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#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/70/4327047.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_4327047
loop_
_publ_author_name
'Yoshiaki Shuku'
'Rie Suizu'
'Kunio Awaga'
_publ_contact_author_address
;Research Centre for Material Science
Nagoya University
Furo-cho
Chikusa
Nagoya
Japan
464-8602
;
_publ_contact_author_email       awaga@mbox.chem.nagoya-u.ac.jp
_publ_contact_author_fax         (+81)52-789-2484
_publ_contact_author_name        'Professor Kunio Awaga'
_publ_contact_author_phone       (+81)52-789-2487
_publ_section_title
;
 Monovalent and Mixed-Valent Potassium Salts of
 [1,2,5]Thiadiazolo[3,4-f][1,10]phenanthroline 1,1-Dioxide: A Radical
 Anion for Multidimensional Network Structures
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11859
_journal_page_last               11861
_journal_paper_doi               10.1021/ic201966t
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C12 H6 K N4 O2 S '
_chemical_formula_sum            'C12 H6 K N4 O2 S'
_chemical_formula_weight         309.36
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.64(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.55(3)
_cell_length_b                   6.606(19)
_cell_length_c                   9.78(3)
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     585(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4507
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       prism
_exptl_crystal_F_000             314.00
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.90
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1436
_refine_ls_R_factor_gt           0.0605
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0826P)²+1.0310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1911
_reflns_number_gt                1025
_reflns_number_total             1436
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ic201966t_si_002_3.cif
_cod_data_source_block           '__KtdapO2'
_cod_original_formula_sum        'C12 H6 K N4 O2 S '
_cod_database_code               4327047
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
3 -X,-Y,-Z
4 +X,1/2-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
K(1) K -0.36058(12) 0.2500 0.62856(12) 0.0338(4) Uani 1.00 2 d S
S(1) S 0.45256(13) 0.2500 1.27757(13) 0.0268(4) Uani 1.00 2 d S
O(1) O 0.5312(2) 0.4308(5) 1.3414(2) 0.0341(7) Uani 1.00 1 d .
N(1) N -0.1958(4) 0.2500 0.9237(5) 0.0233(9) Uani 1.00 2 d S
N(2) N 0.2858(5) 0.2500 1.2940(4) 0.0289(11) Uani 1.00 2 d S
N(3) N 0.4150(5) 0.2500 1.1027(5) 0.0307(11) Uani 1.00 2 d S
N(4) N -0.0561(5) 0.2500 0.7197(4) 0.0270(10) Uani 1.00 2 d S
C(1) C -0.0464(5) 0.2500 0.9691(5) 0.0214(10) Uani 1.00 2 d S
C(2) C -0.2629(6) 0.2500 1.0253(6) 0.0326(14) Uani 1.00 2 d S
C(3) C -0.1886(6) 0.2500 1.1711(6) 0.0331(14) Uani 1.00 2 d S
C(4) C -0.0378(6) 0.2500 1.2188(5) 0.0301(13) Uani 1.00 2 d S
C(5) C 0.0364(5) 0.2500 1.1160(5) 0.0199(10) Uani 1.00 2 d S
C(6) C 0.1949(5) 0.2500 1.1576(5) 0.0211(10) Uani 1.00 2 d S
C(7) C 0.2672(5) 0.2500 1.0497(5) 0.0245(11) Uani 1.00 2 d S
C(8) C 0.1847(5) 0.2500 0.8999(5) 0.0245(11) Uani 1.00 2 d S
C(9) C 0.2506(6) 0.2500 0.7931(6) 0.0395(17) Uani 1.00 2 d S
C(10) C 0.1636(7) 0.2500 0.6502(6) 0.047(2) Uani 1.00 2 d S
C(11) C 0.0113(7) 0.2500 0.6215(6) 0.0380(15) Uani 1.00 2 d S
C(12) C 0.0285(5) 0.2500 0.8589(5) 0.0225(11) Uani 1.00 2 d S
H(1) H -0.3678 0.2500 0.9946 0.039 Uiso 1.00 2 c R
H(2) H -0.2419 0.2500 1.2383 0.040 Uiso 1.00 2 c R
H(3) H 0.0156 0.2500 1.3191 0.036 Uiso 1.00 2 c R
H(4) H 0.3552 0.2500 0.8179 0.047 Uiso 1.00 2 c R
H(5) H 0.2059 0.2500 0.5745 0.057 Uiso 1.00 2 c R
H(6) H -0.0489 0.2500 0.5231 0.046 Uiso 1.00 2 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
K K 0.200 0.250
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
S(1) K(1) O(1) 25.68(6) yes 1_454 1_454
S(1) K(1) O(1) 88.22(5) yes 1_454 2_547
S(1) K(1) O(1) 88.22(5) yes 1_454 3_567
S(1) K(1) O(1) 25.68(6) yes 1_454 4_454
S(1) K(1) N(1) 178.54(10) yes 1_454 .
