#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230462.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_2230462
loop_
_publ_author_name
'Yang, Yan'
'Yuan, Guohui'
_publ_section_title
;
 Bis[μ-1,2-bis(1H-imidazol-1-ylmethyl)benzene-κ²N³:N^3'^]disilver(I)
 bis(4-carboxynaphthalene-1-carboxylate) tetrahydrate
;
_journal_coeditor_code           RZ2589
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m802
_journal_paper_doi               10.1107/S1600536811018691
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Ag2 (C14 H14 N4)2] (C12 H7 O4)2, 4H2 O'
_chemical_formula_moiety         'C28 H28 Ag2 N8 2+, 2(C12 H7 O4 -), 4(H2 O)'
_chemical_formula_sum            'C52 H50 Ag2 N8 O12'
_chemical_formula_weight         1194.74
_chemical_name_systematic
;
Bis[μ-1,2-bis(1H-imidazol-1-ylmethyl)benzene-
κ²N³:N^3'^]disilver(I)
bis(4-carboxynaphthalene-1-carboxylate) tetrahydrate
;
_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                109.376(8)
_cell_angle_beta                 95.783(3)
_cell_angle_gamma                94.442(4)
_cell_formula_units_Z            1
_cell_length_a                   9.6644(5)
_cell_length_b                   11.3769(12)
_cell_length_c                   11.8255(5)
_cell_measurement_reflns_used    4904
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      1.84
_cell_volume                     1211.79(16)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'φ and 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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8572
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  0.59
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4904
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                3384
_reflns_number_total             4904
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2589.cif
_cod_data_source_block           I
_cod_original_cell_volume        1211.79(15)
_cod_database_code               2230462
_cod_database_fobs_code          2230462
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6791(3) -0.0550(2) 0.0091(2) 0.0501(6) Uani d . 1 1 . .
H H1 0.6710 -0.1140 -0.0684 0.060 Uiso calc R 1 1 . .
C C2 0.6045(3) -0.0634(2) 0.0974(2) 0.0458(6) Uani d . 1 1 . .
H H2 0.5361 -0.1279 0.0919 0.055 Uiso calc R 1 1 . .
C C3 0.7469(2) 0.1091(2) 0.1643(2) 0.0424(6) Uani d . 1 1 . .
H H3 0.7937 0.1857 0.2157 0.051 Uiso calc R 1 1 . .
C C4 0.5997(3) 0.0755(2) 0.3151(2) 0.0442(6) Uani d . 1 1 . .
H H4A 0.5347 0.1374 0.3205 0.053 Uiso calc R 1 1 . .
H H4B 0.6790 0.1137 0.3774 0.053 Uiso calc R 1 1 . .
C C5 0.5284(2) -0.0355(2) 0.33815(18) 0.0341(5) Uani d . 1 1 . .
C C6 0.3839(2) -0.0568(2) 0.3188(2) 0.0434(6) Uani d . 1 1 . .
H H6 0.3335 -0.0034 0.2905 0.052 Uiso calc R 1 1 . .
C C7 0.3121(2) -0.1558(3) 0.3405(2) 0.0479(6) Uani d . 1 1 . .
H H7 0.2147 -0.1685 0.3266 0.058 Uiso calc R 1 1 . .
C C8 0.3846(3) -0.2340(2) 0.3823(2) 0.0460(6) Uani d . 1 1 . .
H H8 0.3371 -0.3008 0.3968 0.055 Uiso calc R 1 1 . .
C C9 0.5289(3) -0.2138(2) 0.4032(2) 0.0420(6) Uani d . 1 1 . .
H H9 0.5780 -0.2673 0.4324 0.050 Uiso calc R 1 1 . .
C C10 0.6025(2) -0.1153(2) 0.38161(18) 0.0329(5) Uani d . 1 1 . .
C C11 0.7610(2) -0.0995(2) 0.4061(2) 0.0443(6) Uani d . 1 1 . .
H H11A 0.7950 -0.0110 0.4437 0.053 Uiso calc R 1 1 . .
H H11B 0.7903 -0.1418 0.4618 0.053 Uiso calc R 1 1 . .
C C12 0.9213(2) -0.0917(2) 0.2549(2) 0.0402(6) Uani d . 1 1 . .
H H12 0.9636 -0.0104 0.2967 0.048 Uiso calc R 1 1 . .
C C13 0.7869(2) -0.2677(2) 0.2088(2) 0.0465(6) Uani d . 1 1 . .
H H13 0.7210 -0.3304 0.2117 0.056 Uiso calc R 1 1 . .
C C14 0.8654(3) -0.2743(2) 0.1202(2) 0.0510(7) Uani d . 1 1 . .
H H14 0.8624 -0.3432 0.0500 0.061 Uiso calc R 1 1 . .
C C15 1.0338(2) 0.4758(2) 0.2815(2) 0.0376(5) Uani d . 1 1 . .
C C16 0.87617(19) 0.45208(19) 0.27283(19) 0.0296(5) Uani d . 1 1 . .
