#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008447.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_2008447
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  756
_journal_page_last  759
_publ_section_title
;
 Heterocycle-substituted [2.2]paracyclophanes
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Dix, Ina'
  'Hopf, Henning'
  'Jones, Peter G.'
_chemical_formula_sum  'C20 H18 S'
_chemical_formula_weight  290.40
_symmetry_cell_setting  monoclinic
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  16.850(2)
_cell_length_b  7.6203(10)
_cell_length_c  11.574(2)
_cell_angle_alpha  90.00
_cell_angle_beta  95.523(11)
_cell_angle_gamma  90.00
_cell_volume  1479.3(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.304
_diffrn_ambient_temperature  173(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
  C1  .32632(13)  .7537(3)  .57445(19)  .0474(6) Uani d U 1 . . C
  H1A  .3768  .7726  .6241  .057 Uiso calc R 1 . . H
  H1B  .3141  .8627  .5298  .057 Uiso calc R 1 . . H
  C2  .33842(12)  .5995(2)  .48709(16)  .0342(5) Uani d U 1 . . C
  H2A  .3372  .6481  .4076  .041 Uiso calc R 1 . . H
  H2B  .3916  .5466  .5070  .041 Uiso calc R 1 . . H
  C3  .27540(11)  .4572(2)  .48846(15)  .0271(4) Uani d U 1 . . C
  C4  .28385(11)  .3099(2)  .56260(14)  .0245(4) Uani d U 1 A . C
  C5  .21499(11)  .2348(2)  .60022(16)  .0291(4) Uani d U 1 . . C
  H5  .2204  .1372  .6515  .035 Uiso calc R 1 . . H
  C6  .13911(11)  .2974(2)  .56554(17)  .0325(5) Uani d U 1 . . C
  C7  .13239(12)  .4142(3)  .47262(16)  .0352(5) Uani d U 1 . . C
  H7  .0813  .4407  .4347  .042 Uiso calc R 1 . . H
  C8  .19947(11)  .4921(2)  .43498(15)  .0323(5) Uani d U 1 . . C
  H8  .1936  .5710  .3712  .039 Uiso calc R 1 . . H
  C9  .07093(12)  .2672(3)  .6391(2)  .0466(6) Uani d U 1 . . C
  H9A  .0767  .1493  .6748  .056 Uiso calc R 1 . . H
  H9B  .0202  .2689  .5883  .056 Uiso calc R 1 . . H
  C10  .06645(12)  .4089(3)  .73869(17)  .0432(5) Uani d U 1 . . C
  H10A  .0131  .4647  .7304  .052 Uiso calc R 1 . . H
  H10B  .0731  .3494  .8151  .052 Uiso calc R 1 . . H
  C11  .12959(12)  .5492(3)  .73524(16)  .0336(5) Uani d U 1 . . C
  C12  .11842(12)  .6916(3)  .66072(17)  .0366(5) Uani d U 1 . . C
  H12  .0659  .7321  .6381  .044 Uiso calc R 1 . . H
  C13  .18273(13)  .7757(3)  .61887(17)  .0376(5) Uani d U 1 . . C
  H13  .1738  .8724  .5675  .045 Uiso calc R 1 . . H
  C14  .26017(12)  .7197(3)  .65144(17)  .0358(5) Uani d U 1 . . C
  C15  .27103(12)  .6039(3)  .74405(16)  .0359(5) Uani d U 1 . . C
  H15  .3233  .5823  .7795  .043 Uiso calc R 1 . . H
  C16  .20677(12)  .5194(3)  .78573(16)  .0344(5) Uani d U 1 . . C
  H16  .2155  .4404  .8492  .041 Uiso calc R 1 . . H
  C2'  .36190(11)  .2418(2)  .61151(16)  .0273(4) Uani d DU 1 . . C
  S  .4399(2)  .2163(6)  .5378(4)  .0362(7) Uani d PDU  .514(3) A 1 S
  C3'  .3736(11)  .176(3)  .7259(11)  .042(3) Uani d PDU  .514(3) A 1 C
  H3'  .3366  .1796  .7829  .050 Uiso calc PR  .514(3) A 1 H
  C4'  .4542(8)  .102(3)  .7389(16)  .041(3) Uani d PDU  .514(3) A 1 C
  H4'  .4753  .0485  .8093  .049 Uiso calc PR  .514(3) A 1 H
