# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_4Ao
_database_code_depnum_ccdc_archive 'CCDC 2430995'
loop_
_audit_author_name
_audit_author_address
'Rishukumar Panday'
;Indian Institute of Science Education and Research, Pune
India
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_audit_creation_date             2025-03-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 F3 N3 O2, C3 H6 O'
_chemical_formula_sum            'C18 H18 F3 N3 O3'
_chemical_formula_weight         381.35
_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'
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'

_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                   14.564(5)
_cell_length_b                   11.352(4)
_cell_length_c                   11.354(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.202(9)
_cell_angle_gamma                90
_cell_volume                     1866.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3777
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0903 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.9236.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.185
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24235
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.166
_diffrn_reflns_theta_max         25.166
_diffrn_reflns_theta_min         1.406
_diffrn_ambient_temperature      150(2)
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           19.0
_diffrn_source_power             0.76
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2463
_reflns_number_total             3327
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.700
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+2.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 F1-C15 \\sim F1'-C15
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1') \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Others
 Sof(F1')=1-FVAR(1)
 Sof(F1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
4.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C11(H11), C10(H10)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.34478(11) 0.33324(14) 0.37624(14) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.41562(16) 0.3894(2) 0.78701(19) 0.0258(5) Uani 1 1 d . . . . .
O1 O 0.44859(11) 0.54235(14) 0.67713(15) 0.0245(4) Uani 1 1 d . . . . .
O3 O 0.59872(13) 0.41262(16) 0.93078(18) 0.0372(5) Uani 1 1 d . . . . .
N3 N 0.20308(13) 0.41972(17) 0.32757(18) 0.0224(5) Uani 1 1 d . . . . .
H3 H 0.1849 0.3792 0.2632 0.027 Uiso 1 1 calc R U . . .
N2 N 0.19923(13) 0.27111(19) 0.65754(19) 0.0272(5) Uani 1 1 d . . . . .
F3 F 0.00316(17) 0.3822(2) 0.2308(2) 0.0809(7) Uani 1 1 d . . . . .
F2 F 0.05590(16) 0.5125(3) 0.13111(18) 0.0917(9) Uani 1 1 d . . . . .
C1 C 0.38932(16) 0.4536(2) 0.6908(2) 0.0203(5) Uani 1 1 d . . . . .
C14 C 0.28570(15) 0.4051(2) 0.3939(2) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.25016(16) 0.3451(2) 0.6390(2) 0.0204(5) Uani 1 1 d . . . . .
F1 F -0.0765(4) 0.5269(17) 0.2115(15) 0.072(4) Uani 0.67(4) 1 d D U P A 1
C2 C 0.31150(15) 0.4352(2) 0.6137(2) 0.0194(5) Uani 1 1 d . . . . .
C3 C 0.29317(15) 0.4969(2) 0.4949(2) 0.0193(5) Uani 1 1 d . . . . .
C8 C 0.19966(16) 0.5559(2) 0.4754(2) 0.0217(5) Uani 1 1 d . . . . .
C13 C 0.15055(16) 0.5082(2) 0.3753(2) 0.0232(5) Uani 1 1 d . . . . .
C4 C 0.37725(16) 0.5762(2) 0.4759(2) 0.0224(5) Uani 1 1 d . . . . .
H4 H 0.4265 0.5233 0.4510 0.027 Uiso 1 1 calc R U . . .
C17 C 0.64052(18) 0.5045(2) 0.9487(2) 0.0264(6) Uani 1 1 d . . . . .
C12 C 0.06232(17) 0.5472(2) 0.3341(2) 0.0286(6) Uani 1 1 d . . . . .
C5 C 0.41499(17) 0.6315(2) 0.5922(2) 0.0247(6) Uani 1 1 d . . . . .
H5A H 0.4660 0.6858 0.5788 0.030 Uiso 1 1 calc R U . . .
H5B H 0.3658 0.6778 0.6243 0.030 Uiso 1 1 calc R U . . .
C18 C 0.59599(18) 0.6189(2) 0.9127(2) 0.0283(6) Uani 1 1 d . . . . .
H18A H 0.6120 0.6409 0.8340 0.042 Uiso 1 1 calc R U . . .
