#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:34:24 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179925 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/20/7022035.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_7022035
loop_
_publ_author_name
'Chevrier, Inès'
'Sagué, Jorge L'
'Brunetto, Priscilla S.'
'Khanna, Nina'
'Rajacic, Zarko'
'Fromm, Katharina M.'
_publ_section_title
;
 Rings, chains and helices: new antimicrobial silver coordination
 compounds with (iso-)nicotinic acid derivatives.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              217
_journal_page_last               231
_journal_paper_doi               10.1039/c2dt31259j
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C18 H20 Ag N2 O6,C F3 O3 S'
_chemical_formula_sum            'C19 H20 Ag F3 N2 O9 S'
_chemical_formula_weight         617.30
_chemical_name_common            'bisisonicotinate triethyleneglycol'
_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                 116.134(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.930(5)
_cell_length_b                   14.200(5)
_cell_length_c                   20.264(5)
_cell_measurement_temperature    293(2)
_cell_volume                     2306.9(17)
_computing_cell_refinement       Xarea
_computing_data_collection       Xarea
_computing_data_reduction        Xarea
_computing_molecular_graphics    diamond
_computing_publication_material  word
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.1645
_diffrn_reflns_av_sigmaI/netI    0.1732
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5859
_diffrn_reflns_theta_full        22.61
_diffrn_reflns_theta_max         22.61
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'transparent yellow grey'
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1910
_refine_ls_R_factor_gt           0.0810
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+9.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                1485
_reflns_number_total             3017
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2dt31259j.txt
_cod_data_source_block           comp3defp21np21c
_cod_original_cell_volume        2306.9(16)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7022035
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
Ag1 Ag -1.88800(13) -0.23947(9) -0.92913(7) 0.0595(4) Uani 1 1 d .
O5 O -0.4969(10) -0.3810(7) -0.8189(5) 0.055(3) Uani 1 1 d .
O6 O -0.6033(13) -0.4607(9) -0.9245(6) 0.086(4) Uani 1 1 d .
O4 O -0.6687(10) -0.2648(8) -0.7660(5) 0.056(3) Uani 1 1 d .
O3 O -0.8181(13) -0.0975(8) -0.8009(7) 0.081(4) Uani 1 1 d .
O2 O -1.1392(11) -0.0398(7) -0.9002(5) 0.053(3) Uani 1 1 d .
O1 O -1.2580(12) -0.0615(7) -1.0235(6) 0.061(3) Uani 1 1 d .
N2 N -0.0959(12) -0.2953(7) -0.9156(7) 0.041(3) Uani 1 1 d .
N1 N -1.6733(13) -0.1841(8) -0.9387(6) 0.046(3) Uani 1 1 d .
C14 C -0.2222(17) -0.3403(11) -0.9683(8) 0.055(4) Uani 1 1 d .
H14 H -0.2216 -0.3469 -1.0139 0.065 Uiso 1 1 calc R
C15 C -0.3556(15) -0.3782(10) -0.9591(7) 0.044(4) Uani 1 1 d .
H15 H -0.4422 -0.4088 -0.9977 0.052 Uiso 1 1 calc R
C16 C -0.3565(16) -0.3695(9) -0.8920(8) 0.035(4) Uani 1 1 d .
C17 C -0.2278(15) -0.3227(9) -0.8378(7) 0.043(4) Uani 1 1 d .
H17 H -0.2270 -0.3144 -0.7921 0.051 Uiso 1 1 calc R
C18 C -0.0982(15) -0.2874(9) -0.8504(8) 0.046(4) Uani 1 1 d .
H18 H -0.0100 -0.2572 -0.8122 0.055 Uiso 1 1 calc R
C13 C -0.5008(18) -0.4093(11) -0.8811(9) 0.048(4) Uani 1 1 d .
C12 C -0.6364(16) -0.4121(11) -0.8061(8) 0.059(4) Uani 1 1 d .
H12A H -0.6287 -0.4791 -0.7958 0.070 Uiso 1 1 calc R
H12B H -0.7411 -0.3994 -0.8487 0.070 Uiso 1 1 calc R
C11 C -0.6251(19) -0.3573(13) -0.7413(9) 0.070(5) Uani 1 1 d .
H11A H -0.7012 -0.3826 -0.7234 0.084 Uiso 1 1 calc R
H11B H -0.5127 -0.3597 -0.7019 0.084 Uiso 1 1 calc R
C10 C -0.6688(18) -0.2094(13) -0.7108(9) 0.069(5) Uani 1 1 d .
H10A H -0.5645 -0.2172 -0.6669 0.083 Uiso 1 1 calc R
H10B H -0.7592 -0.2282 -0.6993 0.083 Uiso 1 1 calc R
C9 C -0.690(2) -0.1115(16) -0.7340(11) 0.099(7) Uani 1 1 d .
H9A H -0.7075 -0.0739 -0.6981 0.119 Uiso 1 1 calc R
H9B H -0.5875 -0.0898 -0.7348 0.119 Uiso 1 1 calc R
C8 C -0.848(2) 0.0003(13) -0.8265(9) 0.083(6) Uani 1 1 d .
