data_2008941
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1581
_journal_page_last  1583
_publ_section_title
;
Methyltriphenylphosphonium 1-sulfido-2-methyl-1,2-dicarba-closo-
dodecaborane(12)
;
loop_
_publ_author_name
  'Kivek\"as, Raikko'
  'Benakki, Rajae'
  'Vi\~nas, Clara'
  'Sillanp\"a\"a, Reijo'
_chemical_name_common
;
methyltriphenylphosphonium 1-thiolate-2-methyl-1,2-dicarba-closo-
dodecaborane(12)
;
_chemical_formula_moiety  'C19 H18 P+ , C3 H13 B10 S-'
_chemical_formula_sum  'C22 H31 B10 P S'
_chemical_formula_weight  466.60
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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'
_cell_length_a  12.386(3)
_cell_length_b  15.837(2)
_cell_length_c  14.515(3)
_cell_angle_alpha  90.00
_cell_angle_beta  105.00(2)
_cell_angle_gamma  90.00
_cell_volume  2750.2(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  294(2)
_exptl_crystal_density_diffrn  1.127
_diffrn_ambient_temperature  294(2)
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S -0.13006(11) 0.12196(9) 0.56324(10) 0.0917(5) Uani d . 1 . . S
  P 0.14665(8) 0.14770(6) 0.40485(7) 0.0486(3) Uani d D 1 . . P
  C1 -0.2156(3) 0.2104(2) 0.5473(3) 0.0559(10) Uani d . 1 . . C
  C2 -0.3321(3) 0.2159(2) 0.4442(3) 0.0608(11) Uani d . 1 . . C
  B3 -0.2174(4) 0.2772(3) 0.4528(3) 0.0715(15) Uani d . 1 . . B
  H3 -0.1600 0.2679 0.4072 0.086 Uiso calc R 1 . . H
  B4 -0.1690(5) 0.3101(3) 0.5731(4) 0.0800(16) Uani d . 1 . . B
  H4 -0.0809 0.3252 0.6067 0.096 Uiso calc R 1 . . H
  B5 -0.2538(4) 0.2601(4) 0.6367(4) 0.0774(16) Uani d . 1 . . B
  H5 -0.2225 0.2418 0.7120 0.093 Uiso calc R 1 . . H
  B6 -0.3520(4) 0.1976(4) 0.5536(4) 0.0714(15) Uani d . 1 . . B
  H6 -0.3827 0.1368 0.5734 0.086 Uiso calc R 1 . . H
  B7 -0.3546(5) 0.3152(3) 0.4052(4) 0.0824(16) Uani d . 1 . . B
  H7 -0.3871 0.3324 0.3297 0.099 Uiso calc R 1 . . H
  B8 -0.2536(6) 0.3758(4) 0.4852(4) 0.099(2) Uani d . 1 . . B
  H8 -0.2195 0.4335 0.4615 0.119 Uiso calc R 1 . . H
  B9 -0.2780(6) 0.3663(4) 0.6000(5) 0.114(2) Uani d . 1 . . B
  H9 -0.2619 0.4184 0.6520 0.136 Uiso calc R 1 . . H
  B10 -0.3916(5) 0.2969(5) 0.5900(4) 0.106(2) Uani d . 1 . . B
  H10 -0.4497 0.3026 0.6356 0.127 Uiso calc R 1 . . H
  B11 -0.4389(5) 0.2667(4) 0.4690(4) 0.0919(19) Uani d . 1 . . B
  H11 -0.5275 0.2524 0.4362 0.110 Uiso calc R 1 . . H
  B12 -0.3912(6) 0.3711(4) 0.4959(5) 0.115(2) Uani d . 1 . . B
  H12 -0.4475 0.4260 0.4804 0.138 Uiso calc R 1 . . H
  C13 -0.3474(5) 0.1417(3) 0.3768(3) 0.1046(17) Uani d . 1 . . C
  H13A -0.2868 0.1027 0.3983 0.157 Uiso calc R 1 . . H
  H13B -0.3483 0.1613 0.3140 0.157 Uiso calc R 1 . . H
  H13C -0.4168 0.1140 0.3751 0.157 Uiso calc R 1 . . H
  C14 0.0181(3) 0.0897(2) 0.3690(3) 0.0599(11) Uani d . 1 . . C
  H14A -0.0269 0.1013 0.4123 0.090 Uiso calc R 1 . . H
