# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_crf-10-23a_auto
_database_code_depnum_ccdc_archive 'CCDC 2430771'
loop_
_audit_author_name
_audit_author_address
'renfei Cao'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2025-03-12 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_audit_creation_date             2025-02-20
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O4 Se'
_chemical_formula_sum            'C19 H19 N O4 Se'
_chemical_formula_weight         404.31
_chemical_absolute_configuration R
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Se  CHON'
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'
O O 0.0492 0.0322 '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'

_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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   25.6226(2)
_cell_length_b                   19.4121(2)
_cell_length_c                   7.06020(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3511.66(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23552
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.4220
_cell_measurement_theta_min      2.8300
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.747
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            45936
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.008
_diffrn_reflns_theta_min         2.856
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -72.00   0.50    0.05    --  -47.70   0.00   0.00   80
  2  ω    -54.00  21.00   0.50    0.05    --  -47.70  74.00  68.00  150
  3  ω    -13.00  26.00   0.50    0.05    --  -47.70  19.00 120.00   78
  4  ω    -10.00  27.00   0.50    0.05    --  -47.70  19.00  30.00   74
  5  ω   -108.00 -37.00   0.50    0.22    -- -101.00  77.00 -90.00  142
  6  ω   -108.00 -83.00   0.50    0.22    -- -101.00 111.00 -46.13   50
  7  ω    -99.00 -54.00   0.50    0.22    -- -101.00  74.00  68.00   90
  8  ω    -55.00 -30.00   0.50    0.22    -- -101.00 105.00  19.18   50
  9  ω   -107.00 -81.00   0.50    0.22    -- -101.00 105.00  19.18   52
 10  ω    -76.00 -50.00   0.50    0.22    -- -101.00 111.00 -46.13   52
 11  ω    -63.00 -30.00   0.50    0.22    -- -101.00  57.00 -90.00   66
 12  ω   -174.00-130.00   0.50    0.22    -- -101.00 -19.00 -30.00   88
 13  ω   -168.00 -86.00   0.50    0.22    -- -101.00 -57.00  30.00  164
 14  ω   -165.00 -86.00   0.50    0.22    -- -101.00 -57.00   0.00  158
 15  ω    -86.00 -34.00   0.50    0.05    --  -47.70 -74.00 -59.00  104
 16  ω   -171.00 -80.00   0.50    0.22    -- -101.00 -74.00 -59.00  182
 17  ω   -113.00 -88.00   0.50    0.22    -- -101.00 -19.00 -30.00   50
 18  ω   -128.00 -95.00   0.50    0.22    -- -101.00 -37.00  90.00   66
 19  ω   -174.00-138.00   0.50    0.22    -- -101.00 -37.00  90.00   72
 20  ω    -25.00  19.00   0.50    0.05    --   47.70 -19.00 -60.00   88
 21  ω     12.00  61.00   0.50    0.05    --   47.70 -74.00 -59.00   98
 22  ω     71.00  96.00   0.50    0.22    --  107.11 -74.00 -59.00   50
 23  ω     43.00  70.00   0.50    0.22    --  107.11 -57.00-180.00   54
 24  ω     37.00  69.00   0.50    0.22    --  107.11 -57.00  90.00   64
 25  ω     35.00  70.00   0.50    0.22    --  107.11 -57.00 120.00   70
 26  ω     35.00  69.00   0.50    0.22    --  107.11 -57.00 150.00   68
 27  ω    119.00 144.00   0.50    0.22    --  107.11   0.00  30.00   50
 28  ω     87.00 119.00   0.50    0.22    --  107.11  74.00  68.00   64
 29  ω     27.00 118.00   0.50    0.05    --   47.70  74.00  68.00  182
 30  ω    130.00 174.00   0.50    0.22    --  107.11  74.00  68.00   88
 31  ω    112.00 172.00   0.50    0.22    --  107.11   0.00-120.00  120
 32  ω     19.00  93.00   0.50    0.05    --   47.70-125.00 -60.00  148
 33  ω     42.00  68.00   0.50    0.22    --  107.11-125.00   0.00   52
 34  ω     57.00  97.00   0.50    0.22    --  107.11 -99.00 -60.00   80
 35  ω     40.00  73.00   0.50    0.22    --  107.11 -99.00-150.00   66
 36  ω     86.00 111.00   0.50    0.22    --  107.11-125.00   0.00   50
 37  ω     79.00 104.00   0.50    0.22    --  107.11 -99.00   0.00   50
 38  ω     41.00 104.00   0.50    0.22    --  107.11-125.00  90.00  126
 39  ω     81.00 106.00   0.50    0.22    --  107.11 -99.00 120.00   50
 40  ω     61.00  86.00   0.50    0.22    --  107.11 -99.00 150.00   50
 41  ω     39.00  64.00   0.50    0.22    --  107.11-125.00 150.00   50
 42  ω     38.00  66.00   0.50    0.22    --  107.11 -99.00 120.00   56
 43  ω     73.00 106.00   0.50    0.22    --  107.11 -99.00  90.00   66
 44  ω     81.00 106.00   0.50    0.22    --  107.11 -99.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1224773000
_diffrn_orient_matrix_UB_12      0.0492028000
_diffrn_orient_matrix_UB_13      -0.0097216000
_diffrn_orient_matrix_UB_21      0.0323656000
_diffrn_orient_matrix_UB_22      0.0027865000
_diffrn_orient_matrix_UB_23      0.0784032000
_diffrn_orient_matrix_UB_31      0.1776404000
_diffrn_orient_matrix_UB_32      -0.0344503000
_diffrn_orient_matrix_UB_33      -0.0075620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                6699
_reflns_number_total             7259
_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 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.141a 64-bit (release 04-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 2702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         7259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.052
_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)+(0.0685P)²+2.9046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H6 of C6, H3 of C3, H7 of C7, H36 of C36, H17 of C17,
  H16 of C16, H37 of C37, H38 of C38, H15 of C15, H22 of C22, H35 of C35, H18
  of C18, H25 of C25, H26 of C26, H34 of C34
 At 1.5 times of:
  All C(H,H,H) groups, H19 of C19
2. Uiso/Uaniso restraints and constraints
Uanis(O6) = Uanis(O7)
Uanis(O2) = Uanis(O3)
Uanis(O2) = Uanis(N1)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C27(H27A,H27B),
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22),
 C25(H25), C26(H26), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.30206(2) 0.63115(2) 0.58783(9) 0.04286(16) Uani 1 1 d . . . . .
