# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_exp_2984
_database_code_depnum_ccdc_archive 'CCDC 2469788'
loop_
_audit_author_name
_audit_author_address
'Tianhao Wang'
;Shandong University
China
;
_audit_update_record             
;
2025-07-04 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2024-12-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O Se'
_chemical_formula_sum            'C11 H12 N2 O Se'
_chemical_formula_weight         267.19
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 Se11'
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      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                   4.8143(4)
_cell_length_b                   22.3394(16)
_cell_length_c                   5.5736(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.012(9)
_cell_angle_gamma                90
_cell_volume                     566.73(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1005
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      70.4930
_cell_measurement_theta_min      7.9140
_shelx_estimated_absorpt_T_max   0.674
_shelx_estimated_absorpt_T_min   0.481
_exptl_absorpt_coefficient_mu    4.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2211
_diffrn_reflns_point_group_measured_fraction_full 0.654
_diffrn_reflns_point_group_measured_fraction_max 0.642
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.429
_diffrn_reflns_theta_min         3.958
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -7.00   1.00    1.00    --    0.00  94.00 -21.00   25
  2  ω      1.00  27.00   1.00    1.00    --   54.00 -94.00-132.00   26
  3  ω     61.00 101.00   1.00    1.00    --  108.00 -94.00-132.00   40
  4  ω    123.00 166.00   1.00    1.00    --  108.00  94.00 -21.00   43
  5  ω    -21.00   4.00   1.00    1.00    --    0.00 -77.00  60.00   25
  6  ω    -21.00  26.00   1.00    1.00    --    0.00 -77.00-180.00   47
  7  ω    -16.00  95.00   1.00    1.00    --   54.00 -19.00 -30.00  111
  8  ω     40.00  87.00   1.00    1.00    --   54.00  57.00 -30.00   47
  9  ω      7.00  95.00   1.00    1.00    --   54.00 -99.00 -90.00   88
 10  ω     37.00 101.00   1.00    1.00    --  108.00-111.00  30.00   64
 11  ω     50.00 141.00   1.00    1.00    --  108.00 -25.00  30.00   91
 12  ω     77.00 107.00   1.00    1.00    --  108.00 -91.00 120.00   30
 13  ω     38.00  75.00   1.00    1.00    --  108.00 -91.00-180.00   37
 14  ω     49.00 108.00   1.00    1.00    --  108.00-111.00  90.00   59
 15  ω     78.00 105.00   1.00    1.00    --  108.00 -91.00-180.00   27
 16  ω     63.00 117.00   1.00    1.00    --  108.00 178.00 120.00   54
 17  ω     41.00  75.00   1.00    1.00    --  108.00 -91.00 120.00   34
 18  ω    142.00 178.00   1.00    1.00    --  108.00  77.00-150.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282515000
_diffrn_orient_matrix_UB_12      -0.0144727000
_diffrn_orient_matrix_UB_13      -0.2770904000
_diffrn_orient_matrix_UB_21      -0.1316072000
_diffrn_orient_matrix_UB_22      0.0625793000
_diffrn_orient_matrix_UB_23      -0.0818659000
_diffrn_orient_matrix_UB_31      0.3105678000
_diffrn_orient_matrix_UB_32      0.0251663000
_diffrn_orient_matrix_UB_33      0.0439231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.269
_reflns_Friedel_fraction_full    0.288
_reflns_Friedel_fraction_max     0.280
_reflns_number_gt                1338
_reflns_number_total             1387
_reflns_odcompleteness_completeness 99.91
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details 
;
 Flack x determined using 268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1387
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1331
_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 Ternary CH refined with riding coordinates:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00F(H00F), C007(H007), C00D(H00D), C00C(H00E)
2.d Fitted hexagon refined as free rotating group:
 C00B(C00F,C007,C00D,C00C,C009)
2.e Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O002 O 0.1479(15) 0.4469(4) 0.406(2) 0.052(2) Uani 1 1 d . . . . .
N003 N 0.6019(15) 0.4800(3) 0.4310(14) 0.0260(14) Uani 1 1 d . . . . .
N004 N 0.8190(13) 0.3197(11) 0.8228(12) 0.043(3) Uani 1 1 d . . . . .
C005 C 0.6393(15) 0.3187(9) 0.6315(15) 0.033(2) Uani 1 1 d . . . . .
C006 C 0.3796(16) 0.4412(4) 0.3547(17) 0.0259(18) Uani 1 1 d . . . . .
C008 C 0.607(2) 0.5287(4) 0.609(2) 0.035(2) Uani 1 1 d . . . . .
H008 H 0.407833 0.532165 0.626868 0.042 Uiso 1 1 calc R U . . .
C00A C 0.4242(16) 0.3897(4) 0.1979(15) 0.0251(16) Uani 1 1 d . . . . .
H00A H 0.630618 0.389624 0.199891 0.030 Uiso 1 1 calc R U . . .
H00B H 0.296038 0.395136 0.019999 0.030 Uiso 1 1 calc R U . . .
C00B C 0.4896(17) 0.6077(4) 0.2661(18) 0.120(10) Uani 1 1 d G . . . .
H00C H 0.321739 0.584386 0.179420 0.144 Uiso 1 1 calc R U . . .
C00F C 0.5448(19) 0.6608(4) 0.1600(15) 0.130(11) Uani 1 1 d G . . . .
H00F H 0.414692 0.673839 0.000749 0.155 Uiso 1 1 calc R U . . .
C007 C 0.7904(15) 0.6949(3) 0.2868(13) 0.0308(18) Uani 1 1 d G . . . .
H007 H 0.828092 0.731189 0.214276 0.037 Uiso 1 1 calc R U . . .
C00D C 0.9807(18) 0.6758(4) 0.5198(16) 0.094(7) Uani 1 1 d G . . . .
H00D H 1.148544 0.699087 0.606474 0.113 Uiso 1 1 calc R U . . .
C00C C 0.9255(19) 0.6227(4) 0.6259(13) 0.098(7) Uani 1 1 d G . . . .
H00E H 1.055597 0.609635 0.785149 0.117 Uiso 1 1 calc R U . . .
C009 C 0.6799(14) 0.5886(3) 0.4991(13) 0.0274(17) Uani 1 1 d G . . . .
C00E C 0.829(4) 0.5124(6) 0.868(2) 0.062(4) Uani 1 1 d . . . . .
H00G H 0.767159 0.475189 0.929424 0.093 Uiso 1 1 calc R U . . .
H00H H 0.837361 0.544669 0.989201 0.093 Uiso 1 1 calc R U . . .
H00I H 1.023527 0.506756 0.851227 0.093 Uiso 1 1 calc R U . . .
Se3 Se 0.33645(13) 0.31336(2) 0.32282(11) 0.0269(3) Uani 1 1 d . . . . .
H003 H 0.76(2) 0.475(5) 0.36(2) 0.03(2) Uiso 1 1 d . . . . .


_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
O002 C006 1.246(10) . ?
N003 C006 1.335(11) . ?
N003 C008 1.466(12) . ?
N003 H003 0.98(11) . ?
N004 C005 1.134(10) . ?
C005 Se3 1.862(8) . ?
C006 C00A 1.501(12) . ?
C008 H008 1.0000 . ?
C008 C009 1.558(11) . ?
C008 C00E 1.535(17) . ?
C00A H00A 0.9900 . ?
C00A H00B 0.9900 . ?
C00A Se3 1.941(8) . ?
C00B H00C 0.9500 . ?
C00B C00F 1.3900 . ?
C00B C009 1.3900 . ?
C00F H00F 0.9500 . ?
C00F C007 1.3900 . ?
C007 H007 0.9500 . ?
C007 C00D 1.3900 . ?
C00D H00D 0.9500 . ?
C00D C00C 1.3900 . ?
C00C H00E 0.9500 . ?
C00C C009 1.3900 . ?
C00E H00G 0.9800 . ?
C00E H00H 0.9800 . ?
C00E H00I 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
C006 N003 C008 122.2(7) . . ?
C006 N003 H003 115(6) . . ?
C008 N003 H003 122(7) . . ?
N004 C005 Se3 176.9(19) . . ?
O002 C006 N003 123.0(9) . . ?
O002 C006 C00A 121.5(8) . . ?
N003 C006 C00A 115.5(6) . . ?
N003 C008 H008 108.6 . . ?
N003 C008 C009 109.2(7) . . ?
N003 C008 C00E 108.3(8) . . ?
C009 C008 H008 108.6 . . ?
C00E C008 H008 108.6 . . ?
C00E C008 C009 113.4(9) . . ?
C006 C00A H00A 109.2 . . ?
C006 C00A H00B 109.2 . . ?
C006 C00A Se3 112.0(5) . . ?
H00A C00A H00B 107.9 . . ?
Se3 C00A H00A 109.2 . . ?
Se3 C00A H00B 109.2 . . ?
