#------------------------------------------------------------------------------
#$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $
#$Revision: 120112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/90/7019059.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_7019059
loop_
_publ_author_name
'Wright, Brian D.'
'Shah, Parth N.'
'McDonald, Lucas J.'
'Shaeffer, Michael L.'
'Wagers, Patrick O.'
'Panzner, Matthew J.'
'Smolen, Justin'
'Tagaev, Jasur'
'Tessier, Claire A.'
'Cannon, Carolyn L.'
'Youngs, Wiley J.'
_publ_section_title
;
 Synthesis, characterization, and antimicrobial activity of silver carbene
 complexes derived from 4,5,6,7-tetrachlorobenzimidazole against
 antibiotic resistant bacteria.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6500
_journal_page_last               6506
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C12 H11 Ag Cl4 N2 O3, C1 H2 Cl2'
_chemical_formula_sum            'C13 H13 Ag Cl6 N2 O3'
_chemical_formula_weight         565.82
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.684(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.616(3)
_cell_length_b                   13.028(5)
_cell_length_c                   17.176(6)
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.37
_cell_volume                     1925.9(12)
_computing_cell_refinement       'Bruker SAINT'
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(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  0.0908
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14692
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.895
_exptl_absorpt_correction_T_max  0.9213
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.593
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                3167
_reflns_number_total             3909
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    c2dt00055e.txt
_[local]_cod_data_source_block   bw6
_[local]_cod_cif_authors_sg_H-M  'P2(1)/c '
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_refine_ls_hydrogen_treatment' value 'Constr' changed
to 'constr' 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               7019059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.32137(4) 0.45975(2) 0.99421(2) 0.02786(16) Uani 1 1 d . . .
Cl1 Cl 0.77846(13) 0.14570(9) 1.16302(6) 0.0272(3) Uani 1 1 d . . .
Cl2 Cl 0.74548(13) -0.09320(8) 0.90702(6) 0.0243(3) Uani 1 1 d . . .
Cl3 Cl 0.52032(13) 0.05890(8) 0.82092(6) 0.0235(3) Uani 1 1 d . . .
Cl4 Cl 0.86682(14) -0.05186(8) 1.07664(7) 0.0259(3) Uani 1 1 d . . .
Cl6 Cl -0.0996(3) 0.0227(3) 0.73165(18) 0.0777(14) Uani 0.600(5) 1 d P A 1
Cl7 Cl 0.1256(6) 0.1839(4) 0.6990(3) 0.0696(14) Uani 0.600(5) 1 d P A 1
Cl8 Cl 0.1867(7) 0.1617(5) 0.6827(4) 0.0467(13) Uani 0.400(5) 1 d P A 2
Cl9 Cl -0.0828(4) 0.1538(4) 0.7766(2) 0.0686(19) Uani 0.400(5) 1 d P A 2
O1 O 0.5317(4) 0.4291(2) 0.83167(18) 0.0282(8) Uani 1 1 d . . .
H1 H 0.4832 0.4454 0.8697 0.042 Uiso 1 1 calc R . .
O2 O 0.1669(4) 0.5838(3) 0.9776(3) 0.0483(11) Uani 1 1 d . . .
O3 O 0.1975(6) 0.6198(4) 1.1015(4) 0.0854(19) Uani 1 1 d . . .
N1 N 0.4495(4) 0.2575(3) 0.9351(2) 0.0186(8) Uani 1 1 d . . .
N2 N 0.5377(4) 0.2850(3) 1.0541(2) 0.0185(8) Uani 1 1 d . . .
C1 C 0.4468(5) 0.3240(3) 0.9958(2) 0.0190(9) Uani 1 1 d . . .
C2 C 0.3718(5) 0.2801(3) 0.8594(2) 0.0237(10) Uani 1 1 d . . .
H2A H 0.2834 0.3245 0.8671 0.028 Uiso 1 1 calc R . .
H2B H 0.3332 0.2167 0.8361 0.028 Uiso 1 1 calc R . .
C3 C 0.4798(6) 0.3318(3) 0.8041(2) 0.0252(10) Uani 1 1 d . . .
H3A H 0.5692 0.2879 0.7973 0.030 Uiso 1 1 calc R . .
H3B H 0.4260 0.3402 0.7537 0.030 Uiso 1 1 calc R . .
C4 C 0.5467(5) 0.1748(3) 0.9549(2) 0.0168(8) Uani 1 1 d . . .
C5 C 0.6033(5) 0.1922(3) 1.0309(2) 0.0180(9) Uani 1 1 d . . .
C6 C 0.7030(5) 0.1238(3) 1.0700(2) 0.0194(9) Uani 1 1 d . . .