S(1) K(1) N(4) 119.79(10) yes 1_454 .
O(1) K(1) O(1) 112.22(8) yes 1_454 2_547
O(1) K(1) O(1) 75.40(8) yes 1_454 3_567
O(1) K(1) O(1) 48.30(9) yes 1_454 4_454
O(1) K(1) N(1) 153.81(7) yes 1_454 .
O(1) K(1) N(4) 108.89(10) yes 1_454 .
O(1) K(1) O(1) 100.76(10) yes 2_547 3_567
O(1) K(1) O(1) 75.40(8) yes 2_547 4_454
O(1) K(1) N(1) 92.71(8) yes 2_547 .
O(1) K(1) N(4) 124.62(6) yes 2_547 .
O(1) K(1) O(1) 112.22(8) yes 3_567 4_454
O(1) K(1) N(1) 92.71(8) yes 3_567 .
O(1) K(1) N(4) 124.62(6) yes 3_567 .
O(1) K(1) N(1) 153.81(7) yes 4_454 .
O(1) K(1) N(4) 108.89(10) yes 4_454 .
N(1) K(1) N(4) 58.75(12) yes . .
K(1) S(1) O(1) 61.28(11) yes 1_656 .
K(1) S(1) O(1) 61.28(11) yes 1_656 4_555
K(1) S(1) N(2) 96.67(13) yes 1_656 .
K(1) S(1) N(3) 161.44(18) yes 1_656 .
O(1) S(1) O(1) 111.79(16) yes . 4_555
O(1) S(1) N(2) 110.05(14) yes . .
O(1) S(1) N(3) 111.32(15) yes . .
O(1) S(1) N(2) 110.05(14) yes 4_555 .
O(1) S(1) N(3) 111.32(15) yes 4_555 .
N(2) S(1) N(3) 101.9(2) yes . .
K(1) O(1) K(1) 104.60(9) yes 1_656 2_557
K(1) O(1) S(1) 93.04(14) yes 1_656 .
K(1) O(1) S(1) 116.03(14) yes 2_557 .
K(1) N(1) C(1) 121.5(3) yes . .
K(1) N(1) C(2) 121.1(2) yes . .
C(1) N(1) C(2) 117.4(4) yes . .
S(1) N(2) C(6) 104.0(3) yes . .
S(1) N(3) C(7) 104.9(4) yes . .
K(1) N(4) C(11) 118.4(3) yes . .
K(1) N(4) C(12) 124.0(3) yes . .
C(11) N(4) C(12) 117.6(4) yes . .
N(1) C(1) C(5) 121.8(5) yes . .
N(1) C(1) C(12) 118.0(4) yes . .
C(5) C(1) C(12) 120.2(4) yes . .
N(1) C(2) C(3) 123.8(5) yes . .
C(2) C(3) C(4) 119.5(5) yes . .
C(3) C(4) C(5) 118.4(4) yes . .
C(1) C(5) C(4) 119.0(4) yes . .
C(1) C(5) C(6) 119.3(4) yes . .
C(4) C(5) C(6) 121.7(4) yes . .
N(2) C(6) C(5) 124.8(5) yes . .
N(2) C(6) C(7) 114.9(4) yes . .
C(5) C(6) C(7) 120.2(3) yes . .
N(3) C(7) C(6) 114.3(4) yes . .
N(3) C(7) C(8) 124.5(5) yes . .
C(6) C(7) C(8) 121.2(4) yes . .
C(7) C(8) C(9) 122.8(4) yes . .
C(7) C(8) C(12) 118.5(4) yes . .
C(9) C(8) C(12) 118.7(4) yes . .
C(8) C(9) C(10) 119.6(5) yes . .
C(9) C(10) C(11) 117.2(6) yes . .
N(4) C(11) C(10) 125.2(4) yes . .
N(4) C(12) C(1) 117.8(4) yes . .
N(4) C(12) C(8) 121.7(5) yes . .
C(1) C(12) C(8) 120.5(3) yes . .
N(1) C(2) H(1) 118.1 no . .
C(3) C(2) H(1) 118.1 no . .
C(2) C(3) H(2) 120.2 no . .
C(4) C(3) H(2) 120.2 no . .
C(3) C(4) H(3) 120.8 no . .
C(5) C(4) H(3) 120.8 no . .
