# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20190611
_database_code_depnum_ccdc_archive 'CCDC 2004916'
loop_
_audit_author_name
_audit_author_address
'Hyun Jin Kim'
;Korea Research Institue of Chemical Techonology
South Korea
;
_audit_update_record             
;
2020-05-20 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 F4 N O'
_chemical_formula_weight         261.22

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.1815(8)
_cell_length_b                   9.5647(4)
_cell_length_c                   7.4675(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.801(3)
_cell_angle_gamma                90.00
_cell_volume                     1227.06(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    5173
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      23.00

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2880
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         27.87
_reflns_number_total             2880
_reflns_number_gt                1980
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1258P)²+0.3316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.2321
_refine_ls_wR_factor_gt          0.2119
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.6177(8) 1.078(2) 0.544(2) 0.206(10) Uani 0.47(2) 1 d P A 1
F2A F 0.6454(17) 1.1904(11) 0.7840(18) 0.229(8) Uani 0.47(2) 1 d P A 1
F3A F 0.7221(6) 1.042(2) 0.6692(18) 0.154(6) Uani 0.53(2) 1 d P A 1
F1B F 0.6472(13) 1.031(2) 0.5306(16) 0.243(9) Uani 0.53(2) 1 d P A 2
F2B F 0.6130(4) 1.1844(11) 0.674(3) 0.170(7) Uani 0.53(2) 1 d P A 2
F3B F 0.7157(8) 1.1114(16) 0.744(3) 0.146(6) Uani 0.47(2) 1 d P A 2
F4 F 0.60881(12) 0.7992(3) 1.0257(4) 0.1422(12) Uani 1 1 d . A .
O1 O 1.00946(10) 0.73335(18) 1.1727(3) 0.0693(5) Uani 1 1 d . A .
N1 N 0.95731(11) 0.94868(18) 1.2083(3) 0.0534(5) Uani 1 1 d . A .
H1A H 0.9677 1.0314 1.2468 0.064 Uiso 1 1 calc R . .
C1 C 0.6473(2) 1.0703(4) 0.6994(6) 0.0958(11) Uani 1 1 d . . .
C2 C 0.61011(14) 0.9624(3) 0.8089(4) 0.0676(7) Uani 1 1 d . A .
C3 C 0.64883(14) 0.8974(3) 0.9361(4) 0.0674(7) Uani 1 1 d . . .
C4 C 0.72903(14) 0.9095(3) 1.0047(3) 0.0590(6) Uani 1 1 d . A .
C5 C 0.75149(16) 1.0198(3) 1.1145(4) 0.0708(7) Uani 1 1 d . . .
H5A H 0.7156 1.0888 1.1426 0.085 Uiso 1 1 calc R A .
C6 C 0.82618(14) 1.0283(2) 1.1822(4) 0.0643(7) Uani 1 1 d . A .
H6A H 0.8397 1.1020 1.2578 0.077 Uiso 1 1 calc R . .
C7 C 0.88168(13) 0.9286(2) 1.1394(3) 0.0501(5) Uani 1 1 d . . .
C8 C 0.85951(14) 0.8168(2) 1.0309(3) 0.0569(6) Uani 1 1 d . A .
H8A H 0.8956 0.7483 1.0018 0.068 Uiso 1 1 calc R . .
C9 C 0.78414(14) 0.8076(3) 0.9664(3) 0.0604(6) Uani 1 1 d . . .
H9A H 0.7698 0.7315 0.8956 0.072 Uiso 1 1 calc R A .
C10 C 1.01589(13) 0.8548(2) 1.2220(3) 0.0527(5) Uani 1 1 d . . .
C11 C 1.09036(14) 0.9102(3) 1.3034(4) 0.0669(7) Uani 1 1 d . A .
H11A H 1.1284 0.8368 1.3087 0.100 Uiso 1 1 calc R . .
H11B H 1.0807 0.9438 1.4222 0.100 Uiso 1 1 calc R . .
H11C H 1.1095 0.9855 1.2312 0.100 Uiso 1 1 calc R . .
C12 C 0.52521(17) 0.9362(4) 0.7642(5) 0.0924(10) Uani 1 1 d . . .
H12A H 0.5053 0.8652 0.8422 0.139 Uiso 1 1 calc R A .
H12B H 0.5202 0.9057 0.6421 0.139 Uiso 1 1 calc R . .
H12C H 0.4962 1.0210 0.7800 0.139 Uiso 1 1 calc R . .


