#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/83/2018310.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_2018310
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 H9 Cl N2 Se'
_chemical_formula_moiety         'C14 H9 Cl N2 Se'
_chemical_formula_sum            'C14 H9 Cl N2 Se'
_chemical_formula_weight         319.64
_chemical_name_systematic
;
2-(4-chlorophenyl)-5-phenyl-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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.528(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.382(5)
_cell_length_b                   5.5247(18)
_cell_length_c                   16.524(5)
_cell_measurement_reflns_used    4092
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1217.8(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 OLEX2 (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 0.826
_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  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7679
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    3.282
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         4.874
_refine_diff_density_min         -1.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0786
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1375P)²+2.8891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2124
_refine_ls_wR_factor_ref         0.2257
_reflns_number_gt                2050
_reflns_number_total             2513
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3112.cif
_cod_data_source_block           III
_cod_original_cell_volume        1217.9(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018310
_cod_database_fobs_code          2018310
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 0.58869(4) 0.11522(10) 0.70232(4) 0.0261(3) Uani d . 1 1
Cl Cl1 0.12692(11) 0.0260(3) 0.45025(10) 0.0373(5) Uani d . 1 1
N N3 0.5849(4) -0.2964(10) 0.6164(3) 0.0257(11) Uani d . 1 1
N N4 0.6764(4) -0.2978(10) 0.6608(3) 0.0309(12) Uani d . 1 1
C C2 0.5288(5) -0.1089(10) 0.6283(4) 0.0260(14) Uani d . 1 1
C C5 0.6941(5) -0.1088(10) 0.7076(4) 0.0242(13) Uani d . 1 1
C C11 0.4298(4) -0.0772(11) 0.5848(3) 0.0214(12) Uani d . 1 1
C C12 0.3720(5) 0.1270(11) 0.5985(4) 0.0284(15) Uani d . 1 1
H H12 0.3969 0.2451 0.6368 0.034 Uiso calc R 1 1
C C13 0.2787(5) 0.1596(12) 0.5569(4) 0.0278(14) Uani d . 1 1
H H13 0.2396 0.2994 0.5657 0.033 Uiso calc R 1 1
C C14 0.2441(4) -0.0182(12) 0.5021(4) 0.0307(14) Uani d . 1 1
C C15 0.2990(4) -0.2191(12) 0.4869(4) 0.0272(13) Uani d . 1 1
H H15 0.2745 -0.3350 0.4477 0.033 Uiso calc R 1 1
C C16 0.3917(5) -0.2500(11) 0.5300(4) 0.0288(13) Uani d . 1 1
H H16 0.4296 -0.3921 0.5216 0.035 Uiso calc R 1 1
C C21 0.7874(4) -0.0788(11) 0.7598(4) 0.0242(13) Uani d . 1 1
C C22 0.8030(5) 0.1245(10) 0.8100(4) 0.0268(14) Uani d . 1 1
H H22 0.7539 0.2487 0.8096 0.032 Uiso calc R 1 1
