#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230409.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_2230409
loop_
_publ_author_name
'Muthukumaran, J.'
'Nishandhini, M.'
'Chitra, S.'
'Muthusubramanian, S.'
'Manisankar, P.'
'Bhattacharya, Suman'
'Krishna, R.'
'Jeyakanthan, J.'
_publ_section_title
;
 4-{(4-Chlorophenyl)[4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl]methyl}-4,5,6,7-tetrahydro-1,2,3-benzoselenadiazole
;
_journal_coeditor_code           LH5230
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1421
_journal_page_last               o1422
_journal_paper_doi               10.1107/S160053681101751X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H19 Cl N4 Se2'
_chemical_formula_moiety         'C22 H19 Cl N4 Se2'
_chemical_formula_sum            'C22 H19 Cl N4 Se2'
_chemical_formula_weight         532.78
_chemical_name_systematic
;
4-{(4-Chlorophenyl)[4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl]methyl}-4,5,6,7-
tetrahydro-1,2,3-benzoselenadiazole
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.959(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7226(18)
_cell_length_b                   12.969(4)
_cell_length_c                   17.690(3)
_cell_measurement_reflns_used    2877
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3445
_cell_measurement_theta_min      2.7229
_cell_volume                     2189.9(9)
_computing_cell_refinement       'CrysAlis RED (Oxford  Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford  Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford  Diffraction, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8795
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    3.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.683
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     293
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0508
_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)+(0.0596P)²+0.3633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2590
_reflns_number_total             3849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5230.cif
_cod_data_source_block           I
_cod_original_cell_volume        2189.9(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230409
_cod_database_fobs_code          2230409
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se2 1.09476(5) 0.12061(4) 0.16057(3) 0.0585(2) Uani d . 1 1 A .
Se Se1A 0.8917(3) 0.22707(11) -0.19037(8) 0.0718(5) Uani d PDU 0.802(5) 1 A 1
N N1A 1.0459(4) 0.1859(6) -0.1174(3) 0.0651(10) Uani d PDU 0.802(5) 1 A 1
N N2A 1.0132(5) 0.1456(10) -0.0585(4) 0.0651(10) Uani d PDU 0.802(5) 1 A 1
C C1A 0.8710(5) 0.1372(9) -0.0608(4) 0.0550(7) Uani d PDU 0.802(5) 1 A 1
C C2A 0.7819(4) 0.1715(6) -0.1252(2) 0.0550(7) Uani d PDU 0.802(5) 1 A 1
C C3A 0.6210(4) 0.1768(5) -0.1395(3) 0.0550(7) Uani d PDU 0.802(5) 1 A 1
H H3A1 0.5816 0.1386 -0.1857 0.066 Uiso calc PR 0.802(5) 1 A 1
