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#$Date: 2023-02-14 11:50:18 +0200 (Tue, 14 Feb 2023) $
#$Revision: 280881 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106776.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_8106776
loop_
_publ_author_name
'Jing, Liu'
'Min-Le, Han'
_publ_section_title
;
 Crystal structure of
 trans-1,2-bis(pyridinium-4-yl)ethylene--2-carboxy-4-methylbenzoate (1/2),
 C30H26N2O8
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              31
_journal_page_last               33
_journal_paper_doi               10.1515/ncrs-2014-9081
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C15 H16 N O4'
_chemical_formula_weight         274.29
_chemical_name_systematic
;
 trans-1,2-bis(pyridinium-4-yl)ethylene-2-carboxy-4-methylbenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 124.0840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.567(2)
_cell_length_b                   13.1375(17)
_cell_length_c                   13.4212(17)
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      2.80
_cell_volume                     2565.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9611
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.800
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.00108(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1655
_reflns_number_total             2391
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2014-9081_suppl.cif
_cod_data_source_block           b
_cod_original_cell_volume        2565.3(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106776
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32705(10) 0.57941(11) 0.09352(13) 0.0496(4) Uani 1 1 d . . . . .
O1 O 0.08735(11) 0.26488(10) 0.53453(14) 0.0953(5) Uani 1 1 d . . . . .
O2 O 0.16085(12) 0.29469(10) 0.72598(13) 0.0847(5) Uani 1 1 d . . . . .
H2 H 0.1904 0.3412 0.7729 0.127 Uiso 1 1 calc R U . . .
O3 O 0.23917(10) 0.43545(10) 0.86194(11) 0.0722(4) Uani 1 1 d . . . . .
H3 H -0.113(14) 0.854(19) 0.380(18) 1.30(19) Uiso 1 1 d . . . . .
O4 O 0.22252(10) 0.60091(9) 0.85878(10) 0.0681(4) Uani 1 1 d . . . . .
C1 C 0.36375(13) 0.66003(13) 0.16545(15) 0.0583(5) Uani 1 1 d . . . . .
H1 H 0.3520 0.7249 0.1323 0.070 Uiso 1 1 calc R U . . .
C2 C 0.41842(13) 0.64826(13) 0.28737(15) 0.0549(5) Uani 1 1 d . . . . .
H2A H 0.4444 0.7051 0.3366 0.066 Uiso 1 1 calc R U . . .
C3 C 0.43543(11) 0.55200(12) 0.33826(13) 0.0422(4) Uani 1 1 d . . . . .
C4 C 0.39461(12) 0.46984(12) 0.25990(14) 0.0487(4) Uani 1 1 d . . . . .
H4 H 0.4036 0.4041 0.2902 0.058 Uiso 1 1 calc R U . . .
C5 C 0.34142(12) 0.48588(13) 0.13851(14) 0.0504(4) Uani 1 1 d . . . . .
H5 H 0.3149 0.4306 0.0866 0.060 Uiso 1 1 calc R U . . .
C6 C 0.11740(12) 0.63625(13) 0.50339(15) 0.0503(4) Uani 1 1 d . . . . .
H6 H 0.205(11) 0.888(11) 0.570(13) 0.85(10) Uiso 1 1 d . . . . .
C7 C 0.15605(11) 0.61742(12) 0.62405(14) 0.0463(4) Uani 1 1 d . . . . .
H7 H 0.1791 0.6723 0.6769 0.056 Uiso 1 1 calc R U . . .
C8 C 0.16229(10) 0.52085(12) 0.67057(13) 0.0410(4) Uani 1 1 d . . . . .
H8 H 0.06(2) 0.642(18) 0.30(3) 1.5(3) Uiso 1 1 d . . . . .
C9 C 0.12746(11) 0.43702(12) 0.59095(14) 0.0454(4) Uani 1 1 d . . . . .
C10 C 0.08813(12) 0.45733(14) 0.46967(15) 0.0573(5) Uani 1 1 d . . . . .
H10 H 0.0637 0.4036 0.4153 0.069 Uiso 1 1 calc R U . . .
C11 C 0.08396(13) 0.55353(15) 0.42733(15) 0.0593(5) Uani 1 1 d . . . . .
H11 H 0.0580 0.5631 0.3457 0.071 Uiso 1 1 calc R U . . .
C12 C 0.11366(15) 0.74156(15) 0.45690(18) 0.0735(6) Uani 1 1 d . . . . .
H12A H 0.1148 0.7909 0.5104 0.110 Uiso 0.5 1 calc R U P . .
H12B H 0.0581 0.7492 0.3783 0.110 Uiso 0.5 1 calc R U P . .
H12C H 0.1657 0.7518 0.4523 0.110 Uiso 0.5 1 calc R U P . .
H12D H 0.1110 0.7370 0.3836 0.110 Uiso 0.5 1 calc R U P . .
H12E H 0.1676 0.7787 0.5157 0.110 Uiso 0.5 1 calc R U P . .
H12F H 0.0600 0.7762 0.4417 0.110 Uiso 0.5 1 calc R U P . .
C13 C 0.21092(12) 0.51839(14) 0.80587(15) 0.0492(4) Uani 1 1 d . . . . .
C14 C 0.12437(13) 0.32579(14) 0.61658(19) 0.0606(5) Uani 1 1 d . . . . .
C15 C 0.49534(12) 0.54150(11) 0.46966(14) 0.0467(4) Uani 1 1 d . . . . .
H15 H 0.5295 0.5982 0.5135 0.056 Uiso 1 1 calc R U . . .
H1D H 0.2876(14) 0.5879(15) 0.002(2) 0.094(7) Uiso 1 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 0.0000 0.0000 '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 0.0060 '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
C5 N1 C1 120.96(15) . .