C C17 0.8186(2) 0.4650(2) 0.3765(2) 0.0392(6) Uani d . 1 1 . .
H H17 0.8761 0.4916 0.4503 0.047 Uiso calc R 1 1 . .
C C18 0.6738(2) 0.4386(2) 0.3729(2) 0.0385(5) Uani d . 1 1 . .
H H18 0.6374 0.4426 0.4438 0.046 Uiso calc R 1 1 . .
C C19 0.58560(19) 0.40728(19) 0.26764(19) 0.0294(5) Uani d . 1 1 . .
C C20 0.4319(2) 0.3805(2) 0.2734(2) 0.0353(5) Uani d . 1 1 . .
C C21 0.64007(19) 0.39844(18) 0.15716(18) 0.0255(4) Uani d . 1 1 . .
C C22 0.78814(19) 0.41758(18) 0.16013(18) 0.0246(4) Uani d . 1 1 . .
C C23 0.8428(2) 0.40779(19) 0.05138(19) 0.0314(5) Uani d . 1 1 . .
H H23 0.9393 0.4196 0.0527 0.038 Uiso calc R 1 1 . .
C C24 0.7584(2) 0.3816(2) -0.0548(2) 0.0386(5) Uani d . 1 1 . .
H H24 0.7967 0.3765 -0.1251 0.046 Uiso calc R 1 1 . .
C C25 0.6131(2) 0.3624(2) -0.0577(2) 0.0417(6) Uani d . 1 1 . .
H H25 0.5551 0.3439 -0.1306 0.050 Uiso calc R 1 1 . .
C C26 0.5555(2) 0.3705(2) 0.04427(19) 0.0357(5) Uani d . 1 1 . .
H H26 0.4587 0.3575 0.0400 0.043 Uiso calc R 1 1 . .
O O1 0.39354(17) 0.3166(2) 0.3301(2) 0.0755(7) Uani d . 1 1 . .
O O2 0.35024(15) 0.43133(18) 0.21712(17) 0.0592(5) Uani d . 1 1 . .
H H2A 0.2689 0.4124 0.2246 0.089 Uiso calc R 1 1 . .
O O1W 1.0555(2) 0.7995(2) 0.5309(2) 0.0790(6) Uani d D 1 1 . .
H HW11 1.053(4) 0.725(2) 0.477(3) 0.119 Uiso d D 1 1 . .
H HW12 0.991(3) 0.788(3) 0.569(3) 0.119 Uiso d D 1 1 . .
O O3 1.09219(15) 0.38750(17) 0.21193(16) 0.0525(4) Uani d . 1 1 . .
O O2W 0.1287(2) 0.1769(2) 0.2855(3) 0.0908(7) Uani d D 1 1 . .
H HW21 0.204(3) 0.224(3) 0.313(4) 0.136 Uiso d D 1 1 . .
H HW22 0.086(4) 0.210(4) 0.237(3) 0.136 Uiso d D 1 1 . .
O O4 1.09571(17) 0.57350(19) 0.35306(17) 0.0630(5) Uani d . 1 1 . .
Ag Ag1 0.91046(2) 0.11314(2) -0.04497(2) 0.05935(10) Uani d . 1 1 . .
N N1 0.64894(18) 0.04051(16) 0.19530(16) 0.0346(4) Uani d . 1 1 . .
N N2 0.7687(2) 0.05428(19) 0.05184(18) 0.0461(5) Uani d . 1 1 . .
N N3 0.82247(17) -0.15126(17) 0.29391(16) 0.0350(4) Uani d . 1 1 . .
N N4 0.95103(19) -0.16342(18) 0.14922(18) 0.0443(5) Uani d . 1 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'
O O 0.0106 0.0060 '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'
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
C2 C1 N2 . . 109.2(2) ?
C2 C1 H1 . . 125.4 ?
N2 C1 H1 . . 125.4 ?
C1 C2 N1 . . 106.6(2) ?
C1 C2 H2 . . 126.7 ?
N1 C2 H2 . . 126.7 ?
N2 C3 N1 . . 111.2(2) ?
N2 C3 H3 . . 124.4 ?
N1 C3 H3 . . 124.4 ?
N1 C4 C5 . . 112.57(18) ?
N1 C4 H4A . . 109.1 ?
C5 C4 H4A . . 109.1 ?
N1 C4 H4B . . 109.1 ?
C5 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
C6 C5 C10 . . 118.62(19) ?
C6 C5 C4 . . 118.8(2) ?
C10 C5 C4 . . 122.5(2) ?
C5 C6 C7 . . 121.6(2) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 119.7(2) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 119.7(2) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
C8 C9 C10 . . 121.4(2) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C9 C10 C5 . . 119.0(2) ?
C9 C10 C11 . . 118.4(2) ?
C5 C10 C11 . . 122.57(19) ?
N3 C11 C10 . . 111.23(18) ?
N3 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
N3 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
N4 C12 N3 . . 111.1(2) ?
N4 C12 H12 . . 124.5 ?
N3 C12 H12 . . 124.5 ?
C14 C13 N3 . . 106.6(2) ?