H8A H -0.7483 0.0270 -0.8269 0.099 Uiso 1 1 calc R
H8B H -0.8787 0.0382 -0.7945 0.099 Uiso 1 1 calc R
C7 C -0.9889(17) -0.0025(10) -0.9035(9) 0.060(5) Uani 1 1 d .
H7A H -1.0106 0.0604 -0.9244 0.072 Uiso 1 1 calc R
H7B H -0.9585 -0.0423 -0.9346 0.072 Uiso 1 1 calc R
C6 C -1.2624(17) -0.0652(10) -0.9647(9) 0.046(4) Uani 1 1 d .
C3 C -1.4070(16) -0.1069(8) -0.9535(9) 0.040(4) Uani 1 1 d .
C4 C -1.4061(17) -0.1139(11) -0.8869(8) 0.053(4) Uani 1 1 d .
H4 H -1.3141 -0.0926 -0.8454 0.063 Uiso 1 1 calc R
C5 C -1.5382(18) -0.1517(11) -0.8798(8) 0.053(4) Uani 1 1 d .
H5 H -1.5354 -0.1553 -0.8334 0.064 Uiso 1 1 calc R
C1 C -1.6736(14) -0.1786(9) -1.0046(8) 0.048(4) Uani 1 1 d .
H1 H -1.7663 -0.2004 -1.0456 0.057 Uiso 1 1 calc R
C2 C -1.5406(16) -0.1417(10) -1.0140(8) 0.051(4) Uani 1 1 d .
H2 H -1.5419 -0.1405 -1.0601 0.061 Uiso 1 1 calc R
S1 S -1.0974(4) -0.3030(3) -1.1451(2) 0.0542(11) Uani 1 1 d .
F3 F -1.0246(14) -0.4613(8) -1.0764(8) 0.137(5) Uani 1 1 d .
F1 F -0.8195(10) -0.3973(7) -1.0848(6) 0.107(4) Uani 1 1 d .
F2 F -1.0074(17) -0.4640(10) -1.1784(9) 0.165(7) Uani 1 1 d .
O7 O -1.0708(12) -0.2662(9) -1.0758(6) 0.091(4) Uani 1 1 d .
O9 O -1.2621(11) -0.3325(9) -1.1935(6) 0.102(4) Uani 1 1 d .
O8 O -1.0100(10) -0.2510(8) -1.1773(5) 0.079(3) Uani 1 1 d .
C19 C -0.982(2) -0.4135(14) -1.1241(14) 0.085(7) 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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
N2 Ag1 N1 178.0(5) 1_355 .
C13 O5 C12 114.7(11) . .
C10 O4 C11 110.3(12) . .
C9 O3 C8 115.8(15) . .
C6 O2 C7 115.3(11) . .
C14 N2 C18 117.4(11) . .
C14 N2 Ag1 123.5(10) . 1_755
C18 N2 Ag1 119.1(9) . 1_755
C1 N1 C5 118.1(12) . .
C1 N1 Ag1 120.0(10) . .
C5 N1 Ag1 121.9(9) . .
N2 C14 C15 123.5(13) . .
N2 C14 H14 118.2 . .
C15 C14 H14 118.2 . .
C16 C15 C14 118.5(13) . .
C16 C15 H15 120.8 . .
C14 C15 H15 120.8 . .
C17 C16 C15 118.2(13) . .
C17 C16 C13 122.5(13) . .
C15 C16 C13 119.3(13) . .
C16 C17 C18 120.4(13) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
N2 C18 C17 122.0(13) . .
N2 C18 H18 119.0 . .
C17 C18 H18 119.0 . .
O6 C13 O5 125.7(13) . .
O6 C13 C16 123.1(14) . .
O5 C13 C16 111.3(13) . .
O5 C12 C11 105.6(12) . .
O5 C12 H12A 110.6 . .
C11 C12 H12A 110.6 . .
O5 C12 H12B 110.6 . .
C11 C12 H12B 110.6 . .
H12A C12 H12B 108.7 . .
O4 C11 C12 105.9(13) . .
O4 C11 H11A 110.5 . .
C12 C11 H11A 110.5 . .
O4 C11 H11B 110.5 . .
C12 C11 H11B 110.5 . .
H11A C11 H11B 108.7 . .
O4 C10 C9 109.4(15) . .
O4 C10 H10A 109.8 . .
C9 C10 H10A 109.8 . .
O4 C10 H10B 109.8 . .
C9 C10 H10B 109.8 . .
H10A C10 H10B 108.3 . .
O3 C9 C10 113.3(16) . .
O3 C9 H9A 108.9 . .
C10 C9 H9A 108.9 . .
O3 C9 H9B 108.9 . .
C10 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
O3 C8 C7 106.2(13) . .
O3 C8 H8A 110.5 . .
C7 C8 H8A 110.5 . .
O3 C8 H8B 110.5 . .
C7 C8 H8B 110.5 . .
H8A C8 H8B 108.7 . .
O2 C7 C8 108.9(12) . .
O2 C7 H7A 109.9 . .
C8 C7 H7A 109.9 . .
O2 C7 H7B 109.9 . .
C8 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
O1 C6 O2 125.6(13) . .
