#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/05/1520558.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_1520558
loop_
_publ_author_name
'Laird, Rebecca C.'
'Sinnwell, Michael A.'
'Nguyen, Nam P.'
'Swenson, Dale C.'
'Mariappan, S. V. Santhana'
'MacGillivray, Leonard R.'
_publ_section_title
;
 Intramolecular [2 + 2] Photodimerization Achieved in the Solid State via
 Coordination-Driven Self-Assembly.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3233
_journal_page_last               3235
_journal_paper_doi               10.1021/acs.orglett.5b00527
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C50 H36 Ag2 F6 N4 O6 S2'
_chemical_formula_weight         1182.68
_chemical_name_common            'Ag triflate DEPN'
_chemical_name_systematic
; 
 Silver trifluoromethanesulfonate 1,8-bis[(E)-2-(4-pyridyl)ethenyl] naphthalene 
;
_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                109.430(5)
_cell_angle_beta                 98.185(5)
_cell_angle_gamma                97.328(5)
_cell_formula_units_Z            1
_cell_length_a                   10.3809(11)
_cell_length_b                   10.9748(11)
_cell_length_c                   11.0438(12)
_cell_measurement_reflns_used    5411
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     1153.7(2)
_computing_cell_refinement       'HKL Scalepack (Otwinwski & Minor, 1997)'
_computing_data_collection       'CCD phi and omega scans'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinwski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD phi and omega 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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38166
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_T_max  0.9320
_exptl_absorpt_correction_T_min  0.7993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinwski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0669P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                3513
_reflns_number_total             4053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00527_si_002.cif
_cod_data_source_block           mcg12120
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520555--1520560.cif.
;
_cod_original_sg_symbol_H-M      ' P-1 '
_cod_database_code               1520558
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 0.630240(19) 0.59179(2) 0.62159(2) 0.04172(11) Uani 1 1 d .
S1 S 0.56318(7) 0.66582(8) 0.29501(7) 0.04217(19) Uani 1 1 d .
N2 N 0.5191(2) 0.7337(2) 0.7195(2) 0.0356(5) Uani 1 1 d .
N1 N 0.7656(2) 0.4600(2) 0.5635(2) 0.0359(5) Uani 1 1 d .
C7 C 1.0305(2) 0.1226(3) 0.3247(3) 0.0354(6) Uani 1 1 d .
H7 H 0.9937 0.1560 0.2623 0.042 Uiso 1 1 calc R
C16 C 0.2739(2) 0.9841(3) 0.9187(3) 0.0358(6) Uani 1 1 d .
H16 H 0.2772 0.9982 1.0079 0.043 Uiso 1 1 calc R
C9 C -0.0430(2) 1.0951(3) 0.8429(3) 0.0332(6) Uani 1 1 d .
C4 C 0.8899(3) 0.3506(3) 0.4092(3) 0.0369(6) Uani 1 1 d .
H4 H 0.9150 0.3367 0.3278 0.044 Uiso 1 1 calc R
C2 C 0.8983(3) 0.3118(3) 0.6086(3) 0.0362(6) Uani 1 1 d .
H2 H 0.9305 0.2725 0.6676 0.043 Uiso 1 1 calc R
C11 C 0.1868(3) 1.0372(3) 0.8594(3) 0.0368(6) Uani 1 1 d .
H11 H 0.1892 1.0261 0.7717 0.044 Uiso 1 1 calc R
C5 C 0.8071(3) 0.4361(3) 0.4492(3) 0.0352(6) Uani 1 1 d .
H5 H 0.7775 0.4807 0.3943 0.042 Uiso 1 1 calc R
C10 C 0.0881(3) 1.1111(3) 0.9173(3) 0.0352(6) Uani 1 1 d .
C13 C 0.3966(2) 0.9058(3) 0.7337(3) 0.0383(6) Uani 1 1 d .
H13 H 0.3671 0.9654 0.6965 0.046 Uiso 1 1 calc R
C3 C 0.9381(2) 0.2831(3) 0.4884(3) 0.0320(5) Uani 1 1 d .
C8 C 1.0979(2) 0.0109(3) 0.2782(3) 0.0338(6) Uani 1 1 d .
C15 C 0.4175(2) 0.8178(3) 0.9032(3) 0.0373(6) Uani 1 1 d .
H15 H 0.4031 0.8163 0.9848 0.045 Uiso 1 1 calc R
C12 C 0.4719(2) 0.8199(3) 0.6719(3) 0.0375(6) Uani 1 1 d .
