# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_20220402-d-156-2
_database_code_depnum_ccdc_archive 'CCDC 2178078'
loop_
_audit_author_name
_audit_author_address
'Xiangnan Gong'
;Chongqiang University
China
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_audit_creation_date             2022-04-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O2 Se'
_chemical_formula_sum            'C15 H10 O2 Se'
_chemical_formula_weight         301.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Sn'
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'
O O 0.0106 0.0060 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9033(5)
_cell_length_b                   11.9615(7)
_cell_length_c                   14.6472(9)
_cell_angle_alpha                73.300(5)
_cell_angle_beta                 83.619(5)
_cell_angle_gamma                74.420(5)
_cell_volume                     1276.68(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3380
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3730
_cell_measurement_theta_min      1.8700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.931
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.059
_diffrn_reflns_theta_min         1.835
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  88.00   1.00    5.77    --   18.74  57.00-180.00   89
  2  ω    -49.00  40.00   1.00    5.77    --   18.74 -57.00 -90.00   89
  3  ω     -5.00  41.00   1.00    5.77    --   18.74  77.00-120.00   46
  4  ω     -5.00  36.00   1.00    5.77    --   18.74  77.00 120.00   41
  5  ω    -11.00  33.00   1.00    5.77    --   18.74  77.00  30.00   44
  6  ω    -50.00  22.00   1.00    5.77    --   18.74 -57.00  30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0795550000
_diffrn_orient_matrix_UB_12      -0.0186645000
_diffrn_orient_matrix_UB_13      0.0076186000
_diffrn_orient_matrix_UB_21      0.0424345000
_diffrn_orient_matrix_UB_22      -0.0550891000
_diffrn_orient_matrix_UB_23      0.0317836000
_diffrn_orient_matrix_UB_31      -0.0237254000
_diffrn_orient_matrix_UB_32      0.0264977000
_diffrn_orient_matrix_UB_33      0.0386177000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3696
_reflns_number_total             5792
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_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     325
_refine_ls_number_reflns         5792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.044
_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)+(0.0344P)²+0.7430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1093
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C23(H23), C25(H25), C10(H10), C9(H9), C29(H29), C24(H24), C30(H30),
 C14(H14), C5(H5), C16(H16), C15(H15), C1(H1), C20(H20), C18(H18), C17(H17),
 C3(H3), C4(H4), C19(H19), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.15881(5) 0.76406(4) 0.89882(3) 0.06507(16) Uani 1 1 d . . . . .
Se2 Se 0.28998(6) 0.24797(4) 0.60729(4) 0.07073(17) Uani 1 1 d . . . . .
O4 O 0.6692(4) -0.2060(2) 0.6742(2) 0.0670(8) Uani 1 1 d . . . . .
O2 O 0.6470(4) 0.3955(2) 0.8237(2) 0.0715(8) Uani 1 1 d . . . . .
O3 O 0.6063(4) 0.1357(3) 0.6917(2) 0.0775(9) Uani 1 1 d . . . . .
O1 O 0.1331(4) 0.5752(3) 0.8368(3) 0.0884(11) Uani 1 1 d . . . . .
C12 C 0.4296(4) 0.5642(3) 0.8599(3) 0.0459(8) Uani 1 1 d . . . . .
C27 C 0.4903(4) -0.0003(3) 0.6437(3) 0.0472(9) Uani 1 1 d . . . . .
C11 C 0.6032(5) 0.4992(3) 0.8545(3) 0.0509(9) Uani 1 1 d . . . . .
C7 C 0.3971(4) 0.6694(3) 0.8914(3) 0.0459(8) Uani 1 1 d . . . . .
C26 C 0.5165(5) -0.1207(3) 0.6431(3) 0.0533(9) Uani 1 1 d . . . . .
C6 C 0.2078(4) 0.8934(3) 0.9358(3) 0.0512(9) Uani 1 1 d . . . . .
C22 C 0.3317(5) 0.0809(3) 0.6084(3) 0.0508(9) Uani 1 1 d . . . . .
C8 C 0.5361(4) 0.7021(3) 0.9168(3) 0.0548(10) Uani 1 1 d . . . . .
H8 H 0.515221 0.771544 0.937169 0.066 Uiso 1 1 calc R U . . .
C28 C 0.6265(5) 0.0338(4) 0.6821(3) 0.0539(10) Uani 1 1 d . . . . .
