#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/50/2205072.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_2205072
loop_
_publ_author_name
'Dai-Xi Li'
'Duan-Jun Xu'
'Yuan-Zhi Xu'
_publ_section_title
;
 8-Hydroxyquinolinium--dibromosuccinate--dibromosuccinic acid (2/1/2)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o402
_journal_page_last               o404
_journal_paper_doi               10.1107/S1600536805001704
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac
'2C9 H8 N O +, C4 H2 Br2 O4 2-, 2C4 H4 Br2 O4'
_chemical_formula_moiety
'2C9 H8 N O +, C4 H2 Br2 O4 2-, 2C4 H4 Br2 O4'
_chemical_formula_sum            'C30 H26 Br6 N2 O14'
_chemical_formula_weight         1117.98
_chemical_name_systematic
;
8-Hydroxyquinolinium hemi(dibromosuccinate) dibromosuccinic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'difmap (O-H and N-H) and geom (C-H)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.396(2)
_cell_angle_beta                 100.042(2)
_cell_angle_gamma                100.915(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9687(8)
_cell_length_b                   11.4468(12)
_cell_length_c                   12.6870(13)
_cell_measurement_reflns_used    4238
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.0
_cell_volume                     899.10(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-2 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4687
_diffrn_reflns_theta_full        25.1
_diffrn_reflns_theta_max         25.1
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.768
_exptl_absorpt_correction_T_max  0.292
_exptl_absorpt_correction_T_min  0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.065
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.91
_refine_diff_density_min         -0.96
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.093
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0697P)²+5.0115P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.147
_refine_ls_wR_factor_ref         0.170
_reflns_number_gt                2360
_reflns_number_total             3147
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6142.cif
_cod_data_source_block           I
_cod_database_code               2205072
_cod_database_fobs_code          2205072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_type_symbol
Br1 0.82192(13) 0.58880(9) 0.62382(8) 0.0416(3) Uani d . 1 Br
Br2 0.68209(14) -0.14188(10) -0.07866(10) 0.0525(3) Uani d . 1 Br
Br3 0.69861(16) 0.51918(12) -0.08931(10) 0.0586(4) Uani d . 1 Br
N1 0.6903(10) 0.0796(6) 0.3695(6) 0.0324(15) Uani d . 1 N
O1 0.8055(11) 0.2484(6) 0.5924(6) 0.0540(17) Uani d . 1 O
O11 0.6640(9) 0.3102(6) 0.3460(5) 0.0404(14) Uani d . 1 O
O12 0.6717(9) 0.5056(6) 0.3439(5) 0.0384(14) Uani d . 1 O
O13 0.8228(12) 0.1533(7) -0.0592(6) 0.0568(19) Uani d . 1 O
O14 0.8386(10) 0.2001(6) 0.1283(5) 0.0474(16) Uani d . 1 O
O15 0.7810(10) 0.4240(5) 0.1556(5) 0.0395(14) Uani d . 1 O
O16 0.9551(11) 0.6253(6) 0.1971(5) 0.0488(16) Uani d . 1 O
C2 0.6360(13) 0.0002(9) 0.2567(8) 0.040(2) Uani d . 1 C
H2 0.6110 0.0337 0.2002 0.048 Uiso calc R 1 H
C3 0.6165(15) -0.1308(10) 0.2233(8) 0.051(2) Uani d . 1 C
H3 0.5755 -0.1859 0.1448 0.061 Uiso calc R 1 H
C4 0.6581(13) -0.1783(9) 0.3070(8) 0.042(2) Uani d . 1 C
H4 0.6486 -0.2661 0.2850 0.050 Uiso calc R 1 H
C5 0.7571(13) -0.1406(8) 0.5157(8) 0.041(2) Uani d . 1 C
H5 0.7506 -0.2275 0.4978 0.049 Uiso calc R 1 H
C6 0.8068(13) -0.0580(9) 0.6280(8) 0.042(2) Uani d . 1 C
H6 0.8311 -0.0889 0.6864 0.050 Uiso calc R 1 H
