#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/91/1569106.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_1569106
loop_
_publ_author_name
'Crundwell, Guy'
'Ellis, Kristin M.'
_publ_section_title
;
 Bis[5-methyl-2,3-bis(thiophen-2-yl)quinoxaline-\kN 1](nitrato-κ2
 O,O′)silver(I)
;
_journal_coeditor_code           BT4136
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x230265
_journal_paper_doi               10.1107/S2414314623002651
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          '[Ag (N O3) (C17 H12 N2 S2)2]'
_chemical_formula_moiety         'C34 H24 Ag N5 O3 S4'
_chemical_formula_sum            'C34 H24 Ag N5 O3 S4'
_chemical_formula_weight         786.69
_chemical_name_common
;
Bis-(2,3-di(thiophen-2'-yl)-5-methylquinoxaline)silver(I) nitrate
;
_chemical_name_systematic
Bis[5-methyl-2,3-bis(thiophen-2-yl)quinoxaline-κN¹](nitrato-κ²O,O')silver(I)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90.00
_cell_angle_beta                 120.967(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9246(10)
_cell_length_b                   8.9789(4)
_cell_length_c                   22.2776(13)
_cell_measurement_reflns_used    3173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.6540
_cell_measurement_theta_min      4.5270
_cell_volume                     3245.9(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009) and
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1790
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11880
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         33.50
_diffrn_reflns_theta_min         4.14
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.459
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         5743
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.9845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3896
_reflns_number_total             5743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt4136.cif
_cod_data_source_block           I
_cod_original_cell_volume        3245.9(3)
_cod_database_code               1569106
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
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 0.5000 0.28104(3) 0.7500 0.05147(10) Uani d 1 . .
O O1 0.47816(15) 0.5374(2) 0.78512(12) 0.0785(6) Uani d 1 . .
O O2 0.5000 0.7444(4) 0.7500 0.0920(11) Uani d 1 . .
N N1 0.37028(10) 0.2035(2) 0.67321(9) 0.0397(4) Uani d 1 A .
N N2 0.21614(10) 0.0848(2) 0.57801(9) 0.0404(4) Uani d 1 . .
N N3 0.5000 0.6080(4) 0.7500 0.0537(7) Uani d 1 . .
C C1 0.27757(12) 0.0778(2) 0.56570(10) 0.0386(4) Uani d 1 A .
C C2 0.35742(12) 0.1362(2) 0.61561(10) 0.0378(4) Uani d 1 . .
C C3 0.30625(13) 0.2174(2) 0.68498(11) 0.0396(4) Uani d 1 . .
C C4 0.31805(15) 0.2932(3) 0.74494(12) 0.0517(6) Uani d 1 A .
H H4 0.3686 0.3366 0.7761 0.062 Uiso calc 1 . .
C C5 0.25366(16) 0.3015(3) 0.75613(13) 0.0531(6) Uani d 1 . .
H H5 0.2608 0.3511 0.7955 0.064 Uiso calc 1 A .
C C6 0.17693(15) 0.2370(3) 0.70951(13) 0.0467(5) Uani d 1 A .
H H6 0.1348 0.2435 0.7192 0.056 Uiso calc 1 . .
C C7 0.16241(12) 0.1645(2) 0.64991(11) 0.0406(4) Uani d 1 . .
C C8 0.22894(12) 0.1547(2) 0.63735(10) 0.0367(4) Uani d 1 A .
C C9 0.08016(14) 0.0988(3) 0.59912(13) 0.0571(6) Uani d 1 A .
H H9A 0.0870 -0.0036 0.5906 0.086 Uiso calc 1 . .
H H9B 0.0558 0.1532 0.5559 0.086 Uiso calc 1 . .
H H9C 0.0449 0.1045 0.6182 0.086 Uiso calc 1 . .
C C10 0.25759(13) 0.0051(3) 0.49975(11) 0.0431(5) Uani d 1 . .
C C11 0.29678(16) 0.0086(3) 0.46086(12) 0.0536(6) Uani d 1 A .
H H11 0.3452 0.0600 0.4739 0.064 Uiso calc 1 . .
