#------------------------------------------------------------------------------
#$Date: 2018-02-05 01:16:54 +0200 (Mon, 05 Feb 2018) $
#$Revision: 206172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/11/4021165.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_4021165
loop_
_publ_author_name
'Murray V. Baker'
'Mark J. Bosnich'
'David H. Brown'
'Lindsay T. Byrne'
'Valerie J. Hesler'
'Brian W. Skelton'
'Allan H. White'
'Charlotte C. Williams'
_publ_section_title
;
 Azolium-Linked Cyclophanes: A Comprehensive Examination
 of Conformations by ¹H-NMR Spectroscopy and Structural Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7640
_journal_page_last               7652
_journal_paper_doi               10.1021/jo049097o
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C21 H21 N5, 2Br, C H4 O'
_chemical_formula_sum            'C22 H25 Br2 N5 O'
_chemical_formula_weight         535.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_cell_angle_alpha                80.5080(10)
_cell_angle_beta                 84.6670(10)
_cell_angle_gamma                78.3820(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8032(8)
_cell_length_b                   9.5861(9)
_cell_length_c                   14.0000(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1139.20(17)
_exptl_crystal_density_diffrn    1.56
_cod_original_formula_sum        'C22 H25 Br2 N5 O1'
_cod_database_code               4021165
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 -.04048(3) .74954(3) .666682(18) .03126(18) Uani ? ? 1.00000 ? ?
Br2 -.31571(3) 1.15192(3) .87779(2) .0334(2) Uani ? ? 1.00000 ? ?
C1 -.0386(3) .4169(3) .82569(17) .0248(16) Uani ? ? 1.00000 ? ?
C11 .0906(3) .4065(3) .89084(16) .0251(16) Uani ? ? 1.00000 ? ?
C12 .1564(3) .2764(3) .94603(16) .0262(16) Uani ? ? 1.00000 ? ?
C13 .2739(3) .2741(3) 1.0070(2) .035(2) Uani ? ? 1.00000 ? ?
C14 .3237(3) .3999(4) 1.0137(2) .043(2) Uani ? ? 1.00000 ? ?
C15 .2583(3) .5284(4) .9609(2) .040(2) Uani ? ? 1.00000 ? ?
C16 .1419(3) .5322(3) .8989(2) .0325(19) Uani ? ? 1.00000 ? ?
C2 .2650(3) .3758(3) .51362(18) .0276(17) Uani ? ? 1.00000 ? ?
N21 .0180(2) .3703(2) .73067(13) .0232(13) Uani ? ? 1.00000 ? ?
C22 .1422(3) .4039(3) .67775(17) .0236(15) Uani ? ? 1.00000 ? ?
N23 .1428(2) .3653(2) .59099(14) .0243(13) Uani ? ? 1.00000 ? ?
C24 .0146(3) .3038(3) .58814(19) .0319(18) Uani ? ? 1.00000 ? ?
C25 -.0642(3) .3089(3) .67491(18) .0317(18) Uani ? ? 1.00000 ? ?
C3 .5237(3) -.0563(3) .7136(2) .0328(18) Uani ? ? 1.00000 ? ?
C31 .5341(3) .0646(3) .62959(18) .0276(16) Uani ? ? 1.00000 ? ?
N32 .4038(2) .1607(2) .60978(14) .0250(13) Uani ? ? 1.00000 ? ?
C33 .4127(3) .2685(3) .53655(16) .0255(16) Uani ? ? 1.00000 ? ?
C34 .5495(3) .2844(3) .48145(18) .0317(18) Uani ? ? 1.00000 ? ?
C35 .6831(3) .1833(3) .5024(2) .037(2) Uani ? ? 1.00000 ? ?
C36 .6760(3) .0720(3) .5774(2) .036(2) Uani ? ? 1.00000 ? ?
C4 .1041(3) .1372(3) .94260(19) .0280(17) Uani ? ? 1.00000 ? ?
N41 .3727(2) -.0337(2) .76866(15) .0276(14) Uani ? ? 1.00000 ? ?
C42 .3373(3) .0493(3) .83787(18) .0262(16) Uani ? ? 1.00000 ? ?
C44 .1238(3) -.0174(3) .8076(2) .0326(18) Uani ? ? 1.00000 ? ?
N43 .1863(2) .0616(2) .86280(14) .0252(13) Uani ? ? 1.00000 ? ?
C45 .2384(3) -.0752(3) .7485(2) .034(2) Uani ? ? 1.00000 ? ?
O01 -.5058(3) .4207(2) .71373(16) .0437(16) Uani ? ? 1.00000 ? ?
C01 -.4594(4) .5231(3) .7597(2) .040(2) Uani ? ? 1.00000 ? ?
H1a -.087(3) .509(3) .8078(18) .024(6) Uiso ? ? 1.00000 ? ?
H1b -.110(3) .354(3) .8539(17) .025(6) Uiso ? ? 1.00000 ? ?
