#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/05/2010570.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2010570
loop_
_publ_author_name
'Yuan, Yi'
'Zhou, Haibing'
'Jiang, Zhonlin'
'Yan, Jiaming'
'Xie, Rugang'
_publ_section_title
;
 A new tribridged imidazolium cyclophane
;
_journal_data_validation_number  IUC9900198
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e34
_journal_page_last               e35
_journal_paper_doi               10.1107/S0108270199016406
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C33 H39 N6 3+, 3Br 1-, 2H2 O'
_chemical_formula_sum            'C33 H43 Br3 N6 O2'
_chemical_formula_weight         795.46
_chemical_melting_point_gt       573
_chemical_name_common            none
_chemical_name_systematic
;
2,11,13,21,29,31-hexamethyl-5,16,24-triaza-8,19,27-triazoniaheptacyclo-
[10.10.6.1^1,3^.1^5,8^.1^10,14^.1^16,19^.1^24,27^]tritriaconta-
1,3(29),6,8(30),10,12,14(31),17,19(32),21,25,27(33)-dodecene tribromide
dihydrate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.855(2)
_cell_length_b                   17.306(3)
_cell_length_c                   10.607(2)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.44
_cell_measurement_theta_min      3.16
_cell_volume                     1648.9(6)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Siemens, 1994)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  'SHELXTL (Siemens, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .993
_diffrn_measured_fraction_theta_max .993
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .022
_diffrn_reflns_av_sigmaI/netI    .0602
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3533
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        5.36
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.710
_exptl_absorpt_correction_T_max  .354
_exptl_absorpt_correction_T_min  .227
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SHELXTL; Siemems, 1994)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flake
_exptl_crystal_F_000             808
_exptl_crystal_size_max          .56
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .28
_refine_diff_density_max         .409
_refine_diff_density_min         -.445
_refine_ls_extinction_coef       .0033(4)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .884
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      .884
_refine_ls_R_factor_all          .060
_refine_ls_R_factor_gt           .034
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0376P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .073
_reflns_number_gt                2006
_reflns_number_total             2989
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0198.cif
_cod_data_source_block           I
_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 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>573' was changed to
'573' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified 'more
than' ('>') a certain temperature. The value '>573' was changed to
'573' - it should be numeric and without a unit
designator.

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1648.9(5)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2010570
_cod_database_fobs_code          2010570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 .60411(4) -.04704(2) .27542(4) .03738(14) Uani d . 1 . . Br
Br2 .68478(8) .2500 .34559(7) .0586(2) Uani d S 1 . . Br
