#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/96/7009665.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_7009665
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 H32 Cl2 N6'
_chemical_formula_weight         343.35
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 128.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.892(19)
_cell_length_b                   7.897(4)
_cell_length_c                   19.834(11)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    150
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     3785(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4644
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_interval_count 99
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00054(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0409
_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)+(0.0340P)²+3.5931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                3152
_reflns_number_total             4131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b002554m.txt
_cod_data_source_block           (1b)
_cod_original_sg_symbol_H-M      'C2 /c'
_cod_database_code               7009665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cl1 Cl 0.2500 0.2500 0.0000 0.03288(19) Uani 1 2 d S . .
Cl2 Cl 0.38388(2) -0.06728(7) 0.34637(3) 0.02868(14) Uani 1 1 d . . .
Cl3 Cl 0.5000 0.59936(9) 0.2500 0.03033(18) Uani 1 2 d S . .
N1 N 0.32101(7) 0.6435(2) 0.20237(10) 0.0217(4) Uani 1 1 d . . .
H1 H 0.3408 0.7278 0.2403 0.0326(11) Uiso 1 1 d R . .
N2 N 0.41942(6) 0.9163(2) 0.15126(10) 0.0207(3) Uani 1 1 d . . .
N3 N 0.35310(7) 0.4557(2) 0.31289(11) 0.0262(4) Uani 1 1 d . . .
N4 N 0.26650(7) 0.4132(2) 0.18138(11) 0.0245(4) Uani 1 1 d . . .
H4 H 0.4461 0.8368 0.1782 0.0326(11) Uiso 1 1 d R . .
N5 N 0.45653(7) 1.0288(2) 0.09003(10) 0.0219(4) Uani 1 1 d . . .
N6 N 0.40582(6) 1.2007(2) 0.11406(10) 0.0191(3) Uani 1 1 d . . .
C1 C 0.29982(8) 0.6700(3) 0.11324(12) 0.0221(4) Uani 1 1 d . . .
H1A H 0.2728 0.7591 0.0875 0.0326(11) Uiso 1 1 d R . .
H1B H 0.2820 0.5681 0.0810 0.0326(11) Uiso 1 1 d R . .
C2 C 0.34651(8) 0.7155(2) 0.11027(12) 0.0207(4) Uani 1 1 d . . .
H2A H 0.3328 0.7118 0.0516 0.0326(11) Uiso 1 1 d R . .
H2B H 0.3755 0.6328 0.1423 0.0326(11) Uiso 1 1 d R . .
C3 C 0.37054(8) 0.8901(2) 0.14647(13) 0.0207(4) Uani 1 1 d . . .
H3A H 0.3434 0.9753 0.1104 0.0326(11) Uiso 1 1 d R . .
H3B H 0.3807 0.8995 0.2030 0.0326(11) Uiso 1 1 d R . .
C4 C 0.31327(8) 0.5036(2) 0.23142(13) 0.0210(4) Uani 1 1 d . . .
C5 C 0.41141(9) 0.4969(3) 0.35811(15) 0.0347(5) Uani 1 1 d . . .
H5A H 0.4215 0.5953 0.3935 0.0326(11) Uiso 1 1 d R . .
H5B H 0.4176 0.5158 0.3169 0.0326(11) Uiso 1 1 d R . .
H5C H 0.4334 0.4014 0.3928 0.0326(11) Uiso 1 1 d R . .
C6 C 0.34068(11) 0.3750(3) 0.36532(14) 0.0375(6) Uani 1 1 d . . .
H6A H 0.3586 0.4332 0.4192 0.0326(11) Uiso 1 1 d R . .
H6B H 0.3525 0.2590 0.3752 0.0326(11) Uiso 1 1 d R . .
H6C H 0.3013 0.3758 0.3334 0.0326(11) Uiso 1 1 d R . .
C7 C 0.21396(8) 0.4891(3) 0.11084(14) 0.0287(5) Uani 1 1 d . . .
H7A H 0.2045 0.4472 0.0577 0.0326(11) Uiso 1 1 d R . .
H7B H 0.2168 0.6101 0.1107 0.0326(11) Uiso 1 1 d R . .
H7C H 0.1845 0.4592 0.1125 0.0326(11) Uiso 1 1 d R . .
