#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/36/4323601.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_4323601
loop_
_publ_author_name
'Hitoshi Miyasaka'
'Shingo Okamura'
'Toshio Nakashima'
'Naohide Matsumoto'
_publ_section_title
;
 Copper(II) Complexes of
 N,N'-Bis((2-substituted-imidazol-4-yl)methylene)-3,3'-diaminodi-
 propylamine (2-Substituent = H, Me): Δ and Λ Enantiomorphs of the
 Protonated Complex and Helical Structure of the Deprotonated Complex
 Formed by Hydrogen Bonds
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4329
_journal_page_last               4335
_journal_paper_doi               10.1021/ic970425v
_journal_volume                  36
_journal_year                    1997
_chemical_formula_sum            'C14 H21 Cu N9 O6'
_chemical_formula_weight         474.92
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             'Sun Apr  6 11:17:06 1997'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 98.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4.00
_cell_length_a                   9.610(4)
_cell_length_b                   13.463(5)
_cell_length_c                   15.568(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    20.0
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      29.50
_cell_volume                     1994.0(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan: PROCESS (MSC)'
_computing_publication_material  'teXsan: FINISH (MSC)'
_computing_structure_refinement  'teXsan: LS (MSC)'
_computing_structure_solution    SHELXS86
_diffrn_ambient_temperature      20.0
_diffrn_measurement_device       AFC7R
_diffrn_measurement_method       'omega/2-theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  1.59
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_theta_max         25.0012
_diffrn_standards_decay_%        -0.24
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.1486
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.46460
_refine_diff_density_min         -0.36070
_refine_ls_extinction_coef       0.61032
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_obs   4.750
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0490
_refine_ls_shift/esd_max         0.0080
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0330
_reflns_number_observed          2737
_reflns_number_total             3910
_cod_data_source_file            ic970425v_1.cif
_cod_data_source_block           '[Cu{H2L1}](NO3)2(1b)'
_cod_original_cell_volume        1994(1)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        C14H21O6N9Cu
_cod_database_code               4323601
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,1/2-z'
'   -x,   -y,   -z'
'   +x,1/2-y,1/2+z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
Cu 0.69874(5) 0.23927(5) 0.68822(3) 0.0616 Uij ? ?
O1 0.1851(4) 0.0966(3) 0.3343(2) 0.0991 Uij ? ?
O2 0.1208(3) 0.0534(3) 0.4537(2) 0.1001 Uij ? ?
O3 0.3213(4) 0.0087(3) 0.4256(3) 0.1046 Uij ? ?
O4 0.2707(3) 0.0941(3) 0.8251(2) 0.0911 Uij ? ?
O5 0.1568(4) 0.0478(4) 0.9254(3) 0.1394 Uij ? ?
O6 0.3733(3) 0.0143(3) 0.9358(2) 0.0905 Uij ? ?
N1 0.7364(4) 0.3590(3) 0.7772(2) 0.0563 Uij ? ?
N2 0.7665(5) 0.4605(3) 0.8886(3) 0.0735 Uij ? ?
N3 0.5026(3) 0.2860(3) 0.6874(2) 0.0617 Uij ? ?
N4 0.6821(4) 0.2453(4) 0.5603(2) 0.0929 Uij ? ?
N5 0.8955(3) 0.1928(3) 0.6992(2) 0.0711 Uij ? ?
N6 0.6880(4) 0.0362(3) 0.8952(2) 0.0648 Uij ? ?
N7 0.6901(4) 0.1288(3) 0.7804(2) 0.0526 Uij ? ?
N8 0.2108(4) 0.0538(3) 0.4041(3) 0.0714 Uij ? ?
N9 0.2664(4) 0.0525(3) 0.8951(3) 0.0742 Uij ? ?
C1 0.8293(5) 0.4036(4) 0.8343(3) 0.0656 Uij ? ?
C2 0.6262(6) 0.4531(4) 0.8649(3) 0.0724 Uij ? ?
C3 0.6075(5) 0.3907(4) 0.7960(3) 0.0593 Uij ? ?
C4 0.4863(5) 0.3528(4) 0.7431(3) 0.0658 Uij ? ?
