# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_4227
_database_code_depnum_ccdc_archive 'CCDC 2358178'
loop_
_audit_author_name
_audit_author_address
hy
;Jishou University
China
;
_audit_update_record             
;
2024-05-25 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 F3 N2 S'
_chemical_formula_sum            'C23 H17 F3 N2 S'
_chemical_formula_weight         410.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
S S 0.3331 0.5567 '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                   11.4446(7)
_cell_length_b                   7.4929(4)
_cell_length_c                   22.0408(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.240(5)
_cell_angle_gamma                90
_cell_volume                     1888.63(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9220
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8360
_cell_measurement_theta_min      3.8190
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.753
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13984
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.034
_diffrn_reflns_theta_min         2.006
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  39.00   1.00    1.00    --  -40.92  19.00 -30.00   86
  2  ω    -61.00  31.00   1.00    1.00    --  -40.92  57.00  60.00   92
  3  ω     23.00  50.00   1.00    1.00    --   40.92-125.00-180.00   27
  4  ω     80.00 106.00   1.00    1.00    --  107.58 -94.00 -90.00   26
  5  ω     78.00 119.00   1.00    1.00    --  107.58-125.00 -90.00   41
  6  ω     76.00 137.00   1.00    1.00    --  107.58 -61.00 -30.00   61
  7  ω     69.00 108.00   1.00    1.00    --  107.58 -98.00   8.00   39
  8  ω     42.00  69.00   1.00    1.00    --  107.58-125.00 -90.00   27
  9  ω     37.00 124.00   1.00    1.00    --  107.58 -61.00-150.00   87
 10  ω     84.00 177.00   1.00    1.00    --  107.58  45.00   0.00   93
 11  ω     37.00  62.00   1.00    1.00    --  107.58 -94.00 150.00   25
 12  ω   -109.00 -14.00   1.00    1.00    --  -41.23 -57.00 150.00   95
 13  ω     26.00  52.00   1.00    1.00    --   41.23  57.00-180.00   26
 14  ω     10.00  49.00   1.00    1.00    --   41.23 -99.00-150.00   39
 15  ω     35.00  96.00   1.00    1.00    --   41.23-125.00 -30.00   61
 16  ω     75.00 132.00   1.00    1.00    --  107.58  77.00 150.00   57
 17  ω     75.00 101.00   1.00    1.00    --  107.58  77.00  90.00   26
 18  ω    138.00 173.00   1.00    1.00    --  107.58  15.00-180.00   35
 19  ω     78.00 104.00   1.00    1.00    --  107.58  61.00 120.00   26
 20  ω     82.00 113.00   1.00    1.00    --  107.58  45.00 120.00   31
 21  ω     79.00 107.00   1.00    1.00    --  107.58  61.00  60.00   28
 22  ω     78.00 104.00   1.00    1.00    --  107.58  61.00  90.00   26
 23  ω     79.00 105.00   1.00    1.00    --  107.58  61.00 150.00   26
 24  ω     75.00 101.00   1.00    1.00    --  107.58  77.00 120.00   26
 25  ω     83.00 109.00   1.00    1.00    --  107.58  45.00  90.00   26
 26  ω     77.00 103.00   1.00    1.00    --  107.58  77.00  60.00   26
 27  ω     82.00 118.00   1.00    1.00    --  107.58  45.00 150.00   36
 28  ω     32.00 151.00   1.00    1.00    --  107.58 -15.00-180.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1095409000
_diffrn_orient_matrix_UB_12      -0.0693823000
_diffrn_orient_matrix_UB_13      -0.0308956000
_diffrn_orient_matrix_UB_21      -0.0374483000
_diffrn_orient_matrix_UB_22      0.1004725000
_diffrn_orient_matrix_UB_23      -0.0585403000
_diffrn_orient_matrix_UB_31      0.0687610000
_diffrn_orient_matrix_UB_32      0.1655545000
_diffrn_orient_matrix_UB_33      0.0226040000
_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         0.767
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                6658
_reflns_number_total             7212
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 
;
 Flack x determined using 2594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.250(15)
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         7212
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.102
_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)+(0.1036P)²+1.1472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F9-C46 \\sim F10-C46
 with sigma of 0.02
 C46-F7 \\sim C46-F8
 with sigma of 0.02
 F5-C46 \\sim F6-C46
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F5, F7, F9, C42, C46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
 F6, F8, F10, C46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F6)=Sof(F8)=Sof(F10)=1-FVAR(1)
 Sof(F5)=Sof(F7)=Sof(F9)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37),
 C40(H40), C41(H41), C43(H43), C44(H44)
5.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C45(H45A,H45B,H45C)
;
_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
S1 S 0.21527(10) 0.2184(2) 0.73348(6) 0.0348(3) Uani 1 1 d . . . . .
F1 F 1.0111(4) 0.4927(6) 0.9305(2) 0.0646(13) Uani 1 1 d . . . . .
F2 F 0.9298(3) 0.3407(7) 0.99926(15) 0.0536(11) Uani 1 1 d . . . . .
F3 F 1.0331(3) 0.2107(7) 0.93407(17) 0.0570(11) Uani 1 1 d . . . . .
N1 N 0.4429(3) 0.2373(6) 0.69981(18) 0.0252(8) Uani 1 1 d . . . . .
N2 N 0.5566(3) 0.2446(6) 0.72138(19) 0.0282(9) Uani 1 1 d . . . . .
C1 C 0.4213(4) 0.2309(7) 0.6360(2) 0.0231(9) Uani 1 1 d . . . . .
C2 C 0.4953(4) 0.1330(7) 0.6001(2) 0.0268(10) Uani 1 1 d . . . . .
H2 H 0.559225 0.069219 0.618323 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4759(4) 0.1287(7) 0.5380(2) 0.0261(10) Uani 1 1 d . . . . .
H3 H 0.527647 0.062437 0.513956 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3820(4) 0.2192(7) 0.5092(2) 0.0223(9) Uani 1 1 d . . . . .
C5 C 0.3085(4) 0.3151(7) 0.5466(2) 0.0270(10) Uani 1 1 d . . . . .
