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#$Date: 2023-03-04 20:32:30 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281517 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/21/7062141.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_7062141
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         'C14 H9 F3 N2 Se'
_chemical_formula_sum            'C14 H9 F3 N2 Se'
_chemical_formula_weight         341.19
_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                88.0511(13)
_cell_angle_beta                 88.9630(12)
_cell_angle_gamma                79.6705(12)
_cell_formula_units_Z            2
_cell_length_a                   7.7546(3)
_cell_length_b                   7.7580(3)
_cell_length_c                   10.8750(5)
_cell_measurement_reflns_used    7111
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.67
_cell_volume                     643.22(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      150(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7700
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_min         2.670
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    2.945
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5053
_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    1.762
_exptl_crystal_description       Prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0237P)²+0.4624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0624
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2196
_reflns_number_total             2355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04699g2.cif
_cod_data_source_block           Compound-11-Se
_cod_depositor_comments
'Adding full bibliography for 7062140--7062145.cif.'
_cod_database_code               7062141
_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   0.365
_shelx_estimated_absorpt_t_max   0.734
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 0.57055(3) 0.71369(3) 0.34771(2) 0.03544(10) Uani 1 1 d . . . . .
F1 F 0.22679(19) 0.88135(17) 0.10184(14) 0.0414(3) Uani 1 1 d . . . . .
F2 F 0.1094(2) 0.7976(2) -0.05711(13) 0.0511(4) Uani 1 1 d . . . . .
F3 F -0.01864(17) 0.79322(18) 0.11842(13) 0.0373(3) Uani 1 1 d . . . . .
N2 N 0.2305(2) 0.6215(2) 0.30974(15) 0.0213(4) Uani 1 1 d . . . . .
N8 N 0.2405(2) 0.7633(2) 0.47567(15) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.3401(3) 0.6982(3) 0.37753(19) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.0666(3) 0.6346(3) 0.36505(19) 0.0221(4) Uani 1 1 d . . . . .
H3 H -0.030376 0.589615 0.335301 0.026 Uiso 1 1 calc R U . . .
C4 C -0.0508(3) 0.7799(3) 0.56582(19) 0.0254(5) Uani 1 1 d . . . . .
H4 H -0.166701 0.756231 0.563770 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0002(3) 0.8672(3) 0.6600(2) 0.0293(5) Uani 1 1 d . . . . .
H5 H -0.079185 0.901733 0.725913 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1733(3) 0.9081(3) 0.6615(2) 0.0291(5) Uani 1 1 d . . . . .
H6 H 0.206443 0.971529 0.727731 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2888(3) 0.8584(3) 0.57103(19) 0.0260(5) Uani 1 1 d . . . . .
H7 H 0.402514 0.887876 0.572034 0.031 Uiso 1 1 calc R U . . .
C9 C 0.0708(3) 0.7238(3) 0.46982(19) 0.0217(4) Uani 1 1 d . . . . .
C10 C 0.2825(3) 0.5168(3) 0.20397(19) 0.0229(4) Uani 1 1 d . . . . .
C11 C 0.2342(3) 0.5781(3) 0.0857(2) 0.0249(5) Uani 1 1 d . . . . .
C12 C 0.2795(3) 0.4661(3) -0.0117(2) 0.0315(5) Uani 1 1 d . . . . .
H12 H 0.247395 0.505663 -0.093161 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3704(3) 0.2987(3) 0.0090(2) 0.0359(6) Uani 1 1 d . . . . .
H13 H 0.399357 0.222957 -0.057964 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4198(3) 0.2403(3) 0.1265(2) 0.0356(6) Uani 1 1 d . . . . .
H14 H 0.483690 0.125027 0.140306 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3760(3) 0.3502(3) 0.2244(2) 0.0294(5) Uani 1 1 d . . . . .
H15 H 0.410416 0.310623 0.305389 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1384(3) 0.7609(3) 0.0622(2) 0.0293(5) 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'
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 111.45(17) . . ?
C1 N2 C10 125.02(17) . . ?
C3 N2 C10 122.91(17) . . ?
C1 N8 C7 127.84(18) . . ?