C5 0.3860(4) 0.2484(4) 0.6262(3) 0.0837 Uij ? ?
C6 0.4216(7) 0.2391(8) 0.5403(4) 0.1720 Uij ? ?
C7 0.5489(6) 0.2403(5) 0.5135(3) 0.1023 Uij ? ?
C8 0.8064(6) 0.2572(5) 0.5239(3) 0.0928 Uij ? ?
C9 0.9411(6) 0.2541(8) 0.5642(4) 0.1728 Uij ? ?
C10 0.9992(5) 0.2312(5) 0.6489(3) 0.1009 Uij ? ?
C11 0.9316(4) 0.1296(4) 0.7598(3) 0.0703 Uij ? ?
C12 0.8238(5) 0.0954(3) 0.8082(3) 0.0568 Uij ? ?
C13 0.8238(5) 0.0379(4) 0.8794(3) 0.0650 Uij ? ?
C14 0.6104(5) 0.0912(4) 0.8334(3) 0.0578 Uij ? ?
H1 0.9286 0.3946 0.8379 0.0798 Uij ? ?
H2 0.8131 0.5006 0.9336 0.0918 Uij ? ?
H3 0.5515 0.4872 0.8932 0.0863 Uij ? ?
H4 0.3941 0.3754 0.7472 0.0783 Uij ? ?
H5 0.3561 0.1856 0.6402 0.0989 Uij ? ?
H6 0.3085 0.2942 0.6196 0.0790 Uij ? ?
H7 0.3760 0.2923 0.5048 0.1997 Uij ? ?
H8 0.3843 0.1779 0.5160 0.1997 Uij ? ?
H9 0.5444 0.2926 0.4728 0.1245 Uij ? ?
H10 0.5528 0.1782 0.4841 0.1245 Uij ? ?
H11 0.6717 0.3191 0.5616 0.0989 Uij ? ?
H12 0.7961 0.3185 0.4934 0.1103 Uij ? ?
H13 0.7999 0.2040 0.4829 0.1103 Uij ? ?
H14 0.9677 0.3218 0.5552 0.1985 Uij ? ?
H15 0.9819 0.2120 0.5272 0.1985 Uij ? ?
H16 1.0702 0.1830 0.6427 0.1256 Uij ? ?
H17 1.0424 0.2900 0.6729 0.1256 Uij ? ?
H18 1.0263 0.1084 0.7722 0.0835 Uij ? ?
H19 0.9035 0.0053 0.9131 0.0767 Uij ? ?
H20 0.6541 -0.0008 0.9409 0.0790 Uij ? ?
H21 0.5125 0.1015 0.8309 0.0706 Uij ? ?
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 56 0.003 0.002 'International Tables'
H 0 84 0.000 0.000 'International Tables'
O 0 24 0.011 0.006 'International Tables'
N 0 36 0.006 0.003 'International Tables'
Cu 0 4 0.320 1.265 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
? ? ?
? ? ?
