#------------------------------------------------------------------------------
#$Date: 2019-11-08 04:21:48 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/03/1550350.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_1550350
loop_
_publ_author_name
'Tatikonda, Rajendhraprasad'
'Bulatov, Evgeny'
'Özdemir, Zülal'
'Nonappa, ?'
'Haukka, Matti'
_publ_section_title
;
 Infinite coordination polymer networks: metallogelation of aminopyridine
 conjugates and in situ silver nanoparticle formation.
;
_journal_issue                   3
_journal_name_full               'Soft matter'
_journal_page_first              442
_journal_page_last               451
_journal_paper_doi               10.1039/c8sm02006j
_journal_volume                  15
_journal_year                    2019
_chemical_formula_moiety         'C13 H12 Ag N3 O3'
_chemical_formula_sum            'C13 H12 Ag N3 O3'
_chemical_formula_weight         366.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                102.912(5)
_cell_angle_beta                 95.079(4)
_cell_angle_gamma                108.486(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3603(3)
_cell_length_b                   8.6180(6)
_cell_length_c                   11.0702(6)
_cell_measurement_reflns_used    5857
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.3170
_cell_measurement_theta_min      3.6300
_cell_volume                     639.40(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  73.00   1.00    2.50    --   23.20  57.00   0.00   71
  2  ω      3.00  58.00   1.00    2.50    --   23.20  57.00 -90.00   55
  3  ω      7.00  92.00   1.00    2.50    --   23.20  57.00-180.00   85
  4  ω     23.00  64.00   1.00    2.50    --   23.20 -99.00 -30.00   41
  5  ω     16.00  65.00   1.00    2.50    --   23.20 -99.00  90.00   49
  6  ω    -46.00  32.00   1.00    2.50    --   23.20 -57.00  30.00   78
  7  ω    -44.00  46.00   1.00    2.50    --  -22.10  57.00 -60.00   90
  8  ω     -7.00  90.00   1.00    2.50    --   23.20  77.00  60.00   97
  9  ω    -51.00  48.00   1.00    2.50    --  -22.10  77.00-180.00   99
 10  ω    -65.00  17.00   1.00    2.50    --  -22.10 -19.00-150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205560000
_diffrn_orient_matrix_UB_12      -0.0611045000
_diffrn_orient_matrix_UB_13      0.0270798000
_diffrn_orient_matrix_UB_21      0.0130004000
_diffrn_orient_matrix_UB_22      -0.0429804000
_diffrn_orient_matrix_UB_23      -0.0593677000
_diffrn_orient_matrix_UB_31      0.1002480000
_diffrn_orient_matrix_UB_32      0.0502457000
_diffrn_orient_matrix_UB_33      0.0139855000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9983
_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         27.876
_diffrn_reflns_theta_min         2.962
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0222P)²+0.1463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2825
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sm02006j2.cif
_cod_data_source_block           1.AgOAc
_cod_depositor_comments
'Adding full bibliography for 1550349--1550355.cif.'
_cod_original_cell_volume        639.40(6)
_cod_database_code               1550350
_chemical_oxdiff_formula         'C24 H23 N3 O4 Ag'
_chemical_oxdiff_usercomment     'Clear, Colorless, Block, 0.15 0.1 0.06'
_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.
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C5(H5), C4(H4), C2(H2A), C11(H11), C10(H10), C1(H1), C9(H9)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.908
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Ag01 Ag 0.39924(2) 0.81634(2) 1.08433(2) 0.01844(6) Uani 1 1 d .
O1 O 0.2778(2) 0.26811(18) 0.46228(13) 0.0180(3) Uani 1 1 d .
O3 O 0.7274(2) 0.9957(2) 1.00441(13) 0.0220(3) Uani 1 1 d .
O2 O 0.7046(2) 1.0178(2) 1.20510(14) 0.0215(3) Uani 1 1 d .
N3 N 0.2757(2) -0.2033(2) 0.26563(15) 0.0153(4) Uani 1 1 d .
N2 N 0.2507(2) 0.0673(2) 0.57083(15) 0.0135(3) Uani 1 1 d .
H2 H 0.2407 0.0504 0.6458 0.016 Uiso 1 1 calc R
N1 N 0.3503(2) 0.6038(2) 0.90746(16) 0.0164(4) Uani 1 1 d .
C12 C 0.7966(3) 1.0571(3) 1.11888(19) 0.0168(4) Uani 1 1 d .
