#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023905.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_4023905
loop_
_publ_author_name
'Murray V. Baker'
'David H. Brown'
'Charles H. Heath'
'Brian W. Skelton'
'Allan H. White'
'Charlotte C. Williams'
_publ_contact_author_address
;
   Department of Chemistry
   University of Western Australia
   35 Stirling Highway
   Crawley
   Western Australia 6009
   Australia
;
_publ_contact_author_email       bws@crystal.uwa.edu.au
_publ_contact_author_fax         (+61)_08_6488_1118
_publ_contact_author_name        'Skelton, B. W.'
_publ_contact_author_phone       (+61)_08_6488_7107
_publ_section_title
;
 Azolium-Linked Cyclophanes: Effects of Structure, Solvent,
 and Counteranions on Solution Conformation Behavior
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9340
_journal_page_last               9352
_journal_paper_doi               10.1021/jo801860d
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C46 H58 N4 O4, 4(H2 O), 2(Br)'
_chemical_formula_sum            'C46 H66 Br2 N4 O8'
_chemical_formula_weight         962.86
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             05-11-11
_audit_creation_method           Xtal3.6
_cell_angle_alpha                90.00000
_cell_angle_beta                 126.3340(10)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4
_cell_length_a                   20.524(2)
_cell_length_b                   20.512(2)
_cell_length_c                   13.6070(10)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    170
_cell_measurement_theta_max      32.65
_cell_measurement_theta_min      2.72
_cell_volume                     4614.7(7)
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_data_reduction        'xtal ADDREF SORTRF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type
;
Bruker SMART CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_detector       'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .023
_diffrn_reflns_av_sigmaI/netI    .041
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31846
_diffrn_reflns_theta_full        33.2
_diffrn_reflns_theta_max         33.2
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.812
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  .735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS; Sheldrick, 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          .55
_exptl_crystal_size_mid          .38
_exptl_crystal_size_min          .24
_refine_diff_density_max         .634
_refine_diff_density_min         -.593
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    .990
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     403
_refine_ls_number_reflns         8619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .046
_refine_ls_R_factor_gt           .034
_refine_ls_shift/su_max          .007
_refine_ls_shift/su_mean         .0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .063
_refine_ls_wR_factor_ref         .08
_reflns_d_resolution_high        .645
_reflns_d_resolution_low         12.839
_reflns_Friedel_coverage         0
_reflns_limit_h_max              31
_reflns_limit_h_min              0
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -20
_reflns_number_gt                6926
_reflns_number_total             8619
_reflns_threshold_expression     'I >  2.00 sig(I)'
_cod_data_source_file            jo801860d_si_005.cif
_cod_data_source_block           db236a
_cod_original_sg_symbol_Hall     -c_2yc
_cod_database_code               4023905
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,+y,1/2-z
-x,-y,-z
+x,-y,1/2+z
1/2+x,1/2+y,+z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+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 .564606(12) .260099(9) .489805(18) .03638(8) Uani ? ? 1.00000 ? ?
C11 .65320(8) .28210(6) .87134(12) .0184(4) Uani ? ? 1.00000 ? ?
C12 .64157(8) .29536(7) .96126(13) .0207(5) Uani ? ? 1.00000 ? ?
C13 .63257(9) .24403(8) 1.01932(14) .0248(5) Uani ? ? 1.00000 ? ?
C14 .63303(10) .17981(8) .98685(16) .0274(6) Uani ? ? 1.00000 ? ?
C15 .64393(10) .16643(7) .89788(16) .0274(6) Uani ? ? 1.00000 ? ?
C16 .65461(9) .21727(7) .84103(14) .0231(5) Uani ? ? 1.00000 ? ?
C1 .66358(9) .33506(7) .80456(14) .0229(5) Uani ? ? 1.00000 ? ?
N21 .58628(7) .37050(6) .71965(11) .0199(4) Uani ? ? 1.00000 ? ?
C22 .51567(9) .34005(7) .65019(14) .0228(5) Uani ? ? 1.00000 ? ?
N23 .45498(7) .38262(6) .58840(11) .0197(4) Uani ? ? 1.00000 ? ?
C24 .48856(8) .44508(6) .61630(12) .0174(4) Uani ? ? 1.00000 ? ?
C25 .45265(8) .50705(7) .57785(12) .0187(5) Uani ? ? 1.00000 ? ?
O25 .37045(6) .50954(5) .49804(10) .0229(4) Uani ? ? 1.00000 ? ?
C251 .33474(9) .57367(7) .46766(14) .0227(5) Uani ? ? 1.00000 ? ?
C252 .24417(9) .56488(7) .37742(14) .0239(5) Uani ? ? 1.00000 ? ?
