# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_KRISHNA31_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc24ty86
_database_code_depnum_ccdc_archive 'CCDC 1991138'
loop_
_audit_author_name
_audit_author_address
'Krishna N. Tripathi' 'IIT Delhi'
_audit_update_record             
;
2020-03-18 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 F N O2'
_chemical_formula_sum            'C16 H16 F N O2'
_chemical_formula_weight         273.30

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'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.0253(3)
_cell_length_b                   10.4167(3)
_cell_length_c                   21.3841(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2901.41(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.07

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             1152.0
_exptl_transmission_factor_min   0.981
_exptl_transmission_factor_max   0.986
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.091
_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      296(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            104306
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.147
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3610
_reflns_number_gt                2805
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1000P)²+0.3052P] 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         3591
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_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
O2 O 0.70962(7) 0.50713(9) 0.62455(4) 0.0522(3) Uani 1 1 d . . . . .
F1 F 0.30587(7) 0.37573(10) 0.63547(5) 0.0760(3) Uani 1 1 d . . . . .
O1 O 0.83864(8) 0.62420(13) 0.58947(6) 0.0701(3) Uani 1 1 d . . . . .
C9 C 0.60680(9) 0.47743(11) 0.62510(5) 0.0426(3) Uani 1 1 d . . . . .
C8 C 0.53498(9) 0.54685(11) 0.59049(5) 0.0405(3) Uani 1 1 d . . . . .
C14 C 0.57009(9) 0.65457(11) 0.55338(5) 0.0409(3) Uani 1 1 d . . . . .
C12 C 0.67253(9) 0.67959(12) 0.55357(5) 0.0457(3) Uani 1 1 d . . . . .
C10 C 0.57843(11) 0.37550(12) 0.66323(6) 0.0481(3) Uani 1 1 d . . . . .
H10 H 0.6288 0.3319 0.6856 0.058 Uiso 1 1 calc R U . . .
C7 C 0.43236(9) 0.50840(12) 0.59533(6) 0.0464(3) Uani 1 1 d . . . . .
H7 H 0.3818 0.5515 0.5729 0.056 Uiso 1 1 calc R U . . .
N1 N 0.74242(11) 0.87415(14) 0.49260(7) 0.0746(4) Uani 1 1 d . . . . .
C5 C 0.47733(11) 0.33714(11) 0.66880(6) 0.0482(3) Uani 1 1 d . . . . .
C15 C 0.49574(10) 0.73851(12) 0.51894(6) 0.0486(3) Uani 1 1 d . . . . .
H15A H 0.4398 0.6865 0.5030 0.058 Uiso 1 1 calc R U . . .
H15B H 0.5301 0.7779 0.4836 0.058 Uiso 1 1 calc R U . . .
C11 C 0.74773(10) 0.60516(13) 0.58872(6) 0.0499(3) Uani 1 1 d . . . . .
C6 C 0.40660(10) 0.40739(13) 0.63302(6) 0.0500(3) Uani 1 1 d . . . . .
C13 C 0.71286(10) 0.78689(14) 0.51928(7) 0.0544(3) Uani 1 1 d . . . . .
C4 C 0.44425(14) 0.22705(14) 0.71175(7) 0.0626(4) Uani 1 1 d . . . . .
C16 C 0.45284(15) 0.84281(17) 0.56140(9) 0.0755(5) Uani 1 1 d . . . . .
H16A H 0.4189 0.8039 0.5964 0.113 Uiso 1 1 calc R U . . .
H16B H 0.4047 0.8942 0.5384 0.113 Uiso 1 1 calc R U . . .
H16C H 0.5079 0.8961 0.5761 0.113 Uiso 1 1 calc R U . . .
C1 C 0.53739(18) 0.1702(2) 0.74599(9) 0.0882(6) Uani 1 1 d . . . . .
H1A H 0.5153 0.1012 0.7725 0.132 Uiso 1 1 calc R U . . .
H1B H 0.5693 0.2356 0.7709 0.132 Uiso 1 1 calc R U . . .
H1C H 0.5858 0.1383 0.7159 0.132 Uiso 1 1 calc R U . . .
C3 C 0.37012(19) 0.2784(2) 0.76147(9) 0.0900(6) Uani 1 1 d . . . . .
H3A H 0.3109 0.3146 0.7414 0.135 Uiso 1 1 calc R U . . .
H3B H 0.4039 0.3433 0.7858 0.135 Uiso 1 1 calc R U . . .
H3C H 0.3492 0.2094 0.7884 0.135 Uiso 1 1 calc R U . . .
C2 C 0.3952(2) 0.12073(18) 0.67258(11) 0.1023(8) Uani 1 1 d . . . . .
H2A H 0.3332 0.1522 0.6538 0.153 Uiso 1 1 calc R U . . .
H2B H 0.3795 0.0488 0.6989 0.153 Uiso 1 1 calc R U . . .
H2C H 0.4421 0.0944 0.6404 0.153 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
O2 C11 1.3698(16) . ?
O2 C9 1.3746(15) . ?
F1 C6 1.3539(16) . ?
O1 C11 1.2006(16) . ?
C9 C10 1.3889(17) . ?
C9 C8 1.3949(16) . ?
C8 C7 1.3991(16) . ?
C8 C14 1.4485(16) . ?
C14 C12 1.3595(16) . ?
C14 C15 1.4982(16) . ?
C12 C13 1.4362(18) . ?
C12 C11 1.4580(18) . ?
C10 C5 1.3813(19) . ?
C10 H10 0.9300 . ?
C7 C6 1.3673(17) . ?
C7 H7 0.9300 . ?
N1 C13 1.1402(18) . ?
C5 C6 1.4035(19) . ?
C5 C4 1.5310(18) . ?
C15 C16 1.522(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 C2 1.528(3) . ?
C4 C3 1.532(2) . ?
C4 C1 1.536(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
C11 O2 C9 121.71(10) . . ?
O2 C9 C10 115.87(10) . . ?
O2 C9 C8 122.16(11) . . ?
C10 C9 C8 121.96(12) . . ?
C9 C8 C7 116.94(11) . . ?
C9 C8 C14 118.72(11) . . ?
C7 C8 C14 124.32(10) . . ?
C12 C14 C8 117.18(10) . . ?
C12 C14 C15 121.60(11) . . ?
C8 C14 C15 121.15(11) . . ?
C14 C12 C13 120.44(11) . . ?
C14 C12 C11 123.98(11) . . ?
C13 C12 C11 115.55(11) . . ?
C5 C10 C9 121.70(11) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C6 C7 C8 119.89(11) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C10 C5 C6 115.34(11) . . ?
C10 C5 C4 122.46(12) . . ?
C6 C5 C4 122.19(13) . . ?
C14 C15 C16 111.14(11) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O1 C11 O2 118.23(12) . . ?
O1 C11 C12 125.56(13) . . ?
O2 C11 C12 116.19(11) . . ?
F1 C6 C7 116.62(12) . . ?
F1 C6 C5 119.21(12) . . ?
C7 C6 C5 124.16(12) . . ?
N1 C13 C12 177.97(15) . . ?
C2 C4 C5 109.37(13) . . ?
C2 C4 C3 111.68(18) . . ?
C5 C4 C3 109.40(13) . . ?
C2 C4 C1 108.19(17) . . ?
C5 C4 C1 110.63(14) . . ?
C3 C4 C1 107.54(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030



