# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mo_gs_ab_2_266_0ma
_database_code_depnum_ccdc_archive 'CCDC 2314641'
loop_
_audit_author_name
_audit_author_address
'Ramana babu'
;IITH
India
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-02-02 downloaded from the CCDC.
;
_audit_creation_date             2023-12-15
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl2 O2 Se'
_chemical_formula_sum            'C16 H16 Cl2 O2 Se'
_chemical_formula_weight         390.15
_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'
Cl Cl 0.1484 0.1585 '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/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                   9.4200(18)
_cell_length_b                   25.033(5)
_cell_length_c                   7.5118(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.342(6)
_cell_angle_gamma                90
_cell_volume                     1649.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.599
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1201 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.6791.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25233
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.164
_diffrn_reflns_theta_min         2.321
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-IV Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                2476
_reflns_number_total             3649
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.027
_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)+(0.0175P)²+1.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.32973(4) 0.54333(2) 0.61807(5) 0.05479(12) Uani 1 1 d . . . . .
Cl1 Cl 0.05140(9) 0.75043(4) 0.23290(13) 0.0575(2) Uani 1 1 d . . . . .
Cl2 Cl 0.72349(9) 0.78348(4) 0.31151(14) 0.0614(3) Uani 1 1 d . . . . .
O1 O 0.2642(2) 0.66697(8) 0.2546(3) 0.0515(6) Uani 1 1 d . . . . .
O2 O 0.3201(3) 0.52659(9) 0.1953(3) 0.0566(6) Uani 1 1 d . . . . .
H2 H 0.386014 0.519460 0.298983 0.085 Uiso 1 1 calc R U . . .
C1 C 0.2656(3) 0.47139(12) 0.6295(5) 0.0448(8) Uani 1 1 d . . . . .
C2 C 0.2834(4) 0.45181(15) 0.8081(5) 0.0593(9) Uani 1 1 d . . . . .
H2A H 0.321702 0.473570 0.915398 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2436(4) 0.39958(19) 0.8256(7) 0.0824(14) Uani 1 1 d . . . . .
H3 H 0.256852 0.385999 0.945835 0.099 Uiso 1 1 calc R U . . .
C4 C 0.1846(4) 0.36744(16) 0.6678(9) 0.0836(15) Uani 1 1 d . . . . .
H4 H 0.156919 0.332389 0.680445 0.100 Uiso 1 1 calc R U . . .
C5 C 0.1672(4) 0.38731(15) 0.4933(7) 0.0768(12) Uani 1 1 d . . . . .
H5 H 0.126868 0.365587 0.386148 0.092 Uiso 1 1 calc R U . . .
C6 C 0.2078(4) 0.43882(13) 0.4713(6) 0.0600(9) Uani 1 1 d . . . . .
H6 H 0.196379 0.451681 0.350760 0.072 Uiso 1 1 calc R U . . .
C7 C 0.1780(3) 0.56700(13) 0.3747(4) 0.0488(8) Uani 1 1 d . . . . .
H7A H 0.094720 0.541527 0.335477 0.059 Uiso 1 1 calc R U . . .
H7B H 0.137041 0.601095 0.394430 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2384(3) 0.57303(12) 0.2137(4) 0.0438(7) Uani 1 1 d . . . . .
C9 C 0.1062(4) 0.57947(15) 0.0250(5) 0.0637(10) Uani 1 1 d . . . . .
H9A H 0.144279 0.580965 -0.077355 0.096 Uiso 1 1 calc R U . . .
H9B H 0.052416 0.611902 0.027046 0.096 Uiso 1 1 calc R U . . .
H9C H 0.038223 0.549633 0.005795 0.096 Uiso 1 1 calc R U . . .
C10 C 0.3479(3) 0.61997(11) 0.2483(5) 0.0439(7) Uani 1 1 d . . . . .
H10A H 0.433032 0.615387 0.368173 0.053 Uiso 1 1 calc R U . . .
