#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:49:44 +0100 (Fri 25 de Mar de 2016) $
#$Revision: 179938 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/33/7023376.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_7023376
loop_
_publ_author_name
'Ferlay, Sylvie'
'Dechambenoit, Pierre'
'Kyritsakas, Nathalie'
'Hosseini, Mir Wais'
_publ_section_title
;
 Molecular tectonics: tuning the dimensionality and topology of extended
 cyanocuprate networks using a bisamidinium cation.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11661
_journal_page_last               11671
_journal_paper_doi               10.1039/c3dt51252e
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C13 H22 N2, C3 Cu2 N3, C H4 O'
_chemical_formula_sum            'C17 H26 Cu2 N5 O'
_chemical_formula_weight         443.51
_chemical_name_systematic
;

?

;
_space_group_IT_number           2
_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           SHELXL-97
_cell_angle_alpha                93.171(3)
_cell_angle_beta                 92.107(3)
_cell_angle_gamma                115.690(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3378(7)
_cell_length_b                   8.4859(7)
_cell_length_c                   16.0299(15)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      2.86
_cell_volume                     1018.17(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11641
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  0.8173
_exptl_absorpt_correction_T_min  0.7297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.8169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                3521
_reflns_number_total             4633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt51252e.txt
_cod_data_source_block           e522a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7023376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.6603(3) 0.0820(3) 0.16840(15) 0.0232(5) Uani 1 1 d .
N1 N 0.6118(3) -0.0406(3) 0.22077(13) 0.0288(5) Uani 1 1 d .
H1 H 0.5252 -0.1444 0.2045 0.035 Uiso 1 1 calc R
C2 C 0.6962(4) -0.0118(3) 0.30572(15) 0.0300(6) Uani 1 1 d .
H2A H 0.8027 -0.0350 0.3046 0.036 Uiso 1 1 calc R
H2B H 0.6117 -0.0938 0.3425 0.036 Uiso 1 1 calc R
C3 C 0.7512(3) 0.1779(3) 0.34040(14) 0.0225(5) Uani 1 1 d .
C4 C 0.8668(3) 0.2969(3) 0.27606(14) 0.0261(5) Uani 1 1 d .
H4A H 0.8876 0.4193 0.2909 0.031 Uiso 1 1 calc R
H4B H 0.9841 0.2935 0.2777 0.031 Uiso 1 1 calc R
N2 N 0.7809(3) 0.2412(3) 0.19092(12) 0.0270(5) Uani 1 1 d .
H2 H 0.8123 0.3189 0.1532 0.032 Uiso 1 1 calc R
C5 C 0.8716(3) 0.2168(4) 0.42149(15) 0.0286(5) Uani 1 1 d .
H5A H 0.9732 0.1905 0.4089 0.034 Uiso 1 1 calc R
H5B H 0.9210 0.3439 0.4382 0.034 Uiso 1 1 calc R
C6 C 0.7829(4) 0.1164(4) 0.49619(16) 0.0398(7) Uani 1 1 d .
H6A H 0.7324 -0.0112 0.4804 0.048 Uiso 1 1 calc R
H6B H 0.6835 0.1447 0.5109 0.048 Uiso 1 1 calc R
C7 C 0.9149(5) 0.1623(5) 0.57254(19) 0.0525(9) Uani 1 1 d .
H7A H 1.0182 0.1435 0.5570 0.079 Uiso 1 1 calc R
H7B H 0.8567 0.0872 0.6171 0.079 Uiso 1 1 calc R
H7C H 0.9543 0.2855 0.5924 0.079 Uiso 1 1 calc R
C8 C 0.5821(3) 0.2052(4) 0.35319(16) 0.0316(6) Uani 1 1 d .
H8A H 0.5148 0.1823 0.2982 0.038 Uiso 1 1 calc R
H8B H 0.5061 0.1160 0.3898 0.038 Uiso 1 1 calc R
C9 C 0.6104(4) 0.3843(5) 0.39067(19) 0.0445(8) Uani 1 1 d .
