#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009076.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_2009076
loop_
_publ_author_name
'Shanmuga Sundara Raj, S.'
'Fun, H.-K.'
'Chen, X.-F.'
'Zhu, X.-H.'
'You, X.-Z.'
_publ_section_title
;
 Bis[2-(phenylazo)imidazole-<i>N</i>]silver(I) nitrate methanol solvate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1644
_journal_page_last               1646
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          '[Ag (C9 H8 N4)2] N O3 , C H4 O'
_chemical_formula_sum            'C19 H20 Ag N9 O4'
_chemical_formula_weight         546.31
_chemical_name_systematic
;
bis(2-phenyldiazenyl-1H-imidazole-N)silver(I) nitrate methanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.0770(10)
_cell_angle_beta                 75.3590(10)
_cell_angle_gamma                72.4620(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5447(5)
_cell_length_b                   12.0046(7)
_cell_length_c                   13.7852(8)
_cell_measurement_reflns_used    4099
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      1.56
_cell_volume                     1124.96(12)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Siemens SMART CCD area detector'
_diffrn_measurement_method       '\w 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  0.029
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7937
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.477
_refine_diff_density_min         -0.561
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.094
_refine_ls_R_factor_gt           0.057
_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/[\s^2^(Fo^2^)+(0.0798P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.160
_reflns_number_gt                3463
_reflns_number_total             5431
_reflns_threshold_expression     'I > 2\s(I)'
_[local]_cod_data_source_file    sk1302.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Ag1 -0.23310(6) 0.02537(3) 0.24568(3) 0.07257(19) Uani d . 1 Ag
O1 -0.3683(6) 0.4256(4) -0.1924(3) 0.0827(11) Uani d . 1 O
O2 -0.6569(6) 0.4245(4) -0.1713(3) 0.0861(12) Uani d . 1 O
O3 -0.5311(5) 0.5308(3) -0.3085(2) 0.0733(9) Uani d . 1 O
O4 -0.8951(6) 0.6247(4) -0.3478(3) 0.0865(12) Uani d . 1 O
N1 -0.4044(5) 0.1714(3) 0.1532(2) 0.0489(8) Uani d . 1 N
N2 -0.5027(5) 0.2820(3) 0.0129(2) 0.0564(9) Uani d . 1 N
H2A -0.5229 0.3030 -0.0490 0.068 Uiso calc R 1 H
N3 -0.3295(5) 0.0854(3) -0.0014(2) 0.0524(8) Uani d . 1 N
N4 -0.2510(5) -0.0100(3) 0.0493(3) 0.0544(8) Uani d . 1 N
N5 -0.0434(5) -0.1206(3) 0.3260(3) 0.0511(8) Uani d . 1 N
N6 0.0579(5) -0.2482(3) 0.4616(3) 0.0536(9) Uani d . 1 N
H6A 0.0724 -0.2786 0.5241 0.064 Uiso calc R 1 H