H18B H 0.6178 0.6799 0.9701 0.042 Uiso 1 1 calc R U . . .
H18C H 0.5288 0.6111 0.9103 0.042 Uiso 1 1 calc R U . . .
C9 C 0.16029(18) 0.6417(2) 0.5394(2) 0.0292(6) Uani 1 1 d . . . . .
H9 H 0.1929 0.6733 0.6093 0.035 Uiso 1 1 calc R U . . .
C11 C 0.02394(18) 0.6357(2) 0.3992(3) 0.0328(6) Uani 1 1 d . . . . .
H11 H -0.0361 0.6645 0.3736 0.039 Uiso 1 1 calc R U . . .
C7 C 0.35697(19) 0.6679(2) 0.3784(2) 0.0311(6) Uani 1 1 d . . . . .
H7A H 0.3283 0.6295 0.3064 0.047 Uiso 1 1 calc R U . . .
H7B H 0.4148 0.7056 0.3620 0.047 Uiso 1 1 calc R U . . .
H7C H 0.3148 0.7276 0.4042 0.047 Uiso 1 1 calc R U . . .
C10 C 0.07191(19) 0.6813(2) 0.4998(3) 0.0350(7) Uani 1 1 d . . . . .
H10 H 0.0443 0.7409 0.5430 0.042 Uiso 1 1 calc R U . . .
C15 C 0.01153(19) 0.4978(3) 0.2257(3) 0.0388(7) Uani 1 1 d D . . . .
C16 C 0.73798(19) 0.5061(3) 1.0051(3) 0.0421(7) Uani 1 1 d . . . . .
H16A H 0.7395 0.5350 1.0867 0.063 Uiso 1 1 calc R U . . .
H16B H 0.7749 0.5583 0.9601 0.063 Uiso 1 1 calc R U . . .
H16C H 0.7635 0.4262 1.0057 0.063 Uiso 1 1 calc R U . . .
H1A H 0.386(2) 0.323(3) 0.800(3) 0.040(8) Uiso 1 1 d . . . . .
H1B H 0.467(2) 0.406(3) 0.833(3) 0.039(8) Uiso 1 1 d . . . . .
F1' F -0.055(2) 0.570(2) 0.173(2) 0.068(5) Uani 0.33(4) 1 d D U P A 2


_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
O2 C14 1.218(3) . ?
N1 C1 1.334(3) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.88(3) . ?
O1 C1 1.347(3) . ?
O1 C5 1.446(3) . ?
O3 C17 1.213(3) . ?
N3 H3 0.8800 . ?
N3 C14 1.359(3) . ?
N3 C13 1.406(3) . ?
N2 C6 1.155(3) . ?
F3 C15 1.320(4) . ?
F2 C15 1.322(4) . ?
C1 C2 1.371(3) . ?
C14 C3 1.545(3) . ?
C6 C2 1.408(3) . ?
F1 C15 1.317(5) . ?
C2 C3 1.518(3) . ?
C3 C8 1.512(3) . ?
C3 C4 1.553(3) . ?
C8 C13 1.386(3) . ?
C8 C9 1.377(3) . ?
C13 C12 1.392(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.511(3) . ?
C4 C7 1.526(3) . ?
C17 C18 1.489(4) . ?
C17 C16 1.493(4) . ?
C12 C11 1.399(4) . ?
C12 C15 1.477(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.374(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10 0.9500 . ?
C15 F1' 1.353(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C1 N1 H1A 119.6(19) . . ?
C1 N1 H1B 121.1(19) . . ?
H1A N1 H1B 119(3) . . ?
C1 O1 C5 115.18(18) . . ?
C14 N3 H3 124.5 . . ?
C14 N3 C13 111.1(2) . . ?
C13 N3 H3 124.5 . . ?
N1 C1 O1 111.9(2) . . ?
N1 C1 C2 125.7(2) . . ?
O1 C1 C2 122.4(2) . . ?
O2 C14 N3 126.2(2) . . ?
O2 C14 C3 125.4(2) . . ?
N3 C14 C3 108.42(19) . . ?
N2 C6 C2 178.7(3) . . ?
C1 C2 C6 118.6(2) . . ?
