# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2132533'
loop_
_audit_author_name
_audit_author_address
'Krishna Pada Bhabak'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2022-01-05 deposited with the CCDC.	2022-05-11 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          '145 -- 146 \%C'
_chemical_formula_moiety         'C18  H17  N3  O1  Se2'
_chemical_formula_sum            'C18 H17 N3 O1 Se2'
_chemical_formula_weight         449.26

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.7765(10)
_cell_length_b                   16.086(2)
_cell_length_c                   16.129(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1758.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3090
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      25.0

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    4.216
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.703
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            72031
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.788
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3090
_reflns_number_gt                2755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0185P)²+3.5646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.70004(10) 0.33897(4) 0.76480(4) 0.03413(17) Uani 1 1 d . . . . .
Se2 Se 0.13021(14) 0.39601(6) 0.85513(6) 0.0646(3) Uani 1 1 d . . . . .
N2 N 0.3315(7) 0.2674(3) 0.6946(3) 0.0292(12) Uani 1 1 d . . . . .
O1 O 1.0201(7) 0.0942(3) 0.8958(3) 0.0438(12) Uani 1 1 d . . . . .
N1 N 0.4442(7) 0.3836(3) 0.6421(3) 0.0298(12) Uani 1 1 d . . . . .
C7 C 0.4749(9) 0.3244(4) 0.6991(4) 0.0275(13) Uani 1 1 d . . . . .
C11 C 0.4894(9) 0.1667(4) 0.7895(4) 0.0319(14) Uani 1 1 d . . . . .
C1 C 0.1987(10) 0.2924(4) 0.6323(4) 0.0299(13) Uani 1 1 d . . . . .
C6 C 0.2727(9) 0.3657(4) 0.5987(4) 0.0311(15) Uani 1 1 d . . . . .
C13 C 0.8063(11) 0.0990(4) 0.7829(4) 0.0390(15) Uani 1 1 d . . . . .
H13 H 0.900725 0.069853 0.752808 0.047 Uiso 1 1 calc R U . . .
C14 C 0.8405(10) 0.1190(4) 0.8655(4) 0.0348(16) Uani 1 1 d . . . . .
C12 C 0.6313(10) 0.1227(4) 0.7457(4) 0.0381(16) Uani 1 1 d . . . . .
H12 H 0.608422 0.108980 0.690474 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3021(10) 0.1938(4) 0.7479(4) 0.0403(16) Uani 1 1 d . . . . .
H10A H 0.251583 0.148403 0.714535 0.048 Uiso 1 1 calc R U . . .
H10B H 0.204300 0.206638 0.789936 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6977(10) 0.1607(4) 0.9105(4) 0.0366(14) Uani 1 1 d . . . . .
H15 H 0.718342 0.173143 0.966083 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1781(11) 0.4066(4) 0.5346(4) 0.0398(16) Uani 1 1 d . . . . .
H5 H 0.228161 0.455276 0.511794 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0266(10) 0.2571(5) 0.6041(4) 0.0384(16) Uani 1 1 d . . . . .
H2 H -0.022342 0.208106 0.626740 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0046(12) 0.3709(5) 0.5064(5) 0.050(2) Uani 1 1 d . . . . .
H4 H -0.064233 0.396321 0.463401 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5246(10) 0.1835(4) 0.8719(4) 0.0369(16) Uani 1 1 d . . . . .
H16 H 0.428557 0.211102 0.902544 0.044 Uiso 1 1 calc R U . . .
C18 C -0.0194(12) 0.4842(5) 0.8863(5) 0.0450(18) Uani 1 1 d . . . . .
C3 C -0.0695(10) 0.2974(5) 0.5411(5) 0.046(2) Uani 1 1 d . . . . .
