#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/83/2018312.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_2018312
loop_
_publ_author_name
'Cordes, David B.'
'Hua, Guoxiong'
'Slawin, Alexandra M. Z.'
'Woollins, J. Derek'
_publ_section_title
;
 2,5-Diaryl-1,3,4-selenadiazoles prepared from Woollins' reagent
;
_journal_coeditor_code           BM3112
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o509
_journal_page_last               o514
_journal_paper_doi               10.1107/S0108270111049900
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H10 N2 Se'
_chemical_formula_moiety         'C14 H10 N2 Se'
_chemical_formula_sum            'C14 H10 N2 Se'
_chemical_formula_weight         285.20
_chemical_name_systematic
;
2,5-diphenyl-1,3,4-selenadiazole
;
_space_group_IT_number           14
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.860(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.036(4)
_cell_length_b                   5.4650(14)
_cell_length_c                   16.274(5)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      1.6
_cell_volume                     1134.6(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2010)'
_computing_data_collection       'CrystalClear (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear  (Rigaku, 2010)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and OLEX (Dolomanov et al.,
2003)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_device_type  'Rigaku Mercury CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7425
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    3.285
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.693
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0205P)²+1.2418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                2081
_reflns_number_total             2413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3112.cif
_cod_data_source_block           Ia
_cod_original_cell_volume        1134.6(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018312
_cod_database_fobs_code          2018312
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_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Se Se1 0.91133(2) 0.13109(5) 0.293061(16) 0.02068(14) Uani d . 1 1
N N4 0.82019(19) -0.2835(4) 0.33044(14) 0.0249(6) Uani d . 1 1
N N3 0.91878(19) -0.2871(4) 0.38062(14) 0.0234(5) Uani d . 1 1
C C5 0.7995(2) -0.0927(5) 0.28210(17) 0.0202(6) Uani d . 1 1
C C21 0.6975(2) -0.0548(5) 0.22543(16) 0.0205(6) Uani d . 1 1
C C26 0.6179(2) -0.2262(5) 0.22610(18) 0.0240(6) Uani d . 1 1
H H26 0.6304 -0.3625 0.2630 0.029 Uiso calc R 1 1
C C25 0.5210(2) -0.1981(6) 0.17321(18) 0.0278(7) Uani d . 1 1
H H25 0.4672 -0.3146 0.1744 0.033 Uiso calc R 1 1
C C24 0.5015(2) -0.0003(5) 0.11811(18) 0.0268(7) Uani d . 1 1
H H24 0.4353 0.0173 0.0811 0.032 Uiso calc R 1 1
C C23 0.5801(2) 0.1705(5) 0.11809(18) 0.0249(7) Uani d . 1 1
H H23 0.5673 0.3067 0.0811 0.030 Uiso calc R 1 1
C C22 0.6772(2) 0.1450(5) 0.17125(18) 0.0214(6) Uani d . 1 1
H H22 0.7301 0.2641 0.1708 0.026 Uiso calc R 1 1
