#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:38:34 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179800 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/96/7009666.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_7009666
loop_
_publ_author_name
'Pohl, Siegfried'
'Harmjanz, Michael'
'Schneider, Jörg'
'Saak, Wolfgang'
'Henkel, Gerald'
_publ_section_title
;
 1,3-Bis(N,N,N',N'-tetramethylguanidino)propane: synthesis,
 characterization and bonding properties of the first bidentate,
 peralkylated guanidine ligand †
;
_journal_issue                   19
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              3473
_journal_paper_doi               10.1039/b002554m
_journal_year                    2000
_chemical_formula_sum            'C13 H30 Cu I N6'
_chemical_formula_weight         460.87
_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                 96.72(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.839(2)
_cell_length_b                   9.864(4)
_cell_length_c                   25.026(8)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    150
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     1921.8(11)
_computing_cell_refinement       'P3 (Siemens, 1991)'
_computing_data_collection       'P3 (Siemens, 1991)'
_computing_data_reduction        'P3 (Siemens, 1991)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens P4RA'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4479
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.22
_diffrn_standards_interval_count 99
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            'slightly yellow'
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.296
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0463
_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)+(0.0832P)²+7.8638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                3166
_reflns_number_total             4172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002554m.txt
_cod_data_source_block           (2)
_cod_original_sg_symbol_H-M      'P21 /n'
_cod_database_code               7009666
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.81777(6) 0.59629(5) 0.131054(19) 0.03264(16) Uani 1 1 d . . .
Cu Cu 1.05043(9) 0.76651(8) 0.12663(3) 0.0234(2) Uani 1 1 d . . .
C1 C 1.3442(8) 0.9130(8) 0.1835(2) 0.0292(15) Uani 1 1 d . . .
H1A H 1.3827 0.9789 0.2105 0.044(4) Uiso 1 1 d R . .
H1B H 1.4146 0.8337 0.1897 0.044(4) Uiso 1 1 d R . .
C2 C 1.3648(9) 0.9685(7) 0.1283(2) 0.0276(14) Uani 1 1 d . . .
H2A H 1.4709 1.0178 0.1301 0.044(4) Uiso 1 1 d R . .
H2B H 1.2730 1.0315 0.1186 0.044(4) Uiso 1 1 d R . .
C3 C 1.3608(8) 0.8607(7) 0.0834(3) 0.0261(13) Uani 1 1 d . . .
H3A H 1.4298 0.7848 0.0967 0.044(4) Uiso 1 1 d R . .
H3B H 1.4091 0.8975 0.0530 0.044(4) Uiso 1 1 d R . .
C4 C 1.1076(8) 0.8833(7) 0.2346(3) 0.0262(14) Uani 1 1 d . . .
C5 C 1.3509(9) 0.7837(9) 0.2930(3) 0.0377(17) Uani 1 1 d . . .
H5A H 1.3695 0.7411 0.2597 0.044(4) Uiso 1 1 d R . .
H5B H 1.4526 0.8320 0.3071 0.044(4) Uiso 1 1 d R . .
H5C H 1.3251 0.7158 0.3183 0.044(4) Uiso 1 1 d R . .
C6 C 1.1641(10) 0.9520(9) 0.3304(3) 0.0419(19) Uani 1 1 d . . .
H6A H 1.0687 1.0109 0.3197 0.044(4) Uiso 1 1 d R . .
H6B H 1.1331 0.8888 0.3568 0.044(4) Uiso 1 1 d R . .
H6C H 1.2606 1.0050 0.3456 0.044(4) Uiso 1 1 d R . .
C7 C 0.8295(9) 0.9651(8) 0.1937(3) 0.0346(16) Uani 1 1 d . . .
H7A H 0.8993 1.0207 0.1735 0.044(4) Uiso 1 1 d R . .
H7B H 0.7727 0.8972 0.1706 0.044(4) Uiso 1 1 d R . .
H7C H 0.7452 1.0204 0.2082 0.044(4) Uiso 1 1 d R . .
C8 C 0.8464(9) 0.8127(8) 0.2712(3) 0.0318(15) Uani 1 1 d . . .
H8A H 0.9274 0.7743 0.2989 0.044(4) Uiso 1 1 d R . .
H8B H 0.7626 0.8646 0.2875 0.044(4) Uiso 1 1 d R . .
H8C H 0.7901 0.7413 0.2499 0.044(4) Uiso 1 1 d R . .
C9 C 1.1429(8) 0.7831(6) 0.0159(3) 0.0242(13) Uani 1 1 d . . .
C10 C 1.4018(10) 0.6600(9) -0.0044(4) 0.0429(19) Uani 1 1 d . . .
