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#$Date: 2019-11-17 08:04:10 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228793 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/86/1548637.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_1548637
loop_
_publ_author_name
'Fang, Yinzhi'
'Zhang, Han'
'Huang, Zhen'
'Scinto, Samuel L.'
'Yang, Jeffrey C.'
'Am Ende, Christopher W.'
'Dmitrenko, Olga'
'Johnson, Douglas S.'
'Fox, Joseph M.'
_publ_section_title
;
 Photochemical syntheses, transformations, and bioorthogonal chemistry of
 trans-cycloheptene and sila trans-cycloheptene Ag(i)
 complexes.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1953
_journal_page_last               1963
_journal_paper_doi               10.1039/c7sc04773h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C18 H20 Ag N O3 Si'
_chemical_formula_weight         434.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-04 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.6900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5090(10)
_cell_length_b                   8.4282(5)
_cell_length_c                   13.9655(8)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.50
_cell_volume                     1765.53(18)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0100
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18866
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         2.716
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.194
_refine_diff_density_max         1.796
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0798P)²+1.7044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3743
_reflns_number_total             4077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7sc04773h3.cif
_cod_data_source_block           joef124
_cod_depositor_comments
'Adding full bibliography for 1548636--1548637.cif.'
_cod_database_code               1548637
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.644
_shelx_estimated_absorpt_t_max   0.797
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ag1 Ag 0.39887(2) 0.53145(3) 0.29615(2) 0.04713(12) Uani 1 1 d . .
C1 C 0.3696(2) 0.1563(3) 0.3408(2) 0.0418(6) Uani 1 1 d . .
H1A H 0.4356 0.1584 0.3729 0.050 Uiso 1 1 calc R U
H1B H 0.3485 0.1087 0.2697 0.050 Uiso 1 1 calc R U
C2 C 0.33451(18) 0.0599(3) 0.4111(2) 0.0357(5) Uani 1 1 d . .
H2A H 0.3856 0.0388 0.4793 0.043 Uiso 1 1 calc R U
H2B H 0.3130 -0.0440 0.3768 0.043 Uiso 1 1 calc R U
C3 C 0.2681(2) 0.3532(3) 0.5097(2) 0.0397(5) Uani 1 1 d . .
H3A H 0.2161 0.3857 0.5230 0.048 Uiso 1 1 calc R U
H3B H 0.3191 0.3391 0.5790 0.048 Uiso 1 1 calc R U
C4 C 0.2908(2) 0.4901(3) 0.4509(2) 0.0449(6) Uani 1 1 d . .
H4A H 0.2373 0.5252 0.3887 0.054 Uiso 1 1 calc R U
H4B H 0.3167 0.5819 0.4980 0.054 Uiso 1 1 calc R U
C5 C 0.3582(3) 0.4145(4) 0.4184(3) 0.0561(8) Uani 1 1 d . .
H5 H 0.4199 0.4346 0.4585 0.067 Uiso 1 1 calc R U
C6 C 0.3330(2) 0.3202(4) 0.3346(3) 0.0532(7) Uani 1 1 d . .
H6 H 0.2904 0.3581 0.2687 0.064 Uiso 1 1 calc R U
C7 C 0.13419(19) 0.0931(3) 0.2219(2) 0.0412(6) Uani 1 1 d . .
H7 H 0.1839 0.0324 0.2255 0.049 Uiso 1 1 calc R U
C8 C 0.0588(2) 0.1007(4) 0.1272(2) 0.0537(8) Uani 1 1 d . .
H8 H 0.0572 0.0454 0.0671 0.064 Uiso 1 1 calc R U
C9 C -0.0144(2) 0.1895(5) 0.1204(3) 0.0554(8) Uani 1 1 d . .
H9 H -0.0666 0.1937 0.0562 0.067 Uiso 1 1 calc R U
C10 C -0.0108(2) 0.2718(4) 0.2077(3) 0.0538(8) Uani 1 1 d . .
H10 H -0.0603 0.3340 0.2030 0.065 Uiso 1 1 calc R U
C11 C 0.06543(19) 0.2641(4) 0.3031(2) 0.0440(6) Uani 1 1 d . .
H11 H 0.0671 0.3219 0.3623 0.053 Uiso 1 1 calc R U
C12 C 0.13910(16) 0.1725(3) 0.31253(18) 0.0329(5) Uani 1 1 d . .
C13 C 0.14192(18) 0.0470(3) 0.5522(2) 0.0370(5) Uani 1 1 d . .
