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#$Date: 2020-02-20 02:08:58 +0200 (Thu, 20 Feb 2020) $
#$Revision: 248296 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037943.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4037943
loop_
_publ_author_name
'Chen, Wenqi'
'Zhu, Xiaoming'
'Wang, Fei'
'Yang, Yuan'
'Deng, Guobo'
'Liang, Yun'
_publ_section_title
;
 Iodine-Catalyzed Three-Component Cascade Reaction for the Synthesis of
 Substituted 2-Phenylnaphtho[1,3]selenazoles under Transition-Metal-Free
 Conditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03154
_journal_year                    2020
_chemical_formula_sum            'C18 H13 N Se'
_chemical_formula_weight         322.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.210(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.885(5)
_cell_length_b                   13.354(7)
_cell_length_c                   21.226(10)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.57
_cell_volume                     2785(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27972
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.460
_exptl_absorpt_coefficient_mu    2.684
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0656P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3949
_reflns_number_total             4904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03154_si_002.cif
_cod_data_source_block           zxm334
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037943
_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. 
;
_shelx_estimated_absorpt_t_min   0.500
_shelx_estimated_absorpt_t_max   0.577
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.41451(3) 0.86160(3) 0.03288(2) 0.04881(14) Uani 1 1 d . . . . .
Se2 Se 0.19076(3) 0.10503(2) 1.00294(2) 0.04790(14) Uani 1 1 d . . . . .
N1 N 0.2218(2) 0.83858(19) 0.11344(11) 0.0431(6) Uani 1 1 d . . . . .
N2 N 0.2318(3) 0.20046(19) 0.89382(11) 0.0435(6) Uani 1 1 d . . . . .
C1 C 0.3276(3) 0.8921(2) 0.10636(14) 0.0430(8) Uani 1 1 d . . . . .
C2 C 0.1913(3) 0.7698(2) 0.06522(13) 0.0412(7) Uani 1 1 d . . . . .
C3 C 0.2764(3) 0.7672(2) 0.01695(13) 0.0403(7) Uani 1 1 d . . . . .
C4 C 0.2474(3) 0.7034(2) -0.03628(13) 0.0426(7) Uani 1 1 d . . . . .
C5 C 0.1296(3) 0.6452(2) -0.03937(15) 0.0460(8) Uani 1 1 d . . . . .
C6 C 0.0474(3) 0.6460(2) 0.01146(16) 0.0486(8) Uani 1 1 d . . . . .
H2 H -0.0287 0.6048 0.0097 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0780(3) 0.7057(3) 0.06248(14) 0.0488(8) Uani 1 1 d . . . . .
H1 H 0.0241 0.7043 0.0958 0.059 Uiso 1 1 calc R U . . .
C8 C 0.0931(4) 0.5868(3) -0.09491(16) 0.0555(9) Uani 1 1 d . . . . .
H6 H 0.0142 0.5483 -0.0981 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1730(4) 0.5871(3) -0.14306(17) 0.0637(10) Uani 1 1 d . . . . .
H5 H 0.1478 0.5497 -0.1794 0.076 Uiso 1 1 calc R U . . .
C10 C 0.2926(4) 0.6431(3) -0.13843(17) 0.0633(10) Uani 1 1 d . . . . .
H4 H 0.3478 0.6407 -0.1712 0.076 Uiso 1 1 calc R U . . .
C11 C 0.3300(3) 0.7010(3) -0.08715(15) 0.0516(8) Uani 1 1 d . . . . .
H3 H 0.4092 0.7390 -0.0852 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3794(3) 0.9716(2) 0.14994(14) 0.0445(7) Uani 1 1 d . . . . .
C13 C 0.3054(4) 1.0013(3) 0.19820(15) 0.0581(9) Uani 1 1 d . . . . .
H13 H 0.2217 0.9715 0.2023 0.070 Uiso 1 1 calc R U . . .
C14 C 0.3541(4) 1.0748(3) 0.24054(15) 0.0643(10) Uani 1 1 d . . . . .
H12 H 0.3024 1.0933 0.2727 0.077 Uiso 1 1 calc R U . . .
C15 C 0.4761(4) 1.1211(2) 0.23648(16) 0.0568(9) Uani 1 1 d . . . . .
