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#$Date: 2023-11-02 04:28:56 +0200 (Thu, 02 Nov 2023) $
#$Revision: 287241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247653.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_7247653
loop_
_publ_author_name
'Saito, Erika'
'Yamakado, Ryohei'
'Yasuhara, Taichi'
'Yamaguchi, Hiroto'
'Okada, Shuji'
'Yoshida, Tsukasa'
_publ_section_title
;
 Formation of charge-transfer complexes in ionic crystals composed of
 1,3-bis(dicyanomethylidene)indan anion and viologens bearing alkyl chains
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              32039
_journal_page_last               32044
_journal_paper_doi               10.1039/D3RA06782C
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C15 H5 N4, 0.5(C12 H14 N2)'
_chemical_formula_sum            'C21 H12 N5'
_chemical_formula_weight         334.36
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-09 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.012(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3110(4)
_cell_length_b                   19.5847(4)
_cell_length_c                   11.1122(3)
_cell_measurement_reflns_used    15886
_cell_measurement_temperature    93
_cell_measurement_theta_max      31.1550
_cell_measurement_theta_min      2.6230
_cell_volume                     3375.78(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27672
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.226
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0401
_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)+(0.0639P)²+1.6845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3417
_reflns_number_total             3873
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra06782c2.cif
_cod_data_source_block           160807_MeV_-180
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7247653
_shelx_shelxl_version_number     2018/3
_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
_oxdiff_exptl_absorpt_empirical_full_min 0.736
_oxdiff_exptl_absorpt_empirical_full_max 1.337
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32873(6) 0.27822(5) 0.39192(9) 0.0186(2) Uani 1 1 d . . . . .
C2 C 0.36044(6) 0.28354(5) 0.52357(9) 0.0192(2) Uani 1 1 d . . . . .
H2 H 0.3748(8) 0.3261(7) 0.5691(12) 0.023 Uiso 1 1 d . U . . .
C3 C 0.36801(6) 0.21855(5) 0.57950(9) 0.0187(2) Uani 1 1 d . . . . .
C4 C 0.33317(7) 0.09731(6) 0.47683(11) 0.0259(2) Uani 1 1 d . . . . .
H4 H 0.349845 0.072723 0.554320 0.031 Uiso 1 1 calc R U . . .
C5 C 0.30082(8) 0.06297(6) 0.36020(12) 0.0308(3) Uani 1 1 d . . . . .
H5 H 0.295492 0.014651 0.358883 0.037 Uiso 1 1 calc R U . . .
C6 C 0.27679(7) 0.09900(6) 0.24781(11) 0.0294(3) Uani 1 1 d . . . . .
H6 H 0.255037 0.074976 0.170152 0.035 Uiso 1 1 calc R U . . .
C7 C 0.28391(7) 0.17056(6) 0.24608(10) 0.0240(2) Uani 1 1 d . . . . .
H7 H 0.267522 0.195014 0.168447 0.029 Uiso 1 1 calc R U . . .
C8 C 0.31542(6) 0.20435(5) 0.36048(10) 0.0194(2) Uani 1 1 d . . . . .
C9 C 0.34002(6) 0.16754(5) 0.47569(10) 0.0201(2) Uani 1 1 d . . . . .
C10 C 0.31275(6) 0.33322(5) 0.30725(9) 0.0194(2) Uani 1 1 d . . . . .
C11 C 0.27435(7) 0.32791(5) 0.17400(10) 0.0225(2) Uani 1 1 d . . . . .
N1 N 0.24323(7) 0.32620(5) 0.06578(9) 0.0312(2) Uani 1 1 d . . . . .
C12 C 0.33275(7) 0.40065(5) 0.35561(9) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.35169(7) 0.45446(5) 0.39726(9) 0.0285(2) Uani 1 1 d . . . . .
C13 C 0.39493(6) 0.20582(5) 0.70895(10) 0.0194(2) Uani 1 1 d . . . . .
