# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_exp_1357-2
_database_code_depnum_ccdc_archive 'CCDC 1919367'
loop_
_audit_author_name
_audit_author_address
'Ikyon Kim'
;Yonsei University
South Korea
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2019-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F N3'
_chemical_formula_sum            'C19 H12 F N3'
_chemical_formula_weight         301.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H12 F N3'
_chemical_oxdiff_usercomment     BP-008
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.5685(6)
_cell_length_b                   8.4986(6)
_cell_length_c                   16.7749(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.930(6)
_cell_angle_gamma                90
_cell_volume                     1495.67(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    292.08(10)
_cell_measurement_theta_max      22.2400
_cell_measurement_theta_min      3.0720
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.247
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.579
_diffrn_reflns_theta_min         2.166
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.08(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   0.00   1.00    1.83    --  -11.04 -91.00   2.00   25
  2  ω    -45.00 -20.00   1.00    1.83    --  -11.04  91.00 115.00   25
  3  ω    -14.00  11.00   1.00    1.83    --   11.51 -91.00   2.00   25
  4  ω    -16.00  10.00   1.00    1.83    --  -11.04 -99.00 -90.00   26
  5  ω    -87.00  15.00   1.00    1.83    --  -11.04 -77.00-120.00  102
  6  ω    -50.00  -3.00   1.00    1.83    --  -11.04 -38.00 120.00   47
  7  ω    -12.00  84.00   1.00    1.83    --   11.51  38.00-180.00   96
  8  ω    -60.00  36.00   1.00    1.83    --   11.51 -38.00  90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0067258000
_diffrn_orient_matrix_UB_12      -0.0735470000
_diffrn_orient_matrix_UB_13      0.0200025000
_diffrn_orient_matrix_UB_21      -0.0257459000
_diffrn_orient_matrix_UB_22      0.0329828000
_diffrn_orient_matrix_UB_23      0.0333954000
_diffrn_orient_matrix_UB_31      -0.0621760000
_diffrn_orient_matrix_UB_32      -0.0216436000
_diffrn_orient_matrix_UB_33      -0.0172588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1865
_reflns_number_total             3729
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0079(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.2295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1534
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H00B), C3(H00C), C6(H00D), C21(H00E), C12(H00F), C19(H00G), C22(H00H),
 C15(H00I), C7(H00K), C20(H00L), C16(H00M), C17(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F001 F 0.86098(14) 0.05275(18) 0.43516(10) 0.0975(5) Uani 1 1 d . . . . .
N002 N 0.58082(15) 0.4452(2) 0.60116(10) 0.0525(5) Uani 1 1 d . . . . .
N003 N 0.48210(16) 0.2311(2) 0.54212(11) 0.0582(5) Uani 1 1 d . . . . .
N004 N 0.36891(16) 0.5443(2) 0.66493(11) 0.0625(5) Uani 1 1 d . . . . .
C005 C 0.46938(19) 0.3573(3) 0.58560(12) 0.0526(5) Uani 1 1 d . . . . .
C006 C 0.67259(19) 0.3645(2) 0.56268(12) 0.0529(5) Uani 1 1 d . . . . .
C007 C 0.71330(19) 0.6594(2) 0.66664(13) 0.0556(6) Uani 1 1 d . . . . .
C008 C 0.60781(19) 0.2342(2) 0.52731(12) 0.0538(5) Uani 1 1 d . . . . .
C009 C 0.3585(2) 0.4078(3) 0.61942(13) 0.0566(6) Uani 1 1 d . . . . .
C00A C 0.5880(2) 0.5809(2) 0.64890(13) 0.0570(6) Uani 1 1 d . . . . .
C00B C 0.7499(2) 0.7779(3) 0.61758(14) 0.0633(6) Uani 1 1 d . . . . .
H00B H 0.693264 0.813494 0.574614 0.076 Uiso 1 1 calc R . . . .
C00C C 0.6705(2) 0.1268(3) 0.48309(14) 0.0634(6) Uani 1 1 d . . . . .
H00C H 0.629227 0.039462 0.458764 0.076 Uiso 1 1 calc R . . . .
C00D C 0.8005(2) 0.3915(3) 0.55556(14) 0.0650(6) Uani 1 1 d . . . . .
H00D H 0.843226 0.478474 0.579278 0.078 Uiso 1 1 calc R . . . .
C00E C 0.9539(2) 0.7914(3) 0.69549(16) 0.0696(7) Uani 1 1 d . . . . .
H00E H 1.035243 0.834457 0.704672 0.084 Uiso 1 1 calc R . . . .
