# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 2008191'
loop_
_audit_author_name
_audit_author_address
'Jiawei Hua'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N O3 S Se'
_chemical_formula_weight         456.40

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'
S S 0.3331 0.5567 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.24730(10)
_cell_length_b                   12.2693(2)
_cell_length_c                   10.92510(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.3530(10)
_cell_angle_gamma                90
_cell_volume                     971.43(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9537
_cell_measurement_theta_min      4.0410
_cell_measurement_theta_max      68.5380

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.818
_shelx_estimated_absorpt_T_min   0.516
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.4741
_diffrn_reflns_number            13386
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.046
_diffrn_reflns_theta_max         68.535
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3515
_reflns_number_gt                3469
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.980

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.036(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Se Se 0.47953(4) 0.98273(3) 0.55404(3) 0.01949(15) Uani 1 1 d . . . . .
S S -0.04842(13) 1.18896(7) 0.75077(8) 0.0180(2) Uani 1 1 d . . . . .
N N 0.0344(4) 1.2158(3) 0.6152(3) 0.0169(6) Uani 1 1 d . . . . .
O1 O 0.0440(3) 1.0331(2) 0.5548(2) 0.0146(5) Uani 1 1 d . . . . .
C1 C 0.5914(5) 1.0312(3) 0.4038(4) 0.0191(8) Uani 1 1 d . . . . .
C2 C 0.6615(5) 0.9568(3) 0.3193(4) 0.0231(9) Uani 1 1 d . . . . .
H2A H 0.6564 0.8823 0.3347 0.028 Uiso 1 1 calc R U . . .
O2 O -0.0251(5) 1.2884(2) 0.8180(2) 0.0288(7) Uani 1 1 d . . . . .
O3 O -0.2318(4) 1.1454(3) 0.7413(3) 0.0247(7) Uani 1 1 d . . . . .
C3 C 0.7388(5) 0.9955(4) 0.2122(3) 0.0260(9) Uani 1 1 d . . . . .
H3B H 0.7847 0.9464 0.1552 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7490(5) 1.1066(4) 0.1887(4) 0.0268(9) Uani 1 1 d . . . . .
H4A H 0.7994 1.1317 0.1159 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6829(5) 1.1797(4) 0.2753(4) 0.0226(8) Uani 1 1 d . . . . .
H5A H 0.6917 1.2542 0.2611 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6038(5) 1.1419(3) 0.3830(4) 0.0204(8) Uani 1 1 d . . . . .
H6A H 0.5595 1.1911 0.4406 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2701(5) 0.9013(3) 0.4841(3) 0.0187(8) Uani 1 1 d . . . . .
H7A H 0.3125 0.8614 0.4130 0.022 Uiso 1 1 calc R U . . .
H7B H 0.2286 0.8484 0.5439 0.022 Uiso 1 1 calc R U . . .
C8 C 0.1071(4) 0.9718(3) 0.4463(3) 0.0148(7) Uani 1 1 d . . . . .
H8A H 0.0068 0.9255 0.4156 0.018 Uiso 1 1 calc R U . . .
C9 C 0.1474(5) 1.0590(3) 0.3557(3) 0.0130(7) Uani 1 1 d . . . . .
C10 C 0.2021(5) 1.0510(3) 0.2334(3) 0.0173(7) Uani 1 1 d . . . . .
H10A H 0.2167 0.9837 0.1955 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2336(5) 1.1471(3) 0.1714(3) 0.0187(8) Uani 1 1 d . . . . .
H11A H 0.2687 1.1445 0.0898 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2139(5) 1.2481(4) 0.2286(4) 0.0196(8) Uani 1 1 d . . . . .
H12A H 0.2383 1.3112 0.1843 0.023 Uiso 1 1 calc R U . . .
C13 C 0.1591(5) 1.2570(3) 0.3491(3) 0.0170(8) Uani 1 1 d . . . . .
H13A H 0.1450 1.3244 0.3870 0.020 Uiso 1 1 calc R U . . .
C14 C 0.1262(5) 1.1601(3) 0.4104(3) 0.0145(7) Uani 1 1 d . . . . .
