# Supplementary Information (SI) for RSC Advances.
# 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_bmp_0m
_database_code_depnum_ccdc_archive 'CCDC 1897523'
loop_
_audit_author_name
_audit_author_address
'Dr. Krishna Murthy Polta'
;VRSEC
India
;
_audit_update_record             
;
2024-07-02 deposited with the CCDC.	2024-10-24 downloaded from the CCDC.
;
_audit_creation_date             2024-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H22 F N3 O3 S'
_chemical_formula_sum            'C17 H22 F N3 O3 S'
_chemical_formula_weight         367.44
_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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y+1/2, -z'
3 '-x, y+1/2, -z+1/2'
4 '-x+1/2, -y, z+1/2'
5 '-x, -y, -z'
6 '-x-1/2, y-1/2, z'
7 'x, -y-1/2, z-1/2'
8 'x-1/2, y, -z-1/2'

_cell_length_a                   7.7519(10)
_cell_length_b                   17.548(2)
_cell_length_c                   26.884(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3657.0(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16693
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                2345
_reflns_number_total             4175
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.021
_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)+(0.0764P)²+0.7243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1673
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4790(3) 0.34926(13) 0.10114(9) 0.0415(6) Uani 1 1 d . . .
C2 C 0.3781(3) 0.23332(13) 0.12463(9) 0.0413(6) Uani 1 1 d . . .
C3 C 0.3627(3) 0.21244(13) 0.07429(9) 0.0377(5) Uani 1 1 d . . .
C4 C 0.4132(3) 0.26693(13) 0.03911(8) 0.0371(5) Uani 1 1 d . . .
C5 C 0.4054(3) 0.25576(13) -0.01570(8) 0.0382(5) Uani 1 1 d . . .
C6 C 0.4659(3) 0.19013(14) -0.03859(9) 0.0467(6) Uani 1 1 d . . .
H6 H 0.5101 0.1509 -0.0192 0.056 Uiso 1 1 calc R . .
C7 C 0.4618(4) 0.18196(16) -0.08979(10) 0.0557(7) Uani 1 1 d . . .
H7 H 0.5041 0.1381 -0.1049 0.067 Uiso 1 1 calc R . .
C8 C 0.3937(4) 0.24010(17) -0.11754(9) 0.0568(7) Uani 1 1 d . . .
C9 C 0.3350(4) 0.30587(16) -0.09663(10) 0.0573(8) Uani 1 1 d . . .
H9 H 0.2914 0.3448 -0.1165 0.069 Uiso 1 1 calc R . .
C10 C 0.3409(3) 0.31393(14) -0.04572(9) 0.0474(6) Uani 1 1 d . . .
H10 H 0.3013 0.3587 -0.0312 0.057 Uiso 1 1 calc R . .
C11 C 0.2883(3) 0.13720(13) 0.05927(9) 0.0435(6) Uani 1 1 d . . .
H11A H 0.2044 0.1208 0.0838 0.052 Uiso 1 1 calc R . .
H11B H 0.2301 0.1422 0.0275 0.052 Uiso 1 1 calc R . .
C12 C 0.3584(4) 0.00719(15) 0.05316(13) 0.0707(9) Uani 1 1 d . . .
H12A H 0.2731 0.0038 0.0273 0.106 Uiso 1 1 calc R . .
H12B H 0.3068 -0.0059 0.0845 0.106 Uiso 1 1 calc R . .
H12C H 0.4511 -0.0274 0.0461 0.106 Uiso 1 1 calc R . .
C13 C 0.3284(4) 0.18132(17) 0.16729(10) 0.0583(8) Uani 1 1 d . . .
H13 H 0.2242 0.1537 0.1573 0.070 Uiso 1 1 calc R . .
C14 C 0.2845(6) 0.2263(2) 0.21456(12) 0.0939(12) Uani 1 1 d . . .
H14A H 0.3874 0.2494 0.2275 0.141 Uiso 1 1 calc R . .
