#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2200019.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_2200019
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o1
_journal_page_last  o3
_publ_section_title
;
N,N',N'',N'''-Tetrakis(1-naphthylmethyl)-1,4,8,11-tetraazacyclotetradecane
;
loop_
_publ_author_name
  'Kubo, Kanji'
  'Yamamoto, Emi'
  'Sakurai, Tadamitsu'
  'Mori, Akira'
_chemical_formula_sum  'C54 H56 N4'
_chemical_formula_weight  761.02
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z'
_cell_length_a  11.609(5)
_cell_length_b  18.907(5)
_cell_length_c  9.878(5)
_cell_angle_alpha  90.00
_cell_angle_beta  95.462(5)
_cell_angle_gamma  90.00
_cell_volume  2158.3(15)
_cell_formula_units_Z  2
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.171
_diffrn_ambient_temperature  296(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
  N1  .3121(2)  .05827(13)  .0076(2)  .0517(7) Uani d . 1 . . N
  N2  .6838(2)  .09182(13)  .0833(2)  .0545(7) Uani d . 1 . . N
  C1  .2253(3)  .13761(17)  -.1773(3)  .0600(8) Uani d . 1 . . C
  C2  .1578(3)  .1966(2)  -.1733(3)  .0815(11) Uani d . 1 . . C
  H2  .1032  .1988  -.1104  .098 Uiso calc R 1 . . H
  C3  .1684(4)  .2536(2)  -.2613(4)  .1012(14) Uani d . 1 . . C
  H3  .1210  .2930  -.2565  .121 Uiso calc R 1 . . H
  C4  .2474(4)  .2516(2)  -.3535(4)  .0997(14) Uani d . 1 . . C
  H4  .2543  .2899  -.4113  .120 Uiso calc R 1 . . H
  C5  .3194(4)  .19219(19)  -.3628(4)  .0723(10) Uani d . 1 . . C
  C6  .4000(4)  .1882(2)  -.4605(4)  .0939(13) Uani d . 1 . . C
  H6  .4075  .2261  -.5191  .113 Uiso calc R 1 . . H
  C7  .4668(4)  .1300(3)  -.4701(4)  .0909(13) Uani d . 1 . . C
  H7  .5200  .1282  -.5346  .109 Uiso calc R 1 . . H
  C8  .4557(3)  .0730(2)  -.3836(3)  .0773(11) Uani d . 1 . . C
  H8  .5017  .0332  -.3911  .093 Uiso calc R 1 . . H
  C9  .3787(3)  .07438(17)  -.2879(3)  .0616(9) Uani d . 1 . . C
  H9  .3727  .0357  -.2310  .074 Uiso calc R 1 . . H
  C10  .3082(3)  .13385(18)  -.2747(3)  .0568(8) Uani d . 1 . . C
  C11  .8528(3)  .15078(17)  .2157(3)  .0602(9) Uani d . 1 . . C
  C12  .9450(3)  .18090(17)  .1626(4)  .0756(10) Uani d . 1 . . C
  H12  .9335  .2032  .0784  .091 Uiso calc R 1 . . H
  C13 1.0564(4)  .17953(19)  .2303(5)  .0886(12) Uani d . 1 . . C
  H13 1.1182  .1986  .1892  .106 Uiso calc R 1 . . H
  C14 1.0739(3)  .1507(2)  .3546(5)  .0851(12) Uani d . 1 . . C
  H14 1.1476  .1517  .4005  .102 Uiso calc R 1 . . H
  C15  .9824(3)  .11903(18)  .4170(4)  .0658(9) Uani d . 1 . . C
  C16  .9982(4)  .0900(2)  .5493(4)  .0892(12) Uani d . 1 . . C
  H16 1.0707  .0922  .5980  .107 Uiso calc R 1 . . H
  C17  .9099(4)  .0591(2)  .6061(4)  .0969(13) Uani d . 1 . . C
  H17  .9221  .0402  .6932  .116 Uiso calc R 1 . . H
  C18  .8014(4)  .0555(2)  .5355(4)  .0862(12) Uani d . 1 . . C
  H18  .7412  .0335  .5750  .103 Uiso calc R 1 . . H
  C19  .7816(3)  .08408(17)  .4081(3)  .0683(10) Uani d . 1 . . C
  H19  .7081  .0809  .3619  .082 Uiso calc R 1 . . H
  C20  .8702(3)  .11803(16)  .3461(3)  .0569(8) Uani d . 1 . . C
  C21  .3556(3)  .11911(16)  .0889(3)  .0597(9) Uani d . 1 . . C
  H21A  .3089  .1252  .1645  .072 Uiso calc R 1 . . H
  H21B  .3473  .1614  .0333  .072 Uiso calc R 1 . . H
  C22  .4820(2)  .11107(16)  .1442(3)  .0566(8) Uani d . 1 . . C
  H22A  .5053  .1522  .1989  .068 Uiso calc R 1 . . H
  H22B  .4899  .0698  .2028  .068 Uiso calc R 1 . . H
  C23  .5622(3)  .10323(17)  .0322(3)  .0623(9) Uani d . 1 . . C
  H23A  .5361  .0636  -.0252  .075 Uiso calc R 1 . . H
