#------------------------------------------------------------------------------
#$Date: 2023-12-08 16:16:31 +0200 (Fri, 08 Dec 2023) $
#$Revision: 288183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/69/4316942.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_4316942
loop_
_publ_author_name
'Christian Neis'
'David Petry'
'Alexandre Demangeon'
'Bernd Morgenstern'
'Dirk Kuppert'
'Jochen Huppert'
'Stefan Stucky'
'Kaspar Hegetschweiler'
_publ_section_title
;
 Facially Coordinating Triamine Ligands with a Cyclic Backbone: Some
 Structure-Stability Correlations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10092
_journal_page_last               10107
_journal_paper_doi               10.1021/ic101360d
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C23 H37 N3 O6 S2'
_chemical_formula_weight         515.68
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.45(3)
_cell_angle_beta                 104.09(3)
_cell_angle_gamma                91.03(3)
_cell_formula_units_Z            2
_cell_length_a                   9.280(2)
_cell_length_b                   9.951(2)
_cell_length_c                   15.008(3)
_cell_measurement_temperature    200(2)
_cell_volume                     1309.0(5)
_computing_cell_refinement       'Stoe IPDS Software Vers.2.87, 1997'
_computing_data_collection       'Stoe IPDS Software Vers.2.87, 1997'
_computing_data_reduction        'Stoe IPDS Software Vers.2.87, 1997'
_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      200(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'STOE IPDS, image plate'
_diffrn_measurement_method       'phi 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  0.0859
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8138
_diffrn_reflns_theta_full        24.01
_diffrn_reflns_theta_max         24.01
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0452
_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)+(0.0556P)²+0.5033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                3395
_reflns_number_total             3783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101360d_si_001_1.cif
_cod_data_source_block           H2Me3tach(Tos)2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4316942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.18379(6) 0.74905(5) 0.95000(3) 0.02410(19) Uani 1 1 d . . .
O11 O 0.08621(18) 0.64219(15) 0.96536(10) 0.0290(4) Uani 1 1 d . . .
O12 O 0.12300(18) 0.88276(15) 0.96395(11) 0.0318(4) Uani 1 1 d . . .
O13 O 0.33672(18) 0.74894(17) 1.00227(11) 0.0351(4) Uani 1 1 d . . .
N1 N -0.1881(2) 0.8344(2) 0.96566(13) 0.0239(4) Uani 1 1 d . . .
N3 N -0.1829(2) 0.4836(2) 0.87271(14) 0.0273(4) Uani 1 1 d . . .
N2 N -0.1768(2) 0.7312(2) 0.77491(13) 0.0313(5) Uani 1 1 d . . .
C6 C -0.3822(3) 0.6305(2) 0.92463(14) 0.0238(5) Uani 1 1 d . . .
H6 H -0.4933 0.6191 0.9103 0.029 Uiso 1 1 calc R . .
C3 C -0.3407(3) 0.7072(2) 0.75245(14) 0.0277(5) Uani 1 1 d . . .
H3 H -0.3835 0.7250 0.6885 0.033 Uiso 1 1 calc R . .
C9 C -0.3291(3) 0.6022(2) 1.02320(15) 0.0299(5) Uani 1 1 d . . .
H9A H -0.3575 0.6757 1.0693 0.045 Uiso 1 1 calc R . .
H9B H -0.2205 0.5994 1.0393 0.045 Uiso 1 1 calc R . .
H9C H -0.3753 0.5133 1.0241 0.045 Uiso 1 1 calc R . .
C4 C -0.3880(3) 0.5574(2) 0.75035(14) 0.0297(5) Uani 1 1 d . . .
H4 H -0.4994 0.5513 0.7333 0.036 Uiso 1 1 calc R . .
C1 C -0.3482(2) 0.7825(2) 0.92368(14) 0.0234(5) Uani 1 1 d . . .
H1 H -0.4072 0.8392 0.9635 0.028 Uiso 1 1 calc R . .
C2 C -0.4033(3) 0.8077(2) 0.82410(14) 0.0274(5) Uani 1 1 d . . .
H2 H -0.5134 0.7850 0.8054 0.033 Uiso 1 1 calc R . .
C5 C -0.3419(2) 0.5201(2) 0.84737(14) 0.0252(5) Uani 1 1 d . . .
H5 H -0.4045 0.4344 0.8417 0.030 Uiso 1 1 calc R . .
C7 C -0.3806(3) 0.9584(2) 0.81935(17) 0.0399(6) Uani 1 1 d . . .
H7A H -0.4177 0.9672 0.7541 0.060 Uiso 1 1 calc R . .
