#------------------------------------------------------------------------------
#$Date: 2024-10-06 11:14:28 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/70/7717018.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_7717018
loop_
_publ_author_name
'Kalisch, Tim'
'Schnakenburg, Gregor'
'Nikonov, Georgii I.'
'Streubel, Rainer'
_publ_section_title
;
 [4 + 1]- and [4 + 2]-cycloadditions of a thiazole-2-thione-based
 1,4-diphosphinine - broadening the scope.
;
_journal_issue                   38
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16018
_journal_page_last               16022
_journal_paper_doi               10.1039/d4dt02029d
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C18 H26 N2 P2 S4'
_chemical_formula_sum            'C18 H26 N2 P2 S4'
_chemical_formula_weight         460.62
_chemical_name_systematic        KT-374
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                102.542(3)
_cell_angle_beta                 101.566(3)
_cell_angle_gamma                106.023(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3076(3)
_cell_length_b                   10.2906(4)
_cell_length_c                   15.3615(6)
_cell_measurement_reflns_used    34334
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.03
_cell_measurement_theta_min      4.68
_cell_volume                     1183.70(9)
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)'
_computing_data_reduction
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27308
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.614
_diffrn_reflns_theta_min         4.671
_diffrn_source                   'Axo Cu'
_exptl_absorpt_coefficient_mu    5.00
_exptl_absorpt_correction_T_max  0.4032
_exptl_absorpt_correction_T_min  0.2631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0756P)²+0.5265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             4455
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02029d2.cif
_cod_data_source_block           4f
_cod_depositor_comments
'Adding full bibliography for 7717017--7717018.cif.'
_cod_original_cell_volume        1183.70(8)
_cod_database_code               7717018
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.788
_shelx_estimated_absorpt_t_min   0.434
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B),
 C15(H15A,H15B), C17(H17A,H17B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68438(7) 0.48122(6) 0.44985(4) 0.02768(15) Uani 1 1 d . . . . .
S2 S 0.70894(9) 0.27009(7) 0.55591(4) 0.03775(17) Uani 1 1 d . . . . .
S3 S 0.48001(6) 0.19486(5) 0.03361(4) 0.02448(14) Uani 1 1 d . . . . .
S4 S 0.71813(7) 0.36896(6) -0.05307(4) 0.02918(15) Uani 1 1 d . . . . .
P1 P 0.30658(7) 0.18931(5) 0.19936(4) 0.02255(15) Uani 1 1 d . . . . .
P2 P 0.50625(7) 0.53432(5) 0.26381(4) 0.02439(15) Uani 1 1 d . . . . .
N1 N 0.5102(2) 0.22015(19) 0.38139(13) 0.0248(4) Uani 1 1 d . . . . .
N2 N 0.6195(2) 0.46088(18) 0.10032(13) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.4662(3) 0.2832(2) 0.31263(15) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.6280(3) 0.3105(2) 0.46151(16) 0.0280(5) Uani 1 1 d . . . . .
C3 C 0.5481(3) 0.4242(2) 0.33810(15) 0.0253(4) Uani 1 1 d . . . . .
C4 C 0.4420(3) 0.0668(2) 0.36998(17) 0.0286(5) Uani 1 1 d . . . . .
H4A H 0.327237 0.025251 0.322785 0.034 Uiso 1 1 calc R . . . .
H4B H 0.424285 0.052155 0.429444 0.034 Uiso 1 1 calc R . . . .
C5 C 0.5647(3) -0.0095(2) 0.34030(17) 0.0319(5) Uani 1 1 d . . . . .
H5A H 0.681489 0.037525 0.385260 0.038 Uiso 1 1 calc R . . . .
H5B H 0.521904 -0.107679 0.343610 0.038 Uiso 1 1 calc R . . . .
C6 C 0.5830(3) -0.0141(3) 0.24359(18) 0.0349(5) Uani 1 1 d . . . . .
H6A H 0.468983 -0.063932 0.198034 0.052 Uiso 1 1 calc GR . . . .
H6B H 0.664519 -0.063750 0.230588 0.052 Uiso 1 1 calc GR . . . .
H6C H 0.627443 0.082487 0.239623 0.052 Uiso 1 1 calc GR . . . .
C7 C 0.4383(3) 0.2762(2) 0.13380(15) 0.0235(4) Uani 1 1 d . . . . .
C8 C 0.6143(3) 0.3551(2) 0.02864(16) 0.0246(4) Uani 1 1 d . . . . .
C9 C 0.5230(3) 0.4171(2) 0.15972(15) 0.0238(4) Uani 1 1 d . . . . .
C10 C 0.7275(3) 0.6084(2) 0.11603(16) 0.0253(5) Uani 1 1 d . . . . .
H10A H 0.673236 0.672514 0.147159 0.030 Uiso 1 1 calc R . . . .
H10B H 0.731944 0.625687 0.055475 0.030 Uiso 1 1 calc R . . . .
C11 C 0.9114(3) 0.6414(2) 0.17523(18) 0.0307(5) Uani 1 1 d . . . . .
H11A H 0.963222 0.573523 0.146186 0.037 Uiso 1 1 calc R . . . .
H11B H 0.907729 0.630364 0.237303 0.037 Uiso 1 1 calc R . . . .
C12 C 1.0253(3) 0.7914(2) 0.18593(19) 0.0371(6) Uani 1 1 d . . . . .
H12A H 0.974157 0.858785 0.214631 0.056 Uiso 1 1 calc GR . . . .
