#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:22:16 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281462 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/59/7245942.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_7245942
loop_
_publ_author_name
'Chulanova, Elena A.'
'Radiush, Ekaterina A.'
'Balmohammadi, Yaser'
'Beckmann, Jens'
'Grabowsky, Simon'
'Zibarev, Andrey V.'
_publ_section_title
;
 New charge-transfer complexes of 1,2,5-chalcogenadiazoles with
 tetrathiafulvalenes
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              391
_journal_page_last               402
_journal_paper_doi               10.1039/D2CE01385A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '3(C4 N4 Se), 3(C3 H2 S2)'
_chemical_formula_sum            'C21 H6 N12 S6 Se3'
_chemical_formula_weight         855.62
_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
_audit_creation_date             2021-12-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-07-22 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                95.9690(10)
_cell_angle_beta                 92.9840(10)
_cell_angle_gamma                90.1160(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3298(2)
_cell_length_b                   7.8942(3)
_cell_length_c                   26.3901(9)
_cell_measurement_reflns_used    9646
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.72
_cell_measurement_theta_min      2.33
_cell_volume                     1516.63(9)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            122898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.098
_diffrn_reflns_theta_min         2.331
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.088
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0756 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9087.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         13406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0191P)²+1.0891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10261
_reflns_number_total             13406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01385a2.cif
_cod_data_source_block           chulanovae170821_0m
_cod_depositor_comments
'Adding full bibliography for 7245938--7245942.cif.'
_cod_database_code               7245942
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C18(H18), C19(H19), C21(H21), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -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_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
Se3 Se 0.05817(2) 0.73421(2) 0.49680(2) 0.01155(4) Uani 1 1 d . . . . .
Se1 Se 0.52742(2) 0.62186(2) 0.12731(2) 0.01191(4) Uani 1 1 d . . . . .
Se2 Se 0.39395(2) 0.41724(2) 0.24638(2) 0.01168(4) Uani 1 1 d . . . . .
S2 S 0.42436(6) 0.23428(5) 0.50693(2) 0.01355(8) Uani 1 1 d . . . . .
S3 S 0.07747(6) 0.48964(6) 0.78085(2) 0.01493(8) Uani 1 1 d . . . . .
S1 S 0.40467(6) 0.44385(5) 0.41984(2) 0.01290(8) Uani 1 1 d . . . . .
S6 S -0.10714(6) 0.54271(6) 0.93753(2) 0.01808(9) Uani 1 1 d . . . . .
S5 S -0.05367(6) 0.79082(6) 0.86287(2) 0.01902(9) Uani 1 1 d . . . . .
S4 S 0.00059(6) 0.23381(6) 0.85160(2) 0.01837(9) Uani 1 1 d . . . . .
N1 N 0.60334(19) 0.54860(18) 0.06531(5) 0.0130(3) Uani 1 1 d . . . . .
N9 N 0.1482(2) 0.91228(18) 0.53815(6) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.51144(19) 0.40947(17) 0.14559(5) 0.0135(3) Uani 1 1 d . . . . .
N5 N 0.40152(19) 0.63204(18) 0.22958(5) 0.0132(3) Uani 1 1 d . . . . .
N10 N 0.07785(19) 0.59382(17) 0.54589(5) 0.0120(3) Uani 1 1 d . . . . .
N6 N 0.29703(19) 0.48109(18) 0.30640(5) 0.0128(3) Uani 1 1 d . . . . .
N8 N 0.1198(2) 0.8191(2) 0.38365(6) 0.0206(3) Uani 1 1 d . . . . .
N7 N 0.3061(2) 1.0558(2) 0.26642(7) 0.0255(4) Uani 1 1 d . . . . .
N11 N 0.3294(2) 1.0655(2) 0.65689(7) 0.0310(4) Uani 1 1 d . . . . .
N3 N 0.7096(2) 0.1967(2) -0.01745(7) 0.0273(4) Uani 1 1 d . . . . .