C00F C00B H00C 120.0 . . ?
C00F C00B C009 120.0 . . ?
C009 C00B H00C 120.0 . . ?
C00B C00F H00F 120.0 . . ?
C00B C00F C007 120.0 . . ?
C007 C00F H00F 120.0 . . ?
C00F C007 H007 120.0 . . ?
C00D C007 C00F 120.0 . . ?
C00D C007 H007 120.0 . . ?
C007 C00D H00D 120.0 . . ?
C00C C00D C007 120.0 . . ?
C00C C00D H00D 120.0 . . ?
C00D C00C H00E 120.0 . . ?
C00D C00C C009 120.0 . . ?
C009 C00C H00E 120.0 . . ?
C00B C009 C008 117.8(6) . . ?
C00C C009 C008 122.2(6) . . ?
C00C C009 C00B 120.0 . . ?
C008 C00E H00G 109.5 . . ?
C008 C00E H00H 109.5 . . ?
C008 C00E H00I 109.5 . . ?
H00G C00E H00H 109.5 . . ?
H00G C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
C005 Se3 C00A 94.5(6) . . ?

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
O002 C006 C00A Se3 -50.4(11) . . . . ?
N003 C006 C00A Se3 130.3(7) . . . . ?
N003 C008 C009 C00B 60.0(9) . . . . ?
N003 C008 C009 C00C -120.0(9) . . . . ?
C006 N003 C008 C009 -130.3(8) . . . . ?
C006 N003 C008 C00E 105.7(10) . . . . ?
C008 N003 C006 O002 7.8(14) . . . . ?
C008 N003 C006 C00A -172.9(8) . . . . ?
C00B C00F C007 C00D 0.0 . . . . ?
C00F C00B C009 C008 -180.0(6) . . . . ?
C00F C00B C009 C00C 0.0 . . . . ?
C00F C007 C00D C00C 0.0 . . . . ?
C007 C00D C00C C009 0.0 . . . . ?
C00D C00C C009 C008 180.0(6) . . . . ?
C00D C00C C009 C00B 0.0 . . . . ?
C009 C00B C00F C007 0.0 . . . . ?
C00E C008 C009 C00B -179.2(9) . . . . ?
C00E C008 C009 C00C 0.8(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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.733
####################################################################### 
# 
# 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_b_auto
_database_code_depnum_ccdc_archive 'CCDC 2469791'
loop_
_audit_author_name
_audit_author_address
'Tianhao Wang'
;Shandong University
China
;
_audit_update_record             
;
2025-07-04 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 N2 O Se'
_chemical_formula_sum            'C11 H12 N2 O Se'
_chemical_formula_weight         267.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNOSe
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           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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.71929(18)
_cell_length_b                   11.0228(5)
_cell_length_c                   22.1906(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1154.35(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4116
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.6290
_cell_measurement_theta_min      3.9900
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    4.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6939
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.530
_diffrn_reflns_theta_min         3.984
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_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 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    102.00 178.00   1.00    0.15    --  106.65 116.00 175.00   76
  2  ω     39.00  88.00   1.00    0.15    --  106.65 -98.00 170.00   49
  3  ω     74.00 105.00   1.00    0.15    --  106.65 -77.00 -30.00   31
  4  ω     39.00  69.00   1.00    0.15    --  106.65 -77.00 -30.00   30
  5  ω     34.00 105.00   1.00    0.15    --  106.65 -77.00-180.00   71
  6  ω     34.00  65.00   1.00    0.15    --  106.65 -57.00-120.00   31
  7  ω     96.00 177.00   1.00    0.15    --  106.65  28.00  98.00   81
  8  ω    -64.00 -26.00   1.00    0.15    --  -91.75  57.00 120.00   38
  9  ω    -76.00  -6.00   1.00    0.10    --  -48.67  98.00 -81.00   70
 10  ω    -69.00 -34.00   1.00    0.15    --  -91.75  98.00 -81.00   35
 11  ω   -120.00 -26.00   1.00    0.10    --  -48.67 -77.00-180.00   94
 12  ω     69.00  94.00   1.00    0.15    --  106.65 -98.00 170.00   25
 13  ω   -105.00 -78.00   1.00    0.10    --  -48.42-125.00-150.00   27
 14  ω    -28.00  -3.00   1.00    0.10    --  -48.42  28.00  98.00   25
 15  ω     57.00  83.00   1.00    0.15    --  106.65-165.00 -59.00   26
 16  ω    -66.00 -41.00   1.00    0.15    --  -91.75  57.00  90.00   25
 17  ω    -57.00 -31.00   1.00    0.15    --  -91.75  57.00 -60.00   26
 18  ω     81.00 106.00   1.00    0.15    --  106.65 -99.00 -30.00   25
 19  ω     34.00  59.00   1.00    0.15    --  106.65 -57.00-150.00   25
 20  ω     40.00  66.00   1.00    0.15    --  106.65 -99.00 -30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1143110000
_diffrn_orient_matrix_UB_12      0.0943114000
_diffrn_orient_matrix_UB_13      0.0451772000
_diffrn_orient_matrix_UB_21      0.0363906000
_diffrn_orient_matrix_UB_22      0.0921122000
_diffrn_orient_matrix_UB_23      -0.0516482000
_diffrn_orient_matrix_UB_31      -0.3035933000
_diffrn_orient_matrix_UB_32      0.0464008000
_diffrn_orient_matrix_UB_33      0.0106956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                2188
_reflns_number_total             2318
_reflns_odcompleteness_completeness 99.92
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.305
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0771
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
Se11 Se 0.34127(7) 0.42823(4) 0.49680(2) 0.03213(15) Uani 1 1 d . . . . .
O14 O 0.9859(5) 0.5124(3) 0.40334(14) 0.0333(6) Uani 1 1 d . . . . .
C9 C 0.7253(7) 0.5048(4) 0.40165(17) 0.0246(8) Uani 1 1 d . . . . .
N8 N 0.5586(6) 0.5886(3) 0.37788(15) 0.0290(7) Uani 1 1 d . . . . .
H8 H 0.375406 0.574114 0.376238 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5775(7) 0.3929(4) 0.42586(17) 0.0257(8) Uani 1 1 d . . . . .
H10A H 0.721731 0.331550 0.436876 0.031 Uiso 1 1 calc R U . . .
H10B H 0.456949 0.357835 0.393763 0.031 Uiso 1 1 calc R U . . .
N13 N 0.7814(9) 0.3842(4) 0.59170(19) 0.0515(11) Uani 1 1 d . . . . .
C6 C 0.3224(9) 0.8573(4) 0.3062(2) 0.0417(10) Uani 1 1 d . . . . .
H6 H 0.355424 0.912793 0.338147 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1345(10) 0.8871(5) 0.2593(3) 0.0612(16) Uani 1 1 d . . . . .
H5 H 0.041459 0.963548 0.259920 0.073 Uiso 1 1 calc R U . . .
C7 C 0.6629(8) 0.7039(3) 0.35423(17) 0.0296(8) Uani 1 1 d . . . . .
H7 H 0.850402 0.688186 0.334766 0.036 Uiso 1 1 calc R U . . .
C1 C 0.4594(7) 0.7458(3) 0.30520(19) 0.0289(8) Uani 1 1 d . . . . .
C12 C 0.6189(9) 0.3991(4) 0.55355(19) 0.0350(9) Uani 1 1 d . . . . .
C2 C 0.4072(9) 0.6691(4) 0.2569(2) 0.0409(10) Uani 1 1 d . . . . .
H2 H 0.501298 0.593051 0.254958 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7107(12) 0.7938(5) 0.4049(3) 0.0547(13) Uani 1 1 d . . . . .
H15A H 0.529872 0.811407 0.424780 0.082 Uiso 1 1 calc R U . . .
H15B H 0.790357 0.868931 0.388509 0.082 Uiso 1 1 calc R U . . .
H15C H 0.842975 0.759047 0.434296 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2214(11) 0.7012(6) 0.2116(2) 0.0580(15) Uani 1 1 d . . . . .
H3 H 0.190263 0.647063 0.178968 0.070 Uiso 1 1 calc R U . . .
C4 C 0.0827(11) 0.8089(6) 0.2131(3) 0.0636(18) Uani 1 1 d . . . . .
H4 H -0.048790 0.829442 0.182314 0.076 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
Se11 C10 1.968(4) . ?
Se11 C12 1.845(4) . ?
O14 C9 1.233(4) . ?
C9 N8 1.323(5) . ?
C9 C10 1.516(5) . ?
N8 H8 0.8800 . ?
N8 C7 1.461(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N13 C12 1.154(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.405(8) . ?
C6 C1 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.363(9) . ?
C7 H7 1.0000 . ?
C7 C1 1.523(5) . ?
C7 C15 1.516(6) . ?
C1 C2 1.387(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.356(10) . ?
