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#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/83/2018313.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_2018313
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           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.885(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.763(10)
_cell_length_b                   5.796(2)
_cell_length_c                   7.213(3)
_cell_measurement_reflns_used    1743
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      1.6
_cell_volume                     1086.2(7)
_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 0.987
_diffrn_measured_fraction_theta_max 0.831
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3541
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    3.431
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.921
_refine_diff_density_min         -1.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0655
_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)+(0.0732P)²+8.2817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1665
_reflns_number_gt                1014
_reflns_number_total             1149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3112.cif
_cod_data_source_block           Ib
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018313
_cod_database_fobs_code          2018313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Se Se1 0.0000 0.10447(14) 0.7500 0.0302(4) Uani d S 1 2
N N3 0.02554(18) 0.5566(9) 0.7995(7) 0.0261(11) Uani d . 1 1
C C2 0.0449(2) 0.3517(10) 0.8391(8) 0.0255(12) Uani d . 1 1
C C11 0.0984(2) 0.3062(10) 0.9412(8) 0.0251(12) Uani d . 1 1
C C16 0.1360(2) 0.4744(11) 0.9475(8) 0.0281(13) Uani d . 1 1
H H16 0.1266 0.6183 0.8861 0.034 Uiso calc R 1 1
C C15 0.1858(2) 0.4374(11) 1.0392(9) 0.0291(13) Uani d . 1 1
H H15 0.2109 0.5536 1.0411 0.035 Uiso calc R 1 1
C C14 0.1994(2) 0.2331(12) 1.1283(9) 0.0352(15) Uani d . 1 1
H H14 0.2343 0.2080 1.1926 0.042 Uiso calc R 1 1
C C13 0.1646(2) 0.0640(11) 1.1282(9) 0.0303(13) Uani d . 1 1
H H13 0.1751 -0.0770 1.1931 0.036 Uiso calc R 1 1
C C12 0.1135(2) 0.0974(9) 1.0329(9) 0.0269(13) Uani d . 1 1
H H12 0.0890 -0.0217 1.0302 0.032 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_site_symmetry_3
_geom_angle
C2 Se1 C2 2_556 80.7(4)
C2 N3 N3 2_556 113.9(3)
N3 C2 C11 . 124.2(5)
N3 C2 Se1 . 115.7(4)
C11 C2 Se1 . 120.0(4)
C12 C11 C16 . 117.9(5)
C12 C11 C2 . 122.1(5)
C16 C11 C2 . 120.0(5)
C15 C16 C11 . 121.5(6)
C15 C16 H16 . 119.3
C11 C16 H16 . 119.3
C16 C15 C14 . 119.4(6)
C16 C15 H15 . 120.3
C14 C15 H15 . 120.3
C13 C14 C15 . 121.8(6)
C13 C14 H14 . 119.1
C15 C14 H14 . 119.1
C14 C13 C12 . 119.7(6)
C14 C13 H13 . 120.2
C12 C13 H13 . 120.2
C13 C12 C11 . 119.7(6)
C13 C12 H12 . 120.1
C11 C12 H12 . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Se1 C2 . 1.881(6)
Se1 C2 2_556 1.881(6)
N3 C2 . 1.300(7)
N3 N3 2_556 1.382(9)
C2 C11 . 1.470(8)
C11 C12 . 1.392(8)
C11 C16 . 1.394(8)
C16 C15 . 1.354(8)
C16 H16 . 0.9500
C15 C14 . 1.355(9)
C15 H15 . 0.9500
C14 C13 . 1.352(9)
C14 H14 . 0.9500
C13 C12 . 1.389(9)
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_site_symmetry_1
_geom_torsion
N3 N3 C2 C11 2_556 179.3(5)
N3 N3 C2 Se1 2_556 1.1(8)
C2 Se1 C2 N3 2_556 -0.4(3)
C2 Se1 C2 C11 2_556 -178.7(6)
N3 C2 C11 C12 . 159.3(6)
Se1 C2 C11 C12 . -22.6(7)
N3 C2 C11 C16 . -21.1(9)
Se1 C2 C11 C16 . 157.0(5)
C12 C11 C16 C15 . 0.1(9)
C2 C11 C16 C15 . -179.5(5)
C11 C16 C15 C14 . -0.5(9)
C16 C15 C14 C13 . 0.1(10)
C15 C14 C13 C12 . 0.8(10)
C14 C13 C12 C11 . -1.2(9)
C16 C11 C12 C13 . 0.7(8)
C2 C11 C12 C13 . -179.7(5)