  H23B  .5568  .1455  -.0236  .075 Uiso calc R 1 . . H
  C24  .7531(3)  .06846(16)  -.0259(3)  .0667(9) Uani d . 1 . . C
  H24A  .8326  .0624  .0121  .080 Uiso calc R 1 . . H
  H24B  .7521  .1056  -.0937  .080 Uiso calc R 1 . . H
  C25  .7129(3)  .00008(16)  -.0965(3)  .0622(9) Uani d . 1 . . C
  H25A  .6436  .0101  -.1563  .075 Uiso calc R 1 . . H
  H25B  .7721  -.0152  -.1530  .075 Uiso calc R 1 . . H
  C26  .2080(3)  .07629(17)  -.0830(3)  .0626(9) Uani d . 1 . . C
  H26A  .1458  .0879  -.0278  .075 Uiso calc R 1 . . H
  H26B  .1842  .0351  -.1372  .075 Uiso calc R 1 . . H
  C27  .7342(3)  .15755(16)  .1425(3)  .0660(9) Uani d . 1 . . C
  H27A  .6827  .1761  .2056  .079 Uiso calc R 1 . . H
  H27B  .7373  .1920  .0701  .079 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
  N1  .0585(17)  .0524(16)  .0432(14)  .0026(14)  -.0004(13)  -.0009(13)
  N2  .0562(17)  .0531(16)  .0541(16)  .0029(14)  .0054(14)  -.0063(13)
  C1  .065(2)  .061(2)  .0501(19)  .008(2)  -.0132(18)  -.0023(18)
  C2  .098(3)  .082(3)  .059(2)  .034(2)  -.017(2)  -.012(2)
  C3  .148(4)  .072(3)  .075(3)  .041(3)  -.031(3)  -.006(3)
  C4  .158(4)  .063(3)  .071(3)  .007(3)  -.027(3)  .008(2)
  C5  .097(3)  .062(3)  .054(2)  -.012(2)  -.018(2)  .003(2)
  C6  .111(4)  .103(4)  .063(3)  -.036(3)  -.015(3)  .022(3)
  C7  .091(3)  .129(4)  .052(2)  -.021(3)  .005(2)  .007(3)
  C8  .082(3)  .102(3)  .0471(19)  .007(2)  .0038(19)  -.007(2)
  C9  .072(2)  .065(2)  .0471(19)  .005(2)  -.0003(18)  -.0026(17)
  C10  .064(2)  .057(2)  .0457(18)  -.0007(19)  -.0146(17)  -.0018(17)
  C11  .056(2)  .050(2)  .075(2)  -.0021(18)  .008(2)  -.0099(18)
  C12  .075(3)  .058(2)  .095(3)  -.006(2)  .012(2)  -.002(2)
  C13  .074(3)  .070(3)  .125(4)  -.018(2)  .024(3)  -.009(3)
  C14  .054(2)  .084(3)  .116(3)  -.009(2)  .001(3)  -.031(3)
  C15  .054(2)  .069(2)  .073(3)  -.004(2)  .000(2)  -.017(2)
  C16  .072(3)  .114(3)  .077(3)  .001(3)  -.015(2)  -.026(2)
  C17  .099(3)  .123(4)  .067(3)  .004(3)  -.001(3)  -.003(3)
  C18  .083(3)  .110(3)  .065(2)  -.010(3)  .008(2)  .003(2)
  C19  .059(2)  .076(2)  .069(2)  -.006(2)  .0029(19)  -.0107(19)
  C20  .052(2)  .053(2)  .066(2)  -.0030(18)  .0054(19)  -.0178(18)
  C21  .062(2)  .063(2)  .0519(19)  .0124(19)  -.0042(16)  -.0087(17)
  C22  .061(2)  .058(2)  .0486(18)  .0059(17)  -.0061(16)  -.0018(16)
  C23  .061(2)  .075(2)  .0494(19)  .0057(18)  -.0009(17)  .0039(16)
  C24  .076(2)  .062(2)  .064(2)  .0025(19)  .0152(19)  .0029(18)
  C25  .070(2)  .066(2)  .0521(19)  .0065(19)  .0130(17)  -.0029(18)
  C26  .055(2)  .073(2)  .059(2)  .0061(18)  .0002(17)  -.0067(18)
  C27  .070(2)  .050(2)  .078(2)  .0037(18)  .006(2)  .0025(18)
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
  N1 C25 3_655 1.457(3) yes
  N1 C21 . 1.465(3) yes
  N1 C26 . 1.474(3) yes
  N2 C23 . 1.470(3) yes
  N2 C27 . 1.471(3) yes
  N2 C24 . 1.473(3) yes
  C1 C2 . 1.365(4) ?
  C1 C10 . 1.426(4) ?
  C1 C26 . 1.513(4) ?
  C2 C3 . 1.397(5) ?
  C3 C4 . 1.353(5) ?
  C4 C5 . 1.409(5) ?
  C5 C6 . 1.409(5) ?
  C5 C10 . 1.418(4) ?
  C6 C7 . 1.355(5) ?
  C7 C8 . 1.389(5) ?
  C8 C9 . 1.362(4) ?
  C9 C10 . 1.404(4) ?
  C11 C12 . 1.360(4) ?
  C11 C20 . 1.427(4) ?
  C11 C27 . 1.499(4) ?
  C12 C13 . 1.399(5) ?
  C13 C14 . 1.341(5) ?
  C14 C15 . 1.411(4) ?
  C15 C16 . 1.414(5) ?
  C15 C20 . 1.419(4) ?
  C16 C17 . 1.347(5) ?
  C17 C18 . 1.383(5) ?
  C18 C19 . 1.369(4) ?
  C19 C20 . 1.402(4) ?
  C21 C22 . 1.524(4) yes
  C22 C23 . 1.519(4) yes
  C24 C25 . 1.521(4) yes
  C25 N1 3_655 1.456(3) ?