C15 C 0.0648(5) 1.1406(3) 0.5359(3) 0.0138(7) Uani 1 1 d . . . . .
C16 C 0.0958(6) 1.0900(3) 0.8188(3) 0.0181(8) Uani 1 1 d . . . . .
C17 C 0.0157(5) 0.9979(4) 0.8707(3) 0.0212(8) Uani 1 1 d . . . . .
H17A H -0.1113 0.9877 0.8660 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1257(6) 0.9219(3) 0.9292(3) 0.0212(8) Uani 1 1 d . . . . .
H18A H 0.0716 0.8611 0.9650 0.025 Uiso 1 1 calc R U . . .
C19 C 0.3160(6) 0.9348(4) 0.9353(3) 0.0207(8) Uani 1 1 d . . . . .
C20 C 0.3937(6) 1.0262(4) 0.8813(3) 0.0221(8) Uani 1 1 d . . . . .
H20A H 0.5210 1.0353 0.8840 0.027 Uiso 1 1 calc R U . . .
C21 C 0.2856(6) 1.1042(4) 0.8233(3) 0.0214(8) Uani 1 1 d . . . . .
H21A H 0.3397 1.1652 0.7880 0.026 Uiso 1 1 calc R U . . .
C22 C 0.4337(6) 0.8508(4) 1.0000(4) 0.0265(9) Uani 1 1 d . . . . .
H22A H 0.5610 0.8719 0.9958 0.040 Uiso 1 1 calc R U . . .
H22B H 0.3972 0.8457 1.0841 0.040 Uiso 1 1 calc R U . . .
H22C H 0.4176 0.7812 0.9611 0.040 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
Se C1 1.929(4) . ?
Se C7 1.968(4) . ?
S O2 1.434(3) . ?
S O3 1.436(3) . ?
S N 1.635(3) . ?
S C16 1.763(4) . ?
N C15 1.286(5) . ?
O1 C15 1.344(4) . ?
O1 C8 1.479(4) . ?
C1 C6 1.381(6) . ?
C1 C2 1.396(6) . ?
C2 C3 1.384(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(7) . ?
C3 H3B 0.9300 . ?
C4 C5 1.390(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(6) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.519(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.488(5) . ?
C8 H8A 0.9800 . ?
C9 C14 1.386(5) . ?
C9 C10 1.399(5) . ?
C10 C11 1.379(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.395(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.386(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.463(5) . ?
C16 C17 1.393(6) . ?
C16 C21 1.387(6) . ?
C17 C18 1.381(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.389(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.387(6) . ?
C19 C22 1.511(6) . ?
C20 C21 1.388(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se C7 98.82(16) . . ?
O2 S O3 117.40(19) . . ?
O2 S N 104.44(17) . . ?
O3 S N 110.75(17) . . ?
O2 S C16 107.62(19) . . ?
O3 S C16 108.67(18) . . ?
N S C16 107.50(17) . . ?
C15 N S 122.1(3) . . ?
C15 O1 C8 109.9(3) . . ?
C6 C1 C2 120.7(4) . . ?
C6 C1 Se 118.1(3) . . ?
C2 C1 Se 121.2(3) . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3B 119.5 . . ?
C4 C3 H3B 119.5 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C8 C7 Se 114.4(3) . . ?
C8 C7 H7A 108.7 . . ?
Se C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
Se C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 C9 103.3(3) . . ?
O1 C8 C7 108.4(3) . . ?
C9 C8 C7 115.7(3) . . ?
O1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C14 C9 C10 120.5(3) . . ?
C14 C9 C8 109.5(3) . . ?
C10 C9 C8 130.0(4) . . ?
C11 C10 C9 117.2(3) . . ?
C11 C10 H10A 121.4 . . ?
C9 C10 H10A 121.4 . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11A 119.3 . . ?
C12 C11 H11A 119.3 . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C12 C13 C14 116.3(4) . . ?
C12 C13 H13A 121.8 . . ?
C14 C13 H13A 121.8 . . ?
C9 C14 C13 122.6(3) . . ?
C9 C14 C15 107.0(3) . . ?
C13 C14 C15 130.3(3) . . ?
