#------------------------------------------------------------------------------
#$Date: 2023-07-13 05:07:57 +0300 (Thu, 13 Jul 2023) $
#$Revision: 285196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/21/2312154.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_2312154
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          'C4 N4 Te, C8 H20 P +, Cl -'
_chemical_formula_moiety         'C4 N4 Te, C8 H20 P +, Cl -'
_chemical_formula_sum            'C12 H20 Cl N4 P Te'
_chemical_formula_weight         414.34
_chemical_name_systematic
;
1,2,5-Tellurodiazole-3,4-dicarbonitrile tetraethylphosphonium chloride
;
_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
_atom_sites_solution_primary     direct
_cell_angle_alpha                102.427(2)
_cell_angle_beta                 101.890(2)
_cell_angle_gamma                91.876(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9500(11)
_cell_length_b                   9.5921(15)
_cell_length_c                   13.604(2)
_cell_measurement_reflns_used    9536
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.18
_cell_volume                     863.8(2)
_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      213(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.936
_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  0.0195
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20481
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.658
_diffrn_reflns_theta_min         2.181
_exptl_absorpt_coefficient_mu    1.963
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.717
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.308
_refine_diff_density_max         1.998
_refine_diff_density_min         -1.437
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         5948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0360
_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/[σ²(Fo²)+(0.0118P)²+3.3734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                5740
_reflns_number_total             5948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bs3001sup1.cif
_cod_data_source_block           2b
_cod_database_code               2312154
_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, -z'
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
Te Te1 0.09776(3) 0.78751(2) 0.14068(2) 0.02687(6) Uani d 1 . .
Cl Cl1 0.000000 0.500000 0.000000 0.0513(4) Uani d 1 . .
Cl Cl2 0.000000 0.000000 0.000000 0.0631(5) Uani d 1 . .
P P1 0.69352(14) 0.30361(10) 0.21843(7) 0.03072(17) Uani d 1 . .
N N1 0.1463(5) 0.9557(3) 0.2638(2) 0.0342(6) Uani d 1 . .
N N2 0.1952(5) 0.6719(3) 0.2462(2) 0.0330(6) Uani d 1 . .
N N3 0.2738(9) 1.0727(6) 0.5311(4) 0.0741(15) Uani d 1 . .
N N4 0.3786(10) 0.6562(6) 0.4970(4) 0.0762(16) Uani d 1 . .
C C1 0.2461(7) 1.0040(5) 0.4494(3) 0.0464(9) Uani d 1 . .
C C2 0.2101(6) 0.9088(4) 0.3469(3) 0.0340(7) Uani d 1 . .
C C3 0.2396(6) 0.7571(4) 0.3366(3) 0.0345(7) Uani d 1 . .
C C4 0.3174(8) 0.7015(5) 0.4266(3) 0.0485(10) Uani d 1 . .
C C5 0.6400(7) 0.2837(5) 0.0812(3) 0.0447(9) Uani d 1 . .
H H5A 0.720150 0.357762 0.064619 0.054 Uiso calc 1 . .
H H5AB 0.679124 0.190432 0.049338 0.054 Uiso calc 1 . .
C C6 0.4254(10) 0.2944(9) 0.0344(5) 0.082(2) Uani d 1 . .
H H6A 0.411122 0.298234 -0.037344 0.124 Uiso calc 1 . .
H H6B 0.380116 0.380466 0.071717 0.124 Uiso calc 1 . .
H H6C 0.347336 0.211203 0.038953 0.124 Uiso calc 1 . .
C C7 0.6058(7) 0.4660(4) 0.2809(3) 0.0395(8) Uani d 1 . .
H H7A 0.462620 0.462406 0.255927 0.047 Uiso calc 1 . .
H H7AB 0.631621 0.471097 0.355242 0.047 Uiso calc 1 . .
C C8 0.6992(9) 0.6007(5) 0.2632(5) 0.0590(13) Uani d 1 . .
H H8A 0.666860 0.599915 0.190263 0.089 Uiso calc 1 . .
H H8B 0.841292 0.604662 0.286730 0.089 Uiso calc 1 . .
H H8C 0.649334 0.683947 0.301423 0.089 Uiso calc 1 . .
C C9 0.9574(6) 0.3056(5) 0.2575(4) 0.0480(10) Uani d 1 . .
H H9A 0.999429 0.215866 0.221420 0.058 Uiso calc 1 . .
H H9AB 1.017988 0.384155 0.235725 0.058 Uiso calc 1 . .
C C10 1.0346(10) 0.3230(8) 0.3728(5) 0.083(2) Uani d 1 . .
H H10A 0.996669 0.236863 0.393035 0.125 Uiso calc 1 . .
H H10B 0.979175 0.404187 0.409943 0.125 Uiso calc 1 . .
H H10C 1.177311 0.338997 0.389062 0.125 Uiso calc 1 . .
C C11 0.5701(7) 0.1561(4) 0.2504(4) 0.0439(9) Uani d 1 . .
H H11A 0.599751 0.168791 0.325510 0.053 Uiso calc 1 . .
H H11B 0.427286 0.158849 0.227469 0.053 Uiso calc 1 . .
