#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/27/2222746.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_2222746
loop_
_publ_author_name
'Zhu, Xiao-Fei'
'Zhou, Yan-Hong'
'Guan, Li'
'Zhang, Hong'
_publ_section_title
;Poly[4-(dimethylamino)pyridinium
 [(μ₆-5-carboxybenzene-1,2,4-tricarboxyato-κ⁶O¹:O^1'^:O²:O⁴:O^4'^:O⁵)diargentate(I)]]
;
_journal_coeditor_code           HY2204
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m994
_journal_page_last               m995
_journal_paper_doi               10.1107/S1600536809028839
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '(C7 H11 N2) [Ag2 (C10 H3 O8)]'
_chemical_formula_moiety         'C7 H11 N2 +, C10 H3 Ag2 O8 -'
_chemical_formula_sum            'C17 H14 Ag2 N2 O8'
_chemical_formula_weight         590.04
_chemical_name_systematic
;Poly[4-(dimethylamino)pyridinium
 [(μ₆-5-carboxybenzene-1,2,4-tricarboxylato-
κ⁶O¹:O^1'^:O²:O⁴:O^4'^:
O⁵)diargentate(I)]]
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.304(4)
_cell_angle_beta                 97.140(3)
_cell_angle_gamma                103.260(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7192(3)
_cell_length_b                   9.9936(5)
_cell_length_c                   10.4968(3)
_cell_measurement_reflns_used    3901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      4.39
_cell_volume                     884.65(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_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  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7226
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_T_max  0.725
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.470
_refine_ls_extinction_coef       0.0157(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0251P)²+0.4969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0462
_reflns_number_gt                2808
_reflns_number_total             3124
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2204.cif
_cod_data_source_block           I
_cod_database_code               2222746
_cod_database_fobs_code          2222746
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag Ag1 0.421397(19) 0.410977(18) 0.802682(17) 0.02690(8) Uani d . 1 . .
Ag Ag2 0.421385(19) 0.385653(19) 1.290598(17) 0.02889(9) Uani d . 1 . .
O O1 0.22857(16) 0.20334(17) 0.81649(18) 0.0277(4) Uani d . 1 . .
O O2 0.10698(15) -0.04467(17) 0.71974(19) 0.0329(4) Uani d . 1 . .
H H2 0.0364 -0.0126 0.7220 0.049 Uiso d R 1 . .
O O3 0.57621(18) 0.37804(17) 1.02125(17) 0.0326(4) Uani d . 1 . .
O O4 0.4252(2) 0.21751(18) 1.07819(17) 0.0344(4) Uani d . 1 . .
O O5 0.41174(19) -0.39642(18) 0.45762(18) 0.0357(4) Uani d . 1 . .
O O6 0.5636(2) -0.23946(18) 0.39821(17) 0.0341(4) Uani d . 1 . .
O O7 0.75751(16) -0.21312(17) 0.65497(17) 0.0251(3) Uani d . 1 . .
O O8 0.87465(16) 0.03113(17) 0.7214(2) 0.0336(4) Uani d . 1 . .
C C1 0.2265(2) 0.0702(2) 0.7685(2) 0.0178(4) Uani d . 1 . .
C C2 0.4977(2) 0.2487(2) 0.9985(2) 0.0173(4) Uani d . 1 . .
C C3 0.4930(2) 0.1181(2) 0.8600(2) 0.0160(4) Uani d . 1 . .
C C4 0.3628(2) -0.0996(2) 0.6355(2) 0.0177(4) Uani d . 1 . .
H H4 0.2755 -0.1617 0.5684 0.021 Uiso calc R 1 . .
C C5 0.3627(2) 0.0251(2) 0.7570(2) 0.0160(4) Uani d . 1 . .
C C6 0.6223(2) -0.0377(2) 0.7128(2) 0.0157(4) Uani d . 1 . .
C C7 0.4913(2) -0.1332(2) 0.6121(2) 0.0153(4) Uani d . 1 . .
C C8 0.6218(2) 0.0862(2) 0.8348(2) 0.0185(4) Uani d . 1 . .
H H8 0.7093 0.1493 0.9012 0.022 Uiso calc R 1 . .
C C9 0.4888(2) -0.2673(2) 0.4775(2) 0.0168(4) Uani d . 1 . .
