#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157478.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_7157478
loop_
_publ_author_name
'Recchi, Ana Maria S.'
'Rosa, Pedro H. P.'
'Back, Davi F.'
'Zeni, Gilson'
_publ_section_title
;
 Selenium-promoted electrophilic cyclization of arylpropiolamides:
 synthesis of 3-organoselenyl spiro[4,5]trienones.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3544
_journal_page_last               3551
_journal_paper_doi               10.1039/d0ob00609b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C23 H16 F3 N O2 Se'
_chemical_formula_sum            'C23 H16 F3 N O2 Se'
_chemical_formula_weight         474.33
_chemical_melting_point          421
_chemical_name_common            'phenylselanyl azaspiro decatrienedione'
_chemical_name_systematic
'1-methyl-4-phenyl-3-((3-(trifluoromethyl)phenyl)selanyl)-1-azaspiro        [4.5]deca-3,6,9-triene-2,8-dione'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2019-06-14T16:48:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.147(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7568(4)
_cell_length_b                   25.3971(13)
_cell_length_c                   13.5914(8)
_cell_measurement_reflns_used    7325
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.774
_cell_measurement_theta_min      2.843
_cell_volume                     1967.1(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22029
_diffrn_reflns_theta_full        27.16
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_T_max  0.9358
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0441P)²+1.6050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                3415
_reflns_number_total             4358
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0ob00609b2.cif
_cod_data_source_block           test_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '421K' was changed to '421'
-- the value should be numeric and without a unit designator.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157478--7157479.cif.
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7157478
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se11 Se 0.40415(5) 0.568508(12) 0.39990(2) 0.03602(11) Uani 1 1 d . . .
O13 O 0.2095(4) 0.69088(9) 0.38162(15) 0.0478(6) Uani 1 1 d . . .
N7 N 0.3626(4) 0.70788(9) 0.54354(16) 0.0312(5) Uani 1 1 d . . .
F1 F 0.1853(4) 0.61347(10) -0.02172(16) 0.0787(7) Uani 1 1 d . . .
F3 F 0.2396(6) 0.53255(10) 0.01120(16) 0.1014(10) Uani 1 1 d . . .
F2 F 0.4783(6) 0.57481(12) -0.06409(16) 0.0980(9) Uani 1 1 d . . .
O27 O 0.7185(5) 0.72333(14) 0.91881(17) 0.0750(9) Uani 1 1 d . . .
C10 C 0.5679(4) 0.62917(10) 0.57714(17) 0.0249(5) Uani 1 1 d . . .
C12 C 0.7376(5) 0.59120(10) 0.62858(18) 0.0263(6) Uani 1 1 d . . .
C9 C 0.4524(5) 0.62776(10) 0.48488(18) 0.0278(6) Uani 1 1 d . . .
C8 C 0.3248(5) 0.67817(11) 0.46002(19) 0.0308(6) Uani 1 1 d . . .
C5 C 0.5104(4) 0.68150(10) 0.62593(18) 0.0249(5) Uani 1 1 d . . .
C6 C 0.3638(5) 0.67218(11) 0.70756(19) 0.0287(6) Uani 1 1 d . . .
H6 H 0.2234 0.6539 0.6921 0.034 Uiso 1 1 calc R . .
C3 C 0.7931(5) 0.72689(12) 0.7534(2) 0.0346(6) Uani 1 1 d . . .
H3 H 0.9323 0.7455 0.77 0.042 Uiso 1 1 calc R . .
C4 C 0.7274(5) 0.71250(11) 0.6595(2) 0.0298(6) Uani 1 1 d . . .
H4 H 0.8215 0.7223 0.6123 0.036 Uiso 1 1 calc R . .
C20 C 0.3982(5) 0.57990(11) 0.1926(2) 0.0343(6) Uani 1 1 d . . .
H20 H 0.2574 0.5616 0.1895 0.041 Uiso 1 1 calc R . .
C21 C 0.9140(5) 0.57081(11) 0.5787(2) 0.0355(6) Uani 1 1 d . . .
H21 H 0.9168 0.5797 0.5125 0.043 Uiso 1 1 calc R . .
C15 C 0.5205(5) 0.59468(11) 0.28367(19) 0.0314(6) Uani 1 1 d . . .
C14 C 0.2784(5) 0.76096(11) 0.5524(2) 0.0382(7) Uani 1 1 d . . .
H14A H 0.3278 0.7736 0.6186 0.057 Uiso 1 1 calc R . .
H14B H 0.1102 0.7613 0.5389 0.057 Uiso 1 1 calc R . .
H14C H 0.3413 0.7833 0.5056 0.057 Uiso 1 1 calc R . .
C16 C 0.7253(5) 0.62298(12) 0.2881(2) 0.0400(7) Uani 1 1 d . . .
H16 H 0.8054 0.6333 0.3493 0.048 Uiso 1 1 calc R . .
C25 C 0.7378(6) 0.57702(11) 0.7275(2) 0.0384(7) Uani 1 1 d . . .
H25 H 0.6212 0.5898 0.7621 0.046 Uiso 1 1 calc R . .
C1 C 0.4237(5) 0.68853(12) 0.8002(2) 0.0360(7) Uani 1 1 d . . .