O1 O 0.38764(14) 0.33787(18) 0.5729(9) 0.0593(12) Uani 1 1 d . . . . .
O2 O 0.46410(16) 0.5712(2) 0.6504(10) 0.0820(10) Uani 1 1 d . . . . .
O3 O 0.40603(16) 0.6401(2) 0.5364(10) 0.0820(10) Uani 1 1 d . . . . .
O4 O 0.19286(17) 0.5273(2) 0.3829(6) 0.0654(11) Uani 1 1 d . . . . .
N1 N 0.4201(2) 0.5827(3) 0.5892(14) 0.0820(10) Uani 1 1 d . . . . .
C1 C 0.4417(2) 0.3244(3) 0.5742(13) 0.0671(19) Uani 1 1 d . . . . .
H1A H 0.458391 0.350753 0.476233 0.101 Uiso 1 1 calc R U . . .
H1B H 0.447620 0.276225 0.552290 0.101 Uiso 1 1 calc R U . . .
H1C H 0.456055 0.337109 0.694920 0.101 Uiso 1 1 calc R U . . .
C2 C 0.37158(19) 0.4045(2) 0.5796(9) 0.0399(10) Uani 1 1 d . . . . .
C3 C 0.40452(19) 0.4603(3) 0.5859(10) 0.0480(12) Uani 1 1 d . . . . .
H3 H 0.440517 0.454379 0.590108 0.058 Uiso 1 1 calc R U . . .
C4 C 0.38262(18) 0.5264(2) 0.5859(9) 0.0421(11) Uani 1 1 d . . . . .
C5 C 0.32988(18) 0.5397(2) 0.5856(7) 0.0363(9) Uani 1 1 d . . . . .
C6 C 0.29746(18) 0.4811(2) 0.5835(7) 0.0369(9) Uani 1 1 d . . . . .
H6 H 0.261425 0.486787 0.582987 0.044 Uiso 1 1 calc R U . . .
C7 C 0.31798(18) 0.4155(2) 0.5821(8) 0.0381(10) Uani 1 1 d . . . . .
H7 H 0.295532 0.377833 0.582830 0.046 Uiso 1 1 calc R U . . .
C8 C 0.23087(18) 0.6183(3) 0.6888(7) 0.0385(10) Uani 1 1 d . . . . .
H8A H 0.227057 0.570783 0.728645 0.046 Uiso 1 1 calc R U . . .
H8B H 0.226908 0.647049 0.800371 0.046 Uiso 1 1 calc R U . . .
C9 C 0.18668(18) 0.6355(3) 0.5497(7) 0.0398(10) Uani 1 1 d . . . . .
C10 C 0.1846(2) 0.5870(3) 0.3821(8) 0.0450(12) Uani 1 1 d . . . . .
C11 C 0.1669(3) 0.6264(4) 0.2075(9) 0.0692(19) Uani 1 1 d . . . . .
H11A H 0.192587 0.622649 0.107197 0.083 Uiso 1 1 calc R U . . .
H11B H 0.133881 0.608508 0.161510 0.083 Uiso 1 1 calc R U . . .
C12 C 0.1611(3) 0.6990(4) 0.2679(10) 0.0685(18) Uani 1 1 d . . . . .
H12A H 0.124716 0.709820 0.292007 0.082 Uiso 1 1 calc R U . . .
H12B H 0.174172 0.730004 0.171157 0.082 Uiso 1 1 calc R U . . .
C13 C 0.1936(2) 0.7056(3) 0.4514(8) 0.0506(14) Uani 1 1 d . . . . .
H13A H 0.230020 0.714249 0.422700 0.061 Uiso 1 1 calc R U . . .
H13B H 0.180506 0.742698 0.530444 0.061 Uiso 1 1 calc R U . . .
C14 C 0.13479(18) 0.6308(3) 0.6589(7) 0.0386(10) Uani 1 1 d . . . . .
C15 C 0.1092(2) 0.5678(3) 0.6814(10) 0.0577(16) Uani 1 1 d . . . . .
H15 H 0.122588 0.528341 0.624537 0.069 Uiso 1 1 calc R U . . .
C16 C 0.0639(3) 0.5638(4) 0.7883(13) 0.079(2) Uani 1 1 d . . . . .
H16 H 0.047412 0.521427 0.803942 0.094 Uiso 1 1 calc R U . . .
C17 C 0.0430(3) 0.6212(5) 0.8711(12) 0.080(2) Uani 1 1 d . . . . .
H17 H 0.011955 0.618408 0.938678 0.096 Uiso 1 1 calc R U . . .
C18 C 0.0681(3) 0.6824(4) 0.8536(11) 0.074(2) Uani 1 1 d . . . . .
H18 H 0.054768 0.721248 0.913423 0.088 Uiso 1 1 calc R U . . .
C19 C 0.1135(3) 0.6876(3) 0.7477(10) 0.0578(15) Uani 1 1 d . . . . .
H19 H 0.128(3) 0.725(4) 0.751(12) 0.087 Uiso 1 1 d . U . . .
Se2 Se 0.30361(2) 0.36435(2) 0.09506(8) 0.04121(16) Uani 1 1 d . . . . .
O5 O 0.38463(14) 0.66013(18) 0.0742(8) 0.0553(11) Uani 1 1 d . . . . .
O6 O 0.46532(17) 0.4285(2) 0.1430(12) 0.1003(16) Uani 1 1 d . . . . .
O7 O 0.40743(18) 0.3579(3) 0.0423(13) 0.1003(16) Uani 1 1 d . . . . .
