#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179656 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/09/4510902.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_4510902
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 H46 Bi4 Br18 N10 O10'
_chemical_formula_sum            'C50 H46 Bi4 Br18 N10 O10'
_chemical_formula_weight         3221.2
_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             2011-06-10T09:37:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                115.358(6)
_cell_angle_beta                 98.472(7)
_cell_angle_gamma                92.445(8)
_cell_formula_units_Z            1
_cell_length_a                   9.552(1)
_cell_length_b                   15.0481(5)
_cell_length_c                   15.256(1)
_cell_measurement_reflns_used    19468
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      32.06
_cell_measurement_theta_min      2.55
_cell_volume                     1946.2(3)
_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      300(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0755
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            68012
_diffrn_reflns_theta_full        32.06
_diffrn_reflns_theta_max         32.06
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    18.308
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.107
_refine_diff_density_min         -3.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         13330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+24.0185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                7005
_reflns_number_total             13330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201299n_si_003.cif
_cod_data_source_block           sadp-1
_cod_original_cell_volume        1946.2(2)
_cod_database_code               4510902
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 0.1672(11) 0.5820(8) 0.2102(8) 0.053(3) Uani 1 d .
H1 H 0.2486 0.5752 0.2475 0.064 Uiso 1 calc R
C2 C 0.1378(11) 0.5249(8) 0.1116(8) 0.051(3) Uani 1 d .
H2 H 0.2007 0.4806 0.0821 0.061 Uiso 1 calc R
C3 C 0.0163(9) 0.5307(6) 0.0534(6) 0.0274(18) Uani 1 d .
C4 C -0.0683(11) 0.6012(9) 0.1031(8) 0.051(3) Uani 1 d .
H4 H -0.1505 0.6092 0.0675 0.062 Uiso 1 calc R
C5 C -0.0353(12) 0.6590(9) 0.2016(8) 0.055(3) Uani 1 d .
H5 H -0.0938 0.7063 0.2323 0.065 Uiso 1 calc R
C6 C -0.1830(11) 0.9221(7) 0.5124(8) 0.042(2) Uani 1 d .
H6 H -0.1346 0.9846 0.533 0.05 Uiso 1 calc R
C7 C -0.3136(10) 0.9131(7) 0.5373(8) 0.041(2) Uani 1 d .
H7 H -0.352 0.9697 0.5757 0.05 Uiso 1 calc R
C8 C -0.3887(10) 0.8211(6) 0.5060(7) 0.034(2) Uani 1 d .
C9 C -0.3258(11) 0.7390(7) 0.4485(7) 0.042(2) Uani 1 d .
H9 H -0.374 0.6758 0.4245 0.05 Uiso 1 calc R
C10 C -0.1952(11) 0.7504(7) 0.4272(8) 0.046(3) Uani 1 d .
H10 H -0.1538 0.6946 0.3905 0.055 Uiso 1 calc R
C11 C -0.7373(11) 0.8744(7) 0.5956(8) 0.045(3) Uani 1 d .
H11 H -0.7894 0.9277 0.6211 0.054 Uiso 1 calc R
C12 C -0.6078(11) 0.8879(7) 0.5719(8) 0.043(2) Uani 1 d .
H12 H -0.5723 0.9507 0.5817 0.051 Uiso 1 calc R
C13 C -0.5281(9) 0.8088(6) 0.5331(6) 0.0293(18) Uani 1 d .
C14 C -0.5870(11) 0.7179(7) 0.5221(8) 0.041(2) Uani 1 d .
H14 H -0.5379 0.663 0.4968 0.05 Uiso 1 calc R
C15 C -0.7166(10) 0.7075(8) 0.5478(8) 0.046(3) Uani 1 d .
H15 H -0.7535 0.6463 0.5411 0.056 Uiso 1 calc R
C16 C -0.0687(11) 1.0465(8) 0.8349(10) 0.053(3) Uani 1 d .
