#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012371.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_2012371
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1426
_journal_page_last  1428
_publ_section_title
;
Room-temperature monoclinic and low-temperature triclinic
phase-transition structures of
meso-octamethylcalix[4]pyrrole--dimethyl sulfoxide (1/1)
;
loop_
_publ_author_name
  'Lynch, Vincent M.'
  'Gale, Philip A.'
  'Sessler, Jonathan L.'
  'Madeiros, David'
_chemical_formula_moiety  'C28 H36 N4, C2 H6 O1 S1'
_chemical_formula_sum  'C30 H42 N4 O S'
_chemical_formula_iupac  'C28 H36 N4, C2 H6 O1 S1'
_chemical_formula_weight  506.74
_symmetry_cell_setting  'monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
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  10.411(2)
_cell_length_b  23.586(6)
_cell_length_c  12.482(3)
_cell_angle_alpha  90.00
_cell_angle_beta  107.71(2)
_cell_angle_gamma  90.00
_cell_volume  2919.7(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.153
_diffrn_ambient_temperature  298(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  .4930(2)  .28633(8)  .63083(14)  .0507(5) Uani d P  .65 A 1 S
  C2A  .3930(11)  .3452(7)  .6497(12)  .071(4) Uani d PU  .65 A 1 C
  H2AA  .4155  .3778  .6129  .106 Uiso d PR  .65 A 1 H
  H2AB  .2993  .3363  .6166  .106 Uiso d PR  .65 A 1 H
  H2AC  .4104  .3532  .7282  .106 Uiso d PR  .65 A 1 H
  S1'  .3615(4)  .28649(15)  .5995(3)  .0517(9) Uani d P  .35 A 2 S
  C2A'  .4632(19)  .3441(13)  .667(2)  .071(7) Uani d PU  .35 A 2 C
  H2AD  .4379  .3775  .6216  .106 Uiso d PR  .35 A 2 H
  H2AE  .4428  .3494  .7366  .106 Uiso d PR  .35 A 2 H
  H2AF  .5581  .3375  .6830  .106 Uiso d PR  .35 A 2 H
  O1A  .4304(3)  .27117(11)  .5060(2)  .0636(9) Uani d . 1 . . O
  C1A  .4305(4)  .23387(17)  .7049(3)  .0579(13) Uani d . 1 . . C
  H1AD  .3909  .1977  .6786  .087 Uiso d PR  .35 A . H
  H1AE  .5264  .2318  .7194  .087 Uiso d PR  .35 . . H
  H1AF  .4110  .2437  .7730  .087 Uiso d PR  .35 . . H
  H1AA  .4764  .1987  .7034  .087 Uiso d PR  .65 . . H
  H1AB  .4466  .2457  .7815  .087 Uiso d PR  .65 . . H
  H1AC  .3355  .2288  .6699  .087 Uiso d PR  .65 . . H
  N1  .4188(4)  .14801(15)  .4498(3)  .0405(9) Uani d . 1 . . N
  H1N  .417(4)  .1883(17)  .476(3)  .074(14) Uiso d . 1 . . H
  N2  .1818(4)  .11346(16)  .5853(3)  .0490(10) Uani d . 1 . . N
  H2N  .231(3)  .0825(14)  .583(3)  .037(12) Uiso d . 1 . . H
  N3  .4256(4)  .09858(17)  .8519(3)  .0497(10) Uani d . 1 . . N
  H3N  .427(4)  .1365(16)  .871(3)  .055(14) Uiso d . 1 . . H
  N4  .6635(4)  .10802(18)  .7025(3)  .0507(11) Uani d . 1 . . N
  H4N  .620(4)  .0786(17)  .678(3)  .065(18) Uiso d . 1 . . H
  C1  .5309(4)  .11496(18)  .4599(3)  .0415(11) Uani d . 1 . . C
  C2  .4857(5)  .06287(19)  .4185(3)  .0550(12) Uani d . 1 . . C
  H2  .5414  .0308  .4159  .066 Uiso d R 1 . . H
