#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/81/2228121.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_2228121
loop_
_publ_author_name
'Lush, Shie Fu'
'Shen, Fwu Ming'
_publ_section_title
;
 4,4'-(Ethane-1,2-diyl)dipyridinium bis(2-hydroxybenzoate)
;
_journal_coeditor_code           XU5033
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2701
_journal_paper_doi               10.1107/S160053681003816X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H14 N2 2+, 2C7 H5 O3 -'
_chemical_formula_moiety         'C12 H14 N2 2+, 2(C7 H5 O3 -)'
_chemical_formula_sum            'C26 H24 N2 O6'
_chemical_formula_weight         460.47
_chemical_name_systematic
;
4,4'-(ethane-1,2-diyl)dipyridinium bis(2-hydroxybenzoate)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.324(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.622(3)
_cell_length_b                   6.867(2)
_cell_length_c                   19.566(6)
_cell_measurement_reflns_used    2343
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      3.59
_cell_volume                     1135.9(6)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6165
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.254
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=KFc[1+0.001Fc²λ³/sin(2Θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0470
_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)+(0.0761P)²+0.1342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                1645
_reflns_number_total             2246
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5033.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228121
_cod_database_fobs_code          2228121
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N 0.23112(16) 0.41868(19) 0.59247(7) 0.0507(5) Uani . . 1.000
C C8 0.30204(19) 0.4936(2) 0.54421(9) 0.0508(6) Uani . . 1.000
C C9 0.25306(19) 0.6652(2) 0.51103(9) 0.0502(5) Uani . . 1.000
C C10 0.12421(17) 0.7649(2) 0.52708(8) 0.0419(5) Uani . . 1.000
C C11 0.05191(19) 0.6837(2) 0.57748(9) 0.0504(5) Uani . . 1.000
C C12 0.1084(2) 0.5109(3) 0.60879(10) 0.0545(6) Uani . . 1.000
C C13 0.07080(18) 0.9519(2) 0.48984(9) 0.0483(5) Uani . . 1.000
O O1 0.32265(15) 0.10150(17) 0.65611(7) 0.0612(5) Uani . . 1.000
O O2 0.48925(16) 0.07561(19) 0.58403(7) 0.0689(5) Uani . . 1.000
O O3 0.67244(17) -0.2176(2) 0.59167(8) 0.0822(6) Uani . . 1.000
C C1 0.43333(19) 0.0129(2) 0.63306(9) 0.0463(5) Uani . . 1.000
C C2 0.48956(17) -0.1735(2) 0.66799(8) 0.0425(5) Uani . . 1.000
C C3 0.4252(2) -0.2478(3) 0.72231(9) 0.0515(6) Uani . . 1.000
C C4 0.4772(2) -0.4221(3) 0.75408(10) 0.0660(7) Uani . . 1.000
C C5 0.5946(2) -0.5245(3) 0.73117(11) 0.0696(7) Uani . . 1.000
C C6 0.6594(2) -0.4550(3) 0.67733(12) 0.0670(7) Uani . . 1.000
C C7 0.6078(2) -0.2797(2) 0.64510(10) 0.0515(6) Uani . . 1.000
H H1A 0.26440 0.31150 0.61290 0.0610 Uiso calc R 1.000
H H8 0.38750 0.42790 0.53250 0.0610 Uiso calc R 1.000
H H9 0.30600 0.71500 0.47780 0.0600 Uiso calc R 1.000
H H11 -0.03430 0.74520 0.59020 0.0600 Uiso calc R 1.000
H H12 0.05870 0.45740 0.64250 0.0650 Uiso calc R 1.000
H H13A 0.04610 0.92600 0.44020 0.0580 Uiso calc R 1.000
H H13B 0.15830 1.04320 0.49830 0.0580 Uiso calc R 1.000
