#------------------------------------------------------------------------------
#$Date: 2025-08-21 13:25:49 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301846 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/65/7006542.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_7006542
loop_
_publ_author_name
'Hildebrand, Alexandra'
'Lönnecke, Peter'
'Silaghi-Dumitrescu, Luminita'
'Silaghi-Dumitrescu, Ioan'
'Hey-Hawkins, Evamarie'
_publ_section_title
;
 Co-complexes of ortho-dilithiated thiophenol or
 2-trimethylsilylthiophenol with lithiated TMEDA molecules: synthesis,
 crystal structures and theoretical studies (TMEDA =
 N,N,N',N'-tetramethylethylenediamine).
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              967
_journal_page_last               974
_journal_paper_doi               10.1039/b511827a
_journal_year                    2006
_chemical_formula_sum            'C36 H70 Li6 N8 S2'
_chemical_formula_weight         720.76
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 114.957(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6446(12)
_cell_length_b                   17.4654(17)
_cell_length_c                   11.6050(11)
_cell_measurement_reflns_used    3532
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.26
_cell_volume                     2323.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP3 for Windows (L. J. Farrugia, 1997)'
_computing_publication_material  'WINGX (L.J. Farrugia,1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick,1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_sigmaI/netI    0.0878
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12910
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.030
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.1045
_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)+(0.0792P)²+3.5834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2288
_refine_ls_wR_factor_ref         0.2592
_reflns_number_gt                2955
_reflns_number_total             4748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b511827a.txt
_cod_data_source_block           c1681fin
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7006542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S -0.23914(10) 0.04679(7) 1.49826(12) 0.0473(4) Uani 1 1 d . . .
N1 N 0.0064(3) 0.1828(2) 1.4071(3) 0.0437(9) Uani 1 1 d . . .
N2 N -0.2434(4) 0.1867(2) 1.2509(4) 0.0591(12) Uani 1 1 d . . .
N3 N -0.2225(4) -0.0315(3) 1.7942(4) 0.0641(12) Uani 1 1 d . . .
N4 N -0.3650(4) -0.1433(3) 1.6055(6) 0.0761(15) Uani 1 1 d . . .
C1 C -0.2397(4) -0.0045(3) 1.3638(4) 0.0420(10) Uani 1 1 d . . .
C2 C -0.1336(4) -0.0084(3) 1.3497(4) 0.0418(10) Uani 1 1 d . . .
C3 C -0.1430(5) -0.0504(3) 1.2421(5) 0.0553(13) Uani 1 1 d . . .
H3 H -0.0758 -0.0551 1.2270 0.066 Uiso 1 1 calc R . .
C4 C -0.2442(6) -0.0852(3) 1.1569(5) 0.0707(16) Uani 1 1 d . . .
H4 H -0.2439 -0.1133 1.0881 0.085 Uiso 1 1 calc R . .
C5 C -0.3448(5) -0.0784(4) 1.1735(5) 0.0732(17) Uani 1 1 d . . .
H5 H -0.4142 -0.1013 1.1155 0.088 Uiso 1 1 calc R . .
C6 C -0.3433(4) -0.0377(3) 1.2763(5) 0.0609(14) Uani 1 1 d . . .
H6 H -0.4123 -0.0322 1.2875 0.073 Uiso 1 1 calc R . .
C7 C 0.0572(4) 0.1343(3) 1.3368(5) 0.0434(11) Uani 1 1 d . . .
C8 C 0.0993(5) 0.2073(3) 1.5287(5) 0.0583(14) Uani 1 1 d . . .
C9 C -0.0524(5) 0.2521(3) 1.3365(5) 0.0520(12) Uani 1 1 d . . .
C10 C -0.1622(5) 0.2339(3) 1.2201(5) 0.0566(14) Uani 1 1 d . . .
C11 C -0.3057(7) 0.2345(4) 1.3063(9) 0.081(2) Uani 1 1 d . . .
C12 C -0.3278(8) 0.1483(5) 1.1378(8) 0.094(3) Uani 1 1 d . . .
C13 C -0.2188(9) 0.0513(4) 1.8060(7) 0.135(4) Uani 1 1 d . . .
H13A H -0.2868 0.0732 1.7374 0.202 Uiso 1 1 calc R . .
H13B H -0.1486 0.0705 1.8017 0.202 Uiso 1 1 calc R . .
H13C H -0.2187 0.0655 1.8869 0.202 Uiso 1 1 calc R . .
C14 C -0.1241(5) -0.0648(4) 1.9019(5) 0.0752(17) Uani 1 1 d . . .
H14A H -0.1304 -0.0520 1.9802 0.113 Uiso 1 1 calc R . .