H9A H 0.6834 0.4754 0.3541 0.053 Uiso 1 1 calc R
H9B H 0.6761 0.4092 0.4462 0.053 Uiso 1 1 calc R
C10 C 0.4315(6) 0.3914(7) 0.4001(2) 0.0691(13) Uani 1 1 d .
H10A H 0.3605 0.3530 0.3465 0.104 Uiso 1 1 calc R
H10B H 0.4527 0.5119 0.4171 0.104 Uiso 1 1 calc R
H10C H 0.3668 0.3138 0.4427 0.104 Uiso 1 1 calc R
C11 C 0.5762(3) 0.0395(3) 0.08135(15) 0.0246(5) Uani 1 1 d .
C12 C 0.5374(4) -0.1228(3) 0.04015(16) 0.0300(6) Uani 1 1 d .
H12 H 0.5630 -0.2064 0.0677 0.036 Uiso 1 1 calc R
C13 C 0.5391(4) 0.1627(3) 0.04146(16) 0.0291(5) Uani 1 1 d .
H13 H 0.5659 0.2734 0.0698 0.035 Uiso 1 1 calc R
Cu1 Cu -0.03657(5) 0.19728(5) 0.80229(3) 0.04961(14) Uani 1 1 d .
Cu2 Cu 0.61927(5) 0.55347(5) 0.80928(2) 0.04484(13) Uani 1 1 d .
C14 C 0.3682(4) 0.4282(4) 0.81519(18) 0.0406(6) Uani 0.50 1 d P
N3 N 0.3682(4) 0.4282(4) 0.81519(18) 0.0406(6) Uani 0.50 1 d P
C15 C 0.2158(4) 0.3389(4) 0.81018(19) 0.0424(7) Uani 0.50 1 d P
N4 N 0.2158(4) 0.3389(4) 0.81018(19) 0.0424(7) Uani 0.50 1 d P
C16 C -0.1508(4) -0.0508(4) 0.8073(2) 0.0452(7) Uani 0.50 1 d P
N5 N -0.1508(4) -0.0508(4) 0.8073(2) 0.0452(7) Uani 0.50 1 d P
C17 C -0.1820(4) 0.3209(4) 0.7935(2) 0.0538(8) Uani 0.50 1 d P
N6 N -0.1820(4) 0.3209(4) 0.7935(2) 0.0538(8) Uani 0.50 1 d P
C18 C 0.7637(4) 0.7991(4) 0.81225(19) 0.0426(6) Uani 0.50 1 d P
N7 N 0.7637(4) 0.7991(4) 0.81225(19) 0.0426(6) Uani 0.50 1 d P
C19 C 0.7368(4) 0.4020(4) 0.7952(2) 0.0502(8) Uani 0.50 1 d P
N8 N 0.7368(4) 0.4020(4) 0.7952(2) 0.0502(8) Uani 0.50 1 d P
C20 C 1.0242(7) 0.3230(8) 0.0389(4) 0.0872(15) Uani 1 1 d D
O1A O 0.9796(11) 0.1590(14) 0.0002(6) 0.161(5) Uani 0.50 1 d PD
O1 O 0.9342(8) 0.4180(8) 0.0509(3) 0.0739(18) Uani 0.50 1 d PD
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'
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'
H H 0.0000 0.0000 '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
N2 C1 N1 121.3(2) . .
N2 C1 C11 119.4(2) . .
N1 C1 C11 119.3(2) . .
C1 N1 C2 122.5(2) . .
C1 N1 H1 118.8 . .
C2 N1 H1 118.8 . .
N1 C2 C3 109.9(2) . .
N1 C2 H2A 109.7 . .
C3 C2 H2A 109.7 . .
N1 C2 H2B 109.7 . .
C3 C2 H2B 109.7 . .
H2A C2 H2B 108.2 . .
C2 C3 C5 109.3(2) . .
C2 C3 C4 106.75(19) . .
