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#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/60/7116066.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_7116066
loop_
_publ_author_name
'Dengtai Chen'
'Xijiang Han'
'Wen Jin'
'Yunchen Du'
'Ping Xu'
_publ_section_title
;
 In situ Raman monitoring of [2+2] cycloaddition of pyridine substituted
 olefins induced by visible laser
;
_journal_name_full               Chem.Commun.
_journal_page_first              15631
_journal_paper_doi               10.1039/C4cc06808D
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C13.5 H11 Ag0.5 F1.5 N O3'
_chemical_formula_weight         317.67
_chemical_melting_point          339.15
_chemical_name_common
'[Ag2(PEA)4][TFA]2 (PEA = Ethyl-(pyridine-4-yl)prop-2-enotate, TFA =TFA = trifluoroacetate) '
_chemical_name_systematic
'[Ag2(Ethyl-(pyridine-4-yl)prop-2-enotate)4][trifluoroacetate]2 '
_chemical_properties_physical    'Air-sensitive, Light-sensitive'
_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                112.017(5)
_cell_angle_beta                 93.953(5)
_cell_angle_gamma                94.913(6)
_cell_formula_units_Z            4
_cell_length_a                   7.2173(19)
_cell_length_b                   13.875(4)
_cell_length_c                   14.970(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1376.4(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4727
_diffrn_reflns_theta_full        20.93
_diffrn_reflns_theta_max         20.93
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.795
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method 'liquid-liquid difussion'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     490
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                1535
_reflns_number_total             2913
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06808d2.cif
_cod_data_source_block           x1
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C13.50 H11 Ag0.50 F1.50 N O3'
_cod_database_code               7116066
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_group
Ag1 Ag 0.64621(10) 0.54061(7) 0.44420(4) 0.1148(4) Uani 1 1 d . .
N1 N 0.5173(9) 0.5067(7) 0.3006(5) 0.087(2) Uani 1 1 d . .
N2 N 0.8163(9) 0.5965(7) 0.5810(5) 0.089(2) Uani 1 1 d . .
C1 C 0.4349(12) 0.5769(8) 0.2767(6) 0.095(3) Uani 1 1 d U .
H1A H 0.4315 0.6426 0.3249 0.114 Uiso 1 1 calc R .
C2 C 0.3536(11) 0.5581(7) 0.1841(6) 0.090(2) Uani 1 1 d U .
H2A H 0.2968 0.6100 0.1714 0.108 Uiso 1 1 calc R .
C3 C 0.3578(11) 0.4611(8) 0.1106(6) 0.077(2) Uani 1 1 d U .
C4 C 0.4404(10) 0.3877(7) 0.1348(5) 0.086(2) Uani 1 1 d U .
H4A H 0.4470 0.3216 0.0881 0.104 Uiso 1 1 calc R .
C5 C 0.5147(11) 0.4136(8) 0.2308(6) 0.088(3) Uani 1 1 d U .
H5A H 0.5655 0.3619 0.2464 0.106 Uiso 1 1 calc R .
C6 C 0.2726(10) 0.4406(7) 0.0113(6) 0.087(2) Uani 1 1 d U .
H6A H 0.2061 0.4918 0.0032 0.105 Uiso 1 1 calc R .
C7 C 0.2825(11) 0.3576(7) -0.0653(6) 0.095(3) Uani 1 1 d U .
H7A H 0.3462 0.3041 -0.0601 0.114 Uiso 1 1 calc R .
C8 C 0.1931(15) 0.3475(10) -0.1608(8) 0.103(3) Uani 1 1 d U .
C9 C 0.1441(14) 0.2371(8) -0.3261(6) 0.131(3) Uani 1 1 d DU .
H9A H 0.1878 0.2944 -0.3445 0.157 Uiso 1 1 calc R .
H9B H 0.0086 0.2305 -0.3305 0.157 Uiso 1 1 calc R .
C10 C 0.2092(16) 0.1359(8) -0.3918(7) 0.188(5) Uani 1 1 d DU .
H10A H 0.1596 0.1199 -0.4576 0.282 Uiso 1 1 calc R .
