#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179656 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/09/4510901.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_4510901
loop_
_publ_author_name
'Leblanc, Nicolas'
'Allain, Magali'
'Mercier, Nicolas'
'Cariati, Elena'
_publ_section_title
;
 ProtonatedN,N′-Dioxide-4,4′-bipyridine, an Interesting
 Synthon for the Building of Polar H-Bonded Networks?
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5200
_journal_paper_doi               10.1021/cg201299n
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C50 H50 Bi4 Br18 N10 O12'
_chemical_formula_sum            'C50 H50 Bi4 Br18 N10 O12'
_chemical_formula_weight         3257.2
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2011-06-10T17:37:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                116.111(6)
_cell_angle_beta                 99.342(8)
_cell_angle_gamma                91.892(6)
_cell_formula_units_Z            1
_cell_length_a                   9.522(1)
_cell_length_b                   15.1320(5)
_cell_length_c                   15.646(2)
_cell_measurement_reflns_used    16128
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.01
_cell_measurement_theta_min      2.5
_cell_volume                     1983.5(4)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2g (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            77529
_diffrn_reflns_theta_full        30
_diffrn_reflns_theta_max         32.01
_diffrn_reflns_theta_min         2.5
_exptl_absorpt_coefficient_mu    17.967
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.906
_refine_diff_density_min         -3.944
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         13384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0419P)²+45.8937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1816
_reflns_number_gt                6648
_reflns_number_total             13384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201299n_si_003.cif
_cod_data_source_block           sad
_cod_original_cell_volume        1983.5(3)
_cod_database_code               4510901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
C1 C 0.1701(17) 0.5794(14) 0.2055(14) 0.061(5) Uani 1 d .
H1 H 0.2527 0.5722 0.2416 0.073 Uiso 1 calc R
C2 C 0.1390(17) 0.5238(12) 0.1102(12) 0.055(4) Uani 1 d .
H2 H 0.2014 0.4788 0.0812 0.066 Uiso 1 calc R
C3 C 0.0172(12) 0.5298(8) 0.0516(9) 0.026(2) Uani 1 d .
C4 C -0.0641(17) 0.6031(12) 0.1025(10) 0.050(4) Uani 1 d .
H4 H -0.1456 0.6131 0.0677 0.061 Uiso 1 calc R
C5 C -0.0315(17) 0.6596(14) 0.1982(12) 0.062(5) Uani 1 d .
H5 H -0.0888 0.7082 0.2282 0.074 Uiso 1 calc R
C6 C 0.8251(15) 0.9213(10) 0.5111(11) 0.042(3) Uani 1 d .
H6 H 0.8775 0.9832 0.5349 0.051 Uiso 1 calc R
C7 C 0.6936(15) 0.9148(10) 0.5361(11) 0.042(3) Uani 1 d .
H7 H 0.6587 0.9718 0.5768 0.051 Uiso 1 calc R
C8 C 0.6135(14) 0.8227(10) 0.5003(10) 0.034(3) Uani 1 d .
C9 C 0.6701(14) 0.7394(10) 0.4367(10) 0.039(3) Uani 1 d .
H9 H 0.6168 0.6773 0.4076 0.046 Uiso 1 calc R
C10 C 0.8026(16) 0.7495(11) 0.4177(10) 0.044(3) Uani 1 d .
H10 H 0.8421 0.6934 0.3797 0.053 Uiso 1 calc R
C11 C 0.2687(17) 0.8792(12) 0.5930(13) 0.052(4) Uani 1 d .
H11 H 0.2163 0.9326 0.6176 0.062 Uiso 1 calc R
C12 C 0.3976(17) 0.8920(11) 0.5691(12) 0.050(4) Uani 1 d .
H12 H 0.4335 0.9546 0.5794 0.06 Uiso 1 calc R
C13 C 0.4752(14) 0.8119(10) 0.5294(9) 0.034(3) Uani 1 d .
C14 C 0.4161(16) 0.7211(11) 0.5165(13) 0.052(4) Uani 1 d .
