#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105058.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_2105058
loop_
_publ_author_name
'Molčanov, Krešimir'
'Kojić-Prodić, Biserka'
_publ_section_title
;
 Face-to-face stacking of quinoid rings of alkali salts of bromanilic acid
;
_journal_coeditor_code           GP5046
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              57
_journal_page_last               65
_journal_paper_doi               10.1107/S0108768111051159
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C6 H8 Br2 Na2 O8'
_chemical_formula_sum            'C6 H8 Br2 Na2 O8'
_chemical_formula_weight         413.90
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                108.113(6)
_cell_angle_beta                 110.543(6)
_cell_angle_gamma                91.991(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0223(6)
_cell_length_b                   8.6764(6)
_cell_length_c                   9.9131(6)
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8786
_cell_measurement_theta_min      5.0725
_cell_volume                     606.03(8)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
        (compiled Aug 27 2010,11:50:40)
;
_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    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Oxford Xcalibur Nova'
_diffrn_measurement_method
;
CCD detector, ω scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4617
_diffrn_reflns_theta_full        76.06
_diffrn_reflns_theta_max         76.06
_diffrn_reflns_theta_min         5.08
_exptl_absorpt_coefficient_mu    9.523
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.19381
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.509
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.0514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                1989
_reflns_number_total             2459
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gp5046.cif
_cod_data_source_block           Na2BAx4H2O
_cod_original_cell_volume        606.03(7)
_cod_database_code               2105058
_cod_database_fobs_code          2105058
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
Na Na1 0.79693(16) 0.53269(14) 0.68730(13) 0.0328(3) Uani d . 1
Na Na2 0.63882(17) 0.65270(15) 1.00292(13) 0.0362(3) Uani d . 1
Br Br1 0.73381(5) 1.03516(4) 0.17219(3) 0.03785(15) Uani d . 1
Br Br2 0.75597(5) 0.96537(4) 0.82555(3) 0.03585(15) Uani d . 1
O O1 0.7498(3) 0.7022(2) 0.5312(3) 0.0380(5) Uani d . 1
O O2 0.7467(4) 0.7311(3) 0.2714(3) 0.0403(6) Uani d . 1
