# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_220717h_0m
_database_code_depnum_ccdc_archive 'CCDC 2191956'
loop_
_audit_author_name
_audit_author_address
zhang
;xinjiang university
China
;
_audit_update_record             
;
2022-07-22 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O3 S Se'
_chemical_formula_sum            'C19 H19 N O3 S Se'
_chemical_formula_weight         420.37
_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'
Se Se -0.0929 2.2259 '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                   14.852(3)
_cell_length_b                   8.3709(17)
_cell_length_c                   15.745(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.498(4)
_cell_angle_gamma                90
_cell_volume                     1821.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.810
_shelx_estimated_absorpt_T_min   0.668
_exptl_absorpt_coefficient_mu    2.194
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0808 before and 0.0286 after correction.
The Ratio of minimum to maximum transmission is 0.7822.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10639
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_min         2.627
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2761
_reflns_number_total             4149
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.033
_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)+(0.0453P)²+0.0404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00G,H00H), C00H(H00I,H00J), C00K(H00L,H00M), C00L(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00J(H00K), C00M(H00P),
 C00N(H00Q), C00O(H00R), C00P(H00S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.60030(2) 0.41518(4) 0.32033(2) 0.05158(14) Uani 1 1 d . . . . .
S002 S 0.84644(5) 0.50849(9) 0.53115(5) 0.03764(19) Uani 1 1 d . . . . .
O003 O 0.84660(15) 0.2190(2) 0.35178(12) 0.0461(5) Uani 1 1 d . . . . .
N004 N 0.82905(15) 0.4449(2) 0.42620(13) 0.0296(5) Uani 1 1 d . . . . .
O005 O 0.75920(17) 0.5699(3) 0.53473(14) 0.0575(6) Uani 1 1 d . . . . .
O006 O 0.92996(17) 0.6076(2) 0.56465(14) 0.0581(6) Uani 1 1 d . . . . .
C007 C 0.85029(18) 0.2855(3) 0.42064(17) 0.0317(6) Uani 1 1 d . . . . .
C008 C 0.87335(18) 0.3165(3) 0.57765(16) 0.0302(6) Uani 1 1 d . . . . .
C009 C 0.87617(18) 0.2116(3) 0.51220(16) 0.0304(6) Uani 1 1 d . . . . .
C00A C 0.6856(2) 0.5943(3) 0.32173(19) 0.0371(7) Uani 1 1 d . . . . .
H00A H 0.684955 0.666315 0.370586 0.044 Uiso 1 1 calc R U . . .
C00B C 0.78971(19) 0.5461(3) 0.34365(17) 0.0339(6) Uani 1 1 d . . . . .
H00B H 0.791127 0.481548 0.292229 0.041 Uiso 1 1 calc R U . . .
C00C C 0.89469(19) 0.2730(4) 0.66637(17) 0.0394(7) Uani 1 1 d . . . . .
H00C H 0.892421 0.346442 0.709850 0.047 Uiso 1 1 calc R U . . .
C00D C 0.9014(2) 0.0551(3) 0.53532(19) 0.0420(7) Uani 1 1 d . . . . .
H00D H 0.903331 -0.017629 0.491385 0.050 Uiso 1 1 calc R U . . .
C00E C 0.9235(2) 0.0078(4) 0.6238(2) 0.0491(8) Uani 1 1 d . . . . .
H00E H 0.941191 -0.097612 0.640325 0.059 Uiso 1 1 calc R U . . .
C00F C 0.9197(2) 0.1163(4) 0.6889(2) 0.0469(8) Uani 1 1 d . . . . .
H00F H 0.934213 0.082503 0.748766 0.056 Uiso 1 1 calc R U . . .
C00G C 0.8542(2) 0.6903(4) 0.3500(2) 0.0445(7) Uani 1 1 d . . . . .
H00G H 0.857073 0.755217 0.401983 0.053 Uiso 1 1 calc R U . . .
H00H H 0.919289 0.654425 0.359568 0.053 Uiso 1 1 calc R U . . .
C00H C 0.6503(2) 0.6913(4) 0.23353(18) 0.0434(7) Uani 1 1 d . . . . .
H00I H 0.650601 0.624214 0.183408 0.052 Uiso 1 1 calc R U . . .
H00J H 0.584175 0.725438 0.220727 0.052 Uiso 1 1 calc R U . . .
C00I C 0.5610(2) 0.3485(4) 0.19505(19) 0.0460(8) Uani 1 1 d . . . . .
C00J C 0.4731(2) 0.3984(4) 0.1327(2) 0.0591(10) Uani 1 1 d . . . . .
H00K H 0.434840 0.469081 0.150298 0.071 Uiso 1 1 calc R U . . .
C00K C 0.8162(2) 0.7903(4) 0.2638(2) 0.0586(9) Uani 1 1 d . . . . .
H00L H 0.854951 0.886484 0.272246 0.070 Uiso 1 1 calc R U . . .
H00M H 0.822898 0.730554 0.213671 0.070 Uiso 1 1 calc R U . . .