H3 H -0.186912 0.275419 0.520862 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5886(10) 0.4509(4) 0.6338(5) 0.0396(17) Uani 1 1 d . . . . .
H8A H 0.522364 0.504362 0.635403 0.048 Uiso 1 1 calc R U . . .
H8B H 0.657703 0.446186 0.581384 0.048 Uiso 1 1 calc R U . . .
N3 N -0.1084(13) 0.5376(5) 0.9028(5) 0.071(2) Uani 1 1 d . . . . .
C17 C 1.0682(12) 0.1176(6) 0.9786(5) 0.056(2) Uani 1 1 d . . . . .
H17A H 1.196717 0.096700 0.992462 0.084 Uiso 1 1 calc R U . . .
H17B H 1.067848 0.177090 0.983099 0.084 Uiso 1 1 calc R U . . .
H17C H 0.972331 0.094696 1.016028 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7320(12) 0.4444(4) 0.7043(5) 0.053(2) Uani 1 1 d . . . . .
H9A H 0.711721 0.490474 0.742083 0.064 Uiso 1 1 calc R U . . .
H9B H 0.865482 0.448039 0.682907 0.064 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 C7 1.873(6) . ?
Se1 C9 1.968(7) . ?
Se2 C18 1.814(9) . ?
N2 C7 1.338(7) . ?
N2 C1 1.408(8) . ?
N2 C10 1.477(8) . ?
O1 C14 1.371(8) . ?
O1 C17 1.425(8) . ?
N1 C7 1.340(8) . ?
N1 C6 1.387(8) . ?
N1 C8 1.466(8) . ?
C11 C16 1.378(9) . ?
C11 C12 1.388(9) . ?
C11 C10 1.500(9) . ?
C1 C2 1.374(9) . ?
C1 C6 1.391(9) . ?
C6 C5 1.382(9) . ?
C13 C12 1.383(9) . ?
C13 C14 1.390(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(9) . ?
C12 H12 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 C16 1.377(9) . ?
C15 H15 0.9300 . ?
C5 C4 1.385(11) . ?
C5 H5 0.9300 . ?
C2 C3 1.370(10) . ?
C2 H2 0.9300 . ?
C4 C3 1.401(11) . ?
C4 H4 0.9300 . ?
C16 H16 0.9300 . ?
C18 N3 1.084(10) . ?
C3 H3 0.9300 . ?
C8 C9 1.498(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 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
C7 Se1 C9 85.2(3) . . ?
C7 N2 C1 107.9(5) . . ?
C7 N2 C10 128.0(5) . . ?
C1 N2 C10 123.9(5) . . ?
C14 O1 C17 117.4(5) . . ?
C7 N1 C6 109.2(5) . . ?
C7 N1 C8 118.9(5) . . ?
C6 N1 C8 131.8(5) . . ?
N2 C7 N1 109.7(5) . . ?
N2 C7 Se1 135.1(5) . . ?
N1 C7 Se1 115.2(4) . . ?
C16 C11 C12 118.1(6) . . ?
C16 C11 C10 121.4(6) . . ?
C12 C11 C10 120.5(6) . . ?
C2 C1 C6 121.8(6) . . ?
C2 C1 N2 131.4(6) . . ?
C6 C1 N2 106.8(5) . . ?
C5 C6 N1 131.9(6) . . ?
C5 C6 C1 121.8(6) . . ?
N1 C6 C1 106.4(5) . . ?
C12 C13 C14 119.7(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
O1 C14 C15 125.1(6) . . ?
O1 C14 C13 115.0(6) . . ?
C15 C14 C13 119.9(6) . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N2 C10 C11 112.3(5) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C16 C15 C14 119.3(6) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C6 C5 C4 116.3(7) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 H5 121.9 . . ?
C3 C2 C1 117.0(7) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C5 C4 C3 121.4(7) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C15 C16 C11 122.1(6) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
N3 C18 Se2 178.0(8) . . ?
C2 C3 C4 121.7(7) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
N1 C8 C9 108.2(5) . . ?
N1 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C9 Se1 111.4(5) . . ?
C8 C9 H9A 109.3 . . ?
Se1 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
Se1 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?

_refine_diff_density_max         0.687
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.078