H5 H 0.243780 0.377620 0.528586 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3270(4) 0.3218(7) 0.6088(2) 0.0283(10) Uani 1 1 d . . . . .
H6 H 0.275553 0.388219 0.632975 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3628(4) 0.2173(7) 0.4423(2) 0.0235(9) Uani 1 1 d . . . . .
C8 C 0.2577(4) 0.2780(8) 0.4151(2) 0.0320(11) Uani 1 1 d . . . . .
H8 H 0.196158 0.315685 0.439852 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2424(5) 0.2837(9) 0.3527(3) 0.0410(13) Uani 1 1 d . . . . .
H9 H 0.169958 0.323259 0.334966 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3314(5) 0.2326(9) 0.3155(2) 0.0400(13) Uani 1 1 d . . . . .
H10 H 0.320659 0.239523 0.272605 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4354(5) 0.1719(8) 0.3412(2) 0.0355(12) Uani 1 1 d . . . . .
H11 H 0.496514 0.134886 0.316109 0.043 Uiso 1 1 calc R U . . .
C12 C 0.4509(4) 0.1647(8) 0.4040(2) 0.0306(11) Uani 1 1 d . . . . .
H12 H 0.523109 0.122892 0.421351 0.037 Uiso 1 1 calc R U . . .
C13 C 0.3665(4) 0.2333(8) 0.7464(2) 0.0287(10) Uani 1 1 d . . . . .
C14 C 0.4330(4) 0.2389(8) 0.7993(2) 0.0300(11) Uani 1 1 d . . . . .
H14 H 0.406258 0.238377 0.839525 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5499(4) 0.2457(7) 0.7813(2) 0.0260(10) Uani 1 1 d . . . . .
C16 C 0.6553(4) 0.2637(8) 0.8211(2) 0.0298(11) Uani 1 1 d . . . . .
C17 C 0.6540(4) 0.2093(8) 0.8813(2) 0.0330(11) Uani 1 1 d . . . . .
H17 H 0.586245 0.153027 0.895915 0.040 Uiso 1 1 calc R U . . .
C18 C 0.7502(5) 0.2361(9) 0.9203(2) 0.0358(12) Uani 1 1 d . . . . .
H18 H 0.748351 0.198007 0.961325 0.043 Uiso 1 1 calc R U . . .
C19 C 0.8491(4) 0.3185(8) 0.8993(2) 0.0317(11) Uani 1 1 d . . . . .
C20 C 0.8529(4) 0.3711(8) 0.8389(2) 0.0317(11) Uani 1 1 d . . . . .
H20 H 0.921388 0.425050 0.824273 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7559(4) 0.3442(8) 0.8001(2) 0.0298(11) Uani 1 1 d . . . . .
H21 H 0.758054 0.381123 0.758946 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1709(5) 0.2387(9) 0.8103(2) 0.0388(13) Uani 1 1 d . . . . .
H22A H 0.085741 0.225943 0.811349 0.058 Uiso 1 1 calc R U . . .
H22B H 0.193974 0.356046 0.826275 0.058 Uiso 1 1 calc R U . . .
H22C H 0.208580 0.145147 0.835179 0.058 Uiso 1 1 calc R U . . .
C23 C 0.9534(5) 0.3421(8) 0.9409(2) 0.0341(12) Uani 1 1 d . . . . .
S2 S -0.02771(11) 0.7951(2) 0.77050(6) 0.0375(4) Uani 1 1 d . . . . .
F5 F 0.7547(10) 0.6044(11) 0.9968(8) 0.058(3) Uani 0.57(3) 1 d D . P A 1
F6 F 0.719(2) 0.633(3) 1.0275(11) 0.078(7) Uani 0.43(3) 1 d D . P A 2
F7 F 0.6792(10) 0.805(4) 1.0481(4) 0.095(8) Uani 0.57(3) 1 d D . P A 1
F8 F 0.6979(12) 0.913(2) 1.0292(10) 0.061(5) Uani 0.43(3) 1 d D . P A 2
F9 F 0.7876(13) 0.867(3) 0.9725(10) 0.081(6) Uani 0.57(3) 1 d D . P A 1
F10 F 0.8026(16) 0.799(4) 0.9660(10) 0.073(7) Uani 0.43(3) 1 d D . P A 2
N3 N 0.1989(3) 0.7271(6) 0.74517(17) 0.0260(8) Uani 1 1 d . . . . .
N4 N 0.3107(3) 0.7174(6) 0.76916(18) 0.0263(8) Uani 1 1 d . . . . .
C24 C 0.1221(4) 0.7184(7) 0.4873(2) 0.0244(9) Uani 1 1 d . . . . .
C25 C 0.0188(4) 0.6521(8) 0.4597(2) 0.0314(11) Uani 1 1 d . . . . .
H25 H -0.041400 0.609744 0.484465 0.038 Uiso 1 1 calc R U . . .
C26 C 0.0022(5) 0.6468(9) 0.3972(3) 0.0367(12) Uani 1 1 d . . . . .
H26 H -0.069292 0.602724 0.379686 0.044 Uiso 1 1 calc R U . . .
C27 C 0.0888(5) 0.7052(8) 0.3602(2) 0.0340(11) Uani 1 1 d . . . . .
H27 H 0.078111 0.698254 0.317280 0.041 Uiso 1 1 calc R U . . .
C28 C 0.1920(5) 0.7745(8) 0.3862(2) 0.0354(12) Uani 1 1 d . . . . .
H28 H 0.251228 0.818621 0.361134 0.042 Uiso 1 1 calc R U . . .
C29 C 0.2078(4) 0.7788(8) 0.4488(2) 0.0327(12) Uani 1 1 d . . . . .
H29 H 0.279156 0.824145 0.466101 0.039 Uiso 1 1 calc R U . . .
C30 C 0.1416(4) 0.7207(7) 0.5543(2) 0.0238(9) Uani 1 1 d . . . . .
C31 C 0.2358(4) 0.8139(7) 0.5820(2) 0.0257(10) Uani 1 1 d . . . . .
H31 H 0.287406 0.877926 0.557192 0.031 Uiso 1 1 calc R U . . .