C C10 0.7617(2) -0.0765(2) 0.6939(2) 0.0192(4) Uani d . 1 . .
N N1 0.0720(2) 0.4030(2) 0.1392(2) 0.0333(5) Uani d . 1 . .
N N2 -0.1309(2) 0.6318(3) 0.4369(2) 0.0378(5) Uani d . 1 . .
H H -0.1683 0.6777 0.5021 0.045 Uiso d R 1 . .
C C11 0.0048(2) 0.4765(3) 0.2354(2) 0.0271(5) Uani d . 1 . .
C C12 -0.0362(3) 0.7091(3) 0.3890(3) 0.0354(6) Uani d . 1 . .
H H12 -0.0172 0.8144 0.4240 0.042 Uiso calc R 1 . .
C C13 -0.1624(3) 0.4795(3) 0.3866(3) 0.0375(6) Uani d . 1 . .
H H13 -0.2296 0.4279 0.4204 0.045 Uiso calc R 1 . .
C C14 -0.0985(3) 0.3988(3) 0.2872(3) 0.0343(6) Uani d . 1 . .
H H14 -0.1223 0.2931 0.2533 0.041 Uiso calc R 1 . .
C C15 0.0325(3) 0.6369(3) 0.2906(3) 0.0333(6) Uani d . 1 . .
H H15 0.0981 0.6930 0.2592 0.040 Uiso calc R 1 . .
C C16 0.0426(3) 0.2378(3) 0.0780(3) 0.0407(6) Uani d . 1 . .
H H16A -0.0540 0.1883 0.0172 0.061 Uiso calc R 1 . .
H H16B 0.0505 0.2065 0.1535 0.061 Uiso calc R 1 . .
H H16C 0.1119 0.2095 0.0231 0.061 Uiso calc R 1 . .
C C17 0.1797(3) 0.4867(4) 0.0902(3) 0.0423(7) Uani d . 1 . .
H H17A 0.2588 0.5591 0.1700 0.063 Uiso calc R 1 . .
H H17B 0.1351 0.5400 0.0473 0.063 Uiso calc R 1 . .
H H17C 0.2160 0.4161 0.0210 0.063 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Ag Ag -0.8971 1.1015 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O6 Ag1 O3 2_656 2_667 165.22(6) ?
O6 Ag1 O1 2_656 . 88.08(6) ?
O3 Ag1 O1 2_667 . 104.84(6) ?
O6 Ag1 Ag2 2_656 2_667 82.64(4) ?
O3 Ag1 Ag2 2_667 2_667 83.04(4) ?
O1 Ag1 Ag2 . 2_667 162.98(4) ?
O3 Ag1 O1 . . 80.23(5) ?
O3 Ag1 O3 . 2_667 82.06(6) ?
O3 Ag1 O6 . 2_656 107.63(5) ?
O3 Ag1 Ag2 . 2_667 116.16(4) ?
O4 Ag2 O5 . 1_566 158.69(7) ?
O4 Ag2 O7 . 2_657 97.68(6) ?
O5 Ag2 O7 1_566 2_657 97.08(5) ?
O4 Ag2 Ag1 . 2_667 81.08(4) ?
O5 Ag2 Ag1 1_566 2_667 81.40(4) ?
O7 Ag2 Ag1 2_657 2_667 168.58(4) ?
O5 Ag2 O4 2_657 . 119.23(5) ?
O5 Ag2 O5 2_657 1_566 78.86(6) ?
O5 Ag2 O7 2_657 2_657 78.31(5) ?
O5 Ag2 Ag1 2_657 2_667 112.29(4) ?
C1 O1 Ag1 . . 123.41(13) ?
C1 O2 H2 . . 109.5 ?
C2 O3 Ag1 . 2_667 123.07(13) ?
C2 O4 Ag2 . . 124.47(14) ?
C9 O5 Ag2 . 1_544 123.12(13) ?
C9 O6 Ag1 . 2_656 124.62(14) ?
C10 O7 Ag2 . 2_657 121.06(12) ?
O1 C1 O2 . . 123.50(18) ?
O1 C1 C5 . . 122.02(17) ?
O2 C1 C5 . . 114.46(17) ?
O4 C2 O3 . . 126.86(19) ?