C13 C 0.2883(5) 0.5216(4) 0.8343(3) 0.0600(10) Uani 1 1 d . . . . .
C23 C 0.2092(5) 0.0398(4) 0.5747(3) 0.0600(10) Uani 1 1 d . . . . .
H23 H 0.105122 0.093446 0.550393 0.072 Uiso 1 1 calc R U . . .
C25 C 0.3937(5) -0.1621(4) 0.6107(3) 0.0642(11) Uani 1 1 d . . . . .
H25 H 0.414278 -0.242807 0.611776 0.077 Uiso 1 1 calc R U . . .
C10 C 0.7427(5) 0.5311(3) 0.8804(3) 0.0607(11) Uani 1 1 d . . . . .
H10 H 0.857323 0.485205 0.876406 0.073 Uiso 1 1 calc R U . . .
C9 C 0.7071(5) 0.6323(3) 0.9122(3) 0.0603(11) Uani 1 1 d . . . . .
H9 H 0.798806 0.654824 0.931008 0.072 Uiso 1 1 calc R U . . .
C21 C 0.0694(5) 0.3110(4) 0.5439(4) 0.0646(11) Uani 1 1 d . . . . .
C29 C 0.7845(5) -0.0598(4) 0.7082(3) 0.0629(11) Uani 1 1 d . . . . .
H29 H 0.879338 -0.042068 0.728371 0.076 Uiso 1 1 calc R U . . .
C24 C 0.2411(6) -0.0811(4) 0.5769(3) 0.0677(12) Uani 1 1 d . . . . .
H24 H 0.156737 -0.107405 0.555001 0.081 Uiso 1 1 calc R U . . .
C30 C 0.7971(5) -0.1716(4) 0.7040(3) 0.0704(12) Uani 1 1 d . . . . .
H30 H 0.900963 -0.229506 0.722898 0.084 Uiso 1 1 calc R U . . .
C14 C 0.3486(6) 0.4106(4) 0.8058(3) 0.0735(13) Uani 1 1 d . . . . .
H14 H 0.266369 0.376624 0.790518 0.088 Uiso 1 1 calc R U . . .
C5 C 0.2092(5) 0.8890(4) 1.0301(3) 0.0716(12) Uani 1 1 d . . . . .
H5 H 0.189277 0.822444 1.077367 0.086 Uiso 1 1 calc R U . . .
C16 C 0.0704(6) 0.3700(4) 0.4489(4) 0.0726(13) Uani 1 1 d . . . . .
H16 H 0.176746 0.375339 0.415942 0.087 Uiso 1 1 calc R U . . .
C15 C 0.5164(7) 0.3566(4) 0.8011(3) 0.0776(14) Uani 1 1 d . . . . .
H15 H 0.547167 0.286716 0.780782 0.093 Uiso 1 1 calc R U . . .
C1 C 0.2324(6) 0.9930(4) 0.8658(4) 0.0834(14) Uani 1 1 d . . . . .
H1 H 0.229460 0.995369 0.801945 0.100 Uiso 1 1 calc R U . . .
C20 C -0.0887(6) 0.3035(4) 0.5928(4) 0.0883(15) Uani 1 1 d . . . . .
H20 H -0.090870 0.263938 0.657460 0.106 Uiso 1 1 calc R U . . .
C18 C -0.2410(8) 0.4138(5) 0.4506(5) 0.098(2) Uani 1 1 d . . . . .
H18 H -0.345944 0.448784 0.418981 0.118 Uiso 1 1 calc R U . . .
C17 C -0.0850(8) 0.4219(4) 0.4015(4) 0.0909(16) Uani 1 1 d . . . . .
H17 H -0.083677 0.461814 0.336856 0.109 Uiso 1 1 calc R U . . .
C3 C 0.2676(8) 1.0833(7) 0.9832(8) 0.140(4) Uani 1 1 d . . . . .
H3 H 0.290466 1.147639 0.999118 0.168 Uiso 1 1 calc R U . . .
C4 C 0.2411(7) 0.9859(7) 1.0543(5) 0.118(3) Uani 1 1 d . . . . .
H4 H 0.244299 0.984331 1.117936 0.142 Uiso 1 1 calc R U . . .
C19 C -0.2442(7) 0.3553(5) 0.5447(5) 0.104(2) Uani 1 1 d . . . . .
