#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/26/4322612.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_4322612
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            'C21 H39 N2 Na S'
_chemical_formula_weight         374.59
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.27020(10)
_cell_length_b                   20.1017(2)
_cell_length_c                   25.9256(4)
_cell_measurement_reflns_used    5390
_cell_measurement_temperature    150(2)
_cell_volume                     4831.15(10)
_computing_cell_refinement       'Siemens SMART'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'Siemens SMART CCD'
_diffrn_measurement_method       ω
_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  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16364
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        No
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.030
_exptl_crystal_description       stick
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0010(3)
_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   1.140
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_restrained_S_obs      1.140
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_obs          0.0637
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0430P)²+2.8288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1350
_refine_ls_wR_factor_obs         0.1171
_reflns_number_observed          3292
_reflns_number_total             5032
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic970769l_3.cif
_cod_data_source_block           ube016
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+2.8288P] 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^)+(0.0430P)^2^+2.8288P] 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               4322612
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Na1 Na -0.11027(11) 0.06662(5) 0.28355(3) 0.0337(3) Uani 1 d . .
S1 S 0.18661(8) 0.07218(4) 0.29484(2) 0.0435(2) Uani 1 d . .
C1 C 0.2270(3) 0.10980(12) 0.35596(8) 0.0296(6) Uani 1 d . .
C2 C 0.2525(3) 0.17887(12) 0.36029(7) 0.0295(5) Uani 1 d . .
C3 C 0.2807(3) 0.20632(12) 0.40904(8) 0.0339(6) Uani 1 d . .
H3A H 0.2966(3) 0.25288(12) 0.41169(8) 0.041 Uiso 1 calc R .
C4 C 0.2862(3) 0.16789(12) 0.45364(8) 0.0365(6) Uani 1 d . .
C5 C 0.2620(3) 0.09986(12) 0.44876(8) 0.0355(6) Uani 1 d . .
H5A H 0.2668(3) 0.07287(12) 0.47879(8) 0.043 Uiso 1 calc R .
C6 C 0.2307(3) 0.06944(11) 0.40127(8) 0.0305(5) Uani 1 d . .
C7 C 0.2452(3) 0.22482(13) 0.31332(8) 0.0394(7) Uani 1 d . .
H7A H 0.2697(3) 0.19753(13) 0.28228(8) 0.047 Uiso 1 calc R .
C8 C 0.0906(4) 0.2506(2) 0.30612(12) 0.0670(10) Uani 1 d . .
H8A H 0.0868(4) 0.2800(2) 0.27598(12) 0.101 Uiso 1 calc R .
H8B H 0.0611(4) 0.2754(2) 0.33691(12) 0.101 Uiso 1 calc R .
H8C H 0.0251(4) 0.2130(2) 0.30088(12) 0.101 Uiso 1 calc R .
C9 C 0.3510(4) 0.28322(13) 0.31503(10) 0.0510(8) Uani 1 d . .
H9A H 0.3399(4) 0.31020(13) 0.28380(10) 0.077 Uiso 1 calc R .
H9B H 0.4499(4) 0.26621(13) 0.31696(10) 0.077 Uiso 1 calc R .
H9C H 0.3309(4) 0.31066(13) 0.34544(10) 0.077 Uiso 1 calc R .
C10 C 0.3167(4) 0.19948(14) 0.50608(9) 0.0565(9) Uani 1 d . .
H10A H 0.3276(4) 0.24849(14) 0.50076(9) 0.068 Uiso 1 calc R .
C11 C 0.1900(5) 0.1884(2) 0.54365(10) 0.0743(12) Uani 1 d . .
H11A H 0.2124(5) 0.2091(2) 0.57692(10) 0.111 Uiso 1 calc R .
H11B H 0.1747(5) 0.1406(2) 0.54855(10) 0.111 Uiso 1 calc R .
H11C H 0.1024(5) 0.2085(2) 0.52937(10) 0.111 Uiso 1 calc R .
C12 C 0.4591(5) 0.1731(2) 0.52903(12) 0.0820(13) Uani 1 d . .
H12A H 0.4762(5) 0.1941(2) 0.56260(12) 0.123 Uiso 1 calc R .
H12B H 0.5389(5) 0.1837(2) 0.50566(12) 0.123 Uiso 1 calc R .
H12C H 0.4527(5) 0.1248(2) 0.53341(12) 0.123 Uiso 1 calc R .
C13 C 0.2011(3) -0.00527(12) 0.39895(10) 0.0391(6) Uani 1 d . .
H13A H 0.1278(3) -0.01236(12) 0.37122(10) 0.047 Uiso 1 calc R .
C14 C 0.3372(4) -0.04304(15) 0.3826(2) 0.0718(11) Uani 1 d . .
H14A H 0.3759(4) -0.02334(15) 0.3509(2) 0.108 Uiso 1 calc R .
H14B H 0.3130(4) -0.08982(15) 0.3764(2) 0.108 Uiso 1 calc R .
H14C H 0.4096(4) -0.04013(15) 0.4100(2) 0.108 Uiso 1 calc R .
C15 C 0.1390(4) -0.03531(14) 0.44836(11) 0.0562(9) Uani 1 d . .
H15A H 0.1235(4) -0.08311(14) 0.44344(11) 0.084 Uiso 1 calc R .
H15B H 0.0469(4) -0.01377(14) 0.45647(11) 0.084 Uiso 1 calc R .
H15C H 0.2068(4) -0.02829(14) 0.47686(11) 0.084 Uiso 1 calc R .
N1 N -0.2390(2) 0.10736(10) 0.36129(7) 0.0335(5) Uani 1 d . .
N2 N -0.2216(2) -0.03711(10) 0.31973(7) 0.0346(5) Uani 1 d . .