C14 C 0.40368(7) 0.14030(5) 0.76734(10) 0.0227(2) Uani 1 1 d . . . . .
N3 N 0.41217(7) 0.08899(5) 0.82078(10) 0.0315(2) Uani 1 1 d . . . . .
C15 C 0.41442(6) 0.26228(5) 0.79417(9) 0.0197(2) Uani 1 1 d . . . . .
N4 N 0.42925(6) 0.30849(5) 0.86159(8) 0.0248(2) Uani 1 1 d . . . . .
N5 N 0.500000 0.51707(6) 0.750000 0.0279(3) Uani 1 2 d S T P . .
C16 C 0.54151(7) 0.55096(6) 0.85687(10) 0.0244(2) Uani 1 1 d . . . . .
H16 H 0.570798 0.526153 0.931203 0.029 Uiso 1 1 calc R U . . .
C17 C 0.54189(7) 0.62110(5) 0.85939(9) 0.0203(2) Uani 1 1 d . . . . .
H17 H 0.570688 0.644505 0.935647 0.024 Uiso 1 1 calc R U . . .
C18 C 0.500000 0.65818(7) 0.750000 0.0166(3) Uani 1 2 d S T P . .
C19 C 0.500000 0.73413(7) 0.750000 0.0177(3) Uani 1 2 d S T P . .
C20 C 0.54488(8) 0.77105(6) 0.85724(10) 0.0276(3) Uani 1 1 d . . . . .
H20 H 0.576572 0.747635 0.932024 0.033 Uiso 1 1 calc R U . . .
C21 C 0.54351(8) 0.84132(6) 0.85538(11) 0.0309(3) Uani 1 1 d . . . . .
H21 H 0.573684 0.865985 0.929452 0.037 Uiso 1 1 calc R U . . .
N6 N 0.500000 0.87550(6) 0.750000 0.0255(3) Uani 1 2 d S T P . .
C22 C 0.500000 0.44168(9) 0.750000 0.0634(8) Uani 1 2 d S T P . .
H22 H 0.467251 0.425005 0.665683 0.095 Uiso 0.5 1 calc R U P . .
H22A H 0.559463 0.425005 0.772125 0.095 Uiso 0.5 1 calc R U P . .
H22B H 0.473286 0.425005 0.812192 0.095 Uiso 0.5 1 calc R U P . .
C23 C 0.500000 0.95124(8) 0.750000 0.0382(4) Uani 1 2 d S T P . .
H23 H 0.465538 0.967922 0.666540 0.057 Uiso 0.5 1 calc R U P . .
H23A H 0.475156 0.967923 0.814294 0.057 Uiso 0.5 1 calc R U P . .
H23B H 0.559306 0.967923 0.769166 0.057 Uiso 0.5 1 calc R U P . .
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'
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
C2 C1 C10 125.32(9) . . ?
C2 C1 C8 107.35(9) . . ?
C10 C1 C8 127.34(9) . . ?
C1 C2 C3 110.44(9) . . ?
C1 C2 H2 124.3(8) . . ?
C3 C2 H2 125.2(8) . . ?
C13 C3 C2 125.20(9) . . ?
C13 C3 C9 127.23(9) . . ?
C2 C3 C9 107.54(9) . . ?
C9 C4 C5 118.38(11) . . ?
C9 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 120.55(11) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.30(10) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 118.21(11) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C9 120.56(10) . . ?
C7 C8 C1 131.79(10) . . ?
C9 C8 C1 107.63(9) . . ?
C4 C9 C8 121.00(10) . . ?
C4 C9 C3 131.95(10) . . ?
C8 C9 C3 107.02(9) . . ?
C1 C10 C11 125.02(9) . . ?
C1 C10 C12 119.08(9) . . ?
C11 C10 C12 115.86(9) . . ?
N1 C11 C10 177.47(12) . . ?