H10B H 0.387351 0.622544 0.145966 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3308(3) 0.71531(11) 0.2647(4) 0.0358(7) Uani 1 1 d . . . . .
C12 C 0.4806(3) 0.72318(12) 0.2816(4) 0.0398(7) Uani 1 1 d . . . . .
H12 H 0.543903 0.694153 0.287981 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5346(3) 0.77445(12) 0.2889(4) 0.0394(7) Uani 1 1 d . . . . .
C14 C 0.4447(3) 0.81805(12) 0.2783(4) 0.0471(8) Uani 1 1 d . . . . .
H14 H 0.483507 0.852394 0.282705 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2950(3) 0.81019(12) 0.2609(4) 0.0452(8) Uani 1 1 d . . . . .
H15 H 0.232226 0.839451 0.253265 0.054 Uiso 1 1 calc R U . . .
C16 C 0.2389(3) 0.75962(12) 0.2549(4) 0.0364(7) Uani 1 1 d . . . . .


_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 C1 1.911(3) . ?
Se1 C7 1.958(3) . ?
Cl1 C16 1.728(3) . ?
Cl2 C13 1.740(3) . ?
O1 C10 1.427(3) . ?
O1 C11 1.353(3) . ?
O2 H2 0.8200 . ?
O2 C8 1.428(4) . ?
C1 C2 1.380(5) . ?
C1 C6 1.379(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.355(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.520(4) . ?
C8 C9 1.517(4) . ?
C8 C10 1.522(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.384(4) . ?
C11 C16 1.392(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(4) . ?
C13 C14 1.366(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(4) . ?

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
C1 Se1 C7 101.06(13) . . ?
C11 O1 C10 119.2(2) . . ?
C8 O2 H2 109.5 . . ?
C2 C1 Se1 116.7(3) . . ?
C6 C1 Se1 123.4(3) . . ?
C6 C1 C2 119.8(3) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
Se1 C7 H7A 108.6 . . ?
Se1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 Se1 114.5(2) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
O2 C8 C7 111.6(2) . . ?
O2 C8 C9 106.5(3) . . ?
O2 C8 C10 106.8(2) . . ?
C7 C8 C10 111.6(3) . . ?
C9 C8 C7 109.6(3) . . ?
C9 C8 C10 110.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C8 107.1(2) . . ?
O1 C10 H10A 110.3 . . ?
O1 C10 H10B 110.3 . . ?
C8 C10 H10A 110.3 . . ?
C8 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
O1 C11 C12 124.7(3) . . ?
O1 C11 C16 116.3(2) . . ?
C12 C11 C16 119.0(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 Cl2 118.4(2) . . ?
C14 C13 Cl2 119.5(2) . . ?
C14 C13 C12 122.1(3) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(3) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 Cl1 119.5(2) . . ?
C15 C16 Cl1 119.7(2) . . ?
C15 C16 C11 120.7(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
Se1 C1 C2 C3 -177.9(3) . . . . ?
Se1 C1 C6 C5 178.8(3) . . . . ?
Se1 C7 C8 O2 50.0(3) . . . . ?
Se1 C7 C8 C9 167.7(2) . . . . ?
Se1 C7 C8 C10 -69.4(3) . . . . ?
Cl2 C13 C14 C15 -179.8(2) . . . . ?
O1 C11 C12 C13 179.4(3) . . . . ?
O1 C11 C16 Cl1 0.5(4) . . . . ?
O1 C11 C16 C15 -179.0(3) . . . . ?
O2 C8 C10 O1 176.3(2) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C7 C8 C10 O1 -61.5(3) . . . . ?
C9 C8 C10 O1 60.8(3) . . . . ?
C10 O1 C11 C12 -4.2(4) . . . . ?
C10 O1 C11 C16 175.0(3) . . . . ?
C11 O1 C10 C8 -173.4(2) . . . . ?
C11 C12 C13 Cl2 179.7(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C11 C16 Cl1 179.8(2) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 Cl1 -179.9(2) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'