O8 O 0.22035(14) 0.24888(17) 0.0078(6) 0.0511(9) Uani 1 1 d . . . . .
N2 N 0.42089(16) 0.4157(2) 0.0856(10) 0.0573(13) Uani 1 1 d . . . . .
C20 C 0.4392(2) 0.6753(3) 0.0810(14) 0.071(2) Uani 1 1 d . . . . .
H20A H 0.455061 0.663041 -0.037544 0.107 Uiso 1 1 calc R U . . .
H20B H 0.455171 0.649297 0.181261 0.107 Uiso 1 1 calc R U . . .
H20C H 0.444097 0.723576 0.103939 0.107 Uiso 1 1 calc R U . . .
C21 C 0.36985(19) 0.5925(2) 0.0810(9) 0.0425(11) Uani 1 1 d . . . . .
C22 C 0.40333(18) 0.5375(3) 0.0841(10) 0.0477(12) Uani 1 1 d . . . . .
H22 H 0.439237 0.544520 0.085262 0.057 Uiso 1 1 calc R U . . .
C23 C 0.38304(18) 0.4709(2) 0.0855(9) 0.0430(11) Uani 1 1 d . . . . .
C24 C 0.32995(16) 0.4570(2) 0.0880(7) 0.0340(9) Uani 1 1 d . . . . .
C25 C 0.29732(18) 0.5142(2) 0.0883(7) 0.0380(10) Uani 1 1 d . . . . .
H25 H 0.261391 0.507452 0.090790 0.046 Uiso 1 1 calc R U . . .
C26 C 0.31636(17) 0.5801(2) 0.0850(8) 0.0386(10) Uani 1 1 d . . . . .
H26 H 0.293242 0.617076 0.085307 0.046 Uiso 1 1 calc R U . . .
C27 C 0.23254(18) 0.3774(3) 0.1962(7) 0.0397(10) Uani 1 1 d . . . . .
H27A H 0.227459 0.346041 0.301483 0.048 Uiso 1 1 calc R U . . .
H27B H 0.229590 0.423980 0.244979 0.048 Uiso 1 1 calc R U . . .
C28 C 0.18878(17) 0.3655(2) 0.0505(7) 0.0349(9) Uani 1 1 d . . . . .
C29 C 0.1880(2) 0.4153(3) -0.1184(8) 0.0458(12) Uani 1 1 d . . . . .
H29A H 0.171443 0.458530 -0.084057 0.055 Uiso 1 1 calc R U . . .
H29B H 0.223094 0.424688 -0.162768 0.055 Uiso 1 1 calc R U . . .
C30 C 0.1566(3) 0.3780(3) -0.2682(9) 0.0581(15) Uani 1 1 d . . . . .
H30A H 0.164138 0.396040 -0.393365 0.070 Uiso 1 1 calc R U . . .
H30B H 0.119465 0.382176 -0.244036 0.070 Uiso 1 1 calc R U . . .
C31 C 0.1745(3) 0.3030(3) -0.2504(9) 0.0588(15) Uani 1 1 d . . . . .
H31A H 0.145274 0.271797 -0.266927 0.071 Uiso 1 1 calc R U . . .
H31B H 0.200849 0.292440 -0.344536 0.071 Uiso 1 1 calc R U . . .
C32 C 0.19644(19) 0.2971(2) -0.0551(7) 0.0403(10) Uani 1 1 d . . . . .
C33 C 0.13638(18) 0.3638(3) 0.1598(7) 0.0395(10) Uani 1 1 d . . . . .
C34 C 0.1079(2) 0.4235(3) 0.1858(10) 0.0560(15) Uani 1 1 d . . . . .
H34 H 0.119504 0.464477 0.132127 0.067 Uiso 1 1 calc R U . . .
C35 C 0.0622(3) 0.4228(4) 0.2916(12) 0.071(2) Uani 1 1 d . . . . .
H35 H 0.043674 0.463445 0.309950 0.085 Uiso 1 1 calc R U . . .
C36 C 0.0441(2) 0.3617(4) 0.3702(11) 0.0679(17) Uani 1 1 d . . . . .
H36 H 0.013150 0.361097 0.439042 0.081 Uiso 1 1 calc R U . . .
C37 C 0.0717(3) 0.3030(4) 0.3459(11) 0.0664(18) Uani 1 1 d . . . . .
H37 H 0.059961 0.262172 0.399782 0.080 Uiso 1 1 calc R U . . .
C38 C 0.1178(2) 0.3034(3) 0.2404(9) 0.0528(14) Uani 1 1 d . . . . .
H38 H 0.136265 0.262650 0.223996 0.063 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 C5 1.913(5) . ?
Se1 C8 1.974(5) . ?
O1 C1 1.411(7) . ?
O1 C2 1.358(6) . ?
O2 N1 1.229(8) . ?
O3 N1 1.228(8) . ?
O4 C10 1.177(7) . ?
N1 C4 1.455(6) . ?
C2 C3 1.375(7) . ?
C2 C7 1.390(7) . ?
C3 C4 1.400(7) . ?
C4 C5 1.376(7) . ?
C5 C6 1.409(6) . ?
C6 C7 1.378(6) . ?
C8 C9 1.536(7) . ?
C9 C10 1.513(7) . ?
C9 C13 1.538(7) . ?
C9 C14 1.540(6) . ?
C10 C11 1.520(9) . ?
C11 C12 1.480(10) . ?
C12 C13 1.546(9) . ?
C14 C15 1.397(7) . ?
C14 C19 1.381(8) . ?
C15 C16 1.387(9) . ?
C16 C17 1.368(11) . ?
C17 C18 1.355(11) . ?
C18 C19 1.387(9) . ?
Se2 C24 1.922(4) . ?
Se2 C27 1.973(5) . ?
O5 C20 1.430(6) . ?
O5 C21 1.367(6) . ?
O6 N2 1.233(7) . ?
O7 N2 1.214(7) . ?
O8 C32 1.204(6) . ?
N2 C23 1.445(6) . ?
C21 C22 1.371(7) . ?
