# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 2091413'
loop_
_audit_author_name
_audit_author_address
'Dr. Ruchir Kant'
;CSIR CDRI, Lucknow
India
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 F3 N O2'
_chemical_formula_weight         333.30

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   9.1642(8)
_cell_length_b                   8.5725(7)
_cell_length_c                   19.4137(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.682(3)
_cell_angle_gamma                90
_cell_volume                     1507.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    7548
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.28
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless


_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   SADABS-2016/2

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_diffrn_reflns_number            21870
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3738
_reflns_number_gt                2749
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

#===============================================================================

# 8. REFINEMENT DATA

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0736P)²+1.0684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.5861(2) 0.5981(3) 0.60127(12) 0.0225(5) Uani 1 1 d . . .
H1 H 0.6482 0.5277 0.6278 0.027 Uiso 1 1 calc R . .
C2 C 0.6336(3) 0.6816(3) 0.54679(12) 0.0232(5) Uani 1 1 d . . .
H2 H 0.7298 0.6691 0.5380 0.028 Uiso 1 1 calc R . .
C3 C 0.5394(3) 0.7827(3) 0.50573(12) 0.0239(5) Uani 1 1 d . . .
H3 H 0.5726 0.8349 0.4691 0.029 Uiso 1 1 calc R . .
C4 C 0.3953(3) 0.8071(3) 0.51878(12) 0.0242(5) Uani 1 1 d . . .
H4 H 0.3314 0.8736 0.4909 0.029 Uiso 1 1 calc R . .
C5 C 0.3511(2) 0.7298(3) 0.57409(12) 0.0207(5) Uani 1 1 d . . .
C6 C 0.2061(2) 0.7191(3) 0.60256(11) 0.0205(5) Uani 1 1 d . . .
H6 H 0.1415 0.8102 0.5937 0.025 Uiso 1 1 calc R . .
C7 C 0.1374(2) 0.5630(3) 0.57499(11) 0.0192(4) Uani 1 1 d . . .
H7 H 0.1424 0.5500 0.5252 0.023 Uiso 1 1 calc R . .
C8 C 0.2377(2) 0.4434(2) 0.61966(11) 0.0186(4) Uani 1 1 d . . .
H8 H 0.2863 0.3716 0.5910 0.022 Uiso 1 1 calc R . .
C9 C 0.3487(2) 0.5532(3) 0.66393(11) 0.0199(4) Uani 1 1 d . . .
H9 H 0.4031 0.5062 0.7062 0.024 Uiso 1 1 calc R . .
C10 C 0.4443(2) 0.6238(3) 0.61440(11) 0.0203(4) Uani 1 1 d . . .
C11 C -0.0375(2) 0.5414(2) 0.71029(11) 0.0187(4) Uani 1 1 d . . .
C12 C -0.0839(2) 0.6957(3) 0.70313(12) 0.0218(5) Uani 1 1 d . . .
H12 H -0.0854 0.7469 0.6608 0.026 Uiso 1 1 calc R . .
C13 C -0.1280(2) 0.7734(3) 0.75930(12) 0.0242(5) Uani 1 1 d . . .
H13 H -0.1580 0.8769 0.7545 0.029 Uiso 1 1 calc R . .
C14 C -0.1278(3) 0.6976(3) 0.82261(13) 0.0265(5) Uani 1 1 d . . .
H14 H -0.1594 0.7492 0.8599 0.032 Uiso 1 1 calc R . .
C16 C -0.0799(3) 0.5444(3) 0.82950(12) 0.0258(5) Uani 1 1 d . . .
H16 H -0.0773 0.4938 0.8720 0.031 Uiso 1 1 calc R . .
C17 C -0.0360(2) 0.4656(3) 0.77385(12) 0.0228(5) Uani 1 1 d . . .
H17 H -0.0055 0.3622 0.7789 0.027 Uiso 1 1 calc R . .