H H3A2 0.5902 0.2478 -0.1464 0.066 Uiso calc PR 0.802(5) 1 A 1
C C4A 0.5716(6) 0.1296(5) -0.0694(3) 0.0550(7) Uani d PDU 0.802(5) 1 A 1
H H4A1 0.4790 0.1003 -0.0862 0.066 Uiso calc PR 0.802(5) 1 A 1
H H4A2 0.5637 0.1841 -0.0330 0.066 Uiso calc PR 0.802(5) 1 A 1
C C5A 0.6695(6) 0.0453(5) -0.0280(5) 0.0550(7) Uani d PDU 0.802(5) 1 A 1
H H5A1 0.6280 0.0150 0.0125 0.066 Uiso calc PR 0.802(5) 1 A 1
H H5A2 0.6802 -0.0087 -0.0644 0.066 Uiso calc PR 0.802(5) 1 A 1
C C6A 0.8145(7) 0.0897(9) 0.0070(3) 0.0550(7) Uani d PDU 0.802(5) 1 A 1
H H6A 0.8761 0.0329 0.0284 0.066 Uiso calc PR 0.802(5) 1 A 1
Se Se1B 0.9566(8) 0.2149(5) -0.1767(3) 0.0718(5) Uani d PDU 0.198(5) 1 A 2
N N1B 1.0899(15) 0.176(3) -0.0914(11) 0.0651(10) Uani d PDU 0.198(5) 1 A 2
N N2B 1.0313(16) 0.139(5) -0.0400(17) 0.0651(10) Uani d PDU 0.198(5) 1 A 2
C C1B 0.8867(16) 0.136(3) -0.0542(15) 0.0550(7) Uani d PDU 0.198(5) 1 A 2
C C2B 0.8184(11) 0.179(2) -0.1217(9) 0.0550(7) Uani d PDU 0.198(5) 1 A 2
C C3B 0.6665(17) 0.150(2) -0.1572(10) 0.0550(7) Uani d PDU 0.198(5) 1 A 2
H H3B1 0.6636 0.0825 -0.1811 0.066 Uiso calc PR 0.198(5) 1 A 2
H H3B2 0.6265 0.1999 -0.1961 0.066 Uiso calc PR 0.198(5) 1 A 2
C C4B 0.584(2) 0.1489(19) -0.0911(12) 0.0550(7) Uani d PDU 0.198(5) 1 A 2
H H4B1 0.5922 0.2149 -0.0647 0.066 Uiso calc PR 0.198(5) 1 A 2
H H4B2 0.4856 0.1352 -0.1107 0.066 Uiso calc PR 0.198(5) 1 A 2
C C5B 0.649(2) 0.063(2) -0.0358(17) 0.0550(7) Uani d PDU 0.198(5) 1 A 2
H H5B1 0.5952 0.0559 0.0050 0.066 Uiso calc PR 0.198(5) 1 A 2
H H5B2 0.6416 -0.0022 -0.0637 0.066 Uiso calc PR 0.198(5) 1 A 2
C C6B 0.803(2) 0.083(3) 0.0002(14) 0.0550(7) Uani d PD 0.198(5) 1 A 2
H H6B 0.8495 0.0184 0.0203 0.066 Uiso calc PR 0.198(5) 1 A 2
C C7 0.8116(4) 0.1691(3) 0.0701(2) 0.0381(10) Uani d . 1 1 . .
H H7 0.7625 0.2297 0.0451 0.046 Uiso calc R 1 1 A 1
Cl Cl1 0.46832(17) 0.03231(15) 0.30184(9) 0.0924(6) Uani d . 1 1 A .
N N3 1.1287(4) 0.3213(4) 0.1634(2) 0.0590(11) Uani d . 1 1 A .
C C8 0.7283(4) 0.1319(4) 0.1297(2) 0.0397(11) Uani d . 1 1 A .
C C14 0.9555(4) 0.2050(4) 0.1089(2) 0.0398(11) Uani d . 1 1 A .
C C15 0.9973(4) 0.3053(4) 0.1179(2) 0.0430(11) Uani d . 1 1 . .
N N4 1.1966(4) 0.2421(4) 0.1914(3) 0.0694(13) Uani d . 1 1 . .
C C12 0.6800(5) 0.0107(4) 0.2241(3) 0.0568(13) Uani d . 1 1 A .
H H12 0.7008 -0.0501 0.2517 0.068 Uiso calc R 1 1 . .
C C16 0.9173(5) 0.3976(4) 0.0856(2) 0.0431(11) Uani d . 1 1 A .
C C19 0.7582(6) 0.5702(5) 0.0261(4) 0.0690(16) Uani d . 1 1 . .
C C9 0.6174(5) 0.1898(4) 0.1437(3) 0.0525(13) Uani d . 1 1 . .
H H9 0.5960 0.2510 0.1166 0.063 Uiso calc R 1 1 A .
C C11 0.5706(5) 0.0717(5) 0.2355(3) 0.0596(15) Uani d . 1 1 . .
C C10 0.5379(5) 0.1612(5) 0.1956(3) 0.0563(14) Uani d . 1 1 A .
H H10 0.4630 0.2016 0.2037 0.068 Uiso calc R 1 1 . .
C C13 0.7581(5) 0.0413(4) 0.1711(2) 0.0507(12) Uani d . 1 1 . .
H H13 0.8325 0.0004 0.1629 0.061 Uiso calc R 1 1 A .
C C17 0.8653(6) 0.4074(4) 0.0074(3) 0.0575(14) Uani d . 1 1 . .