H14 H 0.4631 0.6655 0.4886 0.063 Uiso 1 calc R
C15 C 0.2898(18) 0.7118(12) 0.5442(14) 0.061(5) Uani 1 d .
H15 H 0.2531 0.6508 0.5373 0.073 Uiso 1 calc R
C16 C 0.9375(16) 0.0484(12) 0.8322(13) 0.053(4) Uani 1 d .
H16 H 0.8559 0.0556 0.7953 0.063 Uiso 1 calc R
C17 C 0.9698(15) 0.1076(12) 0.9305(13) 0.052(4) Uani 1 d .
H17 H 0.9099 0.1545 0.9595 0.062 Uiso 1 calc R
C18 C 1.0924(12) 0.0982(9) 0.9879(10) 0.029(3) Uani 1 d .
C19 C 1.1798(15) 0.0293(12) 0.9388(12) 0.047(4) Uani 1 d .
H19 H 1.2635 0.0215 0.9734 0.056 Uiso 1 calc R
C20 C 1.1444(16) -0.0276(13) 0.8397(14) 0.054(4) Uani 1 d .
H20 H 1.2054 -0.0721 0.8075 0.064 Uiso 1 calc R
C21 C 1.0687(18) 0.2700(13) 1.2466(11) 0.055(4) Uani 1 d .
H21 H 1.0047 0.3095 1.2809 0.066 Uiso 1 calc R
C22 C 1.0370(16) 0.2193(13) 1.1492(12) 0.052(4) Uani 1 d .
H22 H 0.9491 0.2248 1.117 0.062 Uiso 1 calc R
C23 C 1.1295(12) 0.1583(9) 1.0931(11) 0.032(3) Uani 1 d .
C24 C 1.2603(15) 0.1568(11) 1.1481(12) 0.049(4) Uani 1 d .
H24 H 1.3279 0.1192 1.1164 0.058 Uiso 1 calc R
C25 C 1.2916(17) 0.2093(13) 1.2478(13) 0.054(4) Uani 1 d .
H25 H 1.3795 0.2076 1.2827 0.065 Uiso 1 calc R
Bi1 Bi 0.50267(5) 0.22569(3) 0.86115(4) 0.02943(12) Uani 1 d .
Bi2 Bi 0.61113(5) 0.40295(3) 1.18169(4) 0.02948(12) Uani 1 d .
Br1 Br 0.24355(15) 0.13558(10) 0.74609(12) 0.0435(3) Uani 1 d .
Br2 Br 0.64910(18) 0.16843(12) 0.71276(13) 0.0518(4) Uani 1 d .
Br3 Br 0.54876(17) 0.05781(12) 0.87954(16) 0.0595(5) Uani 1 d .
Br4 Br 0.35337(13) 0.30319(10) 1.03457(11) 0.0372(3) Uani 1 d .
Br5 Br 0.76632(13) 0.33333(11) 1.02125(11) 0.0383(3) Uani 1 d .
Br6 Br 0.43903(17) 0.41127(11) 0.83519(14) 0.0498(4) Uani 1 d .
Br7 Br 0.64870(16) 0.23087(11) 1.19709(13) 0.0485(4) Uani 1 d .
Br8 Br 0.4592(2) 0.46358(13) 1.33459(14) 0.0609(5) Uani 1 d .
Br9 Br 0.87894(17) 0.49156(12) 1.30908(13) 0.0541(4) Uani 1 d .
N1 N 0.0830(11) 0.6467(8) 0.2513(9) 0.033(2) Uani 1 d .
N2 N 0.8780(12) 0.8403(8) 0.4534(8) 0.036(2) Uani 1 d .
N3 N 0.2187(11) 0.7912(8) 0.5813(8) 0.034(2) Uani 1 d .
N4 N 1.0215(11) -0.0188(8) 0.7894(9) 0.036(3) Uani 1 d .
N5 N 1.1961(12) 0.2618(10) 1.2929(9) 0.042(3) Uani 1 d .
O1 O 0.1204(11) 0.7002(8) 0.3497(8) 0.050(3) Uani 1 d .
O2 O 1.0061(10) 0.8510(7) 0.4326(8) 0.046(2) Uani 1 d .
