#------------------------------------------------------------------------------
#$Date: 2020-10-21 08:07:36 +0300 (Wed, 21 Oct 2020) $
#$Revision: 258511 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243631.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243631
loop_
_publ_author_name
'Moon, Dohyun'
'Choi, Jong-Ha'
_publ_section_title
;
 Crystal structure of
 [2,13-bis(acetamido)-5,16-dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12^]docosane-κ⁴N]silver(II)
 dinitrate from synchrotron X-ray data
;
_journal_coeditor_code           SJ5548
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              461
_journal_page_last               464
_journal_paper_doi               10.1107/S2056989018003560
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '[Ag (C24 H46 N6 O2)] (N O3)2'
_chemical_formula_moiety         'C24 H46 Ag N6 O2 2+, 2(N O3 -)'
_chemical_formula_sum            'C24 H46 Ag N8 O8'
_chemical_formula_weight         682.56
_chemical_name_systematic
'[(5,16-Dimethyl-2,6,13,17-tetraazatricyclo[16.4.0.0^7,12^]docosane-2,13-diyl)diacetamide-κ⁴N²,N⁶,N¹³,N¹⁷]silver(II) dinitrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                104.32(3)
_cell_angle_beta                 90.28(3)
_cell_angle_gamma                109.60(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3460(17)
_cell_length_b                   9.2874(19)
_cell_length_c                   10.171(2)
_cell_measurement_reflns_used    46429
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.679
_cell_measurement_theta_min      0.350
_cell_volume                     716.3(3)
_computing_cell_refinement
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
PAL BL2D-SMDC Program (Shin et al., 2016)
;
_computing_data_reduction
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
DIAMOND 4 (Putz & Brandenburg, 2014)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.610
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7431
_diffrn_reflns_theta_full        21.469
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.782
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(HKL3000sm SCALEPACK; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             357
_exptl_crystal_size_max          0.021
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.713
_refine_diff_density_min         -2.172
_refine_ls_extinction_coef       0.065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0747P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                3418
_reflns_number_total             3750
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5548sup1.cif
_cod_data_source_block           I
_cod_database_code               2243631
_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   0.989
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag Ag1 0.500000 0.500000 0.500000 0.01559(13) Uani d 1 . .
O O1 0.2273(3) 0.5401(3) 0.0700(3) 0.0332(6) Uani d 1 . .
N N1 0.3945(3) 0.4502(3) 0.2855(2) 0.0138(4) Uani d 1 . .
N N2 0.3842(3) 0.2496(3) 0.4657(2) 0.0141(4) Uani d 1 . .
H H2 0.480698 0.207953 0.460293 0.017 Uiso calc 1 . .
N N3 -0.0231(4) 0.4445(4) 0.1558(3) 0.0287(6) Uani d 1 . .
H H3A -0.082643 0.448023 0.085766 0.034 Uiso calc 1 . .
H H3B -0.075649 0.410273 0.222782 0.034 Uiso calc 1 . .
C C1 0.5320(4) 0.5522(4) 0.2206(3) 0.0190(6) Uani d 1 . .
H H1A 0.491733 0.531956 0.123804 0.023 Uiso calc 1 . .
H H1AB 0.633336 0.519689 0.222357 0.023 Uiso calc 1 . .
C C2 0.2334(4) 0.4871(4) 0.2920(3) 0.0200(6) Uani d 1 . .
H H2A 0.258145 0.591883 0.357970 0.024 Uiso calc 1 . .
H H2AB 0.149558 0.408176 0.330418 0.024 Uiso calc 1 . .
C C3 0.1459(4) 0.4909(4) 0.1604(3) 0.0223(6) Uani d 1 . .
C C4 0.3680(4) 0.2774(3) 0.2288(3) 0.0167(5) Uani d 1 . .
H H4 0.483624 0.268837 0.217142 0.020 Uiso calc 1 . .
C C5 0.2651(4) 0.2038(4) 0.0888(3) 0.0218(6) Uani d 1 . .
H H5A 0.148066 0.206799 0.096639 0.026 Uiso calc 1 . .
H H5B 0.319617 0.266303 0.024804 0.026 Uiso calc 1 . .
C C6 0.2561(5) 0.0326(4) 0.0329(3) 0.0296(7) Uani d 1 . .
H H6A 0.186557 -0.013650 -0.056301 0.035 Uiso calc 1 . .
H H6B 0.372603 0.030416 0.018612 0.035 Uiso calc 1 . .
C C7 0.1776(5) -0.0665(4) 0.1307(3) 0.0318(8) Uani d 1 . .
H H7A 0.179869 -0.175056 0.095173 0.038 Uiso calc 1 . .
H H7B 0.056864 -0.074055 0.137454 0.038 Uiso calc 1 . .
C C8 0.2763(5) 0.0082(4) 0.2717(3) 0.0249(6) Uani d 1 . .
