#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009068.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_2009068
_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_moiety  'C21 H22 F6 N O 1+, C7 H7 O3 S 1-'
_chemical_formula_sum  'C28 H29 F6 N O4 S'
_chemical_formula_weight  589.58
_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  9.8727(18)
_cell_length_b  8.8917(11)
_cell_length_c  16.527(2)
_cell_angle_alpha  90.00
_cell_angle_beta  102.162(12)
_cell_angle_gamma  90.00
_cell_volume  1418.2(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  134(2)
_exptl_crystal_density_diffrn  1.381
_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
  S  .87045(5)  .34522(5)  .12279(3)  .02393(12) Uani d . 1 . . S
  O1  .37951(14)  .38294(15)  .15830(9)  .0260(3) Uani d . 1 . . O
  C22  .9063(2)  .3431(3)  .23270(12)  .0261(4) Uani d . 1 . . C
  O4  .95892(17)  .22819(17)  .09864(10)  .0314(4) Uani d . 1 . . O
  N  .14346(17)  .53302(18)  .03048(10)  .0219(3) Uani d . 1 . . N
  H01  .1030  .5928  -.0117  .026 Uiso calc R 1 . . H
  H02  .0847  .5218  .0649  .026 Uiso calc R 1 . . H
  O3  .90874(17)  .49438(16)  .09843(10)  .0314(4) Uani d . 1 . . O
  O2  .72433(16)  .31331(19)  .09674(9)  .0375(4) Uani d . 1 . . O
  C1  .1762(2)  .3802(2)  -.00257(13)  .0236(4) Uani d . 1 . . C
  H1  .1487  .2997  .0331  .028 Uiso calc R 1 . . H
  C4  .2783(2)  .6037(2)  .07653(12)  .0231(4) Uani d . 1 . . C
  H4  .3077  .6771  .0377  .028 Uiso calc R 1 . . H
  F1  .6452(2)  -.1360(2)  .19782(10)  .0767(6) Uani d . 1 . . F
  C13  .4614(2)  .2654(2)  .35157(14)  .0315(5) Uani d . 1 . . C
  H13  .4122  .3496  .3677  .038 Uiso calc R 1 . . H
  C3  .3824(2)  .4740(2)  .08761(12)  .0228(4) Uani d . 1 . . C
  H3  .4781  .5130  .0898  .027 Uiso calc R 1 . . H
  F6  .3739(2)  -.0092(2)  .48886(11)  .0730(6) Uani d . 1 . . F
  C8  .5137(2)  .2724(2)  .28012(13)  .0279(5) Uani d . 1 . . C
  C10  .6004(2)  .0201(2)  .30462(13)  .0297(5) Uani d . 1 . . C
  C9  .5837(2)  .1499(2)  .25668(13)  .0288(5) Uani d . 1 . . C
  H9  .6205  .1548  .2074  .035 Uiso calc R 1 . . H
  C5  .0957(2)  .3592(3)  -.09020(14)  .0347(5) Uani d . 1 . . C
  H5A  -.0036  .3700  -.0917  .052 Uiso calc R 1 . . H
  H5B  .1140  .2587  -.1098  .052 Uiso calc R 1 . . H
  H5C  .1245  .4353  -.1260  .052 Uiso calc R 1 . . H
  C2  .3331(2)  .3809(2)  .00915(13)  .0266(4) Uani d . 1 . . C
  H2  .3582  .4356  -.0385  .032 Uiso calc R 1 . . H
  C17  .2033(2)  .6268(3)  .21336(14)  .0366(5) Uani d . 1 . . C
  H17  .1825  .5212  .2116  .044 Uiso calc R 1 . . H
  C27  .8636(3)  .4639(3)  .27480(14)  .0332(5) Uani d . 1 . . C
  H27  .8233  .5513  .2451  .040 Uiso calc R 1 . . H
  C14  .6737(3)  -.1147(3)  .27936(15)  .0391(6) Uani d . 1 . . C
  F4  .3304(2)  .2286(2)  .48227(10)  .0643(5) Uani d . 1 . . F
  F3  .6353(2)  -.24233(18)  .30903(15)  .0831(7) Uani d . 1 . . F