C32 C 0.2557(4) 0.8150(7) 0.6443(2) 0.0265(10) Uani 1 1 d . . . . .
H32 H 0.320531 0.877976 0.661917 0.032 Uiso 1 1 calc R U . . .
C33 C 0.1795(4) 0.7228(7) 0.6810(2) 0.0238(9) Uani 1 1 d . . . . .
C34 C 0.0853(4) 0.6301(7) 0.6549(2) 0.0256(10) Uani 1 1 d . . . . .
H34 H 0.033184 0.567905 0.679940 0.031 Uiso 1 1 calc R U . . .
C35 C 0.0675(4) 0.6286(7) 0.5927(2) 0.0255(10) Uani 1 1 d . . . . .
H35 H 0.003330 0.563302 0.575406 0.031 Uiso 1 1 calc R U . . .
C36 C 0.1201(4) 0.7568(7) 0.7892(2) 0.0267(10) Uani 1 1 d . . . . .
C37 C 0.1824(4) 0.7619(8) 0.8434(2) 0.0299(11) Uani 1 1 d . . . . .
H37 H 0.152824 0.777571 0.882727 0.036 Uiso 1 1 calc R U . . .
C38 C 0.3001(4) 0.7389(8) 0.8283(2) 0.0276(10) Uani 1 1 d . . . . .
C39 C 0.4033(4) 0.7433(7) 0.8700(2) 0.0284(11) Uani 1 1 d . . . . .
C40 C 0.3939(4) 0.8056(9) 0.9288(2) 0.0359(12) Uani 1 1 d . . . . .
H40 H 0.319652 0.842484 0.941907 0.043 Uiso 1 1 calc R U . . .
C41 C 0.4894(5) 0.8156(9) 0.9687(2) 0.0363(12) Uani 1 1 d . . . . .
H41 H 0.481080 0.859698 1.008749 0.044 Uiso 1 1 calc R U . . .
C42 C 0.5979(4) 0.7603(7) 0.9498(2) 0.0296(11) Uani 1 1 d . . . . .
C43 C 0.5130(5) 0.6872(8) 0.8515(2) 0.0345(12) Uani 1 1 d . . . . .
H43 H 0.521229 0.642909 0.811557 0.041 Uiso 1 1 calc R U . . .
C44 C 0.6094(4) 0.6960(9) 0.8913(2) 0.0357(12) Uani 1 1 d . . . . .
H44 H 0.683724 0.657858 0.878455 0.043 Uiso 1 1 calc R U . . .
C45 C -0.0767(5) 0.8708(9) 0.8428(3) 0.0413(14) Uani 1 1 d . . . . .
H45A H -0.157580 0.912948 0.838136 0.062 Uiso 1 1 calc R U . . .
H45B H -0.026477 0.968643 0.857717 0.062 Uiso 1 1 calc R U . . .
H45C H -0.072582 0.771999 0.871970 0.062 Uiso 1 1 calc R U . . .
C46 C 0.7033(5) 0.7668(8) 0.9920(2) 0.0334(9) Uani 1 1 d 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
S1 C13 1.746(5) . ?
S1 C22 1.793(5) . ?
F1 C23 1.332(7) . ?
F2 C23 1.325(6) . ?
F3 C23 1.354(7) . ?
N1 N2 1.369(5) . ?
N1 C1 1.418(6) . ?
N1 C13 1.374(6) . ?
N2 C15 1.325(6) . ?
C1 C2 1.392(6) . ?
C1 C6 1.392(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(6) . ?
C4 C5 1.399(6) . ?
C4 C7 1.482(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(7) . ?
C7 C12 1.396(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.411(6) . ?
C15 C16 1.471(7) . ?
C16 C17 1.388(7) . ?
C16 C21 1.394(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(8) . ?
C19 C20 1.389(7) . ?
C19 C23 1.487(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(7) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S2 C36 1.749(5) . ?
S2 C45 1.802(6) . ?
F5 C46 1.354(9) . ?
F6 C46 1.278(12) . ?
F7 C46 1.310(9) . ?
F8 C46 1.372(11) . ?
F9 C46 1.308(11) . ?
F10 C46 1.316(13) . ?
N3 N4 1.367(5) . ?
N3 C33 1.424(6) . ?
N3 C36 1.368(6) . ?
N4 C38 1.324(6) . ?
C24 C25 1.400(7) . ?
C24 C29 1.398(6) . ?
C24 C30 1.484(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.384(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.379(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.394(8) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.404(7) . ?
C30 C35 1.403(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(7) . ?
C32 H32 0.9500 . ?
C32 C33 1.395(7) . ?
C33 C34 1.388(7) . ?
C34 H34 0.9500 . ?
C34 C35 1.378(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.369(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.411(6) . ?
C38 C39 1.467(7) . ?
C39 C40 1.386(7) . ?
C39 C43 1.399(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.378(7) . ?
C41 H41 0.9500 . ?
C41 C42 1.388(7) . ?
C42 C44 1.389(7) . ?
C42 C46 1.496(7) . ?
C43 H43 0.9500 . ?
C43 C44 1.384(7) . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 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
C13 S1 C22 99.0(2) . . ?
N2 N1 C1 118.2(3) . . ?
N2 N1 C13 111.5(4) . . ?
C13 N1 C1 130.3(4) . . ?
C15 N2 N1 104.8(4) . . ?
C2 C1 N1 119.7(4) . . ?
C2 C1 C6 119.4(4) . . ?
C6 C1 N1 120.9(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C7 121.8(4) . . ?
C5 C4 C3 116.7(4) . . ?
C5 C4 C7 121.5(4) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C4 121.0(4) . . ?
C12 C7 C4 121.4(4) . . ?
C12 C7 C8 117.5(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(5) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(5) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.6(5) . . ?
C11 C12 H12 119.2 . . ?
N1 C13 S1 122.4(4) . . ?
C14 C13 S1 131.0(4) . . ?
C14 C13 N1 106.6(4) . . ?
C13 C14 H14 127.3 . . ?
C13 C14 C15 105.3(4) . . ?
C15 C14 H14 127.3 . . ?
