#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009067.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_2009067
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
(+)-(2S,3S,4S,5S)-3-[3,5-Bis(trifluoromethyl)benzyloxy]-N-(tert-
butoxycarbonyl)-4,5-dimethyl-2-phenylpyrrolidine, (I), and
(+)-(2S,3S,4S,5S)-3-[3,5-bis(trifluoromethyl)benzyloxy]-4,5-dimethyl-2-
phenylpyrrolidinium p-toluenesulfonate, (II), at 134 K
;
loop_
_publ_author_name
  'Bats, Jan W.'
  'Heinrich, Timo'
  'Reggelin, Michael'
_chemical_formula_sum  'C26 H29 F6 N O3'
_chemical_formula_weight  517.50
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  9.0696(15)
_cell_length_b  16.809(2)
_cell_length_c  9.2603(11)
_cell_angle_alpha  90.00
_cell_angle_beta  114.804(12)
_cell_angle_gamma  90.00
_cell_volume  1281.5(3)
_cell_formula_units_Z  2
_cell_measurement_temperature  134(2)
_exptl_crystal_density_diffrn  1.341
_diffrn_ambient_temperature  134(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
  O3  .16619(12)  .06171(6)  .12244(11)  .01714(19) Uani d . 1 . . O
  F6  .49686(13)  .06964(6)  .71888(11)  .0295(2) Uani d . 1 . . F
  O2  -.18058(13)  -.14851(6)  .15462(14)  .0241(2) Uani d . 1 . . O
  F5  .68772(15)  .04823(7)  .64605(14)  .0400(3) Uani d . 1 . . F
  F1  .46907(15)  .39766(7)  .24255(14)  .0409(3) Uani d . 1 . . F
  O1  .05232(14)  -.21959(7)  .21696(14)  .0262(2) Uani d . 1 . . O
  C15  .49299(17)  .27872(8)  .38668(16)  .0187(2) Uani d . 1 . . C
  N  .00469(15)  -.10279(7)  .07934(15)  .0198(2) Uani d . 1 . . N
  C18  .37692(17)  .12896(8)  .40689(17)  .0196(3) Uani d . 1 . . C
  H18  .3383  .0766  .4144  .023 Uiso calc R 1 . . H
  C1  .14088(17)  -.10960(8)  .03221(16)  .0192(2) Uani d . 1 . . C
  H1  .2464  -.1039  .1280  .023 Uiso calc R 1 . . H
  C3  .03766(16)  .02511(8)  -.00940(15)  .0171(2) Uani d . 1 . . C
  H3  -.0249  .0654  -.0917  .020 Uiso calc R 1 . . H
  C4  -.07692(16)  -.02443(8)  .04228(16)  .0176(2) Uani d . 1 . . C
  H4  -.1850  -.0301  -.0503  .021 Uiso calc R 1 . . H
  F3  .70913(16)  .35498(8)  .38243(19)  .0525(4) Uani d . 1 . . F
  F4  .70461(16)  .14736(7)  .79914(13)  .0470(3) Uani d . 1 . . F
  C13  .29318(17)  .17535(8)  .27243(16)  .0174(2) Uani d . 1 . . C
  C16  .57745(17)  .23302(8)  .52229(16)  .0194(2) Uani d . 1 . . C
  H16  .6746  .2526  .6072  .023 Uiso calc R 1 . . H
  C17  .51643(17)  .15828(8)  .53041(16)  .0184(2) Uani d . 1 . . C
  C5  -.03298(18)  -.16197(8)  .15760(17)  .0205(3) Uani d . 1 . . C
  C14  .35188(18)  .25092(8)  .26241(16)  .0190(2) Uani d . 1 . . C
  H14  .2955  .2836  .1705  .023 Uiso calc R 1 . . H
  C19  .5597(2)  .35937(9)  .3769(2)  .0274(3) Uani d . 1 . . C
  C2  .11350(18)  -.03708(8)  -.07760(16)  .0190(2) Uani d . 1 . . C
  H2  .0311  -.0520  -.1861  .023 Uiso calc R 1 . . H