N1 .3727(3) .18781(15) .0343(3) .0246(6) Uani d . 1 . . N
N2 .0796(3) .18738(16) .4093(3) .0294(7) Uani d . 1 . . N
N3 -.2540(3) .18748(15) -.2009(3) .0266(7) Uani d . 1 . . N
C1 .4272(3) .21116(18) -.0585(3) .0289(8) Uani d . 1 . . C
H1 .4585 .1793 -.1119 .035 Uiso calc R 1 . . H
C2 .3421(5) .2500 .0904(5) .0282(12) Uani d S 1 . . C
H2 .3052 .2500 .1582 .034 Uiso calc SR 1 . . H
C3 .3499(4) .10763(18) .0691(4) .0285(9) Uani d . 1 . . C
H3A .4301 .0928 .1561 .034 Uiso calc R 1 . . H
H3B .3507 .0728 -.0022 .034 Uiso calc R 1 . . H
C4 .1563(4) .2112(2) .5422(4) .0477(11) Uani d . 1 . . C
H4 .2007 .1795 .6192 .057 Uiso calc R 1 . . H
C5 .0334(6) .2500 .3306(5) .0332(13) Uani d S 1 . . C
H5 -.0224 .2500 .2354 .040 Uiso calc SR 1 . . H
C6 .0517(4) .10673(18) .3586(4) .0334(9) Uani d . 1 . . C
H6A -.0453 .0902 .3513 .040 Uiso calc R 1 . . H
H6B .1262 .0730 .4238 .040 Uiso calc R 1 . . H
C7 -.3782(4) .2114(2) -.3113(3) .0414(10) Uani d . 1 . . C
H7 -.4500 .1797 -.3751 .050 Uiso calc R 1 . . H
C8 -.1814(6) .2500 -.1362(5) .0328(13) Uani d S 1 . . C
H8 -.0928 .2500 -.0571 .039 Uiso calc SR 1 . . H
C9 -.2092(4) .10568(18) -.1630(4) .0295(9) Uani d . 1 . . C
H9A -.1926 .0807 -.2373 .035 Uiso calc R 1 . . H
H9B -.2885 .0783 -.1502 .035 Uiso calc R 1 . . H
C10 .2014(4) .10158(17) .0810(4) .0231(8) Uani d . 1 . . C
C11 .1973(4) .10027(18) .2113(4) .0249(8) Uani d . 1 . . C
C12 .0575(4) .10082(17) .2187(4) .0252(8) Uani d . 1 . . C
C13 -.0758(4) .10057(17) .0980(4) .0258(8) Uani d . 1 . . C
C14 -.0678(4) .10195(17) -.0305(4) .0258(8) Uani d . 1 . . C
C15 .0699(4) .10317(17) -.0407(3) .0246(8) Uani d . 1 . . C
C16 .0764(4) .1110(2) -.1794(4) .0380(10) Uani d . 1 . . C
H16A .0599 .1639 -.2088 .046 Uiso calc R 1 . . H
H16B .0009 .0791 -.2457 .046 Uiso calc R 1 . . H
H16C .1725 .0948 -.1722 .046 Uiso calc R 1 . . H
C17 .3393(4) .1013(2) .3419(4) .0405(10) Uani d . 1 . . C
H17A .3919 .0536 .3499 .049 Uiso calc R 1 . . H
H17B .3157 .1075 .4206 .049 Uiso calc R 1 . . H
H17C .4007 .1436 .3382 .049 Uiso calc R 1 . . H
C18 -.2246(4) .1027(2) .1085(4) .0411(10) Uani d . 1 . . C
H18A -.2336 .0582 .1585 .049 Uiso calc R 1 . . H
H18B -.3035 .1026 .0173 .049 Uiso calc R 1 . . H
H18C -.2308 .1488 .1563 .049 Uiso calc R 1 . . H
O .7795(5) .0838(3) .5175(4) .0864(12) Uani d D 1 . . O
H1A .727(6) .050(2) .456(5) .12(2) Uiso d D 1 . . H
H1B .749(6) .1280(15) .490(5) .11(2) Uiso d D 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
_geom_angle
C2 N1 C1 . . 108.3(3)
C2 N1 C3 . . 124.5(3)
C1 N1 C3 . . 127.2(3)
C5 N2 C4 . . 107.7(3)
C5 N2 C6 . . 125.2(3)
C4 N2 C6 . . 127.1(3)
C8 N3 C7 . . 107.4(3)
C8 N3 C9 . . 126.9(3)
C7 N3 C9 . . 125.6(3)
C1 C1 N1 4_565 . 107.25(17)
N1 C2 N1 . 4_565 108.9(4)
N1 C3 C10 . . 109.6(3)
C4 C4 N2 4_565 . 107.6(2)
N2 C5 N2 4_565 . 109.3(4)
N2 C6 C12 . . 110.1(3)
C7 C7 N3 4_565 . 107.69(19)
N3 C8 N3 . 4_565 109.8(4)
N3 C9 C14 . . 110.3(3)
C11 C10 C15 . . 121.2(3)
C11 C10 C3 . . 120.1(3)
C15 C10 C3 . . 118.6(3)
C10 C11 C12 . . 118.7(3)
C10 C11 C17 . . 120.9(3)
C12 C11 C17 . . 120.4(3)
C13 C12 C11 . . 121.1(3)
C13 C12 C6 . . 119.7(3)
C11 C12 C6 . . 119.1(3)
C14 C13 C12 . . 118.8(3)
C14 C13 C18 . . 121.0(3)
C12 C13 C18 . . 120.1(3)
C13 C14 C15 . . 121.3(3)
C13 C14 C9 . . 120.3(3)
C15 C14 C9 . . 118.4(3)
C10 C15 C14 . . 119.0(3)
C10 C15 C16 . . 120.4(3)
C14 C15 C16 . . 120.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.323(4) ?
