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#$Date: 2024-07-05 18:20:01 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/86/7248638.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248638
loop_
_publ_author_name
'Alfuth, Jan'
'Czapik, Agnieszka'
'Zadykowicz, Beata'
'Olszewska, Teresa'
_publ_section_title
;
 Hydrogen and chalcogen bonds in crystals of chalcogenadiazolecarboxylic
 acids -- competition or cooperation?
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              2918
_journal_page_last               2927
_journal_paper_doi               10.1039/D4CE00273C
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C7 H4 N2 O2 Se'
_chemical_formula_sum            'C7 H4 N2 O2 Se'
_chemical_formula_weight         227.08
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-02-13 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.529(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8823(6)
_cell_length_b                   3.76622(18)
_cell_length_c                   15.6812(8)
_cell_measurement_reflns_used    2698
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.9340
_cell_measurement_theta_min      2.6450
_cell_volume                     702.75(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5870
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         2.674
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.292
_exptl_absorpt_correction_T_max  0.59779
_exptl_absorpt_correction_T_min  0.59033
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_crystal_size_rad          0.067
_refine_diff_density_max         0.823
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0376
_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)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1217
_reflns_number_total             1487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00273c2.cif
_cod_data_source_block           2Se
_cod_depositor_comments
'Adding full bibliography for 7248632--7248640.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7248638
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_min   0.226
_shelx_estimated_absorpt_t_max   0.902
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se2 Se 0.54101(3) 0.86544(10) 0.40226(2) 0.01214(15) Uani 1 1 d . . . . .
O1 O 0.6826(2) 0.7741(8) 0.71449(17) 0.0184(6) Uani 1 1 d . . . . .
H1 H 0.680022 0.790066 0.767069 0.028 Uiso 1 1 calc R U . . .
O2 O 0.8513(2) 0.5435(8) 0.79465(18) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.6548(2) 0.6720(8) 0.3798(2) 0.0136(7) Uani 1 1 d . . . . .
N3 N 0.6089(3) 0.8141(8) 0.5245(2) 0.0121(7) Uani 1 1 d . . . . .
C4 C 0.7905(3) 0.5639(10) 0.6311(3) 0.0135(8) Uani 1 1 d . . . . .
C5 C 0.8870(3) 0.4016(10) 0.6353(3) 0.0131(8) Uani 1 1 d . . . . .
H5 H 0.941061 0.337221 0.694107 0.016 Uiso 1 1 calc R U . . .
C6 C 0.9104(3) 0.3248(10) 0.5562(3) 0.0151(9) Uani 1 1 d . . . . .
H6 H 0.979262 0.211961 0.563457 0.018 Uiso 1 1 calc R U . . .
C7 C 0.8364(3) 0.4093(10) 0.4699(3) 0.0141(9) Uani 1 1 d . . . . .
H7 H 0.852760 0.357366 0.417073 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7334(3) 0.5779(10) 0.4608(3) 0.0121(8) Uani 1 1 d . . . . .
C9 C 0.7083(3) 0.6569(10) 0.5424(3) 0.0125(8) Uani 1 1 d . . . . .
C10 C 0.7788(3) 0.6241(10) 0.7218(3) 0.0120(8) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Se2 N1 93.74(14) . . ?
C10 O1 H1 109.5 . . ?
C8 N1 Se2 107.5(2) . . ?
C9 N3 Se2 108.0(2) . . ?
C5 C4 C9 118.5(3) . . ?
C5 C4 C10 116.2(3) . . ?
C9 C4 C10 125.2(3) . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.2(3) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
N1 C8 C7 123.4(3) . . ?
N1 C8 C9 115.9(3) . . ?
C7 C8 C9 120.8(3) . . ?
N3 C9 C4 127.2(3) . . ?
N3 C9 C8 114.8(3) . . ?
C4 C9 C8 118.0(3) . . ?
O2 C10 O1 123.2(3) . . ?
O2 C10 C4 122.5(3) . . ?
O1 C10 C4 114.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se2 N3 1.786(3) . ?
Se2 N1 1.789(3) . ?
O1 C10 1.326(4) . ?
O1 H1 0.8400 . ?
O2 C10 1.205(4) . ?
N1 C8 1.334(5) . ?
N3 C9 1.338(5) . ?
C4 C5 1.364(5) . ?
C4 C9 1.432(5) . ?
C4 C10 1.503(5) . ?
C5 C6 1.414(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.362(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.428(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.465(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Se2 N1 C8 1.0(3) . . . . ?
N1 Se2 N3 C9 -1.0(3) . . . . ?
C9 C4 C5 C6 0.8(6) . . . . ?
C10 C4 C5 C6 179.7(3) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
Se2 N1 C8 C7 179.1(3) . . . . ?
Se2 N1 C8 C9 -0.7(4) . . . . ?
C6 C7 C8 N1 -179.9(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
Se2 N3 C9 C4 -179.9(3) . . . . ?
Se2 N3 C9 C8 0.7(4) . . . . ?
C5 C4 C9 N3 179.6(4) . . . . ?
C10 C4 C9 N3 0.8(7) . . . . ?
C5 C4 C9 C8 -1.1(6) . . . . ?
C10 C4 C9 C8 -179.8(3) . . . . ?
N1 C8 C9 N3 0.0(5) . . . . ?
C7 C8 C9 N3 -179.8(3) . . . . ?
N1 C8 C9 C4 -179.4(3) . . . . ?
C7 C8 C9 C4 0.8(6) . . . . ?
C5 C4 C10 O2 1.9(6) . . . . ?
C9 C4 C10 O2 -179.3(4) . . . . ?
C5 C4 C10 O1 -178.4(3) . . . . ?
C9 C4 C10 O1 0.4(6) . . . . ?