  C21  -.10006(17)  .01418(8)  .17915(16)  .0201(3) Uani d . 1 . . C
  C12  .14052(17)  .14405(8)  .14093(16)  .0193(3) Uani d . 1 . . C
  H12A  .0470  .1510  .1686  .023 Uiso calc R 1 . . H
  H12B  .1176  .1731  .0407  .023 Uiso calc R 1 . . H
  C20  .60164(18)  .10634(9)  .67360(17)  .0235(3) Uani d . 1 . . C
  C6  -.2393(2)  -.19430(10)  .2558(2)  .0281(3) Uani d . 1 . . C
  F2  .5724(2)  .40652(7)  .49753(17)  .0546(4) Uani d . 1 . . F
  C22  -.2381(2)  .06005(10)  .1475(2)  .0286(3) Uani d . 1 . . C
  H22  -.3239  .0613  .0421  .034 Uiso calc R 1 . . H
  C10  .1401(2)  -.18718(9)  -.0537(2)  .0283(3) Uani d . 1 . . C
  H10A  .2243  -.1851  -.0938  .042 Uiso calc R 1 . . H
  H10C  .0336  -.1944  -.1430  .042 Uiso calc R 1 . . H
  H10B  .1618  -.2318  .0205  .042 Uiso calc R 1 . . H
  C11  .2659(2)  -.00887(10)  -.0927(2)  .0274(3) Uani d . 1 . . C
  H11A  .3511  .0024  .0133  .041 Uiso calc R 1 . . H
  H11C  .2414  .0396  -.1574  .041 Uiso calc R 1 . . H
  H11B  .3033  -.0504  -.1437  .041 Uiso calc R 1 . . H
  C26  .0195(2)  .00951(10)  .33418(18)  .0251(3) Uani d . 1 . . C
  H26  .1126  -.0240  .3579  .030 Uiso calc R 1 . . H
  C24  -.1302(3)  .10184(13)  .4219(2)  .0414(4) Uani d . 1 . . C
  H24  -.1383  .1334  .5046  .050 Uiso calc R 1 . . H
  C25  .0044(3)  .05330(12)  .4550(2)  .0355(4) Uani d . 1 . . C
  H25  .0873  .0500  .5617  .043 Uiso calc R 1 . . H
  C9  -.1219(3)  -.18664(13)  .4297(2)  .0404(4) Uani d . 1 . . C
  H9A  -.0194  -.2131  .4474  .061 Uiso calc R 1 . . H
  H9B  -.1690  -.2116  .4962  .061 Uiso calc R 1 . . H
  H9C  -.1013  -.1302  .4576  .061 Uiso calc R 1 . . H
  C23  -.2517(3)  .10440(13)  .2698(3)  .0402(4) Uani d . 1 . . C
  H23  -.3462  .1366  .2474  .048 Uiso calc R 1 . . H
  C8  -.2654(3)  -.28101(12)  .2024(3)  .0402(4) Uani d . 1 . . C
  H8A  -.3166  -.3096  .2616  .060 Uiso calc R 1 . . H
  H8B  -.1605  -.3056  .2230  .060 Uiso calc R 1 . . H
  H8C  -.3360  -.2835  .0883  .060 Uiso calc R 1 . . H
  C7  -.3992(3)  -.15346(15)  .2220(3)  .0481(5) Uani d . 1 . . C
  H7C  -.4661  -.1526  .1070  .072 Uiso calc R 1 . . H
  H7B  -.3786  -.0988  .2623  .072 Uiso calc R 1 . . H
  H7A  -.4565  -.1825  .2748  .072 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
  O3  .0162(4)  .0132(4)  .0179(4)  -.0002(3)  .0031(4)  -.0009(3)
  F6  .0312(5)  .0289(5)  .0310(5)  .0021(4)  .0155(4)  .0107(4)
  O2  .0184(5)  .0234(5)  .0325(5)  -.0002(4)  .0127(4)  .0089(4)
  F5  .0369(6)  .0435(6)  .0430(6)  .0218(5)  .0200(5)  .0193(5)
  F1  .0403(6)  .0259(5)  .0408(6)  -.0093(4)  .0017(5)  .0138(4)
  O1  .0238(6)  .0223(5)  .0331(6)  .0039(4)  .0125(5)  .0075(4)
  C15  .0180(6)  .0152(6)  .0220(6)  -.0027(4)  .0075(5)  -.0013(4)
  N  .0185(5)  .0158(5)  .0277(6)  .0012(4)  .0124(5)  .0027(4)
