#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/29/4082920.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_4082920
loop_
_publ_author_name
'Flores, Jaime A.'
'Pal, Kuntal'
'Carroll, Maria E.'
'Pink, Maren'
'Karty, Jonathan A.'
'Mindiola, Daniel J.'
'Caulton, Kenneth G.'
_publ_section_title
;
 Mechanistic Understanding of a Silver Pyridylpyrrolide as a Catalyst for
 3 + 2 Cyclization of a Nitrile with Diazo Ester
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1544
_journal_paper_doi               10.1021/om400756t
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C17 H14 Ag F6 N3 O2'
_chemical_formula_sum            'C17 H14 Ag F6 N3 O2'
_chemical_formula_weight         514.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 97.708(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4411(12)
_cell_length_b                   6.8784(8)
_cell_length_c                   12.5348(14)
_cell_measurement_reflns_used    5097
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.28
_cell_volume                     892.09(18)
_computing_cell_refinement       'APEX II v2009.5.0 (Bruker, 2010)'
_computing_data_collection       'APEX II v2009.5.0 (Bruker, 2010)'
_computing_data_reduction        'APEX II v2009.5.0 (Bruker, 2010)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 83.33
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
'0.30 degree frames measured for 20 seconds each'
_diffrn_measurement_device       'APEX Kappa Duo'
_diffrn_measurement_device_type  Kappa
_diffrn_measurement_method       'omega and phi 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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8344
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  0.8886
_exptl_absorpt_correction_T_min  0.7518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing; 1995'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0203
_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)+(0.0178P)²+0.6595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0500
_reflns_number_gt                2073
_reflns_number_total             2221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400756t_si_002.cif
_cod_data_source_block           p21m
_cod_depositor_comments          'Adding full bibliography for 4082920.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc'
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4082920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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 -0.00900(2) 0.2500 0.506210(15) 0.02265(7) Uani 1 2 d S
F1 F -0.34086(18) 0.2500 0.92249(14) 0.0519(6) Uani 1 2 d S
F2 F -0.16085(13) 0.40529(18) 0.95428(8) 0.0349(3) Uani 1 1 d .
F3 F -0.48186(16) 0.2500 0.50859(14) 0.0401(5) Uani 1 2 d S
F4 F -0.33264(13) 0.0951(2) 0.44113(9) 0.0386(3) Uani 1 1 d .
O1 O 0.08293(17) 0.2500 0.18522(13) 0.0198(4) Uani 1 2 d S
O2 O 0.29647(17) 0.2500 0.17400(14) 0.0241(4) Uani 1 2 d S
N1 N 0.1131(2) 0.2500 0.68437(16) 0.0200(4) Uani 1 2 d S
N2 N -0.1466(2) 0.2500 0.62009(16) 0.0182(4) Uani 1 2 d S
N3 N 0.0700(2) 0.2500 0.35924(16) 0.0199(4) Uani 1 2 d S
C1 C 0.2414(3) 0.2500 0.7102(2) 0.0235(5) Uani 1 2 d S
H1A H 0.2935 0.2500 0.6536 0.028 Uiso 1 2 calc SR
C2 C 0.3021(3) 0.2500 0.8151(2) 0.0236(5) Uani 1 2 d S
H2A H 0.3937 0.2500 0.8305 0.028 Uiso 1 2 calc SR
C3 C 0.2255(3) 0.2500 0.8973(2) 0.0256(6) Uani 1 2 d S
H3A H 0.2639 0.2500 0.9705 0.031 Uiso 1 2 calc SR
C4 C 0.0924(3) 0.2500 0.87134(19) 0.0225(5) Uani 1 2 d S
H4A H 0.0388 0.2500 0.9269 0.027 Uiso 1 2 calc SR
C5 C 0.0369(3) 0.2500 0.76368(19) 0.0183(5) Uani 1 2 d S
C6 C -0.1036(2) 0.2500 0.72780(18) 0.0176(5) Uani 1 2 d S
C7 C -0.2109(3) 0.2500 0.7849(2) 0.0207(5) Uani 1 2 d S
C8 C -0.3221(3) 0.2500 0.7081(2) 0.0212(5) Uani 1 2 d S
H8A H -0.4096 0.2500 0.7214 0.025 Uiso 1 2 calc SR
C9 C -0.2773(2) 0.2500 0.60916(19) 0.0191(5) Uani 1 2 d S
C10 C -0.2176(3) 0.2500 0.9020(2) 0.0272(6) Uani 1 2 d S
C11 C -0.3547(3) 0.2500 0.5022(2) 0.0217(5) Uani 1 2 d S
C12 C 0.0050(2) 0.2500 0.26380(19) 0.0184(5) Uani 1 2 d S
C13 C 0.2055(2) 0.2500 0.23923(19) 0.0198(5) Uani 1 2 d S
C14 C 0.2013(2) 0.2500 0.34558(19) 0.0198(5) Uani 1 2 d S
H14A H 0.2731 0.2500 0.4009 0.024 Uiso 1 2 calc SR
C15 C -0.1360(2) 0.2500 0.2311(2) 0.0212(5) Uani 1 2 d S
H15A H -0.1796 0.2500 0.2939 0.032 Uiso 1 2 d SR
H15B H -0.1601 0.1360 0.1889 0.032 Uiso 1 1 d R
C16 C 0.4265(2) 0.2500 0.2290(2) 0.0251(6) Uani 1 2 d S
H16A H 0.4416 0.1354 0.2741 0.030 Uiso 1 1 d R
C17 C 0.5143(3) 0.2500 0.1429(3) 0.0426(8) Uani 1 2 d S
H17A H 0.6027 0.2500 0.1760 0.064 Uiso 1 2 d SR
H17B H 0.4981 0.3640 0.0989 0.064 Uiso 1 1 d 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'
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'
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
N3 Ag1 N2 161.42(8) . .
