#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/46/2004691.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004691
loop_
_publ_author_name
'Carmalt, C. J.'
'Cowley, A. H.'
'Decken, A.'
'Lawson, Y. G.'
'Norman, N. C.'
_publ_section_title
;
 Bis(diphenylphosphino)methane Disulfide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              931
_journal_page_last               933
_journal_paper_doi               10.1107/S0108270195013230
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C25 H22 P2 S2'
_chemical_formula_sum            'C25 H22 P2 S2'
_chemical_formula_weight         448.49
_chemical_name_systematic
;
 Bisdiphenylphosphino methane disulfide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.63(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.527(1)
_cell_length_b                   10.731(1)
_cell_length_c                   22.525(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     2270.4(4)
_computing_cell_refinement
'Enraf-Nonius CAD-4 EXPRESS (Enraf-Nonius, 1993)'
_computing_data_collection
'Enraf-Nonius CAD-4 EXPRESS (Enraf-Nonius, 1993)'
_computing_data_reduction        'XCAD4 (Siemens, 1993)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1995)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       2θ/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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5331
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.124
_refine_ls_goodness_of_fit_obs   1.138
_refine_ls_hydrogen_treatment    'see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_restrained_S_obs      1.138
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_obs          0.046
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.04P)^2^ + 1.00P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.108
_refine_ls_wR_factor_obs         0.0927
_reflns_number_observed          3052
_reflns_number_total             3976
_reflns_observed_criterion       I>2sigma(I)
_cod_data_source_file            bk1168.cif
_cod_data_source_block           claire8
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2004691
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_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_calc_flag
_atom_site_type_symbol
P(1) 1 0.0083(1) 0.9115(1) 0.2358(1) 0.041(1) Uani d P
P(2) 1 -0.0180(1) 0.7375(1) 0.1222(1) 0.044(1) Uani d P
S(1) 1 0.1454(1) 1.0281(1) 0.2120(1) 0.060(1) Uani d S
S(2) 1 -0.1863(1) 0.8229(1) 0.0812(1) 0.071(1) Uani d S
C 1 0.0171(3) 0.7554(3) 0.2042(1) 0.043(1) Uani d C
C(1) 1 0.0350(3) 0.8840(2) 0.3164(1) 0.045(1) Uani d C
C(2) 1 0.1452(3) 0.8092(3) 0.3432(1) 0.056(1) Uani d C
C(3) 1 0.1691(4) 0.7908(4) 0.4048(1) 0.070(1) Uani d C
C(4) 1 0.0857(4) 0.8476(4) 0.4400(2) 0.076(1) Uani d C
C(5) 1 -0.0233(4) 0.9221(4) 0.4143(2) 0.079(1) Uani d C
C(6) 1 -0.0490(4) 0.9417(3) 0.3525(2) 0.064(1) Uani d C
C(7) 1 -0.1759(3) 0.9570(2) 0.2154(1) 0.045(1) Uani d C
C(8) 1 -0.2833(3) 0.8794(3) 0.2285(1) 0.058(1) Uani d C