H H17 0.8840 0.3561 -0.0259 0.069 Uiso calc R 1 1 A .
C C18 0.7867(6) 0.4917(4) -0.0218(3) 0.0696(16) Uani d . 1 1 A .
H H18 0.7521 0.4959 -0.0745 0.084 Uiso calc R 1 1 . .
C C21 0.8923(6) 0.4772(4) 0.1331(3) 0.0576(13) Uani d . 1 1 . .
H H21 0.9291 0.4741 0.1855 0.069 Uiso calc R 1 1 A .
C C20 0.8137(6) 0.5610(4) 0.1034(3) 0.0709(16) Uani d . 1 1 A .
H H20 0.7975 0.6132 0.1367 0.085 Uiso calc R 1 1 . .
C C22 0.6694(7) 0.6612(6) -0.0055(4) 0.115(3) Uani d . 1 1 . .
H H22A 0.6222 0.6878 0.0333 0.173 Uiso calc R 1 1 . .
H H22B 0.6014 0.6399 -0.0495 0.173 Uiso calc R 1 1 . .
H H22C 0.7280 0.7139 -0.0206 0.173 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 Se2 N4 . . 86.7(2) ?
C2A Se1A N1A . . 86.59(18) ?
N2A N1A Se1A . . 113.4(3) ?
N1A N2A C1A . . 114.7(4) ?
C2A C1A N2A . . 118.1(4) ?
C2A C1A C6A . . 121.0(4) ?
N2A C1A C6A . . 120.9(4) ?
C1A C2A C3A . . 127.9(3) ?
C1A C2A Se1A . . 107.2(3) ?
C3A C2A Se1A . . 124.6(3) ?
C2A C3A C4A . . 108.3(3) ?
C2A C3A H3A1 . . 110.0 ?
C4A C3A H3A1 . . 110.0 ?
C2A C3A H3A2 . . 110.0 ?
C4A C3A H3A2 . . 110.0 ?
H3A1 C3A H3A2 . . 108.4 ?
C3A C4A C5A . . 113.9(5) ?
C3A C4A H4A1 . . 108.8 ?
C5A C4A H4A1 . . 108.8 ?
C3A C4A H4A2 . . 108.8 ?
C5A C4A H4A2 . . 108.8 ?
H4A1 C4A H4A2 . . 107.7 ?
C6A C5A C4A . . 111.2(5) ?
C6A C5A H5A1 . . 109.4 ?
C4A C5A H5A1 . . 109.4 ?
C6A C5A H5A2 . . 109.4 ?
C4A C5A H5A2 . . 109.4 ?
H5A1 C5A H5A2 . . 108.0 ?
C7 C6A C1A . . 111.1(8) ?
C7 C6A C5A . . 113.9(7) ?
C1A C6A C5A . . 105.8(5) ?
C7 C6A H6A . . 108.7 ?
C1A C6A H6A . . 108.7 ?
C5A C6A H6A . . 108.7 ?
C2B Se1B N1B . . 88.3(7) ?
N2B N1B Se1B . . 110.4(11) ?
N1B N2B C1B . . 117.5(14) ?
C2B C1B N2B . . 117.3(12) ?
C2B C1B C6B . . 120.3(12) ?
N2B C1B C6B . . 122.3(14) ?
C1B C2B C3B . . 121.5(15) ?
C1B C2B Se1B . . 106.1(9) ?
C3B C2B Se1B . . 125.5(11) ?
C2B C3B C4B . . 106.9(12) ?
C2B C3B H3B1 . . 110.3 ?
C4B C3B H3B1 . . 110.3 ?
C2B C3B H3B2 . . 110.3 ?
C4B C3B H3B2 . . 110.3 ?
H3B1 C3B H3B2 . . 108.6 ?
C5B C4B C3B . . 106.3(15) ?
C5B C4B H4B1 . . 110.5 ?
C3B C4B H4B1 . . 110.5 ?
C5B C4B H4B2 . . 110.5 ?
C3B C4B H4B2 . . 110.5 ?
H4B1 C4B H4B2 . . 108.7 ?
