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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/41/4114189.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_4114189
loop_
_publ_author_name
'Lihung Pu'
'Andrew D. Phillips'
'Anne F. Richards'
'Matthias Stender'
'Richard S. Simons'
'Marilyn M. Olmstead'
'Philip P. Power'
_publ_section_title
;
 Germanium and Tin Analogues of Alkynes and Their Reduction Products
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11626
_journal_page_last               11636
_journal_paper_doi               10.1021/ja035711m
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C60 H74 Ge2 Li2'
_chemical_formula_weight         954.25
_chemical_name_common            (Dipp*GeLi)2
_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                113.680(5)
_cell_angle_beta                 97.789(9)
_cell_angle_gamma                110.46(2)
_cell_formula_units_Z            1
_cell_length_a                   9.617(2)
_cell_length_b                   12.705(3)
_cell_length_c                   12.833(4)
_cell_measurement_reflns_used    946
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      29.4
_cell_measurement_theta_min      2.84
_cell_volume                     1273.9(6)
_computing_cell_refinement       'Bruker SAINT 6.35A (Bruker 2002)'
_computing_data_collection       'Bruker SMART 5.054 (Bruker 2001)'
_computing_data_reduction        'Bruker SAINT 6.35A (Bruker 2002)'
_computing_molecular_graphics    'SHELXTL 5, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10894
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_time
;
frames measured at beginning and end of data collection
;
_diffrn_standards_number         '50 frames remeasured'
_exptl_absorpt_coefficient_mu    1.217
_exptl_absorpt_correction_T_max  0.8608
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.04 (Bruker 2002)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.909
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0486
_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)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                3896
_reflns_number_total             4995
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            ja035711msi20030421_060217_5.cif
_cod_data_source_block           ar31
_cod_database_code               4114189
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
Ge1 Ge -0.00515(4) 0.09728(3) 0.07092(3) 0.01663(12) Uani 1 1 d .
C1 C 0.2083(4) 0.1940(3) 0.2041(3) 0.0158(7) Uani 1 1 d .
C2 C 0.3392(4) 0.2914(3) 0.2048(3) 0.0146(6) Uani 1 1 d .
C3 C 0.4762(4) 0.3688(3) 0.3020(3) 0.0194(7) Uani 1 1 d .
H3A H 0.5591 0.4317 0.2988 0.023 Uiso 1 1 calc R
C4 C 0.4922(4) 0.3545(3) 0.4039(3) 0.0218(7) Uani 1 1 d .
H4A H 0.5849 0.4057 0.4684 0.026 Uiso 1 1 calc R
C5 C 0.3643(4) 0.2605(3) 0.4065(3) 0.0201(7) Uani 1 1 d .
H5A H 0.3718 0.2494 0.4740 0.024 Uiso 1 1 calc R
C6 C 0.2272(4) 0.1838(3) 0.3103(3) 0.0169(7) Uani 1 1 d .
C7 C 0.3312(3) 0.3184(3) 0.1011(3) 0.0158(7) Uani 1 1 d .
C8 C 0.3945(4) 0.2658(3) 0.0115(3) 0.0190(7) Uani 1 1 d .
C9 C 0.3889(4) 0.2958(3) -0.0818(3) 0.0236(8) Uani 1 1 d .
H9A H 0.4500 0.2740 -0.1351 0.028 Uiso 1 1 calc R
C10 C 0.3234(4) 0.3762(3) -0.0867(3) 0.0246(8) Uani 1 1 d .
H10A H 0.3198 0.3950 -0.1496 0.030 Uiso 1 1 calc R
C11 C 0.2639(4) 0.4278(3) 0.0020(3) 0.0235(8) Uani 1 1 d .
H11A H 0.2202 0.4814 -0.0020 0.028 Uiso 1 1 calc R
C12 C 0.2674(4) 0.4018(3) 0.0977(3) 0.0184(7) Uani 1 1 d .