C00F C 0.4825(2) 0.6273(3) 0.67913(14) 0.0655(6) Uani 1 1 d . . . . .
H00F H 0.485450 0.717777 0.710506 0.079 Uiso 1 1 calc R . . . .
C00G C 0.7975(2) 0.6096(3) 0.73119(14) 0.0693(7) Uani 1 1 d . . . . .
H00G H 0.773410 0.531560 0.765145 0.083 Uiso 1 1 calc R . . . .
C00H C 0.8700(2) 0.8434(3) 0.63212(15) 0.0692(7) Uani 1 1 d . . . . .
H00H H 0.894047 0.922854 0.598938 0.083 Uiso 1 1 calc R . . . .
C00I C 0.2380(2) 0.3495(3) 0.61968(15) 0.0686(7) Uani 1 1 d . . . . .
H00I H 0.205158 0.258985 0.593797 0.082 Uiso 1 1 calc R . . . .
C00J C 0.7954(2) 0.1567(3) 0.47748(15) 0.0693(7) Uani 1 1 d . . . . .
C00K C 0.8614(2) 0.2842(3) 0.51200(16) 0.0720(7) Uani 1 1 d . . . . .
H00K H 0.947017 0.297629 0.505866 0.086 Uiso 1 1 calc R . . . .
C00L C 0.9178(2) 0.6760(3) 0.74533(15) 0.0735(7) Uani 1 1 d . . . . .
H00L H 0.974321 0.642163 0.788742 0.088 Uiso 1 1 calc R . . . .
C00M C 0.1733(2) 0.4517(3) 0.66621(17) 0.0791(8) Uani 1 1 d . . . . .
H00M H 0.089343 0.440737 0.676814 0.095 Uiso 1 1 calc R . . . .
C00N C 0.2542(2) 0.5700(3) 0.69330(16) 0.0788(8) Uani 1 1 d . . . . .
H00N H 0.235083 0.653754 0.725473 0.095 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F001 0.0933(11) 0.0852(10) 0.1222(14) -0.0263(9) 0.0465(9) -0.0093(9)
N002 0.0515(10) 0.0508(10) 0.0540(11) 0.0028(8) 0.0017(8) -0.0087(8)
N003 0.0567(11) 0.0606(12) 0.0566(12) -0.0014(9) 0.0032(8) -0.0101(9)
N004 0.0555(11) 0.0607(12) 0.0715(13) 0.0018(10) 0.0085(9) -0.0016(10)
C005 0.0520(12) 0.0563(13) 0.0478(13) 0.0067(11) -0.0015(9) -0.0058(11)
C006 0.0566(13) 0.0524(13) 0.0494(13) 0.0060(10) 0.0052(10) -0.0059(11)
C007 0.0563(13) 0.0535(13) 0.0558(14) -0.0053(11) 0.0020(10) -0.0065(11)
C008 0.0545(13) 0.0555(13) 0.0506(14) 0.0030(10) 0.0033(10) -0.0065(11)
C009 0.0544(13) 0.0596(14) 0.0546(14) 0.0045(11) 0.0013(10) -0.0022(11)
C00A 0.0622(14) 0.0500(13) 0.0578(14) 0.0003(11) 0.0029(11) -0.0074(11)
C00B 0.0653(14) 0.0633(14) 0.0594(15) -0.0022(11) -0.0008(11) -0.0098(12)
C00C 0.0716(15) 0.0581(14) 0.0606(15) -0.0033(11) 0.0081(11) -0.0110(12)
C00D 0.0572(14) 0.0611(14) 0.0768(17) -0.0024(12) 0.0089(12) -0.0133(12)
C00E 0.0606(14) 0.0724(17) 0.0747(18) -0.0207(14) 0.0039(12) -0.0089(13)
C00F 0.0666(15) 0.0586(14) 0.0704(17) -0.0042(12) 0.0051(12) -0.0047(12)
C00G 0.0742(16) 0.0719(16) 0.0592(16) 0.0046(12) -0.0020(12) -0.0094(13)
C00H 0.0685(15) 0.0651(15) 0.0742(17) -0.0016(12) 0.0099(13) -0.0152(13)
C00I 0.0571(14) 0.0722(16) 0.0758(18) 0.0057(13) 0.0058(12) -0.0065(13)
C00J 0.0747(16) 0.0643(15) 0.0728(17) -0.0038(13) 0.0253(13) -0.0021(14)
C00K 0.0616(14) 0.0681(16) 0.0890(19) -0.0021(14) 0.0203(13) -0.0106(13)
C00L 0.0717(16) 0.0841(18) 0.0601(17) -0.0100(14) -0.0102(12) -0.0032(14)
C00M 0.0583(14) 0.0817(18) 0.099(2) 0.0068(16) 0.0176(14) -0.0037(15)
C00N 0.0701(16) 0.0767(18) 0.093(2) -0.0026(15) 0.0224(14) 0.0090(14)

_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
F001 C00J 1.373(3) . ?