  C18  .0190(6)  .0157(5)  .0217(6)  -.0013(4)  .0064(5)  .0012(5)
  C1  .0185(6)  .0172(6)  .0233(6)  -.0014(5)  .0101(5)  -.0009(5)
  C3  .0159(6)  .0165(6)  .0160(5)  -.0014(4)  .0040(4)  .0010(4)
  C4  .0149(6)  .0165(6)  .0198(5)  .0004(4)  .0058(5)  .0012(4)
  F3  .0308(6)  .0455(7)  .0789(10)  -.0082(5)  .0207(6)  .0224(6)
  F4  .0529(8)  .0342(6)  .0257(5)  -.0161(5)  -.0113(5)  .0080(4)
  C13  .0165(6)  .0153(5)  .0187(6)  -.0010(4)  .0057(5)  -.0011(4)
  C16  .0179(6)  .0187(6)  .0207(6)  -.0024(5)  .0072(5)  -.0014(4)
  C17  .0182(6)  .0172(6)  .0180(6)  .0003(5)  .0058(5)  .0016(4)
  C5  .0180(6)  .0193(6)  .0234(6)  -.0016(5)  .0079(5)  .0012(5)
  C14  .0204(6)  .0154(5)  .0195(6)  .0003(4)  .0067(5)  .0020(4)
  C19  .0289(8)  .0191(6)  .0298(7)  -.0068(5)  .0079(6)  .0038(5)
  C2  .0208(6)  .0180(6)  .0184(6)  -.0030(5)  .0083(5)  -.0031(4)
  C21  .0191(6)  .0197(6)  .0238(6)  .0002(5)  .0113(5)  .0018(5)
  C12  .0170(6)  .0138(6)  .0217(6)  .0016(4)  .0029(5)  .0013(4)
  C20  .0226(7)  .0195(6)  .0235(6)  -.0021(5)  .0048(5)  .0040(5)
  C6  .0271(8)  .0269(7)  .0371(8)  -.0010(6)  .0201(7)  .0084(6)
  F2  .0914(11)  .0254(5)  .0473(7)  -.0234(6)  .0294(7)  -.0115(5)
  C22  .0235(7)  .0315(8)  .0348(8)  .0070(6)  .0160(6)  .0054(6)
  C10  .0329(8)  .0191(6)  .0382(8)  -.0016(5)  .0201(7)  -.0045(6)
  C11  .0325(8)  .0239(7)  .0350(8)  -.0034(6)  .0233(7)  -.0012(5)
  C26  .0252(7)  .0267(7)  .0235(7)  -.0028(5)  .0104(6)  .0012(5)
  C24  .0518(12)  .0448(10)  .0425(10)  -.0026(9)  .0345(9)  -.0103(8)
  C25  .0415(10)  .0427(10)  .0253(7)  -.0073(8)  .0170(7)  -.0045(7)
  C9  .0479(11)  .0462(11)  .0316(8)  -.0051(9)  .0212(8)  .0038(7)
  C23  .0403(10)  .0427(10)  .0514(11)  .0093(8)  .0328(9)  -.0015(8)
  C8  .0450(11)  .0311(9)  .0515(11)  -.0133(8)  .0273(9)  .0014(7)
  C7  .0339(10)  .0524(12)  .0720(14)  .0095(9)  .0362(10)  .0236(11)
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
  O3 C12 . 1.4256(16) ?
  O3 C3 . 1.4262(15) ?
  F6 C20 . 1.3394(18) ?
  O2 C5 . 1.3464(17) ?
  O2 C6 . 1.4738(17) ?
  F5 C20 . 1.3401(19) ?
  F1 C19 . 1.3337(19) ?
  O1 C5 . 1.2174(18) ?
  C15 C14 . 1.3946(19) ?
  C15 C16 . 1.3953(19) ?
  C15 C19 . 1.5025(19) ?
  N C5 . 1.3561(18) ?
  N C1 . 1.4770(17) ?
  N C4 . 1.4791(17) ?
  C18 C17 . 1.3921(19) ?
  C18 C13 . 1.3935(18) ?
  C1 C10 . 1.526(2) ?
  C1 C2 . 1.5395(19) ?
  C3 C2 . 1.5262(18) ?
  C3 C4 . 1.5554(18) ?
  C4 C21 . 1.5149(18) ?
  F3 C19 . 1.337(2) ?
  F4 C20 . 1.3372(18) ?
  C13 C14 . 1.3954(18) ?
  C13 C12 . 1.5040(19) ?
  C16 C17 . 1.3874(19) ?
  C17 C20 . 1.5026(19) ?
  C19 F2 . 1.335(2) ?
  C2 C11 . 1.522(2) ?
  C21 C26 . 1.392(2) ?
  C21 C22 . 1.393(2) ?
  C6 C7 . 1.514(3) ?
  C6 C9 . 1.518(3) ?
  C6 C8 . 1.525(3) ?
  C22 C23 . 1.404(2) ?
  C26 C25 . 1.393(2) ?
  C24 C23 . 1.377(3) ?
  C24 C25 . 1.392(3) ?