C C12 0.25216(19) -0.0774(3) 0.39869(14) 0.0667(7) Uani d 1 . .
H H12 0.2688 -0.0887 0.3663 0.080 Uiso calc 1 A .
C C13 0.18427(16) -0.1403(3) 0.39128(13) 0.0619(7) Uani d 1 A .
H H13 0.1490 -0.2000 0.3534 0.074 Uiso calc 1 . .
S S1 0.16912(4) -0.10019(8) 0.45797(3) 0.06093(18) Uani d 1 A .
C C14 0.42926(12) 0.1231(2) 0.60653(11) 0.0405(4) Uani d 0.647(4) A 1
C C15 0.4616(7) 0.2282(9) 0.5845(7) 0.0562(8) Uani d 0.647(4) A 1
H H15 0.4423 0.3255 0.5739 0.067 Uiso calc 0.647(4) A 1
C C16 0.529(2) 0.173(2) 0.579(3) 0.0586(11) Uani d 0.647(4) A 1
H H16 0.5563 0.2273 0.5614 0.070 Uiso calc 0.647(4) A 1
C C17 0.5493(8) 0.0331(15) 0.6030(10) 0.061(2) Uani d 0.647(4) A 1
H H17 0.5946 -0.0181 0.6076 0.073 Uiso calc 0.647(4) A 1
S S2 0.48188(14) -0.03878(19) 0.62341(13) 0.0742(5) Uani d 0.647(4) A 1
C C14B 0.42926(12) 0.1231(2) 0.60653(11) 0.0405(4) Uani d 0.353(4) A 2
C C15B 0.4753(11) -0.0013(15) 0.6156(11) 0.0742(5) Uani d 0.353(4) A 2
H H15B 0.4699 -0.0908 0.6339 0.089 Uiso calc 0.353(4) A 2
C C16B 0.5332(17) 0.024(3) 0.593(2) 0.061(2) Uani d 0.353(4) A 2
H H16B 0.5654 -0.0503 0.5902 0.073 Uiso calc 0.353(4) A 2
C C17B 0.536(4) 0.167(4) 0.577(5) 0.0586(11) Uani d 0.353(4) A 2
H H17B 0.5746 0.2062 0.5680 0.070 Uiso calc 0.353(4) A 2
S S2B 0.4599(3) 0.2654(4) 0.5764(3) 0.0562(8) Uani d 0.353(4) A 2
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'
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
O1 Ag1 O1 2_656 . 49.30(9) y
N1 Ag1 O1 2_656 . 109.40(7) y
N1 Ag1 O1 . 2_656 109.41(7) y
N1 Ag1 O1 2_656 2_656 103.14(7) y
N1 Ag1 O1 . . 103.14(7) y
N1 Ag1 N1 . 2_656 144.14(9) y
N3 O1 Ag1 . . 96.32(18) no
C2 N1 Ag1 . . 117.43(13) no
C2 N1 C3 . . 119.18(17) no
C3 N1 Ag1 . . 123.33(13) no
C1 N2 C8 . . 118.92(17) no
O1 N3 O1 2_656 . 118.1(3) no
O2 N3 O1 . 2_656 120.97(17) no
O2 N3 O1 . . 120.97(17) no
N2 C1 C2 . . 120.49(18) no
N2 C1 C10 . . 115.22(18) no
C2 C1 C10 . . 124.28(18) no
N1 C2 C1 . . 120.83(18) no
N1 C2 C14 . . 116.47(17) no
C1 C2 C14 . . 122.69(18) no
N1 C3 C4 . . 120.00(19) no
N1 C3 C8 . . 119.80(18) no
C8 C3 C4 . . 120.20(19) no
C3 C4 H4 . . 120.7 no
C5 C4 C3 . . 118.5(2) no
C5 C4 H4 . . 120.7 no
C4 C5 H5 . . 119.2 no
C4 C5 C6 . . 121.5(2) no
C6 C5 H5 . . 119.2 no
C5 C6 H6 . . 119.1 no
C7 C6 C5 . . 121.8(2) no
C7 C6 H6 . . 119.1 no
C6 C7 C8 . . 117.46(19) no
C6 C7 C9 . . 122.07(19) no
