#------------------------------------------------------------------------------
#$Date: 2021-01-01 02:10:43 +0200 (Fri, 01 Jan 2021) $
#$Revision: 260310 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135463.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_4135463
loop_
_publ_author_name
'Abe, Haruka'
'Kawasaki, Ayumi'
'Takeda, Takashi'
'Hoshino, Norihisa'
'Matsuda, Wakana'
'Seki, Shu'
'Akutagawa, Tomoyuki'
_publ_section_title
;
 Crystal Lattice Design of H2O-Tolerant n-Type Semiconducting Dianionic
 Naphthalenediimide Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c11545
_journal_year                    2020
_chemical_formula_moiety         'C20 H20 K2 N2 O12'
_chemical_formula_sum            'C20 H20 K2 N2 O12'
_chemical_formula_weight         558.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.2120
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   16.2707
_cell_length_b                   8.4478
_cell_length_c                   8.1981
_cell_measurement_reflns_used    2181
_cell_measurement_temperature    100
_cell_measurement_theta_max      61.52
_cell_measurement_theta_min      5.24
_cell_volume                     1126.590
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1572
_diffrn_reflns_av_unetI/netI     0.1353
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12205
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.110
_diffrn_reflns_theta_max         68.110
_diffrn_reflns_theta_min         5.439
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.376
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             576.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1692P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2266
_refine_ls_wR_factor_ref         0.3068
_reflns_number_gt                826
_reflns_number_total             2043
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja0c11545_si_003.cif
_cod_data_source_block           181219_NDI_K_recrystallized
_cod_original_cell_volume        1126.5888
_cod_database_code               4135463
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+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
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.40686(10) 0.6365(2) 1.01675(19) 0.0781(8) Uani 1 1 d . . .
O1 O 0.2558(3) -0.0206(7) 0.5841(6) 0.0807(17) Uani 1 1 d . . .
O2 O 0.0765(3) 0.1524(6) 0.9665(6) 0.0731(15) Uani 1 1 d . . .
O3 O 0.3466(4) 0.1244(8) 1.1491(6) 0.0873(19) Uani 1 1 d . . .
O4 O 0.3430(3) -0.1313(8) 1.2051(7) 0.090(2) Uani 1 1 d . . .
O5 O 0.4264(3) 0.3077(8) 0.9306(7) 0.0823(18) Uani 1 1 d . . .
O6 O 0.4642(4) -0.0241(11) 0.8196(8) 0.121(3) Uani 1 1 d . . .
N1 N 0.1668(4) 0.0737(8) 0.7730(7) 0.0664(17) Uani 1 1 d . . .
C1 C -0.0616(5) 0.1123(9) 0.7551(8) 0.066(2) Uani 1 1 d . . .
H1 H -0.0717 0.1553 0.8598 0.080 Uiso 1 1 calc R . .
C2 C 0.0180(5) 0.0769(9) 0.7115(8) 0.0623(19) Uani 1 1 d . . .
C3 C 0.0328(4) 0.0138(8) 0.5544(7) 0.0583(19) Uani 1 1 d . . .
C4 C 0.1142(4) -0.0242(9) 0.5066(8) 0.0583(18) Uani 1 1 d . . .
C5 C 0.1274(4) -0.0852(10) 0.3540(8) 0.067(2) Uani 1 1 d . . .
H5 H 0.1818 -0.1092 0.3222 0.080 Uiso 1 1 calc R . .
C6 C 0.1842(5) 0.0081(10) 0.6187(8) 0.072(2) Uani 1 1 d . . .
C7 C 0.0878(5) 0.1046(9) 0.8260(9) 0.068(2) Uani 1 1 d . . .
C8 C 0.2360(5) 0.1037(10) 0.8857(9) 0.075(2) Uani 1 1 d . . .
H8A H 0.2213 0.1897 0.9617 0.090 Uiso 1 1 calc R . .
H8B H 0.2841 0.1391 0.8231 0.090 Uiso 1 1 calc R . .
