#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/79/2217991.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_2217991
loop_
_publ_author_name
'Liu, Ping'
'Deng, Dong-Sheng'
_publ_section_title
;
 Bis[bis(1H-imidazole-κN³)silver(I)]
 naphthalene-1,5-disulfonate
;
_journal_coeditor_code           RK2068
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m556
_journal_paper_doi               10.1107/S1600536808006855
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Ag (C3 H4 N2)2] (C10 H6 O6 S2)'
_chemical_formula_moiety         '2(C6 H8 Ag N4 +), C10 H6 O6 S2 2-'
_chemical_formula_sum            'C22 H22 Ag2 N8 O6 S2'
_chemical_formula_weight         774.36
_chemical_name_systematic
;
Bis[bis(1H-imidazole-\kN³)silver(I)] naphthalene-1,5-disulfonate
;
_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           SHELXL97
_cell_angle_alpha                65.286(2)
_cell_angle_beta                 76.311(2)
_cell_angle_gamma                66.791(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6491(11)
_cell_length_b                   9.0196(12)
_cell_length_c                   10.2620(13)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.19
_cell_volume                     665.89(15)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker Smart 1000 CCD diffractometer'
_diffrn_measurement_method       'φ-- and ω--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  0.0102
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4267
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.682
_exptl_absorpt_correction_T_max  0.8110
_exptl_absorpt_correction_T_min  0.4867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.671
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0259
_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)+(0.0388P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                2417
_reflns_number_total             2962
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            rk2068.cif
_cod_data_source_block           I
_cod_database_code               2217991
_cod_database_fobs_code          2217991
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
Ag Ag1 0.27879(2) 1.03409(3) 0.79027(2) 0.05010(9) Uani d . 1
S S1 0.26541(6) 0.60865(7) 0.78924(5) 0.02831(12) Uani d . 1
O O1 0.2153(2) 0.7948(2) 0.71897(19) 0.0442(4) Uani d . 1
O O2 0.1257(2) 0.5487(2) 0.87280(17) 0.0403(4) Uani d . 1
O O3 0.40789(19) 0.5352(2) 0.87452(17) 0.0394(4) Uani d . 1
N N1 0.0163(2) 1.1487(3) 0.8293(2) 0.0375(5) Uani d . 1
N N2 -0.2347(3) 1.2925(3) 0.9009(2) 0.0432(5) Uani d . 1
H H2A -0.3130 1.3607 0.9392 0.052 Uiso calc R 1
N N3 0.5433(3) 0.9312(3) 0.7528(2) 0.0452(5) Uani d . 1
N N4 0.8038(3) 0.7606(3) 0.7855(3) 0.0526(6) Uani d . 1
H H4A 0.8907 0.6797 0.8272 0.063 Uiso calc R 1
C C1 -0.0695(3) 1.2583(3) 0.8957(3) 0.0400(6) Uani d . 1
H H1A -0.0211 1.3053 0.9338 0.048 Uiso calc R 1
C C2 -0.2576(3) 1.2010(4) 0.8351(3) 0.0478(6) Uani d . 1
H H2B -0.3600 1.1994 0.8230 0.057 Uiso calc R 1
C C3 -0.1029(3) 1.1132(3) 0.7907(3) 0.0441(6) Uani d . 1
H H3A -0.0801 1.0397 0.7415 0.053 Uiso calc R 1
C C4 0.6465(4) 0.8000(4) 0.8461(3) 0.0521(7) Uani d . 1
H H4B 0.6136 0.7427 0.9413 0.063 Uiso calc R 1
C C5 0.8032(3) 0.8703(4) 0.6468(3) 0.0500(7) Uani d . 1
H H5A 0.8953 0.8729 0.5783 0.060 Uiso calc R 1
C C6 0.6423(3) 0.9747(4) 0.6280(3) 0.0454(6) Uani d . 1
H H6A 0.6041 1.0637 0.5423 0.054 Uiso calc R 1
C C7 0.3281(2) 0.5262(3) 0.6470(2) 0.0261(4) Uani d . 1
C C8 0.2202(3) 0.4654(3) 0.6223(2) 0.0315(5) Uani d . 1
H H8A 0.1202 0.4645 0.6810 0.038 Uiso calc R 1
