#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206638.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_2206638
loop_
_publ_author_name
'Uttecht, Jan-Georg'
'Tuczek, Felix'
'Näther, Christian'
_publ_section_title
;
 Tris[2-(methylsulfanyl)phenyl]phosphine
;
_journal_coeditor_code           BT6715
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2916
_journal_page_last               o2917
_journal_paper_doi               10.1107/S1600536805025602
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C21 H21 P S3'
_chemical_formula_moiety         'C21 H21 P S3'
_chemical_formula_sum            'C21 H21 P S3'
_chemical_formula_weight         400.53
_chemical_name_common            Tris(o-methylthiophenyl)phosphine
_chemical_name_systematic
;
Tris[2-(methylsulfanyl)phenyl]phosphine
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            24
_cell_length_a                   23.4523(15)
_cell_length_b                   23.4523(15)
_cell_length_c                   25.4022(18)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      12.5
_cell_volume                     12099.7(14)
_computing_cell_refinement       IPDS
_computing_data_collection       'IPDS (Stoe & Cie, 1998)'
_computing_data_reduction        IPDS
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'CIFTAB in SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDS-1'
_diffrn_measurement_method       φ
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34061
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.77
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.518
_refine_diff_density_min         -0.573
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         6469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0539
_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)+(0.0594P)²+57.688P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                5279
_reflns_number_total             6469
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6715.cif
_cod_data_source_block           I
_cod_original_cell_volume        12099.6(14)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2206638
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
P1 0.51266(3) 0.45658(3) 0.69623(2) 0.02139(15) Uani d . 1 P
C1 0.43921(13) 0.37446(12) 0.69091(9) 0.0218(5) Uani d . 1 C
C2 0.37735(13) 0.36515(12) 0.70739(9) 0.0224(5) Uani d . 1 C
C3 0.32066(14) 0.30435(13) 0.70169(11) 0.0289(6) Uani d . 1 C
H3 0.2798 0.2979 0.7145 0.035 Uiso calc R 1 H
C4 0.32349(15) 0.25270(14) 0.67714(12) 0.0339(6) Uani d . 1 C
H4 0.2844 0.2115 0.6723 0.041 Uiso calc R 1 H
C5 0.38259(16) 0.26147(14) 0.66005(11) 0.0352(6) Uani d . 1 C
H5 0.3843 0.2263 0.6430 0.042 Uiso calc R 1 H
C6 0.44014(15) 0.32115(13) 0.66724(10) 0.0276(5) Uani d . 1 C
H6 0.4809 0.3258 0.6559 0.033 Uiso calc R 1 H
S1 0.37626(4) 0.43366(4) 0.73565(3) 0.03288(17) Uani d . 1 S
C7 0.29011(16) 0.40440(17) 0.74383(14) 0.0428(7) Uani d . 1 C
H7A 0.2841 0.4392 0.7596 0.064 Uiso calc R 1 H
H7B 0.2709 0.3658 0.7670 0.064 Uiso calc R 1 H
H7C 0.2683 0.3923 0.7094 0.064 Uiso calc R 1 H
C11 0.57859(13) 0.44365(13) 0.67020(10) 0.0247(5) Uani d . 1 C
C12 0.58826(13) 0.44396(13) 0.61566(10) 0.0251(5) Uani d . 1 C