H13 .325(3) .180(3) 1.042(2) .033(7) Uiso ? ? 1.00000 ? ?
H14 .401(4) .387(3) 1.052(2) .056(10) Uiso ? ? 1.00000 ? ?
H15 .296(4) .613(4) .964(2) .058(10) Uiso ? ? 1.00000 ? ?
H16 .097(3) .617(3) .859(2) .034(8) Uiso ? ? 1.00000 ? ?
H2a .287(3) .474(3) .505(2) .033(7) Uiso ? ? 1.00000 ? ?
H2b .220(2) .355(2) .4565(16) .011(5) Uiso ? ? 1.00000 ? ?
H22 .217(3) .447(2) .6984(17) .019(6) Uiso ? ? 1.00000 ? ?
H24 .001(3) .271(3) .531(2) .035(7) Uiso ? ? 1.00000 ? ?
H25 -.151(3) .278(3) .698(2) .042(8) Uiso ? ? 1.00000 ? ?
H3a .600(3) -.058(3) .760(2) .040(8) Uiso ? ? 1.00000 ? ?
H3b .531(3) -.148(3) .685(2) .043(8) Uiso ? ? 1.00000 ? ?
H34 .554(4) .366(3) .433(2) .051(9) Uiso ? ? 1.00000 ? ?
H35 .785(4) .199(3) .464(2) .051(9) Uiso ? ? 1.00000 ? ?
H36 .765(4) .004(3) .595(2) .054(9) Uiso ? ? 1.00000 ? ?
H4a -.003(3) .149(3) .9329(18) .026(6) Uiso ? ? 1.00000 ? ?
H4b .129(3) .077(3) .9972(19) .022(6) Uiso ? ? 1.00000 ? ?
H42 .412(3) .092(3) .8654(18) .028(7) Uiso ? ? 1.00000 ? ?
H44 .022(4) -.023(3) .813(2) .046(8) Uiso ? ? 1.00000 ? ?
H45 .230(3) -.128(3) .699(2) .043(8) Uiso ? ? 1.00000 ? ?
H01 -.468(4) .349(3) .741(2) .045(10) Uiso ? ? 1.00000 ? ?
H01a -.376(4) .560(3) .721(2) .054(9) Uiso ? ? 1.00000 ? ?
H01b -.554(4) .608(3) .762(2) .047(8) Uiso ? ? 1.00000 ? ?
H01c -.456(4) .485(4) .828(3) .060(10) Uiso ? ? 1.00000 ? ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C11 . . 1.500(4) ?
C1 N21 . . 1.484(3) ?
C1 H1a . . .90(2) ?
C1 H1b . . .98(3) ?
C11 C12 . . 1.401(3) ?
C11 C16 . . 1.394(4) ?
C12 C13 . . 1.395(4) ?
C12 C4 . . 1.506(4) ?
C13 C14 . . 1.383(5) ?
C13 H13 . . .99(2) ?
C14 C15 . . 1.373(4) ?
C14 H14 . . .88(4) ?
C15 C16 . . 1.395(4) ?
C15 H15 . . .94(4) ?
C16 H16 . . .94(2) ?
C2 N23 . . 1.460(3) ?
C2 C33 . . 1.510(3) ?
C2 H2a . . .99(3) ?
C2 H2b . . .99(2) ?
N21 C22 . . 1.328(3) ?
N21 C25 . . 1.381(4) ?
C22 N23 . . 1.326(3) ?
C22 H22 . . .93(3) ?
N23 C24 . . 1.381(4) ?
C24 C25 . . 1.345(4) ?
C24 H24 . . .93(3) ?
C25 H25 . . .89(3) ?
C3 C31 . . 1.519(3) ?
C3 N41 . . 1.469(3) ?
C3 H3a . . .97(3) ?
C3 H3b . . 1.02(3) ?
C31 N32 . . 1.338(3) ?
C31 C36 . . 1.396(4) ?
N32 C33 . . 1.339(3) ?
C33 C34 . . 1.389(3) ?
C34 C35 . . 1.386(3) ?
C34 H34 . . .95(3) ?
C35 C36 . . 1.376(4) ?
C35 H35 . . 1.03(3) ?
C36 H36 . . .94(3) ?
C4 N43 . . 1.484(3) ?
C4 H4a . . .94(3) ?
C4 H4b . . .89(2) ?
N41 C42 . . 1.329(3) ?
N41 C45 . . 1.387(4) ?
C42 N43 . . 1.329(3) ?
C42 H42 . . .97(3) ?
C44 N43 . . 1.383(4) ?
C44 C45 . . 1.335(4) ?
C44 H44 . . .91(3) ?
C45 H45 . . .94(3) ?
O01 C01 . . 1.401(4) ?
O01 H01 . . .75(3) ?
C01 H01a . . .96(3) ?
C01 H01b . . 1.04(3) ?
C01 H01c . . .97(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21155160
