#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119989.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_4119989
loop_
_publ_author_name
'Ying-Feng Han'
'Guo-Xin Jin'
'F. Ekkehardt Hahn'
_publ_section_title
;
 Postsynthetic Modification of Dicarbene-Derived Metallacycles via
 Photochemical [2 + 2] Cycloaddition
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9263
_journal_page_last               9266
_journal_paper_doi               10.1021/ja4032067
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C56 H64 Ag2 N8, 2(F6 P), 2(C2 H3 N)'
_chemical_formula_sum            'C60 H70 Ag2 F12 N10 P2'
_chemical_formula_weight         1436.94
_chemical_name_systematic
; 
 ? 
;
_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                102.6720(10)
_cell_angle_beta                 109.0550(10)
_cell_angle_gamma                111.0600(10)
_cell_formula_units_Z            1
_cell_length_a                   11.7685(2)
_cell_length_b                   12.2958(2)
_cell_length_c                   13.1428(2)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.34706
_cell_measurement_theta_min      2.5955
_cell_volume                     1550.51(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Goebel mirror'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22567
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_correction_T_min  0.8605
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 numerical correction included in APEX2 package (Bruker AXS, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       prism
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.342
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         8980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0434
_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)+(0.0596P)²+2.2504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                7844
_reflns_number_total             8980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4032067_si_002.cif
_cod_data_source_block           structureneu
_cod_original_cell_volume        1550.51(4)
_cod_database_code               4119989
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
Ag1 Ag 0.92333(2) 0.629377(17) -0.513903(15) 0.02805(7) Uani 1 1 d .
N1 N 0.7260(2) 0.46931(19) -0.43525(18) 0.0275(4) Uani 1 1 d .
N2 N 0.7136(2) 0.3496(2) -0.58775(18) 0.0301(5) Uani 1 1 d .
N3 N 0.8541(2) 1.0967(2) 0.43475(18) 0.0275(4) Uani 1 1 d .
N4 N 0.8706(2) 1.2151(2) 0.58989(19) 0.0292(4) Uani 1 1 d .
C1 C 0.7818(3) 0.4705(2) -0.5107(2) 0.0274(5) Uani 1 1 d .
C2 C 0.6159(3) 0.2752(3) -0.5624(2) 0.0358(6) Uani 1 1 d .
H2 H 0.5548 0.1878 -0.6047 0.043 Uiso 1 1 calc R
C3 C 0.6238(3) 0.3505(2) -0.4660(3) 0.0357(6) Uani 1 1 d .
H3 H 0.5697 0.3264 -0.4269 0.043 Uiso 1 1 calc R
C4 C 0.7364(3) 0.3038(3) -0.6882(2) 0.0375(6) Uani 1 1 d .
H4A H 0.7475 0.2276 -0.6887 0.045 Uiso 1 1 calc R
H4B H 0.8218 0.3691 -0.6802 0.045 Uiso 1 1 calc R
C5 C 0.6209(4) 0.2720(3) -0.8028(3) 0.0408(7) Uani 1 1 d .
H5A H 0.6388 0.2358 -0.8674 0.049 Uiso 1 1 calc R
H5B H 0.5356 0.2067 -0.8106 0.049 Uiso 1 1 calc R
C6 C 0.6013(4) 0.3838(3) -0.8145(3) 0.0441(7) Uani 1 1 d .
H6A H 0.6863 0.4496 -0.8067 0.053 Uiso 1 1 calc R
H6B H 0.5817 0.4195 -0.7511 0.053 Uiso 1 1 calc R
C7 C 0.4853(4) 0.3471(4) -0.9313(3) 0.0523(8) Uani 1 1 d .
H7A H 0.5018 0.3068 -0.9943 0.079 Uiso 1 1 calc R
H7B H 0.4798 0.4228 -0.9390 0.079 Uiso 1 1 calc R
H7C H 0.3996 0.2882 -0.9361 0.079 Uiso 1 1 calc R
C8 C 0.7676(3) 0.5787(2) -0.3372(2) 0.0278(5) Uani 1 1 d .
C9 C 0.8995(3) 0.6408(2) -0.2510(2) 0.0311(5) Uani 1 1 d .
H9 H 0.9620 0.6098 -0.2539 0.037 Uiso 1 1 calc R
C10 C 0.9398(3) 0.7507(2) -0.1587(2) 0.0311(5) Uani 1 1 d .
H10 H 1.0300 0.7931 -0.0979 0.037 Uiso 1 1 calc R
C11 C 0.8500(3) 0.7989(2) -0.1546(2) 0.0289(5) Uani 1 1 d .
C12 C 0.7177(3) 0.7325(3) -0.2411(2) 0.0364(6) Uani 1 1 d .
H12 H 0.6546 0.7626 -0.2381 0.044 Uiso 1 1 calc R
C13 C 0.6751(3) 0.6224(3) -0.3324(2) 0.0361(6) Uani 1 1 d .