N002 C005 1.392(2) . ?
N002 C006 1.407(3) . ?
N002 C00A 1.401(3) . ?
N003 C005 1.313(3) . ?
N003 C008 1.381(3) . ?
N004 C009 1.386(3) . ?
N004 C00F 1.388(3) . ?
N004 C00N 1.372(3) . ?
C005 C009 1.428(3) . ?
C006 C008 1.397(3) . ?
C006 C00D 1.391(3) . ?
C007 C00A 1.481(3) . ?
C007 C00B 1.385(3) . ?
C007 C00G 1.382(3) . ?
C008 C00C 1.393(3) . ?
C009 C00I 1.367(3) . ?
C00A C00F 1.339(3) . ?
C00B H00B 0.9300 . ?
C00B C00H 1.380(3) . ?
C00C H00C 0.9300 . ?
C00C C00J 1.358(3) . ?
C00D H00D 0.9300 . ?
C00D C00K 1.376(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.373(3) . ?
C00E C00L 1.373(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00L 1.384(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00M 1.400(3) . ?
C00J C00K 1.377(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.362(3) . ?
C00N H00N 0.9300 . ?

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
C005 N002 C006 105.49(17) . . ?
C005 N002 C00A 122.34(18) . . ?
C00A N002 C006 132.13(17) . . ?
C005 N003 C008 104.48(17) . . ?
C009 N004 C00F 122.0(2) . . ?
C00N N004 C009 108.05(19) . . ?
C00N N004 C00F 129.9(2) . . ?
N002 C005 C009 118.70(19) . . ?
N003 C005 N002 113.66(19) . . ?
N003 C005 C009 127.61(19) . . ?
C008 C006 N002 104.58(17) . . ?
C00D C006 N002 133.7(2) . . ?
C00D C006 C008 121.7(2) . . ?
C00B C007 C00A 121.02(19) . . ?
C00G C007 C00A 119.7(2) . . ?
C00G C007 C00B 119.2(2) . . ?
N003 C008 C006 111.80(19) . . ?
N003 C008 C00C 127.8(2) . . ?
C00C C008 C006 120.4(2) . . ?
N004 C009 C005 117.15(19) . . ?
C00I C009 N004 108.3(2) . . ?
C00I C009 C005 134.6(2) . . ?
N002 C00A C007 118.12(19) . . ?
C00F C00A N002 118.00(19) . . ?
C00F C00A C007 123.8(2) . . ?
C007 C00B H00B 119.8 . . ?
C00H C00B C007 120.3(2) . . ?
C00H C00B H00B 119.8 . . ?
C008 C00C H00C 121.9 . . ?
C00J C00C C008 116.3(2) . . ?
C00J C00C H00C 121.9 . . ?
C006 C00D H00D 121.4 . . ?
C00K C00D C006 117.3(2) . . ?
C00K C00D H00D 121.4 . . ?
C00H C00E H00E 120.0 . . ?
C00H C00E C00L 120.0(2) . . ?
C00L C00E H00E 120.0 . . ?
N004 C00F H00F 119.1 . . ?
C00A C00F N004 121.8(2) . . ?
C00A C00F H00F 119.1 . . ?
C007 C00G H00G 120.0 . . ?
C007 C00G C00L 120.1(2) . . ?
C00L C00G H00G 120.0 . . ?
C00B C00H H00H 120.0 . . ?
C00E C00H C00B 120.1(2) . . ?
C00E C00H H00H 120.0 . . ?
C009 C00I H00I 126.4 . . ?
C009 C00I C00M 107.2(2) . . ?
C00M C00I H00I 126.4 . . ?
F001 C00J C00K 117.5(2) . . ?
C00C C00J F001 118.1(2) . . ?
C00C C00J C00K 124.4(2) . . ?
C00D C00K C00J 119.9(2) . . ?
C00D C00K H00K 120.0 . . ?
C00J C00K H00K 120.0 . . ?
C00E C00L C00G 120.2(2) . . ?
C00E C00L H00L 119.9 . . ?
C00G C00L H00L 119.9 . . ?
C00I C00M H00M 125.8 . . ?
C00N C00M C00I 108.3(2) . . ?
C00N C00M H00M 125.8 . . ?
N004 C00N H00N 125.9 . . ?
C00M C00N N004 108.2(2) . . ?
C00M C00N H00N 125.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.763