C4 H4 0.9500 . ?

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
C12 Se11 C10 96.27(17) . . ?
O14 C9 N8 123.9(4) . . ?
O14 C9 C10 120.2(4) . . ?
N8 C9 C10 115.8(3) . . ?
C9 N8 H8 118.3 . . ?
C9 N8 C7 123.4(3) . . ?
C7 N8 H8 118.3 . . ?
Se11 C10 H10A 109.1 . . ?
Se11 C10 H10B 109.1 . . ?
C9 C10 Se11 112.5(3) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C1 C6 C5 119.3(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.3 . . ?
N8 C7 H7 107.6 . . ?
N8 C7 C1 108.0(3) . . ?
N8 C7 C15 110.6(3) . . ?
C1 C7 H7 107.6 . . ?
C15 C7 H7 107.6 . . ?
C15 C7 C1 115.2(4) . . ?
C6 C1 C7 123.4(4) . . ?
C2 C1 C6 117.9(4) . . ?
C2 C1 C7 118.6(4) . . ?
N13 C12 Se11 175.7(4) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(5) . . ?
C3 C2 H2 119.4 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?

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
O14 C9 N8 C7 -4.1(6) . . . . ?
O14 C9 C10 Se11 114.8(4) . . . . ?
C9 N8 C7 C1 152.1(4) . . . . ?
C9 N8 C7 C15 -81.0(5) . . . . ?
N8 C9 C10 Se11 -67.1(4) . . . . ?
N8 C7 C1 C6 123.5(4) . . . . ?
N8 C7 C1 C2 -56.6(4) . . . . ?
C10 C9 N8 C7 177.9(3) . . . . ?
C6 C5 C4 C3 -1.7(8) . . . . ?
C6 C1 C2 C3 -1.1(6) . . . . ?
C5 C6 C1 C7 -178.9(4) . . . . ?
C5 C6 C1 C2 1.1(6) . . . . ?
C7 C1 C2 C3 178.9(4) . . . . ?
C1 C6 C5 C4 0.3(7) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C15 C7 C1 C6 -0.7(5) . . . . ?
C15 C7 C1 C2 179.3(4) . . . . ?

_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 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.515
####################################################################### 
# 
# 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_c_auto
_database_code_depnum_ccdc_archive 'CCDC 2469790'
loop_
_audit_author_name
_audit_author_address
'Tianhao Wang'
;Shandong University
China
;
_audit_update_record             
;
2025-07-04 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C76 H42 N4 O2'
_chemical_formula_sum            'C76 H42 N4 O2'
_chemical_formula_weight         1043.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNO
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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.4150(2)
_cell_length_b                   46.5563(11)
_cell_length_c                   25.3648(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11118.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10837
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      62.4160
_cell_measurement_theta_min      3.9570
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4336
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38387
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.986
_diffrn_reflns_theta_min         3.969
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -151.00 -64.00   1.00   19.00    --  -76.98 -24.00-151.00   87
  2  ω     54.00  82.00   1.00   19.00    --   79.17-104.00  26.00   28
  3  ω     18.00  50.00   1.00   19.00    --   79.17-104.00  26.00   32
  4  ω    -13.00  74.00   1.00    1.20    --    1.09  57.00 150.00   87
  5  ω    -43.00  -4.00   1.00   19.00    --  -76.98  38.00-150.00   39
  6  ω    -27.00  -1.00   1.00   19.00    --  -76.98  19.00-150.00   26
  7  ω    -46.00  -4.00   1.00   19.00    --  -76.98  57.00 150.00   42
  8  ω      7.00  40.00   1.00   19.00    --   79.17 -38.00  30.00   33
  9  ω      9.00  64.00   1.00   19.00    --   79.17 -99.00 120.00   55
 10  ω     67.00 103.00   1.00   19.00    --   79.17 -99.00 120.00   36
 11  ω    107.00 151.00   1.00   19.00    --   79.17 114.00-145.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0179826000
_diffrn_orient_matrix_UB_12      0.0074189000
_diffrn_orient_matrix_UB_13      0.0588082000
_diffrn_orient_matrix_UB_21      -0.0489720000
_diffrn_orient_matrix_UB_22      0.0309835000
_diffrn_orient_matrix_UB_23      -0.0110819000
_diffrn_orient_matrix_UB_31      -0.1551838000
_diffrn_orient_matrix_UB_32      -0.0089154000
_diffrn_orient_matrix_UB_33      0.0103038000
_diffrn_oxdiff_digest_frames     
;
0166607893bf4a49773b32a7397fb8fd1d000258830
;
_diffrn_oxdiff_digest_hkl        
;
01f5a10623784e6303a168521b917f27d388cc
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7080
_reflns_number_total             8774
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.276
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     739
_refine_ls_number_reflns         8774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0303P)²+22.3598P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1818
_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:
 C00K(H00K), C00M(H00M), C00S(H00S), C00U(H00U), C00W(H00W), C011(H011),
 C012(H012), C014(H014), C016(H016), C017(H017), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01E(H01E), C01F(H01F), C01H(H01H), C01I(H01I),
 C01J(H01J), C01K(H01K), C01L(H01L), C01N(H01N), C01P(H01P), C01R(H01R),
 C01S(H01S), C01T(H01T), C01U(H01U), C01V(H01V), C01W(H01W), C01X(H01X),
 C01Z(H01Z), C020(H020), C021(H021), C023(H023), C024(H024), C025(H025),
 C026(H026), C027(H027), C028(H028), C029(H029), C02A(H02A), C02C(H02C)
;
_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
O001 O 0.4618(3) 0.62858(6) 0.56967(10) 0.0451(6) Uani 1 1 d . . . . .
O002 O 0.2146(3) 0.61441(5) 0.48030(11) 0.0458(7) Uani 1 1 d . . . . .
N003 N 0.2729(3) 0.65743(6) 0.59428(12) 0.0401(7) Uani 1 1 d . . . . .
N004 N 0.1175(3) 0.59692(7) 0.55748(13) 0.0405(7) Uani 1 1 d . . . . .
N005 N 0.1232(3) 0.55868(7) 0.63912(13) 0.0428(8) Uani 1 1 d . . . . .
N006 N 0.0621(3) 0.69613(6) 0.57141(14) 0.0452(8) Uani 1 1 d . . . . .
C007 C 0.1064(4) 0.61375(8) 0.51656(16) 0.0410(9) Uani 1 1 d . . . . .
C008 C -0.1061(4) 0.61666(8) 0.58871(16) 0.0429(9) Uani 1 1 d . . . . .
C009 C 0.3131(4) 0.59179(8) 0.47913(15) 0.0405(9) Uani 1 1 d . . . . .
C00A C 0.3662(4) 0.63780(8) 0.60615(16) 0.0413(9) Uani 1 1 d . . . . .
C00B C 0.4936(4) 0.64450(8) 0.52476(16) 0.0400(9) Uani 1 1 d . . . . .
C00C C 0.5006(4) 0.62973(8) 0.47820(15) 0.0389(9) Uani 1 1 d . . . . .
C00D C 0.4542(4) 0.59911(8) 0.47491(15) 0.0374(8) Uani 1 1 d . . . . .
C00E C 0.0105(4) 0.59782(8) 0.59346(15) 0.0387(9) Uani 1 1 d . . . . .
C00F C 0.5551(4) 0.57628(8) 0.46893(15) 0.0406(9) Uani 1 1 d . . . . .
C00G C 0.3765(4) 0.52108(8) 0.65595(15) 0.0414(9) Uani 1 1 d . . . . .
C00H C 0.1736(4) 0.66374(8) 0.63228(16) 0.0416(9) Uani 1 1 d . . . . .
C00I C 0.5074(4) 0.54737(8) 0.46596(16) 0.0432(9) Uani 1 1 d . . . . .
C00J C 0.2409(4) 0.51791(9) 0.67840(16) 0.0446(9) Uani 1 1 d . . . . .
C00K C -0.0076(4) 0.63269(8) 0.50668(17) 0.0428(9) Uani 1 1 d . . . . .
H00K H -0.0110 0.6440 0.4755 0.051 Uiso 1 1 calc R . . . .
C00L C 0.1306(4) 0.54083(9) 0.67988(16) 0.0454(10) Uani 1 1 d . . . . .
C00M C 0.2651(4) 0.56325(8) 0.47671(16) 0.0439(10) Uani 1 1 d . . . . .
H00M H 0.1666 0.5591 0.4794 0.053 Uiso 1 1 calc R . . . .
C00N C 0.0171(4) 0.57864(8) 0.63844(16) 0.0420(9) Uani 1 1 d . . . . .
C00O C 0.0611(4) 0.68355(8) 0.61956(17) 0.0441(10) Uani 1 1 d . . . . .
C00P C -0.0900(4) 0.58002(9) 0.67723(16) 0.0457(10) Uani 1 1 d . . . . .
