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#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/83/4328397.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.
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data_4328397
loop_
_publ_author_name
'Ying Yang'
'Na Zhao'
'Yile Wu'
'Hongping Zhu'
'Herbert W. Roesky'
_publ_contact_author
;
Herbert W. ROESKY
;
_publ_contact_author_address
;
Institut fuer Anorganische Chemie
Universitaet Goettingen
Tammannstrasse 4, 37077 Goettingen (Germany)
;
_publ_contact_author_email       hroesky@gwdg.de
_publ_section_title
;
 Synthesis and Characterization of β-Diketiminate Germanium(II) Compounds
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2425
_journal_page_last               2431
_journal_paper_doi               10.1021/ic202388d
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C33 H44 Ge N2 S'
_chemical_formula_weight         573.35
_chemical_name_common            LGe-(2-thienyl)
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.3720(13)
_cell_length_b                   9.3145(7)
_cell_length_c                   28.869(3)
_cell_measurement_reflns_used    1767
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.9218
_cell_measurement_theta_min      2.7580
_cell_volume                     6015.8(8)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8440
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_T_max  0.9445
_exptl_absorpt_correction_T_min  0.5941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'Bright yellow'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       Block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.867
_refine_diff_density_min         -1.627
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0895
_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)+(0.0497P)²+58.1457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1924
_reflns_number_gt                2056
_reflns_number_total             2709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202388d_si_001_3.cif
_cod_data_source_block           yy220_mi
_cod_database_code               4328397
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ge1 Ge 0.0000 0.65565(12) 0.85384(4) 0.0508(4) Uani 1 2 d SD . .
N1 N 0.06394(18) 0.5353(5) 0.88218(15) 0.0280(10) Uani 1 1 d . . .
C1 C 0.1089(3) 0.3829(7) 0.9419(2) 0.0497(18) Uani 1 1 d . . .
H1A H 0.1382 0.4557 0.9512 0.075 Uiso 1 1 calc R . .
H1B H 0.1274 0.3165 0.9198 0.075 Uiso 1 1 calc R . .
H1C H 0.0957 0.3295 0.9693 0.075 Uiso 1 1 calc R . .
C2 C 0.0563(2) 0.4547(6) 0.91974(18) 0.0298(13) Uani 1 1 d . . .
C3 C 0.0000 0.4280(8) 0.9390(3) 0.0342(19) Uani 1 2 d S . .
H3 H 0.0000 0.3862 0.9690 0.041 Uiso 1 2 calc SR . .
C4 C 0.1219(2) 0.5464(7) 0.85989(18) 0.0332(14) Uani 1 1 d . . .
C5 C 0.1642(3) 0.6456(8) 0.8750(2) 0.0446(16) Uani 1 1 d . . .
C6 C 0.2183(3) 0.6536(9) 0.8498(2) 0.059(2) Uani 1 1 d . . .
H6 H 0.2477 0.7210 0.8592 0.071 Uiso 1 1 calc R . .
C7 C 0.2297(3) 0.5682(10) 0.8126(2) 0.064(2) Uani 1 1 d . . .
H7 H 0.2666 0.5757 0.7966 0.077 Uiso 1 1 calc R . .
C8 C 0.1880(3) 0.4728(9) 0.7987(2) 0.057(2) Uani 1 1 d . . .
H8 H 0.1965 0.4131 0.7729 0.069 Uiso 1 1 calc R . .
C9 C 0.1325(3) 0.4582(7) 0.8210(2) 0.0407(15) Uani 1 1 d . B .
C10 C 0.0873(3) 0.3516(8) 0.8028(2) 0.0520(18) Uani 1 1 d . . .
H10 H 0.0519 0.3826 0.8214 0.062 Uiso 1 1 calc R A 1
C11 C 0.0958(5) 0.2085(11) 0.8229(5) 0.123(4) Uani 1 1 d . B .
H11A H 0.0935 0.2149 0.8568 0.185 Uiso 1 1 calc R . .
H11B H 0.1351 0.1712 0.8139 0.185 Uiso 1 1 calc R . .
H11C H 0.0645 0.1439 0.8116 0.185 Uiso 1 1 calc R . .
C12 C 0.0968(13) 0.322(2) 0.7490(6) 0.073(6) Uani 0.61(4) 1 d P B 2
H12A H 0.1317 0.2599 0.7447 0.109 Uiso 0.61(4) 1 calc PR B 2
H12B H 0.1033 0.4134 0.7329 0.109 Uiso 0.61(4) 1 calc PR B 2
H12C H 0.0612 0.2748 0.7364 0.109 Uiso 0.61(4) 1 calc PR B 2
C12' C 0.0634(17) 0.381(5) 0.7556(6) 0.069(13) Uani 0.39(4) 1 d P B 1
H12D H 0.0287 0.4446 0.7579 0.104 Uiso 0.39(4) 1 calc PR B 1
H12E H 0.0513 0.2902 0.7411 0.104 Uiso 0.39(4) 1 calc PR B 1
H12F H 0.0944 0.4268 0.7368 0.104 Uiso 0.39(4) 1 calc PR B 1
C13 C 0.1549(3) 0.7434(8) 0.9160(2) 0.0532(18) Uani 1 1 d . . .
H13 H 0.1159 0.7168 0.9306 0.064 Uiso 1 1 calc R . .
C14 C 0.2040(3) 0.7254(12) 0.9529(3) 0.089(3) Uani 1 1 d . . .
H14A H 0.1935 0.7814 0.9805 0.134 Uiso 1 1 calc R . .