C16 C 0.5497(4) 1.0927(3) 0.18756(17) 0.0605(10) Uani 1 1 d . . . . .
H8 H 0.6329 1.1232 0.1834 0.073 Uiso 1 1 calc R U . . .
C17 C 0.5016(3) 1.0195(3) 0.14468(16) 0.0567(9) Uani 1 1 d . . . . .
H7 H 0.5523 1.0023 0.1118 0.068 Uiso 1 1 calc R U . . .
C18 C 0.5304(4) 1.2003(3) 0.28341(17) 0.0805(13) Uani 1 1 d . . . . .
H9 H 0.4720 1.2053 0.3166 0.121 Uiso 1 1 calc R U . . .
H11 H 0.5333 1.2636 0.2622 0.121 Uiso 1 1 calc R U . . .
H10 H 0.6205 1.1823 0.3013 0.121 Uiso 1 1 calc R U . . .
C19 C 0.2561(3) 0.2353(2) 1.00372(13) 0.0411(7) Uani 1 1 d . . . . .
C20 C 0.2682(3) 0.2676(2) 0.94268(13) 0.0407(7) Uani 1 1 d . . . . .
C21 C 0.1891(3) 0.1161(2) 0.91355(13) 0.0415(7) Uani 1 1 d . . . . .
C22 C 0.1421(3) 0.0327(2) 0.87167(13) 0.0404(7) Uani 1 1 d . . . . .
C23 C 0.1028(3) -0.0581(2) 0.89467(14) 0.0477(8) Uani 1 1 d . . . . .
H14 H 0.1052 -0.0675 0.9382 0.057 Uiso 1 1 calc R U . . .
C24 C 0.0600(3) -0.1349(3) 0.85412(16) 0.0533(9) Uani 1 1 d . . . . .
H15 H 0.0338 -0.1954 0.8708 0.064 Uiso 1 1 calc R U . . .
C25 C 0.0553(3) -0.1240(3) 0.78941(16) 0.0522(8) Uani 1 1 d . . . . .
C26 C 0.0130(5) -0.2103(3) 0.74547(18) 0.0800(12) Uani 1 1 d . . . . .
H18 H -0.0556 -0.1881 0.7130 0.120 Uiso 1 1 calc R U . . .
H17 H -0.0228 -0.2635 0.7692 0.120 Uiso 1 1 calc R U . . .
H16 H 0.0905 -0.2342 0.7263 0.120 Uiso 1 1 calc R U . . .
C27 C 0.0938(4) -0.0329(3) 0.76665(15) 0.0586(9) Uani 1 1 d . . . . .
H20 H 0.0903 -0.0234 0.7231 0.070 Uiso 1 1 calc R U . . .
C28 C 0.1369(3) 0.0436(3) 0.80648(14) 0.0518(8) Uani 1 1 d . . . . .
H19 H 0.1631 0.1039 0.7896 0.062 Uiso 1 1 calc R U . . .
C29 C 0.3131(4) 0.3655(2) 0.93237(17) 0.0524(9) Uani 1 1 d . . . . .
H21 H 0.3245 0.3864 0.8915 0.063 Uiso 1 1 calc R U . . .
C30 C 0.3396(3) 0.4289(3) 0.98117(16) 0.0532(8) Uani 1 1 d . . . . .
H22 H 0.3674 0.4938 0.9735 0.064 Uiso 1 1 calc R U . . .
C31 C 0.3258(3) 0.3986(2) 1.04451(16) 0.0499(8) Uani 1 1 d . . . . .
C32 C 0.2848(3) 0.2997(2) 1.05667(14) 0.0437(7) Uani 1 1 d . . . . .
C33 C 0.2736(3) 0.2702(3) 1.11954(15) 0.0558(9) Uani 1 1 d . . . . .
H26 H 0.2479 0.2049 1.1279 0.067 Uiso 1 1 calc R U . . .
C34 C 0.2997(4) 0.3359(3) 1.16800(17) 0.0677(11) Uani 1 1 d . . . . .
H25 H 0.2929 0.3154 1.2094 0.081 Uiso 1 1 calc R U . . .
C35 C 0.3371(4) 0.4345(3) 1.1558(2) 0.0722(11) Uani 1 1 d . . . . .
H24 H 0.3535 0.4795 1.1892 0.087 Uiso 1 1 calc R U . . .