H16 H -0.1518 1.0519 0.7981 0.063 Uiso 1 calc R
C17 C -0.0340(11) 1.1068(8) 0.9323(10) 0.051(3) Uani 1 d .
H17 H -0.0933 1.1542 0.9615 0.061 Uiso 1 calc R
C18 C 0.0891(9) 1.1000(7) 0.9906(8) 0.036(2) Uani 1 d .
C19 C 0.1741(10) 1.0284(8) 0.9393(9) 0.044(3) Uani 1 d .
H19 H 0.2583 1.0212 0.9737 0.053 Uiso 1 calc R
C20 C 0.1363(10) 0.9691(8) 0.8403(9) 0.047(3) Uani 1 d .
H20 H 0.1946 0.9223 0.8081 0.056 Uiso 1 calc R
C21 C 0.0721(14) 1.2859(10) 1.2484(10) 0.063(3) Uani 1 d .
H21 H 0.0111 1.3293 1.2823 0.076 Uiso 1 calc R
C22 C 0.0347(13) 1.2270(9) 1.1490(10) 0.059(3) Uani 1 d .
H22 H -0.0531 1.2302 1.1156 0.071 Uiso 1 calc R
C23 C 0.1264(9) 1.1616(7) 1.0963(8) 0.037(2) Uani 1 d .
C24 C 0.2543(11) 1.1598(8) 1.1524(9) 0.051(3) Uani 1 d .
H24 H 0.3182 1.117 1.1219 0.061 Uiso 1 calc R
C25 C 0.2870(13) 1.2192(9) 1.2506(10) 0.057(3) Uani 1 d .
H25 H 0.3732 1.2176 1.2869 0.069 Uiso 1 calc R
Bi1 Bi 0.49864(3) 0.22444(2) -0.13860(3) 0.02908(9) Uani 1 d .
Bi2 Bi 0.61100(4) 0.40503(2) 0.18722(3) 0.03062(9) Uani 1 d .
Br1 Br 0.24412(11) 0.13347(7) -0.25478(8) 0.0435(2) Uani 1 d .
Br2 Br 0.64958(13) 0.16752(8) -0.28911(9) 0.0543(3) Uani 1 d .
Br3 Br 0.54514(12) 0.05801(8) -0.11530(11) 0.0582(3) Uani 1 d .
Br4 Br 0.34944(9) 0.30527(7) 0.03601(8) 0.0367(2) Uani 1 d .
Br5 Br 0.76145(10) 0.33720(7) 0.02492(8) 0.0398(2) Uani 1 d .
Br6 Br 0.56071(12) 0.59178(8) 0.17024(10) 0.0516(3) Uani 1 d .
Br7 Br 0.64035(11) 0.22901(7) 0.19807(9) 0.0448(3) Uani 1 d .
Br8 Br 0.45638(16) 0.46871(9) 0.34772(11) 0.0687(4) Uani 1 d .
Br9 Br 0.86253(14) 0.49187(9) 0.31979(11) 0.0706(4) Uani 1 d .
N1 N 0.0809(8) 0.6483(6) 0.2550(6) 0.0329(17) Uani 1 d .
N2 N -0.1244(8) 0.8408(5) 0.4581(6) 0.0332(17) Uani 1 d .
N3 N -0.7887(8) 0.7847(6) 0.5820(6) 0.0365(18) Uani 1 d .
N4 N 0.0175(9) 0.9780(6) 0.7905(7) 0.0404(19) Uani 1 d .
N5 N 0.1957(10) 1.2798(7) 1.2949(7) 0.051(2) Uani 1 d .
O1 O 0.1138(7) 0.7006(5) 0.3539(5) 0.0460(17) Uani 1 d .
O2 O 0.0042(7) 0.8527(5) 0.4368(5) 0.0407(16) Uani 1 d .
O3 O -0.9169(7) 0.7693(5) 0.6051(6) 0.0522(19) Uani 1 d .
O4 O -0.0228(8) 0.9193(6) 0.6949(6) 0.059(2) Uani 1 d .
