#------------------------------------------------------------------------------
#$Date: 2019-11-23 06:28:39 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/74/4347459.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_4347459
loop_
_publ_author_name
'Jaros, Sabina W.'
'Guedes da Silva, M Fátima C'
'Florek, Magdalena'
'Smoleński, Piotr'
'Pombeiro, Armando J. L.'
'Kirillov, Alexander M.'
_publ_section_title
;
 Silver(I) 1,3,5-Triaza-7-phosphaadamantane Coordination Polymers Driven
 by Substituted Glutarate and Malonate Building Blocks: Self-Assembly
 Synthesis, Structural Features, and Antimicrobial Properties.
;
_journal_issue                   12
_journal_name_full               'Inorganic chemistry'
_journal_page_first              5886
_journal_page_last               5894
_journal_paper_doi               10.1021/acs.inorgchem.6b00186
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C13 H23 Ag N3 O4 P'
_chemical_formula_sum            'C13 H23 Ag N3 O4 P'
_chemical_formula_weight         424.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.743(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6652(15)
_cell_length_b                   6.8368(4)
_cell_length_c                   11.2541(7)
_cell_measurement_reflns_used    6307
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      3.14
_cell_volume                     1596.30(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7040
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.394
_diffrn_reflns_theta_min         3.137
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0203
_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)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0537
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3189
_reflns_number_total             3220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b00186_si_002.cif
_cod_data_source_block           JAR459
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4347459
_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   0.789
_shelx_estimated_absorpt_t_max   0.852
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
C1 C 0.69748(18) 1.2697(3) 0.0035(3) 0.0121(7) Uani 1 1 d . .
H11 H 0.7447 1.2815 0.0395 0.015 Uiso 1 1 calc R U
H12 H 0.6878 1.2760 -0.0879 0.015 Uiso 1 1 calc R U
C2 C 0.68185(14) 1.4377(4) 0.1830(2) 0.0117(5) Uani 1 1 d . .
H9 H 0.6656 1.5608 0.2094 0.014 Uiso 1 1 calc R U
H10 H 0.7293 1.4370 0.2181 0.014 Uiso 1 1 calc R U
C3 C 0.58457(18) 1.2673(4) 0.1772(4) 0.0146(6) Uani 1 1 d . .
H5 H 0.5665 1.1515 0.2081 0.018 Uiso 1 1 calc R U
H6 H 0.5655 1.3852 0.2037 0.018 Uiso 1 1 calc R U
C4 C 0.59440(14) 1.4258(5) -0.0048(3) 0.0134(6) Uani 1 1 d . .
H1 H 0.5755 1.5486 0.0158 0.016 Uiso 1 1 calc R U
H2 H 0.5832 1.4163 -0.0963 0.016 Uiso 1 1 calc R U
C5 C 0.58324(14) 1.0741(5) -0.0039(3) 0.0156(6) Uani 1 1 d . .
H3 H 0.5681 1.0736 -0.0957 0.019 Uiso 1 1 calc R U
H4 H 0.5612 0.9663 0.0263 0.019 Uiso 1 1 calc R U
C6 C 0.68467(14) 1.0850(4) 0.2137(2) 0.0139(6) Uani 1 1 d . .
H7 H 0.6668 0.9771 0.2523 0.017 Uiso 1 1 calc R U
H8 H 0.7316 1.0911 0.2548 0.017 Uiso 1 1 calc R U
C7 C 0.83782(14) 0.5284(4) -0.0077(2) 0.0134(5) Uani 1 1 d . .
C8 C 0.88774(14) 0.4526(4) -0.0690(2) 0.0131(5) Uani 1 1 d . .
H22 H 0.9291 0.5203 -0.0310 0.016 Uiso 1 1 calc R U
H23 H 0.8735 0.4885 -0.1579 0.016 Uiso 1 1 calc R U
C9 C 0.83700(14) 0.1198(5) -0.1211(3) 0.0202(6) Uani 1 1 d . .
H13 H 0.8203 0.1624 -0.2076 0.030 Uiso 1 1 calc R U
H14 H 0.8051 0.1483 -0.0769 0.030 Uiso 1 1 calc R U
H15 H 0.8454 -0.0211 -0.1185 0.030 Uiso 1 1 calc R U
C10 C 0.92544(14) 0.1536(4) 0.0761(3) 0.0174(5) Uani 1 1 d . .