C6B C5B C4B . . 112.9(16) ?
C6B C5B H5B1 . . 109.0 ?
C4B C5B H5B1 . . 109.0 ?
C6B C5B H5B2 . . 109.0 ?
C4B C5B H5B2 . . 109.0 ?
H5B1 C5B H5B2 . . 107.8 ?
C1B C6B C5B . . 114.0(14) ?
C1B C6B C7 . . 102(3) ?
C5B C6B C7 . . 109(3) ?
C1B C6B H6B . . 110.6 ?
C5B C6B H6B . . 110.6 ?
C7 C6B H6B . . 110.6 ?
C14 C7 C6A . . 113.4(4) ?
C14 C7 C8 . . 110.6(3) ?
C6A C7 C8 . . 112.3(4) ?
C14 C7 C6B . . 117.2(8) ?
C8 C7 C6B . . 110.1(7) ?
C14 C7 H7 . . 106.7 ?
C6A C7 H7 . . 106.7 ?
C8 C7 H7 . . 106.7 ?
C6B C7 H7 . . 104.9 ?
N4 N3 C15 . . 117.2(4) ?
C9 C8 C13 . . 117.4(4) ?
C9 C8 C7 . . 119.3(4) ?
C13 C8 C7 . . 123.3(4) ?
C15 C14 C7 . . 125.3(4) ?
C15 C14 Se2 . . 109.5(3) ?
C7 C14 Se2 . . 124.9(3) ?
C14 C15 N3 . . 115.6(4) ?
C14 C15 C16 . . 127.1(4) ?
N3 C15 C16 . . 117.4(4) ?
N3 N4 Se2 . . 111.0(3) ?
C11 C12 C13 . . 118.6(5) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C21 C16 C17 . . 117.7(5) ?
C21 C16 C15 . . 120.7(4) ?
C17 C16 C15 . . 121.6(4) ?
C20 C19 C18 . . 117.2(5) ?
C20 C19 C22 . . 121.8(6) ?
C18 C19 C22 . . 121.0(6) ?
C10 C9 C8 . . 122.6(5) ?
C10 C9 H9 . . 118.7 ?
C8 C9 H9 . . 118.7 ?
C10 C11 C12 . . 121.7(5) ?
C10 C11 Cl1 . . 119.2(4) ?
C12 C11 Cl1 . . 119.0(5) ?
C9 C10 C11 . . 118.4(5) ?
C9 C10 H10 . . 120.8 ?
C11 C10 H10 . . 120.8 ?
C12 C13 C8 . . 121.2(4) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C18 C17 C16 . . 121.3(5) ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C17 C18 C19 . . 121.0(5) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C20 C21 C16 . . 120.6(5) ?
C20 C21 H21 . . 119.7 ?
C16 C21 H21 . . 119.7 ?
C21 C20 C19 . . 122.2(5) ?
C21 C20 H20 . . 118.9 ?
C19 C20 H20 . . 118.9 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
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
Se2 C14 . 1.843(4) ?
Se2 N4 . 1.886(5) ?
Se1A C2A . 1.8585(10) ?
Se1A N1A . 1.8605(11) ?
N1A N2A . 1.2601(10) ?
N2A C1A . 1.3790(10) ?
C1A C2A . 1.3688(10) ?
C1A C6A . 1.5387(10) ?
C2A C3A . 1.5385(10) ?
C3A C4A . 1.5394(10) ?
C3A H3A1 . 0.9700 ?
C3A H3A2 . 0.9700 ?
C4A C5A . 1.5396(10) ?
C4A H4A1 . 0.9700 ?
C4A H4A2 . 0.9700 ?
C5A C6A . 1.5394(10) ?
C5A H5A1 . 0.9700 ?
C5A H5A2 . 0.9700 ?
C6A C7 . 1.523(11) ?
C6A H6A . 0.9800 ?
Se1B C2B . 1.8597(11) ?
Se1B N1B . 1.8602(11) ?
N1B N2B . 1.2600(10) ?
N2B C1B . 1.3798(10) ?
C1B C2B . 1.3698(10) ?
C1B C6B . 1.5397(10) ?