C00L C 0.7128(3) 0.8357(4) 0.2397(2) 0.0574(9) Uani 1 1 d . . . . .
H00N H 0.690170 0.891180 0.181571 0.069 Uiso 1 1 calc R U . . .
H00O H 0.707245 0.908176 0.285595 0.069 Uiso 1 1 calc R U . . .
C00M C 0.6172(3) 0.2474(4) 0.1672(2) 0.0587(9) Uani 1 1 d . . . . .
H00P H 0.676447 0.213060 0.208955 0.070 Uiso 1 1 calc R U . . .
C00N C 0.4421(3) 0.3427(6) 0.0439(2) 0.0727(11) Uani 1 1 d . . . . .
H00Q H 0.382142 0.373530 0.001855 0.087 Uiso 1 1 calc R U . . .
C00O C 0.4996(4) 0.2429(5) 0.0185(3) 0.0783(12) Uani 1 1 d . . . . .
H00R H 0.478444 0.205797 -0.041299 0.094 Uiso 1 1 calc R U . . .
C00P C 0.5873(3) 0.1960(5) 0.0784(2) 0.0742(11) Uani 1 1 d . . . . .
H00S H 0.626620 0.129819 0.059529 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C00A 1.957(3) . ?
Se01 C00I 1.923(3) . ?
S002 N004 1.664(2) . ?
S002 O005 1.414(2) . ?
S002 O006 1.423(2) . ?
S002 C008 1.751(3) . ?
O003 C007 1.202(3) . ?
N004 C007 1.381(3) . ?
N004 C00B 1.480(3) . ?
C007 C009 1.484(3) . ?
C008 C009 1.366(3) . ?
C008 C00C 1.364(3) . ?
C009 C00D 1.374(4) . ?
C00A H00A 0.9800 . ?
C00A C00B 1.511(4) . ?
C00A C00H 1.526(4) . ?
C00B H00B 0.9800 . ?
C00B C00G 1.521(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.374(4) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.367(4) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.387(4) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9700 . ?
C00G H00H 0.9700 . ?
C00G C00K 1.517(4) . ?
C00H H00I 0.9700 . ?
C00H H00J 0.9700 . ?
C00H C00L 1.506(4) . ?
C00I C00J 1.380(4) . ?
C00I C00M 1.369(5) . ?
C00J H00K 0.9300 . ?
C00J C00N 1.383(5) . ?
C00K H00L 0.9700 . ?
C00K H00M 0.9700 . ?
C00K C00L 1.489(5) . ?
C00L H00N 0.9700 . ?
C00L H00O 0.9700 . ?
C00M H00P 0.9300 . ?
C00M C00P 1.371(5) . ?
C00N H00Q 0.9300 . ?
C00N C00O 1.355(6) . ?
C00O H00R 0.9300 . ?
C00O C00P 1.357(5) . ?
C00P H00S 0.9300 . ?

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
C00I Se01 C00A 100.70(12) . . ?
N004 S002 C008 92.88(11) . . ?
O005 S002 N004 110.17(12) . . ?
O005 S002 O006 117.40(14) . . ?
O005 S002 C008 112.90(13) . . ?
O006 S002 N004 110.58(13) . . ?
O006 S002 C008 110.23(13) . . ?
C007 N004 S002 114.59(17) . . ?
C007 N004 C00B 121.5(2) . . ?
C00B N004 S002 123.82(18) . . ?
O003 C007 N004 124.7(2) . . ?
O003 C007 C009 126.4(2) . . ?
N004 C007 C009 109.0(2) . . ?
C009 C008 S002 109.87(18) . . ?
C00C C008 S002 127.2(2) . . ?
C00C C008 C009 122.8(3) . . ?
C008 C009 C007 113.3(2) . . ?
C008 C009 C00D 119.6(2) . . ?
C00D C009 C007 127.1(2) . . ?
Se01 C00A H00A 106.7 . . ?
C00B C00A Se01 113.71(18) . . ?
C00B C00A H00A 106.7 . . ?
C00B C00A C00H 109.4(2) . . ?
C00H C00A Se01 113.09(19) . . ?
C00H C00A H00A 106.7 . . ?
N004 C00B C00A 113.3(2) . . ?
N004 C00B H00B 106.8 . . ?
N004 C00B C00G 111.1(2) . . ?
C00A C00B H00B 106.8 . . ?
C00A C00B C00G 111.7(2) . . ?
C00G C00B H00B 106.8 . . ?
C008 C00C H00C 121.3 . . ?
C008 C00C C00F 117.3(3) . . ?
C00F C00C H00C 121.3 . . ?
C009 C00D H00D 120.4 . . ?
C00E C00D C009 119.1(3) . . ?
C00E C00D H00D 120.4 . . ?
C00D C00E H00E 119.9 . . ?
C00D C00E C00F 120.3(3) . . ?
C00F C00E H00E 119.9 . . ?
C00C C00F C00E 121.0(3) . . ?
