#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/86/1508609.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_1508609
loop_
_publ_author_name
'Habata, Yoichi'
'Ikeda, Mari'
'Yamada, Sachiko'
'Takahashi, Hiroki'
'Ueno, Sumiko'
'Suzuki, Takatoshi'
'Kuwahara, Shunsuke'
_publ_section_title
;
 Argentivorous molecules: structural evidence for Ag(+)-π interactions in
 solution.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4576
_journal_page_last               4579
_journal_paper_doi               10.1021/ol3019538
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C37 H44 Ag F3 N4 O3 S'
_chemical_formula_weight         789.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 134.152(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.471(2)
_cell_length_b                   9.2889(14)
_cell_length_c                   19.222(2)
_cell_measurement_temperature    223
_cell_volume                     1725.8(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      223
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11495
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.7309
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.47
_refine_diff_density_max         1.207
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0888P)²+0.7647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                3797
_reflns_number_total             4240
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3019538_si_002.cif
_cod_data_source_block           5a/AgOTf
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               1508609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
_atom_site_disorder_group
Ag1 Ag 0.0000 0.21860(2) 0.2500 0.03698(12) Uani 1 2 d S .
C1 C 0.2283(3) 0.4102(3) 0.2827(2) 0.0438(6) Uani 1 1 d . .
H1A H 0.2632 0.3368 0.2676 0.053 Uiso 1 1 calc R .
H1B H 0.2937 0.4907 0.3141 0.053 Uiso 1 1 calc R .
C2 C 0.0891(3) 0.4635(3) 0.1881(2) 0.0435(6) Uani 1 1 d . .
H2A H 0.0541 0.5378 0.2027 0.052 Uiso 1 1 calc R .
H2B H 0.1021 0.5078 0.1487 0.052 Uiso 1 1 calc R .
C3 C -0.1574(3) 0.4063(3) 0.0589(2) 0.0444(6) Uani 1 1 d . .
H3A H -0.2198 0.3306 0.0119 0.053 Uiso 1 1 calc R .
H3B H -0.1597 0.4848 0.0238 0.053 Uiso 1 1 calc R .
C4 C 0.2112(3) 0.4627(3) 0.3981(2) 0.0440(6) Uani 1 1 d . .
H4A H 0.1479 0.5369 0.3499 0.053 Uiso 1 1 calc R .
H4B H 0.3017 0.5078 0.4497 0.053 Uiso 1 1 calc R .
C9 C 0.3553(3) 0.2655(3) 0.4275(2) 0.0450(6) Uani 1 1 d . .
H9A H 0.3695 0.2543 0.4847 0.054 Uiso 1 1 calc R .
H9B H 0.4337 0.3202 0.4472 0.054 Uiso 1 1 calc R .
C10 C 0.3524(3) 0.1195(3) 0.3927(2) 0.0431(6) Uani 1 1 d . .
C11 C 0.2853(4) 0.0070(4) 0.3939(3) 0.0516(7) Uani 1 1 d . .
H11 H 0.2419 0.0238 0.4157 0.062 Uiso 1 1 calc R .
C12 C 0.2818(5) -0.1295(4) 0.3631(3) 0.0620(9) Uani 1 1 d . .
H12 H 0.2371 -0.2048 0.3650 0.074 Uiso 1 1 calc R .
C13 C 0.3431(5) -0.1552(4) 0.3301(3) 0.0627(9) Uani 1 1 d . .
H13 H 0.3391 -0.2476 0.3084 0.075 Uiso 1 1 calc R .
C14 C 0.4103(4) -0.0463(4) 0.3287(3) 0.0595(8) Uani 1 1 d . .
H14 H 0.4524 -0.0642 0.3060 0.071 Uiso 1 1 calc R .
C15 C 0.4165(4) 0.0917(4) 0.3610(3) 0.0515(7) Uani 1 1 d . .
H15 H 0.4643 0.1656 0.3611 0.062 Uiso 1 1 calc R .
C16 C 0.0108(4) 0.2618(4) 0.0801(3) 0.0451(6) Uani 1 1 d . .
H16A H 0.1108 0.2510 0.1221 0.054 Uiso 1 1 calc R .
H16B H -0.0265 0.3136 0.0216 0.054 Uiso 1 1 calc R .
C17 C -0.0550(3) 0.1143(3) 0.0519(2) 0.0434(6) Uani 1 1 d . .
