#------------------------------------------------------------------------------
#$Date: 2022-02-15 05:00:01 +0200 (Tue, 15 Feb 2022) $
#$Revision: 272961 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022547.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_2022547
loop_
_publ_author_name
'Blake, Alexander J.'
'Lippolis, Vito'
'Schroder, Martin'
_publ_section_title
;
 Coordination chemistry of nitrile-functionalized mixed thia-aza
 macrocycles [9]aneN₂S and [9]aneNS₂ towards silver(I)
;
_journal_coeditor_code           KY3213
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322962200105X
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          '[Ag (C12 H20 N4 S) (N C S)]'
_chemical_formula_moiety         'C13 H20 Ag N5 S2'
_chemical_formula_sum            'C13 H20 Ag N5 S2'
_chemical_formula_weight         418.33
_chemical_name_systematic
;
[4,7-Bis(2-cyanoethyl)-1-thia-4,7-diazacyclononane-\
κ³N,N',S](thiocyanato-κS)silver(I)
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                96.5850(10)
_cell_angle_beta                 99.0230(10)
_cell_angle_gamma                95.3130(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4426(6)
_cell_length_b                   8.5739(6)
_cell_length_c                   11.8497(8)
_cell_measurement_reflns_used    4102
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      2.4
_cell_volume                     836.19(10)
_computing_cell_refinement
;
SMART (Bruker, 1998)
;
_computing_data_collection
;
SMART (Bruker, 1998)
;
_computing_data_reduction
;
SAINT (Bruker, 1999)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.336
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area-detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.019
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3668
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.683
_diffrn_reflns_theta_min         1.755
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SHELXTL; Sheldrick, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       Block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.406
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0208
_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)+(0.0321P)²+0.1835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0554
_reflns_number_gt                3401
_reflns_number_total             5159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ky3213sup1.cif
_cod_data_source_block           AgL2SCN
_cod_original_cell_volume        836.190(10)
_cod_database_code               2022547
_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.
;
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 0.45271(2) 0.67967(2) 0.39303(2) 0.02735(6) Uani d 1 . .
C C 0.5932(2) 0.4009(2) 0.26281(19) 0.0313(4) Uani d 1 . .
N N 0.5567(2) 0.3379(2) 0.16981(19) 0.0448(5) Uani d 1 . .
S S1 0.30887(6) 0.91065(6) 0.45249(4) 0.02851(11) Uani d 1 . .
C C2 0.1077(2) 0.8015(2) 0.41856(16) 0.0284(4) Uani d 1 . .
H H2A 0.099204 0.725699 0.474927 0.034 Uiso calc 1 . .
H H2B 0.027710 0.877085 0.429162 0.034 Uiso calc 1 . .
S S 0.65402(7) 0.49300(7) 0.39676(4) 0.03595(12) Uani d 1 . .
C C3 0.0617(2) 0.7106(2) 0.29747(16) 0.0248(4) Uani d 1 . .
H H3A -0.046607 0.651542 0.290188 0.030 Uiso calc 1 . .
H H3B 0.054769 0.787191 0.240856 0.030 Uiso calc 1 . .
N N4 0.17585(17) 0.59921(17) 0.26873(13) 0.0223(3) Uani d 1 . .
C C5 0.2127(2) 0.5974(2) 0.15067(15) 0.0244(4) Uani d 1 . .
H H5A 0.111349 0.567238 0.094771 0.029 Uiso calc 1 . .
H H5B 0.285671 0.515680 0.137477 0.029 Uiso calc 1 . .
C C6 0.2913(2) 0.7554(2) 0.12755(15) 0.0243(4) Uani d 1 . .
H H6A 0.320174 0.742555 0.049455 0.029 Uiso calc 1 . .
H H6B 0.212044 0.833452 0.128798 0.029 Uiso calc 1 . .
N N7 0.43751(17) 0.81746(17) 0.21205(13) 0.0222(3) Uani d 1 . .
C C8 0.4433(2) 0.9845(2) 0.25684(16) 0.0262(4) Uani d 1 . .
H H8A 0.429733 1.045962 0.190860 0.031 Uiso calc 1 . .
H H8B 0.551691 1.020002 0.302759 0.031 Uiso calc 1 . .
C C71 0.5874(2) 0.7824(2) 0.17176(16) 0.0241(4) Uani d 1 . .
H H71A 0.577751 0.668412 0.142763 0.029 Uiso calc 1 . .