  C5'  .4979(11)  .114(3)  .6453(14)  .038(3) Uani d PDU  .514(3) A 1 C
  H5'  .5508  .0728  .6413  .045 Uiso calc PR  .514(3) A 1 H
  S"  .3792(3)  .1578(7)  .7444(3)  .0347(7) Uani d PDU  .486(3) A 2 S
  C3"  .4290(8)  .225(2)  .5462(14)  .045(4) Uani d PDU  .486(3) A 2 C
  H3"  .4324  .2613  .4682  .054 Uiso calc PR  .486(3) A 2 H
  C4"  .4921(10)  .141(3)  .6242(15)  .037(3) Uani d PDU  .486(3) A 2 C
  H4"  .5433  .1186  .5995  .044 Uiso calc PR  .486(3) A 2 H
  C5"  .4745(8)  .097(4)  .7332(16)  .037(2) Uani d PDU  .486(3) A 2 C
  H5"  .5094  .0429  .7918  .044 Uiso calc PR  .486(3) A 2 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
  C1  .0507(14)  .0383(13)  .0545(14)  -.0155(11)  .0117(11)  -.0114(11)
  C2  .0427(12)  .0245(10)  .0361(11)  -.0005(9)  .0082(9)  .0072(9)
  C3  .0377(11)  .0219(10)  .0222(10)  .0033(9)  .0050(8)  -.0027(8)
  C4  .0310(10)  .0199(10)  .0221(9)  -.0011(8)  .0002(8)  -.0048(8)
  C5  .0354(11)  .0170(10)  .0346(11)  -.0027(9)  .0024(9)  -.0014(8)
  C6  .0329(11)  .0198(10)  .0443(12)  -.0037(9)  .0001(9)  -.0064(9)
  C7  .0344(12)  .0309(11)  .0378(11)  .0039(10)  -.0092(9)  -.0102(10)
  C8  .0457(13)  .0273(11)  .0233(10)  .0042(10)  -.0008(9)  -.0022(9)
  C9  .0330(12)  .0348(12)  .0729(16)  -.0047(10)  .0092(11)  .0008(11)
  C10  .0383(12)  .0482(14)  .0443(13)  .0000(11)  .0096(10)  .0083(11)
  C11  .0380(12)  .0336(12)  .0304(11)  .0046(10)  .0095(9)  -.0027(9)
  C12  .0384(12)  .0309(12)  .0405(12)  .0109(10)  .0041(10)  -.0059(10)
  C13  .0530(14)  .0201(10)  .0396(12)  -.0004(10)  .0045(10)  -.0035(9)
  C14  .0461(13)  .0239(10)  .0375(11)  -.0087(10)  .0043(10)  -.0137(9)
  C15  .0349(12)  .0344(12)  .0369(11)  -.0002(10)  -.0049(9)  -.0175(10)
  C16  .0440(12)  .0338(11)  .0252(10)  .0047(10)  .0016(9)  -.0049(9)
  C2'  .0326(11)  .0188(10)  .0297(10)  -.0010(9)  -.0007(9)  .0007(8)
  S  .0264(9)  .0440(14)  .0391(12)  .0059(9)  .0086(9)  .0000(9)
  C3'  .033(5)  .040(6)  .052(6)  .012(4)  .002(4)  .004(5)
  C4'  .040(7)  .039(4)  .040(4)  .005(6)  -.011(4)  .009(3)
  C5'  .031(3)  .037(8)  .043(5)  .012(3)  -.013(3)  .000(4)
  S"  .0408(15)  .0392(13)  .0234(8)  .0050(11)  -.0013(7)  .0055(8)
  C3"  .046(6)  .054(7)  .033(5)  .021(5)  -.008(4)  .012(5)
  C4"  .026(5)  .033(7)  .051(7)  .006(4)  .004(5)  -.001(5)
  C5"  .031(6)  .035(4)  .040(5)  .001(5)  -.020(4)  .004(4)
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
  C1 C14 . 1.515(3) ?
  C1 C2 . 1.576(3) ?
  C2 C3 . 1.519(3) ?
  C3 C8 . 1.392(2) ?
  C3 C4 . 1.412(2) ?
  C4 C5 . 1.400(2) ?
  C4 C2' . 1.475(2) Y
  C5 C6 . 1.387(3) ?
  C6 C7 . 1.392(3) ?
  C6 C9 . 1.512(3) ?
  C7 C8 . 1.384(3) ?
  C9 C10 . 1.586(3) ?
  C10 C11 . 1.512(3) ?
  C11 C12 . 1.388(3) ?
  C11 C16 . 1.392(3) ?
  C12 C13 . 1.386(3) ?
  C13 C14 . 1.390(3) ?
  C14 C15 . 1.387(3) ?
  C15 C16 . 1.386(3) ?
  C2' C3' . 1.410(11) ?
  C2' C3" . 1.425(12) ?
  C2' S . 1.646(4) ?
  C2' S" . 1.666(4) ?
  S C5' . 1.695(12) ?
  C3' C4' . 1.465(17) ?
  C4' C5' . 1.371(10) ?
  S" C5" . 1.688(12) ?
  C3" C4" . 1.473(17) ?
  C4" C5" . 1.365(10) ?