C C9 0.2585(3) 0.4046(3) 0.5098(3) 0.0356(5) Uani d . 1
H H9A 0.1838 0.3637 0.4942 0.043 Uiso calc R 1
C C10 0.4037(3) 0.4044(3) 0.4227(2) 0.0303(5) Uani d . 1
H H10A 0.4281 0.3617 0.3492 0.036 Uiso calc R 1
C C11 0.5190(2) 0.4687(3) 0.4427(2) 0.0244(4) 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 0.0033 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'
S S 0.1246 0.1234 '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'
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
N1 Ag1 N3 . . 176.72(8)
N1 Ag1 O1 . . 89.09(7)
N3 Ag1 O1 . . 94.16(7)
O1 S1 O3 . . 113.46(11)
O1 S1 O2 . . 113.10(11)
O3 S1 O2 . . 111.15(10)
O1 S1 C7 . . 105.46(10)
O3 S1 C7 . . 107.98(9)
O2 S1 C7 . . 105.03(10)
S1 O1 Ag1 . . 128.71(10)
C1 N1 C3 . . 105.4(2)
C1 N1 Ag1 . . 130.79(18)
C3 N1 Ag1 . . 123.79(16)
C1 N2 C2 . . 107.9(2)
C1 N2 H2A . . 126.1
C2 N2 H2A . . 126.1
C4 N3 C6 . . 105.3(2)
C4 N3 Ag1 . . 126.0(2)
C6 N3 Ag1 . . 128.55(18)
C4 N4 C5 . . 108.0(2)
C4 N4 H4A . . 126.0
C5 N4 H4A . . 126.0
N1 C1 N2 . . 110.9(2)
N1 C1 H1A . . 124.5
N2 C1 H1A . . 124.5
C3 C2 N2 . . 106.3(2)
C3 C2 H2B . . 126.8
N2 C2 H2B . . 126.8
C2 C3 N1 . . 109.5(2)
C2 C3 H3A . . 125.2
N1 C3 H3A . . 125.2
N3 C4 N4 . . 110.8(3)
N3 C4 H4B . . 124.6
N4 C4 H4B . . 124.6
C6 C5 N4 . . 105.9(3)
C6 C5 H5A . . 127.0
N4 C5 H5A . . 127.0
C5 C6 N3 . . 110.0(3)
C5 C6 H6A . . 125.0
N3 C6 H6A . . 125.0
C8 C7 C11 . 2_666 120.85(19)
C8 C7 S1 . . 117.59(16)
C11 C7 S1 2_666 . 121.48(16)
C7 C8 C9 . . 120.6(2)
C7 C8 H8A . . 119.7
C9 C8 H8A . . 119.7
C10 C9 C8 . . 120.8(2)
C10 C9 H9A . . 119.6
C8 C9 H9A . . 119.6
C9 C10 C11 . . 120.8(2)
C9 C10 H10A . . 119.6
C11 C10 H10A . . 119.6
C10 C11 C7 . 2_666 123.01(18)
C10 C11 C11 . 2_666 118.9(2)
C7 C11 C11 2_666 2_666 118.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ag1 N1 . 2.1092(19)
Ag1 N3 . 2.110(2)
Ag1 O1 . 2.8180(19)
S1 O1 . 1.4451(19)
S1 O3 . 1.4511(16)
S1 O2 . 1.4573(18)
S1 C7 . 1.787(2)
N1 C1 . 1.318(3)
N1 C3 . 1.371(3)
N2 C1 . 1.329(3)
N2 C2 . 1.354(4)
N2 H2A . 0.8600
N3 C4 . 1.318(3)
N3 C6 . 1.361(4)
N4 C4 . 1.330(4)
N4 C5 . 1.351(4)
N4 H4A . 0.8600
C1 H1A . 0.9300
C2 C3 . 1.342(4)
C2 H2B . 0.9300
C3 H3A . 0.9300
C4 H4B . 0.9300
C5 C6 . 1.343(4)
C5 H5A . 0.9300
C6 H6A . 0.9300
C7 C8 . 1.367(3)
C7 C11 2_666 1.426(3)
C8 C9 . 1.396(3)
C8 H8A . 0.9300
C9 C10 . 1.358(3)
C9 H9A . 0.9300
C10 C11 . 1.423(3)
C10 H10A . 0.9300
C11 C7 2_666 1.426(3)
C11 C11 2_666 1.428(4)
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
N4 H4A O2 1_655 0.86 1.96 2.786(3) 160.7
N2 H2A O3 1_465 0.86 2.37 2.998(3) 129.8
N2 H2A O3 2_577 0.86 2.32 3.082(3) 148.6
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
O3 S1 O1 Ag1 . . -21.44(16)
O2 S1 O1 Ag1 . . 106.34(13)
C7 S1 O1 Ag1 . . -139.42(11)
N1 Ag1 O1 S1 . . -117.49(14)
N3 Ag1 O1 S1 . . 62.94(14)
O1 Ag1 N1 C1 . . 165.5(2)
O1 Ag1 N1 C3 . . -11.9(2)
O1 Ag1 N3 C4 . . -85.4(2)
O1 Ag1 N3 C6 . . 89.4(2)
C3 N1 C1 N2 . . 0.1(3)
Ag1 N1 C1 N2 . . -177.57(16)
C2 N2 C1 N1 . . 0.1(3)
C1 N2 C2 C3 . . -0.3(3)
N2 C2 C3 N1 . . 0.4(3)
C1 N1 C3 C2 . . -0.3(3)
Ag1 N1 C3 C2 . . 177.61(18)
C6 N3 C4 N4 . . 0.1(3)
Ag1 N3 C4 N4 . . 175.93(19)
C5 N4 C4 N3 . . -0.2(3)
C4 N4 C5 C6 . . 0.2(3)
N4 C5 C6 N3 . . -0.1(3)
C4 N3 C6 C5 . . 0.0(3)
Ag1 N3 C6 C5 . . -175.65(19)
O1 S1 C7 C8 . . -105.14(19)
O3 S1 C7 C8 . . 133.26(18)
O2 S1 C7 C8 . . 14.6(2)
O1 S1 C7 C11 . 2_666 71.72(19)
O3 S1 C7 C11 . 2_666 -49.88(19)
O2 S1 C7 C11 . 2_666 -168.56(16)
C11 C7 C8 C9 2_666 . 0.9(3)
S1 C7 C8 C9 . . 177.80(18)
C7 C8 C9 C10 . . 0.1(4)
C8 C9 C10 C11 . . -1.0(4)
C9 C10 C11 C7 . 2_666 -179.0(2)
C9 C10 C11 C11 . 2_666 0.9(4)
