#------------------------------------------------------------------------------
#$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/16/2001684.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2001684
loop_
_publ_author_name
'Agmon, I.'
'Ashkenazi, P.'
'Kaftory, M.'
_publ_section_title
;
 Structures of Diels--Alder reaction bis-adducts of 4-phenyl- or
 4-methyl-1,2,4-triazoline-3,5-dione with 1,6-methano[10]annulene
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              911
_journal_page_last               914
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C28 H23 N6 O5'
_chemical_formula_weight         515.53
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                68.49(3)
_cell_angle_beta                 111.39(3)
_cell_angle_gamma                97.72(3)
_cell_formula_units_Z            2
_cell_length_a                   12.673(6)
_cell_length_b                   11.431(6)
_cell_length_c                   9.439(5)
_cell_volume                     1184.5(11)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_exptl_absorpt_coefficient_mu    0.058
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             538
_[local]_cod_data_source_file    al1019.cif
_[local]_cod_data_source_block   al1019_structure_3_of_3
_cod_original_cell_volume        1184.52
_cod_database_code               2001684
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O(1) .5068(2) .4274(2) .7649(3) .0332(8)
O(2) .8673(2) .4420(3) 1.1262(3) .0422(9)
O(3) .9394(2) .1711(3) 1.0359(3) .0431(8)
O(4) .5803(2) .1767(2) .6714(3) .0424(8)
N(1) .6618(2) .5580(3) .7486(3) .0277(8)
N(2) .6755(2) .4131(3) .9852(3) .0276(8)
N(3) .7722(2) .5611(3) .8597(3) .0289(8)
N(4) .8234(2) .3319(3) .8283(3) .0264(8)
N(5) .7531(2) .1375(3) .8861(4) .0305(8)
N(6) .7116(2) .3337(3) .7129(3) .0263(8)
C(1) .7369(3) .5461(3) .5499(4) .0294(8)
C(2) .6550(3) .6168(3) .5771(4) .0314(8)
C(3) .7010(4) .7487(4) .5676(5) .0385(11)
C(4) .8041(4) .7501(4) .6706(5) .0400(11)
C(5) .8557(3) .6209(3) .7780(4) .0324(8)
C(6) .8555(3) .5459(3) .6722(4) .0298(8)
C(7) .9037(3) .4121(4) .7498(5) .0318(8)
C(8) .8994(3) .3603(4) .6220(5) .0390(12)
C(9) .7973(4) .3609(4) .5153(5) .0390(11)
C(10) .7067(3) .4125(4) .5446(4) .0311(8)
C(11) .8321(3) .6136(4) .4952(5) .0367(8)
C(12) .6022(3) .4615(3) .8234(4) .0274(8)
C(13) .7836(3) .4679(3) 1.0051(4) .0300(8)
C(14) .6476(3) .3115(3) 1.1106(4) .0280(8)
C(15) .8500(3) .2081(3) .9272(4) .0307(8)
C(16) .6715(3) .2111(3) .7457(4) .0302(8)
C(17) .7191(3) .2095(4) 1.2029(5) .0372(10)
C(18) .6925(4) .1132(4) 1.3231(5) .0462(12)
C(19) .5939(4) .1168(4) 1.3520(5) .0484(13)
C(20) .5227(4) .2182(4) 1.2596(6) .0469(12)
C(21) .5502(3) .3167(4) 1.1389(5) .0371(10)
C(22) .7415(3) .0058(3) .9634(4) .0329(8)
C(23) .8134(4) -.0780(4) .9710(5) .0425(12)
C(24) .7982(4) -.2061(4) 1.0450(6) .0545(14)
C(25) .7123(5) -.2480(4) 1.1080(6) .0550(15)
C(26) .6432(4) -.1633(4) 1.1009(5) .0518(12)
C(27) .6558(3) -.0350(4) 1.0292(5) .0431(12)
C(E) .0112(7) .0474(5) .5406(10) .098(3)
O(E) -.0410(8) .0239(9) .6579(14) .109(3)
H(2) .572(3) .609(3) .524(4) ?
H(3) .659(3) .820(3) .481(5) ?
H(4) .844(3) .831(3) .670(4) ?
H(5) .924(3) .614(3) .871(4) ?
H(7) .975(3) .395(3) .847(4) ?
H(8) .965(3) .334(4) .618(5) ?
H(9) .780(3) .332(3) .423(4) ?
H(10) .628(3) .405(3) .482(4) ?
H(111) .825(3) .701(3) .463(4) ?
H(112) .856(3) .568(4) .446(5) ?
H(17) .789(3) .209(4) 1.182(5) ?
H(18) .745(4) .051(4) 1.376(6) ?
H(19) .578(3) .046(3) 1.435(4) ?
H(20) .449(4) .219(4) 1.292(6) ?
H(21) .500(3) .379(3) 1.081(4) ?
H(23) .868(3) -.052(3) .937(4) ?
H(24) .847(4) -.253(4) 1.029(5) ?
H(25) .707(4) -.334(4) 1.140(5) ?
H(26) .587(3) -.186(4) 1.135(5) ?
H(27) .603(4) .027(4) 1.042(6) ?
H(81) -.024(4) .123(5) .476(6) ?