H19 H -0.351040 0.349989 0.577157 0.125 Uiso 1 1 calc R U . . .
C2 C 0.2611(8) 1.0880(5) 0.8894(7) 0.135(3) Uani 1 1 d . . . . .
H2 H 0.276167 1.155772 0.841967 0.162 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C7 1.929(3) . ?
Se1 C6 1.921(4) . ?
Se2 C22 1.931(4) . ?
Se2 C21 1.929(4) . ?
O4 C26 1.378(4) . ?
O4 C30 1.344(5) . ?
O2 C11 1.385(4) . ?
O2 C15 1.346(5) . ?
O3 C28 1.233(4) . ?
O1 C13 1.224(4) . ?
C12 C11 1.390(5) . ?
C12 C7 1.413(4) . ?
C12 C13 1.468(5) . ?
C27 C26 1.401(5) . ?
C27 C22 1.408(5) . ?
C27 C28 1.463(5) . ?
C11 C10 1.382(5) . ?
C7 C8 1.379(4) . ?
C26 C25 1.381(5) . ?
C6 C5 1.368(5) . ?
C6 C1 1.374(6) . ?
C22 C23 1.387(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(5) . ?
C28 C29 1.438(5) . ?
C13 C14 1.448(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.392(5) . ?
C25 H25 0.9300 . ?
C25 C24 1.366(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.369(5) . ?
C9 H9 0.9300 . ?
C21 C16 1.367(6) . ?
C21 C20 1.381(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.333(5) . ?
C24 H24 0.9300 . ?
C30 H30 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.314(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.394(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(6) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.357(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.387(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.368(8) . ?
C18 C19 1.356(8) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.367(10) . ?
C3 C2 1.366(11) . ?
C4 H4 0.9300 . ?
C19 H19 0.9300 . ?
C2 H2 0.9300 . ?

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
C6 Se1 C7 98.27(14) . . ?
C21 Se2 C22 99.17(16) . . ?
C30 O4 C26 118.8(3) . . ?
C15 O2 C11 118.4(3) . . ?
C11 C12 C7 117.6(3) . . ?
C11 C12 C13 119.7(3) . . ?
C7 C12 C13 122.7(3) . . ?
C26 C27 C22 117.6(3) . . ?
C26 C27 C28 118.7(3) . . ?
C22 C27 C28 123.7(3) . . ?
O2 C11 C12 121.4(3) . . ?
C10 C11 O2 115.4(3) . . ?
C10 C11 C12 123.2(3) . . ?
C12 C7 Se1 119.3(2) . . ?
C8 C7 Se1 121.3(3) . . ?
C8 C7 C12 119.4(3) . . ?
O4 C26 C27 121.7(3) . . ?
O4 C26 C25 115.4(3) . . ?
C25 C26 C27 123.0(4) . . ?
C5 C6 Se1 120.6(3) . . ?
C5 C6 C1 120.7(4) . . ?
C1 C6 Se1 118.6(3) . . ?
C27 C22 Se2 119.1(3) . . ?
C23 C22 Se2 121.3(3) . . ?
C23 C22 C27 119.6(3) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
O3 C28 C27 122.2(3) . . ?
O3 C28 C29 122.4(4) . . ?
C29 C28 C27 115.4(3) . . ?
O1 C13 C12 122.9(3) . . ?
O1 C13 C14 122.9(4) . . ?
C14 C13 C12 114.2(3) . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C26 C25 H25 121.0 . . ?
C24 C25 C26 118.0(4) . . ?
C24 C25 H25 121.0 . . ?
C11 C10 H10 121.0 . . ?
C9 C10 C11 118.0(3) . . ?
C9 C10 H10 121.0 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C16 C21 Se2 118.5(4) . . ?
C16 C21 C20 119.5(4) . . ?
C20 C21 Se2 121.8(4) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.5(4) . . ?
C25 C24 H24 119.3 . . ?
O4 C30 H30 117.9 . . ?
C29 C30 O4 124.1(4) . . ?
C29 C30 H30 117.9 . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.7(4) . . ?
C15 C14 H14 119.1 . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.0(5) . . ?
C4 C5 H5 120.5 . . ?
C21 C16 H16 119.7 . . ?
C21 C16 C17 120.7(5) . . ?
C17 C16 H16 119.7 . . ?
O2 C15 H15 117.7 . . ?
