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

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

data_2007018687_0m
_database_code_depnum_ccdc_archive 'CCDC 2020489'
loop_
_audit_author_name
_audit_author_address
'Mixue Bian'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-07-31 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O3 S Se'
_chemical_formula_sum            'C23 H21 N O3 S Se'
_chemical_formula_weight         470.43
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -1.0986 0.9246 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5825(11)
_cell_length_b                   11.7312(12)
_cell_length_c                   16.2936(16)
_cell_angle_alpha                90
_cell_angle_beta                 110.128(4)
_cell_angle_gamma                90
_cell_volume                     2078.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.911
_cell_measurement_theta_min      4.133
_shelx_estimated_absorpt_T_max   0.794
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    2.416
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1568 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.5932. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21511
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.961
_diffrn_reflns_theta_min         4.132
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3680
_reflns_number_total             3934
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.294
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.077
_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)+(0.0484P)²+1.5490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0946
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C23(H23A,H23B,H23C)
;
_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 0.43591(2) 0.83369(2) 0.45088(2) 0.02332(11) Uani 1 1 d . . . . .
S1 S 0.26614(5) 0.66305(4) 0.16062(4) 0.02434(15) Uani 1 1 d . . . . .
O1 O 0.47679(13) 0.79903(13) 0.26786(9) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.19869(15) 0.56108(15) 0.12562(11) 0.0361(4) Uani 1 1 d . . . . .
O3 O 0.28070(15) 0.74668(15) 0.10065(10) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.39852(16) 0.61638(15) 0.22805(12) 0.0226(4) Uani 1 1 d . . . . .
C1 C 0.5828(2) 0.85001(18) 0.33608(14) 0.0222(5) Uani 1 1 d . . . . .
H1 H 0.629109 0.900357 0.308714 0.027 Uiso 1 1 calc R . . . .
C2 C 0.65973(19) 0.74927(18) 0.37737(14) 0.0205(4) Uani 1 1 d . . . . .
C3 C 0.7714(2) 0.7436(2) 0.44539(15) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.814239 0.811168 0.470453 0.031 Uiso 1 1 calc R . . . .
C4 C 0.8199(2) 0.6366(2) 0.47643(15) 0.0274(5) Uani 1 1 d . . . . .
C5 C 0.7549(2) 0.5383(2) 0.43869(15) 0.0270(5) Uani 1 1 d . . . . .
H5 H 0.788017 0.465901 0.460721 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6435(2) 0.54325(19) 0.37010(14) 0.0237(5) Uani 1 1 d . . . . .
H6 H 0.600398 0.476003 0.344509 0.028 Uiso 1 1 calc R . . . .
C7 C 0.59789(19) 0.65074(18) 0.34047(14) 0.0196(4) Uani 1 1 d . . . . .
C8 C 0.48288(19) 0.68535(18) 0.27364(13) 0.0186(4) Uani 1 1 d . . . . .
C9 C 0.9403(2) 0.6291(3) 0.55165(18) 0.0403(6) Uani 1 1 d . . . . .
H9A H 1.006500 0.659516 0.533424 0.060 Uiso 1 1 calc GR . . . .
H9B H 0.957689 0.549264 0.569277 0.060 Uiso 1 1 calc GR . . . .
H9C H 0.934835 0.673618 0.601075 0.060 Uiso 1 1 calc GR . . . .
C10 C 0.5352(2) 0.91945(18) 0.39595(14) 0.0239(5) Uani 1 1 d . . . . .
H10A H 0.485018 0.983025 0.361910 0.029 Uiso 1 1 calc R . . . .
H10B H 0.606279 0.953172 0.442538 0.029 Uiso 1 1 calc R . . . .
C11 C 0.56409(19) 0.7662(2) 0.54730(13) 0.0226(5) Uani 1 1 d . . . . .
C12 C 0.6606(2) 0.82958(19) 0.60380(17) 0.0308(5) Uani 1 1 d . . . . .
H12 H 0.666281 0.909068 0.594703 0.037 Uiso 1 1 calc R . . . .
C13 C 0.7480(2) 0.7761(2) 0.67306(17) 0.0365(6) Uani 1 1 d . . . . .
H13 H 0.814135 0.819071 0.711460 0.044 Uiso 1 1 calc R . . . .
C14 C 0.7402(3) 0.6603(2) 0.68712(17) 0.0352(6) Uani 1 1 d . . . . .
H14 H 0.800583 0.624021 0.734937 0.042 Uiso 1 1 calc R . . . .
C15 C 0.6447(2) 0.5985(2) 0.63161(17) 0.0370(6) Uani 1 1 d . . . . .
H15 H 0.639154 0.519112 0.641230 0.044 Uiso 1 1 calc R . . . .
C16 C 0.5561(2) 0.6507(2) 0.56141(17) 0.0306(5) Uani 1 1 d . . . . .
H16 H 0.490257 0.607230 0.523232 0.037 Uiso 1 1 calc R . . . .
C17 C 0.19633(19) 0.72866(19) 0.22899(14) 0.0245(5) Uani 1 1 d . . . . .
C18 C 0.1956(2) 0.84636(19) 0.23543(16) 0.0261(5) Uani 1 1 d . . . . .
H18 H 0.230242 0.892145 0.201728 0.031 Uiso 1 1 calc R . . . .
C19 C 0.1438(2) 0.8967(2) 0.29162(16) 0.0313(5) Uani 1 1 d . . . . .
H19 H 0.142528 0.977499 0.295517 0.038 Uiso 1 1 calc R . . . .
C20 C 0.0938(2) 0.8317(2) 0.34228(17) 0.0353(6) Uani 1 1 d . . . . .
C21 C 0.0940(2) 0.7141(3) 0.33352(18) 0.0411(6) Uani 1 1 d . . . . .
H21 H 0.058739 0.668368 0.366868 0.049 Uiso 1 1 calc R . . . .
C22 C 0.1439(2) 0.6619(2) 0.27765(19) 0.0355(6) Uani 1 1 d . . . . .
H22 H 0.142671 0.581268 0.272395 0.043 Uiso 1 1 calc R . . . .
C23 C 0.0437(3) 0.8878(3) 0.4063(2) 0.0544(8) Uani 1 1 d . . . . .
H23A H 0.108052 0.890629 0.464075 0.082 Uiso 1 1 calc GR . . . .
H23B H -0.026398 0.843888 0.409705 0.082 Uiso 1 1 calc GR . . . .
H23C H 0.017040 0.965504 0.386579 0.082 Uiso 1 1 calc GR . . . .


