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#$Date: 2023-03-04 19:32:30 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281517 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/21/7062145.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_7062145
loop_
_publ_author_name
'Turcio-García, Luis Ángel'
'Valdés, Hugo'
'Arenaza-Corona, Antonino'
'Hernández-Ortega, Simón'
'Morales-Morales, David'
_publ_section_title
;
 Electronic properties and supramolecular study of selenoureas with
 fluorinated-NHC ligands derived from imidazo[1,5-a]pyridines
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2090
_journal_page_last               2095
_journal_paper_doi               10.1039/D2NJ04699G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C13 H9 F N2 Se'
_chemical_formula_sum            'C13 H9 F N2 Se'
_chemical_formula_weight         291.18
_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_method           SHELXL-2018/3
_audit_update_record
;
2022-08-04 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                74.399(2)
_cell_angle_beta                 77.913(2)
_cell_angle_gamma                68.957(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9606(3)
_cell_length_b                   7.4230(4)
_cell_length_c                   12.5160(6)
_cell_measurement_reflns_used    5509
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      3.01
_cell_volume                     576.72(5)
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_molecular_graphics
'Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7046
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_min         3.009
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    3.244
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       Prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0330
_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)+(0.0381P)²+0.2073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1803
_reflns_number_total             2108
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04699g2.cif
_cod_data_source_block           Compound-4-Se
_cod_depositor_comments
'Adding full bibliography for 7062140--7062145.cif.'
_cod_database_code               7062145
_shelx_shelxl_version_number     2018/3
_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   0.337
_shelx_estimated_absorpt_t_max   0.689
_exptl_absorpt_special_details
; 
 The following wavelength and cell were deduced by SADABS from the 
 direction cosines etc. They are given here for emergency use only: 
 CELL 0.70988    6.950    7.415   12.507   74.418   77.869   68.976 

;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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 0.16497(5) 0.99709(4) 0.29909(2) 0.05133(15) Uani 1 1 d . . . . .
F1 F 0.5902(3) 0.7199(3) 0.12091(17) 0.0757(6) Uani 1 1 d . . . . .
N2 N 0.2690(3) 0.6092(3) 0.25492(18) 0.0399(5) Uani 1 1 d . . . . .
N8 N 0.2414(3) 0.6029(3) 0.43046(17) 0.0360(5) Uani 1 1 d . . . . .
C1 C 0.2299(4) 0.7286(4) 0.3279(2) 0.0376(6) Uani 1 1 d . . . . .
C3 C 0.3010(4) 0.4150(4) 0.3099(2) 0.0445(7) Uani 1 1 d . . . . .
H3 H 0.329987 0.308013 0.277131 0.053 Uiso 1 1 calc R U . . .
C4 C 0.2945(4) 0.2602(5) 0.5203(3) 0.0534(8) Uani 1 1 d . . . . .
H4 H 0.317302 0.130147 0.517425 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2730(4) 0.3091(5) 0.6189(3) 0.0566(9) Uani 1 1 d . . . . .
H5 H 0.283448 0.211710 0.684187 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2345(4) 0.5066(5) 0.6246(2) 0.0519(8) Uani 1 1 d . . . . .
H6 H 0.220766 0.536783 0.693843 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2173(4) 0.6519(5) 0.5326(2) 0.0441(7) Uani 1 1 d . . . . .
H7 H 0.189978 0.781865 0.537364 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2823(4) 0.4091(4) 0.4200(2) 0.0406(6) Uani 1 1 d . . . . .
C10 C 0.2686(4) 0.6773(4) 0.1368(2) 0.0412(6) Uani 1 1 d . . . . .
C11 C 0.4302(5) 0.7338(5) 0.0710(2) 0.0476(7) Uani 1 1 d . . . . .
C12 C 0.4330(5) 0.8006(5) -0.0423(3) 0.0590(9) Uani 1 1 d . . . . .
H12 H 0.543131 0.839604 -0.085496 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2707(6) 0.8085(5) -0.0905(3) 0.0650(9) Uani 1 1 d . . . . .
H13 H 0.269822 0.854357 -0.167353 0.078 Uiso 1 1 calc R U . . .