H14B H 0.2422 0.7596 0.9405 0.134 Uiso 1 1 calc R . .
H14C H 0.2076 0.6238 0.9613 0.134 Uiso 1 1 calc R . .
C15 C 0.1504(4) 0.8991(9) 0.9006(3) 0.091(3) Uani 1 1 d . . .
H15A H 0.1163 0.9102 0.8796 0.137 Uiso 1 1 calc R . .
H15B H 0.1872 0.9268 0.8845 0.137 Uiso 1 1 calc R . .
H15C H 0.1447 0.9607 0.9278 0.137 Uiso 1 1 calc R . .
C16 C 0.0000 0.8170(11) 0.8978(5) 0.119(7) Uani 1 2 d SD . .
C18 C 0.0000 1.0667(18) 0.9080(9) 0.186(6) Uani 1 2 d SU . .
H18 H 0.0000 1.1669 0.9018 0.224 Uiso 1 2 calc SR . .
C19 C 0.0000 1.0055(17) 0.9455(5) 0.186(6) Uani 1 2 d SU . .
H19 H 0.0000 1.0579 0.9738 0.224 Uiso 1 2 calc SRD . .
S1 S 0.0000 0.8114(4) 0.94514(19) 0.0952(13) Uani 1 2 d SU . .
C17 C 0.0000 0.9464(17) 0.8748(9) 0.186(6) Uani 1 2 d SU . .
H17 H 0.0000 0.9568 0.8421 0.223 Uiso 1 2 calc SR . .
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'
S S 0.1246 0.1234 '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'
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
C16 Ge1 N1 99.5(3) . .
C16 Ge1 N1 99.5(3) . 12
N1 Ge1 N1 91.7(2) . 12
C2 N1 C4 121.1(4) . .
C2 N1 Ge1 124.0(4) . .
C4 N1 Ge1 114.8(3) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C3 122.7(5) . .
N1 C2 C1 120.0(5) . .
C3 C2 C1 117.3(5) . .
C2 C3 C2 128.5(7) . 12
C2 C3 H3 115.8 . .
C2 C3 H3 115.8 12 .
C5 C4 C9 121.4(5) . .
C5 C4 N1 121.0(5) . .
C9 C4 N1 117.5(5) . .
C4 C5 C6 117.1(6) . .
C4 C5 C13 123.5(5) . .
C6 C5 C13 119.4(6) . .
C7 C6 C5 122.4(7) . .
C7 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
C8 C7 C6 119.3(6) . .
C8 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
C7 C8 C9 122.6(7) . .
C7 C8 H8 118.7 . .
C9 C8 H8 118.7 . .
C8 C9 C4 117.1(6) . .
C8 C9 C10 119.7(6) . .
C4 C9 C10 123.1(5) . .
C11 C10 C12' 125.1(18) . .
C11 C10 C9 111.9(6) . .
C12' C10 C9 116.0(12) . .
C11 C10 C12 102.3(10) . .
C12' C10 C12 35.5(13) . .
C9 C10 C12 111.3(9) . .
C11 C10 H10 98.8 . .
C12' C10 H10 98.8 . .
C9 C10 H10 98.8 . .
C12 C10 H10 132.8 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C12' H12D 109.5 . .
C10 C12' H12E 109.5 . .
H12D C12' H12E 109.5 . .
C10 C12' H12F 109.5 . .
H12D C12' H12F 109.5 . .
H12E C12' H12F 109.5 . .
C5 C13 C15 110.9(6) . .
C5 C13 C14 112.2(7) . .
C15 C13 C14 110.7(7) . .
C5 C13 H13 107.6 . .
C15 C13 H13 107.6 . .
C14 C13 H13 107.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
S1 C16 C17 121.0(12) . .
S1 C16 Ge1 128.0(8) . .
C17 C16 Ge1 111.0(13) . .
C19 C18 C17 102.8(16) . .
C19 C18 H18 128.6 . .
C17 C18 H18 128.6 . .
C18 C19 S1 117.4(17) . .
C18 C19 H19 121.3 . .
S1 C19 H19 121.3 . .
C16 S1 C19 88.2(7) . .
C16 C17 C18 111(2) . .
C16 C17 H17 124.7 . .
C18 C17 H17 124.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ge1 C16 1.966(9) .
Ge1 N1 1.993(4) .
Ge1 N1 1.993(4) 12
N1 C2 1.329(7) .
N1 C4 1.451(7) .
C1 C2 1.498(8) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.399(6) .
C3 C2 1.399(6) 12
C3 H3 0.9500 .
C4 C5 1.394(8) .
C4 C9 1.411(8) .
C5 C6 1.413(9) .
C5 C13 1.508(9) .
C6 C7 1.360(10) .
C6 H6 0.9500 .
C7 C8 1.349(10) .
C7 H7 0.9500 .
C8 C9 1.406(9) .
C8 H8 0.9500 .
C9 C10 1.511(9) .
C10 C11 1.466(12) .
C10 C12' 1.49(3) .
C10 C12 1.59(2) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C12' H12D 0.9800 .
C12' H12E 0.9800 .
C12' H12F 0.9800 .
C13 C15 1.520(11) .
C13 C14 1.540(10) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 S1 1.369(14) .
C16 C17 1.38(2) .
C18 C19 1.22(2) .
C18 C17 1.48(3) .
C18 H18 0.9500 .
C19 S1 1.808(16) .
C19 H19 0.9500 .
C17 H17 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139136978
