# 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_AKBKKD_2
_database_code_depnum_ccdc_archive 'CCDC 2308886'
loop_
_audit_author_name
_audit_author_address
'SUVAM BHATTACHARJEE'
;VISVA BHARATI
India
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 F N2 O Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         500.63

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.840(2)
_cell_length_b                   12.074(3)
_cell_length_c                   13.093(3)
_cell_angle_alpha                102.890(7)
_cell_angle_beta                 107.408(7)
_cell_angle_gamma                110.200(6)
_cell_volume                     1297.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.3328
_cell_measurement_theta_max      28.4329
_cell_measurement_temperature    302.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524

_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.9237
_exptl_absorpt_correction_T_max  1.0000

_exptl_special_details           
;
;

_diffrn_ambient_temperature      302.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  BRUKER
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            21957
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.61
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5770
_reflns_number_gt                4502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2039
_refine_ls_goodness_of_fit_ref   1.461
_refine_ls_restrained_S_all      1.461
_refine_ls_number_reflns         5770
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.004
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1365)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si1 0.41354(5) 0.70666(4) 0.75071(4) 0.03802(19) Uani d . . . 1 . .
F F1 0.55255(17) 0.92225(12) 0.42231(13) 0.0798(4) Uani d . . . 1 . .
O O1 -0.0322(2) 0.10085(15) 0.66453(17) 0.0822(6) Uani d . . . 1 . .
N N3 0.24133(16) 0.49313(12) 0.52846(12) 0.0402(4) Uani d . . . 1 . .
N N4 0.21733(19) 0.45835(14) 0.41826(13) 0.0488(4) Uani d . . . 1 . .
C C1 0.3813(2) 0.85182(16) 0.76656(15) 0.0430(4) Uani d . . . 1 . .
C C2 0.2354(2) 0.84386(18) 0.70192(18) 0.0556(5) Uani d . . . 1 . .
H H2 0.155361 0.765562 0.648467 0.067000 Uiso calc U . R 1 . .
C C3 0.2057(3) 0.9483(2) 0.7146(2) 0.0664(6) Uani d . . . 1 . .
H H3 0.106821 0.940362 0.670302 0.080000 Uiso calc U . R 1 . .
C C4 0.3228(3) 1.0640(2) 0.7927(2) 0.0676(6) Uani d . . . 1 . .
H H4 0.303448 1.134919 0.801803 0.081000 Uiso calc U . R 1 . .
C C5 0.4672(3) 1.07562(19) 0.8572(2) 0.0701(7) Uani d . . . 1 . .
H H5 0.546435 1.154599 0.909966 0.084000 Uiso calc U . R 1 . .
C C6 0.4975(3) 0.97010(18) 0.84470(18) 0.0571(5) Uani d . . . 1 . .
H H6 0.596795 0.979190 0.889387 0.069000 Uiso calc U . R 1 . .
C C7 0.3614(2) 0.5227(2) 0.85467(19) 0.0600(6) Uani d . . . 1 . .
H H7 0.435838 0.506613 0.832023 0.072000 Uiso calc U . R 1 . .
C C8 0.2958(3) 0.4545(3) 0.9136(2) 0.0796(8) Uani d . . . 1 . .
H H8 0.324416 0.392263 0.929021 0.095000 Uiso calc U . R 1 . .
C C9 0.1892(3) 0.4791(3) 0.9488(3) 0.0925(9) Uani d . . . 1 . .
H H9 0.145583 0.433714 0.989139 0.111000 Uiso calc U . R 1 . .
C C10 0.1451(4) 0.5697(3) 0.9257(3) 0.0938(9) Uani d . . . 1 . .
H H10 0.072870 0.586523 0.950866 0.113000 Uiso calc U . R 1 . .
C C11 0.2095(3) 0.6367(2) 0.8642(2) 0.0661(6) Uani d . . . 1 . .
H H11 0.177904 0.697017 0.847097 0.079000 Uiso calc U . R 1 . .
C C12 0.2990(2) 0.56768(17) 0.40771(16) 0.0456(4) Uani d . . . 1 . .
C C13 0.37161(19) 0.67062(15) 0.51347(15) 0.0400(4) Uani d . . . 1 . .
C C14 0.7216(2) 0.74313(18) 0.75749(19) 0.0540(5) Uani d . . . 1 . .