O4 C2 C3 . . 117.34(18) ?
O3 C2 C3 . . 115.79(17) ?
C8 C3 C5 . . 118.74(18) ?
C8 C3 C2 . . 119.06(17) ?
C5 C3 C2 . . 122.18(17) ?
C5 C4 C7 . . 121.14(18) ?
C5 C4 H4 . . 119.4 ?
C7 C4 H4 . . 119.4 ?
C4 C5 C3 . . 119.97(18) ?
C4 C5 C1 . . 119.38(17) ?
C3 C5 C1 . . 120.24(17) ?
C8 C6 C7 . . 119.81(18) ?
C8 C6 C10 . . 120.10(17) ?
C7 C6 C10 . . 119.93(17) ?
C4 C7 C6 . . 118.95(18) ?
C4 C7 C9 . . 120.01(17) ?
C6 C7 C9 . . 120.99(17) ?
C6 C8 C3 . . 121.33(18) ?
C6 C8 H8 . . 119.3 ?
C3 C8 H8 . . 119.3 ?
O6 C9 O5 . . 126.56(19) ?
O6 C9 C7 . . 117.07(18) ?
O5 C9 C7 . . 116.36(17) ?
O7 C10 O8 . . 124.57(19) ?
O7 C10 C6 . . 117.63(17) ?
O8 C10 C6 . . 117.78(18) ?
C11 N1 C16 . . 122.5(2) ?
C11 N1 C17 . . 120.8(2) ?
C16 N1 C17 . . 116.8(2) ?
C12 N2 C13 . . 120.7(2) ?
C12 N2 H . . 120.9 ?
C13 N2 H . . 118.3 ?
N1 C11 C15 . . 121.4(2) ?
N1 C11 C14 . . 122.1(2) ?
C15 C11 C14 . . 116.4(2) ?
N2 C12 C15 . . 121.3(2) ?
N2 C12 H12 . . 119.3 ?
C15 C12 H12 . . 119.3 ?
N2 C13 C14 . . 121.5(2) ?
N2 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C13 C14 C11 . . 119.7(2) ?
C13 C14 H14 . . 120.1 ?
C11 C14 H14 . . 120.1 ?
C12 C15 C11 . . 120.3(2) ?
C12 C15 H15 . . 119.8 ?
C11 C15 H15 . . 119.8 ?
N1 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ag1 O1 . 2.5220(15) y
Ag1 O3 2_667 2.1784(15) y
Ag1 O3 . 2.7573(19) y
Ag1 O6 2_656 2.1765(15) y
Ag2 O4 . 2.2091(15) y
Ag2 O5 1_566 2.2224(16) y
Ag2 O5 2_657 2.873(2) y
Ag2 O7 2_657 2.4442(15) y
Ag1 Ag2 2_667 2.8189(3) y
O1 C1 . 1.216(3) ?
O2 C1 . 1.306(2) ?
O2 H2 . 0.82 ?
O3 C2 . 1.252(3) ?
O4 C2 . 1.244(3) ?
O5 C9 . 1.255(3) ?
O6 C9 . 1.240(3) ?
O7 C10 . 1.249(3) ?
O8 C10 . 1.257(2) ?
C1 C5 . 1.496(3) ?
C2 C3 . 1.508(3) ?
C3 C8 . 1.392(3) ?
C3 C5 . 1.401(3) ?
C4 C5 . 1.387(3) ?
C4 C7 . 1.392(3) ?
C4 H4 . 0.9300 ?
C6 C8 . 1.387(3) ?
C6 C7 . 1.400(3) ?
C6 C10 . 1.507(3) ?
C7 C9 . 1.507(3) ?
C8 H8 . 0.9300 ?
N1 C11 . 1.336(3) ?
N1 C16 . 1.455(3) ?
N1 C17 . 1.460(3) ?
N2 C12 . 1.339(3) ?
N2 C13 . 1.341(3) ?
N2 H . 0.84 ?
C11 C15 . 1.417(3) ?
C11 C14 . 1.420(3) ?
C12 C15 . 1.355(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.361(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
N2 H O7 1_465 0.84 1.88 2.720(2) 177 y
O2 H2 O8 1_455 0.82 1.73 2.541(2) 173 y
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
O6 Ag1 O1 C1 2_656 . . . 31.61(18) ?