N2 C15 C14 111.9(4) . . ?
N2 C15 C16 121.1(4) . . ?
C14 C15 C16 126.9(4) . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 C21 119.0(5) . . ?
C21 C16 C15 120.7(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(5) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 120.2(5) . . ?
C18 C19 C23 119.6(5) . . ?
C20 C19 C23 120.2(5) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.6(5) . . ?
C20 C21 H21 119.7 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 F3 104.9(5) . . ?
F1 C23 C19 112.7(5) . . ?
F2 C23 F1 107.1(5) . . ?
F2 C23 F3 105.4(4) . . ?
F2 C23 C19 114.1(5) . . ?
F3 C23 C19 111.9(5) . . ?
C36 S2 C45 100.1(3) . . ?
N4 N3 C33 119.4(3) . . ?
N4 N3 C36 111.6(4) . . ?
C36 N3 C33 128.8(4) . . ?
C38 N4 N3 104.8(4) . . ?
C25 C24 C30 121.9(4) . . ?
C29 C24 C25 116.8(4) . . ?
C29 C24 C30 121.3(4) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.6(5) . . ?
C26 C25 H25 119.2 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.5(5) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(5) . . ?
C29 C28 H28 120.2 . . ?
C24 C29 H29 119.0 . . ?
C28 C29 C24 122.0(5) . . ?
C28 C29 H29 119.0 . . ?
C31 C30 C24 121.3(4) . . ?
C35 C30 C24 121.6(4) . . ?
C35 C30 C31 117.0(4) . . ?
C30 C31 H31 119.1 . . ?
C32 C31 C30 121.8(4) . . ?
C32 C31 H31 119.1 . . ?
C31 C32 H32 120.3 . . ?
C31 C32 C33 119.4(4) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 N3 119.2(4) . . ?
C34 C33 N3 120.7(4) . . ?
C34 C33 C32 120.1(4) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.9(4) . . ?
C35 C34 H34 120.1 . . ?
C30 C35 H35 119.1 . . ?
C34 C35 C30 121.8(4) . . ?
C34 C35 H35 119.1 . . ?
N3 C36 S2 121.2(4) . . ?
N3 C36 C37 106.8(4) . . ?
C37 C36 S2 131.8(4) . . ?
C36 C37 H37 127.5 . . ?
C36 C37 C38 105.1(4) . . ?
C38 C37 H37 127.5 . . ?
N4 C38 C37 111.8(4) . . ?
N4 C38 C39 121.1(4) . . ?
C37 C38 C39 127.0(4) . . ?
C40 C39 C38 120.2(4) . . ?
C40 C39 C43 118.4(5) . . ?
C43 C39 C38 121.4(4) . . ?
C39 C40 H40 119.1 . . ?
C41 C40 C39 121.9(5) . . ?
C41 C40 H40 119.1 . . ?
C40 C41 H41 120.4 . . ?
C40 C41 C42 119.2(5) . . ?
C42 C41 H41 120.4 . . ?
C41 C42 C44 120.1(5) . . ?
C41 C42 C46 120.8(5) . . ?
C44 C42 C46 119.1(5) . . ?
C39 C43 H43 119.8 . . ?
C44 C43 C39 120.3(5) . . ?
C44 C43 H43 119.8 . . ?
C42 C44 H44 120.0 . . ?
C43 C44 C42 120.1(5) . . ?
C43 C44 H44 120.0 . . ?
S2 C45 H45A 109.5 . . ?
S2 C45 H45B 109.5 . . ?
S2 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
F5 C46 C42 111.0(6) . . ?
F6 C46 F8 105.6(10) . . ?
F6 C46 F10 107.8(14) . . ?
F6 C46 C42 116.6(8) . . ?
F7 C46 F5 103.4(9) . . ?
F7 C46 C42 113.6(6) . . ?
F8 C46 C42 110.1(7) . . ?
F9 C46 F5 102.5(10) . . ?
F9 C46 F7 111.7(13) . . ?
F9 C46 C42 113.6(10) . . ?
F10 C46 F8 100.0(13) . . ?
F10 C46 C42 115.1(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C13 C14 C15 178.3(5) . . . . ?
N1 N2 C15 C14 0.1(6) . . . . ?
N1 N2 C15 C16 -176.4(5) . . . . ?
N1 C1 C2 C3 -178.9(5) . . . . ?
N1 C1 C6 C5 179.3(4) . . . . ?
N1 C13 C14 C15 -0.2(6) . . . . ?
N2 N1 C1 C2 37.6(7) . . . . ?
N2 N1 C1 C6 -142.2(5) . . . . ?
N2 N1 C13 S1 -178.4(4) . . . . ?
N2 N1 C13 C14 0.2(6) . . . . ?
N2 C15 C16 C17 -159.5(5) . . . . ?
N2 C15 C16 C21 24.1(8) . . . . ?
C1 N1 N2 C15 -178.8(4) . . . . ?
C1 N1 C13 S1 0.0(8) . . . . ?
C1 N1 C13 C14 178.6(5) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C1 C6 C5 -0.5(8) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C2 C3 C4 C7 178.7(5) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C3 C4 C7 C8 167.5(5) . . . . ?
C3 C4 C7 C12 -16.1(8) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C4 C7 C8 C9 176.9(5) . . . . ?
C4 C7 C12 C11 -176.5(5) . . . . ?
C5 C4 C7 C8 -14.0(7) . . . . ?
C5 C4 C7 C12 162.4(5) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C7 C4 C5 C6 -178.3(5) . . . . ?
C7 C8 C9 C10 -1.2(9) . . . . ?
C8 C7 C12 C11 0.0(8) . . . . ?
C8 C9 C10 C11 1.4(10) . . . . ?
C9 C10 C11 C12 -0.9(10) . . . . ?
C10 C11 C12 C7 0.2(9) . . . . ?
C12 C7 C8 C9 0.4(8) . . . . ?
C13 N1 N2 C15 -0.2(6) . . . . ?
C13 N1 C1 C2 -140.7(6) . . . . ?
C13 N1 C1 C6 39.4(8) . . . . ?
