#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/10/4021018.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_4021018
loop_
_publ_author_name
'Sigitas Stončius'
'Eugenius Butkus'
'Albinas Žilinskas'
'Krister Larsson'
'Lars Öhrströrn'
'Ulf Berg'
'Kenneth Wärnmark'
_publ_section_title
;
 Design and Synthesis of a C₂Symmetric Self-Complementary
 Hydrogen-Bonding Cleft Molecule Based on the
 Bicyclo[3.3.1]nonane and 4-Oxo-5-azaindole Framework.
 Formation of Channels and Inclusion Complexes in the Solid State
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5196
_journal_page_last               5203
_journal_paper_doi               10.1021/jo035869p
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         ' C21 H18 N4 O2, (C3 H7 N O)2.5'
_chemical_formula_sum            'C28.5 H37 N6.5 O4.5'
_chemical_formula_weight         543.14
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                80.63(2)
_cell_angle_beta                 73.94(2)
_cell_angle_gamma                80.70(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5265(2)
_cell_length_b                   11.831(3)
_cell_length_c                   13.775(3)
_cell_measurement_wavelength     0.886
_cell_volume                     1460.9(5)
_diffrn_ambient_temperature      210
_exptl_crystal_density_diffrn    1.235
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_formula_sum        'C28.50 H37 N6.50 O4.50'
_cod_database_code               4021018
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C11 C 0.9102(2) 0.3107(2) 0.2956(2) 0.0430(7) Uani 1 1 d . . .
C10 C 1.0379(2) 0.2534(2) 0.3253(2) 0.0409(6) Uani 1 1 d . . .
C14 C 1.4802(2) 0.2264(2) -0.0377(2) 0.0414(7) Uani 1 1 d . . .
C12 C 1.3710(2) 0.3138(2) -0.0624(2) 0.0403(6) Uani 1 1 d . . .
N1 N 0.9489(2) 0.40830(18) 0.23029(18) 0.0476(6) Uani 1 1 d . . .
H1 H 0.8907 0.4568 0.2014 0.057 Uiso 1 1 calc R . .
N2 N 1.5068(2) 0.24434(19) 0.05042(18) 0.0441(6) Uani 1 1 d . . .
H2 H 1.5689 0.2021 0.0802 0.053 Uiso 1 1 calc R . .
C20 C 1.4917(3) 0.1347(2) -0.1806(2) 0.0503(7) Uani 1 1 d . . .
C19 C 1.5428(2) 0.1358(2) -0.0976(2) 0.0472(7) Uani 1 1 d . . .
H19 H 1.6156 0.0794 -0.0812 0.057 Uiso 1 1 calc R . .
C15 C 0.7704(3) 0.2672(2) 0.3316(2) 0.0503(7) Uani 1 1 d . . .
H15 H 0.6877 0.3065 0.3123 0.06 Uiso 1 1 calc R . .
C21 C 1.3192(3) 0.3133(2) -0.1501(2) 0.0457(7) Uani 1 1 d . . .
C17 C 1.0303(2) 0.1464(2) 0.3926(2) 0.0417(6) Uani 1 1 d . . .
C18 C 0.6250(3) 0.1051(3) 0.4388(3) 0.0632(9) Uani 1 1 d . . .
H18A H 0.5426 0.1546 0.422 0.095 Uiso 1 1 calc R . .
H18B H 0.6071 0.0887 0.5115 0.095 Uiso 1 1 calc R . .
H18C H 0.6381 0.0343 0.41 0.095 Uiso 1 1 calc R . .
C22 C 1.5444(4) 0.0443(3) -0.2515(3) 0.0686(10) Uani 1 1 d . . .
H22A H 1.5874 0.0797 -0.3188 0.103 Uiso 1 1 calc R . .
H22B H 1.4628 0.0069 -0.2528 0.103 Uiso 1 1 calc R . .
H22C H 1.6167 -0.0118 -0.2283 0.103 Uiso 1 1 calc R . .
C16 C 0.7634(3) 0.1648(2) 0.3959(2) 0.0480(7) Uani 1 1 d . . .
