#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:11:09 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179443 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/40/4334008.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_4334008
loop_
_publ_author_name
'Yoichi Habata'
'Aya Taniguchi'
'Mari Ikeda'
'Takao Hiraoka'
'Noriko Matsuyama'
'Sakiko Otsuka'
'Shunsuke Kuwahara'
_publ_section_title
;
 Argentivorous Molecules Bearing Two Aromatic Side-Arms: Ag+-π and CH-π
 Interactions in the Solid State and in Solution
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2542
_journal_page_last               2549
_journal_paper_doi               10.1021/ic302511e
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C31 H36 Ag F3 N4 O3 S'
_chemical_formula_weight         709.57
_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                 107.748(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.298(2)
_cell_length_b                   14.800(2)
_cell_length_c                   17.760(3)
_cell_measurement_temperature    298
_cell_volume                     3329.0(9)
_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      298
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12224
_diffrn_reflns_theta_full        28.42
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.9121
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.576
_refine_diff_density_min         -3.114
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.393
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.395
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.1150
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1076P)²+16.0013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2698
_refine_ls_wR_factor_ref         0.2769
_reflns_number_gt                3702
_reflns_number_total             4165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302511e_si_002_05.cif
_cod_data_source_block           5a_AgOTf
_cod_database_code               4334008
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 0.09877(5) 0.2500 0.0410(3) Uani 1 2 d S
N1 N 0.0458(6) 0.1838(5) 0.3812(4) 0.0533(17) Uani 1 1 d .
N2 N -0.1543(7) 0.1855(7) 0.2455(5) 0.064(2) Uani 1 1 d .
C1 C -0.0332(11) 0.2560(7) 0.3687(7) 0.078(3) Uani 1 1 d .
H1A H -0.0149 0.3040 0.3380 0.094 Uiso 1 1 calc R
H1B H -0.0321 0.2809 0.4194 0.094 Uiso 1 1 calc R
C2 C -0.1446(10) 0.2217(9) 0.3253(7) 0.082(3) Uani 1 1 d .
H2A H -0.1632 0.1746 0.3567 0.098 Uiso 1 1 calc R
H2B H -0.1944 0.2709 0.3203 0.098 Uiso 1 1 calc R
C3 C -0.1635(9) 0.2577(8) 0.1854(6) 0.072(3) Uani 1 1 d .
H3A H -0.1097 0.3032 0.2065 0.087 Uiso 1 1 calc R
H3B H -0.2320 0.2867 0.1743 0.087 Uiso 1 1 calc R
C4 C 0.1512(9) 0.2205(7) 0.3900(6) 0.069(3) Uani 1 1 d .
H4A H 0.2030 0.1731 0.4094 0.082 Uiso 1 1 calc R
H4B H 0.1659 0.2681 0.4294 0.082 Uiso 1 1 calc R
C5 C 0.0465(9) 0.1307(7) 0.4515(5) 0.064(2) Uani 1 1 d .
H5A H -0.0258 0.1187 0.4499 0.077 Uiso 1 1 calc R
H5B H 0.0791 0.1665 0.4984 0.077 Uiso 1 1 calc R
C6 C 0.1049(8) 0.0416(7) 0.4585(6) 0.064(2) Uani 1 1 d .
C7 C 0.2017(10) 0.0298(9) 0.5133(7) 0.083(3) Uani 1 1 d .
H7 H 0.2325 0.0768 0.5473 0.100 Uiso 1 1 calc R
C8 C 0.2550(12) -0.0537(12) 0.5184(10) 0.103(5) Uani 1 1 d .
H8 H 0.3212 -0.0604 0.5555 0.124 Uiso 1 1 calc R
C9 C 0.2137(13) -0.1220(10) 0.4723(10) 0.098(4) Uani 1 1 d .
H9 H 0.2518 -0.1754 0.4759 0.118 Uiso 1 1 calc R
C10 C 0.1136(12) -0.1154(8) 0.4182(8) 0.080(3) Uani 1 1 d .
C11 C 0.0627(14) -0.1900(9) 0.3756(9) 0.094(4) Uani 1 1 d .
