# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_se
_database_code_depnum_ccdc_archive 'CCDC 2093778'
loop_
_audit_author_name
_audit_author_address
'G-Q Liu'
;Nantong University
China
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_audit_creation_date             2021-06-24
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 Br N O3 Se'
_chemical_formula_sum            'C17 H14 Br N O3 Se'
_chemical_formula_weight         439.16
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   12.5541(7)
_cell_length_b                   6.6650(4)
_cell_length_c                   20.2899(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.002(6)
_cell_angle_gamma                90
_cell_volume                     1654.19(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      27.9230
_cell_measurement_theta_min      3.1460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0461
_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       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.060
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00   6.00   1.00    5.00    --  -11.27 -38.00  30.00   85
  2  ω    -14.00  25.00   1.00    5.00    --  -11.27 -99.00-120.00   39
  3  ω    -80.00   9.00   1.00    5.00    --  -11.27 -38.00 -60.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068999000
_diffrn_orient_matrix_UB_12      -0.0394106000
_diffrn_orient_matrix_UB_13      -0.0312510000
_diffrn_orient_matrix_UB_21      -0.0571209000
_diffrn_orient_matrix_UB_22      0.0076475000
_diffrn_orient_matrix_UB_23      -0.0134098000
_diffrn_orient_matrix_UB_31      0.0071467000
_diffrn_orient_matrix_UB_32      0.0985789000
_diffrn_orient_matrix_UB_33      -0.0114393000
_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                2327
_reflns_number_total             2898
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.037
_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)+(0.0174P)²+1.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
Br1 Br 0.06995(3) 0.15842(6) 0.43546(2) 0.04128(13) Uani 1 1 d . . . . .
Se1 Se 0.64044(3) 0.35181(5) 0.76239(2) 0.02818(12) Uani 1 1 d . . . . .
O1 O 0.43410(18) 0.7644(3) 0.65115(11) 0.0259(6) Uani 1 1 d . . . . .
O2 O 0.42986(17) 0.5229(3) 0.80388(11) 0.0203(5) Uani 1 1 d . . . . .
O3 O 0.30421(18) 0.2820(3) 0.77149(12) 0.0280(6) Uani 1 1 d . . . . .
N1 N 0.3578(2) 0.4904(4) 0.69333(13) 0.0156(6) Uani 1 1 d . . . . .
C1 C 0.6256(3) 0.3424(5) 0.66647(18) 0.0236(8) Uani 1 1 d . . . . .
C2 C 0.6436(3) 0.5023(5) 0.62680(19) 0.0295(9) Uani 1 1 d . . . . .
H2 H 0.660204 0.628459 0.645961 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6365(3) 0.4732(6) 0.5582(2) 0.0395(10) Uani 1 1 d . . . . .
H3 H 0.646442 0.581470 0.531348 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6151(3) 0.2867(6) 0.5295(2) 0.0429(11) Uani 1 1 d . . . . .
H4 H 0.611416 0.267919 0.483649 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5992(3) 0.1277(6) 0.5697(2) 0.0424(10) Uani 1 1 d . . . . .
H5 H 0.586010 0.000448 0.550838 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6026(3) 0.1548(5) 0.63740(19) 0.0307(9) Uani 1 1 d . . . . .
H6 H 0.589348 0.047180 0.663617 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6036(3) 0.6277(5) 0.78052(18) 0.0222(8) Uani 1 1 d . . . . .
H7A H 0.639283 0.659664 0.826861 0.027 Uiso 1 1 calc R U . . .
H7B H 0.634048 0.715688 0.751398 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4825(2) 0.6755(4) 0.77061(16) 0.0182(7) Uani 1 1 d . . . . .
C9 C 0.4666(3) 0.8779(5) 0.80058(19) 0.0294(9) Uani 1 1 d . . . . .
H9A H 0.389922 0.907276 0.792715 0.044 Uiso 1 1 calc R U . . .
H9B H 0.502287 0.979228 0.779684 0.044 Uiso 1 1 calc R U . . .
H9C H 0.497538 0.875829 0.848362 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4237(2) 0.6570(4) 0.69738(17) 0.0174(7) Uani 1 1 d . . . . .
C11 C 0.3581(3) 0.4159(5) 0.75779(17) 0.0191(7) Uani 1 1 d . . . . .
C12 C 0.2892(2) 0.4116(5) 0.63266(16) 0.0174(7) Uani 1 1 d . . . . .