C00C C00F H00F 119.5 . . ?
C00E C00F H00F 119.5 . . ?
C00B C00G H00G 109.4 . . ?
C00B C00G H00H 109.4 . . ?
H00G C00G H00H 108.0 . . ?
C00K C00G C00B 111.1(2) . . ?
C00K C00G H00G 109.4 . . ?
C00K C00G H00H 109.4 . . ?
C00A C00H H00I 109.3 . . ?
C00A C00H H00J 109.3 . . ?
H00I C00H H00J 107.9 . . ?
C00L C00H C00A 111.7(2) . . ?
C00L C00H H00I 109.3 . . ?
C00L C00H H00J 109.3 . . ?
C00J C00I Se01 119.6(3) . . ?
C00M C00I Se01 121.1(2) . . ?
C00M C00I C00J 119.2(3) . . ?
C00I C00J H00K 120.2 . . ?
C00I C00J C00N 119.7(4) . . ?
C00N C00J H00K 120.2 . . ?
C00G C00K H00L 109.1 . . ?
C00G C00K H00M 109.1 . . ?
H00L C00K H00M 107.9 . . ?
C00L C00K C00G 112.3(3) . . ?
C00L C00K H00L 109.1 . . ?
C00L C00K H00M 109.1 . . ?
C00H C00L H00N 109.3 . . ?
C00H C00L H00O 109.3 . . ?
C00K C00L C00H 111.4(3) . . ?
C00K C00L H00N 109.3 . . ?
C00K C00L H00O 109.3 . . ?
H00N C00L H00O 108.0 . . ?
C00I C00M H00P 119.6 . . ?
C00I C00M C00P 120.8(3) . . ?
C00P C00M H00P 119.6 . . ?
C00J C00N H00Q 120.2 . . ?
C00O C00N C00J 119.6(4) . . ?
C00O C00N H00Q 120.2 . . ?
C00N C00O H00R 119.3 . . ?
C00N C00O C00P 121.4(4) . . ?
C00P C00O H00R 119.3 . . ?
C00M C00P H00S 120.4 . . ?
C00O C00P C00M 119.2(4) . . ?
C00O C00P H00S 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 C00A C00B N004 -49.9(3) . . . . ?
Se01 C00A C00B C00G -176.29(19) . . . . ?
Se01 C00A C00H C00L 175.3(2) . . . . ?
Se01 C00I C00J C00N -176.0(3) . . . . ?
Se01 C00I C00M C00P 177.8(3) . . . . ?
S002 N004 C007 O003 -176.5(2) . . . . ?
S002 N004 C007 C009 4.5(3) . . . . ?
S002 N004 C00B C00A -66.5(3) . . . . ?
S002 N004 C00B C00G 60.3(3) . . . . ?
S002 C008 C009 C007 -3.5(3) . . . . ?
S002 C008 C009 C00D 176.5(2) . . . . ?
S002 C008 C00C C00F -175.9(2) . . . . ?
O003 C007 C009 C008 -179.4(3) . . . . ?
O003 C007 C009 C00D 0.6(5) . . . . ?
N004 S002 C008 C009 5.2(2) . . . . ?
N004 S002 C008 C00C -178.6(3) . . . . ?
N004 C007 C009 C008 -0.4(3) . . . . ?
N004 C007 C009 C00D 179.6(3) . . . . ?
N004 C00B C00G C00K 177.6(2) . . . . ?
O005 S002 N004 C007 -121.4(2) . . . . ?
O005 S002 N004 C00B 55.9(2) . . . . ?
O005 S002 C008 C009 118.5(2) . . . . ?
O005 S002 C008 C00C -65.3(3) . . . . ?
O006 S002 N004 C007 107.2(2) . . . . ?
O006 S002 N004 C00B -75.6(2) . . . . ?
O006 S002 C008 C009 -108.0(2) . . . . ?
O006 S002 C008 C00C 68.2(3) . . . . ?
C007 N004 C00B C00A 110.6(3) . . . . ?
C007 N004 C00B C00G -122.7(3) . . . . ?
C007 C009 C00D C00E 179.7(3) . . . . ?
C008 S002 N004 C007 -5.7(2) . . . . ?
C008 S002 N004 C00B 171.6(2) . . . . ?
C008 C009 C00D C00E -0.2(4) . . . . ?
C008 C00C C00F C00E 0.4(4) . . . . ?
C009 C008 C00C C00F -0.1(4) . . . . ?
C009 C00D C00E C00F 0.6(5) . . . . ?
C00A C00B C00G C00K -54.8(3) . . . . ?
C00A C00H C00L C00K 56.2(4) . . . . ?
C00B N004 C007 O003 6.2(4) . . . . ?
C00B N004 C007 C009 -172.8(2) . . . . ?
C00B C00A C00H C00L -56.9(3) . . . . ?
C00B C00G C00K C00L 53.2(4) . . . . ?
C00C C008 C009 C007 -180.0(2) . . . . ?