C C2 0.9772(2) -0.0997(5) 0.37245(16) 0.0190(6) Uani d . 1 1
C C11 1.0842(2) -0.0686(5) 0.42239(16) 0.0189(6) Uani d . 1 1
C C16 1.1249(2) -0.2410(5) 0.48439(17) 0.0219(6) Uani d . 1 1
H H16 1.0839 -0.3790 0.4929 0.026 Uiso calc R 1 1
C C15 1.2240(2) -0.2115(5) 0.53317(18) 0.0256(7) Uani d . 1 1
H H15 1.2505 -0.3285 0.5754 0.031 Uiso calc R 1 1
C C14 1.2853(2) -0.0119(5) 0.52103(17) 0.0246(6) Uani d . 1 1
H H14 1.3536 0.0075 0.5546 0.029 Uiso calc R 1 1
C C13 1.2458(2) 0.1584(5) 0.45956(18) 0.0247(7) Uani d . 1 1
H H13 1.2873 0.2953 0.4510 0.030 Uiso calc R 1 1
C C12 1.1461(2) 0.1305(5) 0.41050(17) 0.0212(7) Uani d . 1 1
H H12 1.1199 0.2481 0.3685 0.025 Uiso calc R 1 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'
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
C2 Se1 C5 82.25(12)
C5 N4 N3 115.1(2)
C2 N3 N4 115.1(2)
N4 C5 C21 122.8(3)
N4 C5 Se1 113.8(2)
C21 C5 Se1 123.5(2)
C22 C21 C26 119.0(3)
C22 C21 C5 122.5(3)
C26 C21 C5 118.6(3)
C25 C26 C21 120.3(3)
C25 C26 H26 119.9
C21 C26 H26 119.9
C26 C25 C24 120.6(3)
C26 C25 H25 119.7
C24 C25 H25 119.7
C23 C24 C25 119.0(3)
C23 C24 H24 120.5
C25 C24 H24 120.5
C22 C23 C24 120.9(3)
C22 C23 H23 119.6
C24 C23 H23 119.6
C23 C22 C21 120.2(3)
C23 C22 H22 119.9
C21 C22 H22 119.9
N3 C2 C11 122.9(2)
N3 C2 Se1 113.8(2)
C11 C2 Se1 123.3(2)
C12 C11 C16 118.8(3)
C12 C11 C2 121.6(2)
C16 C11 C2 119.6(3)
C15 C16 C11 120.4(3)
C15 C16 H16 119.8
C11 C16 H16 119.8
C16 C15 C14 120.5(3)
C16 C15 H15 119.7
C14 C15 H15 119.7
C13 C14 C15 119.4(3)
C13 C14 H14 120.3
C15 C14 H14 120.3
C14 C13 C12 120.4(3)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C12 C11 120.5(3)
C13 C12 H12 119.7
C11 C12 H12 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C2 1.882(3)
Se1 C5 1.883(3)
N4 C5 1.301(3)
N4 N3 1.374(3)
N3 C2 1.300(3)
C5 C21 1.469(4)
C21 C22 1.394(4)
C21 C26 1.400(4)
C26 C25 1.383(4)
C26 H26 0.9500
C25 C24 1.394(4)
C25 H25 0.9500
C24 C23 1.386(4)
C24 H24 0.9500
C23 C22 1.385(4)
C23 H23 0.9500
C22 H22 0.9500
C2 C11 1.473(4)
C11 C12 1.391(4)
C11 C16 1.403(4)
C16 C15 1.380(4)
C16 H16 0.9500
C15 C14 1.390(4)
C15 H15 0.9500
C14 C13 1.386(4)
C14 H14 0.9500
C13 C12 1.387(4)
C13 H13 0.9500
C12 H12 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
C5 N4 N3 C2 -0.1(3)
N3 N4 C5 C21 -178.8(2)
N3 N4 C5 Se1 0.3(3)
C2 Se1 C5 N4 -0.2(2)
C2 Se1 C5 C21 178.8(2)
N4 C5 C21 C22 -177.3(3)
Se1 C5 C21 C22 3.8(4)
N4 C5 C21 C26 2.7(4)
Se1 C5 C21 C26 -176.2(2)
C22 C21 C26 C25 0.5(4)
C5 C21 C26 C25 -179.5(3)
C21 C26 C25 C24 0.5(4)
C26 C25 C24 C23 -1.1(4)
C25 C24 C23 C22 0.6(4)
C24 C23 C22 C21 0.5(4)
C26 C21 C22 C23 -1.0(4)
C5 C21 C22 C23 179.0(3)
N4 N3 C2 C11 178.5(2)
N4 N3 C2 Se1 -0.1(3)
C5 Se1 C2 N3 0.2(2)
C5 Se1 C2 C11 -178.4(2)
N3 C2 C11 C12 178.1(2)
Se1 C2 C11 C12 -3.5(4)
N3 C2 C11 C16 -2.9(4)
Se1 C2 C11 C16 175.58(19)
C12 C11 C16 C15 0.7(4)
C2 C11 C16 C15 -178.4(2)
C11 C16 C15 C14 -0.6(4)
C16 C15 C14 C13 0.3(4)
C15 C14 C13 C12 0.0(4)
C14 C13 C12 C11 0.1(4)
C16 C11 C12 C13 -0.5(4)
C2 C11 C12 C13 178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10587101
