# 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_23novb_a
_database_code_depnum_ccdc_archive 'CCDC 2322591'
loop_
_audit_author_name
_audit_author_address
'SHIVANI ARORA'
;INDIAN INSTITUTE OF TECHNOLOGY KANPUR
India
;
_audit_update_record             
;
2023-12-29 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.182(C12 H12 F3 N)'
_chemical_formula_sum            'C2.18 H2.18 F0.55 N0.18'
_chemical_formula_weight         41.31
_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'

_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                   9.4607(3)
_cell_length_b                   11.8094(4)
_cell_length_c                   10.5546(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.8790(10)
_cell_angle_gamma                90
_cell_volume                     1078.28(6)
_cell_formula_units_Z            22
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1398 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8808.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       square
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.705
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17338
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.705
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.193
_diffrn_reflns_theta_min         2.354
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.705
_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           1.0
_diffrn_source_power             0.05
_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                2496
_reflns_number_total             2683
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.075
_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)+(0.0777P)²+0.5907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1455
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00F), C00C(H00G), C00F(H00K), C00G(H00L)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00E(H00H,H00I,H00J)
;
_atom_sites_solution_hydrogens   mixed
_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
F3 F 0.87600(11) 0.18683(8) 0.71301(13) 0.0434(3) Uani 1 1 d . . . . .
F2 F 0.94944(10) 0.29766(10) 0.90909(11) 0.0379(3) Uani 1 1 d . . . . .
F1 F 1.06314(10) 0.28179(10) 0.76609(13) 0.0454(3) Uani 1 1 d . . . . .
N004 N 0.59756(12) 0.34288(10) 0.56703(13) 0.0205(3) Uani 1 1 d . . . . .
C005 C 0.53747(15) 0.45672(11) 0.72167(15) 0.0214(3) Uani 1 1 d . . . . .
C006 C 0.71465(14) 0.40051(11) 0.66536(15) 0.0201(3) Uani 1 1 d . . . . .
C007 C 0.48765(14) 0.37629(11) 0.60079(14) 0.0198(3) Uani 1 1 d . . . . .
C008 C 0.68176(14) 0.47077(11) 0.76100(15) 0.0211(3) Uani 1 1 d . . . . .
C009 C 0.58886(16) 0.26124(12) 0.44802(16) 0.0249(3) Uani 1 1 d . . . . .
H00A H 0.659168 0.286480 0.409068 0.037 Uiso 1 1 calc R U . . .
H00B H 0.485514 0.260881 0.377396 0.037 Uiso 1 1 calc R U . . .
H00C H 0.616557 0.186100 0.484308 0.037 Uiso 1 1 calc R U . . .
C00A C 0.85377(15) 0.38421(13) 0.66183(17) 0.0259(3) Uani 1 1 d . . . . .
C00B C 0.34967(15) 0.34038(13) 0.53745(17) 0.0277(3) Uani 1 1 d . . . . .
H00F H 0.315285 0.291304 0.462089 0.033 Uiso 1 1 calc R U . . .
C00C C 0.44569(18) 0.50209(13) 0.78006(18) 0.0296(3) Uani 1 1 d . . . . .
H00G H 0.478490 0.552274 0.854316 0.036 Uiso 1 1 calc R U . . .
C00D C 0.93473(15) 0.28788(13) 0.76216(17) 0.0283(3) Uani 1 1 d . . . . .
C00E C 0.77732(18) 0.54761(13) 0.88276(19) 0.0335(4) Uani 1 1 d . . . . .
H00H H 0.727264 0.619835 0.872296 0.050 Uiso 1 1 calc R U . . .
H00I H 0.878620 0.557793 0.884178 0.050 Uiso 1 1 calc R U . . .
H00J H 0.785886 0.513303 0.968029 0.050 Uiso 1 1 calc R U . . .
C00F C 0.26216(17) 0.38563(15) 0.5983(2) 0.0366(4) Uani 1 1 d . . . . .
H00K H 0.158695 0.364244 0.560795 0.044 Uiso 1 1 calc R U . . .
C00G C 0.30922(19) 0.46565(15) 0.7181(2) 0.0380(4) Uani 1 1 d . . . . .
H00L H 0.234573 0.489754 0.748364 0.046 Uiso 1 1 calc R U . . .
H00D H 0.908(2) 0.4501(17) 0.700(2) 0.028(5) Uiso 1 1 d . . . . .
H00E H 0.849(2) 0.3688(17) 0.562(2) 0.029(5) 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
F3 C00D 1.3298(18) . ?
F2 C00D 1.504(2) . ?
F1 C00D 1.2008(15) . ?
N004 C006 1.3552(16) . ?
N004 C007 1.2899(16) . ?
N004 C009 1.5590(18) . ?
C005 C007 1.505(2) . ?
C005 C008 1.2667(17) . ?
C005 C00C 1.3616(19) . ?
C006 C007 1.9933(16) . ?
C006 C008 1.4347(19) . ?
C006 C00A 1.3455(17) . ?
C007 C00B 1.2745(18) . ?
C008 C00E 1.534(2) . ?
C009 H00A 0.9600 . ?
C009 H00B 0.9600 . ?
C009 H00C 0.9600 . ?
C00A C00D 1.532(2) . ?
C00A H00D 0.93(2) . ?
C00A H00E 1.06(2) . ?
C00B H00F 0.9300 . ?
C00B C00F 1.347(2) . ?
C00C H00G 0.9300 . ?
C00C C00G 1.263(2) . ?
C00E H00H 0.9600 . ?
C00E H00I 0.9600 . ?
C00E H00J 0.9600 . ?
C00F H00K 0.9300 . ?
C00F C00G 1.494(3) . ?
C00G H00L 0.9300 . ?