C00Q C -0.0450(4) 0.72599(8) 0.50369(19) 0.0500(11) Uani 1 1 d . . . . .
C00R C 0.5566(4) 0.64412(9) 0.43335(18) 0.0520(11) Uani 1 1 d . . . . .
C00S C -0.1119(4) 0.63415(8) 0.54327(17) 0.0460(10) Uani 1 1 d . . . . .
H00S H -0.1893 0.6470 0.5384 0.055 Uiso 1 1 calc R . . . .
C00T C -0.0471(4) 0.71228(9) 0.55627(19) 0.0508(11) Uani 1 1 d . . . . .
C00U C 0.6074(4) 0.52524(9) 0.45848(17) 0.0504(10) Uani 1 1 d . . . . .
H00U H 0.5757 0.5059 0.4564 0.060 Uiso 1 1 calc R . . . .
C00V C 0.4775(4) 0.49839(9) 0.66068(16) 0.0465(10) Uani 1 1 d . . . . .
C00W C 0.3598(4) 0.54174(9) 0.47053(17) 0.0477(10) Uani 1 1 d . . . . .
H00W H 0.3270 0.5225 0.4692 0.057 Uiso 1 1 calc R . . . .
C00X C 0.0402(4) 0.71710(8) 0.45989(18) 0.0479(10) Uani 1 1 d . . . . .
C00Y C 0.1748(4) 0.65077(9) 0.68248(17) 0.0504(10) Uani 1 1 d . . . . .
C00Z C 0.6589(4) 0.52694(9) 0.61411(17) 0.0493(10) Uani 1 1 d . . . . .
C010 C -0.0479(4) 0.68820(10) 0.65659(19) 0.0558(12) Uani 1 1 d . . . . .
C011 C 0.5557(4) 0.54895(9) 0.60787(17) 0.0476(10) Uani 1 1 d . . . . .
H011 H 0.5807 0.5659 0.5893 0.057 Uiso 1 1 calc R . . . .
C012 C 0.4224(4) 0.54646(8) 0.62771(17) 0.0456(10) Uani 1 1 d . . . . .
H012 H 0.3573 0.5618 0.6229 0.055 Uiso 1 1 calc R . . . .
C013 C 0.6190(4) 0.50157(9) 0.64071(16) 0.0487(10) Uani 1 1 d . . . . .
C014 C 0.1433(4) 0.69423(8) 0.46221(18) 0.0493(10) Uani 1 1 d . . . . .
H014 H 0.1530 0.6836 0.4940 0.059 Uiso 1 1 calc R . . . .
C015 C 0.0265(4) 0.73156(9) 0.4106(2) 0.0522(11) Uani 1 1 d . . . . .
C016 C 0.7033(4) 0.58153(9) 0.46511(17) 0.0500(10) Uani 1 1 d . . . . .
H016 H 0.7380 0.6007 0.4673 0.060 Uiso 1 1 calc R . . . .
C017 C -0.2060(4) 0.59932(9) 0.67055(17) 0.0505(11) Uani 1 1 d . . . . .
H017 H -0.2792 0.5998 0.6963 0.061 Uiso 1 1 calc R . . . .
C018 C 0.1125(5) 0.72394(9) 0.36650(19) 0.0554(11) Uani 1 1 d . . . . .
C019 C 0.3776(5) 0.62361(9) 0.65510(17) 0.0497(10) Uani 1 1 d . . . . .
H019 H 0.4496 0.6097 0.6613 0.060 Uiso 1 1 calc R . . . .
C01A C 0.5366(4) 0.67322(9) 0.52994(19) 0.0501(11) Uani 1 1 d . . . . .
H01A H 0.5274 0.6830 0.5627 0.060 Uiso 1 1 calc R . . . .
C01B C -0.2140(4) 0.61686(9) 0.62837(18) 0.0512(11) Uani 1 1 d . . . . .
H01B H -0.2925 0.6295 0.6249 0.061 Uiso 1 1 calc R . . . .
C01C C -0.0746(4) 0.56194(10) 0.72074(18) 0.0569(11) Uani 1 1 d . . . . .
H01C H -0.1403 0.5630 0.7491 0.068 Uiso 1 1 calc R . . . .
C01D C 0.4385(5) 0.47202(9) 0.68482(17) 0.0544(11) Uani 1 1 d . . . . .
C01E C 0.2262(5) 0.68737(9) 0.42085(18) 0.0555(11) Uani 1 1 d . . . . .
H01E H 0.2935 0.6723 0.4247 0.067 Uiso 1 1 calc R . . . .
C01F C 0.2071(5) 0.49180(9) 0.70249(18) 0.0577(11) Uani 1 1 d . . . . .
H01F H 0.1158 0.4895 0.7179 0.069 Uiso 1 1 calc R . . . .
C01G C 0.7205(5) 0.47927(10) 0.64664(18) 0.0584(12) Uani 1 1 d . . . . .
C01H C 0.0354(4) 0.54264(10) 0.72261(18) 0.0557(11) Uani 1 1 d . . . . .
H01H H 0.0474 0.5306 0.7525 0.067 Uiso 1 1 calc R . . . .
C01I C 0.3020(5) 0.46922(10) 0.70463(18) 0.0609(12) Uani 1 1 d . . . . .
H01I H 0.2733 0.4515 0.7199 0.073 Uiso 1 1 calc R . . . .
C01J C -0.1353(5) 0.74976(10) 0.4963(2) 0.0638(13) Uani 1 1 d . . . . .
H01J H -0.1892 0.7566 0.5254 0.077 Uiso 1 1 calc R . . . .
C01K C 0.5917(4) 0.68684(10) 0.4873(2) 0.0617(13) Uani 1 1 d . . . . .
H01K H 0.6212 0.7063 0.4905 0.074 Uiso 1 1 calc R . . . .
C01L C 0.2818(5) 0.63053(10) 0.69292(18) 0.0564(11) Uani 1 1 d . . . . .
H01L H 0.2871 0.6217 0.7266 0.068 Uiso 1 1 calc R . . . .
C01M C 0.6064(5) 0.67296(10) 0.4383(2) 0.0615(13) Uani 1 1 d . . . . .
C01N C 0.7482(5) 0.53096(10) 0.45415(19) 0.0616(13) Uani 1 1 d . . . . .
H01N H 0.8137 0.5158 0.4483 0.074 Uiso 1 1 calc R . . . .
C01O C 0.2168(5) 0.70194(10) 0.37117(19) 0.0562(11) Uani 1 1 d . . . . .
C01P C 0.7971(4) 0.52950(10) 0.5937(2) 0.0604(12) Uani 1 1 d . . . . .
H01P H 0.8232 0.5463 0.5748 0.073 Uiso 1 1 calc R . . . .
C01Q C -0.0719(5) 0.75483(9) 0.4053(2) 0.0626(13) Uani 1 1 d . . . . .
C01R C 0.0670(5) 0.65750(11) 0.72010(19) 0.0626(12) Uani 1 1 d . . . . .
H01R H 0.0713 0.6494 0.7544 0.075 Uiso 1 1 calc R . . . .
C01S C 0.7967(4) 0.55929(10) 0.45826(19) 0.0600(12) Uani 1 1 d . . . . .
H01S H 0.8957 0.5631 0.4563 0.072 Uiso 1 1 calc R . . . .
C01T C -0.0402(5) 0.67520(11) 0.7075(2) 0.0665(13) Uani 1 1 d . . . . .
H01T H -0.1120 0.6791 0.7328 0.080 Uiso 1 1 calc R . . . .
C01U C -0.1486(5) 0.76351(10) 0.4486(2) 0.0661(14) Uani 1 1 d . . . . .
H01U H -0.2120 0.7793 0.4454 0.079 Uiso 1 1 calc R . . . .
C01V C 0.8950(5) 0.50790(12) 0.6011(2) 0.0685(14) Uani 1 1 d . . . . .
H01V H 0.9886 0.5101 0.5878 0.082 Uiso 1 1 calc R . . . .
C01W C -0.1631(5) 0.70477(11) 0.6407(2) 0.0665(13) Uani 1 1 d . . . . .
H01W H -0.2397 0.7082 0.6642 0.080 Uiso 1 1 calc R . . . .
C01X C 0.5412(6) 0.44930(10) 0.6885(2) 0.0673(14) Uani 1 1 d . . . . .
H01X H 0.5144 0.4314 0.7036 0.081 Uiso 1 1 calc R . . . .
C01Y C 0.0992(5) 0.73860(10) 0.3173(2) 0.0670(13) Uani 1 1 d . . . . .
C01Z C -0.1656(5) 0.71607(10) 0.5915(2) 0.0675(14) Uani 1 1 d . . . . .
H01Z H -0.2464 0.7266 0.5801 0.081 Uiso 1 1 calc R . . . .