C1 C2 C3 123.5(2) . . ?
C6 C2 C3 117.5(2) . . ?
C14 C3 C4 106.34(18) . . ?
C2 C3 C14 109.89(19) . . ?
C2 C3 C4 108.96(19) . . ?
C8 C3 C14 101.55(18) . . ?
C8 C3 C2 113.78(19) . . ?
C8 C3 C4 115.74(19) . . ?
C13 C8 C3 108.9(2) . . ?
C9 C8 C3 131.0(2) . . ?
C9 C8 C13 120.1(2) . . ?
C8 C13 N3 110.0(2) . . ?
C8 C13 C12 121.8(2) . . ?
C12 C13 N3 128.2(2) . . ?
C3 C4 H4 107.0 . . ?
C5 C4 C3 109.72(19) . . ?
C5 C4 H4 107.0 . . ?
C5 C4 C7 112.0(2) . . ?
C7 C4 C3 113.7(2) . . ?
C7 C4 H4 107.0 . . ?
O3 C17 C18 120.5(2) . . ?
O3 C17 C16 121.3(2) . . ?
C18 C17 C16 118.2(2) . . ?
C13 C12 C11 117.2(2) . . ?
C13 C12 C15 121.4(2) . . ?
C11 C12 C15 121.4(2) . . ?
O1 C5 C4 110.93(19) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
F3 C15 F2 102.5(3) . . ?
F3 C15 C12 112.5(3) . . ?
F3 C15 F1' 123.6(13) . . ?
F2 C15 C12 112.6(3) . . ?
F2 C15 F1' 87.4(16) . . ?
F1 C15 F3 99.3(9) . . ?
F1 C15 F2 115.1(10) . . ?
F1 C15 C12 113.6(4) . . ?
F1' C15 C12 114.1(6) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O2 C14 C3 C2 -56.8(3) . . . . ?
O2 C14 C3 C8 -177.6(2) . . . . ?
O2 C14 C3 C4 61.0(3) . . . . ?
N1 C1 C2 C6 3.4(4) . . . . ?
N1 C1 C2 C3 -169.0(2) . . . . ?
O1 C1 C2 C6 -175.9(2) . . . . ?
O1 C1 C2 C3 11.7(3) . . . . ?
N3 C14 C3 C2 124.2(2) . . . . ?
N3 C14 C3 C8 3.4(2) . . . . ?
N3 C14 C3 C4 -118.0(2) . . . . ?
N3 C13 C12 C11 178.8(2) . . . . ?
N3 C13 C12 C15 -1.5(4) . . . . ?
C1 O1 C5 C4 -50.4(3) . . . . ?
C1 C2 C3 C14 118.6(2) . . . . ?
C1 C2 C3 C8 -128.3(2) . . . . ?
C1 C2 C3 C4 2.5(3) . . . . ?
C14 N3 C13 C8 1.0(3) . . . . ?
C14 N3 C13 C12 -178.9(2) . . . . ?
C14 C3 C8 C13 -2.8(2) . . . . ?
C14 C3 C8 C9 176.2(3) . . . . ?
C14 C3 C4 C5 -155.80(19) . . . . ?
C14 C3 C4 C7 77.9(2) . . . . ?
C6 C2 C3 C14 -53.9(3) . . . . ?
C6 C2 C3 C8 59.2(3) . . . . ?
C6 C2 C3 C4 -170.0(2) . . . . ?
C2 C3 C8 C13 -120.8(2) . . . . ?
C2 C3 C8 C9 58.2(3) . . . . ?
C2 C3 C4 C5 -37.4(3) . . . . ?
C2 C3 C4 C7 -163.7(2) . . . . ?
C3 C8 C13 N3 1.3(3) . . . . ?
C3 C8 C13 C12 -178.7(2) . . . . ?
C3 C8 C9 C10 179.3(2) . . . . ?
C3 C4 C5 O1 62.7(2) . . . . ?
C8 C3 C4 C5 92.3(2) . . . . ?
C8 C3 C4 C7 -34.0(3) . . . . ?
C8 C13 C12 C11 -1.2(4) . . . . ?
C8 C13 C12 C15 178.5(2) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C13 N3 C14 O2 178.1(2) . . . . ?