C00C C008 C009 C00D 0.0(4) . . . . ?
C00D C00E C00F C00C -0.7(5) . . . . ?
C00G C00K C00L C00H -54.0(4) . . . . ?
C00H C00A C00B N004 -177.4(2) . . . . ?
C00H C00A C00B C00G 56.3(3) . . . . ?
C00I C00J C00N C00O -1.7(6) . . . . ?
C00I C00M C00P C00O -1.9(6) . . . . ?
C00J C00I C00M C00P 0.2(5) . . . . ?
C00J C00N C00O C00P 0.0(6) . . . . ?
C00M C00I C00J C00N 1.5(5) . . . . ?
C00N C00O C00P C00M 1.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_221215znn406_0m
_database_code_depnum_ccdc_archive 'CCDC 2227321'
loop_
_audit_author_name
_audit_author_address
zhang
;xinjiang university
China
;
_audit_update_record             
;
2022-12-19 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;
_audit_creation_date             2022-12-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O4 Se'
_chemical_formula_sum            'C19 H19 N O4 Se'
_chemical_formula_weight         404.31
_chemical_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'
Se Se -0.0929 2.2259 '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                   6.0420(6)
_cell_length_b                   7.1534(7)
_cell_length_c                   41.598(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.970(2)
_cell_angle_gamma                90
_cell_volume                     1796.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2287
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.527
_cell_measurement_theta_min      3.011
_shelx_estimated_absorpt_T_max   0.817
_shelx_estimated_absorpt_T_min   0.252
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0744 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.7937.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            10475
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.626
_diffrn_reflns_theta_min         2.889
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2812
_reflns_number_total             4080
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²+0.7258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18)
;
_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 0.11687(6) -0.05787(4) 0.65397(2) 0.05003(12) Uani 1 1 d . . . . .
O1 O 0.8011(4) 0.6944(5) 0.51629(6) 0.0882(9) Uani 1 1 d . . . . .
O2 O 0.5692(3) 0.4632(4) 0.67174(5) 0.0606(6) Uani 1 1 d . . . . .
O3 O 0.4533(4) 0.7142(4) 0.50369(5) 0.0729(7) Uani 1 1 d . . . . .
O4 O 0.2297(3) 0.3787(3) 0.65393(4) 0.0360(4) Uani 1 1 d . . . . .
N1 N 0.6062(5) 0.6839(4) 0.52281(6) 0.0537(7) Uani 1 1 d . . . . .
C1 C 0.6678(4) 0.5999(4) 0.61055(7) 0.0381(7) Uani 1 1 d . . . . .
H1 H 0.772452 0.618473 0.627162 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4646(4) 0.5179(4) 0.61689(6) 0.0319(6) Uani 1 1 d . . . . .
C3 C -0.0646(5) 0.0709(5) 0.71190(7) 0.0498(8) Uani 1 1 d . . . . .
H3A H -0.190104 -0.011400 0.707849 0.060 Uiso 1 1 calc R U . . .
H3B H 0.054811 -0.003093 0.721512 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7134(4) 0.6531(4) 0.57976(7) 0.0408(7) Uani 1 1 d . . . . .
H4 H 0.849579 0.705754 0.575229 0.049 Uiso 1 1 calc R U . . .
C5 C -0.2035(5) 0.1541(4) 0.57080(7) 0.0452(7) Uani 1 1 d . . . . .
H5 H -0.340140 0.206603 0.565134 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4299(4) 0.4530(4) 0.65043(7) 0.0368(6) Uani 1 1 d . . . . .
C7 C -0.1294(5) 0.2225(5) 0.73546(7) 0.0534(8) Uani 1 1 d . . . . .
H7A H -0.263337 0.283968 0.727450 0.064 Uiso 1 1 calc R U . . .
H7B H -0.160123 0.165905 0.756021 0.064 Uiso 1 1 calc R U . . .
C8 C 0.5544(5) 0.6274(4) 0.55578(6) 0.0376(6) Uani 1 1 d . . . . .
C9 C 0.0483(4) 0.0277(3) 0.61117(6) 0.0349(6) Uani 1 1 d . . . . .
C10 C 0.0096(4) 0.1512(4) 0.67990(6) 0.0354(6) Uani 1 1 d . . . . .
H10 H -0.118743 0.207693 0.668605 0.042 Uiso 1 1 calc R U . . .
C11 C -0.0471(5) 0.1274(4) 0.54785(7) 0.0483(8) Uani 1 1 d . . . . .
H11 H -0.079030 0.160120 0.526558 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3494(4) 0.5504(4) 0.56113(7) 0.0394(6) Uani 1 1 d . . . . .
H12 H 0.243670 0.537378 0.544503 0.047 Uiso 1 1 calc R U . . .
C13 C 0.1555(5) 0.0526(5) 0.55644(7) 0.0507(8) Uani 1 1 d . . . . .
H13 H 0.260523 0.034604 0.540898 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2047(5) 0.0037(4) 0.58806(7) 0.0422(7) Uani 1 1 d . . . . .
