#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:18:00 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179446 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/43/4334378.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_4334378
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         'C20 H12 Ag N5 O3'
_chemical_formula_sum            'C20 H12 Ag N5 O3'
_chemical_formula_weight         478.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.828(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.249(3)
_cell_length_b                   9.9554(12)
_cell_length_c                   7.5745(10)
_cell_measurement_reflns_used    4010
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.33
_cell_measurement_theta_min      2.23
_cell_volume                     1752.2(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13903
_diffrn_reflns_theta_full        30.77
_diffrn_reflns_theta_max         30.77
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_correction_T_min  0.8907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_description       irregular
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.553
_refine_diff_density_min         -1.571
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0417
_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)+(0.0626P)²+0.5586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2076
_reflns_number_total             2721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400081v_si_002_5.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4334378
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Ag1 Ag 0.0000 0.79287(3) 0.2500 0.02659(12) Uani 1 2 d S
O1 O -0.04031(11) 0.5516(3) 0.1741(4) 0.0388(6) Uani 1 1 d .
O2 O 0.0000 0.3633(3) 0.2500 0.0366(8) Uani 1 2 d S
N1 N 0.07525(11) 0.8250(2) 0.0758(3) 0.0204(5) Uani 1 1 d .
N2 N 0.20007(13) 0.5025(3) -0.1857(4) 0.0333(6) Uani 1 1 d .
N3 N 0.0000 0.4877(4) 0.2500 0.0253(8) Uani 1 2 d S
C2 C 0.10200(12) 0.7153(3) 0.0235(4) 0.0207(5) Uani 1 1 d .
H2 H 0.0852 0.6322 0.0440 0.033(10) Uiso 1 1 calc R
C3 C 0.15537(13) 0.7197(3) -0.0627(4) 0.0211(6) Uani 1 1 d .
C4 C 0.18219(12) 0.8412(3) -0.0890(4) 0.0214(6) Uani 1 1 d .
H4 H 0.2180 0.8450 -0.1402 0.005(7) Uiso 1 1 calc R
C5 C 0.17780(14) 1.0891(3) -0.0678(4) 0.0244(6) Uani 1 1 d .
H5 H 0.2138 1.0970 -0.1169 0.028(10) Uiso 1 1 calc R
C6 C 0.14753(15) 1.2025(3) -0.0255(4) 0.0272(6) Uani 1 1 d .
H6 H 0.1629 1.2869 -0.0471 0.031(11) Uiso 1 1 calc R
C7 C 0.09293(14) 1.1910(3) 0.0508(4) 0.0262(6) Uani 1 1 d .
H7 H 0.0724 1.2682 0.0775 0.038(12) Uiso 1 1 calc R
C8 C 0.07000(13) 1.0668(3) 0.0857(4) 0.0222(6) Uani 1 1 d .
H8 H 0.0345 1.0607 0.1383 0.028(10) Uiso 1 1 calc R
C9 C 0.09985(12) 0.9484(3) 0.0424(4) 0.0186(5) Uani 1 1 d .
C10 C 0.15429(12) 0.9592(3) -0.0367(4) 0.0199(6) Uani 1 1 d .
C11 C 0.18035(13) 0.5950(3) -0.1291(4) 0.0244(6) 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 Ag1 N1 163.62(13) . 2
C2 N1 C9 118.5(2) . .
C2 N1 Ag1 116.10(19) . .
C9 N1 Ag1 124.66(19) . .
O2 N3 O1 120.45(18) . 2
O2 N3 O1 120.45(18) . .
O1 N3 O1 119.1(4) 2 .
N1 C2 C3 122.5(3) . .
N1 C2 H2 118.7 . .
C3 C2 H2 118.7 . .
C4 C3 C2 119.9(3) . .
C4 C3 C11 120.5(3) . .
C2 C3 C11 119.5(3) . .
C3 C4 C10 118.6(3) . .
C3 C4 H4 120.7 . .
C10 C4 H4 120.7 . .
C6 C5 C10 120.3(3) . .
C6 C5 H5 119.8 . .
C10 C5 H5 119.8 . .
C5 C6 C7 120.1(3) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C8 C7 C6 120.6(3) . .
C8 C7 H7 119.7 . .
C6 C7 H7 119.7 . .
C7 C8 C9 120.6(3) . .
C7 C8 H8 119.7 . .
C9 C8 H8 119.7 . .
N1 C9 C10 121.6(2) . .
N1 C9 C8 119.3(3) . .
C10 C9 C8 119.0(3) . .
C4 C10 C9 118.7(3) . .
C4 C10 C5 121.9(3) . .
C9 C10 C5 119.3(3) . .
N2 C11 C3 177.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N1 2.247(3) .
Ag1 N1 2.248(3) 2
O1 N3 1.257(3) .
O2 N3 1.238(5) .
N1 C2 1.324(4) .
N1 C9 1.382(4) .
N2 C11 1.120(4) .
N3 O1 1.257(3) 2
C2 C3 1.421(4) .
C2 H2 0.9300 .
C3 C4 1.379(4) .
C3 C11 1.466(4) .
C4 C10 1.405(4) .
C4 H4 0.9300 .
C5 C6 1.373(4) .
C5 C10 1.426(4) .
C5 H5 0.9300 .
C6 C7 1.416(5) .
C6 H6 0.9300 .
C7 C8 1.376(4) .
C7 H7 0.9300 .
C8 C9 1.411(4) .
C8 H8 0.9300 .
C9 C10 1.422(4) .
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 O1 0.93 2.54 3.188(4) 127.4 2
C6 H6 N2 0.93 2.55 3.461(4) 165.8 1_565
C7 H7 O2 0.93 2.36 3.177(4) 146.3 1_565
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 Ag1 N1 C2 177.2(2) 2
N1 Ag1 N1 C9 7.1(2) 2
C9 N1 C2 C3 1.1(4) .
Ag1 N1 C2 C3 -169.7(2) .
N1 C2 C3 C4 2.4(5) .
N1 C2 C3 C11 -175.3(3) .
C2 C3 C4 C10 -3.1(4) .
C11 C3 C4 C10 174.6(3) .
C10 C5 C6 C7 0.6(5) .
C5 C6 C7 C8 0.9(5) .
C6 C7 C8 C9 -1.5(5) .
C2 N1 C9 C10 -3.7(4) .
Ag1 N1 C9 C10 166.2(2) .
C2 N1 C9 C8 175.5(3) .
Ag1 N1 C9 C8 -14.6(4) .
C7 C8 C9 N1 -178.7(3) .
C7 C8 C9 C10 0.5(5) .
C3 C4 C10 C9 0.5(4) .
C3 C4 C10 C5 -176.6(3) .
N1 C9 C10 C4 2.9(4) .
C8 C9 C10 C4 -176.3(3) .
N1 C9 C10 C5 -179.8(3) .
C8 C9 C10 C5 1.0(4) .
C6 C5 C10 C4 175.7(3) .
C6 C5 C10 C9 -1.5(5) .
C4 C3 C11 N2 -38(8) .
C2 C3 C11 N2 139(8) .
