#------------------------------------------------------------------------------
#$Date: 2020-07-01 02:22:20 +0300 (Wed, 01 Jul 2020) $
#$Revision: 253581 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038538.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_4038538
loop_
_publ_author_name
'Zhu, Yu-Shen'
'Xue, Yuting'
'Liu, Wannian'
'Zhu, Xinju'
'Hao, Xin-Qi'
'Song, Mao-Ping'
_publ_section_title
;
 Temperature-Controlled Chalcogenation and Chalcogenocyanation of
 Imidazopyridines in Water under Transition Metal-Free Conditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01035
_journal_year                    2020
_chemical_formula_moiety         'C26 H18 N4 Se'
_chemical_formula_sum            'C26 H18 N4 Se'
_chemical_formula_weight         465.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.552(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3346(4)
_cell_length_b                   13.8650(5)
_cell_length_c                   12.6601(4)
_cell_measurement_reflns_used    2627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5720
_cell_measurement_theta_min      4.5240
_cell_volume                     2113.37(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00  -63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   13.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 77

#__ type_ start__ end____ width___ exp.time_
  8 omega   62.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   64.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega  -24.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega  -23.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  167.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 13 omega  102.00  176.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
 14 omega   52.00   91.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   84.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00   97.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 17 omega   55.00   94.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00  100.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 19 omega   94.00  166.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
 20 omega  103.00  165.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0320556000
_diffrn_orient_matrix_UB_12      -0.0556877000
_diffrn_orient_matrix_UB_13      -0.0940254000
_diffrn_orient_matrix_UB_21      0.0945529000
_diffrn_orient_matrix_UB_22      0.0724237000
_diffrn_orient_matrix_UB_23      -0.0007389000
_diffrn_orient_matrix_UB_31      0.0800025000
_diffrn_orient_matrix_UB_32      -0.0632181000
_diffrn_orient_matrix_UB_33      0.0819098000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.536
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2936
_reflns_number_total             3779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01035_si_002.cif
_cod_data_source_block           201904107
_cod_original_cell_volume        2113.36(11)
_cod_database_code               4038538
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_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_max   0.766
_shelx_estimated_absorpt_t_min   0.685
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_olex2_date_sample_data_collection 1556273592.03
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.0785(3) 0.3943(2) 0.3498(3) 0.0518(8) Uani 1 1 d . . . . .
H1 H 0.0927 0.3532 0.4093 0.062 Uiso 1 1 calc R . . . .
C2 C 0.0395(3) 0.3590(3) 0.2501(3) 0.0650(10) Uani 1 1 d . . . . .
H2 H 0.0277 0.2931 0.2402 0.078 Uiso 1 1 calc R . . . .
C3 C 0.0165(3) 0.4214(3) 0.1608(3) 0.0750(12) Uani 1 1 d . . . . .
H3 H -0.0130 0.3966 0.0923 0.090 Uiso 1 1 calc R . . . .
C4 C 0.0369(3) 0.5175(3) 0.1730(3) 0.0694(11) Uani 1 1 d . . . . .
H4 H 0.0230 0.5582 0.1132 0.083 Uiso 1 1 calc R . . . .
C5 C 0.0791(3) 0.5545(3) 0.2773(3) 0.0482(8) Uani 1 1 d . . . . .
C6 C 0.1360(2) 0.5463(2) 0.4563(2) 0.0414(7) Uani 1 1 d . . . . .
C7 C 0.1405(2) 0.6397(2) 0.4197(2) 0.0416(7) Uani 1 1 d . . . . .
C8 C 0.1771(3) 0.7278(2) 0.4818(2) 0.0448(7) Uani 1 1 d . . . . .
C9 C 0.1526(3) 0.7454(3) 0.5816(3) 0.0582(9) Uani 1 1 d . . . . .
H9 H 0.1143 0.6992 0.6124 0.070 Uiso 1 1 calc R . . . .
C10 C 0.1843(3) 0.8308(3) 0.6364(3) 0.0709(11) Uani 1 1 d . . . . .
H10 H 0.1672 0.8417 0.7034 0.085 Uiso 1 1 calc R . . . .
C11 C 0.2409(4) 0.8990(3) 0.5918(4) 0.0817(13) Uani 1 1 d . . . . .
H11 H 0.2614 0.9569 0.6278 0.098 Uiso 1 1 calc R . . . .
C12 C 0.2670(4) 0.8818(3) 0.4945(4) 0.0852(14) Uani 1 1 d . . . . .
H12 H 0.3067 0.9277 0.4650 0.102 Uiso 1 1 calc R . . . .
C13 C 0.2353(3) 0.7973(3) 0.4393(3) 0.0658(10) Uani 1 1 d . . . . .
H13 H 0.2533 0.7870 0.3726 0.079 Uiso 1 1 calc R . . . .
C14 C 0.4226(3) 0.5839(2) 0.6608(3) 0.0507(8) Uani 1 1 d . . . . .
H14 H 0.3632 0.6238 0.6656 0.061 Uiso 1 1 calc R . . . .