O5 O 0.2320(10) 1.3411(8) 1.3937(7) 0.079(3) Uani 1 d .
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
N1 C1 C2 121.0(10) . .
N1 C1 H1 119.5 . .
C2 C1 H1 119.5 . .
C1 C2 C3 121.6(9) . .
C1 C2 H2 119.2 . .
C3 C2 H2 119.2 . .
C4 C3 C2 115.1(9) . .
C4 C3 C3 122.9(10) . 2_565
C2 C3 C3 121.9(9) . 2_565
C5 C4 C3 122.3(9) . .
C5 C4 H4 118.9 . .
C3 C4 H4 118.9 . .
N1 C5 C4 120.3(9) . .
N1 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
N2 C6 C7 120.5(9) . .
N2 C6 H6 119.8 . .
C7 C6 H6 119.8 . .
C6 C7 C8 120.8(8) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C7 C8 C9 116.9(9) . .
C7 C8 C13 122.2(8) . .
C9 C8 C13 120.9(8) . .
C10 C9 C8 120.7(9) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
N2 C10 C9 121.2(9) . .
N2 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
N3 C11 C12 119.9(9) . .
N3 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C11 C12 C13 121.0(9) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C14 C13 C12 116.1(8) . .
C14 C13 C8 121.8(8) . .
C12 C13 C8 122.1(8) . .
C15 C14 C13 121.3(9) . .
C15 C14 H14 119.4 . .
C13 C14 H14 119.4 . .
N3 C15 C14 119.9(9) . .
N3 C15 H15 120 . .
C14 C15 H15 120 . .
C17 C16 N4 120.0(10) . .
C17 C16 H16 120 . .
N4 C16 H16 120 . .
C16 C17 C18 121.8(10) . .
C16 C17 H17 119.1 . .
C18 C17 H17 119.1 . .
C17 C18 C19 115.0(10) . .
C17 C18 C23 122.9(9) . .
C19 C18 C23 122.1(9) . .
C20 C19 C18 121.7(9) . .
C20 C19 H19 119.1 . .
C18 C19 H19 119.1 . .
N4 C20 C19 120.0(9) . .
N4 C20 H20 120 . .
C19 C20 H20 120 . .
N5 C21 C22 118.6(11) . .
N5 C21 H21 120.7 . .
C22 C21 H21 120.7 . .
C21 C22 C23 121.5(11) . .
C21 C22 H22 119.3 . .
C23 C22 H22 119.3 . .
C24 C23 C22 115.5(11) . .
C24 C23 C18 122.5(9) . .
C22 C23 C18 122.0(10) . .
C25 C24 C23 121.1(10) . .
C25 C24 H24 119.4 . .
C23 C24 H24 119.4 . .
N5 C25 C24 119.8(11) . .
N5 C25 H25 120.1 . .
C24 C25 H25 120.1 . .
Br1 Bi1 Br3 89.73(4) . .
Br1 Bi1 Br2 95.51(4) . .
Br3 Bi1 Br2 90.91(4) . .
Br1 Bi1 Br4 88.68(3) . .
Br3 Bi1 Br4 92.34(4) . .
Br2 Bi1 Br4 174.71(3) . .
Br1 Bi1 Br6 88.64(3) . 2_665
Br3 Bi1 Br6 178.29(4) . 2_665
Br2 Bi1 Br6 88.74(4) . 2_665
Br4 Bi1 Br6 88.14(3) . 2_665
Br1 Bi1 Br5 169.90(3) . .
Br3 Bi1 Br5 89.24(4) . .
Br2 Bi1 Br5 94.55(4) . .
Br4 Bi1 Br5 81.32(3) . .
Br6 Bi1 Br5 92.46(3) 2_665 .
Br7 Bi2 Br9 91.04(4) . .
Br7 Bi2 Br5 88.53(3) . .
Br9 Bi2 Br5 91.06(4) . .
Br7 Bi2 Br8 90.58(4) . .
Br9 Bi2 Br8 89.91(5) . .