C13 N3 C14 C3 -2.9(3) . . . . ?
C13 C8 C9 C10 -1.7(4) . . . . ?
C13 C12 C11 C10 -0.1(4) . . . . ?
C13 C12 C15 F3 55.8(4) . . . . ?
C13 C12 C15 F2 -59.5(4) . . . . ?
C13 C12 C15 F1 167.5(12) . . . . ?
C13 C12 C15 F1' -157(2) . . . . ?
C4 C3 C8 C13 111.8(2) . . . . ?
C4 C3 C8 C9 -69.1(3) . . . . ?
C12 C11 C10 C9 0.5(4) . . . . ?
C5 O1 C1 N1 -166.4(2) . . . . ?
C5 O1 C1 C2 13.0(3) . . . . ?
C9 C8 C13 N3 -177.8(2) . . . . ?
C9 C8 C13 C12 2.2(4) . . . . ?
C11 C12 C15 F3 -124.5(3) . . . . ?
C11 C12 C15 F2 120.2(3) . . . . ?
C11 C12 C15 F1 -12.8(13) . . . . ?
C11 C12 C15 F1' 23(2) . . . . ?
C7 C4 C5 O1 -170.0(2) . . . . ?
C15 C12 C11 C10 -179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4Bb
_database_code_depnum_ccdc_archive 'CCDC 2434923'
loop_
_audit_author_name
_audit_author_address
'Rishukumar Panday'
;Indian Institute of Science Education and Research, Pune
India
;
_audit_update_record             
;
2025-03-28 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_audit_creation_date             2025-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N3 O2'
_chemical_formula_sum            'C16 H17 N3 O2'
_chemical_formula_weight         283.32
_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'
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'

_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                   9.3030(13)
_cell_length_b                   8.9537(13)
_cell_length_c                   17.411(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.146(4)
_cell_angle_gamma                90
_cell_volume                     1439.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1139 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.8080.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.215
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21631
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.030
_diffrn_reflns_theta_max         25.030
_diffrn_reflns_theta_min         2.206
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_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                1832
_reflns_number_total             2546
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    ?
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+1.0106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C4(H4)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C15(H15A,H15B)
1.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C11(H11)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.74314(19) 0.57322(19) 0.71917(9) 0.0216(4) Uani 1 1 d . . . . .
O1 O 0.79847(19) 1.06137(19) 0.72386(10) 0.0233(5) Uani 1 1 d . . . . .
N3 N 0.7704(2) 0.5348(2) 0.59164(12) 0.0216(5) Uani 1 1 d . . . . .
N1 N 0.5648(3) 1.0731(3) 0.73615(14) 0.0291(6) Uani 1 1 d . . . . .
N2 N 0.3885(3) 0.7850(2) 0.61621(13) 0.0273(6) Uani 1 1 d . . . . .
C6 C 0.5039(3) 0.8291(3) 0.63419(13) 0.0160(6) Uani 1 1 d . . . . .
C8 C 0.7697(3) 0.7740(3) 0.54488(13) 0.0145(6) Uani 1 1 d . . . . .
C3 C 0.7697(3) 0.7864(3) 0.63148(13) 0.0134(6) Uani 1 1 d . . . . .
C14 C 0.7572(3) 0.6207(3) 0.65455(14) 0.0159(6) Uani 1 1 d . . . . .
C2 C 0.6471(3) 0.8785(3) 0.65626(13) 0.0139(6) Uani 1 1 d . . . . .
C1 C 0.6675(3) 1.0001(3) 0.70373(13) 0.0181(6) Uani 1 1 d . . . . .
C5 C 0.9109(3) 1.0112(3) 0.67982(15) 0.0204(6) Uani 1 1 d . . . . .
H5A H 1.0059 1.0482 0.7045 0.024 Uiso 1 1 calc R U . . .
H5B H 0.8936 1.0532 0.6269 0.024 Uiso 1 1 calc R U . . .
C4 C 0.9146(3) 0.8430(3) 0.67519(14) 0.0163(6) Uani 1 1 d . . . . .