C18 C 0.0092(4) 0.0078(4) 0.1225(3) 0.0508(7) Uani 1 1 d . .
H18 H 0.0912 0.0288 0.1868 0.061 Uiso 1 1 calc R .
C19 C -0.0468(5) -0.1285(4) 0.0987(3) 0.0622(9) Uani 1 1 d . .
H19 H -0.0031 -0.1998 0.1469 0.075 Uiso 1 1 calc R .
C20 C -0.1666(4) -0.1608(4) 0.0044(3) 0.0625(9) Uani 1 1 d . .
H20 H -0.2043 -0.2539 -0.0113 0.075 Uiso 1 1 calc R .
C21 C -0.2311(4) -0.0571(4) -0.0669(3) 0.0604(9) Uani 1 1 d . .
H21 H -0.3129 -0.0789 -0.1311 0.072 Uiso 1 1 calc R .
C22 C -0.1739(4) 0.0801(4) -0.0426(3) 0.0522(7) Uani 1 1 d . .
H22 H -0.2166 0.1506 -0.0912 0.063 Uiso 1 1 calc R .
F1 F 0.5000 0.6944(5) 0.2500 0.185(4) Uani 1 2 d S 2
F2 F 0.3287(7) 0.5749(12) 0.1806(5) 0.113(3) Uani 0.50 1 d P 2
F3 F 0.4636(7) 0.5575(12) 0.1451(5) 0.112(3) Uani 0.50 1 d P 2
N1 N 0.2251(2) 0.3488(2) 0.35184(18) 0.0385(5) Uani 1 1 d . .
N2 N -0.0148(3) 0.3476(2) 0.13158(18) 0.0389(5) Uani 1 1 d . .
O1 O 0.4533(7) 0.4397(9) 0.1360(5) 0.0710(17) Uani 0.50 1 d P 1
O2 O 0.5000 0.3025(6) 0.2500 0.178(5) Uani 1 2 d S 1
O3 O 0.3184(8) 0.4370(14) 0.1681(6) 0.112(4) Uani 0.50 1 d P 1
C37 C 0.4581(9) 0.5676(8) 0.2133(5) 0.0596(18) Uani 0.50 1 d P .
S1 S 0.4494(4) 0.4236(3) 0.2037(2) 0.0964(9) Uani 0.50 1 d P .
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 121.56(11) 2 .
N2 Ag1 N1 76.49(8) 2 .
N2 Ag1 N1 76.13(8) . .
N2 Ag1 N1 76.13(8) 2 2
N2 Ag1 N1 76.49(8) . 2
N1 Ag1 N1 122.00(11) . 2
N1 C1 C2 114.7(2) . .
N1 C1 H1A 108.6 . .
C2 C1 H1A 108.6 . .
N1 C1 H1B 108.6 . .
C2 C1 H1B 108.6 . .
H1A C1 H1B 107.6 . .
N2 C2 C1 112.9(2) . .
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 114.2(2) . 2
N2 C3 H3A 108.7 . .
C4 C3 H3A 108.7 2 .
N2 C3 H3B 108.7 . .
C4 C3 H3B 108.7 2 .
H3A C3 H3B 107.6 . .
N1 C4 C3 112.9(2) . 2
N1 C4 H4A 109.0 . .
C3 C4 H4A 109.0 2 .
N1 C4 H4B 109.0 . .
C3 C4 H4B 109.0 2 .
H4A C4 H4B 107.8 . .
N1 C9 C10 112.6(3) . .
N1 C9 H9A 109.1 . .
C10 C9 H9A 109.1 . .
N1 C9 H9B 109.1 . .
C10 C9 H9B 109.1 . .
H9A C9 H9B 107.8 . .
C15 C10 C11 118.5(3) . .
C15 C10 C9 122.3(3) . .
C11 C10 C9 119.2(3) . .
C12 C11 C10 120.7(3) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C13 C12 C11 120.3(3) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C14 120.1(3) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C13 C14 C15 120.1(4) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C10 C15 C14 120.2(3) . .
C10 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
N2 C16 C17 112.0(2) . .
N2 C16 H16A 109.2 . .
C17 C16 H16A 109.2 . .
N2 C16 H16B 109.2 . .
C17 C16 H16B 109.2 . .
H16A C16 H16B 107.9 . .
C22 C17 C18 118.8(3) . .
C22 C17 C16 122.2(3) . .
C18 C17 C16 118.9(3) . .
