#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/07/4020741.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_4020741
loop_
_publ_author_name
'Panchami Prabhakaran'
'Vedavati G. Puranik'
'Gangadhar J. Sanjayan'
_publ_section_title
;
 Preorganizing Linear (Self-Complementary) Quadruple
 Hydrogen-Bonding Arrays Using Intramolecular
 Hydrogen Bonding as the Sole Force
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10067
_journal_page_last               10072
_journal_paper_doi               10.1021/jo051768a
_journal_volume                  70
_journal_year                    2005
_chemical_formula_moiety         '2(C14 H20 N4 O3)'
_chemical_formula_sum            'C14 H20 N4 O3'
_chemical_formula_weight         292.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.5470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1570(4)
_cell_length_b                   10.0700(4)
_cell_length_c                   31.9910(13)
_cell_measurement_temperature    293(2)
_cell_volume                     3181.0(2)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.221
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020741
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36955(18) 0.4897(2) 0.89843(6) 0.0668(5) Uani 1 1 d . . .
O2 O 0.67939(16) 0.7326(2) 1.03162(6) 0.0696(6) Uani 1 1 d . . .
O3 O 0.54156(16) 0.85207(19) 1.06315(6) 0.0605(5) Uani 1 1 d . . .
N1 N 0.1531(2) 0.5595(3) 0.89111(7) 0.0614(6) Uani 1 1 d . . .
H1 H 0.0968 0.6024 0.9024 0.074 Uiso 1 1 calc R . .
N2 N 0.31378(19) 0.6153(2) 0.95207(7) 0.0513(5) Uani 1 1 d . . .
H2 H 0.2463 0.6368 0.9626 0.062 Uiso 1 1 calc R . .
N3 N 0.5473(2) 0.6182(2) 0.95976(7) 0.0617(6) Uani 1 1 d . . .
H3A H 0.6274 0.6417 0.9732 0.074 Uiso 1 1 calc R . .
H3B H 0.5355 0.5751 0.9360 0.074 Uiso 1 1 calc R . .
N4 N 0.44373(18) 0.7138(2) 1.01166(7) 0.0482(5) Uani 1 1 d . . .
C1 C 0.2850(2) 0.5506(3) 0.91286(8) 0.0519(6) Uani 1 1 d . . .
C2 C 0.4417(2) 0.6485(2) 0.97575(8) 0.0465(6) Uani 1 1 d . . .
C3 C 0.5658(2) 0.7633(3) 1.03485(8) 0.0498(6) Uani 1 1 d . . .
C4 C 0.6519(3) 0.9401(3) 1.08645(9) 0.0644(7) Uani 1 1 d . . .
C5 C 0.7201(3) 1.0105(4) 1.05488(12) 0.0904(11) Uani 1 1 d . . .
H5A H 0.7738 0.9479 1.0435 0.136 Uiso 1 1 calc R . .
H5B H 0.7771 1.0803 1.0695 0.136 Uiso 1 1 calc R . .
H5C H 0.6521 1.0475 1.0318 0.136 Uiso 1 1 calc R . .
C6 C 0.7516(3) 0.8595(4) 1.11941(11) 0.0851(10) Uani 1 1 d . . .
H6A H 0.7035 0.8097 1.1367 0.128 Uiso 1 1 calc R . .
H6B H 0.8148 0.9181 1.1375 0.128 Uiso 1 1 calc R . .
H6C H 0.7996 0.7996 1.1049 0.128 Uiso 1 1 calc R . .
C7 C 0.5747(4) 1.0386(5) 1.10758(16) 0.1214(16) Uani 1 1 d . . .
H7C H 0.5072 1.0822 1.0859 0.182 Uiso 1 1 calc R . .
H7D H 0.6364 1.1034 1.1232 0.182 Uiso 1 1 calc R . .
H7E H 0.5317 0.9924 1.1270 0.182 Uiso 1 1 calc R . .
C8 C 0.1058(3) 0.4983(3) 0.84937(9) 0.0675(8) Uani 1 1 d . . .
H8A H 0.0109 0.4762 0.8458 0.081 Uiso 1 1 calc R . .
H8B H 0.1547 0.4156 0.8491 0.081 Uiso 1 1 calc R . .
C9 C 0.1206(3) 0.5800(3) 0.81111(9) 0.0594(7) Uani 1 1 d . . .
C10 C 0.0388(4) 0.5552(4) 0.77119(11) 0.0934(11) Uani 1 1 d . . .
H10 H -0.0281 0.4905 0.7682 0.112 Uiso 1 1 calc R . .
C11 C 0.0543(6) 0.6255(6) 0.73502(13) 0.1223(17) Uani 1 1 d . . .
H11 H -0.0024 0.6078 0.7083 0.147 Uiso 1 1 calc R . .
C12 C 0.1526(6) 0.7201(6) 0.73887(17) 0.1228(17) Uani 1 1 d . . .
H12 H 0.1629 0.7676 0.7149 0.147 Uiso 1 1 calc R . .
C13 C 0.2347(5) 0.7439(5) 0.77778(16) 0.1210(15) Uani 1 1 d . . .
H13 H 0.3026 0.8075 0.7806 0.145 Uiso 1 1 calc R . .
C14 C 0.2188(4) 0.6746(4) 0.81363(12) 0.0903(11) Uani 1 1 d . . .
H14 H 0.2765 0.6928 0.8402 0.108 Uiso 1 1 calc R . .
O4 O 0.84111(19) 0.3772(3) 0.88268(7) 0.0913(8) Uani 1 1 d . . .
O5 O 1.15644(18) 0.2853(3) 1.03438(7) 0.1055(10) Uani 1 1 d . . .
O6 O 1.02698(16) 0.2340(2) 1.08031(6) 0.0609(5) Uani 1 1 d . . .
