# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ga_201116aa_a
_database_code_depnum_ccdc_archive 'CCDC 2102437'
loop_
_audit_author_name
_audit_author_address
'Fusheng He'
;Taizhou University
China
;
_audit_update_record             
;
2021-08-10 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br N O2 S Se'
_chemical_formula_weight         469.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -1.0833 0.8881 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3416(9)
_cell_length_b                   18.4062(16)
_cell_length_c                   10.3029(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.267(3)
_cell_angle_gamma                90
_cell_volume                     1814.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      60.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    4.329
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15494
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.019
_diffrn_reflns_theta_max         59.490
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3975
_reflns_number_gt                3499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0793P)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_number_reflns         3975
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_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
Se1 Se 0.57438(3) 0.59328(2) 0.58989(4) 0.02702(13) Uani 1 1 d . . . . .
Br1 Br 0.00549(3) 0.52529(2) 0.17427(4) 0.03611(14) Uani 1 1 d . . . . .
S1 S 0.26927(7) 0.70398(3) 0.74640(8) 0.02436(17) Uani 1 1 d . . . . .
N1 N 0.3553(3) 0.46136(14) 1.0261(4) 0.0392(7) Uani 1 1 d . . . . .
O1 O 0.3031(3) 0.77592(10) 0.8045(3) 0.0401(6) Uani 1 1 d . . . . .
O2 O 0.1455(2) 0.69399(12) 0.6210(3) 0.0377(5) Uani 1 1 d . . . . .
C1 C 0.3569(3) 0.51809(16) 1.0694(4) 0.0324(7) Uani 1 1 d . . . . .
C2 C 0.3600(4) 0.59308(15) 1.1199(4) 0.0370(7) Uani 1 1 d . . . . .
H2A H 0.438573 0.598522 1.211498 0.044 Uiso 1 1 calc R U . . .
H2B H 0.272163 0.603372 1.133768 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3771(3) 0.64783(14) 1.0152(3) 0.0300(6) Uani 1 1 d . . . . .
H3A H 0.387750 0.697289 1.055662 0.036 Uiso 1 1 calc R U . . .
H3B H 0.462818 0.636208 0.998179 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2524(3) 0.64629(14) 0.8773(4) 0.0268(6) Uani 1 1 d . . . . .
H4A H 0.168079 0.660826 0.894553 0.032 Uiso 1 1 calc R U . . .
H4B H 0.238022 0.595820 0.841433 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4177(3) 0.67487(13) 0.7173(3) 0.0221(5) Uani 1 1 d . . . . .
H5 H 0.502486 0.700739 0.762292 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4187(3) 0.61866(12) 0.6360(3) 0.0202(5) Uani 1 1 d . . . . .
C7 C 0.3039(3) 0.56511(12) 0.5692(3) 0.0196(5) Uani 1 1 d . . . . .
C8 C 0.2183(3) 0.57147(12) 0.4277(3) 0.0194(5) Uani 1 1 d . . . . .
H8 H 0.225299 0.612417 0.374658 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1227(3) 0.51668(13) 0.3664(3) 0.0233(5) Uani 1 1 d . . . . .
C10 C 0.1099(3) 0.45576(13) 0.4410(4) 0.0272(6) Uani 1 1 d . . . . .
H10 H 0.044121 0.418666 0.396662 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1955(3) 0.45078(13) 0.5811(4) 0.0290(6) Uani 1 1 d . . . . .
H11 H 0.188060 0.409798 0.633891 0.035 Uiso 1 1 calc R U . . .
C12 C 0.2926(3) 0.50491(13) 0.6462(3) 0.0231(5) Uani 1 1 d . . . . .
H12 H 0.350811 0.500800 0.742670 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7037(3) 0.66986(13) 0.6802(3) 0.0237(5) Uani 1 1 d . . . . .
C14 C 0.7025(4) 0.73308(15) 0.6070(4) 0.0340(7) Uani 1 1 d . . . . .
H14 H 0.635227 0.739955 0.514686 0.041 Uiso 1 1 calc R U . . .
C15 C 0.8021(4) 0.78657(16) 0.6713(4) 0.0397(8) Uani 1 1 d . . . . .