H H8A 0.393756 0.005616 0.265973 0.030 Uiso calc 1 . .
H H8B 0.220186 -0.054797 0.334862 0.030 Uiso calc 1 . .
C C9 0.2852(4) 0.1794(3) 0.3284(3) 0.0148(5) Uani d 1 . .
H H9 0.166364 0.180502 0.337656 0.018 Uiso calc 1 . .
C C10 0.2906(4) 0.2024(3) 0.5819(3) 0.0182(5) Uani d 1 . .
H H10 0.252172 0.084275 0.560973 0.022 Uiso calc 1 . .
C C11 0.4128(4) 0.2696(4) 0.7127(3) 0.0207(6) Uani d 1 . .
H H11A 0.357944 0.213455 0.780635 0.025 Uiso calc 1 . .
H H11B 0.517100 0.243381 0.692138 0.025 Uiso calc 1 . .
C C12 0.1312(4) 0.2481(4) 0.5968(3) 0.0269(7) Uani d 1 . .
H H12A 0.159371 0.357672 0.591454 0.040 Uiso calc 1 . .
H H12B 0.088753 0.238874 0.685098 0.040 Uiso calc 1 . .
H H12C 0.042823 0.177157 0.523376 0.040 Uiso calc 1 . .
O O1N 0.7629(4) 0.3507(3) 0.3690(3) 0.0343(6) Uani d 1 . .
O O2N 0.8673(3) 0.1611(3) 0.3122(3) 0.0338(6) Uani d 1 . .
O O3N 0.6869(3) 0.1576(3) 0.4643(3) 0.0328(6) Uani d 1 . .
N N1N 0.7737(3) 0.2225(3) 0.3815(3) 0.0237(5) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0074 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -1.2704 0.8398 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Ag1 N2 2_666 . 180.0 ?
N2 Ag1 N1 2_666 . 96.57(9) ?
N2 Ag1 N1 . . 83.43(9) ?
N2 Ag1 N1 2_666 2_666 83.43(9) ?
N2 Ag1 N1 . 2_666 96.57(9) ?
N1 Ag1 N1 . 2_666 180.0(2) ?
C2 N1 C1 . . 114.7(2) ?
C2 N1 C4 . . 114.1(2) ?
C1 N1 C4 . . 111.6(2) ?
C2 N1 Ag1 . . 106.66(16) ?
C1 N1 Ag1 . . 105.59(17) ?
C4 N1 Ag1 . . 102.92(15) ?
C9 N2 C10 . . 115.8(2) ?
C9 N2 Ag1 . . 109.76(16) ?
C10 N2 Ag1 . . 113.18(17) ?
C9 N2 H2 . . 105.7 ?
C10 N2 H2 . . 105.7 ?
Ag1 N2 H2 . . 105.7 ?
C3 N3 H3A . . 120.0 ?
C3 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
N1 C1 C11 . 2_666 115.2(2) ?
N1 C1 H1A . . 108.5 ?
C11 C1 H1A 2_666 . 108.5 ?
N1 C1 H1AB . . 108.5 ?
C11 C1 H1AB 2_666 . 108.5 ?
H1A C1 H1AB . . 107.5 ?
N1 C2 C3 . . 119.0(2) ?
N1 C2 H2A . . 107.6 ?
C3 C2 H2A . . 107.6 ?
N1 C2 H2AB . . 107.6 ?
C3 C2 H2AB . . 107.6 ?
H2A C2 H2AB . . 107.0 ?
O1 C3 N3 . . 123.2(3) ?
O1 C3 C2 . . 122.4(3) ?
N3 C3 C2 . . 114.3(3) ?
N1 C4 C5 . . 113.8(2) ?
N1 C4 C9 . . 111.8(2) ?
C5 C4 C9 . . 109.8(2) ?
N1 C4 H4 . . 107.0 ?
C5 C4 H4 . . 107.0 ?
C9 C4 H4 . . 107.0 ?
C6 C5 C4 . . 110.7(3) ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C7 C6 C5 . . 111.1(3) ?
C7 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
C7 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
C6 C7 C8 . . 110.4(3) ?
C6 C7 H7A . . 109.6 ?
C8 C7 H7A . . 109.6 ?
C6 C7 H7B . . 109.6 ?
C8 C7 H7B . . 109.6 ?
H7A C7 H7B . . 108.1 ?
C7 C8 C9 . . 111.9(3) ?
C7 C8 H8A . . 109.2 ?
C9 C8 H8A . . 109.2 ?
C7 C8 H8B . . 109.2 ?
C9 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
N2 C9 C8 . . 110.5(2) ?
N2 C9 C4 . . 110.5(2) ?
C8 C9 C4 . . 109.6(2) ?
N2 C9 H9 . . 108.7 ?
C8 C9 H9 . . 108.7 ?
C4 C9 H9 . . 108.7 ?
