#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:08:21 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 299118 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/37/1573716.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_1573716
loop_
_publ_author_name
'Telo, João P'
'Veiros, Luis F.'
'André, Vânia'
'da Silva, João Ferreira'
'Justino, Gonçalo C'
'Antunes, Alexandra M. M.'
_publ_section_title
;
 Monoterpenoid selenophenes derived from (-)-carvone with GPx-like
 activity.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2153
_journal_page_last               2161
_journal_paper_doi               10.1039/d4ob01942c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C10 H11 Br O Se'
_chemical_formula_weight         306.05
_chemical_name_common
6-bromo-3,6-dimethyl-5,6-dihydrobenzo[b]selenophen-7(4H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-10-30 deposited with the CCDC.	2025-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.80(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.767(3)
_cell_length_b                   10.906(4)
_cell_length_c                   12.122(4)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      3.10
_cell_volume                     1026.7(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6465
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         3.095
_exptl_absorpt_coefficient_mu    7.506
_exptl_absorpt_correction_T_max  0.399
_exptl_absorpt_correction_T_min  0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0376
_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)+(0.0417P)²+1.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1496
_reflns_number_total             1949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01942c3.cif
_cod_data_source_block           compound2
_cod_depositor_comments
'Adding full bibliography for 1573716--1573718.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1573716
_shelx_shelxl_version_number     2014/7
_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   0.315
_shelx_estimated_absorpt_t_max   0.399
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
Br1 Br 0.08521(6) 0.48096(5) 0.73414(4) 0.04058(18) Uani 1 1 d . . . . .
Se1 Se 0.65701(7) 0.28544(5) 0.81219(4) 0.04273(18) Uani 1 1 d . . . . .
O1 O 0.3960(5) 0.3087(3) 0.6119(3) 0.0478(10) Uani 1 1 d . . . . .
C2 C 0.7455(6) 0.3963(5) 0.9133(4) 0.0413(13) Uani 1 1 d . . . . .
H2 H 0.8297 0.3760 0.9655 0.050 Uiso 1 1 calc R U . . .
C3 C 0.6763(6) 0.5099(5) 0.9042(4) 0.0336(11) Uani 1 1 d . . . . .
C4 C 0.4446(6) 0.6314(4) 0.7958(4) 0.0326(11) Uani 1 1 d . . . . .
H4A H 0.5166 0.7032 0.8063 0.039 Uiso 1 1 calc R U . . .
H4B H 0.3504 0.6364 0.8473 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3726(6) 0.6308(4) 0.6787(4) 0.0340(11) Uani 1 1 d . . . . .
H5A H 0.2871 0.6953 0.6721 0.041 Uiso 1 1 calc R U . . .
H5B H 0.4651 0.6504 0.6287 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2912(6) 0.5114(4) 0.6422(4) 0.0311(11) Uani 1 1 d . . . . .
C7 C 0.4040(6) 0.4002(5) 0.6678(4) 0.0319(11) Uani 1 1 d . . . . .
C7A C 0.5212(6) 0.4145(4) 0.7609(4) 0.0295(10) Uani 1 1 d . . . . .
C3A C 0.5479(6) 0.5191(4) 0.8197(3) 0.0279(10) Uani 1 1 d . . . . .
C8 C 0.7291(7) 0.6158(5) 0.9753(4) 0.0467(14) Uani 1 1 d . . . . .
H8A H 0.6634 0.6870 0.9545 0.070 Uiso 1 1 calc R U . . .
H8B H 0.7083 0.5964 1.0512 0.070 Uiso 1 1 calc R U . . .
H8C H 0.8494 0.6321 0.9657 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2333(6) 0.5133(5) 0.5183(4) 0.0380(12) Uani 1 1 d . . . . .
H9A H 0.1826 0.4357 0.4991 0.057 Uiso 1 1 calc R U . . .
H9B H 0.1502 0.5774 0.5068 0.057 Uiso 1 1 calc R U . . .
H9C H 0.3314 0.5279 0.4729 0.057 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'
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'
Br Br -0.2901 2.4595 '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
C2 Se1 C7A 86.0(2) . . ?
C3 C2 Se1 113.7(4) . . ?
C3 C2 H2 123.2 . . ?
Se1 C2 H2 123.2 . . ?
C2 C3 C3A 113.3(4) . . ?
C2 C3 C8 123.7(5) . . ?
C3A C3 C8 123.0(5) . . ?
C3A C4 C5 111.6(4) . . ?
C3A C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3A C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 115.2(4) . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 C7 112.8(4) . . ?
C5 C6 C9 112.6(4) . . ?
C7 C6 C9 111.3(4) . . ?
C5 C6 Br1 108.4(3) . . ?
C7 C6 Br1 102.5(3) . . ?
C9 C6 Br1 108.5(3) . . ?
O1 C7 C7A 123.6(5) . . ?
O1 C7 C6 121.1(4) . . ?
C7A C7 C6 115.2(4) . . ?
C3A C7A C7 126.1(4) . . ?
C3A C7A Se1 112.2(3) . . ?
C7 C7A Se1 121.8(3) . . ?
C7A C3A C3 114.8(4) . . ?
C7A C3A C4 120.6(4) . . ?
C3 C3A C4 124.6(4) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Br1 C6 1.991(4) . ?
Se1 C2 1.847(5) . ?
Se1 C7A 1.860(5) . ?
O1 C7 1.208(6) . ?
C2 C3 1.355(7) . ?
C2 H2 0.9300 . ?
C3 C3A 1.423(6) . ?
C3 C8 1.494(7) . ?
C4 C3A 1.490(6) . ?
C4 C5 1.518(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.512(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.526(7) . ?
C6 C9 1.561(6) . ?
C7 C7A 1.447(6) . ?
C7A C3A 1.360(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