C13 C14 C15 N2 0.0(6) . . . . ?
C13 C14 C15 C16 176.3(5) . . . . ?
C14 C15 C16 C17 24.6(8) . . . . ?
C14 C15 C16 C21 -151.8(6) . . . . ?
C15 C16 C17 C18 -175.8(5) . . . . ?
C15 C16 C21 C20 176.0(5) . . . . ?
C16 C17 C18 C19 0.2(9) . . . . ?
C17 C16 C21 C20 -0.5(8) . . . . ?
C17 C18 C19 C20 -1.3(9) . . . . ?
C17 C18 C19 C23 -178.2(5) . . . . ?
C18 C19 C20 C21 1.5(9) . . . . ?
C18 C19 C23 F1 -145.6(6) . . . . ?
C18 C19 C23 F2 -23.1(8) . . . . ?
C18 C19 C23 F3 96.5(6) . . . . ?
C19 C20 C21 C16 -0.6(8) . . . . ?
C20 C19 C23 F1 37.5(7) . . . . ?
C20 C19 C23 F2 160.0(5) . . . . ?
C20 C19 C23 F3 -80.4(7) . . . . ?
C21 C16 C17 C18 0.7(9) . . . . ?
C22 S1 C13 N1 -175.3(5) . . . . ?
C22 S1 C13 C14 6.4(6) . . . . ?
C23 C19 C20 C21 178.4(5) . . . . ?
S2 C36 C37 C38 -173.5(4) . . . . ?
N3 N4 C38 C37 0.2(6) . . . . ?
N3 N4 C38 C39 -177.7(5) . . . . ?
N3 C33 C34 C35 179.6(4) . . . . ?
N3 C36 C37 C38 1.6(6) . . . . ?
N4 N3 C33 C32 -39.7(7) . . . . ?
N4 N3 C33 C34 141.1(5) . . . . ?
N4 N3 C36 S2 174.2(4) . . . . ?
N4 N3 C36 C37 -1.6(6) . . . . ?
N4 C38 C39 C40 165.2(6) . . . . ?
N4 C38 C39 C43 -14.1(8) . . . . ?
C24 C25 C26 C27 0.9(9) . . . . ?
C24 C30 C31 C32 -179.2(5) . . . . ?
C24 C30 C35 C34 179.9(4) . . . . ?
C25 C24 C29 C28 0.3(9) . . . . ?
C25 C24 C30 C31 -169.1(5) . . . . ?
C25 C24 C30 C35 11.5(8) . . . . ?
C25 C26 C27 C28 -1.8(9) . . . . ?
C26 C27 C28 C29 2.0(9) . . . . ?
C27 C28 C29 C24 -1.2(9) . . . . ?
C29 C24 C25 C26 -0.1(8) . . . . ?
C29 C24 C30 C31 12.5(8) . . . . ?
C29 C24 C30 C35 -166.9(5) . . . . ?
C30 C24 C25 C26 -178.6(5) . . . . ?
C30 C24 C29 C28 178.8(5) . . . . ?
C30 C31 C32 C33 -0.7(8) . . . . ?
C31 C30 C35 C34 0.6(7) . . . . ?
C31 C32 C33 N3 -178.8(4) . . . . ?
C31 C32 C33 C34 0.4(8) . . . . ?
C32 C33 C34 C35 0.3(8) . . . . ?
C33 N3 N4 C38 175.1(5) . . . . ?
C33 N3 C36 S2 0.5(8) . . . . ?
C33 N3 C36 C37 -175.2(5) . . . . ?
C33 C34 C35 C30 -0.8(8) . . . . ?
C35 C30 C31 C32 0.2(7) . . . . ?
C36 N3 N4 C38 0.9(6) . . . . ?
C36 N3 C33 C32 133.5(6) . . . . ?
C36 N3 C33 C34 -45.7(8) . . . . ?
C36 C37 C38 N4 -1.2(7) . . . . ?
C36 C37 C38 C39 176.6(5) . . . . ?
C37 C38 C39 C40 -12.3(9) . . . . ?
C37 C38 C39 C43 168.4(6) . . . . ?
C38 C39 C40 C41 -178.5(6) . . . . ?
C38 C39 C43 C44 178.7(5) . . . . ?
C39 C40 C41 C42 -0.5(10) . . . . ?
C39 C43 C44 C42 0.1(9) . . . . ?
C40 C39 C43 C44 -0.6(9) . . . . ?
C40 C41 C42 C44 0.0(9) . . . . ?
C40 C41 C42 C46 -179.2(6) . . . . ?
C41 C42 C44 C43 0.2(9) . . . . ?
C41 C42 C46 F5 124.3(10) . . . . ?
C41 C42 C46 F6 84.7(19) . . . . ?
C41 C42 C46 F7 8.4(17) . . . . ?
C41 C42 C46 F8 -35.6(13) . . . . ?
C41 C42 C46 F9 -120.7(13) . . . . ?
C41 C42 C46 F10 -147.6(16) . . . . ?
C43 C39 C40 C41 0.8(9) . . . . ?
C44 C42 C46 F5 -54.9(11) . . . . ?
C44 C42 C46 F6 -94.5(19) . . . . ?
C44 C42 C46 F7 -170.8(16) . . . . ?
C44 C42 C46 F8 145.2(12) . . . . ?
C44 C42 C46 F9 60.1(14) . . . . ?
C44 C42 C46 F10 33.2(17) . . . . ?
C45 S2 C36 N3 -168.2(5) . . . . ?
C45 S2 C36 C37 6.4(6) . . . . ?
C46 C42 C44 C43 179.4(5) . . . . ?