C8 C 0.26460(10) 0.2299(3) 0.19002(15) 0.0349(5) Uani 1 1 d . . .
H8A H 0.3018 0.1873 0.2253 0.0326(11) Uiso 1 1 d R . .
H8B H 0.2439 0.1750 0.1349 0.0326(11) Uiso 1 1 d R . .
H8C H 0.2484 0.2026 0.2171 0.0326(11) Uiso 1 1 d R . .
C9 C 0.42724(7) 1.0491(2) 0.11847(11) 0.0169(4) Uani 1 1 d . . .
C10 C 0.46322(9) 0.8637(3) 0.06422(14) 0.0300(5) Uani 1 1 d . . .
H10A H 0.4515 0.8731 0.0068 0.0326(11) Uiso 1 1 d R . .
H10B H 0.4406 0.7798 0.0640 0.0326(11) Uiso 1 1 d R . .
H10C H 0.5011 0.8272 0.1014 0.0326(11) Uiso 1 1 d R . .
C11 C 0.48882(8) 1.1654(3) 0.09079(14) 0.0274(5) Uani 1 1 d . . .
H11A H 0.5259 1.1278 0.1182 0.0326(11) Uiso 1 1 d R . .
H11B H 0.4895 1.2612 0.1212 0.0326(11) Uiso 1 1 d R . .
H11C H 0.4717 1.1996 0.0327 0.0326(11) Uiso 1 1 d R . .
C12 C 0.40011(8) 1.2562(3) 0.17857(12) 0.0239(4) Uani 1 1 d . . .
H12A H 0.4188 1.1768 0.2254 0.0326(11) Uiso 1 1 d R . .
H12B H 0.3618 1.2629 0.1536 0.0326(11) Uiso 1 1 d R . .
H12C H 0.4161 1.3667 0.1995 0.0326(11) Uiso 1 1 d R . .
C13 C 0.38704(8) 1.3231(3) 0.04572(12) 0.0244(4) Uani 1 1 d . . .
H13A H 0.3837 1.2677 -0.0004 0.0326(11) Uiso 1 1 d R . .
H13B H 0.4130 1.4146 0.0671 0.0326(11) Uiso 1 1 d R . .
H13C H 0.3517 1.3687 0.0242 0.0326(11) Uiso 1 1 d R . .
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'
Cl Cl 0.1484 0.1585 '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
C4 N1 C1 124.89(16) . . ?
C9 N2 C3 124.82(15) . . ?
C4 N3 C6 122.10(19) . . ?
C4 N3 C5 122.14(17) . . ?
C6 N3 C5 115.45(19) . . ?
C4 N4 C7 122.33(18) . . ?
C4 N4 C8 122.92(19) . . ?
C7 N4 C8 114.67(18) . . ?
C9 N5 C10 122.25(16) . . ?
C9 N5 C11 122.81(17) . . ?
C10 N5 C11 114.65(16) . . ?
C9 N6 C13 123.04(16) . . ?
C9 N6 C12 122.18(16) . . ?
C13 N6 C12 114.78(16) . . ?
N1 C1 C2 110.94(15) . . ?
C3 C2 C1 113.07(16) . . ?
N2 C3 C2 109.81(15) . . ?
N1 C4 N3 118.55(18) . . ?
N1 C4 N4 121.43(18) . . ?
N3 C4 N4 120.01(18) . . ?
N2 C9 N5 119.05(17) . . ?
N2 C9 N6 120.09(16) . . ?
N5 C9 N6 120.87(16) . . ?
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
N1 C4 1.335(2) . ?
N1 C1 1.468(2) . ?
N2 C9 1.333(2) . ?
N2 C3 1.467(2) . ?
N3 C4 1.338(3) . ?
N3 C6 1.460(3) . ?
N3 C5 1.463(3) . ?
N4 C4 1.340(3) . ?
N4 C7 1.456(3) . ?
N4 C8 1.463(3) . ?
N5 C9 1.341(2) . ?
N5 C10 1.461(3) . ?
N5 C11 1.462(2) . ?
N6 C9 1.344(2) . ?
N6 C13 1.459(2) . ?
N6 C12 1.463(2) . ?
C1 C2 1.523(3) . ?
C2 C3 1.518(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652723
