#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/13/2211374.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_2211374
loop_
_publ_author_name
'Boyd, Peter D. W.'
'Rickard, C. E. F.'
_publ_section_title
;[μ-N,N'-Bis(3-aminopropyl)oxamidato(2{-})]bis[(2,2'-bipyridine)copper(II)]
 dinitrate
;
_journal_coeditor_code           EZ2047
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3200
_journal_page_last               m3202
_journal_paper_doi               10.1107/S1600536806045351
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu2 (C8 H16 N4 O2) (C10 H8 N2)2] (N O3)2'
_chemical_formula_moiety         'C28 H32 Cu2 N8 O2 2+ , 2N O3 -'
_chemical_formula_sum            'C28 H32 Cu2 N10 O8'
_chemical_formula_weight         763.72
_chemical_name_systematic
;
[μ-N,N'-Bis(3-aminopropyl)oxamidato(2-)]bis[(2,2'-bipyridine)copper(II)]
dinitrate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                103.2900(10)
_cell_angle_beta                 107.6050(10)
_cell_angle_gamma                112.4360(10)
_cell_formula_units_Z            1
_cell_length_a                   8.9069(3)
_cell_length_b                   10.3003(4)
_cell_length_c                   10.3457(4)
_cell_measurement_reflns_used    6676
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     769.31(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and MERCURY (Macrae et al.,
2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_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  0.015
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7305
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.50
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.026
_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+0.358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.070
_refine_ls_wR_factor_ref         0.072
_reflns_number_gt                3123
_reflns_number_total             3353
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2047.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2211374
_cod_database_fobs_code          2211374
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.10320(3) 0.40253(2) 0.20585(2) 0.01786(8) Uani d . 1
N N1 0.2431(2) 0.53032(17) 0.42419(15) 0.0232(3) Uani d . 1
H H1A 0.1744 0.5656 0.4533 0.028 Uiso calc R 1
H H1D 0.2555 0.4673 0.4705 0.028 Uiso calc R 1
N N2 0.20273(19) 0.57748(16) 0.15575(15) 0.0191(3) Uani d . 1
N N3 -0.01608(19) 0.21416(16) 0.24350(15) 0.0187(3) Uani d . 1
N N4 0.2446(2) 0.27415(17) 0.15503(16) 0.0216(3) Uani d . 1
N N5 -0.1802(2) 0.60015(18) 0.30460(19) 0.0301(3) Uani d . 1
O O1 0.11293(16) 0.67549(13) -0.01459(13) 0.0214(2) Uani d . 1
O O2 -0.1022(2) 0.5290(2) 0.3461(2) 0.0470(4) Uani d . 1
O O3 -0.1975(4) 0.6196(3) 0.1884(2) 0.0735(7) Uani d . 1
O O4 -0.2512(2) 0.64577(19) 0.37818(18) 0.0392(4) Uani d . 1
C C1 0.4234(3) 0.6621(2) 0.4793(2) 0.0311(4) Uani d . 1
H H1B 0.5051 0.6253 0.4624 0.037 Uiso calc R 1
H H1C 0.4704 0.7160 0.5859 0.037 Uiso calc R 1
C C2 0.4207(3) 0.7728(2) 0.4049(2) 0.0306(4) Uani d . 1
H H2A 0.5378 0.8663 0.4580 0.037 Uiso calc R 1
H H2B 0.3291 0.8004 0.4128 0.037 Uiso calc R 1
C C3 0.3817(2) 0.7111(2) 0.24318(19) 0.0242(4) Uani d . 1
H H3A 0.3895 0.7909 0.2049 0.029 Uiso calc R 1
H H3B 0.4727 0.6833 0.2340 0.029 Uiso calc R 1
C C4 0.0898(2) 0.57342(17) 0.03905(17) 0.0172(3) Uani d . 1
C C5 -0.1415(2) 0.1950(2) 0.2941(2) 0.0243(3) Uani d . 1
H H5A -0.1807 0.2679 0.3056 0.029 Uiso calc R 1
C C6 -0.2153(3) 0.0716(2) 0.3301(2) 0.0301(4) Uani d . 1
H H6A -0.3026 0.0610 0.3660 0.036 Uiso calc R 1
C C7 -0.1584(3) -0.0357(2) 0.3123(2) 0.0319(4) Uani d . 1
H H7A -0.2065 -0.1205 0.3361 0.038 Uiso calc R 1
C C8 -0.0300(3) -0.0171(2) 0.2591(2) 0.0283(4) Uani d . 1
H H8A 0.0096 -0.0896 0.2457 0.034 Uiso calc R 1
C C9 0.0402(2) 0.10982(18) 0.22559(18) 0.0195(3) Uani d . 1
C C10 0.1805(2) 0.14022(19) 0.17008(18) 0.0199(3) Uani d . 1
C C11 0.2427(3) 0.0377(2) 0.1363(2) 0.0270(4) Uani d . 1
H H11A 0.1926 -0.0575 0.1434 0.032 Uiso calc R 1
C C12 0.3800(3) 0.0791(2) 0.0922(2) 0.0330(4) Uani d . 1
H H12A 0.4257 0.0126 0.0703 0.040 Uiso calc R 1
C C13 0.4497(3) 0.2185(3) 0.0803(2) 0.0329(4) Uani d . 1
H H13A 0.5447 0.2491 0.0525 0.039 Uiso calc R 1
C C14 0.3762(3) 0.3119(2) 0.1102(2) 0.0274(4) Uani d . 1
H H14A 0.4200 0.4051 0.0988 0.033 Uiso calc R 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
_geom_angle_publ_flag
N2 Cu O1 . 2_565 83.86(5) y
N2 Cu N1 . . 92.71(6) y
O1 Cu N1 2_565 . 149.59(6) y
N2 Cu N3 . . 175.79(5) y
O1 Cu N3 2_565 . 91.94(5) y
N1 Cu N3 . . 91.03(6) y
N2 Cu N4 . . 103.52(6) ?