H14B H 0.2368 0.1925 0.2390 0.141 Uiso 1 1 calc R . .
H14C H 0.2019 0.2653 0.2067 0.141 Uiso 1 1 calc R . .
C16 C 0.6305(4) 0.46930(15) 0.07855(11) 0.0648(8) Uani 1 1 d . . .
H16A H 0.6934 0.4372 0.0560 0.097 Uiso 1 1 calc R . .
H16B H 0.7091 0.5028 0.0954 0.097 Uiso 1 1 calc R . .
H16C H 0.5479 0.4989 0.0603 0.097 Uiso 1 1 calc R . .
C15 C 0.4679(5) 0.1226(2) 0.17695(12) 0.0848(11) Uani 1 1 d . . .
H15A H 0.4907 0.0947 0.1469 0.127 Uiso 1 1 calc R . .
H15B H 0.4300 0.0880 0.2024 0.127 Uiso 1 1 calc R . .
H15C H 0.5714 0.1478 0.1877 0.127 Uiso 1 1 calc R . .
C17 C 0.6139(6) 0.4136(2) 0.21358(13) 0.0996(13) Uani 1 1 d . . .
H17A H 0.5814 0.3609 0.2153 0.149 Uiso 1 1 calc R . .
H17B H 0.5976 0.4370 0.2455 0.149 Uiso 1 1 calc R . .
H17C H 0.7330 0.4175 0.2042 0.149 Uiso 1 1 calc R . .
O1 O 0.5391(4) 0.53775(12) 0.16616(8) 0.0954(9) Uani 1 1 d . . .
O2 O 0.3093(3) 0.44364(13) 0.17912(8) 0.0844(7) Uani 1 1 d . . .
O3 O 0.4229(2) 0.08203(9) 0.05545(6) 0.0515(5) Uani 1 1 d . . .
F1 F 0.3851(3) 0.23138(11) -0.16754(6) 0.0903(6) Uani 1 1 d . . .
S1 S 0.48612(12) 0.46013(4) 0.16950(3) 0.0651(3) Uani 1 1 d . . .
N1 N 0.4401(3) 0.30160(11) 0.13776(7) 0.0455(5) Uani 1 1 d . . .
N2 N 0.4692(3) 0.33663(11) 0.05260(7) 0.0410(5) Uani 1 1 d . . .
N3 N 0.5404(3) 0.42192(11) 0.11514(8) 0.0521(6) 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
C1 N1 1.327(3) . ?
C1 N2 1.326(3) . ?
C1 N3 1.412(3) . ?
C2 C3 1.407(3) . ?
C2 C13 1.515(3) . ?
C2 N1 1.338(3) . ?
C3 C4 1.401(3) . ?
C3 C11 1.496(3) . ?
C4 C5 1.488(3) . ?
C4 N2 1.348(3) . ?
C5 C6 1.388(3) . ?
C5 C10 1.394(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(4) . ?
C8 C9 1.362(4) . ?
C8 F1 1.355(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 O3 1.427(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 O3 1.407(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.535(4) . ?
C13 C15 1.517(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 N3 1.465(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 S1 1.747(3) . ?
O1 S1 1.426(2) . ?
O2 S1 1.424(2) . ?
S1 N3 1.662(2) . ?

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
N1 C1 N3 116.6(2) . . ?
N2 C1 N1 127.7(2) . . ?
N2 C1 N3 115.6(2) . . ?
C3 C2 C13 123.3(2) . . ?
N1 C2 C3 121.1(2) . . ?
N1 C2 C13 115.5(2) . . ?
C2 C3 C11 121.5(2) . . ?
C4 C3 C2 116.6(2) . . ?
C4 C3 C11 121.8(2) . . ?
C3 C4 C5 124.6(2) . . ?
N2 C4 C3 121.9(2) . . ?
N2 C4 C5 113.5(2) . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 C10 118.2(2) . . ?
C10 C5 C4 119.4(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.3(3) . . ?