O O3 0.7387(3) 1.2968(2) 0.4649(2) 0.0331(5) Uani d . 1
O O4 0.7663(3) 1.2728(2) 0.7332(2) 0.0342(5) Uani d . 1
O O5 1.0990(3) 0.5507(3) 0.7037(3) 0.0363(5) Uani d D 1
H H5A 1.134(6) 0.611(4) 0.654(4) 0.063(13) Uiso d D 1
H H5B 1.129(6) 0.448(3) 0.671(5) 0.076(15) Uiso d D 1
O O6 0.9278(3) 0.6716(3) 0.9812(3) 0.0424(5) Uani d D 1
H H6A 1.009(8) 0.664(7) 1.073(5) 0.17(3) Uiso d D 1
H H6B 0.973(8) 0.775(4) 0.985(7) 0.13(2) Uiso d D 1
O O7 0.6512(3) 0.3758(3) 0.9931(3) 0.0376(5) Uani d D 1
H H7A 0.678(5) 0.313(4) 0.914(3) 0.065(13) Uiso d D 1
H H7B 0.749(5) 0.391(6) 1.084(3) 0.10(2) Uiso d D 1
O O8 0.5214(3) 0.5664(3) 0.7288(2) 0.0341(5) Uani d D 1
H H8A 0.463(6) 0.644(4) 0.690(5) 0.11(2) Uiso d D 1
H H8B 0.442(5) 0.468(3) 0.684(5) 0.073(15) Uiso d D 1
C C1 0.7520(4) 0.8425(3) 0.5243(3) 0.0247(5) Uani d . 1
C C2 0.7488(4) 0.8580(3) 0.3728(3) 0.0269(6) Uani d . 1
C C3 0.7457(4) 1.0143(3) 0.3599(3) 0.0267(6) Uani d . 1
C C4 0.7463(4) 1.1570(3) 0.4757(3) 0.0237(5) Uani d . 1
C C5 0.7564(4) 1.1434(3) 0.6297(3) 0.0234(5) Uani d . 1
C C6 0.7534(4) 0.9867(3) 0.6399(3) 0.0249(5) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 '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'
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
Na1 O5 H5A . . 118(3)
Na1 O5 H5B . . 111(3)
Na1 O6 H6A . . 144(4)
Na1 O6 H6B . . 98(4)
Na1 O8 H8A . . 112(3)
Na1 O8 H8B . . 111(3)
Na2 Na2 Na1 2_667 . 113.25(5)
Na2 O6 Na1 . . 94.22(9)
Na2 O6 H6A . . 104(4)
Na2 O6 H6B . . 115(4)
Na2 O7 Na2 2_667 . 91.10(9)
Na2 O7 H7A 2_667 . 122(3)
Na2 O7 H7A . . 113(3)
Na2 O7 H7B 2_667 . 118(3)
Na2 O7 H7B . . 101(3)
Na2 O8 Na1 . . 99.36(8)
Na2 O8 H8A . . 114(3)
Na2 O8 H8B . . 112(3)
Br1 Na2 Na1 1_556 . 110.39(4)
Br1 Na2 Na2 1_556 2_667 134.95(6)
O1 Na1 Na2 . . 116.87(7)
O1 Na1 O4 . 1_545 154.48(9)
O1 Na1 O6 . . 118.74(9)
O1 Na1 O8 . . 94.47(9)
O1 C1 C2 . . 116.3(2)
O1 C1 C6 . . 126.2(3)
O2 Na2 Na1 1_556 . 140.84(8)
O2 Na2 Na2 1_556 2_667 86.02(8)
O2 Na2 Br1 1_556 1_556 66.49(6)
O2 Na2 O6 1_556 . 97.15(10)
O2 Na2 O7 1_556 . 87.88(9)
O2 Na2 O8 1_556 . 178.14(10)
O2 C2 C3 . . 125.1(3)
O2 C2 C1 . . 117.3(3)
O3 Na1 Na2 1_545 . 136.17(7)
O3 Na1 O1 1_545 . 89.47(8)
O3 Na1 O4 1_545 1_545 66.84(8)
O3 Na1 O6 1_545 . 150.14(9)
O3 Na1 O8 1_545 . 108.43(9)
O3 C4 C3 . . 125.3(3)
O3 C4 C5 . . 116.4(2)
O4 Na1 Na2 1_545 . 78.31(6)
O4 Na1 O6 1_545 . 86.38(9)
O4 C5 C4 . . 117.1(2)
O4 C5 C6 . . 125.9(3)
O5 Na1 Na2 . . 127.62(7)
O5 Na1 O1 . . 87.19(9)
O5 Na1 O1 . . 87.19(9)
O5 Na1 O3 . 1_545 85.15(9)
O5 Na1 O4 . 1_545 99.54(9)
O5 Na1 O6 . . 86.63(9)
