#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/36/7023600.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_7023600
loop_
_publ_author_name
'Majhi, Paresh Kumar'
'Sauerbrey, Susanne'
'Leiendecker, Alexander'
'Schnakenburg, Gregor'
'Arduengo, 3rd, Anthony J'
'Streubel, Rainer'
_publ_section_title
;
 Synthesis and first complexes of C(4/5) P-bifunctional
 imidazole-2-thiones.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13126
_journal_page_last               13136
_journal_paper_doi               10.1039/c3dt51557e
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C29 H26 N2 P2 S3'
_chemical_formula_sum            'C29 H26 N2 P2 S3'
_chemical_formula_weight         560.64
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.742(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6164(16)
_cell_length_b                   12.2568(12)
_cell_length_c                   14.9796(14)
_cell_measurement_reflns_used    8200
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.83
_cell_volume                     2644.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'φ and ω CCD rotation images, thin slices'
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17773
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.7849
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (2009/2), Bruker AXS 2009'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0286
_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)+(0.0339P)²+3.1751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                2866
_reflns_number_total             3185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt51557e.txt
_cod_data_source_block           Greg1402f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7023600
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.0000 0.24125(15) 0.2500 0.0138(3) Uani 1 2 d S
C2 C 0.95692(9) 0.41799(11) 0.25258(9) 0.0133(3) Uani 1 1 d .
C3 C 0.85280(9) 0.26457(11) 0.27307(10) 0.0164(3) Uani 1 1 d .
H3C H 0.8276 0.3211 0.3024 0.025 Uiso 1 1 calc R
H3B H 0.8724 0.2017 0.3167 0.025 Uiso 1 1 calc R
H3A H 0.8049 0.2418 0.2112 0.025 Uiso 1 1 calc R
C4 C 0.76610(9) 0.46565(11) 0.15424(10) 0.0144(3) Uani 1 1 d .
C5 C 0.68339(9) 0.47713(11) 0.16837(10) 0.0165(3) Uani 1 1 d .
H5A H 0.6834 0.5125 0.2248 0.020 Uiso 1 1 calc R
C6 C 0.60132(10) 0.43700(12) 0.10016(11) 0.0194(3) Uani 1 1 d .
H6A H 0.5451 0.4447 0.1100 0.023 Uiso 1 1 calc R
C7 C 0.60083(10) 0.38542(12) 0.01732(11) 0.0219(3) Uani 1 1 d .
H7A H 0.5444 0.3574 -0.0290 0.026 Uiso 1 1 calc R
C8 C 0.68282(10) 0.37491(12) 0.00227(11) 0.0216(3) Uani 1 1 d .
H8A H 0.6822 0.3406 -0.0548 0.026 Uiso 1 1 calc R
C9 C 0.76560(10) 0.41436(12) 0.07036(10) 0.0188(3) Uani 1 1 d .
H9A H 0.8217 0.4067 0.0602 0.023 Uiso 1 1 calc R
C10 C 0.89190(9) 0.63883(11) 0.18022(10) 0.0153(3) Uani 1 1 d .
C11 C 0.90810(10) 0.62451(12) 0.09553(10) 0.0191(3) Uani 1 1 d .
H11A H 0.9216 0.5540 0.0780 0.023 Uiso 1 1 calc R
C12 C 0.90445(11) 0.71355(13) 0.03709(11) 0.0233(3) Uani 1 1 d .
H12A H 0.9169 0.7041 -0.0197 0.028 Uiso 1 1 calc R
C13 C 0.88273(11) 0.81646(13) 0.06092(12) 0.0255(3) Uani 1 1 d .
H13A H 0.8773 0.8765 0.0189 0.031 Uiso 1 1 calc R
C14 C 0.86896(11) 0.83145(12) 0.14646(12) 0.0254(3) Uani 1 1 d .
H14A H 0.8563 0.9023 0.1639 0.031 Uiso 1 1 calc R
C15 C 0.87362(10) 0.74327(12) 0.20646(11) 0.0192(3) Uani 1 1 d .
H15A H 0.8645 0.7538 0.2650 0.023 Uiso 1 1 calc R
N N 0.93291(7) 0.30836(9) 0.25651(8) 0.0143(2) Uani 1 1 d .
P P 0.87190(2) 0.52327(3) 0.24470(2) 0.01310(9) Uani 1 1 d .
S1 S 1.0000 0.10444(4) 0.2500 0.01675(11) Uani 1 2 d S
S2 S 0.86093(2) 0.55497(3) 0.36742(2) 0.01890(10) Uani 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'
P P 0.1023 0.0942 '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
N C1 N 105.88(16) . 2_755
N C1 S1 127.06(8) . .
N C1 S1 127.06(8) 2_755 .
C2 C2 N 106.57(7) 2_755 .
C2 C2 P 134.39(5) 2_755 .
N C2 P 118.77(9) . .
N C3 H3C 109.5 . .
N C3 H3B 109.5 . .
H3C C3 H3B 109.5 . .
N C3 H3A 109.5 . .
H3C C3 H3A 109.5 . .
H3B C3 H3A 109.5 . .
C5 C4 C9 119.77(12) . .