C21 C26 1.392(6) . ?
C22 C23 1.393(7) . ?
C23 C24 1.387(6) . ?
C24 C25 1.389(6) . ?
C25 C26 1.370(6) . ?
C27 C28 1.539(6) . ?
C28 C29 1.535(7) . ?
C28 C32 1.536(6) . ?
C28 C33 1.549(6) . ?
C29 C30 1.513(8) . ?
C30 C31 1.531(9) . ?
C31 C32 1.494(8) . ?
C33 C34 1.382(7) . ?
C33 C38 1.387(7) . ?
C34 C35 1.389(9) . ?
C35 C36 1.390(10) . ?
C36 C37 1.351(10) . ?
C37 C38 1.395(8) . ?

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
C5 Se1 C8 103.3(2) . . ?
C2 O1 C1 118.3(4) . . ?
O2 N1 C4 118.3(6) . . ?
O3 N1 O2 122.8(5) . . ?
O3 N1 C4 118.9(5) . . ?
O1 C2 C3 124.5(5) . . ?
O1 C2 C7 116.5(4) . . ?
C3 C2 C7 119.0(4) . . ?
C2 C3 C4 118.5(4) . . ?
C3 C4 N1 115.1(4) . . ?
C5 C4 N1 120.5(5) . . ?
C5 C4 C3 124.4(4) . . ?
C4 C5 Se1 122.7(3) . . ?
C4 C5 C6 115.3(4) . . ?
C6 C5 Se1 122.0(3) . . ?
C7 C6 C5 121.4(4) . . ?
C6 C7 C2 121.3(4) . . ?
C9 C8 Se1 115.0(3) . . ?
C8 C9 C13 113.3(4) . . ?
C8 C9 C14 107.7(4) . . ?
C10 C9 C8 113.0(4) . . ?
C10 C9 C13 101.7(4) . . ?
C10 C9 C14 108.9(4) . . ?
C13 C9 C14 112.2(4) . . ?
O4 C10 C9 127.0(6) . . ?
O4 C10 C11 123.6(6) . . ?
C9 C10 C11 109.3(5) . . ?
C12 C11 C10 106.0(5) . . ?
C11 C12 C13 105.5(5) . . ?
C9 C13 C12 104.0(5) . . ?
C15 C14 C9 121.0(5) . . ?
C19 C14 C9 121.4(5) . . ?
C19 C14 C15 117.5(5) . . ?
C16 C15 C14 120.3(6) . . ?
C17 C16 C15 120.9(7) . . ?
C18 C17 C16 119.4(6) . . ?
C17 C18 C19 120.7(7) . . ?
C14 C19 C18 121.2(6) . . ?
C24 Se2 C27 102.3(2) . . ?
C21 O5 C20 117.8(4) . . ?
O6 N2 C23 118.1(5) . . ?
O7 N2 O6 122.1(5) . . ?
O7 N2 C23 119.7(5) . . ?
O5 C21 C22 125.1(4) . . ?
O5 C21 C26 116.1(4) . . ?
C22 C21 C26 118.8(4) . . ?
C21 C22 C23 119.3(4) . . ?
C22 C23 N2 115.9(4) . . ?
C24 C23 N2 120.9(4) . . ?
C24 C23 C22 123.1(4) . . ?
C23 C24 Se2 121.8(3) . . ?
C23 C24 C25 115.8(4) . . ?
C25 C24 Se2 122.4(3) . . ?
C26 C25 C24 122.1(4) . . ?
C25 C26 C21 120.8(4) . . ?
C28 C27 Se2 114.3(3) . . ?
C27 C28 C33 107.6(4) . . ?
C29 C28 C27 115.8(4) . . ?
C29 C28 C32 99.8(4) . . ?
C29 C28 C33 112.9(4) . . ?
C32 C28 C27 111.2(4) . . ?
C32 C28 C33 109.5(4) . . ?
C30 C29 C28 104.4(4) . . ?
C29 C30 C31 103.8(5) . . ?
C32 C31 C30 105.2(5) . . ?
O8 C32 C28 124.0(5) . . ?
O8 C32 C31 126.3(5) . . ?
C31 C32 C28 109.5(4) . . ?
C34 C33 C28 120.3(5) . . ?
C34 C33 C38 118.2(5) . . ?
C38 C33 C28 121.4(4) . . ?
C33 C34 C35 120.6(6) . . ?
C34 C35 C36 120.3(6) . . ?
C37 C36 C35 119.6(6) . . ?
C36 C37 C38 120.4(6) . . ?
C33 C38 C37 121.0(6) . . ?