N4 N 0.5731(2) -0.0197(2) 0.11104(7) 0.0284(4) Uani 1 1 d . . . . .
N12 N 0.1947(2) 0.5393(2) 0.67076(6) 0.0278(4) Uani 1 1 d . . . . .
C1 C 0.6095(2) 0.3818(2) 0.06251(6) 0.0132(3) Uani 1 1 d . . . . .
C9 C 0.1854(2) 0.8590(2) 0.58303(6) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.5595(2) 0.3049(2) 0.10678(6) 0.0129(3) Uani 1 1 d . . . . .
C6 C 0.2732(2) 0.6464(2) 0.30896(6) 0.0123(3) Uani 1 1 d . . . . .
C12 C 0.1738(2) 0.6024(2) 0.63393(7) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.3396(2) 0.1389(2) 0.44776(7) 0.0154(3) Uani 1 1 d . . . . .
H15 H 0.301284 0.023072 0.443553 0.019 Uiso 1 1 calc R U . . .
C13 C 0.4645(2) 0.4329(2) 0.48477(6) 0.0105(3) Uani 1 1 d . . . . .
C5 C 0.3317(2) 0.7297(2) 0.26673(6) 0.0128(3) Uani 1 1 d . . . . .
C7 C 0.3180(2) 0.9114(2) 0.26502(7) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.1887(2) 0.7388(2) 0.35148(6) 0.0149(3) Uani 1 1 d . . . . .
C16 C 0.0057(2) 0.4504(2) 0.84120(6) 0.0130(3) Uani 1 1 d . . . . .
C4 C 0.5650(2) 0.1239(2) 0.10996(7) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.3301(2) 0.2330(2) 0.40862(7) 0.0147(3) Uani 1 1 d . . . . .
H14 H 0.284248 0.186646 0.375747 0.018 Uiso 1 1 calc R U . . .
C10 C 0.1459(2) 0.6835(2) 0.58750(6) 0.0127(3) Uani 1 1 d . . . . .
C3 C 0.6658(2) 0.2816(2) 0.01739(7) 0.0170(3) Uani 1 1 d . . . . .
C17 C -0.0433(2) 0.5766(2) 0.87601(6) 0.0137(3) Uani 1 1 d . . . . .
C18 C 0.1444(2) 0.2799(2) 0.76413(7) 0.0191(4) Uani 1 1 d . . . . .
H18 H 0.202919 0.248553 0.733293 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2644(3) 0.9754(2) 0.62433(7) 0.0204(4) Uani 1 1 d . . . . .
C19 C 0.1103(3) 0.1659(2) 0.79614(7) 0.0210(4) Uani 1 1 d . . . . .
H19 H 0.144902 0.050288 0.788977 0.025 Uiso 1 1 calc R U . . .
C21 C -0.1340(3) 0.7584(3) 0.95752(8) 0.0247(4) Uani 1 1 d . . . . .
H21 H -0.165889 0.795023 0.991318 0.030 Uiso 1 1 calc R U . . .
C20 C -0.1086(3) 0.8693(3) 0.92431(8) 0.0251(4) Uani 1 1 d . . . . .
H20 H -0.119932 0.988181 0.933648 0.030 Uiso 1 1 calc R U . . .
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'
Se Se -0.0929 2.2259 '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
N9 Se3 N10 92.94(6) . . ?
N1 Se1 N2 92.91(6) . . ?
N6 Se2 N5 92.88(6) . . ?
C15 S2 C13 94.36(8) . . ?
C18 S3 C16 94.52(9) . . ?
C14 S1 C13 94.72(8) . . ?
C21 S6 C17 94.70(9) . . ?
C20 S5 C17 94.75(9) . . ?
C19 S4 C16 94.28(9) . . ?
C1 N1 Se1 106.95(11) . . ?
C9 N9 Se3 107.31(12) . . ?
C2 N2 Se1 107.23(11) . . ?
C5 N5 Se2 107.14(11) . . ?
C10 N10 Se3 107.25(11) . . ?
C6 N6 Se2 107.01(11) . . ?
