#------------------------------------------------------------------------------
#$Date: 2018-02-05 01:16:54 +0200 (Mon, 05 Feb 2018) $
#$Revision: 206172 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/11/4021169.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_4021169
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         'C30 H38 N4, 2Br, 3(C H4 O)'
_chemical_formula_sum            'C33 H50 Br2 N4 O5'
_chemical_formula_weight         742.59
_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                92.181(2)
_cell_angle_beta                 105.020(2)
_cell_angle_gamma                112.622(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5409(7)
_cell_length_b                   13.3867(9)
_cell_length_c                   14.1980(10)
_cell_measurement_temperature    150(2)
_cell_volume                     1764.7(2)
_exptl_crystal_density_diffrn    1.398
_cod_database_code               4021169
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 .20187(3) .68302(2) .21598(2) .02724(10) Uani ? ? 1.00000 ? ?
Br2 -.20353(3) .83944(3) .56556(2) .02724(10) Uani ? ? 1.00000 ? ?
C1 .3995(2) .78111(18) .50906(16) .0168(6) Uani ? ? 1.00000 ? ?
C11 .3460(2) .68647(18) .56342(16) .0158(6) Uani ? ? 1.00000 ? ?
C12 .2088(2) .64954(18) .57634(16) .0161(6) Uani ? ? 1.00000 ? ?
O12 .1105(2) .69152(16) .53901(14) .0216(6) Uani ? ? 1.00000 ? ?
C13 .1687(2) .56700(18) .63392(17) .0166(7) Uani ? ? 1.00000 ? ?
C14 .2639(3) .52079(18) .67616(18) .0186(7) Uani ? ? 1.00000 ? ?
C15 .4000(2) .55372(18) .66273(17) .0171(7) Uani ? ? 1.00000 ? ?
C151 .5030(3) .49970(19) .70429(18) .0199(7) Uani ? ? 1.00000 ? ?
C152 .6544(4) .5863(3) .7586(4) .0454(14) Uani ? ? 1.00000 ? ?
C153 .4552(5) .4249(5) .7777(4) .055(2) Uani ? ? 1.00000 ? ?
C154 .5146(6) .4336(4) .6195(3) .0598(19) Uani ? ? 1.00000 ? ?
C16 .4381(2) .63761(18) .60641(17) .0175(7) Uani ? ? 1.00000 ? ?
C2 .3904(3) 1.11195(19) .67527(17) .0175(7) Uani ? ? 1.00000 ? ?
N21 .4436(2) .88651(15) .57220(14) .0154(6) Uani ? ? 1.00000 ? ?
C22 .3682(2) .94762(18) .57026(17) .0170(7) Uani ? ? 1.00000 ? ?
N23 .4402(2) 1.03019(15) .64515(14) .0162(6) Uani ? ? 1.00000 ? ?
C24 .5642(3) 1.0211(2) .6972(2) .0219(8) Uani ? ? 1.00000 ? ?
C25 .5665(3) .9314(2) .65212(19) .0219(8) Uani ? ? 1.00000 ? ?
C3 .0111(2) .86245(19) .81476(19) .0182(7) Uani ? ? 1.00000 ? ?
C31 .1500(2) .96092(18) .82682(17) .0165(6) Uani ? ? 1.00000 ? ?
C32 .2013(2) .99259(18) .74643(16) .0156(6) Uani ? ? 1.00000 ? ?
O32 .13423(19) .93779(15) .65236(13) .0212(6) Uani ? ? 1.00000 ? ?
C33 .3332(2) 1.08219(17) .76192(17) .0159(6) Uani ? ? 1.00000 ? ?
C34 .4104(2) 1.14153(18) .85615(17) .0172(7) Uani ? ? 1.00000 ? ?
C35 .3600(2) 1.11376(18) .93765(17) .0167(7) Uani ? ? 1.00000 ? ?
C351 .4469(3) 1.17785(19) 1.04171(18) .0202(7) Uani ? ? 1.00000 ? ?
C352 .3491(4) 1.1687(3) 1.1068(2) .0340(11) Uani ? ? 1.00000 ? ?
C353 .5299(4) 1.2988(2) 1.0382(2) .0346(10) Uani ? ? 1.00000 ? ?
C354 .5541(4) 1.1294(3) 1.0891(2) .0336(10) Uani ? ? 1.00000 ? ?
C36 .2303(2) 1.02208(18) .92065(17) .0173(7) Uani ? ? 1.00000 ? ?
C4 .0242(2) .53313(18) .65181(19) .0185(7) Uani ? ? 1.00000 ? ?
N41 .0259(2) .75796(16) .79916(14) .0168(6) Uani ? ? 1.00000 ? ?
C42 -.0025(2) .70030(19) .71192(18) .0180(7) Uani ? ? 1.00000 ? ?
N43 .0284(2) .61357(16) .72822(15) .0165(6) Uani ? ? 1.00000 ? ?
C44 .0779(3) .6161(2) .82857(19) .0229(8) Uani ? ? 1.00000 ? ?
