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_7061686
_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         'C6 N6 Se, Cl, C4 H8 O, C8 H20 N'
_chemical_formula_sum            'C18 H28 Cl N7 O Se'
_chemical_formula_weight         472.88
_chemical_name_common
;
tetraethilammonium 1-chloro-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic
;
tetraethilammonium 1-chloro-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 91.892(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0780(3)
_cell_length_b                   15.0011(8)
_cell_length_c                   21.4924(11)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.41
_cell_measurement_theta_min      2.33
_cell_volume                     2280.77(19)
_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      200.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_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  0.0486
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            50168
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.282
_diffrn_reflns_theta_min         2.332
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0867 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+1.0199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5405
_reflns_number_total             6518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02345h2.cif
_cod_data_source_block           1-Cl_Et4N
_cod_database_code               7061686
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.786
_shelx_estimated_absorpt_t_min   0.541
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C15 \\sim C18 \\sim C17: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01 within 2A
3. Others
 Fixed Sof: H16C(0.5) H16D(0.5) H16A(0.5) H16B(0.5) H17C(0.5) H17D(0.5)
 H17A(0.5) H17B(0.5) C19(0.5) H19A(0.5) H19B(0.5) C18(0.5) H18A(0.5) H18B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16C,H16D), C16(H16A,H16B), C17(H17C,H17D), C17(H17A,
 H17B), C19(H19A,H19B), C18(H18A,H18B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,
 H11B), C13(H13A,H13B)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              11594