C5 C4 P 118.28(10) . .
C9 C4 P 121.90(10) . .
C6 C5 C4 119.99(13) . .
C6 C5 H5A 120.0 . .
C4 C5 H5A 120.0 . .
C5 C6 C7 120.30(13) . .
C5 C6 H6A 119.8 . .
C7 C6 H6A 119.8 . .
C8 C7 C6 119.97(13) . .
C8 C7 H7A 120.0 . .
C6 C7 H7A 120.0 . .
C9 C8 C7 120.24(14) . .
C9 C8 H8A 119.9 . .
C7 C8 H8A 119.9 . .
C8 C9 C4 119.72(13) . .
C8 C9 H9A 120.1 . .
C4 C9 H9A 120.1 . .
C11 C10 C15 119.85(13) . .
C11 C10 P 121.06(11) . .
C15 C10 P 118.04(10) . .
C12 C11 C10 119.79(13) . .
C12 C11 H11A 120.1 . .
C10 C11 H11A 120.1 . .
C11 C12 C13 120.49(14) . .
C11 C12 H12A 119.8 . .
C13 C12 H12A 119.8 . .
C12 C13 C14 119.80(14) . .
C12 C13 H13A 120.1 . .
C14 C13 H13A 120.1 . .
C15 C14 C13 120.33(14) . .
C15 C14 H14A 119.8 . .
C13 C14 H14A 119.8 . .
C14 C15 C10 119.66(14) . .
C14 C15 H15A 120.2 . .
C10 C15 H15A 120.2 . .
C1 N C2 110.45(11) . .
C1 N C3 121.31(11) . .
C2 N C3 128.07(11) . .
C10 P C2 108.49(6) . .
C10 P C4 101.54(6) . .
C2 P C4 101.64(6) . .
C10 P S2 116.34(5) . .
C2 P S2 114.04(5) . .
C4 P S2 113.12(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N 1.3648(15) .
C1 N 1.3649(15) 2_755
C1 S1 1.6768(19) .
C2 C2 1.377(3) 2_755
C2 N 1.4025(16) .
C2 P 1.8223(13) .
C3 N 1.4679(16) .
C3 H3C 0.9800 .
C3 H3B 0.9800 .
C3 H3A 0.9800 .
C4 C5 1.3944(18) .
C4 C9 1.4022(19) .
C4 P 1.8259(14) .
C5 C6 1.384(2) .
C5 H5A 0.9500 .
C6 C7 1.390(2) .
C6 H6A 0.9500 .
C7 C8 1.389(2) .
C7 H7A 0.9500 .
C8 C9 1.388(2) .
C8 H8A 0.9500 .
C9 H9A 0.9500 .
C10 C11 1.3973(19) .
C10 C15 1.4005(19) .
C10 P 1.8083(14) .
C11 C12 1.386(2) .
C11 H11A 0.9500 .
C12 C13 1.388(2) .
C12 H12A 0.9500 .
C13 C14 1.391(2) .
C13 H13A 0.9500 .
C14 C15 1.390(2) .
C14 H14A 0.9500 .
C15 H15A 0.9500 .
P S2 1.9501(5) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C9 C4 C5 C6 0.6(2) .
P C4 C5 C6 178.35(11) .
C4 C5 C6 C7 -0.2(2) .
C5 C6 C7 C8 -0.6(2) .
C6 C7 C8 C9 0.9(2) .
C7 C8 C9 C4 -0.4(2) .
C5 C4 C9 C8 -0.3(2) .
P C4 C9 C8 -177.97(11) .
C15 C10 C11 C12 -1.1(2) .
P C10 C11 C12 166.91(11) .
C10 C11 C12 C13 -1.5(2) .
C11 C12 C13 C14 3.1(2) .
C12 C13 C14 C15 -2.3(2) .
C13 C14 C15 C10 -0.3(2) .
C11 C10 C15 C14 1.9(2) .
P C10 C15 C14 -166.41(11) .
N C1 N C2 0.93(6) 2_755
S1 C1 N C2 -179.07(6) .
N C1 N C3 -174.66(13) 2_755
S1 C1 N C3 5.34(13) .
C2 C2 N C1 -2.44(17) 2_755
P C2 N C1 172.44(7) .
C2 C2 N C3 172.78(14) 2_755
P C2 N C3 -12.34(18) .
C11 C10 P C2 44.75(13) .
C15 C10 P C2 -147.04(11) .
C11 C10 P C4 -61.84(12) .
C15 C10 P C4 106.37(11) .
C11 C10 P S2 174.91(10) .
C15 C10 P S2 -16.88(12) .
C2 C2 P C10 22.5(2) 2_755
N C2 P C10 -150.63(10) .
C2 C2 P C4 129.01(19) 2_755
N C2 P C4 -44.11(11) .
C2 C2 P S2 -108.92(19) 2_755
N C2 P S2 77.96(11) .
C5 C4 P C10 -108.14(11) .
C9 C4 P C10 69.53(13) .
C5 C4 P C2 139.98(11) .
C9 C4 P C2 -42.35(13) .
C5 C4 P S2 17.28(12) .
C9 C4 P S2 -165.05(10) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102527851