H15 H 0.801346 0.830647 0.623011 0.048 Uiso 1 1 calc R U . . .
C16 C 0.9008(3) 0.77608(15) 0.8033(4) 0.0335(7) Uani 1 1 d . . . . .
H16 H 0.969653 0.812274 0.844672 0.040 Uiso 1 1 calc R U . . .
C17 C 0.9010(3) 0.71333(16) 0.8766(4) 0.0318(6) Uani 1 1 d . . . . .
H17 H 0.968480 0.706783 0.968825 0.038 Uiso 1 1 calc R U . . .
C18 C 0.8015(3) 0.65943(14) 0.8146(3) 0.0281(6) Uani 1 1 d . . . . .
H18 H 0.800958 0.616019 0.864320 0.034 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 C6 1.901(2) . ?
Se1 C13 1.923(3) . ?
Br1 C9 1.896(3) . ?
S1 O1 1.440(2) . ?
S1 O2 1.445(3) . ?
S1 C5 1.755(3) . ?
S1 C4 1.776(3) . ?
N1 C1 1.133(4) . ?
C1 C2 1.471(4) . ?
C2 C3 1.535(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.515(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.334(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.495(3) . ?
C7 C12 1.393(4) . ?
C7 C8 1.395(4) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(4) . ?
C10 C11 1.381(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.384(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.397(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Se1 C13 101.45(10) . . ?
O1 S1 O2 118.82(15) . . ?
O1 S1 C5 105.11(13) . . ?
O2 S1 C5 110.13(13) . . ?
O1 S1 C4 108.21(15) . . ?
O2 S1 C4 107.10(15) . . ?
C5 S1 C4 106.92(12) . . ?
N1 C1 C2 177.3(4) . . ?
C1 C2 C3 111.1(3) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 111.3(3) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 S1 114.0(2) . . ?
C3 C4 H4A 108.7 . . ?
S1 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
S1 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 S1 124.0(2) . . ?
C6 C5 H5 118.0 . . ?
S1 C5 H5 118.0 . . ?
C5 C6 C7 127.3(2) . . ?
C5 C6 Se1 123.82(19) . . ?
C7 C6 Se1 108.84(17) . . ?
C12 C7 C8 120.3(2) . . ?
C12 C7 C6 119.1(2) . . ?
C8 C7 C6 120.3(2) . . ?
C9 C8 C7 118.5(2) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 Br1 118.6(2) . . ?
C10 C9 Br1 119.1(2) . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 119.7(3) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C18 C13 C14 121.0(3) . . ?
C18 C13 Se1 119.5(2) . . ?
C14 C13 Se1 119.4(2) . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 119.4(3) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?

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
C1 C2 C3 C4 64.3(4) . . . . ?
C2 C3 C4 S1 -176.10(19) . . . . ?
O1 S1 C4 C3 -53.1(2) . . . . ?
O2 S1 C4 C3 177.66(19) . . . . ?
C5 S1 C4 C3 59.6(2) . . . . ?
O1 S1 C5 C6 -164.1(3) . . . . ?
O2 S1 C5 C6 -35.0(3) . . . . ?
C4 S1 C5 C6 81.1(3) . . . . ?
S1 C5 C6 C7 -7.9(4) . . . . ?
S1 C5 C6 Se1 173.47(14) . . . . ?
C5 C6 C7 C12 -85.2(3) . . . . ?
Se1 C6 C7 C12 93.6(2) . . . . ?
C5 C6 C7 C8 101.1(3) . . . . ?
Se1 C6 C7 C8 -80.1(2) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 173.4(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C7 C8 C9 Br1 179.73(17) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
Br1 C9 C10 C11 -179.51(19) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C8 C7 C12 C11 0.2(4) . . . . ?
C6 C7 C12 C11 -173.4(2) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
Se1 C13 C14 C15 -176.5(2) . . . . ?
C13 C14 C15 C16 1.3(5) . . . . ?
C14 C15 C16 C17 -1.9(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
C14 C13 C18 C17 -0.5(4) . . . . ?
Se1 C13 C18 C17 176.0(2) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.166