H1 H 0.32 0.6838 0.846 0.043 Uiso 1 1 calc R . .
C22 C 1.0838(5) 0.53772(12) 0.6263(3) 0.0434(7) Uani 1 1 d . . .
H22 H 1.1994 0.5242 0.5921 0.052 Uiso 1 1 calc R . .
C19 C 0.4877(6) 0.59259(12) 0.1066(2) 0.0395(7) Uani 1 1 d . . .
C23 C 1.0825(6) 0.52458(12) 0.7247(2) 0.0453(8) Uani 1 1 d . . .
H23 H 1.198 0.5026 0.757 0.054 Uiso 1 1 calc R . .
C2 C 0.6493(5) 0.71390(13) 0.8316(2) 0.0406(7) Uani 1 1 d . . .
C17 C 0.8120(6) 0.63599(13) 0.2016(3) 0.0477(8) Uani 1 1 d . . .
H17 H 0.9502 0.6553 0.2048 0.057 Uiso 1 1 calc R . .
C18 C 0.6948(6) 0.62060(13) 0.1105(2) 0.0475(8) Uani 1 1 d . . .
H18 H 0.7545 0.629 0.0524 0.057 Uiso 1 1 calc R . .
C24 C 0.9092(6) 0.54422(13) 0.7748(2) 0.0452(8) Uani 1 1 d . . .
H24 H 0.908 0.5353 0.8411 0.054 Uiso 1 1 calc R . .
C26 C 0.3506(7) 0.57760(14) 0.0090(2) 0.0548(9) 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 0 '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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.006 '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
C9 Se11 C15 100.87(11) . . ?
C8 N7 C14 125.0(2) . . ?
C8 N7 C5 113.1(2) . . ?
C14 N7 C5 121.8(2) . . ?
C9 C10 C12 129.5(2) . . ?
C9 C10 C5 108.6(2) . . ?
C12 C10 C5 121.8(2) . . ?
C25 C12 C21 118.2(3) . . ?
C25 C12 C10 122.4(2) . . ?
C21 C12 C10 119.3(2) . . ?
C10 C9 C8 110.7(2) . . ?
C10 C9 Se11 127.3(2) . . ?
C8 C9 Se11 121.29(18) . . ?
O13 C8 N7 126.1(3) . . ?
O13 C8 C9 128.1(3) . . ?
N7 C8 C9 105.8(2) . . ?
N7 C5 C4 111.2(2) . . ?
N7 C5 C6 108.0(2) . . ?
C4 C5 C6 113.0(2) . . ?
N7 C5 C10 101.63(19) . . ?
C4 C5 C10 111.4(2) . . ?
C6 C5 C10 111.0(2) . . ?
C1 C6 C5 123.7(2) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C5 123.4(3) . . ?
C19 C20 C15 119.3(3) . . ?
C22 C21 C12 120.9(3) . . ?
C16 C15 C20 120.3(3) . . ?
C16 C15 Se11 122.8(2) . . ?
C20 C15 Se11 116.7(2) . . ?
C15 C16 C17 119.9(3) . . ?
C24 C25 C12 120.6(3) . . ?
C6 C1 C2 121.2(3) . . ?
C23 C22 C21 120.1(3) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 C26 118.6(3) . . ?
C18 C19 C26 120.7(3) . . ?
C22 C23 C24 119.7(3) . . ?
O27 C2 C1 121.7(3) . . ?
O27 C2 C3 121.2(3) . . ?
C1 C2 C3 117.1(2) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C19 119.4(3) . . ?
C25 C24 C23 120.6(3) . . ?
F3 C26 F2 107.2(3) . . ?
F3 C26 F1 105.8(3) . . ?
F2 C26 F1 104.4(3) . . ?
F3 C26 C19 113.6(3) . . ?
F2 C26 C19 113.7(3) . . ?
F1 C26 C19 111.5(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
Se11 C9 1.893(3) . ?
Se11 C15 1.920(3) . ?
O13 C8 1.217(3) . ?
N7 C8 1.355(3) . ?
N7 C14 1.443(4) . ?
N7 C5 1.469(3) . ?
F1 C26 1.341(4) . ?
F3 C26 1.313(4) . ?
F2 C26 1.319(4) . ?
O27 C2 1.219(3) . ?
C10 C9 1.334(3) . ?
C10 C12 1.477(4) . ?
C10 C5 1.542(4) . ?
C12 C25 1.392(4) . ?
C12 C21 1.398(4) . ?
C9 C8 1.491(4) . ?
C5 C4 1.492(4) . ?
C5 C6 1.505(4) . ?
C6 C1 1.324(4) . ?
C3 C4 1.329(4) . ?
C3 C2 1.475(4) . ?
C20 C19 1.381(4) . ?
C20 C15 1.386(4) . ?
C21 C22 1.379(4) . ?
C15 C16 1.375(4) . ?
C16 C17 1.381(4) . ?
C25 C24 1.379(4) . ?
C1 C2 1.459(4) . ?
C22 C23 1.379(5) . ?
C19 C18 1.382(5) . ?
C19 C26 1.493(4) . ?
C23 C24 1.379(5) . ?
C17 C18 1.380(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353387
