#------------------------------------------------------------------------------
#$Date: 2025-01-08 03:36:59 +0100 (Wed, 08 Jan 2025) $
#$Revision: 297207 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/33/2023345.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_2023345
loop_
_publ_author_name
'Gurbanov, Atash V.'
'H\"okelek, Tuncer'
'Mammadova, Gunay Z.'
'Hasanov, Khudayar I.'
'Javadzade, Tahir A.'
'Belay, Alebel N.'
_publ_section_title
;
Crystal structure, Hirshfeld surface analysis and crystal voids of
4-nitrobenzo[c][1,2,5]selenadiazole
;
_journal_coeditor_code VU2008
_journal_issue 2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi 10.1107/S2056989024012398
_journal_volume 81
_journal_year 2025
_chemical_formula_iupac 'C6 H3 N3 O2 Se'
_chemical_formula_moiety 'C6 H3 N3 O2 Se'
_chemical_formula_sum 'C6 H3 N3 O2 Se'
_chemical_formula_weight 228.07
_chemical_name_systematic
;
4-Nitrobenzo[c][1,2,5]selenadiazole
;
_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
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2019/1
_cell_angle_alpha 90
_cell_angle_beta 114.808(3)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.0105(4)
_cell_length_b 13.2765(8)
_cell_length_c 8.1311(5)
_cell_measurement_reflns_used 2556
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 26.65
_cell_measurement_theta_min 3.07
_cell_volume 686.96(7)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX4 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2019/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2019/1 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type 'Bruker APEXII CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_unetI/netI 0.0326
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 5894
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.869
_diffrn_reflns_theta_min 3.069
_exptl_absorpt_coefficient_mu 5.418
_exptl_absorpt_correction_T_max 0.473
_exptl_absorpt_correction_T_min 0.284
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 2.205
_exptl_crystal_description prism
_exptl_crystal_F_000 440
_exptl_crystal_size_max 0.280
_exptl_crystal_size_mid 0.210
_exptl_crystal_size_min 0.140
_refine_diff_density_max 1.240
_refine_diff_density_min -1.270
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.172
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 109
_refine_ls_number_reflns 1475
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.172
_refine_ls_R_factor_all 0.0507
_refine_ls_R_factor_gt 0.0435
_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^)+6.1884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1013
_refine_ls_wR_factor_ref 0.1038
_reflns_number_gt 1297
_reflns_number_total 1475
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file vu2008.cif
_cod_data_source_block I
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 2023345
_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 0.312
