#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/65/7016563.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_7016563
loop_
_publ_author_name
'Amendola, Valeria'
'Bergamaschi, Greta'
'Boiocchi, Massimo'
'Fabbrizzi, Luigi'
'Fusco, Nadia'
_publ_section_title
;
 The solution stability of copper(i) and silver(i) complexes with
 N-heterocyclic carbenes.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8367
_journal_page_last               8376
_journal_paper_doi               10.1039/c1dt10894h
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C45 H45 N6, 7.70 (H2 O), 3 (Br)'
_chemical_formula_sum            'C45 H60.4 Br3 N6 O7.7'
_chemical_formula_weight         1048.38
_chemical_name_common
;
12,14,16,52,54,56-Hexamethyl-1,5(1,3,5)-tribenzena-
3,7,10(1,3)-tri-benzimidazoliabicyclo(3.3.3)undecaphane tribromide
7.7hydrate
;
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      12
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.487(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.808(2)
_cell_length_b                   17.0480(18)
_cell_length_c                   15.9333(17)
_cell_measurement_reflns_used    4342
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     5104.7(9)
_computing_cell_refinement       'SAINT (Bruker-Axs Inc)'
_computing_data_collection       'SMART (Bruker-Axs Inc)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20614
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'platy prism'
_exptl_crystal_F_000             2156
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.995
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1556P)²+3.8700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2331
_reflns_number_gt                3442
_reflns_number_total             4666
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1dt10894h.txt
_cod_data_source_block           '[LH3]_Br'
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C45 H60.40 Br3 N6 O7.70'
_cod_database_code               7016563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C1 C 0.2632(2) 0.14812(18) 0.1716(3) 0.0418(8) Uani 1 1 d . . .
C2 C 0.2251(2) 0.14655(19) 0.0694(3) 0.0447(9) Uani 1 1 d . . .
C3 C 0.2631(2) 0.14752(19) 0.0196(3) 0.0420(8) Uani 1 1 d . . .
C4 C 0.3374(2) 0.14603(19) 0.0706(3) 0.0446(9) Uani 1 1 d . . .
C5 C 0.3747(2) 0.14802(19) 0.1731(3) 0.0420(8) Uani 1 1 d . . .
C6 C 0.3377(2) 0.14837(19) 0.2243(3) 0.0428(9) Uani 1 1 d . . .
C7 C 0.2233(2) 0.1462(2) 0.2260(3) 0.0484(9) Uani 1 1 d . . .
H7A H 0.2502 0.1743 0.2870 0.058 Uiso 1 1 calc R . .
H7B H 0.1777 0.1721 0.1877 0.058 Uiso 1 1 calc R . .
C8 C 0.1455(2) 0.1389(3) 0.0145(3) 0.0611(11) Uani 1 1 d . . .
H8A H 0.1305 0.1149 0.0556 0.092 Uiso 1 1 calc R . .
H8B H 0.1309 0.1068 -0.0422 0.092 Uiso 1 1 calc R . .
H8C H 0.1244 0.1899 -0.0052 0.092 Uiso 1 1 calc R . .
C9 C 0.2223(2) 0.1453(2) -0.0916(3) 0.0501(10) Uani 1 1 d . . .
H9A H 0.1776 0.1731 -0.1164 0.060 Uiso 1 1 calc R . .
H9B H 0.2498 0.1716 -0.1157 0.060 Uiso 1 1 calc R . .
C10 C 0.3773(3) 0.1371(3) 0.0164(3) 0.0630(12) Uani 1 1 d . . .
H10A H 0.3450 0.1204 -0.0491 0.095 Uiso 1 1 calc R . .
H10B H 0.4143 0.0988 0.0487 0.095 Uiso 1 1 calc R . .
H10C H 0.3980 0.1866 0.0154 0.095 Uiso 1 1 calc R . .
C11 C 0.4547(2) 0.1459(2) 0.2295(3) 0.0496(9) Uani 1 1 d . . .
H11A H 0.4729 0.1682 0.1904 0.060 Uiso 1 1 calc R . .
H11B H 0.4723 0.1773 0.2880 0.060 Uiso 1 1 calc R . .
C12 C 0.3781(2) 0.1439(3) 0.3343(3) 0.0609(11) Uani 1 1 d . . .
H12A H 0.4229 0.1184 0.3565 0.091 Uiso 1 1 calc R . .
H12B H 0.3507 0.1146 0.3555 0.091 Uiso 1 1 calc R . .
H12C H 0.3861 0.1959 0.3609 0.091 Uiso 1 1 calc R . .
C13 C 0.17992(19) 0.0410(2) 0.2983(3) 0.0453(8) Uani 1 1 d . . .
C14 C 0.1521(2) 0.0843(3) 0.3446(3) 0.0590(11) Uani 1 1 d . . .
H14 H 0.1522 0.1389 0.3449 0.071 Uiso 1 1 calc R . .
C15 C 0.1243(3) 0.0408(3) 0.3902(4) 0.0736(13) Uani 1 1 d . . .
