# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_aks4s
_database_code_depnum_ccdc_archive 'CCDC 1983076'
loop_
_audit_author_name
_audit_author_address
'Carlos Aydillo'
;Universidad de Navarra
Spain
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2020-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        
((E)-1-(2,6-dichlorophenyl)-3-((methylselanyl)methylene)indolin-2-one
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H11 Cl2 N O Se'
_chemical_formula_sum            'C16 H11 Cl2 N O Se'
_chemical_compound_source        synthesis
_chemical_formula_weight         383.12
_chemical_melting_point          446
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      298(2)
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'
Cl Cl 0.1484 0.1585 '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'

_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'
_chemical_absolute_configuration ?
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.3923(9)
_cell_length_b                   12.7253(14)
_cell_length_c                   14.6560(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.072(2)
_cell_angle_gamma                90.00
_cell_volume                     1565.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.238
_cell_measurement_theta_min      2.427
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.717833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS V2.05 (BRUKER, 2001) was used for absorption correction. R(int) was 0.0808 before and 0.0187 after correction. The Ratio of minimum to maximum transmission is 0.7178. The λ/2 correction factor is 0.0015.'
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_special_details           
'The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.'
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13375
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.12
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_number_gt                2893
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2016)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.1981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.10067(3) 0.50093(2) 0.662168(16) 0.05351(12) Uani 1 d . . .
Cl2 Cl 0.20025(9) 0.39022(5) 0.20020(5) 0.0635(2) Uani 1 d . . .
Cl3 Cl 0.44198(10) 0.08956(7) 0.41979(5) 0.0758(2) Uani 1 d . . .
O1 O 0.4211(2) 0.42263(14) 0.40139(12) 0.0589(5) Uani 1 d . . .
N1 N 0.2510(2) 0.28258(15) 0.38009(12) 0.0427(4) Uani 1 d . . .
C1 C 0.3345(2) 0.23897(18) 0.30454(14) 0.0406(5) Uani 1 d . . .
C2 C 0.4319(3) 0.1525(2) 0.31470(16) 0.0481(5) Uani 1 d . . .
C3 C 0.5210(3) 0.1137(2) 0.24283(18) 0.0580(7) Uani 1 d . . .
H3 H 0.5845 0.0545 0.2507 0.070 Uiso 1 calc . . R
C4 C 0.5147(3) 0.1634(2) 0.15967(17) 0.0569(7) Uani 1 d . . .
H4 H 0.5763 0.1386 0.1116 0.068 Uiso 1 calc . . R
C5 C 0.4182(3) 0.2493(2) 0.14698(16) 0.0520(6) Uani 1 d . . .
H5 H 0.4141 0.2827 0.0906 0.062 Uiso 1 calc . . R
C6 C 0.3273(3) 0.28561(18) 0.21908(15) 0.0427(5) Uani 1 d . . .
C7 C 0.1144(3) 0.24171(18) 0.42308(14) 0.0421(5) Uani 1 d . . .
C8 C 0.0283(3) 0.1534(2) 0.40109(19) 0.0604(7) Uani 1 d . . .
H8 H 0.0567 0.1108 0.3522 0.072 Uiso 1 calc . . R
C9 C -0.1031(4) 0.1304(2) 0.4552(2) 0.0706(8) Uani 1 d . . .
H9 H -0.1635 0.0710 0.4424 0.085 Uiso 1 calc . . R
C10 C -0.1455(3) 0.1938(2) 0.5270(2) 0.0669(8) Uani 1 d . . .
H10 H -0.2349 0.1769 0.5615 0.080 Uiso 1 calc . . R
C11 C -0.0580(3) 0.2818(2) 0.54884(17) 0.0542(6) Uani 1 d . . .
H11 H -0.0878 0.3240 0.5977 0.065 Uiso 1 calc . . R
C12 C 0.0749(3) 0.30694(18) 0.49728(14) 0.0402(5) Uani 1 d . . .
C13 C 0.1920(3) 0.39089(17) 0.50090(13) 0.0384(5) Uani 1 d . . .
C14 C 0.3039(3) 0.37290(18) 0.42393(14) 0.0426(5) Uani 1 d . . .
C15 C 0.2191(3) 0.46994(19) 0.55940(14) 0.0420(5) Uani 1 d . . .
H15 H 0.3057 0.5133 0.5471 0.050 Uiso 1 calc . . R
C16 C 0.2231(4) 0.6197(3) 0.7057(2) 0.0811(10) Uani 1 d . . .