_shelx_estimated_absorpt_t_max 0.518
_shelx_hkl_file
;
1 0 0 50.99 2.30
-1 0 0 49.60 2.30
-1 0 0 49.60 2.30
1 0 0 47.70 2.30
-2 0 0 9440.16 431.36
-2 0 0 9999.00 431.86
2 0 0 9966.10 431.96
2 0 0 9738.73 431.76
-3 0 0 130.49 6.00
-3 0 0 134.29 6.20
3 0 0 119.79 6.20
3 0 0 138.99 6.30
4 0 0 2456.45 112.69
4 0 0 2579.04 112.79
-4 0 0 2614.04 112.39
-5 0 0 140.79 6.40
5 0 0 147.09 7.30
6 0 0 563.04 25.80
7 0 0 82.99 5.90
8 0 0 110.29 7.10
0 -1 0 0.20 0.10
0 -1 0 0.00 0.10
0 1 0 0.00 0.10
0 1 0 0.00 0.10
-1 -1 0 1220.08 57.49
1 -1 0 1388.96 57.59
-1 -1 0 1271.47 57.49
1 -1 0 1330.97 57.49
1 1 0 1302.57 57.59
-1 1 0 1390.56 57.69
-1 1 0 1305.67 57.59
1 1 0 1214.38 57.49
1 1 0 1317.17 57.49
-2 -1 0 275.27 12.50
2 -1 0 280.97 12.60
-2 -1 0 272.27 12.60
2 -1 0 282.77 12.60
2 1 0 286.67 12.60
-2 1 0 285.57 12.60
2 1 0 273.67 12.50
-2 1 0 280.77 12.60
-3 -1 0 607.24 27.10
3 -1 0 608.54 27.20
-3 -1 0 584.94 26.90
3 -1 0 601.84 27.10
3 1 0 579.84 27.10
3 1 0 621.24 27.20
-3 1 0 639.44 27.10
-3 1 0 614.94 27.00
-4 -1 0 386.36 17.40
4 -1 0 392.06 17.80
4 -1 0 379.36 17.70
4 1 0 385.66 17.70
4 1 0 400.16 17.70
-4 1 0 388.06 17.40
-5 -1 0 185.78 8.30
5 -1 0 191.68 9.00
-5 1 0 180.68 8.30
5 1 0 175.48 8.70
5 1 0 185.78 9.00
6 -1 0 255.07 12.40
6 1 0 257.57 12.50
7 -1 0 39.00 3.60
7 1 0 39.50 3.90
8 -1 0 129.89 7.80
8 1 0 124.39 7.90
0 -2 0 101.09 4.20
0 -2 0 90.09 4.20
0 2 0 85.59 4.20
0 2 0 91.89 4.20
-1 -2 0 29.90 1.60
1 -2 0 30.60 1.60
-1 -2 0 31.40 1.40
-1 -2 0 30.80 1.60
1 -2 0 32.10 1.60
-1 2 0 31.80 1.60
-1 2 0 32.50 1.60
1 2 0 29.10 1.60
1 2 0 31.00 1.60
-1 2 0 29.50 1.60
-2 -2 0 88.59 4.40
2 -2 0 90.99 4.40
-2 -2 0 89.29 4.30
2 -2 0 94.89 4.50
2 2 0 90.59 4.20
2 2 0 90.19 4.40
2 2 0 98.59 4.50
-2 2 0 96.29 4.50
-2 2 0 96.69 4.30
-2 2 0 94.29 4.40
3 -2 0 135.19 6.60
3 -2 0 136.89 6.60
-3 -2 0 137.69 6.40
-3 -2 0 136.29 6.50
3 2 0 140.59 6.50
-3 2 0 129.29 6.30
-3 2 0 137.59 6.50
-3 2 0 144.19 6.50
3 2 0 142.59 6.60
3 2 0 136.39 6.30
4 -2 0 50.49 3.50
4 -2 0 61.29 3.40
-4 -2 0 60.79 3.00
4 2 0 61.19 3.50
4 2 0 60.29 3.30
-4 2 0 50.99 3.10
4 2 0 58.79 3.10
-4 2 0 61.09 3.00
5 -2 0 177.98 8.20
-5 -2 0 166.58 7.40
5 2 0 167.68 8.20
5 2 0 153.58 7.80
-5 2 0 164.68 7.50
-5 2 0 154.78 7.40
6 -2 0 9.30 2.00
6 2 0 11.30 2.10
7 -2 0 122.19 7.10
7 2 0 110.79 6.90
8 -2 0 3.80 2.80
8 2 0 -3.80 2.50
0 -3 0 0.90 0.40
0 -3 0 0.90 0.40
0 3 0 1.00 0.50
0 3 0 0.80 0.40
1 -3 0 1917.61 83.99
-1 -3 0 1763.52 83.89
1 -3 0 2080.59 83.99
-1 -3 0 1862.71 83.89
1 -3 0 1868.71 83.89
-1 3 0 1804.92 83.89
1 3 0 1883.01 83.89
-1 3 0 2158.08 84.09
-1 3 0 1770.82 83.89
1 3 0 1922.21 83.89
-2 -3 0 24.70 1.50
-2 -3 0 23.30 1.50
2 -3 0 24.90 1.60
2 -3 0 25.60 1.60
2 3 0 25.20 1.50
-2 3 0 24.80 1.50
2 3 0 23.00 1.30
-2 3 0 25.60 1.70
2 3 0 23.80 1.60
-2 3 0 24.90 1.40
-3 -3 0 810.12 34.90
-3 -3 0 741.83 35.30
3 -3 0 808.62 35.20
3 -3 0 773.22 35.10
-3 3 0 804.32 35.10