H4 H 0.9215 0.8039 0.7293 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7650(3) 0.8815(3) 0.48791(14) 0.0195(6) Uani 1 1 d . . . . .
H9 H 0.7590 0.9843 0.5005 0.023 Uiso 1 1 calc R U . . .
C13 C 0.7741(3) 0.6242(3) 0.52483(14) 0.0199(6) Uani 1 1 d . . . . .
C10 C 0.7693(3) 0.8368(3) 0.41148(14) 0.0266(7) Uani 1 1 d . . . . .
H10 H 0.7673 0.9097 0.3717 0.032 Uiso 1 1 calc R U . . .
C7 C 1.0485(3) 0.7909(3) 0.64145(15) 0.0231(6) Uani 1 1 d . . . . .
H7A H 1.0471 0.6818 0.6371 0.035 Uiso 1 1 calc R U . . .
H7B H 1.1353 0.8221 0.6754 0.035 Uiso 1 1 calc R U . . .
H7C H 1.0498 0.8351 0.5900 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7779(3) 0.5771(3) 0.44955(15) 0.0321(7) Uani 1 1 d . . . . .
H12 H 0.7814 0.4741 0.4368 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7623(3) 0.3716(3) 0.59237(17) 0.0331(7) Uani 1 1 d . . . . .
H15A H 0.8038 0.3342 0.6439 0.040 Uiso 1 1 calc R U . . .
H15B H 0.8208 0.3306 0.5535 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7764(3) 0.6874(3) 0.39342(15) 0.0350(8) Uani 1 1 d . . . . .
H11 H 0.7804 0.6591 0.3411 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6100(4) 0.3180(3) 0.57484(18) 0.0441(9) Uani 1 1 d . . . . .
H16A H 0.5679 0.3566 0.5243 0.066 Uiso 1 1 calc R U . . .
H16B H 0.5531 0.3535 0.6149 0.066 Uiso 1 1 calc R U . . .
H16C H 0.6089 0.2085 0.5737 0.066 Uiso 1 1 calc R U . . .
H1A H 0.478(4) 1.037(3) 0.7343(16) 0.034(9) Uiso 1 1 d . . . . .
H1B H 0.595(3) 1.150(4) 0.7680(18) 0.039(9) Uiso 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
O2 C14 1.225(3) . ?
O1 C1 1.342(3) . ?
O1 C5 1.443(3) . ?
N3 C14 1.356(3) . ?
N3 C13 1.416(3) . ?
N3 C15 1.463(3) . ?
N1 C1 1.339(3) . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.90(3) . ?
N2 C6 1.150(3) . ?
C6 C2 1.411(4) . ?
C8 C3 1.512(3) . ?
C8 C9 1.379(3) . ?
C8 C13 1.388(3) . ?
C3 C14 1.546(3) . ?
C3 C2 1.514(3) . ?
C3 C4 1.548(3) . ?
C2 C1 1.366(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.508(3) . ?
C4 H4 1.0000 . ?
C4 C7 1.515(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(3) . ?
C13 C12 1.382(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.389(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.491(4) . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C1 O1 C5 115.35(18) . . ?
C14 N3 C13 110.9(2) . . ?
C14 N3 C15 123.3(2) . . ?
C13 N3 C15 125.3(2) . . ?
C1 N1 H1A 121(2) . . ?
C1 N1 H1B 117(2) . . ?
H1A N1 H1B 121(3) . . ?
N2 C6 C2 178.1(3) . . ?
C9 C8 C3 131.5(2) . . ?
C9 C8 C13 119.5(2) . . ?
C13 C8 C3 109.0(2) . . ?
C8 C3 C14 101.41(18) . . ?
C8 C3 C2 114.71(19) . . ?
C8 C3 C4 113.97(19) . . ?
C14 C3 C4 105.99(19) . . ?
C2 C3 C14 111.42(19) . . ?
C2 C3 C4 108.83(19) . . ?
O2 C14 N3 125.2(2) . . ?
O2 C14 C3 126.3(2) . . ?
N3 C14 C3 108.49(19) . . ?
C6 C2 C3 118.1(2) . . ?
C1 C2 C6 118.0(2) . . ?
C1 C2 C3 123.6(2) . . ?
O1 C1 C2 122.5(2) . . ?