O3 Ag1 O1 C1 2_667 . . . -155.65(17) ?
Ag2 Ag1 O1 C1 2_667 . . . 88.4(2) ?
O5 Ag2 O4 C2 1_566 . . . 43.7(3) ?
O7 Ag2 O4 C2 2_657 . . . 177.18(18) ?
Ag1 Ag2 O4 C2 2_667 . . . 8.66(17) ?
Ag1 O1 C1 O2 . . . . -150.04(16) ?
Ag1 O1 C1 C5 . . . . 28.3(3) ?
Ag2 O4 C2 O3 . . . . -2.3(3) ?
Ag2 O4 C2 C3 . . . . 177.08(13) ?
Ag1 O3 C2 O4 2_667 . . . -9.4(3) ?
Ag1 O3 C2 C3 2_667 . . . 171.21(13) ?
O4 C2 C3 C8 . . . . -119.5(2) ?
O3 C2 C3 C8 . . . . 60.0(3) ?
O4 C2 C3 C5 . . . . 59.0(3) ?
O3 C2 C3 C5 . . . . -121.6(2) ?
C7 C4 C5 C3 . . . . -1.1(3) ?
C7 C4 C5 C1 . . . . 171.50(18) ?
C8 C3 C5 C4 . . . . 2.6(3) ?
C2 C3 C5 C4 . . . . -175.89(19) ?
C8 C3 C5 C1 . . . . -170.00(18) ?
C2 C3 C5 C1 . . . . 11.5(3) ?
O1 C1 C5 C4 . . . . -138.5(2) ?
O2 C1 C5 C4 . . . . 39.9(3) ?
O1 C1 C5 C3 . . . . 34.1(3) ?
O2 C1 C5 C3 . . . . -147.48(19) ?
C5 C4 C7 C6 . . . . -0.8(3) ?
C5 C4 C7 C9 . . . . -178.56(19) ?
C8 C6 C7 C4 . . . . 1.3(3) ?
C10 C6 C7 C4 . . . . 176.73(18) ?
C8 C6 C7 C9 . . . . 179.04(19) ?
C10 C6 C7 C9 . . . . -5.6(3) ?
C7 C6 C8 C3 . . . . 0.1(3) ?
C10 C6 C8 C3 . . . . -175.26(19) ?
C5 C3 C8 C6 . . . . -2.1(3) ?
C2 C3 C8 C6 . . . . 176.43(19) ?
Ag1 O6 C9 O5 2_656 . . . 1.1(3) ?
Ag1 O6 C9 C7 2_656 . . . -179.62(13) ?
Ag2 O5 C9 O6 1_544 . . . 11.0(3) ?
Ag2 O5 C9 C7 1_544 . . . -168.32(13) ?
C4 C7 C9 O6 . . . . 120.2(2) ?
C6 C7 C9 O6 . . . . -57.5(3) ?
C4 C7 C9 O5 . . . . -60.4(3) ?
C6 C7 C9 O5 . . . . 121.9(2) ?
Ag2 O7 C10 O8 2_657 . . . 151.16(17) ?
Ag2 O7 C10 C6 2_657 . . . -27.2(2) ?
C8 C6 C10 O7 . . . . 132.8(2) ?
C7 C6 C10 O7 . . . . -42.6(3) ?
C8 C6 C10 O8 . . . . -45.6(3) ?
C7 C6 C10 O8 . . . . 139.0(2) ?
C16 N1 C11 C15 . . . . -178.3(2) ?
C17 N1 C11 C15 . . . . 1.6(3) ?
C16 N1 C11 C14 . . . . 1.2(4) ?
C17 N1 C11 C14 . . . . -178.8(2) ?
C13 N2 C12 C15 . . . . -1.2(4) ?
C12 N2 C13 C14 . . . . 0.9(4) ?
N2 C13 C14 C11 . . . . 0.3(4) ?
N1 C11 C14 C13 . . . . 179.2(2) ?
C15 C11 C14 C13 . . . . -1.2(3) ?
N2 C12 C15 C11 . . . . 0.2(4) ?
N1 C11 C15 C12 . . . . -179.5(2) ?
C14 C11 C15 C12 . . . . 0.9(3) ?
