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_7061690
_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, Br, C10 H16 N'
_chemical_formula_sum            'C16 H16 Br N7 Se'
_chemical_formula_weight         465.23
_chemical_name_common
;
trimethylbenzilammonium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic
;
trimethylbenzilammonium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 92.018(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8387(14)
_cell_length_b                   6.5947(7)
_cell_length_c                   14.4796(19)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.46
_cell_volume                     938.9(2)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_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  0.0340
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9256
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         2.463
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.141
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.7051.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       needle-plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0309
_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/[\s^2^(Fo^2^)+(0.0265P)^2^+0.1148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0691
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2904
_reflns_number_total             3864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj02345h2.cif
_cod_data_source_block           1-Br_Me3BnN
_cod_database_code               7061690
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.190
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.77(2)
 0.23(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C13(H13), C14(H14), C18(H18)
;
_shelx_res_checksum              65762
_olex2_submission_special_instructions 'No special instructions were received'