C253 .19808(11) .62874(9) .3468(2) .0374(7) Uani ? ? 1.00000 ? ?
C254 .10728(11) .61892(11) .2540(2) .0412(8) Uani ? ? 1.00000 ? ?
C26 .50476(9) .55970(7) .62542(14) .0215(5) Uani ? ? 1.00000 ? ?
C27 .58944(9) .55170(7) .70794(13) .0207(5) Uani ? ? 1.00000 ? ?
C28 .62503(8) .49113(7) .74763(12) .0189(5) Uani ? ? 1.00000 ? ?
O28 .70598(6) .47853(5) .82893(10) .0232(4) Uani ? ? 1.00000 ? ?
C281 .75956(9) .53296(7) .86051(14) .0220(5) Uani ? ? 1.00000 ? ?
C282 .84527(9) .50828(8) .94842(14) .0247(5) Uani ? ? 1.00000 ? ?
C283 .90803(10) .56100(9) .98262(18) .0351(7) Uani ? ? 1.00000 ? ?
C284 .91271(14) .57975(11) .8796(3) .0437(9) Uani ? ? 1.00000 ? ?
C29 .57222(8) .43741(6) .69979(12) .0182(4) Uani ? ? 1.00000 ? ?
C2 .63219(9) .36402(7) .99142(14) .0245(5) Uani ? ? 1.00000 ? ?
O1 .60860(10) .29287(8) .29138(18) .0446(7) Uani ? ? 1.00000 ? ?
O2 .74947(11) .30962(9) .30470(16) .0452(7) Uani ? ? 1.00000 ? ?
H13 .6252(13) .2535(11) 1.084(2) .036(6) Uiso ? ? 1.00000 ? ?
H14 .6248(14) .1452(12) 1.026(2) .043(6) Uiso ? ? 1.00000 ? ?
H15 .6439(14) .1220(12) .876(2) .040(6) Uiso ? ? 1.00000 ? ?
H16 .6632(13) .2078(11) .781(2) .035(6) Uiso ? ? 1.00000 ? ?
H1a .7035(13) .3672(11) .861(2) .033(6) Uiso ? ? 1.00000 ? ?
H1b .6798(13) .3178(10) .7544(19) .029(5) Uiso ? ? 1.00000 ? ?
H22 .5097(12) .2960(10) .6500(18) .026(5) Uiso ? ? 1.00000 ? ?
H251a .3494(11) .5964(9) .5431(17) .017(4) Uiso ? ? 1.00000 ? ?
H251b .3552(12) .5995(10) .4301(19) .029(5) Uiso ? ? 1.00000 ? ?
H252a .2327(13) .5455(11) .302(2) .033(6) Uiso ? ? 1.00000 ? ?
H252b .2262(13) .5360(11) .412(2) .031(5) Uiso ? ? 1.00000 ? ?
H253a .2089(16) .6470(14) .424(3) .059(8) Uiso ? ? 1.00000 ? ?
H253b .2179(16) .6596(14) .315(2) .057(8) Uiso ? ? 1.00000 ? ?
H254a .0796(17) .6570(15) .239(3) .066(9) Uiso ? ? 1.00000 ? ?
H254b .0926(16) .6021(13) .173(3) .056(8) Uiso ? ? 1.00000 ? ?
H254c .0889(16) .5871(13) .289(3) .061(8) Uiso ? ? 1.00000 ? ?
H26 .4847(12) .6028(10) .6038(18) .022(5) Uiso ? ? 1.00000 ? ?
H27 .6194(13) .5890(10) .7387(19) .028(5) Uiso ? ? 1.00000 ? ?
H281a .7496(11) .5504(9) .7828(17) .020(5) Uiso ? ? 1.00000 ? ?
H281b .7485(12) .5661(10) .8978(18) .026(5) Uiso ? ? 1.00000 ? ?
H282a .8530(12) .4925(10) 1.0207(18) .024(5) Uiso ? ? 1.00000 ? ?
H282b .8548(12) .4707(10) .9110(19) .029(5) Uiso ? ? 1.00000 ? ?
H283a .8948(14) .6006(12) 1.007(2) .039(6) Uiso ? ? 1.00000 ? ?
H283b .9613(15) .5457(12) 1.049(2) .047(7) Uiso ? ? 1.00000 ? ?
H284a .9523(18) .6133(15) .907(3) .069(9) Uiso ? ? 1.00000 ? ?
H284b .9251(16) .5443(14) .852(2) .053(8) Uiso ? ? 1.00000 ? ?
H284c .8615(16) .5975(13) .812(2) .049(7) Uiso ? ? 1.00000 ? ?
H2a .6506(13) .3663(11) 1.077(2) .034(6) Uiso ? ? 1.00000 ? ?