  H14B 0.0340 0.0303 0.3696 0.090 Uiso calc R 1 . . H
  H14C -0.0217 0.1064 0.3057 0.090 Uiso calc R 1 . . H
  C15A 0.1095(6) 0.2578(3) 0.4077(5) 0.050(4) Uani d PGD 0.619(19) A 1 C
  C16A 0.0446(9) 0.2934(4) 0.3239(5) 0.044(3) Uani d PG 0.619(19) A 1 C
  H16A 0.0232 0.2610 0.2688 0.053 Uiso calc PR 0.619(19) A 1 H
  C17A 0.0120(8) 0.3768(5) 0.3227(5) 0.071(5) Uani d PR 0.619(19) A 1 C
  H17A -0.0314 0.4007 0.2668 0.085 Uiso calc PR 0.619(19) A 1 H
  C18A 0.0443(8) 0.4246(3) 0.4051(6) 0.077(4) Uani d PR 0.619(19) A 1 C
  H18A 0.0225 0.4808 0.4045 0.092 Uiso calc PR 0.619(19) A 1 H
  C19A 0.1092(10) 0.3890(4) 0.4889(5) 0.087(3) Uani d PR 0.619(19) A 1 C
  H19A 0.1307 0.4215 0.5440 0.104 Uiso calc PR 0.619(19) A 1 H
  C20A 0.1418(8) 0.3057(4) 0.4901(5) 0.069(3) Uani d PR 0.619(19) A 1 C
  H20A 0.1853 0.2817 0.5460 0.083 Uiso calc PR 0.619(19) A 1 H
  C15B 0.1225(13) 0.2589(4) 0.3968(10) 0.052(7) Uani d PGD 0.381(19) A 2 C
  C16B 0.0257(11) 0.2934(8) 0.3380(14) 0.090(8) Uani d PG 0.381(19) A 2 C
  H16B -0.0269 0.2586 0.2984 0.109 Uiso calc PR 0.381(19) A 2 H
  C17B 0.0081(11) 0.3792(8) 0.3385(15) 0.076(8) Uani d PR 0.381(19) A 2 C
  H17B -0.0564 0.4026 0.2993 0.091 Uiso calc PR 0.381(19) A 2 H
  C18B 0.0872(18) 0.4306(4) 0.3977(11) 0.088(7) Uani d PR 0.381(19) A 2 C
  H18B 0.0754 0.4886 0.3981 0.105 Uiso calc PR 0.381(19) A 2 H
  C19B 0.184(2) 0.3961(6) 0.4566(14) 0.122(11) Uani d PR 0.381(19) A 2 C
  H19B 0.2366 0.4310 0.4961 0.147 Uiso calc PR 0.381(19) A 2 H
  C20B 0.2016(18) 0.3103(7) 0.4560(13) 0.099(8) Uani d PR 0.381(19) A 2 C
  H20B 0.2661 0.2869 0.4952 0.119 Uiso calc PR 0.381(19) A 2 H
  C21 0.2281(3) 0.1265(2) 0.3228(2) 0.0502(9) Uani d . 1 . . C
  C22 0.2747(3) 0.1903(3) 0.2809(3) 0.0652(11) Uani d . 1 . . C
  H22 0.2621 0.2465 0.2936 0.078 Uiso calc R 1 . . H
  C23 0.3399(4) 0.1704(4) 0.2204(3) 0.0797(14) Uani d . 1 . . C
  H23 0.3718 0.2134 0.1926 0.096 Uiso calc R 1 . . H
  C24 0.3583(4) 0.0883(4) 0.2008(3) 0.0860(15) Uani d . 1 . . C
  H24 0.4025 0.0758 0.1597 0.103 Uiso calc R 1 . . H
  C25 0.3120(4) 0.0238(3) 0.2413(3) 0.0788(14) Uani d . 1 . . C
  H25 0.3244 -0.0321 0.2272 0.095 Uiso calc R 1 . . H
  C26 0.2472(3) 0.0423(3) 0.3026(3) 0.0658(11) Uani d . 1 . . C
  H26 0.2162 -0.0010 0.3305 0.079 Uiso calc R 1 . . H
  C27 0.2261(3) 0.1174(2) 0.5233(2) 0.0469(9) Uani d . 1 . . C
  C28 0.1721(3) 0.1035(2) 0.5940(3) 0.0656(11) Uani d . 1 . . C
  H28 0.0947 0.1083 0.5804 0.079 Uiso calc R 1 . . H
  C29 0.2336(4) 0.0823(3) 0.6857(3) 0.0746(13) Uani d . 1 . . C
  H29 0.1963 0.0722 0.7326 0.089 Uiso calc R 1 . . H
  C30 0.3474(4) 0.0761(3) 0.7083(3) 0.0734(13) Uani d D 1 . . C
  H30 0.3876 0.0627 0.7700 0.088 Uiso calc R 1 . . H
  C31 0.4010(4) 0.0900(3) 0.6385(3) 0.0823(14) Uani d D 1 . . C
  H31 0.4784 0.0858 0.6529 0.099 Uiso calc R 1 . . H
