#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/26/4322610.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_4322610
loop_
_publ_author_name
'Ulrich Englich'
'Scott Chadwick'
'Karin Ruhlandt-Senge'
_publ_section_title
;
 Sodium and Potassium Triisopropylbenzenethiolates: Influence on
 Solid-State Structure by Metal and Donor
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              283
_journal_page_last               293
_journal_paper_doi               10.1021/ic970769l
_journal_volume                  37
_journal_year                    1998
_chemical_formula_sum            'C24 H46 N3 Na S'
_chemical_formula_weight         431.69
_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                 100.4490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.23000(10)
_cell_length_b                   10.61760(10)
_cell_length_c                   19.6262(3)
_cell_measurement_reflns_used    6408
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.57
_cell_volume                     2711.19(5)
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measurement_device       'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15997
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        no
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.053
_refine_ls_goodness_of_fit_obs   1.129
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_restrained_S_obs      1.129
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_obs          0.0625
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+2.0949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1297
_refine_ls_wR_factor_obs         0.1153
_reflns_number_observed          4403
_reflns_number_total             6309
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic970769l_1.cif
_cod_data_source_block           ube026
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+2.0949P] 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^)+(0.0343P)^2^+2.0949P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4322610
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
Na1 Na 0.38665(6) 0.87924(9) -0.00294(4) 0.0282(2) Uani 1 d . .
S1 S 0.60393(4) 0.85750(6) 0.01371(3) 0.02723(15) Uani 1 d . .
C1 C 0.7069(2) 0.7686(2) 0.06175(11) 0.0228(4) Uani 1 d . .
C2 C 0.7812(2) 0.7114(2) 0.02779(11) 0.0232(5) Uani 1 d . .
C3 C 0.8630(2) 0.6462(2) 0.06689(11) 0.0282(5) Uani 1 d . .
H3A H 0.9111(2) 0.6091(2) 0.04403(11) 0.034 Uiso 1 calc R .
C4 C 0.8763(2) 0.6337(2) 0.13886(11) 0.0286(5) Uani 1 d . .
C5 C 0.8021(2) 0.6885(2) 0.17093(11) 0.0279(5) Uani 1 d . .
H5A H 0.8088(2) 0.6813(2) 0.21876(11) 0.034 Uiso 1 calc R .
C6 C 0.7178(2) 0.7540(2) 0.13466(11) 0.0246(5) Uani 1 d . .
C7 C 0.7714(2) 0.7158(2) -0.05072(10) 0.0260(5) Uani 1 d . .
H7A H 0.7243(2) 0.7848(2) -0.06776(10) 0.031 Uiso 1 calc R .
C8 C 0.8726(2) 0.7408(3) -0.07546(13) 0.0430(7) Uani 1 d . .
H8A H 0.8606(2) 0.7423(3) -0.12518(13) 0.064 Uiso 1 calc R .
H8B H 0.9208(2) 0.6753(3) -0.05888(13) 0.064 Uiso 1 calc R .
H8C H 0.8999(2) 0.8206(3) -0.05785(13) 0.064 Uiso 1 calc R .
C9 C 0.7230(2) 0.5941(3) -0.08242(12) 0.0439(7) Uani 1 d . .
H9A H 0.7170(2) 0.5974(3) -0.13187(12) 0.066 Uiso 1 calc R .
H9B H 0.6560(2) 0.5842(3) -0.07081(12) 0.066 Uiso 1 calc R .
H9C H 0.7655(2) 0.5240(3) -0.06455(12) 0.066 Uiso 1 calc R .
C10 C 0.9703(2) 0.5654(2) 0.17854(12) 0.0352(6) Uani 1 d . .
H10A H 0.9838(2) 0.4937(2) 0.15006(12) 0.042 Uiso 1 calc R .
C11 C 0.9573(2) 0.5136(3) 0.2479(2) 0.0627(10) Uani 1 d . .
H11A H 0.8977(2) 0.4603(3) 0.2421(2) 0.094 Uiso 1 calc R .
H11B H 0.9488(2) 0.5819(3) 0.2784(2) 0.094 Uiso 1 calc R .
H11C H 1.0170(2) 0.4656(3) 0.2674(2) 0.094 Uiso 1 calc R .
C12 C 1.0633(2) 0.6487(4) 0.1875(2) 0.0791(13) Uani 1 d . .
H12A H 1.0714(2) 0.6816(4) 0.1432(2) 0.119 Uiso 1 calc R .
H12B H 1.1231(2) 0.6008(4) 0.2069(2) 0.119 Uiso 1 calc R .
H12C H 1.0549(2) 0.7171(4) 0.2179(2) 0.119 Uiso 1 calc R .
C13 C 0.6402(2) 0.8102(2) 0.17428(11) 0.0280(5) Uani 1 d . .