N C15 O1 125.5(3) . . ?
N C15 C14 124.6(3) . . ?
O1 C15 C14 109.9(3) . . ?
C17 C16 C21 120.2(4) . . ?
C17 C16 S 118.9(3) . . ?
C21 C16 S 120.9(3) . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
C18 C19 C20 118.5(4) . . ?
C18 C19 C22 120.1(4) . . ?
C20 C19 C22 121.4(4) . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C20 C21 C16 119.1(4) . . ?
C20 C21 H21A 120.5 . . ?
C16 C21 H21A 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 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
O2 S N C15 168.2(3) . . . . ?
O3 S N C15 -64.5(3) . . . . ?
C16 S N C15 54.1(3) . . . . ?
C6 C1 C2 C3 -2.0(6) . . . . ?
Se C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
Se C1 C6 C5 -179.7(3) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C15 O1 C8 C9 -6.3(3) . . . . ?
C15 O1 C8 C7 117.0(3) . . . . ?
Se C7 C8 O1 -57.9(3) . . . . ?
Se C7 C8 C9 57.5(4) . . . . ?
O1 C8 C9 C14 5.0(4) . . . . ?
C7 C8 C9 C14 -113.3(3) . . . . ?
O1 C8 C9 C10 -176.1(4) . . . . ?
C7 C8 C9 C10 65.7(5) . . . . ?
C14 C9 C10 C11 0.1(6) . . . . ?
C8 C9 C10 C11 -178.7(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C10 C9 C14 C13 -0.7(5) . . . . ?
C8 C9 C14 C13 178.3(3) . . . . ?
C10 C9 C14 C15 178.8(3) . . . . ?
C8 C9 C14 C15 -2.1(4) . . . . ?
C12 C13 C14 C9 0.4(5) . . . . ?
C12 C13 C14 C15 -179.0(4) . . . . ?
S N C15 O1 -4.0(5) . . . . ?
S N C15 C14 175.4(3) . . . . ?
C8 O1 C15 N -175.2(3) . . . . ?
C8 O1 C15 C14 5.3(4) . . . . ?
C9 C14 C15 N 178.5(3) . . . . ?
C13 C14 C15 N -2.0(6) . . . . ?
C9 C14 C15 O1 -2.0(4) . . . . ?
C13 C14 C15 O1 177.5(3) . . . . ?
O2 S C16 C17 117.4(3) . . . . ?
O3 S C16 C17 -10.7(3) . . . . ?
N S C16 C17 -130.6(3) . . . . ?
O2 S C16 C21 -61.1(3) . . . . ?
O3 S C16 C21 170.8(3) . . . . ?
N S C16 C21 50.9(4) . . . . ?
C21 C16 C17 C18 1.4(5) . . . . ?
S C16 C17 C18 -177.1(3) . . . . ?
C16 C17 C18 C19 -1.1(6) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C17 C18 C19 C22 179.9(4) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C22 C19 C20 C21 -179.1(4) . . . . ?
C19 C20 C21 C16 -0.4(6) . . . . ?
C17 C16 C21 C20 -0.7(6) . . . . ?
S C16 C21 C20 177.8(3) . . . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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. 
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#######################################################################

data_2009141304_0m
_database_code_depnum_ccdc_archive 'CCDC 2038929'
loop_
_audit_author_name
_audit_author_address
'Jiawei Hua'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_audit_creation_date             2020-09-16
_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         'C22 H19 N O3 S Se'
_chemical_formula_sum            'C22 H19 N O3 S Se'
_chemical_formula_weight         456.40
_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 0.0148 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/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                   5.8297(4)
_cell_length_b                   16.2078(10)
_cell_length_c                   20.9813(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.402(3)
_cell_angle_gamma                90
_cell_volume                     1979.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.935
_cell_measurement_theta_min      4.375
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    2.526
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1347 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.7913. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21746
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.911
_diffrn_reflns_theta_min         2.999
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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                3507
_reflns_number_total             3717
_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         2.595
_refine_diff_density_min         -2.001
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.045
_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)+(0.0714P)²+6.8320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1612
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.d 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 0.64057(11) 0.76046(4) 0.17528(2) 0.0588(2) Uani 1 1 d . . . . .