-3 3 0 783.32 34.90
3 3 0 831.22 35.20
3 3 0 742.83 35.00
3 3 0 778.22 34.80
-3 3 0 797.52 35.00
4 -3 0 61.09 3.70
4 -3 0 64.29 3.60
-4 -3 0 68.49 3.30
-4 3 0 62.49 3.50
-4 3 0 61.09 3.50
4 3 0 62.49 3.30
4 3 0 68.09 3.80
4 3 0 66.59 3.60
-4 3 0 66.89 3.30
5 -3 0 220.68 10.50
-5 -3 0 221.58 9.80
5 3 0 204.98 10.00
-5 3 0 207.98 9.80
5 3 0 215.78 10.50
-5 3 0 227.08 9.90
6 -3 0 56.29 4.20
6 3 0 55.99 4.20
7 -3 0 32.50 3.50
7 3 0 31.60 3.50
0 -4 0 577.74 24.80
0 -4 0 488.15 24.80
0 4 0 615.64 24.90
0 4 0 551.34 24.80
1 -4 0 48.30 2.50
-1 -4 0 52.29 2.60
-1 4 0 50.29 2.40
1 4 0 46.40 2.60
-1 4 0 54.49 2.60
-1 4 0 48.50 2.50
1 4 0 47.70 2.50
1 4 0 49.40 2.50
2 -4 0 419.76 17.60
2 -4 0 378.26 17.50
-2 -4 0 357.26 17.50
-2 -4 0 372.66 17.50
-2 4 0 414.36 17.60
2 4 0 388.16 17.60
-2 4 0 429.46 17.50
2 4 0 371.36 17.50
-2 4 0 382.76 17.40
-3 -4 0 209.38 9.70
3 -4 0 200.68 9.80
3 -4 0 211.18 9.70
3 4 0 202.08 9.70
-3 4 0 205.98 9.60
-3 4 0 208.78 9.80
-3 4 0 220.58 9.70
3 4 0 211.58 9.80
3 4 0 217.38 9.50
-4 -4 0 166.58 7.90
4 -4 0 164.28 8.10
4 4 0 165.28 7.70
-4 4 0 171.48 7.80
-4 4 0 164.48 7.90
4 4 0 176.98 8.20
-4 4 0 168.38 8.00
-5 -4 0 202.88 9.40
5 -4 0 202.58 9.90
-5 4 0 211.38 9.50
5 4 0 200.08 9.40
-5 4 0 199.68 9.40
5 4 0 208.58 10.00
6 -4 0 41.30 3.40
6 4 0 44.80 3.70
7 -4 0 113.39 6.90
7 4 0 119.29 7.20
0 -5 0 1.50 0.60
0 -5 0 1.10 0.60
0 5 0 1.70 0.70
0 5 0 2.40 0.70
1 -5 0 1008.40 46.70
-1 -5 0 1172.38 46.70
1 -5 0 1063.79 46.70
1 5 0 1025.80 46.70
-1 5 0 1080.09 46.70
-1 5 0 1055.69 46.70
1 5 0 1026.40 46.60
1 5 0 1008.60 46.70
-1 5 0 1036.40 46.50
-2 -5 0 46.90 2.30
2 -5 0 51.09 2.50
-2 -5 0 52.69 2.80
2 -5 0 53.29 2.80
-2 5 0 51.79 2.80
2 5 0 46.40 2.70
-2 5 0 50.09 2.60
-2 5 0 48.80 2.70
2 5 0 49.30 2.70
-3 -5 0 448.36 20.40
3 -5 0 428.76 20.50
3 -5 0 472.65 20.40
-3 5 0 471.55 20.40
3 5 0 429.56 20.50
-3 5 0 467.95 20.60
-3 5 0 449.56 20.40
3 5 0 466.05 20.60
4 -5 0 101.99 5.10
-4 -5 0 91.59 4.90
4 5 0 100.69 5.30
-4 5 0 97.59 5.10
-4 5 0 98.19 4.90
-4 5 0 97.89 4.90
-5 -5 0 121.19 6.00
5 -5 0 124.39 6.50
-5 5 0 130.09 6.20
-5 5 0 124.19 5.90
5 5 0 111.49 6.10
5 5 0 129.09 6.60
6 -5 0 81.89 5.10
6 5 0 82.29 5.40
7 -5 0 19.00 2.80
7 5 0 18.80 3.10
0 -6 0 416.06 18.40
0 -6 0 433.66 18.50
0 6 0 356.56 18.40
0 6 0 431.56 18.50
1 -6 0 16.50 1.40
1 -6 0 12.10 1.30
-1 -6 0 18.30 1.50
1 6 0 13.30 1.10
-1 6 0 15.50 1.00
-1 6 0 14.70 1.30
1 6 0 14.80 1.40
1 6 0 12.90 1.30
-1 6 0 14.80 1.40
-2 -6 0 339.07 14.80
2 -6 0 315.97 15.20
-2 -6 0 370.76 15.20
2 6 0 328.97 15.10
-2 6 0 354.56 15.20
-2 6 0 329.37 15.20
2 6 0 315.07 15.20
2 6 0 327.97 15.20
-2 6 0 317.97 15.00
-3 -6 0 80.19 4.30
3 -6 0 81.59 4.10
-3 6 0 79.79 4.00
-3 6 0 78.19 4.20
-3 6 0 83.39 4.40
3 6 0 85.49 4.40
-4 -6 0 158.68 8.00
4 -6 0 175.58 8.10
-4 6 0 168.18 8.30
4 6 0 169.78 8.30
-4 6 0 166.08 7.90
-4 6 0 171.08 8.00
5 -6 0 99.99 5.50
-5 -6 0 101.19 5.10
-5 6 0 100.19 5.40