C13 C 0.4766(4) 0.1854(3) 0.0203(3) 0.0220(7) Uani 1 1 d .
H13A H 0.4393 0.1517 0.0729 0.026 Uiso 1 1 calc R
C14 C 0.4423(4) 0.0705(4) -0.1008(4) 0.0309(9) Uani 1 1 d .
H14A H 0.3315 0.0157 -0.1350 0.046 Uiso 1 1 calc R
H14B H 0.4960 0.0232 -0.0887 0.046 Uiso 1 1 calc R
H14C H 0.4779 0.1008 -0.1544 0.046 Uiso 1 1 calc R
C15 C 0.6528(4) 0.2701(4) 0.0790(4) 0.0308(9) Uani 1 1 d .
H15A H 0.6738 0.3339 0.1596 0.046 Uiso 1 1 calc R
H15B H 0.6910 0.3115 0.0336 0.046 Uiso 1 1 calc R
H15C H 0.7045 0.2182 0.0810 0.046 Uiso 1 1 calc R
C16 C 0.2148(4) 0.4692(3) 0.2008(3) 0.0238(8) Uani 1 1 d .
H16A H 0.2042 0.4246 0.2484 0.029 Uiso 1 1 calc R
C17 C 0.3414(4) 0.6074(4) 0.2821(3) 0.0309(9) Uani 1 1 d .
H17A H 0.3103 0.6488 0.3491 0.046 Uiso 1 1 calc R
H17B H 0.3548 0.6532 0.2373 0.046 Uiso 1 1 calc R
H17C H 0.4385 0.6068 0.3109 0.046 Uiso 1 1 calc R
C18 C 0.0578(4) 0.4668(4) 0.1591(4) 0.0341(9) Uani 1 1 d .
H18A H -0.0217 0.3795 0.1139 0.051 Uiso 1 1 calc R
H18B H 0.0637 0.5069 0.1093 0.051 Uiso 1 1 calc R
H18C H 0.0322 0.5126 0.2277 0.051 Uiso 1 1 calc R
C19 C 0.0948(4) 0.0887(3) 0.3249(3) 0.0173(7) Uani 1 1 d .
C20 C 0.0930(4) -0.0287(3) 0.3048(3) 0.0176(7) Uani 1 1 d .
C21 C -0.0262(4) -0.1125(3) 0.3250(3) 0.0208(7) Uani 1 1 d .
H21A H -0.0276 -0.1900 0.3133 0.025 Uiso 1 1 calc R
C22 C -0.1413(4) -0.0817(3) 0.3619(3) 0.0218(7) Uani 1 1 d .
H22A H -0.2208 -0.1388 0.3736 0.026 Uiso 1 1 calc R
C23 C -0.1377(4) 0.0346(3) 0.3813(3) 0.0220(7) Uani 1 1 d .
H23A H -0.2156 0.0550 0.4065 0.026 Uiso 1 1 calc R
C24 C -0.0207(4) 0.1221(3) 0.3642(3) 0.0182(7) Uani 1 1 d .
C25 C 0.2220(4) -0.0640(3) 0.2676(3) 0.0210(7) Uani 1 1 d .
H25A H 0.2757 -0.0086 0.2359 0.025 Uiso 1 1 calc R
C26 C 0.3433(5) -0.0384(4) 0.3762(4) 0.0352(9) Uani 1 1 d .
H26A H 0.4247 -0.0586 0.3514 0.053 Uiso 1 1 calc R
H26B H 0.2935 -0.0911 0.4096 0.053 Uiso 1 1 calc R
H26C H 0.3878 0.0504 0.4358 0.053 Uiso 1 1 calc R
C27 C 0.1576(4) -0.2025(3) 0.1696(3) 0.0277(8) Uani 1 1 d .