N5 N 0.6222(2) 0.3667(3) 0.88570(7) 0.0637(6) Uani 1 1 d . . .
H5 H 0.5657 0.3473 0.9010 0.076 Uiso 1 1 calc R . .
N6 N 0.78759(18) 0.3274(2) 0.94690(7) 0.0560(6) Uani 1 1 d . . .
H6 H 0.7209 0.3144 0.9587 0.067 Uiso 1 1 calc R . .
N7 N 1.0205(2) 0.3282(3) 0.95509(8) 0.0832(9) Uani 1 1 d . . .
H7A H 1.1017 0.3209 0.9706 0.100 Uiso 1 1 calc R . .
H7B H 1.0070 0.3433 0.9280 0.100 Uiso 1 1 calc R . .
N8 N 0.92083(18) 0.2929(2) 1.01409(7) 0.0530(5) Uani 1 1 d . . .
C15 C 0.7560(2) 0.3574(3) 0.90362(9) 0.0582(7) Uani 1 1 d . . .
C16 C 0.9163(2) 0.3161(3) 0.97304(8) 0.0527(6) Uani 1 1 d . . .
C17 C 1.0446(2) 0.2718(3) 1.04147(9) 0.0618(7) Uani 1 1 d . . .
C18 C 1.1381(3) 0.1665(3) 1.11133(10) 0.0693(8) Uani 1 1 d . . .
C19 C 1.1781(5) 0.0432(5) 1.09001(15) 0.1309(18) Uani 1 1 d . . .
H19A H 1.0996 -0.0111 1.0796 0.196 Uiso 1 1 calc R . .
H19B H 1.2441 -0.0062 1.1106 0.196 Uiso 1 1 calc R . .
H19C H 1.2161 0.0687 1.0664 0.196 Uiso 1 1 calc R . .
C20 C 1.2563(3) 0.2595(4) 1.12741(11) 0.0902(11) Uani 1 1 d . . .
H20A H 1.3023 0.2753 1.1049 0.135 Uiso 1 1 calc R . .
H20B H 1.3180 0.2201 1.1516 0.135 Uiso 1 1 calc R . .
H20C H 1.2236 0.3422 1.1360 0.135 Uiso 1 1 calc R . .
C21 C 1.0724(4) 0.1313(5) 1.14766(12) 0.1083(15) Uani 1 1 d . . .
H21A H 1.0448 0.2111 1.1596 0.163 Uiso 1 1 calc R . .
H21B H 1.1361 0.0841 1.1695 0.163 Uiso 1 1 calc R . .
H21C H 0.9947 0.0763 1.1369 0.163 Uiso 1 1 calc R . .
C22 C 0.5701(3) 0.4081(3) 0.84161(9) 0.0638(7) Uani 1 1 d . . .
H22A H 0.6446 0.4420 0.8306 0.077 Uiso 1 1 calc R . .
H22B H 0.5069 0.4806 0.8413 0.077 Uiso 1 1 calc R . .
C23 C 0.4999(3) 0.3012(3) 0.81200(8) 0.0600(7) Uani 1 1 d . . .
C24 C 0.3712(3) 0.3221(4) 0.78669(10) 0.0780(9) Uani 1 1 d . . .
H24 H 0.3279 0.4025 0.7885 0.094 Uiso 1 1 calc R . .
C25 C 0.3061(5) 0.2257(6) 0.75880(13) 0.1109(15) Uani 1 1 d . . .
H25 H 0.2201 0.2420 0.7418 0.133 Uiso 1 1 calc R . .
C26 C 0.3665(8) 0.1079(7) 0.75606(15) 0.139(2) Uani 1 1 d . . .
H26 H 0.3219 0.0432 0.7372 0.166 Uiso 1 1 calc R . .
C27 C 0.4937(7) 0.0830(5) 0.78099(18) 0.1348(19) Uani 1 1 d . . .
H27 H 0.5352 0.0016 0.7791 0.162 Uiso 1 1 calc R . .
C28 C 0.5599(4) 0.1800(4) 0.80893(13) 0.0959(11) Uani 1 1 d . . .
H28 H 0.6459 0.1630 0.8258 0.115 Uiso 1 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.229(3) . ?
O2 C3 1.222(3) . ?
O3 C3 1.335(3) . ?
O3 C4 1.486(3) . ?
N1 C1 1.360(3) . ?
N1 C8 1.447(3) . ?
N1 H1 0.8600 . ?
N2 C1 1.383(3) . ?
N2 C2 1.383(3) . ?
N2 H2 0.8600 . ?
N3 C2 1.327(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C2 1.320(3) . ?
N4 C3 1.380(3) . ?
C4 C6 1.515(4) . ?
C4 C7 1.517(5) . ?
C4 C5 1.526(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7C 0.9600 . ?
C7 H7D 0.9600 . ?
C7 H7E 0.9600 . ?
C8 C9 1.511(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.368(4) . ?
C9 C10 1.374(4) . ?
C10 C11 1.396(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.347(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
O4 C15 1.228(3) . ?
O5 C17 1.217(3) . ?
O6 C17 1.350(3) . ?
O6 C18 1.482(3) . ?
N5 C15 1.349(3) . ?
N5 C22 1.447(3) . ?
N5 H5 0.8600 . ?
N6 C15 1.380(3) . ?
N6 C16 1.382(3) . ?
N6 H6 0.8600 . ?
N7 C16 1.322(3) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C16 1.324(3) . ?
N8 C17 1.370(3) . ?
C18 C21 1.512(5) . ?
C18 C20 1.515(4) . ?
C18 C19 1.517(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.499(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C28 1.377(5) . ?
C23 C24 1.384(4) . ?
C24 C25 1.378(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.348(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.387(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9675065
