data_2010605
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  239
_journal_page_last  241
_publ_section_title
;
 Meso- and chiral bis([2.2]paracyclophan-4-yl)methane and
 meso-bis([2.2]paracyclophan-4-yl)sulfide
;
loop_
_publ_author_name
  'Jones, Peter G.'
  'Ernst, Ludger'
  'Dix, Ina'
  'Wittkowski, Lars'
_chemical_formula_sum  'C33 H32'
_chemical_formula_weight  428.59
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  25.969(3)
_cell_length_b  7.7200(10)
_cell_length_c  23.329(3)
_cell_angle_alpha  90.00
_cell_angle_beta  94.044(6)
_cell_angle_gamma  90.00
_cell_volume  4665.3(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.220
_diffrn_ambient_temperature  173(2)
_refine_ls_R_factor_obs  .0416
_refine_ls_wR_factor_obs  .1097
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  C1  .25939(7)  .5062(2)  .36923(8)  .0481(5) Uani d . 1 . C
  H1A  .26576(7)  .3806(2)  .37444(8)  .058 Uiso calc R 1 . H
  H1B  .22473(7)  .5204(2)  .34925(8)  .058 Uiso calc R 1 . H
  C2  .25972(6)  .5949(2)  .43025(8)  .0413(4) Uani d . 1 . C
  H2A  .22594(6)  .6515(2)  .43416(8)  .050 Uiso calc R 1 . H
  H2B  .26416(6)  .5045(2)  .46029(8)  .050 Uiso calc R 1 . H
  C3  .30194(6)  .7277(2)  .44000(6)  .0289(3) Uani d . 1 . C
  C4  .35295(6)  .6819(2)  .45757(6)  .0265(3) Uani d . 1 . C
  C5  .39265(6)  .7900(2)  .44350(6)  .0302(3) Uani d . 1 . C
  H5  .42716(6)  .7597(2)  .45565(6)  .036 Uiso calc R 1 . H
  C6  .38366(6)  .9420(2)  .41208(7)  .0332(4) Uani d . 1 . C
  C7  .33305(6) 1.0014(2)  .40624(7)  .0339(4) Uani d . 1 . C
  H7  .32603(6) 1.1153(2)  .39247(7)  .041 Uiso calc R 1 . H
  C8  .29286(6)  .8959(2)  .42031(6)  .0318(4) Uani d . 1 . C
  H8  .25850(6)  .9388(2)  .41648(6)  .038 Uiso calc R 1 . H
  C9  .42438(7) 1.0126(2)  .37517(9)  .0491(5) Uani d . 1 . C
  H9A  .45895(7)  .9868(2)  .39385(9)  .059 Uiso calc R 1 . H
  H9B  .42077(7) 1.1401(2)  .37261(9)  .059 Uiso calc R 1 . H
  C10  .42059(7)  .9340(3)  .31237(8)  .0567(6) Uani d . 1 . C
  H10A  .41258(7) 1.0285(3)  .28445(8)  .068 Uiso calc R 1 . H
  H10B  .45459(7)  .8852(3)  .30433(8)  .068 Uiso calc R 1 . H
  C11  .38035(6)  .7951(3)  .30351(6)  .0392(4) Uani d . 1 . C
  C12  .32927(6)  .8363(2)  .28597(6)  .0375(4) Uani d . 1 . C
  H12  .32201(6)  .9385(2)  .26420(6)  .045 Uiso calc R 1 . H
  C13  .28921(6)  .7302(2)  .29990(7)  .0366(4) Uani d . 1 . C
  H13  .25466(6)  .7599(2)  .28770(7)  .044 Uiso calc R 1 . H
  C14  .29923(6)  .5797(2)  .33179(7)  .0369(4) Uani d . 1 . C
  C15  .34991(7)  .5219(2)  .33725(7)  .0376(4) Uani d . 1 . C
  H15  .35710(7)  .4075(2)  .35052(7)  .045 Uiso calc R 1 . H
  C16  .38997(7)  .6279(3)  .32373(6)  .0404(4) Uani d . 1 . C