C16 C -0.3290(3) 0.16559(13) 0.34763(10) 0.0491(8) Uani 1 d . .
H16A H -0.2665(3) 0.20295(13) 0.33809(10) 0.074 Uiso 1 calc R .
H16B H -0.3885(3) 0.17817(13) 0.37730(10) 0.074 Uiso 1 calc R .
H16C H -0.3915(3) 0.15423(13) 0.31844(10) 0.074 Uiso 1 calc R .
C17 C -0.1430(3) 0.12568(14) 0.40453(9) 0.0431(7) Uani 1 d . .
H17A H -0.0815(3) 0.16301(14) 0.39417(9) 0.065 Uiso 1 calc R .
H17B H -0.0825(3) 0.08749(14) 0.41370(9) 0.065 Uiso 1 calc R .
H17C H -0.2013(3) 0.13869(14) 0.43440(9) 0.065 Uiso 1 calc R .
C18 C -0.3330(3) 0.05141(12) 0.37558(9) 0.0387(6) Uani 1 d . .
H18A H -0.4176(3) 0.05088(12) 0.35228(9) 0.046 Uiso 1 calc R .
H18B H -0.3687(3) 0.05846(12) 0.41114(9) 0.046 Uiso 1 calc R .
C19 C -0.2578(3) -0.01614(12) 0.37283(8) 0.0365(6) Uani 1 d . .
H19A H -0.1679(3) -0.01417(12) 0.39343(8) 0.044 Uiso 1 calc R .
H19B H -0.3212(3) -0.05013(12) 0.38863(8) 0.044 Uiso 1 calc R .
C20 C -0.1220(4) -0.09410(13) 0.32061(11) 0.0493(7) Uani 1 d . .
H20A H -0.0991(4) -0.10740(13) 0.28518(11) 0.074 Uiso 1 calc R .
H20C H -0.1674(4) -0.13141(13) 0.33872(11) 0.074 Uiso 1 calc R .
H20D H -0.0330(4) -0.08144(13) 0.33853(11) 0.074 Uiso 1 calc R .
C21 C -0.3529(3) -0.05804(13) 0.29152(9) 0.0435(7) Uani 1 d . .
H21C H -0.4215(3) -0.02098(13) 0.29029(9) 0.065 Uiso 1 calc R .
H21D H -0.3972(3) -0.09590(13) 0.30929(9) 0.065 Uiso 1 calc R .
H21A H -0.3268(3) -0.07110(13) 0.25632(9) 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 N2 76.86(7) . . ?
N1 Na1 S1 112.26(6) . . ?
N2 Na1 S1 113.76(6) . . ?
N1 Na1 S1 104.79(6) . 6_556 ?
N2 Na1 S1 91.61(6) . 6_556 ?
S1 Na1 S1 138.64(3) . 6_556 ?
C1 S1 Na1 108.51(8) . . ?
C1 S1 Na1 121.48(9) . 6_656 ?
Na1 S1 Na1 126.57(3) . 6_656 ?
C2 C1 C6 119.3(2) . . ?
C2 C1 S1 121.3(2) . . ?
C6 C1 S1 119.5(2) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 C7 119.2(2) . . ?
C1 C2 C7 121.5(2) . . ?
C4 C3 C2 122.5(2) . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 C10 121.1(2) . . ?
C5 C4 C10 121.3(2) . . ?
C4 C5 C6 122.7(2) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C13 120.0(2) . . ?
C1 C6 C13 121.4(2) . . ?
C2 C7 C9 114.3(2) . . ?
C2 C7 C8 110.0(2) . . ?
C9 C7 C8 110.0(2) . . ?
C4 C10 C12 111.1(3) . . ?
C4 C10 C11 111.2(3) . . ?
C12 C10 C11 111.0(3) . . ?
C15 C13 C6 115.0(2) . . ?
C15 C13 C14 110.3(2) . . ?
C6 C13 C14 110.5(2) . . ?
C18 N1 C17 110.9(2) . . ?
C18 N1 C16 109.4(2) . . ?
C17 N1 C16 108.9(2) . . ?
C18 N1 Na1 103.72(13) . . ?
C17 N1 Na1 114.1(2) . . ?
C16 N1 Na1 109.73(14) . . ?
C20 N2 C19 110.5(2) . . ?
C20 N2 C21 107.6(2) . . ?
C19 N2 C21 110.8(2) . . ?
C20 N2 Na1 113.2(2) . . ?
C19 N2 Na1 101.79(14) . . ?
C21 N2 Na1 112.94(14) . . ?
N1 C18 C19 113.5(2) . . ?
N2 C19 C18 113.6(2) . . ?
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 2.481(2) . ?
Na1 N2 2.509(2) . ?
Na1 S1 2.7699(12) . ?
Na1 S1 2.7727(11) 6_556 ?
S1 C1 1.795(2) . ?
S1 Na1 2.7726(11) 6_656 ?
C1 C2 1.413(3) . ?
C1 C6 1.428(3) . ?
C2 C3 1.404(3) . ?
C2 C7 1.530(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.392(3) . ?
C4 C10 1.527(3) . ?
C5 C6 1.405(3) . ?
C6 C13 1.528(3) . ?
C7 C9 1.530(4) . ?
C7 C8 1.536(4) . ?
C10 C12 1.542(5) . ?
C10 C11 1.542(5) . ?
C13 C15 1.529(4) . ?
C13 C14 1.532(4) . ?
N1 C18 1.470(3) . ?
N1 C17 1.478(3) . ?
N1 C16 1.480(3) . ?
N2 C20 1.472(3) . ?
N2 C19 1.478(3) . ?
N2 C21 1.480(3) . ?
C18 C19 1.528(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 168337484