N7 -0.1635(5) -0.0708(3) 0.4965(3) 0.0498(8) Uani d . 1 N
N8 -0.2634(5) 0.0257(3) 0.4553(3) 0.0506(8) Uani d . 1 N
N9 -0.5193(6) 0.4602(3) -0.2240(3) 0.0549(9) Uani d . 1 N
C1 -0.5611(6) 0.3517(4) 0.0817(3) 0.0575(11) Uani d . 1 C
H1A -0.6297 0.4312 0.0718 0.069 Uiso calc R 1 H
C2 -0.4999(7) 0.2829(4) 0.1688(3) 0.0569(10) Uani d . 1 C
H2B -0.5200 0.3079 0.2297 0.068 Uiso calc R 1 H
C3 -0.4079(6) 0.1742(3) 0.0569(3) 0.0455(9) Uani d . 1 C
C4 -0.1646(6) -0.1039(4) -0.0088(3) 0.0513(10) Uani d . 1 C
C5 -0.0842(7) -0.2118(4) 0.0479(4) 0.0610(11) Uani d . 1 C
H5A -0.0902 -0.2202 0.1177 0.073 Uiso calc R 1 H
C6 0.0059(8) -0.3084(5) 0.0026(4) 0.0726(13) Uani d . 1 C
H6B 0.0615 -0.3815 0.0413 0.087 Uiso calc R 1 H
C7 0.0124(7) -0.2951(5) -0.1001(4) 0.0685(13) Uani d . 1 C
H7B 0.0737 -0.3597 -0.1312 0.082 Uiso calc R 1 H
C8 -0.0697(7) -0.1886(5) -0.1572(4) 0.0685(13) Uani d . 1 C
H8B -0.0652 -0.1818 -0.2266 0.082 Uiso calc R 1 H
C9 -0.1607(7) -0.0894(4) -0.1130(3) 0.0593(11) Uani d . 1 C
H9A -0.2166 -0.0164 -0.1517 0.071 Uiso calc R 1 H
C10 0.1449(6) -0.2986(4) 0.3806(3) 0.0580(11) Uani d . 1 C
H10A 0.2310 -0.3728 0.3814 0.070 Uiso calc R 1 H
C11 0.0818(6) -0.2192(4) 0.2971(3) 0.0568(10) Uani d . 1 C
H11A 0.1190 -0.2309 0.2303 0.068 Uiso calc R 1 H
C12 -0.0554(6) -0.1419(4) 0.4274(3) 0.0463(9) Uani d . 1 C
C13 -0.3756(6) 0.1007(4) 0.5254(3) 0.0490(9) Uani d . 1 C
C14 -0.4743(7) 0.2121(4) 0.4814(3) 0.0605(11) Uani d . 1 C
H14A -0.4662 0.2339 0.4105 0.073 Uiso calc R 1 H
C15 -0.5855(7) 0.2918(4) 0.5418(4) 0.0679(13) Uani d . 1 C
H15A -0.6525 0.3670 0.5119 0.082 Uiso calc R 1 H
C16 -0.5961(7) 0.2591(5) 0.6461(4) 0.0669(12) Uani d . 1 C
H16A -0.6691 0.3128 0.6870 0.080 Uiso calc R 1 H
C17 -0.4995(7) 0.1475(5) 0.6907(4) 0.0656(12) Uani d . 1 C
H17A -0.5101 0.1259 0.7617 0.079 Uiso calc R 1 H
C18 -0.3876(6) 0.0675(4) 0.6318(3) 0.0557(11) Uani d . 1 C
H18A -0.3211 -0.0074 0.6622 0.067 Uiso calc R 1 H
C19 -1.0173(11) 0.5506(8) -0.3092(6) 0.093(2) Uani d . 1 C
H1O4 -0.774(10) 0.586(6) -0.332(5) 0.11(2) Uiso d . 1 H
H19C -0.987(16) 0.521(10) -0.375(8) 0.22(5) Uiso d . 1 H
H19B -1.137(14) 0.595(8) -0.329(7) 0.16(3) Uiso d . 1 H
H19A -1.011(12) 0.497(8) -0.244(6) 0.15(3) Uiso d . 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ag1 0.0733(3) 0.0593(3) 0.0757(3) -0.00068(18) -0.0419(2) 0.00859(17)
O1 0.073(2) 0.090(3) 0.063(2) 0.008(2) -0.0220(17) -0.0054(18)
O2 0.093(3) 0.107(3) 0.062(2) -0.047(3) -0.016(2) 0.002(2)
O3 0.090(3) 0.066(2) 0.0510(17) -0.0134(19) -0.0232(16) 0.0110(15)
O4 0.077(3) 0.094(3) 0.076(2) -0.020(2) -0.034(2) 0.020(2)
N1 0.054(2) 0.0404(18) 0.0492(18) -0.0019(15) -0.0213(15) -0.0047(14)
N2 0.069(2) 0.051(2) 0.0412(18) -0.0043(18) -0.0194(16) -0.0003(15)