H13A H 0.5757(2) 0.8214(2) 0.14132(11) 0.034 Uiso 1 calc R .
C14 C 0.6172(2) 0.7261(3) 0.23254(12) 0.0383(6) Uani 1 d . .
H14A H 0.5679(2) 0.7667(3) 0.25547(12) 0.058 Uiso 1 calc R .
H14B H 0.6794(2) 0.7114(3) 0.26523(12) 0.058 Uiso 1 calc R .
H14C H 0.5899(2) 0.6472(3) 0.21363(12) 0.058 Uiso 1 calc R .
C15 C 0.6749(2) 0.9400(3) 0.20263(14) 0.0444(7) Uani 1 d . .
H15A H 0.6248(2) 0.9738(3) 0.22746(14) 0.067 Uiso 1 calc R .
H15B H 0.6817(2) 0.9951(3) 0.16494(14) 0.067 Uiso 1 calc R .
H15C H 0.7399(2) 0.9328(3) 0.23334(14) 0.067 Uiso 1 calc R .
C16 C 0.3917(3) 0.6016(3) -0.0506(2) 0.0577(8) Uani 1 d . .
H16A H 0.3492(3) 0.5955(3) -0.0159(2) 0.087 Uiso 1 calc R .
H16B H 0.4622(3) 0.6104(3) -0.0285(2) 0.087 Uiso 1 calc R .
H16C H 0.3839(3) 0.5269(3) -0.0785(2) 0.087 Uiso 1 calc R .
C17 C 0.4263(2) 0.7185(3) -0.14637(13) 0.0441(7) Uani 1 d . .
H17A H 0.4069(2) 0.7903(3) -0.17557(13) 0.066 Uiso 1 calc R .
H17B H 0.4184(2) 0.6433(3) -0.17398(13) 0.066 Uiso 1 calc R .
H17C H 0.4967(2) 0.7269(3) -0.12391(13) 0.066 Uiso 1 calc R .
N1 N 0.3608(2) 0.7111(2) -0.09421(10) 0.0344(5) Uani 1 d . .
C18 C 0.2522(2) 0.7069(3) -0.12906(14) 0.0472(7) Uani 1 d . .
H18A H 0.2398(2) 0.6283(3) -0.15444(14) 0.057 Uiso 1 calc R .
H18B H 0.2396(2) 0.7752(3) -0.16235(14) 0.057 Uiso 1 calc R .
C19 C 0.1775(2) 0.7174(3) -0.07979(14) 0.0470(7) Uani 1 d . .
H19A H 0.1081(2) 0.7194(3) -0.10633(14) 0.056 Uiso 1 calc R .
H19B H 0.1836(2) 0.6430(3) -0.05060(14) 0.056 Uiso 1 calc R .
N2 N 0.19393(15) 0.8302(2) -0.03534(10) 0.0334(5) Uani 1 d . .
C20 C 0.1480(2) 0.9415(3) -0.07220(13) 0.0457(7) Uani 1 d . .
H20A H 0.1746(2) 0.9517(3) -0.11423(13) 0.069 Uiso 1 calc R .
H20B H 0.1645(2) 1.0145(3) -0.04349(13) 0.069 Uiso 1 calc R .
H20C H 0.0747(2) 0.9314(3) -0.08312(13) 0.069 Uiso 1 calc R .
C21 C 0.1543(2) 0.8127(3) 0.02919(12) 0.0357(6) Uani 1 d . .
H21A H 0.1623(2) 0.7252(3) 0.04324(12) 0.043 Uiso 1 calc R .
H21B H 0.0815(2) 0.8324(3) 0.02099(12) 0.043 Uiso 1 calc R .
C22 C 0.2099(2) 0.8959(2) 0.08748(12) 0.0334(5) Uani 1 d . .
H22A H 0.2051(2) 0.9829(2) 0.07220(12) 0.040 Uiso 1 calc R .
H22B H 0.1755(2) 0.8891(2) 0.12699(12) 0.040 Uiso 1 calc R .
N3 N 0.31883(14) 0.8628(2) 0.10947(9) 0.0285(4) Uani 1 d . .
C23 C 0.3680(2) 0.9607(2) 0.15682(12) 0.0356(6) Uani 1 d . .
H23A H 0.3604(2) 1.0409(2) 0.13378(12) 0.053 Uiso 1 calc R .
H23B H 0.4397(2) 0.9418(2) 0.17072(12) 0.053 Uiso 1 calc R .
H23C H 0.3361(2) 0.9638(2) 0.19698(12) 0.053 Uiso 1 calc R .
C24 C 0.3309(2) 0.7414(2) 0.14514(14) 0.0431(7) Uani 1 d . .
H24A H 0.2989(2) 0.6767(2) 0.11446(14) 0.065 Uiso 1 calc R .
H24B H 0.2990(2) 0.7449(2) 0.18532(14) 0.065 Uiso 1 calc R .