H H14 0.674220 0.711539 0.677575 0.065000 Uiso calc U . R 1 . .
C C15 0.8830(3) 0.7812(2) 0.8139(2) 0.0705(7) Uani d . . . 1 . .
H H15 0.942613 0.774664 0.771526 0.085000 Uiso calc U . R 1 . .
C C16 0.9549(2) 0.8280(2) 0.9306(2) 0.0711(7) Uani d . . . 1 . .
H H16 1.063277 0.853736 0.967899 0.085000 Uiso calc U . R 1 . .
C C17 0.8670(3) 0.8373(2) 0.9935(2) 0.0717(7) Uani d . . . 1 . .
H H17 0.915460 0.869609 1.073378 0.086000 Uiso calc U . R 1 . .
C C18 0.7075(2) 0.7986(2) 0.93726(19) 0.0615(6) Uani d . . . 1 . .
H H18 0.648602 0.804127 0.980430 0.074000 Uiso calc U . R 1 . .
C C19 0.1674(2) 0.39373(14) 0.56517(15) 0.0418(4) Uani d . . . 1 . .
C C20 0.0506(2) 0.39194(15) 0.60091(16) 0.0432(4) Uani d . . . 1 . .
H H20 0.018374 0.455944 0.602308 0.052000 Uiso calc U . R 1 . .
C C21 -0.0206(2) 0.29472(16) 0.63533(17) 0.0498(5) Uani d . . . 1 . .
H H21 -0.099208 0.293817 0.661134 0.060000 Uiso calc U . R 1 . .
C C22 0.0274(2) 0.19896(17) 0.63064(19) 0.0563(5) Uani d . . . 1 . .
C C23 0.1407(3) 0.19929(18) 0.5908(2) 0.0642(6) Uani d . . . 1 . .
H H23 0.169043 0.132938 0.585220 0.077000 Uiso calc U . R 1 . .
C C24 0.2138(3) 0.29721(18) 0.55868(19) 0.0577(5) Uani d . . . 1 . .
H H24 0.292759 0.298345 0.533161 0.069000 Uiso calc U . R 1 . .
C C25 0.3134(3) 0.5854(2) 0.30797(19) 0.0601(5) Uani d . . . 1 . .
H H25 0.265168 0.517361 0.238581 0.072000 Uiso calc U . R 1 . .
C C26 0.3995(3) 0.7042(2) 0.3164(2) 0.0617(6) Uani d . . . 1 . .
H H26 0.412201 0.719021 0.252337 0.074000 Uiso calc U . R 1 . .
C C27 0.4693(2) 0.80491(19) 0.4213(2) 0.0553(5) Uani d . . . 1 . .
C C28 0.4588(2) 0.79456(17) 0.51919(17) 0.0476(5) Uani d . . . 1 . .
H H28 0.505997 0.864803 0.586745 0.057000 Uiso calc U . R 1 . .
C C29 -0.1527(3) 0.0937(2) 0.7032(3) 0.0855(9) Uani d . . . 1 . .
H H29A -0.179262 0.023215 0.728151 0.128000 Uiso calc U . R 1 . .
H H29B -0.245093 0.082436 0.641588 0.128000 Uiso calc U . R 1 . .
H H29C -0.116120 0.170621 0.766144 0.128000 Uiso calc U . R 1 . .
C C30 0.33338(19) 0.61980(14) 0.59268(15) 0.0378(4) Uani d . . . 1 . .
C C31 0.3191(2) 0.61478(17) 0.82823(16) 0.0461(4) Uani d . . . 1 . .
C C32 0.6302(2) 0.75146(15) 0.81832(15) 0.0410(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 C31 . 1.8654(19) ?
Si1 C1 . 1.8644(19) ?
Si1 C30 . 1.8675(18) ?
Si1 C32 . 1.8660(19) ?
F1 C27 . 1.365(2) ?
O1 C22 . 1.362(2) ?
O1 C29 . 1.406(3) ?
N3 N4 . 1.331(2) ?
N3 C30 . 1.3714(19) ?
N3 C19 . 1.437(2) ?
N4 C12 . 1.350(2) ?
C1 C2 . 1.388(3) ?
C1 C6 . 1.383(3) ?
C2 C3 . 1.377(3) ?
C3 C4 . 1.368(3) ?
C4 C5 . 1.357(4) ?