C(9) 1 -0.4241(3) 0.9100(4) 0.2073(2) 0.070(1) Uani d C
C(10) 1 -0.4567(4) 1.0162(4) 0.1745(2) 0.079(1) Uani d C
C(11) 1 -0.3523(4) 1.0932(4) 0.1625(2) 0.076(1) Uani d C
C(12) 1 -0.2110(4) 1.0643(3) 0.1833(1) 0.059(1) Uani d C
C(13) 1 0.1439(3) 0.7815(2) 0.0956(1) 0.047(1) Uani d C
C(14) 1 0.1431(4) 0.8785(3) 0.0553(1) 0.065(1) Uani d C
C(15) 1 0.2635(5) 0.9086(4) 0.0323(2) 0.083(1) Uani d C
C(16) 1 0.3861(5) 0.8432(4) 0.0497(2) 0.079(1) Uani d C
C(17) 1 0.3898(4) 0.7484(4) 0.0897(2) 0.070(1) Uani d C
C(18) 1 0.2704(3) 0.7160(3) 0.1129(1) 0.055(1) Uani d C
C(19) 1 -0.0338(3) 0.5697(3) 0.1118(1) 0.044(1) Uani d C
C(20) 1 -0.1043(3) 0.5269(3) 0.0567(1) 0.060(1) Uani d C
C(21) 1 -0.1212(4) 0.4011(4) 0.0460(2) 0.072(1) Uani d C
C(22) 1 -0.0712(4) 0.3173(3) 0.0897(2) 0.070(1) Uani d C
C(23) 1 -0.0011(4) 0.3576(3) 0.1441(2) 0.067(1) Uani d C
C(24) 1 0.0188(3) 0.4837(3) 0.1555(1) 0.056(1) Uani d C
H1A 1 0.1026(36) 0.7296(30) 0.2178(14) 0.072(2) Uiso d H
H1B 1 -0.0509(33) 0.7085(30) 0.2188(14) 0.072(2) Uiso d H
H2 1 0.2026(34) 0.7692(30) 0.3207(15) 0.072(2) Uiso d H
H3 1 0.2428(34) 0.7447(31) 0.4207(15) 0.072(2) Uiso d H
H4 1 0.1006(33) 0.8391(30) 0.4808(15) 0.072(2) Uiso d H
H5 1 -0.0806(34) 0.9586(30) 0.4364(14) 0.072(2) Uiso d H
H6 1 -0.1197(35) 0.9902(32) 0.3352(14) 0.072(2) Uiso d H
H8 1 -0.2616(34) 0.8053(31) 0.2502(14) 0.072(2) Uiso d H
H9 1 -0.4944(35) 0.8554(31) 0.2161(14) 0.072(2) Uiso d H
H10 1 -0.5493(36) 1.0317(30) 0.1618(14) 0.072(2) Uiso d H
H11 1 -0.3685(34) 1.1634(32) 0.1375(14) 0.072(2) Uiso d H
H12 1 -0.1350(34) 1.1133(30) 0.1751(14) 0.072(2) Uiso d H
H14 1 0.0599(35) 0.9193(31) 0.0468(14) 0.072(2) Uiso d H
H15 1 0.2577(35) 0.9706(31) 0.0065(14) 0.072(2) Uiso d H
H16 1 0.4649(35) 0.8679(30) 0.0344(14) 0.072(2) Uiso d H
H17 1 0.4666(35) 0.7077(31) 0.1013(15) 0.072(2) Uiso d H
H18 1 0.2704(33) 0.6511(30) 0.1402(14) 0.072(2) Uiso d H
H20 1 -0.1387(34) 0.5868(30) 0.0286(14) 0.072(2) Uiso d H
H21 1 -0.1718(33) 0.3749(30) 0.0088(14) 0.072(2) Uiso d H
H22 1 -0.0846(33) 0.2298(32) 0.0824(14) 0.072(2) Uiso d H
H23 1 0.0352(34) 0.2994(31) 0.1735(14) 0.072(2) Uiso d H
H24 1 0.0685(34) 0.5089(30) 0.1929(14) 0.072(2) Uiso d H
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'
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_publ_flag
C(7) P(1) C(1) 105.40(10) yes
C(7) P(1) C 104.80(10) yes
C(1) P(1) C 103.50(10) yes
C(7) P(1) S(1) 115.10(10) yes
C(1) P(1) S(1) 113.09(9) yes
C P(1) S(1) 113.90(10) yes
C(13) P(2) C(19) 105.80(10) yes
C(13) P(2) C 106.50(10) yes
C(19) P(2) C 103.40(10) yes
C(13) P(2) S(2) 113.70(10) yes
C(19) P(2) S(2) 111.22(9) yes
C P(2) S(2) 115.30(10) yes
P(1) C P(2) 118.4(2) yes
C(2) C(1) C(6) 118.6(3) no
C(2) C(1) P(1) 120.1(2) yes
C(6) C(1) P(1) 121.3(2) yes
C(1) C(2) C(3) 120.5(3) no
C(4) C(3) C(2) 120.6(4) no
C(3) C(4) C(5) 119.7(3) no
C(4) C(5) C(6) 120.7(3) no
C(1) C(6) C(5) 120.0(3) no
C(12) C(7) C(8) 119.5(3) no
C(12) C(7) P(1) 120.1(2) yes
C(8) C(7) P(1) 120.2(2) yes
C(9) C(8) C(7) 119.4(3) no