C5 C3 C4 106.65(19) . .
C2 C3 C8 109.2(2) . .
C5 C3 C8 113.1(2) . .
C4 C3 C8 111.7(2) . .
N2 C4 C3 111.33(19) . .
N2 C4 H4A 109.4 . .
C3 C4 H4A 109.4 . .
N2 C4 H4B 109.4 . .
C3 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
C1 N2 C4 123.3(2) . .
C1 N2 H2 118.4 . .
C4 N2 H2 118.4 . .
C6 C5 C3 116.2(2) . .
C6 C5 H5A 108.2 . .
C3 C5 H5A 108.2 . .
C6 C5 H5B 108.2 . .
C3 C5 H5B 108.2 . .
H5A C5 H5B 107.4 . .
C5 C6 C7 111.8(2) . .
C5 C6 H6A 109.3 . .
C7 C6 H6A 109.3 . .
C5 C6 H6B 109.3 . .
C7 C6 H6B 109.3 . .
H6A C6 H6B 107.9 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C3 116.7(2) . .
C9 C8 H8A 108.1 . .
C3 C8 H8A 108.1 . .
C9 C8 H8B 108.1 . .
C3 C8 H8B 108.1 . .
H8A C8 H8B 107.3 . .
C8 C9 C10 110.7(3) . .
C8 C9 H9A 109.5 . .
C10 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C13 C11 C12 120.4(2) . .
C13 C11 C1 120.0(2) . .
C12 C11 C1 119.6(2) . .
C11 C12 C13 119.9(2) . 2_655
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 2_655 .
C11 C13 C12 119.6(2) . 2_655
C11 C13 H13 120.2 . .
C12 C13 H13 120.2 2_655 .
C16 Cu1 C15 125.19(11) . .
C16 Cu1 C17 118.71(12) . .
C15 Cu1 C17 116.04(11) . .
C14 Cu2 C18 129.45(11) . .
C14 Cu2 C19 113.19(12) . .
C18 Cu2 C19 117.33(12) . .
C15 C14 Cu2 171.4(3) . .
C14 C15 Cu1 178.5(3) . .
N7 C16 Cu1 173.1(3) 1_445 .
C18 C16 Cu1 173.1(3) 1_445 .
N8 C17 Cu1 174.0(4) 1_455 .
C19 C17 Cu1 174.0(4) 1_455 .
N5 C18 Cu2 174.6(3) 1_665 .
C16 C18 Cu2 174.6(3) 1_665 .
N6 C19 Cu2 173.3(3) 1_655 .
C17 C19 Cu2 173.3(3) 1_655 .
O1 C20 O1A 133.3(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.307(3) .
C1 N1 1.307(3) .
C1 C11 1.491(3) .
N1 C2 1.467(3) .
N1 H1 0.8800 .
C2 C3 1.534(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C5 1.541(3) .
C3 C4 1.535(3) .
C3 C8 1.543(3) .
C4 N2 1.470(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
N2 H2 0.8800 .
C5 C6 1.529(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.529(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.518(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.532(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C13 1.392(4) .
C11 C12 1.391(4) .
C12 C13 1.391(4) 2_655
C12 H12 0.9500 .
C13 C12 1.391(4) 2_655
C13 H13 0.9500 .
Cu1 C16 1.906(3) .
Cu1 C15 1.913(3) .
Cu1 C17 1.923(3) .
Cu2 C14 1.902(3) .
Cu2 C18 1.899(3) .
Cu2 C19 1.933(3) .
C14 C15 1.160(4) .
C16 N7 1.168(4) 1_445
C16 C18 1.168(4) 1_445
C17 N8 1.156(4) 1_455
C17 C19 1.156(4) 1_455
C18 N5 1.168(4) 1_665
C18 C16 1.168(4) 1_665
C19 N6 1.156(4) 1_655
C19 C17 1.156(4) 1_655
C20 O1 1.330(7) .
C20 O1A 1.378(8) .