C18 C 0.1299(2) 0.3591(2) 0.66040(12) 0.0197(4) Uani 1 1 d . . .
H18 H 0.1723 0.3516 0.7097 0.024 Uiso 1 1 calc R . .
C19 C 0.0930(3) 0.1977(3) 0.63091(13) 0.0263(5) Uani 1 1 d . . .
F1 F 0.03626(18) 0.20055(17) 0.56278(8) 0.0354(4) Uani 1 1 d . . .
F2 F 0.21463(16) 0.10771(16) 0.63692(9) 0.0372(4) Uani 1 1 d . . .
F3 F -0.00427(16) 0.12332(16) 0.66400(8) 0.0341(4) Uani 1 1 d . . .
N1 N -0.0070(2) 0.4503(2) 0.65259(9) 0.0204(4) Uani 1 1 d . . .
O1 O 0.25505(17) 0.68397(18) 0.67563(8) 0.0212(4) Uani 1 1 d . . .
O2 O -0.01028(16) 0.53900(18) 0.58955(8) 0.0209(3) 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 C10 1.379(3) . ?
C1 C2 1.399(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.402(3) . ?
C5 C6 1.517(3) . ?
C6 O1 1.453(3) . ?
C6 C7 1.540(3) . ?
C6 H6 0.9800 . ?
C7 O2 1.438(3) . ?
C7 C8 1.552(3) . ?
C7 H7 0.9800 . ?
C8 C18 1.536(3) . ?
C8 C9 1.548(3) . ?
C8 H8 0.9800 . ?
C9 O1 1.451(3) . ?
C9 C10 1.521(3) . ?
C9 H9 0.9800 . ?
C11 C12 1.390(3) . ?
C11 C17 1.393(3) . ?
C11 N1 1.427(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 C16 1.385(3) . ?
C14 H14 0.9300 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.466(3) . ?
C18 C19 1.516(3) . ?
C18 H18 0.9800 . ?
C19 F3 1.336(3) . ?
C19 F2 1.346(3) . ?
C19 F1 1.346(3) . ?
N1 O2 1.437(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
C10 C1 C2 117.8(2) . . ?
C10 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 117.9(2) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C10 121.5(2) . . ?
C4 C5 C6 133.8(2) . . ?
C10 C5 C6 104.50(19) . . ?
O1 C6 C5 102.14(17) . . ?
O1 C6 C7 102.08(16) . . ?
C5 C6 C7 105.14(17) . . ?
O1 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C7 C6 H6 115.2 . . ?
O2 C7 C6 113.81(18) . . ?
O2 C7 C8 106.93(17) . . ?
C6 C7 C8 101.70(16) . . ?
O2 C7 H7 111.3 . . ?
C6 C7 H7 111.3 . . ?
C8 C7 H7 111.3 . . ?
C18 C8 C9 114.84(18) . . ?
C18 C8 C7 103.04(17) . . ?
C9 C8 C7 101.12(16) . . ?
C18 C8 H8 112.3 . . ?
C9 C8 H8 112.3 . . ?
C7 C8 H8 112.3 . . ?
O1 C9 C10 101.66(17) . . ?
O1 C9 C8 101.66(16) . . ?
C10 C9 C8 106.50(17) . . ?
O1 C9 H9 115.1 . . ?
C10 C9 H9 115.1 . . ?
C8 C9 H9 115.1 . . ?
C1 C10 C5 120.8(2) . . ?
C1 C10 C9 134.6(2) . . ?
C5 C10 C9 104.49(19) . . ?
C12 C11 C17 119.6(2) . . ?
C12 C11 N1 122.4(2) . . ?
C17 C11 N1 117.59(19) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C16 C14 C13 119.1(2) . . ?
C16 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C17 C16 C14 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C14 C16 H16 119.6 . . ?
C16 C17 C11 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
C11 C17 H17 120.0 . . ?
N1 C18 C19 108.03(18) . . ?
N1 C18 C8 107.61(17) . . ?
C19 C18 C8 111.04(18) . . ?
N1 C18 H18 110.0 . . ?
C19 C18 H18 110.0 . . ?
C8 C18 H18 110.0 . . ?
F3 C19 F2 106.79(19) . . ?
F3 C19 F1 107.12(19) . . ?
F2 C19 F1 106.7(2) . . ?
F3 C19 C18 112.4(2) . . ?
F2 C19 C18 110.84(19) . . ?
F1 C19 C18 112.65(19) . . ?
C11 N1 O2 113.40(16) . . ?
C11 N1 C18 118.46(17) . . ?
O2 N1 C18 106.15(16) . . ?
C9 O1 C6 96.31(15) . . ?
N1 O2 C7 110.09(15) . . ?