C(10) C(9) C(8) 120.2(4) no
C(11) C(10) C(9) 120.7(3) no
C(10) C(11) C(12) 120.0(4) no
C(7) C(12) C(11) 120.3(3) no
C(14) C(13) C(18) 118.3(3) no
C(14) C(13) P(2) 120.2(2) yes
C(18) C(13) P(2) 121.5(2) yes
C(15) C(14) C(13) 120.8(4) no
C(16) C(15) C(14) 120.0(4) no
C(17) C(16) C(15) 120.2(4) no
C(16) C(17) C(18) 120.8(4) no
C(17) C(18) C(13) 119.9(3) no
C(24) C(19) C(20) 118.7(3) no
C(24) C(19) P(2) 123.9(2) yes
C(20) C(19) P(2) 117.4(2) yes
C(21) C(20) C(19) 120.5(3) no
C(22) C(21) C(20) 120.3(3) no
C(21) C(22) C(23) 120.1(3) no
C(22) C(23) C(24) 120.5(3) no
C(19) C(24) C(23) 120.0(3) no
P(1) C H1A 105(2) no
P(2) C H1A 109(2) no
P(1) C H1B 106(2) no
P(2) C H1B 106(2) no
H1A C H1B 112(3) no
C(1) C(2) H2 121(2) no
C(3) C(2) H2 119(2) no
C(4) C(3) H3 121(2) no
C(2) C(3) H3 118(2) no
C(3) C(4) H4 123(2) no
C(5) C(4) H4 118(2) no
C(4) C(5) H5 121(2) no
C(6) C(5) H5 118(2) no
C(1) C(6) H6 118(2) no
C(5) C(6) H6 122(2) no
C(9) C(8) H8 120(2) no
C(7) C(8) H8 121(2) no
C(10) C(9) H9 122(2) no
C(8) C(9) H9 118(2) no
C(11) C(10) H10 123(2) no
C(9) C(10) H10 117(2) no
C(10) C(11) H11 124(2) no
C(12) C(11) H11 116(2) no
C(7) C(12) H12 117(2) no
C(11) C(12) H12 123(2) no
C(15) C(14) H14 125(2) no
C(13) C(14) H14 115(2) no
C(16) C(15) H15 122(2) no
C(14) C(15) H15 118(2) no
C(17) C(16) H16 123(2) no
C(15) C(16) H16 117(2) no
C(16) C(17) H17 121(2) no
C(18) C(17) H17 119(2) no
C(17) C(18) H18 122(2) no
C(13) C(18) H18 118(2) no
C(21) C(20) H20 123(2) no
C(19) C(20) H20 117(2) no
C(22) C(21) H21 121(2) no
C(20) C(21) H21 119(2) no
C(21) C(22) H22 120(2) no
C(23) C(22) H22 120(2) no
C(22) C(23) H23 120(2) no
C(24) C(23) H23 120(2) no
C(19) C(24) H24 121(2) no
C(23) C(24) H24 119(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P(1) C(7) 1.806(3) yes
P(1) C(1) 1.814(3) yes
P(1) C 1.827(3) yes
P(1) S(1) 1.9480(10) yes
P(2) C(13) 1.808(3) yes
P(2) C(19) 1.819(3) yes
P(2) C 1.831(3) yes
P(2) S(2) 1.9410(10) yes
C(1) C(2) 1.378(4) no
C(1) C(6) 1.380(4) no
C(2) C(3) 1.384(4) no
C(3) C(4) 1.357(5) no
C(4) C(5) 1.360(6) no
C(5) C(6) 1.388(5) no
C(7) C(12) 1.371(4) no
C(7) C(8) 1.388(4) no
C(8) C(9) 1.386(5) no
C(9) C(10) 1.365(5) no
C(10) C(11) 1.354(6) no
C(11) C(12) 1.384(5) no
C(13) C(14) 1.380(4) no
C(13) C(18) 1.393(4) no
C(14) C(15) 1.374(5) no
C(15) C(16) 1.362(6) no
C(16) C(17) 1.356(5) no
C(17) C(18) 1.373(5) no
C(19) C(24) 1.380(4) no
C(19) C(20) 1.387(4) no
C(20) C(21) 1.376(5) no
C(21) C(22) 1.360(5) no
C(22) C(23) 1.363(5) no
C(23) C(24) 1.385(4) no
C H1A 0.87(3) no
C H1B 0.92(3) no
C(2) H2 0.91(3) no
C(3) H3 0.88(3) no
C(4) H4 0.91(3) no
C(5) H5 0.89(3) no
C(6) H6 0.89(3) no
C(8) H8 0.94(3) no
C(9) H9 0.94(3) no
C(10) H10 0.90(3) no
C(11) H11 0.94(3) no
C(12) H12 0.94(3) no
C(14) H14 0.90(3) no
C(15) H15 0.88(3) no
C(16) H16 0.93(3) no
C(17) H17 0.85(3) no
C(18) H18 0.93(3) no
C(20) H20 0.92(3) no
C(21) H21 0.94(3) no
C(22) H22 0.96(3) no
C(23) H23 0.93(3) no
C(24) H24 0.94(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 377367