_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.424
####################################################################### 
# 
# 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_chenzmwzw-ii-167b_auto
_database_code_depnum_ccdc_archive 'CCDC 2440328'
loop_
_audit_author_name
_audit_author_address
'zhengwei wei'
;shanghai jiaotong university
China
;
_audit_update_record             
;
2025-04-02 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_audit_creation_date             2025-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
(1S,2R)-2-(((4-fluoro-2-nitrophenyl)selanyl)methyl)-2-phenylcyclopentan-1-ol
_chemical_name_systematic        
(1S,2R)-2-(((4-fluoro-2-nitrophenyl)selanyl)methyl)-2-phenylcyclopentan-1-ol
_chemical_formula_moiety         'C18 H18 F N O3 Se'
_chemical_formula_sum            'C18 H18 F N O3 Se'
_chemical_formula_weight         394.29
_chemical_absolute_configuration R
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONSe
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.23267(6)
_cell_length_b                   28.5347(2)
_cell_length_c                   8.41764(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.3528(9)
_cell_angle_gamma                90
_cell_volume                     1690.29(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7710
_cell_measurement_theta_min      3.0630
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.697
_exptl_absorpt_coefficient_mu    3.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            34526
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.948
_diffrn_reflns_theta_min         3.097
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -31.00   0.50    0.05    -- -101.00  57.00 120.00   60
  2  ω    -63.00 -28.00   0.50    0.05    -- -101.00  57.00  30.00   70
  3  ω    -63.00 -28.00   0.50    0.05    -- -101.00  57.00 -30.00   70
  4  ω    -62.00 -29.00   0.50    0.05    -- -101.00  57.00-120.00   66
  5  ω    107.00 132.00   0.50    0.05    --  107.11 116.00 -56.00   50
  6  ω     36.00  82.00   0.50    0.05    --   47.70  37.00 -60.00   92
  7  ω     25.00  61.00   0.50    0.05    --   47.70  77.00 -60.00   72
  8  ω     87.00 112.00   0.50    0.05    --   47.70  37.00 -60.00   50
  9  ω     38.00  91.00   0.50    0.05    --   47.70  37.00  60.00  106
 10  ω     36.00  81.00   0.50    0.05    --   47.70  57.00  90.00   90
 11  ω     79.00 112.00   0.50    0.05    --  107.11 163.00  92.00   66
 12  ω     63.00  88.00   0.50    0.05    --   47.70 163.00  92.00   50
 13  ω     36.00  96.00   0.50    0.05    --   47.70  37.00-150.00  120
 14  ω    -97.00 -72.00   0.50    0.05    --  -47.70 163.00  92.00   50
 15  ω   -124.00 -98.00   0.50    0.05    -- -101.00 163.00  92.00   52
 16  ω   -101.00 -75.00   0.50    0.05    -- -101.00 116.00 -56.00   52
 17  ω    -75.00  -9.00   0.50    0.05    --  -47.70 116.00 -56.00  132
 18  ω     47.00 106.00   0.50    0.05    --  107.11 -99.00 -90.00  118
 19  ω     82.00 107.00   0.50    0.05    --  107.11-116.00-145.00   50
 20  ω     41.00  77.00   0.50    0.05    --  107.11-116.00-145.00   72
 21  ω     45.00  96.00   0.50    0.05    --  107.11 -99.00-120.00  102
 22  ω    106.00 137.00   0.50    0.05    --  107.11-163.00  65.00   62
 23  ω     42.00 109.00   0.50    0.05    --  107.11-125.00 150.00  134
 24  ω     53.00  94.00   0.50    0.05    --  107.11-125.00  60.00   82
 25  ω     37.00 106.00   0.50    0.05    --  107.11 -99.00  60.00  138
 26  ω     40.00  67.00   0.50    0.05    --  107.11 -57.00 120.00   54
 27  ω     59.00  84.00   0.50    0.05    --   47.70-163.00  65.00   50
 28  ω     91.00 116.00   0.50    0.05    --   47.70-163.00  65.00   50
 29  ω     13.00  88.00   0.50    0.05    --   47.70-116.00-145.00  150
 30  ω    -58.00 -25.00   0.50    0.05    --  -47.70 -77.00-150.00   66
 31  ω    -83.00 -25.00   0.50    0.05    --  -47.70 -77.00 -30.00  116
 32  ω    -84.00 -28.00   0.50    0.05    --  -47.70 -77.00 -60.00  112
 33  ω    -69.00 -25.00   0.50    0.05    --  -47.70 -77.00-180.00   88
 34  ω    -65.00 -25.00   0.50    0.05    --  -47.70 -77.00  30.00   80
 35  ω    -80.00 -33.00   0.50    0.05    --  -47.70 -57.00   0.00   94
 36  ω   -101.00 -76.00   0.50    0.05    --  -47.70 -77.00  90.00   50
 37  ω    -92.00 -26.00   0.50    0.05    --  -47.70 -77.00 120.00  132
 38  ω    -63.00 -25.00   0.50    0.05    --  -47.70 -77.00 150.00   76
 39  ω    -65.00 -25.00   0.50    0.05    --  -47.70 -77.00  90.00   80
 40  ω    -62.00 -33.00   0.50    0.05    --  -47.70 -57.00  60.00   58
 41  ω   -100.00 -68.00   0.50    0.05    --  -47.70 -57.00  60.00   64
 42  ω   -122.00 -43.00   0.50    0.05    --  -47.70 -19.00-180.00  158
 43  ω    -64.00 -33.00   0.50    0.05    --  -47.70 -57.00-120.00   62
 44  ω   -111.00 -78.00   0.50    0.05    -- -101.00 -77.00  -9.26   66
 45  ω   -105.00 -79.00   0.50    0.05    -- -101.00 -77.00 150.00   52
 46  ω   -163.00-137.00   0.50    0.05    -- -101.00 -77.00  -9.26   52
 47  ω   -173.00-114.00   0.50    0.05    -- -101.00 -77.00 -60.00  118
 48  ω   -104.00 -78.00   0.50    0.05    -- -101.00 -77.00 -90.00   52
 49  ω   -107.00 -79.00   0.50    0.05    -- -101.00 -77.00-150.00   56