5 6 0 100.89 5.70
6 -6 0 44.60 3.50
6 6 0 41.90 3.70
7 6 0 73.19 5.60
0 -7 0 0.90 0.90
0 -7 0 0.50 0.70
0 7 0 0.40 0.80
0 7 0 0.60 0.90
0 7 0 0.00 0.50
1 -7 0 380.46 17.50
-1 -7 0 371.26 17.50
1 -7 0 393.06 17.50
-1 7 0 410.96 17.50
-1 7 0 373.06 17.50
1 7 0 382.16 17.50
1 7 0 383.76 17.30
1 7 0 388.66 17.50
-2 -7 0 56.49 3.00
-2 7 0 41.20 2.50
-2 7 0 46.00 2.80
2 7 0 40.60 3.00
2 7 0 48.40 2.70
-2 7 0 48.80 2.90
-3 -7 0 253.87 11.30
-3 7 0 244.18 11.00
-3 7 0 222.78 11.30
-3 7 0 236.88 11.20
3 7 0 247.98 11.30
-4 -7 0 103.69 5.40
4 -7 0 104.09 5.30
4 7 0 103.39 5.60
-4 7 0 97.29 5.10
-4 7 0 106.49 5.30
-4 7 0 108.89 5.60
5 -7 0 94.79 5.30
-5 -7 0 95.69 5.10
-5 7 0 96.69 5.40
5 7 0 99.59 5.70
6 -7 0 89.59 5.40
6 7 0 89.99 5.80
7 7 0 18.90 3.40
0 -8 0 781.32 35.80
0 8 0 814.02 35.50
0 8 0 804.02 35.80
-1 -8 0 8.60 1.50
1 -8 0 8.20 1.40
1 8 0 8.30 1.40
1 8 0 8.00 1.00
-1 8 0 8.30 1.30
-2 -8 0 534.05 25.10
-2 8 0 591.94 25.20
2 8 0 562.54 25.20
-2 8 0 518.65 24.80
2 8 0 576.74 25.00
-3 -8 0 44.40 3.20
-3 8 0 43.90 3.10
-3 8 0 47.70 2.60
3 8 0 47.70 3.20
3 8 0 52.39 3.10
-3 8 0 43.20 3.00
-4 -8 0 190.88 9.50
-4 8 0 193.88 9.10
4 8 0 205.58 9.70
-4 8 0 195.58 9.70
-4 8 0 202.68 9.50
5 -8 0 57.19 3.50
-5 -8 0 54.09 3.60
-5 8 0 56.59 3.90
5 8 0 53.89 4.10
6 8 0 25.30 3.20
7 8 0 32.00 3.90
0 -9 0 -1.10 1.10
0 9 0 0.70 0.60
0 9 0 0.80 1.10
1 -9 0 312.07 15.10
-1 -9 0 328.87 15.10
-1 9 0 320.87 15.10
1 9 0 330.57 15.10
1 9 0 335.97 14.80
-2 -9 0 93.09 4.90
-2 9 0 95.19 4.90
2 9 0 81.29 4.80
2 9 0 93.49 4.60
-2 9 0 79.99 4.30
-3 -9 0 161.28 8.20
-3 9 0 157.18 8.20
3 9 0 184.18 8.30
-3 9 0 157.58 7.50
3 9 0 160.58 8.10
-4 -9 0 179.48 9.10
-4 9 0 178.08 9.20
4 9 0 196.38 9.40
4 9 0 189.38 9.30
-5 -9 0 38.60 3.30
-5 9 0 48.30 3.80
5 9 0 36.60 3.40
6 9 0 152.18 8.60
0 -10 0 1300.57 57.49
0 10 0 1267.97 57.39
0 10 0 1294.07 56.99
-1 -10 0 14.60 2.00
-1 10 0 21.30 2.10
1 10 0 14.40 1.90
1 10 0 16.00 1.50
-2 -10 0 1003.00 44.50
-2 10 0 998.80 44.40
2 10 0 1054.19 44.50
2 10 0 982.60 44.20
-2 10 0 921.01 43.90
-3 -10 0 86.19 5.00
-3 10 0 75.49 3.90
-3 10 0 88.19 4.80
3 10 0 78.69 4.60
3 10 0 82.09 4.90
-4 -10 0 501.75 21.80
-4 10 0 444.46 21.80
4 10 0 459.05 21.90
4 10 0 480.95 21.80
-5 -10 0 107.69 6.00
5 10 0 104.39 6.60
5 10 0 110.09 6.60
-5 10 0 105.69 6.20
6 10 0 161.48 9.00
6 10 0 159.58 9.20
0 -11 0 4.00 1.70
0 11 0 1.20 0.80
0 11 0 3.10 1.50
-1 -11 0 769.42 36.50
-1 11 0 800.92 35.90
1 11 0 861.71 36.60
1 11 0 800.72 36.10
-1 11 0 815.02 36.50
-2 -11 0 17.00 2.30
-2 11 0 13.70 1.30
-2 11 0 17.10 2.20
2 11 0 13.70 2.10
2 11 0 11.40 1.70
-3 -11 0 539.05 23.00
3 11 0 494.45 23.00
3 11 0 498.55 22.80
-3 11 0 459.55 22.80
-4 -11 0 23.10 2.80
4 11 0 34.80 3.40
4 11 0 33.40 3.10
-4 11 0 35.80 3.20
-5 11 0 193.98 10.10
5 11 0 202.28 10.30
5 11 0 196.68 10.50
6 11 0 25.80 3.50
6 11 0 26.60 3.80
0 -12 0 46.70 3.60
0 12 0 43.70 3.50
0 12 0 43.60 2.70