H27A H 0.2427 -0.2202 0.1500 0.042 Uiso 1 1 calc R
H27B H 0.0882 -0.2159 0.0994 0.042 Uiso 1 1 calc R
H27C H 0.1014 -0.2589 0.1975 0.042 Uiso 1 1 calc R
C28 C -0.0111(4) 0.2546(3) 0.3976(3) 0.0244(8) Uani 1 1 d .
H28A H 0.0482 0.2875 0.3521 0.029 Uiso 1 1 calc R
C29 C -0.1686(5) 0.2552(4) 0.3684(4) 0.0395(10) Uani 1 1 d .
H29A H -0.2220 0.2029 0.2835 0.059 Uiso 1 1 calc R
H29B H -0.1534 0.3415 0.3929 0.059 Uiso 1 1 calc R
H29C H -0.2304 0.2214 0.4104 0.059 Uiso 1 1 calc R
C30 C 0.0799(5) 0.3452(4) 0.5305(4) 0.0392(10) Uani 1 1 d .
H30A H 0.0932 0.4302 0.5502 0.059 Uiso 1 1 calc R
H30B H 0.1808 0.3463 0.5478 0.059 Uiso 1 1 calc R
H30C H 0.0232 0.3164 0.5775 0.059 Uiso 1 1 calc R
Li1 Li 0.1199(7) 0.1156(6) -0.1171(6) 0.0327(15) 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'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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
C1 Ge1 Ge1 102.97(9) . 2
C1 Ge1 Li1 94.91(15) . 2
Ge1 Ge1 Li1 65.16(15) 2 2
C1 Ge1 Li1 96.07(15) . .
Ge1 Ge1 Li1 64.39(14) 2 .
Li1 Ge1 Li1 129.55(10) 2 .
C6 C1 C2 115.1(3) . .
C6 C1 Ge1 122.3(2) . .
C2 C1 Ge1 121.8(2) . .
C3 C2 C1 122.1(3) . .
C3 C2 C7 117.2(3) . .
C1 C2 C7 120.7(3) . .
C2 C3 C4 121.4(3) . .
C3 C4 C5 117.8(3) . .
C6 C5 C4 121.1(3) . .
C5 C6 C1 122.6(3) . .
C5 C6 C19 116.5(3) . .
C1 C6 C19 121.0(3) . .
C12 C7 C8 120.7(3) . .
C12 C7 C2 119.2(3) . .
C8 C7 C2 120.0(3) . .
C12 C7 Li1 93.9(3) . .
C8 C7 Li1 63.3(2) . .
C2 C7 Li1 115.5(2) . .
C9 C8 C7 118.5(3) . .
C9 C8 C13 120.3(3) . .
C7 C8 C13 121.1(3) . .
C9 C8 Li1 80.0(2) . .
C7 C8 Li1 86.0(3) . .
C13 C8 Li1 107.2(3) . .
C10 C9 C8 121.0(3) . .
C10 C9 Li1 93.1(3) . .
C8 C9 Li1 68.4(2) . .
C11 C10 C9 119.7(3) . .
C10 C11 C12 121.7(3) . .
C11 C12 C7 118.4(3) . .
C11 C12 C16 120.9(3) . .
C7 C12 C16 120.6(3) . .
C8 C13 C15 109.9(3) . .
C8 C13 C14 113.7(3) . .
C15 C13 C14 110.2(3) . .
C18 C16 C12 113.2(3) . .
C18 C16 C17 110.6(3) . .
C12 C16 C17 109.5(3) . .
C20 C19 C24 120.9(3) . .
C20 C19 C6 119.7(3) . .
C24 C19 C6 119.4(3) . .
C20 C19 Li1 65.7(2) . 2
C24 C19 Li1 92.0(3) . 2
C6 C19 Li1 115.1(2) . 2
C19 C20 C21 118.7(3) . .
C19 C20 C25 121.6(3) . .
C21 C20 C25 119.6(3) . .