C13 0.64102(14) 0.43905(15) 0.59571(12) 0.0323(6) Uani d . 1 C
H13 0.6464 0.4380 0.5587 0.039 Uiso calc R 1 H
C14 0.68578(16) 0.43570(17) 0.62950(13) 0.0385(7) Uani d . 1 C
H14 0.7220 0.4331 0.6157 0.046 Uiso calc R 1 H
C15 0.67745(17) 0.43615(19) 0.68329(13) 0.0444(8) Uani d . 1 C
H15 0.7080 0.4340 0.7067 0.053 Uiso calc R 1 H
C16 0.62523(15) 0.43966(15) 0.70243(11) 0.0343(6) Uani d . 1 C
H16 0.6199 0.4394 0.7395 0.041 Uiso calc R 1 H
S2 0.52944(4) 0.44698(4) 0.57320(3) 0.03663(19) Uani d . 1 S
C17 0.57505(15) 0.47832(15) 0.51307(11) 0.0345(6) Uani d . 1 C
H17A 0.5469 0.4820 0.4864 0.052 Uiso calc R 1 H
H17B 0.5897 0.4482 0.5005 0.052 Uiso calc R 1 H
H17C 0.6135 0.5218 0.5195 0.052 Uiso calc R 1 H
C21 0.52869(12) 0.46206(13) 0.76742(10) 0.0238(5) Uani d . 1 C
C22 0.56950(12) 0.52423(14) 0.79038(10) 0.0261(5) Uani d . 1 C
C23 0.57700(14) 0.53094(18) 0.84464(11) 0.0381(7) Uani d . 1 C
H23 0.6032 0.5732 0.8600 0.046 Uiso calc R 1 H
C24 0.54551(16) 0.4748(2) 0.87647(11) 0.0485(9) Uani d . 1 C
H24 0.5505 0.4785 0.9136 0.058 Uiso calc R 1 H
C25 0.50718(15) 0.41413(18) 0.85336(12) 0.0447(9) Uani d . 1 C
H25 0.4860 0.3761 0.8750 0.054 Uiso calc R 1 H
C26 0.49894(15) 0.40736(16) 0.80014(11) 0.0382(7) Uani d . 1 C
H26 0.4726 0.3648 0.7853 0.046 Uiso calc R 1 H
S3 0.61283(3) 0.59034(3) 0.74626(3) 0.03353(17) Uani d . 1 S
C27 0.65616(18) 0.66151(17) 0.78796(19) 0.0593(11) Uani d . 1 C
H27A 0.6816 0.7007 0.7661 0.089 Uiso calc R 1 H
H27B 0.6860 0.6554 0.8113 0.089 Uiso calc R 1 H
H27C 0.6244 0.6671 0.8092 0.089 Uiso calc R 1 H
P2 0.3333 0.6667 0.80038(4) 0.0162(2) Uani d S 1 P
C31 0.40202(11) 0.66402(11) 0.76817(9) 0.0167(4) Uani d . 1 C
C32 0.42020(11) 0.61806(11) 0.78545(9) 0.0183(4) Uani d . 1 C
C33 0.47485(12) 0.61832(12) 0.76346(10) 0.0221(5) Uani d . 1 C
H33 0.4867 0.5870 0.7749 0.027 Uiso calc R 1 H
C34 0.51213(12) 0.66402(13) 0.72502(10) 0.0233(5) Uani d . 1 C
H34 0.5498 0.6644 0.7108 0.028 Uiso calc R 1 H
C35 0.49475(12) 0.70913(12) 0.70729(9) 0.0215(5) Uani d . 1 C
H35 0.5201 0.7402 0.6808 0.026 Uiso calc R 1 H
C36 0.43992(12) 0.70863(12) 0.72854(9) 0.0194(5) Uani d . 1 C
H36 0.4278 0.7392 0.7159 0.023 Uiso calc R 1 H
S4 0.36891(3) 0.55893(3) 0.83254(3) 0.02691(15) Uani d . 1 S
C37 0.42004(15) 0.52982(15) 0.86033(11) 0.0320(6) Uani d . 1 C
H37A 0.3951 0.4963 0.8871 0.048 Uiso calc R 1 H
H37B 0.4589 0.5667 0.8766 0.048 Uiso calc R 1 H
H37C 0.4340 0.5105 0.8325 0.048 Uiso calc R 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C21 . . 101.39(11) y
C1 P1 C11 . . 103.03(12) y
C21 P1 C11 . . 101.87(12) y
C6 C1 C2 . . 117.5(2) n
C6 C1 P1 . . 122.9(2) n
C2 C1 P1 . . 119.37(19) n
C3 C2 C1 . . 120.5(2) n
C3 C2 S1 . . 122.2(2) n
C1 C2 S1 . . 117.23(19) n
C2 C3 C4 . . 120.2(3) n
C2 C3 H3 . . 119.9 n
C4 C3 H3 . . 119.9 n
C5 C4 C3 . . 119.8(3) n
C5 C4 H4 . . 120.1 n
C3 C4 H4 . . 120.1 n
C4 C5 C6 . . 120.8(3) n
C4 C5 H5 . . 119.6 n
C6 C5 H5 . . 119.6 n
C5 C6 C1 . . 121.1(3) n
C5 C6 H6 . . 119.4 n
C1 C6 H6 . . 119.4 n
C2 S1 C7 . . 102.98(15) n
S1 C7 H7A . . 109.5 n
S1 C7 H7B . . 109.5 n
H7A C7 H7B . . 109.5 n
S1 C7 H7C . . 109.5 n
H7A C7 H7C . . 109.5 n
H7B C7 H7C . . 109.5 n
C12 C11 C16 . . 116.5(2) n
C12 C11 P1 . . 120.0(2) n
C16 C11 P1 . . 123.2(2) n
C13 C12 C11 . . 120.4(3) n
C13 C12 S2 . . 121.4(2) n