H7B H -0.2743 0.9884 0.8416 0.060 Uiso 1 1 calc R . .
H7C H -0.4354 1.0162 0.8594 0.060 Uiso 1 1 calc R . .
C8 C -0.3455(3) 0.4534(3) 0.67111(16) 0.0458(7) Uani 1 1 d . . .
H8A H -0.3777 0.3597 0.6725 0.069 Uiso 1 1 calc R . .
H8B H -0.2373 0.4611 0.6801 0.069 Uiso 1 1 calc R . .
H8C H -0.3945 0.4729 0.6101 0.069 Uiso 1 1 calc R . .
C13 C 0.1943(3) 0.7677(2) 0.68499(16) 0.0353(6) Uani 1 1 d . . .
H13 H 0.1987 0.8375 0.6512 0.042 Uiso 1 1 calc R . .
C14 C 0.1947(3) 0.6303(3) 0.64055(16) 0.0350(6) Uani 1 1 d . . .
C12 C 0.1874(3) 0.8044(2) 0.77915(16) 0.0304(5) Uani 1 1 d . . .
H12 H 0.1870 0.8986 0.8093 0.036 Uiso 1 1 calc R . .
C15 C 0.1850(3) 0.5292(2) 0.69033(16) 0.0360(6) Uani 1 1 d . . .
H15 H 0.1831 0.4347 0.6599 0.043 Uiso 1 1 calc R . .
C11 C 0.1812(2) 0.7019(2) 0.82798(14) 0.0245(5) Uani 1 1 d . . .
C16 C 0.1780(3) 0.5642(2) 0.78381(15) 0.0309(5) Uani 1 1 d . . .
H16 H 0.1710 0.4942 0.8171 0.037 Uiso 1 1 calc R . .
C17 C 0.2089(4) 0.5905(3) 0.53984(18) 0.0575(8) Uani 1 1 d . . .
H17A H 0.2073 0.4899 0.5202 0.086 Uiso 1 1 calc R . .
H17B H 0.3031 0.6323 0.5361 0.086 Uiso 1 1 calc R . .
H17C H 0.1256 0.6238 0.4982 0.086 Uiso 1 1 calc R . .
S2 S -0.01523(8) 0.14622(6) 0.75267(4) 0.0351(2) Uani 1 1 d . . .
O21 O 0.0845(3) 0.1491(3) 0.84346(12) 0.0682(7) Uani 1 1 d . A .
C21 C 0.1041(3) 0.1539(2) 0.67650(15) 0.0323(6) Uani 1 1 d . A .
O23A O -0.0626(12) 0.2782(15) 0.7611(11) 0.065(3) Uani 0.45 1 d P A 1
O23B O -0.1242(9) 0.2537(11) 0.7440(7) 0.054(2) Uani 0.55 1 d P A 2
O22 O -0.1025(3) 0.0166(2) 0.71486(14) 0.0620(6) Uani 1 1 d . A .
C26 C 0.0402(3) 0.1584(3) 0.58318(15) 0.0393(6) Uani 1 1 d . . .
H26 H -0.0648 0.1589 0.5611 0.047 Uiso 1 1 calc R A .
C22 C 0.2560(3) 0.1524(3) 0.70735(17) 0.0407(6) Uani 1 1 d . . .
H22 H 0.2997 0.1495 0.7710 0.049 Uiso 1 1 calc R A .
C24 C 0.2844(4) 0.1602(3) 0.55238(17) 0.0462(7) Uani 1 1 d . . .
C23 C 0.3468(3) 0.1553(3) 0.64588(19) 0.0461(7) Uani 1 1 d . A .
H23 H 0.4517 0.1539 0.6679 0.055 Uiso 1 1 calc R . .
C27 C 0.3807(4) 0.1647(4) 0.4846(2) 0.0702(10) Uani 1 1 d . A .
H27A H 0.4856 0.1627 0.5173 0.105 Uiso 1 1 calc R . .
H27B H 0.3669 0.2498 0.4616 0.105 Uiso 1 1 calc R . .
H27C H 0.3519 0.0848 0.4312 0.105 Uiso 1 1 calc R . .
C25 C 0.1314(4) 0.1623(3) 0.52265(17) 0.0477(7) Uani 1 1 d . A .
H25 H 0.0876 0.1666 0.4592 0.057 Uiso 1 1 calc R . .
H3NA H -0.118(3) 0.559(3) 0.8784(19) 0.043(7) Uiso 1 1 d . . .
H3NB H -0.166(4) 0.409(3) 0.830(2) 0.054(9) Uiso 1 1 d . . .
H3NC H -0.166(3) 0.452(3) 0.928(2) 0.044(7) Uiso 1 1 d . . .