-1 -12 0 10.70 2.30
1 12 0 12.40 2.30
-1 12 0 8.50 2.00
-1 12 0 11.50 1.10
1 12 0 13.40 1.50
-2 -12 0 31.40 3.20
2 12 0 36.10 2.70
-2 12 0 33.90 3.20
2 12 0 28.30 3.00
-2 12 0 32.90 1.90
-3 -12 0 66.99 4.70
-3 12 0 59.59 4.60
3 12 0 68.99 4.90
3 12 0 60.39 4.10
-4 -12 0 11.80 2.40
-4 12 0 10.30 2.30
4 12 0 9.20 2.50
4 12 0 10.50 2.20
-5 12 0 92.99 5.90
5 12 0 86.39 6.00
5 12 0 79.79 6.00
0 13 0 2.40 1.80
0 13 0 -0.30 1.00
-1 -13 0 244.38 12.10
1 13 0 253.67 11.50
1 13 0 224.18 12.10
-1 13 0 250.67 11.20
-2 -13 0 14.00 2.50
-2 13 0 18.70 2.70
2 13 0 19.70 2.80
2 13 0 8.60 1.70
-3 -13 0 135.09 7.50
3 13 0 126.39 7.00
-3 13 0 124.79 7.30
3 13 0 141.39 7.50
4 13 0 31.90 3.60
4 13 0 33.10 3.20
-4 13 0 30.00 3.40
5 13 0 32.50 3.90
-5 13 0 33.10 3.60
5 13 0 33.20 3.60
0 14 0 155.18 7.90
0 14 0 178.38 8.80
-1 14 0 5.40 2.10
1 14 0 6.40 2.40
1 14 0 3.20 1.40
2 14 0 120.29 6.40
2 14 0 117.69 7.00
-2 14 0 117.79 6.90
3 14 0 18.00 3.00
-3 14 0 16.70 2.80
3 14 0 10.90 2.30
4 14 0 51.69 4.10
4 14 0 39.70 4.40
-4 14 0 59.39 4.60
0 15 0 2.20 2.20
1 15 0 20.50 3.20
1 15 0 17.30 2.80
-1 15 0 16.30 2.80
-2 15 0 9.00 2.70
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5 0 -9 -0.50 2.80
-4 0 9 2.80 2.60
4 0 -9 -1.70 2.60
-3 0 9 -1.80 2.20
3 0 -9 -3.30 2.50
-2 0 9 1.50 2.00
2 0 -9 1.10 2.80
1 0 -9 -1.10 2.80
0 0 -9 -1.00 2.60
-7 -1 9 2.30 3.10
7 -1 -9 -0.10 2.80
-7 1 9 5.50 3.20
7 1 -9 2.90 2.90
-6 -1 9 1.10 2.80
6 -1 -9 2.70 3.00
6 1 -9 -1.10 2.50
-6 1 9 3.70 2.80
-5 -1 9 2.10 2.80
5 -1 -9 -0.70 2.60
5 1 -9 1.00 2.80
-5 1 9 4.40 2.90
4 -1 -9 0.50 2.70
-4 -1 9 -0.30 2.50
-4 1 9 2.60 2.50
4 1 -9 -4.20 2.40
3 -1 -9 1.60 2.70
-3 -1 9 1.90 2.30
3 1 -9 -0.10 2.50
-3 1 9 1.00 2.20
-2 -1 9 2.40 2.20
2 -1 -9 5.30 2.90
-2 1 9 1.10 2.00
2 1 -9 -0.70 2.50
1 -1 -9 -1.40 2.60
1 1 -9 1.90 2.60
0 -1 -9 1.60 2.70
0 1 -9 -1.30 2.60
-7 -2 9 3.00 3.20
7 -2 -9 -6.80 2.80
7 2 -9 2.20 2.70
-7 2 9 1.70 3.40
-6 -2 9 3.50 3.20
6 -2 -9 0.60 2.80
-6 2 9 -0.40 2.60
6 2 -9 0.80 2.80
5 -2 -9 1.70 3.00
-5 -2 9 0.10 2.50
5 2 -9 1.60 2.80
-5 2 9 -1.20 2.30
4 -2 -9 2.60 3.10
-4 -2 9 0.40 2.60
-4 2 9 2.10 2.30
4 2 -9 -0.40 2.50
3 -2 -9 2.10 2.90
-3 -2 9 2.50 2.40
3 2 -9 -1.60 2.50
-3 2 9 5.40 2.40
-2 -2 9 1.30 2.20
2 -2 -9 0.90 2.70
2 2 -9 1.20 2.80
-2 2 9 -0.50 2.00
1 -2 -9 -1.90 2.60
1 2 -9 -1.80 2.60
0 -2 -9 -0.70 2.70
0 2 -9 0.50 2.80
6 -3 -9 4.40 3.10
-6 -3 9 0.50 2.90
-6 3 9 3.90 2.90
6 3 -9 -0.30 2.30
-5 -3 9 7.00 2.90
5 -3 -9 9.40 3.60
5 3 -9 5.10 2.60
-5 3 9 8.20 2.80
-4 -3 9 1.40 2.60
4 -3 -9 1.20 3.10
4 3 -9 -0.60 2.60
-4 3 9 4.30 2.50
4 3 -9 2.40 2.00
-3 -3 9 4.40 2.60
3 -3 -9 0.20 2.80
3 3 -9 1.80 2.50
-3 3 9 3.10 2.40
-2 -3 9 2.40 2.30
2 -3 -9 -2.00 2.80
-2 3 9 2.00 2.10
2 3 -9 1.30 2.70
1 -3 -9 -0.10 3.00
1 3 -9 -0.40 2.50
0 -3 -9 1.30 2.90
0 3 -9 -2.20 2.60
-6 -4 9 -0.30 2.80
6 -4 -9 2.90 3.30
-6 4 9 1.20 2.60
6 4 -9 -0.80 2.40
-5 -4 9 17.70 3.60
5 -4 -9 6.00 3.50
-5 4 9 12.20 3.20