  C32 0.3412(3) 0.1102(3) 0.5463(3) 0.0647(11) Uani d . 1 . . C
  H32 0.3790 0.1191 0.4995 0.078 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  S 0.0846(9) 0.0984(10) 0.1009(10) 0.0370(7) 0.0399(7) 0.0319(8)
  P 0.0471(6) 0.0441(6) 0.0522(6) -0.0028(5) 0.0085(4) -0.0016(5)
  C1 0.050(2) 0.068(3) 0.053(2) 0.002(2) 0.0181(19) 0.010(2)
  C2 0.062(3) 0.059(3) 0.056(2) -0.002(2) 0.005(2) 0.006(2)
  B3 0.083(4) 0.076(4) 0.057(3) -0.007(3) 0.020(3) 0.020(3)
  B4 0.080(4) 0.071(4) 0.081(4) -0.019(3) 0.007(3) 0.000(3)
  B5 0.080(4) 0.104(4) 0.051(3) 0.019(3) 0.022(3) -0.001(3)
  B6 0.051(3) 0.091(4) 0.076(4) 0.001(3) 0.024(3) 0.017(3)
  B7 0.098(4) 0.063(3) 0.074(4) 0.009(3) 0.001(3) 0.013(3)
  B8 0.131(6) 0.061(4) 0.093(4) -0.014(4) 0.006(4) 0.009(3)
  B9 0.144(6) 0.084(4) 0.098(5) 0.021(4) 0.005(4) -0.034(4)
  B10 0.088(5) 0.146(6) 0.090(5) 0.036(4) 0.034(4) -0.014(4)
  B11 0.058(4) 0.108(5) 0.104(5) 0.019(3) 0.009(3) 0.015(4)
  B12 0.129(6) 0.079(5) 0.127(6) 0.044(4) 0.016(5) 0.000(4)
  C13 0.133(5) 0.074(3) 0.094(4) -0.008(3) 0.007(3) -0.025(3)
  C14 0.046(2) 0.056(2) 0.075(3) -0.0029(19) 0.011(2) -0.002(2)
  C15A 0.054(8) 0.037(7) 0.055(8) -0.003(6) 0.009(6) 0.012(6)
  C16A 0.039(5) 0.054(7) 0.032(4) 0.001(4) -0.007(4) -0.001(4)
  C17A 0.084(11) 0.065(12) 0.066(7) 0.009(9) 0.024(7) 0.029(6)
  C18A 0.086(8) 0.053(6) 0.083(8) 0.000(5) 0.009(6) 0.004(6)
  C19A 0.116(9) 0.050(5) 0.082(6) 0.005(5) 0.003(6) -0.009(5)
  C20A 0.087(7) 0.051(5) 0.056(5) 0.001(4) -0.003(5) -0.009(4)
  C15B 0.046(11) 0.069(15) 0.041(11) -0.007(10) 0.013(10) -0.027(10)
  C16B 0.069(12) 0.060(14) 0.17(2) 0.010(9) 0.071(13) -0.006(13)
  C17B 0.047(13) 0.07(2) 0.096(13) 0.014(12) -0.012(10) -0.014(12)
  C18B 0.116(17) 0.030(8) 0.110(15) 0.011(8) 0.017(11) -0.006(8)
  C19B 0.17(2) 0.037(9) 0.112(14) -0.013(10) -0.056(15) -0.003(8)
  C20B 0.129(16) 0.053(9) 0.082(12) -0.001(10) -0.033(12) 0.002(8)
  C21 0.047(2) 0.054(3) 0.046(2) -0.0031(19) 0.0047(18) 0.0008(18)
  C22 0.064(3) 0.067(3) 0.065(3) -0.003(2) 0.017(2) 0.007(2)
  C23 0.064(3) 0.105(4) 0.074(3) -0.002(3) 0.026(3) 0.023(3)
  C24 0.068(3) 0.137(5) 0.056(3) 0.015(3) 0.021(2) 0.000(3)
  C25 0.077(3) 0.091(4) 0.068(3) 0.014(3) 0.018(3) -0.013(3)
  C26 0.069(3) 0.068(3) 0.063(3) -0.002(2) 0.022(2) -0.002(2)
  C27 0.050(2) 0.042(2) 0.051(2) -0.0012(18) 0.0170(19) 0.0016(17)
  C28 0.057(3) 0.075(3) 0.068(3) 0.005(2) 0.023(2) 0.004(2)
  C29 0.079(3) 0.090(3) 0.059(3) -0.002(3) 0.026(3) 0.010(2)
  C30 0.082(3) 0.079(3) 0.052(3) 0.000(3) 0.003(3) 0.012(2)
  C31 0.055(3) 0.117(4) 0.071(3) -0.001(3) 0.007(3) 0.022(3)
  C32 0.051(3) 0.083(3) 0.061(3) -0.007(2) 0.016(2) 0.019(2)
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
  S C1 . 1.735(4) y
  P C15B . 1.785(6) y
  P C21 . 1.780(4) y
  P C14 . 1.795(3) y
  P C27 . 1.811(4) y
  P C15A . 1.807(4) y
  C1 B5 . 1.687(6) ?