O5 Na1 O8 . . 166.31(9)
O6 Na1 Na2 . . 41.10(6)
O6 Na2 Na1 . . 44.68(6)
O6 Na2 Na2 . 2_667 134.12(9)
O6 Na2 Br1 . 1_556 86.15(7)
O7 Na2 Na1 2_667 . 131.62(7)
O7 Na2 Na1 . . 84.54(7)
O7 Na2 Na2 2_667 2_667 44.85(6)
O7 Na2 Na2 . 2_667 44.05(6)
O7 Na2 Br1 2_667 1_556 96.27(7)
O7 Na2 Br1 . 1_556 153.36(8)
O7 Na2 O2 2_667 1_556 86.43(10)
O7 Na2 O6 2_667 . 176.27(10)
O7 Na2 O6 . . 90.18(9)
O7 Na2 O7 2_667 . 88.90(9)
O7 Na2 O8 2_667 . 92.10(9)
O7 Na2 O8 . . 90.95(9)
O8 Na2 Na1 . . 40.38(6)
O8 Na1 Na2 . . 40.26(6)
O8 Na1 O4 . 1_545 84.78(8)
O8 Na1 O6 . . 80.66(8)
O8 Na2 Na2 . 2_667 92.13(7)
O8 Na2 Br1 . 1_556 114.85(7)
O8 Na2 O6 . . 84.30(9)
C1 O1 Na1 . . 148.1(2)
C1 C6 Br2 . . 117.0(2)
C2 O2 Na2 . 1_554 132.6(2)
C2 C3 Br1 . . 118.3(2)
C3 Br1 Na2 . 1_554 92.02(9)
C3 C2 C1 . . 117.6(2)
C3 C4 C5 . . 118.2(2)
C4 O3 Na1 . 1_565 120.30(18)
C4 C3 Br1 . . 117.2(2)
C4 C3 C2 . . 124.4(3)
C5 O4 Na1 . 1_565 118.02(19)
C5 C6 Br2 . . 117.8(2)
C5 C6 C1 . . 125.2(3)
C6 C1 C2 . . 117.5(2)
C6 C5 C4 . . 117.0(2)
H5A O5 H5B . . 107(3)
H6B O6 H6A . . 102(3)
H7B O7 H7A . . 108(3)
H8A O8 H8B . . 108(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Na1 O3 1_545 2.382(2)
Na1 O4 1_545 2.456(2)
Na1 O5 . 2.368(3)
Na1 O6 . 2.574(3)
Na1 O8 . 2.397(3)
Na2 Na2 2_667 3.375(2)
Na2 Br1 1_556 3.1421(12)
Na2 O2 1_556 2.348(2)
Na2 O6 . 2.407(3)
Na2 O7 2_667 2.347(3)
Na2 O7 . 2.381(3)
Na2 O8 . 2.392(2)
Br1 Na2 1_554 3.1421(12)
Br1 C3 . 1.895(3)
Br2 C6 . 1.899(3)
O1 Na1 . 2.396(2)
O1 C1 . 1.240(4)
O2 Na2 1_554 2.348(2)
O2 C2 . 1.233(3)
O3 Na1 1_565 2.382(2)
O3 C4 . 1.252(3)
O4 Na1 1_565 2.456(2)
O4 C5 . 1.241(3)
O5 H5A . 0.921(19)
O5 H5B . 0.918(18)
O6 H6A . 0.94(2)
O6 H6B . 0.935(19)
O7 Na2 2_667 2.347(3)
O7 H7A . 0.908(18)
O7 H7B . 0.929(19)
O8 H8A . 0.938(14)
O8 H8B . 0.928(14)
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
Na1 Na2 O7 Na2 . 2_667 -132.00(8)
Na1 O1 C1 C6 . . -17.3(6)
Na1 O1 C1 C2 . . 164.1(3)
Na1 O3 C4 C3 1_565 . -168.4(2)
Na1 O3 C4 C5 1_565 . 11.9(3)
Na1 O4 C5 C4 1_565 . -5.6(3)
Na1 O4 C5 C6 1_565 . 174.5(2)
Na2 Na2 Na1 O1 2_667 . 126.13(9)
Na2 Na2 Na1 O3 2_667 1_545 5.28(13)
Na2 Na2 Na1 O4 2_667 1_545 -32.03(8)
Na2 Na2 Na1 O5 2_667 . -125.15(9)
Na2 Na2 Na1 O6 2_667 . -130.02(12)
Na2 Na2 Na1 O8 2_667 . 63.73(10)
Na2 Na2 O6 Na1 2_667 . 78.54(13)
Na2 Na2 O8 Na1 2_667 . -124.47(8)
Na2 Br1 C3 C2 1_554 . 12.5(2)
Na2 Br1 C3 C4 1_554 . -166.0(2)
Na2 O2 C2 C1 1_554 . 153.8(2)
Na2 O2 C2 C3 1_554 . -25.2(5)
Br1 Na2 Na1 O1 1_556 . -42.38(9)
Br1 Na2 Na1 O3 1_556 1_545 -163.23(9)
Br1 Na2 Na1 O4 1_556 1_545 159.46(7)