C8 C7 C9 . . 120.47(19) no
N2 C8 C3 . . 120.67(17) no
N2 C8 C7 . . 118.87(18) no
C3 C8 C7 . . 120.46(18) no
C7 C9 H9A . . 109.5 no
C7 C9 H9B . . 109.5 no
C7 C9 H9C . . 109.5 no
H9A C9 H9B . . 109.5 no
H9A C9 H9C . . 109.5 no
H9B C9 H9C . . 109.5 no
C1 C10 S1 . . 117.63(16) no
C11 C10 C1 . . 131.5(2) no
C11 C10 S1 . . 110.81(16) no
C10 C11 H11 . . 124.7 no
C10 C11 C12 . . 110.6(2) no
C12 C11 H11 . . 124.7 no
C11 C12 H12 . . 123.2 no
C13 C12 C11 . . 113.7(2) no
C13 C12 H12 . . 123.2 no
C12 C13 H13 . . 123.5 no
C12 C13 S1 . . 112.9(2) no
S1 C13 H13 . . 123.5 no
C13 S1 C10 . . 91.99(13) no
C2 C14 S2 . . 121.03(17) no
C15 C14 C2 . . 128.1(5) no
C15 C14 S2 . . 110.9(4) no
C14 C15 H15 . . 123.8 no
C14 C15 C16 . . 112.3(8) no
C16 C15 H15 . . 123.8 no
C15 C16 H16 . . 124.0 no
C17 C16 C15 . . 112.0(10) no
C17 C16 H16 . . 124.0 no
C16 C17 H17 . . 124.2 no
C16 C17 S2 . . 111.6(8) no
S2 C17 H17 . . 124.2 no
C17 S2 C14 . . 93.0(4) no
C16B C15B H15B . . 124.4 no
C15B C16B H16B . . 123.7 no
C17B C16B C15B . . 112.6(18) no
C17B C16B H16B . . 123.7 no
C16B C17B H17B . . 124.4 no
C16B C17B S2B . . 111.1(17) no
S2B C17B H17B . . 124.4 no
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 O1 . 2.533(2) y
Ag1 O1 2_656 2.533(2) y
Ag1 N1 2_656 2.2619(17) y
Ag1 N1 . 2.2619(17) y
O1 N3 . 1.232(3) y
O2 N3 . 1.224(4) y
N1 C2 . 1.323(3) no
N1 C3 . 1.371(3) no
N2 C1 . 1.326(3) n
N2 C8 . 1.367(3) n
N3 O1 2_656 1.232(3) n
C1 C2 . 1.437(3) n
C1 C10 . 1.468(3) n
C2 C14 . 1.479(3) n
C3 C4 . 1.411(3) n
C3 C8 . 1.409(3) n
C4 H4 . 0.9300 no
C4 C5 . 1.366(3) n
C5 H5 . 0.9300 no
C5 C6 . 1.404(4) n
C6 H6 . 0.9300 no
C6 C7 . 1.373(3) n
C7 C8 . 1.426(3) n
C7 C9 . 1.496(3) n
C9 H9A . 0.9600 no
C9 H9B . 0.9600 no
C9 H9C . 0.9600 no
C10 C11 . 1.401(3) n
C10 S1 . 1.720(2) n
C11 H11 . 0.9300 no
C11 C12 . 1.423(3) n
C12 H12 . 0.9300 no
C12 C13 . 1.334(4) n
C13 H13 . 0.9300 no
C13 S1 . 1.690(3) n
C14 C15 . 1.348(8) n
C14 S2 . 1.692(2) n
C15 H15 . 0.9300 no
C15 C16 . 1.437(11) n
C16 H16 . 0.9300 no
C16 C17 . 1.337(9) n
C17 H17 . 0.9300 no
C17 S2 . 1.688(10) n
C15B H15B . 0.9300 no
C15B C16B . 1.437(16) n
C16B H16B . 0.9300 no
C16B C17B . 1.335(14) n
C17B H17B . 0.9300 no
C17B S2B . 1.679(16) n
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 O1 N3 O1 . . . 2_656 -0.002(2) ?
Ag1 O1 N3 O2 . . . . 180.000(2) ?