N2 C10 C12 . . 111.9(2) ?
N2 C10 C11 . . 109.9(2) ?
C12 C10 C11 . . 113.0(2) ?
N2 C10 H10 . . 107.3 ?
C12 C10 H10 . . 107.3 ?
C11 C10 H10 . . 107.3 ?
C1 C11 C10 2_666 . 117.6(2) ?
C1 C11 H11A 2_666 . 107.9 ?
C10 C11 H11A . . 107.9 ?
C1 C11 H11B 2_666 . 107.9 ?
C10 C11 H11B . . 107.9 ?
H11A C11 H11B . . 107.2 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O2N N1N O3N . . 120.6(3) ?
O2N N1N O1N . . 120.7(3) ?
O3N N1N O1N . . 118.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ag1 N2 2_666 2.134(2) ?
Ag1 N2 . 2.134(2) ?
Ag1 N1 . 2.227(2) ?
Ag1 N1 2_666 2.227(2) ?
O1 C3 . 1.234(4) ?
N1 C2 . 1.493(4) ?
N1 C1 . 1.496(4) ?
N1 C4 . 1.504(4) ?
N2 C9 . 1.494(3) ?
N2 C10 . 1.495(3) ?
N2 H2 . 1.0000 ?
N3 C3 . 1.326(4) ?
N3 H3A . 0.8800 ?
N3 H3B . 0.8800 ?
C1 C11 2_666 1.530(4) ?
C1 H1A . 0.9900 ?
C1 H1AB . 0.9900 ?
C2 C3 . 1.535(4) ?
C2 H2A . 0.9900 ?
C2 H2AB . 0.9900 ?
C4 C5 . 1.531(4) ?
C4 C9 . 1.540(4) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.526(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.523(5) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.527(4) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.527(4) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9 . 1.0000 ?
C10 C12 . 1.524(4) ?
C10 C11 . 1.532(4) ?
C10 H10 . 1.0000 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
O1N N1N . 1.261(4) ?
O2N N1N . 1.240(4) ?
O3N N1N . 1.249(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1N . 1.00 2.59 3.214(4) 120.6 yes
N2 H2 O3N . 1.00 1.93 2.925(4) 171.9 yes
N3 H3A O1 2_565 0.88 2.03 2.913(4) 177.3 yes
N3 H3B O1N 1_455 0.88 2.06 2.930(4) 167.5 yes
N3 H3B O2N 1_455 0.88 2.59 3.281(4) 135.9 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C11 . . . 2_666 57.5(3) ?
C4 N1 C1 C11 . . . 2_666 -170.8(2) ?
Ag1 N1 C1 C11 . . . 2_666 -59.7(3) ?
C1 N1 C2 C3 . . . . 53.5(3) ?
C4 N1 C2 C3 . . . . -77.0(3) ?
Ag1 N1 C2 C3 . . . . 170.0(2) ?
N1 C2 C3 O1 . . . . -35.8(4) ?
N1 C2 C3 N3 . . . . 147.4(3) ?
C2 N1 C4 C5 . . . . 54.2(3) ?
C1 N1 C4 C5 . . . . -77.8(3) ?
Ag1 N1 C4 C5 . . . . 169.4(2) ?
C2 N1 C4 C9 . . . . -70.9(3) ?
C1 N1 C4 C9 . . . . 157.1(2) ?
Ag1 N1 C4 C9 . . . . 44.3(2) ?
N1 C4 C5 C6 . . . . 175.4(3) ?
C9 C4 C5 C6 . . . . -58.5(3) ?
C4 C5 C6 C7 . . . . 57.5(4) ?
C5 C6 C7 C8 . . . . -55.6(4) ?
C6 C7 C8 C9 . . . . 56.2(4) ?
C10 N2 C9 C8 . . . . -78.2(3) ?
Ag1 N2 C9 C8 . . . . 152.1(2) ?
C10 N2 C9 C4 . . . . 160.3(2) ?
Ag1 N2 C9 C4 . . . . 30.6(3) ?
C7 C8 C9 N2 . . . . -179.4(3) ?
C7 C8 C9 C4 . . . . -57.4(4) ?
N1 C4 C9 N2 . . . . -52.8(3) ?
C5 C4 C9 N2 . . . . 179.9(2) ?
N1 C4 C9 C8 . . . . -174.8(2) ?
C5 C4 C9 C8 . . . . 57.9(3) ?
C9 N2 C10 C12 . . . . -59.3(3) ?
Ag1 N2 C10 C12 . . . . 68.7(3) ?
C9 N2 C10 C11 . . . . 174.3(2) ?
Ag1 N2 C10 C11 . . . . -57.7(3) ?
N2 C10 C11 C1 . . . 2_666 73.2(3) ?
C12 C10 C11 C1 . . . 2_666 -52.5(3) ?

_cod_database_fobs_code 2243631