H11 H 0.0978 -0.2452 0.3825 0.112 Uiso 1 1 calc R
C12 C -0.0352(17) -0.1846(10) 0.3252(9) 0.110(6) Uani 1 1 d .
H12 H -0.0672 -0.2356 0.2975 0.133 Uiso 1 1 calc R
C13 C -0.0904(12) -0.1006(10) 0.3139(8) 0.091(4) Uani 1 1 d .
H13 H -0.1577 -0.0969 0.2780 0.110 Uiso 1 1 calc R
C14 C -0.0455(8) -0.0260(7) 0.3552(5) 0.063(2) Uani 1 1 d .
H14 H -0.0823 0.0284 0.3475 0.075 Uiso 1 1 calc R
C15 C 0.0582(8) -0.0312(7) 0.4103(5) 0.060(2) Uani 1 1 d .
S1 S 0.4339(5) 0.0406(4) 0.2710(4) 0.0747(14) Uani 0.50 1 d PD
F1 F 0.476(2) -0.0227(13) 0.4084(9) 0.151(9) Uani 0.50 1 d PD
F2 F 0.3240(17) -0.014(2) 0.3510(14) 0.186(12) Uani 0.50 1 d PD
F3 F 0.402(2) 0.0908(16) 0.3955(11) 0.159(10) Uani 0.50 1 d PD
O1 O 0.349(2) 0.0936(17) 0.2304(13) 0.22(2) Uani 0.50 1 d PD
O2 O 0.5314(17) 0.0857(15) 0.2917(13) 0.124(8) Uani 0.50 1 d PD
O3 O 0.441(2) -0.0442(13) 0.2403(14) 0.156(12) Uani 0.50 1 d PD
C16 C 0.4082(15) 0.0212(12) 0.3636(14) 0.085(7) Uani 0.50 1 d PD
H2 H -0.199(9) 0.142(8) 0.229(7) 0.07(3) 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'
F F 0.0171 0.0103 '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
N2 Ag1 N2 115.3(5) 2 .
N2 Ag1 N1 75.1(3) 2 .
N2 Ag1 N1 74.4(3) . .
N2 Ag1 N1 74.4(3) 2 2
N2 Ag1 N1 75.1(3) . 2
N1 Ag1 N1 120.9(3) . 2
C4 N1 C1 111.3(8) . .
C4 N1 C5 110.3(8) . .
C1 N1 C5 109.7(8) . .
C4 N1 Ag1 103.6(5) . .
C1 N1 Ag1 105.1(6) . .
C5 N1 Ag1 116.7(5) . .
C2 N2 C3 112.9(9) . .
C2 N2 Ag1 109.7(6) . .
C3 N2 Ag1 106.9(6) . .
C2 N2 H2 117(8) . .
C3 N2 H2 113(8) . .
Ag1 N2 H2 96(8) . .
N1 C1 C2 111.9(9) . .
N1 C1 H1A 109.2 . .
C2 C1 H1A 109.2 . .
N1 C1 H1B 109.2 . .
C2 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
N2 C2 C1 112.8(9) . .
N2 C2 H2A 109.0 . .
C1 C2 H2A 109.0 . .
N2 C2 H2B 109.0 . .
C1 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
N2 C3 C4 111.6(8) . 2
N2 C3 H3A 109.3 . .
C4 C3 H3A 109.3 2 .
N2 C3 H3B 109.3 . .
C4 C3 H3B 109.3 2 .
H3A C3 H3B 108.0 . .
N1 C4 C3 113.7(8) . 2
N1 C4 H4A 108.8 . .
C3 C4 H4A 108.8 2 .
N1 C4 H4B 108.8 . .
C3 C4 H4B 108.8 2 .
H4A C4 H4B 107.7 . .
N1 C5 C6 113.8(8) . .
N1 C5 H5A 108.8 . .
C6 C5 H5A 108.8 . .
N1 C5 H5B 108.8 . .
C6 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
C7 C6 C15 119.0(11) . .
C7 C6 C5 121.0(10) . .
C15 C6 C5 120.0(9) . .
C6 C7 C8 120.1(13) . .
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 . .
C9 C8 C7 121.8(14) . .
C9 C8 H8 119.1 . .