H13 H 0.1051 0.1358 0.5201 0.044 Uiso 1 1 calc R U
C14 C 0.1214(2) -0.0476(3) 0.6211(2) 0.0414(6) Uani 1 1 d . .
H14 H 0.0717 -0.0227 0.6359 0.050 Uiso 1 1 calc R U
C15 C 0.17389(19) -0.1773(3) 0.6673(2) 0.0412(6) Uani 1 1 d . .
H15 H 0.1605 -0.2418 0.7146 0.049 Uiso 1 1 calc R U
C16 C 0.24652(18) -0.2145(3) 0.6450(2) 0.0382(5) Uani 1 1 d . .
H16 H 0.2821 -0.3049 0.6764 0.046 Uiso 1 1 calc R U
C17 C 0.26678(16) -0.1189(3) 0.57661(19) 0.0331(5) Uani 1 1 d . .
H17 H 0.3165 -0.1446 0.5619 0.040 Uiso 1 1 calc R U
C18 C 0.21477(16) 0.0154(3) 0.52890(19) 0.0309(5) Uani 1 1 d . .
N1 N 0.49119(15) 0.8436(3) 0.29131(18) 0.0378(5) Uani 1 1 d . .
O1 O 0.47117(17) 0.7654(3) 0.35397(18) 0.0573(6) Uani 1 1 d . .
O2 O 0.45072(17) 0.8296(4) 0.19530(18) 0.0672(7) Uani 1 1 d . .
O3 O 0.55254(19) 0.9425(4) 0.32796(19) 0.0640(7) Uani 1 1 d . .
Si1 Si 0.24195(4) 0.15278(7) 0.43957(5) 0.02923(15) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C6 Ag1 O1 146.23(10) .
C6 Ag1 C5 33.84(12) .
O1 Ag1 C5 112.40(11) .
C6 Ag1 O3 105.86(12) 2_645
O1 Ag1 O3 104.61(11) 2_645
C5 Ag1 O3 135.69(14) 2_645
C6 C1 C2 105.7(2) .
C6 C1 H1A 110.6 .
C2 C1 H1A 110.6 .
C6 C1 H1B 110.6 .
C2 C1 H1B 110.6 .
H1A C1 H1B 108.7 .
C1 C2 Si1 117.36(18) .
C1 C2 H2A 108.0 .
Si1 C2 H2A 108.0 .
C1 C2 H2B 108.0 .
Si1 C2 H2B 108.0 .
H2A C2 H2B 107.2 .
C4 C3 Si1 116.11(17) .
C4 C3 H3A 108.3 .
Si1 C3 H3A 108.3 .
C4 C3 H3B 108.3 .
Si1 C3 H3B 108.3 .
H3A C3 H3B 107.4 .
C5 C4 C3 102.5(2) .
C5 C4 H4A 111.3 .
C3 C4 H4A 111.3 .
C5 C4 H4B 111.3 .
C3 C4 H4B 111.3 .
H4A C4 H4B 109.2 .
C6 C5 C4 121.2(3) .
C6 C5 Ag1 71.60(19) .
C4 C5 Ag1 121.6(2) .
C6 C5 H5 119.4 .
C4 C5 H5 119.4 .
Ag1 C5 H5 77.8 .
C5 C6 C1 122.0(3) .
C5 C6 Ag1 74.6(2) .
C1 C6 Ag1 121.1(2) .
C5 C6 H6 119.0 .
C1 C6 H6 119.0 .
Ag1 C6 H6 75.0 .
C8 C7 C12 121.9(3) .
C8 C7 H7 119.1 .
C12 C7 H7 119.1 .
C9 C8 C7 119.8(3) .
C9 C8 H8 120.1 .
C7 C8 H8 120.1 .
C10 C9 C8 119.6(3) .
C10 C9 H9 120.2 .
C8 C9 H9 120.2 .
C9 C10 C11 120.4(3) .
C9 C10 H10 119.8 .
C11 C10 H10 119.8 .
C12 C11 C10 121.0(3) .
C12 C11 H11 119.5 .
C10 C11 H11 119.5 .
C11 C12 C7 117.2(2) .
C11 C12 Si1 123.0(2) .
C7 C12 Si1 119.81(19) .
C14 C13 C18 122.1(2) .
C14 C13 H13 118.9 .
C18 C13 H13 118.9 .
C15 C14 C13 119.4(3) .
C15 C14 H14 120.3 .
C13 C14 H14 120.3 .
