#------------------------------------------------------------------------------
#$Date: 2025-08-20 15:05:43 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/34/4063494.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_4063494
loop_
_publ_author_name
'Chen, Tianniu'
'Hunks, William'
'Chen, Philip S.'
'Xu, Chongying'
'DiPasquale, Antonio G.'
'Rheingold, Arnold L.'
_publ_section_title
;
 Synthesis, Structural Characterization, and Thermal Properties of the
 First Germanium N,N,N',N'-Tetraalkylguanidinates
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              501
_journal_page_last               504
_journal_paper_doi               10.1021/om900801w
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C14 H36 Ge N8'
_chemical_formula_weight         389.10
_chemical_name_common            BH1518-81-2
_space_group.centring_type       P
_space_group_IT_number           14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.3190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6692(4)
_cell_length_b                   15.7430(7)
_cell_length_c                   14.9497(7)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      2.81
_cell_volume                     2007.32(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.976
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         0.5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15557
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.91
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.8460
_exptl_absorpt_correction_T_min  0.7813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0277P)²+1.4849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                3550
_reflns_number_total             3645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900801w_si_002.cif
_cod_data_source_block           atmi64
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4063494
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
C1 C 0.9818(2) 0.33537(11) 0.24966(12) 0.0215(4) Uani 1 1 d . . .
H1A H 1.0270 0.2785 0.2611 0.032 Uiso 1 1 calc R . .
H1B H 1.0169 0.3715 0.3028 0.032 Uiso 1 1 calc R . .
H1C H 1.0163 0.3601 0.1964 0.032 Uiso 1 1 calc R . .
C2 C 0.7543(2) 0.27846(15) 0.15352(13) 0.0345(5) Uani 1 1 d . . .
H2A H 0.7833 0.3052 0.0997 0.052 Uiso 1 1 calc R . .
H2B H 0.6399 0.2741 0.1455 0.052 Uiso 1 1 calc R . .
H2C H 0.8005 0.2216 0.1616 0.052 Uiso 1 1 calc R . .
C3 C 0.3697(2) 0.38344(13) 0.28777(13) 0.0264(4) Uani 1 1 d . . .
H3A H 0.3518 0.4211 0.3371 0.040 Uiso 1 1 calc R . .
H3B H 0.3562 0.3243 0.3052 0.040 Uiso 1 1 calc R . .
H3C H 0.2942 0.3967 0.2325 0.040 Uiso 1 1 calc R . .
C4 C 0.5574(2) 0.48273(12) 0.24802(13) 0.0266(4) Uani 1 1 d . . .
H4A H 0.4788 0.5007 0.1960 0.040 Uiso 1 1 calc R . .
H4B H 0.6622 0.4871 0.2324 0.040 Uiso 1 1 calc R . .
H4C H 0.5513 0.5194 0.3002 0.040 Uiso 1 1 calc R . .
C5 C 0.6460(2) 0.16737(10) 0.39456(12) 0.0189(3) Uani 1 1 d . . .
C6 C 0.5487(2) 0.02152(11) 0.38764(12) 0.0271(4) Uani 1 1 d . . .
H6A H 0.4944 0.0148 0.3247 0.041 Uiso 1 1 calc R . .
H6B H 0.5019 -0.0166 0.4272 0.041 Uiso 1 1 calc R . .
H6C H 0.6599 0.0075 0.3917 0.041 Uiso 1 1 calc R . .
C7 C 0.3723(2) 0.13855(13) 0.39696(13) 0.0281(4) Uani 1 1 d . . .
H7A H 0.3655 0.1959 0.4215 0.042 Uiso 1 1 calc R . .
H7B H 0.3064 0.0999 0.4251 0.042 Uiso 1 1 calc R . .
H7C H 0.3358 0.1394 0.3310 0.042 Uiso 1 1 calc R . .
C8 C 0.8350(2) 0.09499(13) 0.51642(15) 0.0341(5) Uani 1 1 d . . .
H8A H 0.7416 0.0893 0.5444 0.051 Uiso 1 1 calc R . .
H8B H 0.9176 0.1243 0.5586 0.051 Uiso 1 1 calc R . .
H8C H 0.8720 0.0385 0.5027 0.051 Uiso 1 1 calc R . .
C9 C 0.9295(2) 0.17470(12) 0.39615(15) 0.0296(4) Uani 1 1 d . . .
H9A H 0.8960 0.1893 0.3319 0.044 Uiso 1 1 calc R . .
H9B H 1.0102 0.1305 0.4019 0.044 Uiso 1 1 calc R . .
H9C H 0.9725 0.2253 0.4299 0.044 Uiso 1 1 calc R . .
C10 C 0.84348(19) 0.37375(10) 0.50160(11) 0.0158(3) Uani 1 1 d . . .
C11 C 0.5633(2) 0.37647(13) 0.50810(13) 0.0260(4) Uani 1 1 d . . .
H11A H 0.5618 0.4245 0.4663 0.039 Uiso 1 1 calc R . .
H11B H 0.5028 0.3909 0.5554 0.039 Uiso 1 1 calc R . .