H10B H 0.1658 0.0800 -0.3725 0.282 Uiso 1 1 calc R .
H10C H 0.3434 0.1437 -0.3870 0.282 Uiso 1 1 calc R .
C11 C 0.8295(12) 0.6952(9) 0.6468(7) 0.105(3) Uani 1 1 d U .
H11A H 0.7791 0.7450 0.6280 0.126 Uiso 1 1 calc R .
C12 C 0.9119(12) 0.7266(8) 0.7393(6) 0.105(3) Uani 1 1 d U .
H12A H 0.9144 0.7959 0.7817 0.126 Uiso 1 1 calc R .
C13 C 0.9909(12) 0.6573(9) 0.7703(6) 0.091(3) Uani 1 1 d U .
C14 C 0.9825(11) 0.5550(8) 0.7043(6) 0.093(3) Uani 1 1 d U .
H14A H 1.0340 0.5046 0.7220 0.111 Uiso 1 1 calc R .
C15 C 0.8957(11) 0.5292(7) 0.6115(6) 0.092(3) Uani 1 1 d U .
H15A H 0.8926 0.4606 0.5676 0.110 Uiso 1 1 calc R .
C16 C 1.0768(12) 0.6805(8) 0.8712(7) 0.112(3) Uani 1 1 d U .
H16A H 1.1235 0.6245 0.8812 0.134 Uiso 1 1 calc R .
C17 C 1.0941(13) 0.7613(9) 0.9411(7) 0.119(3) Uani 1 1 d U .
H17A H 1.0495 0.8195 0.9345 0.143 Uiso 1 1 calc R .
C18 C 1.1833(15) 0.7729(11) 1.0379(7) 0.109(3) Uani 1 1 d U .
C19 C 1.2509(15) 0.8882(8) 1.1983(7) 0.154(4) Uani 1 1 d DU .
H19A H 1.3861 0.8956 1.1995 0.184 Uiso 1 1 calc R .
H19B H 1.2127 0.8319 1.2191 0.184 Uiso 1 1 calc R .
C20 C 1.1875(18) 0.9880(9) 1.2622(8) 0.224(6) Uani 1 1 d DU .
H20A H 1.2435 1.0069 1.3274 0.337 Uiso 1 1 calc R .
H20B H 1.0538 0.9791 1.2605 0.337 Uiso 1 1 calc R .
H20C H 1.2243 1.0425 1.2397 0.337 Uiso 1 1 calc R .
C23 C 0.541(3) 0.9207(11) 0.9337(13) 0.165(5) Uani 1 1 d U .
C24 C 0.395(2) 0.9784(14) 0.9177(11) 0.142(4) Uani 1 1 d U .
C25 C 0.3466(19) 1.0615(11) 0.9850(11) 0.159(4) Uani 1 1 d U .
C26 C 0.2986(18) 0.9416(10) 0.8255(10) 0.192(5) Uani 1 1 d U .
C27 C 0.5660(19) 0.8447(11) 0.8568(10) 0.190(5) Uani 1 1 d U .
O1 O 0.2230(9) 0.2561(5) -0.2280(4) 0.116(2) Uani 1 1 d D .
O2 O 0.1076(9) 0.4086(6) -0.1779(4) 0.121(3) Uani 1 1 d . .
O3 O 1.1616(10) 0.8672(6) 1.1016(5) 0.135(3) Uani 1 1 d D .
O4 O 1.2626(11) 0.7128(6) 1.0593(4) 0.138(3) Uani 1 1 d . .
C21 C 0.3494(17) 0.7258(13) 0.5934(8) 0.132(4) Uani 1 1 d DU .
C22 C 0.2864(16) 0.8086(11) 0.5561(8) 0.173(6) Uani 1 1 d DU .