H(82) .105(3) .063(3) .634(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) C(12) 1.210(4)
O(2) C(13) 1.213(3)
O(3) C(15) 1.215(3)
O(4) C(16) 1.213(3)
N(1) N(3) 1.415(3)
N(1) C(2) 1.482(4)
N(1) C(12) 1.370(4)
N(2) C(12) 1.409(3)
N(2) C(13) 1.405(4)
N(2) C(14) 1.436(4)
N(3) C(5) 1.481(4)
N(3) C(13) 1.365(3)
N(4) N(6) 1.435(3)
N(4) C(7) 1.492(4)
N(4) C(15) 1.384(4)
N(5) C(15) 1.388(4)
N(5) C(16) 1.396(3)
N(5) C(22) 1.426(4)
N(6) C(10) 1.494(4)
N(6) C(16) 1.386(4)
C(1) C(2) 1.540(6)
C(1) C(6) 1.525(4)
C(1) C(10) 1.538(5)
C(1) C(11) 1.493(5)
C(2) C(3) 1.525(5)
C(3) C(4) 1.317(5)
C(4) C(5) 1.520(4)
C(5) C(6) 1.536(6)
C(6) C(7) 1.534(5)
C(6) C(11) 1.493(5)
C(7) C(8) 1.509(7)
C(8) C(9) 1.317(5)
C(9) C(10) 1.509(7)
C(14) C(17) 1.379(4)
C(14) C(21) 1.367(6)
C(17) C(18) 1.370(5)
C(18) C(19) 1.382(8)
C(19) C(20) 1.373(5)
C(20) C(21) 1.390(6)
C(22) C(23) 1.373(6)
C(22) C(27) 1.388(6)
C(23) C(24) 1.394(5)
C(24) C(25) 1.376(8)
C(25) C(26) 1.359(8)
C(26) C(27) 1.387(5)
C(E) O(E) 1.420(10)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(3) N(1) C(2) 113.1(2)
N(3) N(1) C(12) 109.0(3)
C(2) N(1) C(12) 132.0(3)
C(12) N(2) C(13) 111.4(3)
C(12) N(2) C(14) 124.5(3)
C(13) N(2) C(14) 123.8(3)
N(1) N(3) C(5) 112.6(3)
N(1) N(3) C(13) 109.8(3)
C(5) N(3) C(13) 131.5(3)
N(6) N(4) C(7) 111.8(3)
N(6) N(4) C(15) 107.8(3)
C(7) N(4) C(15) 120.6(3)
C(15) N(5) C(16) 110.0(3)
C(15) N(5) C(22) 125.6(4)
C(16) N(5) C(22) 124.0(3)
N(4) N(6) C(10) 111.6(2)
N(4) N(6) C(16) 107.8(3)
C(10) N(6) C(16) 120.2(3)
C(2) C(1) C(6) 109.7(2)
C(2) C(1) C(10) 119.4(3)
C(2) C(1) C(11) 120.7(3)
C(6) C(1) C(10) 109.4(3)
C(6) C(1) C(11) 59.3(3)
C(10) C(1) C(11) 118.7(2)
N(1) C(2) C(1) 107.9(3)
N(1) C(2) C(3) 102.7(3)
C(1) C(2) C(3) 109.0(3)
C(2) C(3) C(4) 113.6(5)
C(3) C(4) C(5) 114.8(4)
N(3) C(5) C(4) 102.5(3)
N(3) C(5) C(6) 107.4(2)
C(4) C(5) C(6) 109.7(3)
C(1) C(6) C(5) 109.9(3)
C(1) C(6) C(7) 109.2(3)
C(1) C(6) C(11) 59.3(2)
C(5) C(6) C(7) 120.6(4)
C(5) C(6) C(11) 118.8(3)
C(7) C(6) C(11) 119.2(3)
N(4) C(7) C(6) 106.1(2)
N(4) C(7) C(8) 104.7(3)
C(6) C(7) C(8) 110.9(4)
C(7) C(8) C(9) 113.8(3)
C(8) C(9) C(10) 114.0(3)
N(6) C(10) C(1) 104.9(3)
N(6) C(10) C(9) 105.5(4)
C(1) C(10) C(9) 110.9(3)
C(1) C(11) C(6) 61.4(3)
O(1) C(12) N(1) 127.8(4)
O(1) C(12) N(2) 127.5(3)
N(1) C(12) N(2) 104.7(3)
O(2) C(13) N(2) 127.8(4)
O(2) C(13) N(3) 127.5(3)
N(2) C(13) N(3) 104.6(3)
N(2) C(14) C(17) 120.1(3)
N(2) C(14) C(21) 119.7(4)
C(17) C(14) C(21) 120.2(4)
O(3) C(15) N(4) 125.8(3)
O(3) C(15) N(5) 127.1(4)
N(4) C(15) N(5) 106.9(3)
O(4) C(16) N(5) 127.1(3)
O(4) C(16) N(6) 126.2(4)
N(5) C(16) N(6) 106.6(3)
C(14) C(17) C(18) 119.9(3)
C(17) C(18) C(19) 120.5(5)
C(18) C(19) C(20) 119.5(5)
C(19) C(20) C(21) 120.1(4)
C(14) C(21) C(20) 119.9(4)
N(5) C(22) C(23) 120.4(3)
N(5) C(22) C(27) 118.3(3)
C(23) C(22) C(27) 121.2(4)
C(22) C(23) C(24) 118.8(4)
C(23) C(24) C(25) 120.6(4)
C(24) C(25) C(26) 119.5(5)
C(25) C(26) C(27) 121.7(4)
C(22) C(27) C(26) 118.1(3)