H10A H 1.4068 0.6410 0.0334 0.044(4) Uiso 1 1 d R . .
H10B H 1.3857 0.5769 -0.0243 0.044(4) Uiso 1 1 d R . .
H10C H 1.5072 0.7020 -0.0116 0.044(4) Uiso 1 1 d R . .
C11 C 1.2320(11) 0.7893(8) -0.0756(3) 0.0395(18) Uani 1 1 d . . .
H11A H 1.1350 0.8491 -0.0816 0.044(4) Uiso 1 1 d R . .
H11B H 1.3326 0.8350 -0.0849 0.044(4) Uiso 1 1 d R . .
H11C H 1.2112 0.7099 -0.0976 0.044(4) Uiso 1 1 d R . .
C12 C 0.8499(9) 0.8696(7) 0.0189(3) 0.0316(15) Uani 1 1 d . . .
H12A H 0.9099 0.9412 0.0392 0.044(4) Uiso 1 1 d R . .
H12B H 0.7685 0.9079 -0.0086 0.044(4) Uiso 1 1 d R . .
H12C H 0.7906 0.8147 0.0424 0.044(4) Uiso 1 1 d R . .
C13 C 0.8986(10) 0.6758(8) -0.0383(3) 0.0377(17) Uani 1 1 d . . .
H13A H 0.9879 0.6266 -0.0530 0.044(4) Uiso 1 1 d R . .
H13B H 0.8403 0.6166 -0.0160 0.044(4) Uiso 1 1 d R . .
H13C H 0.8182 0.7098 -0.0671 0.044(4) Uiso 1 1 d R . .
N1 N 1.1648(7) 0.8756(6) 0.1886(2) 0.0253(12) Uani 1 1 d . . .
N2 N 1.1864(6) 0.8134(6) 0.0663(2) 0.0224(11) Uani 1 1 d . . .
N3 N 1.2096(7) 0.8786(7) 0.2837(2) 0.0317(13) Uani 1 1 d . . .
N4 N 0.9366(7) 0.9008(6) 0.2379(2) 0.0287(12) Uani 1 1 d . . .
N5 N 1.2570(7) 0.7506(6) -0.0197(2) 0.0309(13) Uani 1 1 d . . .
N6 N 0.9735(7) 0.7874(6) -0.0059(2) 0.0250(11) Uani 1 1 d . . .
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_publ_flag
N2 Cu N1 103.3(2) . . ?
N2 Cu I 130.27(16) . . ?
N1 Cu I 126.12(16) . . ?
N1 C1 C2 111.9(5) . . ?
C1 C2 C3 114.8(6) . . ?
N2 C3 C2 111.9(5) . . ?
N1 C4 N4 120.7(6) . . ?
N1 C4 N3 124.5(6) . . ?
N4 C4 N3 114.8(6) . . ?
N2 C9 N6 120.5(6) . . ?
N2 C9 N5 124.4(6) . . ?
N6 C9 N5 115.0(6) . . ?
C4 N1 C1 119.8(5) . . ?
C4 N1 Cu 123.5(4) . . ?
C1 N1 Cu 114.4(4) . . ?
C9 N2 C3 119.2(5) . . ?
C9 N2 Cu 125.2(4) . . ?
C3 N2 Cu 114.5(4) . . ?
C4 N3 C5 121.0(6) . . ?
C4 N3 C6 121.7(6) . . ?
C5 N3 C6 116.6(6) . . ?
C4 N4 C7 119.5(6) . . ?
C4 N4 C8 120.7(6) . . ?
C7 N4 C8 115.0(6) . . ?
C9 N5 C10 121.3(6) . . ?
C9 N5 C11 122.9(6) . . ?
C10 N5 C11 115.5(6) . . ?
C9 N6 C13 120.5(6) . . ?
C9 N6 C12 120.5(5) . . ?
C13 N6 C12 114.5(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I Cu 2.4911(10) . ?
Cu N2 2.002(5) . ?
Cu N1 2.010(5) . ?
C1 N1 1.474(8) . ?
C1 C2 1.512(8) . ?
C2 C3 1.545(10) . ?
C3 N2 1.461(8) . ?
C4 N1 1.287(8) . ?
C4 N4 1.363(8) . ?
C4 N3 1.387(8) . ?
C5 N3 1.448(9) . ?
C6 N3 1.454(10) . ?
C7 N4 1.454(9) . ?
C8 N4 1.445(9) . ?
C9 N2 1.302(8) . ?
C9 N6 1.376(8) . ?
C9 N5 1.371(8) . ?
C10 N5 1.460(9) . ?
C11 N5 1.442(9) . ?
C12 N6 1.457(9) . ?
C13 N6 1.450(9) . ?