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N(1) Cu N(3) 80.7(1) ? ? ? yes
N(1) Cu N(4) 127.5(2) ? ? ? yes
N(1) Cu N(5) 96.4(2) ? ? ? yes
N(1) Cu N(7) 96.5(1) ? ? ? yes
N(3) Cu N(4) 92.2(2) ? ? ? yes
N(3) Cu N(5) 175.5(2) ? ? ? yes
N(3) Cu N(7) 95.8(1) ? ? ? yes
N(4) Cu N(5) 92.3(2) ? ? ? yes
N(4) Cu N(7) 136.1(2) ? ? ? yes
N(5) Cu N(7) 81.1(1) ? ? ? yes
Cu N(1) C(1) 145.7(4) ? ? ? yes
Cu N(1) C(3) 107.3(3) ? ? ? yes
C(1) N(1) C(3) 105.1(4) ? ? ? yes
C(1) N(2) C(2) 107.8(4) ? ? ? yes
Cu N(3) C(4) 115.3(3) ? ? ? yes
Cu N(3) C(5) 122.5(3) ? ? ? yes
C(4) N(3) C(5) 122.2(4) ? ? ? yes
Cu N(4) C(7) 117.7(3) ? ? ? yes
Cu N(4) C(8) 117.4(3) ? ? ? yes
C(7) N(4) C(8) 124.9(4) ? ? ? yes
Cu N(5) C(10) 124.3(3) ? ? ? yes
Cu N(5) C(11) 115.4(3) ? ? ? yes
C(10) N(5) C(11) 120.0(4) ? ? ? yes
C(13) N(6) C(14) 108.0(4) ? ? ? yes
Cu N(7) C(12) 108.9(3) ? ? ? yes
Cu N(7) C(14) 143.1(3) ? ? ? yes
C(12) N(7) C(14) 106.4(4) ? ? ? yes
O(1) N(8) O(2) 119.0(5) ? ? ? yes
O(1) N(8) O(3) 122.3(5) ? ? ? yes
O(2) N(8) O(3) 118.7(5) ? ? ? yes
O(4) N(9) O(5) 120.5(4) ? ? ? yes
O(4) N(9) O(6) 120.8(4) ? ? ? yes
O(5) N(9) O(6) 118.7(4) ? ? ? yes
N(1) C(1) N(2) 111.3(4) ? ? ? yes
N(2) C(2) C(3) 106.2(4) ? ? ? yes
N(1) C(3) C(2) 109.7(4) ? ? ? yes
N(1) C(3) C(4) 117.0(4) ? ? ? yes
C(2) C(3) C(4) 133.4(5) ? ? ? yes
N(3) C(4) C(3) 118.5(4) ? ? ? yes
N(3) C(5) C(6) 112.2(4) ? ? ? yes
C(5) C(6) C(7) 129.5(5) ? ? ? yes
N(4) C(7) C(6) 130.7(5) ? ? ? yes
N(4) C(8) C(9) 128.4(5) ? ? ? yes
C(8) C(9) C(10) 132.4(5) ? ? ? yes
N(5) C(10) C(9) 112.1(4) ? ? ? yes
N(5) C(11) C(12) 117.3(4) ? ? ? yes
N(7) C(12) C(11) 116.2(4) ? ? ? yes
N(7) C(12) C(13) 109.7(4) ? ? ? yes
C(11) C(12) C(13) 134.1(5) ? ? ? yes
N(6) C(13) C(12) 105.6(4) ? ? ? yes
N(6) C(14) N(7) 110.4(4) ? ? ? yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N(1) 2.124(4) ? ? yes
Cu N(3) 1.985(3) ? ? yes
Cu N(4) 1.978(3) ? ? yes
Cu N(5) 1.977(4) ? ? yes
Cu N(7) 2.078(4) ? ? yes
O(1) N(8) 1.224(5) ? ? yes
O(2) N(8) 1.239(5) ? ? yes
O(3) N(8) 1.228(5) ? ? yes
O(4) N(9) 1.231(4) ? ? yes
O(5) N(9) 1.216(4) ? ? yes
O(6) N(9) 1.239(4) ? ? yes
N(1) C(1) 1.312(5) ? ? yes
N(1) C(3) 1.380(5) ? ? yes
N(2) C(1) 1.345(6) ? ? yes
N(2) C(2) 1.350(6) ? ? yes
N(3) C(4) 1.275(5) ? ? yes
N(3) C(5) 1.455(5) ? ? yes
N(4) C(7) 1.382(6) ? ? yes
N(4) C(8) 1.401(6) ? ? yes
N(5) C(10) 1.446(5) ? ? yes
N(5) C(11) 1.281(5) ? ? yes
N(6) C(13) 1.361(5) ? ? yes
N(6) C(14) 1.352(5) ? ? yes
N(7) C(12) 1.372(5) ? ? yes
N(7) C(14) 1.304(5) ? ? yes
C(2) C(3) 1.354(6) ? ? yes
C(3) C(4) 1.423(6) ? ? yes
C(5) C(6) 1.432(7) ? ? yes
C(6) C(7) 1.347(7) ? ? yes
C(8) C(9) 1.357(7) ? ? yes
C(9) C(10) 1.392(7) ? ? yes
C(11) C(12) 1.440(6) ? ? yes
C(12) C(13) 1.353(6) ? ? yes