C5 C6 . 1.392(3) ?
C7 C31 . 1.391(3) ?
C7 C8 . 1.379(3) ?
C8 C9 . 1.358(4) ?
C9 C10 . 1.369(4) ?
C10 C11 . 1.395(3) ?
C11 C31 . 1.378(3) ?
C12 C13 . 1.414(2) ?
C12 C25 . 1.409(3) ?
C13 C30 . 1.397(2) ?
C13 C28 . 1.416(2) ?
C14 C32 . 1.382(3) ?
C14 C15 . 1.386(3) ?
C15 C16 . 1.359(4) ?
C16 C17 . 1.374(4) ?
C17 C18 . 1.369(3) ?
C18 C32 . 1.387(3) ?
C19 C20 . 1.360(3) ?
C19 C24 . 1.386(3) ?
C20 C21 . 1.389(2) ?
C21 C22 . 1.388(3) ?
C22 C23 . 1.365(3) ?
C23 C24 . 1.381(3) ?
C25 C26 . 1.350(3) ?
C26 C27 . 1.397(3) ?
C27 C28 . 1.346(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C31 Si1 C1 . . 110.01(9) ?
C31 Si1 C30 . . 114.65(8) ?
C1 Si1 C30 . . 105.74(8) ?
C31 Si1 C32 . . 106.65(8) ?
C1 Si1 C32 . . 110.08(8) ?
C30 Si1 C32 . . 109.72(8) ?
C22 O1 C29 . . 118.30(19) ?
N4 N3 C30 . . 115.71(14) ?
N4 N3 C19 . . 116.14(13) ?
C30 N3 C19 . . 128.15(15) ?
N3 N4 C12 . . 103.80(14) ?
C2 C1 C6 . . 117.18(18) ?
C2 C1 Si1 . . 120.49(13) ?
C6 C1 Si1 . . 122.30(15) ?
C1 C2 C3 . . 122.0(2) ?
C4 C3 C2 . . 119.5(2) ?
C5 C4 C3 . . 120.3(2) ?
C4 C5 C6 . . 120.4(2) ?
C1 C6 C5 . . 120.7(2) ?
C31 C7 C8 . . 121.8(2) ?
C9 C8 C7 . . 119.5(3) ?
C10 C9 C8 . . 120.8(2) ?
C9 C10 C11 . . 119.5(3) ?
C31 C11 C10 . . 121.0(2) ?
N4 C12 C13 . . 110.86(16) ?
N4 C12 C25 . . 127.70(18) ?
C13 C12 C25 . . 121.43(18) ?
C30 C13 C12 . . 106.28(14) ?
C30 C13 C28 . . 134.26(16) ?
C12 C13 C28 . . 119.45(17) ?
C32 C14 C15 . . 120.9(2) ?
C16 C15 C14 . . 120.5(2) ?
C17 C16 C15 . . 119.9(2) ?
C16 C17 C18 . . 119.3(2) ?
C32 C18 C17 . . 122.5(2) ?
C20 C19 C24 . . 120.99(17) ?
C20 C19 N3 . . 120.77(15) ?
C24 C19 N3 . . 118.18(17) ?
C19 C20 C21 . . 120.14(16) ?
C22 C21 C20 . . 118.99(19) ?
O1 C22 C23 . . 115.87(19) ?
O1 C22 C21 . . 123.7(2) ?
C23 C22 C21 . . 120.39(17) ?
C22 C23 C24 . . 120.64(19) ?
C19 C24 C23 . . 118.8(2) ?
C26 C25 C12 . . 117.9(2) ?
C25 C26 C27 . . 119.95(19) ?
C28 C27 F1 . . 118.5(2) ?
C28 C27 C26 . . 125.09(18) ?
F1 C27 C26 . . 116.37(18) ?
C27 C28 C13 . . 116.21(18) ?
N3 C30 C13 . . 103.33(14) ?
N3 C30 Si1 . . 130.16(13) ?
C13 C30 Si1 . . 126.12(12) ?
C11 C31 C7 . . 117.41(19) ?
C11 C31 Si1 . . 122.29(16) ?
C7 C31 Si1 . . 120.27(15) ?
C14 C32 C18 . . 116.86(18) ?
C14 C32 Si1 . . 124.22(15) ?
C18 C32 Si1 . . 118.90(15) ?

