(9) ?
Cl1 O4 . 1.310(6) ?
Cl1 O4 2_556 1.310(6) ?
Cl2 O6 2_656 1.240(10) ?
Cl2 O6 . 1.240(10) ?
Cl2 O5 2_656 1.243(7) ?
Cl2 O5 . 1.243(7) ?
O1 C16 . 1.227(4) yes
O1 Cu 3_566 2.405(3) ?
O2 C16 . 1.284(4) yes
O6 O6 2_656 1.37(4) ?
N1 C5 . 1.323(5) ?
N1 C1 . 1.347(5) ?
N2 C6 . 1.451(5) ?
N2 C7 . 1.497(5) ?
N3 C8 . 1.473(5) ?
N3 C9 . 1.489(6) ?
N4 C10 . 1.316(7) ?
N4 C14 . 1.318(6) ?
C1 C2 . 1.373(6) ?
C1 H1 . 0.930 ?
C2 C3 . 1.343(7) ?
C2 H2 . 0.930 ?
C3 C4 . 1.382(7) ?
C3 H3 . 0.930 ?
C4 C5 . 1.392(6) ?
C4 H4 . 0.930 ?
C5 C6 . 1.507(6) ?
C6 H6 . 0.930 ?
C7 C8 . 1.515(6) ?
C7 C15 . 1.533(5) ?
C7 H7 . 0.980 ?
C8 H8A . 0.970 ?
C8 H8B . 0.970 ?
C9 C10 . 1.523(8) ?
C9 H9 . 0.930 ?
C10 C11 . 1.406(8) ?
C11 C12 . 1.354(13) ?
C11 H11 . 0.930 ?
C12 C13 . 1.323(14) ?
C12 H12 . 0.930 ?
C13 C14 . 1.382(10) ?
C13 H13 . 0.930 ?
C14 H14 . 0.930 ?
C15 H15A . 0.960 ?
C15 H15B . 0.960 ?
C15 H15C . 0.960 ?
C16 C16 3_566 1.549(7) yes
