#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/39/4323963.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_4323963
loop_
_publ_author_name
'Maurits D. Janssen'
'Evelien Rijnberg'
'Corine A. de Wolf'
'Marinus P. Hogerheide'
'Dennis Kruis'
'Huub Kooijman'
'Anthony L. Spek'
'David M. Grove'
'Gerard van Koten'
_publ_section_title
;
 Structural Aspects of Lithium Arenethiolate Complexes with Intramolecular
 Coordinating Amine Donors
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6735
_journal_page_last               6741
_journal_paper_doi               10.1021/ic960075x
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C22 H32 Li2 N2 O2 S2'
_chemical_formula_weight         434.49
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 108.288(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.7963(9)
_cell_length_b                   8.1281(7)
_cell_length_c                   17.1340(10)
_cell_measurement_temperature    150(2)
_cell_volume                     2353.3(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10603
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.246
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             928
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.061
_refine_ls_goodness_of_fit_obs   1.150
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_restrained_S_obs      1.150
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_obs          0.0471
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.0763P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1381
_refine_ls_wR_factor_obs         0.1288
_reflns_number_observed          4051
_reflns_number_total             5396
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic960075x_3.cif
_cod_data_source_block           complex5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0763P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[s^2^(Fo^2^)+( 0.0763P)^2^+0.0000P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

2020-11-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C88 H128 Li8 N8 O8 S8'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     1737.98
_cod_database_code               4323963
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Li1 Li 0.2633(2) 0.3924(3) 0.3193(2) 0.0248(6) Uani 1 d . .
Li2 Li 0.2238(2) 0.6093(4) 0.1779(2) 0.0258(6) Uani 1 d . .
S1 S 0.22237(3) 0.31086(5) 0.17602(2) 0.02418(14) Uani 1 d . .
S2 S 0.26220(3) 0.69135(5) 0.32121(2) 0.02284(13) Uani 1 d . .
N1 N 0.19600(8) 0.2338(2) 0.36447(8) 0.0198(3) Uani 1 d . .
N2 N 0.30136(8) 0.7493(2) 0.13760(8) 0.0210(3) Uani 1 d . .
O1 O 0.35744(7) 0.26791(14) 0.38419(7) 0.0239(3) Uani 1 d . .
O2 O 0.13795(7) 0.74233(14) 0.10597(7) 0.0222(3) Uani 1 d . .
C11 C 0.12170(11) 0.2808(2) 0.16752(10) 0.0220(4) Uani 1 d . .
C12 C 0.09745(10) 0.1910(2) 0.22600(10) 0.0212(3) Uani 1 d . .
C13 C 0.01717(11) 0.1669(2) 0.21359(11) 0.0268(4) Uani 1 d . .
H13 H 0.00160(11) 0.1040(2) 0.25264(11) 0.032 Uiso 1 calc R .
C14 C -0.04080(12) 0.2310(2) 0.14664(12) 0.0326(4) Uani 1 d . .
H14 H -0.09529(12) 0.2147(2) 0.14013(12) 0.039 Uiso 1 calc R .
C15 C -0.01724(12) 0.3198(2) 0.08921(12) 0.0367(5) Uani 1 d . .
H15 H -0.05597(12) 0.3651(2) 0.04261(12) 0.044 Uiso 1 calc R .
C16 C 0.06212(12) 0.3429(2) 0.09929(11) 0.0319(4) Uani 1 d . .
H16 H 0.07684(12) 0.4027(2) 0.05872(11) 0.038 Uiso 1 calc R .
C17 C 0.15635(10) 0.1139(2) 0.29982(9) 0.0208(3) Uani 1 d . .
H17A H 0.12885(10) 0.0311(2) 0.32340(9) 0.025 Uiso 1 calc R .
H17B H 0.19701(10) 0.0557(2) 0.28195(9) 0.025 Uiso 1 calc R .
C18 C 0.13851(12) 0.3074(2) 0.39896(12) 0.0346(4) Uani 1 d . .
H18A H 0.0956(4) 0.3576(15) 0.3548(2) 0.052 Uiso 1 calc R .
H18B H 0.1646(2) 0.3919(12) 0.4391(6) 0.052 Uiso 1 calc R .
H18C H 0.1168(6) 0.2220(4) 0.4261(7) 0.052 Uiso 1 calc R .
C19 C 0.25781(10) 0.1502(2) 0.43072(10) 0.0253(4) Uani 1 d . .
H19A H 0.23640(10) 0.0458(2) 0.44470(10) 0.030 Uiso 1 calc R .
H19B H 0.27283(10) 0.2206(2) 0.48037(10) 0.030 Uiso 1 calc R .
C110 C 0.32982(10) 0.1145(2) 0.40610(11) 0.0266(4) Uani 1 d . .
H11A H 0.37131(10) 0.0631(2) 0.45233(11) 0.032 Uiso 1 calc R .
H11B H 0.31646(10) 0.0380(2) 0.35876(11) 0.032 Uiso 1 calc R .
C111 C 0.42070(13) 0.2452(3) 0.35177(15) 0.0433(5) Uani 1 d . .