C(8) C(9) H(4) 120.2 no . .
C(10) C(9) H(4) 120.2 no . .
C(9) C(10) H(5) 121.4 no . .
C(11) C(10) H(5) 121.4 no . .
N(4) C(11) H(6) 117.4 no . .
C(10) C(11) H(6) 117.4 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
K(1) S(1) 3.3235(15) yes 1_454
K(1) O(1) 2.919(2) yes 1_454
K(1) O(1) 2.738(3) yes 2_547
K(1) O(1) 2.738(3) yes 3_567
K(1) O(1) 2.919(2) yes 4_454
K(1) N(1) 2.811(4) yes .
K(1) N(4) 2.757(4) yes .
S(1) O(1) 1.442(3) yes .
S(1) O(1) 1.442(3) yes 4_555
S(1) N(2) 1.651(5) yes .
S(1) N(3) 1.631(4) yes .
N(1) C(1) 1.352(5) yes .
N(1) C(2) 1.343(8) yes .
N(2) C(6) 1.339(5) yes .
N(3) C(7) 1.340(6) yes .
N(4) C(11) 1.316(8) yes .
N(4) C(12) 1.342(5) yes .
C(1) C(5) 1.401(6) yes .
C(1) C(12) 1.472(7) yes .
C(2) C(3) 1.374(7) yes .
C(3) C(4) 1.365(7) yes .
C(4) C(5) 1.403(8) yes .
C(5) C(6) 1.437(6) yes .
C(6) C(7) 1.434(7) yes .
C(7) C(8) 1.424(6) yes .
C(8) C(9) 1.381(8) yes .
C(8) C(12) 1.416(6) yes .
C(9) C(10) 1.379(7) yes .
C(10) C(11) 1.391(9) yes .
C(2) H(1) 0.950 no .
C(3) H(2) 0.951 no .
C(4) H(3) 0.950 no .
C(9) H(4) 0.950 no .
C(10) H(5) 0.950 no .
C(11) H(6) 0.950 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(1) 3.462(4) 3_668
O(1) C(9) 3.504(6) 2_657
O(1) C(10) 3.578(6) 2_657
N(3) C(2) 3.396(8) 1_655
C(2) N(3) 3.396(8) 1_455
C(9) O(1) 3.504(6) 2_647
C(9) O(1) 3.504(6) 3_667
C(10) O(1) 3.578(6) 2_647
C(10) O(1) 3.578(6) 3_667
S(1) H(2) 3.064 1_655
O(1) H(2) 2.923 1_655
O(1) H(4) 3.022 2_657
O(1) H(5) 3.180 2_657
N(2) H(5) 3.073 1_556
N(3) H(1) 2.612 1_655
N(3) H(2) 3.119 1_655
C(2) H(4) 3.563 1_455
C(3) H(6) 3.269 1_556
C(4) H(5) 3.512 1_556
C(4) H(6) 3.011 1_556
C(9) H(1) 3.547 1_655
C(10) H(3) 3.091 1_554
C(11) H(3) 2.970 1_554
H(1) N(3) 2.612 1_455
H(1) C(9) 3.547 1_455
H(1) H(4) 2.658 1_455
H(2) S(1) 3.064 1_455
H(2) O(1) 2.923 1_455
H(2) O(1) 2.923 4_455
H(2) N(3) 3.119 1_455
H(2) H(6) 2.806 1_556
H(3) C(10) 3.091 1_556
H(3) C(11) 2.970 1_556
H(3) H(5) 2.576 1_556
H(3) H(6) 2.268 1_556
H(4) O(1) 3.022 2_647
H(4) O(1) 3.022 3_667
H(4) C(2) 3.563 1_655
H(4) H(1) 2.658 1_655
H(5) O(1) 3.180 2_647
H(5) O(1) 3.180 3_667
H(5) N(2) 3.073 1_554
H(5) C(4) 3.512 1_554
H(5) H(3) 2.576 1_554
H(6) C(3) 3.269 1_554
H(6) C(4) 3.011 1_554
H(6) H(2) 2.806 1_554
H(6) H(3) 2.268 1_554
H(6) H(6) 3.501 2_546
H(6) H(6) 3.501 2_556
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
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O(1) K(1) S(1) N(2) -109.24(14) 1_454 1_454 1_454
O(1) K(1) S(1) N(3) 70.76(14) 1_454 1_454 1_454
S(1) K(1) O(1) S(1) 123.38(16) 1_454 2_547 2_547