C14 C15 O2 124.5(4) . . ?
C14 C15 H15 117.7 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.2(6) . . ?
C2 C1 H1 119.9 . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.5(5) . . ?
C19 C20 H20 120.2 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C19 C18 C17 120.8(5) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.3(6) . . ?
C18 C17 H17 120.3 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(6) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(6) . . ?
C3 C4 H4 120.4 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.2(5) . . ?
C18 C19 H19 119.9 . . ?
C1 C2 C3 119.6(7) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?

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
Se1 C7 C8 C9 179.2(3) . . . . ?
Se1 C6 C5 C4 -178.5(3) . . . . ?
Se1 C6 C1 C2 177.7(4) . . . . ?
Se2 C22 C23 C24 -179.4(3) . . . . ?
Se2 C21 C16 C17 -176.8(3) . . . . ?
Se2 C21 C20 C19 176.9(4) . . . . ?
O4 C26 C25 C24 -178.6(4) . . . . ?
O2 C11 C10 C9 -179.5(4) . . . . ?
O3 C28 C29 C30 174.6(4) . . . . ?
O1 C13 C14 C15 178.0(5) . . . . ?
C12 C11 C10 C9 -0.6(6) . . . . ?
C12 C7 C8 C9 -0.3(6) . . . . ?
C12 C13 C14 C15 -2.1(7) . . . . ?
C27 C26 C25 C24 0.7(6) . . . . ?
C27 C22 C23 C24 1.0(6) . . . . ?
C27 C28 C29 C30 -4.9(6) . . . . ?
C11 O2 C15 C14 0.3(7) . . . . ?
C11 C12 C7 Se1 179.3(3) . . . . ?
C11 C12 C7 C8 -1.2(6) . . . . ?
C11 C12 C13 O1 -179.4(4) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C11 C10 C9 C8 -1.0(6) . . . . ?
C7 C12 C11 O2 -179.5(3) . . . . ?
C7 C12 C11 C10 1.7(6) . . . . ?
C7 C12 C13 O1 1.2(7) . . . . ?
C7 C12 C13 C14 -178.7(4) . . . . ?
C7 C8 C9 C10 1.5(7) . . . . ?
C26 O4 C30 C29 2.0(6) . . . . ?
C26 C27 C22 Se2 -179.7(3) . . . . ?
C26 C27 C22 C23 -0.1(5) . . . . ?
C26 C27 C28 O3 -174.2(4) . . . . ?
C26 C27 C28 C29 5.4(5) . . . . ?
C26 C25 C24 C23 0.2(7) . . . . ?
C6 C5 C4 C3 0.9(8) . . . . ?
C6 C1 C2 C3 0.9(9) . . . . ?
C22 C27 C26 O4 178.5(3) . . . . ?
C22 C27 C26 C25 -0.8(6) . . . . ?
C22 C27 C28 O3 4.8(6) . . . . ?
C22 C27 C28 C29 -175.6(4) . . . . ?
C22 C23 C24 C25 -1.0(7) . . . . ?
C28 C27 C26 O4 -2.4(5) . . . . ?
C28 C27 C26 C25 178.3(4) . . . . ?
C28 C27 C22 Se2 1.3(5) . . . . ?
C28 C27 C22 C23 -179.1(4) . . . . ?
C28 C29 C30 O4 1.3(7) . . . . ?
C13 C12 C11 O2 1.1(6) . . . . ?
C13 C12 C11 C10 -177.8(4) . . . . ?
C13 C12 C7 Se1 -1.3(5) . . . . ?
C13 C12 C7 C8 178.2(4) . . . . ?
C13 C14 C15 O2 1.7(8) . . . . ?
C21 C16 C17 C18 0.1(7) . . . . ?
C21 C20 C19 C18 -0.5(8) . . . . ?
C30 O4 C26 C27 -1.4(5) . . . . ?
C30 O4 C26 C25 178.0(4) . . . . ?
C5 C6 C1 C2 0.9(7) . . . . ?
C16 C21 C20 C19 0.4(7) . . . . ?
C15 O2 C11 C12 -1.6(6) . . . . ?
C15 O2 C11 C10 177.3(4) . . . . ?
C1 C6 C5 C4 -1.8(6) . . . . ?
C20 C21 C16 C17 -0.2(6) . . . . ?
C17 C18 C19 C20 0.4(8) . . . . ?