H19 H 0.8896 0.1541 0.1144 0.021 Uiso 1 1 calc R U
H21 H 0.9397 0.0164 0.0741 0.021 Uiso 1 1 calc R U
C11 C 0.98116(18) 0.2727(4) 0.1574(3) 0.0159(6) Uani 1 1 d . .
C12 C 0.94792(14) 0.1790(5) -0.1312(3) 0.0153(5) Uani 1 1 d . .
H16 H 0.9291 0.2125 -0.2188 0.023 Uiso 1 1 calc R U
H17 H 0.9575 0.0387 -0.1236 0.023 Uiso 1 1 calc R U
H18 H 0.9878 0.2534 -0.0973 0.023 Uiso 1 1 calc R U
C13 C 0.89985(17) 0.2295(4) -0.0587(3) 0.0124(6) Uani 1 1 d . .
N1 N 0.66578(13) 1.4358(4) 0.0465(2) 0.0108(5) Uani 1 1 d . .
N2 N 0.65492(15) 1.2710(3) 0.2351(3) 0.0118(5) Uani 1 1 d . .
N3 N 0.56563(16) 1.2610(3) 0.0420(3) 0.0150(6) Uani 1 1 d . .
O1 O 0.78757(10) 0.6036(3) -0.07623(19) 0.0184(4) Uani 1 1 d . .
O2 O 0.84935(12) 0.5145(4) 0.1086(2) 0.0257(5) Uani 1 1 d . .
O3 O 1.03746(15) 0.2254(3) 0.1793(3) 0.0221(5) Uani 1 1 d . .
O4 O 0.96555(11) 0.4328(4) 0.2058(2) 0.0227(5) Uani 1 1 d . .
P1 P 0.67097(4) 1.03075(11) 0.04741(7) 0.01089(14) Uani 1 1 d . .
Ag1 Ag 0.70708(2) 0.73439(2) -0.01521(3) 0.01596(8) Uani 1 1 d . .
H20 H 0.9343(19) 0.449(6) 0.183(3) 0.024 Uiso 1 1 d . U
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'
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
N1 C1 P1 112.5(2) .
N1 C1 H11 109.1 .
P1 C1 H11 109.1 .
N1 C1 H12 109.1 .
P1 C1 H12 109.1 .
H11 C1 H12 107.8 .
N1 C2 N2 113.9(2) .
N1 C2 H9 108.8 .
N2 C2 H9 108.8 .
N1 C2 H10 108.8 .
N2 C2 H10 108.8 .
H9 C2 H10 107.7 .
N3 C3 N2 113.9(3) .
N3 C3 H5 108.8 .
N2 C3 H5 108.8 .
N3 C3 H6 108.8 .
N2 C3 H6 108.8 .
H5 C3 H6 107.7 .
N3 C4 N1 113.6(3) .
N3 C4 H1 108.8 .
N1 C4 H1 108.8 .
N3 C4 H2 108.8 .
N1 C4 H2 108.8 .
H1 C4 H2 107.7 .
N3 C5 P1 112.2(2) .
N3 C5 H3 109.2 .
P1 C5 H3 109.2 .
N3 C5 H4 109.2 .
P1 C5 H4 109.2 .
H3 C5 H4 107.9 .
N2 C6 P1 112.83(19) .
N2 C6 H7 109.0 .
P1 C6 H7 109.0 .
N2 C6 H8 109.0 .
P1 C6 H8 109.0 .
H7 C6 H8 107.8 .
O1 C7 O2 123.2(2) .
O1 C7 C8 117.7(2) .
O2 C7 C8 119.1(2) .
C7 C8 C13 115.3(2) .
C7 C8 H22 108.4 .
C13 C8 H22 108.4 .
C7 C8 H23 108.4 .
C13 C8 H23 108.4 .
H22 C8 H23 107.5 .
C13 C9 H13 109.5 .
C13 C9 H14 109.5 .
H13 C9 H14 109.5 .
C13 C9 H15 109.5 .
H13 C9 H15 109.5 .
H14 C9 H15 109.5 .
C11 C10 C13 114.1(2) .
C11 C10 H19 108.7 .