C7 C 0.7458(5) 0.0363(3) 1.0301(3) 0.0172(9) Uani 1 1 d . . .
C8 C 0.6893(5) 0.0176(3) 0.9529(2) 0.0171(9) Uani 1 1 d . . .
C9 C 0.5896(5) 0.0864(3) 0.9143(2) 0.0175(9) Uani 1 1 d . . .
C10 C 0.5626(6) 0.3360(3) 1.1293(3) 0.0274(10) Uani 1 1 d . . .
H10A H 0.5051 0.3992 1.1292 0.041 Uiso 1 1 calc R . .
H10B H 0.6713 0.3503 1.1384 0.041 Uiso 1 1 calc R . .
H10C H 0.5278 0.2921 1.1699 0.041 Uiso 1 1 calc R . .
C11 C 0.1369(6) 0.6335(4) 1.0371(5) 0.0507(17) Uani 1 1 d . . .
C12 C 0.0189(7) 0.7191(4) 1.0281(5) 0.068(2) Uani 1 1 d . . .
H12A H 0.0103 0.7535 1.0771 0.102 Uiso 1 1 calc R . .
H12B H -0.0802 0.6910 1.0116 0.102 Uiso 1 1 calc R . .
H12C H 0.0517 0.7672 0.9898 0.102 Uiso 1 1 calc R . .
C13 C 0.0520(17) 0.0577(10) 0.6749(9) 0.051(3) Uani 0.600(5) 1 d P A 1
H13A H 0.0167 0.0565 0.6204 0.061 Uiso 0.600(5) 1 calc PR A 1
H13B H 0.1354 0.0081 0.6820 0.061 Uiso 0.600(5) 1 calc PR A 1
C14 C 0.027(2) 0.0922(14) 0.7065(12) 0.049(5) Uani 0.400(5) 1 d P A 2
H14A H 0.0608 0.0257 0.7265 0.059 Uiso 0.400(5) 1 calc PR A 2
H14B H -0.0383 0.0806 0.6598 0.059 Uiso 0.400(5) 1 calc PR A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ag1 0.0299(3) 0.0156(2) 0.0385(3) 0.00372(14) 0.00636(17) 0.00628(13)
Cl1 0.0337(6) 0.0254(6) 0.0217(6) -0.0037(4) -0.0075(5) 0.0022(5)
Cl2 0.0288(6) 0.0156(5) 0.0288(6) -0.0053(4) 0.0039(5) 0.0033(4)
Cl3 0.0318(6) 0.0203(5) 0.0181(5) -0.0029(4) -0.0011(4) -0.0010(4)
Cl4 0.0265(6) 0.0212(6) 0.0296(6) 0.0028(4) -0.0017(5) 0.0071(4)
Cl6 0.0346(15) 0.141(4) 0.0571(19) 0.048(2) -0.0031(13) -0.0052(17)
Cl7 0.077(3) 0.048(2) 0.080(3) 0.004(2) -0.041(3) -0.003(2)
Cl8 0.038(3) 0.053(3) 0.049(2) -0.001(2) 0.002(2) -0.004(2)
Cl9 0.040(2) 0.120(4) 0.047(2) 0.049(3) 0.0115(17) 0.035(2)
O1 0.050(2) 0.0118(15) 0.0230(18) -0.0002(13) 0.0078(15) 0.0004(14)
O2 0.039(2) 0.024(2) 0.083(3) 0.012(2) 0.018(2) 0.0152(16)
O3 0.056(3) 0.082(4) 0.114(4) -0.063(3) -0.036(3) 0.029(3)
N1 0.0196(19) 0.0153(18) 0.0212(18) 0.0026(14) 0.0029(14) 0.0024(14)
N2 0.027(2) 0.0099(16) 0.0192(18) 0.0023(14) 0.0043(15) 0.0024(14)
C1 0.024(2) 0.015(2) 0.018(2) 0.0030(17) 0.0042(17) -0.0003(17)
C2 0.027(2) 0.024(2) 0.019(2) -0.0002(19) -0.0079(18) 0.0020(19)
C3 0.045(3) 0.015(2) 0.015(2) 0.0003(17) -0.0017(19) 0.0006(19)
C4 0.017(2) 0.013(2) 0.021(2) 0.0024(17) 0.0024(16) -0.0016(16)
C5 0.022(2) 0.0105(19) 0.022(2) -0.0002(16) 0.0052(17) -0.0006(16)
C6 0.019(2) 0.020(2) 0.019(2) -0.0011(17) 0.0019(17) -0.0033(17)
C7 0.018(2) 0.014(2) 0.019(2) 0.0048(16) -0.0005(17) 0.0007(15)
C8 0.015(2) 0.0129(19) 0.024(2) -0.0013(17) 0.0076(17) 0.0004(16)
C9 0.022(2) 0.018(2) 0.012(2) -0.0003(16) 0.0002(16) -0.0010(17)
C10 0.045(3) 0.020(2) 0.018(2) 0.0019(18) 0.003(2) 0.002(2)
C11 0.024(3) 0.021(3) 0.107(6) -0.012(3) -0.003(3) -0.004(2)
C12 0.030(3) 0.025(3) 0.150(7) -0.003(4) 0.012(4) 0.008(2)
C13 0.048(7) 0.044(8) 0.062(9) -0.009(6) 0.005(7) -0.011(6)
C14 0.054(12) 0.035(11) 0.058(13) 0.005(9) -0.009(10) -0.008(8)
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_3
C1 Ag1 O2 169.53(17) .