C020 C -0.0848(6) 0.76875(11) 0.3551(3) 0.0749(15) Uani 1 1 d . . . . .
H020 H -0.1518 0.7839 0.3512 0.090 Uiso 1 1 calc R . . . .
C021 C -0.0060(6) 0.76121(11) 0.3137(3) 0.0766(16) Uani 1 1 d . . . . .
H021 H -0.0191 0.7709 0.2811 0.092 Uiso 1 1 calc R . . . .
C023 C 0.5676(5) 0.63045(12) 0.3833(2) 0.0707(14) Uani 1 1 d . . . . .
H023 H 0.5327 0.6115 0.3789 0.085 Uiso 1 1 calc R . . . .
C024 C 0.6752(6) 0.45291(11) 0.6707(2) 0.0695(14) Uani 1 1 d . . . . .
H024 H 0.7413 0.4376 0.6742 0.083 Uiso 1 1 calc R . . . .
C025 C 0.8586(5) 0.48319(12) 0.6274(2) 0.0725(16) Uani 1 1 d . . . . .
H025 H 0.9278 0.4686 0.6327 0.087 Uiso 1 1 calc R . . . .
C026 C 0.3077(6) 0.69556(11) 0.3297(2) 0.0721(14) Uani 1 1 d . . . . .
H026 H 0.3785 0.6812 0.3337 0.086 Uiso 1 1 calc R . . . .
C027 C 0.2947(6) 0.71049(12) 0.2816(2) 0.0781(15) Uani 1 1 d . . . . .
H027 H 0.3567 0.7062 0.2531 0.094 Uiso 1 1 calc R . . . .
C028 C 0.1912(6) 0.73141(12) 0.2761(2) 0.0782(16) Uani 1 1 d . . . . .
H028 H 0.1824 0.7412 0.2433 0.094 Uiso 1 1 calc R . . . .
C029 C 0.6678(6) 0.68649(14) 0.3942(3) 0.0909(19) Uani 1 1 d . . . . .
H029 H 0.7024 0.7056 0.3973 0.109 Uiso 1 1 calc R . . . .
C02A C 0.6275(8) 0.64429(16) 0.3419(2) 0.103(2) Uani 1 1 d . . . . .
H02A H 0.6352 0.6348 0.3088 0.124 Uiso 1 1 calc R . . . .
C02C C 0.6783(8) 0.67260(18) 0.3472(3) 0.114(3) Uani 1 1 d . . . . .
H02C H 0.7202 0.6820 0.3179 0.137 Uiso 1 1 calc R . . . .


_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
O001 C00A 1.360(4) . ?
O001 C00B 1.392(5) . ?
O002 C007 1.373(4) . ?
O002 C009 1.404(4) . ?
N003 C00A 1.303(5) . ?
N003 C00H 1.375(5) . ?
N004 C007 1.305(5) . ?
N004 C00E 1.360(5) . ?
N005 C00L 1.328(5) . ?
N005 C00N 1.365(5) . ?
N006 C00O 1.355(5) . ?
N006 C00T 1.330(5) . ?
C007 C00K 1.411(5) . ?
C008 C00E 1.411(5) . ?
C008 C00S 1.412(6) . ?
C008 C01B 1.429(6) . ?
C009 C00D 1.375(5) . ?
C009 C00M 1.405(5) . ?
C00A C019 1.411(6) . ?
C00B C00C 1.368(5) . ?
C00B C01A 1.403(5) . ?
C00C C00D 1.493(5) . ?
C00C C00R 1.422(6) . ?
C00D C00F 1.434(5) . ?
C00E C00N 1.450(5) . ?
C00F C00I 1.421(5) . ?
C00F C016 1.420(5) . ?
C00G C00J 1.406(5) . ?
C00G C00V 1.426(5) . ?
C00G C012 1.448(5) . ?
C00H C00O 1.441(5) . ?
C00H C00Y 1.409(6) . ?
C00I C00U 1.409(5) . ?
C00I C00W 1.419(5) . ?
C00J C00L 1.490(5) . ?
C00J C01F 1.397(6) . ?
C00K H00K 0.9500 . ?
C00K C00S 1.353(5) . ?
C00L C01H 1.409(6) . ?
C00M H00M 0.9500 . ?
C00M C00W 1.350(5) . ?
C00N C00P 1.410(5) . ?
C00O C010 1.408(6) . ?
C00P C017 1.425(6) . ?
C00P C01C 1.396(6) . ?
C00Q C00T 1.478(6) . ?
C00Q C00X 1.431(6) . ?
C00Q C01J 1.409(6) . ?
C00R C01M 1.428(6) . ?
C00R C023 1.423(6) . ?
C00S H00S 0.9500 . ?
C00T C01Z 1.440(6) . ?
C00U H00U 0.9500 . ?
C00U C01N 1.356(6) . ?
C00V C013 1.433(6) . ?
C00V C01D 1.420(6) . ?
C00W H00W 0.9500 . ?
C00X C014 1.442(5) . ?
C00X C015 1.427(6) . ?
C00Y C01L 1.404(6) . ?
C00Y C01R 1.428(6) . ?
C00Z C011 1.421(6) . ?
C00Z C013 1.411(6) . ?
C00Z C01P 1.405(6) . ?
C010 C01T 1.428(7) . ?
C010 C01W 1.391(6) . ?
C011 H011 0.9500 . ?
C011 C012 1.357(5) . ?
C012 H012 0.9500 . ?
C013 C01G 1.419(6) . ?
C014 H014 0.9500 . ?
C014 C01E 1.346(6) . ?
C015 C018 1.425(6) . ?
C015 C01Q 1.431(6) . ?
C016 H016 0.9500 . ?
C016 C01S 1.370(6) . ?
C017 H017 0.9500 . ?
C017 C01B 1.348(6) . ?
C018 C01O 1.424(6) . ?
C018 C01Y 1.427(7) . ?
C019 H019 0.9500 . ?
C019 C01L 1.355(6) . ?
C01A H01A 0.9500 . ?
C01A C01K 1.357(6) . ?
C01B H01B 0.9500 . ?
C01C H01C 0.9500 . ?
C01C C01H 1.372(6) . ?
C01D C01I 1.386(6) . ?
C01D C01X 1.436(6) . ?
C01E H01E 0.9500 . ?
C01E C01O 1.434(6) . ?
C01F H01F 0.9500 . ?
C01F C01I 1.381(6) . ?
C01G C024 1.435(7) . ?
C01G C025 1.401(7) . ?
C01H H01H 0.9500 . ?
C01I H01I 0.9500 . ?
C01J H01J 0.9500 . ?
C01J C01U 1.375(7) . ?
C01K H01K 0.9500 . ?
C01K C01M 1.407(7) . ?
C01L H01L 0.9500 . ?
C01M C029 1.408(7) . ?
C01N H01N 0.9500 . ?
C01N C01S 1.400(6) . ?
C01O C026 1.389(7) . ?
C01P H01P 0.9500 . ?
C01P C01V 1.376(7) . ?
C01Q C01U 1.374(7) . ?
C01Q C020 1.435(7) . ?
C01R H01R 0.9500 . ?
C01R C01T 1.342(7) . ?
C01S H01S 0.9500 . ?
C01T H01T 0.9500 . ?
C01U H01U 0.9500 . ?
C01V H01V 0.9500 . ?
C01V C025 1.374(7) . ?
C01W H01W 0.9500 . ?
C01W C01Z 1.354(7) . ?
C01X H01X 0.9500 . ?
C01X C024 1.351(7) . ?
C01Y C021 1.448(7) . ?
C01Y C028 1.399(7) . ?
C01Z H01Z 0.9500 . ?
C020 H020 0.9500 . ?
C020 C021 1.332(8) . ?
C021 H021 0.9500 . ?
C023 H023 0.9500 . ?
C023 C02A 1.356(7) . ?
C024 H024 0.9500 . ?
C025 H025 0.9500 . ?
C026 H026 0.9500 . ?
C026 C027 1.409(7) . ?
C027 H027 0.9500 . ?
C027 C028 1.385(7) . ?
C028 H028 0.9500 . ?
C029 H029 0.9500 . ?
C029 C02C 1.360(9) . ?
C02A H02A 0.9500 . ?
C02A C02C 1.409(10) . ?
C02C H02C 0.9500 . ?

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
C00A O001 C00B 122.1(3) . . ?
C007 O002 C009 119.2(3) . . ?
C00A N003 C00H 116.5(3) . . ?
C007 N004 C00E 117.1(3) . . ?
C00L N005 C00N 118.3(3) . . ?
C00T N006 C00O 120.0(4) . . ?
O002 C007 C00K 115.5(4) . . ?
N004 C007 O002 119.2(3) . . ?
N004 C007 C00K 125.3(4) . . ?
C00E C008 C00S 117.3(4) . . ?
C00E C008 C01B 119.8(4) . . ?