O1 Cu N4 2_565 . 104.96(5) y
N1 Cu N4 . . 105.21(6) y
N3 Cu N4 . . 77.33(6) y
C1 N1 Cu . . 118.87(11) ?
C1 N1 H1A . . 107.6 ?
Cu N1 H1A . . 107.6 ?
C1 N1 H1D . . 107.6 ?
Cu N1 H1D . . 107.6 ?
H1A N1 H1D . . 107.0 ?
C4 N2 C3 . . 120.14(13) ?
C4 N2 Cu . . 113.98(11) ?
C3 N2 Cu . . 125.69(11) ?
C5 N3 C9 . . 119.43(14) ?
C5 N3 Cu . . 121.63(12) ?
C9 N3 Cu . . 118.82(11) ?
C14 N4 C10 . . 118.89(15) ?
C14 N4 Cu . . 128.93(12) ?
C10 N4 Cu . . 112.17(11) ?
O3 N5 O4 . . 118.99(18) ?
O3 N5 O2 . . 121.84(19) ?
O4 N5 O2 . . 119.05(16) ?
C4 O1 Cu . 2_565 109.76(10) ?
N1 C1 C2 . . 112.38(15) ?
N1 C1 H1B . . 109.1 ?
C2 C1 H1B . . 109.1 ?
N1 C1 H1C . . 109.1 ?
C2 C1 H1C . . 109.1 ?
H1B C1 H1C . . 107.9 ?
C1 C2 C3 . . 114.27(16) ?
C1 C2 H2A . . 108.7 ?
C3 C2 H2A . . 108.7 ?
C1 C2 H2B . . 108.7 ?
C3 C2 H2B . . 108.7 ?
H2A C2 H2B . . 107.6 ?
N2 C3 C2 . . 111.39(14) ?
N2 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
N2 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
O1 C4 N2 . . 128.00(14) ?
O1 C4 C4 . 2_565 118.54(17) ?
N2 C4 C4 . 2_565 113.46(16) ?
N3 C5 C6 . . 122.18(17) ?
N3 C5 H5A . . 118.9 ?
C6 C5 H5A . . 118.9 ?
C7 C6 C5 . . 118.87(18) ?
C7 C6 H6A . . 120.6 ?
C5 C6 H6A . . 120.6 ?
C6 C7 C8 . . 119.18(17) ?
C6 C7 H7A . . 120.4 ?
C8 C7 H7A . . 120.4 ?
C7 C8 C9 . . 119.45(17) ?
C7 C8 H8A . . 120.3 ?
C9 C8 H8A . . 120.3 ?
N3 C9 C8 . . 120.89(16) ?
N3 C9 C10 . . 116.00(14) ?
C8 C9 C10 . . 123.11(16) ?
N4 C10 C11 . . 121.92(16) ?
N4 C10 C9 . . 115.52(14) ?
C11 C10 C9 . . 122.56(16) ?
C12 C11 C10 . . 118.44(18) ?
C12 C11 H11A . . 120.8 ?
C10 C11 H11A . . 120.8 ?
C13 C12 C11 . . 119.83(18) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C12 C13 C14 . . 118.41(18) ?
C12 C13 H13A . . 120.8 ?
C14 C13 H13A . . 120.8 ?
N4 C14 C13 . . 122.44(18) ?
N4 C14 H14A . . 118.8 ?
C13 C14 H14A . . 118.8 ?
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 N2 . 1.9468(13) y
Cu O1 2_565 2.0126(12) y
Cu N1 . 2.0166(14) y
Cu N3 . 2.0173(14) y
Cu N4 . 2.2276(15) y
N1 C1 . 1.474(2) ?
N1 H1A . 0.9100 ?
N1 H1D . 0.9100 ?
N2 C4 . 1.297(2) ?
N2 C3 . 1.461(2) ?
N3 C5 . 1.340(2) ?
N3 C9 . 1.348(2) ?
N4 C14 . 1.343(2) ?
N4 C10 . 1.343(2) ?
N5 O3 . 1.237(2) ?