H12 H 0.4914 0.8216 0.5919 0.045 Uiso 1 1 calc R
C6 C 1.0173(2) 0.1807(3) 0.4483(3) 0.0376(6) Uani 1 1 d .
H6 H 1.0614 0.1544 0.5132 0.045 Uiso 1 1 calc R
C14 C 0.3636(2) 0.9054(2) 0.8517(3) 0.0339(6) Uani 1 1 d .
C1 C 0.8127(3) 0.3966(3) 0.6412(3) 0.0391(6) Uani 1 1 d .
H1 H 0.7853 0.4117 0.7216 0.047 Uiso 1 1 calc R
F3 F 0.79919(18) 0.7037(2) 0.2419(2) 0.0758(6) Uani 1 1 d .
F2 F 0.6417(2) 0.6635(3) 0.0816(2) 0.0819(7) Uani 1 1 d .
O3 O 0.4407(2) 0.5851(2) 0.2156(3) 0.0648(6) Uani 1 1 d .
O1 O 0.5689(2) 0.8040(2) 0.3335(3) 0.0694(7) Uani 1 1 d .
C001 C -0.2466(3) 1.1837(3) 0.8166(3) 0.0419(7) Uani 1 1 d .
H001 H -0.2978 1.2477 0.8484 0.050 Uiso 1 1 calc R
C002 C -0.1221(3) 1.1904(3) 0.8927(3) 0.0375(6) Uani 1 1 d .
F1 F 0.6907(3) 0.5079(2) 0.1438(3) 0.0846(7) Uani 1 1 d .
C003 C 0.4905(3) 0.7351(3) 0.8349(3) 0.0392(6) Uani 1 1 d .
H003 H 0.5228 0.6755 0.8704 0.047 Uiso 1 1 calc R
C004 C -0.0751(3) 1.2900(3) 1.0173(3) 0.0463(7) Uani 1 1 d .
H004 H -0.1270 1.3530 1.0499 0.056 Uiso 1 1 calc R
C005 C 0.0440(3) 1.2960(3) 1.0908(3) 0.0494(8) Uani 1 1 d .
H005 H 0.0709 1.3593 1.1758 0.059 Uiso 1 1 calc R
C006 C 1.2201(3) 0.0125(3) 0.3481(3) 0.0428(7) Uani 1 1 d .
H006 H 1.2550 0.0814 0.4286 0.051 Uiso 1 1 calc R
C007 C 0.6795(3) 0.6328(3) 0.1841(3) 0.0502(8) Uani 1 1 d .
O2 O 0.6181(3) 0.6242(3) 0.3979(3) 0.0835(9) Uani 1 1 d .
C008 C -0.2929(3) 1.0862(3) 0.6986(3) 0.0457(7) Uani 1 1 d .
H008 H -0.3742 1.0850 0.6478 0.055 Uiso 1 1 calc R
C009 C 0.1272(3) 1.2080(3) 1.0400(3) 0.0444(7) Uani 1 1 d .
H009 H 0.2107 1.2153 1.0906 0.053 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'
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'
S S 0.1246 0.1234 '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
N2 Ag1 N1 168.13(8) . .
N2 Ag1 O2 101.66(8) . .
N1 Ag1 O2 88.20(8) . .
O1 S1 O2 114.24(18) . .
O1 S1 O3 115.77(15) . .
O2 S1 O3 114.43(18) . .
O1 S1 C007 103.88(16) . .
O2 S1 C007 102.96(14) . .
O3 S1 C007 103.30(15) . .
C12 N2 C003 116.6(2) . .
C12 N2 Ag1 124.53(18) . .
C003 N2 Ag1 118.84(18) . .
C1 N1 C5 116.7(2) . .
C1 N1 Ag1 120.97(18) . .
C5 N1 Ag1 122.30(17) . .
C6 C7 C8 125.4(2) . .
C6 C7 H7 117.3 . .
C8 C7 H7 117.3 . .
C11 C16 C14 123.5(3) . .
C11 C16 H16 118.3 . .
C14 C16 H16 118.3 . .
C002 C9 C8 118.2(2) . 2_666
C002 C9 C10 118.3(3) . .
C8 C9 C10 123.6(2) 2_666 .
C5 C4 C3 120.5(2) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C1 C2 C3 120.4(2) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C16 C11 C10 126.9(3) . .