O3 O 0.0902(11) 0.7764(9) 0.6031(9) 0.054(3) Uani 1 d .
O4 O 0.9852(11) -0.0746(9) 0.6945(8) 0.053(3) Uani 1 d .
O5 O 1.2257(14) 0.3062(12) 1.3919(9) 0.078(4) Uani 1 d .
O6A O 1.140(4) 0.477(2) 1.4714(19) 0.100(13) Uani 0.5 d P
O6B O 1.242(4) 0.481(2) 1.497(3) 0.092(11) Uani 0.5 d P
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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 0.006 '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
C2 C1 N1 120.9(14) . .
C2 C1 H1 119.5 . .
N1 C1 H1 119.5 . .
C1 C2 C3 122.8(13) . .
C1 C2 H2 118.6 . .
C3 C2 H2 118.6 . .
C2 C3 C4 113.3(12) . .
C2 C3 C3 123.3(13) . 2_565
C4 C3 C3 123.3(13) . 2_565
C5 C4 C3 123.6(13) . .
C5 C4 H4 118.2 . .
C3 C4 H4 118.2 . .
C4 C5 N1 120.3(13) . .
C4 C5 H5 119.8 . .
N1 C5 H5 119.8 . .
N2 C6 C7 121.1(13) . .
N2 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C6 C7 C8 120.0(12) . .
C6 C7 H7 120 . .
C8 C7 H7 120 . .
C7 C8 C9 117.3(12) . .
C7 C8 C13 121.7(11) . .
C9 C8 C13 121.0(12) . .
C10 C9 C8 120.2(13) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
N2 C10 C9 121.0(13) . .
N2 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
N3 C11 C12 120.2(14) . .
N3 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C11 C12 C13 120.5(14) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 116.8(13) . .
C14 C13 C8 121.4(12) . .
C12 C13 C8 121.8(12) . .
C15 C14 C13 121.1(13) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
N3 C15 C14 119.7(14) . .
N3 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
N4 C16 C17 120.5(14) . .
N4 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C16 C17 C18 120.8(13) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C19 C18 C17 116.2(13) . .
C19 C18 C23 121.1(12) . .
C17 C18 C23 122.7(12) . .
C20 C19 C18 121.0(12) . .
C20 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
N4 C20 C19 119.9(14) . .
N4 C20 H20 120.1 . .
C19 C20 H20 120.1 . .
C22 C21 N5 118.0(15) . .
C22 C21 H21 121 . .
N5 C21 H21 121 . .
C21 C22 C23 123.7(14) . .
C21 C22 H22 118.1 . .
C23 C22 H22 118.1 . .
C24 C23 C22 113.7(14) . .
C24 C23 C18 122.1(12) . .
C22 C23 C18 124.1(12) . .
C25 C24 C23 122.0(14) . .
C25 C24 H24 119 . .
C23 C24 H24 119 . .
N5 C25 C24 119.2(14) . .
N5 C25 H25 120.4 . .
C24 C25 H25 120.4 . .
Br1 Bi1 Br3 89.38(5) . .
Br1 Bi1 Br2 95.34(6) . .
Br3 Bi1 Br2 90.86(6) . .
Br1 Bi1 Br4 88.03(5) . .
Br3 Bi1 Br4 91.38(5) . .
Br2 Bi1 Br4 175.97(5) . .
Br1 Bi1 Br5 169.50(5) . .
Br3 Bi1 Br5 88.83(5) . .
Br2 Bi1 Br5 95.03(5) . .
Br4 Bi1 Br5 81.67(4) . .
Br1 Bi1 Br6 88.35(4) . .
Br3 Bi1 Br6 177.73(5) . .
Br2 Bi1 Br6 89.34(5) . .
Br4 Bi1 Br6 88.55(4) . .
Br5 Bi1 Br6 93.41(4) . .
Br7 Bi2 Br8 89.28(5) . .
Br7 Bi2 Br9 89.77(5) . .
Br8 Bi2 Br9 93.17(6) . .
Br7 Bi2 Br4 89.59(5) . .