N3 0.058(2) 0.047(2) 0.0482(18) -0.0105(16) -0.0163(16) 0.0003(15)
N4 0.058(2) 0.053(2) 0.0484(19) -0.0117(17) -0.0148(16) -0.0031(16)
N5 0.0502(19) 0.0461(19) 0.0548(19) -0.0048(16) -0.0222(15) -0.0040(15)
N6 0.055(2) 0.048(2) 0.055(2) -0.0087(16) -0.0247(17) 0.0018(16)
N7 0.0506(19) 0.0447(19) 0.056(2) -0.0125(16) -0.0211(16) -0.0029(15)
N8 0.053(2) 0.0473(19) 0.0542(19) -0.0153(16) -0.0225(16) 0.0002(15)
N9 0.071(3) 0.0442(19) 0.0453(19) -0.0050(18) -0.0143(18) -0.0106(15)
C1 0.061(3) 0.043(2) 0.059(2) 0.001(2) -0.018(2) -0.0051(19)
C2 0.066(3) 0.052(3) 0.050(2) 0.001(2) -0.019(2) -0.0157(19)
C3 0.046(2) 0.041(2) 0.045(2) -0.0050(17) -0.0104(17) -0.0077(16)
C4 0.047(2) 0.050(2) 0.058(2) -0.0118(19) -0.0071(19) -0.0158(19)
C5 0.067(3) 0.056(3) 0.058(3) -0.009(2) -0.019(2) -0.009(2)
C6 0.070(3) 0.054(3) 0.085(4) 0.001(2) -0.019(3) -0.014(2)
C7 0.062(3) 0.062(3) 0.085(4) -0.009(2) -0.007(3) -0.034(3)
C8 0.068(3) 0.084(4) 0.056(3) -0.019(3) -0.001(2) -0.028(3)
C9 0.056(3) 0.054(3) 0.063(3) -0.009(2) -0.016(2) -0.007(2)
C10 0.055(2) 0.043(2) 0.072(3) -0.0043(19) -0.025(2) -0.002(2)
C11 0.055(2) 0.058(3) 0.056(2) -0.004(2) -0.020(2) -0.013(2)
C12 0.045(2) 0.043(2) 0.050(2) -0.0094(17) -0.0201(17) -0.0010(17)
C13 0.047(2) 0.045(2) 0.058(2) -0.0158(18) -0.0186(18) -0.0052(18)
C14 0.071(3) 0.052(3) 0.058(3) -0.011(2) -0.026(2) -0.001(2)
C15 0.068(3) 0.049(3) 0.082(3) -0.006(2) -0.024(3) -0.007(2)
C16 0.061(3) 0.061(3) 0.082(3) -0.011(2) -0.013(2) -0.026(3)
C17 0.064(3) 0.083(4) 0.055(3) -0.024(3) -0.011(2) -0.016(2)
C18 0.056(3) 0.051(2) 0.058(2) -0.015(2) -0.018(2) 0.001(2)
C19 0.080(4) 0.105(5) 0.091(5) -0.033(4) -0.022(4) 0.003(4)
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'
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
_geom_angle_publ_flag
N5 Ag1 N1 174.90(10) y
C3 N1 C2 105.6(3) ?
C3 N1 Ag1 123.0(3) ?
C2 N1 Ag1 130.4(3) ?
C3 N2 C1 108.3(3) ?
N4 N3 C3 111.9(3) y
N3 N4 C4 113.7(3) y
C12 N5 C11 104.8(3) ?
C12 N5 Ag1 122.5(3) ?
C11 N5 Ag1 131.6(3) ?
C12 N6 C10 107.8(3) ?
N8 N7 C12 113.3(3) y
N7 N8 C13 114.2(3) y
O2 N9 O1 119.4(4) y
O2 N9 O3 120.5(4) y
O1 N9 O3 120.1(4) y
N2 C1 C2 106.2(4) ?
C1 C2 N1 109.4(4) ?
N1 C3 N2 110.4(3) ?
N1 C3 N3 130.7(3) ?
N2 C3 N3 118.9(3) ?
C5 C4 C9 120.9(4) ?
C5 C4 N4 114.2(4) ?
C9 C4 N4 124.9(4) ?
C4 C5 C6 120.6(4) ?
C7 C6 C5 119.1(5) ?
C8 C7 C6 120.9(4) ?
C7 C8 C9 120.9(5) ?
C4 C9 C8 117.6(4) ?
N6 C10 C11 106.3(4) ?
N5 C11 C10 110.1(4) ?
N5 C12 N6 111.1(4) ?
N5 C12 N7 129.4(4) ?
N6 C12 N7 119.5(3) ?
C14 C13 C18 120.0(4) ?
C14 C13 N8 115.7(4) ?
C18 C13 N8 124.3(4) ?
C13 C14 C15 120.4(4) ?
C16 C15 C14 119.4(5) ?
C15 C16 C17 120.4(5) ?
C18 C17 C16 120.9(4) ?