C C12 0.6282(8) 0.0105(5) 0.2025(5) 0.0608(14) Uani d 1 . .
H H12A 0.610193 0.000174 0.128577 0.091 Uiso calc 1 . .
H H12B 0.546162 -0.063657 0.216209 0.091 Uiso calc 1 . .
H H12C 0.765531 0.001795 0.232005 0.091 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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.5308 1.6751 '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
N2 Te1 N1 . . 84.57(13) ?
C5 P1 C7 . . 110.9(2) ?
C5 P1 C9 . . 106.0(2) ?
C7 P1 C9 . . 111.1(2) ?
C5 P1 C11 . . 109.7(2) ?
C7 P1 C11 . . 107.54(19) ?
C9 P1 C11 . . 111.5(2) ?
C2 N1 Te1 . . 108.5(2) ?
C3 N2 Te1 . . 108.7(2) ?
N3 C1 C2 . . 176.8(6) ?
N1 C2 C3 . . 118.8(3) ?
N1 C2 C1 . . 121.4(4) ?
C3 C2 C1 . . 119.7(4) ?
N2 C3 C4 . . 120.0(4) ?
N2 C3 C2 . . 119.4(3) ?
C4 C3 C2 . . 120.6(4) ?
N4 C4 C3 . . 179.3(5) ?
C6 C5 P1 . . 114.1(4) ?
C6 C5 H5A . . 108.7 ?
P1 C5 H5A . . 108.7 ?
C6 C5 H5AB . . 108.7 ?
P1 C5 H5AB . . 108.7 ?
H5A C5 H5AB . . 107.6 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 P1 . . 114.0(3) ?
C8 C7 H7A . . 108.8 ?
P1 C7 H7A . . 108.8 ?
C8 C7 H7AB . . 108.8 ?
P1 C7 H7AB . . 108.8 ?
H7A C7 H7AB . . 107.6 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 P1 . . 114.5(4) ?
C10 C9 H9A . . 108.6 ?
P1 C9 H9A . . 108.6 ?
C10 C9 H9AB . . 108.6 ?
P1 C9 H9AB . . 108.6 ?
H9A C9 H9AB . . 107.6 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 P1 . . 113.9(3) ?
C12 C11 H11A . . 108.8 ?
P1 C11 H11A . . 108.8 ?
C12 C11 H11B . . 108.8 ?
P1 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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
Te1 N2 . 2.020(3) ?
Te1 N1 . 2.023(3) ?
P1 C5 . 1.793(4) ?
P1 C7 . 1.796(4) ?
P1 C9 . 1.800(4) ?
P1 C11 . 1.807(4) ?
N1 C2 . 1.305(5) ?
N2 C3 . 1.293(5) ?
N3 C1 . 1.138(6) ?
N4 C4 . 1.145(6) ?
C1 C2 . 1.460(5) ?
C2 C3 . 1.457(5) ?
C3 C4 . 1.450(6) ?
C5 C6 . 1.512(7) ?
C5 H5A . 0.9800 ?
C5 H5AB . 0.9800 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C6 H6C . 0.9700 ?
C7 C8 . 1.514(6) ?
C7 H7A . 0.9800 ?
C7 H7AB . 0.9800 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C8 H8C . 0.9700 ?
C9 C10 . 1.520(8) ?
C9 H9A . 0.9800 ?
C9 H9AB . 0.9800 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C10 H10C . 0.9700 ?
C11 C12 . 1.514(6) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 H12C . 0.9700 ?
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
C5 H5A Cl1 1_655 0.98 2.73 3.684(5) 163.9 yes
C7 H7AB N4 2_666 0.98 2.58 3.451(6) 148.4 yes
C11 H11A N4 2_666 0.98 2.60 3.460(7) 146.5 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
Te1 N1 C2 C3 . . . . 2.1(4) ?
Te1 N1 C2 C1 . . . . -175.9(3) ?
Te1 N2 C3 C4 . . . . -178.8(3) ?
Te1 N2 C3 C2 . . . . 1.4(4) ?
N1 C2 C3 N2 . . . . -2.6(6) ?
C1 C2 C3 N2 . . . . 175.5(4) ?
N1 C2 C3 C4 . . . . 177.7(4) ?
C1 C2 C3 C4 . . . . -4.3(6) ?
C7 P1 C5 C6 . . . . -53.5(5) ?
C9 P1 C5 C6 . . . . -174.3(4) ?
C11 P1 C5 C6 . . . . 65.2(5) ?
C5 P1 C7 C8 . . . . -61.2(4) ?
C9 P1 C7 C8 . . . . 56.5(5) ?
C11 P1 C7 C8 . . . . 178.8(4) ?
C5 P1 C9 C10 . . . . 179.5(4) ?
C7 P1 C9 C10 . . . . 58.9(5) ?
C11 P1 C9 C10 . . . . -61.1(5) ?
C5 P1 C11 C12 . . . . 59.0(5) ?
C7 P1 C11 C12 . . . . 179.7(4) ?
C9 P1 C11 C12 . . . . -58.2(5) ?

_cod_database_fobs_code 2312154