  H16  .42446(7)  .5864(3)  .32825(6)  .049 Uiso calc R 1 . H
  C17  .36547(6)  .5087(2)  .48558(6)  .0304(4) Uani d . 1 . C
  H17A  .40214(6)  .4811(2)  .48080(6)  .037 Uiso calc R 1 . H
  H17B  .34419(6)  .4183(2)  .46527(6)  .037 Uiso calc R 1 . H
  C1'  .42562(7)  .1488(2)  .55630(7)  .0395(4) Uani d . 1 . C
  H1'1  .43425(7)  .0305(2)  .57025(7)  .047 Uiso calc R 1 . H
  H1'2  .43797(7)  .1605(2)  .51730(7)  .047 Uiso calc R 1 . H
  C2'  .36508(6)  .1727(2)  .55273(7)  .0345(4) Uani d . 1 . C
  H2'1  .35165(6)  .1644(2)  .51204(7)  .041 Uiso calc R 1 . H
  H2'2  .34958(6)  .0772(2)  .57403(7)  .041 Uiso calc R 1 . H
  C3'  .34851(5)  .3432(2)  .57694(6)  .0265(3) Uani d . 1 . C
  C4'  .35626(5)  .5017(2)  .54920(6)  .0239(3) Uani d . 1 . C
  C5'  .36212(5)  .6504(2)  .58257(6)  .0246(3) Uani d . 1 . C
  H5'  .36813(5)  .7576(2)  .56420(6)  .029 Uiso calc R 1 . H
  C6'  .35949(5)  .6480(2)  .64205(6)  .0251(3) Uani d . 1 . C
  C7'  .33998(5)  .4994(2)  .66614(6)  .0281(3) Uani d . 1 . C
  H7'  .33019(5)  .5008(2)  .70462(6)  .034 Uiso calc R 1 . H
  C8'  .33489(5)  .3495(2)  .63377(6)  .0295(3) Uani d . 1 . C
  H8'  .32177(5)  .2481(2)  .65064(6)  .035 Uiso calc R 1 . H
  C9'  .38728(6)  .7831(2)  .67935(7)  .0340(4) Uani d . 1 . C
  H9'1  .37168(6)  .7876(2)  .71684(7)  .041 Uiso calc R 1 . H
  H9'2  .38231(6)  .8978(2)  .66084(7)  .041 Uiso calc R 1 . H
  C10'  .44693(7)  .7468(2)  .69008(9)  .0495(5) Uani d . 1 . C
  H10C  .46624(7)  .8455(2)  .67507(9)  .059 Uiso calc R 1 . H
  H10D  .45577(7)  .7397(2)  .73199(9)  .059 Uiso calc R 1 . H
  C11'  .46415(6)  .5821(2)  .66221(7)  .0328(4) Uani d . 1 . C
  C12'  .45500(6)  .4229(2)  .68766(7)  .0323(4) Uani d . 1 . C
  H12'  .45243(6)  .4165(2)  .72803(7)  .039 Uiso calc R 1 . H
  C13'  .44961(6)  .2743(2)  .65493(7)  .0316(4) Uani d . 1 . C
  H13'  .44317(6)  .1671(2)  .67304(7)  .038 Uiso calc R 1 . H
  C14'  .45348(5)  .2794(2)  .59582(6)  .0295(3) Uani d . 1 . C
  C15'  .47424(6)  .4289(2)  .57379(7)  .0319(4) Uani d . 1 . C
  H15'  .48528(6)  .4283(2)  .53583(7)  .038 Uiso calc R 1 . H
  C16'  .47912(6)  .5789(2)  .60628(7)  .0349(4) Uani d . 1 . C
  H16'  .49284(6)  .6804(2)  .59014(7)  .042 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
  C1  .0393(10)  .0420(10)  .0622(12)  -.0127(8)  -.0024(8)  .0024(9)
  C2  .0272(8)  .0495(11)  .0482(10)  .0007(7)  .0093(7)  .0145(8)
  C3  .0284(8)  .0388(9)  .0202(7)  .0052(7)  .0066(6)  .0034(6)
  C4  .0310(8)  .0324(8)  .0162(6)  .0060(6)  .0012(6)  -.0015(6)
  C5  .0277(8)  .0344(8)  .0272(7)  .0029(7)  -.0061(6)  -.0045(7)
  C6  .0363(9)  .0278(8)  .0347(8)  -.0042(7)  -.0036(7)  -.0038(7)
  C7  .0437(9)  .0262(8)  .0311(8)  .0058(7)  -.0032(7)  -.0022(7)