  C3  .3439(5)  .06408(19)  .3840(3)  .0560(13) Uani d . 1 . . C
  H3  .2850  .0335  .3498  .067 Uiso d R 1 . . H
  C4  .3034(4)  .11668(18)  .4038(3)  .0423(11) Uani d . 1 . . C
  C5  .1651(4)  .14086(18)  .3871(3)  .0466(11) Uani d . 1 . . C
  C6  .1447(4)  .15290(18)  .5001(3)  .0436(11) Uani d . 1 . . C
  C7  .0855(4)  .19645(18)  .5393(4)  .0525(12) Uani d . 1 . . C
  H7  .0477  .2299  .4980  .063 Uiso d R 1 . . H
  C8  .0877(4)  .1829(2)  .6500(4)  .0569(13) Uani d . 1 . . C
  H8  .0532  .2057  .6987  .068 Uiso d R 1 . . H
  C9  .1466(4)  .13169(19)  .6781(3)  .0476(12) Uani d . 1 . . C
  C10  .1703(5)  .09393(19)  .7805(3)  .0569(13) Uani d . 1 . . C
  C11  .3089(5)  .0677(2)  .8091(3)  .0540(13) Uani d . 1 . . C
  C12  .3480(7)  .0141(2)  .7939(4)  .0829(18) Uani d . 1 . . C
  H12  .2866  -.0167  .7666  .099 Uiso d R 1 . . H
  C13  .4898(7)  .0123(2)  .8288(4)  .0842(19) Uani d . 1 . . C
  H13  .5444  -.0200  .8258  .101 Uiso d R 1 . . H
  C14  .5381(5)  .0650(2)  .8650(3)  .0558(14) Uani d . 1 . . C
  C15  .6793(5)  .0885(2)  .9042(4)  .0627(14) Uani d . 1 . . C
  C16  .7033(4)  .1255(2)  .8130(3)  .0501(12) Uani d . 1 . . C
  C17  .7665(4)  .1757(2)  .8159(4)  .0598(13) Uani d . 1 . . C
  H17  .8060  .1984  .8815  .072 Uiso d R 1 . . H
  C18  .7639(4)  .18995(19)  .7051(4)  .0550(12) Uani d . 1 . . C
  H18  .8008  .2233  .6815  .066 Uiso d R 1 . . H
  C19  .6992(4)  .14756(18)  .6354(3)  .0448(11) Uani d . 1 . . C
  C20  .6714(4)  .13673(17)  .5106(3)  .0449(11) Uani d . 1 . . C
  C21  .0566(4)  .0980(2)  .3243(4)  .0759(16) Uani d . 1 . . C
  H21A  .0691  .0633  .3663  .114 Uiso d R 1 . . H
  H21B  .0628  .0907  .2504  .114 Uiso d R 1 . . H
  H21C  -.0306  .1134  .3184  .114 Uiso d R 1 . . H
  C22  .1442(5)  .19630(18)  .3190(3)  .0686(15) Uani d . 1 . . C
  H22A  .2132  .2225  .3579  .103 Uiso d R 1 . . H
  H22B  .0574  .2121  .3131  .103 Uiso d R 1 . . H
  H22C  .1507  .1894  .2451  .103 Uiso d R 1 . . H
  C23  .0614(5)  .0473(2)  .7528(4)  .0907(19) Uani d . 1 . . C
  H23A  .0703  .0256  .6904  .136 Uiso d R 1 . . H
  H23B  -.0271  .0637  .7334  .136 Uiso d R 1 . . H
  H23C  .0746  .0231  .8170  .136 Uiso d R 1 . . H
  C24  .1543(5)  .1292(2)  .8786(3)  .0745(16) Uani d . 1 . . C
  H24A  .2216  .1584  .8941  .112 Uiso d R 1 . . H
  H24B  .1683  .1055  .9436  .112 Uiso d R 1 . . H
  H24C  .0665  .1461  .8601  .112 Uiso d R 1 . . H
  C25  .7807(5)  .0382(2)  .9287(4)  .099(2) Uani d . 1 . . C
  H25A  .7676  .0165  .8611  .149 Uiso d R 1 . . H
  H25B  .7674  .0143  .9866  .149 Uiso d R 1 . . H
  H25C  .8706  .0532  .9526  .149 Uiso d R 1 . . H
  C26  .7013(5)  .1233(2) 1.0124(3)  .0875(18) Uani d . 1 . . C
  H26A  .6363  .1534  .9949  .131 Uiso d R 1 . . H
  H26B  .7904  .1391 1.0370  .131 Uiso d R 1 . . H
  H26C  .6873  .1002 1.0710  .131 Uiso d R 1 . . H
