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#$Date: 2023-07-13 05:07:57 +0300 (Thu, 13 Jul 2023) $
#$Revision: 285196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/21/2312155.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312155
loop_
_publ_author_name
'Nag, Tamali'
'Ovens, Jeffrey S.'
'Bryce, David L.'
_publ_section_title
;
 ⁷⁷Se and ¹²⁵Te solid-state NMR and X-ray
 diffraction structural study of chalcogen-bonded
 3,4-dicyano-1,2,5-chalcogenodiazole cocrystals.
;
_journal_coeditor_code           BS3001
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              517
_journal_page_last               523
_journal_paper_doi               10.1107/S2053229622008518
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          '2C4 N4 Se, C6 H6 O2'
_chemical_formula_moiety         '2(C4 N4 Se), C6 H6 O2'
_chemical_formula_sum            'C14 H6 N8 O2 Se2'
_chemical_formula_weight         476.19
_chemical_name_systematic
;
1,2,5-Selenodiazole-3,4-dicarbonitrile--hydroquinone (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.420(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2634(16)
_cell_length_b                   7.4089(19)
_cell_length_c                   18.320(5)
_cell_measurement_reflns_used    5992
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      37.64
_cell_measurement_theta_min      2.97
_cell_volume                     844.8(4)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX3 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17649
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.090
_diffrn_reflns_theta_min         2.237
_exptl_absorpt_coefficient_mu    4.405
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.4777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.492
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.545
_refine_ls_abs_structure_details none
_refine_ls_extinction_coef       0.0216(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0331
_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/[σ²(Fo²)+(0.0302P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                3289
_reflns_number_total             4607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bs3001sup1.cif
_cod_data_source_block           1a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312155
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.72849(2) 0.36938(2) 0.97332(2) 0.02089(5) Uani d 1 . .
O O1 0.38261(18) 0.32324(16) 0.54309(6) 0.0253(2) Uani d 1 . .
H H1 0.410146 0.326207 0.588459 0.038 Uiso calc 1 . .
N N1 0.9199(2) 0.48058(17) 0.92321(6) 0.0212(2) Uani d 1 . .
N N2 1.0510(3) 0.6182(2) 0.75384(9) 0.0459(5) Uani d 1 . .
N N3 0.5560(2) 0.31610(19) 0.89180(7) 0.0250(3) Uani d 1 . .
N N4 0.4783(3) 0.3335(3) 0.70232(9) 0.0428(4) Uani d 1 . .
C C1 0.9651(3) 0.5513(2) 0.79843(8) 0.0289(3) Uani d 1 . .
C C2 0.8484(2) 0.47000(19) 0.85316(7) 0.0203(3) Uani d 1 . .
C C3 0.6477(2) 0.3788(2) 0.83607(8) 0.0217(3) Uani d 1 . .
C C4 0.5494(3) 0.3530(2) 0.76190(9) 0.0293(3) Uani d 1 . .
C C5 0.1915(2) 0.41095(19) 0.52294(8) 0.0189(2) Uani d 1 . .
C C6 0.1351(2) 0.44688(19) 0.44862(7) 0.0198(3) Uani d 1 . .
H H6 0.226185 0.410757 0.413872 0.024 Uiso calc 1 . .
C C7 -0.0553(2) 0.53587(19) 0.42603(7) 0.0204(3) Uani d 1 . .
H H7 -0.092749 0.560488 0.375902 0.025 Uiso calc 1 . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Se1 N1 . . 92.87(6) ?
C5 O1 H1 . . 109.5 ?
C2 N1 Se1 . . 107.40(10) ?
C3 N3 Se1 . . 107.20(10) ?
N2 C1 C2 . . 177.6(2) ?
N1 C2 C3 . . 115.92(13) ?
N1 C2 C1 . . 120.83(14) ?
C3 C2 C1 . . 123.23(13) ?
N3 C3 C2 . . 116.60(13) ?
N3 C3 C4 . . 120.63(14) ?
C2 C3 C4 . . 122.77(14) ?
N4 C4 C3 . . 177.64(19) ?
O1 C5 C7 . 3_566 122.27(13) ?
O1 C5 C6 . . 118.04(13) ?
C7 C5 C6 3_566 . 119.68(13) ?
C7 C6 C5 . . 119.90(13) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C5 . 3_566 120.42(12) ?
C6 C7 H7 . . 119.8 ?
C5 C7 H7 3_566 . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 N3 . 1.7869(13) ?
Se1 N1 . 1.7901(13) ?
O1 C5 . 1.3760(19) ?
O1 H1 . 0.8300 ?
N1 C2 . 1.3134(18) ?
N2 C1 . 1.141(2) ?
N3 C3 . 1.311(2) ?
N4 C4 . 1.141(2) ?
C1 C2 . 1.437(2) ?
C2 C3 . 1.431(2) ?
C3 C4 . 1.440(2) ?
C5 C7 3_566 1.391(2) ?
C5 C6 . 1.3934(19) ?
C6 C7 . 1.385(2) ?
C6 H6 . 0.9400 ?
C7 H7 . 0.9400 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N4 . 0.83 2.08 2.913(2) 179.8 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 Se1 N1 C2 . . . . -0.58(11) ?
N1 Se1 N3 C3 . . . . 0.71(11) ?
Se1 N1 C2 C3 . . . . 0.32(16) ?
Se1 N1 C2 C1 . . . . 178.50(12) ?
Se1 N3 C3 C2 . . . . -0.67(17) ?
Se1 N3 C3 C4 . . . . 178.50(12) ?
N1 C2 C3 N3 . . . . 0.2(2) ?
C1 C2 C3 N3 . . . . -177.88(15) ?
N1 C2 C3 C4 . . . . -178.91(14) ?
C1 C2 C3 C4 . . . . 3.0(2) ?
O1 C5 C6 C7 . . . . -179.61(13) ?
C7 C5 C6 C7 3_566 . . . 0.3(2) ?
C5 C6 C7 C5 . . . 3_566 -0.3(2) ?

_cod_database_fobs_code 2312155