C17 C18 C13 118.8(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ag1 N5 2.138(3) y
Ag1 N1 2.147(3) y
O1 N9 1.236(5) y
O2 N9 1.226(5) y
O3 N9 1.245(4) y
O4 C19 1.382(8) y
N1 C3 1.325(5) ?
N1 C2 1.362(5) ?
N2 C3 1.336(5) ?
N2 C1 1.341(6) ?
N3 N4 1.229(5) y
N3 C3 1.408(5) ?
N4 C4 1.458(6) ?
N5 C12 1.335(5) ?
N5 C11 1.359(6) ?
N6 C12 1.341(5) ?
N6 C10 1.343(6) ?
N7 N8 1.250(5) y
N7 C12 1.390(5) y
N8 C13 1.438(6) y
C1 C2 1.357(6) ?
C4 C5 1.367(6) ?
C4 C9 1.392(6) ?
C5 C6 1.379(7) ?
C6 C7 1.371(7) ?
C7 C8 1.363(7) ?
C8 C9 1.399(7) ?
C10 C11 1.365(6) ?
C13 C14 1.376(6) ?
C13 C18 1.396(6) ?
C14 C15 1.384(7) ?
C15 C16 1.371(7) ?
C16 C17 1.374(7) ?
C17 C18 1.374(7) ?
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 H2A O2 1_555 0.86 2.148 2.939(5) 153 yes
O4 H1O4 O3 1_555 0.94(8) 1.83(8) 2.767(6) 172(7) yes
N6 H6A O4 1_646 0.86 1.857 2.702(6) 167 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
_geom_torsion_publ_flag
N5 Ag1 N1 C3 39.3(16) ?
N5 Ag1 N1 C2 -127.9(14) ?
C3 N3 N4 C4 -178.9(3) y
N1 Ag1 N5 C12 155.3(13) ?
N1 Ag1 N5 C11 -38.5(16) ?
C12 N7 N8 C13 -179.7(3) y
C3 N2 C1 C2 -0.4(5) ?
N2 C1 C2 N1 0.0(5) ?
C3 N1 C2 C1 0.4(5) ?
Ag1 N1 C2 C1 169.3(3) ?
C2 N1 C3 N2 -0.6(5) ?
Ag1 N1 C3 N2 -170.5(3) ?
C2 N1 C3 N3 179.0(4) ?
Ag1 N1 C3 N3 9.0(6) ?
C1 N2 C3 N1 0.6(5) ?
C1 N2 C3 N3 -179.0(4) ?
N4 N3 C3 N1 2.3(6) ?
N4 N3 C3 N2 -178.1(4) ?
N3 N4 C4 C5 -177.2(4) ?
N3 N4 C4 C9 2.8(6) ?
C9 C4 C5 C6 1.2(7) ?
N4 C4 C5 C6 -178.8(4) ?
C4 C5 C6 C7 -0.6(8) ?
C5 C6 C7 C8 -0.5(8) ?
C6 C7 C8 C9 0.9(8) ?
C5 C4 C9 C8 -0.8(7) ?
N4 C4 C9 C8 179.2(4) ?
C7 C8 C9 C4 -0.3(7) ?
C12 N6 C10 C11 0.5(5) ?
C12 N5 C11 C10 -0.3(5) ?
Ag1 N5 C11 C10 -168.3(3) ?
N6 C10 C11 N5 -0.1(5) ?
C11 N5 C12 N6 0.6(5) ?
Ag1 N5 C12 N6 170.0(3) ?
C11 N5 C12 N7 -179.9(4) ?
Ag1 N5 C12 N7 -10.5(6) ?
C10 N6 C12 N5 -0.7(5) ?
C10 N6 C12 N7 179.7(4) ?
N8 N7 C12 N5 0.7(6) ?
N8 N7 C12 N6 -179.8(3) ?
N7 N8 C13 C14 174.4(4) ?
N7 N8 C13 C18 -5.2(5) ?
C18 C13 C14 C15 0.2(7) ?
N8 C13 C14 C15 -179.5(4) ?
C13 C14 C15 C16 0.2(7) ?
C14 C15 C16 C17 -1.0(7) ?
C15 C16 C17 C18 1.4(7) ?
C16 C17 C18 C13 -1.0(7) ?
C14 C13 C18 C17 0.2(6) ?
N8 C13 C18 C17 179.8(4) ?