O1 O 1.2226(2) 0.38504(18) -0.18177(18) 0.0620(6) Uani 1 1 d . . .
O2 O 1.13577(18) 0.08764(16) 0.42318(16) 0.0513(6) Uani 1 1 d . . .
N4 N 0.8895(2) 0.10915(19) 0.42379(19) 0.0464(6) Uani 1 1 d . . .
H4 H 0.8806 0.0456 0.4642 0.056 Uiso 1 1 calc R . .
N3 N 1.3833(2) 0.2210(2) -0.20422(19) 0.0510(6) Uani 1 1 d . . .
H3 H 1.3539 0.2164 -0.2569 0.061 Uiso 1 1 calc R . .
N100 N 0.9813(2) 0.1283(2) 0.0775(2) 0.0638(8) Uani 1 1 d . . .
O100 O 0.7384(2) 0.0995(3) 0.1192(3) 0.1016(11) Uani 1 1 d . . .
C102 C 0.8608(3) 0.0870(3) 0.1346(4) 0.0818(12) Uani 1 1 d . . .
H102 H 0.87 0.0421 0.1951 0.098 Uiso 1 1 calc R . .
C100 C 1.1235(4) 0.1113(4) 0.1000(4) 0.0905(13) Uani 1 1 d . . .
H10A H 1.1183 0.0631 0.1638 0.136 Uiso 1 1 calc R . .
H10B H 1.1509 0.1846 0.1041 0.136 Uiso 1 1 calc R . .
H10C H 1.1957 0.0748 0.0469 0.136 Uiso 1 1 calc R . .
C101 C 0.9744(6) 0.2033(5) -0.0207(5) 0.133(2) Uani 1 1 d . . .
H10D H 0.8787 0.2062 -0.0319 0.2 Uiso 1 1 calc R . .
H10E H 1.0479 0.1718 -0.0759 0.2 Uiso 1 1 calc R . .
H10F H 0.9922 0.2799 -0.0169 0.2 Uiso 1 1 calc R . .
N200 N 0.0171(5) 0.2538(3) 0.6294(3) 0.0869(11) Uani 1 1 d . . .
N300 N 0.5 0.5 0.5 0.147(3) Uani 1 2 d S . .
C301 C 0.5106(13) 0.4545(9) 0.5888(7) 0.206(4) Uani 1 1 d . . .
C300 C 0.6772(16) 0.5272(12) 0.4647(11) 0.128(4) Uiso 0.5 1 d P . .
O300 O 0.7539(13) 0.5014(10) 0.5326(10) 0.178(4) Uiso 0.5 1 d P . .
C202 C -0.0544(11) 0.3533(11) 0.5599(8) 0.105(3) Uani 0.5 1 d P . .
C201 C 0.0561(13) 0.3735(9) 0.6065(11) 0.127(4) Uani 0.5 1 d P . .
C203 C -0.127(3) 0.216(4) 0.643(4) 0.31(3) Uani 0.67(3) 1 d P . .
C210 C 0.1550(13) 0.2255(11) 0.6107(10) 0.104(4) Uani 0.6 1 d P . .
O201 O 0.2859(10) 0.1983(9) 0.6183(10) 0.097(3) Uani 0.4 1 d P . .
O200 O 0.2104(11) 0.1564(8) 0.6707(9) 0.116(3) Uani 0.6 1 d P . .
C211 C 0.154(3) 0.1689(17) 0.6350(16) 0.105(7) Uani 0.4 1 d P . .
C204 C -0.106(6) 0.200(3) 0.719(2) 0.28(4) Uani 0.38 1 d P . .
C205 C -0.106(2) 0.209(3) 0.668(5) 0.150(17) Uani 0.34 1 d P . .
C2 C 1.1577(2) 0.3227(2) 0.2741(2) 0.0407(6) Uani 1 1 d . . .
C9 C 1.4171(2) 0.3422(2) 0.0841(2) 0.0426(7) Uani 1 1 d . . .