C16 C11 H11 116.5 . .
C10 C11 H11 116.5 . .
N1 C5 C4 123.2(2) . .
N1 C5 H5 118.4 . .
C4 C5 H5 118.4 . .
C009 C10 C9 119.4(2) . .
C009 C10 C11 118.8(2) . .
C9 C10 C11 121.4(2) . .
C12 C13 C14 120.3(2) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C2 C3 C4 115.9(2) . .
C2 C3 C6 119.8(2) . .
C4 C3 C6 124.1(2) . .
C006 C8 C9 119.6(2) . 2_666
C006 C8 C7 119.5(3) . .
C9 C8 C7 120.8(2) 2_666 .
C003 C15 C14 120.0(2) . .
C003 C15 H15 120.0 . .
C14 C15 H15 120.0 . .
N2 C12 C13 123.4(2) . .
N2 C12 H12 118.3 . .
C13 C12 H12 118.3 . .
C7 C6 C3 123.7(2) . .
C7 C6 H6 118.2 . .
C3 C6 H6 118.2 . .
C13 C14 C15 115.8(2) . .
C13 C14 C16 124.4(2) . .
C15 C14 C16 119.7(2) . .
N1 C1 C2 123.2(2) . .
N1 C1 H1 118.4 . .
C2 C1 H1 118.4 . .
C008 C001 C002 120.9(2) . .
C008 C001 H001 119.5 . .
C002 C001 H001 119.5 . .
C004 C002 C001 121.0(2) . .
C004 C002 C9 119.5(3) . .
C001 C002 C9 119.5(3) . .
N2 C003 C15 123.8(3) . .
N2 C003 H003 118.1 . .
C15 C003 H003 118.1 . .
C005 C004 C002 121.1(3) . .
C005 C004 H004 119.5 . .
C002 C004 H004 119.5 . .
C004 C005 C009 120.3(3) . .
C004 C005 H005 119.9 . .
C009 C005 H005 119.9 . .
C8 C006 C008 121.3(3) . 2_666
C8 C006 H006 119.3 . .
C008 C006 H006 119.3 2_666 .
F2 C007 F1 108.6(3) . .
F2 C007 F3 107.0(3) . .
F1 C007 F3 107.5(3) . .
F2 C007 S1 110.8(2) . .
F1 C007 S1 111.6(2) . .
F3 C007 S1 111.2(2) . .
S1 O2 Ag1 154.62(15) . .
C001 C008 C006 120.2(3) . 2_666
C001 C008 H008 119.9 . .
C006 C008 H008 119.9 2_666 .
C10 C009 C005 121.1(3) . .
C10 C009 H009 119.5 . .
C005 C009 H009 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N2 2.149(2) .
Ag1 N1 2.153(2) .
Ag1 O2 2.599(2) .
S1 O1 1.423(2) .
S1 O2 1.432(2) .
S1 O3 1.432(2) .
S1 C007 1.824(3) .
N2 C12 1.336(3) .
N2 C003 1.345(4) .
N1 C1 1.350(4) .
N1 C5 1.347(3) .
C7 C6 1.337(4) .
C7 C8 1.469(4) .
C7 H7 0.9400 .
C16 C11 1.344(4) .
C16 C14 1.462(4) .
C16 H16 0.9400 .
C9 C002 1.427(3) .
C9 C8 1.430(4) 2_666
C9 C10 1.443(4) .
C4 C5 1.361(4) .
C4 C3 1.403(4) .
C4 H4 0.9400 .
C2 C1 1.366(4) .
C2 C3 1.394(4) .
C2 H2 0.9400 .
C11 C10 1.472(4) .
C11 H11 0.9400 .
C5 H5 0.9400 .
C10 C009 1.381(4) .
C13 C12 1.370(4) .
C13 C14 1.395(4) .
C13 H13 0.9400 .
C3 C6 1.464(4) .
C8 C006 1.383(4) .
C8 C9 1.430(4) 2_666
C15 C003 1.360(4) .
C15 C14 1.404(4) .
C15 H15 0.9400 .
C12 H12 0.9400 .
C6 H6 0.9400 .
C1 H1 0.9400 .
F3 C007 1.325(4) .
F2 C007 1.307(4) .
C001 C008 1.355(5) .
C001 C002 1.417(4) .
C001 H001 0.9400 .
C002 C004 1.414(4) .
F1 C007 1.319(4) .