 50  ω   -103.00 -78.00   0.50    0.05    -- -101.00 -77.00 -60.00   50
 51  ω   -114.00 -79.00   0.50    0.05    -- -101.00 -77.00 -30.00   70
 52  ω   -103.00 -78.00   0.50    0.05    -- -101.00 -77.00   0.00   50
 53  ω   -104.00 -78.00   0.50    0.05    -- -101.00 -77.00  30.00   52
 54  ω   -104.00 -79.00   0.50    0.05    -- -101.00 -74.00 122.71   50
 55  ω   -107.00 -82.00   0.50    0.05    -- -101.00 -72.00  96.84   50
 56  ω   -105.00 -78.00   0.50    0.05    -- -101.00 -76.00 162.40   54
 57  ω   -106.00 -80.00   0.50    0.05    -- -101.00 -72.00 171.00   52
 58  ω   -138.00-112.00   0.50    0.05    -- -101.00 -76.00 162.40   52
 59  ω   -172.00-113.00   0.50    0.05    -- -101.00 -72.00 171.00  118
 60  ω   -172.00-146.00   0.50    0.05    -- -101.00 -74.00 122.71   52
 61  ω   -173.00-118.00   0.50    0.05    -- -101.00 -67.00 145.64  110
 62  ω   -165.00 -82.00   0.50    0.05    -- -101.00 -67.00 -29.22  166
 63  ω   -150.00 -81.00   0.50    0.05    -- -101.00 -71.00-109.32  138
 64  ω   -107.00 -82.00   0.50    0.05    -- -101.00 -67.00-128.48   50
 65  ω   -106.00 -81.00   0.50    0.05    -- -101.00 -69.00-140.10   50
 66  ω   -107.00 -82.00   0.50    0.05    -- -101.00 -70.00-174.14   50
 67  ω   -119.00 -84.00   0.50    0.05    -- -101.00 -63.00  31.38   70
 68  ω   -166.00 -82.00   0.50    0.05    -- -101.00 -67.00  69.05  168
 69  ω   -154.00 -83.00   0.50    0.05    -- -101.00 -65.00  82.58  142
 70  ω   -112.00 -82.00   0.50    0.05    -- -101.00 -67.00 145.64   60
 71  ω   -109.00 -84.00   0.50    0.05    -- -101.00 -63.00 123.82   50
 72  ω   -165.00 -84.00   0.50    0.05    -- -101.00 -62.00  96.08  162
 73  ω   -167.00-144.50   0.50    0.05    -- -101.00 -62.00  46.63   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1781487000
_diffrn_orient_matrix_UB_12      -0.0102626000
_diffrn_orient_matrix_UB_13      -0.0651518000
_diffrn_orient_matrix_UB_21      -0.0152456000
_diffrn_orient_matrix_UB_22      -0.0523723000
_diffrn_orient_matrix_UB_23      0.0395826000
_diffrn_orient_matrix_UB_31      -0.1263098000
_diffrn_orient_matrix_UB_32      -0.0081638000
_diffrn_orient_matrix_UB_33      -0.1719649000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                6556
_reflns_number_total             6810
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 3025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6810
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.043
_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)+(0.0460P)²+0.8358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 H3-O3
 0.88 with sigma of 0.02
 H6A-O6
 0.88 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2) = Uanis(F1)
Uanis(C16) = Uanis(C17)
Uanis(C15) = Uanis(C14)
Uanis(F2) = Uanis(C22)
4.a Ternary CH refined with riding coordinates:
 C12(H12), C30(H30)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C25(H25A,H25B),
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C23(H23), C24(H24), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   mixed
_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 0.49876(8) 0.21416(2) -0.31495(7) 0.05978(15) Uani 1 1 d . . . . .
F1 F -0.1258(5) 0.34419(15) -0.2195(6) 0.0944(8) Uani 1 1 d . . . . .
O1 O 0.4514(7) 0.36470(14) -0.4199(6) 0.0770(12) Uani 1 1 d . . . . .
O2 O 0.5329(7) 0.29459(14) -0.4716(6) 0.0775(12) Uani 1 1 d . . . . .
O3 O 0.4866(7) 0.05860(14) -0.0380(5) 0.0704(10) Uani 1 1 d D . . . .
N1 N 0.4369(6) 0.32201(14) -0.4133(5) 0.0560(10) Uani 1 1 d . . . . .
C1 C 0.3025(7) 0.25550(16) -0.2845(5) 0.0481(9) Uani 1 1 d . . . . .
C2 C 0.2950(7) 0.30250(16) -0.3331(6) 0.0494(10) Uani 1 1 d . . . . .
C3 C 0.1531(7) 0.33301(17) -0.3105(6) 0.0542(11) Uani 1 1 d . . . . .
H3A H 0.151986 0.364181 -0.342998 0.065 Uiso 1 1 calc R . . . .
C4 C 0.0170(8) 0.3160(2) -0.2400(7) 0.0608(13) Uani 1 1 d . . . . .
C5 C 0.0150(7) 0.2694(2) -0.1900(7) 0.0617(13) Uani 1 1 d . . . . .
H5 H -0.081713 0.258392 -0.143820 0.074 Uiso 1 1 calc R . . . .
C6 C 0.1590(7) 0.24016(18) -0.2104(7) 0.0574(12) Uani 1 1 d . . . . .
H6 H 0.160911 0.209353 -0.173997 0.069 Uiso 1 1 calc R . . . .
C7 C 0.4829(8) 0.16370(17) -0.1589(7) 0.0588(12) Uani 1 1 d . . . . .
H7A H 0.522451 0.175232 -0.047786 0.071 Uiso 1 1 calc R . . . .
H7B H 0.353221 0.152434 -0.176180 0.071 Uiso 1 1 calc R . . . .
C8 C 0.6151(7) 0.12379(15) -0.1873(6) 0.0488(10) Uani 1 1 d . . . . .
C9 C 0.8212(8) 0.1406(2) -0.1635(8) 0.0672(14) Uani 1 1 d . . . . .
H9A H 0.841800 0.154209 -0.263611 0.081 Uiso 1 1 calc R . . . .
H9B H 0.850633 0.163932 -0.077637 0.081 Uiso 1 1 calc R . . . .
C10 C 0.9449(10) 0.0971(3) -0.1168(12) 0.099(3) Uani 1 1 d . . . . .
H10A H 1.055784 0.104553 -0.031153 0.118 Uiso 1 1 calc R . . . .
H10B H 0.987026 0.085282 -0.210526 0.118 Uiso 1 1 calc R . . . .
C11 C 0.8201(10) 0.0603(2) -0.0562(9) 0.0767(16) Uani 1 1 d . . . . .
H11A H 0.788975 0.034550 -0.132873 0.092 Uiso 1 1 calc R . . . .
H11B H 0.883920 0.048030 0.049749 0.092 Uiso 1 1 calc R . . . .
C12 C 0.6432(8) 0.08761(18) -0.0454(6) 0.0567(12) Uani 1 1 d . . . . .
H12 H 0.674667 0.105469 0.056713 0.068 Uiso 1 1 calc R . . . .
C13 C 0.5326(7) 0.10136(15) -0.3522(6) 0.0463(9) Uani 1 1 d . . . . .