C19 C18 C17 120.3(4) . .
C19 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
C18 C19 C20 120.3(3) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C21 C20 C19 120.3(3) . .
C21 C20 H20 119.9 . .
C19 C20 H20 119.9 . .
C20 C21 C22 119.2(4) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
C17 C22 C21 121.0(3) . .
C17 C22 H22 119.5 . .
C21 C22 H22 119.5 . .
C37 F1 C37 46.9(6) . 2_655
C1 N1 C4 111.2(2) . .
C1 N1 C9 109.0(2) . .
C4 N1 C9 109.8(2) . .
C1 N1 Ag1 105.25(17) . .
C4 N1 Ag1 103.05(16) . .
C9 N1 Ag1 118.30(17) . .
C2 N2 C3 111.5(2) . .
C2 N2 C16 109.9(2) . .
C3 N2 C16 108.6(2) . .
C2 N2 Ag1 104.49(17) . .
C3 N2 Ag1 105.56(16) . .
C16 N2 Ag1 116.70(18) . .
S1 O2 S1 59.4(4) 2_655 .
C37 C37 F1 66.5(3) 2_655 .
C37 C37 S1 95.5(4) 2_655 .
F1 C37 S1 162.0(6) . .
C37 C37 F3 125.4(11) 2_655 .
F1 C37 F3 107.0(7) . .
S1 C37 F3 81.8(6) . .
C37 C37 F2 117.1(10) 2_655 .
F1 C37 F2 97.9(7) . .
S1 C37 F2 91.4(7) . .
F3 C37 F2 117.4(7) . .
C37 C37 S1 49.3(3) 2_655 2_655
F1 C37 S1 115.8(5) . 2_655
S1 C37 S1 46.3(3) . 2_655
F3 C37 S1 109.9(5) . 2_655
F2 C37 S1 108.7(5) . 2_655
S1 S1 O2 60.31(18) 2_655 .
S1 S1 C37 84.4(4) 2_655 .
O2 S1 C37 144.7(4) . .
S1 S1 O1 128.5(5) 2_655 .
O2 S1 O1 113.9(4) . .
C37 S1 O1 87.9(5) . .
S1 S1 O3 116.2(4) 2_655 .
O2 S1 O3 107.3(6) . .
C37 S1 O3 86.4(7) . .
O1 S1 O3 114.0(5) . .
S1 S1 C37 49.3(3) 2_655 2_655
O2 S1 C37 109.6(4) . 2_655
C37 S1 C37 35.2(6) . 2_655
O1 S1 C37 108.2(4) . 2_655
O3 S1 C37 103.5(5) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N2 2.454(2) 2
Ag1 N2 2.454(2) .
Ag1 N1 2.494(2) .
Ag1 N1 2.494(2) 2
C1 N1 1.475(4) .
C1 C2 1.522(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C2 N2 1.476(4) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C3 N2 1.483(4) .
C3 C4 1.522(4) 2
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C4 N1 1.476(4) .
C4 C3 1.522(4) 2
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C9 N1 1.495(4) .
C9 C10 1.501(4) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C10 C15 1.385(4) .
C10 C11 1.391(4) .
C11 C12 1.386(5) .
C11 H11 0.9400 .
C12 C13 1.368(6) .
C12 H12 0.9400 .
C13 C14 1.371(6) .
C13 H13 0.9400 .
C14 C15 1.401(5) .
C14 H14 0.9400 .
C15 H15 0.9400 .
C16 N2 1.487(4) .
C16 C17 1.512(4) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C17 C22 1.383(5) .
C17 C18 1.391(4) .
C18 C19 1.378(5) .
C18 H18 0.9400 .
C19 C20 1.380(6) .
C19 H19 0.9400 .
C20 C21 1.378(6) .
C20 H20 0.9400 .
C21 C22 1.392(5) .
C21 H21 0.9400 .
C22 H22 0.9400 .
F1 C37 1.284(10) .
F1 C37 1.284(10) 2_655
F2 C37 1.383(10) .
F3 C37 1.367(9) .
O1 S1 1.347(6) .
O2 S1 1.295(6) 2_655
O2 S1 1.295(6) .
O3 S1 1.384(8) .
C37 C37 1.023(16) 2_655
C37 S1 1.344(8) .
C37 S1 1.766(6) 2_655
S1 S1 1.283(7) 2_655
S1 C37 1.766(6) 2_655