C11 C12 S2 . . 118.2(2) n
C14 C13 C12 . . 120.5(3) n
C14 C13 H13 . . 119.8 n
C12 C13 H13 . . 119.8 n
C15 C14 C13 . . 119.8(3) n
C15 C14 H14 . . 120.1 n
C13 C14 H14 . . 120.1 n
C16 C15 C14 . . 119.3(3) n
C16 C15 H15 . . 120.3 n
C14 C15 H15 . . 120.3 n
C15 C16 C11 . . 123.4(3) n
C15 C16 H16 . . 118.3 n
C11 C16 H16 . . 118.3 n
C12 S2 C17 . . 102.52(14) n
S2 C17 H17A . . 109.5 n
S2 C17 H17B . . 109.5 n
H17A C17 H17B . . 109.5 n
S2 C17 H17C . . 109.5 n
H17A C17 H17C . . 109.5 n
H17B C17 H17C . . 109.5 n
C26 C21 C22 . . 118.4(2) n
C26 C21 P1 . . 122.2(2) n
C22 C21 P1 . . 119.3(2) n
C23 C22 C21 . . 120.7(3) n
C23 C22 S3 . . 123.1(2) n
C21 C22 S3 . . 116.2(2) n
C22 C23 C24 . . 119.3(3) n
C22 C23 H23 . . 120.3 n
C24 C23 H23 . . 120.3 n
C25 C24 C23 . . 119.3(3) n
C25 C24 H24 . . 120.3 n
C23 C24 H24 . . 120.3 n
C26 C25 C24 . . 121.6(3) n
C26 C25 H25 . . 119.2 n
C24 C25 H25 . . 119.2 n
C25 C26 C21 . . 120.6(3) n
C25 C26 H26 . . 119.7 n
C21 C26 H26 . . 119.7 n
C22 S3 C27 . . 104.53(18) n
S3 C27 H27A . . 109.5 n
S3 C27 H27B . . 109.5 n
H27A C27 H27B . . 109.5 n
S3 C27 H27C . . 109.5 n
H27A C27 H27C . . 109.5 n
H27B C27 H27C . . 109.5 n
C31 P2 C31 2_665 3_565 101.65(9) n
C31 P2 C31 2_665 . 101.65(9) y
C31 P2 C31 3_565 . 101.65(9) n
C36 C31 C32 . . 118.1(2) n
C36 C31 P2 . . 122.29(17) n
C32 C31 P2 . . 119.49(17) n
C33 C32 C31 . . 120.0(2) n
C33 C32 S4 . . 122.47(18) n
C31 C32 S4 . . 117.48(17) n
C34 C33 C32 . . 120.5(2) n
C34 C33 H33 . . 119.8 n
C32 C33 H33 . . 119.8 n
C35 C34 C33 . . 120.4(2) n
C35 C34 H34 . . 119.8 n
C33 C34 H34 . . 119.8 n
C34 C35 C36 . . 119.5(2) n
C34 C35 H35 . . 120.3 n
C36 C35 H35 . . 120.3 n
C35 C36 C31 . . 121.6(2) n
C35 C36 H36 . . 119.2 n
C31 C36 H36 . . 119.2 n
C32 S4 C37 . . 104.02(13) n
S4 C37 H37A . . 109.5 n
S4 C37 H37B . . 109.5 n
H37A C37 H37B . . 109.5 n
S4 C37 H37C . . 109.5 n
H37A C37 H37C . . 109.5 n
H37B C37 H37C . . 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 . 1.838(3) y
P1 C21 . 1.838(3) y
P1 C11 . 1.841(3) y
C1 C6 . 1.397(4) n
C1 C2 . 1.418(4) n
C2 C3 . 1.388(4) n
C2 S1 . 1.772(3) n
C3 C4 . 1.393(4) n
C3 H3 . 0.9500 n
C4 C5 . 1.366(5) n
C4 H4 . 0.9500 n
C5 C6 . 1.387(4) n
C5 H5 . 0.9500 n
C6 H6 . 0.9500 n
S1 C7 . 1.792(3) n
C7 H7A . 0.9800 n
C7 H7B . 0.9800 n
C7 H7C . 0.9800 n
C11 C12 . 1.403(4) n
C11 C16 . 1.406(4) n
C12 C13 . 1.394(4) n
C12 S2 . 1.780(3) n
C13 C14 . 1.388(4) n
C13 H13 . 0.9500 n
C14 C15 . 1.381(5) n
C14 H14 . 0.9500 n
C15 C16 . 1.358(4) n
C15 H15 . 0.9500 n
C16 H16 . 0.9500 n
S2 C17 . 1.798(3) n
C17 H17A . 0.9800 n
C17 H17B . 0.9800 n
C17 H17C . 0.9800 n
C21 C26 . 1.389(4) n
C21 C22 . 1.409(4) n
C22 C23 . 1.389(4) n
C22 S3 . 1.765(3) n
C23 C24 . 1.400(5) n
C23 H23 . 0.9500 n
C24 C25 . 1.378(5) n
C24 H24 . 0.9500 n
C25 C26 . 1.364(4) n
C25 H25 . 0.9500 n
C26 H26 . 0.9500 n
S3 C27 . 1.801(3) n
C27 H27A . 0.9800 n
C27 H27B . 0.9800 n
C27 H27C . 0.9800 n
P2 C31 2_665 1.835(2) n
P2 C31 3_565 1.835(2) n
P2 C31 . 1.835(2) y
C31 C36 . 1.403(3) n
C31 C32 . 1.413(3) n
C32 C33 . 1.395(3) n
C32 S4 . 1.770(2) n
C33 C34 . 1.389(3) n
C33 H33 . 0.9500 n
C34 C35 . 1.385(4) n
C34 H34 . 0.9500 n
C35 C36 . 1.389(3) n
C35 H35 . 0.9500 n
C36 H36 . 0.9500 n
S4 C37 . 1.795(3) n
C37 H37A . 0.9800 n
C37 H37B . 0.9800 n
C37 H37C . 0.9800 n
