# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_FAKMAG_EITDB00401
_database_code_depnum_ccdc_archive 'CCDC 1914375'
loop_
_audit_author_name
_audit_author_address
'K .Faust'
;Johannes Kepler University Linz
Austria
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            EIT_DB_004_01
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 F N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         282.27

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0852(7)
_cell_length_b                   7.8019(6)
_cell_length_c                   21.7718(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.796(3)
_cell_angle_gamma                90
_cell_volume                     1360.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    796
_cell_measurement_theta_min      1.9488
_cell_measurement_theta_max      19.4789
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.888
_exptl_crystal_size_mid          0.843
_exptl_crystal_size_min          0.754
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   Mo
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 Quest Eco'
_diffrn_measurement_method       omega

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            39934
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             2499
_reflns_number_gt                2070
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1099
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         2499
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.4302P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.043(4)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'publCIF, Diamond 3.2k'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.42778(12) 0.63827(15) 0.47494(5) 0.0656(3) Uani d . . . 1 . .
C C1 0.30151(19) 0.7284(2) 0.43898(7) 0.0452(4) Uani d . . . 1 . .
N N1 0.23909(16) 0.63471(18) 0.38447(6) 0.0467(4) Uani d . . . 1 . .
O O1 -0.01337(15) 0.53004(19) 0.33836(6) 0.0667(4) Uani d . . . 1 . .
O O2 0.61511(18) 0.51277(19) 0.19367(6) 0.0700(4) Uani d . . . 1 . .
C C2 0.15210(19) 0.7484(2) 0.47278(7) 0.0432(4) Uani d . . . 1 . .
N N2 0.4378(2) 1.0185(2) 0.41221(10) 0.0804(6) Uani d . . . 1 . .
C C6 -0.1380(2) 0.6705(2) 0.45834(8) 0.0531(4) Uani d . . . 1 . .
H H6 -0.230222 0.621902 0.434438 0.064 Uiso calc U . R 1 . .
C C5 -0.1501(2) 0.7399(2) 0.51582(9) 0.0575(5) Uani d . . . 1 . .
H H5 -0.2523 0.738601 0.530927 0.069 Uiso calc U . R 1 . .
C C4 -0.0127(3) 0.8113(2) 0.55131(8) 0.0588(5) Uani d . . . 1 . .
H H4 -0.02407 0.856868 0.589997 0.071 Uiso calc U . R 1 . .
C C3 0.1418(2) 0.8165(2) 0.53036(8) 0.0527(4) Uani d . . . 1 . .
H H3 0.234562 0.864028 0.554273 0.063 Uiso calc U . R 1 . .
C C7 0.01580(19) 0.6757(2) 0.43754(7) 0.0439(4) Uani d . . . 1 . .
C C9 0.3801(2) 0.8916(2) 0.42398(8) 0.0538(4) Uani d . . . 1 . .
C C8 0.06822(19) 0.6034(2) 0.38059(8) 0.0471(4) Uani d . . . 1 . .
C C10 0.33703(19) 0.5983(2) 0.33594(7) 0.0441(4) Uani d . . . 1 . .
C C11 0.4622(2) 0.4776(2) 0.34424(8) 0.0487(4) Uani d . . . 1 . .
H H11 0.481806 0.417042 0.381307 0.058 Uiso calc U . R 1 . .
C C12 0.5593(2) 0.4457(2) 0.29769(8) 0.0502(4) Uani d . . . 1 . .
H H12 0.645139 0.36558 0.303739 0.06 Uiso calc U . R 1 . .
C C13 0.5281(2) 0.5331(2) 0.24256(8) 0.0477(4) Uani d . . . 1 . .
C C14 0.4003(2) 0.6519(2) 0.23405(9) 0.0613(5) Uani d . . . 1 . .
H H14 0.377933 0.709956 0.196525 0.074 Uiso calc U . R 1 . .
C C15 0.3065(2) 0.6847(2) 0.28060(8) 0.0591(5) Uani d . . . 1 . .
H H15 0.221586 0.765952 0.274695 0.071 Uiso calc U . R 1 . .
C C16 0.7576(2) 0.4037(3) 0.20127(10) 0.0714(6) Uani d . . . 1 . .
H H16A 0.723493 0.288474 0.208666 0.107 Uiso calc U . R 1 . .
H H16B 0.834795 0.442334 0.235901 0.107 Uiso calc U . R 1 . .
H H16C 0.810424 0.406657 0.164382 0.107 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.3903(18) ?
C1 N1 . 1.427(2) ?
C1 C9 . 1.479(2) ?
C1 C2 . 1.505(2) ?
N1 C8 . 1.394(2) ?
N1 C10 . 1.432(2) ?
O1 C8 . 1.201(2) ?
O2 C13 . 1.362(2) ?
O2 C16 . 1.424(2) ?
C2 C3 . 1.374(2) ?
C2 C7 . 1.377(2) ?
N2 C9 . 1.138(2) ?
C6 C5 . 1.379(3) ?
C6 C7 . 1.381(2) ?
C6 H6 . 0.93 ?
C5 C4 . 1.381(3) ?
C5 H5 . 0.93 ?
C4 C3 . 1.388(3) ?
C4 H4 . 0.93 ?
C3 H3 . 0.93 ?
C7 C8 . 1.476(2) ?
C10 C15 . 1.373(2) ?
C10 C11 . 1.377(2) ?
C11 C12 . 1.386(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.374(2) ?
C12 H12 . 0.93 ?
C13 C14 . 1.382(2) ?
C14 C15 . 1.370(3) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 C1 N1 . . 111.05(13) ?
F1 C1 C9 . . 104.78(13) ?
N1 C1 C9 . . 111.81(14) ?
F1 C1 C2 . . 110.72(13) ?
N1 C1 C2 . . 104.06(12) ?
C9 C1 C2 . . 114.58(14) ?
C8 N1 C1 . . 112.09(13) ?
C8 N1 C10 . . 124.28(13) ?
C1 N1 C10 . . 123.14(13) ?
C13 O2 C16 . . 118.31(15) ?
C3 C2 C7 . . 121.65(15) ?
C3 C2 C1 . . 129.62(15) ?
C7 C2 C1 . . 108.65(13) ?
C5 C6 C7 . . 117.63(16) ?
C5 C6 H6 . . 121.2 ?
C7 C6 H6 . . 121.2 ?
C6 C5 C4 . . 121.04(17) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C4 C3 . . 121.28(17) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C2 C3 C4 . . 117.20(16) ?
C2 C3 H3 . . 121.4 ?
C4 C3 H3 . . 121.4 ?
C2 C7 C6 . . 121.20(15) ?
C2 C7 C8 . . 109.04(14) ?
C6 C7 C8 . . 129.67(15) ?
N2 C9 C1 . . 178.8(2) ?
O1 C8 N1 . . 124.51(15) ?
O1 C8 C7 . . 129.39(15) ?
N1 C8 C7 . . 106.10(13) ?
C15 C10 C11 . . 119.51(16) ?
C15 C10 N1 . . 119.88(14) ?
C11 C10 N1 . . 120.61(15) ?
C10 C11 C12 . . 120.40(15) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 119.65(15) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
O2 C13 C12 . . 124.86(15) ?
O2 C13 C14 . . 115.42(15) ?
C12 C13 C14 . . 119.72(16) ?
C15 C14 C13 . . 120.34(16) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C10 . . 120.36(16) ?
C14 C15 H15 . . 119.8 ?
C10 C15 H15 . . 119.8 ?
O2 C16 H16A . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?




_publcif_funding_html            
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