C19 C20 Li1 83.3(3) . 2
C21 C20 Li1 82.1(2) . 2
C25 C20 Li1 107.0(3) . 2
C22 C21 C20 121.0(3) . .
C22 C21 Li1 91.4(3) . 2
C20 C21 Li1 66.6(2) . 2
C21 C22 C23 119.6(3) . .
C22 C23 C24 121.7(3) . .
C23 C24 C19 118.1(3) . .
C23 C24 C28 120.5(3) . .
C19 C24 C28 121.2(3) . .
C27 C25 C26 110.0(3) . .
C27 C25 C20 112.6(3) . .
C26 C25 C20 110.9(3) . .
C29 C28 C30 110.0(3) . .
C29 C28 C24 114.2(3) . .
C30 C28 C24 109.4(3) . .
C8 Li1 C20 148.1(3) . 2
C8 Li1 C9 31.65(13) . .
C20 Li1 C9 116.5(3) 2 .
C8 Li1 C21 116.9(3) . 2
C20 Li1 C21 31.23(12) 2 2
C9 Li1 C21 85.3(2) . 2
C8 Li1 C19 151.2(3) . 2
C20 Li1 C19 30.95(12) 2 2
C9 Li1 C19 129.6(3) . 2
C21 Li1 C19 53.21(15) 2 2
C8 Li1 C7 30.73(12) . .
C20 Li1 C7 150.3(3) 2 .
C9 Li1 C7 53.25(15) . .
C21 Li1 C7 129.3(3) 2 .
C19 Li1 C7 177.1(3) 2 .
C8 Li1 Ge1 110.6(2) . 2
C20 Li1 Ge1 98.8(2) 2 2
C9 Li1 Ge1 138.6(3) . 2
C21 Li1 Ge1 126.3(2) 2 2
C19 Li1 Ge1 73.15(17) 2 2
C7 Li1 Ge1 104.3(2) . 2
C8 Li1 Ge1 97.3(2) . .
C20 Li1 Ge1 111.2(2) 2 .
C9 Li1 Ge1 124.9(3) . .
C21 Li1 Ge1 138.3(3) 2 .
C19 Li1 Ge1 105.6(2) 2 .
C7 Li1 Ge1 71.61(17) . .
Ge1 Li1 Ge1 50.45(10) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C1 2.060(3) .
Ge1 Ge1 2.4575(9) 2
Ge1 Li1 2.874(6) 2
Ge1 Li1 2.892(7) .
C1 C6 1.414(4) .
C1 C2 1.420(4) .
C2 C3 1.387(5) .
C2 C7 1.501(4) .
C3 C4 1.387(5) .
C4 C5 1.399(5) .
C5 C6 1.380(5) .
C6 C19 1.512(4) .
C7 C12 1.408(4) .
C7 C8 1.413(5) .
C7 Li1 2.759(7) .
C8 C9 1.394(5) .
C8 C13 1.520(5) .
C8 Li1 2.470(7) .
C9 C10 1.392(5) .
C9 Li1 2.617(7) .
C10 C11 1.375(5) .
C11 C12 1.393(5) .
C12 C16 1.521(5) .
C13 C15 1.524(5) .
C13 C14 1.535(5) .
C16 C18 1.517(5) .
C16 C17 1.531(5) .
C19 C20 1.400(4) .
C19 C24 1.407(5) .
C19 Li1 2.704(7) 2
C20 C21 1.401(4) .
C20 C25 1.532(5) .
C20 Li1 2.482(7) 2
C21 C22 1.377(5) .
C21 Li1 2.678(7) 2
C22 C23 1.384(5) .
C23 C24 1.392(5) .
C24 C28 1.526(4) .
C25 C27 1.521(5) .
C25 C26 1.529(5) .
C28 C29 1.513(5) .
C28 C30 1.521(5) .
Li1 C20 2.482(7) 2
Li1 C21 2.678(7) 2
Li1 C19 2.704(7) 2
Li1 Ge1 2.874(6) 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139119742