C9 C 0.2588(5) -0.0423(10) 0.9821(8) 0.073(2) Uani 1 1 d . . .
H9A H 0.2813 -0.1219 0.9064 0.088 Uiso 1 1 calc R . .
H9B H 0.2082 -0.0872 1.0283 0.088 Uiso 1 1 calc R . .
C10 C 0.3225(5) -0.0153(14) 1.1234(9) 0.076(3) Uani 1 1 d . . .
H2 H 0.488(6) 0.097(11) 0.787(10) 0.10(3) Uiso 1 1 d . . .
H3 H 0.537(7) -0.029(11) 0.847(12) 0.14(3) Uiso 1 1 d . . .
H4 H 0.409(4) 0.424(8) 1.014(8) 0.07(2) Uiso 1 1 d . . .
H6 H 0.401(5) 0.265(10) 1.020(10) 0.09(3) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
K K 0.3868 1.0657
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 O4 77.64(18) 4_566 1_565 ?
O1 K1 O4 81.77(16) 4_566 4_565 ?
O4 K1 O4 113.57(16) 1_565 4_565 ?
O1 K1 O5 156.25(18) 4_566 3_667 ?
O4 K1 O5 99.97(19) 1_565 3_667 ?
O4 K1 O5 119.85(18) 4_565 3_667 ?
O1 K1 O6 89.04(17) 4_566 4_566 ?
O4 K1 O6 82.2(2) 1_565 4_566 ?
O4 K1 O6 159.2(3) 4_565 4_566 ?
O5 K1 O6 67.28(18) 3_667 4_566 ?
O1 K1 O5 78.88(18) 4_566 . ?
O4 K1 O5 151.6(2) 1_565 . ?
O4 K1 O5 78.33(19) 4_565 . ?
O5 K1 O5 95.12(18) 3_667 . ?
O6 K1 O5 81.6(2) 4_566 . ?
O1 K1 C10 83.5(2) 4_566 1_565 ?
O4 K1 C10 19.84(15) 1_565 1_565 ?
O4 K1 C10 96.16(17) 4_565 1_565 ?
O5 K1 C10 102.3(2) 3_667 1_565 ?
O6 K1 C10 101.3(2) 4_566 1_565 ?
O5 K1 C10 162.1(2) . 1_565 ?
O1 K1 K1 121.32(15) 4_566 3_667 ?
O4 K1 K1 142.16(13) 1_565 3_667 ?
O4 K1 K1 102.07(15) 4_565 3_667 ?
O5 K1 K1 48.73(15) 3_667 3_667 ?
O6 K1 K1 67.01(19) 4_566 3_667 ?
O5 K1 K1 46.39(11) . 3_667 ?
C10 K1 K1 150.85(17) 1_565 3_667 ?
O1 K1 K1 87.20(11) 4_566 4_576 ?
O4 K1 K1 34.08(12) 1_565 4_576 ?
O4 K1 K1 147.64(15) 4_565 4_576 ?
O5 K1 K1 78.82(13) 3_667 4_576 ?
O6 K1 K1 49.2(2) 4_566 4_576 ?
O5 K1 K1 129.19(13) . 4_576 ?
C10 K1 K1 52.21(14) 1_565 4_576 ?
K1 K1 K1 109.63(5) 3_667 4_576 ?
O1 K1 K1 110.78(11) 4_566 4_575 ?
O4 K1 K1 102.49(15) 1_565 4_575 ?
O4 K1 K1 33.78(13) 4_565 4_575 ?
O5 K1 K1 92.88(13) 3_667 4_575 ?
O6 K1 K1 160.16(13) 4_566 4_575 ?
O5 K1 K1 100.61(13) . 4_575 ?
C10 K1 K1 82.69(15) 1_565 4_575 ?
K1 K1 K1 100.10(5) 3_667 4_575 ?
K1 K1 K1 129.85(9) 4_576 4_575 ?
O1 K1 H4 70.2(19) 4_566 . ?
O4 K1 H4 138(2) 1_565 . ?
O4 K1 H4 89(2) 4_565 . ?