_olex2_date_sample_data_collection 2023-05-17
_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 2.240
_oxdiff_exptl_absorpt_empirical_full_min 0.447
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_se_1
_database_code_depnum_ccdc_archive 'CCDC 2373476'
loop_
_audit_author_name
_audit_author_address
'Yuyang Xie'
;Xuzhou Medical University
China
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2024-07-25
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N2 Se'
_chemical_formula_sum            'C22 H18 N2 Se'
_chemical_formula_weight         389.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6690(4)
_cell_length_b                   13.8133(4)
_cell_length_c                   13.9111(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.261(3)
_cell_angle_gamma                90
_cell_volume                     1822.21(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2774
_cell_measurement_temperature    219.99(10)
_cell_measurement_theta_max      73.6050
_cell_measurement_theta_min      4.5220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7179
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.750
_diffrn_reflns_theta_min         4.555
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      219.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  56.00   1.00    1.00    --   41.11 -38.00 -60.00   85
  2  ω     23.00  97.00   1.00    1.00    --   41.11-125.00 -90.00   74
  3  ω     38.00 125.00   1.00    1.50    --  107.58 -45.00  30.00   87
  4  ω     93.00 158.00   1.00    1.50    --  107.58  45.00 -90.00   65
  5  ω    105.00 177.00   1.00    1.50    --  107.58 125.00  60.00   72
  6  ω     99.00 174.00   1.00    1.50    --  107.58  77.00 146.00   75
  7  ω     47.00  92.00   1.00    1.50    --  107.58 -94.00  60.00   45
  8  ω     37.00  89.00   1.00    1.00    --   41.11-125.00 150.00   52
  9  ω     75.00 169.00   1.00    1.50    --  107.58  77.00-180.00   94
 10  ω    -37.00  -8.00   1.00    1.00    --  -41.11 125.00 150.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0876421000
_diffrn_orient_matrix_UB_12      -0.0103799000
_diffrn_orient_matrix_UB_13      -0.1046477000
_diffrn_orient_matrix_UB_21      -0.0694595000
_diffrn_orient_matrix_UB_22      -0.0920289000
_diffrn_orient_matrix_UB_23      0.0312983000
_diffrn_orient_matrix_UB_31      -0.1178991000
_diffrn_orient_matrix_UB_32      0.0619767000
_diffrn_orient_matrix_UB_33      0.0289005000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2814
_reflns_number_total             3572
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.083
_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     227
_refine_ls_number_reflns         3572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.048
_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)+(0.0818P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1514
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.30146(5) 0.41364(3) 0.51745(3) 0.05720(19) Uani 1 1 d . . . . .
N1 N 0.4472(3) 0.31439(18) 0.68858(18) 0.0330(5) Uani 1 1 d . . . . .
N2 N 0.4847(2) 0.22723(19) 0.72951(16) 0.0322(5) Uani 1 1 d . . . . .
C1 C 0.6282(3) 0.6513(2) 0.9138(2) 0.0316(6) Uani 1 1 d . . . . .
C2 C 0.5638(3) 0.6746(2) 0.9919(2) 0.0416(7) Uani 1 1 d . . . . .
H2 H 0.490489 0.634501 1.006148 0.050 Uiso 1 1 calc R U . . .
C3 C 0.6051(4) 0.7554(3) 1.0491(2) 0.0478(8) Uani 1 1 d . . . . .
H3 H 0.559575 0.770591 1.101827 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7125(4) 0.8142(2) 1.0300(2) 0.0442(8) Uani 1 1 d . . . . .
H4 H 0.741629 0.869217 1.069762 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7769(3) 0.7917(2) 0.9520(2) 0.0396(7) Uani 1 1 d . . . . .
H5 H 0.849856 0.832109 0.937770 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7357(3) 0.7111(2) 0.8951(2) 0.0349(6) Uani 1 1 d . . . . .
H6 H 0.781360 0.696224 0.842286 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5826(3) 0.5647(2) 0.8534(2) 0.0310(6) Uani 1 1 d . . . . .
C8 C 0.6787(3) 0.4957(2) 0.8343(2) 0.0340(6) Uani 1 1 d . . . . .
H8 H 0.776381 0.504969 0.859684 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6350(3) 0.4138(2) 0.7789(2) 0.0339(6) Uani 1 1 d . . . . .
H9 H 0.702025 0.367745 0.766023 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4925(3) 0.4000(2) 0.7425(2) 0.0322(6) Uani 1 1 d . . . . .
C11 C 0.3950(3) 0.4672(3) 0.7607(2) 0.0409(7) Uani 1 1 d . . . . .
H11 H 0.297349 0.457305 0.735699 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4401(3) 0.5489(2) 0.8154(3) 0.0410(7) Uani 1 1 d . . . . .
H12 H 0.372652 0.595040 0.827358 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3635(3) 0.3051(2) 0.5975(2) 0.0356(6) Uani 1 1 d . . . . .
C14 C 0.3473(3) 0.2074(2) 0.5802(2) 0.0369(6) Uani 1 1 d . . . . .
H14 H 0.295130 0.176928 0.523247 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4239(3) 0.1622(2) 0.6638(2) 0.0320(6) Uani 1 1 d . . . . .
C16 C 0.4405(3) 0.0581(2) 0.6848(2) 0.0325(6) Uani 1 1 d . . . . .
C17 C 0.4855(3) 0.0255(2) 0.7811(2) 0.0384(7) Uani 1 1 d . . . . .
H17 H 0.506529 0.071037 0.833108 0.046 Uiso 1 1 calc R U . . .
C18 C 0.4997(4) -0.0729(3) 0.8013(3) 0.0487(8) Uani 1 1 d . . . . .
H18 H 0.529102 -0.094403 0.866971 0.058 Uiso 1 1 calc R U . . .
C19 C 0.4709(4) -0.1396(3) 0.7257(3) 0.0509(8) Uani 1 1 d . . . . .
H19 H 0.480762 -0.206939 0.739045 0.061 Uiso 1 1 calc R U . . .
C20 C 0.4279(4) -0.1071(3) 0.6310(3) 0.0505(9) Uani 1 1 d . . . . .
H20 H 0.408882 -0.152595 0.578850 0.061 Uiso 1 1 calc R U . . .
C21 C 0.4122(3) -0.0100(3) 0.6108(2) 0.0409(7) Uani 1 1 d . . . . .
H21 H 0.381395 0.010744 0.545011 0.049 Uiso 1 1 calc R U . . .
C22 C 0.3320(6) 0.3589(4) 0.3947(3) 0.0756(14) Uani 1 1 d . . . . .
