#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (Tue 16 de Feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/20/7022029.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_7022029
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 Ag1 N2 O6, N O3, 2(H2 O)'
_chemical_formula_sum            'C18 H24 Ag N3 O11'
_chemical_formula_weight         566.27
_chemical_name_common            'bisisonicotinate triethyleneglycol'
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.062(15)
_cell_angle_beta                 107.033(15)
_cell_angle_gamma                99.711(15)
_cell_formula_units_Z            2
_cell_length_a                   9.1377(18)
_cell_length_b                   10.794(2)
_cell_length_c                   11.988(2)
_cell_measurement_reflns_used    13382
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      1.82
_cell_volume                     1082.4(4)
_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      200(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1485
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22829
_diffrn_reflns_theta_full        26.71
_diffrn_reflns_theta_max         26.71
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bloc
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.676
_refine_diff_density_min         -2.073
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0596
_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)+(0.1026P)²+0.2873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                4070
_reflns_number_total             4584
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2dt31259j.txt
_cod_data_source_block           l3iagno3
_cod_original_cell_volume        1082.4(3)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C18 H24 Ag1 N3 O11'
_cod_database_code               7022029
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.71217(3) 0.26282(3) 0.73150(3) 0.04495(15) Uani 1 1 d .
O3 O 0.3489(3) 0.7120(3) 0.0387(3) 0.0430(6) Uani 1 1 d .
O2 O 0.5972(3) 0.8095(3) 0.2580(3) 0.0414(6) Uani 1 1 d .
O4 O 0.0380(3) 0.7443(3) -0.0837(3) 0.0395(6) Uani 1 1 d .
O5 O -0.1967(3) 0.6918(3) -0.0576(3) 0.0474(7) Uani 1 1 d .
O1 O 0.6892(3) 0.8251(3) 0.5133(3) 0.0444(6) Uani 1 1 d .
O6 O 0.4650(4) 0.8190(4) 0.5566(4) 0.0650(10) Uani 1 1 d .
N1 N 0.6685(4) 0.4433(3) 0.6868(3) 0.0411(7) Uani 1 1 d .
N2 N -0.2227(4) 1.0911(3) -0.2169(3) 0.0414(7) Uani 1 1 d .
C8 C 0.4989(4) 0.6821(4) 0.0568(4) 0.0413(8) Uani 1 1 d .
H8A H 0.5191 0.6667 -0.0189 0.050 Uiso 1 1 calc R
H8B H 0.4998 0.6040 0.0863 0.050 Uiso 1 1 calc R
C7 C 0.6247(4) 0.7920(4) 0.1458(4) 0.0442(9) Uani 1 1 d .
H7A H 0.7273 0.7732 0.1556 0.053 Uiso 1 1 calc R
H7B H 0.6231 0.8706 0.1171 0.053 Uiso 1 1 calc R
C11 C -0.1036(4) 0.7635(4) -0.0873(3) 0.0368(8) Uani 1 1 d .
C12 C -0.1393(4) 0.8790(4) -0.1318(3) 0.0358(7) Uani 1 1 d .
C1 C 0.7744(5) 0.5150(4) 0.6523(4) 0.0426(9) Uani 1 1 d .
H1 H 0.8677 0.4894 0.6565 0.051 Uiso 1 1 calc R
C2 C 0.7532(4) 0.6239(4) 0.6112(4) 0.0427(9) Uani 1 1 d .
H2 H 0.8288 0.6695 0.5865 0.051 Uiso 1 1 calc R
C3 C 0.6149(4) 0.6644(3) 0.6076(3) 0.0348(7) Uani 1 1 d .
C17 C 0.5062(4) 0.5940(4) 0.6464(4) 0.0401(8) Uani 1 1 d .
H17 H 0.4144 0.6202 0.6468 0.048 Uiso 1 1 calc R
C18 C 0.5360(4) 0.4850(4) 0.6843(4) 0.0425(9) Uani 1 1 d .
H18 H 0.4619 0.4377 0.7093 0.051 Uiso 1 1 calc R
C14 C -0.0855(4) 1.0585(4) -0.2158(4) 0.0421(8) Uani 1 1 d .
H14 H -0.0187 1.1088 -0.2447 0.050 Uiso 1 1 calc R
C13 C -0.0396(4) 0.9557(4) -0.1747(4) 0.0399(8) Uani 1 1 d .
H13 H 0.0560 0.9374 -0.1753 0.048 Uiso 1 1 calc R
C15 C -0.3174(4) 1.0154(4) -0.1752(4) 0.0414(8) Uani 1 1 d .
H15 H -0.4129 1.0350 -0.1758 0.050 Uiso 1 1 calc R
C16 C -0.2803(4) 0.9114(4) -0.1323(4) 0.0414(8) Uani 1 1 d .
H16 H -0.3488 0.8626 -0.1037 0.050 Uiso 1 1 calc R
C4 C 0.5793(4) 0.7778(4) 0.5580(4) 0.0408(8) Uani 1 1 d .
