# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 2107600'
loop_
_audit_author_name
_audit_author_address
'Raju Saravanan'
;Department of Chemistry, IIT Bombay
India
;
_audit_update_record             
;
2021-09-04 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N O3 Se'
_chemical_formula_weight         359.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.7511(5)
_cell_length_b                   23.9217(13)
_cell_length_c                   8.4244(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.099(8)
_cell_angle_gamma                90
_cell_volume                     1466.92(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7966
_cell_measurement_theta_min      2.7050
_cell_measurement_theta_max      30.8650

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    2.572
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31198
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.1384
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3776
_reflns_number_gt                2527
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0699P)²+2.7908P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3776
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1771
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_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 0.40746(7) 0.33978(2) 0.65792(7) 0.02998(19) Uani 1 1 d . . . . .
O1 O 0.4908(6) 0.23387(17) 0.8034(6) 0.0483(11) Uani 1 1 d . . . . .
O2 O 0.5990(4) 0.44036(15) 0.8400(4) 0.0247(7) Uani 1 1 d . . . . .
O3 O 0.8433(6) 0.45636(19) 1.0626(5) 0.0475(11) Uani 1 1 d . . . . .
N1 N 0.0949(6) 0.39367(18) 0.3442(5) 0.0316(10) Uani 1 1 d . . . . .
H1A H 0.021004 0.378698 0.388299 0.038 Uiso 1 1 d R U . . .
H1B H 0.031890 0.410354 0.251997 0.038 Uiso 1 1 d R U . . .
C1 C 0.3752(10) 0.2331(3) 0.8702(9) 0.0496(16) Uani 1 1 d . . . . .
H1 H 0.377215 0.202374 0.942241 0.060 Uiso 1 1 calc R U . . .
C2 C 0.2314(8) 0.2758(2) 0.8495(8) 0.0387(13) Uani 1 1 d . . . . .
C3 C 0.1018(10) 0.2651(3) 0.9257(10) 0.0581(19) Uani 1 1 d . . . . .
H3 H 0.110701 0.231979 0.990068 0.070 Uiso 1 1 calc R U . . .
C4 C -0.0400(10) 0.3024(3) 0.9087(9) 0.0545(18) Uani 1 1 d . . . . .
H4 H -0.130060 0.294603 0.958807 0.065 Uiso 1 1 calc R U . . .
C5 C -0.0488(8) 0.3506(3) 0.8184(8) 0.0401(14) Uani 1 1 d . . . . .
H5 H -0.146118 0.376363 0.805033 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0839(7) 0.3622(2) 0.7462(6) 0.0284(11) Uani 1 1 d . . . . .
H6 H 0.078675 0.396418 0.687645 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2243(7) 0.3242(2) 0.7587(6) 0.0296(11) Uani 1 1 d . . . . .
C8 C 0.3479(6) 0.4164(2) 0.5993(6) 0.0223(10) Uani 1 1 d . . . . .
C9 C 0.2027(6) 0.4321(2) 0.4523(6) 0.0223(10) Uani 1 1 d . . . . .
C10 C 0.1670(6) 0.4901(2) 0.4204(6) 0.0245(10) Uani 1 1 d . . . . .
H10 H 0.070150 0.501591 0.321593 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2691(7) 0.52936(19) 0.5289(6) 0.0227(10) Uani 1 1 d . . . . .
H11 H 0.239429 0.567712 0.505277 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4168(6) 0.5151(2) 0.6745(5) 0.0221(10) Uani 1 1 d . . . . .
C13 C 0.4529(6) 0.4579(2) 0.7047(6) 0.0218(10) Uani 1 1 d . . . . .
C14 C 0.7163(7) 0.4771(2) 0.9514(6) 0.0321(12) Uani 1 1 d . . . . .
C15 C 0.6732(8) 0.5355(2) 0.9256(6) 0.0342(12) Uani 1 1 d . . . . .
H15 H 0.748697 0.561625 1.003673 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5289(7) 0.5548(2) 0.7942(6) 0.0282(11) Uani 1 1 d . . . . .
C17 C 0.4883(8) 0.6158(2) 0.7739(7) 0.0392(14) Uani 1 1 d . . . . .
H17A H 0.494417 0.628408 0.665349 0.059 Uiso 1 1 calc R U . . .
H17B H 0.578899 0.636240 0.866024 0.059 Uiso 1 1 calc R U . . .
H17C H 0.364979 0.622738 0.777129 0.059 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 C8 1.912(5) . ?
Se1 C7 1.924(5) . ?
O1 C1 1.211(8) . ?
O2 C13 1.368(5) . ?
O2 C14 1.377(6) . ?
O3 C14 1.208(6) . ?
N1 C9 1.360(6) . ?
N1 H1A 0.8605 . ?
N1 H1B 0.8606 . ?
C1 C2 1.478(8) . ?
C1 H1 0.9500 . ?