H11C H 0.4434(6) 0.3523(3) 0.3454(9) 0.065 Uiso 1 calc R .
H11D H 0.4010(2) 0.1911(17) 0.2981(4) 0.065 Uiso 1 calc R .
H11E H 0.4615(4) 0.1764(15) 0.3893(5) 0.065 Uiso 1 calc R .
C21 C 0.36400(10) 0.7185(2) 0.33646(10) 0.0216(3) Uani 1 d . .
C22 C 0.39385(10) 0.7990(2) 0.27925(10) 0.0223(3) Uani 1 d . .
C23 C 0.47515(11) 0.8184(2) 0.29686(11) 0.0303(4) Uani 1 d . .
H23 H 0.49457(11) 0.8737(2) 0.25826(11) 0.036 Uiso 1 calc R .
C24 C 0.52863(12) 0.7598(2) 0.36871(13) 0.0380(5) Uani 1 d . .
H24 H 0.58397(12) 0.7724(2) 0.37894(13) 0.046 Uiso 1 calc R .
C25 C 0.49978(13) 0.6825(2) 0.42532(12) 0.0391(5) Uani 1 d . .
H25 H 0.53557(13) 0.6425(2) 0.47531(12) 0.047 Uiso 1 calc R .
C26 C 0.41941(12) 0.6630(2) 0.40974(11) 0.0315(4) Uani 1 d . .
H26 H 0.40094(12) 0.6104(2) 0.44977(11) 0.038 Uiso 1 calc R .
C27 C 0.33988(10) 0.8724(2) 0.20105(9) 0.0221(3) Uani 1 d . .
H27A H 0.29837(10) 0.9374(2) 0.21423(9) 0.026 Uiso 1 calc R .
H27B H 0.37089(10) 0.9490(2) 0.17821(9) 0.026 Uiso 1 calc R .
C28 C 0.36097(12) 0.6599(3) 0.11212(12) 0.0376(5) Uani 1 d . .
H28A H 0.3994(5) 0.6102(15) 0.1604(2) 0.056 Uiso 1 calc R .
H28B H 0.3883(6) 0.7362(4) 0.0858(8) 0.056 Uiso 1 calc R .
H28C H 0.3352(2) 0.5734(12) 0.0731(7) 0.056 Uiso 1 calc R .
C29 C 0.24640(10) 0.8316(2) 0.06571(10) 0.0267(4) Uani 1 d . .
H29A H 0.23275(10) 0.7553(2) 0.01827(10) 0.032 Uiso 1 calc R .
H29B H 0.27275(10) 0.9289(2) 0.05123(10) 0.032 Uiso 1 calc R .
C210 C 0.17192(10) 0.8851(2) 0.08197(11) 0.0259(4) Uani 1 d . .
H21A H 0.18414(10) 0.9685(2) 0.12631(11) 0.031 Uiso 1 calc R .
H21B H 0.13455(10) 0.9339(2) 0.03180(11) 0.031 Uiso 1 calc R .
C211 C 0.06797(12) 0.7807(2) 0.12470(13) 0.0380(5) Uani 1 d . .
H21C H 0.0413(5) 0.6787(2) 0.1313(9) 0.057 Uiso 1 calc R .
H21D H 0.0328(4) 0.8458(15) 0.0799(4) 0.057 Uiso 1 calc R .
H21E H 0.08144(14) 0.8442(15) 0.1759(5) 0.057 Uiso 1 calc 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'
Li Li -0.0003 0.0001 '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'
O O 0.0106 0.0060 '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'
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
O1 Li1 N1 87.62(12) . . ?
O1 Li1 S1 111.27(13) . . ?
N1 Li1 S1 100.59(12) . . ?
O1 Li1 S2 120.89(14) . . ?
N1 Li1 S2 127.60(14) . . ?
S1 Li1 S2 106.62(11) . . ?
O1 Li1 C110 29.77(6) . . ?
N1 Li1 C110 59.25(9) . . ?
S1 Li1 C110 105.31(11) . . ?
S2 Li1 C110 144.59(12) . . ?
O1 Li1 C19 56.90(8) . . ?
N1 Li1 C19 31.55(6) . . ?
S1 Li1 C19 116.13(11) . . ?
S2 Li1 C19 134.43(12) . . ?
C110 Li1 C19 31.46(6) . . ?
O1 Li1 Li2 136.3(2) . . ?
N1 Li1 Li2 132.5(2) . . ?
S1 Li1 Li2 53.32(8) . . ?
S2 Li1 Li2 53.31(8) . . ?
C110 Li1 Li2 154.03(14) . . ?
C19 Li1 Li2 163.38(14) . . ?
O2 Li2 N2 87.52(12) . . ?
O2 Li2 S1 122.73(14) . . ?
N2 Li2 S1 123.48(14) . . ?
O2 Li2 S2 113.62(14) . . ?
N2 Li2 S2 100.42(12) . . ?
S1 Li2 S2 106.66(10) . . ?
O2 Li2 C29 57.02(8) . . ?
N2 Li2 C29 31.57(6) . . ?
S1 Li2 C29 130.49(12) . . ?