O5 K1 H4 98.7(19) 3_667 . ?
O6 K1 H4 71(2) 4_566 . ?
O5 K1 H4 14(2) . . ?
C10 K1 H4 152(2) 1_565 . ?
K1 K1 H4 51.6(19) 3_667 . ?
K1 K1 H4 116(2) 4_576 . ?
K1 K1 H4 114(2) 4_575 . ?
C6 O1 K1 170.1(6) . 4_565 ?
C10 O4 K1 111.6(5) . 1_545 ?
C10 O4 K1 127.9(6) . 4_566 ?
K1 O4 K1 112.1(2) 1_545 4_566 ?
K1 O5 K1 84.88(18) 3_667 . ?
K1 O5 H4 91(3) 3_667 . ?
K1 O5 H4 21(3) . . ?
K1 O5 H6 113(5) 3_667 . ?
K1 O5 H6 97(5) . . ?
H4 O5 H6 76(5) . . ?
K1 O6 H2 102(4) 4_565 . ?
K1 O6 H3 118(5) 4_565 . ?
H2 O6 H3 75(5) . . ?
C7 N1 C6 123.8(6) . . ?
C7 N1 C8 118.3(6) . . ?
C6 N1 C8 117.8(6) . . ?
C2 C1 C5 120.5(7) . 3_556 ?
C2 C1 H1 119.7 . . ?
C5 C1 H1 119.7 3_556 . ?
C1 C2 C3 119.5(7) . . ?
C1 C2 C7 120.9(7) . . ?
C3 C2 C7 119.6(7) . . ?
C3 C3 C2 120.0(8) 3_556 . ?
C3 C3 C4 119.3(8) 3_556 . ?
C2 C3 C4 120.7(6) . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 C6 120.3(7) . . ?
C3 C4 C6 119.8(6) . . ?
C4 C5 C1 120.8(7) . 3_556 ?
C4 C5 H5 119.6 . . ?
C1 C5 H5 119.6 3_556 . ?
O1 C6 N1 119.4(7) . . ?
O1 C6 C4 123.0(7) . . ?
N1 C6 C4 117.6(7) . . ?
O2 C7 N1 120.5(7) . . ?
O2 C7 C2 121.1(7) . . ?
N1 C7 C2 118.4(6) . . ?
N1 C8 C9 111.5(6) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 115.1(7) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
O4 C10 O3 125.1(8) . . ?
O4 C10 C9 117.3(9) . . ?
O3 C10 C9 117.6(8) . . ?
O4 C10 K1 48.6(5) . 1_545 ?
O3 C10 K1 137.2(6) . 1_545 ?
C9 C10 K1 87.0(5) . 1_545 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1 2.713(5) 4_566 ?
K1 O4 2.717(6) 1_565 ?
K1 O4 2.738(5) 4_565 ?
K1 O5 2.779(5) 3_667 ?
K1 O6 2.799(6) 4_566 ?
K1 O5 2.885(7) . ?
K1 C10 3.370(11) 1_565 ?
K1 K1 3.823(3) 3_667 ?
K1 K1 4.5255(16) 4_576 ?
K1 K1 4.5255(16) 4_575 ?
K1 H4 1.80(7) . ?
O1 C6 1.230(8) . ?
O1 K1 2.713(5) 4_565 ?
O2 C7 1.238(8) . ?
O3 C10 1.260(10) . ?
O4 C10 1.230(10) . ?
O4 K1 2.717(6) 1_545 ?
O4 K1 2.738(5) 4_566 ?
O5 K1 2.779(5) 3_667 ?
O5 H4 1.23(7) . ?
O5 H6 0.92(8) . ?
O6 K1 2.799(6) 4_565 ?
O6 H2 1.13(9) . ?
O6 H3 1.20(11) . ?
N1 C7 1.390(9) . ?
N1 C6 1.415(9) . ?
N1 C8 1.464(8) . ?
C1 C2 1.384(9) . ?
C1 C5 1.398(9) 3_556 ?
C1 H1 0.9500 . ?
C2 C3 1.419(9) . ?