N1 C1 O1 111.3(2) . . ?
N1 C1 C2 126.2(3) . . ?
O1 C5 H5A 109.4 . . ?
O1 C5 H5B 109.4 . . ?
O1 C5 C4 111.2(2) . . ?
H5A C5 H5B 108.0 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C3 C4 H4 107.4 . . ?
C5 C4 C3 109.2(2) . . ?
C5 C4 H4 107.4 . . ?
C5 C4 C7 110.7(2) . . ?
C7 C4 C3 114.6(2) . . ?
C7 C4 H4 107.4 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C13 N3 109.6(2) . . ?
C12 C13 N3 127.8(2) . . ?
C12 C13 C8 122.6(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C12 H12 121.6 . . ?
C13 C12 C11 116.8(3) . . ?
C11 C12 H12 121.6 . . ?
N3 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
N3 C15 C16 111.6(3) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C5 C4 C3 63.0(3) . . . . ?
O1 C5 C4 C7 -170.0(2) . . . . ?
N3 C13 C12 C11 178.0(3) . . . . ?
C6 C2 C1 O1 -175.6(2) . . . . ?
C6 C2 C1 N1 4.6(4) . . . . ?
C8 C3 C14 O2 -174.7(2) . . . . ?
C8 C3 C14 N3 7.7(2) . . . . ?
C8 C3 C2 C6 62.1(3) . . . . ?
C8 C3 C2 C1 -123.1(2) . . . . ?
C8 C3 C4 C5 89.7(2) . . . . ?
C8 C3 C4 C7 -35.0(3) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C8 C13 C12 C11 -0.3(4) . . . . ?
C3 C8 C9 C10 178.8(2) . . . . ?
C3 C8 C13 N3 2.6(3) . . . . ?
C3 C8 C13 C12 -178.8(2) . . . . ?
C3 C2 C1 O1 9.7(4) . . . . ?
C3 C2 C1 N1 -170.1(2) . . . . ?
C14 N3 C13 C8 2.7(3) . . . . ?
C14 N3 C13 C12 -175.8(3) . . . . ?
C14 N3 C15 C16 87.5(3) . . . . ?
C14 C3 C2 C6 -52.4(3) . . . . ?
C14 C3 C2 C1 122.4(2) . . . . ?
C14 C3 C4 C5 -159.60(19) . . . . ?
C14 C3 C4 C7 75.6(2) . . . . ?
C2 C3 C14 O2 -52.2(3) . . . . ?
C2 C3 C14 N3 130.2(2) . . . . ?
C2 C3 C4 C5 -39.7(3) . . . . ?
C2 C3 C4 C7 -164.5(2) . . . . ?
C1 O1 C5 C4 -49.2(3) . . . . ?
C5 O1 C1 N1 -167.7(2) . . . . ?
C5 O1 C1 C2 12.5(3) . . . . ?
C4 C3 C14 O2 66.0(3) . . . . ?
C4 C3 C14 N3 -111.5(2) . . . . ?
C4 C3 C2 C6 -168.9(2) . . . . ?
C4 C3 C2 C1 5.9(3) . . . . ?
C9 C8 C3 C14 173.2(3) . . . . ?
C9 C8 C3 C2 53.0(4) . . . . ?
C9 C8 C3 C4 -73.4(3) . . . . ?
C9 C8 C13 N3 -176.8(2) . . . . ?
C9 C8 C13 C12 1.8(4) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C13 N3 C14 O2 175.7(2) . . . . ?
C13 N3 C14 C3 -6.7(3) . . . . ?
C13 N3 C15 C16 -84.0(3) . . . . ?
C13 C8 C3 C14 -6.1(2) . . . . ?
C13 C8 C3 C2 -126.3(2) . . . . ?
C13 C8 C3 C4 107.3(2) . . . . ?
C13 C8 C9 C10 -2.0(4) . . . . ?
C13 C12 C11 C10 -1.0(4) . . . . ?
C15 N3 C14 O2 3.1(4) . . . . ?
C15 N3 C14 C3 -179.3(2) . . . . ?
C15 N3 C13 C8 175.1(2) . . . . ?
C15 N3 C13 C12 -3.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