S1 S 0.72068(15) 0.72155(5) 0.36637(4) 0.0272(2) Uani 1 1 d . . . . .
O1 O 0.9255(5) 0.56125(19) 0.32226(14) 0.0411(7) Uani 1 1 d . . . . .
O2 O 0.9638(5) 0.73217(18) 0.36314(13) 0.0357(6) Uani 1 1 d . . . . .
O3 O 0.5718(5) 0.79143(16) 0.36052(13) 0.0336(6) Uani 1 1 d . . . . .
N1 N 0.6331(5) 0.65870(19) 0.30737(14) 0.0277(7) Uani 1 1 d . . . . .
C1 C 0.7461(7) 0.5834(2) 0.29570(17) 0.0309(8) Uani 1 1 d . . . . .
C2 C 0.5942(7) 0.5398(2) 0.24836(18) 0.0326(8) Uani 1 1 d . . . . .
C3 C 0.6249(9) 0.4626(3) 0.2213(2) 0.0454(11) Uani 1 1 d . . . . .
H3 H 0.762296 0.432078 0.230006 0.054 Uiso 1 1 calc R . . . .
C4 C 0.4480(10) 0.4318(3) 0.1812(2) 0.0525(13) Uani 1 1 d . . . . .
H4 H 0.463483 0.379086 0.162097 0.063 Uiso 1 1 calc R . . . .
C5 C 0.2488(10) 0.4770(3) 0.1686(2) 0.0515(12) Uani 1 1 d . . . . .
H5 H 0.130051 0.454715 0.140783 0.062 Uiso 1 1 calc R . . . .
C6 C 0.2186(8) 0.5541(3) 0.1957(2) 0.0413(10) Uani 1 1 d . . . . .
H6 H 0.081032 0.584630 0.187136 0.050 Uiso 1 1 calc R . . . .
C7 C 0.3960(7) 0.5852(2) 0.23585(17) 0.0311(8) Uani 1 1 d . . . . .
C8 C 0.4048(6) 0.6651(2) 0.27241(17) 0.0300(8) Uani 1 1 d . . . . .
H8 H 0.281104 0.665984 0.303447 0.036 Uiso 1 1 calc R . . . .
C9 C 0.3842(8) 0.7416(3) 0.2292(2) 0.0416(10) Uani 1 1 d . . . . .
H9A H 0.367207 0.790778 0.256464 0.050 Uiso 1 1 calc R . . . .
H9B H 0.241775 0.736487 0.201310 0.050 Uiso 1 1 calc R . . . .
C10 C 0.5569(8) 0.6950(3) 0.1026(2) 0.0445(10) Uani 1 1 d . . . . .
C11 C 0.3469(9) 0.6994(3) 0.0704(2) 0.0467(11) Uani 1 1 d . . . . .
H11 H 0.231265 0.734140 0.085875 0.056 Uiso 1 1 calc R . . . .
C12 C 0.3008(12) 0.6537(3) 0.0154(2) 0.0599(14) Uani 1 1 d . . . . .
H12 H 0.151802 0.656793 -0.005404 0.072 Uiso 1 1 calc R . . . .
C13 C 0.4584(15) 0.6055(4) -0.0094(3) 0.0783(19) Uani 1 1 d . . . . .
H13 H 0.422345 0.574763 -0.047210 0.094 Uiso 1 1 calc R . . . .
C14 C 0.6682(15) 0.6012(5) 0.0201(4) 0.091(2) Uani 1 1 d . . . . .
H14 H 0.781929 0.568167 0.001891 0.109 Uiso 1 1 calc R . . . .
C15 C 0.7253(11) 0.6439(4) 0.0768(3) 0.0750(18) Uani 1 1 d . . . . .
H15 H 0.873834 0.638591 0.097635 0.090 Uiso 1 1 calc R . . . .
C16 C 0.6676(6) 0.6686(2) 0.43688(16) 0.0259(7) Uani 1 1 d . . . . .
C17 C 0.8398(6) 0.6192(2) 0.46560(18) 0.0301(8) Uani 1 1 d . . . . .