C5 C 0.6690(5) 0.9331(4) 0.4589(4) 0.0454(9) Uani 1 1 d .
H5A H 0.7347 1.0130 0.5147 0.054 Uiso 1 1 calc R
H5B H 0.5602 0.9397 0.4382 0.054 Uiso 1 1 calc R
C9 C 0.2270(5) 0.6097(4) -0.0486(4) 0.0453(9) Uani 1 1 d .
H9A H 0.2409 0.5269 -0.0317 0.054 Uiso 1 1 calc R
H9B H 0.2327 0.6096 -0.1281 0.054 Uiso 1 1 calc R
C6 C 0.7148(4) 0.9115(4) 0.3480(4) 0.0418(8) Uani 1 1 d .
H6A H 0.7239 0.9901 0.3193 0.050 Uiso 1 1 calc R
H6B H 0.8159 0.8885 0.3660 0.050 Uiso 1 1 calc R
C10 C 0.0694(5) 0.6287(4) -0.0445(4) 0.0443(9) Uani 1 1 d .
H10A H -0.0121 0.5539 -0.0960 0.053 Uiso 1 1 calc R
H10B H 0.0676 0.6362 0.0369 0.053 Uiso 1 1 calc R
O7 O -0.0515(5) 0.2390(4) 0.5756(4) 0.0773(11) Uani 1 1 d .
O8 O 0.1208(5) 0.4182(4) 0.6183(4) 0.0796(12) Uani 1 1 d .
O9 O 0.0507(4) 0.3482(4) 0.7579(3) 0.0634(9) Uani 1 1 d .
N3 N 0.0414(4) 0.3351(4) 0.6505(4) 0.0498(9) Uani 1 1 d .
O10 O 0.8463(5) 0.3054(4) 0.3450(4) 0.0718(10) Uani 1 1 d .
O11 O 0.6483(4) 0.1179(4) 0.1395(4) 0.0623(9) Uani 1 1 d D
H12A H 0.8588 0.2912 0.4149 0.050 Uiso 1 1 d .
H12B H 0.8618 0.3890 0.3556 0.050 Uiso 1 1 d .
H11A H 0.717(5) 0.175(4) 0.200(2) 0.050 Uiso 1 1 d D
H11B H 0.655(5) 0.144(4) 0.077(2) 0.050 Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 -0.8970 1.1020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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 175.01(11) 1_646 .
C8 O3 C9 110.9(3) . .
C7 O2 C6 112.0(3) . .
C11 O4 C10 113.7(3) . .
C4 O1 C5 118.0(3) . .
C1 N1 C18 117.1(4) . .
C1 N1 Ag1 118.5(3) . .
C18 N1 Ag1 124.3(3) . .
C15 N2 C14 116.5(4) . .
C15 N2 Ag1 119.4(2) . 1_464
C14 N2 Ag1 124.0(3) . 1_464
O3 C8 C7 109.9(3) . .
O3 C8 H8A 109.7 . .
C7 C8 H8A 109.7 . .
O3 C8 H8B 109.7 . .
C7 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
O2 C7 C8 109.0(3) . .
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 . .
O5 C11 O4 123.1(4) . .
O5 C11 C12 122.9(3) . .
O4 C11 C12 114.1(3) . .
C16 C12 C13 118.1(4) . .
C16 C12 C11 118.4(3) . .
C13 C12 C11 123.5(3) . .
N1 C1 C2 123.8(3) . .
N1 C1 H1 118.1 . .
C2 C1 H1 118.1 . .
C1 C2 C3 118.2(3) . .
C1 C2 H2 120.9 . .
C3 C2 H2 120.9 . .
C17 C3 C2 118.8(4) . .
C17 C3 C4 119.8(3) . .
C2 C3 C4 121.4(3) . .
C18 C17 C3 119.0(3) . .
C18 C17 H17 120.5 . .
C3 C17 H17 120.5 . .
N1 C18 C17 123.0(4) . .
N1 C18 H18 118.5 . .
C17 C18 H18 118.5 . .
N2 C14 C13 123.8(3) . .
N2 C14 H14 118.1 . .
C13 C14 H14 118.1 . .
C14 C13 C12 118.7(3) . .
C14 C13 H13 120.7 . .
C12 C13 H13 120.7 . .
N2 C15 C16 123.4(3) . .
N2 C15 H15 118.3 . .
C16 C15 H15 118.3 . .
C15 C16 C12 119.5(3) . .
C15 C16 H16 120.3 . .
C12 C16 H16 120.3 . .
O6 C4 O1 124.7(4) . .
O6 C4 C3 123.9(4) . .
O1 C4 C3 111.4(3) . .
O1 C5 C6 108.3(3) . .
O1 C5 H5A 110.0 . .
C6 C5 H5A 110.0 . .
O1 C5 H5B 110.0 . .
C6 C5 H5B 110.0 . .
H5A C5 H5B 108.4 . .