H2b .6588(11) .3954(9) .9739(17) .019(4) Uiso ? ? 1.00000 ? ?
H1aO .6036(19) .2799(16) .343(3) .068(10) Uiso ? ? 1.00000 ? ?
H1bO .5709(18) .2816(14) .232(3) .051(8) Uiso ? ? 1.00000 ? ?
H2aO .7174(16) .2987(13) .311(2) .043(7) Uiso ? ? 1.00000 ? ?
H2bO .7897(18) .2904(14) .358(3) .058(9) Uiso ? ? 1.00000 ? ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C ? 0 184 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H ? 0 264 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
Br ? 0 8 -.374 2.456 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N ? 0 16 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O ? 0 32 .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 C11 C16 . . . 119.03(16) ?
C12 C11 C1 . . . 122.82(13) ?
C16 C11 C1 . . . 118.15(18) ?
C11 C12 C13 . . . 119.70(15) ?
C11 C12 C2 . . . 122.13(15) ?
C13 C12 C2 . . . 118.01(19) ?
C12 C13 C14 . . . 120.5(2) ?
C12 C13 H13 . . . 119.6(14) ?
C14 C13 H13 . . . 119.9(14) ?
C13 C14 C15 . . . 120.07(19) ?
C13 C14 H14 . . . 119.0(18) ?
C15 C14 H14 . . . 120.9(18) ?
C14 C15 C16 . . . 119.91(16) ?
C14 C15 H15 . . . 120(2) ?
C16 C15 H15 . . . 120(2) ?
C11 C16 C15 . . . 120.8(2) ?
C11 C16 H16 . . . 119.5(14) ?
C15 C16 H16 . . . 119.7(14) ?
C11 C1 N21 . . . 110.70(15) ?
C11 C1 H1a . . . 111.7(16) ?
C11 C1 H1b . . . 112.6(13) ?
N21 C1 H1a . . . 107.1(13) ?
N21 C1 H1b . . . 106.3(10) ?
H1a C1 H1b . . . 108(2) ?
C1 N21 C22 . . . 122.40(12) ?
C1 N21 C29 . . . 129.39(11) ?
C22 N21 C29 . . . 108.18(11) ?
N21 C22 N23 . . . 111.01(12) ?
N21 C22 H22 . . . 123.9(12) ?
N23 C22 H22 . . . 125.0(12) ?
C22 N23 C24 . . . 107.64(11) ?
C22 N23 C2 . . '2 656' 124.12(12) ?
C24 N23 C2 . . '2 656' 128.21(11) ?
N23 C24 C25 . . . 131.53(12) ?
N23 C24 C29 . . . 106.76(11) ?
C25 C24 C29 . . . 121.69(12) ?
C24 C25 O25 . . . 117.32(12) ?
C24 C25 C26 . . . 116.28(12) ?
O25 C25 C26 . . . 126.40(12) ?
C25 O25 C251 . . . 116.20(10) ?
O25 C251 C252 . . . 107.17(11) ?
O25 C251 H251a . . . 109.8(10) ?
O25 C251 H251b . . . 109.8(14) ?
C252 C251 H251a . . . 111.5(12) ?
C252 C251 H251b . . . 109.8(10) ?
H251a C251 H251b . . . 108.7(18) ?
C251 C252 C253 . . . 112.64(13) ?
C251 C252 H252a . . . 108.2(15) ?
C251 C252 H252b . . . 108.6(10) ?
C253 C252 H252a . . . 109.4(12) ?
C253 C252 H252b . . . 108.0(15) ?
H252a C252 H252b . . . 110(2) ?
C252 C253 C254 . . . 111.71(15) ?
C252 C253 H253a . . . 108.5(15) ?
C252 C253 H253b . . . 109(2) ?
C254 C253 H253a . . . 108.6(18) ?
C254 C253 H253b . . . 110.2(13) ?
H253a C253 H253b . . . 109(3) ?
C253 C254 H254a . . . 111.5(16) ?
C253 C254 H254b . . . 112.0(18) ?
C253 C254 H254c . . . 108.3(13) ?
H254a C254 H254b . . . 107(3) ?
H254a C254 H254c . . . 108(3) ?
H254b C254 H254c . . . 110(3) ?
C25 C26 C27 . . . 121.88(12) ?
C25 C26 H26 . . . 120.8(11) ?
C27 C26 H26 . . . 117.3(11) ?
C26 C27 C28 . . . 122.18(13) ?
C26 C27 H27 . . . 116.3(13) ?
C28 C27 H27 . . . 121.3(12) ?
C27 C28 O28 . . . 126.47(12) ?
C27 C28 C29 . . . 116.15(12) ?
O28 C28 C29 . . . 117.38(12) ?
C28 O28 C281 . . . 116.15(11) ?