C2 C7 1.379(7) . ?
C2 C3 1.389(8) . ?
C3 C4 1.383(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(7) . ?
C6 H6 0.9500 . ?
C8 C13 1.393(7) . ?
C8 C9 1.408(6) . ?
C9 C10 1.423(7) . ?
C10 C11 1.359(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(7) . ?
C12 C16 1.438(7) . ?
C14 C15 1.434(8) . ?
C15 C16 1.356(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.490(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C8 Se1 C7 98.6(2) . . ?
C13 O2 C14 122.4(4) . . ?
C9 N1 H1A 109.8 . . ?
C9 N1 H1B 108.6 . . ?
H1A N1 H1B 109.1 . . ?
O1 C1 C2 125.7(6) . . ?
O1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C7 C2 C3 120.9(5) . . ?
C7 C2 C1 122.1(5) . . ?
C3 C2 C1 117.0(5) . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.0(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 118.0(5) . . ?
C2 C7 Se1 120.8(4) . . ?
C6 C7 Se1 121.1(4) . . ?
C13 C8 C9 119.0(4) . . ?
C13 C8 Se1 118.8(3) . . ?
C9 C8 Se1 122.1(4) . . ?
N1 C9 C8 122.0(4) . . ?
N1 C9 C10 119.8(4) . . ?
C8 C9 C10 118.1(4) . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 116.6(4) . . ?
C11 C12 C16 124.6(5) . . ?
C13 C12 C16 118.8(4) . . ?
O2 C13 C8 116.6(4) . . ?
O2 C13 C12 120.4(4) . . ?
C8 C13 C12 123.0(4) . . ?
O3 C14 O2 115.9(5) . . ?
O3 C14 C15 127.1(5) . . ?
O2 C14 C15 117.0(4) . . ?
C16 C15 C14 122.6(5) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C12 118.5(5) . . ?
C15 C16 C17 120.6(5) . . ?
C12 C16 C17 120.8(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C1 C2 C7 -5.1(10) . . . . ?
O1 C1 C2 C3 174.8(7) . . . . ?
C7 C2 C3 C4 1.5(11) . . . . ?
C1 C2 C3 C4 -178.3(7) . . . . ?
C2 C3 C4 C5 -1.4(11) . . . . ?
C3 C4 C5 C6 -0.5(10) . . . . ?
C4 C5 C6 C7 2.3(9) . . . . ?
C3 C2 C7 C6 0.3(9) . . . . ?
C1 C2 C7 C6 -179.9(5) . . . . ?
C3 C2 C7 Se1 178.5(5) . . . . ?
C1 C2 C7 Se1 -1.7(8) . . . . ?
C5 C6 C7 C2 -2.2(8) . . . . ?
C5 C6 C7 Se1 179.6(4) . . . . ?
C13 C8 C9 N1 -179.9(4) . . . . ?
Se1 C8 C9 N1 0.7(6) . . . . ?
C13 C8 C9 C10 -1.5(7) . . . . ?
Se1 C8 C9 C10 179.1(3) . . . . ?
N1 C9 C10 C11 178.0(4) . . . . ?
C8 C9 C10 C11 -0.4(7) . . . . ?
C9 C10 C11 C12 1.7(7) . . . . ?
C10 C11 C12 C13 -1.0(7) . . . . ?
C10 C11 C12 C16 -179.6(5) . . . . ?
C14 O2 C13 C8 178.3(4) . . . . ?
C14 O2 C13 C12 -0.2(6) . . . . ?
C9 C8 C13 O2 -176.1(4) . . . . ?
Se1 C8 C13 O2 3.2(6) . . . . ?
C9 C8 C13 C12 2.3(7) . . . . ?
Se1 C8 C13 C12 -178.3(3) . . . . ?
C11 C12 C13 O2 177.3(4) . . . . ?
C16 C12 C13 O2 -3.9(6) . . . . ?
C11 C12 C13 C8 -1.1(7) . . . . ?
C16 C12 C13 C8 177.7(4) . . . . ?
C13 O2 C14 O3 -177.8(4) . . . . ?
C13 O2 C14 C15 3.5(6) . . . . ?
O3 C14 C15 C16 178.6(5) . . . . ?
O2 C14 C15 C16 -2.9(8) . . . . ?
C14 C15 C16 C12 -1.1(8) . . . . ?
C14 C15 C16 C17 179.3(5) . . . . ?
C11 C12 C16 C15 -176.9(5) . . . . ?
C13 C12 C16 C15 4.5(7) . . . . ?
C11 C12 C16 C17 2.8(7) . . . . ?
C13 C12 C16 C17 -175.9(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
_geom_hbond_publ_flag
N1 H1B O3 0.86 2.07 2.916(6) 166.7 1_454 yes
C10 H10 O3 0.95 2.53 3.292(6) 137.6 1_454 yes

_refine_diff_density_max         1.623
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.144