  C8  .0310(8)  .0401(9)  .0243(7)  .0115(7)  .0030(6)  -.0007(7)
  C9  .0391(10)  .0364(10)  .0715(13)  -.0105(8)  .0012(9)  .0109(9)
  C10  .0392(10)  .084(2)  .0471(11)  -.0105(10)  .0044(8)  .0317(11)
  C11  .0337(9)  .0649(12)  .0197(7)  .0016(8)  .0071(6)  .0065(8)
  C12  .0403(9)  .0507(11)  .0213(7)  .0057(8)  .0000(6)  .0033(7)
  C13  .0306(8)  .0483(10)  .0299(8)  .0028(7)  -.0054(6)  -.0080(7)
  C14  .0399(9)  .0384(9)  .0314(8)  -.0035(7)  -.0039(7)  -.0114(7)
  C15  .0485(10)  .0387(9)  .0255(8)  .0095(8)  .0016(7)  -.0081(7)
  C16  .0372(9)  .0641(12)  .0206(7)  .0157(8)  .0062(6)  .0018(8)
  C17  .0367(8)  .0323(8)  .0221(7)  .0078(7)  .0012(6)  .0007(6)
  C1'  .0465(10)  .0322(9)  .0397(9)  .0051(8)  .0029(7)  -.0069(8)
  C2'  .0447(9)  .0257(8)  .0319(8)  -.0036(7)  -.0063(7)  -.0021(7)
  C3'  .0238(7)  .0277(8)  .0272(7)  -.0031(6)  -.0055(6)  .0006(6)
  C4'  .0205(7)  .0286(8)  .0222(7)  .0029(6)  -.0019(5)  .0009(6)
  C5'  .0224(7)  .0245(7)  .0264(7)  .0035(6)  -.0007(6)  .0032(6)
  C6'  .0218(7)  .0286(8)  .0243(7)  .0058(6)  -.0011(5)  -.0018(6)
  C7'  .0223(7)  .0411(9)  .0208(7)  .0016(6)  .0013(5)  .0016(6)
  C8'  .0259(8)  .0337(9)  .0285(8)  -.0074(6)  -.0007(6)  .0064(7)
  C9'  .0383(9)  .0328(9)  .0301(8)  .0039(7)  -.0024(7)  -.0076(7)
  C10'  .0391(10)  .0426(10)  .0644(12)  .0021(8)  -.0138(8)  -.0231(9)
  C11'  .0208(7)  .0344(9)  .0418(9)  -.0014(6)  -.0072(6)  -.0060(7)
  C12'  .0251(8)  .0448(10)  .0264(7)  .0025(7)  -.0026(6)  .0003(7)
  C13'  .0302(8)  .0300(8)  .0345(8)  .0029(6)  .0011(6)  .0077(7)
  C14'  .0254(8)  .0297(8)  .0334(8)  .0070(6)  .0020(6)  -.0002(7)
  C15'  .0234(7)  .0407(9)  .0322(8)  .0032(7)  .0061(6)  .0040(7)
  C16'  .0223(7)  .0342(9)  .0479(10)  -.0054(7)  .0004(7)  .0088(8)
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 . 1.511(2) ?
  C1 C2 . 1.579(3) ?
  C2 C3 . 1.507(2) ?
  C3 C8 . 1.392(2) ?
  C3 C4 . 1.404(2) ?
  C4 C5 . 1.384(2) ?
  C4 C17 . 1.513(2) Y
  C5 C6 . 1.394(2) ?
  C6 C7 . 1.390(2) ?
  C6 C9 . 1.512(2) ?
  C7 C8 . 1.382(2) ?
  C9 C10 . 1.582(3) ?
  C10 C11 . 1.501(3) ?
  C11 C16 . 1.391(3) ?
  C11 C12 . 1.397(2) ?
  C12 C13 . 1.381(2) ?
  C13 C14 . 1.394(2) ?
  C14 C15 . 1.387(2) ?
  C15 C16 . 1.377(3) ?
  C17 C4' . 1.521(2) Y
  C1' C14' . 1.515(2) ?
  C1' C2' . 1.579(2) ?
  C2' C3' . 1.507(2) ?
  C3' C8' . 1.397(2) ?
  C3' C4' . 1.405(2) ?
  C4' C5' . 1.389(2) ?
  C5' C6' . 1.394(2) ?
  C6' C7' . 1.388(2) ?
  C6' C9' . 1.509(2) ?
  C7' C8' . 1.383(2) ?
  C9' C10' . 1.577(2) ?
  C10' C11' . 1.510(2) ?
  C11' C16' . 1.388(2) ?
  C11' C12' . 1.393(2) ?
  C12' C13' . 1.379(2) ?
  C13' C14' . 1.390(2) ?
  C14' C15' . 1.388(2) ?
  C15' C16' . 1.385(2) ?