C C23 0.8912(5) 0.1431(12) 0.8605(4) 0.0306(15) Uani d . 1 1
H H23 0.9009 0.2825 0.8939 0.037 Uiso calc R 1 1
C C24 0.9644(4) -0.0303(11) 0.8642(4) 0.0253(12) Uani d . 1 1
H H24 1.0231 -0.0167 0.9001 0.030 Uiso calc R 1 1
C C25 0.9475(5) -0.2357(13) 0.8104(4) 0.0314(14) Uani d . 1 1
H H25 0.9971 -0.3583 0.8093 0.038 Uiso calc R 1 1
C C26 0.8609(5) -0.2551(11) 0.7612(4) 0.0265(13) Uani d . 1 1
H H26 0.8509 -0.3928 0.7271 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'
Cl Cl 0.1484 0.1585 '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
C5 Se1 C2 82.9(3)
C2 N3 N4 115.0(5)
C5 N4 N3 115.0(5)
N3 C2 C11 122.0(6)
N3 C2 Se1 113.7(5)
C11 C2 Se1 124.3(4)
N4 C5 C21 122.8(5)
N4 C5 Se1 113.5(5)
C21 C5 Se1 123.7(4)
C16 C11 C12 118.9(6)
C16 C11 C2 120.6(5)
C12 C11 C2 120.5(6)
C13 C12 C11 120.8(6)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 118.1(6)
C12 C13 H13 121.0
C14 C13 H13 121.0
C15 C14 C13 122.6(6)
C15 C14 Cl1 119.9(5)
C13 C14 Cl1 117.5(5)
C14 C15 C16 118.4(6)
C14 C15 H15 120.8
C16 C15 H15 120.8
C11 C16 C15 121.1(6)
C11 C16 H16 119.4
C15 C16 H16 119.4
C26 C21 C22 118.8(6)
C26 C21 C5 120.0(6)
C22 C21 C5 121.2(5)
C23 C22 C21 119.5(6)
C23 C22 H22 120.2
C21 C22 H22 120.2
C24 C23 C22 122.9(6)
C24 C23 H23 118.5
C22 C23 H23 118.5
C23 C24 C25 116.4(6)
C23 C24 H24 121.8
C25 C24 H24 121.8
C26 C25 C24 120.7(6)
C26 C25 H25 119.6
C24 C25 H25 119.6
C25 C26 C21 121.5(6)
C25 C26 H26 119.2
C21 C26 H26 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C5 1.874(6)
Se1 C2 1.875(6)
Cl1 C14 1.744(7)
N3 C2 1.304(8)
N3 N4 1.378(7)
N4 C5 1.309(8)
C2 C11 1.467(9)
C5 C21 1.470(9)
C11 C16 1.386(8)
C11 C12 1.396(9)
C12 C13 1.389(9)
C12 H12 0.9500
C13 C14 1.390(10)
C13 H13 0.9500
C14 C15 1.366(9)
C15 C16 1.391(9)
C15 H15 0.9500
C16 H16 0.9500
C21 C26 1.383(9)
C21 C22 1.402(8)
C22 C23 1.394(10)
C22 H22 0.9500
C23 C24 1.368(9)
C23 H23 0.9500
C24 C25 1.448(9)
C24 H24 0.9500
C25 C26 1.366(9)
C25 H25 0.9500
C26 H26 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
C2 N3 N4 C5 -1.0(8)
N4 N3 C2 C11 179.0(5)
N4 N3 C2 Se1 1.0(7)
C5 Se1 C2 N3 -0.6(5)
C5 Se1 C2 C11 -178.5(5)
N3 N4 C5 C21 179.7(5)
N3 N4 C5 Se1 0.5(7)
C2 Se1 C5 N4 0.1(5)
C2 Se1 C5 C21 -179.2(5)
N3 C2 C11 C16 1.1(9)
Se1 C2 C11 C16 178.9(5)
N3 C2 C11 C12 -179.4(6)
Se1 C2 C11 C12 -1.6(8)
C16 C11 C12 C13 -1.2(9)
C2 C11 C12 C13 179.3(6)
C11 C12 C13 C14 0.8(10)
C12 C13 C14 C15 -1.3(10)
C12 C13 C14 Cl1 -179.8(5)
C13 C14 C15 C16 2.2(10)
Cl1 C14 C15 C16 -179.3(5)
C12 C11 C16 C15 2.1(9)
C2 C11 C16 C15 -178.4(5)
C14 C15 C16 C11 -2.6(9)
N4 C5 C21 C26 -0.3(9)
Se1 C5 C21 C26 178.9(5)
N4 C5 C21 C22 -179.1(6)
Se1 C5 C21 C22 0.1(8)
C26 C21 C22 C23 -0.7(9)
C5 C21 C22 C23 178.1(6)
C21 C22 C23 C24 -0.4(10)
C22 C23 C24 C25 1.8(10)
C23 C24 C25 C26 -2.1(9)
C24 C25 C26 C21 1.1(9)
C22 C21 C26 C25 0.4(9)
C5 C21 C26 C25 -178.4(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654342