N5 O4 . 1.247(2) ?
N5 O2 . 1.248(2) ?
O1 C4 . 1.2759(19) ?
O1 Cu 2_565 2.0126(12) ?
C1 C2 . 1.520(3) ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.521(3) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C4 C4 2_565 1.520(3) ?
C5 C6 . 1.384(2) ?
C5 H5A . 0.9400 ?
C6 C7 . 1.379(3) ?
C6 H6A . 0.9400 ?
C7 C8 . 1.382(3) ?
C7 H7A . 0.9400 ?
C8 C9 . 1.392(2) ?
C8 H8A . 0.9400 ?
C9 C10 . 1.485(2) ?
C10 C11 . 1.392(2) ?
C11 C12 . 1.384(3) ?
C11 H11A . 0.9400 ?
C12 C13 . 1.381(3) ?
C12 H12A . 0.9400 ?
C13 C14 . 1.384(3) ?
C13 H13A . 0.9400 ?
C14 H14A . 0.9400 ?
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
N1 H1A O2 . 0.91 2.21 2.928(2) 135.2
N1 H1A O2 2_566 0.91 2.63 3.080(2) 111.1
N1 H1D O4 2_566 0.91 2.16 3.032(2) 161.1
C1 H1B O4 1_655 0.98 2.53 3.413(3) 150.0
C3 H3B O4 1_655 0.98 2.68 3.528(2) 144.8
C7 H7A O4 1_545 0.94 2.45 3.348(2) 160.0
C8 H8A O3 1_545 0.94 2.65 3.253(3) 122.4
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
N2 Cu N1 C1 . . -33.22(14)
O1 Cu N1 C1 2_565 . -115.69(15)
N3 Cu N1 C1 . . 148.72(14)
N4 Cu N1 C1 . . 71.58(14)
O1 Cu N2 C4 2_565 . 5.67(12)
N1 Cu N2 C4 . . -144.03(12)
N4 Cu N2 C4 . . 109.62(12)
O1 Cu N2 C3 2_565 . -179.34(15)
N1 Cu N2 C3 . . 30.96(15)
N4 Cu N2 C3 . . -75.39(15)
O1 Cu N3 C5 2_565 . -78.01(14)
N1 Cu N3 C5 . . 71.72(14)
N4 Cu N3 C5 . . 177.08(14)
O1 Cu N3 C9 2_565 . 106.07(12)
N1 Cu N3 C9 . . -104.20(13)
N4 Cu N3 C9 . . 1.17(12)
N2 Cu N4 C14 . . 4.13(16)
O1 Cu N4 C14 2_565 . 91.28(15)
N1 Cu N4 C14 . . -92.52(15)
N3 Cu N4 C14 . . 179.89(16)
N2 Cu N4 C10 . . -174.20(11)
O1 Cu N4 C10 2_565 . -87.05(12)
N1 Cu N4 C10 . . 89.15(12)
N3 Cu N4 C10 . . 1.56(11)
Cu N1 C1 C2 . . 55.2(2)
N1 C1 C2 C3 . . -68.9(2)
C4 N2 C3 C2 . . 127.05(17)
Cu N2 C3 C2 . . -47.7(2)
C1 C2 C3 N2 . . 62.5(2)
Cu O1 C4 N2 2_565 . 175.56(14)
Cu O1 C4 C4 2_565 2_565 -4.4(2)
C3 N2 C4 O1 . . 0.0(3)
Cu N2 C4 O1 . . 175.28(14)
C3 N2 C4 C4 . 2_565 179.98(17)
Cu N2 C4 C4 . 2_565 -4.7(2)
C9 N3 C5 C6 . . 0.5(3)
Cu N3 C5 C6 . . -175.42(14)
N3 C5 C6 C7 . . -0.4(3)
C5 C6 C7 C8 . . -0.1(3)
C6 C7 C8 C9 . . 0.5(3)
C5 N3 C9 C8 . . -0.1(2)
Cu N3 C9 C8 . . 175.93(13)
C5 N3 C9 C10 . . -179.56(14)
Cu N3 C9 C10 . . -3.55(19)
C7 C8 C9 N3 . . -0.4(3)
C7 C8 C9 C10 . . 179.05(17)
C14 N4 C10 C11 . . -2.0(2)
Cu N4 C10 C11 . . 176.53(13)
C14 N4 C10 C9 . . 177.72(15)
Cu N4 C10 C9 . . -3.76(17)
N3 C9 C10 N4 . . 4.9(2)
C8 C9 C10 N4 . . -174.57(16)
N3 C9 C10 C11 . . -175.39(15)
C8 C9 C10 C11 . . 5.1(3)
N4 C10 C11 C12 . . 2.8(3)
C9 C10 C11 C12 . . -176.87(16)
C10 C11 C12 C13 . . -1.0(3)
C11 C12 C13 C14 . . -1.4(3)
C10 N4 C14 C13 . . -0.7(3)
Cu N4 C14 C13 . . -178.88(14)
C12 C13 C14 N4 . . 2.3(3)