H13 H 0.5836 0.5775 -0.3910 0.043 Uiso 1 1 calc R
C14 C 0.8956(3) 0.9248(2) -0.0642(2) 0.0274(5) Uani 1 1 d .
H14 H 0.8156 0.9380 -0.0681 0.033 Uiso 1 1 calc R
C15 C 0.9287(3) 1.2160(2) 0.5167(2) 0.0273(5) Uani 1 1 d .
C16 C 0.7613(3) 1.0994(3) 0.5543(2) 0.0340(6) Uani 1 1 d .
H16 H 0.7048 1.0768 0.5918 0.041 Uiso 1 1 calc R
C17 C 0.7500(3) 1.0244(3) 0.4555(2) 0.0331(5) Uani 1 1 d .
H17 H 0.6837 0.9389 0.4095 0.040 Uiso 1 1 calc R
C18 C 0.9203(3) 1.3242(3) 0.6952(2) 0.0345(6) Uani 1 1 d .
H18A H 0.8446 1.3166 0.7156 0.041 Uiso 1 1 calc R
H18B H 0.9505 1.4019 0.6789 0.041 Uiso 1 1 calc R
C19 C 1.0366(3) 1.3361(3) 0.7978(2) 0.0342(6) Uani 1 1 d .
H19A H 1.1120 1.3427 0.7773 0.041 Uiso 1 1 calc R
H19B H 1.0063 1.2591 0.8152 0.041 Uiso 1 1 calc R
C20 C 1.0880(3) 1.4505(3) 0.9052(3) 0.0434(7) Uani 1 1 d .
H20A H 1.0122 1.4437 0.9253 0.052 Uiso 1 1 calc R
H20B H 1.1180 1.5272 0.8875 0.052 Uiso 1 1 calc R
C21 C 1.2050(4) 1.4643(4) 1.0095(3) 0.0566(9) Uani 1 1 d .
H21A H 1.1762 1.3884 1.0273 0.085 Uiso 1 1 calc R
H21B H 1.2322 1.5379 1.0769 0.085 Uiso 1 1 calc R
H21C H 1.2821 1.4756 0.9918 0.085 Uiso 1 1 calc R
C22 C 0.8821(3) 1.0537(2) 0.3393(2) 0.0288(5) Uani 1 1 d .
C23 C 1.0083(3) 1.0585(3) 0.3625(2) 0.0323(5) Uani 1 1 d .
H23 H 1.0736 1.0870 0.4407 0.039 Uiso 1 1 calc R
C24 C 1.0388(3) 1.0217(3) 0.2717(2) 0.0338(6) Uani 1 1 d .
H24 H 1.1248 1.0245 0.2881 0.041 Uiso 1 1 calc R
C25 C 0.9450(3) 0.9809(2) 0.1569(2) 0.0294(5) Uani 1 1 d .
C26 C 0.8184(3) 0.9735(3) 0.1353(2) 0.0349(6) Uani 1 1 d .
H26 H 0.7525 0.9433 0.0570 0.042 Uiso 1 1 calc R
C27 C 0.7853(3) 1.0096(3) 0.2266(2) 0.0342(6) Uani 1 1 d .
H27 H 0.6980 1.0037 0.2106 0.041 Uiso 1 1 calc R
C28 C 0.9914(3) 0.9558(2) 0.0635(2) 0.0272(5) Uani 1 1 d .
H28 H 1.0222 0.8902 0.0667 0.033 Uiso 1 1 calc R
P1 P 0.64900(7) 0.11974(7) 0.83196(6) 0.03102(15) Uani 1 1 d .
F1 F 0.7965(3) 0.2305(3) 0.8939(4) 0.1152(13) Uani 1 1 d .
F2 F 0.6818(3) 0.0670(3) 0.9323(2) 0.0779(8) Uani 1 1 d .
F3 F 0.7008(4) 0.0368(3) 0.7681(3) 0.0844(9) Uani 1 1 d .
F4 F 0.6160(3) 0.1681(3) 0.7296(3) 0.0838(9) Uani 1 1 d .
F5 F 0.5961(3) 0.1980(3) 0.8959(3) 0.0813(8) Uani 1 1 d .
F6 F 0.4998(2) 0.0039(2) 0.7666(3) 0.0718(7) Uani 1 1 d .
N60 N 0.6514(6) 0.6772(5) 0.4152(5) 0.0925(15) Uani 1 1 d .
C60 C 0.6368(9) 0.7047(6) 0.2249(5) 0.110(3) Uani 1 1 d .
H60A H 0.7249 0.7706 0.2401 0.166 Uiso 1 1 calc R
H60B H 0.5663 0.7299 0.1955 0.166 Uiso 1 1 calc R
H60C H 0.6145 0.6255 0.1666 0.166 Uiso 1 1 calc R
C61 C 0.6438(4) 0.6873(4) 0.3310(4) 0.0562(9) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C1 Ag1 C15 177.09(10) 2_775
C1 N1 C3 111.3(2) .
