#------------------------------------------------------------------------------
#$Date: 2025-12-12 02:54:57 +0100 (Fri 12 de Dec de 2025) $
#$Revision: 304186 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/42/7064213.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_7064213
loop_
_publ_author_name
'MacDougall, Phillip'
'Zeng, Mich Wenshi'
'Wang, Jin'
'Ho, Peter Cheng-Wei'
'Vargas-Baca, Ignacio'
_publ_section_title
;
 From Fluorine Chemistry to Noncovalent Interactions: Celebrating Prof.
 Giuseppe Resnati
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03688G
_journal_year                    2026
_chemical_formula_moiety         'C7 H5 Cl4 N O Se'
_chemical_formula_sum            'C7 H5 Cl4 N O Se'
_chemical_formula_weight         339.88
_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_date             2023-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9518(5)
_cell_length_b                   16.4650(9)
_cell_length_c                   8.8983(5)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.654
_cell_measurement_theta_min      2.474
_cell_volume                     1157.45(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            38774
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_min         2.474
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.132
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0579 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8646.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.870
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0229
_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)+(0.0278P)²+0.7884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0550
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2681
_reflns_number_total             3027
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj03688g2.cif
_cod_data_source_block           pm2_7a_0m_a
_cod_database_code               7064213
_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_max   0.683
_shelx_estimated_absorpt_t_min   0.523
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C5(H5)
1.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Se1 Se 0.32819(2) 0.45380(2) 0.30814(2) 0.01411(6) Uani 1 1 d . . . . .
Cl1 Cl 0.65091(6) 0.44590(3) 0.34387(6) 0.02116(10) Uani 1 1 d . . . . .
Cl2 Cl 0.04152(6) 0.45315(3) 0.29465(6) 0.02219(10) Uani 1 1 d . . . . .
Cl3 Cl 0.32888(6) 0.53192(3) 0.10490(5) 0.02385(11) Uani 1 1 d . . . . .
Cl4 Cl 0.37318(9) 0.20601(3) 0.58097(6) 0.03462(14) Uani 1 1 d . . . . .
O1 O 0.3201(2) 0.37177(8) 0.66111(15) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.319084 0.421738 0.680057 0.037 Uiso 1 1 calc R U . . .
N1 N 0.3301(2) 0.36044(9) 0.50954(17) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.3600(2) 0.27931(11) 0.3000(2) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.3420(2) 0.34854(11) 0.2071(2) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.3527(2) 0.28866(11) 0.4632(2) 0.0188(4) Uani 1 1 d . . . . .
C4 C 0.3430(3) 0.34299(12) 0.0520(2) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.328602 0.390088 -0.009809 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3858(3) 0.20409(12) 0.2336(2) 0.0224(4) Uani 1 1 d . . . . .
H7 H 0.401142 0.156851 0.294932 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3893(3) 0.19809(13) 0.0779(2) 0.0273(4) Uani 1 1 d . . . . .
H6 H 0.407746 0.146911 0.033328 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3657(3) 0.26687(13) -0.0120(2) 0.0296(5) Uani 1 1 d . . . . .
H5 H 0.364950 0.262139 -0.118468 0.035 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'
Cl Cl 0.1484 0.1585 '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'
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'
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
Cl2 Se1 Cl1 174.805(18) . . ?
Cl2 Se1 N1 87.51(4) . . ?
Cl3 Se1 Cl1 92.024(18) . . ?
Cl3 Se1 Cl2 93.166(19) . . ?
Cl3 Se1 N1 174.74(4) . . ?
N1 Se1 Cl1 87.30(4) . . ?
C1 Se1 Cl1 84.50(5) . . ?
C1 Se1 Cl2 94.58(5) . . ?
C1 Se1 Cl3 97.65(5) . . ?
C1 Se1 N1 77.10(6) . . ?
N1 O1 H1 109.5 . . ?
O1 N1 Se1 131.41(11) . . ?
C3 N1 Se1 110.38(12) . . ?
C3 N1 O1 118.11(15) . . ?
C1 C2 C3 118.94(16) . . ?
C7 C2 C1 118.68(16) . . ?
C7 C2 C3 122.37(17) . . ?
C2 C1 Se1 117.01(13) . . ?
C4 C1 Se1 121.50(14) . . ?
C4 C1 C2 121.40(17) . . ?
N1 C3 Cl4 123.16(15) . . ?
N1 C3 C2 116.18(16) . . ?
C2 C3 Cl4 120.66(14) . . ?
C1 C4 H4 120.6 . . ?
C1 C4 C5 118.78(18) . . ?
C5 C4 H4 120.6 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.27(18) . . ?
C6 C7 H7 119.9 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 119.97(19) . . ?
C5 C6 H6 120.0 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.85(18) . . ?
C6 C5 H5 119.6 . . ?
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 Cl1 2.5529(5) . ?
Se1 Cl2 2.2691(5) . ?
Se1 Cl3 2.2198(5) . ?
Se1 N1 2.3598(15) . ?
Se1 C1 1.9612(18) . ?
Cl4 C3 1.7139(18) . ?
O1 H1 0.8400 . ?
O1 N1 1.3727(19) . ?
N1 C3 1.271(2) . ?
C2 C1 1.406(3) . ?
C2 C3 1.468(2) . ?
C2 C7 1.398(3) . ?
C1 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(3) . ?
C5 H5 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
Se1 N1 C3 Cl4 176.13(11) . . . . ?
Se1 N1 C3 C2 -4.1(2) . . . . ?
Se1 C1 C4 C5 175.31(16) . . . . ?
O1 N1 C3 Cl4 -0.6(3) . . . . ?
O1 N1 C3 C2 179.14(15) . . . . ?
C2 C1 C4 C5 -1.2(3) . . . . ?
C2 C7 C6 C5 -0.5(3) . . . . ?
C1 C2 C3 Cl4 179.77(14) . . . . ?
C1 C2 C3 N1 0.0(3) . . . . ?
C1 C2 C7 C6 -1.6(3) . . . . ?
C1 C4 C5 C6 -0.9(3) . . . . ?
C3 C2 C1 Se1 5.2(2) . . . . ?
C3 C2 C1 C4 -178.14(18) . . . . ?
C3 C2 C7 C6 179.03(19) . . . . ?
C7 C2 C1 Se1 -174.20(14) . . . . ?
C7 C2 C1 C4 2.5(3) . . . . ?
C7 C2 C3 Cl4 -0.9(3) . . . . ?
C7 C2 C3 N1 179.36(18) . . . . ?
C7 C6 C5 C4 1.8(3) . . . . ?