C15 C 0.5276(3) 0.6180(3) 0.6857(3) 0.0589(9) Uani 1 1 d . . . . .
H15 H 0.5408 0.6814 0.7092 0.071 Uiso 1 1 calc R . . . .
C16 C 0.6172(3) 0.5581(3) 0.6762(3) 0.0646(10) Uani 1 1 d . . . . .
H16 H 0.6891 0.5824 0.6931 0.077 Uiso 1 1 calc R . . . .
C17 C 0.5997(3) 0.4653(3) 0.6426(3) 0.0570(9) Uani 1 1 d . . . . .
H17 H 0.6591 0.4266 0.6351 0.068 Uiso 1 1 calc R . . . .
C18 C 0.4905(3) 0.4280(2) 0.6192(2) 0.0456(8) Uani 1 1 d . . . . .
C19 C 0.3070(2) 0.4366(2) 0.5996(2) 0.0411(7) Uani 1 1 d . . . . .
C20 C 0.3402(3) 0.3450(2) 0.5761(2) 0.0439(7) Uani 1 1 d . . . . .
C21 C 0.2685(3) 0.2612(2) 0.5391(3) 0.0477(8) Uani 1 1 d . . . . .
C22 C 0.1800(3) 0.2360(3) 0.5847(3) 0.0612(10) Uani 1 1 d . . . . .
H22 H 0.1672 0.2695 0.6444 0.073 Uiso 1 1 calc R . . . .
C23 C 0.1106(3) 0.1605(3) 0.5412(4) 0.0742(12) Uani 1 1 d . . . . .
H23 H 0.0515 0.1438 0.5723 0.089 Uiso 1 1 calc R . . . .
C24 C 0.1279(4) 0.1105(3) 0.4537(4) 0.0822(14) Uani 1 1 d . . . . .
H24 H 0.0800 0.0610 0.4241 0.099 Uiso 1 1 calc R . . . .
C25 C 0.2177(4) 0.1342(3) 0.4093(4) 0.0800(13) Uani 1 1 d . . . . .
H25 H 0.2306 0.0993 0.3505 0.096 Uiso 1 1 calc R . . . .
C26 C 0.2879(3) 0.2084(2) 0.4507(3) 0.0611(10) Uani 1 1 d . . . . .
H26 H 0.3479 0.2234 0.4203 0.073 Uiso 1 1 calc R . . . .
N1 N 0.09719(19) 0.49155(18) 0.36343(19) 0.0411(6) Uani 1 1 d . . . . .
N2 N 0.1063(2) 0.6450(2) 0.3094(2) 0.0515(7) Uani 1 1 d . . . . .
N3 N 0.4042(2) 0.48991(18) 0.62855(19) 0.0417(6) Uani 1 1 d . . . . .
N4 N 0.4530(2) 0.3401(2) 0.5879(2) 0.0506(7) Uani 1 1 d . . . . .
Se1 Se 0.16596(3) 0.49047(2) 0.59630(3) 0.04526(13) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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
C2 C1 H1 120.3 . . ?
C2 C1 N1 119.5(3) . . ?
N1 C1 H1 120.3 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 118.4(3) . . ?
N2 C5 C4 130.1(3) . . ?
N2 C5 N1 111.5(3) . . ?
C7 C6 N1 105.0(3) . . ?
C7 C6 Se1 133.1(2) . . ?
N1 C6 Se1 121.8(2) . . ?
C6 C7 C8 129.1(3) . . ?
N2 C7 C6 111.5(3) . . ?
N2 C7 C8 119.5(3) . . ?
C9 C8 C7 122.2(3) . . ?
C13 C8 C7 119.9(3) . . ?
C13 C8 C9 117.9(3) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 N3 119.4(3) . . ?
N3 C14 H14 120.3 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
N3 C18 C17 117.9(3) . . ?
N4 C18 C17 130.5(3) . . ?
N4 C18 N3 111.6(3) . . ?
C20 C19 N3 105.4(3) . . ?
C20 C19 Se1 132.3(2) . . ?
N3 C19 Se1 122.3(2) . . ?
C19 C20 C21 127.3(3) . . ?
N4 C20 C19 111.3(3) . . ?
N4 C20 C21 121.4(3) . . ?
C22 C21 C20 122.6(3) . . ?
C22 C21 C26 119.1(3) . . ?
C26 C21 C20 118.2(3) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.9(4) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.3(4) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25 119.5 . . ?
C21 C26 H26 120.2 . . ?
C25 C26 C21 119.6(4) . . ?
C25 C26 H26 120.2 . . ?
C1 N1 C5 122.0(3) . . ?
C1 N1 C6 131.2(3) . . ?
C5 N1 C6 106.8(3) . . ?
C5 N2 C7 105.1(3) . . ?
C14 N3 C18 122.2(3) . . ?
C14 N3 C19 131.5(3) . . ?
C19 N3 C18 106.4(3) . . ?
C18 N4 C20 105.4(3) . . ?
C19 Se1 C6 100.03(12) . . ?
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
C1 H1 0.9300 . ?
C1 C2 1.342(5) . ?
C1 N1 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.403(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.407(5) . ?