H14B H -0.0517 -0.0444 1.9047 0.113 Uiso 1 1 calc R . .
H14C H -0.1249 -0.1200 1.8924 0.113 Uiso 1 1 calc R . .
C15 C -0.3307(6) -0.0614(8) 1.7879(8) 0.148(5) Uani 1 1 d . . .
H15A H -0.3208 -0.0693 1.8755 0.177 Uiso 1 1 calc R . .
H15B H -0.3896 -0.0213 1.7514 0.177 Uiso 1 1 calc R . .
C16 C -0.3743(10) -0.1239(8) 1.7261(12) 0.178(6) Uani 1 1 d . . .
H16A H -0.4576 -0.1238 1.7070 0.214 Uiso 1 1 calc R . .
H16B H -0.3391 -0.1664 1.7850 0.214 Uiso 1 1 calc R . .
C17 C -0.4694(5) -0.1183(4) 1.4988(7) 0.098(2) Uani 1 1 d . . .
H17A H -0.4599 -0.1255 1.4208 0.147 Uiso 1 1 calc R . .
H17B H -0.4829 -0.0645 1.5087 0.147 Uiso 1 1 calc R . .
H17C H -0.5354 -0.1481 1.4953 0.147 Uiso 1 1 calc R . .
C18 C -0.3537(6) -0.2235(4) 1.6003(13) 0.181(6) Uani 1 1 d . . .
H18A H -0.4156 -0.2483 1.6149 0.271 Uiso 1 1 calc R . .
H18B H -0.2787 -0.2393 1.6652 0.271 Uiso 1 1 calc R . .
H18C H -0.3591 -0.2379 1.5173 0.271 Uiso 1 1 calc R . .
Li1 Li -0.1313(7) 0.1143(4) 1.3948(7) 0.0462(18) Uani 1 1 d . . .
Li2 Li -0.2197(6) -0.0725(4) 1.6214(8) 0.0484(19) Uani 1 1 d . . .
Li3 Li 0.0528(7) 0.0249(4) 1.4333(7) 0.0463(18) Uani 1 1 d . . .
H7A H -0.010(4) 0.116(3) 1.257(5) 0.063(15) Uiso 1 1 d . . .
H7B H 0.101(4) 0.172(3) 1.303(4) 0.058(14) Uiso 1 1 d . . .
H8A H 0.069(5) 0.241(3) 1.579(5) 0.072(17) Uiso 1 1 d . . .
H8B H 0.145(5) 0.164(3) 1.585(5) 0.073(17) Uiso 1 1 d . . .
H8C H 0.174(5) 0.243(3) 1.517(5) 0.072(16) Uiso 1 1 d . . .
H9A H -0.076(4) 0.289(3) 1.394(4) 0.045(12) Uiso 1 1 d . . .
H9B H 0.001(4) 0.289(3) 1.312(5) 0.070(16) Uiso 1 1 d . . .
H10A H -0.205(4) 0.288(3) 1.173(5) 0.067(15) Uiso 1 1 d . . .
H10B H -0.145(4) 0.207(3) 1.165(5) 0.057(15) Uiso 1 1 d . . .
H11A H -0.359(7) 0.202(4) 1.333(7) 0.13(3) Uiso 1 1 d . . .
H11B H -0.363(5) 0.281(4) 1.234(6) 0.093(19) Uiso 1 1 d . . .
H11C H -0.253(6) 0.261(4) 1.371(6) 0.09(3) Uiso 1 1 d . . .
H12A H -0.371(5) 0.112(4) 1.162(6) 0.09(2) Uiso 1 1 d . . .
H12B H -0.290(6) 0.119(4) 1.101(6) 0.08(2) Uiso 1 1 d . . .
H12C H -0.379(6) 0.183(4) 1.065(7) 0.10(2) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
C1 S1 Li1 67.4(2) . . ?
C1 S1 Li2 92.6(2) . . ?
Li1 S1 Li2 137.9(2) . . ?
C1 S1 Li3 71.4(2) . 3_558 ?
Li1 S1 Li3 75.6(2) . 3_558 ?
Li2 S1 Li3 62.8(2) . 3_558 ?
C8 N1 C9 107.8(4) . . ?
C8 N1 C7 109.6(4) . . ?
C9 N1 C7 113.2(4) . . ?
C8 N1 Li1 123.0(4) . . ?
C9 N1 Li1 102.9(3) . . ?
C7 N1 Li1 100.2(3) . . ?
C12 N2 C11 109.4(7) . . ?
C12 N2 C10 111.0(6) . . ?
C11 N2 C10 110.2(5) . . ?
C12 N2 Li1 115.5(5) . . ?