O5 O 0.370(3) 0.6336(10) 0.5470(15) 0.151(8) Uani 0.591(16) 1 d PDU 1
O6 O 0.370(5) 0.7894(19) 0.6796(8) 0.190(12) Uani 0.591(16) 1 d PDU 1
F1 F 0.226(4) 0.8908(17) 0.6185(14) 0.260(12) Uani 0.591(16) 1 d PDU 1
F2 F 0.142(3) 0.7584(12) 0.4917(17) 0.228(9) Uani 0.591(16) 1 d PDU 1
F3 F 0.409(3) 0.842(2) 0.511(2) 0.298(12) Uani 0.591(16) 1 d PDU 1
O5B O 0.432(4) 0.692(3) 0.5199(13) 0.210(16) Uani 0.409(16) 1 d PDU 2
O6B O 0.379(7) 0.750(3) 0.6822(12) 0.149(10) Uani 0.409(16) 1 d PDU 2
F1B F 0.403(3) 0.8963(16) 0.595(2) 0.230(12) Uani 0.409(16) 1 d PDU 2
F2B F 0.121(3) 0.838(2) 0.580(3) 0.192(11) Uani 0.409(16) 1 d PDU 2
F3B F 0.277(5) 0.786(3) 0.4618(9) 0.248(13) Uani 0.409(16) 1 d PDU 2
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'
Ag Ag -0.8971 1.1015 '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'
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
N1 Ag1 N2 167.9(3) . .
N1 Ag1 O5 102.8(5) . 2_666
N2 Ag1 O5 86.3(5) . 2_666
N1 Ag1 Ag1 107.96(18) . 2_666
N2 Ag1 Ag1 83.64(18) . 2_666
O5 Ag1 Ag1 56.2(5) 2_666 2_666
C5 N1 C1 116.2(8) . .
C5 N1 Ag1 121.4(7) . .
C1 N1 Ag1 122.5(7) . .
C15 N2 C11 115.2(8) . .
C15 N2 Ag1 120.2(7) . .
C11 N2 Ag1 124.0(7) . .
N1 C1 C2 123.8(9) . .
N1 C1 H1A 118.1 . .
C2 C1 H1A 118.1 . .
C1 C2 C3 119.4(8) . .
C1 C2 H2A 120.3 . .
C3 C2 H2A 120.3 . .
C4 C3 C2 117.2(8) . .
C4 C3 C6 123.1(9) . .
C2 C3 C6 119.7(8) . .
C3 C4 C5 119.1(9) . .
C3 C4 H4A 120.5 . .
C5 C4 H4A 120.5 . .
N1 C5 C4 124.3(8) . .
N1 C5 H5A 117.9 . .
C4 C5 H5A 117.9 . .
C7 C6 C3 125.8(9) . .
C7 C6 H6A 117.1 . .
C3 C6 H6A 117.1 . .
C6 C7 C8 120.4(10) . .
C6 C7 H7A 119.8 . .
C8 C7 H7A 119.8 . .
O2 C8 O1 123.6(10) . .
O2 C8 C7 127.1(11) . .
O1 C8 C7 109.3(10) . .
O1 C9 C10 106.6(8) . .
O1 C9 H9A 110.4 . .
C10 C9 H9A 110.4 . .
O1 C9 H9B 110.4 . .
C10 C9 H9B 110.4 . .
H9A C9 H9B 108.6 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N2 C11 C12 124.1(9) . .
N2 C11 H11A 118.0 . .
C12 C11 H11A 118.0 . .
C13 C12 C11 120.5(10) . .
C13 C12 H12A 119.8 . .
C11 C12 H12A 119.8 . .
C12 C13 C14 117.4(9) . .
C12 C13 C16 125.7(10) . .
C14 C13 C16 116.9(10) . .
C15 C14 C13 118.6(9) . .
C15 C14 H14A 120.7 . .
C13 C14 H14A 120.7 . .
N2 C15 C14 124.3(9) . .
N2 C15 H15A 117.8 . .
C14 C15 H15A 117.8 . .
C17 C16 C13 129.2(12) . .
C17 C16 H16A 115.4 . .
C13 C16 H16A 115.4 . .
C16 C17 C18 123.3(13) . .
C16 C17 H17A 118.4 . .
C18 C17 H17A 118.4 . .
O4 C18 O3 122.7(10) . .
O4 C18 C17 128.9(12) . .
O3 C18 C17 108.5(11) . .
O3 C19 C20 105.4(9) . .