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
C10 C1 C2 C3 -2.2(3) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C10 -3.0(3) . . . . ?
C3 C4 C5 C6 -176.6(2) . . . . ?
C4 C5 C6 O1 -153.8(2) . . . . ?
C10 C5 C6 O1 31.9(2) . . . . ?
C4 C5 C6 C7 99.9(3) . . . . ?
C10 C5 C6 C7 -74.4(2) . . . . ?
O1 C6 C7 O2 80.7(2) . . . . ?
C5 C6 C7 O2 -173.05(17) . . . . ?
O1 C6 C7 C8 -34.0(2) . . . . ?
C5 C6 C7 C8 72.3(2) . . . . ?
O2 C7 C8 C18 -1.8(2) . . . . ?
C6 C7 C8 C18 117.82(17) . . . . ?
O2 C7 C8 C9 -120.80(17) . . . . ?
C6 C7 C8 C9 -1.2(2) . . . . ?
C18 C8 C9 O1 -74.1(2) . . . . ?
C7 C8 C9 O1 36.05(19) . . . . ?
C18 C8 C9 C10 179.86(17) . . . . ?
C7 C8 C9 C10 -70.0(2) . . . . ?
C2 C1 C10 C5 0.2(3) . . . . ?
C2 C1 C10 C9 175.6(2) . . . . ?
C4 C5 C10 C1 2.5(3) . . . . ?
C6 C5 C10 C1 177.7(2) . . . . ?
C4 C5 C10 C9 -174.1(2) . . . . ?
C6 C5 C10 C9 1.0(2) . . . . ?
O1 C9 C10 C1 150.4(2) . . . . ?
C8 C9 C10 C1 -103.5(3) . . . . ?
O1 C9 C10 C5 -33.7(2) . . . . ?
C8 C9 C10 C5 72.4(2) . . . . ?
C17 C11 C12 C13 0.2(3) . . . . ?
N1 C11 C12 C13 172.7(2) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C16 1.4(3) . . . . ?
C13 C14 C16 C17 -1.5(4) . . . . ?
C14 C16 C17 C11 1.0(3) . . . . ?
C12 C11 C17 C16 -0.3(3) . . . . ?
N1 C11 C17 C16 -173.2(2) . . . . ?
C9 C8 C18 N1 95.7(2) . . . . ?
C7 C8 C18 N1 -13.3(2) . . . . ?
C9 C8 C18 C19 -146.25(19) . . . . ?
C7 C8 C18 C19 104.8(2) . . . . ?
N1 C18 C19 F3 -60.3(2) . . . . ?
C8 C18 C19 F3 -178.07(18) . . . . ?
N1 C18 C19 F2 -179.69(18) . . . . ?
C8 C18 C19 F2 62.5(2) . . . . ?
N1 C18 C19 F1 60.8(2) . . . . ?
C8 C18 C19 F1 -57.0(2) . . . . ?
C12 C11 N1 O2 7.7(3) . . . . ?
C17 C11 N1 O2 -179.68(17) . . . . ?
C12 C11 N1 C18 133.1(2) . . . . ?
C17 C11 N1 C18 -54.3(3) . . . . ?
C19 C18 N1 C11 134.8(2) . . . . ?
C8 C18 N1 C11 -105.2(2) . . . . ?
C19 C18 N1 O2 -96.3(2) . . . . ?
C8 C18 N1 O2 23.6(2) . . . . ?
C10 C9 O1 C6 51.99(18) . . . . ?
C8 C9 O1 C6 -57.82(18) . . . . ?
C5 C6 O1 C9 -51.53(18) . . . . ?
C7 C6 O1 C9 57.08(18) . . . . ?
C11 N1 O2 C7 106.25(19) . . . . ?
C18 N1 O2 C7 -25.5(2) . . . . ?
C6 C7 O2 N1 -94.68(19) . . . . ?
C8 C7 O2 N1 16.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.119

####################################################################
#                         END of data
####################################################################