H17 H 0.981139 0.611557 0.446040 0.036 Uiso 1 1 calc R . . . .
C18 C 0.8013(7) 0.5815(2) 0.52304(18) 0.0315(8) Uani 1 1 d . . . . .
H18 H 0.918453 0.548100 0.543158 0.038 Uiso 1 1 calc R . . . .
C19 C 0.5941(7) 0.5913(2) 0.55208(17) 0.0308(8) Uani 1 1 d . . . . .
C20 C 0.4249(6) 0.6403(3) 0.52207(18) 0.0318(8) Uani 1 1 d . . . . .
H20 H 0.283173 0.647490 0.541516 0.038 Uiso 1 1 calc R . . . .
C21 C 0.4579(6) 0.6790(2) 0.46433(17) 0.0289(8) Uani 1 1 d . . . . .
H21 H 0.339981 0.711762 0.443985 0.035 Uiso 1 1 calc R . . . .
C22 C 0.5580(8) 0.5508(3) 0.6151(2) 0.0424(10) Uani 1 1 d . . . . .
H22A H 0.562893 0.490712 0.610066 0.064 Uiso 1 1 calc GR . . . .
H22B H 0.408126 0.567064 0.629792 0.064 Uiso 1 1 calc GR . . . .
H22C H 0.679532 0.568148 0.646528 0.064 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 C9 1.951(5) . ?
Se1 C10 1.897(5) . ?
S1 O2 1.433(3) . ?
S1 O3 1.428(3) . ?
S1 N1 1.660(3) . ?
S1 C16 1.754(4) . ?
O1 C1 1.210(5) . ?
N1 C1 1.415(5) . ?
N1 C8 1.485(5) . ?
C1 C2 1.472(6) . ?
C2 C3 1.389(6) . ?
C2 C7 1.382(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(6) . ?
C7 C8 1.505(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.536(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.365(6) . ?
C10 C15 1.417(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.335(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.339(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.400(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(5) . ?
C16 C21 1.392(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(6) . ?
C19 C20 1.388(6) . ?
C19 C22 1.502(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(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
C10 Se1 C9 102.05(19) . . ?
O2 S1 N1 107.44(17) . . ?
O2 S1 C16 108.85(17) . . ?
O3 S1 O2 119.89(17) . . ?
O3 S1 N1 105.31(16) . . ?
O3 S1 C16 108.90(17) . . ?
N1 S1 C16 105.49(16) . . ?
C1 N1 S1 122.2(3) . . ?
C1 N1 C8 112.8(3) . . ?
C8 N1 S1 123.5(2) . . ?
O1 C1 N1 125.1(4) . . ?
O1 C1 C2 129.5(4) . . ?
N1 C1 C2 105.3(3) . . ?
C3 C2 C1 128.4(4) . . ?
C7 C2 C1 109.6(3) . . ?
C7 C2 C3 121.9(4) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.5(5) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.8(5) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C6 120.4(4) . . ?
C2 C7 C8 111.0(3) . . ?
C6 C7 C8 128.5(4) . . ?
N1 C8 C7 101.2(3) . . ?
N1 C8 H8 109.8 . . ?
N1 C8 C9 112.6(3) . . ?
C7 C8 H8 109.8 . . ?
C7 C8 C9 113.2(3) . . ?
C9 C8 H8 109.8 . . ?
Se1 C9 H9A 108.4 . . ?
Se1 C9 H9B 108.4 . . ?
C8 C9 Se1 115.6(3) . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 Se1 123.3(4) . . ?
C11 C10 C15 117.6(5) . . ?
C15 C10 Se1 118.9(4) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(6) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.1(7) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 H15 120.7 . . ?
C14 C15 C10 118.6(6) . . ?
C14 C15 H15 120.7 . . ?
C17 C16 S1 119.2(3) . . ?
C21 C16 S1 119.6(3) . . ?
C21 C16 C17 121.2(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C22 120.3(4) . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 C22 121.1(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 120.7 . . ?
C20 C21 C16 118.5(3) . . ?
C20 C21 H21 120.7 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