H16A H 0.2238 0.6737 0.6601 0.122 Uiso 1 calc . . GR
H16B H 0.3304 0.5978 0.7181 0.122 Uiso 1 calc . . GR
H16C H 0.1757 0.6464 0.7606 0.122 Uiso 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 C15 1.848(2) . ?
Se1 C16 1.935(3) . ?
Cl2 C6 1.728(2) . ?
Cl3 C2 1.738(3) . ?
O1 C14 1.216(3) . ?
N1 C1 1.424(3) . ?
N1 C7 1.408(3) . ?
N1 C14 1.389(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C7 C8 1.375(3) . ?
C7 C12 1.408(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C12 C13 1.453(3) . ?
C13 C14 1.487(3) . ?
C13 C15 1.341(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C15 Se1 C16 98.62(12) . . ?
C7 N1 C1 127.27(18) . . ?
C14 N1 C1 121.66(18) . . ?
C14 N1 C7 111.01(17) . . ?
C2 C1 N1 121.3(2) . . ?
C2 C1 C6 117.6(2) . . ?
C6 C1 N1 121.0(2) . . ?
C1 C2 Cl3 119.44(18) . . ?
C1 C2 C3 121.6(2) . . ?
C3 C2 Cl3 119.0(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 Cl2 120.03(17) . . ?
C5 C6 Cl2 118.40(18) . . ?
C5 C6 C1 121.6(2) . . ?
N1 C7 C12 108.71(19) . . ?
C8 C7 N1 128.7(2) . . ?
C8 C7 C12 122.6(2) . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 117.1(2) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C13 107.54(18) . . ?
C11 C12 C7 118.4(2) . . ?
C11 C12 C13 134.0(2) . . ?
C12 C13 C14 106.69(18) . . ?
C15 C13 C12 133.6(2) . . ?
C15 C13 C14 119.6(2) . . ?
O1 C14 N1 124.3(2) . . ?
O1 C14 C13 129.7(2) . . ?
N1 C14 C13 106.05(18) . . ?
Se1 C15 H15 116.9 . . ?
C13 C15 Se1 126.18(19) . . ?
C13 C15 H15 116.9 . . ?
Se1 C16 H16A 109.5 . . ?
Se1 C16 H16B 109.5 . . ?
Se1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 O1 0.93 2.55 3.363(3) 146.7 3_666

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
Cl3 C2 C3 C4 -179.5(2) . . . . ?
N1 C1 C2 Cl3 4.8(3) . . . . ?
N1 C1 C2 C3 -175.9(2) . . . . ?
N1 C1 C6 Cl2 -6.6(3) . . . . ?
N1 C1 C6 C5 174.5(2) . . . . ?
N1 C7 C8 C9 -179.9(3) . . . . ?
N1 C7 C12 C11 179.2(2) . . . . ?
N1 C7 C12 C13 -0.5(2) . . . . ?
C1 N1 C7 C8 -2.0(4) . . . . ?
C1 N1 C7 C12 177.5(2) . . . . ?
C1 N1 C14 O1 1.4(4) . . . . ?
C1 N1 C14 C13 -177.38(19) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C1 C6 Cl2 176.84(17) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 Cl2 -177.18(19) . . . . ?
C4 C5 C6 C1 1.8(4) . . . . ?
C6 C1 C2 Cl3 -178.70(17) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C7 N1 C1 C2 -75.1(3) . . . . ?
C7 N1 C1 C6 108.5(3) . . . . ?
C7 N1 C14 O1 178.8(2) . . . . ?
C7 N1 C14 C13 0.0(2) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C7 C12 C13 C14 0.5(2) . . . . ?
C7 C12 C13 C15 -175.0(2) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
C8 C7 C12 C13 179.1(2) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C7 0.9(4) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 -179.1(3) . . . . ?
C11 C12 C13 C15 5.4(4) . . . . ?
C12 C7 C8 C9 0.6(4) . . . . ?
C12 C13 C14 O1 -179.0(2) . . . . ?
C12 C13 C14 N1 -0.3(2) . . . . ?
C12 C13 C15 Se1 -1.7(4) . . . . ?
C14 N1 C1 C2 101.8(3) . . . . ?
C14 N1 C1 C6 -74.6(3) . . . . ?
C14 N1 C7 C8 -179.2(3) . . . . ?
C14 N1 C7 C12 0.3(3) . . . . ?
C14 C13 C15 Se1 -176.67(16) . . . . ?
C15 C13 C14 O1 -2.8(4) . . . . ?
C15 C13 C14 N1 176.0(2) . . . . ?
C16 Se1 C15 C13 178.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

