##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2017-06-11
_journal_date_accepted     2017-06-14
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      6
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314617008823
_journal_coeditor_code     HB4154
_publ_contact_author_name     'Zhiqiang Guo'
_publ_contact_author_address
;
Scientific Instrument Center, Shanxi University, Taiyuan 030006,
People's Republic of China
;
_publ_contact_author_email     gzq@sxu.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
2,2'-(Diselane-1,2-diyl)bis(N,N-dimethylnicotinamide)
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Guo, Zhiqiang' .
;
Scientific Instrument Center, Shanxi University, Taiyuan 030006,
People's Republic of China
;
    'Wang, Yakong' .
;
School of Chemistry and Chemical Engineering, Shanxi University,
Taiyuan 030006, People's Republic of China
;
    'Xu, Ying' .
;
School of Chemistry and Chemical Engineering, Shanxi University,
Taiyuan 030006, People's Republic of China
;
    'Wei, Xuehong' .
;
Scientific Instrument Center, Shanxi University, Taiyuan 030006,
People's Republic of China
;
_publ_section_synopsis
;
The title compound is centrosymmetric and the C---Se---Se bond angle is
92.77(8)°.
;
_chemical_name_systematic
;
2,2'-(Diselane-1,2-diyl)bis(N,N-dimethylnicotinamide)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H18 N4 O2 Se2'
_chemical_formula_sum     'C16 H18 N4 O2 Se2'
_chemical_formula_iupac     'C16 H18 N4 O2 Se2'
_chemical_formula_weight     456.26
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     7.167(2)
_cell_length_b     8.726(3)
_cell_length_c     13.947(4)
_cell_angle_alpha     90
_cell_angle_beta     96.375(4)
_cell_angle_gamma     90
_cell_volume     866.8(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2532
_cell_measurement_theta_min     2.75
_cell_measurement_theta_max     27.46
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.748
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     452
_exptl_absorpt_coefficient_mu     4.282
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_shelx_estimated_absorpt_T_min     0.223
_shelx_estimated_absorpt_T_max     0.481
_exptl_absorpt_correction_T_min     0.2233
_exptl_absorpt_correction_T_max     0.4813
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3376
_diffrn_reflns_av_R_equivalents     0.0349
_diffrn_reflns_theta_min     2.758
_diffrn_reflns_theta_max     24.996
_diffrn_reflns_theta_full     24.996
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
All H atoms were positioned geometrically(C---H = 0.93--0.96 Å),
and refined as riding with Uiso(H) = 1.2Ueq of the adjacent
carbon atom (1.5Ueq for methyl H atoms).
;
_reflns_number_total     1524
_reflns_number_gt     1300
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0358
_refine_ls_R_factor_gt     0.0301
_refine_ls_wR_factor_gt     0.0742
_refine_ls_wR_factor_ref     0.0769
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     1524
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0337P)²+0.0053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.643
_refine_diff_density_min     -0.434
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    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_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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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_
    _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