5 4 -9 8.20 3.00
4 -4 -9 4.60 3.30
-4 -4 9 -2.70 2.60
4 4 -9 -1.90 2.50
4 4 -9 0.60 1.90
-4 4 9 1.20 2.60
3 -4 -9 7.60 3.20
-3 -4 9 0.70 2.50
-3 4 9 11.10 2.70
3 4 -9 1.50 2.80
2 -4 -9 1.20 2.90
-2 -4 9 2.00 2.40
2 4 -9 0.40 2.50
-2 4 9 -0.40 2.10
1 -4 -9 4.10 3.10
1 4 -9 6.00 3.10
0 -4 -9 3.10 3.10
6 -5 -9 5.20 3.30
-6 -5 9 1.00 3.00
-6 5 9 2.60 2.90
5 -5 -9 10.40 3.50
-5 -5 9 12.00 3.60
-5 5 9 10.90 3.10
5 5 -9 9.60 3.00
4 -5 -9 -1.80 3.00
-4 -5 9 2.30 2.70
4 5 -9 -0.40 2.00
4 5 -9 -0.30 2.60
-4 5 9 0.50 2.40
3 -5 -9 5.60 3.60
-3 -5 9 4.70 2.70
-3 5 9 5.10 2.50
3 5 -9 3.70 2.80
2 -5 -9 0.00 3.30
-2 -5 9 -2.60 2.20
-2 5 9 1.90 2.20
2 5 -9 3.10 2.90
1 -5 -9 -1.10 2.90
1 5 -9 1.30 2.80
-6 -6 9 8.90 3.60
-6 6 9 15.80 3.70
5 -6 -9 39.50 4.90
-5 -6 9 37.40 4.50
5 6 -9 33.80 3.80
-5 6 9 35.00 4.40
5 6 -9 29.10 3.80
4 -6 -9 23.90 4.50
-4 -6 9 16.30 3.40
4 6 -9 16.10 2.70
-4 6 9 23.30 3.50
4 6 -9 14.90 3.20
-3 -6 9 60.09 5.30
3 -6 -9 48.20 5.50
3 6 -9 50.09 4.70
-3 6 9 56.89 4.90
2 -6 -9 8.50 3.60
-2 -6 9 11.70 3.10
-2 6 9 14.40 2.90
2 6 -9 9.80 3.30
1 -6 -9 54.99 5.50
5 -7 -9 70.59 6.40
-5 -7 9 66.89 6.00
5 7 -9 55.69 4.90
-5 7 9 62.19 5.70
4 -7 -9 3.70 3.50
-4 -7 9 6.30 3.00
4 7 -9 4.10 2.30
4 7 -9 2.60 2.60
-4 7 9 6.50 2.60
3 -7 -9 56.89 5.90
-3 -7 9 64.19 5.50
-3 7 9 57.59 5.00
3 7 -9 57.99 5.10
-2 -7 9 8.40 2.90
2 -7 -9 13.50 3.90
-2 7 9 11.30 3.00
-4 -8 9 23.80 4.20
4 -8 -9 23.60 5.20
-4 8 9 18.60 3.60
-3 -8 9 2.40 3.10
3 -8 -9 -2.10 3.40
-3 8 9 -1.20 2.60
-5 0 10 31.20 4.30
5 0 -10 22.90 4.10
4 0 -10 74.69 6.70
-4 0 10 90.49 6.70
3 0 -10 51.59 5.50
-3 0 10 60.29 5.70
2 0 -10 41.50 4.90
-5 -1 10 67.49 6.00
5 -1 -10 66.79 6.30
-5 1 10 84.49 6.20
5 1 -10 68.69 6.20
4 -1 -10 12.40 3.70
-4 -1 10 23.80 3.70
-4 1 10 21.20 3.30
4 1 -10 12.70 3.50
-3 -1 10 43.70 5.00
3 -1 -10 36.70 4.80
-3 1 10 47.80 5.10
3 1 -10 40.30 4.80
2 -1 -10 34.30 4.50
2 1 -10 27.90 4.30
5 -2 -10 28.10 4.30
-5 -2 10 30.30 4.30
-5 2 10 24.00 3.80
5 2 -10 24.20 4.10
4 -2 -10 37.70 4.90
-4 -2 10 39.50 4.40
-4 2 10 42.30 4.50
4 2 -10 36.60 4.70
-3 -2 10 60.39 5.80
3 -2 -10 57.79 5.70
3 2 -10 45.40 5.30
-3 2 10 64.19 5.90
2 -2 -10 19.40 4.60
2 2 -10 15.70 3.90
-5 -3 10 46.80 4.90
-5 3 10 45.30 4.70
-4 -3 10 37.60 4.30
4 -3 -10 28.00 4.60
-4 3 10 44.40 4.60
4 3 -10 30.00 4.60
3 -3 -10 38.80 5.00
-3 -3 10 28.30 4.40
-3 3 10 36.40 5.10
3 3 -10 33.50 4.40
4 -4 -10 96.69 11.40
-4 -4 10 81.09 6.60
-4 4 10 96.69 7.00
4 4 -10 89.69 6.90
-3 -4 10 22.30 4.60
-3 4 10 21.20 4.50
0 0 0 0.00 0.00
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
;
_shelx_hkl_checksum 43949
_shelx_res_file
;
TITL AK2_a.res in P2(1)/c
AK2_A.res
created by SHELXL-2019/1 at 22:02:30 on 21-Mar-2024
CELL 0.71073 7.0105 13.2765 8.1311 90.000 114.808 90.000
ZERR 4.00 0.0004 0.0008 0.0005 0.000 0.003 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H N O SE
UNIT 24 12 12 8 4
TEMP -123.000
SIZE 0.140 0.210 0.280