C36 C 0.3497(3) 0.4650(3) 1.09598(18) 0.0637(10) Uani 1 1 d . . . . .
H23 H 0.3744 0.5309 1.0887 0.076 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Se1 C1 84.66(13) . . ?
C19 Se2 C21 84.35(13) . . ?
C1 N1 C2 113.4(3) . . ?
C21 N2 C20 112.9(2) . . ?
N1 C1 C12 124.1(3) . . ?
N1 C1 Se1 114.9(2) . . ?
C12 C1 Se1 121.0(2) . . ?
N1 C2 C3 117.3(3) . . ?
N1 C2 C7 122.9(3) . . ?
C3 C2 C7 119.7(3) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 Se1 109.8(2) . . ?
C4 C3 Se1 129.2(2) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C11 119.8(3) . . ?
C3 C4 C11 122.3(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 C8 118.6(3) . . ?
C6 C5 C8 121.2(3) . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H2 119.5 . . ?
C5 C6 H2 119.5 . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H1 120.0 . . ?
C2 C7 H1 120.0 . . ?
C9 C8 C5 120.3(4) . . ?
C9 C8 H6 119.9 . . ?
C5 C8 H6 119.9 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H5 119.8 . . ?
C10 C9 H5 119.8 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H4 119.4 . . ?
C9 C10 H4 119.4 . . ?
C10 C11 C4 119.6(3) . . ?
C10 C11 H3 120.2 . . ?
C4 C11 H3 120.2 . . ?
C13 C12 C17 117.7(3) . . ?
C13 C12 C1 120.0(3) . . ?
C17 C12 C1 122.3(3) . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H12 119.1 . . ?
C13 C14 H12 119.1 . . ?
C14 C15 C16 117.6(3) . . ?
C14 C15 C18 121.9(4) . . ?
C16 C15 C18 120.6(4) . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H8 119.5 . . ?
C17 C16 H8 119.5 . . ?
C12 C17 C16 121.0(3) . . ?
C12 C17 H7 119.5 . . ?
C16 C17 H7 119.5 . . ?
C15 C18 H9 109.5 . . ?
C15 C18 H11 109.5 . . ?
H9 C18 H11 109.5 . . ?
C15 C18 H10 109.5 . . ?
H9 C18 H10 109.5 . . ?
H11 C18 H10 109.5 . . ?
C20 C19 C32 121.5(3) . . ?
C20 C19 Se2 110.4(2) . . ?
C32 C19 Se2 127.9(2) . . ?
C19 C20 N2 117.2(3) . . ?
C19 C20 C29 119.8(3) . . ?
N2 C20 C29 123.0(3) . . ?
N2 C21 C22 124.0(3) . . ?
N2 C21 Se2 115.1(2) . . ?
C22 C21 Se2 120.9(2) . . ?
C23 C22 C28 117.7(3) . . ?
C23 C22 C21 122.4(3) . . ?
C28 C22 C21 120.0(3) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H14 119.6 . . ?
C22 C23 H14 119.6 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 H15 119.3 . . ?
C25 C24 H15 119.3 . . ?
C27 C25 C24 117.5(3) . . ?
C27 C25 C26 121.7(3) . . ?
C24 C25 C26 120.8(3) . . ?
C25 C26 H18 109.5 . . ?
C25 C26 H17 109.5 . . ?
H18 C26 H17 109.5 . . ?
C25 C26 H16 109.5 . . ?
H18 C26 H16 109.5 . . ?
H17 C26 H16 109.5 . . ?
C28 C27 C25 121.6(3) . . ?
C28 C27 H20 119.2 . . ?
C25 C27 H20 119.2 . . ?
C27 C28 C22 121.0(3) . . ?
C27 C28 H19 119.5 . . ?
C22 C28 H19 119.5 . . ?
C30 C29 C20 120.3(3) . . ?
C30 C29 H21 119.8 . . ?
C20 C29 H21 119.8 . . ?
C29 C30 C31 121.3(3) . . ?
C29 C30 H22 119.4 . . ?
C31 C30 H22 119.4 . . ?
C36 C31 C32 118.3(3) . . ?
C36 C31 C30 121.9(3) . . ?
C32 C31 C30 119.8(3) . . ?
C33 C32 C31 119.2(3) . . ?