H15 H 0.1047 0.0670 0.4223 0.088 Uiso 1 1 calc R . .
C16 C 0.2296(3) 0.0000 0.2163(4) 0.0478(13) Uani 1 2 d S . .
H16 H 0.2517 0.0000 0.1794 0.057 Uiso 1 2 calc SR . .
C17 C 0.1688(2) 0.0406(2) -0.2240(3) 0.0470(9) Uani 1 1 d . . .
C18 C 0.1315(2) 0.0841(3) -0.3097(3) 0.0606(11) Uani 1 1 d . . .
H18 H 0.1312 0.1386 -0.3099 0.073 Uiso 1 1 calc R . .
C19 C 0.0954(3) 0.0411(3) -0.3933(3) 0.0748(14) Uani 1 1 d . . .
H19 H 0.0700 0.0674 -0.4524 0.090 Uiso 1 1 calc R . .
C20 C 0.2297(3) 0.0000 -0.0733(4) 0.0481(13) Uani 1 2 d S . .
H20 H 0.2567 0.0000 -0.0056 0.058 Uiso 1 2 calc SR . .
C21 C 0.5490(2) 0.0410(3) 0.3229(3) 0.0585(10) Uani 1 1 d . . .
C22 C 0.6101(3) 0.0842(4) 0.3814(4) 0.0881(17) Uani 1 1 d . . .
H22 H 0.6106 0.1387 0.3823 0.106 Uiso 1 1 calc R . .
C23 C 0.6702(3) 0.0396(4) 0.4384(6) 0.128(3) Uani 1 1 d . . .
H23 H 0.7128 0.0655 0.4787 0.154 Uiso 1 1 calc R . .
C24 C 0.4420(3) 0.0000 0.2171(4) 0.0481(13) Uani 1 2 d S . .
H24 H 0.3943 0.0000 0.1685 0.058 Uiso 1 2 calc SR . .
N1 N 0.21184(17) 0.06411(18) 0.2458(2) 0.0453(7) Uani 1 1 d . . .
N2 N 0.20828(16) 0.06392(17) -0.1271(2) 0.0427(7) Uani 1 1 d . . .
N3 N 0.48066(17) 0.06398(18) 0.2564(2) 0.0484(8) Uani 1 1 d . . .
Br1 Br 0.54609(5) 0.25675(6) 0.12103(7) 0.0670(3) Uani 0.50 1 d P . .
Br2 Br 0.54491(5) 0.27900(6) 0.44847(7) 0.0670(3) Uani 0.50 1 d P . .
Br3 Br 0.28981(8) 0.26773(8) 0.45057(10) 0.0809(5) Uani 0.4255(18) 1 d P S 1
Br4 Br 0.5764(4) 0.0000 0.1344(4) 0.0596(18) Uani 0.149(4) 2 d SP S 2
O1W O 0.1919(4) 0.3393(3) 0.2372(3) 0.1285(19) Uani 1 1 d D . .
H1WA H 0.1454 0.3284 0.2280 0.154 Uiso 1 1 d RD . .
H1WB H 0.2304 0.3390 0.3037 0.154 Uiso 1 1 d RD . .
O2W O 0.4691(2) 0.3408(2) 0.2284(3) 0.0863(11) Uani 1 1 d D . .
H2WA H 0.498(3) 0.327(4) 0.200(4) 0.104 Uiso 1 1 d D . .
H2WB H 0.491(3) 0.341(4) 0.2983(9) 0.104 Uiso 1 1 d D . .
O3W O 0.4539(3) 0.5000 0.1675(5) 0.0925(16) Uani 1 2 d SD . .
H3W H 0.469(3) 0.457(3) 0.213(4) 0.111 Uiso 1 1 d D . .
O4W O 0.5394(5) 0.5365(6) 0.0911(8) 0.119(3) Uani 0.50 1 d P B -1
O5W O 0.6706(5) 0.0000 0.1840(7) 0.114(2) Uani 0.851(4) 2 d SP S 1
O6W O 0.5371(8) -0.0339(10) 0.1044(10) 0.123(5) Uani 0.4245(18) 1 d P S 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 121.3(3) . .
C6 C1 C7 119.2(3) . .
C2 C1 C7 119.5(3) . .
C1 C2 C3 118.8(3) . .
C1 C2 C8 120.5(4) . .
C3 C2 C8 120.6(3) . .
C4 C3 C2 120.8(3) . .
C4 C3 C9 119.7(3) . .
C2 C3 C9 119.4(3) . .
C3 C4 C5 119.5(3) . .
C3 C4 C10 120.2(3) . .
C5 C4 C10 120.2(4) . .
C4 C5 C6 120.5(3) . .
C4 C5 C11 120.4(3) . .
C6 C5 C11 119.0(3) . .
C1 C6 C5 119.0(3) . .
C1 C6 C12 120.6(3) . .
C5 C6 C12 120.3(3) . .