C8 C7 H7 120.9 . . ?
C9 C8 C7 122.4(2) . . ?
F1 C8 C7 118.4(3) . . ?
F1 C8 C9 119.2(3) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C3 C11 H11A 109.7 . . ?
C3 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O3 C11 C3 109.66(19) . . ?
O3 C11 H11A 109.7 . . ?
O3 C11 H11B 109.7 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
C2 C13 H13 107.4 . . ?
C2 C13 C14 111.9(2) . . ?
C2 C13 C15 111.0(2) . . ?
C14 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C15 C13 C14 111.5(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
C12 O3 C11 112.1(2) . . ?
O1 S1 C17 108.99(18) . . ?
O1 S1 N3 104.90(13) . . ?
O2 S1 C17 109.13(19) . . ?
O2 S1 O1 118.87(16) . . ?
O2 S1 N3 108.74(13) . . ?
N3 S1 C17 105.35(16) . . ?
C1 N1 C2 116.8(2) . . ?
C1 N2 C4 115.8(2) . . ?
C1 N3 C16 119.6(2) . . ?
C1 N3 S1 120.90(17) . . ?
C16 N3 S1 118.82(17) . . ?

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
C2 C3 C4 C5 -179.5(2) . . . . ?
C2 C3 C4 N2 -1.8(3) . . . . ?
C2 C3 C11 O3 -90.6(3) . . . . ?
C3 C2 C13 C14 -155.8(3) . . . . ?
C3 C2 C13 C15 79.0(3) . . . . ?
C3 C2 N1 C1 2.8(3) . . . . ?
C3 C4 C5 C6 -46.8(3) . . . . ?
C3 C4 C5 C10 135.5(3) . . . . ?
C3 C4 N2 C1 2.3(3) . . . . ?
C3 C11 O3 C12 165.9(2) . . . . ?
C4 C3 C11 O3 92.4(3) . . . . ?
C4 C5 C6 C7 -178.1(2) . . . . ?
C4 C5 C10 C9 178.8(2) . . . . ?
C5 C4 N2 C1 -179.7(2) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C6 C5 C10 C9 1.0(4) . . . . ?
C6 C7 C8 C9 1.8(4) . . . . ?
C6 C7 C8 F1 -178.2(2) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C5 -0.2(4) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C11 C3 C4 C5 -2.4(4) . . . . ?
C11 C3 C4 N2 175.4(2) . . . . ?
C13 C2 C3 C4 179.7(2) . . . . ?
C13 C2 C3 C11 2.5(4) . . . . ?
C13 C2 N1 C1 -177.7(2) . . . . ?
C17 S1 N3 C1 77.0(3) . . . . ?
C17 S1 N3 C16 -112.4(3) . . . . ?
O1 S1 N3 C1 -168.0(2) . . . . ?
O1 S1 N3 C16 2.5(3) . . . . ?
O2 S1 N3 C1 -39.8(2) . . . . ?
O2 S1 N3 C16 130.7(2) . . . . ?
F1 C8 C9 C10 178.8(2) . . . . ?
N1 C1 N2 C4 -0.1(4) . . . . ?
N1 C1 N3 C16 162.9(2) . . . . ?
N1 C1 N3 S1 -26.6(3) . . . . ?
N1 C2 C3 C4 -0.9(3) . . . . ?
N1 C2 C3 C11 -178.0(2) . . . . ?
N1 C2 C13 C14 24.8(4) . . . . ?
N1 C2 C13 C15 -100.5(3) . . . . ?
N2 C1 N1 C2 -2.4(4) . . . . ?
N2 C1 N3 C16 -16.3(3) . . . . ?
N2 C1 N3 S1 154.14(18) . . . . ?
N2 C4 C5 C6 135.3(2) . . . . ?
N2 C4 C5 C10 -42.4(3) . . . . ?
N3 C1 N1 C2 178.5(2) . . . . ?
N3 C1 N2 C4 179.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