H14 H 0.343072 -0.045375 0.593762 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3065(4) 0.4931(4) 0.59220(6) 0.0350(6) Uani 1 1 d . . . . .
H15 H 0.171332 0.437872 0.596500 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1110(5) 0.4520(4) 0.70786(6) 0.0432(7) Uani 1 1 d . . . . .
H16A H -0.017273 0.516111 0.698523 0.052 Uiso 1 1 calc R U . . .
H16B H 0.229057 0.542686 0.711090 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1845(4) 0.2986(4) 0.68520(6) 0.0339(6) Uani 1 1 d . . . . .
H17 H 0.319693 0.240191 0.694176 0.041 Uiso 1 1 calc R U . . .
C18 C -0.1558(5) 0.1025(4) 0.60214(7) 0.0408(7) Uani 1 1 d . . . . .
H18 H -0.262433 0.118044 0.617514 0.049 Uiso 1 1 calc R U . . .
C19 C 0.0532(5) 0.3657(5) 0.74004(7) 0.0478(8) Uani 1 1 d . . . . .
H19A H 0.183520 0.306351 0.749721 0.057 Uiso 1 1 calc R U . . .
H19B H 0.005604 0.463061 0.754482 0.057 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 C9 1.915(3) . ?
Se1 C10 1.967(3) . ?
O1 N1 1.219(3) . ?
O2 C6 1.204(3) . ?
O3 N1 1.218(3) . ?
O4 C6 1.334(3) . ?
O4 C17 1.456(3) . ?
N1 C8 1.474(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.394(4) . ?
C1 C4 1.373(4) . ?
C2 C6 1.492(4) . ?
C2 C15 1.390(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C7 1.522(4) . ?
C3 C10 1.531(4) . ?
C4 H4 0.9300 . ?
C4 C8 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C11 1.379(4) . ?
C5 C18 1.376(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C19 1.513(4) . ?
C8 C12 1.381(4) . ?
C9 C14 1.382(4) . ?
C9 C18 1.384(4) . ?
C10 H10 0.9800 . ?
C10 C17 1.504(4) . ?
C11 H11 0.9300 . ?
C11 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C12 C15 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.523(4) . ?
C16 C19 1.526(4) . ?
C17 H17 0.9800 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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 Se1 C10 101.66(11) . . ?
C6 O4 C17 116.95(19) . . ?
O1 N1 C8 117.5(3) . . ?
O3 N1 O1 124.1(3) . . ?
O3 N1 C8 118.4(3) . . ?
C2 C1 H1 120.0 . . ?
C4 C1 H1 120.0 . . ?
C4 C1 C2 120.0(3) . . ?
C1 C2 C6 117.5(2) . . ?
C15 C2 C1 120.1(2) . . ?
C15 C2 C6 122.4(2) . . ?
H3A C3 H3B 107.8 . . ?
C7 C3 H3A 109.1 . . ?
C7 C3 H3B 109.1 . . ?
C7 C3 C10 112.5(3) . . ?
C10 C3 H3A 109.1 . . ?
C10 C3 H3B 109.1 . . ?
C1 C4 H4 120.6 . . ?
C1 C4 C8 118.9(3) . . ?
C8 C4 H4 120.6 . . ?
C11 C5 H5 120.3 . . ?
C18 C5 H5 120.3 . . ?
C18 C5 C11 119.5(3) . . ?
O2 C6 O4 123.9(2) . . ?
O2 C6 C2 123.6(2) . . ?
O4 C6 C2 112.6(2) . . ?
C3 C7 H7A 109.4 . . ?
C3 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C19 C7 C3 111.2(2) . . ?
C19 C7 H7A 109.4 . . ?
C19 C7 H7B 109.4 . . ?
C4 C8 N1 118.3(3) . . ?
C4 C8 C12 123.1(3) . . ?
C12 C8 N1 118.7(3) . . ?
C14 C9 Se1 118.4(2) . . ?
C14 C9 C18 118.9(3) . . ?
C18 C9 Se1 122.6(2) . . ?
Se1 C10 H10 108.7 . . ?
C3 C10 Se1 107.68(19) . . ?
C3 C10 H10 108.7 . . ?
C17 C10 Se1 111.75(17) . . ?
C17 C10 C3 111.2(2) . . ?
C17 C10 H10 108.7 . . ?
C5 C11 H11 120.0 . . ?
C13 C11 C5 120.0(3) . . ?
C13 C11 H11 120.0 . . ?
C8 C12 H12 121.1 . . ?
C8 C12 C15 117.7(2) . . ?
C15 C12 H12 121.1 . . ?
C11 C13 H13 119.8 . . ?
C11 C13 C14 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.0(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C2 C15 H15 119.9 . . ?
C12 C15 C2 120.3(2) . . ?
C12 C15 H15 119.9 . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C17 C16 C19 109.4(2) . . ?
C19 C16 H16A 109.8 . . ?
C19 C16 H16B 109.8 . . ?
