# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BM2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2232229'
loop_
_audit_author_name
_audit_author_address
'SUVAM BHATTACHARJEE'
;VISVA BHARATI
India
;
_audit_update_record             
;
2022-12-22 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 F3 N3 O2'
_chemical_formula_weight         447.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.571(4)
_cell_length_b                   21.464(8)
_cell_length_c                   8.872(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.385(9)
_cell_angle_gamma                90
_cell_volume                     2102.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9494
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      25.57

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68780
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3681
_reflns_number_gt                3100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.5980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3681
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F2 F 0.97990(12) 0.45088(5) 0.83757(16) 0.0865(4) Uani 1 1 d . . . . .
O1 O 0.71593(11) 0.66733(6) 0.88345(18) 0.0665(4) Uani 1 1 d . . . . .
F1 F 0.80042(12) 0.44358(5) 0.68263(17) 0.0866(4) Uani 1 1 d . . . . .
O2 O 1.06561(11) 0.58828(6) 0.82751(17) 0.0689(4) Uani 1 1 d . . . . .
F3 F 0.93790(15) 0.48665(6) 0.60478(17) 0.1012(5) Uani 1 1 d . . . . .
N2 N 0.60747(12) 0.48786(6) 0.82339(17) 0.0510(3) Uani 1 1 d . . . . .
N1 N 0.90406(12) 0.64578(6) 0.85638(19) 0.0555(4) Uani 1 1 d . . . . .
N3 N 0.43413(12) 0.53220(7) 0.67651(17) 0.0565(4) Uani 1 1 d . . . . .
C9 C 0.75968(14) 0.56589(7) 0.7883(2) 0.0492(4) Uani 1 1 d . . . . .
C10 C 0.78405(14) 0.63287(7) 0.8456(2) 0.0518(4) Uani 1 1 d . . . . .
C8 C 0.63876(14) 0.54170(7) 0.7570(2) 0.0498(4) Uani 1 1 d . . . . .
C7 C 0.52920(14) 0.56732(7) 0.66719(19) 0.0499(4) Uani 1 1 d . . . . .
C18 C 0.86651(15) 0.54279(8) 0.7825(2) 0.0515(4) Uani 1 1 d . . . . .
C6 C 0.51015(15) 0.62327(8) 0.5675(2) 0.0535(4) Uani 1 1 d . . . . .
C20 C 0.67642(17) 0.44616(8) 0.9304(2) 0.0608(5) Uani 1 1 d . . . . .
H00F H 0.760421 0.449240 0.964085 0.073 Uiso 1 1 calc R U . . .
C17 C 0.96072(15) 0.59221(8) 0.8237(2) 0.0542(4) Uani 1 1 d . . . . .
C11 C 0.96115(15) 0.70478(8) 0.9072(2) 0.0560(4) Uani 1 1 d . . . . .
C25 C 0.48193(15) 0.48525(8) 0.7743(2) 0.0536(4) Uani 1 1 d . . . . .
C23 C 0.42244(18) 0.43788(9) 0.8333(2) 0.0639(5) Uani 1 1 d . . . . .
C19 C 0.89479(17) 0.48118(8) 0.7258(2) 0.0595(4) Uani 1 1 d . . . . .
C5 C 0.5983(2) 0.64627(10) 0.5049(2) 0.0701(5) Uani 1 1 d . . . . .
H00L H 0.671371 0.625109 0.523370 0.084 Uiso 1 1 calc R U . . .
C24 C 0.28683(19) 0.43658(12) 0.7793(3) 0.0835(7) Uani 1 1 d . . . . .
H00A H 0.258631 0.430283 0.667104 0.125 Uiso 1 1 calc R U . . .
H00B H 0.256237 0.475448 0.805006 0.125 Uiso 1 1 calc R U . . .
H00C H 0.258719 0.403172 0.831218 0.125 Uiso 1 1 calc R U . . .
C22 C 0.4924(2) 0.39641(9) 0.9371(3) 0.0729(6) Uani 1 1 d . . . . .
H00N H 0.455457 0.364546 0.976781 0.087 Uiso 1 1 calc R U . . .
C1 C 0.40113(18) 0.65483(10) 0.5344(2) 0.0704(5) Uani 1 1 d . . . . .
H00O H 0.340042 0.639869 0.573011 0.084 Uiso 1 1 calc R U . . .
C21 C 0.6196(2) 0.40071(9) 0.9856(3) 0.0714(5) Uani 1 1 d . . . . .
H00P H 0.665172 0.371720 1.056785 0.086 Uiso 1 1 calc R U . . .
C12 C 0.91000(18) 0.75777(9) 0.8289(3) 0.0758(6) Uani 1 1 d . . . . .
H00Q H 0.841086 0.755335 0.742097 0.091 Uiso 1 1 calc R U . . .
C16 C 1.0643(2) 0.70809(10) 1.0328(3) 0.0777(6) Uani 1 1 d . . . . .
H00R H 1.099796 0.672067 1.084526 0.093 Uiso 1 1 calc R U . . .
C4 C 0.5791(2) 0.69993(10) 0.4158(3) 0.0825(6) Uani 1 1 d . . . . .
H00S H 0.639390 0.715128 0.376065 0.099 Uiso 1 1 calc R U . . .
C14 C 1.0634(2) 0.81903(10) 1.0071(3) 0.0829(6) Uani 1 1 d . . . . .
H00T H 1.096970 0.857693 1.042259 0.100 Uiso 1 1 calc R U . . .
C13 C 0.9623(2) 0.81498(10) 0.8808(4) 0.0893(8) Uani 1 1 d . . . . .
H00U H 0.927784 0.851090 0.828476 0.107 Uiso 1 1 calc R U . . .
C2 C 0.3827(2) 0.70838(12) 0.4443(3) 0.0923(7) Uani 1 1 d . . . . .
H00V H 0.309309 0.729428 0.423203 0.111 Uiso 1 1 calc R U . . .
C3 C 0.4715(3) 0.73083(11) 0.3857(3) 0.0889(7) Uani 1 1 d . . . . .
H00W H 0.458500 0.767072 0.325524 0.107 Uiso 1 1 calc R U . . .
C15 C 1.1149(2) 0.76605(12) 1.0816(3) 0.0937(8) Uani 1 1 d . . . . .
H00X H 1.185084 0.768697 1.166575 0.112 Uiso 1 1 calc R U . . .