N1 C1 . 1.362(4) ?
N1 C3 . 1.477(4) ?
N2 C5 . 1.329(4) ?
N2 C4 . 1.361(4) ?
N2 C6 . 1.480(4) ?
N3 C8 . 1.323(4) ?
N3 C7 . 1.365(4) ?
N3 C9 . 1.488(4) ?
C1 C1 4_565 1.344(6) ?
C2 N1 4_565 1.323(4) ?
C3 C10 . 1.524(5) ?
C4 C4 4_565 1.343(7) ?
C5 N2 4_565 1.329(4) ?
C6 C12 . 1.511(5) ?
C7 C7 4_565 1.335(7) ?
C8 N3 4_565 1.323(4) ?
C9 C14 . 1.520(5) ?
C10 C11 . 1.400(4) ?
C10 C15 . 1.404(4) ?
C11 C12 . 1.412(5) ?
C11 C17 . 1.511(5) ?
C12 C13 . 1.408(5) ?
C13 C14 . 1.397(5) ?
C13 C18 . 1.516(5) ?
C14 C15 . 1.404(5) ?
C15 C16 . 1.505(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O H1A Br1 .87(3) 2.46(3) 3.326(4) 173(5)
O H1B Br2 .83(2) 2.53(3) 3.326(4) 161(5)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C2 N1 C1 C1 4_565 -.7(3)
C3 N1 C1 C1 4_565 179.2(3)
C1 N1 C2 N1 4_565 1.2(5)
C3 N1 C2 N1 4_565 -178.8(2)
C2 N1 C3 C10 . 42.2(5)
C1 N1 C3 C10 . -137.7(3)
C5 N2 C4 C4 4_565 -.4(3)
C6 N2 C4 C4 4_565 179.4(3)
C4 N2 C5 N2 4_565 .6(6)
C6 N2 C5 N2 4_565 -179.2(3)
C5 N2 C6 C12 . 36.3(5)
C4 N2 C6 C12 . -143.3(4)
C8 N3 C7 C7 4_565 .1(3)
C9 N3 C7 C7 4_565 -179.2(3)
C7 N3 C8 N3 4_565 -.2(5)
C9 N3 C8 N3 4_565 179.1(2)
C8 N3 C9 C14 . 3.1(5)
C7 N3 C9 C14 . -177.7(3)
N1 C3 C10 C11 . -101.5(3)
N1 C3 C10 C15 . 73.8(4)
C15 C10 C11 C12 . -.2(5)
C3 C10 C11 C12 . 175.0(3)
C15 C10 C11 C17 . -177.9(3)
C3 C10 C11 C17 . -2.6(5)
C10 C11 C12 C13 . 1.7(5)
C17 C11 C12 C13 . 179.4(3)
C10 C11 C12 C6 . -174.5(3)
C17 C11 C12 C6 . 3.2(5)
N2 C6 C12 C13 . -99.0(4)
N2 C6 C12 C11 . 77.3(4)
C11 C12 C13 C14 . -1.8(5)
C6 C12 C13 C14 . 174.4(3)
C11 C12 C13 C18 . -178.8(3)
C6 C12 C13 C18 . -2.6(5)
C12 C13 C14 C15 . .3(5)
C18 C13 C14 C15 . 177.3(3)
C12 C13 C14 C9 . -177.0(3)
C18 C13 C14 C9 . .0(5)
N3 C9 C14 C13 . 88.2(4)
N3 C9 C14 C15 . -89.2(4)
C11 C10 C15 C14 . -1.2(5)
C3 C10 C15 C14 . -176.5(3)
C11 C10 C15 C16 . 175.1(3)
C3 C10 C15 C16 . -.2(4)
C13 C14 C15 C10 . 1.2(5)
C9 C14 C15 C10 . 178.5(3)
C13 C14 C15 C16 . -175.2(3)
C9 C14 C15 C16 . 2.2(5)