C2B C3B . 1.5398(11) ?
C3B C4B . 1.5399(10) ?
C3B H3B1 . 0.9700 ?
C3B H3B2 . 0.9700 ?
C4B C5B . 1.5398(10) ?
C4B H4B1 . 0.9700 ?
C4B H4B2 . 0.9700 ?
C5B C6B . 1.5398(11) ?
C5B H5B1 . 0.9700 ?
C5B H5B2 . 0.9700 ?
C6B C7 . 1.66(4) ?
C6B H6B . 0.9800 ?
C7 C14 . 1.510(6) ?
C7 C8 . 1.526(6) ?
C7 H7 . 0.9800 ?
Cl1 C11 . 1.753(5) ?
N3 N4 . 1.270(6) ?
N3 C15 . 1.390(6) ?
C8 C9 . 1.375(6) ?
C8 C13 . 1.386(6) ?
C14 C15 . 1.363(6) ?
C15 C16 . 1.482(6) ?
C12 C11 . 1.371(7) ?
C12 C13 . 1.372(6) ?
C12 H12 . 0.9300 ?
C16 C21 . 1.381(6) ?
C16 C17 . 1.385(6) ?
C19 C20 . 1.377(8) ?
C19 C18 . 1.387(8) ?
C19 C22 . 1.506(8) ?
C9 C10 . 1.360(7) ?
C9 H9 . 0.9300 ?
C11 C10 . 1.364(7) ?
C10 H10 . 0.9300 ?
C13 H13 . 0.9300 ?
C17 C18 . 1.377(7) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C21 C20 . 1.373(7) ?
C21 H21 . 0.9300 ?
C20 H20 . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 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
C6A H6A N2A 3_755 0.98 2.57 3.517(16) 164
C10 H10 N4 1_455 0.93 2.61 3.467(7) 153
C12 H12 N3 2_745 0.93 2.61 3.470(7) 153
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
C2A Se1A N1A N2A . . . . -2.8(7) ?
Se1A N1A N2A C1A . . . . 1.9(13) ?
N1A N2A C1A C2A . . . . 0.5(17) ?
N1A N2A C1A C6A . . . . -179.9(10) ?
N2A C1A C2A C3A . . . . -175.9(10) ?
C6A C1A C2A C3A . . . . 4.5(16) ?
N2A C1A C2A Se1A . . . . -2.6(14) ?
C6A C1A C2A Se1A . . . . 177.8(9) ?
N1A Se1A C2A C1A . . . . 2.8(7) ?
N1A Se1A C2A C3A . . . . 176.3(7) ?
C1A C2A C3A C4A . . . . -3.4(12) ?
Se1A C2A C3A C4A . . . . -175.6(5) ?
C2A C3A C4A C5A . . . . -29.7(8) ?
C3A C4A C5A C6A . . . . 64.0(7) ?
C2A C1A C6A C7 . . . . -97.8(10) ?
N2A C1A C6A C7 . . . . 82.7(14) ?
C2A C1A C6A C5A . . . . 26.3(14) ?
N2A C1A C6A C5A . . . . -153.3(12) ?
C4A C5A C6A C7 . . . . 64.0(7) ?
C4A C5A C6A C1A . . . . -58.3(10) ?
C2B Se1B N1B N2B . . . . 5(3) ?
Se1B N1B N2B C1B . . . . -2(5) ?
N1B N2B C1B C2B . . . . -3(7) ?
N1B N2B C1B C6B . . . . 174(4) ?
N2B C1B C2B C3B . . . . 158(4) ?
C6B C1B C2B C3B . . . . -18(6) ?
N2B C1B C2B Se1B . . . . 6(5) ?
C6B C1B C2B Se1B . . . . -170(4) ?
N1B Se1B C2B C1B . . . . -6(3) ?
N1B Se1B C2B C3B . . . . -157(3) ?
C1B C2B C3B C4B . . . . 45(4) ?
Se1B C2B C3B C4B . . . . -169(2) ?
C2B C3B C4B C5B . . . . -64(2) ?
C3B C4B C5B C6B . . . . 63(3) ?
C2B C1B C6B C5B . . . . 12(6) ?