C00S C008 C01B 122.9(4) . . ?
O002 C009 C00M 119.8(3) . . ?
C00D C009 O002 117.0(3) . . ?
C00D C009 C00M 122.8(3) . . ?
O001 C00A C019 113.6(3) . . ?
N003 C00A O001 120.7(4) . . ?
N003 C00A C019 125.7(4) . . ?
O001 C00B C01A 119.5(4) . . ?
C00C C00B O001 116.7(3) . . ?
C00C C00B C01A 123.1(4) . . ?
C00B C00C C00D 120.9(3) . . ?
C00B C00C C00R 118.1(4) . . ?
C00R C00C C00D 120.9(4) . . ?
C009 C00D C00C 121.0(3) . . ?
C009 C00D C00F 117.7(3) . . ?
C00F C00D C00C 121.3(3) . . ?
N004 C00E C008 122.6(4) . . ?
N004 C00E C00N 118.5(3) . . ?
C008 C00E C00N 118.9(3) . . ?
C00I C00F C00D 119.9(3) . . ?
C016 C00F C00D 122.0(4) . . ?
C016 C00F C00I 118.0(3) . . ?
C00J C00G C00V 119.6(4) . . ?
C00J C00G C012 123.8(4) . . ?
C00V C00G C012 116.6(4) . . ?
N003 C00H C00O 118.7(4) . . ?
N003 C00H C00Y 122.4(4) . . ?
C00Y C00H C00O 118.9(4) . . ?
C00U C00I C00F 119.2(4) . . ?
C00U C00I C00W 122.1(4) . . ?
C00W C00I C00F 118.7(3) . . ?
C00G C00J C00L 124.6(4) . . ?
C01F C00J C00G 118.4(4) . . ?
C01F C00J C00L 117.0(4) . . ?
C007 C00K H00K 121.3 . . ?
C00S C00K C007 117.5(4) . . ?
C00S C00K H00K 121.3 . . ?
N005 C00L C00J 117.7(4) . . ?
N005 C00L C01H 121.9(4) . . ?
C01H C00L C00J 120.4(4) . . ?
C009 C00M H00M 120.2 . . ?
C00W C00M C009 119.6(4) . . ?
C00W C00M H00M 120.2 . . ?
N005 C00N C00E 117.4(3) . . ?
N005 C00N C00P 123.1(4) . . ?
C00P C00N C00E 119.4(3) . . ?
N006 C00O C00H 118.3(3) . . ?
N006 C00O C010 122.7(4) . . ?
C010 C00O C00H 119.0(4) . . ?
C00N C00P C017 119.6(4) . . ?
C01C C00P C00N 116.7(4) . . ?
C01C C00P C017 123.7(4) . . ?
C00X C00Q C00T 125.7(4) . . ?
C01J C00Q C00T 116.8(4) . . ?
C01J C00Q C00X 117.5(5) . . ?
C00C C00R C01M 119.6(4) . . ?
C00C C00R C023 122.0(4) . . ?
C023 C00R C01M 118.4(4) . . ?
C008 C00S H00S 119.9 . . ?
C00K C00S C008 120.2(4) . . ?
C00K C00S H00S 119.9 . . ?
N006 C00T C00Q 119.6(4) . . ?
N006 C00T C01Z 119.3(4) . . ?
C01Z C00T C00Q 121.1(4) . . ?
C00I C00U H00U 119.3 . . ?
C01N C00U C00I 121.4(4) . . ?
C01N C00U H00U 119.3 . . ?
C00G C00V C013 120.9(4) . . ?
C01D C00V C00G 120.3(4) . . ?
C01D C00V C013 118.8(4) . . ?
C00I C00W H00W 119.4 . . ?
C00M C00W C00I 121.3(4) . . ?
C00M C00W H00W 119.4 . . ?
C00Q C00X C014 124.0(4) . . ?
C015 C00X C00Q 119.6(4) . . ?
C015 C00X C014 116.4(4) . . ?
C00H C00Y C01R 120.2(4) . . ?
C01L C00Y C00H 117.6(4) . . ?
C01L C00Y C01R 122.1(4) . . ?
C013 C00Z C011 118.3(4) . . ?
C01P C00Z C011 122.1(4) . . ?
C01P C00Z C013 119.6(4) . . ?
C00O C010 C01T 120.1(4) . . ?
C01W C010 C00O 117.4(5) . . ?
C01W C010 C01T 122.5(4) . . ?
C00Z C011 H011 119.0 . . ?
C012 C011 C00Z 122.0(4) . . ?
C012 C011 H011 119.0 . . ?
C00G C012 H012 119.0 . . ?
C011 C012 C00G 121.9(4) . . ?
C011 C012 H012 119.0 . . ?
C00Z C013 C00V 120.2(4) . . ?
C00Z C013 C01G 118.9(4) . . ?
C01G C013 C00V 120.9(4) . . ?
C00X C014 H014 118.9 . . ?
C01E C014 C00X 122.3(4) . . ?
C01E C014 H014 118.9 . . ?
C00X C015 C01Q 119.8(5) . . ?
C018 C015 C00X 121.3(4) . . ?
C018 C015 C01Q 118.9(5) . . ?
C00F C016 H016 119.7 . . ?
C01S C016 C00F 120.6(4) . . ?
C01S C016 H016 119.7 . . ?
C00P C017 H017 119.4 . . ?
C01B C017 C00P 121.3(4) . . ?
C01B C017 H017 119.4 . . ?
C015 C018 C01Y 121.1(4) . . ?
C01O C018 C015 120.4(4) . . ?
C01O C018 C01Y 118.5(5) . . ?
C00A C019 H019 121.3 . . ?
C01L C019 C00A 117.5(4) . . ?
C01L C019 H019 121.3 . . ?
C00B C01A H01A 120.6 . . ?
C01K C01A C00B 118.7(4) . . ?
C01K C01A H01A 120.6 . . ?
C008 C01B H01B 119.5 . . ?
C017 C01B C008 121.0(4) . . ?
C017 C01B H01B 119.5 . . ?
C00P C01C H01C 120.0 . . ?
C01H C01C C00P 120.1(4) . . ?
C01H C01C H01C 120.0 . . ?
C00V C01D C01X 119.4(4) . . ?
C01I C01D C00V 118.5(4) . . ?
C01I C01D C01X 122.1(4) . . ?
C014 C01E H01E 118.8 . . ?
C014 C01E C01O 122.5(4) . . ?
C01O C01E H01E 118.8 . . ?
C00J C01F H01F 118.9 . . ?
C01I C01F C00J 122.1(4) . . ?
C01I C01F H01F 118.9 . . ?
C013 C01G C024 118.1(4) . . ?
C025 C01G C013 119.6(5) . . ?
C025 C01G C024 122.3(4) . . ?
C00L C01H H01H 120.2 . . ?
C01C C01H C00L 119.5(4) . . ?
C01C C01H H01H 120.2 . . ?
C01D C01I H01I 119.5 . . ?
C01F C01I C01D 120.9(4) . . ?
C01F C01I H01I 119.5 . . ?
C00Q C01J H01J 118.7 . . ?
C01U C01J C00Q 122.6(5) . . ?
C01U C01J H01J 118.7 . . ?
C01A C01K H01K 119.1 . . ?
C01A C01K C01M 121.8(4) . . ?
C01M C01K H01K 119.1 . . ?
C00Y C01L H01L 119.9 . . ?
C019 C01L C00Y 120.2(4) . . ?
C019 C01L H01L 119.9 . . ?
C01K C01M C00R 118.5(4) . . ?
C01K C01M C029 122.4(5) . . ?
C029 C01M C00R 119.1(5) . . ?
C00U C01N H01N 120.1 . . ?
C00U C01N C01S 119.9(4) . . ?
C01S C01N H01N 120.1 . . ?
C018 C01O C01E 117.1(4) . . ?
C026 C01O C018 121.1(5) . . ?
C026 C01O C01E 121.8(4) . . ?
C00Z C01P H01P 119.7 . . ?
C01V C01P C00Z 120.6(5) . . ?
C01V C01P H01P 119.7 . . ?
C015 C01Q C020 118.6(5) . . ?
C01U C01Q C015 119.3(5) . . ?
C01U C01Q C020 122.1(5) . . ?
C00Y C01R H01R 119.6 . . ?
C01T C01R C00Y 120.7(5) . . ?
C01T C01R H01R 119.6 . . ?
C016 C01S C01N 120.8(4) . . ?
C016 C01S H01S 119.6 . . ?
C01N C01S H01S 119.6 . . ?
C010 C01T H01T 119.6 . . ?
C01R C01T C010 120.9(4) . . ?
C01R C01T H01T 119.6 . . ?
C01J C01U H01U 119.4 . . ?
C01Q C01U C01J 121.2(4) . . ?
C01Q C01U H01U 119.4 . . ?