  C12  .4806(3)  .1352(2)  .40011(13)  .0324(5) Uani d . 1 . . C
  C16  .2570(2)  .6920(2)  .15034(14)  .0298(5) Uani d . 1 . . C
  F2  .80897(19)  -.1078(2)  .30150(15)  .0857(7) Uani d . 1 . . F
  C15  .4271(3)  .1259(3)  .47797(16)  .0445(6) Uani d . 1 . . C
  F5  .5269(2)  .1468(2)  .54538(9)  .0658(5) Uani d . 1 . . F
  C23  .9661(3)  .2183(3)  .27533(16)  .0433(6) Uani d . 1 . . C
  H23  .9960  .1355  .2462  .052 Uiso calc R 1 . . H
  C21  .2864(2)  .8458(3)  .15421(17)  .0424(6) Uani d . 1 . . C
  H21  .3243  .8921  .1114  .051 Uiso calc R 1 . . H
  C6  .3915(3)  .2223(3)  .01173(18)  .0434(6) Uani d . 1 . . C
  H6A  .3593  .1739  -.0422  .065 Uiso calc R 1 . . H
  H6B  .3598  .1641  .0546  .065 Uiso calc R 1 . . H
  H6C  .4929  .2267  .0244  .065 Uiso calc R 1 . . H
  C11  .5503(3)  .0123(2)  .37705(14)  .0326(5) Uani d . 1 . . C
  H11  .5637  -.0769  .4106  .039 Uiso calc R 1 . . H
  C26  .8799(3)  .4565(3)  .35995(16)  .0444(6) Uani d . 1 . . C
  H26  .8494  .5392  .3889  .053 Uiso calc R 1 . . H
  C25  .9393(3)  .3325(4)  .40412(15)  .0582(8) Uani d . 1 . . C
  C7  .4933(2)  .4109(2)  .22669(14)  .0334(5) Uani d . 1 . . C
  H7A  .4726  .4985  .2590  .040 Uiso calc R 1 . . H
  H7B  .5785  .4329  .2062  .040 Uiso calc R 1 . . H
  C19  .2081(3)  .8657(4)  .2817(2)  .0667(10) Uani d . 1 . . C
  H19  .1911  .9255  .3270  .080 Uiso calc R 1 . . H
  C20  .2611(3)  .9324(4)  .2195(2)  .0644(10) Uani d . 1 . . C
  H20  .2805 1.0383  .2214  .077 Uiso calc R 1 . . H
  C24  .9823(4)  .2139(3)  .35982(17)  .0600(9) Uani d . 1 . . C
  H24 1.0242  .1270  .3894  .072 Uiso calc R 1 . . H
  C28  .9566(5)  .3227(5)  .4972(2)  .0924(14) Uani d . 1 . . C
  H28A  .8959  .3964  .5157  .139 Uiso calc R 1 . . H
  H28B 1.0532  .3441  .5236  .139 Uiso calc R 1 . . H
  H28C  .9321  .2213  .5124  .139 Uiso calc R 1 . . H
  C18  .1794(3)  .7139(4)  .27920(17)  .0538(8) Uani d . 1 . . C
  H18  .1430  .6681  .3227  .065 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  .0239(2)  .0227(2)  .0254(2)  -.0052(2)  .00559(18)  -.0033(2)
  O1  .0231(7)  .0231(7)  .0290(7)  -.0031(5)  -.0009(6)  .0062(5)
  C22  .0259(10)  .0262(9)  .0256(9)  -.0048(9)  .0042(8)  -.0031(9)
  O4  .0354(9)  .0273(7)  .0327(8)  -.0018(6)  .0101(7)  -.0056(6)
  N  .0186(8)  .0210(8)  .0259(9)  .0023(6)  .0042(7)  .0038(6)
  O3  .0353(9)  .0240(7)  .0373(8)  -.0026(7)  .0133(7)  .0008(6)
  O2  .0285(8)  .0527(11)  .0311(8)  -.0114(7)  .0063(6)  -.0063(7)
  C1  .0235(10)  .0154(9)  .0316(11)  .0000(7)  .0055(8)  .0001(7)
  C4  .0216(11)  .0191(9)  .0277(10)  -.0023(8)  .0029(8)  .0047(8)
  F1  .1050(15)  .0774(13)  .0503(10)  .0484(12)  .0218(9)  -.0036(9)
  C13  .0348(12)  .0259(10)  .0304(11)  .0003(9)  -.0008(9)  -.0037(8)
  C3  .0177(10)  .0237(10)  .0280(10)  -.0015(8)  .0070(8)  .0021(8)
  F6  .1218(17)  .0566(11)  .0555(11)  -.0296(11)  .0526(11)  -.0109(8)