C33 C32 C19 123.5(3) . . ?
C31 C32 C19 117.3(3) . . ?
C34 C33 C32 120.7(3) . . ?
C34 C33 H26 119.7 . . ?
C32 C33 H26 119.7 . . ?
C33 C34 C35 120.1(4) . . ?
C33 C34 H25 119.9 . . ?
C35 C34 H25 119.9 . . ?
C36 C35 C34 120.6(4) . . ?
C36 C35 H24 119.7 . . ?
C34 C35 H24 119.7 . . ?
C35 C36 C31 121.0(4) . . ?
C35 C36 H23 119.5 . . ?
C31 C36 H23 119.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C3 1.862(3) . ?
Se1 C1 1.904(3) . ?
Se2 C19 1.855(3) . ?
Se2 C21 1.901(3) . ?
N1 C1 1.289(4) . ?
N1 C2 1.384(4) . ?
N2 C21 1.289(4) . ?
N2 C20 1.388(4) . ?
C1 C12 1.463(4) . ?
C2 C3 1.395(4) . ?
C2 C7 1.406(4) . ?
C3 C4 1.419(4) . ?
C4 C5 1.395(4) . ?
C4 C11 1.423(4) . ?
C5 C6 1.419(5) . ?
C5 C8 1.427(5) . ?
C6 C7 1.352(4) . ?
C6 H2 0.9300 . ?
C7 H1 0.9300 . ?
C8 C9 1.358(5) . ?
C8 H6 0.9300 . ?
C9 C10 1.393(5) . ?
C9 H5 0.9300 . ?
C10 C11 1.354(5) . ?
C10 H4 0.9300 . ?
C11 H3 0.9300 . ?
C12 C13 1.380(4) . ?
C12 C17 1.382(4) . ?
C13 C14 1.382(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(5) . ?
C14 H12 0.9300 . ?
C15 C16 1.384(5) . ?
C15 C18 1.511(5) . ?
C16 C17 1.384(5) . ?
C16 H8 0.9300 . ?
C17 H7 0.9300 . ?
C18 H9 0.9600 . ?
C18 H11 0.9600 . ?
C18 H10 0.9600 . ?
C19 C20 1.383(4) . ?
C19 C32 1.419(4) . ?
C20 C29 1.406(4) . ?
C21 C22 1.469(4) . ?
C22 C23 1.378(4) . ?
C22 C28 1.387(4) . ?
C23 C24 1.376(4) . ?
C23 H14 0.9300 . ?
C24 C25 1.377(5) . ?
C24 H15 0.9300 . ?
C25 C27 1.377(5) . ?
C25 C26 1.513(5) . ?
C26 H18 0.9600 . ?
C26 H17 0.9600 . ?
C26 H16 0.9600 . ?
C27 C28 1.365(5) . ?
C27 H20 0.9300 . ?
C28 H19 0.9300 . ?
C29 C30 1.341(5) . ?
C29 H21 0.9300 . ?
C30 C31 1.424(5) . ?
C30 H22 0.9300 . ?
C31 C36 1.408(5) . ?
C31 C32 1.413(4) . ?
C32 C33 1.407(4) . ?
C33 C34 1.355(5) . ?
C33 H26 0.9300 . ?
C34 C35 1.400(6) . ?
C34 H25 0.9300 . ?
C35 C36 1.353(5) . ?
C35 H24 0.9300 . ?
C36 H23 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C12 178.6(3) . . . . ?
C2 N1 C1 Se1 -0.8(3) . . . . ?
C1 N1 C2 C3 0.2(4) . . . . ?
C1 N1 C2 C7 -178.2(3) . . . . ?
N1 C2 C3 C4 -176.0(3) . . . . ?
C7 C2 C3 C4 2.5(4) . . . . ?
N1 C2 C3 Se1 0.4(3) . . . . ?
C7 C2 C3 Se1 178.9(2) . . . . ?
C1 Se1 C3 C2 -0.7(2) . . . . ?
C1 Se1 C3 C4 175.3(3) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
Se1 C3 C4 C5 -174.3(2) . . . . ?
C2 C3 C4 C11 178.2(3) . . . . ?
Se1 C3 C4 C11 2.5(4) . . . . ?
C3 C4 C5 C6 -3.9(4) . . . . ?
C11 C4 C5 C6 179.2(3) . . . . ?