C7 0.8227(12) 0.0770(9) 0.6587(8) 0.042(2) Uani d . 1 C
H7 0.8571 0.1331 0.7367 0.050 Uiso calc R 1 H
C8 0.7874(12) 0.1238(8) 0.5734(7) 0.0349(19) Uani d . 1 C
C9 0.7293(11) 0.0357(7) 0.4559(7) 0.0282(17) Uani d . 1 C
C10 0.7142(11) -0.0981(8) 0.4238(7) 0.0310(18) Uani d . 1 C
C11 0.6438(12) 0.4194(8) 0.3889(7) 0.0287(17) Uani d . 1 C
C12 0.5832(11) 0.4658(8) 0.5027(7) 0.0297(17) Uani d . 1 C
H12 0.5378 0.3919 0.5229 0.036 Uiso calc R 1 H
C13 0.8557(13) 0.1305(8) 0.0270(8) 0.0358(19) Uani d . 1 C
C14 0.9144(14) 0.0087(9) 0.0245(8) 0.044(2) Uani d . 1 C
H14 0.9443 0.0099 0.1033 0.052 Uiso calc R 1 H
C15 0.8866(14) 0.5106(9) 0.1317(8) 0.040(2) Uani d . 1 C
C16 0.920(2) 0.4655(10) 0.0112(10) 0.086(5) Uani d . 1 C
H16 0.9055 0.3722 -0.0219 0.104 Uiso calc R 1 H
H1 0.7007 0.1629 0.3881 0.050 Uiso d . 1 H
H1A 0.9110 0.3099 0.6587 0.050 Uiso d . 1 H
H12A 0.7080 0.4750 0.2740 0.050 Uiso d . 1 H
H14A 0.7950 0.2730 0.1310 0.050 Uiso 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 0.0033 0.0000 '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'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 0.0000 '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 C9 . . 122.0(7)
C2 N1 H1 . . 118.6
C9 N1 H1 . . 119.4
C8 O1 H1A . . 115.8
C11 O12 H12A . . 112.5
C13 O14 H14A . . 114.3
N1 C2 C3 . . 120.8(8)
N1 C2 H2 . . 119.6
C3 C2 H2 . . 119.6
C4 C3 C2 . . 119.1(9)
C4 C3 H3 . . 120.5
C2 C3 H3 . . 120.5
C3 C4 C10 . . 121.0(8)
C3 C4 H4 . . 119.5
C10 C4 H4 . . 119.5
C6 C5 C10 . . 121.4(8)
C6 C5 H5 . . 119.3
C10 C5 H5 . . 119.3
C5 C6 C7 . . 120.8(8)
C5 C6 H6 . . 119.6
C7 C6 H6 . . 119.6
C8 C7 C6 . . 120.1(8)
C8 C7 H7 . . 119.9
C6 C7 H7 . . 119.9
O1 C8 C7 . . 125.0(8)
O1 C8 C9 . . 116.4(7)
C7 C8 C9 . . 118.6(8)
N1 C9 C8 . . 119.6(7)
N1 C9 C10 . . 118.3(7)
C8 C9 C10 . . 122.0(7)
C4 C10 C9 . . 118.8(8)
C4 C10 C5 . . 124.2(8)
C9 C10 C5 . . 117.0(7)
O11 C11 O12 . . 124.6(7)
O11 C11 C12 . . 121.5(7)
O12 C11 C12 . . 114.0(6)
C11 C12 C12 . 2_666 112.7(8)
C11 C12 Br1 . . 107.8(5)
C12 C12 Br1 2_666 . 108.1(7)
C11 C12 H12 . . 109.4
C12 C12 H12 2_666 . 109.4
Br1 C12 H12 . . 109.4
O13 C13 O14 . . 125.9(8)
O13 C13 C14 . . 121.6(8)
O14 C13 C14 . . 112.5(8)
C14 C14 C13 2_755 . 113.0(10)
C14 C14 Br2 2_755 . 106.4(8)
C13 C14 Br2 . . 107.7(6)
C14 C14 H14 2_755 . 109.9
C13 C14 H14 . . 109.9
Br2 C14 H14 . . 109.9
O16 C15 O15 . . 125.1(8)
O16 C15 C16 . . 119.3(8)
O15 C15 C16 . . 115.6(8)
C16 C16 C15 2_765 . 120.1(14)
C16 C16 Br3 2_765 . 93.8(13)
C15 C16 Br3 . . 105.0(8)
C16 C16 H16 2_765 . 112.0
C15 C16 H16 . . 112.0
Br3 C16 H16 . . 112.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C12 . 1.955(8)
Br2 C14 . 1.984(10)
Br3 C16 . 2.144(17)
N1 C2 . 1.339(11)
N1 C9 . 1.364(10)
N1 H1 . 0.884
O1 C8 . 1.338(10)
O1 H1A . 0.959
O11 C11 . 1.223(9)
O12 C11 . 1.303(9)
O12 H12A . 0.932
O13 C13 . 1.204(10)
O14 C13 . 1.295(10)
O14 H14A . 0.932
O15 C15 . 1.276(10)
O16 C15 . 1.226(10)
C2 C3 . 1.381(13)
C2 H2 . 0.9300
C3 C4 . 1.365(13)
C3 H3 . 0.9300
C4 C10 . 1.381(12)
C4 H4 . 0.9300
C5 C6 . 1.345(13)
C5 C10 . 1.419(12)
C5 H5 . 0.9300
C6 C7 . 1.433(13)
C6 H6 . 0.9300
C7 C8 . 1.371(12)
C7 H7 . 0.9300
C8 C9 . 1.411(12)
C9 C10 . 1.418(11)
C11 C12 . 1.519(11)
C12 C12 2_666 1.522(15)
C12 H12 . 0.9800
C13 C14 . 1.516(12)
C14 C14 2_755 1.454(17)
C14 H14 . 0.9800
C15 C16 . 1.509(13)
C16 C16 2_765 1.38(2)
C16 H16 . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O11 . 0.88 1.98 2.793(10) 152 y
O1 H1A O16 2_766 0.96 1.72 2.617(9) 154 y
O12 H12A O15 . 0.93 1.62 2.551(9) 178 y
O14 H14A O15 . 0.93 1.67 2.582(10) 165 y