N1 C1 C2 116.73(15) . . ?
N1 C1 C3 121.41(15) . . ?
C2 C1 C3 121.86(15) . . ?
N9 C9 C10 116.38(15) . . ?
N9 C9 C11 119.89(16) . . ?
C10 C9 C11 123.72(16) . . ?
N2 C2 C1 116.18(14) . . ?
N2 C2 C4 120.73(16) . . ?
C1 C2 C4 123.07(16) . . ?
N6 C6 C5 116.58(15) . . ?
N6 C6 C8 121.66(15) . . ?
C5 C6 C8 121.74(15) . . ?
N12 C12 C10 179.4(2) . . ?
S2 C15 H15 120.9 . . ?
C14 C15 S2 118.22(13) . . ?
C14 C15 H15 120.9 . . ?
S1 C13 S2 115.02(9) . . ?
C13 C13 S2 122.65(16) 2_666 . ?
C13 C13 S1 122.32(16) 2_666 . ?
N5 C5 C6 116.35(15) . . ?
N5 C5 C7 121.10(15) . . ?
C6 C5 C7 122.55(15) . . ?
N7 C7 C5 176.34(19) . . ?
N8 C8 C6 176.36(18) . . ?
S4 C16 S3 114.55(9) . . ?
C17 C16 S3 122.25(13) . . ?
C17 C16 S4 123.20(13) . . ?
N4 C4 C2 177.6(2) . . ?
S1 C14 H14 121.2 . . ?
C15 C14 S1 117.67(13) . . ?
C15 C14 H14 121.2 . . ?
N10 C10 C9 116.12(15) . . ?
N10 C10 C12 119.35(15) . . ?
C9 C10 C12 124.53(15) . . ?
N3 C3 C1 177.3(2) . . ?
S6 C17 S5 114.27(10) . . ?
C16 C17 S6 123.43(13) . . ?
C16 C17 S5 122.28(13) . . ?
S3 C18 H18 121.2 . . ?
C19 C18 S3 117.52(14) . . ?
C19 C18 H18 121.2 . . ?
N11 C11 C9 178.8(2) . . ?
S4 C19 H19 120.9 . . ?
C18 C19 S4 118.28(14) . . ?
C18 C19 H19 120.9 . . ?
S6 C21 H21 120.9 . . ?
C20 C21 S6 118.10(15) . . ?
C20 C21 H21 120.9 . . ?
S5 C20 H20 121.0 . . ?
C21 C20 S5 117.92(15) . . ?
C21 C20 H20 121.0 . . ?
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
Se3 N9 1.7902(14) . ?
Se3 N10 1.7909(14) . ?
Se1 N1 1.7946(14) . ?
Se1 N2 1.7975(14) . ?
Se2 N5 1.7982(14) . ?
Se2 N6 1.7945(14) . ?
S2 C15 1.7447(17) . ?
S2 C13 1.7588(16) . ?
S3 C16 1.7604(17) . ?
S3 C18 1.7464(19) . ?
S1 C13 1.7575(16) . ?
S1 C14 1.7420(17) . ?
S6 C17 1.7595(17) . ?
S6 C21 1.744(2) . ?
S5 C17 1.7626(17) . ?
S5 C20 1.742(2) . ?
S4 C16 1.7602(17) . ?
S4 C19 1.743(2) . ?
N1 C1 1.313(2) . ?
N9 C9 1.313(2) . ?
N2 C2 1.311(2) . ?
N5 C5 1.309(2) . ?
N10 C10 1.318(2) . ?
N6 C6 1.312(2) . ?
N8 C8 1.145(2) . ?
N7 C7 1.140(2) . ?
N11 C11 1.140(2) . ?
N3 C3 1.141(2) . ?
N4 C4 1.139(2) . ?
N12 C12 1.141(2) . ?
C1 C2 1.435(2) . ?
C1 C3 1.439(2) . ?
C9 C10 1.433(2) . ?
C9 C11 1.446(2) . ?