C13 C 0.2994(3) 0.2122(5) 0.61630(18) 0.0260(8) Uani 1 1 d . . . . .
H13 H 0.350146 0.129909 0.644222 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2330(3) 0.1374(5) 0.55766(19) 0.0310(9) Uani 1 1 d . . . . .
H14 H 0.237738 0.003123 0.546200 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1601(3) 0.2616(5) 0.51656(17) 0.0262(8) Uani 1 1 d . . . . .
C16 C 0.1507(3) 0.4602(5) 0.53239(17) 0.0247(8) Uani 1 1 d . . . . .
H16 H 0.101452 0.542974 0.503595 0.030 Uiso 1 1 calc R U . . .
C17 C 0.2152(3) 0.5362(5) 0.59163(17) 0.0211(8) Uani 1 1 d . . . . .
H17 H 0.208570 0.669589 0.603554 0.025 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
Br1 C15 1.904(3) . ?
Se1 C1 1.914(3) . ?
Se1 C7 1.951(3) . ?
O1 C10 1.210(4) . ?
O2 C8 1.458(4) . ?
O2 C11 1.347(4) . ?
O3 C11 1.190(4) . ?
N1 C10 1.377(4) . ?
N1 C11 1.398(4) . ?
N1 C12 1.434(4) . ?
C1 C2 1.384(5) . ?
C1 C6 1.385(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(4) . ?
C8 C9 1.512(4) . ?
C8 C10 1.508(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 C13 1.383(4) . ?
C12 C17 1.377(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(5) . ?
C15 C16 1.374(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 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
C1 Se1 C7 104.46(14) . . ?
C11 O2 C8 110.5(2) . . ?
C10 N1 C11 110.8(3) . . ?
C10 N1 C12 125.7(3) . . ?
C11 N1 C12 123.2(3) . . ?
C2 C1 Se1 125.1(3) . . ?
C2 C1 C6 119.6(3) . . ?
C6 C1 Se1 115.2(3) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
Se1 C7 H7A 108.2 . . ?
Se1 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 Se1 116.4(2) . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
O2 C8 C7 109.7(2) . . ?
O2 C8 C9 108.8(3) . . ?
O2 C8 C10 103.1(2) . . ?
C9 C8 C7 110.6(3) . . ?
C10 C8 C7 111.5(3) . . ?
C10 C8 C9 112.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N1 126.8(3) . . ?
O1 C10 C8 127.0(3) . . ?
N1 C10 C8 106.2(3) . . ?
O2 C11 N1 108.8(3) . . ?
O3 C11 O2 124.1(3) . . ?
O3 C11 N1 127.1(3) . . ?
C13 C12 N1 119.2(3) . . ?
C17 C12 N1 119.4(3) . . ?
C17 C12 C13 121.4(3) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 Br1 119.6(3) . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 Br1 119.0(3) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 119.2(3) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?

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
Br1 C15 C16 C17 179.3(2) . . . . ?
Se1 C1 C2 C3 176.1(3) . . . . ?
Se1 C1 C6 C5 -174.6(3) . . . . ?
Se1 C7 C8 O2 47.7(3) . . . . ?
Se1 C7 C8 C9 167.6(2) . . . . ?
Se1 C7 C8 C10 -65.9(3) . . . . ?
O2 C8 C10 O1 173.9(3) . . . . ?
O2 C8 C10 N1 -7.5(3) . . . . ?
N1 C12 C13 C14 -180.0(3) . . . . ?
N1 C12 C17 C16 178.7(3) . . . . ?
C1 C2 C3 C4 -1.9(6) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C1 -2.1(6) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C7 C8 C10 O1 -68.5(4) . . . . ?
C7 C8 C10 N1 110.1(3) . . . . ?
C8 O2 C11 O3 180.0(3) . . . . ?
C8 O2 C11 N1 -0.8(3) . . . . ?
C9 C8 C10 O1 56.8(4) . . . . ?
C9 C8 C10 N1 -124.7(3) . . . . ?
C10 N1 C11 O2 -4.5(3) . . . . ?
C10 N1 C11 O3 174.8(3) . . . . ?
C10 N1 C12 C13 126.1(3) . . . . ?
C10 N1 C12 C17 -53.3(4) . . . . ?
C11 O2 C8 C7 -113.7(3) . . . . ?
C11 O2 C8 C9 125.2(3) . . . . ?
C11 O2 C8 C10 5.1(3) . . . . ?
C11 N1 C10 O1 -173.9(3) . . . . ?
