#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:08:17 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179715 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/17/7001711.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_7001711
loop_
_publ_author_name
'Qureshi, Naseem'
'Yufit, Dmitry S.'
'Howard, Judith A. K.'
'Steed, Jonathan W.'
_publ_section_title
;
 Ion-pair binding by mixed N,S-donor 2-ureidopyridine ligands
;
_journal_issue                   29
_journal_name_full               'Dalton Transactions'
_journal_page_first              5708
_journal_paper_doi               10.1039/b905555j
_journal_year                    2009
_chemical_formula_moiety         'C13 H13 N3 O S, Ag, NO3'
_chemical_formula_sum            'C13 H13 Ag N4 O4 S'
_chemical_formula_weight         429.20
_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   difmap
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.97(1)
_cell_angle_beta                 69.83(1)
_cell_angle_gamma                75.89(1)
_cell_formula_units_Z            2
_cell_length_a                   7.9094(2)
_cell_length_b                   9.6883(3)
_cell_length_c                   10.6752(3)
_cell_measurement_reflns_used    7100
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      31.404
_cell_measurement_theta_min      2.176
_cell_volume                     741.55(7)
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    Olex2
_computing_publication_material  Olex2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0235
_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            9809
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.04
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.5158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.142
_refine_diff_density_min         -1.517
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0758
_reflns_number_gt                3884
_reflns_number_total             4302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905555j.txt
_cod_data_source_block           2_202A
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        741.53(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7001711
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.68266(2) 0.944887(14) 0.581142(14) 0.02302(6) Uani 1 1 d . . .
S1 S 0.80353(7) 1.15860(5) 0.53372(5) 0.01988(10) Uani 1 1 d . . .
O1 O 1.2779(2) 0.88093(18) 0.11884(16) 0.0336(4) Uani 1 1 d . . .
O2 O 0.7712(3) 0.74519(18) 0.40430(16) 0.0362(4) Uani 1 1 d . . .
O3 O 0.6717(2) 0.93938(15) 0.32225(16) 0.0242(3) Uani 1 1 d . . .
O4 O 0.8037(3) 0.73995(18) 0.19443(16) 0.0330(4) Uani 1 1 d . . .
N1 N 1.1588(2) 1.07545(19) 0.02450(17) 0.0225(3) Uani 1 1 d . . .
N2 N 1.4163(3) 0.90707(19) -0.10505(17) 0.0239(3) Uani 1 1 d . . .
N3 N 1.6672(2) 0.77122(17) -0.27654(16) 0.0185(3) Uani 1 1 d . . .
N4 N 0.7502(2) 0.80707(18) 0.30615(17) 0.0226(3) Uani 1 1 d . . .
C1 C 0.6291(4) 1.3072(2) 0.6410(2) 0.0286(4) Uani 1 1 d . . .
C2 C 0.8255(3) 1.20708(19) 0.36939(19) 0.0178(3) Uani 1 1 d . . .
C3 C 0.9703(3) 1.1165(2) 0.26577(18) 0.0180(3) Uani 1 1 d . . .
C4 C 1.0102(3) 1.1536(2) 0.13571(19) 0.0204(4) Uani 1 1 d . . .
C5 C 0.9014(3) 1.2800(3) 0.1095(2) 0.0304(5) Uani 1 1 d . . .
C6 C 0.7565(3) 1.3665(3) 0.2130(2) 0.0335(5) Uani 1 1 d . . .
C7 C 0.7160(3) 1.3317(2) 0.3448(2) 0.0259(4) Uani 1 1 d . . .
C8 C 1.2827(3) 0.9483(2) 0.0223(2) 0.0230(4) Uani 1 1 d . . .
C9 C 1.5593(3) 0.7826(2) -0.1468(2) 0.0219(4) Uani 1 1 d . . .
C10 C 1.5893(4) 0.6751(3) -0.0632(2) 0.0362(6) Uani 1 1 d . . .
C11 C 1.7370(4) 0.5563(3) -0.1173(3) 0.0393(6) Uani 1 1 d . . .
C12 C 1.8501(3) 0.5436(2) -0.2506(2) 0.0277(4) Uani 1 1 d . . .
C13 C 1.8089(3) 0.6526(2) -0.3259(2) 0.0205(3) Uani 1 1 d . . .
H1N H 1.176(4) 1.115(3) -0.045(3) 0.029(7) Uiso 1 1 d . . .
H2N H 1.398(4) 0.954(4) -0.165(3) 0.035(8) Uiso 1 1 d . . .
H1A H 0.622(5) 1.279(4) 0.727(4) 0.044(9) Uiso 1 1 d . . .
H1B H 0.508(4) 1.327(3) 0.622(3) 0.034(8) Uiso 1 1 d . . .
H1C H 0.675(5) 1.395(4) 0.626(3) 0.044(9) Uiso 1 1 d . . .
H12 H 1.953(4) 0.466(3) -0.290(3) 0.020(6) Uiso 1 1 d . . .
H3 H 1.049(4) 1.034(3) 0.280(3) 0.027(7) Uiso 1 1 d . . .
H5 H 0.931(5) 1.303(4) 0.021(3) 0.041(9) Uiso 1 1 d . . .
H6 H 0.681(5) 1.449(4) 0.193(4) 0.056(11) Uiso 1 1 d . . .
