#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/76/4517657.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_4517657
loop_
_publ_author_name
'Hua, Guoxiong'
'Cordes, David B.'
'Slawin, Alexandra M. Z.'
'Woollins, J. Derek'
_publ_section_title
;
 Novel Five- and Six-Membered Rings of Phosphorus-Selenium Heterocycles
 from Selenation of Amido-Schiff Bases.
;
_journal_issue                   20
_journal_name_full               'ACS omega'
_journal_page_first              11737
_journal_page_last               11744
_journal_paper_doi               10.1021/acsomega.0c01064
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C16 H12 N2 O2 Se'
_chemical_formula_sum            'C16 H12 N2 O2 Se'
_chemical_formula_weight         343.24
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-16
_audit_creation_method           'by CrystalStructure 4.3'
_cell_angle_alpha                95.836(13)
_cell_angle_beta                 96.199(7)
_cell_angle_gamma                107.677(14)
_cell_formula_units_Z            2
_cell_length_a                   7.495(4)
_cell_length_b                   7.590(4)
_cell_length_c                   12.690(6)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      1.60
_cell_volume                     676.9(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5498
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.409
_diffrn_reflns_theta_min         1.631
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.780
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.06
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0685P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1811
_reflns_number_total             2362
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ao0c01064_si_001.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 4517654--4517661.cif.'
_cod_database_code               4517657
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
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
Se1 Se 0.20806(7) 0.16189(7) 0.44761(4) 0.0347(2) Uani 1 1 d . . . . .
O9 O 1.1144(5) 0.4572(6) 0.6605(3) 0.0478(10) Uani 1 1 d . . . . .
O11 O 1.0101(5) 0.5632(5) 0.8132(3) 0.0445(9) Uani 1 1 d . . . . .
N3 N 0.5223(6) 0.1491(6) 0.3688(3) 0.0385(10) Uani 1 1 d . . . . .
N4 N 0.3760(6) 0.0648(6) 0.2860(3) 0.0373(10) Uani 1 1 d . . . . .
C2 C 0.4702(7) 0.2086(7) 0.4561(4) 0.0321(11) Uani 1 1 d . . . . .
C5 C 0.2077(7) 0.0534(7) 0.3082(4) 0.0312(11) Uani 1 1 d . . . . .
C6 C 0.6081(6) 0.3049(6) 0.5526(4) 0.0290(11) Uani 1 1 d . . . . .
C7 C 0.7993(7) 0.3294(6) 0.5511(4) 0.0359(12) Uani 1 1 d . . . . .
H7 H 0.843462 0.287262 0.488943 0.043 Uiso 1 1 calc R U . . .
C8 C 0.9207(7) 0.4163(7) 0.6424(4) 0.0320(11) Uani 1 1 d . . . . .
C10 C 1.1762(8) 0.5495(8) 0.7691(4) 0.0427(13) Uani 1 1 d . . . . .
H10A H 1.267492 0.675538 0.770527 0.051 Uiso 1 1 calc R U . . .
H10B H 1.238955 0.476666 0.811547 0.051 Uiso 1 1 calc R U . . .
C12 C 0.8613(7) 0.4814(7) 0.7336(4) 0.0358(12) Uani 1 1 d . . . . .
C13 C 0.6708(8) 0.4556(7) 0.7359(4) 0.0418(13) Uani 1 1 d . . . . .
H13 H 0.627307 0.496123 0.798615 0.050 Uiso 1 1 calc R U . . .
C14 C 0.5474(7) 0.3695(7) 0.6444(4) 0.0392(12) Uani 1 1 d . . . . .
H14 H 0.416523 0.353428 0.643595 0.047 Uiso 1 1 calc R U . . .
C15 C 0.0371(7) -0.0280(6) 0.2289(4) 0.0309(11) Uani 1 1 d . . . . .
C16 C 0.0464(7) -0.1210(7) 0.1307(4) 0.0371(12) Uani 1 1 d . . . . .
H16 H 0.163141 -0.135605 0.116020 0.045 Uiso 1 1 calc R U . . .
C17 C -0.1150(8) -0.1935(7) 0.0530(4) 0.0406(13) Uani 1 1 d . . . . .
H17 H -0.107313 -0.259715 -0.013166 0.049 Uiso 1 1 calc R U . . .
C18 C -0.2838(8) -0.1700(7) 0.0714(4) 0.0376(12) Uani 1 1 d . . . . .
C19 C -0.2954(7) -0.0825(7) 0.1704(4) 0.0376(12) Uani 1 1 d . . . . .
H19 H -0.412818 -0.069416 0.185032 0.045 Uiso 1 1 calc R U . . .
C20 C -0.1395(7) -0.0147(7) 0.2475(4) 0.0377(12) Uani 1 1 d . . . . .
H20 H -0.151333 0.042922 0.315305 0.045 Uiso 1 1 calc R U . . .
C21 C -0.4588(8) -0.2415(8) -0.0153(4) 0.0457(14) Uani 1 1 d . . . . .
H21A H -0.493736 -0.377497 -0.032688 0.055 Uiso 1 1 calc R U . . .
H21B H -0.429995 -0.183698 -0.079702 0.055 Uiso 1 1 calc R U . . .
H21C H -0.564357 -0.208767 0.011228 0.055 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(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
C5 Se1 C2 82.6(2) . . ?
C8 O9 C10 106.6(4) . . ?
C12 O11 C10 105.8(4) . . ?
C2 N3 N4 114.5(4) . . ?