L.S. 34
FMAP 2
PLAN 5
HTAB
BOND $H
CONF
ACTA
WGHT 0.000000 6.188400
FVAR 0.31990
SE1 5 0.774408 0.258346 0.821432 11.00000 0.02492 0.01075 =
0.02327 0.00169 0.01064 0.00008
O1 4 0.773713 0.473914 0.394355 11.00000 0.06584 0.01907 =
0.03439 -0.00303 0.02872 0.00061
O2 4 0.740815 0.634811 0.407931 11.00000 0.05357 0.01914 =
0.02933 0.00810 0.02207 0.00171
N1 3 0.771329 0.351983 0.660677 11.00000 0.02271 0.01177 =
0.01976 -0.00010 0.00948 0.00166
N2 3 0.756431 0.347591 0.978342 11.00000 0.02186 0.01448 =
0.02447 0.00179 0.01114 0.00001
N3 3 0.754830 0.549633 0.473082 11.00000 0.02824 0.01979 =
0.02005 0.00110 0.01249 0.00034
C1 1 0.756984 0.440518 0.730436 11.00000 0.01306 0.01413 =
0.01786 0.00040 0.00594 -0.00097
C2 1 0.747734 0.538049 0.650289 11.00000 0.01654 0.01454 =
0.01677 0.00098 0.00825 0.00010
C3 1 0.728755 0.623285 0.735875 11.00000 0.01860 0.01538 =
0.01737 0.00348 0.00643 0.00062
AFIX 43
H3 2 0.720824 0.686805 0.679574 11.00000 -1.20000
AFIX 0
C4 1 0.720674 0.619176 0.905627 11.00000 0.02221 0.01436 =
0.01887 -0.00552 0.01190 0.00134
AFIX 43
H4 2 0.707675 0.680103 0.961342 11.00000 -1.20000
AFIX 0
C5 1 0.731007 0.529967 0.992563 11.00000 0.01853 0.01830 =
0.01518 -0.00158 0.00982 0.00056
AFIX 43
H5 2 0.726556 0.528392 1.107708 11.00000 -1.20000
AFIX 0
C6 1 0.748743 0.438742 0.905645 11.00000 0.01642 0.01522 =
0.01838 0.00113 0.00887 0.00050
HKLF 4
REM AK2_a.res in P2(1)/c
REM wR2 = 0.1038, GooF = S = 1.172, Restrained GooF = 1.172 for all data
REM R1 = 0.0435 for 1297 Fo > 4sig(Fo) and 0.0507 for all 1475 data
REM 109 parameters refined using 0 restraints
END
WGHT 0.0000 6.1878
REM Instructions for potential hydrogen bonds
EQIV $1 x, y, z+1
HTAB C5 O1_$1
REM Highest difference peak 1.240, deepest hole -1.270, 1-sigma level 0.141
Q1 1 0.7232 0.6319 0.2530 11.00000 0.05 1.24
Q2 1 0.7494 0.5487 1.1929 11.00000 0.05 1.20
Q3 1 0.7916 0.2570 0.9198 11.00000 0.05 1.12
Q4 1 0.7893 0.4718 0.2751 11.00000 0.05 1.03
Q5 1 0.6698 0.2468 0.9524 11.00000 0.05 0.80
;
_shelx_res_checksum 13417
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 0.77441(9) 0.25835(4) 0.82143(8) 0.01947(18) Uani d 1 . .
O O1 0.7737(8) 0.4739(3) 0.3944(6) 0.0372(11) Uani d 1 . .
O O2 0.7408(8) 0.6348(3) 0.4079(6) 0.0324(11) Uani d 1 . .
N N1 0.7713(7) 0.3520(3) 0.6607(6) 0.0179(10) Uani d 1 . .
N N2 0.7564(7) 0.3476(3) 0.9783(6) 0.0198(10) Uani d 1 . .
N N3 0.7548(8) 0.5496(3) 0.4731(6) 0.0219(10) Uani d 1 . .
C C1 0.7570(8) 0.4405(4) 0.7304(7) 0.0152(10) Uani d 1 . .
C C2 0.7477(8) 0.5380(4) 0.6503(7) 0.0155(10) Uani d 1 . .
C C3 0.7288(8) 0.6233(4) 0.7359(7) 0.0175(11) Uani d 1 . .
H H3 0.720824 0.686805 0.679574 0.021 Uiso calc 1 . .
C C4 0.7207(8) 0.6192(4) 0.9056(7) 0.0174(11) Uani d 1 . .
H H4 0.707675 0.680103 0.961342 0.021 Uiso calc 1 . .
C C5 0.7310(8) 0.5300(4) 0.9926(7) 0.0164(10) Uani d 1 . .
H H5 0.726556 0.528392 1.107708 0.020 Uiso calc 1 . .