C8 C 1.3322(2) 0.3871(2) 0.0170(2) 0.0417(7) Uani 1 1 d . . .
C7 C 1.2168(3) 0.4911(2) 0.0338(2) 0.0458(7) Uani 1 1 d . . .
H7A H 1.1286 0.478 0.0174 0.055 Uiso 1 1 calc R . .
H7B H 1.2535 0.5588 -0.0096 0.055 Uiso 1 1 calc R . .
C3 C 1.3190(2) 0.3029(2) 0.2759(2) 0.0430(6) Uani 1 1 d . . .
H3A H 1.3576 0.2225 0.2704 0.052 Uiso 1 1 calc R . .
H3B H 1.3289 0.3218 0.3394 0.052 Uiso 1 1 calc R . .
C4 C 1.4070(2) 0.3824(2) 0.1833(2) 0.0452(7) Uani 1 1 d . . .
H4A H 1.5062 0.3829 0.1908 0.054 Uiso 1 1 calc R . .
C5 C 1.3268(3) 0.5072(2) 0.1790(2) 0.0519(8) Uani 1 1 d . . .
H5A H 1.3897 0.5582 0.1299 0.062 Uiso 1 1 calc R . .
H5B H 1.3051 0.5338 0.2451 0.062 Uiso 1 1 calc R . .
C1 C 1.0981(2) 0.4162(2) 0.2183(2) 0.0420(7) Uani 1 1 d . . .
C6 C 1.1812(3) 0.5101(2) 0.1478(2) 0.0450(7) Uani 1 1 d . . .
H6 H 1.1223 0.5853 0.1573 0.054 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
C11 N1 1.377(3) . ?
C11 C10 1.424(3) . ?
C11 C15 1.434(4) . ?
C10 C17 1.442(4) . ?
C10 C2 1.463(3) . ?
C14 N2 1.362(4) . ?
C14 C19 1.412(4) . ?
C14 C12 1.415(3) . ?
C12 C21 1.427(4) . ?
C12 C8 1.437(4) . ?
N1 C1 1.401(3) . ?
N2 C9 1.387(3) . ?
C20 C19 1.363(4) . ?
C20 N3 1.397(4) . ?
C20 C22 1.499(4) . ?
C15 C16 1.378(4) . ?
C21 O1 1.267(3) . ?
C21 N3 1.386(4) . ?
C17 O2 1.258(3) . ?
C17 N4 1.410(3) . ?
C18 C16 1.524(4) . ?
C16 N4 1.394(4) . ?
N100 C102 1.315(5) . ?
N100 C100 1.448(4) . ?
N100 C101 1.504(6) . ?
O100 C102 1.224(4) . ?
N200 C210 1.267(11) . ?
N200 C205 1.30(3) . ?
N200 C203 1.47(3) . ?
N200 C201 1.484(11) . ?
N200 C211 1.53(2) . ?
N200 C202 1.581(10) . ?
N200 C204 1.58(3) . ?
N300 C301 1.278(10) . ?
N300 C301 1.278(10) 2_666 ?
N300 C300 1.691(15) 2_666 ?
N300 C300 1.691(15) . ?
C300 O300 1.310(16) . ?
C202 C201 1.444(17) . ?
C202 C203 1.94(5) . ?
C201 C210 1.849(15) . ?
C203 C205 0.44(10) . ?
C203 C204 1.10(7) . ?
C210 C211 0.70(2) . ?
C210 O200 1.229(13) . ?
C210 O201 1.265(15) . ?
O201 O200 0.997(14) . ?
O201 C211 1.30(3) . ?
O200 C211 0.80(2) . ?
C204 C205 0.69(8) . ?
C2 C1 1.378(4) . ?
C2 C3 1.523(3) . ?
C9 C8 1.381(4) . ?
C9 C4 1.492(4) . ?
C8 C7 1.514(3) . ?
C7 C6 1.557(4) . ?
C3 C4 1.577(4) . ?
C4 C5 1.549(4) . ?
C5 C6 1.555(4) . ?
C1 C6 1.521(3) . ?