C5 N1 1.376(4) . ?
C5 N2 1.338(4) . ?
C6 C7 1.381(4) . ?
C6 N1 1.394(4) . ?
C6 Se1 1.896(3) . ?
C7 C8 1.469(4) . ?
C7 N2 1.369(4) . ?
C8 C9 1.384(4) . ?
C8 C13 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.359(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.351(4) . ?
C14 N3 1.369(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.408(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.357(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.413(4) . ?
C18 N3 1.392(4) . ?
C18 N4 1.333(4) . ?
C19 C20 1.386(4) . ?
C19 N3 1.389(4) . ?
C19 Se1 1.885(3) . ?
C20 C21 1.474(4) . ?
C20 N4 1.369(4) . ?
C21 C22 1.386(5) . ?
C21 C26 1.400(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.362(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(5) . ?
C26 H26 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
C1 C2 C3 C4 2.3(6) . . . . ?
C2 C1 N1 C5 -1.2(5) . . . . ?
C2 C1 N1 C6 179.6(3) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 N1 -0.6(6) . . . . ?
C3 C4 C5 N2 179.4(4) . . . . ?
C4 C5 N1 C1 2.0(5) . . . . ?
C4 C5 N1 C6 -178.6(3) . . . . ?
C4 C5 N2 C7 178.7(4) . . . . ?
C6 C7 C8 C9 -39.2(5) . . . . ?
C6 C7 C8 C13 142.6(4) . . . . ?
C6 C7 N2 C5 0.7(4) . . . . ?
C7 C6 N1 C1 178.5(3) . . . . ?
C7 C6 N1 C5 -0.9(3) . . . . ?
C7 C6 Se1 C19 -102.6(3) . . . . ?
C7 C8 C9 C10 -177.4(3) . . . . ?
C7 C8 C13 C12 177.7(3) . . . . ?
C8 C7 N2 C5 179.8(3) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C9 C8 C13 C12 -0.6(6) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
C10 C11 C12 C13 1.3(7) . . . . ?
C11 C12 C13 C8 -0.5(7) . . . . ?
C13 C8 C9 C10 0.9(5) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C14 N3 C18 -0.7(5) . . . . ?
C15 C14 N3 C19 179.3(3) . . . . ?
C15 C16 C17 C18 -1.3(5) . . . . ?
C16 C17 C18 N3 2.0(5) . . . . ?
C16 C17 C18 N4 -178.3(3) . . . . ?
C17 C18 N3 C14 -1.0(4) . . . . ?
C17 C18 N3 C19 179.0(3) . . . . ?
C17 C18 N4 C20 -179.5(3) . . . . ?
C19 C20 C21 C22 -44.2(5) . . . . ?
C19 C20 C21 C26 132.6(3) . . . . ?
C19 C20 N4 C18 0.3(4) . . . . ?
C20 C19 N3 C14 -179.1(3) . . . . ?
C20 C19 N3 C18 0.9(3) . . . . ?
C20 C19 Se1 C6 -94.9(3) . . . . ?
C20 C21 C22 C23 175.4(3) . . . . ?
C20 C21 C26 C25 -175.4(3) . . . . ?
C21 C20 N4 C18 178.3(3) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C22 C21 C26 C25 1.5(5) . . . . ?
C22 C23 C24 C25 1.5(6) . . . . ?
C23 C24 C25 C26 -1.4(7) . . . . ?
C24 C25 C26 C21 -0.2(6) . . . . ?
C26 C21 C22 C23 -1.4(5) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
N1 C5 N2 C7 -1.3(4) . . . . ?
N1 C6 C7 C8 -178.9(3) . . . . ?
N1 C6 C7 N2 0.1(3) . . . . ?
N1 C6 Se1 C19 80.2(2) . . . . ?
N2 C5 N1 C1 -178.0(3) . . . . ?
N2 C5 N1 C6 1.4(3) . . . . ?
N2 C7 C8 C9 141.9(3) . . . . ?
N2 C7 C8 C13 -36.3(4) . . . . ?
N3 C14 C15 C16 1.4(5) . . . . ?
N3 C18 N4 C20 0.3(3) . . . . ?
N3 C19 C20 C21 -178.7(3) . . . . ?
N3 C19 C20 N4 -0.8(3) . . . . ?
N3 C19 Se1 C6 84.3(3) . . . . ?
N4 C18 N3 C14 179.2(3) . . . . ?
N4 C18 N3 C19 -0.8(3) . . . . ?
N4 C20 C21 C22 138.1(3) . . . . ?
N4 C20 C21 C26 -45.1(4) . . . . ?
Se1 C6 C7 C8 3.5(5) . . . . ?
Se1 C6 C7 N2 -177.5(2) . . . . ?
Se1 C6 N1 C1 -3.6(4) . . . . ?
Se1 C6 N1 C5 177.1(2) . . . . ?
Se1 C19 C20 C21 0.7(5) . . . . ?
Se1 C19 C20 N4 178.5(2) . . . . ?
Se1 C19 N3 C14 1.5(4) . . . . ?
Se1 C19 N3 C18 -178.5(2) . . . . ?