C11 N2 Li1 107.5(5) . . ?
C10 N2 Li1 102.9(4) . . ?
C15 N3 C13 111.0(7) . . ?
C15 N3 C14 110.3(6) . . ?
C13 N3 C14 109.5(6) . . ?
C15 N3 Li2 102.8(5) . . ?
C13 N3 Li2 114.1(4) . . ?
C14 N3 Li2 108.9(4) . . ?
C18 N4 C17 109.6(6) . . ?
C18 N4 C16 108.3(8) . . ?
C17 N4 C16 109.3(7) . . ?
C18 N4 Li2 118.4(5) . . ?
C17 N4 Li2 109.7(4) . . ?
C16 N4 Li2 101.0(5) . . ?
C6 C1 C2 122.5(4) . . ?
C6 C1 S1 119.7(4) . . ?
C2 C1 S1 117.8(3) . . ?
C6 C1 Li1 139.3(4) . . ?
C2 C1 Li1 63.7(3) . . ?
S1 C1 Li1 69.5(2) . . ?
C6 C1 Li3 145.8(4) . 3_558 ?
C2 C1 Li3 63.2(3) . 3_558 ?
S1 C1 Li3 66.8(2) . 3_558 ?
Li1 C1 Li3 74.8(3) . 3_558 ?
C3 C2 C1 113.4(4) . . ?
C3 C2 Li1 134.7(4) . . ?
C1 C2 Li1 81.1(3) . . ?
C3 C2 Li3 101.6(4) . . ?
C1 C2 Li3 145.0(4) . . ?
Li1 C2 Li3 74.7(3) . . ?
C3 C2 Li3 137.5(4) . 3_558 ?
C1 C2 Li3 83.4(3) . 3_558 ?
Li1 C2 Li3 84.6(3) . 3_558 ?
Li3 C2 Li3 69.8(3) . 3_558 ?
C4 C3 C2 124.6(5) . . ?
C5 C4 C3 119.7(5) . . ?
C4 C5 C6 119.4(5) . . ?
C5 C6 C1 120.4(5) . . ?
N1 C7 Li2 137.6(4) . 3_558 ?
N1 C7 Li3 96.0(3) . . ?
Li2 C7 Li3 71.7(3) 3_558 . ?
N1 C7 Li1 47.5(3) . . ?
Li2 C7 Li1 135.4(3) 3_558 . ?
Li3 C7 Li1 64.0(3) . . ?
N1 C9 C10 112.5(4) . . ?
N2 C10 C9 111.9(4) . . ?
C16 C15 N3 120.6(9) . . ?
C15 C16 N4 121.8(8) . . ?
N1 Li1 N2 88.5(3) . . ?
N1 Li1 C2 120.3(4) . . ?
N2 Li1 C2 117.4(4) . . ?
N1 Li1 C1 155.6(4) . . ?
N2 Li1 C1 104.3(4) . . ?
C2 Li1 C1 35.26(19) . . ?
N1 Li1 S1 150.0(4) . . ?
N2 Li1 S1 110.5(3) . . ?
C2 Li1 S1 72.3(2) . . ?
C1 Li1 S1 43.08(17) . . ?
N1 Li1 Li3 71.2(3) . . ?
N2 Li1 Li3 137.1(4) . . ?
C2 Li1 Li3 52.8(3) . . ?
C1 Li1 Li3 85.6(3) . . ?
S1 Li1 Li3 105.1(3) . . ?
N1 Li1 C7 32.25(18) . . ?
N2 Li1 C7 95.3(3) . . ?
C2 Li1 C7 89.5(3) . . ?
C1 Li1 C7 124.3(3) . . ?
S1 Li1 C7 153.1(3) . . ?
Li3 Li1 C7 48.3(2) . . ?
N1 Li1 Li3 112.7(3) . 3_558 ?
N2 Li1 Li3 158.5(4) . 3_558 ?
C2 Li1 Li3 49.0(2) . 3_558 ?
C1 Li1 Li3 54.6(2) . 3_558 ?
S1 Li1 Li3 52.5(2) . 3_558 ?
Li3 Li1 Li3 53.3(3) . 3_558 ?
C7 Li1 Li3 100.6(3) . 3_558 ?
N3 Li2 N4 85.5(3) . . ?
N3 Li2 C7 110.0(4) . 3_558 ?
N4 Li2 C7 115.0(4) . 3_558 ?
N3 Li2 S1 102.8(3) . . ?
N4 Li2 S1 124.0(4) . . ?
C7 Li2 S1 113.4(3) 3_558 . ?
N3 Li2 Li3 117.4(4) . 3_558 ?
N4 Li2 Li3 156.6(5) . 3_558 ?