C4 C3 C2 C1 -1.8(11) . . . . ?
C19 C18 C17 C16 -0.2(8) . . . . ?
C2 C3 C4 C5 0.9(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.135
_oxdiff_exptl_absorpt_empirical_full_min 0.828
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20220829-d-276-1-200k
_database_code_depnum_ccdc_archive 'CCDC 2205235'
loop_
_audit_author_name
_audit_author_address
'Xiangnan Gong'
;Chongqiang University
China
;
_audit_update_record             
;
2022-09-05 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_audit_creation_date             2022-08-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O2 Se'
_chemical_formula_sum            'C20 H19 N O2 Se'
_chemical_formula_weight         384.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H19 N O2 Se'
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'
O O 0.0106 0.0060 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0338(3)
_cell_length_b                   8.4987(4)
_cell_length_c                   13.3369(5)
_cell_angle_alpha                74.087(4)
_cell_angle_beta                 74.630(3)
_cell_angle_gamma                81.377(4)
_cell_volume                     841.45(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6393
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.9770
_cell_measurement_theta_min      3.5790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.101
_diffrn_reflns_theta_min         3.307
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  14.00   1.00    1.44    --   18.74  77.00 -60.00   25
  2  ω    -50.00  44.00   1.00    1.44    --   18.74 -38.00 120.00   94
  3  ω     26.00  86.00   1.00    1.44    --   18.74  38.00 -60.00   60
  4  ω     -9.00  31.00   1.00    1.44    --   18.74  77.00 150.00   40
  5  ω    -48.00  38.00   1.00    1.44    --   18.74 -57.00  30.00   86
  6  ω     -7.00  19.00   1.00    1.44    --   18.74  38.00 -60.00   26
  7  ω    -42.00  10.00   1.00    1.44    --  -18.85 -77.00 -60.00   52
  8  ω     16.00  87.00   1.00    1.44    --   18.58  57.00-180.00   71
  9  ω    -40.00  49.00   1.00    1.44    --   18.58 -77.00 -90.00   89
 10  ω     -5.00  59.00   1.00    1.44    --   18.58 -99.00   0.00   64
 11  ω     25.00  60.00   1.00    1.44    --   18.58 -99.00-180.00   35
 12  ω     -1.00  87.00   1.00    1.44    --   18.58  57.00  60.00   88
 13  ω     16.00  46.00   1.00    1.44    --  -18.78  57.00 -60.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0685907000
_diffrn_orient_matrix_UB_12      0.0607868000
_diffrn_orient_matrix_UB_13      0.0103760000
_diffrn_orient_matrix_UB_21      -0.0570391000
_diffrn_orient_matrix_UB_22      -0.0623198000
_diffrn_orient_matrix_UB_23      0.0278397000
_diffrn_orient_matrix_UB_31      0.0220098000
_diffrn_orient_matrix_UB_32      -0.0023585000
_diffrn_orient_matrix_UB_33      0.0485316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3500
_reflns_number_total             3985
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.078
_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)+(0.0259P)²+0.2014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0708
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C20(H20), C9(H9), C17(H17), C8(H8), C7(H7), C19(H19),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.45244(3) 0.79590(3) 0.95251(2) 0.02989(8) Uani 1 1 d . . . . .
O2 O 0.63139(18) 0.8244(2) 0.75130(11) 0.0339(4) Uani 1 1 d . . . . .
O1 O 0.1974(2) 0.6781(2) 0.55788(12) 0.0485(5) Uani 1 1 d . . . . .
N1 N 0.4975(2) 0.7578(3) 0.43767(13) 0.0374(5) Uani 1 1 d . . . . .
H1 H 0.404458 0.742399 0.419793 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3516(2) 0.7560(2) 0.76825(14) 0.0220(4) Uani 1 1 d . . . . .
C15 C 0.3054(2) 0.7595(3) 1.09572(15) 0.0262(4) Uani 1 1 d . . . . .
C10 C 0.2978(2) 0.7525(2) 0.87764(15) 0.0231(4) Uani 1 1 d . . . . .
C12 C 0.5292(2) 0.7963(2) 0.70498(15) 0.0240(4) Uani 1 1 d . . . . .
C16 C 0.2235(3) 0.8941(3) 1.13573(17) 0.0293(4) Uani 1 1 d . . . . .