N3 Ag1 N1 125.78(8) . .
N2 Ag1 N1 72.80(8) . .
C12 O1 C13 104.67(19) . .
C13 O2 C16 114.21(19) . .
C1 N1 C5 119.4(2) . .
C1 N1 Ag1 127.69(16) . .
C5 N1 Ag1 112.87(16) . .
C9 N2 C6 107.1(2) . .
C9 N2 Ag1 133.26(16) . .
C6 N2 Ag1 119.66(17) . .
C12 N3 C14 106.7(2) . .
C12 N3 Ag1 125.94(18) . .
C14 N3 Ag1 127.37(16) . .
N1 C1 C2 123.2(2) . .
N1 C1 H1A 118.4 . .
C2 C1 H1A 118.4 . .
C1 C2 C3 118.1(3) . .
C1 C2 H2A 121.0 . .
C3 C2 H2A 121.0 . .
C4 C3 C2 119.1(2) . .
C4 C3 H3A 120.5 . .
C2 C3 H3A 120.5 . .
C3 C4 C5 120.1(2) . .
C3 C4 H4A 119.9 . .
C5 C4 H4A 119.9 . .
N1 C5 C4 120.0(2) . .
N1 C5 C6 115.8(2) . .
C4 C5 C6 124.2(2) . .
N2 C6 C7 108.9(2) . .
N2 C6 C5 118.9(2) . .
C7 C6 C5 132.2(2) . .
C8 C7 C6 107.0(2) . .
C8 C7 C10 122.3(2) . .
C6 C7 C10 130.6(2) . .
C9 C8 C7 105.4(2) . .
C9 C8 H8A 127.3 . .
C7 C8 H8A 127.3 . .
N2 C9 C8 111.5(2) . .
N2 C9 C11 121.1(2) . .
C8 C9 C11 127.4(2) . .
F1 C10 F2 106.01(15) . .
F1 C10 F2 106.01(15) . 4_565
F2 C10 F2 104.8(2) . 4_565
F1 C10 C7 111.3(2) . .
F2 C10 C7 114.01(14) . .
F2 C10 C7 114.01(14) 4_565 .
F3 C11 F4 106.25(15) . .
F3 C11 F4 106.26(15) . 4_565
F4 C11 F4 104.3(2) . 4_565
F3 C11 C9 111.9(2) . .
F4 C11 C9 113.73(15) . .
F4 C11 C9 113.73(15) 4_565 .
N3 C12 O1 112.3(2) . .
N3 C12 C15 129.6(2) . .
O1 C12 C15 118.1(2) . .
O2 C13 C14 137.0(2) . .
O2 C13 O1 113.2(2) . .
C14 C13 O1 109.8(2) . .
C13 C14 N3 106.5(2) . .
C13 C14 H14A 126.7 . .
N3 C14 H14A 126.7 . .
C12 C15 H15A 109.7 . .
C12 C15 H15B 109.3 . .
H15A C15 H15B 109.5 . .
O2 C16 C17 106.4(2) . .
O2 C16 H16A 110.4 . .
C17 C16 H16A 110.5 . .
C16 C17 H17A 109.4 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N3 2.117(2) .
Ag1 N2 2.157(2) .
Ag1 N1 2.419(2) .
F1 C10 1.346(3) .
F2 C10 1.348(2) .