H H3 0.34550 -0.17890 0.73760 0.0620 Uiso calc R 1.000
H H3A 0.62520 -0.11430 0.58230 0.1230 Uiso . R 1.000
H H4 0.43350 -0.46980 0.79060 0.0790 Uiso calc R 1.000
H H5 0.63030 -0.64170 0.75240 0.0830 Uiso calc R 1.000
H H6 0.73840 -0.52550 0.66230 0.0800 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O3 H3A . . . 101.00 no
C8 N C12 . . . 119.22(15) no
C8 N H1A . . . 120.00 no
C12 N H1A . . . 120.00 no
N C8 C9 . . . 121.90(15) no
C8 C9 C10 . . . 120.06(15) no
C9 C10 C13 . . . 119.52(14) no
C11 C10 C13 . . . 123.49(14) no
C9 C10 C11 . . . 116.99(13) no
C10 C11 C12 . . . 119.61(15) no
N C12 C11 . . . 122.22(17) no
C10 C13 C13 . . 3_576 115.66(13) no
N C8 H8 . . . 119.00 no
C9 C8 H8 . . . 119.00 no
C8 C9 H9 . . . 120.00 no
C10 C9 H9 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
N C12 H12 . . . 119.00 no
C11 C12 H12 . . . 119.00 no
C10 C13 H13B . . . 108.00 no
H13A C13 H13B . . . 107.00 no
C10 C13 H13A . . . 108.00 no
C13 C13 H13B 3_576 . . 108.00 no
C13 C13 H13A 3_576 . . 108.00 no
O1 C1 C2 . . . 116.34(14) no
O2 C1 C2 . . . 121.09(15) no
O1 C1 O2 . . . 122.57(14) no
C1 C2 C7 . . . 119.65(14) no
C3 C2 C7 . . . 118.68(15) no
C1 C2 C3 . . . 121.65(15) no
C2 C3 C4 . . . 121.27(16) no
C3 C4 C5 . . . 119.33(18) no
C4 C5 C6 . . . 120.56(19) no
C5 C6 C7 . . . 120.48(18) no
O3 C7 C6 . . . 118.79(16) no
C2 C7 C6 . . . 119.68(16) no
O3 C7 C2 . . . 121.52(14) no
C2 C3 H3 . . . 119.00 no
C4 C3 H3 . . . 119.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C7 C6 H6 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.286(2) no
O2 C1 . . 1.233(2) no
O3 C7 . . 1.347(2) no
O3 H3A . . 0.8200 no
N C8 . . 1.326(2) no
N C12 . . 1.325(2) no
N H1A . . 0.8600 no
C8 C9 . . 1.371(2) no
C9 C10 . . 1.392(2) no
C10 C11 . . 1.383(2) no
C10 C13 . . 1.503(2) no
C11 C12 . . 1.380(3) no
C13 C13 . 3_576 1.509(2) no
C8 H8 . . 0.9300 no
C9 H9 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
C1 C2 . . 1.487(2) no
C2 C7 . . 1.397(2) no
C2 C3 . . 1.389(2) no
C3 C4 . . 1.382(3) no
C4 C5 . . 1.378(3) no
C5 C6 . . 1.371(3) no
C6 C7 . . 1.391(3) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
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
N H1A O1 . 0.86 1.70 2.556(2) 177 yes
O3 H3A O2 . 0.82 1.76 2.545(2) 160 yes
C11 H11 O3 1_465 0.93 2.55 3.406(3) 154 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N C8 C9 . . . . 0.7(2) no
C8 N C12 C11 . . . . -0.4(3) no
N C8 C9 C10 . . . . -0.8(3) no
C8 C9 C10 C11 . . . . 0.6(2) no
C8 C9 C10 C13 . . . . -179.43(15) no
C9 C10 C11 C12 . . . . -0.4(2) no
C13 C10 C11 C12 . . . . 179.70(16) no
C9 C10 C13 C13 . . . 3_576 179.34(14) no
C11 C10 C13 C13 . . . 3_576 -0.7(2) no
C10 C11 C12 N . . . . 0.2(3) no
C10 C13 C13 C10 . . 3_576 3_576 -179.97(17) no
O1 C1 C2 C3 . . . . 0.3(2) no
O1 C1 C2 C7 . . . . 178.98(15) no
O2 C1 C2 C3 . . . . -178.62(16) no
O2 C1 C2 C7 . . . . 0.1(2) no
C1 C2 C3 C4 . . . . 179.41(16) no
C7 C2 C3 C4 . . . . 0.7(3) no
C1 C2 C7 O3 . . . . -0.2(2) no
C1 C2 C7 C6 . . . . -179.40(16) no
C3 C2 C7 O3 . . . . 178.52(16) no
C3 C2 C7 C6 . . . . -0.7(3) no
C2 C3 C4 C5 . . . . -0.3(3) no
C3 C4 C5 C6 . . . . -0.1(3) no
C4 C5 C6 C7 . . . . 0.1(3) no
C5 C6 C7 O3 . . . . -178.96(18) no
C5 C6 C7 C2 . . . . 0.3(3) no
