#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008383.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_2008383
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  687
_journal_page_last  689
_publ_section_title
;
(1S,R~S~)-6,7-dimethoxy-N-methyl-1-(p-tolylsulfinylmethyl)
 -1-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
;
loop_
_publ_author_name
  'Pierfrancesco Bravo'
  'Eleonora Corradi'
  'Marcello Crucianelli'
  'Stefano Valdo Meille'
  'Matteo Zanda'
_chemical_formula_moiety  'C21 H24 F3 N O3 S'
_chemical_formula_sum  'C21 H24 F3 N O3 S'
_chemical_formula_weight  427.47
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  9.1850(10)
_cell_length_b  12.0520(10)
_cell_length_c  18.8990(10)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2092.1(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.357
_diffrn_ambient_temperature  293(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
  S1 0.94702(16) 0.07848(12) 0.06172(8) 0.0704(5) Uani d . 1 . . S
  F1 0.5006(3) -0.0916(3) 0.06367(15) 0.0782(10) Uani d . 1 . . F
  F2 0.4437(4) -0.0276(3) 0.16475(18) 0.0908(11) Uani d . 1 . . F
  F3 0.6051(4) -0.1523(3) 0.15543(18) 0.0813(10) Uani d . 1 . . F
  O1 0.8797(4) 0.1376(3) 0.39473(16) 0.0625(10) Uani d . 1 . . O
  O2 0.9259(4) -0.0569(3) 0.34364(16) 0.0604(9) Uani d . 1 . . O
  O3 1.0503(5) 0.0640(5) 0.1211(2) 0.1079(18) Uani d . 1 . . O
  N2 0.6157(5) 0.1285(4) 0.08068(19) 0.0597(11) Uani d . 1 . . N
  C2 0.5736(8) 0.1199(5) 0.0063(3) 0.0793(18) Uani d . 1 . . C
  H2A 0.5411 0.1910 -0.0103 0.120(8) Uiso calc R 1 . . H
  H2B 0.4962 0.0669 0.0015 0.120(8) Uiso calc R 1 . . H
  H2C 0.6558 0.0962 -0.0212 0.120(8) Uiso calc R 1 . . H
  C7 0.8270(5) 0.1241(3) 0.3279(2) 0.0488(12) Uani d D 1 . . C
  C22 0.8524(9) 0.2452(5) 0.4242(3) 0.089(2) Uani d . 1 . . C
  H22A 0.8932 0.2492 0.4709 0.120(8) Uiso calc R 1 . . H
  H22B 0.7492 0.2577 0.4266 0.120(8) Uiso calc R 1 . . H
  H22C 0.8964 0.3009 0.3948 0.120(8) Uiso calc R 1 . . H
  C8 0.8531(5) 0.0112(3) 0.2997(2) 0.0442(11) Uani d D 1 . . C
  C23 0.9565(9) -0.1641(5) 0.3172(3) 0.100(3) Uani d . 1 . . C
  H23A 1.0097 -0.2055 0.3521 0.120(8) Uiso calc R 1 . . H
  H23B 1.0137 -0.1581 0.2748 0.120(8) Uiso calc R 1 . . H
  H23C 0.8668 -0.2017 0.3067 0.120(8) Uiso calc R 1 . . H
  C9 0.8024(5) -0.0129(4) 0.2333(2) 0.0460(11) Uani d . 1 . . C
  H9 0.8195 -0.0831 0.2147 0.062(6) Uiso calc R 1 . . H
  C10 0.7260(5) 0.0645(4) 0.1923(2) 0.0447(11) Uani d . 1 . . C
  C5 0.7003(6) 0.1698(4) 0.2201(2) 0.0498(12) Uani d . 1 . . C
  C6 0.7524(6) 0.1960(4) 0.2873(2) 0.0501(12) Uani d . 1 . . C
  H6 0.7347 0.2667 0.3050 0.062(6) Uiso calc R 1 . . H
  C4 0.6177(7) 0.2556(5) 0.1792(3) 0.0677(15) Uani d . 1 . . C
  H4A 0.5505 0.2930 0.2108 0.081 Uiso calc R 1 . . H
  H4B 0.6856 0.3106 0.1614 0.081 Uiso calc R 1 . . H
  C3 0.5354(10) 0.2086(6) 0.1192(3) 0.105(3) Uani d . 1 . . C
  H3A 0.4469 0.1746 0.1370 0.126 Uiso calc R 1 . . H
  H3B 0.5075 0.2683 0.0875 0.126 Uiso calc R 1 . . H
  C1 0.6738(5) 0.0316(4) 0.1176(2) 0.0451(11) Uani d . 1 . . C
  C21 0.5560(6) -0.0598(5) 0.1258(2) 0.0568(13) Uani d . 1 . . C
  C20 0.7998(5) -0.0198(4) 0.0745(2) 0.0466(11) Uani d . 1 . . C
  H20A 0.7635 -0.0435 0.0287 0.058(10) Uiso calc R 1 . . H
  H20B 0.8366 -0.0847 0.0991 0.058(10) Uiso calc R 1 . . H
  C11 1.0300(5) 0.0133(4) -0.0140(2) 0.0509(12) Uani d . 1 . . C