H22A H 0.329472 0.410687 0.346239 0.113 Uiso 1 1 calc R U . . .
H22B H 0.257808 0.311588 0.370640 0.113 Uiso 1 1 calc R U . . .
H22C H 0.424150 0.326851 0.405337 0.113 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 C13 1.894(3) . ?
Se1 C22 1.942(4) . ?
N1 N2 1.351(3) . ?
N1 C10 1.423(4) . ?
N1 C13 1.369(4) . ?
N2 C15 1.333(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.392(4) . ?
C1 C7 1.478(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(4) . ?
C7 C12 1.393(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(4) . ?
C10 C11 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.399(4) . ?
C15 C16 1.469(4) . ?
C16 C17 1.400(4) . ?
C16 C21 1.381(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C13 Se1 C22 97.12(17) . . ?
N2 N1 C10 119.3(2) . . ?
N2 N1 C13 111.6(2) . . ?
C13 N1 C10 129.1(3) . . ?
C15 N2 N1 105.4(2) . . ?
C2 C1 C7 120.1(3) . . ?
C6 C1 C2 118.3(3) . . ?
C6 C1 C7 121.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C1 121.7(3) . . ?
C12 C7 C1 120.4(3) . . ?
C12 C7 C8 117.8(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 N1 119.2(3) . . ?
C11 C10 N1 120.3(3) . . ?
C11 C10 C9 120.4(3) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.3(3) . . ?
C11 C12 H12 119.3 . . ?
N1 C13 Se1 122.1(2) . . ?
N1 C13 C14 106.3(3) . . ?
C14 C13 Se1 131.4(2) . . ?
C13 C14 H14 127.2 . . ?
C13 C14 C15 105.6(3) . . ?
C15 C14 H14 127.2 . . ?
N2 C15 C14 111.1(3) . . ?
N2 C15 C16 120.5(3) . . ?
C14 C15 C16 128.4(3) . . ?
C17 C16 C15 120.4(3) . . ?
C21 C16 C15 121.3(3) . . ?
C21 C16 C17 118.3(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.2(4) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
Se1 C22 H22A 109.5 . . ?
Se1 C22 H22B 109.5 . . ?
Se1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C13 C14 C15 176.0(2) . . . . ?
N1 N2 C15 C14 0.2(3) . . . . ?
N1 N2 C15 C16 -179.0(2) . . . . ?
N1 C10 C11 C12 178.2(3) . . . . ?
N1 C13 C14 C15 0.1(3) . . . . ?
N2 N1 C10 C9 55.0(4) . . . . ?
N2 N1 C10 C11 -123.1(3) . . . . ?
N2 N1 C13 Se1 -176.40(19) . . . . ?
N2 N1 C13 C14 0.0(3) . . . . ?
N2 C15 C16 C17 17.6(4) . . . . ?
N2 C15 C16 C21 -162.5(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C7 C8 C9 179.0(3) . . . . ?
C1 C7 C12 C11 -178.5(3) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C7 C8 -128.8(3) . . . . ?
C2 C1 C7 C12 49.9(4) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C6 C1 C7 C8 50.9(4) . . . . ?
C6 C1 C7 C12 -130.4(3) . . . . ?
C7 C1 C2 C3 -180.0(3) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C7 C12 C11 0.2(5) . . . . ?
C8 C9 C10 N1 -177.8(3) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 N1 N2 C15 178.1(2) . . . . ?
C10 N1 C13 Se1 5.6(4) . . . . ?
C10 N1 C13 C14 -178.0(3) . . . . ?
C10 C11 C12 C7 -0.4(5) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?
C13 N1 N2 C15 -0.1(3) . . . . ?
C13 N1 C10 C9 -127.2(3) . . . . ?
C13 N1 C10 C11 54.7(4) . . . . ?
C13 C14 C15 N2 -0.2(3) . . . . ?
C13 C14 C15 C16 179.0(3) . . . . ?
C14 C15 C16 C17 -161.5(3) . . . . ?
C14 C15 C16 C21 18.4(4) . . . . ?
C15 C16 C17 C18 179.2(3) . . . . ?
C15 C16 C21 C20 -180.0(3) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C16 C21 C20 -0.1(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C16 0.7(5) . . . . ?
C21 C16 C17 C18 -0.7(4) . . . . ?
C22 Se1 C13 N1 137.5(3) . . . . ?
C22 Se1 C13 C14 -37.9(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.413
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2358179'
loop_
_audit_author_name
_audit_author_address
hy
;Jishou University
China
;
_audit_update_record             
;
2024-05-25 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2022-12-04
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O2 S'
_chemical_formula_sum            'C20 H17 N O2 S'
_chemical_formula_weight         335.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.053(4)
_cell_length_b                   10.667(4)
_cell_length_c                   11.338(6)
_cell_angle_alpha                111.696(14)
_cell_angle_beta                 95.674(19)
_cell_angle_gamma                101.888(16)
_cell_volume                     869.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4711
_cell_measurement_temperature    296.30
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1284 before and 0.0815 after correction.
The Ratio of minimum to maximum transmission is 0.8241.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22643
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.707
_diffrn_reflns_theta_min         1.970
_diffrn_ambient_temperature      296.30
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3094
_reflns_number_total             4397
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.010
_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)+(0.0462P)²+0.1960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
S1 S 0.06726(7) 0.20325(5) 0.82983(5) 0.03097(15) Uani 1 1 d . . . . .
O1 O 0.3107(2) 0.21760(14) 0.34023(13) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.37667(18) 0.36070(13) 0.23780(12) 0.0320(3) Uani 1 1 d . . . . .
N1 N 0.0643(2) 0.39099(15) 0.72683(14) 0.0259(3) Uani 1 1 d . . . . .
C1 C 0.4024(2) 0.69608(18) 1.15404(16) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.4017(2) 0.82665(19) 1.15317(18) 0.0282(4) Uani 1 1 d . . . . .
H2 H 0.341274 0.831706 1.081507 0.034 Uiso 1 1 calc R U . . .
C3 C 0.4899(3) 0.94836(19) 1.25775(19) 0.0319(4) Uani 1 1 d . . . . .