Br1 Na2 Na1 O5 1_556 . 66.35(9)
Br1 Na2 Na1 O6 1_556 . 61.47(10)
Br1 Na2 Na1 O8 1_556 . -104.78(9)
Br1 Na2 O6 Na1 1_556 . -124.37(7)
Br1 Na2 O7 Na2 1_556 2_667 101.84(16)
Br1 Na2 O8 Na1 1_556 . 92.75(8)
Br1 C3 C2 C1 . . -178.00(19)
Br1 C3 C2 O2 . . 1.0(4)
Br2 C6 C1 O1 . . 1.1(4)
Br2 C6 C1 C2 . . 179.63(19)
O1 C1 C2 O2 . . -1.0(4)
O1 C1 C2 C3 . . 178.1(3)
O1 Na1 O6 Na2 . . 98.94(11)
O1 Na1 O8 Na2 . . -127.54(9)
O2 Na2 Na1 O1 1_556 . -119.80(13)
O2 Na2 Na1 O5 1_556 . -11.08(15)
O2 Na2 Na1 O3 1_556 1_545 119.35(14)
O2 Na2 Na1 O4 1_556 1_545 82.03(13)
O2 Na2 Na1 O6 1_556 . -15.96(14)
O2 Na2 Na1 O8 1_556 . 177.79(15)
O2 Na2 O6 Na1 1_556 . 169.92(9)
O2 Na2 O7 Na2 1_556 2_667 86.47(10)
O2 Na2 O8 Na1 1_556 . -132(3)
O3 Na1 O6 Na2 1_545 . -101.96(19)
O3 Na1 O8 Na2 1_545 . 141.53(9)
O3 C4 C3 Br1 . . 0.4(4)
O3 C4 C3 C2 . . -178.0(3)
O4 Na1 O6 Na2 1_545 . -76.34(10)
O4 Na1 O8 Na2 1_545 . 78.07(9)
O4 C5 C4 O3 . . -3.9(4)
O4 C5 C4 C3 . . 176.4(3)
O4 C5 C6 Br2 . . 2.4(4)
O4 C5 C6 C1 . . -176.4(3)
O5 Na1 O6 Na2 . . -176.13(10)
O5 Na1 O8 Na2 . . -31.1(4)
O6 Na1 O8 Na2 . . -9.11(9)
O6 Na2 Na1 O1 . . -103.84(12)
O6 Na2 Na1 O3 . 1_545 135.30(14)
O6 Na2 Na1 O4 . 1_545 97.99(11)
O6 Na2 Na1 O5 . . 4.88(12)
O6 Na2 Na1 O8 . . -166.25(13)
O6 Na2 O7 Na2 . 2_667 -176.39(10)
O6 Na2 O8 Na1 . . 9.67(9)
O7 Na2 Na1 O1 2_667 . 76.70(13)
O7 Na2 Na1 O1 . . 160.35(10)
O7 Na2 Na1 O3 2_667 1_545 -44.15(15)
O7 Na2 Na1 O3 . 1_545 39.49(12)
O7 Na2 Na1 O4 2_667 1_545 -81.46(12)
O7 Na2 Na1 O4 . 1_545 2.18(9)
O7 Na2 Na1 O5 2_667 . -174.58(12)
O7 Na2 Na1 O5 . . -90.93(10)
O7 Na2 Na1 O6 2_667 . -179.45(14)
O7 Na2 Na1 O6 . . -95.81(11)
O7 Na2 Na1 O8 2_667 . 14.30(12)
O7 Na2 Na1 O8 . . 97.94(11)
O7 Na2 O6 Na1 2_667 . 6.3(17)
O7 Na2 O6 Na1 . . 82.04(9)
O7 Na2 O7 Na2 2_667 2_667 0
O7 Na2 O8 Na1 2_667 . -169.35(9)
O7 Na2 O8 Na1 . . -80.42(9)
O8 Na1 O6 Na2 . . 8.96(8)
O8 Na2 Na1 O1 . . 62.41(11)
O8 Na2 Na1 O3 . 1_545 -58.45(13)
O8 Na2 Na1 O4 . 1_545 -95.76(11)
O8 Na2 Na1 O5 . . 171.13(13)
O8 Na2 Na1 O6 . . 166.25(13)
O8 Na2 O6 Na1 . . -8.90(8)
O8 Na2 O7 Na2 . 2_667 -92.08(9)
C1 O1 Na1 O5 . . -90.1(4)
C1 O1 Na1 O3 . 1_545 -175.3(4)
C1 O1 Na1 O8 . . 76.3(4)
C1 O1 Na1 O4 . 1_545 163.5(4)
C1 O1 Na1 O6 . . -5.5(5)
C1 O1 Na1 Na2 . . 41.2(5)
C4 C3 C2 O2 . . 179.3(3)
C4 C3 C2 C1 . . 0.4(5)
C4 C5 C6 Br2 . . -177.53(18)
C4 C5 C6 C1 . . 3.7(4)
C5 C4 C3 Br1 . . -179.83(19)
C5 C4 C3 C2 . . 1.8(5)
C6 C1 C2 O2 . . -179.7(3)
C6 C1 C2 C3 . . -0.6(4)
C5 C6 C1 O1 . . 179.8(3)
C5 C6 C1 C2 . . -1.6(4)
C6 C5 C4 O3 . . 176.0(3)
C6 C5 C4 C3 . . -3.7(4)