H1NA H -0.184(3) 0.929(3) 0.9757(16) 0.026(6) Uiso 1 1 d . . .
H1NB H -0.132(3) 0.799(3) 0.931(2) 0.039(7) Uiso 1 1 d . . .
H1NC H -0.152(3) 0.806(3) 1.022(2) 0.043(7) Uiso 1 1 d . . .
H2NA H -0.143(4) 0.667(3) 0.737(2) 0.052(8) Uiso 1 1 d . . .
H2NB H -0.150(3) 0.819(3) 0.7694(19) 0.041(7) 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
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'
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'
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
O13 S1 O12 114.31(10) . . ?
O13 S1 O11 112.12(10) . . ?
O12 S1 O11 111.57(10) . . ?
O13 S1 C11 106.73(10) . . ?
O12 S1 C11 105.78(10) . . ?
O11 S1 C11 105.61(10) . . ?
C9 C6 C5 113.15(17) . . ?
C9 C6 C1 112.39(17) . . ?
C5 C6 C1 116.68(17) . . ?
N2 C3 C2 110.22(18) . . ?
N2 C3 C4 111.56(19) . . ?
C2 C3 C4 110.20(18) . . ?
C8 C4 C3 112.33(19) . . ?
C8 C4 C5 113.80(19) . . ?
C3 C4 C5 113.68(17) . . ?
N1 C1 C2 110.93(18) . . ?
N1 C1 C6 114.24(17) . . ?
C2 C1 C6 111.13(17) . . ?
C7 C2 C1 113.68(18) . . ?
C7 C2 C3 112.97(19) . . ?
C1 C2 C3 111.48(17) . . ?
N3 C5 C6 113.52(17) . . ?
N3 C5 C4 113.25(17) . . ?
C6 C5 C4 111.50(17) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 C17 120.7(2) . . ?
C15 C14 C17 120.3(2) . . ?
C11 C12 C13 119.4(2) . . ?
C16 C15 C14 121.0(2) . . ?
C16 C11 C12 120.67(19) . . ?
C16 C11 S1 119.92(17) . . ?
C12 C11 S1 119.37(17) . . ?
C11 C16 C15 119.4(2) . . ?
O23A S2 O22 128.7(5) . . ?
O23A S2 O21 104.1(6) . . ?
O22 S2 O21 111.49(14) . . ?
O23A S2 O23B 23.4(6) . . ?
O22 S2 O23B 105.3(4) . . ?
O21 S2 O23B 119.2(4) . . ?
O23A S2 C21 99.1(5) . . ?
O22 S2 C21 105.86(11) . . ?
O21 S2 C21 104.77(13) . . ?
O23B S2 C21 109.6(4) . . ?
C22 C21 C26 119.7(2) . . ?
C22 C21 S2 121.60(17) . . ?
C26 C21 S2 118.7(2) . . ?
C25 C26 C21 119.4(3) . . ?
C21 C22 C23 120.6(2) . . ?
C25 C24 C23 118.3(2) . . ?
C25 C24 C27 120.3(3) . . ?
C23 C24 C27 121.3(3) . . ?
C24 C23 C22 120.4(3) . . ?
C24 C25 C26 121.7(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
S1 O13 1.4450(18) . ?
S1 O12 1.4481(16) . ?
S1 O11 1.4753(17) . ?
S1 C11 1.784(2) . ?
N1 C1 1.499(3) . ?
N3 C5 1.503(3) . ?
N2 C3 1.478(3) . ?
C6 C9 1.530(3) . ?
C6 C5 1.539(3) . ?
C6 C1 1.543(3) . ?
C3 C2 1.535(3) . ?
C3 C4 1.538(3) . ?
C4 C8 1.534(3) . ?
C4 C5 1.542(3) . ?
C1 C2 1.533(3) . ?
C2 C7 1.530(3) . ?
C13 C14 1.386(3) . ?
C13 C12 1.399(3) . ?
C14 C15 1.390(4) . ?
C14 C17 1.516(3) . ?
C12 C11 1.386(3) . ?
C15 C16 1.389(3) . ?
C11 C16 1.384(3) . ?
S2 O23A 1.382(15) . ?
S2 O22 1.437(2) . ?
S2 O21 1.443(2) . ?
S2 O23B 1.490(11) . ?
S2 C21 1.786(2) . ?
C21 C22 1.374(4) . ?
C21 C26 1.393(3) . ?
C26 C25 1.390(4) . ?
C22 C23 1.397(4) . ?
C24 C25 1.383(4) . ?
C24 C23 1.393(4) . ?
C24 C27 1.515(4) . ?