_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
F2 C19 1.339(2) . ?
O1 C10 1.200(2) . ?
F1 C19 1.319(2) . ?
O2 C17 1.207(2) . ?
F3 C19 1.317(2) . ?
N2 C20 1.373(2) . ?
N2 C25 1.387(2) . ?
N2 C8 1.393(2) . ?
N1 C10 1.391(2) . ?
N1 C17 1.396(2) . ?
N1 C11 1.437(2) . ?
N3 C25 1.337(2) . ?
N3 C7 1.356(2) . ?
C9 C18 1.347(2) . ?
C9 C8 1.440(2) . ?
C9 C10 1.523(2) . ?
C8 C7 1.393(2) . ?
C7 C6 1.468(2) . ?
C18 C19 1.486(2) . ?
C18 C17 1.486(2) . ?
C6 C1 1.384(3) . ?
C6 C5 1.390(3) . ?
C20 C21 1.347(3) . ?
C11 C16 1.369(3) . ?
C11 C12 1.371(3) . ?
C25 C23 1.413(2) . ?
C23 C22 1.360(3) . ?
C23 C24 1.498(3) . ?
C5 C4 1.377(3) . ?
C22 C21 1.408(3) . ?
C1 C2 1.380(3) . ?
C12 C13 1.385(3) . ?
C16 C15 1.388(3) . ?
C4 C3 1.364(4) . ?
C14 C13 1.359(4) . ?
C14 C15 1.360(3) . ?
C2 C3 1.371(4) . ?

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
C20 N2 C25 121.90(15) . . ?
C20 N2 C8 131.46(15) . . ?
C25 N2 C8 106.29(13) . . ?
C10 N1 C17 110.05(13) . . ?
C10 N1 C11 123.56(14) . . ?
C17 N1 C11 126.19(14) . . ?
C25 N3 C7 105.82(14) . . ?
C18 C9 C8 135.23(16) . . ?
C18 C9 C10 106.25(14) . . ?
C8 C9 C10 118.50(13) . . ?
O1 C10 N1 125.74(16) . . ?
O1 C10 C9 127.15(15) . . ?
N1 C10 C9 106.99(13) . . ?
C7 C8 N2 105.19(14) . . ?
C7 C8 C9 129.34(15) . . ?
N2 C8 C9 125.31(14) . . ?
N3 C7 C8 111.22(15) . . ?
N3 C7 C6 120.84(15) . . ?
C8 C7 C6 127.90(15) . . ?
C9 C18 C19 129.65(16) . . ?
C9 C18 C17 109.99(15) . . ?
C19 C18 C17 119.93(15) . . ?
C1 C6 C5 118.20(18) . . ?
C1 C6 C7 119.44(16) . . ?
C5 C6 C7 122.37(16) . . ?
C21 C20 N2 118.51(18) . . ?
O2 C17 N1 125.61(17) . . ?
O2 C17 C18 127.92(16) . . ?
N1 C17 C18 106.47(13) . . ?
C16 C11 C12 120.55(18) . . ?
C16 C11 N1 120.53(16) . . ?
C12 C11 N1 118.91(17) . . ?
N3 C25 N2 111.40(14) . . ?
N3 C25 C23 129.04(17) . . ?
N2 C25 C23 119.52(17) . . ?
C22 C23 C25 117.66(18) . . ?
C22 C23 C24 124.00(18) . . ?
C25 C23 C24 118.33(19) . . ?
F3 C19 F1 107.49(17) . . ?
F3 C19 F2 105.86(16) . . ?
F1 C19 F2 106.23(15) . . ?
F3 C19 C18 111.84(15) . . ?
F1 C19 C18 113.31(15) . . ?
F2 C19 C18 111.66(16) . . ?
C4 C5 C6 121.0(2) . . ?
C23 C22 C21 121.38(18) . . ?
C2 C1 C6 120.3(2) . . ?
C20 C21 C22 121.01(19) . . ?
C11 C12 C13 119.2(2) . . ?
C11 C16 C15 119.0(2) . . ?
C3 C4 C5 120.0(2) . . ?
C13 C14 C15 119.4(2) . . ?
C14 C13 C12 120.9(2) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 119.9(2) . . ?
C14 C15 C16 121.0(2) . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.029