C11 N1 C10 C8 7.6(3) . . . . ?
C11 N1 C12 C13 -60.1(4) . . . . ?
C11 N1 C12 C17 120.5(3) . . . . ?
C12 N1 C10 O1 0.6(5) . . . . ?
C12 N1 C10 C8 -178.0(3) . . . . ?
C12 N1 C11 O2 -179.1(2) . . . . ?
C12 N1 C11 O3 0.1(5) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C13 C12 C17 C16 -0.7(5) . . . . ?
C13 C14 C15 Br1 179.3(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C12 1.4(5) . . . . ?
C17 C12 C13 C14 -0.6(5) . . . . ?

_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 1.915
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_se2
_database_code_depnum_ccdc_archive 'CCDC 2116754'
loop_
_audit_author_name
_audit_author_address
'G-Q Liu'
;Nantong University
China
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N O2 S2 Se'
_chemical_formula_sum            'C15 H17 N O2 S2 Se'
_chemical_formula_weight         386.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0638(5)
_cell_length_b                   8.2150(7)
_cell_length_c                   24.112(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1597.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2285
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      24.7130
_cell_measurement_theta_min      2.6090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7121
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.619
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  47.00   1.00    8.00    --  -11.59   0.00  60.00   70
  2  ω   -100.00 -58.00   1.00    8.00    --  -11.59   0.00  60.00   42
  3  ω    -13.00  19.00   1.00    8.00    --  -11.59  19.00   0.00   32
  4  ω     39.00  99.00   1.00    8.00    --   11.74-178.00   0.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0017509000
_diffrn_orient_matrix_UB_12      -0.0853979000
_diffrn_orient_matrix_UB_13      -0.0042730000
_diffrn_orient_matrix_UB_21      -0.0272348000
_diffrn_orient_matrix_UB_22      0.0112488000
_diffrn_orient_matrix_UB_23      -0.0277145000
_diffrn_orient_matrix_UB_31      0.0836084000
_diffrn_orient_matrix_UB_32      0.0054530000
_diffrn_orient_matrix_UB_33      -0.0089316000
_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         0.704
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2471
_reflns_number_total             2808
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.065
_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)+(0.0341P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.51(2)
 0.49(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(S2A) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.2
4. Others
 Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(S2A)=1-FVAR(1)
 Sof(S2)=Sof(H15A)=Sof(H15B)=Sof(H14)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C3(H3), C4(H4), C14(H14), C5(H5)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
Se01 Se 0.89570(8) 0.73376(10) 0.48052(3) 0.0220(2) Uani 1 1 d . . . . .
S1 S 0.7789(2) 0.6074(2) 0.68865(8) 0.0176(5) Uani 1 1 d . . . . .
S2 S 0.4738(3) 0.7498(4) 0.74067(10) 0.0302(8) Uani 0.842(5) 1 d . . P A 1
O1 O 0.8081(6) 0.4677(6) 0.6551(2) 0.0241(14) Uani 1 1 d . . . . .
O2 O 0.8398(6) 0.6141(7) 0.7442(2) 0.0285(14) Uani 1 1 d . . . . .
C15 C 0.4440(12) 0.5541(12) 0.6560(4) 0.017(3) Uani 1 1 d . U . . .
H15A H 0.451564 0.436502 0.658489 0.020 Uiso 0.842(5) 1 calc R U P A 1
H15B H 0.466089 0.586171 0.618022 0.020 Uiso 0.842(5) 1 calc R U P A 1
N1 N 0.8541(5) 0.7628(8) 0.6560(2) 0.0161(13) Uani 1 1 d . . . . .
C2 C 0.7125(8) 0.4305(9) 0.5001(3) 0.0198(19) Uani 1 1 d . . . . .
H2 H 0.708045 0.459573 0.537327 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7957(9) 0.4856(10) 0.4064(3) 0.0210(19) Uani 1 1 d . . . . .
H6 H 0.848570 0.552273 0.380739 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8069(7) 0.7829(9) 0.5961(3) 0.0161(17) Uani 1 1 d . . . . .
H8 H 0.699291 0.731018 0.589425 0.019 Uiso 1 1 calc R U . . .
C7 C 0.9387(8) 0.7032(10) 0.5594(3) 0.024(2) Uani 1 1 d . . . . .
H7A H 0.942634 0.587569 0.567481 0.029 Uiso 1 1 calc R U . . .
