#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:50:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178919 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/48/4114852.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_4114852
loop_
_publ_author_name
'Antonio Codina'
'Eduardo J. Fernández'
'Peter G. Jones'
'Antonio Laguna'
'José M. López-de-Luzuriaga'
'Miguel Monge'
'M. Elena Olmos'
'Javier Pérez'
'Miguel A. Rodríguez'
_publ_section_title
;
 Do Aurophilic Interactions Compete against Hydrogen Bonds? Experimental
 Evidence and Rationalization Based on ab Initio Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6781
_journal_page_last               6786
_journal_paper_doi               10.1021/ja025765g
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C19 H11 Ag F5 N'
_chemical_formula_weight         456.16
_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                 95.168(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5320(16)
_cell_length_b                   5.6217(8)
_cell_length_c                   21.626(3)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      3
_cell_volume                     1638.5(4)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω-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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4295
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.285
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   Psi-scans
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_description       tablet
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    'NH free, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0187
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0476
_reflns_number_gt                2518
_reflns_number_total             2884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja025765g_s1_1.cif
_cod_data_source_block           agimin
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4114852
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
Ag Ag 0.022704(11) 0.40098(3) 0.065816(7) 0.02409(7) Uani 1 1 d .
N N 0.17715(13) 0.3500(3) 0.09112(8) 0.0240(4) Uani 1 1 d .
H0 H 0.2136(16) 0.267(4) 0.0662(10) 0.029(6) Uiso 1 1 d .
C1 C 0.23196(15) 0.4324(4) 0.13796(9) 0.0212(4) Uani 1 1 d .
C11 C -0.13087(15) 0.4541(4) 0.05559(9) 0.0224(5) Uani 1 1 d .
C12 C -0.16969(15) 0.6527(4) 0.08216(9) 0.0239(5) Uani 1 1 d .
C13 C -0.26935(16) 0.7041(4) 0.07958(9) 0.0270(5) Uani 1 1 d .
C14 C -0.33640(15) 0.5539(4) 0.04784(10) 0.0292(5) Uani 1 1 d .
C15 C -0.30196(16) 0.3521(4) 0.02075(10) 0.0294(5) Uani 1 1 d .
C16 C -0.20106(15) 0.3081(4) 0.02532(9) 0.0242(4) Uani 1 1 d .
F1 F -0.10771(9) 0.8119(2) 0.11318(6) 0.0347(3) Uani 1 1 d .
F2 F -0.30276(10) 0.9002(2) 0.10736(7) 0.0401(3) Uani 1 1 d .
F3 F -0.43333(9) 0.6042(3) 0.04414(7) 0.0438(4) Uani 1 1 d .
F4 F -0.36703(10) 0.2024(3) -0.01022(6) 0.0465(4) Uani 1 1 d .
F5 F -0.17228(10) 0.1070(2) -0.00378(6) 0.0351(3) Uani 1 1 d .
C21 C 0.33968(15) 0.3725(4) 0.14882(9) 0.0227(4) Uani 1 1 d .
C22 C 0.40541(16) 0.5299(4) 0.18159(10) 0.0272(5) Uani 1 1 d .
H22 H 0.3809 0.6710 0.1990 0.033 Uiso 1 1 calc R
C23 C 0.50603(16) 0.4803(5) 0.18871(11) 0.0336(5) Uani 1 1 d .
H23 H 0.5502 0.5873 0.2111 0.040 Uiso 1 1 calc R
C24 C 0.54259(16) 0.2759(5) 0.16335(10) 0.0349(5) Uani 1 1 d .
H24 H 0.6117 0.2430 0.1681 0.042 Uiso 1 1 calc R
C25 C 0.47781(17) 0.1192(4) 0.13093(11) 0.0358(6) Uani 1 1 d .
H25 H 0.5028 -0.0209 0.1133 0.043 Uiso 1 1 calc R
C26 C 0.37751(17) 0.1658(4) 0.12416(10) 0.0306(5) Uani 1 1 d .
