Chalcogen-bonded donor–acceptor complexes of 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions
Radiush, Ekaterina A.; Pritchina, Elena A.; Chulanova, Elena A.; Dmitriev, Alexey A.; Bagryanskaya, Irina Yu; Slawin, Alexandra M. Z.; Woollins, J. Derek; Gritsan, Nina P.; Zibarev, Andrey V.; Semenov, Nikolay A.; New Journal of Chemistry 46 (2022) 14490–14501; doi:10.1039/D2NJ02345H

data_7061693
_publ_section_title
;
 Chalcogen-bonded donor--acceptor complexes of
 5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine with halide ions
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14490
_journal_page_last               14501
_journal_paper_doi               10.1039/D2NJ02345H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         '2(C6 N6 Se), Cl, C8 H20 N'
_chemical_formula_sum            'C20 H20 Cl N13 Se2'
_chemical_formula_weight         635.86
_chemical_name_common
;
tetraethilammonium 1-chloro-(5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide)4
;
_chemical_name_systematic
;
tetraethilammonium 1-chloro-(5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide)4
;
_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             2022-04-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                92.513(3)
_cell_angle_beta                 94.141(3)
_cell_angle_gamma                111.522(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8914(9)
_cell_length_b                   12.6394(10)
_cell_length_c                   22.800(2)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.58
_cell_measurement_theta_min      2.22
_cell_volume                     2637.2(4)
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.04
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.808
_diffrn_reflns_theta_min         2.015
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.942
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5816
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.7803.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         11155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0397
_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/[\s^2^(Fo^2^)+(0.0454P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8039
_reflns_number_total             11155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02345h2.cif
_cod_data_source_block           1_4-Cl_Et4N
_cod_database_code               7061693
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.757
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C01C(H01A,H01B), C01G(H01C,H01D), C01K(H01E,H01F), C01L(H01G,H01H), C01R(H01U,
 H01V), C01T(H01W,H01X), C01V(H01Y,H), C01W(H01Z,HA)
2.b Idealised Me refined as rotating group:
 C01N(H01I,H01J,H01K), C01P(H01L,H01M,H01N), C01S(H01O,H01P,H01Q), C01U(H01R,
 H01S,H01T), C01X(H01,HB,HC), C01Y(H1,HD,HE), C01Z(H2,HF,HG), C020(H02A,H02B,
 H02C)
;
_shelx_res_checksum              13400
_olex2_submission_special_instructions 'No special instructions were received'