Br8 Bi2 Br4 92.85(5) . .
Br9 Bi2 Br4 173.93(5) . .
Br7 Bi2 Br5 89.08(5) . .
Br8 Bi2 Br5 178.17(5) . .
Br9 Bi2 Br5 87.64(5) . .
Br4 Bi2 Br5 86.32(4) . .
Br7 Bi2 Br6 178.28(5) . 2_667
Br8 Bi2 Br6 89.61(5) . 2_667
Br9 Bi2 Br6 91.61(5) . 2_667
Br4 Bi2 Br6 89.15(4) . 2_667
Br5 Bi2 Br6 92.01(5) . 2_667
Bi2 Br4 Bi1 96.22(4) . .
Bi2 Br5 Bi1 95.80(4) . .
Bi2 Br6 Bi1 177.19(7) 2_667 .
C5 N1 C1 118.9(14) . .
C5 N1 O1 123.3(11) . .
C1 N1 O1 117.7(12) . .
O2 N2 C6 118.5(11) . .
O2 N2 C10 121.3(11) . .
C6 N2 C10 120.2(12) . .
C11 N3 C15 121.7(13) . .
C11 N3 O3 121.3(12) . .
C15 N3 O3 117.0(12) . .
O4 N4 C16 118.2(12) . .
O4 N4 C20 120.3(12) . .
C16 N4 C20 121.4(14) . .
C25 N5 C21 123.4(14) . .
C25 N5 O5 117.6(13) . .
C21 N5 O5 118.9(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.33(2) .
C1 N1 1.358(18) .
C1 H1 0.93 .
C2 C3 1.388(18) .
C2 H2 0.93 .
C3 C4 1.394(16) .
C3 C3 1.43(3) 2_565
C4 C5 1.33(2) .
C4 H4 0.93 .
C5 N1 1.334(18) .
C5 H5 0.93 .
C6 N2 1.337(17) .
C6 C7 1.384(19) .
C6 H6 0.93 .
C7 C8 1.392(18) .
C7 H7 0.93 .
C8 C9 1.409(18) .
C8 C13 1.489(18) .
C9 C10 1.360(19) .
C9 H9 0.93 .
C10 N2 1.358(17) .
C10 H10 0.93 .
C11 N3 1.322(18) .
C11 C12 1.37(2) .
C11 H11 0.93 .
C12 C13 1.396(19) .
C12 H12 0.93 .
C13 C14 1.383(19) .
C14 C15 1.37(2) .
C14 H14 0.93 .
C15 N3 1.344(18) .
C15 H15 0.93 .
C16 N4 1.323(17) .
C16 C17 1.37(2) .
C16 H16 0.93 .
C17 C18 1.405(18) .
C17 H17 0.93 .
C18 C19 1.389(17) .
C18 C23 1.46(2) .
C19 C20 1.38(2) .
C19 H19 0.93 .
C20 N4 1.345(17) .
C20 H20 0.93 .
C21 C22 1.34(2) .
C21 N5 1.347(19) .
C21 H21 0.93 .
C22 C23 1.411(19) .
C22 H22 0.93 .
C23 C24 1.401(18) .
C24 C25 1.38(2) .
C24 H24 0.93 .
C25 N5 1.312(19) .
C25 H25 0.93 .
Bi1 Br1 2.7135(15) .
Bi1 Br3 2.7212(14) .
Bi1 Br2 2.7287(17) .
Bi1 Br4 3.0528(16) .
Bi1 Br5 3.0540(16) .
Bi1 Br6 3.0749(14) .
Bi2 Br7 2.7481(13) .
Bi2 Br8 2.8171(18) .
Bi2 Br9 2.8364(17) .
Bi2 Br4 2.9093(15) .
Bi2 Br5 2.9281(16) .
Bi2 Br6 2.9835(14) 2_667
Br6 Bi2 2.9835(14) 2_667
N1 O1 1.362(15) .
N2 O2 1.335(14) .
N3 O3 1.360(14) .
N4 O4 1.323(15) .
N5 O5 1.363(17) .
O6A O6B 0.98(4) .