O4 C17 C10 107.3(2) . . ?
O4 C17 C16 109.7(2) . . ?
O4 C17 H17 109.2 . . ?
C10 C17 C16 112.2(2) . . ?
C10 C17 H17 109.2 . . ?
C16 C17 H17 109.2 . . ?
C5 C18 C9 121.1(3) . . ?
C5 C18 H18 119.5 . . ?
C9 C18 H18 119.5 . . ?
C7 C19 C16 110.6(2) . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?

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 C9 C14 C13 175.8(2) . . . . ?
Se1 C9 C18 C5 -176.7(2) . . . . ?
Se1 C10 C17 O4 64.9(2) . . . . ?
Se1 C10 C17 C16 -174.56(18) . . . . ?
O1 N1 C8 C4 22.5(4) . . . . ?
O1 N1 C8 C12 -157.2(3) . . . . ?
O3 N1 C8 C4 -158.6(3) . . . . ?
O3 N1 C8 C12 21.7(4) . . . . ?
N1 C8 C12 C15 178.2(2) . . . . ?
C1 C2 C6 O2 -2.1(4) . . . . ?
C1 C2 C6 O4 179.3(2) . . . . ?
C1 C2 C15 C12 -0.3(4) . . . . ?
C1 C4 C8 N1 -179.6(3) . . . . ?
C1 C4 C8 C12 0.1(4) . . . . ?
C2 C1 C4 C8 1.2(4) . . . . ?
C3 C7 C19 C16 57.0(3) . . . . ?
C3 C10 C17 O4 -174.8(2) . . . . ?
C3 C10 C17 C16 -54.2(3) . . . . ?
C4 C1 C2 C6 176.5(3) . . . . ?
C4 C1 C2 C15 -1.2(4) . . . . ?
C4 C8 C12 C15 -1.5(4) . . . . ?
C5 C11 C13 C14 -0.1(5) . . . . ?
C6 O4 C17 C10 -153.8(2) . . . . ?
C6 O4 C17 C16 84.0(3) . . . . ?
C6 C2 C15 C12 -177.9(3) . . . . ?
C7 C3 C10 Se1 174.1(2) . . . . ?
C7 C3 C10 C17 51.4(3) . . . . ?
C8 C12 C15 C2 1.6(4) . . . . ?
C10 C3 C7 C19 -53.2(3) . . . . ?
C11 C5 C18 C9 1.4(4) . . . . ?
C11 C13 C14 C9 0.9(5) . . . . ?
C14 C9 C18 C5 -0.6(4) . . . . ?
C15 C2 C6 O2 175.5(3) . . . . ?
C15 C2 C6 O4 -3.0(4) . . . . ?
C17 O4 C6 O2 -2.8(4) . . . . ?
C17 O4 C6 C2 175.7(2) . . . . ?
C17 C16 C19 C7 -58.9(3) . . . . ?
C18 C5 C11 C13 -1.0(5) . . . . ?
C18 C9 C14 C13 -0.5(4) . . . . ?
C19 C16 C17 O4 177.3(2) . . . . ?
C19 C16 C17 C10 58.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_230101znn_0m
_database_code_depnum_ccdc_archive 'CCDC 2233790'
loop_
_audit_author_name
_audit_author_address
zhang
;xinjiang university
China
;
_audit_update_record             
;
2023-01-01 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;
_audit_creation_date             2023-01-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Br N O3 S Se'
_chemical_formula_sum            'C23 H18 Br N O3 S Se'
_chemical_formula_weight         547.31
_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'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.9532(9)
_cell_length_b                   24.647(2)
_cell_length_c                   17.5152(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4296.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3587
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.837
_cell_measurement_theta_min      2.494
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.707
_exptl_absorpt_coefficient_mu    3.730
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0325 after correction.
The Ratio of minimum to maximum transmission is 0.6892.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.853
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2669
_reflns_number_total             3771
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.006
_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)+(0.0243P)²+3.4635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(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:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
Br1 Br 0.88802(4) 0.65630(2) 0.54741(2) 0.04956(13) Uani 1 1 d . . . . .
Se1 Se 0.68245(4) 0.66937(2) 0.80078(2) 0.04540(12) Uani 1 1 d . . . . .
S1 S 0.52036(9) 0.58076(3) 0.54056(6) 0.0374(2) Uani 1 1 d . . . . .
O1 O 0.4864(2) 0.73104(9) 0.56477(14) 0.0454(7) Uani 1 1 d . . . . .
O2 O 0.6238(2) 0.56127(10) 0.49156(15) 0.0543(7) Uani 1 1 d . . . . .
O3 O 0.4818(3) 0.54738(9) 0.60269(15) 0.0546(7) Uani 1 1 d . . . . .
N1 N 0.5579(3) 0.64297(10) 0.57312(16) 0.0314(7) Uani 1 1 d . . . . .
C1 C 0.2696(4) 0.68742(14) 0.4581(2) 0.0455(10) Uani 1 1 d . . . . .