C3 C4 C5 C8 175.0(3) . . . . ?
C11 C4 C5 C8 -1.9(4) . . . . ?
C4 C5 C6 C7 2.7(5) . . . . ?
C8 C5 C6 C7 -176.2(3) . . . . ?
C5 C6 C7 C2 1.3(5) . . . . ?
N1 C2 C7 C6 174.6(3) . . . . ?
C3 C2 C7 C6 -3.9(5) . . . . ?
C4 C5 C8 C9 1.0(5) . . . . ?
C6 C5 C8 C9 179.9(3) . . . . ?
C5 C8 C9 C10 1.0(5) . . . . ?
C8 C9 C10 C11 -2.2(6) . . . . ?
C9 C10 C11 C4 1.3(5) . . . . ?
C5 C4 C11 C10 0.8(5) . . . . ?
C3 C4 C11 C10 -176.0(3) . . . . ?
N1 C1 C12 C13 -7.8(5) . . . . ?
Se1 C1 C12 C13 171.6(2) . . . . ?
N1 C1 C12 C17 172.5(3) . . . . ?
Se1 C1 C12 C17 -8.2(4) . . . . ?
C17 C12 C13 C14 -1.6(5) . . . . ?
C1 C12 C13 C14 178.7(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C13 C14 C15 C18 -179.0(3) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C18 C15 C16 C17 179.4(3) . . . . ?
C13 C12 C17 C16 1.9(5) . . . . ?
C1 C12 C17 C16 -178.4(3) . . . . ?
C15 C16 C17 C12 -0.9(5) . . . . ?
C21 Se2 C19 C20 -0.3(2) . . . . ?
C21 Se2 C19 C32 176.3(3) . . . . ?
C32 C19 C20 N2 -177.1(3) . . . . ?
Se2 C19 C20 N2 -0.2(3) . . . . ?
C32 C19 C20 C29 1.6(4) . . . . ?
Se2 C19 C20 C29 178.5(2) . . . . ?
C21 N2 C20 C19 0.9(4) . . . . ?
C21 N2 C20 C29 -177.7(3) . . . . ?
C20 N2 C21 C22 178.9(3) . . . . ?
C20 N2 C21 Se2 -1.2(3) . . . . ?
N2 C21 C22 C23 177.1(3) . . . . ?
Se2 C21 C22 C23 -2.8(4) . . . . ?
N2 C21 C22 C28 -2.5(5) . . . . ?
Se2 C21 C22 C28 177.6(2) . . . . ?
C28 C22 C23 C24 0.0(5) . . . . ?
C21 C22 C23 C24 -179.6(3) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
C23 C24 C25 C27 -0.6(5) . . . . ?
C23 C24 C25 C26 177.8(4) . . . . ?
C24 C25 C27 C28 0.9(5) . . . . ?
C26 C25 C27 C28 -177.5(3) . . . . ?
C25 C27 C28 C22 -0.7(5) . . . . ?
C23 C22 C28 C27 0.2(5) . . . . ?
C21 C22 C28 C27 179.9(3) . . . . ?
C19 C20 C29 C30 -2.4(5) . . . . ?
N2 C20 C29 C30 176.2(3) . . . . ?
C20 C29 C30 C31 1.3(5) . . . . ?
C29 C30 C31 C36 -178.2(3) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
C36 C31 C32 C33 -2.0(5) . . . . ?
C30 C31 C32 C33 179.1(3) . . . . ?
C36 C31 C32 C19 177.5(3) . . . . ?
C30 C31 C32 C19 -1.4(5) . . . . ?
C20 C19 C32 C33 179.8(3) . . . . ?
Se2 C19 C32 C33 3.5(4) . . . . ?
C20 C19 C32 C31 0.3(4) . . . . ?
Se2 C19 C32 C31 -176.0(2) . . . . ?
C31 C32 C33 C34 0.9(5) . . . . ?
C19 C32 C33 C34 -178.6(3) . . . . ?
C32 C33 C34 C35 0.6(6) . . . . ?
C33 C34 C35 C36 -1.0(6) . . . . ?
C34 C35 C36 C31 -0.1(6) . . . . ?
C32 C31 C36 C35 1.6(5) . . . . ?
C30 C31 C36 C35 -179.5(3) . . . . ?