N2B C1B C6B C5B . . . . -164(5) ?
C2B C1B C6B C7 . . . . -105(4) ?
N2B C1B C6B C7 . . . . 79(5) ?
C4B C5B C6B C1B . . . . -36(5) ?
C4B C5B C6B C7 . . . . 77(2) ?
C1A C6A C7 C14 . . . . -65.9(6) ?
C5A C6A C7 C14 . . . . 174.8(4) ?
C1A C6A C7 C8 . . . . 167.9(4) ?
C5A C6A C7 C8 . . . . 48.6(7) ?
C1A C6A C7 C6B . . . . 112(16) ?
C5A C6A C7 C6B . . . . -7(16) ?
C1B C6B C7 C14 . . . . -54.9(18) ?
C5B C6B C7 C14 . . . . -175.7(10) ?
C1B C6B C7 C6A . . . . -57(15) ?
C5B C6B C7 C6A . . . . -177(17) ?
C1B C6B C7 C8 . . . . 177.6(12) ?
C5B C6B C7 C8 . . . . 56.9(16) ?
C14 C7 C8 C9 . . . . 109.2(4) ?
C6A C7 C8 C9 . . . . -123.1(5) ?
C6B C7 C8 C9 . . . . -119.7(11) ?
C14 C7 C8 C13 . . . . -71.1(5) ?
C6A C7 C8 C13 . . . . 56.7(6) ?
C6B C7 C8 C13 . . . . 60.0(12) ?
C6A C7 C14 C15 . . . . 127.4(5) ?
C8 C7 C14 C15 . . . . -105.5(5) ?
C6B C7 C14 C15 . . . . 127.3(10) ?
C6A C7 C14 Se2 . . . . -59.8(5) ?
C8 C7 C14 Se2 . . . . 67.3(4) ?
C6B C7 C14 Se2 . . . . -59.9(10) ?
N4 Se2 C14 C15 . . . . 1.2(3) ?
N4 Se2 C14 C7 . . . . -172.6(4) ?
C7 C14 C15 N3 . . . . 172.5(4) ?
Se2 C14 C15 N3 . . . . -1.2(5) ?
C7 C14 C15 C16 . . . . -6.5(7) ?
Se2 C14 C15 C16 . . . . 179.8(3) ?
N4 N3 C15 C14 . . . . 0.5(6) ?
N4 N3 C15 C16 . . . . 179.6(4) ?
C15 N3 N4 Se2 . . . . 0.5(5) ?
C14 Se2 N4 N3 . . . . -1.0(4) ?
C14 C15 C16 C21 . . . . 125.1(5) ?
N3 C15 C16 C21 . . . . -53.8(6) ?
C14 C15 C16 C17 . . . . -55.1(7) ?
N3 C15 C16 C17 . . . . 126.0(5) ?
C13 C8 C9 C10 . . . . -0.2(7) ?
C7 C8 C9 C10 . . . . 179.5(4) ?
C13 C12 C11 C10 . . . . 0.1(8) ?
C13 C12 C11 Cl1 . . . . 179.0(4) ?
C8 C9 C10 C11 . . . . 0.5(7) ?
C12 C11 C10 C9 . . . . -0.4(8) ?
Cl1 C11 C10 C9 . . . . -179.3(4) ?
C11 C12 C13 C8 . . . . 0.1(7) ?
C9 C8 C13 C12 . . . . -0.1(7) ?
C7 C8 C13 C12 . . . . -179.8(4) ?
C21 C16 C17 C18 . . . . -2.6(7) ?
C15 C16 C17 C18 . . . . 177.6(5) ?
C16 C17 C18 C19 . . . . 0.8(9) ?
C20 C19 C18 C17 . . . . 1.1(9) ?
C22 C19 C18 C17 . . . . -178.6(6) ?
C17 C16 C21 C20 . . . . 2.6(8) ?
C15 C16 C21 C20 . . . . -177.6(5) ?
C16 C21 C20 C19 . . . . -0.8(9) ?
C18 C19 C20 C21 . . . . -1.1(9) ?
C22 C19 C20 C21 . . . . 178.6(6) ?