N2 C12 C10 177.65(12) . . ?
C3 C13 C14 125.99(9) . . ?
C3 C13 C15 118.82(9) . . ?
C14 C13 C15 115.18(9) . . ?
N3 C14 C13 176.35(12) . . ?
N4 C15 C13 178.93(12) . . ?
C16 N5 C16 120.92(13) . 2_656 ?
C16 N5 C22 119.54(7) . . ?
C16 N5 C22 119.54(7) 2_656 . ?
N5 C16 C17 120.59(10) . . ?
N5 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.21(10) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C17 117.48(13) . 2_656 ?
C17 C18 C19 121.26(6) . . ?
C17 C18 C19 121.26(6) 2_656 . ?
C20 C19 C20 117.43(14) . 2_656 ?
C20 C19 C18 121.28(7) . . ?
C20 C19 C18 121.28(7) 2_656 . ?
C21 C20 C19 120.30(11) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
N6 C21 C20 120.82(11) . . ?
N6 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 N6 C21 120.31(14) . 2_656 ?
C21 N6 C23 119.85(7) . . ?
C21 N6 C23 119.84(7) 2_656 . ?
N5 C22 H22 109.5 . . ?
N5 C22 H22A 109.5 . . ?
H22 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22 109.473(1) . 2_656 ?
H22 C22 H22 141.1 . 2_656 ?
H22A C22 H22 56.2 . 2_656 ?
H22B C22 H22 56.3 . 2_656 ?
N5 C22 H22A 109.473(1) . 2_656 ?
H22 C22 H22A 56.3 . 2_656 ?
H22A C22 H22A 141.1 . 2_656 ?
H22B C22 H22A 56.3 . 2_656 ?
H22 C22 H22A 109.5 2_656 2_656 ?
N5 C22 H22B 109.474(2) . 2_656 ?
H22 C22 H22B 56.2 . 2_656 ?
H22A C22 H22B 56.3 . 2_656 ?
H22B C22 H22B 141.1 . 2_656 ?
H22 C22 H22B 109.5 2_656 2_656 ?
H22A C22 H22B 109.5 2_656 2_656 ?
N6 C23 H23 109.5 . . ?
N6 C23 H23A 109.5 . . ?
H23 C23 H23A 109.5 . . ?
N6 C23 H23B 109.5 . . ?
H23 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N6 C23 H23 109.475(2) . 2_656 ?
H23 C23 H23 141.1 . 2_656 ?
H23A C23 H23 56.3 . 2_656 ?
H23B C23 H23 56.2 . 2_656 ?
N6 C23 H23A 109.475(2) . 2_656 ?
H23 C23 H23A 56.2 . 2_656 ?
H23A C23 H23A 141.1 . 2_656 ?
H23B C23 H23A 56.3 . 2_656 ?
H23 C23 H23A 109.5 2_656 2_656 ?
N6 C23 H23B 109.475(1) . 2_656 ?
H23 C23 H23B 56.3 . 2_656 ?
H23A C23 H23B 56.3 . 2_656 ?
H23B C23 H23B 141.1 . 2_656 ?
H23 C23 H23B 109.5 2_656 2_656 ?
H23A C23 H23B 109.5 2_656 2_656 ?
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
C1 C2 1.3965(14) . ?
C1 C10 1.4007(14) . ?
C1 C8 1.4885(14) . ?
C2 C3 1.4051(14) . ?
C2 H2 0.966(13) . ?
C3 C13 1.3905(14) . ?
C3 C9 1.4872(14) . ?
C4 C9 1.3802(15) . ?
C4 C5 1.4099(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3815(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4069(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3836(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4149(15) . ?
C10 C11 1.4220(14) . ?
C10 C12 1.4250(14) . ?
C11 N1 1.1522(15) . ?
C12 N2 1.1541(14) . ?
C13 C14 1.4250(14) . ?
C13 C15 1.4264(14) . ?