C1 Ag1 Ag1 77.45(12) 3_667
O2 Ag1 Ag1 110.59(11) 3_667
C3 O1 H1 109.5 .
C11 O2 Ag1 116.2(4) .
C1 N1 C4 109.7(3) .
C1 N1 C2 122.0(4) .
C4 N1 C2 128.0(4) .
C1 N2 C5 110.1(3) .
C1 N2 C10 123.0(4) .
C5 N2 C10 126.9(4) .
N2 C1 N1 107.5(4) .
N2 C1 Ag1 128.2(3) .
N1 C1 Ag1 124.2(3) .
N1 C2 C3 112.1(4) .
N1 C2 H2A 109.2 .
C3 C2 H2A 109.2 .
N1 C2 H2B 109.2 .
C3 C2 H2B 109.2 .
H2A C2 H2B 107.9 .
O1 C3 C2 112.4(4) .
O1 C3 H3A 109.1 .
C2 C3 H3A 109.1 .
O1 C3 H3B 109.1 .
C2 C3 H3B 109.1 .
H3A C3 H3B 107.9 .
C5 C4 N1 106.4(3) .
C5 C4 C9 120.7(4) .
N1 C4 C9 132.9(4) .
C6 C5 C4 122.1(4) .
C6 C5 N2 131.6(4) .
C4 C5 N2 106.3(4) .
C7 C6 C5 117.4(4) .
C7 C6 Cl1 119.8(3) .
C5 C6 Cl1 122.8(3) .
C6 C7 C8 121.2(4) .
C6 C7 Cl4 119.1(3) .
C8 C7 Cl4 119.7(3) .
C9 C8 C7 121.0(4) .
C9 C8 Cl2 120.2(3) .
C7 C8 Cl2 118.8(3) .
C8 C9 C4 117.7(4) .
C8 C9 Cl3 119.3(3) .
C4 C9 Cl3 123.0(3) .
N2 C10 H10A 109.5 .
N2 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
N2 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
O3 C11 O2 125.0(5) .
O3 C11 C12 117.4(7) .
O2 C11 C12 117.6(7) .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
Cl6 C13 Cl7 112.2(8) .
Cl6 C13 H13A 109.2 .
Cl7 C13 H13A 109.2 .
Cl6 C13 H13B 109.2 .
Cl7 C13 H13B 109.2 .
H13A C13 H13B 107.9 .
Cl8 C14 Cl9 112.7(11) .
Cl8 C14 H14A 109.1 .
Cl9 C14 H14A 109.1 .
Cl8 C14 H14B 109.1 .
Cl9 C14 H14B 109.1 .
H14A C14 H14B 107.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C1 2.072(4) .
Ag1 O2 2.104(4) .
Ag1 Ag1 3.2494(13) 3_667
Cl1 C6 1.720(4) .
Cl2 C8 1.725(4) .
Cl3 C9 1.723(4) .
Cl4 C7 1.723(4) .
Cl6 C13 1.728(15) .
Cl7 C13 1.803(14) .
Cl8 C14 1.71(2) .
Cl9 C14 1.76(2) .
O1 C3 1.418(5) .
O1 H1 0.8200 .
O2 C11 1.248(8) .
O3 C11 1.214(8) .
N1 C1 1.357(5) .
N1 C4 1.397(5) .
N1 C2 1.464(5) .
N2 C1 1.342(5) .
N2 C5 1.401(5) .
N2 C10 1.460(5) .
C2 C3 1.518(6) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.390(6) .
C4 C9 1.404(6) .
C5 C6 1.389(6) .
C6 C7 1.389(6) .
C7 C8 1.412(6) .
C8 C9 1.388(6) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.512(7) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
_journal_paper_doi 10.1039/c2dt00055e