C1 N1 C8 123.9(2) .
C3 N1 C8 124.9(2) .
C1 N2 C2 111.4(2) .
C1 N2 C4 124.7(3) .
C2 N2 C4 123.9(2) .
C15 N3 C17 111.4(2) .
C15 N3 C22 123.3(2) .
C17 N3 C22 125.3(2) .
C15 N4 C16 111.8(2) .
C15 N4 C18 123.6(2) .
C16 N4 C18 124.7(2) .
N2 C1 N1 104.1(2) .
N2 C1 Ag1 129.3(2) .
N1 C1 Ag1 126.19(17) .
C3 C2 N2 106.7(2) .
C2 C3 N1 106.5(3) .
N2 C4 C5 112.6(2) .
C6 C5 C4 113.4(3) .
C5 C6 C7 111.3(3) .
C9 C8 C13 120.9(2) .
C9 C8 N1 119.6(2) .
C13 C8 N1 119.5(2) .
C8 C9 C10 118.8(3) .
C11 C10 C9 121.2(2) .
C12 C11 C10 118.4(2) .
C12 C11 C14 119.5(2) .
C10 C11 C14 122.0(2) .
C11 C12 C13 121.3(3) .
C8 C13 C12 119.4(3) .
C11 C14 C28 117.8(2) .
C11 C14 C28 116.7(2) 2_775
C28 C14 C28 89.41(19) 2_775
N4 C15 N3 104.0(2) .
N4 C15 Ag1 127.94(19) 2_775
N3 C15 Ag1 127.41(18) 2_775
C17 C16 N4 106.6(2) .
C16 C17 N3 106.3(2) .
N4 C18 C19 112.7(2) .
C18 C19 C20 111.9(2) .
C19 C20 C21 112.9(3) .
C27 C22 C23 120.7(2) .
C27 C22 N3 120.0(3) .
C23 C22 N3 119.3(2) .
C24 C23 C22 120.1(3) .
C23 C24 C25 120.7(3) .
C26 C25 C24 118.4(2) .
C26 C25 C28 124.0(2) .
C24 C25 C28 117.5(2) .
C25 C26 C27 121.6(3) .
C22 C27 C26 118.4(3) .
C25 C28 C14 119.1(2) .
C25 C28 C14 115.9(2) 2_775
C14 C28 C14 90.59(19) 2_775
F1 P1 F5 92.7(2) .
F1 P1 F4 89.5(2) .
F5 P1 F4 90.96(16) .
F1 P1 F3 88.4(2) .
F5 P1 F3 178.28(17) .
F4 P1 F3 90.39(15) .
F1 P1 F6 178.3(2) .
F5 P1 F6 89.04(17) .
F4 P1 F6 90.50(18) .
F3 P1 F6 89.88(18) .
F1 P1 F2 91.2(2) .
F5 P1 F2 90.73(16) .
F4 P1 F2 178.14(17) .
F3 P1 F2 87.90(15) .
F6 P1 F2 88.74(17) .
N60 C61 C60 178.1(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C1 2.082(3) .
Ag1 C15 2.084(3) 2_775
N1 C1 1.357(3) .
N1 C3 1.380(3) .
N1 C8 1.437(3) .
N2 C1 1.353(3) .
N2 C2 1.378(4) .
N2 C4 1.465(3) .
N3 C15 1.359(3) .
N3 C17 1.381(4) .
N3 C22 1.437(3) .
N4 C15 1.349(3) .
N4 C16 1.377(4) .
N4 C18 1.467(3) .
C2 C3 1.348(4) .
C4 C5 1.515(4) .
C5 C6 1.505(5) .
C6 C7 1.520(5) .
C8 C9 1.377(4) .
C8 C13 1.388(4) .
C9 C10 1.402(3) .
C10 C11 1.395(4) .
C11 C12 1.380(4) .
C11 C14 1.508(3) .
C12 C13 1.389(4) .
C14 C28 1.551(3) .
C14 C28 1.583(4) 2_775
C15 Ag1 2.084(3) 2_775
C16 C17 1.352(4) .
C18 C19 1.509(4) .
C19 C20 1.516(4) .
C20 C21 1.517(5) .
C22 C27 1.374(4) .
C22 C23 1.391(4) .
C23 C24 1.385(4) .
C24 C25 1.389(4) .
C25 C26 1.387(4) .
C25 C28 1.514(3) .
C26 C27 1.409(4) .
C28 C14 1.583(4) 2_775
P1 F1 1.557(3) .
P1 F5 1.561(2) .
P1 F4 1.577(2) .
P1 F3 1.587(2) .
P1 F6 1.591(2) .
P1 F2 1.591(2) .
N60 C61 1.118(6) .
C60 C61 1.439(7) .