C01P C01V H01V 119.7 . . ?
C025 C01V C01P 120.7(5) . . ?
C025 C01V H01V 119.7 . . ?
C010 C01W H01W 120.1 . . ?
C01Z C01W C010 119.8(4) . . ?
C01Z C01W H01W 120.1 . . ?
C01D C01X H01X 119.5 . . ?
C024 C01X C01D 121.1(5) . . ?
C024 C01X H01X 119.5 . . ?
C018 C01Y C021 117.5(5) . . ?
C028 C01Y C018 119.0(5) . . ?
C028 C01Y C021 123.4(5) . . ?
C00T C01Z H01Z 119.7 . . ?
C01W C01Z C00T 120.7(4) . . ?
C01W C01Z H01Z 119.7 . . ?
C01Q C020 H020 118.9 . . ?
C021 C020 C01Q 122.3(5) . . ?
C021 C020 H020 118.9 . . ?
C01Y C021 H021 119.2 . . ?
C020 C021 C01Y 121.5(5) . . ?
C020 C021 H021 119.2 . . ?
C00R C023 H023 119.7 . . ?
C02A C023 C00R 120.6(6) . . ?
C02A C023 H023 119.7 . . ?
C01G C024 H024 119.1 . . ?
C01X C024 C01G 121.7(4) . . ?
C01X C024 H024 119.1 . . ?
C01G C025 H025 119.7 . . ?
C01V C025 C01G 120.6(5) . . ?
C01V C025 H025 119.7 . . ?
C01O C026 H026 120.1 . . ?
C01O C026 C027 119.8(5) . . ?
C027 C026 H026 120.1 . . ?
C026 C027 H027 120.1 . . ?
C028 C027 C026 119.7(5) . . ?
C028 C027 H027 120.1 . . ?
C01Y C028 H028 119.0 . . ?
C027 C028 C01Y 121.9(5) . . ?
C027 C028 H028 119.0 . . ?
C01M C029 H029 119.6 . . ?
C02C C029 C01M 120.9(6) . . ?
C02C C029 H029 119.6 . . ?
C023 C02A H02A 119.6 . . ?
C023 C02A C02C 120.7(6) . . ?
C02C C02A H02A 119.6 . . ?
C029 C02C C02A 120.3(6) . . ?
C029 C02C H02C 119.8 . . ?
C02A C02C H02C 119.8 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 0.0 0.0 ?
2 0.468 0.117 0.250 332.8 74.4 ?
3 -0.073 0.174 0.667 8.6 0.0 ?
4 -0.072 0.247 0.345 22.5 0.0 ?
5 -0.072 0.253 0.845 22.5 0.0 ?
6 -0.063 0.383 0.750 332.8 74.4 ?
7 -0.073 0.326 0.167 8.6 0.0 ?
8 0.000 0.500 0.500 0.0 0.0 ?
9 -0.292 0.617 0.250 332.8 74.4 ?
10 0.073 0.674 0.833 8.6 0.0 ?
11 0.072 0.747 0.155 22.5 0.0 ?
12 0.072 0.753 0.655 22.5 0.0 ?
13 -0.059 0.883 0.750 332.8 74.4 ?
14 0.073 0.826 0.333 8.6 0.0 ?
15 0.042 0.005 0.004 0.0 0.0 ?
16 0.042 0.495 0.504 0.0 0.0 ?
17 0.250 0.208 0.733 7.3 0.0 ?
18 0.250 0.292 0.233 7.3 0.0 ?
19 0.250 0.708 0.733 7.3 0.0 ?
20 0.250 0.792 0.233 7.3 0.0 ?
21 0.428 0.247 0.155 22.5 0.0 ?
22 0.428 0.253 0.655 22.5 0.0 ?
23 0.427 0.174 0.833 8.6 0.0 ?
24 0.427 0.326 0.333 8.6 0.0 ?
25 0.572 0.747 0.345 22.5 0.0 ?
26 0.572 0.753 0.845 22.5 0.0 ?
27 0.573 0.674 0.667 8.6 0.0 ?
28 0.573 0.826 0.167 8.6 0.0 ?
29 0.458 0.505 0.004 0.0 0.0 ?
30 0.458 0.995 0.504 0.0 0.0 ?
31 0.500 0.000 0.500 0.0 0.0 ?
32 0.500 0.500 0.000 0.0 0.0 ?
33 0.542 0.005 0.496 0.0 0.0 ?
34 0.542 0.495 -0.004 0.0 0.0 ?
35 0.750 0.208 0.767 7.3 0.0 ?
36 0.750 0.292 0.267 7.3 0.0 ?
37 0.750 0.708 0.767 7.3 0.0 ?
38 0.750 0.792 0.267 7.3 0.0 ?
39 0.958 0.505 0.496 0.0 0.0 ?
40 0.958 0.995 -0.004 0.0 0.0 ?

_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.640
####################################################################### 
# 
# 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_g_auto
_database_code_depnum_ccdc_archive 'CCDC 2469789'
loop_
_audit_author_name
_audit_author_address
'Tianhao Wang'
;Shandong University
China
;
_audit_update_record             
;
2025-07-04 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-03-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2 O Se'
_chemical_formula_sum            'C12 H12 N2 O Se'
_chemical_formula_weight         279.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNOSe
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      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                   6.9368(2)
_cell_length_b                   4.78530(10)
_cell_length_c                   17.3245(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.194(3)
_cell_angle_gamma                90
_cell_volume                     569.21(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2754
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.6370
_cell_measurement_theta_min      2.5550
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.480
_exptl_absorpt_coefficient_mu    4.300
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.2
_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  0.0481
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5054
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.929
_diffrn_reflns_theta_min         2.577
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   6.00   1.00    0.10    --  -48.42  42.00-168.00   26
  2  ω    -23.00  22.00   1.00    0.10    --  -48.42  19.00   0.00   45
  3  ω     81.00 106.00   1.00    0.12    --  106.65 -99.00  30.00   25
  4  ω     42.00  77.00   1.00    0.12    --  106.65 -99.00  30.00   35
  5  ω     38.00 103.00   1.00    0.12    --  106.65 -77.00  60.00   65
  6  ω     41.00  66.00   1.00    0.12    --  106.65 -57.00 150.00   25
  7  ω     41.00  66.00   1.00    0.12    --  106.65 -57.00 120.00   25
  8  ω    -10.00  40.00   1.00    0.10    --   48.42 -42.00  39.00   50
  9  ω     35.00  60.00   1.00    0.12    --  106.65 -57.00 -90.00   25
 10  ω     38.00  63.00   1.00    0.12    --  106.65 -57.00-150.00   25
 11  ω     38.00  64.00   1.00    0.12    --  106.65 -57.00-180.00   26
 12  ω     45.00  75.00   1.00    0.10    --   48.42  42.00-168.00   30
 13  ω     80.00 118.00   1.00    0.10    --   48.42  42.00-168.00   38
 14  ω     95.00 151.00   1.00    0.12    --  106.65  42.00-168.00   56
 15  ω     30.00  96.00   1.00    0.10    --   48.42  77.00 -90.00   66
 16  ω    -65.00 -30.00   1.00    0.12    --  -91.75  57.00 -60.00   35
 17  ω    -47.00 -22.00   1.00    0.12    --  -91.75  42.00-168.00   25
 18  ω    -60.00 -33.00   1.00    0.12    --  -91.75  57.00   0.00   27
 19  ω    -60.00 -21.00   1.00    0.12    --  -91.75  57.00 150.00   39
 20  ω   -120.00 -56.00   1.00    0.10    --  -48.42 -42.00  39.00   64
 21  ω   -160.00-132.00   1.00    0.12    --  -91.75 -77.00 -30.00   28
 22  ω   -149.00-124.00   1.00    0.12    --  -91.75 -77.00 -60.00   25
 23  ω   -159.00 -69.00   1.00    0.12    --  -91.75 -77.00 -90.00   90
 24  ω   -113.00 -69.00   1.00    0.12    --  -91.75 -77.00 -30.00   44
 25  ω   -114.00 -71.00   1.00    0.12    --  -91.75 -77.00 -60.00   43
 26  ω   -151.00-123.00   1.00    0.12    --  -91.75 -57.00 -30.00   28
 27  ω   -159.00-120.00   1.00    0.12    --  -91.75 -57.00   0.00   39
 28  ω   -110.00 -79.00   1.00    0.12    --  -91.75 -42.00  39.00   31
 29  ω   -109.00 -77.00   1.00    0.12    --  -91.75 -57.00   0.00   32
 30  ω   -115.00 -78.00   1.00    0.12    --  -91.75 -57.00 -30.00   37
 31  ω   -125.00 -86.00   1.00    0.12    --  -91.75 -99.00-180.00   39
 32  ω   -158.00-132.00   1.00    0.12    --  -91.75 -99.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0738365000
_diffrn_orient_matrix_UB_12      0.0742804000
_diffrn_orient_matrix_UB_13      0.0856474000
_diffrn_orient_matrix_UB_21      0.1929994000
_diffrn_orient_matrix_UB_22      -0.1525445000
_diffrn_orient_matrix_UB_23      -0.0058498000
_diffrn_orient_matrix_UB_31      0.0874364000
_diffrn_orient_matrix_UB_32      0.2735637000
_diffrn_orient_matrix_UB_33      -0.0265219000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                2001
_reflns_number_total             2137
_reflns_odcompleteness_completeness 99.39
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      0.857
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1138
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00D(H00D,H00E), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C008(H008), C00C(H00C), C3(H3)
;
_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 0.26634(7) 0.7592(3) 0.50175(3) 0.0308(2) Uani 1 1 d . . . . .