O28 C281 C282 . . . 107.49(12) ?
O28 C281 H281a . . . 108.3(10) ?
O28 C281 H281b . . . 109.3(15) ?
C282 C281 H281a . . . 111.4(13) ?
C282 C281 H281b . . . 110.5(10) ?
H281a C281 H281b . . . 109.8(19) ?
C281 C282 C283 . . . 112.31(13) ?
C281 C282 H282a . . . 109.5(14) ?
C281 C282 H282b . . . 109.9(10) ?
C283 C282 H282a . . . 109.3(11) ?
C283 C282 H282b . . . 108.4(15) ?
H282a C282 H282b . . . 107(2) ?
C282 C283 C284 . . . 113.78(16) ?
C282 C283 H283a . . . 109.7(17) ?
C282 C283 H283b . . . 109.6(17) ?
C284 C283 H283a . . . 106.9(18) ?
C284 C283 H283b . . . 107(2) ?
H283a C283 H283b . . . 110(2) ?
C283 C284 H284a . . . 110(2) ?
C283 C284 H284b . . . 111(2) ?
C283 C284 H284c . . . 111(2) ?
H284a C284 H284b . . . 110(3) ?
H284a C284 H284c . . . 107(2) ?
H284b C284 H284c . . . 108(2) ?
N21 C29 C24 . . . 106.36(11) ?
N21 C29 C28 . . . 131.83(11) ?
C24 C29 C28 . . . 121.80(12) ?
C12 C2 H2a . . . 110.0(13) ?
C12 C2 H2b . . . 112.0(15) ?
C12 C2 N23 . . '2 656' 109.37(10) ?
H2a C2 H2b . . . 112.6(18) ?
H2a C2 N23 . . '2 656' 107.6(15) ?
H2b C2 N23 . . '2 656' 105.1(10) ?
H1aO O1 H1bO . . . 105(4) ?
H2aO O2 H2bO . . . 105(4) ?
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
C11 C12 . . 1.405(3) ?
C11 C16 . . 1.398(2) ?
C11 C1 . . 1.510(3) ?
C12 C13 . . 1.393(3) ?
C12 C2 . . 1.511(2) ?
C13 C14 . . 1.391(2) ?
C13 H13 . . .99(3) ?
C14 C15 . . 1.383(4) ?
C14 H14 . . .96(3) ?
C15 C16 . . 1.391(3) ?
C15 H15 . . .96(2) ?
C16 H16 . . .96(3) ?
C1 N21 . . 1.4862(17) ?
C1 H1a . . .97(2) ?
C1 H1b . . .99(3) ?
N21 C22 . . 1.3269(18) ?
N21 C29 . . 1.3954(18) ?
C22 N23 . . 1.3341(18) ?
C22 H22 . . .91(2) ?
N23 C24 . . 1.3967(18) ?
N23 C2 . '2 656' 1.4910(18) ?
C24 C25 . . 1.4057(18) ?
C24 C29 . . 1.3973(17) ?
C25 O25 . . 1.3627(16) ?
C25 C26 . . 1.382(2) ?
O25 C251 . . 1.4420(18) ?
C251 C252 . . 1.514(2) ?
C251 H251a . . 1.00(2) ?
C251 H251b . . .99(3) ?
C252 C253 . . 1.522(2) ?
C252 H252a . . 1.00(3) ?
C252 H252b . . .96(3) ?
C253 C254 . . 1.523(2) ?
C253 H253a . . 1.01(4) ?
C253 H253b . . .98(4) ?
C254 H254a . . .91(3) ?
C254 H254b . . 1.02(3) ?
C254 H254c . . 1.00(4) ?
C26 C27 . . 1.413(2) ?
C26 H26 . . .95(2) ?
C27 C28 . . 1.379(2) ?
C27 H27 . . .91(2) ?
C28 O28 . . 1.3685(16) ?
C28 C29 . . 1.4059(19) ?
O28 C281 . . 1.4424(19) ?
C281 C282 . . 1.513(2) ?
C281 H281a . . 1.01(2) ?
C281 H281b . . .95(3) ?
C282 C283 . . 1.528(3) ?
C282 H282a . . .96(3) ?
C282 H282b . . 1.00(3) ?
C283 C284 . . 1.510(5) ?
C283 H283a . . .98(3) ?
C283 H283b . . .97(2) ?
C284 H284a . . .96(3) ?
C284 H284b . . .92(3) ?
C284 H284c . . .97(2) ?
C2 H2a . . .99(3) ?
C2 H2b . . .96(2) ?
O1 H1aO . . .81(5) ?
O1 H1bO . . .75(2) ?
O2 H2aO . . .74(4) ?
O2 H2bO . . .81(3) ?