C14 C 0.6299(13) 0.0980(2) -0.4753(7) 0.0830(14) Uani 1 1 d . . . . .
H14 H 0.754061 0.109026 -0.457387 0.100 Uiso 1 1 calc R . . . .
C15 C 0.5441(13) 0.0785(2) -0.6256(8) 0.0830(14) Uani 1 1 d . . . . .
H15 H 0.611046 0.077235 -0.707506 0.100 Uiso 1 1 calc R . . . .
C16 C 0.3645(13) 0.0612(2) -0.6550(9) 0.0943(18) Uani 1 1 d . . . . .
H16 H 0.310299 0.047627 -0.755435 0.113 Uiso 1 1 calc R . . . .
C17 C 0.2647(14) 0.0638(2) -0.5376(9) 0.0943(18) Uani 1 1 d . . . . .
H17 H 0.141393 0.052135 -0.557278 0.113 Uiso 1 1 calc R . . . .
C18 C 0.3470(8) 0.08381(19) -0.3876(7) 0.0634(13) Uani 1 1 d . . . . .
H18 H 0.276548 0.085631 -0.308322 0.076 Uiso 1 1 calc R . . . .
Se2 Se 1.02565(7) 0.34352(2) 0.22702(7) 0.05376(13) Uani 1 1 d . . . . .
F2 F 0.9594(6) 0.13604(13) 0.3445(6) 0.0944(8) Uani 1 1 d . . . . .
O4 O 1.3372(6) 0.30290(15) 0.1697(6) 0.0785(12) Uani 1 1 d . . . . .
O5 O 1.4219(6) 0.23106(17) 0.1583(6) 0.0820(13) Uani 1 1 d . . . . .
O6 O 0.5286(5) 0.47968(12) 0.2549(5) 0.0599(9) Uani 1 1 d D . . . .
N2 N 1.3125(6) 0.26073(16) 0.1878(6) 0.0602(10) Uani 1 1 d . . . . .
C19 C 1.0072(6) 0.27845(17) 0.2637(6) 0.0477(9) Uani 1 1 d . . . . .
C20 C 1.1472(6) 0.24595(17) 0.2443(6) 0.0491(10) Uani 1 1 d . . . . .
C21 C 1.1344(8) 0.19822(19) 0.2722(8) 0.0685(15) Uani 1 1 d . . . . .
H21 H 1.228109 0.177590 0.256407 0.082 Uiso 1 1 calc R . . . .
C22 C 0.9797(11) 0.1827(3) 0.3235(12) 0.0944(8) Uani 1 1 d . . . . .
C23 C 0.8392(8) 0.2125(2) 0.3466(9) 0.0766(16) Uani 1 1 d . . . . .
H23 H 0.734782 0.200903 0.381069 0.092 Uiso 1 1 calc R . . . .
C24 C 0.8540(7) 0.25975(18) 0.3185(7) 0.0600(12) Uani 1 1 d . . . . .
H24 H 0.759547 0.279816 0.336402 0.072 Uiso 1 1 calc R . . . .
C25 C 0.7720(6) 0.36359(16) 0.2524(6) 0.0491(10) Uani 1 1 d . . . . .
H25A H 0.673745 0.349112 0.168655 0.059 Uiso 1 1 calc R . . . .
H25B H 0.754016 0.353861 0.358172 0.059 Uiso 1 1 calc R . . . .
C26 C 0.7576(7) 0.41762(15) 0.2372(5) 0.0450(9) Uani 1 1 d . . . . .
C27 C 0.7775(8) 0.43500(19) 0.0686(6) 0.0564(11) Uani 1 1 d . . . . .
H27A H 0.798904 0.468569 0.070284 0.068 Uiso 1 1 calc R . . . .
H27B H 0.882834 0.419489 0.036933 0.068 Uiso 1 1 calc R . . . .
C28 C 0.5914(10) 0.4227(3) -0.0484(7) 0.0826(19) Uani 1 1 d . . . . .
H28A H 0.601441 0.392891 -0.100897 0.099 Uiso 1 1 calc R . . . .
H28B H 0.556891 0.446634 -0.131930 0.099 Uiso 1 1 calc R . . . .
C29 C 0.4421(8) 0.4200(2) 0.0557(7) 0.0656(13) Uani 1 1 d . . . . .
H29A H 0.342232 0.442892 0.018619 0.079 Uiso 1 1 calc R . . . .
H29B H 0.385359 0.389049 0.048236 0.079 Uiso 1 1 calc R . . . .
C30 C 0.5468(7) 0.43033(16) 0.2296(6) 0.0505(10) Uani 1 1 d . . . . .
H30 H 0.495930 0.411895 0.308027 0.061 Uiso 1 1 calc R . . . .
C31 C 0.8951(6) 0.43921(15) 0.3824(6) 0.0450(9) Uani 1 1 d . . . . .
C32 C 1.0655(8) 0.45962(18) 0.3680(7) 0.0591(12) Uani 1 1 d . . . . .
H32 H 1.095342 0.460866 0.266383 0.071 Uiso 1 1 calc R . . . .
C33 C 1.1913(9) 0.4781(2) 0.5034(9) 0.0727(16) Uani 1 1 d . . . . .
H33 H 1.303612 0.491914 0.491017 0.087 Uiso 1 1 calc R . . . .
C34 C 1.1525(9) 0.4763(2) 0.6542(8) 0.0689(14) Uani 1 1 d . . . . .
H34 H 1.237668 0.488663 0.744389 0.083 Uiso 1 1 calc R . . . .
C35 C 0.9860(9) 0.4560(2) 0.6712(6) 0.0646(14) Uani 1 1 d . . . . .
H35 H 0.958474 0.454693 0.773744 0.078 Uiso 1 1 calc R . . . .
C36 C 0.8577(7) 0.43732(18) 0.5364(6) 0.0536(11) Uani 1 1 d . . . . .
H36 H 0.746046 0.423467 0.550071 0.064 Uiso 1 1 calc R . . . .
H6A H 0.612(7) 0.488(2) 0.342(5) 0.064 Uiso 1 1 d DR . . . .