H11C H 0.5167 0.3266 0.4744 0.039 Uiso 1 1 calc R . .
C12 C 0.7395(2) 0.29440(13) 0.62146(13) 0.0293(4) Uani 1 1 d . . .
H12A H 0.6806 0.2433 0.5988 0.044 Uiso 1 1 calc R . .
H12B H 0.6983 0.3172 0.6735 0.044 Uiso 1 1 calc R . .
H12C H 0.8505 0.2800 0.6405 0.044 Uiso 1 1 calc R . .
C13 C 1.0045(2) 0.42282(11) 0.64750(11) 0.0230(4) Uani 1 1 d . . .
H13A H 0.9006 0.4366 0.6607 0.035 Uiso 1 1 calc R . .
H13B H 1.0672 0.4748 0.6495 0.035 Uiso 1 1 calc R . .
H13C H 1.0570 0.3825 0.6929 0.035 Uiso 1 1 calc R . .
C14 C 1.12332(19) 0.39483(11) 0.51290(12) 0.0200(3) Uani 1 1 d . . .
H14A H 1.1227 0.3501 0.4673 0.030 Uiso 1 1 calc R . .
H14B H 1.2195 0.3906 0.5585 0.030 Uiso 1 1 calc R . .
H14C H 1.1191 0.4505 0.4833 0.030 Uiso 1 1 calc R . .
N1 N 0.81209(17) 0.32957(9) 0.23299(10) 0.0191(3) Uani 1 1 d . . .
N2 N 0.52773(16) 0.39564(9) 0.27081(10) 0.0196(3) Uani 1 1 d . . .
N3 N 0.60167(16) 0.23133(9) 0.34385(9) 0.0177(3) Uani 1 1 d . . .
N4 N 0.83119(15) 0.38186(8) 0.41514(9) 0.0159(3) Uani 1 1 d . . .
N5 N 0.53371(17) 0.10961(9) 0.41663(10) 0.0210(3) Uani 1 1 d . . .
N6 N 0.79632(17) 0.14380(10) 0.43285(11) 0.0267(3) Uani 1 1 d . . .
N7 N 0.72333(17) 0.35780(10) 0.54972(10) 0.0222(3) Uani 1 1 d . . .
N8 N 0.98756(16) 0.38483(9) 0.55702(9) 0.0182(3) Uani 1 1 d . . .
Ge1 Ge 0.69587(2) 0.331640(11) 0.323892(12) 0.01365(7) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge -1.0885 0.8855 '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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 N6 128.38(16) . . ?
N3 C5 N5 119.93(16) . . ?
N6 C5 N5 111.69(15) . . ?
N5 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N6 C8 H8A 109.5 . . ?
N6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 N8 119.64(14) . . ?
N4 C10 N7 127.15(15) . . ?
N8 C10 N7 113.15(14) . . ?
N7 C11 H11A 109.5 . . ?
N7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N7 C12 H12A 109.5 . . ?
N7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N8 C14 H14A 109.5 . . ?
N8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 N1 C1 111.55(14) . . ?
C2 N1 Ge1 117.60(11) . . ?
C1 N1 Ge1 123.19(12) . . ?
C4 N2 C3 112.33(14) . . ?
C4 N2 Ge1 117.53(11) . . ?
C3 N2 Ge1 123.70(12) . . ?
C5 N3 Ge1 133.04(12) . . ?
C10 N4 Ge1 129.77(12) . . ?
C5 N5 C7 115.49(14) . . ?
C5 N5 C6 115.99(14) . . ?
C7 N5 C6 111.77(15) . . ?
C5 N6 C9 120.75(15) . . ?
C5 N6 C8 123.73(15) . . ?
C9 N6 C8 115.21(16) . . ?
C10 N7 C11 119.40(14) . . ?
C10 N7 C12 121.57(15) . . ?
C11 N7 C12 114.54(15) . . ?
C10 N8 C14 117.33(13) . . ?
C10 N8 C13 122.48(14) . . ?
C14 N8 C13 114.79(13) . . ?
N4 Ge1 N3 120.12(6) . . ?
N4 Ge1 N1 101.43(6) . . ?
N3 Ge1 N1 115.30(6) . . ?
N4 Ge1 N2 116.32(6) . . ?
N3 Ge1 N2 101.65(6) . . ?
N1 Ge1 N2 100.91(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
C1 N1 1.451(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.448(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N2 1.450(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N2 1.447(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N3 1.277(2) . ?
C5 N6 1.377(2) . ?
C5 N5 1.414(2) . ?
C6 N5 1.466(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N5 1.451(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N6 1.454(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N6 1.449(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N4 1.284(2) . ?
C10 N8 1.381(2) . ?
C10 N7 1.391(2) . ?
C11 N7 1.446(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N7 1.453(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N8 1.462(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N8 1.457(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 Ge1 1.8312(14) . ?
N2 Ge1 1.8317(14) . ?
N3 Ge1 1.8268(14) . ?
N4 Ge1 1.8135(13) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659635
2 PubChem 139097076