C7 C 0.2426(3) -0.0738(3) 0.47398(18) 0.0126(4) Uani 1 1 d .
C8 C 0.2778(3) -0.0659(3) 0.35335(19) 0.0146(4) Uani 1 1 d .
H8 H 0.3039 0.0392 0.3324 0.017 Uiso 1 1 calc R
C5 C 0.2420(3) 0.4421(3) 0.89381(19) 0.0178(4) Uani 1 1 d .
H5 H 0.1832 0.4135 0.9626 0.021 Uiso 1 1 calc R
C4 C 0.2102(3) 0.3136(3) 0.78544(19) 0.0155(4) Uani 1 1 d .
H4 H 0.1332 0.2000 0.7807 0.019 Uiso 1 1 calc R
C6 C 0.2721(3) 0.2260(3) 0.56114(18) 0.0127(4) Uani 1 1 d .
C2 C 0.4038(3) 0.5235(3) 0.69563(19) 0.0153(4) Uani 1 1 d .
H2A H 0.4605 0.5564 0.6274 0.018 Uiso 1 1 calc R
C11 C 0.2047(3) -0.2273(3) 0.50383(19) 0.0162(4) Uani 1 1 d .
H11 H 0.1808 -0.2357 0.5855 0.019 Uiso 1 1 calc R
C10 C 0.2018(3) -0.3687(3) 0.4136(2) 0.0180(4) Uani 1 1 d .
H10 H 0.1757 -0.4755 0.4319 0.022 Uiso 1 1 calc R
C3 C 0.2936(3) 0.3545(3) 0.68344(18) 0.0125(4) Uani 1 1 d .
C1 C 0.4296(3) 0.6425(3) 0.80841(19) 0.0166(4) Uani 1 1 d .
H1 H 0.5069 0.7570 0.8163 0.020 Uiso 1 1 calc R
C9 C 0.2381(3) -0.3505(3) 0.29598(19) 0.0168(4) Uani 1 1 d .
H9 H 0.2361 -0.4473 0.2339 0.020 Uiso 1 1 calc R
C13 C 0.9989(3) 1.1881(3) 1.1570(2) 0.0276(5) Uani 1 1 d .
H13A H 1.0858 1.1500 1.1052 0.041 Uiso 1 1 calc GR
H13B H 1.0466 1.2029 1.2458 0.041 Uiso 1 1 calc GR
H13C H 0.9956 1.2964 1.1448 0.041 Uiso 1 1 calc GR
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'
Ag Ag -0.8971 1.1015 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -3 -13 0.0608
0 11 -6 0.0396
10 -6 4 0.0951
0 -12 6 0.0470
-9 7 -5 0.1114
-9 -1 8 0.1074
9 3 -2 0.0775
1 3 13 0.0697
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
O2 Ag01 O3 100.12(5) . 2_677
N3 Ag01 O3 107.21(6) 1_566 2_677
N3 Ag01 O2 90.54(6) 1_566 .
N1 Ag01 O3 99.86(6) . 2_677
N1 Ag01 O2 127.87(6) . .
N1 Ag01 N3 127.65(6) . 1_566
C12 O3 Ag01 112.35(13) . 2_677
C12 O2 Ag01 101.33(13) . .
C8 N3 Ag01 122.43(14) . 1_544
C9 N3 Ag01 117.58(13) . 1_544
C9 N3 C8 118.55(18) . .
C7 N2 H2 116.4 . .
C6 N2 H2 116.4 . .
C6 N2 C7 127.23(17) . .
C5 N1 Ag01 124.04(14) . .
C5 N1 C1 117.26(18) . .
C1 N1 Ag01 118.67(14) . .
O3 C12 O2 123.4(2) . .
O3 C12 C13 118.6(2) . .
O2 C12 C13 117.97(19) . .
C8 C7 N2 124.17(19) . .
C11 C7 N2 116.99(18) . .
C11 C7 C8 118.79(18) . .
N3 C8 C7 121.82(19) . .
N3 C8 H8 119.1 . .
C7 C8 H8 119.1 . .
N1 C5 H5 118.1 . .
N1 C5 C4 123.87(19) . .
C4 C5 H5 118.1 . .
C5 C4 H4 120.7 . .
C5 C4 C3 118.5(2) . .
C3 C4 H4 120.7 . .
O1 C6 N2 124.48(18) . .
O1 C6 C3 120.43(18) . .
N2 C6 C3 115.08(17) . .