  C1 B4 . 1.690(6) ?
  C1 B6 . 1.727(6) ?
  C1 B3 . 1.729(6) ?
  C1 C2 . 1.792(5) y
  C2 C13 . 1.510(5) y
  C2 B11 . 1.666(7) ?
  C2 B7 . 1.670(6) ?
  C2 B6 . 1.694(6) ?
  C2 B3 . 1.699(6) ?
  B3 B8 . 1.722(8) ?
  B3 B7 . 1.766(7) ?
  B3 B4 . 1.772(7) ?
  B3 H3 . 1.1000 ?
  B4 B9 . 1.743(9) ?
  B4 B5 . 1.756(7) ?
  B4 B8 . 1.765(8) ?
  B4 H4 . 1.1000 ?
  B5 B10 . 1.765(8) ?
  B5 B9 . 1.766(8) ?
  B5 B6 . 1.777(7) ?
  B5 H5 . 1.1000 ?
  B6 B10 . 1.769(8) ?
  B6 B11 . 1.784(7) ?
  B6 H6 . 1.1000 ?
  B7 B12 . 1.741(9) ?
  B7 B11 . 1.742(8) ?
  B7 B8 . 1.756(8) ?
  B7 H7 . 1.1000 ?
  B8 B12 . 1.752(10) ?
  B8 B9 . 1.775(10) ?
  B8 H8 . 1.1000 ?
  B9 B10 . 1.762(10) ?
  B9 B12 . 1.777(9) ?
  B9 H9 . 1.1000 ?
  B10 B11 . 1.767(8) ?
  B10 B12 . 1.803(9) ?
  B10 H10 . 1.1000 ?
  B11 B12 . 1.765(9) ?
  B11 H11 . 1.1000 ?
  B12 H12 . 1.1000 ?
  C13 H13A . 0.9600 ?
  C13 H13B . 0.9600 ?
  C13 H13C . 0.9600 ?
  C14 H14A . 0.9600 ?
  C14 H14B . 0.9600 ?
  C14 H14C . 0.9600 ?
  C15A C20A . 1.3850 ?
  C15A C16A . 1.3915 ?
  C16A C17A . 1.3793 ?
  C16A H16A . 0.9300 ?
  C17A C18A . 1.3847 ?
  C17A H17A . 0.9300 ?
  C18A C19A . 1.3914 ?
  C18A H18A . 0.9300 ?
  C19A C20A . 1.3792 ?
  C19A H19A . 0.9300 ?
  C20A H20A . 0.9300 ?
  C15B C20B . 1.3877 ?
  C15B C16B . 1.3902 ?
  C16B C17B . 1.3775 ?
  C16B H16B . 0.9300 ?
  C17B C18B . 1.3877 ?
  C17B H17B . 0.9300 ?
  C18B C19B . 1.3902 ?
  C18B H18B . 0.9300 ?
  C19B C20B . 1.3775 ?
  C19B H19B . 0.9300 ?
  C20B H20B . 0.9300 ?
  C21 C22 . 1.380(5) ?
  C21 C26 . 1.399(5) ?
  C22 C23 . 1.374(6) ?
  C22 H22 . 0.9300 ?
  C23 C24 . 1.362(6) ?
  C23 H23 . 0.9300 ?
  C24 C25 . 1.376(6) ?
  C24 H24 . 0.9300 ?
  C25 C26 . 1.375(5) ?
  C25 H25 . 0.9300 ?
  C26 H26 . 0.9300 ?
  C27 C28 . 1.379(5) ?
  C27 C32 . 1.382(5) ?
  C28 C29 . 1.393(5) ?
  C28 H28 . 0.9300 ?
  C29 C30 . 1.366(5) ?
  C29 H29 . 0.9300 ?
  C30 C31 . 1.365(4) ?
  C30 H30 . 0.9300 ?
  C31 C32 . 1.390(5) ?
  C31 H31 . 0.9300 ?
  C32 H32 . 0.9300 ?