H16 H 0.225632 1.001299 1.089427 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2982(3) 0.6032(3) 1.16303(16) 0.0296(5) Uani 1 1 d . . . . .
H20 H 0.352528 0.511078 1.135972 0.036 Uiso 1 1 calc R U . . .
C9 C 0.1264(3) 0.7195(3) 0.93159(16) 0.0283(4) Uani 1 1 d . . . . .
H9 H 0.088447 0.716816 1.005794 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2338(2) 0.7241(2) 0.71653(15) 0.0243(4) Uani 1 1 d . . . . .
C4 C 0.4722(3) 0.7642(3) 0.54065(15) 0.0281(4) Uani 1 1 d . . . . .
C13 C 0.5821(2) 0.8050(3) 0.59064(15) 0.0256(4) Uani 1 1 d . . . . .
C17 C 0.1390(3) 0.8710(3) 1.24312(17) 0.0360(5) Uani 1 1 d . . . . .
H17 H 0.084523 0.962689 1.270613 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0120(3) 0.6911(3) 0.87848(16) 0.0298(5) Uani 1 1 d . . . . .
H8 H -0.103808 0.670240 0.916179 0.036 Uiso 1 1 calc R U . . .
C7 C 0.0652(3) 0.6927(3) 0.77104(16) 0.0294(5) Uani 1 1 d . . . . .
H7 H -0.013378 0.672436 0.734742 0.035 Uiso 1 1 calc R U . . .
C19 C 0.2112(3) 0.5812(3) 1.27027(16) 0.0321(5) Uani 1 1 d . . . . .
H19 H 0.204843 0.473739 1.316238 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2916(3) 0.7189(3) 0.60294(16) 0.0296(5) Uani 1 1 d . . . . .
C18 C 0.1339(3) 0.7150(3) 1.31024(17) 0.0342(5) Uani 1 1 d . . . . .
H18 H 0.077141 0.699644 1.384008 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7618(3) 0.8602(3) 0.53693(16) 0.0351(5) Uani 1 1 d . . . . .
H14A H 0.786154 0.939354 0.571455 0.053 Uiso 1 1 calc R U . . .
H14B H 0.768372 0.912007 0.460827 0.053 Uiso 1 1 calc R U . . .
H14C H 0.847201 0.764949 0.543705 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6541(3) 0.7724(3) 0.35109(16) 0.0320(5) Uani 1 1 d . . . . .
H3A H 0.749157 0.695032 0.375007 0.038 Uiso 1 1 calc R U . . .
H3B H 0.690713 0.885236 0.330933 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6167(3) 0.7337(3) 0.25640(16) 0.0365(5) Uani 1 1 d . . . . .
H2A H 0.519709 0.810181 0.234419 0.044 Uiso 1 1 calc R U . . .
H2B H 0.579671 0.620856 0.277776 0.044 Uiso 1 1 calc R U . . .
C1 C 0.7723(3) 0.7471(3) 0.16154(17) 0.0402(6) Uani 1 1 d . . . . .
H1A H 0.742428 0.717707 0.102736 0.060 Uiso 1 1 calc R U . . .
H1B H 0.869054 0.672264 0.182950 0.060 Uiso 1 1 calc R U . . .
H1C H 0.805903 0.860083 0.137659 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C15 1.9309(19) . ?
Se1 C10 1.9169(18) . ?
O2 C12 1.233(2) . ?
O1 C5 1.220(2) . ?
N1 H1 0.8800 . ?
N1 C4 1.349(2) . ?
N1 C3 1.459(3) . ?
C11 C10 1.401(3) . ?
C11 C12 1.488(3) . ?
C11 C6 1.404(2) . ?
C15 C16 1.396(3) . ?
C15 C20 1.384(3) . ?
C10 C9 1.404(3) . ?
C12 C13 1.455(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.390(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.382(3) . ?
C6 C7 1.384(3) . ?
C6 C5 1.473(3) . ?
C4 C13 1.369(3) . ?
C4 C5 1.516(3) . ?
C13 C14 1.512(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.379(3) . ?
C7 H7 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.381(3) . ?
C18 H18 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.501(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.517(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C10 Se1 C15 99.76(8) . . ?
C4 N1 H1 114.7 . . ?
C4 N1 C3 130.52(17) . . ?
C3 N1 H1 114.7 . . ?
C10 C11 C12 121.67(16) . . ?