O3 C9 C10 109.5(3) . .
O3 C9 H9A 109.8 . .
C10 C9 H9A 109.8 . .
O3 C9 H9B 109.8 . .
C10 C9 H9B 109.8 . .
H9A C9 H9B 108.2 . .
O2 C6 C5 108.9(3) . .
O2 C6 H6A 109.9 . .
C5 C6 H6A 109.9 . .
O2 C6 H6B 109.9 . .
C5 C6 H6B 109.9 . .
H6A C6 H6B 108.3 . .
O4 C10 C9 110.7(3) . .
O4 C10 H10A 109.5 . .
C9 C10 H10A 109.5 . .
O4 C10 H10B 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
O7 N3 O8 120.3(5) . .
O7 N3 O9 118.8(4) . .
O8 N3 O9 120.9(4) . .
H12A O10 H12B 105.3(4) . .
H11A O11 H11B 105(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N2 2.175(4) 1_646
Ag1 N1 2.178(4) .
O3 C8 1.424(4) .
O3 C9 1.433(5) .
O2 C7 1.426(5) .
O2 C6 1.427(5) .
O4 C11 1.334(4) .
O4 C10 1.452(5) .
O5 C11 1.225(4) .
O1 C4 1.339(5) .
O1 C5 1.445(5) .
O6 C4 1.199(5) .
N1 C1 1.341(5) .
N1 C18 1.355(5) .
N2 C15 1.351(5) .
N2 C14 1.355(5) .
N2 Ag1 2.175(4) 1_464
C8 C7 1.499(6) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C11 C12 1.487(5) .
C12 C16 1.389(5) .
C12 C13 1.396(5) .
C1 C2 1.373(6) .
C1 H1 0.9300 .
C2 C3 1.397(5) .
C2 H2 0.9300 .
C3 C17 1.386(5) .
C3 C4 1.494(6) .
C17 C18 1.373(6) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C14 C13 1.371(6) .
C14 H14 0.9300 .
C13 H13 0.9300 .
C15 C16 1.367(6) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C5 C6 1.499(6) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C9 C10 1.502(6) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
O7 N3 1.239(5) .
O8 N3 1.244(5) .
O9 N3 1.246(5) .
O10 H12A 0.857(4) .
O10 H12B 0.870(5) .
O11 H11A 0.866(19) .
O11 H11B 0.866(18) .
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
O10 H12A O7 0.857(4) 2.076(4) 2.904(6) 162.4(3) 1_655
O10 H12B O8 0.870(5) 2.021(4) 2.888(6) 175.0(3) 2_666
O11 H11A O10 0.866(19) 1.94(2) 2.802(5) 171(5) .
O11 H11B O3 0.866(18) 2.25(3) 3.052(5) 155(4) 2_665
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 37.7(15) 1_646
N2 Ag1 N1 C18 -146.5(12) 1_646
C9 O3 C8 C7 178.4(3) .
C6 O2 C7 C8 178.9(3) .
O3 C8 C7 O2 61.9(4) .
C10 O4 C11 O5 1.6(5) .
C10 O4 C11 C12 -177.8(3) .
O5 C11 C12 C16 4.2(6) .
O4 C11 C12 C16 -176.3(4) .
O5 C11 C12 C13 -174.8(4) .
O4 C11 C12 C13 4.6(5) .
C18 N1 C1 C2 -2.4(6) .
Ag1 N1 C1 C2 173.7(3) .
N1 C1 C2 C3 1.5(7) .
C1 C2 C3 C17 0.6(6) .
C1 C2 C3 C4 -176.8(4) .
C2 C3 C17 C18 -1.7(6) .
C4 C3 C17 C18 175.7(4) .
C1 N1 C18 C17 1.2(6) .
Ag1 N1 C18 C17 -174.6(3) .
C3 C17 C18 N1 0.8(6) .
C15 N2 C14 C13 -0.5(6) .
Ag1 N2 C14 C13 174.9(3) 1_464
N2 C14 C13 C12 0.4(7) .
C16 C12 C13 C14 -0.4(6) .
C11 C12 C13 C14 178.7(4) .
C14 N2 C15 C16 0.7(6) .
Ag1 N2 C15 C16 -174.9(3) 1_464
N2 C15 C16 C12 -0.7(7) .
C13 C12 C16 C15 0.5(6) .
C11 C12 C16 C15 -178.5(4) .
C5 O1 C4 O6 -0.2(6) .
C5 O1 C4 C3 178.3(3) .
C17 C3 C4 O6 5.3(6) .
C2 C3 C4 O6 -177.4(5) .
C17 C3 C4 O1 -173.3(4) .
C2 C3 C4 O1 4.1(5) .
C4 O1 C5 C6 -139.2(4) .
C8 O3 C9 C10 166.7(3) .
C7 O2 C6 C5 174.2(3) .
O1 C5 C6 O2 71.6(4) .
C11 O4 C10 C9 177.1(3) .
O3 C9 C10 O4 66.4(4) .