H3 H 0.467(8) 0.0361(16) -0.114(6) 0.064 Uiso 1 1 d DR . . . .


_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 C1 1.908(5) . ?
Se1 C7 1.970(5) . ?
F1 C4 1.351(6) . ?
O1 N1 1.225(5) . ?
O2 N1 1.222(6) . ?
O3 C12 1.416(7) . ?
N1 C2 1.463(6) . ?
C1 C2 1.399(7) . ?
C1 C6 1.399(7) . ?
C2 C3 1.392(7) . ?
C3 C4 1.351(8) . ?
C4 C5 1.395(8) . ?
C5 C6 1.377(7) . ?
C7 C8 1.541(7) . ?
C8 C9 1.534(7) . ?
C8 C12 1.556(7) . ?
C8 C13 1.519(7) . ?
C9 C10 1.527(9) . ?
C10 C11 1.546(9) . ?
C11 C12 1.518(8) . ?
C13 C14 1.384(7) . ?
C13 C18 1.399(8) . ?
C14 C15 1.391(10) . ?
C15 C16 1.358(12) . ?
C16 C17 1.354(12) . ?
C17 C18 1.388(9) . ?
Se2 C19 1.892(5) . ?
Se2 C25 1.980(4) . ?
F2 C22 1.355(8) . ?
O4 N2 1.231(6) . ?
O5 N2 1.222(6) . ?
O6 C30 1.435(6) . ?
N2 C20 1.448(7) . ?
C19 C20 1.410(6) . ?
C19 C24 1.400(7) . ?
C20 C21 1.389(8) . ?
C21 C22 1.363(10) . ?
C22 C23 1.374(9) . ?
C23 C24 1.377(8) . ?
C25 C26 1.548(6) . ?
C26 C27 1.541(6) . ?
C26 C30 1.553(6) . ?
C26 C31 1.517(7) . ?
C27 C28 1.514(9) . ?
C28 C29 1.542(9) . ?
C29 C30 1.513(7) . ?
C31 C32 1.394(7) . ?
C31 C36 1.385(7) . ?
C32 C33 1.387(9) . ?
C33 C34 1.363(9) . ?
C34 C35 1.373(9) . ?
C35 C36 1.395(8) . ?

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 101.7(2) . . ?
O1 N1 C2 118.4(5) . . ?
O2 N1 O1 123.8(5) . . ?
O2 N1 C2 117.8(4) . . ?
C2 C1 Se1 122.2(4) . . ?
C6 C1 Se1 121.2(4) . . ?
C6 C1 C2 116.6(4) . . ?
C1 C2 N1 121.0(4) . . ?
C3 C2 N1 116.3(4) . . ?
C3 C2 C1 122.7(4) . . ?
C4 C3 C2 118.1(5) . . ?
F1 C4 C3 119.9(5) . . ?
F1 C4 C5 117.8(5) . . ?
C3 C4 C5 122.3(5) . . ?
C6 C5 C4 118.7(5) . . ?
C5 C6 C1 121.8(5) . . ?
C8 C7 Se1 107.6(3) . . ?
C7 C8 C12 110.3(4) . . ?
C9 C8 C7 111.6(4) . . ?
C9 C8 C12 99.0(4) . . ?
C13 C8 C7 109.0(4) . . ?
C13 C8 C9 114.6(4) . . ?
C13 C8 C12 112.1(4) . . ?
C10 C9 C8 105.9(5) . . ?
C9 C10 C11 106.6(5) . . ?
C12 C11 C10 103.6(5) . . ?
O3 C12 C8 117.2(5) . . ?
O3 C12 C11 113.4(5) . . ?
C11 C12 C8 104.9(4) . . ?
C14 C13 C8 123.5(5) . . ?
C14 C13 C18 116.4(6) . . ?
C18 C13 C8 120.1(4) . . ?
C13 C14 C15 120.8(8) . . ?
C16 C15 C14 121.2(7) . . ?
C17 C16 C15 119.7(7) . . ?
C16 C17 C18 119.8(9) . . ?
C17 C18 C13 122.0(7) . . ?
C19 Se2 C25 99.46(19) . . ?
O4 N2 C20 118.7(4) . . ?
O5 N2 O4 122.2(5) . . ?
O5 N2 C20 119.1(5) . . ?
C20 C19 Se2 123.2(4) . . ?
C24 C19 Se2 121.2(4) . . ?
C24 C19 C20 115.6(5) . . ?
C19 C20 N2 121.1(4) . . ?
C21 C20 N2 115.7(4) . . ?
C21 C20 C19 123.2(5) . . ?
C22 C21 C20 117.7(5) . . ?
F2 C22 C21 118.9(6) . . ?
F2 C22 C23 119.0(6) . . ?
C21 C22 C23 122.1(7) . . ?
C22 C23 C24 119.5(6) . . ?
C23 C24 C19 121.9(5) . . ?
C26 C25 Se2 109.0(3) . . ?
C25 C26 C30 106.4(4) . . ?
C27 C26 C25 112.2(4) . . ?
C27 C26 C30 100.8(4) . . ?
C31 C26 C25 108.6(4) . . ?
C31 C26 C27 115.3(4) . . ?
C31 C26 C30 113.1(4) . . ?
C28 C27 C26 105.4(5) . . ?
C27 C28 C29 106.0(5) . . ?
C30 C29 C28 106.2(5) . . ?
O6 C30 C26 110.3(4) . . ?
O6 C30 C29 107.0(4) . . ?
C29 C30 C26 105.2(4) . . ?
C32 C31 C26 121.9(4) . . ?
C36 C31 C26 120.3(4) . . ?
C36 C31 C32 117.7(5) . . ?
C33 C32 C31 120.9(5) . . ?
C34 C33 C32 120.9(6) . . ?
C33 C34 C35 119.2(6) . . ?
C34 C35 C36 120.7(5) . . ?
C31 C36 C35 120.6(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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.867
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/DCM'
_chemical_properties_physical    Air-sensitive