C14 C15 C16 120.4(2) .
C14 C15 H15 119.8 .
C16 C15 H15 119.8 .
C17 C16 C15 119.8(2) .
C17 C16 H16 120.1 .
C15 C16 H16 120.1 .
C16 C17 C18 121.0(2) .
C16 C17 H17 119.5 .
C18 C17 H17 119.5 .
C13 C18 C17 117.2(2) .
C13 C18 Si1 120.13(19) .
C17 C18 Si1 122.62(19) .
O2 N1 O1 122.2(2) .
O2 N1 O3 119.4(3) .
O1 N1 O3 118.3(2) .
N1 O1 Ag1 117.64(18) .
N1 O3 Ag1 112.67(18) 2_655
C12 Si1 C18 107.90(11) .
C12 Si1 C2 109.07(11) .
C18 Si1 C2 108.62(11) .
C12 Si1 C3 109.08(12) .
C18 Si1 C3 105.61(11) .
C2 Si1 C3 116.24(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C6 2.264(3) .
Ag1 O1 2.271(2) .
Ag1 C5 2.300(3) .
Ag1 O3 2.318(3) 2_645
C1 C6 1.496(4) .
C1 C2 1.561(4) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 Si1 1.901(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.550(4) .
C3 Si1 1.909(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.508(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.329(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.388(4) .
C7 C12 1.404(3) .
C7 H7 0.9500 .
C8 C9 1.391(5) .
C8 H8 0.9500 .
C9 C10 1.381(5) .
C9 H9 0.9500 .
C10 C11 1.400(4) .
C10 H10 0.9500 .
C11 C12 1.399(4) .
C11 H11 0.9500 .
C12 Si1 1.882(2) .
C13 C14 1.396(4) .
C13 C18 1.396(4) .
C13 H13 0.9500 .
C14 C15 1.377(4) .
C14 H14 0.9500 .
C15 C16 1.394(4) .
C15 H15 0.9500 .
C16 C17 1.394(4) .
C16 H16 0.9500 .
C17 C18 1.408(4) .
C17 H17 0.9500 .
C18 Si1 1.889(3) .
N1 O2 1.229(3) .
N1 O1 1.246(3) .
N1 O3 1.244(3) .
O3 Ag1 2.318(3) 2_655
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
C6 C1 C2 Si1 13.1(3) .
Si1 C3 C4 C5 -48.0(3) .
C3 C4 C5 C6 79.8(4) .
C3 C4 C5 Ag1 166.3(2) .
C4 C5 C6 C1 -126.3(4) .
Ag1 C5 C6 C1 117.4(3) .
C4 C5 C6 Ag1 116.3(3) .
C2 C1 C6 C5 66.6(4) .
C2 C1 C6 Ag1 157.3(2) .
C12 C7 C8 C9 0.2(5) .
C7 C8 C9 C10 1.1(5) .
C8 C9 C10 C11 -1.0(5) .
C9 C10 C11 C12 -0.4(5) .
C10 C11 C12 C7 1.8(4) .
C10 C11 C12 Si1 -178.2(2) .
C8 C7 C12 C11 -1.7(4) .
C8 C7 C12 Si1 178.3(2) .
C18 C13 C14 C15 -0.5(4) .
C13 C14 C15 C16 -0.4(4) .
C14 C15 C16 C17 0.8(4) .
C15 C16 C17 C18 -0.2(4) .
C14 C13 C18 C17 1.1(4) .
C14 C13 C18 Si1 -177.4(2) .
C16 C17 C18 C13 -0.7(4) .
C16 C17 C18 Si1 177.74(19) .
O2 N1 O1 Ag1 24.1(4) .
O3 N1 O1 Ag1 -158.1(2) .
O2 N1 O3 Ag1 -15.6(4) 2_655
O1 N1 O3 Ag1 166.6(2) 2_655
C11 C12 Si1 C18 75.2(2) .
C7 C12 Si1 C18 -104.7(2) .
C11 C12 Si1 C2 -167.0(2) .
C7 C12 Si1 C2 13.1(2) .
C11 C12 Si1 C3 -39.1(3) .
C7 C12 Si1 C3 141.0(2) .
C13 C18 Si1 C12 -54.5(2) .
C17 C18 Si1 C12 127.1(2) .
C13 C18 Si1 C2 -172.6(2) .
C17 C18 Si1 C2 9.0(2) .
C13 C18 Si1 C3 62.0(2) .
C17 C18 Si1 C3 -116.4(2) .