C003 H003 0.9400 .
C004 C005 1.359(5) .
C004 H004 0.9400 .
C005 C009 1.409(4) .
C005 H005 0.9400 .
C006 C008 1.400(4) 2_666
C006 H006 0.9400 .
C008 C006 1.400(4) 2_666
C008 H008 0.9400 .
C009 H009 0.9400 .
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_1
_geom_torsion_site_symmetry_4
N1 Ag1 N2 C12 140.1(4) . .
O2 Ag1 N2 C12 -5.6(2) . .
N1 Ag1 N2 C003 -42.0(5) . .
O2 Ag1 N2 C003 172.3(2) . .
N2 Ag1 N1 C1 36.2(5) . .
O2 Ag1 N1 C1 -177.3(2) . .
N2 Ag1 N1 C5 -143.9(4) . .
O2 Ag1 N1 C5 2.6(2) . .
C14 C16 C11 C10 176.3(2) . .
C1 N1 C5 C4 1.6(4) . .
Ag1 N1 C5 C4 -178.3(2) . .
C3 C4 C5 N1 -0.8(4) . .
C002 C9 C10 C009 7.3(4) . .
C8 C9 C10 C009 -172.9(3) 2_666 .
C002 C9 C10 C11 -165.4(2) . .
C8 C9 C10 C11 14.5(4) 2_666 .
C16 C11 C10 C009 46.4(4) . .
C16 C11 C10 C9 -141.0(3) . .
C1 C2 C3 C4 2.8(4) . .
C1 C2 C3 C6 -172.9(3) . .
C5 C4 C3 C2 -1.4(4) . .
C5 C4 C3 C6 174.1(3) . .
C6 C7 C8 C006 -46.0(4) . .
C6 C7 C8 C9 138.3(3) . 2_666
C003 N2 C12 C13 -0.7(4) . .
Ag1 N2 C12 C13 177.2(2) . .
C14 C13 C12 N2 -1.0(4) . .
C8 C7 C6 C3 -173.6(2) . .
C2 C3 C6 C7 161.7(3) . .
C4 C3 C6 C7 -13.6(4) . .
C12 C13 C14 C15 3.1(4) . .
C12 C13 C14 C16 -174.0(2) . .
C003 C15 C14 C13 -3.6(4) . .
C003 C15 C14 C16 173.6(3) . .
C11 C16 C14 C13 18.6(4) . .
C11 C16 C14 C15 -158.3(3) . .
C5 N1 C1 C2 -0.1(4) . .
Ag1 N1 C1 C2 179.7(2) . .
C3 C2 C1 N1 -2.2(4) . .
C008 C001 C002 C004 -178.4(3) . .
C008 C001 C002 C9 1.6(4) . .
C8 C9 C002 C004 174.7(2) 2_666 .
C10 C9 C002 C004 -5.4(4) . .
C8 C9 C002 C001 -5.2(4) 2_666 .
C10 C9 C002 C001 174.6(2) . .
C12 N2 C003 C15 0.2(4) . .
Ag1 N2 C003 C15 -177.9(2) . .
C14 C15 C003 N2 2.1(4) . .
C001 C002 C004 C005 179.6(3) . .
C9 C002 C004 C005 -0.4(4) . .
C002 C004 C005 C009 4.3(4) . .
C9 C8 C006 C008 1.4(4) 2_666 2_666
C7 C8 C006 C008 -174.4(3) . 2_666
O1 S1 C007 F2 -61.9(3) . .
O2 S1 C007 F2 178.7(3) . .
O3 S1 C007 F2 59.4(3) . .
O1 S1 C007 F1 177.0(2) . .
O2 S1 C007 F1 57.6(3) . .
O3 S1 C007 F1 -61.8(3) . .
O1 S1 C007 F3 57.0(3) . .
O2 S1 C007 F3 -62.4(3) . .
O3 S1 C007 F3 178.2(2) . .
O1 S1 O2 Ag1 63.6(6) . .
O3 S1 O2 Ag1 -73.1(5) . .
C007 S1 O2 Ag1 175.5(5) . .
N2 Ag1 O2 S1 -20.6(5) . .
N1 Ag1 O2 S1 166.1(5) . .
C002 C001 C008 C006 2.3(4) . 2_666
C9 C10 C009 C005 -3.5(4) . .
C11 C10 C009 C005 169.3(3) . .
C004 C005 C009 C10 -2.3(5) . .