C7 C8 H8 119.1 . .
C8 C9 C10 120.6(14) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C11 121.6(13) . .
C9 C10 C15 119.0(12) . .
C11 C10 C15 119.2(13) . .
C12 C11 C10 121.9(13) . .
C12 C11 H11 119.0 . .
C10 C11 H11 119.0 . .
C11 C12 C13 119.9(13) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C14 C13 C12 120.7(15) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 120.0(12) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C6 C15 C14 122.3(10) . .
C6 C15 C10 119.4(11) . .
C14 C15 C10 118.2(10) . .
O3 S1 O1 116.8(16) . .
O3 S1 O2 111.8(16) . .
O1 S1 O2 114.1(18) . .
O3 S1 O2 92.3(13) . 2_655
O1 S1 O2 75.3(16) . 2_655
O2 S1 O2 60.7(18) . 2_655
O3 S1 C16 105.6(11) . .
O1 S1 C16 102.3(11) . .
O2 S1 C16 104.6(10) . .
O2 S1 C16 160.6(12) 2_655 .
O3 S1 S1 72.5(12) . 2_655
O1 S1 S1 116.9(14) . 2_655
O2 S1 S1 44.8(9) . 2_655
O2 S1 S1 41.7(7) 2_655 2_655
C16 S1 S1 137.2(7) . 2_655
O3 S1 O3 44.5(17) . 2_655
O1 S1 O3 144.9(11) . 2_655
O2 S1 O3 67.7(12) . 2_655
O2 S1 O3 76.4(10) 2_655 2_655
C16 S1 O3 111.2(9) . 2_655
S1 S1 O3 37.9(5) 2_655 2_655
S1 O1 O2 55.0(10) . 2_655
S1 O2 O2 62.5(14) . 2_655
S1 O2 S1 93.6(12) . 2_655
O2 O2 S1 56.8(11) 2_655 2_655
S1 O2 O1 143.2(18) . 2_655
O2 O2 O1 93(2) 2_655 2_655
S1 O2 O1 49.7(11) 2_655 2_655
S1 O3 O3 95.6(15) . 2_655
S1 O3 S1 69.6(11) . 2_655
O3 O3 S1 39.8(6) 2_655 2_655
F3 C16 F2 106(3) . .
F3 C16 F1 107(2) . .
F2 C16 F1 111(3) . .
F3 C16 S1 110.9(16) . .
F2 C16 S1 109.0(17) . .
F1 C16 S1 112.4(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N2 2.400(8) 2
Ag1 N2 2.400(8) .
Ag1 N1 2.552(7) .
Ag1 N1 2.552(7) 2
N1 C4 1.466(12) .
N1 C1 1.467(14) .
N1 C5 1.473(11) .
N2 C2 1.484(14) .
N2 C3 1.489(14) .
N2 H2 0.86(11) .
C1 C2 1.533(18) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.503(14) 2
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C3 1.503(14) 2
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.516(15) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.368(15) .
C6 C15 1.397(14) .
C7 C8 1.41(2) .
C7 H7 0.9300 .
C8 C9 1.31(2) .
C8 H8 0.9300 .
C9 C10 1.39(2) .
C9 H9 0.9300 .
C10 C11 1.391(19) .
C10 C15 1.433(15) .
C11 C12 1.34(2) .
C11 H11 0.9300 .
C12 C13 1.43(2) .
C12 H12 0.9300 .
C13 C14 1.358(16) .
C13 H13 0.9300 .
C14 C15 1.429(15) .
C14 H14 0.9300 .
S1 O3 1.381(16) .
S1 O1 1.384(15) .
S1 O2 1.404(16) .
S1 O2 1.49(2) 2_655
S1 C16 1.80(3) .
S1 S1 2.108(12) 2_655
S1 O3 2.15(3) 2_655
F1 C16 1.196(18) .
F2 C16 1.190(18) .
F3 C16 1.189(18) .
O1 O2 1.76(4) 2_655
O2 O2 1.46(4) 2_655
O2 S1 1.49(2) 2_655
O2 O1 1.76(4) 2_655
O3 O3 1.51(6) 2_655
O3 S1 2.15(3) 2_655