H24C H 0.4027(2) 0.7229(2) 0.15906(14) 0.065 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'
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'
Na Na 0.0362 0.0249 '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'
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 Na1 N3 123.30(7) . . ?
N1 Na1 N2 71.22(7) . . ?
N3 Na1 N2 73.09(6) . . ?
N1 Na1 S1 131.07(6) . 3_675 ?
N3 Na1 S1 99.30(5) . 3_675 ?
N2 Na1 S1 103.83(6) . 3_675 ?
N1 Na1 S1 91.62(5) . . ?
N3 Na1 S1 113.87(5) . . ?
N2 Na1 S1 161.85(6) . . ?
S1 Na1 S1 91.82(3) 3_675 . ?
N1 Na1 Na1 119.31(6) . 3_675 ?
N3 Na1 Na1 114.08(5) . 3_675 ?
N2 Na1 Na1 149.07(7) . 3_675 ?
S1 Na1 Na1 46.28(2) 3_675 3_675 ?
S1 Na1 Na1 45.54(2) . 3_675 ?
C1 S1 Na1 121.83(7) . 3_675 ?
C1 S1 Na1 139.87(7) . . ?
Na1 S1 Na1 88.18(3) 3_675 . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 S1 120.4(2) . . ?
C6 C1 S1 121.3(2) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 C7 119.2(2) . . ?
C1 C2 C7 121.5(2) . . ?
C2 C3 C4 123.1(2) . . ?
C5 C4 C3 116.7(2) . . ?
C5 C4 C10 123.1(2) . . ?
C3 C4 C10 120.1(2) . . ?
C4 C5 C6 122.9(2) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C13 119.1(2) . . ?
C1 C6 C13 121.3(2) . . ?
C2 C7 C9 109.8(2) . . ?
C2 C7 C8 114.1(2) . . ?
C9 C7 C8 110.2(2) . . ?
C12 C10 C11 109.6(2) . . ?
C12 C10 C4 110.8(2) . . ?
C11 C10 C4 114.8(2) . . ?
C6 C13 C14 113.5(2) . . ?
C6 C13 C15 110.8(2) . . ?
C14 C13 C15 110.1(2) . . ?
C16 N1 C17 108.5(2) . . ?
C16 N1 C18 113.2(2) . . ?
C17 N1 C18 109.2(2) . . ?
C16 N1 Na1 99.2(2) . . ?
C17 N1 Na1 116.2(2) . . ?
C18 N1 Na1 110.4(2) . . ?
N1 C18 C19 113.4(2) . . ?
N2 C19 C18 113.3(2) . . ?
C20 N2 C21 110.4(2) . . ?
C20 N2 C19 111.2(2) . . ?
C21 N2 C19 111.7(2) . . ?
C20 N2 Na1 105.31(14) . . ?
C21 N2 Na1 107.83(13) . . ?
C19 N2 Na1 110.18(15) . . ?
N2 C21 C22 112.0(2) . . ?
N3 C22 C21 113.3(2) . . ?
C24 N3 C23 108.9(2) . . ?
C24 N3 C22 111.5(2) . . ?
C23 N3 C22 108.4(2) . . ?
C24 N3 Na1 116.9(2) . . ?
C23 N3 Na1 108.47(14) . . ?
C22 N3 Na1 102.19(13) . . ?
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
Na1 N1 2.508(2) . ?
Na1 N3 2.534(2) . ?
Na1 N2 2.567(2) . ?
Na1 S1 2.8076(11) 3_675 ?
Na1 S1 2.8431(10) . ?
Na1 Na1 3.932(2) 3_675 ?
S1 C1 1.781(2) . ?
S1 Na1 2.8076(11) 3_675 ?
C1 C2 1.420(3) . ?
C1 C6 1.421(3) . ?
C2 C3 1.392(3) . ?
C2 C7 1.523(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.386(3) . ?
C4 C10 1.526(3) . ?
C5 C6 1.395(3) . ?
C6 C13 1.518(3) . ?
C7 C9 1.524(3) . ?
C7 C8 1.528(3) . ?
C10 C12 1.500(4) . ?
C10 C11 1.507(4) . ?
C13 C14 1.524(3) . ?
C13 C15 1.525(3) . ?
C16 N1 1.458(3) . ?
C17 N1 1.458(3) . ?
N1 C18 1.476(3) . ?
C18 C19 1.508(4) . ?
C19 N2 1.474(3) . ?
N2 C20 1.459(3) . ?
N2 C21 1.468(3) . ?
C21 C22 1.525(3) . ?
C22 N3 1.470(3) . ?
N3 C24 1.462(3) . ?
N3 C23 1.466(3) . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2024-11-17T23:38:10+02:00
;
 Replaced the '&G' character sequence with the backslash character ('\')
 in the '_diffrn_measurement_method' data value.
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337483