H7 H 0.625(4) 1.394(3) 0.413(3) 0.027(7) Uiso 1 1 d . . .
H10 H 1.514(5) 0.689(4) 0.026(4) 0.046(9) Uiso 1 1 d . . .
H11 H 1.760(5) 0.479(4) -0.066(4) 0.057(11) Uiso 1 1 d . . .
H13 H 1.878(4) 0.649(3) -0.413(3) 0.026(7) Uiso 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
N3 Ag1 S1 140.33(4) 1_456 . ?
N3 Ag1 O2 84.73(6) 1_456 . ?
S1 Ag1 O2 121.58(5) . . ?
N3 Ag1 O3 93.66(5) 1_456 2_676 ?
S1 Ag1 O3 100.90(3) . 2_676 ?
O2 Ag1 O3 112.80(6) . 2_676 ?
C2 S1 C1 103.91(9) . . ?
C2 S1 Ag1 111.59(6) . . ?
C1 S1 Ag1 107.58(8) . . ?
N4 O2 Ag1 103.72(12) . . ?
N4 O3 Ag1 126.18(13) . 2_676 ?
C8 N1 C4 127.49(17) . . ?
C8 N1 H1N 118(2) . . ?
C4 N1 H1N 114(2) . . ?
C9 N2 C8 127.45(17) . . ?
C9 N2 H2N 115(2) . . ?
C8 N2 H2N 116(2) . . ?
C9 N3 C13 118.17(17) . . ?
C9 N3 Ag1 127.89(13) . 1_654 ?
C13 N3 Ag1 112.73(13) . 1_654 ?
O4 N4 O2 120.79(17) . . ?
O4 N4 O3 120.26(17) . . ?
O2 N4 O3 118.95(17) . . ?
S1 C1 H1A 102(2) . . ?
S1 C1 H1B 111.6(17) . . ?
H1A C1 H1B 116(3) . . ?
S1 C1 H1C 110(2) . . ?
H1A C1 H1C 110(3) . . ?
H1B C1 H1C 108(3) . . ?
C7 C2 C3 121.60(18) . . ?
C7 C2 S1 122.84(15) . . ?
C3 C2 S1 115.40(14) . . ?
C4 C3 C2 119.41(17) . . ?
C4 C3 H3 117.4(18) . . ?
C2 C3 H3 123.0(18) . . ?
C3 C4 N1 124.56(17) . . ?
C3 C4 C5 119.55(18) . . ?
N1 C4 C5 115.86(17) . . ?
C6 C5 C4 120.11(19) . . ?
C6 C5 H5 122(2) . . ?
C4 C5 H5 118(2) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119(2) . . ?
C7 C6 H6 120(2) . . ?
C2 C7 C6 118.20(19) . . ?
C2 C7 H7 121.9(18) . . ?
C6 C7 H7 119.8(18) . . ?
O1 C8 N1 124.68(19) . . ?
O1 C8 N2 124.33(18) . . ?
N1 C8 N2 110.98(17) . . ?
N3 C9 N2 114.23(17) . . ?
N3 C9 C10 121.89(19) . . ?
N2 C9 C10 123.87(19) . . ?
C11 C10 C9 118.1(2) . . ?
C11 C10 H10 123(2) . . ?
C9 C10 H10 119(2) . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 121(2) . . ?
C12 C11 H11 118(2) . . ?
C13 C12 C11 117.5(2) . . ?
C13 C12 H12 119.7(16) . . ?
C11 C12 H12 122.8(16) . . ?
N3 C13 C12 123.72(19) . . ?
N3 C13 H13 115.5(19) . . ?
C12 C13 H13 120.8(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 N3 2.2636(16) 1_456 ?
Ag1 S1 2.4674(5) . ?
Ag1 O2 2.4957(17) . ?
Ag1 O3 2.5789(15) 2_676 ?
S1 C2 1.7768(19) . ?
S1 C1 1.798(2) . ?
O1 C8 1.215(2) . ?
O2 N4 1.247(2) . ?
O3 N4 1.264(2) . ?
O3 Ag1 2.5789(15) 2_676 ?
O4 N4 1.242(2) . ?
N1 C8 1.369(2) . ?
N1 C4 1.403(2) . ?
N1 H1N 0.82(3) . ?
N2 C9 1.386(2) . ?
N2 C8 1.388(3) . ?
N2 H2N 0.82(3) . ?
N3 C9 1.341(3) . ?
N3 C13 1.349(2) . ?
N3 Ag1 2.2637(16) 1_654 ?
C1 H1A 0.95(3) . ?
C1 H1B 1.02(3) . ?
C1 H1C 1.00(4) . ?
C2 C7 1.387(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.94(3) . ?
C4 C5 1.404(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.93(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.95(4) . ?
C7 H7 0.92(3) . ?
C9 C10 1.401(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.92(4) . ?
C11 C12 1.382(3) . ?
C11 H11 0.95(4) . ?
C12 C13 1.371(3) . ?
C12 H12 0.93(3) . ?
C13 H13 0.90(3) . ?
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
N1 H1N O4 0.82(3) 2.11(3) 2.920(2) 167(3) 2_775
N2 H2N O3 0.82(3) 2.13(3) 2.946(2) 173(3) 2_775
