#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/10/4111000.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_4111000
loop_
_publ_author_name
'Natalie E. Mansfield'
'Joanna Grundy'
'Martyn P. Coles'
'Anthony G. Avent'
'Peter B. Hitchcock'
_publ_section_title
;
 A Conformational Study of Phospha(III)- and Phospha(V)-guanidine
 Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13879
_journal_page_last               13893
_journal_paper_doi               10.1021/ja064212t
_journal_volume                  128
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C25 H33 N2 P S'
_chemical_formula_sum            'C25 H33 N2 P S'
_chemical_formula_weight         424.56
_chemical_name_common            '[Ph2P(S){C(Ncy)(NHcy)}]'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2003-09-16T11:39:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.495(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3934(2)
_cell_length_b                   9.6078(2)
_cell_length_c                   17.3407(3)
_cell_measurement_reflns_used    19926
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      3.705
_cell_measurement_wavelength     0.71073
_cell_volume                     2357.91(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.394403E-1
_diffrn_orient_matrix_UB_12      -0.793557E-1
_diffrn_orient_matrix_UB_13      0.248378E-1
_diffrn_orient_matrix_UB_21      -0.47304E-1
_diffrn_orient_matrix_UB_22      -0.673292E-1
_diffrn_orient_matrix_UB_23      -0.282098E-1
_diffrn_orient_matrix_UB_31      0.346323E-1
_diffrn_orient_matrix_UB_32      -0.15919E-2
_diffrn_orient_matrix_UB_33      -0.450221E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23714
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.93
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0288P)²+1.3403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                3539
_reflns_number_total             4118
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja064212tsi20060615_042934.cif
_cod_data_source_block           sep1203
_cod_database_code               4111000
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S S 0.44431(3) 0.32344(5) 0.29501(3) 0.03148(13) Uani 1 1 d .
P P 0.35926(3) 0.30587(4) 0.19395(2) 0.02108(12) Uani 1 1 d .
N1 N 0.27960(11) 0.10797(15) 0.26877(9) 0.0296(3) Uani 1 1 d .
H1N H 0.3235(14) 0.147(2) 0.3040(11) 0.032(5) Uiso 1 1 d .
N2 N 0.22439(10) 0.09262(14) 0.13599(8) 0.0263(3) Uani 1 1 d .
C1 C 0.28955(11) 0.46074(17) 0.16769(9) 0.0235(4) Uani 1 1 d .
C2 C 0.33773(12) 0.58687(17) 0.16610(10) 0.0266(4) Uani 1 1 d .
H2 H 0.4048 0.5885 0.1781 0.032 Uiso 1 1 calc R
C3 C 0.28839(13) 0.70896(18) 0.14712(10) 0.0308(4) Uani 1 1 d .
H3 H 0.3215 0.7943 0.1459 0.037 Uiso 1 1 calc R
C4 C 0.19074(13) 0.70705(19) 0.12993(12) 0.0376(5) Uani 1 1 d .
H4 H 0.1567 0.791 0.1166 0.045 Uiso 1 1 calc R
C5 C 0.14264(14) 0.5833(2) 0.13218(13) 0.0442(5) Uani 1 1 d .
H5 H 0.0755 0.5825 0.1206 0.053 Uiso 1 1 calc R
C6 C 0.19155(12) 0.46006(19) 0.15128(11) 0.0337(4) Uani 1 1 d .
H6 H 0.158 0.3753 0.1531 0.04 Uiso 1 1 calc R
C7 C 0.42440(11) 0.27271(17) 0.11584(9) 0.0216(3) Uani 1 1 d .
C8 C 0.41453(12) 0.35193(17) 0.04770(9) 0.0254(4) Uani 1 1 d .
H8 H 0.3711 0.4273 0.0397 0.03 Uiso 1 1 calc R
C9 C 0.46861(12) 0.32017(19) -0.00862(10) 0.0311(4) Uani 1 1 d .
H9 H 0.4623 0.3744 -0.0551 0.037 Uiso 1 1 calc R
C10 C 0.53122(12) 0.2107(2) 0.00245(11) 0.0341(4) Uani 1 1 d .
H10 H 0.5676 0.1893 -0.0365 0.041 Uiso 1 1 calc R
C11 C 0.54142(12) 0.1316(2) 0.07002(11) 0.0336(4) Uani 1 1 d .
H11 H 0.5847 0.056 0.0774 0.04 Uiso 1 1 calc R
C12 C 0.48843(12) 0.16280(18) 0.12696(10) 0.0292(4) Uani 1 1 d .
H12 H 0.4958 0.1091 0.1737 0.035 Uiso 1 1 calc R
C13 C 0.27629(11) 0.15330(16) 0.19399(10) 0.0236(4) Uani 1 1 d .
C14 C 0.22993(12) -0.01556(18) 0.28888(10) 0.0285(4) Uani 1 1 d .
H14 H 0.2407 -0.0928 0.2529 0.034 Uiso 1 1 calc R
C15 C 0.12381(13) 0.0082(2) 0.28009(11) 0.0365(4) Uani 1 1 d .
H15A H 0.0971 0.0299 0.2247 0.044 Uiso 1 1 calc R
H15B H 0.1119 0.0889 0.3125 0.044 Uiso 1 1 calc R
C16 C 0.07500(14) -0.1209(2) 0.30566(13) 0.0464(5) Uani 1 1 d .