Br5 Bi2 Br8 178.70(3) . .
Br7 Bi2 Br4 88.07(3) . .
Br9 Bi2 Br4 176.83(4) . .
Br5 Bi2 Br4 85.88(3) . .
Br8 Bi2 Br4 93.15(4) . .
Br7 Bi2 Br6 176.56(4) . .
Br9 Bi2 Br6 92.24(4) . .
Br5 Bi2 Br6 92.44(3) . .
Br8 Bi2 Br6 88.39(4) . .
Br4 Bi2 Br6 88.71(3) . .
Bi2 Br4 Bi1 96.16(3) . .
Bi2 Br5 Bi1 96.58(3) . .
Bi2 Br6 Bi1 176.31(5) . 2_665
C5 N1 C1 119.6(9) . .
C5 N1 O1 122.3(8) . .
C1 N1 O1 118.0(8) . .
O2 N2 C10 121.6(7) . .
O2 N2 C6 118.6(7) . .
C10 N2 C6 119.8(8) . .
C15 N3 C11 121.9(8) . .
C15 N3 O3 117.0(8) . .
C11 N3 O3 121.1(8) . .
C20 N4 O4 120.9(8) . .
C20 N4 C16 121.4(10) . .
O4 N4 C16 117.6(9) . .
C21 N5 C25 123.4(11) . .
C21 N5 O5 117.5(10) . .
C25 N5 O5 119.0(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.339(12) .
C1 C2 1.353(14) .
C1 H1 0.93 .
C2 C3 1.384(13) .
C2 H2 0.93 .
C3 C4 1.384(12) .
C3 C3 1.465(17) 2_565
C4 C5 1.354(14) .
C4 H4 0.93 .
C5 N1 1.335(12) .
C5 H5 0.93 .
C6 N2 1.350(11) .
C6 C7 1.375(13) .
C6 H6 0.93 .
C7 C8 1.381(13) .
C7 H7 0.93 .
C8 C9 1.395(12) .
C8 C13 1.478(12) .
C9 C10 1.357(13) .
C9 H9 0.93 .
C10 N2 1.344(12) .
C10 H10 0.93 .
C11 N3 1.334(12) .
C11 C12 1.370(13) .
C11 H11 0.93 .
C12 C13 1.398(12) .
C12 H12 0.93 .
C13 C14 1.387(12) .
C14 C15 1.375(13) .
C14 H14 0.93 .
C15 N3 1.323(12) .
C15 H15 0.93 .
C16 C17 1.347(16) .
C16 N4 1.356(12) .
C16 H16 0.93 .
C17 C18 1.402(14) .
C17 H17 0.93 .
C18 C19 1.404(13) .
C18 C23 1.451(15) .
C19 C20 1.366(15) .
C19 H19 0.93 .
C20 N4 1.316(12) .
C20 H20 0.93 .
C21 N5 1.313(15) .
C21 C22 1.369(17) .
C21 H21 0.93 .
C22 C23 1.409(14) .
C22 H22 0.93 .
C23 C24 1.392(14) .
C24 C25 1.354(16) .
C24 H24 0.93 .
C25 N5 1.328(14) .
C25 H25 0.93 .
Bi1 Br1 2.7008(11) .
Bi1 Br3 2.7216(10) .
Bi1 Br2 2.7352(11) .
Bi1 Br4 3.0164(11) .
Bi1 Br6 3.0658(10) 2_665
Bi1 Br5 3.0936(12) .
Bi2 Br7 2.7473(9) .
Bi2 Br9 2.7581(13) .
Bi2 Br5 2.8718(11) .
Bi2 Br8 2.8760(13) .
Bi2 Br4 2.9720(11) .
Bi2 Br6 2.9828(10) .
Br6 Bi1 3.0658(10) 2_665
N1 O1 1.347(10) .
N2 O2 1.340(9) .
N3 O3 1.360(10) .
N4 O4 1.325(11) .
N5 O5 1.367(13) .
