#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:18:00 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179446 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/43/4334377.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_4334377
loop_
_publ_author_name
'Alshima'a A. Massoud'
'Vratislav Langer'
'Yousry M. Gohar'
'Morsy A. M. Abu-Youssef'
'Janne Jänis'
'Gabriella Lindberg'
'Karl Hansson'
'Lars Öhrström'
_publ_section_title
;
 Effects of Different Substituents on the Crystal Structures and
 Antimicrobial Activities of Six Ag(I) Quinoline Compounds
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4046
_journal_page_last               4060
_journal_paper_doi               10.1021/ic400081v
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C10 H6 Ag N3 O3'
_chemical_formula_sum            'C10 H6 Ag N3 O3'
_chemical_formula_weight         324.05
_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                 98.177(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.140(4)
_cell_length_b                   9.621(3)
_cell_length_c                   7.429(2)
_cell_measurement_reflns_used    3273
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.57
_cell_volume                     1000.4(5)
_computing_cell_refinement       'Bruker SMART'
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean '120 \mm'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens CCD area detector'
_diffrn_measurement_method       '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  0.0828
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10537
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.013
_exptl_absorpt_correction_T_max  0.8887
_exptl_absorpt_correction_T_min  0.3590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.152
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.795
_refine_diff_density_min         -1.694
_refine_diff_density_rms         0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0540
_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)+(0.1147P)²+0.1432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                1438
_reflns_number_total             1771
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400081v_si_002_4.cif
_cod_data_source_block           4
_cod_original_cell_volume        1000.3(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4334377
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
Ag Ag -0.08056(3) 0.55231(5) 0.34953(7) 0.0313(3) Uani 1 1 d .
O1 O 0.0597(3) 0.6115(4) 0.2574(6) 0.0289(10) Uani 1 1 d .
O2 O 0.1511(3) 0.7744(4) 0.1850(6) 0.0361(11) Uani 1 1 d .
O3 O 0.0093(3) 0.8249(5) 0.2396(6) 0.0386(12) Uani 1 1 d .
N1 N -0.2060(3) 0.5914(5) 0.4923(6) 0.0204(10) Uani 1 1 d .
N2 N -0.4304(4) 0.2826(7) 0.6958(8) 0.0359(13) Uani 1 1 d .
N3 N 0.0734(4) 0.7388(5) 0.2274(7) 0.0252(11) Uani 1 1 d .
C2 C -0.2564(4) 0.4853(7) 0.5348(8) 0.0248(13) Uani 1 1 d .
H2 H -0.2328 0.3942 0.5193 0.030 Uiso 1 1 calc R
C3 C -0.3436(4) 0.5001(6) 0.6021(7) 0.0222(12) Uani 1 1 d .
C4 C -0.3800(4) 0.6318(6) 0.6237(7) 0.0239(13) Uani 1 1 d .
H4 H -0.4395 0.6437 0.6670 0.029 Uiso 1 1 calc R
C5 C -0.3578(4) 0.8868(6) 0.6016(7) 0.0263(13) Uani 1 1 d .
H5 H -0.4177 0.9046 0.6407 0.032 Uiso 1 1 calc R
C6 C -0.3008(5) 0.9937(6) 0.5658(7) 0.0268(13) Uani 1 1 d .
H6 H -0.3215 1.0863 0.5812 0.032 Uiso 1 1 calc R
C7 C -0.2127(5) 0.9717(6) 0.5070(8) 0.0252(13) Uani 1 1 d .
H7 H -0.1742 1.0488 0.4842 0.030 Uiso 1 1 calc R
C8 C -0.1809(4) 0.8372(6) 0.4815(7) 0.0238(12) Uani 1 1 d .
H8 H -0.1214 0.8222 0.4392 0.029 Uiso 1 1 calc R
C9 C -0.2378(4) 0.7237(6) 0.5190(7) 0.0196(12) Uani 1 1 d .
C10 C -0.3270(4) 0.7473(6) 0.5803(7) 0.0213(12) Uani 1 1 d .
C11 C -0.3939(5) 0.3778(7) 0.6544(8) 0.0273(14) Uani 1 1 d .
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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Ag O1 153.51(18) . .
N1 Ag O3 130.08(16) . 2_545
O1 Ag O3 74.93(15) . 2_545
N1 Ag Ag 105.26(13) . 3_566
O1 Ag Ag 73.49(11) . 3_566
O3 Ag Ag 68.42(11) 2_545 3_566
N3 O1 Ag 117.4(3) . .
N3 O3 Ag 103.6(4) . 2
C2 N1 C9 119.2(5) . .