F3 C11 1.341(3) .
F4 C11 1.3496(19) .
O1 C12 1.359(3) .
O1 C13 1.365(3) .
O2 C13 1.333(3) .
O2 C16 1.438(3) .
N1 C1 1.335(3) .
N1 C5 1.354(3) .
N2 C9 1.354(3) .
N2 C6 1.365(3) .
N3 C12 1.294(3) .
N3 C14 1.404(3) .
C1 C2 1.381(4) .
C1 H1A 0.9500 .
C2 C3 1.386(4) .
C2 H2A 0.9500 .
C3 C4 1.384(4) .
C3 H3A 0.9500 .
C4 C5 1.396(3) .
C4 H4A 0.9500 .
C5 C6 1.475(4) .
C6 C7 1.408(3) .
C7 C8 1.405(4) .
C7 C10 1.479(3) .
C8 C9 1.383(3) .
C8 H8A 0.9500 .
C9 C11 1.470(3) .
C10 F2 1.348(2) 4_565
C11 F4 1.3497(19) 4_565
C12 C15 1.475(4) .
C13 C14 1.340(3) .
C14 H14A 0.9500 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C16 C17 1.507(4) .
C16 H16A 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
N3 Ag1 N1 C1 0.0 .
N2 Ag1 N1 C1 180.0 .
N3 Ag1 N1 C5 180.0 .
N2 Ag1 N1 C5 0.0 .
N3 Ag1 N2 C9 0.000(1) .
N1 Ag1 N2 C9 180.0 .
N3 Ag1 N2 C6 180.0 .
N1 Ag1 N2 C6 0.0 .
N2 Ag1 N3 C12 0.0 .
N1 Ag1 N3 C12 180.0 .
N2 Ag1 N3 C14 180.0 .
N1 Ag1 N3 C14 0.0 .
C5 N1 C1 C2 0.000(1) .
Ag1 N1 C1 C2 180.0 .
N1 C1 C2 C3 0.000(1) .
C1 C2 C3 C4 0.000(1) .
C2 C3 C4 C5 0.000(1) .
C1 N1 C5 C4 0.0 .
Ag1 N1 C5 C4 180.0 .
C1 N1 C5 C6 180.0 .
Ag1 N1 C5 C6 0.0 .
C3 C4 C5 N1 0.000(1) .
C3 C4 C5 C6 180.0 .
C9 N2 C6 C7 0.0 .
Ag1 N2 C6 C7 180.0 .
C9 N2 C6 C5 180.0 .
Ag1 N2 C6 C5 0.0 .
N1 C5 C6 N2 0.0 .
C4 C5 C6 N2 180.0 .
N1 C5 C6 C7 180.0 .
C4 C5 C6 C7 0.000(1) .
N2 C6 C7 C8 0.0 .
C5 C6 C7 C8 180.0 .
N2 C6 C7 C10 180.000(1) .
C5 C6 C7 C10 0.000(1) .
C6 C7 C8 C9 0.0 .
C10 C7 C8 C9 180.0 .
C6 N2 C9 C8 0.0 .
Ag1 N2 C9 C8 180.0 .
C6 N2 C9 C11 180.0 .
Ag1 N2 C9 C11 0.0 .
C7 C8 C9 N2 0.0 .
C7 C8 C9 C11 180.0 .
C8 C7 C10 F1 0.000(1) .
C6 C7 C10 F1 180.0 .
C8 C7 C10 F2 -119.86(18) .
C6 C7 C10 F2 60.14(17) .
C8 C7 C10 F2 119.86(18) 4_565
C6 C7 C10 F2 -60.14(18) 4_565
N2 C9 C11 F3 180.0 .
C8 C9 C11 F3 0.0 .
N2 C9 C11 F4 59.60(16) .
C8 C9 C11 F4 -120.40(16) .
N2 C9 C11 F4 -59.60(16) 4_565
C8 C9 C11 F4 120.40(16) 4_565
C14 N3 C12 O1 0.0 .
Ag1 N3 C12 O1 180.0 .
C14 N3 C12 C15 180.0 .
Ag1 N3 C12 C15 0.0 .
C13 O1 C12 N3 0.0 .
C13 O1 C12 C15 180.0 .
C16 O2 C13 C14 0.0 .
C16 O2 C13 O1 180.0 .
C12 O1 C13 O2 180.0 .
C12 O1 C13 C14 0.0 .
O2 C13 C14 N3 180.0 .
O1 C13 C14 N3 0.0 .
C12 N3 C14 C13 0.0 .
Ag1 N3 C14 C13 180.0 .
C13 O2 C16 C17 180.0 .