C1 N8 C9 110.76(17) . . ?
C7 N8 C9 121.40(18) . . ?
N2 C1 N8 104.56(17) . . ?
N2 C1 Se1 129.11(16) . . ?
N8 C1 Se1 126.33(15) . . ?
C9 C3 N2 106.98(17) . . ?
C9 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C5 C4 C9 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C9 C4 H4 120.4 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 N8 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
N8 C7 H7 120.4 . . ?
C3 C9 N8 106.23(18) . . ?
C3 C9 C4 135.2(2) . . ?
N8 C9 C4 118.55(19) . . ?
C15 C10 C11 120.8(2) . . ?
C15 C10 N2 117.62(19) . . ?
C11 C10 N2 121.49(19) . . ?
C10 C11 C12 118.6(2) . . ?
C10 C11 C16 121.18(19) . . ?
C12 C11 C16 120.2(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 119.9(2) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
F2 C16 F3 106.26(19) . . ?
F2 C16 F1 106.43(19) . . ?
F3 C16 F1 105.77(18) . . ?
F2 C16 C11 112.45(19) . . ?
F3 C16 C11 113.10(18) . . ?
F1 C16 C11 112.29(18) . . ?
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 1.835(2) . ?
F1 C16 1.341(3) . ?
F2 C16 1.333(3) . ?
F3 C16 1.340(3) . ?
N2 C1 1.361(3) . ?
N2 C3 1.385(3) . ?
N2 C10 1.441(3) . ?
N8 C1 1.363(3) . ?
N8 C7 1.388(3) . ?
N8 C9 1.407(3) . ?
C3 C9 1.357(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.350(3) . ?
C4 C9 1.420(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.434(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.338(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C10 C15 1.377(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.494(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
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 -1.3(2) . . . . ?
C10 N2 C1 N8 -172.42(18) . . . . ?
C3 N2 C1 Se1 178.68(15) . . . . ?
C10 N2 C1 Se1 7.5(3) . . . . ?
C7 N8 C1 N2 -177.98(18) . . . . ?
C9 N8 C1 N2 1.2(2) . . . . ?
C7 N8 C1 Se1 2.1(3) . . . . ?
C9 N8 C1 Se1 -178.73(15) . . . . ?
C1 N2 C3 C9 0.8(2) . . . . ?
C10 N2 C3 C9 172.22(18) . . . . ?
C9 C4 C5 C6 2.0(3) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 N8 -1.1(3) . . . . ?
C1 N8 C7 C6 -178.5(2) . . . . ?
C9 N8 C7 C6 2.4(3) . . . . ?
N2 C3 C9 N8 -0.1(2) . . . . ?
N2 C3 C9 C4 180.0(2) . . . . ?
C1 N8 C9 C3 -0.7(2) . . . . ?
C7 N8 C9 C3 178.52(18) . . . . ?
C1 N8 C9 C4 179.24(18) . . . . ?
C7 N8 C9 C4 -1.5(3) . . . . ?
C5 C4 C9 C3 179.2(2) . . . . ?
C5 C4 C9 N8 -0.7(3) . . . . ?
C1 N2 C10 C15 74.0(3) . . . . ?
C3 N2 C10 C15 -96.2(2) . . . . ?
C1 N2 C10 C11 -108.6(2) . . . . ?
C3 N2 C10 C11 81.2(3) . . . . ?
C15 C10 C11 C12 1.2(3) . . . . ?
N2 C10 C11 C12 -176.08(19) . . . . ?
C15 C10 C11 C16 -177.73(19) . . . . ?
N2 C10 C11 C16 5.0(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C16 C11 C12 C13 178.8(2) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
N2 C10 C15 C14 176.05(19) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C10 C11 C16 F2 177.6(2) . . . . ?
C12 C11 C16 F2 -1.3(3) . . . . ?
C10 C11 C16 F3 -62.0(3) . . . . ?
C12 C11 C16 F3 119.0(2) . . . . ?
C10 C11 C16 F1 57.6(3) . . . . ?
C12 C11 C16 F1 -121.3(2) . . . . ?