C2 C7 1.476(10) . ?
C3 C3 1.397(12) 3_556 ?
C3 C4 1.425(9) . ?
C4 C5 1.374(9) . ?
C4 C6 1.473(10) . ?
C5 C1 1.398(9) 3_556 ?
C5 H5 0.9500 . ?
C8 C9 1.506(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.554(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 K1 3.370(11) 1_545 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H6 O3 . . . 2.718(9) 0.92(8) 1.83(8) 160(8) no
O6 H2 O5 . . . 3.015(11) 1.13(9) 2.37(9) 114(6) no
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 K1 O5 K1 -156.77(18) 4_566 . . 3_667 ?
O4 K1 O5 K1 -122.1(3) 1_565 . . 3_667 ?
O4 K1 O5 K1 119.45(18) 4_565 . . 3_667 ?
O5 K1 O5 K1 0.0 3_667 . . 3_667 ?
O6 K1 O5 K1 -66.10(16) 4_566 . . 3_667 ?
C10 K1 O5 K1 -167.0(5) 1_565 . . 3_667 ?
K1 K1 O5 K1 -79.74(16) 4_576 . . 3_667 ?
K1 K1 O5 K1 93.90(12) 4_575 . . 3_667 ?
C5 C1 C2 C3 0.5(11) 3_556 . . . ?
C5 C1 C2 C7 -179.8(7) 3_556 . . . ?
C1 C2 C3 C3 -0.7(13) . . . 3_556 ?
C7 C2 C3 C3 179.6(8) . . . 3_556 ?
C1 C2 C3 C4 -179.8(7) . . . . ?
C7 C2 C3 C4 0.5(11) . . . . ?
C3 C3 C4 C5 0.9(13) 3_556 . . . ?
C2 C3 C4 C5 180.0(7) . . . . ?
C3 C3 C4 C6 178.5(8) 3_556 . . . ?
C2 C3 C4 C6 -2.4(11) . . . . ?
C3 C4 C5 C1 -0.7(12) . . . 3_556 ?
C6 C4 C5 C1 -178.3(7) . . . 3_556 ?
K1 O1 C6 N1 105(3) 4_565 . . . ?
K1 O1 C6 C4 -75(3) 4_565 . . . ?
C7 N1 C6 O1 -177.4(7) . . . . ?
C8 N1 C6 O1 -0.4(11) . . . . ?
C7 N1 C6 C4 2.0(11) . . . . ?
C8 N1 C6 C4 179.1(7) . . . . ?
C5 C4 C6 O1 -1.7(12) . . . . ?
C3 C4 C6 O1 -179.3(7) . . . . ?
C5 C4 C6 N1 178.8(7) . . . . ?
C3 C4 C6 N1 1.2(11) . . . . ?
C6 N1 C7 O2 175.2(7) . . . . ?
C8 N1 C7 O2 -1.8(11) . . . . ?
C6 N1 C7 C2 -3.9(11) . . . . ?
C8 N1 C7 C2 179.0(7) . . . . ?
C1 C2 C7 O2 3.8(12) . . . . ?
C3 C2 C7 O2 -176.5(7) . . . . ?
C1 C2 C7 N1 -177.1(7) . . . . ?
C3 C2 C7 N1 2.6(11) . . . . ?
C7 N1 C8 C9 92.4(8) . . . . ?
C6 N1 C8 C9 -84.8(8) . . . . ?
N1 C8 C9 C10 -170.9(6) . . . . ?
K1 O4 C10 O3 -125.1(7) 1_545 . . . ?
K1 O4 C10 O3 20.3(12) 4_566 . . . ?
K1 O4 C10 C9 57.7(8) 1_545 . . . ?
K1 O4 C10 C9 -156.9(5) 4_566 . . . ?
K1 O4 C10 K1 145.4(8) 4_566 . . 1_545 ?
C8 C9 C10 O4 -179.8(7) . . . . ?
C8 C9 C10 O3 2.7(10) . . . . ?
C8 C9 C10 K1 -140.5(6) . . . 1_545 ?