N1 C7 C1 110.6(3) . .
N1 C7 H7A 109.5 . .
C1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
C1 C7 H7B 109.5 . .
H7A C7 H7B 108.1 . .
C2 C8 H8A 109.5 . .
C2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 C3 110.7(3) . .
N2 C9 H9A 109.5 . .
C3 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
C3 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
C4 C10 H10A 109.5 . .
C4 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C4 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N3 C11 C5 110.6(3) . .
N3 C11 H11A 109.5 . .
C5 C11 H11A 109.5 . .
N3 C11 H11B 109.5 . .
C5 C11 H11B 109.5 . .
H11A C11 H11B 108.1 . .
C6 C12 H12A 109.5 . .
C6 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C6 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 N1 131.3(4) . .
C14 C13 C13 122.3(3) . 6
N1 C13 C13 106.4(2) . 6
C15 C14 C13 115.1(4) . .
C15 C14 H14 122.4 . .
C13 C14 H14 122.4 . .
C14 C15 C15 122.6(3) . 6
C14 C15 H15 118.7 . .
C15 C15 H15 118.7 6 .
N1 C16 N1 111.4(5) . 6
N1 C16 H16 124.3 . .
N1 C16 H16 124.3 6 .
C17 C17 N2 106.6(2) 6 .
C17 C17 C18 122.1(2) 6 .
N2 C17 C18 131.3(4) . .
C19 C18 C17 115.5(4) . .
C19 C18 H18 122.2 . .
C17 C18 H18 122.2 . .
C18 C19 C19 122.4(3) . 6
C18 C19 H19 118.8 . .
C19 C19 H19 118.8 6 .
N2 C20 N2 111.7(4) 6 .
N2 C20 H20 124.2 6 .
N2 C20 H20 124.2 . .
N3 C21 C22 131.4(5) . .
N3 C21 C21 106.6(2) . 6
C22 C21 C21 122.0(3) . 6
C23 C22 C21 114.6(6) . .
C23 C22 H22 122.7 . .
C21 C22 H22 122.7 . .
C23 C23 C22 123.3(4) 6 .
C23 C23 H23 118.3 6 .
C22 C23 H23 118.3 . .
N3 C24 N3 110.8(5) 6 .
N3 C24 H24 124.6 6 .
N3 C24 H24 124.6 . .
C16 N1 C13 107.9(3) . .
C16 N1 C7 126.3(3) . .
C13 N1 C7 125.8(3) . .
C20 N2 C17 107.6(3) . .
C20 N2 C9 126.5(3) . .
C17 N2 C9 125.9(3) . .
C24 N3 C21 108.0(3) . .
C24 N3 C11 125.4(3) . .
C21 N3 C11 126.5(3) . .
O6W Br4 O6W 75.9(18) . 6
O6W Br4 O5W 140.6(9) . .
O6W Br4 O5W 140.6(9) 6 .
H1WA O1W H1WB 115.4 . .
H2WA O2W H2WB 118(6) . .
Br4 O6W O6W 52.1(9) . 6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.401(5) .
C1 C2 1.404(5) .
C1 C7 1.508(5) .
C2 C3 1.408(5) .
C2 C8 1.500(6) .
C3 C4 1.397(6) .
C3 C9 1.527(5) .
C4 C5 1.407(5) .
C4 C10 1.513(6) .
C5 C6 1.408(5) .
C5 C11 1.504(6) .
C6 C12 1.513(5) .
C7 N1 1.483(5) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 N2 1.471(5) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N3 1.486(5) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C14 1.381(6) .
C13 N1 1.389(5) .
C13 C13 1.399(8) 6
C14 C15 1.377(7) .
C14 H14 0.9300 .
C15 C15 1.391(11) 6
C15 H15 0.9300 .
C16 N1 1.323(4) .
C16 N1 1.323(4) 6
C16 H16 0.9300 .
C17 C17 1.385(8) 6
C17 N2 1.391(5) .
C17 C18 1.395(6) .
C18 C19 1.366(6) .
C18 H18 0.9300 .
C19 C19 1.402(10) 6
C19 H19 0.9300 .
C20 N2 1.317(4) 6
C20 N2 1.317(4) .
C20 H20 0.9300 .
C21 N3 1.377(5) .
C21 C22 1.388(7) .
C21 C21 1.396(9) 6
C22 C23 1.383(8) .
C22 H22 0.9300 .
C23 C23 1.351(14) 6
C23 H23 0.9300 .
C24 N3 1.325(4) 6
C24 N3 1.325(4) .
C24 H24 0.9300 .
Br4 O6W 0.939(17) .
Br4 O6W 0.939(17) 6
Br4 O5W 1.787(11) .
O1W H1WA 0.9664 .
O1W H1WB 0.9621 .
O2W H2WA 0.97(7) .
O2W H2WB 0.97(7) .
O3W H3W 0.96(5) .
O4W O4W 1.25(2) 6_565
O6W O6W 1.15(4) 6