C5 N4 N3 115.3(4) . . ?
N3 C2 C6 122.0(4) . . ?
N3 C2 Se1 114.0(4) . . ?
C6 C2 Se1 123.9(3) . . ?
N4 C5 C15 122.5(4) . . ?
N4 C5 Se1 113.5(4) . . ?
C15 C5 Se1 123.9(4) . . ?
C7 C6 C14 120.2(4) . . ?
C7 C6 C2 119.3(4) . . ?
C14 C6 C2 120.5(4) . . ?
C8 C7 C6 117.2(4) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C7 C8 O9 128.1(5) . . ?
C7 C8 C12 122.8(5) . . ?
O9 C8 C12 109.1(4) . . ?
O9 C10 O11 107.3(4) . . ?
O9 C10 H10A 110.3 . . ?
O11 C10 H10A 110.3 . . ?
O9 C10 H10B 110.3 . . ?
O11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
O11 C12 C8 111.2(4) . . ?
O11 C12 C13 128.7(5) . . ?
C8 C12 C13 120.2(4) . . ?
C14 C13 C12 117.6(5) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C6 122.0(5) . . ?
C13 C14 H14 119.0 . . ?
C6 C14 H14 119.0 . . ?
C16 C15 C20 117.4(5) . . ?
C16 C15 C5 120.3(4) . . ?
C20 C15 C5 122.4(5) . . ?
C15 C16 C17 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.7(5) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 118.9(5) . . ?
C17 C18 C21 121.0(5) . . ?
C19 C18 C21 120.1(5) . . ?
C20 C19 C18 120.6(5) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 121.6(5) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
Se1 C5 1.873(5) . ?
Se1 C2 1.876(5) . ?
O9 C8 1.377(6) . ?
O9 C10 1.440(6) . ?
O11 C12 1.363(6) . ?
O11 C10 1.446(7) . ?
N3 C2 1.297(6) . ?
N3 N4 1.380(6) . ?
N4 C5 1.301(6) . ?
C2 C6 1.480(7) . ?
C5 C15 1.464(7) . ?
C6 C7 1.391(7) . ?
C6 C14 1.392(7) . ?
C7 C8 1.364(7) . ?
C7 H7 0.9500 . ?
C8 C12 1.382(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C13 1.384(7) . ?
C13 C14 1.370(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.388(7) . ?
C15 C20 1.400(7) . ?
C16 C17 1.403(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.370(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(7) . ?
C18 C21 1.536(7) . ?
C19 C20 1.368(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
C2 N3 N4 C5 -1.6(6) . . . . ?
N4 N3 C2 C6 -179.1(4) . . . . ?
N4 N3 C2 Se1 0.7(5) . . . . ?
C5 Se1 C2 N3 0.1(4) . . . . ?
C5 Se1 C2 C6 180.0(4) . . . . ?
N3 N4 C5 C15 178.6(4) . . . . ?
N3 N4 C5 Se1 1.7(5) . . . . ?
C2 Se1 C5 N4 -1.0(4) . . . . ?
C2 Se1 C5 C15 -177.9(4) . . . . ?
N3 C2 C6 C7 -1.4(7) . . . . ?
Se1 C2 C6 C7 178.8(3) . . . . ?
N3 C2 C6 C14 179.0(4) . . . . ?
Se1 C2 C6 C14 -0.8(7) . . . . ?
C14 C6 C7 C8 0.6(7) . . . . ?
C2 C6 C7 C8 -179.0(4) . . . . ?
C6 C7 C8 O9 -179.7(4) . . . . ?
C6 C7 C8 C12 -0.9(7) . . . . ?
C10 O9 C8 C7 179.9(5) . . . . ?
C10 O9 C8 C12 1.0(5) . . . . ?
C8 O9 C10 O11 -0.9(5) . . . . ?
C12 O11 C10 O9 0.4(5) . . . . ?
C10 O11 C12 C8 0.2(5) . . . . ?
C10 O11 C12 C13 178.7(5) . . . . ?
C7 C8 C12 O11 -179.7(4) . . . . ?
O9 C8 C12 O11 -0.7(6) . . . . ?
C7 C8 C12 C13 1.6(8) . . . . ?
O9 C8 C12 C13 -179.4(4) . . . . ?
O11 C12 C13 C14 179.6(5) . . . . ?
C8 C12 C13 C14 -1.9(8) . . . . ?
C12 C13 C14 C6 1.7(8) . . . . ?
C7 C6 C14 C13 -1.0(8) . . . . ?
C2 C6 C14 C13 178.5(5) . . . . ?
N4 C5 C15 C16 9.4(7) . . . . ?
Se1 C5 C15 C16 -174.0(3) . . . . ?
N4 C5 C15 C20 -170.0(5) . . . . ?
Se1 C5 C15 C20 6.6(7) . . . . ?
C20 C15 C16 C17 1.6(7) . . . . ?
C5 C15 C16 C17 -177.7(4) . . . . ?
C15 C16 C17 C18 1.7(8) . . . . ?
C16 C17 C18 C19 -3.6(8) . . . . ?
C16 C17 C18 C21 177.3(4) . . . . ?
C17 C18 C19 C20 2.3(8) . . . . ?
C21 C18 C19 C20 -178.6(5) . . . . ?
C18 C19 C20 C15 1.1(8) . . . . ?
C16 C15 C20 C19 -3.0(7) . . . . ?
C5 C15 C20 C19 176.4(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346647