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
C006 N004 C009 133.45(11) . . ?
C007 N004 C006 97.77(11) . . ?
C007 N004 C009 128.77(11) . . ?
C008 C005 C007 106.65(12) . . ?
C008 C005 C00C 126.88(15) . . ?
C00C C005 C007 126.43(13) . . ?
N004 C006 C007 39.88(7) . . ?
N004 C006 C008 119.10(11) . . ?
C008 C006 C007 79.22(9) . . ?
C00A C006 N004 114.35(13) . . ?
C00A C006 C007 154.23(13) . . ?
C00A C006 C008 126.54(13) . . ?
N004 C007 C005 114.61(11) . . ?
N004 C007 C006 42.35(7) . . ?
C005 C007 C006 72.26(8) . . ?
C00B C007 N004 121.49(15) . . ?
C00B C007 C005 123.88(13) . . ?
C00B C007 C006 163.75(13) . . ?
C005 C008 C006 101.86(12) . . ?
C005 C008 C00E 122.93(14) . . ?
C006 C008 C00E 135.20(12) . . ?
N004 C009 H00A 109.5 . . ?
N004 C009 H00B 109.5 . . ?
N004 C009 H00C 109.5 . . ?
H00A C009 H00B 109.5 . . ?
H00A C009 H00C 109.5 . . ?
H00B C009 H00C 109.5 . . ?
C006 C00A C00D 107.95(12) . . ?
C006 C00A H00D 104.3(12) . . ?
C006 C00A H00E 113.9(10) . . ?
C00D C00A H00D 106.8(12) . . ?
C00D C00A H00E 111.8(11) . . ?
H00D C00A H00E 111.6(16) . . ?
C007 C00B H00F 125.8 . . ?
C007 C00B C00F 108.34(16) . . ?
C00F C00B H00F 125.8 . . ?
C005 C00C H00G 125.2 . . ?
C00G C00C C005 109.68(16) . . ?
C00G C00C H00G 125.2 . . ?
F3 C00D F2 108.71(12) . . ?
F3 C00D C00A 112.57(13) . . ?
F2 C00D C00A 117.87(13) . . ?
F1 C00D F3 102.52(13) . . ?
F1 C00D F2 107.39(13) . . ?
F1 C00D C00A 106.51(13) . . ?
C008 C00E H00H 109.5 . . ?
C008 C00E H00I 109.5 . . ?
C008 C00E H00J 109.5 . . ?
H00H C00E H00I 109.5 . . ?
H00H C00E H00J 109.5 . . ?
H00I C00E H00J 109.5 . . ?
C00B C00F H00K 115.7 . . ?
C00B C00F C00G 128.61(14) . . ?
C00G C00F H00K 115.7 . . ?
C00C C00G C00F 123.06(14) . . ?
C00C C00G H00L 118.5 . . ?
C00F C00G H00L 118.5 . . ?

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
N004 C006 C008 C005 0.19(17) . . . . ?
N004 C006 C008 C00E -179.66(15) . . . . ?
N004 C006 C00A C00D -93.60(16) . . . . ?
N004 C007 C00B C00F 177.45(14) . . . . ?
C005 C007 C00B C00F -0.6(2) . . . . ?
C005 C00C C00G C00F -0.5(2) . . . . ?
C006 N004 C007 C005 0.40(15) . . . . ?
C006 N004 C007 C00B -177.84(14) . . . . ?
C006 C007 C00B C00F 172.2(4) . . . . ?
C006 C00A C00D F3 74.28(17) . . . . ?
C006 C00A C00D F2 -53.50(17) . . . . ?
C006 C00A C00D F1 -174.12(14) . . . . ?
C007 N004 C006 C008 -0.37(16) . . . . ?
C007 N004 C006 C00A 179.47(13) . . . . ?
C007 C005 C008 C006 0.08(14) . . . . ?
C007 C005 C008 C00E 179.95(13) . . . . ?
C007 C005 C00C C00G 0.6(2) . . . . ?
C007 C006 C008 C005 -0.06(10) . . . . ?
C007 C006 C008 C00E -179.91(17) . . . . ?
C007 C006 C00A C00D -92.8(3) . . . . ?
C007 C00B C00F C00G 0.8(2) . . . . ?
C008 C005 C007 N004 -0.34(17) . . . . ?
C008 C005 C007 C006 -0.06(11) . . . . ?
C008 C005 C007 C00B 177.85(14) . . . . ?
C008 C005 C00C C00G -176.83(15) . . . . ?
C008 C006 C00A C00D 86.23(17) . . . . ?
C009 N004 C006 C007 179.9(2) . . . . ?
C009 N004 C006 C008 179.54(13) . . . . ?
C009 N004 C006 C00A -0.6(2) . . . . ?
C009 N004 C007 C005 -179.52(12) . . . . ?
C009 N004 C007 C006 -179.92(19) . . . . ?
C009 N004 C007 C00B 2.2(2) . . . . ?
C00A C006 C008 C005 -179.64(15) . . . . ?
C00A C006 C008 C00E 0.5(3) . . . . ?
C00B C00F C00G C00C -0.2(3) . . . . ?
C00C C005 C007 N004 -178.22(14) . . . . ?
C00C C005 C007 C006 -177.94(15) . . . . ?
C00C C005 C007 C00B 0.0(2) . . . . ?
C00C C005 C008 C006 177.95(14) . . . . ?
C00C C005 C008 C00E -2.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