C10 C11 C6 119.11(17) . . ?
C6 C11 C12 119.21(16) . . ?
C16 C15 Se1 119.43(16) . . ?
C20 C15 Se1 120.33(16) . . ?
C20 C15 C16 119.74(19) . . ?
C11 C10 Se1 121.04(14) . . ?
C11 C10 C9 118.73(17) . . ?
C9 C10 Se1 120.22(14) . . ?
O2 C12 C11 118.58(17) . . ?
O2 C12 C13 120.15(17) . . ?
C13 C12 C11 121.27(17) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C20 H20 120.1 . . ?
C15 C20 C19 119.9(2) . . ?
C19 C20 H20 120.1 . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.07(18) . . ?
C8 C9 H9 119.5 . . ?
C11 C6 C5 119.58(17) . . ?
C7 C6 C11 121.25(17) . . ?
C7 C6 C5 119.15(17) . . ?
N1 C4 C13 129.60(19) . . ?
N1 C4 C5 110.30(17) . . ?
C13 C4 C5 120.10(17) . . ?
C12 C13 C14 114.48(17) . . ?
C4 C13 C12 120.05(17) . . ?
C4 C13 C14 125.47(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.34(18) . . ?
C7 C8 H8 119.8 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.49(18) . . ?
C8 C7 H7 120.3 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
O1 C5 C6 121.41(18) . . ?
O1 C5 C4 119.15(18) . . ?
C6 C5 C4 119.44(17) . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
N1 C3 C2 108.75(17) . . ?
H3A C3 H3B 108.3 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C3 C2 C1 112.58(18) . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
Se1 C15 C16 C17 -170.41(15) . . . . ?
Se1 C15 C20 C19 171.17(14) . . . . ?
Se1 C10 C9 C8 178.74(16) . . . . ?
O2 C12 C13 C4 176.06(19) . . . . ?
O2 C12 C13 C14 -3.7(3) . . . . ?
N1 C4 C13 C12 -177.3(2) . . . . ?
N1 C4 C13 C14 2.5(4) . . . . ?
N1 C4 C5 O1 2.7(3) . . . . ?
N1 C4 C5 C6 -177.66(19) . . . . ?
N1 C3 C2 C1 179.5(2) . . . . ?
C11 C10 C9 C8 0.0(3) . . . . ?
C11 C12 C13 C4 -4.7(3) . . . . ?
C11 C12 C13 C14 175.49(18) . . . . ?
C11 C6 C7 C8 -0.7(3) . . . . ?
C11 C6 C5 O1 173.8(2) . . . . ?
C11 C6 C5 C4 -5.8(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 C20 C19 C18 -0.8(3) . . . . ?
C10 C11 C12 O2 1.3(3) . . . . ?
C10 C11 C12 C13 -177.97(19) . . . . ?
C10 C11 C6 C7 1.4(3) . . . . ?
C10 C11 C6 C5 -176.82(19) . . . . ?
C10 C9 C8 C7 0.7(3) . . . . ?
C12 C11 C10 Se1 -1.1(3) . . . . ?
C12 C11 C10 C9 177.63(18) . . . . ?
C12 C11 C6 C7 -177.31(19) . . . . ?
C12 C11 C6 C5 4.5(3) . . . . ?
C16 C15 C20 C19 -0.8(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C20 C15 C16 C17 1.6(3) . . . . ?
C20 C19 C18 C17 1.6(3) . . . . ?
C9 C8 C7 C6 -0.4(3) . . . . ?
C6 C11 C10 Se1 -179.74(14) . . . . ?
C6 C11 C10 C9 -1.0(3) . . . . ?
C6 C11 C12 O2 179.89(19) . . . . ?
C6 C11 C12 C13 0.7(3) . . . . ?
C4 N1 C3 C2 172.4(2) . . . . ?
C13 C4 C5 O1 -177.8(2) . . . . ?
C13 C4 C5 C6 1.8(3) . . . . ?
C7 C6 C5 O1 -4.4(3) . . . . ?
C7 C6 C5 C4 175.95(19) . . . . ?
C5 C6 C7 C8 177.5(2) . . . . ?
C5 C4 C13 C12 3.3(3) . . . . ?
C5 C4 C13 C14 -176.9(2) . . . . ?
C3 N1 C4 C13 8.4(4) . . . . ?
C3 N1 C4 C5 -172.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.888