  C27  .7738(4)  .09273(18)  .4948(3)  .0637(14) Uani d . 1 . . C
  H27A  .7600  .0578  .5291  .096 Uiso d R 1 . . H
  H27B  .8643  .1057  .5294  .096 Uiso d R 1 . . H
  H27C  .7596  .0867  .4159  .096 Uiso d R 1 . . H
  C28  .6953(4)  .19200(18)  .4539(3)  .0636(14) Uani d . 1 . . C
  H28A  .6327  .2197  .4641  .095 Uiso d R 1 . . H
  H28B  .6809  .1862  .3750  .095 Uiso d R 1 . . H
  H28C  .7856  .2052  .4885  .095 Uiso d 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  .0548(13)  .0511(12)  .0472(11)  -.0043(11)  .0171(10)  -.0039(9)
  C2A  .107(10)  .055(6)  .045(6)  .032(9)  .016(8)  -.003(5)
  S1'  .055(2)  .054(2)  .046(2)  .006(2)  .0151(18)  .0003(17)
  C2A'  .091(15)  .066(12)  .054(11)  .012(14)  .019(13)  .003(9)
  O1A  .089(2)  .059(2)  .0457(17)  .0039(19)  .0248(18)  -.0082(15)
  C1A  .063(3)  .060(3)  .052(3)  -.004(3)  .019(3)  .011(2)
  N1  .050(2)  .037(2)  .0364(19)  .000(2)  .0156(18)  -.0019(17)
  N2  .065(3)  .041(2)  .044(2)  .004(2)  .021(2)  .003(2)
  N3  .066(3)  .040(2)  .046(2)  .002(3)  .020(2)  .002(2)
  N4  .064(3)  .052(3)  .037(2)  .002(2)  .015(2)  .001(2)
  C1  .051(3)  .044(3)  .032(2)  .002(3)  .017(2)  .003(2)
  C2  .071(4)  .041(3)  .053(3)  .007(3)  .020(3)  .000(2)
  C3  .074(4)  .038(3)  .055(3)  -.010(3)  .018(3)  -.008(2)
  C4  .047(3)  .048(3)  .029(2)  -.006(3)  .007(2)  .003(2)
  C5  .050(3)  .048(3)  .039(3)  -.010(2)  .008(2)  .004(2)
  C6  .042(3)  .041(3)  .045(3)  -.006(2)  .011(2)  .003(2)
  C7  .049(3)  .046(3)  .062(3)  -.003(3)  .016(3)  .010(2)
  C8  .055(3)  .053(3)  .066(3)  -.013(3)  .023(3)  -.019(3)
  C9  .051(3)  .057(3)  .038(3)  -.020(3)  .018(2)  -.011(2)
  C10  .065(4)  .065(3)  .042(3)  -.023(3)  .017(3)  -.005(2)
  C11  .084(4)  .043(3)  .038(3)  -.014(3)  .024(3)  .003(2)
  C12  .136(6)  .052(4)  .064(4)  -.019(4)  .035(4)  -.009(3)
  C13  .136(6)  .051(4)  .075(4)  .025(4)  .046(4)  .005(3)
  C14  .084(4)  .054(3)  .038(3)  .026(3)  .032(3)  .016(2)
  C15  .072(4)  .075(4)  .042(3)  .027(3)  .019(3)  .010(3)
  C16  .050(3)  .063(3)  .035(3)  .015(3)  .010(2)  .001(2)
  C17  .049(3)  .079(4)  .046(3)  .010(3)  .007(2)  -.020(3)
  C18  .047(3)  .059(3)  .058(3)  .001(3)  .014(2)  -.004(3)
  C19  .044(3)  .049(3)  .040(3)  .006(2)  .010(2)  .007(2)
  C20  .045(3)  .051(3)  .041(3)  .008(2)  .016(2)  .006(2)
  C21  .065(3)  .098(4)  .059(3)  -.027(3)  .009(3)  -.015(3)
  C22  .064(3)  .084(4)  .061(3)  .018(3)  .023(3)  .029(3)
  C23  .098(4)  .106(4)  .061(3)  -.062(4)  .013(3)  .013(3)
  C24  .063(3)  .118(5)  .050(3)  -.002(3)  .028(3)  -.010(3)
  C25  .120(5)  .119(5)  .070(4)  .071(4)  .045(4)  .045(3)
  C26  .082(4)  .138(5)  .040(3)  .014(4)  .015(3)  -.002(3)
  C27  .057(3)  .083(4)  .053(3)  .013(3)  .020(3)  .000(3)
  C28  .052(3)  .078(4)  .058(3)  -.007(3)  .014(2)  .017(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 O1A . 1.537(3) ?