S2 Li2 C29 117.95(11) . . ?
O2 Li2 C210 29.40(6) . . ?
N2 Li2 C210 59.20(9) . . ?
S1 Li2 C210 143.49(12) . . ?
S2 Li2 C210 108.31(11) . . ?
C29 Li2 C210 31.58(6) . . ?
O2 Li2 Li1 142.9(2) . . ?
N2 Li2 Li1 127.00(15) . . ?
S1 Li2 Li1 53.25(8) . . ?
S2 Li2 Li1 53.42(8) . . ?
C29 Li2 Li1 158.57(14) . . ?
C210 Li2 Li1 159.90(14) . . ?
C11 S1 Li1 95.49(9) . . ?
C11 S1 Li2 98.37(9) . . ?
Li1 S1 Li2 73.43(9) . . ?
C21 S2 Li2 97.72(9) . . ?
C21 S2 Li1 96.61(9) . . ?
Li2 S2 Li1 73.27(10) . . ?
C18 N1 C19 108.98(13) . . ?
C18 N1 C17 110.06(13) . . ?
C19 N1 C17 109.79(13) . . ?
C18 N1 Li1 117.23(14) . . ?
C19 N1 Li1 101.27(13) . . ?
C17 N1 Li1 109.06(12) . . ?
C28 N2 C29 109.28(13) . . ?
C28 N2 C27 110.11(14) . . ?
C29 N2 C27 109.95(13) . . ?
C28 N2 Li2 116.68(15) . . ?
C29 N2 Li2 101.05(13) . . ?
C27 N2 Li2 109.34(12) . . ?
C111 O1 C110 111.70(14) . . ?
C111 O1 Li1 119.00(15) . . ?
C110 O1 Li1 107.05(13) . . ?
C211 O2 C210 111.63(13) . . ?
C211 O2 Li2 123.17(14) . . ?
C210 O2 Li2 108.22(13) . . ?
C16 C11 C12 117.3(2) . . ?
C16 C11 S1 120.01(14) . . ?
C12 C11 S1 122.71(13) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 C17 118.81(15) . . ?
C11 C12 C17 121.7(2) . . ?
C14 C13 C12 122.5(2) . . ?
C13 C14 C15 118.2(2) . . ?
C16 C15 C14 120.5(2) . . ?
C15 C16 C11 122.1(2) . . ?
N1 C17 C12 113.50(12) . . ?
N1 C19 C110 111.71(13) . . ?
N1 C19 Li1 47.18(9) . . ?
C110 C19 Li1 74.04(11) . . ?
O1 C110 C19 107.40(13) . . ?
O1 C110 Li1 43.18(9) . . ?
C19 C110 Li1 74.49(11) . . ?
C26 C21 C22 117.2(2) . . ?
C26 C21 S2 119.54(14) . . ?
C22 C21 S2 123.23(13) . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 C27 118.5(2) . . ?
C21 C22 C27 121.8(2) . . ?
C24 C23 C22 122.2(2) . . ?
C25 C24 C23 118.5(2) . . ?
C26 C25 C24 120.5(2) . . ?
C25 C26 C21 122.0(2) . . ?
N2 C27 C22 113.90(13) . . ?
N2 C29 C210 111.70(13) . . ?
N2 C29 Li2 47.38(10) . . ?
C210 C29 Li2 74.35(11) . . ?
O2 C210 C29 107.23(13) . . ?
O2 C210 Li2 42.38(9) . . ?
C29 C210 Li2 74.07(11) . . ?
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
Li1 O1 1.975(3) . ?
Li1 N1 2.068(3) . ?
Li1 S1 2.423(3) . ?
Li1 S2 2.431(3) . ?
Li1 C110 2.759(3) . ?
Li1 C19 2.765(3) . ?
Li1 Li2 2.899(4) . ?
Li2 O2 1.960(3) . ?
Li2 N2 2.068(3) . ?
Li2 S1 2.426(3) . ?
Li2 S2 2.427(3) . ?
Li2 C29 2.758(3) . ?
Li2 C210 2.762(3) . ?
S1 C11 1.768(2) . ?
S2 C21 1.761(2) . ?
N1 C18 1.460(2) . ?
N1 C19 1.475(2) . ?
N1 C17 1.478(2) . ?
N2 C28 1.461(2) . ?
N2 C29 1.471(2) . ?
N2 C27 1.478(2) . ?
O1 C111 1.415(2) . ?
O1 C110 1.433(2) . ?
O2 C211 1.415(2) . ?
O2 C210 1.427(2) . ?
C11 C16 1.403(2) . ?
C11 C12 1.412(2) . ?
C12 C13 1.391(2) . ?
C12 C17 1.503(2) . ?
C13 C14 1.382(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.381(3) . ?
C19 C110 1.498(2) . ?
C21 C26 1.405(2) . ?
C21 C22 1.413(2) . ?
C22 C23 1.391(3) . ?
C22 C27 1.506(2) . ?
C23 C24 1.383(3) . ?
C24 C25 1.383(3) . ?
C25 C26 1.379(3) . ?
C29 C210 1.502(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337555