O(1) K(1) S(1) O(1) 159.66(16) 2_547 1_454 1_454
O(1) K(1) S(1) N(2) 50.41(6) 2_547 1_454 1_454
O(1) K(1) S(1) N(3) -129.59(6) 2_547 1_454 1_454
S(1) K(1) O(1) S(1) -123.38(16) 1_454 3_567 2_557
O(1) K(1) S(1) O(1) 58.83(15) 3_567 1_454 1_454
O(1) K(1) S(1) N(2) -50.41(6) 3_567 1_454 1_454
O(1) K(1) S(1) N(3) 129.59(6) 3_567 1_454 1_454
O(1) K(1) S(1) O(1) -141.5(2) 4_454 1_454 1_454
O(1) K(1) S(1) N(2) 109.24(14) 4_454 1_454 1_454
O(1) K(1) S(1) N(3) -70.76(14) 4_454 1_454 1_454
N(1) K(1) S(1) O(1) -70.76(14) . 1_454 1_454
N(4) K(1) S(1) O(1) -70.76(14) . 1_454 1_454
O(1) K(1) O(1) S(1) 132.74(16) 1_454 2_547 2_547
O(1) K(1) O(1) S(1) -22.04(17) 2_547 1_454 1_454
O(1) K(1) O(1) S(1) -100.85(18) 1_454 3_567 2_557
O(1) K(1) O(1) S(1) -117.90(15) 3_567 1_454 1_454
O(1) K(1) O(1) S(1) 21.17(12) 4_454 1_454 1_454
O(1) K(1) N(1) C(1) -67.9(2) 1_454 . .
O(1) K(1) N(1) C(2) 112.1(2) 1_454 . .
N(1) K(1) O(1) S(1) 176.9(2) . 1_454 1_454
O(1) K(1) N(4) C(11) -25.62(7) 1_454 . .
O(1) K(1) N(4) C(12) 154.38(7) 1_454 . .
N(4) K(1) O(1) S(1) 120.00(12) . 1_454 1_454
O(1) K(1) O(1) S(1) 148.77(16) 2_547 3_567 2_557
O(1) K(1) O(1) S(1) -148.77(16) 3_567 2_547 2_547
O(1) K(1) O(1) S(1) 100.85(18) 4_454 2_547 2_547
O(1) K(1) N(1) C(1) 129.54(6) 2_547 . .
O(1) K(1) N(1) C(2) -50.46(6) 2_547 . .
N(1) K(1) O(1) S(1) -55.50(18) . 2_547 2_547
O(1) K(1) N(4) C(11) 110.60(10) 2_547 . .
O(1) K(1) N(4) C(12) -69.40(10) 2_547 . .
N(4) K(1) O(1) S(1) -2.3(2) . 2_547 2_547
O(1) K(1) O(1) S(1) -132.74(16) 4_454 3_567 2_557
O(1) K(1) N(1) C(1) -129.54(6) 3_567 . .
O(1) K(1) N(1) C(2) 50.46(6) 3_567 . .
N(1) K(1) O(1) S(1) 55.50(18) . 3_567 2_557
O(1) K(1) N(4) C(11) -110.60(10) 3_567 . .
O(1) K(1) N(4) C(12) 69.40(10) 3_567 . .
N(4) K(1) O(1) S(1) 2.3(2) . 3_567 2_557
O(1) K(1) N(1) C(1) 67.9(2) 4_454 . .
O(1) K(1) N(1) C(2) -112.1(2) 4_454 . .
O(1) K(1) N(4) C(11) 25.62(7) 4_454 . .
O(1) K(1) N(4) C(12) -154.38(7) 4_454 . .
K(1) S(1) O(1) K(1) -107.87(16) 1_656 . 2_557
O(1) S(1) O(1) K(1) 36.00(19) . 4_555 1_656
O(1) S(1) O(1) K(1) -36.00(19) 4_555 . 1_656
O(1) S(1) O(1) K(1) -143.87(16) 4_555 . 2_557
O(1) S(1) N(2) C(6) 118.19(13) . . .
N(2) S(1) O(1) K(1) 86.61(15) . . 1_656
N(2) S(1) O(1) K(1) -21.3(2) . . 2_557
O(1) S(1) N(3) C(7) -117.28(15) . . .
N(3) S(1) O(1) K(1) -161.18(17) . . 1_656
N(3) S(1) O(1) K(1) 90.9(2) . . 2_557
O(1) S(1) N(2) C(6) -118.19(13) 4_555 . .
N(2) S(1) O(1) K(1) -86.61(15) . 4_555 1_656
O(1) S(1) N(3) C(7) 117.28(15) 4_555 . .
N(3) S(1) O(1) K(1) 161.18(17) . 4_555 1_656