H1 H 0.259536 0.724734 0.463541 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1829(4) 0.65788(15) 0.4126(2) 0.0530(11) Uani 1 1 d . . . . .
H2 H 0.113307 0.675598 0.387451 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1978(4) 0.60242(15) 0.4039(2) 0.0514(11) Uani 1 1 d . . . . .
H3 H 0.138783 0.583478 0.372546 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2991(4) 0.57481(14) 0.4413(2) 0.0427(9) Uani 1 1 d . . . . .
H4 H 0.310183 0.537570 0.435420 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3831(3) 0.60469(13) 0.48744(19) 0.0321(8) Uani 1 1 d . . . . .
C6 C 0.3712(3) 0.66030(13) 0.4952(2) 0.0330(8) Uani 1 1 d . . . . .
C7 C 0.4743(3) 0.68398(13) 0.5463(2) 0.0317(8) Uani 1 1 d . . . . .
C8 C 0.6525(3) 0.65281(13) 0.63743(19) 0.0333(8) Uani 1 1 d . . . . .
H8 H 0.675272 0.691484 0.636135 0.040 Uiso 1 1 calc R U . . .
C9 C 0.5842(3) 0.64252(14) 0.71321(19) 0.0387(9) Uani 1 1 d . . . . .
H9A H 0.570904 0.603762 0.719149 0.046 Uiso 1 1 calc R U . . .
H9B H 0.496240 0.659466 0.712380 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6260(3) 0.74367(14) 0.8056(2) 0.0371(9) Uani 1 1 d . . . . .
C11 C 0.6979(4) 0.77664(15) 0.8537(2) 0.0468(10) Uani 1 1 d . . . . .
H11 H 0.770364 0.762416 0.880642 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6646(4) 0.83023(16) 0.8627(2) 0.0562(11) Uani 1 1 d . . . . .
H12 H 0.713925 0.851950 0.895811 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5592(4) 0.85182(16) 0.8231(2) 0.0581(12) Uani 1 1 d . . . . .
H13 H 0.537335 0.888293 0.828607 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4866(5) 0.81970(16) 0.7757(3) 0.0663(13) Uani 1 1 d . . . . .
H14 H 0.414256 0.834284 0.749060 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5189(4) 0.76537(16) 0.7663(2) 0.0591(12) Uani 1 1 d . . . . .
H15 H 0.468442 0.743684 0.733668 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7827(3) 0.62187(13) 0.62379(19) 0.0318(8) Uani 1 1 d . . . . .
C17 C 0.8181(3) 0.57747(13) 0.66020(19) 0.0346(8) Uani 1 1 d . . . . .
H17 H 0.755356 0.566277 0.696269 0.042 Uiso 1 1 calc R U . . .
C18 C 0.9361(3) 0.54190(13) 0.6557(2) 0.0320(8) Uani 1 1 d . . . . .
C19 C 0.9672(4) 0.51151(13) 0.7200(2) 0.0405(9) Uani 1 1 d . . . . .
H19 H 0.912216 0.513789 0.762832 0.049 Uiso 1 1 calc R U . . .
C20 C 1.0784(4) 0.47786(14) 0.7216(3) 0.0524(11) Uani 1 1 d . . . . .
H20 H 1.099254 0.458559 0.765659 0.063 Uiso 1 1 calc R U . . .
C21 C 1.1573(4) 0.47310(16) 0.6585(3) 0.0617(13) Uani 1 1 d . . . . .
H21 H 1.231774 0.450337 0.659259 0.074 Uiso 1 1 calc R U . . .
C22 C 1.1271(4) 0.50158(17) 0.5946(3) 0.0707(14) Uani 1 1 d . . . . .
H22 H 1.180824 0.498025 0.551499 0.085 Uiso 1 1 calc R U . . .
C23 C 1.0178(4) 0.53567(16) 0.5929(2) 0.0599(12) Uani 1 1 d . . . . .
H23 H 0.998765 0.554856 0.548442 0.072 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
Br1 C16 1.900(3) . ?
Se1 C9 1.936(3) . ?
Se1 C10 1.917(3) . ?
S1 O2 1.424(3) . ?
S1 O3 1.417(3) . ?
S1 N1 1.678(3) . ?
S1 C5 1.755(3) . ?
O1 C7 1.210(4) . ?
N1 C7 1.391(4) . ?
N1 C8 1.488(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(5) . ?
C1 C6 1.375(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.382(4) . ?
C6 C7 1.481(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.513(5) . ?
C8 C16 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.373(5) . ?
C10 C15 1.376(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.356(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.315(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.468(4) . ?
C18 C19 1.387(4) . ?
C18 C23 1.377(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.360(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.355(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(5) . ?
C23 H23 0.9300 . ?

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 102.30(15) . . ?
O2 S1 N1 110.61(15) . . ?
O2 S1 C5 110.91(16) . . ?
O3 S1 O2 117.56(16) . . ?
O3 S1 N1 109.25(15) . . ?