_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
F1A C1 1.264(10) . ?
F2A C1 1.312(10) . ?
F3A C1 1.336(12) . ?
F1B C1 1.317(14) . ?
F2B C1 1.254(8) . ?
F3B C1 1.278(12) . ?
F4 C3 1.348(3) . ?
O1 C10 1.224(3) . ?
N1 C10 1.351(3) . ?
N1 C7 1.404(3) . ?
N1 H1A 0.8600 . ?
C1 C2 1.468(5) . ?
C2 C3 1.309(4) . ?
C2 C12 1.513(4) . ?
C3 C4 1.468(3) . ?
C4 C5 1.388(4) . ?
C4 C9 1.391(3) . ?
C5 C6 1.375(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.389(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.392(3) . ?
C8 C9 1.378(3) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.505(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C10 N1 C7 128.43(18) . . ?
C10 N1 H1A 115.8 . . ?
C7 N1 H1A 115.8 . . ?
F2B C1 F1A 67.9(9) . . ?
F2B C1 F3B 101.6(9) . . ?
F1A C1 F3B 125.1(11) . . ?
F2B C1 F2A 45.3(7) . . ?
F1A C1 F2A 112.2(11) . . ?
F3B C1 F2A 68.6(17) . . ?
F2B C1 F1B 96.2(10) . . ?
F1A C1 F1B 30.9(14) . . ?
F3B C1 F1B 108.9(15) . . ?
F2A C1 F1B 135.5(9) . . ?
F2B C1 F3A 127.0(8) . . ?
F1A C1 F3A 103.5(12) . . ?
F3B C1 F3A 39.0(8) . . ?
F2A C1 F3A 106.8(17) . . ?
F1B C1 F3A 76.6(13) . . ?
F2B C1 C2 119.4(5) . . ?
F1A C1 C2 112.4(6) . . ?
F3B C1 C2 118.6(6) . . ?
F2A C1 C2 109.5(7) . . ?
F1B C1 C2 109.6(8) . . ?
F3A C1 C2 112.3(7) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 C12 124.1(3) . . ?
C1 C2 C12 114.8(3) . . ?
C2 C3 F4 115.7(2) . . ?
C2 C3 C4 132.9(2) . . ?
F4 C3 C4 111.4(2) . . ?
C5 C4 C9 118.0(2) . . ?
C5 C4 C3 121.2(2) . . ?
C9 C4 C3 120.8(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 N1 117.19(19) . . ?
C8 C7 N1 124.2(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C4 121.5(2) . . ?
C8 C9 H9A 119.3 . . ?
C4 C9 H9A 119.3 . . ?
O1 C10 N1 123.0(2) . . ?
O1 C10 C11 121.9(2) . . ?
N1 C10 C11 115.1(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
F2B C1 C2 C3 -132.6(11) . . . . ?
F1A C1 C2 C3 151.1(13) . . . . ?
F3B C1 C2 C3 -7.9(13) . . . . ?
F2A C1 C2 C3 -83.6(15) . . . . ?
F1B C1 C2 C3 118.0(12) . . . . ?
F3A C1 C2 C3 34.9(10) . . . . ?
F2B C1 C2 C12 46.5(12) . . . . ?
F1A C1 C2 C12 -29.9(14) . . . . ?
F3B C1 C2 C12 171.1(12) . . . . ?
F2A C1 C2 C12 95.4(14) . . . . ?
F1B C1 C2 C12 -63.0(12) . . . . ?
F3A C1 C2 C12 -146.1(9) . . . . ?
C1 C2 C3 F4 -179.1(3) . . . . ?
C12 C2 C3 F4 2.0(4) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C12 C2 C3 C4 -177.8(3) . . . . ?
C2 C3 C4 C5 76.1(4) . . . . ?
F4 C3 C4 C5 -103.6(3) . . . . ?
C2 C3 C4 C9 -106.2(4) . . . . ?
F4 C3 C4 C9 74.1(3) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 C6 178.2(3) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C5 C6 C7 C8 -2.1(4) . . . . ?
C5 C6 C7 N1 177.4(2) . . . . ?
C10 N1 C7 C6 163.3(2) . . . . ?
C10 N1 C7 C8 -17.2(4) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
N1 C7 C8 C9 -178.6(2) . . . . ?
C7 C8 C9 C4 1.1(4) . . . . ?
C5 C4 C9 C8 -1.7(4) . . . . ?
C3 C4 C9 C8 -179.5(2) . . . . ?
C7 N1 C10 O1 0.0(4) . . . . ?
C7 N1 C10 C11 -179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.048