C2 C4 1.440(2) . ?
C6 C5 1.435(2) . ?
C6 C8 1.442(2) . ?
C12 C10 1.446(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.332(2) . ?
C13 C13 1.348(3) 2_666 ?
C5 C7 1.443(2) . ?
C16 C17 1.345(2) . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.329(3) . ?
C19 H19 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.321(3) . ?
C20 H20 0.9500 . ?
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
Se3 N9 C9 C10 -0.40(18) . . . . ?
Se3 N9 C9 C11 178.67(13) . . . . ?
Se3 N10 C10 C9 -0.37(17) . . . . ?
Se3 N10 C10 C12 178.93(13) . . . . ?
Se1 N1 C1 C2 -0.61(18) . . . . ?
Se1 N1 C1 C3 -179.92(13) . . . . ?
Se1 N2 C2 C1 0.05(18) . . . . ?
Se1 N2 C2 C4 178.56(13) . . . . ?
Se2 N5 C5 C6 0.83(18) . . . . ?
Se2 N5 C5 C7 179.88(13) . . . . ?
Se2 N6 C6 C5 -1.69(18) . . . . ?
Se2 N6 C6 C8 176.89(13) . . . . ?
S2 C15 C14 S1 0.4(2) . . . . ?
S3 C16 C17 S6 -177.44(9) . . . . ?
S3 C16 C17 S5 4.1(2) . . . . ?
S3 C18 C19 S4 0.5(2) . . . . ?
S6 C21 C20 S5 0.9(2) . . . . ?
S4 C16 C17 S6 3.5(2) . . . . ?
S4 C16 C17 S5 -175.04(9) . . . . ?
N1 Se1 N2 C2 -0.32(12) . . . . ?
N1 C1 C2 N2 0.4(2) . . . . ?
N1 C1 C2 C4 -178.08(15) . . . . ?
N9 Se3 N10 C10 0.12(12) . . . . ?
N9 C9 C10 N10 0.5(2) . . . . ?
N9 C9 C10 C12 -178.72(16) . . . . ?
N2 Se1 N1 C1 0.53(12) . . . . ?
N5 Se2 N6 C6 1.79(12) . . . . ?
N10 Se3 N9 C9 0.16(12) . . . . ?
N6 Se2 N5 C5 -1.48(12) . . . . ?
N6 C6 C5 N5 0.6(2) . . . . ?
N6 C6 C5 C7 -178.42(15) . . . . ?
C15 S2 C13 S1 0.57(10) . . . . ?
C15 S2 C13 C13 -179.6(2) . . . 2_666 ?
C13 S2 C15 C14 -0.56(16) . . . . ?
C13 S1 C14 C15 0.05(15) . . . . ?
C8 C6 C5 N5 -177.97(15) . . . . ?
C8 C6 C5 C7 3.0(3) . . . . ?
C16 S3 C18 C19 5.08(16) . . . . ?
C16 S4 C19 C18 -5.86(16) . . . . ?
C14 S1 C13 S2 -0.43(10) . . . . ?
C14 S1 C13 C13 179.70(19) . . . 2_666 ?
C3 C1 C2 N2 179.71(15) . . . . ?
C3 C1 C2 C4 1.2(3) . . . . ?
C17 S6 C21 C20 2.24(18) . . . . ?
C17 S5 C20 C21 -3.58(18) . . . . ?
C18 S3 C16 S4 -8.86(11) . . . . ?
C18 S3 C16 C17 171.97(15) . . . . ?
C11 C9 C10 N10 -178.49(16) . . . . ?
C11 C9 C10 C12 2.2(3) . . . . ?
C19 S4 C16 S3 9.06(11) . . . . ?
C19 S4 C16 C17 -171.78(15) . . . . ?
C21 S6 C17 S5 -4.56(11) . . . . ?
C21 S6 C17 C16 176.83(16) . . . . ?
C20 S5 C17 S6 4.94(11) . . . . ?
C20 S5 C17 C16 -176.43(15) . . . . ?