  C12 0.9581(5) 0.0020(5) -0.0777(2) 0.0594(13) Uani d . 1 . . C
  H12 0.8600 0.0206 -0.0810 0.062(6) Uiso calc R 1 . . H
  C13 1.0314(5) -0.0367(5) -0.1366(3) 0.0599(14) Uani d . 1 . . C
  H13 0.9822 -0.0440 -0.1793 0.062(6) Uiso calc R 1 . . H
  C14 1.1767(5) -0.0646(4) -0.1326(2) 0.0537(12) Uani d . 1 . . C
  C15 1.2472(6) -0.0505(5) -0.0694(3) 0.0655(15) Uani d . 1 . . C
  H15 1.3457 -0.0678 -0.0663 0.062(6) Uiso calc R 1 . . H
  C16 1.1761(6) -0.0111(5) -0.0099(3) 0.0599(14) Uani d . 1 . . C
  H16 1.2265 -0.0013 0.0323 0.062(6) Uiso calc R 1 . . H
  C17 1.2569(7) -0.1039(6) -0.1974(3) 0.0758(18) Uani d . 1 . . C
  H17A 1.3566 -0.1189 -0.1853 0.120(8) Uiso calc R 1 . . H
  H17B 1.2533 -0.0475 -0.2332 0.120(8) Uiso calc R 1 . . H
  H17C 1.2122 -0.1705 -0.2149 0.120(8) 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
  S1 0.0674(8) 0.0704(9) 0.0733(9) -0.0202(8) 0.0208(7) -0.0237(7)
  F1 0.0721(18) 0.103(3) 0.0590(17) -0.0221(18) -0.0116(15) -0.0051(17)
  F2 0.069(2) 0.112(3) 0.092(2) -0.013(2) 0.0310(19) -0.010(2)
  F3 0.083(2) 0.0656(19) 0.095(2) -0.0132(19) -0.0183(19) 0.0213(18)
  O1 0.074(2) 0.067(2) 0.0465(17) 0.005(2) -0.0146(16) -0.0124(17)
  O2 0.075(2) 0.061(2) 0.0450(16) 0.021(2) -0.0125(17) 0.0016(15)
  O3 0.073(3) 0.186(5) 0.065(2) -0.042(3) 0.001(2) -0.053(3)
  N2 0.077(3) 0.066(3) 0.0357(18) 0.018(2) -0.0032(19) 0.0039(19)
  C2 0.103(4) 0.092(4) 0.043(3) 0.014(4) -0.020(3) 0.011(3)
  C7 0.045(2) 0.060(3) 0.041(2) -0.002(2) 0.001(2) -0.007(2)
  C22 0.131(6) 0.069(4) 0.066(3) 0.005(4) -0.026(4) -0.023(3)
  C8 0.042(2) 0.053(3) 0.0373(19) 0.002(2) 0.0008(18) 0.005(2)
  C23 0.163(7) 0.079(4) 0.058(3) 0.064(5) -0.031(4) -0.010(3)
  C9 0.054(3) 0.045(3) 0.039(2) 0.012(2) 0.000(2) -0.004(2)
  C10 0.052(3) 0.048(3) 0.034(2) 0.001(2) 0.0022(19) 0.001(2)
  C5 0.058(3) 0.050(3) 0.042(2) 0.001(3) 0.001(2) 0.008(2)
  C6 0.063(3) 0.041(3) 0.047(2) 0.004(2) 0.002(2) -0.004(2)
  C4 0.092(4) 0.055(3) 0.057(3) 0.023(3) -0.008(3) 0.004(3)
  C3 0.163(8) 0.090(5) 0.063(3) 0.051(5) -0.025(4) 0.001(3)
  C1 0.049(2) 0.051(3) 0.036(2) 0.007(2) 0.0020(19) 0.007(2)
  C21 0.058(3) 0.070(4) 0.042(2) 0.000(3) 0.001(2) 0.000(2)
  C20 0.052(3) 0.047(3) 0.041(2) -0.005(2) 0.002(2) -0.007(2)
  C11 0.057(3) 0.049(3) 0.047(2) -0.008(3) 0.006(2) 0.000(2)
  C12 0.043(2) 0.079(4) 0.057(3) -0.004(3) -0.001(2) 0.004(3)
  C13 0.051(3) 0.082(4) 0.047(2) -0.012(3) -0.003(2) -0.002(2)
  C14 0.050(3) 0.058(3) 0.053(2) -0.010(3) 0.006(2) 0.002(2)
  C15 0.048(3) 0.095(4) 0.054(3) 0.006(3) -0.002(2) 0.001(3)
  C16 0.051(3) 0.081(4) 0.048(2) -0.004(3) -0.006(2) 0.002(3)
  C17 0.072(4) 0.095(5) 0.060(3) -0.012(4) 0.011(3) -0.013(3)
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
  S1 O3 . 1.479(5) ?
  S1 C11 . 1.800(5) ?
  S1 C20 . 1.813(5) ?
  F1 C21 . 1.336(5) ?
  F2 C21 . 1.325(6) ?
  F3 C21 . 1.327(6) ?
  O1 C7 . 1.361(5) ?
  O1 C22 . 1.434(7) ?
  O2 C8 . 1.345(5) ?
  O2 C23 . 1.414(6) ?
  N2 C3 . 1.416(8) y
  N2 C1 . 1.462(6) y
  N2 C2 . 1.461(6) y
  C7 C6 . 1.345(6) ?
  C7 C8 . 1.481(5) ?
  C8 C9 . 1.370(6) ?
  C9 C10 . 1.400(6) ?
  C10 C5 . 1.394(7) ?
  C10 C1 . 1.542(6) y
  C5 C6 . 1.393(6) ?
  C5 C4 . 1.497(7) y
  C4 C3 . 1.474(9) y
  C1 C21 . 1.551(7) y
  C1 C20 . 1.544(6) y
  C11 C16 . 1.375(7) ?
  C11 C12 . 1.380(6) ?
  C12 C13 . 1.381(7) ?
  C13 C14 . 1.378(7) ?
  C14 C15 . 1.369(7) ?
  C14 C17 . 1.505(7) ?
  C15 C16 . 1.383(7) ?
_cod_database_code 2008383