O3 S1 C5 113.04(16) . . ?
N1 S1 C5 92.66(14) . . ?
C7 N1 S1 114.6(2) . . ?
C7 N1 C8 121.1(3) . . ?
C8 N1 S1 123.2(2) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.4(3) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 S1 127.2(3) . . ?
C4 C5 C6 122.4(3) . . ?
C6 C5 S1 110.4(2) . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 C7 127.1(3) . . ?
C5 C6 C7 113.0(3) . . ?
O1 C7 N1 123.1(3) . . ?
O1 C7 C6 127.5(3) . . ?
N1 C7 C6 109.4(3) . . ?
N1 C8 H8 106.7 . . ?
N1 C8 C9 110.6(3) . . ?
N1 C8 C16 109.8(3) . . ?
C9 C8 H8 106.7 . . ?
C9 C8 C16 115.9(3) . . ?
C16 C8 H8 106.7 . . ?
Se1 C9 H9A 108.7 . . ?
Se1 C9 H9B 108.7 . . ?
C8 C9 Se1 114.2(2) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 Se1 116.1(3) . . ?
C11 C10 C15 118.7(3) . . ?
C15 C10 Se1 125.2(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 119.7(4) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C8 C16 Br1 110.9(2) . . ?
C17 C16 Br1 124.4(3) . . ?
C17 C16 C8 124.7(3) . . ?
C16 C17 H17 113.4 . . ?
C16 C17 C18 133.3(3) . . ?
C18 C17 H17 113.4 . . ?
C19 C18 C17 117.2(3) . . ?
C23 C18 C17 125.6(3) . . ?
C23 C18 C19 117.2(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.9(4) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.7(4) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.1(4) . . ?
C22 C23 H23 119.4 . . ?

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
Br1 C16 C17 C18 -0.7(6) . . . . ?
Se1 C10 C11 C12 -178.7(3) . . . . ?
Se1 C10 C15 C14 178.8(3) . . . . ?
S1 N1 C7 O1 179.1(3) . . . . ?
S1 N1 C7 C6 0.5(3) . . . . ?
S1 N1 C8 C9 -79.1(3) . . . . ?
S1 N1 C8 C16 50.0(4) . . . . ?
S1 C5 C6 C1 -180.0(3) . . . . ?
S1 C5 C6 C7 -0.9(4) . . . . ?
O2 S1 N1 C7 112.7(2) . . . . ?
O2 S1 N1 C8 -79.8(3) . . . . ?
O2 S1 C5 C4 65.3(4) . . . . ?
O2 S1 C5 C6 -112.3(3) . . . . ?
O3 S1 N1 C7 -116.4(2) . . . . ?
O3 S1 N1 C8 51.1(3) . . . . ?
O3 S1 C5 C4 -69.2(4) . . . . ?
O3 S1 C5 C6 113.2(3) . . . . ?
N1 S1 C5 C4 178.5(3) . . . . ?
N1 S1 C5 C6 1.0(3) . . . . ?
N1 C8 C9 Se1 -166.7(2) . . . . ?
N1 C8 C16 Br1 74.7(3) . . . . ?
N1 C8 C16 C17 -105.6(4) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C1 C6 C7 O1 0.8(6) . . . . ?
C1 C6 C7 N1 179.3(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C2 C1 C6 C7 180.0(4) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 S1 -179.3(3) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C4 C5 C6 C1 2.3(5) . . . . ?
C4 C5 C6 C7 -178.6(3) . . . . ?
C5 S1 N1 C7 -0.9(3) . . . . ?
C5 S1 N1 C8 166.7(3) . . . . ?
C5 C6 C7 O1 -178.3(3) . . . . ?
C5 C6 C7 N1 0.3(4) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C7 N1 C8 C9 87.7(4) . . . . ?
C7 N1 C8 C16 -143.2(3) . . . . ?
C8 N1 C7 O1 11.3(5) . . . . ?
C8 N1 C7 C6 -167.3(3) . . . . ?
C8 C16 C17 C18 179.7(3) . . . . ?
C9 C8 C16 Br1 -159.1(2) . . . . ?
C9 C8 C16 C17 20.5(5) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C11 C10 C15 C14 0.4(6) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C13 C14 C15 C10 0.0(7) . . . . ?
C15 C10 C11 C12 -0.2(6) . . . . ?
C16 C8 C9 Se1 67.5(3) . . . . ?
C16 C17 C18 C19 155.6(4) . . . . ?
C16 C17 C18 C23 -25.2(6) . . . . ?
C17 C18 C19 C20 -178.5(3) . . . . ?
C17 C18 C23 C22 179.4(4) . . . . ?
C18 C19 C20 C21 -1.8(5) . . . . ?
C19 C18 C23 C22 -1.3(6) . . . . ?
C19 C20 C21 C22 0.4(6) . . . . ?
C20 C21 C22 C23 0.5(7) . . . . ?
C21 C22 C23 C18 0.0(7) . . . . ?
C23 C18 C19 C20 2.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