H16A H 0.0067 -0.1018 0.3016 0.056 Uiso 1 1 calc R
H16B H 0.082 -0.1992 0.2701 0.056 Uiso 1 1 calc R
C17 C 0.11696(16) -0.1615(2) 0.38933(13) 0.0510(6) Uani 1 1 d .
H17A H 0.1045 -0.0869 0.4255 0.061 Uiso 1 1 calc R
H17B H 0.0863 -0.2478 0.4034 0.061 Uiso 1 1 calc R
C18 C 0.22268(16) -0.1848(2) 0.39860(15) 0.0539(6) Uani 1 1 d .
H18A H 0.2347 -0.2664 0.367 0.065 Uiso 1 1 calc R
H18B H 0.249 -0.2052 0.4543 0.065 Uiso 1 1 calc R
C19 C 0.27246(14) -0.0576(2) 0.37243(12) 0.0414(5) Uani 1 1 d .
H19A H 0.2672 0.0211 0.4082 0.05 Uiso 1 1 calc R
H19B H 0.3404 -0.0787 0.3757 0.05 Uiso 1 1 calc R
C20 C 0.20940(11) 0.14525(17) 0.05572(9) 0.0235(4) Uani 1 1 d .
H20 H 0.2357 0.2415 0.0554 0.028 Uiso 1 1 calc R
C21 C 0.10293(12) 0.1485(2) 0.02534(11) 0.0350(4) Uani 1 1 d .
H21A H 0.0765 0.0545 0.0304 0.042 Uiso 1 1 calc R
H21B H 0.073 0.2131 0.058 0.042 Uiso 1 1 calc R
C22 C 0.07906(14) 0.1946(2) -0.05997(12) 0.0448(5) Uani 1 1 d .
H22A H 0.0098 0.1897 -0.0781 0.054 Uiso 1 1 calc R
H22B H 0.0989 0.2926 -0.0642 0.054 Uiso 1 1 calc R
C23 C 0.12795(15) 0.1038(2) -0.11217(11) 0.0446(5) Uani 1 1 d .
H23A H 0.1016 0.0084 -0.1138 0.054 Uiso 1 1 calc R
H23B H 0.1157 0.1414 -0.1662 0.054 Uiso 1 1 calc R
C24 C 0.23369(13) 0.0983(2) -0.08211(10) 0.0360(4) Uani 1 1 d .
H24A H 0.2611 0.1918 -0.0867 0.043 Uiso 1 1 calc R
H24B H 0.263 0.0334 -0.115 0.043 Uiso 1 1 calc R
C25 C 0.25646(12) 0.05085(18) 0.00318(10) 0.0282(4) Uani 1 1 d .
H25A H 0.3258 0.0521 0.0214 0.034 Uiso 1 1 calc R
H25B H 0.2342 -0.0459 0.0071 0.034 Uiso 1 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 0 '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
C1 P C7 107.22(7)
C1 P C13 108.47(7)
C7 P C13 106.09(7)
C1 P S 112.55(6)
C7 P S 111.17(6)
C13 P S 111.05(6)
C13 N1 C14 123.65(15)
C13 N2 C20 123.76(14)
C6 C1 C2 119.29(15)
C6 C1 P 123.04(13)
C2 C1 P 117.65(12)
C3 C2 C1 120.38(16)
C2 C3 C4 119.93(16)
C5 C4 C3 120.05(17)
C4 C5 C6 120.47(17)
C5 C6 C1 119.87(17)
C8 C7 C12 119.70(15)
C8 C7 P 123.55(12)
C12 C7 P 116.74(12)
C9 C8 C7 119.57(16)
C10 C9 C8 120.43(16)
C9 C10 C11 120.30(15)
C10 C11 C12 119.88(16)
C11 C12 C7 120.12(16)
N2 C13 N1 121.18(15)
N2 C13 P 129.16(12)
N1 C13 P 109.64(12)
N1 C14 C19 108.28(15)
N1 C14 C15 112.30(15)
C19 C14 C15 110.93(14)
C14 C15 C16 110.73(16)
C17 C16 C15 111.21(17)
C18 C17 C16 110.85(17)
C17 C18 C19 111.49(18)
C14 C19 C18 111.49(17)
N2 C20 C21 107.50(13)
N2 C20 C25 111.00(13)
C21 C20 C25 109.41(14)
C22 C21 C20 112.07(15)
C23 C22 C21 111.40(16)
C24 C23 C22 111.07(16)
C23 C24 C25 111.62(15)
C24 C25 C20 111.12(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S P 1.9536(6)
P C1 1.8061(16)
P C7 1.8103(15)
P C13 1.8909(16)
N1 C13 1.361(2)
N1 C14 1.460(2)
N2 C13 1.279(2)
N2 C20 1.460(2)
C1 C6 1.387(2)
C1 C2 1.399(2)
C2 C3 1.380(2)
C3 C4 1.383(3)
C4 C5 1.380(3)
C5 C6 1.386(3)
C7 C8 1.391(2)
C7 C12 1.392(2)
C8 C9 1.389(2)
C9 C10 1.376(3)
C10 C11 1.381(3)
C11 C12 1.386(2)
C14 C19 1.521(3)
C14 C15 1.524(2)
C15 C16 1.530(3)
C16 C17 1.518(3)
C17 C18 1.517(3)
C18 C19 1.527(3)
C20 C21 1.527(2)
C20 C25 1.529(2)
C21 C22 1.522(3)
C22 C23 1.519(3)
C23 C24 1.517(3)
C24 C25 1.525(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660420
