#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546627.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1546627
loop_
_publ_author_name
'Guo, Zhiqiang'
'Wang, Yakong'
'Xu, Ying'
'Wei, Xuehong'
_publ_section_title
;
 2,2'-(Diselane-1,2-diyl)bis(N,N-dimethylnicotinamide)
;
_journal_coeditor_code           HB4154
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x170882
_journal_paper_doi               10.1107/S2414314617008823
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C16 H18 N4 O2 Se2'
_chemical_formula_moiety         'C16 H18 N4 O2 Se2'
_chemical_formula_sum            'C16 H18 N4 O2 Se2'
_chemical_formula_weight         456.26
_chemical_name_systematic
;
2,2'-(Diselane-1,2-diyl)bis(N,N-dimethylnicotinamide)
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.375(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.167(2)
_cell_length_b                   8.726(3)
_cell_length_c                   13.947(4)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.75
_cell_volume                     866.8(5)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3376
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.758
_exptl_absorpt_coefficient_mu    4.282
_exptl_absorpt_correction_T_max  0.4813
_exptl_absorpt_correction_T_min  0.2233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.434
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0301
_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)+(0.0337P)²+0.0053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                1300
_reflns_number_total             1524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4154sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        866.8(4)
_cod_database_code               1546627
_cod_database_fobs_code          1546627
_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   0.223
_shelx_estimated_absorpt_t_max   0.481
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Se Se 0.52041(4) 0.56001(3) 0.92626(2) 0.04189(16) Uani d 1
N N1 0.1797(4) 0.6437(3) 0.99097(18) 0.0386(6) Uani d 1
N N2 0.4942(4) 0.9794(3) 0.79999(18) 0.0403(6) Uani d 1
O O 0.4595(4) 0.7382(3) 0.74625(17) 0.0541(7) Uani d 1
C C1 0.2981(4) 0.6827(3) 0.9288(2) 0.0313(6) Uani d 1
C C2 0.2725(4) 0.8092(3) 0.8665(2) 0.0341(7) Uani d 1
C C3 0.1072(5) 0.8902(4) 0.8669(2) 0.0423(8) Uani d 1
H H3 0.0823 0.9734 0.8257 0.051 Uiso calc 1
C C4 -0.0211(5) 0.8469(4) 0.9289(2) 0.0450(8) Uani d 1
H H4 -0.1344 0.8987 0.9289 0.054 Uiso calc 1
C C5 0.0220(4) 0.7258(4) 0.9903(2) 0.0433(8) Uani d 1
H H5 -0.0627 0.6996 1.0335 0.052 Uiso calc 1
C C6 0.4161(4) 0.8408(3) 0.7996(2) 0.0349(7) Uani d 1
C C7 0.4669(5) 1.1022(4) 0.8681(3) 0.0546(9) Uani d 1
H H7A 0.3853 1.1787 0.8368 0.082 Uiso calc 1
H H7B 0.5860 1.1477 0.8902 0.082 Uiso calc 1
H H7C 0.4116 1.0610 0.9222 0.082 Uiso calc 1
C C8 0.6280(5) 1.0111(4) 0.7320(3) 0.0535(9) Uani d 1
H H8A 0.7067 0.9231 0.7268 0.080 Uiso calc 1
H H8B 0.7042 1.0973 0.7541 0.080 Uiso calc 1
H H8C 0.5619 1.0339 0.6699 0.080 Uiso calc 1
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'
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_site_symmetry_3
_geom_angle
C1 Se Se 3_667 92.77(8)
C1 N1 C5 . 117.4(3)
C6 N2 C8 . 118.6(3)
C6 N2 C7 . 125.6(3)
C8 N2 C7 . 115.6(3)
N1 C1 C2 . 124.0(3)
N1 C1 Se . 117.5(2)
C2 C1 Se . 118.6(2)
C3 C2 C1 . 117.0(3)
C3 C2 C6 . 124.1(3)
C1 C2 C6 . 118.8(3)
C2 C3 C4 . 119.5(3)
C2 C3 H3 . 120.2
C4 C3 H3 . 120.2
C5 C4 C3 . 118.8(3)
C5 C4 H4 . 120.6
C3 C4 H4 . 120.6
N1 C5 C4 . 123.2(3)
N1 C5 H5 . 118.4
C4 C5 H5 . 118.4
O C6 N2 . 122.0(3)
O C6 C2 . 118.9(3)
N2 C6 C2 . 119.0(3)
N2 C7 H7A . 109.5
N2 C7 H7B . 109.5
H7A C7 H7B . 109.5
N2 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N2 C8 H8A . 109.5
N2 C8 H8B . 109.5
H8A C8 H8B . 109.5
N2 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Se C1 . 1.923(3)
Se Se 3_667 2.3551(8)
N1 C1 . 1.324(4)
N1 C5 . 1.338(4)
N2 C6 . 1.332(4)
N2 C8 . 1.449(4)
N2 C7 . 1.460(4)
O C6 . 1.226(3)
C1 C2 . 1.403(4)
C2 C3 . 1.381(4)
C2 C6 . 1.490(4)
C3 C4 . 1.383(4)
C3 H3 . 0.9300
C4 C5 . 1.373(4)
C4 H4 . 0.9300
C5 H5 . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 O 2_556 0.93 2.52 3.431(4) 165
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
C5 N1 C1 C2 3.6(4)
C5 N1 C1 Se -177.7(2)
N1 C1 C2 C3 -4.4(4)
Se C1 C2 C3 176.9(2)
N1 C1 C2 C6 -179.9(3)
Se C1 C2 C6 1.4(4)
C1 C2 C3 C4 1.6(4)
C6 C2 C3 C4 176.9(3)
C2 C3 C4 C5 1.5(5)
C1 N1 C5 C4 -0.1(5)
C3 C4 C5 N1 -2.4(5)
C8 N2 C6 O 2.9(5)
C7 N2 C6 O -172.7(3)
C8 N2 C6 C2 -177.5(3)
C7 N2 C6 C2 6.9(5)
C3 C2 C6 O -121.7(3)
C1 C2 C6 O 53.5(4)
C3 C2 C6 N2 58.7(4)
C1 C2 C6 N2 -126.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139050476