C14 C 0.1100(6) 0.7502(6) -0.0278(3) 0.0687(10) Uani 1 1 d . . . . .
H14 H 0.001313 0.755044 -0.061966 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1080(5) 0.6839(5) 0.0863(3) 0.0578(8) Uani 1 1 d . . . . .
H15 H -0.001801 0.643826 0.128998 0.069 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 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'
F F 0.0171 0.0103 '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
C1 N2 C3 111.4(2) . . ?
C1 N2 C10 124.3(2) . . ?
C3 N2 C10 124.2(2) . . ?
C1 N8 C7 126.9(2) . . ?
C1 N8 C9 110.5(2) . . ?
C7 N8 C9 122.6(2) . . ?
N2 C1 N8 104.3(2) . . ?
N2 C1 Se1 128.8(2) . . ?
N8 C1 Se1 126.85(19) . . ?
C9 C3 N2 107.2(2) . . ?
C9 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C5 C4 C9 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C9 C4 H4 120.2 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 N8 118.1(3) . . ?
C6 C7 H7 120.9 . . ?
N8 C7 H7 120.9 . . ?
C3 C9 N8 106.6(2) . . ?
C3 C9 C4 136.0(3) . . ?
N8 C9 C4 117.4(3) . . ?
C11 C10 C15 118.6(3) . . ?
C11 C10 N2 120.8(2) . . ?
C15 C10 N2 120.6(3) . . ?
F1 C11 C12 120.0(3) . . ?
F1 C11 C10 118.1(3) . . ?
C12 C11 C10 121.9(3) . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.8(3) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
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 C1 1.828(3) . ?
F1 C11 1.347(3) . ?
N2 C1 1.361(3) . ?
N2 C3 1.379(4) . ?
N2 C10 1.429(3) . ?
N8 C1 1.367(3) . ?
N8 C7 1.382(3) . ?
N8 C9 1.399(3) . ?
C3 C9 1.347(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(5) . ?
C4 C9 1.428(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.342(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C10 C11 1.373(4) . ?
C10 C15 1.375(4) . ?
C11 C12 1.369(4) . ?
C12 C13 1.365(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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
C3 N2 C1 N8 0.9(3) . . . . ?
C10 N2 C1 N8 178.5(2) . . . . ?
C3 N2 C1 Se1 -176.66(19) . . . . ?
C10 N2 C1 Se1 1.0(4) . . . . ?
C7 N8 C1 N2 178.6(2) . . . . ?
C9 N8 C1 N2 -1.4(3) . . . . ?
C7 N8 C1 Se1 -3.8(4) . . . . ?
C9 N8 C1 Se1 176.22(18) . . . . ?
C1 N2 C3 C9 0.0(3) . . . . ?
C10 N2 C3 C9 -177.7(2) . . . . ?
C9 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 N8 -0.9(4) . . . . ?
C1 N8 C7 C6 -179.9(2) . . . . ?
C9 N8 C7 C6 0.1(4) . . . . ?
N2 C3 C9 N8 -0.8(3) . . . . ?
N2 C3 C9 C4 179.3(3) . . . . ?
C1 N8 C9 C3 1.4(3) . . . . ?
C7 N8 C9 C3 -178.6(2) . . . . ?
C1 N8 C9 C4 -178.7(2) . . . . ?
C7 N8 C9 C4 1.3(4) . . . . ?
C5 C4 C9 C3 177.9(3) . . . . ?
C5 C4 C9 N8 -1.9(4) . . . . ?
C1 N2 C10 C11 75.2(4) . . . . ?
C3 N2 C10 C11 -107.5(3) . . . . ?
C1 N2 C10 C15 -106.1(3) . . . . ?
C3 N2 C10 C15 71.2(4) . . . . ?
C15 C10 C11 F1 -177.6(3) . . . . ?
N2 C10 C11 F1 1.1(4) . . . . ?
C15 C10 C11 C12 1.6(5) . . . . ?
N2 C10 C11 C12 -179.7(3) . . . . ?
F1 C11 C12 C13 178.5(3) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C12 C13 C14 C15 0.7(6) . . . . ?
C11 C10 C15 C14 -1.3(5) . . . . ?
N2 C10 C15 C14 179.9(3) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