C45 .0761(3) .7066(2) .87276(19) .0230(8) Uani ? ? 1.00000 ? ?
O01 .1339(3) .8551(2) .08175(17) .0359(9) Uani ? ? 1.00000 ? ?
C01 .0461(4) .8917(3) .1204(3) .0370(12) Uani ? ? 1.00000 ? ?
O02 .1002(2) .7921(2) .38038(16) .0323(8) Uani ? ? 1.00000 ? ?
C02 -.0254(4) .8143(3) .3559(3) .0384(13) Uani ? ? 1.00000 ? ?
O03 -.1473(3) .5988(2) .12741(19) .0393(9) Uani ? ? 1.00000 ? ?
C03 -.1983(5) .5836(4) .0231(3) .0498(15) Uani ? ? 1.00000 ? ?
H1a .479(4) .784(3) .491(3) .028(9) Uiso ? ? 1.00000 ? ?
H1b .328(3) .776(3) .447(2) .016(7) Uiso ? ? 1.00000 ? ?
H12 .123(4) .720(3) .494(3) .033(10) Uiso ? ? 1.00000 ? ?
H14 .237(3) .470(3) .713(2) .017(7) Uiso ? ? 1.00000 ? ?
H152a .721(5) .545(4) .778(3) .050(12) Uiso ? ? 1.00000 ? ?
H152b .686(5) .628(4) .710(4) .059(14) Uiso ? ? 1.00000 ? ?
H152c .649(7) .638(5) .826(5) .11(2) Uiso ? ? 1.00000 ? ?
H153a .523(5) .395(3) .803(3) .043(11) Uiso ? ? 1.00000 ? ?
H153b .451(5) .468(4) .828(3) .045(12) Uiso ? ? 1.00000 ? ?
H153c .351(8) .359(6) .738(5) .12(2) Uiso ? ? 1.00000 ? ?
H154a .578(6) .390(4) .648(4) .079(17) Uiso ? ? 1.00000 ? ?
H154b .418(4) .377(3) .591(3) .045(12) Uiso ? ? 1.00000 ? ?
H154c .564(7) .495(5) .566(5) .10(2) Uiso ? ? 1.00000 ? ?
H16 .530(4) .663(3) .597(2) .020(8) Uiso ? ? 1.00000 ? ?
H2a .471(4) 1.178(3) .693(3) .031(9) Uiso ? ? 1.00000 ? ?
H2b .321(4) 1.115(3) .621(2) .023(8) Uiso ? ? 1.00000 ? ?
H22 .284(4) .934(3) .525(3) .024(8) Uiso ? ? 1.00000 ? ?
H24 .624(4) 1.070(3) .751(3) .036(10) Uiso ? ? 1.00000 ? ?
H25 .631(4) .899(3) .663(3) .032(9) Uiso ? ? 1.00000 ? ?
H3a -.016(4) .861(3) .868(3) .028(9) Uiso ? ? 1.00000 ? ?
H3b -.067(3) .861(3) .760(2) .018(7) Uiso ? ? 1.00000 ? ?
H32 .049(4) .914(3) .639(3) .036(10) Uiso ? ? 1.00000 ? ?
H34 .500(4) 1.204(3) .863(2) .021(8) Uiso ? ? 1.00000 ? ?
H352a .404(4) 1.211(3) 1.171(3) .040(11) Uiso ? ? 1.00000 ? ?
H352b .276(4) 1.191(3) 1.075(3) .034(10) Uiso ? ? 1.00000 ? ?
H352c .296(5) 1.094(4) 1.118(3) .046(11) Uiso ? ? 1.00000 ? ?
H353a .577(4) 1.338(3) 1.104(3) .033(10) Uiso ? ? 1.00000 ? ?
H353b .603(5) 1.312(3) 1.005(3) .043(11) Uiso ? ? 1.00000 ? ?
H353c .465(5) 1.329(4) 1.005(3) .050(12) Uiso ? ? 1.00000 ? ?
H354a .613(4) 1.165(3) 1.157(3) .039(10) Uiso ? ? 1.00000 ? ?
H354b .498(5) 1.054(4) 1.095(3) .053(13) Uiso ? ? 1.00000 ? ?
H354c .617(5) 1.134(4) 1.048(3) .048(12) Uiso ? ? 1.00000 ? ?
H36 .191(3) .997(2) -.028(2) .014(7) Uiso ? ? 1.00000 ? ?
H4a -.048(4) .531(3) .591(3) .026(8) Uiso ? ? 1.00000 ? ?
H4b -.002(3) .469(3) .672(2) .020(8) Uiso ? ? 1.00000 ? ?
H42 -.039(4) .718(3) .651(3) .035(10) Uiso ? ? 1.00000 ? ?
H44 .108(4) .563(3) .852(3) .028(9) Uiso ? ? 1.00000 ? ?
H45 .106(4) .734(3) -.061(3) .029(9) Uiso ? ? 1.00000 ? ?
H01 .143(6) .799(5) .116(4) .081(17) Uiso ? ? 1.00000 ? ?
H01a -.035(5) .831(4) .121(3) .046(12) Uiso ? ? 1.00000 ? ?