H3 H 0.488643 1.034901 1.256632 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5800(3) 0.9404(2) 1.36418(18) 0.0313(4) Uani 1 1 d . . . . .
H4 H 0.640315 1.022079 1.434405 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5810(3) 0.8114(2) 1.36683(18) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.640656 0.807220 1.439221 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4931(2) 0.68849(19) 1.26169(17) 0.0282(4) Uani 1 1 d . . . . .
H6 H 0.494748 0.602135 1.263097 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3072(2) 0.57214(18) 1.04343(17) 0.0266(4) Uani 1 1 d . . . . .
C8 C 0.2222(2) 0.47749(19) 0.94677(17) 0.0271(4) Uani 1 1 d . . . . .
C9 C 0.1170(2) 0.37102(18) 0.82763(17) 0.0249(4) Uani 1 1 d . . . . .
C10 C 0.0970(2) 0.52870(18) 0.73085(17) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.0469(2) 0.63410(19) 0.82430(17) 0.0283(4) Uani 1 1 d . . . . .
H11 H -0.003328 0.615563 0.888543 0.034 Uiso 1 1 calc R U . . .
C12 C 0.0704(2) 0.7657(2) 0.82332(18) 0.0321(5) Uani 1 1 d . . . . .
H12 H 0.037437 0.834999 0.887185 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1434(3) 0.7947(2) 0.7270(2) 0.0328(5) Uani 1 1 d . . . . .
H13 H 0.159517 0.883203 0.726132 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1918(2) 0.6905(2) 0.63261(19) 0.0299(4) Uani 1 1 d . . . . .
H14 H 0.240258 0.710066 0.568178 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1695(2) 0.55585(18) 0.63156(17) 0.0242(4) Uani 1 1 d . . . . .
C16 C 0.2179(2) 0.44465(19) 0.53130(17) 0.0249(4) Uani 1 1 d . . . . .
H16 H 0.195756 0.357999 0.536593 0.030 Uiso 1 1 calc R U . . .
C17 C 0.2901(2) 0.45371(19) 0.43343(17) 0.0269(4) Uani 1 1 d . . . . .
H17 H 0.318645 0.539348 0.426366 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3259(2) 0.33145(19) 0.33611(17) 0.0258(4) Uani 1 1 d . . . . .
C19 C 0.4085(3) 0.2483(2) 0.13199(19) 0.0360(5) Uani 1 1 d . . . . .
H19A H 0.418378 0.274623 0.060109 0.054 Uiso 1 1 calc R U . . .
H19B H 0.314425 0.166239 0.106737 0.054 Uiso 1 1 calc R U . . .
H19C H 0.514097 0.229112 0.158457 0.054 Uiso 1 1 calc R U . . .
C20 C -0.0606(3) 0.1008(2) 0.67047(19) 0.0386(5) Uani 1 1 d . . . . .
H20A H 0.010316 0.100882 0.607234 0.058 Uiso 1 1 calc R U . . .
H20B H -0.154205 0.140301 0.657425 0.058 Uiso 1 1 calc R U . . .
H20C H -0.106352 0.006600 0.661597 0.058 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
S1 C9 1.762(2) . ?
S1 C20 1.797(2) . ?
O1 C18 1.214(2) . ?
O2 C18 1.342(2) . ?
O2 C19 1.437(2) . ?
N1 C9 1.286(2) . ?
N1 C10 1.421(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.397(3) . ?
C1 C7 1.441(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.199(3) . ?
C8 C9 1.440(3) . ?
C10 C11 1.393(2) . ?
C10 C15 1.412(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.406(3) . ?
C15 C16 1.460(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.328(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.468(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C20 100.90(10) . . ?
C18 O2 C19 116.93(15) . . ?
C9 N1 C10 120.06(15) . . ?
C2 C1 C7 118.69(17) . . ?
C6 C1 C2 119.66(17) . . ?
C6 C1 C7 121.65(17) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.68(18) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.50(18) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.48(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.33(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.34(18) . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C1 173.6(2) . . ?
C7 C8 C9 176.0(2) . . ?
N1 C9 S1 121.42(14) . . ?
N1 C9 C8 125.42(17) . . ?
C8 C9 S1 113.15(14) . . ?
C11 C10 N1 121.54(17) . . ?
C11 C10 C15 119.40(17) . . ?
C15 C10 N1 118.86(15) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.21(18) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.15(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.28(18) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.69(18) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C16 119.66(17) . . ?
C14 C15 C10 118.25(16) . . ?
C14 C15 C16 122.10(17) . . ?
C15 C16 H16 116.4 . . ?
C17 C16 C15 127.11(18) . . ?
C17 C16 H16 116.4 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.41(17) . . ?
C18 C17 H17 119.3 . . ?
O1 C18 O2 123.18(16) . . ?
O1 C18 C17 126.06(17) . . ?
O2 C18 C17 110.76(16) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C10 C11 C12 -176.38(17) . . . . ?
N1 C10 C15 C14 176.35(16) . . . . ?
N1 C10 C15 C16 -3.3(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C1 C2 C3 179.34(17) . . . . ?
C7 C1 C6 C5 -179.06(17) . . . . ?
C9 N1 C10 C11 -54.7(2) . . . . ?
C9 N1 C10 C15 130.34(19) . . . . ?
C10 N1 C9 S1 175.90(13) . . . . ?
C10 N1 C9 C8 -5.3(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C10 C15 C16 C17 -178.61(18) . . . . ?
C11 C10 C15 C14 1.3(3) . . . . ?
C11 C10 C15 C16 -178.33(16) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C13 C14 C15 C16 179.12(18) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C15 C10 C11 C12 -1.5(3) . . . . ?
C15 C16 C17 C18 -177.52(17) . . . . ?
C16 C17 C18 O1 -7.5(3) . . . . ?
C16 C17 C18 O2 171.62(17) . . . . ?
C19 O2 C18 O1 1.9(3) . . . . ?
C19 O2 C18 C17 -177.18(15) . . . . ?
C20 S1 C9 N1 -0.94(18) . . . . ?
C20 S1 C9 C8 -179.85(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