C7 Li2 Li3 54.9(3) 3_558 3_558 ?
S1 Li2 Li3 58.7(2) . 3_558 ?
C2 Li3 C7 104.6(4) . . ?
C2 Li3 C2 110.2(3) . 3_558 ?
C7 Li3 C2 124.3(4) . 3_558 ?
C2 Li3 S1 134.3(4) . 3_558 ?
C7 Li3 S1 111.8(3) . 3_558 ?
C2 Li3 S1 70.4(2) 3_558 3_558 ?
C2 Li3 C1 139.9(4) . 3_558 ?
C7 Li3 C1 111.9(3) . 3_558 ?
C2 Li3 C1 33.41(18) 3_558 3_558 ?
S1 Li3 C1 41.71(16) 3_558 3_558 ?
C2 Li3 Li3 56.7(3) . 3_558 ?
C7 Li3 Li3 135.9(5) . 3_558 ?
C2 Li3 Li3 53.5(3) 3_558 3_558 ?
S1 Li3 Li3 107.4(4) 3_558 3_558 ?
C1 Li3 Li3 85.0(4) 3_558 3_558 ?
C2 Li3 Li2 143.6(4) . 3_558 ?
C7 Li3 Li2 53.4(3) . 3_558 ?
C2 Li3 Li2 106.1(4) 3_558 3_558 ?
S1 Li3 Li2 58.5(2) 3_558 3_558 ?
C1 Li3 Li2 74.8(3) 3_558 3_558 ?
Li3 Li3 Li2 159.6(5) 3_558 3_558 ?
C2 Li3 Li1 52.5(3) . . ?
C7 Li3 Li1 67.7(3) . . ?
C2 Li3 Li1 102.0(3) 3_558 . ?
S1 Li3 Li1 170.8(4) 3_558 . ?
C1 Li3 Li1 129.3(4) 3_558 . ?
Li3 Li3 Li1 70.4(4) 3_558 . ?
Li2 Li3 Li1 120.9(4) 3_558 . ?
C2 Li3 Li1 94.0(3) . 3_558 ?
C7 Li3 Li1 161.3(4) . 3_558 ?
C2 Li3 Li1 46.3(2) 3_558 3_558 ?
S1 Li3 Li1 51.9(2) 3_558 3_558 ?
C1 Li3 Li1 50.6(2) 3_558 3_558 ?
Li3 Li3 Li1 56.3(3) 3_558 3_558 ?
Li2 Li3 Li1 110.2(3) 3_558 3_558 ?
Li1 Li3 Li1 126.7(3) . 3_558 ?
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
S1 C1 1.797(5) . ?
S1 Li1 2.465(7) . ?
S1 Li2 2.479(8) . ?
S1 Li3 2.484(8) 3_558 ?
N1 C8 1.468(6) . ?
N1 C9 1.476(6) . ?
N1 C7 1.496(6) . ?
N1 Li1 2.067(9) . ?
N2 C12 1.459(9) . ?
N2 C11 1.468(8) . ?
N2 C10 1.473(7) . ?
N2 Li1 2.098(8) . ?
N3 C15 1.437(9) . ?
N3 C13 1.452(8) . ?
N3 C14 1.461(7) . ?
N3 Li2 2.143(9) . ?
N4 C18 1.412(9) . ?
N4 C17 1.444(8) . ?
N4 C16 1.492(12) . ?
N4 Li2 2.156(9) . ?
C1 C6 1.400(6) . ?
C1 C2 1.420(6) . ?
C1 Li1 2.429(9) . ?
C1 Li3 2.561(9) 3_558 ?
C2 C3 1.409(6) . ?
C2 Li1 2.204(9) . ?
C2 Li3 2.215(9) . ?
C2 Li3 2.301(9) 3_558 ?
C3 C4 1.384(7) . ?
C4 C5 1.369(8) . ?
C5 C6 1.382(8) . ?
C7 Li2 2.187(9) 3_558 ?
C7 Li3 2.227(9) . ?
C7 Li1 2.758(9) . ?
C9 C10 1.507(8) . ?
C15 C16 1.294(14) . ?
Li1 Li3 2.680(10) . ?
Li1 Li3 3.034(11) 3_558 ?
Li2 C7 2.187(9) 3_558 ?
Li2 Li3 2.584(10) 3_558 ?
Li3 C2 2.301(9) 3_558 ?
Li3 S1 2.484(8) 3_558 ?
Li3 C1 2.561(9) 3_558 ?
Li3 Li3 2.584(14) 3_558 ?
Li3 Li2 2.584(10) 3_558 ?
Li3 Li1 3.034(11) 3_558 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139152244