C3 C2 H2A 120.5 . .
C1 C2 H2A 120.5 . .
C1 C2 C3 119.07(19) . .
C7 C11 H11 120.3 . .
C7 C11 C10 119.43(19) . .
C10 C11 H11 120.3 . .
C11 C10 H10 120.9 . .
C9 C10 C11 118.3(2) . .
C9 C10 H10 120.9 . .
C4 C3 C6 123.62(18) . .
C4 C3 C2 118.14(18) . .
C2 C3 C6 118.24(18) . .
N1 C1 C2 123.1(2) . .
N1 C1 H1 118.4 . .
C2 C1 H1 118.4 . .
N3 C9 C10 123.12(19) . .
N3 C9 H9 118.4 . .
C10 C9 H9 118.4 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag01 O3 2.4426(16) 2_677
Ag01 O2 2.4101(16) .
Ag01 N3 2.2937(17) 1_566
Ag01 N1 2.2742(17) .
O1 C6 1.228(2) .
O3 Ag01 2.4426(16) 2_677
O3 C12 1.249(2) .
O2 C12 1.264(3) .
N3 Ag01 2.2937(17) 1_544
N3 C8 1.348(3) .
N3 C9 1.335(3) .
N2 H2 0.8800 .
N2 C7 1.411(2) .
N2 C6 1.357(3) .
N1 C5 1.334(3) .
N1 C1 1.344(3) .
C12 C13 1.510(3) .
C7 C8 1.395(3) .
C7 C11 1.384(3) .
C8 H8 0.9500 .
C5 H5 0.9500 .
C5 C4 1.383(3) .
C4 H4 0.9500 .
C4 C3 1.392(3) .
C6 C3 1.505(3) .
C2 H2A 0.9500 .
C2 C3 1.393(3) .
C2 C1 1.382(3) .
C11 H11 0.9500 .
C11 C10 1.385(3) .
C10 H10 0.9500 .
C10 C9 1.385(3) .
C1 H1 0.9500 .
C9 H9 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.88 1.92 2.760(2) 158.6 2_667
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
Ag01 O3 C12 O2 98.7(2) 2_677
Ag01 O3 C12 C13 -79.9(2) 2_677
Ag01 O2 C12 O3 -0.3(2) .
Ag01 O2 C12 C13 178.34(16) .
Ag01 N3 C8 C7 -165.70(14) 1_544
Ag01 N3 C9 C10 166.35(16) 1_544
Ag01 N1 C5 C4 179.00(15) .
Ag01 N1 C1 C2 -178.12(15) .
O1 C6 C3 C4 151.2(2) .
O1 C6 C3 C2 -29.1(3) .
N2 C7 C8 N3 177.34(17) .
N2 C7 C11 C10 -177.77(18) .
N2 C6 C3 C4 -30.0(3) .
N2 C6 C3 C2 149.68(18) .
N1 C5 C4 C3 -0.8(3) .
C7 N2 C6 O1 4.0(3) .
C7 N2 C6 C3 -174.77(17) .
C7 C11 C10 C9 0.2(3) .
C8 N3 C9 C10 -0.3(3) .
C8 C7 C11 C10 -0.2(3) .
C5 N1 C1 C2 -0.1(3) .
C5 C4 C3 C6 179.16(18) .
C5 C4 C3 C2 -0.5(3) .
C6 N2 C7 C8 7.5(3) .
C6 N2 C7 C11 -175.07(19) .
C11 C7 C8 N3 0.0(3) .
C11 C10 C9 N3 0.1(3) .
C3 C2 C1 N1 -1.1(3) .
C1 N1 C5 C4 1.1(3) .
C1 C2 C3 C4 1.4(3) .
C1 C2 C3 C6 -178.27(18) .
C9 N3 C8 C7 0.3(3) .
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -3.0000 -13.0000 -0.1893 0.8877 -0.4328
0.0000 11.0000 -6.0000 -0.8346 -0.1166 0.4688
10.0000 -6.0000 4.0000 0.6805 0.1504 0.7569
-0.0000 -12.0000 6.0000 0.8957 0.1596 -0.5190
-9.0000 7.0000 -5.0000 -0.7481 -0.1210 -0.6204
-9.0000 -1.0000 8.0000 0.0927 -0.5490 -0.8406
9.0000 3.0000 -2.0000 -0.0525 0.1068 1.0250
1.0000 3.0000 13.0000 0.1893 -0.8877 0.4328