H7B H 1.046280 0.749000 0.568420 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6386(8) 0.2886(9) 0.4823(4) 0.0287(19) Uani 1 1 d . . . . .
H3 H 0.587319 0.220789 0.507972 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7907(9) 0.9651(10) 0.5884(3) 0.027(2) Uani 1 1 d . . . . .
H9A H 0.892795 1.010687 0.573869 0.033 Uiso 1 1 calc R U . . .
H9B H 0.700976 0.990419 0.563096 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5623(8) 0.6284(8) 0.6927(3) 0.0168(17) Uani 1 1 d . . . . .
C1 C 0.7939(8) 0.5301(10) 0.4622(3) 0.0228(19) Uani 1 1 d . . . . .
C4 C 0.6393(9) 0.2451(11) 0.4267(3) 0.035(2) Uani 1 1 d . . . . .
H4 H 0.586065 0.150755 0.415009 0.042 Uiso 1 1 calc R U . . .
C14 C 0.2790(9) 0.6084(11) 0.6727(3) 0.028(2) Uani 1 1 d . . . . .
H14 H 0.182058 0.576750 0.654808 0.034 Uiso 0.842(5) 1 calc R U P A 1
C11 C 0.8575(8) 0.9235(9) 0.6834(3) 0.023(2) Uani 1 1 d . . . . .
H11A H 0.970147 0.963767 0.686502 0.027 Uiso 1 1 calc R U . . .
H11B H 0.808714 0.917854 0.720094 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7549(10) 1.0317(10) 0.6454(4) 0.029(2) Uani 1 1 d . . . . .
H10A H 0.637697 1.023665 0.654090 0.035 Uiso 1 1 calc R U . . .
H10B H 0.789070 1.144582 0.648342 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7205(10) 0.3444(10) 0.3888(4) 0.033(2) Uani 1 1 d . . . . .
H5 H 0.724034 0.315457 0.351503 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2819(9) 0.7092(10) 0.7168(4) 0.030(2) Uani 1 1 d . . . . .
H13A H 0.345400 0.660519 0.746089 0.044 Uiso 0.158(5) 1 calc R U P A 2
H13B H 0.170628 0.728231 0.729398 0.044 Uiso 0.158(5) 1 calc R U P A 2
H13C H 0.331690 0.810805 0.706285 0.044 Uiso 0.158(5) 1 calc R U P A 2
S2A S 0.4463(19) 0.518(2) 0.6434(7) 0.008(4) Uani 0.158(5) 1 d . U P A 2


_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
Se01 C7 1.951(7) . ?
Se01 C1 1.915(8) . ?
S1 O1 1.423(6) . ?
S1 O2 1.428(5) . ?
S1 N1 1.617(6) . ?
S1 C12 1.758(7) . ?
S2 C12 1.686(7) . ?
S2 C13 1.685(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C12 1.436(12) . ?
C15 C14 1.460(12) . ?
N1 C8 1.504(8) . ?
N1 C11 1.476(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(10) . ?
C2 C1 1.391(10) . ?
C6 H6 0.9300 . ?
C6 C1 1.394(11) . ?
C6 C5 1.376(11) . ?
C8 H8 0.9800 . ?
C8 C7 1.530(9) . ?
C8 C9 1.514(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.386(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.506(12) . ?
C12 S2A 1.763(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(11) . ?
C14 H14 0.9300 . ?
C14 C13 1.348(11) . ?
C14 S2A 1.695(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.521(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 H5 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C1 Se01 C7 100.9(3) . . ?
O1 S1 O2 120.4(3) . . ?
O1 S1 N1 107.4(3) . . ?
O1 S1 C12 106.0(3) . . ?
O2 S1 N1 107.3(3) . . ?
O2 S1 C12 106.6(3) . . ?
N1 S1 C12 108.8(3) . . ?
C13 S2 C12 92.1(4) . . ?
H15A C15 H15B 108.5 . . ?
C12 C15 H15A 110.1 . . ?
C12 C15 H15B 110.1 . . ?
C12 C15 C14 107.8(8) . . ?
C14 C15 H15A 110.1 . . ?
C14 C15 H15B 110.1 . . ?
C8 N1 S1 117.3(5) . . ?
C11 N1 S1 119.7(5) . . ?
C11 N1 C8 109.6(6) . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.8(7) . . ?
C1 C2 H2 120.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C1 121.0(8) . . ?
N1 C8 H8 109.5 . . ?
N1 C8 C7 109.4(5) . . ?