  C8  .0255(11)  .0239(10)  .0301(11)  -.0032(9)  -.0035(9)  .0028(8)
  C10  .0297(12)  .0291(11)  .0286(11)  -.0013(9)  .0023(9)  .0007(8)
  C9  .0235(11)  .0316(11)  .0298(11)  -.0029(9)  .0025(8)  .0039(9)
  C5  .0318(12)  .0248(10)  .0416(12)  .0003(9)  -.0054(9)  -.0106(10)
  C2  .0204(10)  .0311(11)  .0291(10)  -.0022(8)  .0070(8)  -.0044(8)
  C17  .0283(12)  .0510(14)  .0295(12)  .0033(11)  .0036(9)  -.0048(10)
  C27  .0351(13)  .0293(11)  .0325(12)  -.0003(10)  .0012(10)  -.0070(9)
  C14  .0437(15)  .0351(13)  .0396(13)  .0075(10)  .0109(11)  .0067(9)
  F4  .0759(12)  .0733(12)  .0493(10)  .0194(10)  .0261(9)  -.0029(8)
  F3  .1231(19)  .0276(9)  .1210(18)  .0115(9)  .0769(15)  .0050(9)
  C12  .0409(14)  .0283(10)  .0260(11)  -.0036(10)  .0023(9)  -.0035(8)
  C16  .0196(11)  .0287(11)  .0367(12)  .0033(9)  -.0041(9)  -.0058(9)
  F2  .0429(10)  .0702(13)  .1344(19)  .0213(9)  -.0035(11)  -.0284(12)
  C15  .0613(18)  .0405(14)  .0346(13)  .0004(13)  .0166(12)  -.0059(10)
  F5  .0891(14)  .0783(12)  .0265(8)  .0045(10)  .0041(8)  -.0050(8)
  C23  .0572(17)  .0369(13)  .0348(13)  .0162(12)  .0078(11)  .0002(10)
  C21  .0230(11)  .0308(11)  .0689(16)  -.0007(11)  -.0006(10)  -.0115(13)
  C6  .0268(12)  .0398(14)  .0611(16)  .0068(10)  .0037(11)  -.0225(12)
  C11  .0408(14)  .0260(10)  .0292(11)  .0010(9)  .0031(10)  .0047(8)
  C26  .0540(17)  .0433(14)  .0354(14)  .0059(12)  .0085(12)  -.0133(10)
  C25  .076(2)  .0685(19)  .0277(12)  .0220(18)  .0049(13)  -.0052(14)
  C7  .0322(12)  .0242(10)  .0364(12)  -.0050(9)  -.0095(10)  .0069(9)
  C19  .0358(15)  .087(3)  .071(2)  .0021(16)  -.0027(14)  -.053(2)
  C20  .0338(16)  .0483(17)  .101(3)  .0012(13)  -.0075(17)  -.0418(17)
  C24  .089(2)  .0526(17)  .0346(15)  .0322(17)  .0052(14)  .0051(12)
  C28  .140(4)  .100(3)  .0358(16)  .045(3)  .0138(19)  -.0008(18)
  C18  .0364(15)  .087(2)  .0376(15)  .0083(15)  .0066(12)  -.0162(14)
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 O2 . 1.4440(16) ?
  S O3 . 1.4588(15) ?
  S O4 . 1.4670(16) ?
  S C22 . 1.776(2) ?
  O1 C3 . 1.426(2) ?
  O1 C7 . 1.438(2) ?
  C22 C23 . 1.379(3) ?
  C22 C27 . 1.392(3) ?
  N C4 . 1.523(3) ?
  N C1 . 1.524(2) ?
  C1 C5 . 1.509(3) ?
  C1 C2 . 1.520(3) ?
  C4 C16 . 1.502(3) ?
  C4 C3 . 1.530(3) ?
  F1 C14 . 1.331(3) ?
  C13 C8 . 1.386(3) ?
  C13 C12 . 1.399(3) ?
  C3 C2 . 1.529(3) ?
  F6 C15 . 1.338(3) ?
  C8 C9 . 1.388(3) ?
  C8 C7 . 1.504(3) ?
  C10 C9 . 1.389(3) ?
  C10 C11 . 1.390(3) ?
  C10 C14 . 1.504(3) ?
  C2 C6 . 1.521(3) ?
  C17 C16 . 1.391(3) ?
  C17 C18 . 1.395(4) ?
  C27 C26 . 1.384(3) ?
  C14 F2 . 1.310(3) ?
  C14 F3 . 1.323(3) ?
  F4 C15 . 1.333(3) ?
  C12 C11 . 1.387(3) ?
  C12 C15 . 1.493(4) ?
  C16 C21 . 1.396(3) ?
  C15 F5 . 1.336(3) ?
  C23 C24 . 1.372(4) ?
  C21 C20 . 1.391(4) ?
  C26 C25 . 1.382(4) ?
  C25 C24 . 1.400(4) ?
  C25 C28 . 1.514(4) ?
  C19 C18 . 1.378(5) ?
  C19 C20 . 1.382(6) ?