C5 N1 H1D 118.3(12) . .
C1 N1 H1D 120.7(12) . .
C14 O2 H2 109.5 . .
N1 C1 C2 120.59(16) . .
N1 C1 H1 119.7 . .
C2 C1 H1 119.7 . .
C1 C2 C3 120.41(16) . .
C1 C2 H2A 119.8 . .
C3 C2 H2A 119.8 . .
C2 C3 C4 117.18(14) . .
C2 C3 C15 119.23(14) . .
C4 C3 C15 123.58(14) . .
C5 C4 C3 119.97(15) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
N1 C5 C4 120.88(15) . .
N1 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C11 C6 C7 116.91(16) . .
C11 C6 C12 121.14(16) . .
C7 C6 C12 121.94(16) . .
C6 C7 C8 123.52(15) . .
C6 C7 H7 118.2 . .
C8 C7 H7 118.2 . .
C7 C8 C9 118.66(14) . .
C7 C8 C13 114.06(14) . .
C9 C8 C13 127.23(14) . .
C10 C9 C8 117.12(15) . .
C10 C9 C14 113.24(15) . .
C8 C9 C14 129.63(16) . .
C11 C10 C9 122.53(16) . .
C11 C10 H10 118.7 . .
C9 C10 H10 118.7 . .
C10 C11 C6 121.26(16) . .
C10 C11 H11 119.4 . .
C6 C11 H11 119.4 . .
C6 C12 H12A 109.5 . .
C6 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C6 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C6 C12 H12D 109.5 . .
H12A C12 H12D 141.1 . .
H12B C12 H12D 56.3 . .
H12C C12 H12D 56.3 . .
C6 C12 H12E 109.5 . .
H12A C12 H12E 56.3 . .
H12B C12 H12E 141.1 . .
H12C C12 H12E 56.3 . .
H12D C12 H12E 109.5 . .
C6 C12 H12F 109.5 . .
H12A C12 H12F 56.3 . .
H12B C12 H12F 56.3 . .
H12C C12 H12F 141.1 . .
H12D C12 H12F 109.5 . .
H12E C12 H12F 109.5 . .
O4 C13 O3 121.88(15) . .
O4 C13 C8 117.81(15) . .
O3 C13 C8 120.31(15) . .
O1 C14 O2 119.57(18) . .
O1 C14 C9 120.06(19) . .
O2 C14 C9 120.37(17) . .
C15 C15 C3 125.33(19) 5_666 .
C15 C15 H15 117.3 5_666 .
C3 C15 H15 117.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.329(2) .
N1 C1 1.331(2) .
N1 H1D 1.02(2) .
O1 C14 1.214(2) .
O2 C14 1.296(2) .
O2 H2 0.8200 .
O3 C13 1.258(2) .
O4 C13 1.249(2) .
C1 C2 1.365(2) .
C1 H1 0.9300 .
C2 C3 1.388(2) .
C2 H2A 0.9300 .
C3 C4 1.393(2) .
C3 C15 1.468(2) .
C4 C5 1.366(2) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C11 1.377(2) .
C6 C7 1.383(2) .
C6 C12 1.504(2) .
C7 C8 1.391(2) .
C7 H7 0.9300 .
C8 C9 1.413(2) .
C8 C13 1.513(2) .
C9 C10 1.392(2) .
C9 C14 1.509(2) .
C10 C11 1.371(2) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C12 H12D 0.9600 .
C12 H12E 0.9600 .
C12 H12F 0.9600 .
C15 C15 1.315(3) 5_666
C15 H15 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1D O3 1.02(2) 2.55(2) 3.2004(19) 121.5(14) 1_554
N1 H1D O4 1.02(2) 1.61(2) 2.6254(18) 178.2(18) 1_554
O2 H2 O3 0.82 1.60 2.4141(19) 174.8 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 1.1(3) . . . .
N1 C1 C2 C3 -1.0(3) . . . .
C1 C2 C3 C4 0.0(3) . . . .
C1 C2 C3 C15 179.33(17) . . . .
C2 C3 C4 C5 0.8(3) . . . .
C15 C3 C4 C5 -178.48(16) . . . .
C1 N1 C5 C4 -0.3(3) . . . .
C3 C4 C5 N1 -0.7(3) . . . .
C11 C6 C7 C8 -0.1(3) . . . .
C12 C6 C7 C8 -178.74(17) . . . .
C6 C7 C8 C9 0.0(3) . . . .
C6 C7 C8 C13 177.51(16) . . . .
C7 C8 C9 C10 -0.5(2) . . . .
C13 C8 C9 C10 -177.63(16) . . . .
C7 C8 C9 C14 -179.23(17) . . . .
C13 C8 C9 C14 3.7(3) . . . .
C8 C9 C10 C11 1.1(3) . . . .
C14 C9 C10 C11 -179.96(17) . . . .
C9 C10 C11 C6 -1.2(3) . . . .
C7 C6 C11 C10 0.7(3) . . . .
C12 C6 C11 C10 179.33(18) . . . .
C7 C8 C13 O4 15.0(2) . . . .
C9 C8 C13 O4 -167.74(17) . . . .
C7 C8 C13 O3 -164.23(17) . . . .
C9 C8 C13 O3 13.0(3) . . . .
C10 C9 C14 O1 -2.3(3) . . . .
C8 C9 C14 O1 176.46(18) . . . .
C10 C9 C14 O2 177.91(18) . . . .
C8 C9 C14 O2 -3.3(3) . . . .
C2 C3 C15 C15 167.7(2) . . . 5_666
C4 C3 C15 C15 -13.0(3) . . . 5_666