H H71B 0.677022 0.803938 0.238190 0.029 Uiso calc 1 . .
C C72 0.6311(2) 0.8775(2) 0.07605(16) 0.0261(4) Uani d 1 . .
H H72A 0.543288 0.855754 0.008450 0.031 Uiso calc 1 . .
H H72B 0.642522 0.991918 0.104194 0.031 Uiso calc 1 . .
C C73 0.7826(2) 0.8348(2) 0.04165(16) 0.0304(4) Uani d 1 . .
N N74 0.8999(2) 0.7988(3) 0.01779(17) 0.0445(5) Uani d 1 . .
C C41 0.1307(2) 0.4406(2) 0.29564(16) 0.0253(4) Uani d 1 . .
H H41A 0.111982 0.448886 0.376417 0.030 Uiso calc 1 . .
H H41B 0.222344 0.377595 0.289955 0.030 Uiso calc 1 . .
C C42 -0.0216(2) 0.3510(2) 0.21647(16) 0.0277(4) Uani d 1 . .
H H42A -0.111695 0.417330 0.215439 0.033 Uiso calc 1 . .
H H42B 0.000236 0.330067 0.136780 0.033 Uiso calc 1 . .
C C43 -0.0679(2) 0.2013(2) 0.25739(17) 0.0283(4) Uani d 1 . .
N N44 -0.1000(2) 0.0852(2) 0.29014(16) 0.0380(4) Uani d 1 . .
C C9 0.3168(2) 1.0231(2) 0.33171(17) 0.0290(4) Uani d 1 . .
H H9A 0.209310 1.005667 0.281911 0.035 Uiso calc 1 . .
H H9B 0.337299 1.136793 0.362339 0.035 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 Ag1 N4 . . 79.60(4) ?
S1 Ag1 N7 . . 79.77(4) ?
S Ag1 S1 . . 160.21(2) ?
S Ag1 N4 . . 119.16(4) ?
S Ag1 N7 . . 111.02(4) ?
N4 Ag1 N7 . . 71.15(5) ?
N C S . . 177.7(2) ?
C2 S1 Ag1 . . 95.16(7) ?
C9 S1 Ag1 . . 101.15(6) ?
C9 S1 C2 . . 103.37(9) ?
S1 C2 H2A . . 108.3 ?
S1 C2 H2B . . 108.3 ?
H2A C2 H2B . . 107.4 ?
C3 C2 S1 . . 115.81(13) ?
C3 C2 H2A . . 108.3 ?
C3 C2 H2B . . 108.3 ?
C S Ag1 . . 97.17(7) ?
C2 C3 H3A . . 108.8 ?
C2 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
N4 C3 C2 . . 113.77(15) ?
N4 C3 H3A . . 108.8 ?
N4 C3 H3B . . 108.8 ?
C3 N4 Ag1 . . 110.77(10) ?
C3 N4 C5 . . 114.32(14) ?
C5 N4 Ag1 . . 102.34(10) ?
C41 N4 Ag1 . . 103.42(10) ?
C41 N4 C3 . . 112.58(14) ?
C41 N4 C5 . . 112.35(14) ?
N4 C5 H5A . . 108.8 ?
N4 C5 H5B . . 108.8 ?
N4 C5 C6 . . 113.72(14) ?
H5A C5 H5B . . 107.7 ?
C6 C5 H5A . . 108.8 ?
C6 C5 H5B . . 108.8 ?
C5 C6 H6A . . 108.9 ?
C5 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
N7 C6 C5 . . 113.24(14) ?
N7 C6 H6A . . 108.9 ?
N7 C6 H6B . . 108.9 ?
C6 N7 Ag1 . . 111.38(10) ?
C8 N7 Ag1 . . 103.40(10) ?
C8 N7 C6 . . 114.09(14) ?
C8 N7 C71 . . 111.70(14) ?
C71 N7 Ag1 . . 101.89(10) ?
C71 N7 C6 . . 113.25(14) ?
N7 C8 H8A . . 108.5 ?
N7 C8 H8B . . 108.5 ?
N7 C8 C9 . . 115.13(15) ?
H8A C8 H8B . . 107.5 ?
C9 C8 H8A . . 108.5 ?
C9 C8 H8B . . 108.5 ?
N7 C71 H71A . . 108.6 ?
N7 C71 H71B . . 108.6 ?
N7 C71 C72 . . 114.52(14) ?