C2 N1 Ag 118.8(4) . .
C9 N1 Ag 121.7(4) . .
O2 N3 O3 121.3(5) . .
O2 N3 O1 118.6(5) . .
O3 N3 O1 120.1(5) . .
N1 C2 C3 122.9(6) . .
N1 C2 H2 118.6 . .
C3 C2 H2 118.6 . .
C4 C3 C2 119.6(6) . .
C4 C3 C11 120.4(5) . .
C2 C3 C11 120.0(6) . .
C3 C4 C10 118.6(6) . .
C3 C4 H4 120.7 . .
C10 C4 H4 120.7 . .
C6 C5 C10 119.5(6) . .
C6 C5 H5 120.3 . .
C10 C5 H5 120.3 . .
C5 C6 C7 121.9(6) . .
C5 C6 H6 119.0 . .
C7 C6 H6 119.0 . .
C6 C7 C8 120.3(6) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C7 C8 C9 119.3(6) . .
C7 C8 H8 120.3 . .
C9 C8 H8 120.3 . .
N1 C9 C8 118.8(5) . .
N1 C9 C10 121.2(5) . .
C8 C9 C10 119.9(5) . .
C4 C10 C9 118.4(5) . .
C4 C10 C5 122.5(5) . .
C9 C10 C5 119.0(5) . .
N2 C11 C3 178.4(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag N1 2.224(5) .
Ag O1 2.261(4) .
Ag O3 2.536(5) 2_545
Ag Ag 3.1230(12) 3_566
O1 N3 1.264(6) .
O2 N3 1.234(6) .
O3 N3 1.241(6) .
O3 Ag 2.536(5) 2
N1 C2 1.309(8) .
N1 C9 1.374(7) .
N2 C11 1.116(9) .
C2 C3 1.403(8) .
C2 H2 0.9500 .
C3 C4 1.385(9) .
C3 C11 1.456(9) .
C4 C10 1.403(8) .
C4 H4 0.9500 .
C5 C6 1.357(9) .
C5 C10 1.427(8) .
C5 H5 0.9500 .
C6 C7 1.393(9) .
C6 H6 0.9500 .
C7 C8 1.391(8) .
C7 H7 0.9500 .
C8 C9 1.407(8) .
C8 H8 0.9500 .
C9 C10 1.418(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.95 2.34 3.112(8) 138.3 2_545
C4 H4 N2 0.95 2.60 3.481(8) 155.0 2_456
C7 H7 O2 0.95 2.55 3.410(8) 150.3 2
C8 H8 O3 0.95 2.53 3.442(8) 161.4 .
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_site_symmetry_1
N1 Ag O1 N3 -31.1(6) .
O3 Ag O1 N3 166.2(4) 2_545
Ag Ag O1 N3 -122.3(4) 3_566
O1 Ag N1 C2 -160.9(4) .
O3 Ag N1 C2 -3.0(5) 2_545
Ag Ag N1 C2 -77.4(4) 3_566
O1 Ag N1 C9 26.2(6) .
O3 Ag N1 C9 -175.8(4) 2_545
Ag Ag N1 C9 109.8(4) 3_566
Ag O3 N3 O2 1.9(6) 2
Ag O3 N3 O1 -177.6(4) 2
Ag O1 N3 O2 176.8(4) .
Ag O1 N3 O3 -3.7(7) .
C9 N1 C2 C3 1.9(8) .
Ag N1 C2 C3 -171.1(4) .
N1 C2 C3 C4 0.8(9) .
N1 C2 C3 C11 -177.2(5) .
C2 C3 C4 C10 -1.2(8) .
C11 C3 C4 C10 176.8(5) .
C10 C5 C6 C7 0.5(9) .
C5 C6 C7 C8 0.6(9) .
C6 C7 C8 C9 -1.2(9) .
C2 N1 C9 C8 176.9(5) .
Ag N1 C9 C8 -10.3(7) .
C2 N1 C9 C10 -4.2(8) .
Ag N1 C9 C10 168.6(4) .
C7 C8 C9 N1 179.6(5) .
C7 C8 C9 C10 0.6(8) .
C3 C4 C10 C9 -1.0(8) .
C3 C4 C10 C5 -178.7(5) .
N1 C9 C10 C4 3.7(8) .
C8 C9 C10 C4 -177.4(5) .
N1 C9 C10 C5 -178.5(5) .
C8 C9 C10 C5 0.4(8) .
C6 C5 C10 C4 176.7(5) .
C6 C5 C10 C9 -1.0(8) .
C4 C3 C11 N2 -144(23) .
C2 C3 C11 N2 34(24) .