  S1 C1A . 1.782(4) ?
  S1 C2A . 1.794(13) ?
  C2A H2AA .  .96 ?
  C2A H2AB .  .96 ?
  C2A H2AC .  .96 ?
  S1' O1A . 1.587(4) ?
  S1' C2A' . 1.77(3) ?
  S1' C1A . 1.792(5) ?
  C2A' H2AD .  .96 ?
  C2A' H2AE .  .96 ?
  C2A' H2AF .  .96 ?
  C1A H1AD .  .96 ?
  C1A H1AE .  .96 ?
  C1A H1AF .  .96 ?
  C1A H1AA .  .96 ?
  C1A H1AB .  .96 ?
  C1A H1AC .  .96 ?
  N1 C1 . 1.377(5) ?
  N1 C4 . 1.378(5) ?
  N1 H1N . 1.01(4) ?
  N2 C6 . 1.377(5) ?
  N2 C9 . 1.386(5) ?
  N2 H2N .  .90(3) ?
  N3 C11 . 1.378(5) ?
  N3 C14 . 1.382(5) ?
  N3 H3N .  .93(4) ?
  N4 C16 . 1.377(5) ?
  N4 C19 . 1.378(5) ?
  N4 H4N .  .83(4) ?
  C1 C2 . 1.360(5) ?
  C1 C20 . 1.497(5) ?
  C2 C3 . 1.407(6) ?
  C2 H2 .  .96 ?
  C3 C4 . 1.357(5) ?
  C3 H3 .  .96 ?
  C4 C5 . 1.503(6) ?
  C5 C6 . 1.515(5) ?
  C5 C22 . 1.538(5) ?
  C5 C21 . 1.541(5) ?
  C6 C7 . 1.363(5) ?
  C7 C8 . 1.412(5) ?
  C7 H7 .  .96 ?
  C8 C9 . 1.352(5) ?
  C8 H8 .  .96 ?
  C9 C10 . 1.515(5) ?
  C10 C11 . 1.510(6) ?
  C10 C24 . 1.530(5) ?
  C10 C23 . 1.541(5) ?
  C11 C12 . 1.359(6) ?
  C12 C13 . 1.407(7) ?
  C12 H12 .  .96 ?
  C13 C14 . 1.365(6) ?
  C13 H13 .  .96 ?
  C14 C15 . 1.507(6) ?
  C15 C16 . 1.515(6) ?
  C15 C26 . 1.536(5) ?
  C15 C25 . 1.556(5) ?
  C16 C17 . 1.349(6) ?
  C17 C18 . 1.415(5) ?
  C17 H17 .  .96 ?
  C18 C19 . 1.362(5) ?
  C18 H18 .  .96 ?
  C19 C20 . 1.517(5) ?
  C20 C28 . 1.539(5) ?
  C20 C27 . 1.543(5) ?
  C21 H21A .  .96 ?
  C21 H21B .  .96 ?
  C21 H21C .  .96 ?
  C22 H22A .  .96 ?
  C22 H22B .  .96 ?
  C22 H22C .  .96 ?
  C23 H23A .  .96 ?
  C23 H23B .  .96 ?
  C23 H23C .  .96 ?
  C24 H24A .  .96 ?
  C24 H24B .  .96 ?
  C24 H24C .  .96 ?
  C25 H25A .  .96 ?
  C25 H25B .  .96 ?
  C25 H25C .  .96 ?
  C26 H26A .  .96 ?
  C26 H26B .  .96 ?
  C26 H26C .  .96 ?
  C27 H27A .  .96 ?
  C27 H27B .  .96 ?
  C27 H27C .  .96 ?
  C28 H28A .  .96 ?
  C28 H28B .  .96 ?
  C28 H28C .  .96 ?