H01b .022(5) .943(4) .081(4) .061(14) Uiso ? ? 1.00000 ? ?
H01c .100(5) .934(4) .189(3) .047(12) Uiso ? ? 1.00000 ? ?
H02 .110(4) .765(3) .335(3) .038(11) Uiso ? ? 1.00000 ? ?
H02a -.065(6) .806(4) .405(4) .068(15) Uiso ? ? 1.00000 ? ?
H02b -.097(5) .770(4) .289(4) .060(14) Uiso ? ? 1.00000 ? ?
H02c .002(5) .891(4) .350(4) .063(14) Uiso ? ? 1.00000 ? ?
H03 -.048(5) .630(4) .142(3) .051(13) Uiso ? ? 1.00000 ? ?
H03a -.157(6) .534(5) -.010(4) .09(2) Uiso ? ? 1.00000 ? ?
H03b -.165(6) .657(4) -.004(4) .072(16) Uiso ? ? 1.00000 ? ?
H03c -.302(6) .552(4) .003(4) .074(16) 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 . . 1.507(3) ?
C1 N21 . . 1.481(3) ?
C1 H1a . . .92(4) ?
C1 H1b . . .98(3) ?
C11 C12 . . 1.401(3) ?
C11 C16 . . 1.398(4) ?
C12 O12 . . 1.363(4) ?
C12 C13 . . 1.399(3) ?
O12 H12 . . .77(4) ?
C13 C14 . . 1.393(4) ?
C13 C4 . . 1.506(4) ?
C14 C15 . . 1.397(4) ?
C14 H14 . . .88(3) ?
C15 C151 . . 1.535(4) ?
C15 C16 . . 1.396(3) ?
C151 C152 . . 1.535(3) ?
C151 C153 . . 1.519(6) ?
C151 C154 . . 1.525(6) ?
C152 H152a . . 1.04(6) ?
C152 H152b . . .95(5) ?
C152 H152c . . 1.18(8) ?
C153 H153a . . .95(5) ?
C153 H153b . . .92(5) ?
C153 H153c . . 1.09(6) ?
C154 H154a . . 1.07(7) ?
C154 H154b . . .97(3) ?
C154 H154c . . 1.20(7) ?
C16 H16 . . .95(4) ?
C2 N23 . . 1.477(4) ?
C2 C33 . . 1.508(4) ?
C2 H2a . . .93(3) ?
C2 H2b . . .93(3) ?
N21 C22 . . 1.338(4) ?
N21 C25 . . 1.384(3) ?
C22 N23 . . 1.332(3) ?
C22 H22 . . .90(3) ?
N23 C24 . . 1.377(3) ?
C24 C25 . . 1.351(4) ?
C24 H24 . . .90(3) ?
C25 H25 . . .93(5) ?
C3 C31 . . 1.510(3) ?
C3 N41 . . 1.480(4) ?
C3 H3a . . .87(4) ?
C3 H3b . . .97(3) ?
C31 C32 . . 1.398(4) ?
C31 C36 . . 1.400(3) ?
C32 O32 . . 1.363(3) ?
C32 C33 . . 1.400(3) ?
O32 H32 . . .80(4) ?
C33 C34 . . 1.393(3) ?
C34 C35 . . 1.399(4) ?
C34 H34 . . .97(3) ?
C35 C351 . . 1.535(3) ?
C35 C36 . . 1.396(3) ?
C351 C352 . . 1.529(5) ?
C351 C353 . . 1.526(4) ?
C351 C354 . . 1.534(5) ?
C352 H352a . . .96(4) ?
C352 H352b . . .94(5) ?
C352 H352c . . .98(4) ?
C353 H353a . . .96(4) ?
C353 H353b . . .97(5) ?
C353 H353c . . .95(5) ?
C354 H354a . . .98(4) ?
C354 H354b . . .97(5) ?
C354 H354c . . .98(5) ?
C36 H36 . '1 556' .94(3) ?
C4 N43 . . 1.479(4) ?
C4 H4a . . .98(3) ?
C4 H4b . . .88(4) ?
N41 C42 . . 1.333(3) ?
N41 C45 . . 1.376(4) ?
C42 N43 . . 1.334(4) ?
C42 H42 . . .93(4) ?
N43 C44 . . 1.379(3) ?
C44 C45 . . 1.353(4) ?
C44 H44 . . .92(4) ?
C45 H45 . '1 556' .92(4) ?
O01 C01 . . 1.410(6) ?
O01 H01 . . .93(6) ?
C01 H01a . . .93(4) ?
C01 H01b . . .97(6) ?
C01 H01c . . 1.01(4) ?
O02 C02 . . 1.427(5) ?
O02 H02 . . .77(5) ?
C02 H02a . . .89(6) ?
C02 H02b . . 1.03(4) ?
C02 H02c . . .96(6) ?
O03 C03 . . 1.415(5) ?
O03 H03 . . .93(5) ?
C03 H03a . . 1.07(8) ?
C03 H03b . . 1.03(6) ?
C03 H03c . . .96(6) ?