N1 C8 C9 104.3(6) . . ?
C7 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C9 C8 C7 114.4(6) . . ?
Se01 C7 H7A 109.1 . . ?
Se01 C7 H7B 109.1 . . ?
C8 C7 Se01 112.6(5) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(8) . . ?
C4 C3 H3 119.4 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 105.3(7) . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
S1 C12 S2A 116.0(7) . . ?
S2 C12 S1 121.1(4) . . ?
C15 C12 S1 125.7(6) . . ?
C15 C12 S2 113.1(6) . . ?
C15 C12 S2A 9.8(8) . . ?
C2 C1 Se01 124.4(6) . . ?
C2 C1 C6 118.9(7) . . ?
C6 C1 Se01 116.6(6) . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(9) . . ?
C5 C4 H4 120.4 . . ?
C15 C14 H14 123.6 . . ?
C15 C14 S2A 13.0(8) . . ?
C13 C14 C15 112.9(8) . . ?
C13 C14 H14 123.6 . . ?
C13 C14 S2A 125.8(9) . . ?
N1 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
N1 C11 C10 104.1(6) . . ?
H11A C11 H11B 109.0 . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C9 C10 C11 103.4(7) . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C6 C5 C4 119.9(8) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C14 C13 S2 114.0(6) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 S2A C12 85.2(9) . . ?

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
S1 N1 C8 C7 -93.5(6) . . . . ?
S1 N1 C8 C9 143.7(5) . . . . ?
S1 N1 C11 C10 -120.6(6) . . . . ?
S1 C12 S2A C14 -177.4(6) . . . . ?
O1 S1 N1 C8 49.4(5) . . . . ?
O1 S1 N1 C11 -173.7(5) . . . . ?
O1 S1 C12 S2 164.8(4) . . . . ?
O1 S1 C12 C15 -17.9(8) . . . . ?
O1 S1 C12 S2A -16.0(8) . . . . ?
O2 S1 N1 C8 -179.9(5) . . . . ?
O2 S1 N1 C11 -43.0(5) . . . . ?
O2 S1 C12 S2 35.4(6) . . . . ?
O2 S1 C12 C15 -147.3(7) . . . . ?
O2 S1 C12 S2A -145.4(7) . . . . ?
C15 C12 S2A C14 -6(4) . . . . ?
C15 C14 C13 S2 1.1(10) . . . . ?
C15 C14 S2A C12 5(3) . . . . ?
N1 S1 C12 S2 -80.0(5) . . . . ?
N1 S1 C12 C15 97.3(7) . . . . ?
N1 S1 C12 S2A 99.2(7) . . . . ?
N1 C8 C7 Se01 -176.6(5) . . . . ?
N1 C8 C9 C10 -24.0(7) . . . . ?
N1 C11 C10 C9 -33.7(7) . . . . ?
C2 C3 C4 C5 2.0(11) . . . . ?
C8 N1 C11 C10 19.3(7) . . . . ?
C8 C9 C10 C11 35.9(8) . . . . ?
C7 C8 C9 C10 -143.6(6) . . . . ?
C3 C2 C1 Se01 177.9(5) . . . . ?
C3 C2 C1 C6 1.4(10) . . . . ?
C3 C4 C5 C6 -1.4(11) . . . . ?
C9 C8 C7 Se01 -60.0(7) . . . . ?
C12 S1 N1 C8 -64.9(6) . . . . ?
C12 S1 N1 C11 72.0(5) . . . . ?
C12 S2 C13 C14 -1.1(7) . . . . ?
C12 C15 C14 C13 -0.5(10) . . . . ?
C12 C15 C14 S2A -174(4) . . . . ?
C1 C2 C3 C4 -2.0(11) . . . . ?
C1 C6 C5 C4 0.9(11) . . . . ?
C14 C15 C12 S1 -177.8(6) . . . . ?
C14 C15 C12 S2 -0.3(9) . . . . ?
C14 C15 C12 S2A 172(5) . . . . ?
C11 N1 C8 C7 125.5(6) . . . . ?
C11 N1 C8 C9 2.7(7) . . . . ?
C5 C6 C1 Se01 -177.6(5) . . . . ?
C5 C6 C1 C2 -0.9(11) . . . . ?
C13 S2 C12 S1 178.4(5) . . . . ?
C13 S2 C12 C15 0.8(7) . . . . ?
C13 C14 S2A C12 -2.8(11) . . . . ?

_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.831
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51(2)
2 0.49(2)