Ag1 N1 C2 C1 . . . . 177.25(14) ?
Ag1 N1 C2 C14 . . . . -1.9(2) ?
Ag1 N1 C3 C4 . . . . 5.0(3) ?
Ag1 N1 C3 C8 . . . . -174.50(14) ?
O1 Ag1 O1 N3 2_656 . . . 0.001(2) ?
O1 Ag1 N1 C2 2_656 . . . 85.90(16) ?
O1 Ag1 N1 C2 . . . . 137.02(15) ?
O1 Ag1 N1 C3 2_656 . . . -96.90(16) ?
O1 Ag1 N1 C3 . . . . -45.79(17) ?
N1 Ag1 O1 N3 2_656 . . . 90.85(13) ?
N1 Ag1 O1 N3 . . . . -104.43(13) ?
N1 Ag1 N1 C2 2_656 . . . -68.10(14) ?
N1 Ag1 N1 C3 2_656 . . . 109.09(16) ?
N1 C2 C14 C15 . . . . -79.2(8) ?
N1 C2 C14 S2 . . . . 101.6(2) ?
N1 C3 C4 C5 . . . . -178.2(2) ?
N1 C3 C8 N2 . . . . -2.5(3) ?
N1 C3 C8 C7 . . . . 178.19(19) ?
N2 C1 C2 N1 . . . . -2.9(3) ?
N2 C1 C2 C14 . . . . 176.19(19) ?
N2 C1 C10 C11 . . . . 161.8(2) ?
N2 C1 C10 S1 . . . . -15.5(3) ?
C1 N2 C8 C3 . . . . -0.4(3) ?
C1 N2 C8 C7 . . . . 178.89(19) ?
C1 C2 C14 C15 . . . . 101.7(8) ?
C1 C2 C14 S2 . . . . -77.6(3) ?
C1 C10 C11 C12 . . . . -178.1(2) ?
C1 C10 S1 C13 . . . . 178.55(18) ?
C2 N1 C3 C4 . . . . -177.9(2) ?
C2 N1 C3 C8 . . . . 2.6(3) ?
C2 C1 C10 C11 . . . . -19.4(4) ?
C2 C1 C10 S1 . . . . 163.24(17) ?
C2 C14 C15 C16 . . . . -177(2) ?
C2 C14 S2 C17 . . . . -179.4(7) ?
C3 N1 C2 C1 . . . . -0.1(3) ?
C3 N1 C2 C14 . . . . -179.20(18) ?
C3 C4 C5 C6 . . . . -0.1(4) ?
C4 C3 C8 N2 . . . . 178.0(2) ?
C4 C3 C8 C7 . . . . -1.3(3) ?
C4 C5 C6 C7 . . . . -1.0(4) ?
C5 C6 C7 C8 . . . . 1.0(3) ?
C5 C6 C7 C9 . . . . -178.4(2) ?
C6 C7 C8 N2 . . . . -179.2(2) ?
C6 C7 C8 C3 . . . . 0.2(3) ?
C8 N2 C1 C2 . . . . 3.0(3) ?
C8 N2 C1 C10 . . . . -178.15(18) ?
C8 C3 C4 C5 . . . . 1.3(4) ?
C9 C7 C8 N2 . . . . 0.3(3) ?
C9 C7 C8 C3 . . . . 179.6(2) ?
C10 C1 C2 N1 . . . . 178.41(19) ?
C10 C1 C2 C14 . . . . -2.5(3) ?
C10 C11 C12 C13 . . . . 0.3(4) ?
C11 C10 S1 C13 . . . . 0.7(2) ?
C11 C12 C13 S1 . . . . 0.2(3) ?
C12 C13 S1 C10 . . . . -0.5(2) ?
S1 C10 C11 C12 . . . . -0.6(3) ?
C14 C15 C16 C17 . . . . -5(4) ?
C15 C14 S2 C17 . . . . 1.2(9) ?
C15 C16 C17 S2 . . . . 6(4) ?
C16 C17 S2 C14 . . . . -4(3) ?
S2 C14 C15 C16 . . . . 2(2) ?
C15B C16B C17B S2B . . . . -9(7) ?