O002 O 0.3921(8) 0.9143(10) 0.6623(3) 0.0332(12) Uani 1 1 d . . . . .
N003 N 0.4916(7) 0.4907(11) 0.7116(3) 0.0270(10) Uani 1 1 d . . . . .
H003 H 0.486285 0.309200 0.703470 0.032 Uiso 1 1 calc R U . . .
C004 C 0.7714(8) 0.3942(13) 0.8107(3) 0.0238(11) Uani 1 1 d . . . . .
C005 C 0.9034(9) 0.1227(15) 0.9223(4) 0.0347(14) Uani 1 1 d . . . . .
H005 H 0.902641 0.068983 0.975068 0.042 Uiso 1 1 calc R U . . .
C006 C 0.7675(8) 0.3115(14) 0.8873(3) 0.0284(14) Uani 1 1 d . . . . .
N007 N 0.1526(9) 0.3123(15) 0.3830(3) 0.0443(15) Uani 1 1 d . . . . .
C008 C 0.9096(8) 0.2857(18) 0.7682(3) 0.0307(12) Uani 1 1 d . . . . .
H008 H 0.910942 0.341086 0.715582 0.037 Uiso 1 1 calc R U . . .
C009 C 0.2751(9) 0.5091(14) 0.5910(3) 0.0282(13) Uani 1 1 d . . . . .
H00A H 0.141913 0.471511 0.602678 0.034 Uiso 1 1 calc R U . . .
H00B H 0.336385 0.329195 0.580169 0.034 Uiso 1 1 calc R U . . .
C00A C 0.3949(11) 0.6557(13) 0.6594(4) 0.0247(14) Uani 1 1 d . . . . .
C00B C 0.1951(9) 0.4830(15) 0.4286(4) 0.0304(13) Uani 1 1 d . . . . .
C00C C 1.0458(10) 0.0953(15) 0.8035(4) 0.0369(15) Uani 1 1 d . . . . .
H00C H 1.142568 0.021359 0.775544 0.044 Uiso 1 1 calc R U . . .
C00D C 0.4919(10) 0.6181(16) 0.8525(4) 0.0376(16) Uani 1 1 d . . . . .
H00D H 0.473764 0.816751 0.865697 0.045 Uiso 1 1 calc R U . . .
H00E H 0.361939 0.531058 0.839007 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6083(8) 0.5952(13) 0.7830(3) 0.0247(12) Uani 1 1 d . . . . .
H2 H 0.664023 0.781921 0.772687 0.030 Uiso 1 1 calc R U . . .
C3 C 1.0391(10) 0.0137(17) 0.8806(4) 0.0370(15) Uani 1 1 d . . . . .
H3 H 1.130239 -0.119695 0.904367 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6080(11) 0.4664(18) 0.9214(4) 0.0438(17) Uani 1 1 d . . . . .
H4A H 0.664733 0.601338 0.961713 0.053 Uiso 1 1 calc R U . . .
H4B H 0.523945 0.333960 0.945243 0.053 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
Se01 C009 1.950(6) . ?
Se01 C00B 1.849(7) . ?
O002 C00A 1.239(7) . ?
N003 H003 0.8800 . ?
N003 C00A 1.312(8) . ?
N003 C2 1.466(7) . ?
C004 C006 1.389(7) . ?
C004 C008 1.390(8) . ?
C004 C2 1.510(8) . ?
C005 H005 0.9500 . ?
C005 C006 1.382(9) . ?
C005 C3 1.370(9) . ?
C006 C4 1.520(8) . ?
N007 C00B 1.144(10) . ?
C008 H008 0.9500 . ?
C008 C00C 1.391(9) . ?
C009 H00A 0.9900 . ?
C009 H00B 0.9900 . ?
C009 C00A 1.517(9) . ?
C00C H00C 0.9500 . ?
C00C C3 1.398(10) . ?
C00D H00D 0.9900 . ?
C00D H00E 0.9900 . ?
C00D C2 1.546(8) . ?
C00D C4 1.526(10) . ?
C2 H2 1.0000 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
C00B Se01 C009 94.6(3) . . ?
C00A N003 H003 118.5 . . ?
C00A N003 C2 123.0(5) . . ?
C2 N003 H003 118.5 . . ?
C006 C004 C008 120.6(5) . . ?
C006 C004 C2 111.6(5) . . ?
C008 C004 C2 127.7(5) . . ?
C006 C005 H005 120.2 . . ?
C3 C005 H005 120.2 . . ?
C3 C005 C006 119.6(6) . . ?
C004 C006 C4 110.3(5) . . ?
C005 C006 C004 120.1(5) . . ?
C005 C006 C4 129.5(5) . . ?
C004 C008 H008 120.4 . . ?
C004 C008 C00C 119.2(5) . . ?
C00C C008 H008 120.4 . . ?
Se01 C009 H00A 110.4 . . ?
Se01 C009 H00B 110.4 . . ?
H00A C009 H00B 108.6 . . ?
C00A C009 Se01 106.7(4) . . ?
C00A C009 H00A 110.4 . . ?
C00A C009 H00B 110.4 . . ?
O002 C00A N003 125.6(7) . . ?
O002 C00A C009 118.9(7) . . ?
N003 C00A C009 115.4(5) . . ?
N007 C00B Se01 179.4(6) . . ?
C008 C00C H00C 120.3 . . ?
C008 C00C C3 119.4(6) . . ?
C3 C00C H00C 120.3 . . ?
H00D C00D H00E 108.5 . . ?
C2 C00D H00D 110.2 . . ?
C2 C00D H00E 110.2 . . ?
C4 C00D H00D 110.2 . . ?
C4 C00D H00E 110.2 . . ?
C4 C00D C2 107.4(5) . . ?
N003 C2 C004 110.4(5) . . ?
N003 C2 C00D 113.2(5) . . ?
N003 C2 H2 109.5 . . ?
C004 C2 C00D 104.4(5) . . ?
C004 C2 H2 109.5 . . ?
C00D C2 H2 109.5 . . ?
C005 C3 C00C 121.1(6) . . ?
C005 C3 H3 119.4 . . ?
C00C C3 H3 119.4 . . ?
C006 C4 C00D 105.0(5) . . ?
C006 C4 H4A 110.7 . . ?
C006 C4 H4B 110.7 . . ?
C00D C4 H4A 110.7 . . ?
C00D C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?

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
Se01 C009 C00A O002 31.1(9) . . . . ?
Se01 C009 C00A N003 -150.0(5) . . . . ?
C004 C006 C4 C00D 9.3(8) . . . . ?
C004 C008 C00C C3 1.0(10) . . . . ?
C005 C006 C4 C00D -173.8(7) . . . . ?
C006 C004 C008 C00C -0.7(10) . . . . ?
C006 C004 C2 N003 -124.8(5) . . . . ?
C006 C004 C2 C00D -2.7(6) . . . . ?
C006 C005 C3 C00C 1.6(11) . . . . ?
C008 C004 C006 C005 0.9(9) . . . . ?
C008 C004 C006 C4 178.1(7) . . . . ?
C008 C004 C2 N003 52.8(8) . . . . ?
C008 C004 C2 C00D 174.8(6) . . . . ?
C008 C00C C3 C005 -1.4(11) . . . . ?
C00A N003 C2 C004 -152.7(6) . . . . ?
C00A N003 C2 C00D 90.6(8) . . . . ?
C2 N003 C00A O002 1.5(12) . . . . ?
C2 N003 C00A C009 -177.4(5) . . . . ?
C2 C004 C006 C005 178.7(6) . . . . ?
C2 C004 C006 C4 -4.1(7) . . . . ?
C2 C004 C008 C00C -178.1(6) . . . . ?
C2 C00D C4 C006 -10.7(8) . . . . ?
C3 C005 C006 C004 -1.4(10) . . . . ?
C3 C005 C006 C4 -178.0(8) . . . . ?
C4 C00D C2 N003 128.6(6) . . . . ?
C4 C00D C2 C004 8.4(7) . . . . ?

_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.790