O3 C19 H19A 110.7 . .
C20 C19 H19A 110.7 . .
O3 C19 H19B 110.7 . .
C20 C19 H19B 110.7 . .
H19A C19 H19B 108.8 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C27 C23 C25 118(2) . 2_677
C27 C23 C24 112(2) . .
C25 C23 C24 129.2(16) 2_677 .
C25 C24 C26 119.1(19) . .
C25 C24 C23 123.7(15) . .
C26 C24 C23 117(2) . .
C24 C25 C23 107.0(15) . 2_677
C8 O1 C9 114.9(8) . .
C18 O3 C19 112.9(8) . .
O5 C21 O5B 53.3(16) . .
O5 C21 O6B 112(3) . .
O5B C21 O6B 139(2) . .
O5 C21 O6 139(2) . .
O5B C21 O6 143(3) . .
O6B C21 O6 27(2) . .
O5 C21 C22 129.1(14) . .
O5B C21 C22 87(2) . .
O6B C21 C22 119(2) . .
O6 C21 C22 92.3(15) . .
F3 C22 F1 107.2(12) . .
F3 C22 F2 107.1(12) . .
F1 C22 F2 106.0(12) . .
F3 C22 F2B 131(2) . .
F1 C22 F2B 44.1(11) . .
F2 C22 F2B 63.9(10) . .
F3 C22 F3B 53.9(11) . .
F1 C22 F3B 124(3) . .
F2 C22 F3B 53.6(11) . .
F2B C22 F3B 104.5(12) . .
F3 C22 F1B 54.2(10) . .
F1 C22 F1B 61.9(10) . .
F2 C22 F1B 145(2) . .
F2B C22 F1B 104.4(12) . .
F3B C22 F1B 104.2(12) . .
F3 C22 C21 114.7(17) . .
F1 C22 C21 117.3(16) . .
F2 C22 C21 103.8(12) . .
F2B C22 C21 114.2(15) . .
F3B C22 C21 117.8(18) . .
F1B C22 C21 110.5(19) . .
C21 O5 Ag1 143.1(19) . 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N1 2.145(6) .
Ag1 N2 2.145(6) .
Ag1 O5 2.464(15) 2_666
Ag1 Ag1 3.1631(15) 2_666
N1 C5 1.319(9) .
N1 C1 1.328(9) .
N2 C15 1.336(9) .
N2 C11 1.345(10) .
C1 C2 1.387(9) .
C1 H1A 0.9300 .
C2 C3 1.387(10) .
C2 H2A 0.9300 .
C3 C4 1.369(10) .
C3 C6 1.482(9) .
C4 C5 1.398(9) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C6 C7 1.297(9) .
C6 H6A 0.9300 .
C7 C8 1.478(11) .
C7 H7A 0.9300 .
C8 O2 1.182(10) .
C8 O1 1.337(11) .
C9 O1 1.455(7) .
C9 C10 1.517(8) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.360(10) .
C11 H11A 0.9300 .
C12 C13 1.362(11) .
C12 H12A 0.9300 .
C13 C14 1.387(11) .
C13 C16 1.497(11) .
C14 C15 1.385(9) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
C16 C17 1.203(10) .
C16 H16A 0.9300 .
C17 C18 1.489(12) .
C17 H17A 0.9300 .
C18 O4 1.177(11) .
C18 O3 1.329(12) .
C19 O3 1.456(7) .
C19 C20 1.489(8) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C23 C27 1.272(15) .
C23 C25 1.34(2) 2_677
C23 C24 1.441(19) .
C24 C25 1.307(17) .
C24 C26 1.387(15) .
C25 C23 1.34(2) 2_677
C21 O5 1.232(9) .
C21 O5B 1.238(10) .
C21 O6B 1.242(10) .
C21 O6 1.251(9) .
C21 C22 1.541(15) .
C22 F3 1.299(10) .
C22 F1 1.305(10) .
C22 F2 1.315(10) .
C22 F2B 1.320(10) .
C22 F3B 1.322(11) .
C22 F1B 1.324(11) .
O5 Ag1 2.464(15) 2_666