_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 C10 1.961(2) . ?
Se1 C11 1.922(2) . ?
S1 O2 1.4352(17) . ?
S1 O3 1.4350(18) . ?
S1 N1 1.6427(18) . ?
S1 C17 1.763(2) . ?
O1 C1 1.470(3) . ?
O1 C8 1.337(3) . ?
N1 C8 1.289(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.494(3) . ?
C1 C10 1.513(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(3) . ?
C4 C5 1.399(3) . ?
C4 C9 1.509(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C7 C8 1.458(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.394(3) . ?
C11 C16 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.370(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 C22 1.393(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(4) . ?
C20 C21 1.386(4) . ?
C20 C23 1.508(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(4) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C11 Se1 C10 100.08(9) . . ?
O2 S1 N1 104.07(10) . . ?
O2 S1 C17 108.04(11) . . ?
O3 S1 O2 118.34(11) . . ?
O3 S1 N1 112.45(10) . . ?
O3 S1 C17 108.59(10) . . ?
N1 S1 C17 104.39(10) . . ?
C8 O1 C1 110.02(16) . . ?
C8 N1 S1 121.61(16) . . ?
O1 C1 H1 109.9 . . ?
O1 C1 C2 103.43(16) . . ?
O1 C1 C10 108.17(17) . . ?
C2 C1 H1 109.9 . . ?
C2 C1 C10 115.39(18) . . ?
C10 C1 H1 109.9 . . ?
C3 C2 C1 130.3(2) . . ?
C7 C2 C1 109.02(18) . . ?
C7 C2 C3 120.6(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 C9 119.4(2) . . ?
C5 C4 C9 121.0(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.1(2) . . ?
C7 C6 H6 121.4 . . ?
C2 C7 C6 122.0(2) . . ?
C2 C7 C8 107.17(18) . . ?
C6 C7 C8 130.8(2) . . ?
O1 C8 C7 110.04(18) . . ?
N1 C8 O1 125.05(19) . . ?
N1 C8 C7 124.89(19) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Se1 C10 H10A 108.6 . . ?
Se1 C10 H10B 108.6 . . ?
C1 C10 Se1 114.78(15) . . ?
C1 C10 H10A 108.6 . . ?
C1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 Se1 122.57(18) . . ?
C16 C11 Se1 117.57(17) . . ?
C16 C11 C12 119.8(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.8(2) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 S1 119.95(18) . . ?
C18 C17 C22 120.1(2) . . ?
C22 C17 S1 119.91(19) . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C23 120.6(3) . . ?
C21 C20 C19 118.0(2) . . ?
C21 C20 C23 121.4(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.7(2) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 H22 120.3 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