C13 C10 H19 108.7 .
C11 C10 H21 108.7 .
C13 C10 H21 108.7 .
H19 C10 H21 107.6 .
O3 C11 O4 120.1(3) .
O3 C11 C10 123.7(3) .
O4 C11 C10 116.2(3) .
C13 C12 H16 109.5 .
C13 C12 H17 109.5 .
H16 C12 H17 109.5 .
C13 C12 H18 109.5 .
H16 C12 H18 109.5 .
H17 C12 H18 109.5 .
C9 C13 C12 107.2(2) .
C9 C13 C8 109.8(3) .
C12 C13 C8 108.0(2) .
C9 C13 C10 107.7(2) .
C12 C13 C10 109.8(3) .
C8 C13 C10 114.1(3) .
C2 N1 C1 110.8(2) .
C2 N1 C4 108.1(2) .
C1 N1 C4 111.5(3) .
C2 N1 Ag1 107.26(17) 1_565
C1 N1 Ag1 108.08(18) 1_565
C4 N1 Ag1 110.99(18) 1_565
C6 N2 C2 111.1(3) .
C6 N2 C3 111.0(2) .
C2 N2 C3 108.3(2) .
C4 N3 C3 109.5(2) .
C4 N3 C5 111.3(3) .
C3 N3 C5 111.6(2) .
C7 O1 Ag1 126.36(16) .
C11 O4 H20 110(4) .
C1 P1 C6 97.00(14) .
C1 P1 C5 98.39(16) .
C6 P1 C5 97.77(14) .
C1 P1 Ag1 121.76(10) .
C6 P1 Ag1 120.44(9) .
C5 P1 Ag1 116.53(10) .
O1 Ag1 P1 142.43(7) .
O1 Ag1 N1 97.86(9) 1_545
P1 Ag1 N1 117.40(7) 1_545
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.479(4) .
C1 P1 1.846(3) .
C1 H11 0.9900 .
C1 H12 0.9900 .
C2 N1 1.475(4) .
C2 N2 1.477(4) .
C2 H9 0.9900 .
C2 H10 0.9900 .
C3 N3 1.458(5) .
C3 N2 1.475(5) .
C3 H5 0.9900 .
C3 H6 0.9900 .
C4 N3 1.457(4) .
C4 N1 1.488(4) .
C4 H1 0.9900 .
C4 H2 0.9900 .
C5 N3 1.469(4) .
C5 P1 1.844(3) .
C5 H3 0.9900 .
C5 H4 0.9900 .
C6 N2 1.476(4) .
C6 P1 1.846(3) .
C6 H7 0.9900 .
C6 H8 0.9900 .
C7 O1 1.249(3) .
C7 O2 1.263(3) .
C7 C8 1.531(4) .
C8 C13 1.546(4) .
C8 H22 0.9900 .
C8 H23 0.9900 .
C9 C13 1.536(4) .
C9 H13 0.9800 .
C9 H14 0.9800 .
C9 H15 0.9800 .
C10 C11 1.524(4) .
C10 C13 1.548(4) .
C10 H19 0.9900 .
C10 H21 0.9900 .
C11 O3 1.216(5) .
C11 O4 1.309(4) .
C12 C13 1.535(4) .
C12 H16 0.9800 .
C12 H17 0.9800 .
C12 H18 0.9800 .
N1 Ag1 2.410(2) 1_565
O1 Ag1 2.237(2) .
O4 H20 0.66(4) .
P1 Ag1 2.3520(8) .
Ag1 N1 2.410(2) 1_545
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
C2 H10 O1 0.99 2.31 3.015(3) 127.2 2_575
C3 H5 O4 0.99 2.64 3.530(4) 149.2 3_455
C3 H6 O3 0.99 2.40 3.296(3) 150.3 3_465
C4 H1 O3 0.99 2.53 3.389(4) 144.9 3_465
C4 H2 O3 0.99 2.62 3.564(4) 159.9 4_464
C5 H3 O4 0.99 2.66 3.519(4) 145.4 4_464
C5 H4 O3 0.99 2.54 3.478(4) 158.0 3_455
C8 H23 O2 0.99 2.53 3.489(3) 163.8 2_564
O4 H20 O2 0.66(4) 1.84(4) 2.502(3) 173(5) .