C14 N3 1.1537(14) . ?
C15 N4 1.1518(14) . ?
N5 C16 1.3460(13) . ?
N5 C16 1.3461(12) 2_656 ?
N5 C22 1.476(2) . ?
C16 C17 1.3741(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3994(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.4875(19) . ?
C19 C20 1.3926(13) . ?
C19 C20 1.3926(13) 2_656 ?
C20 C21 1.3764(16) . ?
C20 H20 0.9500 . ?
C21 N6 1.3450(14) . ?
C21 H21 0.9500 . ?
N6 C23 1.4834(19) . ?
C22 H22 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22 0.9801 2_656 ?
C22 H22A 0.9800 2_656 ?
C22 H22B 0.9800 2_656 ?
C23 H23 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23 0.9800 2_656 ?
C23 H23A 0.9800 2_656 ?
C23 H23B 0.9800 2_656 ?
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
C10 C1 C2 C3 179.42(9) . . . . ?
C8 C1 C2 C3 -0.42(11) . . . . ?
C1 C2 C3 C13 -177.79(9) . . . . ?
C1 C2 C3 C9 0.75(11) . . . . ?
C9 C4 C5 C6 0.10(17) . . . . ?
C4 C5 C6 C7 0.11(18) . . . . ?
C5 C6 C7 C8 -0.29(17) . . . . ?
C6 C7 C8 C9 0.26(15) . . . . ?
C6 C7 C8 C1 -178.20(10) . . . . ?
C2 C1 C8 C7 178.52(10) . . . . ?
C10 C1 C8 C7 -1.32(18) . . . . ?
C2 C1 C8 C9 -0.09(11) . . . . ?
C10 C1 C8 C9 -179.93(10) . . . . ?
C5 C4 C9 C8 -0.12(16) . . . . ?
C5 C4 C9 C3 177.57(10) . . . . ?
C7 C8 C9 C4 -0.06(15) . . . . ?
C1 C8 C9 C4 178.74(9) . . . . ?
C7 C8 C9 C3 -178.27(9) . . . . ?
C1 C8 C9 C3 0.52(10) . . . . ?
C13 C3 C9 C4 -0.22(18) . . . . ?
C2 C3 C9 C4 -178.72(11) . . . . ?
C13 C3 C9 C8 177.72(10) . . . . ?
C2 C3 C9 C8 -0.78(11) . . . . ?
C2 C1 C10 C11 -174.95(10) . . . . ?
C8 C1 C10 C11 4.86(17) . . . . ?
C2 C1 C10 C12 2.53(15) . . . . ?
C8 C1 C10 C12 -177.65(9) . . . . ?
C2 C3 C13 C14 -179.43(10) . . . . ?
C9 C3 C13 C14 2.32(17) . . . . ?
C2 C3 C13 C15 1.98(15) . . . . ?
C9 C3 C13 C15 -176.27(9) . . . . ?
C16 N5 C16 C17 0.45(7) 2_656 . . . ?
C22 N5 C16 C17 -179.54(7) . . . . ?
N5 C16 C17 C18 -0.91(15) . . . . ?
C16 C17 C18 C17 0.45(7) . . . 2_656 ?
C16 C17 C18 C19 -179.56(7) . . . . ?
C17 C18 C19 C20 2.89(8) . . . . ?
C17 C18 C19 C20 -177.11(8) 2_656 . . . ?
C17 C18 C19 C20 -177.11(8) . . . 2_656 ?
C17 C18 C19 C20 2.89(8) 2_656 . . 2_656 ?
C20 C19 C20 C21 0.43(9) 2_656 . . . ?
C18 C19 C20 C21 -179.56(9) . . . . ?
C19 C20 C21 N6 -0.89(17) . . . . ?
C20 C21 N6 C21 0.45(9) . . . 2_656 ?
C20 C21 N6 C23 -179.55(9) . . . . ?