H26 H 0.3336 0.0561 0.1025 0.037 Uiso 1 1 calc R
C31 C 0.18732(14) 0.5972(4) 0.18118(9) 0.0203(4) Uani 1 1 d .
C32 C 0.12983(14) 0.7876(4) 0.15803(9) 0.0234(4) Uani 1 1 d .
H32 H 0.1190 0.8111 0.1144 0.028 Uiso 1 1 calc R
C33 C 0.08814(15) 0.9435(4) 0.19802(10) 0.0266(5) Uani 1 1 d .
H33 H 0.0498 1.0746 0.1818 0.032 Uiso 1 1 calc R
C34 C 0.10225(15) 0.9083(4) 0.26158(10) 0.0270(5) Uani 1 1 d .
H34 H 0.0732 1.0143 0.2889 0.032 Uiso 1 1 calc R
C35 C 0.15886(16) 0.7181(4) 0.28516(9) 0.0279(5) Uani 1 1 d .
H35 H 0.1681 0.6934 0.3288 0.034 Uiso 1 1 calc R
C36 C 0.20207(15) 0.5637(4) 0.24557(9) 0.0246(5) Uani 1 1 d .
H36 H 0.2417 0.4351 0.2621 0.029 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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_3
C11 Ag N 171.23(7) .
C11 Ag Ag 74.68(5) 3_565
N Ag Ag 113.38(5) 3_565
C1 N Ag 129.50(15) .
N C1 C31 118.85(18) .
N C1 C21 121.85(18) .
C31 C1 C21 119.27(17) .
C16 C11 C12 114.09(19) .
C16 C11 Ag 127.02(16) .
C12 C11 Ag 118.89(15) .
F1 C12 C13 116.11(19) .
F1 C12 C11 119.74(18) .
C13 C12 C11 124.15(19) .
F2 C13 C12 121.26(19) .
F2 C13 C14 119.32(19) .
C12 C13 C14 119.4(2) .
F3 C14 C13 119.9(2) .
F3 C14 C15 121.10(19) .
C13 C14 C15 119.0(2) .
F4 C15 C14 119.6(2) .
F4 C15 C16 121.3(2) .
C14 C15 C16 119.1(2) .
F5 C16 C11 119.95(19) .
F5 C16 C15 115.81(18) .
C11 C16 C15 124.2(2) .
C26 C21 C22 118.78(19) .
C26 C21 C1 120.95(19) .
C22 C21 C1 120.20(19) .
C23 C22 C21 120.1(2) .
C24 C23 C22 120.4(2) .
C23 C24 C25 119.7(2) .
C26 C25 C24 120.3(2) .
C25 C26 C21 120.7(2) .
C32 C31 C36 119.10(19) .
C32 C31 C1 120.05(17) .
C36 C31 C1 120.85(18) .
C33 C32 C31 120.54(19) .
C34 C33 C32 120.1(2) .
C33 C34 C35 119.86(19) .
C36 C35 C34 120.41(19) .
C35 C36 C31 120.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag C11 2.091(2) .
Ag N 2.1315(17) .
Ag Ag 3.0668(4) 3_565
N C1 1.287(3) .
C1 C31 1.483(3) .
C1 C21 1.494(3) .
C11 C16 1.376(3) .
C11 C12 1.381(3) .
C12 F1 1.362(2) .
C12 C13 1.375(3) .
C13 F2 1.353(3) .
C13 C14 1.377(3) .
C14 F3 1.337(2) .
C14 C15 1.377(3) .
C15 F4 1.351(2) .
C15 C16 1.382(3) .
C16 F5 1.368(2) .
C21 C26 1.395(3) .
C21 C22 1.401(3) .
C22 C23 1.385(3) .
C23 C24 1.384(4) .
C24 C25 1.388(3) .
C25 C26 1.377(3) .
C31 C32 1.390(3) .
C31 C36 1.402(3) .
C32 C33 1.386(3) .
C33 C34 1.385(3) .
C34 C35 1.385(3) .
C35 C36 1.385(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
N H0 F5 0.89(2) 2.53(2) 3.186(2) 130.4(18) 3