C14 C13 H13 . . 126.7 ?
N3 C13 H13 . . 126.7 ?
C13 C14 N4 . . 109.5(2) ?
C13 C14 H14 . . 125.3 ?
N4 C14 H14 . . 125.3 ?
O4 C15 O3 . . 124.9(2) ?
O4 C15 C16 . . 119.4(2) ?
O3 C15 C16 . . 115.7(2) ?
C17 C16 C22 . . 119.93(18) ?
C17 C16 C15 . . 118.49(18) ?
C22 C16 C15 . . 121.58(17) ?
C16 C17 C18 . . 120.8(2) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C19 C18 C17 . . 121.12(19) ?
C19 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C18 C19 C21 . . 120.19(17) ?
C18 C19 C20 . . 117.02(18) ?
C21 C19 C20 . . 122.78(18) ?
O1 C20 O2 . . 124.30(19) ?
O1 C20 C19 . . 120.2(2) ?
O2 C20 C19 . . 115.45(18) ?
C26 C21 C22 . . 117.74(17) ?
C26 C21 C19 . . 123.92(17) ?
C22 C21 C19 . . 118.34(17) ?
C23 C22 C16 . . 121.85(17) ?
C23 C22 C21 . . 118.69(18) ?
C16 C22 C21 . . 119.38(17) ?
C24 C23 C22 . . 121.85(19) ?
C24 C23 H23 . . 119.1 ?
C22 C23 H23 . . 119.1 ?
C23 C24 C25 . . 119.4(2) ?
C23 C24 H24 . . 120.3 ?
C25 C24 H24 . . 120.3 ?
C26 C25 C24 . . 121.0(2) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 C21 . . 121.34(19) ?
C25 C26 H26 . . 119.3 ?
C21 C26 H26 . . 119.3 ?
C20 O2 H2A . . 109.5 ?
HW11 O1W HW12 . . 101(2) ?
HW21 O2W HW22 . . 103(2) ?
N2 Ag1 N4 . 2_755 177.04(8) ?
C3 N1 C2 . . 107.41(18) ?
C3 N1 C4 . . 124.93(19) ?
C2 N1 C4 . . 127.65(18) ?
C3 N2 C1 . . 105.65(18) ?
C3 N2 Ag1 . . 128.88(16) ?
C1 N2 Ag1 . . 125.46(16) ?
C12 N3 C13 . . 107.32(19) ?
C12 N3 C11 . . 126.2(2) ?
C13 N3 C11 . . 126.49(18) ?
C12 N4 C14 . . 105.53(18) ?
C12 N4 Ag1 . 2_755 126.65(15) ?
C14 N4 Ag1 . 2_755 127.71(16) ?
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
C1 C2 . 1.351(3) ?
C1 N2 . 1.371(3) ?
C1 H1 . 0.9300 ?
C2 N1 . 1.355(3) ?
C2 H2 . 0.9300 ?
C3 N2 . 1.315(3) ?
C3 N1 . 1.336(3) ?
C3 H3 . 0.9300 ?
C4 N1 . 1.477(3) ?
C4 C5 . 1.508(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.381(3) ?
C5 C10 . 1.393(3) ?
C6 C7 . 1.387(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.359(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.379(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.515(3) ?
C11 N3 . 1.468(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 N4 . 1.320(3) ?
C12 N3 . 1.334(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.340(3) ?
C13 N3 . 1.364(3) ?
C13 H13 . 0.9300 ?
C14 N4 . 1.373(3) ?
C14 H14 . 0.9300 ?
C15 O4 . 1.217(3) ?
C15 O3 . 1.279(3) ?
C15 C16 . 1.513(3) ?
C16 C17 . 1.365(3) ?
C16 C22 . 1.424(3) ?
C17 C18 . 1.402(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.360(3) ?
C18 H18 . 0.9300 ?
C19 C21 . 1.433(3) ?
C19 C20 . 1.506(3) ?
C20 O1 . 1.203(3) ?
C20 O2 . 1.273(3) ?
C21 C26 . 1.417(3) ?
C21 C22 . 1.426(3) ?
C22 C23 . 1.413(3) ?
C23 C24 . 1.356(3) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.400(3) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.357(3) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O2 H2A . 0.8200 ?
O1W HW11 . 0.874(17) ?
O1W HW12 . 0.833(17) ?
O2W HW21 . 0.838(18) ?
O2W HW22 . 0.882(18) ?
Ag1 N2 . 2.0783(17) ?
Ag1 N4 2_755 2.0787(17) ?
N4 Ag1 2_755 2.0787(17) ?
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
O2 H2A O3 1_455 0.82 1.69 2.496(2) 166
O1W HW11 O4 . 0.874(17) 1.959(18) 2.814(3) 166(3)
O1W HW12 O2W 2_666 0.833(17) 2.115(19) 2.902(3) 158(3)
O2W HW21 O1 . 0.838(18) 1.99(2) 2.810(3) 164(4)
O2W HW22 O3 1_455 0.882(18) 2.13(3) 2.841(3) 138(3)