C C6 0.7487(8) 0.4387(4) 0.9056(7) 0.0161(10) Uani d 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Se1 0.0249(3) 0.0107(2) 0.0233(3) 0.0001(2) 0.0106(2) 0.0017(2)
O1 0.066(3) 0.019(2) 0.034(3) 0.001(2) 0.029(2) -0.0030(18)
O2 0.054(3) 0.019(2) 0.029(2) 0.0017(19) 0.022(2) 0.0081(17)
N1 0.023(3) 0.012(2) 0.020(2) 0.0017(17) 0.009(2) -0.0001(17)
N2 0.022(2) 0.014(2) 0.024(3) 0.0000(17) 0.011(2) 0.0018(18)
N3 0.028(3) 0.020(2) 0.020(3) 0.0003(19) 0.012(2) 0.0011(19)
C1 0.013(2) 0.014(2) 0.018(3) -0.0010(18) 0.006(2) 0.0004(19)
C2 0.017(3) 0.015(2) 0.017(3) 0.0001(19) 0.008(2) 0.0010(19)
C3 0.019(3) 0.015(2) 0.017(3) 0.001(2) 0.006(2) 0.003(2)
C4 0.022(3) 0.014(2) 0.019(3) 0.001(2) 0.012(2) -0.0055(19)
C5 0.019(3) 0.018(2) 0.015(3) 0.001(2) 0.010(2) -0.002(2)
C6 0.016(3) 0.015(2) 0.018(3) 0.0005(19) 0.009(2) 0.0011(19)
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
N2 Se1 N1 . . 94.46(19) ?
C1 N1 Se1 . . 106.4(3) ?
C6 N2 Se1 . . 106.7(4) ?
O1 N3 O2 . . 122.2(5) ?
O1 N3 C2 . . 118.7(4) ?
O2 N3 C2 . . 119.1(4) ?
N1 C1 C2 . . 126.9(5) ?
N1 C1 C6 . . 116.5(5) ?
C2 C1 C6 . . 116.5(4) ?
C3 C2 C1 . . 120.7(5) ?
C3 C2 N3 . . 117.6(4) ?
C1 C2 N3 . . 121.6(4) ?
C2 C3 C4 . . 121.4(5) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 121.8(5) ?
C5 C4 H4 . . 119.1 ?
C3 C4 H4 . . 119.1 ?
C4 C5 C6 . . 118.3(5) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
N2 C6 C5 . . 122.8(5) ?
N2 C6 C1 . . 116.0(5) ?
C5 C6 C1 . . 121.2(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
Se1 N2 . 1.784(5) ?
Se1 N1 . 1.797(4) ?
O1 N3 . 1.228(6) ?
O2 N3 . 1.235(6) ?
N1 C1 . 1.327(6) ?
N2 C6 . 1.338(7) ?
N3 C2 . 1.471(7) ?
C1 C2 . 1.439(7) ?
C1 C6 . 1.450(7) ?
C2 C3 . 1.364(7) ?
C3 C4 . 1.406(7) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.366(7) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.434(7) ?
C5 H5 . 0.9500 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Se1 O1 3.140(4) . 4_566 yes
Se1 N1 3.132(5) . 4_566 yes
Se1 N2 3.079(5) . 4_565 yes
O1 N1 2.709(6) . . yes
H5 O1 2.33 . 1_556 yes
O2 H3 2.37 . . yes
H4 O2 2.52 . 4_576 yes
N1 N3 3.012(6) . . yes
N1 N2 3.017(6) . 4_565 yes
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
C4 H4 O2 4_576 0.95 2.52 3.269(7) 135 yes
C5 H5 O1 1_556 0.95 2.33 3.240(7) 161 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
N2 Se1 N1 C1 . . . . -0.2(4) ?
N1 Se1 N2 C6 . . . . 0.2(4) ?
Se1 N1 C1 C2 . . . . -179.5(4) ?
Se1 N1 C1 C6 . . . . 0.2(6) ?
N1 C1 C2 C3 . . . . 178.7(5) ?
C6 C1 C2 C3 . . . . -1.0(7) ?
N1 C1 C2 N3 . . . . -0.3(8) ?
C6 C1 C2 N3 . . . . 180.0(5) ?
O1 N3 C2 C3 . . . . 179.4(5) ?
O2 N3 C2 C3 . . . . -0.9(8) ?
O1 N3 C2 C1 . . . . -1.6(8) ?
O2 N3 C2 C1 . . . . 178.1(5) ?
C1 C2 C3 C4 . . . . 0.9(8) ?
N3 C2 C3 C4 . . . . 180.0(5) ?
C2 C3 C4 C5 . . . . -0.1(9) ?
C3 C4 C5 C6 . . . . -0.5(8) ?
Se1 N2 C6 C5 . . . . 179.2(4) ?
Se1 N2 C6 C1 . . . . -0.1(6) ?
C4 C5 C6 N2 . . . . -178.9(5) ?
C4 C5 C6 C1 . . . . 0.4(8) ?
N1 C1 C6 N2 . . . . 0.0(7) ?
C2 C1 C6 N2 . . . . 179.7(5) ?
N1 C1 C6 C5 . . . . -179.4(5) ?
C2 C1 C6 C5 . . . . 0.4(7) ?