H71A C71 H71B . . 107.6 ?
C72 C71 H71A . . 108.6 ?
C72 C71 H71B . . 108.6 ?
C71 C72 H72A . . 109.5 ?
C71 C72 H72B . . 109.5 ?
H72A C72 H72B . . 108.1 ?
C73 C72 C71 . . 110.56(15) ?
C73 C72 H72A . . 109.5 ?
C73 C72 H72B . . 109.5 ?
N74 C73 C72 . . 177.8(2) ?
N4 C41 H41A . . 108.7 ?
N4 C41 H41B . . 108.7 ?
N4 C41 C42 . . 114.42(15) ?
H41A C41 H41B . . 107.6 ?
C42 C41 H41A . . 108.7 ?
C42 C41 H41B . . 108.7 ?
C41 C42 H42A . . 109.5 ?
C41 C42 H42B . . 109.5 ?
H42A C42 H42B . . 108.1 ?
C43 C42 C41 . . 110.59(16) ?
C43 C42 H42A . . 109.5 ?
C43 C42 H42B . . 109.5 ?
N44 C43 C42 . . 178.4(2) ?
S1 C9 H9A . . 108.3 ?
S1 C9 H9B . . 108.3 ?
C8 C9 S1 . . 116.03(14) ?
C8 C9 H9A . . 108.3 ?
C8 C9 H9B . . 108.3 ?
H9A C9 H9B . . 107.4 ?
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 S1 . 2.5074(5) ?
Ag1 S . 2.4390(5) ?
Ag1 N4 . 2.5490(14) ?
Ag1 N7 . 2.5561(15) ?
C N . 1.152(3) ?
C S . 1.670(2) ?
S1 C2 . 1.8241(19) ?
S1 C9 . 1.8211(19) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.526(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C3 N4 . 1.468(2) ?
N4 C5 . 1.479(2) ?
N4 C41 . 1.462(2) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5 C6 . 1.525(2) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C6 N7 . 1.476(2) ?
N7 C8 . 1.462(2) ?
N7 C71 . 1.465(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C8 C9 . 1.528(3) ?
C71 H71A . 0.9900 ?
C71 H71B . 0.9900 ?
C71 C72 . 1.541(2) ?
C72 H72A . 0.9900 ?
C72 H72B . 0.9900 ?
C72 C73 . 1.467(3) ?
C73 N74 . 1.132(3) ?
C41 H41A . 0.9900 ?
C41 H41B . 0.9900 ?
C41 C42 . 1.548(2) ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C42 C43 . 1.464(3) ?
C43 N44 . 1.135(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
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
Ag1 S1 C2 C3 . . . . -52.45(14) ?
Ag1 S1 C9 C8 . . . . -18.86(15) ?
Ag1 N4 C5 C6 . . . . -58.42(15) ?
Ag1 N4 C41 C42 . . . . -170.34(13) ?
Ag1 N7 C8 C9 . . . . -54.08(16) ?
Ag1 N7 C71 C72 . . . . -168.44(12) ?
S1 C2 C3 N4 . . . . 55.39(19) ?
C2 S1 C9 C8 . . . . -116.97(15) ?
C2 C3 N4 Ag1 . . . . -23.22(17) ?
C2 C3 N4 C5 . . . . -138.19(15) ?
C2 C3 N4 C41 . . . . 92.03(18) ?
C3 N4 C5 C6 . . . . 61.40(19) ?
C3 N4 C41 C42 . . . . 70.1(2) ?
N4 C5 C6 N7 . . . . 54.1(2) ?
N4 C41 C42 C43 . . . . -173.76(16) ?
C5 N4 C41 C42 . . . . -60.7(2) ?
C5 C6 N7 Ag1 . . . . -16.69(18) ?
C5 C6 N7 C8 . . . . -133.28(16) ?
C5 C6 N7 C71 . . . . 97.45(17) ?
C6 N7 C8 C9 . . . . 67.1(2) ?
C6 N7 C71 C72 . . . . 71.83(19) ?
N7 C8 C9 S1 . . . . 53.5(2) ?
N7 C71 C72 C73 . . . . 179.87(15) ?
C8 N7 C71 C72 . . . . -58.6(2) ?
C71 N7 C8 C9 . . . . -162.91(15) ?
C41 N4 C5 C6 . . . . -168.71(14) ?
C9 S1 C2 C3 . . . . 50.32(16) ?

_cod_database_fobs_code 2022547