H12B H 1.032405 0.801590 0.124704 0.056 Uiso 1 1 calc GR . . . .
H12C H 1.142525 0.810303 0.225311 0.056 Uiso 1 1 calc GR . . . .
C13 C 0.1636(3) 0.3048(2) 0.20940(15) 0.0242(4) Uani 1 1 d . . . . .
C14 C 0.2644(3) 0.4659(2) 0.23666(16) 0.0266(5) Uani 1 1 d . . . . .
H14A H 0.232969 0.511110 0.291556 0.032 Uiso 1 1 calc R . . . .
H14B H 0.217657 0.500904 0.185300 0.032 Uiso 1 1 calc R . . . .
C15 C 0.0740(3) 0.2679(2) 0.28449(16) 0.0273(5) Uani 1 1 d . . . . .
H15A H 0.019491 0.164060 0.267673 0.033 Uiso 1 1 calc R . . . .
H15B H 0.164396 0.298138 0.344508 0.033 Uiso 1 1 calc R . . . .
C16 C -0.0653(3) 0.3356(3) 0.29745(18) 0.0331(5) Uani 1 1 d . . . . .
H16A H -0.153145 0.309863 0.237866 0.050 Uiso 1 1 calc GR . . . .
H16B H -0.010838 0.438561 0.320252 0.050 Uiso 1 1 calc GR . . . .
H16C H -0.121179 0.301782 0.342521 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.0318(3) 0.2618(2) 0.11312(16) 0.0278(5) Uani 1 1 d . . . . .
H17A H -0.037124 0.326417 0.114878 0.033 Uiso 1 1 calc R . . . .
H17B H 0.098058 0.276683 0.067202 0.033 Uiso 1 1 calc R . . . .
C18 C -0.0952(3) 0.1100(2) 0.07818(17) 0.0310(5) Uani 1 1 d . . . . .
H18A H -0.165330 0.092055 0.014644 0.046 Uiso 1 1 calc GR . . . .
H18B H -0.172175 0.096434 0.118581 0.046 Uiso 1 1 calc GR . . . .
H18C H -0.029612 0.044180 0.078947 0.046 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C3 S1 C2 92.36(11) . . ?
C7 S3 C8 92.08(10) . . ?
C1 P1 C13 96.35(10) . . ?
C7 P1 C1 95.11(10) . . ?
C7 P1 C13 98.31(9) . . ?
C3 P2 C9 94.54(10) . . ?
C3 P2 C14 96.38(10) . . ?
C9 P2 C14 96.60(10) . . ?
C1 N1 C4 124.20(18) . . ?
C2 N1 C1 114.85(18) . . ?
C2 N1 C4 120.91(19) . . ?
C8 N2 C9 114.59(17) . . ?
C8 N2 C10 121.75(17) . . ?
C9 N2 C10 123.57(17) . . ?
N1 C1 P1 124.61(16) . . ?
C3 C1 P1 121.70(17) . . ?
C3 C1 N1 113.6(2) . . ?
S2 C2 S1 124.20(14) . . ?
N1 C2 S1 108.71(17) . . ?
N1 C2 S2 127.10(18) . . ?
S1 C3 P2 126.69(13) . . ?
C1 C3 S1 110.44(17) . . ?
C1 C3 P2 122.80(18) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
N1 C4 C5 112.39(17) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 114.9(2) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
S3 C7 P1 126.42(12) . . ?
C9 C7 S3 110.27(16) . . ?
C9 C7 P1 123.28(17) . . ?
S4 C8 S3 123.41(13) . . ?
N2 C8 S3 109.35(15) . . ?
N2 C8 S4 127.24(16) . . ?
N2 C9 P2 125.14(16) . . ?
C7 C9 P2 121.17(16) . . ?
C7 C9 N2 113.68(19) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 C11 111.70(18) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.3(2) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 P1 114.38(14) . . ?
C15 C13 P1 104.58(14) . . ?
C15 C13 C14 110.71(17) . . ?
C17 C13 P1 106.59(14) . . ?
C17 C13 C14 108.33(18) . . ?
C17 C13 C15 112.23(17) . . ?
P2 C14 H14A 107.1 . . ?
P2 C14 H14B 107.1 . . ?
C13 C14 P2 120.95(15) . . ?
C13 C14 H14A 107.1 . . ?
C13 C14 H14B 107.1 . . ?
H14A C14 H14B 106.8 . . ?
C13 C15 H15A 108.6 . . ?
C13 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C13 114.60(19) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 108.1 . . ?
C13 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
C18 C17 C13 116.59(19) . . ?
C18 C17 H17A 108.1 . . ?
C18 C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C2 1.747(2) . ?
S1 C3 1.729(2) . ?
S2 C2 1.659(2) . ?
S3 C7 1.733(2) . ?
S3 C8 1.744(2) . ?
S4 C8 1.669(2) . ?
P1 C1 1.832(2) . ?
P1 C7 1.818(2) . ?
P1 C13 1.903(2) . ?
P2 C3 1.824(2) . ?
P2 C9 1.837(2) . ?
P2 C14 1.861(2) . ?
N1 C1 1.394(3) . ?
N1 C2 1.362(3) . ?
N1 C4 1.479(3) . ?
N2 C8 1.354(3) . ?
N2 C9 1.397(3) . ?
N2 C10 1.473(3) . ?
C1 C3 1.351(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.529(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.516(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C9 1.352(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.554(3) . ?
C13 C15 1.552(3) . ?
C13 C17 1.543(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.530(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.530(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 144.2 41.1 ?