O1 C6 C3 124.0(14) . .
O2 C6 C3 110.3(13) . .
C4 C3 C2 119.1(13) . .
C4 C3 C6 123.0(14) . .
C2 C3 C6 117.8(14) . .
C5 C4 C3 120.8(15) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 N1 121.3(14) . .
C4 C5 H5 119.3 . .
N1 C5 H5 119.3 . .
N1 C1 C2 122.3(13) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 118.3(13) . .
C3 C2 H2 120.9 . .
C1 C2 H2 120.9 . .
O7 S1 O9 117.5(7) . .
O7 S1 O8 112.1(7) . .
O9 S1 O8 116.4(7) . .
O7 S1 C19 104.8(10) . .
O9 S1 C19 102.4(9) . .
O8 S1 C19 100.6(8) . .
F2 C19 F1 111.0(18) . .
F2 C19 F3 109.8(18) . .
F1 C19 F3 103.5(17) . .
F2 C19 S1 115.0(16) . .
F1 C19 S1 110.3(14) . .
F3 C19 S1 106.5(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N2 2.145(10) 1_355
Ag1 N1 2.158(10) .
O5 C13 1.308(16) .
O5 C12 1.448(13) .
O6 C13 1.197(16) .
O4 C10 1.368(16) .
O4 C11 1.398(18) .
O3 C9 1.351(19) .
O3 C8 1.466(18) .
O2 C6 1.334(16) .
O2 C7 1.472(14) .
O1 C6 1.212(16) .
N2 C14 1.327(15) .
N2 C18 1.335(15) .
N2 Ag1 2.145(9) 1_755
N1 C1 1.337(15) .
N1 C5 1.350(16) .
C14 C15 1.393(16) .
C14 H14 0.9300 .
C15 C16 1.371(17) .
C15 H15 0.9300 .
C16 C17 1.362(16) .
C16 C13 1.510(17) .
C17 C18 1.384(15) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C12 C11 1.490(19) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C10 C9 1.45(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C8 C7 1.515(19) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C6 C3 1.525(17) .
C3 C4 1.350(18) .
C3 C2 1.372(17) .
C4 C5 1.361(17) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C1 C2 1.386(16) .
C1 H1 0.9300 .
C2 H2 0.9300 .
S1 O7 1.417(10) .
S1 O9 1.425(10) .
S1 O8 1.424(9) .
S1 C19 1.824(18) .
F3 C19 1.37(2) .
F1 C19 1.329(17) .
F2 C19 1.25(2) .
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
N2 Ag1 N1 C1 162(12) 1_355
N2 Ag1 N1 C5 -20(13) 1_355
C18 N2 C14 C15 1(2) .
Ag1 N2 C14 C15 178.7(10) 1_755
N2 C14 C15 C16 -1(2) .
C14 C15 C16 C17 1(2) .
C14 C15 C16 C13 179.4(13) .
C15 C16 C17 C18 -2(2) .
C13 C16 C17 C18 -180.0(12) .
C14 N2 C18 C17 -1.2(19) .
Ag1 N2 C18 C17 -179.3(10) 1_755
C16 C17 C18 N2 2(2) .
C12 O5 C13 O6 -4(2) .
C12 O5 C13 C16 176.8(11) .
C17 C16 C13 O6 -170.2(15) .
C15 C16 C13 O6 12(2) .
C17 C16 C13 O5 9(2) .
C15 C16 C13 O5 -168.9(13) .
C13 O5 C12 C11 -169.1(13) .
C10 O4 C11 C12 177.5(11) .
O5 C12 C11 O4 71.2(14) .
C11 O4 C10 C9 171.5(13) .
C8 O3 C9 C10 178.5(14) .
O4 C10 C9 O3 50(2) .
C9 O3 C8 C7 176.6(14) .
C6 O2 C7 C8 -166.2(13) .
O3 C8 C7 O2 62.4(16) .
C7 O2 C6 O1 1(2) .
C7 O2 C6 C3 177.3(10) .
O1 C6 C3 C4 177.1(15) .
O2 C6 C3 C4 1.3(18) .
O1 C6 C3 C2 0(2) .
O2 C6 C3 C2 -176.3(12) .
C2 C3 C4 C5 -2(2) .
C6 C3 C4 C5 -180.0(13) .
C3 C4 C5 N1 1(2) .
C1 N1 C5 C4 0(2) .
Ag1 N1 C5 C4 -177.6(11) .
C5 N1 C1 C2 0(2) .
Ag1 N1 C1 C2 178.5(10) .
C4 C3 C2 C1 3(2) .
C6 C3 C2 C1 -179.2(12) .
N1 C1 C2 C3 -2(2) .
O7 S1 C19 F2 170.4(15) .
O9 S1 C19 F2 47.2(18) .
O8 S1 C19 F2 -73.2(17) .
O7 S1 C19 F1 -63.2(17) .
O9 S1 C19 F1 173.6(15) .
O8 S1 C19 F1 53.3(17) .
O7 S1 C19 F3 48.5(15) .
O9 S1 C19 F3 -74.7(16) .
O8 S1 C19 F3 165.0(13) .
